diff --git a/.agents/skills/launch/SKILL.md b/.agents/skills/launch/SKILL.md
new file mode 100644
index 0000000000000..f967f6d0c1d30
--- /dev/null
+++ b/.agents/skills/launch/SKILL.md
@@ -0,0 +1,350 @@
+---
+name: launch
+description: "Launch and automate VS Code (Code OSS) using agent-browser via Chrome DevTools Protocol. Use when you need to interact with the VS Code UI, automate the chat panel, test UI features, or take screenshots of VS Code. Triggers include 'automate VS Code', 'interact with chat', 'test the UI', 'take a screenshot', 'launch Code OSS with debugging'."
+metadata:
+  allowed-tools: Bash(agent-browser:*), Bash(npx agent-browser:*)
+---
+
+# VS Code Automation
+
+Automate VS Code (Code OSS) using agent-browser. VS Code is built on Electron/Chromium and exposes a Chrome DevTools Protocol (CDP) port that agent-browser can connect to, enabling the same snapshot-interact workflow used for web pages.
+
+## Prerequisites
+
+- **`agent-browser` must be installed.** It's listed in devDependencies — run `npm install` in the repo root. Use `npx agent-browser` if it's not on your PATH, or install globally with `npm install -g agent-browser`.
+- **For Code OSS (VS Code dev build):** The repo must be built before launching. `./scripts/code.sh` runs the build automatically if needed, or set `VSCODE_SKIP_PRELAUNCH=1` to skip the compile step if you've already built.
+- **CSS selectors are internal implementation details.** Selectors like `.interactive-input-part`, `.interactive-input-editor`, and `.part.auxiliarybar` used in `eval` commands are VS Code internals that may change across versions. If they stop working, use `agent-browser snapshot -i` to re-discover the current DOM structure.
+
+## Core Workflow
+
+1. **Launch** Code OSS with remote debugging enabled
+2. **Connect** agent-browser to the CDP port
+3. **Snapshot** to discover interactive elements
+4. **Interact** using element refs
+5. **Re-snapshot** after navigation or state changes
+
+> **📸 Take screenshots for a paper trail.** Use `agent-browser screenshot <path>` at key moments — after launch, before/after interactions, and when something goes wrong. Screenshots provide visual proof of what the UI looked like and are invaluable for debugging failures or documenting what was accomplished.
+>
+> Save screenshots inside a timestamped subfolder so each run is isolated and nothing gets overwritten:
+>
+> ```bash
+> # Create a timestamped folder for this run's screenshots
+> SCREENSHOT_DIR="/tmp/code-oss-screenshots/$(date +%Y-%m-%dT%H-%M-%S)"
+> mkdir -p "$SCREENSHOT_DIR"
+>
+> # Save a screenshot (path is a positional argument — use ./ or absolute paths)
+> # Bare filenames without ./ may be misinterpreted as CSS selectors
+> agent-browser screenshot "$SCREENSHOT_DIR/after-launch.png"
+> ```
+
+```bash
+# Launch Code OSS with remote debugging
+./scripts/code.sh --remote-debugging-port=9224
+
+# Wait for Code OSS to start, retry until connected
+for i in 1 2 3 4 5; do agent-browser connect 9224 2>/dev/null && break || sleep 3; done
+
+# Verify you're connected to the right target (not about:blank)
+# If `tab` shows the wrong target, run `agent-browser close` and reconnect
+agent-browser tab
+
+# Discover UI elements
+agent-browser snapshot -i
+
+# Focus the chat input (macOS)
+agent-browser press Control+Meta+i
+```
+
+## Connecting
+
+```bash
+# Connect to a specific port
+agent-browser connect 9222
+
+# Or use --cdp on each command
+agent-browser --cdp 9222 snapshot -i
+
+# Auto-discover a running Chromium-based app
+agent-browser --auto-connect snapshot -i
+```
+
+After `connect`, all subsequent commands target the connected app without needing `--cdp`.
+
+## Tab Management
+
+Electron apps often have multiple windows or webviews. Use tab commands to list and switch between them:
+
+```bash
+# List all available targets (windows, webviews, etc.)
+agent-browser tab
+
+# Switch to a specific tab by index
+agent-browser tab 2
+
+# Switch by URL pattern
+agent-browser tab --url "*settings*"
+```
+
+## Launching Code OSS (VS Code Dev Build)
+
+The VS Code repository includes `scripts/code.sh` which launches Code OSS from source. It passes all arguments through to the Electron binary, so `--remote-debugging-port` works directly:
+
+```bash
+cd <repo-root>  # the root of your VS Code checkout
+./scripts/code.sh --remote-debugging-port=9224
+```
+
+Wait for the window to fully initialize, then connect:
+
+```bash
+# Wait for Code OSS to start, retry until connected
+for i in 1 2 3 4 5; do agent-browser connect 9224 2>/dev/null && break || sleep 3; done
+
+# Verify you're connected to the right target (not about:blank)
+# If `tab` shows the wrong target, run `agent-browser close` and reconnect
+agent-browser tab
+agent-browser snapshot -i
+```
+
+**Tips:**
+- Set `VSCODE_SKIP_PRELAUNCH=1` to skip the compile step if you've already built: `VSCODE_SKIP_PRELAUNCH=1 ./scripts/code.sh --remote-debugging-port=9224` (from the repo root)
+- Code OSS uses the default user data directory. Unlike VS Code Insiders, you don't typically need `--user-data-dir` since there's usually only one Code OSS instance running.
+- If you see "Sent env to running instance. Terminating..." it means Code OSS is already running and forwarded your args to the existing instance. Quit Code OSS and relaunch with the flag, or use `--user-data-dir=/tmp/code-oss-debug` to force a new instance.
+
+## Launching VS Code Extensions for Debugging
+
+To debug a VS Code extension via agent-browser, launch VS Code Insiders with `--extensionDevelopmentPath` and `--remote-debugging-port`. Use `--user-data-dir` to avoid conflicting with an already-running instance.
+
+```bash
+# Build the extension first
+cd <extension-repo-root>  # e.g., the root of your extension checkout
+npm run compile
+
+# Launch VS Code Insiders with the extension and CDP
+code-insiders \
+  --extensionDevelopmentPath="<extension-repo-root>" \
+  --remote-debugging-port=9223 \
+  --user-data-dir=/tmp/vscode-ext-debug
+
+# Wait for VS Code to start, retry until connected
+for i in 1 2 3 4 5; do agent-browser connect 9223 2>/dev/null && break || sleep 3; done
+
+# Verify you're connected to the right target (not about:blank)
+# If `tab` shows the wrong target, run `agent-browser close` and reconnect
+agent-browser tab
+agent-browser snapshot -i
+```
+
+**Key flags:**
+- `--extensionDevelopmentPath=<path>` — loads your extension from source (must be compiled first)
+- `--remote-debugging-port=9223` — enables CDP (use 9223 to avoid conflicts with other apps on 9222)
+- `--user-data-dir=<path>` — uses a separate profile so it starts a new process instead of sending to an existing VS Code instance
+
+**Without `--user-data-dir`**, VS Code detects the running instance, forwards the args to it, and exits immediately — you'll see "Sent env to running instance. Terminating..." and CDP never starts.
+
+## Restarting After Code Changes
+
+**After making changes to Code OSS source code, you must restart to pick up the new build.** The workbench loads the compiled JavaScript at startup — changes are not hot-reloaded.
+
+### Restart Workflow
+
+1. **Rebuild** the changed code
+2. **Kill** the running Code OSS instance
+3. **Relaunch** with the same flags
+
+```bash
+# 1. Ensure your build is up to date.
+#    Normally you can skip a manual step here and let ./scripts/code.sh in step 3
+#    trigger the build when needed (or run `npm run watch` in another terminal).
+
+# 2. Kill the Code OSS instance listening on the debug port (if running)
+pids=$(lsof -t -i :9224)
+if [ -n "$pids" ]; then
+	kill $pids
+fi
+
+# 3. Relaunch
+./scripts/code.sh --remote-debugging-port=9224
+
+# 4. Reconnect agent-browser
+for i in 1 2 3 4 5; do agent-browser connect 9224 2>/dev/null && break || sleep 3; done
+agent-browser tab
+agent-browser snapshot -i
+```
+
+> **Tip:** If you're iterating frequently, run `npm run watch` in a separate terminal so compilation happens automatically. You still need to kill and relaunch Code OSS to load the new build.
+
+## Interacting with Monaco Editor (Chat Input, Code Editors)
+
+VS Code uses Monaco Editor for all text inputs including the Copilot Chat input. Monaco editors require specific agent-browser techniques — standard `click`, `fill`, and `keyboard type` commands may not work depending on the VS Code build.
+
+### The Universal Pattern: Focus via Keyboard Shortcut + `press`
+
+This works on **all** VS Code builds (Code OSS, Insiders, stable):
+
+```bash
+# 1. Open and focus the chat input with the keyboard shortcut
+# macOS:
+agent-browser press Control+Meta+i
+# Linux / Windows:
+agent-browser press Control+Alt+i
+
+# 2. Type using individual press commands
+agent-browser press H
+agent-browser press e
+agent-browser press l
+agent-browser press l
+agent-browser press o
+agent-browser press Space  # Use "Space" for spaces
+agent-browser press w
+agent-browser press o
+agent-browser press r
+agent-browser press l
+agent-browser press d
+
+# Verify text appeared (optional)
+agent-browser eval '
+(() => {
+  const sidebar = document.querySelector(".part.auxiliarybar");
+  const viewLines = sidebar.querySelectorAll(".interactive-input-editor .view-line");
+  return Array.from(viewLines).map(vl => vl.textContent).join("|");
+})()'
+
+# 3. Send the message (same on all platforms)
+agent-browser press Enter
+```
+
+**Chat focus shortcut by platform:**
+- **macOS:** `Ctrl+Cmd+I` → `agent-browser press Control+Meta+i`
+- **Linux:** `Ctrl+Alt+I` → `agent-browser press Control+Alt+i`
+- **Windows:** `Ctrl+Alt+I` → `agent-browser press Control+Alt+i`
+
+This shortcut focuses the chat input and sets `document.activeElement` to a `DIV` with class `native-edit-context` — VS Code's native text editing surface that correctly processes key events from `agent-browser press`.
+
+### `type @ref` — Works on Some Builds
+
+On VS Code Insiders (extension debug mode), `type @ref` handles focus and input in one step:
+
+```bash
+agent-browser snapshot -i
+# Look for: textbox "The editor is not accessible..." [ref=e62]
+agent-browser type @e62 "Hello from George!"
+```
+
+> **Tip:** If `type @ref` silently drops text (the editor stays empty), the ref may be stale or the editor not yet ready. Re-snapshot to get a fresh ref and try again. You can verify text was entered using the snippet in "Verifying Text and Clearing" below.
+
+However, **`type @ref` silently fails on Code OSS** — the command completes without error but no text appears. This also applies to `keyboard type` and `keyboard inserttext`. Always verify text appeared after typing, and fall back to the keyboard shortcut + `press` pattern if it didn't. The `press`-per-key approach works universally across all builds.
+
+> **⚠️ Warning:** `keyboard type` can hang indefinitely in some focus states (e.g., after JS mouse events). If it doesn't return within a few seconds, interrupt it and fall back to `press` for individual keystrokes.
+
+### Compatibility Matrix
+
+| Method | VS Code Insiders | Code OSS |
+|--------|-----------------|----------|
+| `press` per key (after focus shortcut) | ✅ Works | ✅ Works |
+| `type @ref` | ✅ Works | ❌ Silent fail |
+| `keyboard type` (after focus) | ✅ Works | ❌ Silent fail |
+| `keyboard inserttext` (after focus) | ✅ Works | ❌ Silent fail |
+| `click @ref` | ❌ Blocked by overlay | ❌ Blocked by overlay |
+| `fill @ref` | ❌ Element not visible | ❌ Element not visible |
+
+### Fallback: Focus via JavaScript Mouse Events
+
+If the keyboard shortcut doesn't work (e.g., chat panel isn't configured), you can focus the editor via JavaScript:
+
+```bash
+agent-browser eval '
+(() => {
+  const inputPart = document.querySelector(".interactive-input-part");
+  const editor = inputPart.querySelector(".monaco-editor");
+  const rect = editor.getBoundingClientRect();
+  const x = rect.x + rect.width / 2;
+  const y = rect.y + rect.height / 2;
+  editor.dispatchEvent(new MouseEvent("mousedown", { bubbles: true, clientX: x, clientY: y }));
+  editor.dispatchEvent(new MouseEvent("mouseup", { bubbles: true, clientX: x, clientY: y }));
+  editor.dispatchEvent(new MouseEvent("click", { bubbles: true, clientX: x, clientY: y }));
+  return "activeElement: " + document.activeElement?.className;
+})()'
+
+# Then use press for each character
+agent-browser press H
+agent-browser press e
+# ...
+```
+
+### Verifying Text and Clearing
+
+```bash
+# Verify text in the chat input
+agent-browser eval '
+(() => {
+  const sidebar = document.querySelector(".part.auxiliarybar");
+  const viewLines = sidebar.querySelectorAll(".interactive-input-editor .view-line");
+  return Array.from(viewLines).map(vl => vl.textContent).join("|");
+})()'
+
+# Clear the input (Select All + Backspace)
+# macOS:
+agent-browser press Meta+a
+# Linux / Windows:
+agent-browser press Control+a
+# Then delete:
+agent-browser press Backspace
+```
+
+### Screenshot Tips for VS Code
+
+On ultrawide monitors, the chat sidebar may be in the far-right corner of the CDP screenshot. Options:
+- Use `agent-browser screenshot --full` to capture the entire window
+- Use element screenshots: `agent-browser screenshot ".part.auxiliarybar" sidebar.png`
+- Use `agent-browser screenshot --annotate` to see labeled element positions
+- Maximize the sidebar first: click the "Maximize Secondary Side Bar" button
+
+> **macOS:** If `agent-browser screenshot` returns "Permission denied", your terminal needs Screen Recording permission. Grant it in **System Settings → Privacy & Security → Screen Recording**. As a fallback, use the `eval` verification snippet to confirm text was entered — this doesn't require screen permissions.
+
+## Troubleshooting
+
+### "Connection refused" or "Cannot connect"
+
+- Make sure Code OSS was launched with `--remote-debugging-port=NNNN`
+- If Code OSS was already running, quit and relaunch with the flag
+- Check that the port isn't in use by another process:
+  - macOS / Linux: `lsof -i :9224`
+  - Windows: `netstat -ano | findstr 9224`
+
+### Elements not appearing in snapshot
+
+- VS Code uses multiple webviews. Use `agent-browser tab` to list targets and switch to the right one
+- Use `agent-browser snapshot -i -C` to include cursor-interactive elements (divs with onclick handlers)
+
+### Cannot type in Monaco Editor inputs
+
+- Use `agent-browser press` for individual keystrokes after focusing the input. Focus the chat input with the keyboard shortcut (macOS: `Ctrl+Cmd+I`, Linux/Windows: `Ctrl+Alt+I`).
+- `type @ref`, `keyboard type`, and `keyboard inserttext` work on VS Code Insiders but **silently fail on Code OSS** — they complete without error but no text appears. The `press`-per-key approach works universally.
+- See the "Interacting with Monaco Editor" section above for the full compatibility matrix.
+
+## Cleanup
+
+**Always kill the Code OSS instance when you're done.** Code OSS is a full Electron app that consumes significant memory (often 1–4 GB+). Leaving it running wastes resources and holds the CDP port.
+
+```bash
+# Disconnect agent-browser
+agent-browser close
+
+# Kill the Code OSS instance listening on the debug port (if running)
+# macOS / Linux:
+pids=$(lsof -t -i :9224)
+if [ -n "$pids" ]; then
+	kill $pids
+fi
+
+# Windows:
+# taskkill /F /PID <PID>
+# Or use Task Manager to end "Code - OSS"
+```
+
+Verify it's gone:
+```bash
+# Confirm no process is listening on the debug port
+lsof -i :9224  # should return nothing
+```
diff --git a/.claude/skills/launch b/.claude/skills/launch
new file mode 120000
index 0000000000000..b41e2b420ad03
--- /dev/null
+++ b/.claude/skills/launch
@@ -0,0 +1 @@
+../../.agents/skills/launch
\ No newline at end of file
diff --git a/.eslint-ignore b/.eslint-ignore
index 4736eb5621dd7..8b8cdd1c2c707 100644
--- a/.eslint-ignore
+++ b/.eslint-ignore
@@ -18,8 +18,6 @@
 **/extensions/terminal-suggest/src/shell/fishBuiltinsCache.ts
 **/extensions/terminal-suggest/third_party/**
 **/extensions/typescript-language-features/test-workspace/**
-**/extensions/typescript-language-features/extension.webpack.config.js
-**/extensions/typescript-language-features/extension-browser.webpack.config.js
 **/extensions/typescript-language-features/package-manager/node-maintainer/**
 **/extensions/vscode-api-tests/testWorkspace/**
 **/extensions/vscode-api-tests/testWorkspace2/**
diff --git a/.eslint-plugin-local/code-translation-remind.ts b/.eslint-plugin-local/code-translation-remind.ts
index 4203232116710..ed636ec0cb689 100644
--- a/.eslint-plugin-local/code-translation-remind.ts
+++ b/.eslint-plugin-local/code-translation-remind.ts
@@ -26,18 +26,19 @@ export default new class TranslationRemind implements eslint.Rule.RuleModule {
 
 	private _checkImport(context: eslint.Rule.RuleContext, node: TSESTree.Node, path: string) {
 
-		if (path !== TranslationRemind.NLS_MODULE) {
+		if (path !== TranslationRemind.NLS_MODULE && !path.endsWith('/nls.js')) {
 			return;
 		}
 
 		const currentFile = context.getFilename();
 		const matchService = currentFile.match(/vs\/workbench\/services\/\w+/);
 		const matchPart = currentFile.match(/vs\/workbench\/contrib\/\w+/);
-		if (!matchService && !matchPart) {
+		const matchSessionsPart = currentFile.match(/vs\/sessions\/contrib\/\w+/);
+		if (!matchService && !matchPart && !matchSessionsPart) {
 			return;
 		}
 
-		const resource = matchService ? matchService[0] : matchPart![0];
+		const resource = matchService ? matchService[0] : matchPart ? matchPart[0] : matchSessionsPart![0];
 		let resourceDefined = false;
 
 		let json;
@@ -47,9 +48,10 @@ export default new class TranslationRemind implements eslint.Rule.RuleModule {
 			console.error('[translation-remind rule]: File with resources to pull from Transifex was not found. Aborting translation resource check for newly defined workbench part/service.');
 			return;
 		}
-		const workbenchResources = JSON.parse(json).workbench;
+		const parsed = JSON.parse(json);
+		const resources = [...parsed.workbench, ...parsed.sessions];
 
-		workbenchResources.forEach((existingResource: any) => {
+		resources.forEach((existingResource: any) => {
 			if (existingResource.name === resource) {
 				resourceDefined = true;
 				return;
diff --git a/.github/CODENOTIFY b/.github/CODENOTIFY
index 7aba51a470b27..eaf90f0dd1afd 100644
--- a/.github/CODENOTIFY
+++ b/.github/CODENOTIFY
@@ -26,6 +26,7 @@ src/vs/base/browser/ui/tree/** @joaomoreno @benibenj
 # Platform
 src/vs/platform/auxiliaryWindow/** @bpasero
 src/vs/platform/backup/** @bpasero
+src/vs/platform/browserView/** @kycutler @jruales
 src/vs/platform/dialogs/** @bpasero
 src/vs/platform/editor/** @bpasero
 src/vs/platform/environment/** @bpasero
@@ -65,6 +66,7 @@ src/vs/code/** @bpasero @deepak1556
 src/vs/workbench/services/activity/** @bpasero
 src/vs/workbench/services/authentication/** @TylerLeonhardt
 src/vs/workbench/services/auxiliaryWindow/** @bpasero
+src/vs/workbench/services/browserView/** @kycutler @jruales
 src/vs/workbench/services/contextmenu/** @bpasero
 src/vs/workbench/services/dialogs/** @alexr00 @bpasero
 src/vs/workbench/services/editor/** @bpasero
@@ -97,6 +99,7 @@ src/vs/workbench/electron-browser/** @bpasero
 
 # Workbench Contributions
 src/vs/workbench/contrib/authentication/** @TylerLeonhardt
+src/vs/workbench/contrib/browserView/** @kycutler @jruales
 src/vs/workbench/contrib/files/** @bpasero
 src/vs/workbench/contrib/chat/browser/chatListRenderer.ts @roblourens
 src/vs/workbench/contrib/localization/** @TylerLeonhardt
diff --git a/.github/agents/data.md b/.github/agents/data.md
index 605bd276ef9a3..37f83c638cb79 100644
--- a/.github/agents/data.md
+++ b/.github/agents/data.md
@@ -42,3 +42,7 @@ Your response should include:
 - Interpretation and analysis of the results
 - References to specific documentation files when applicable
 - Additional context or insights from the telemetry data
+
+# Troubleshooting
+
+If the connection to the Kusto cluster is timing out consistently, stop and ask the user to check whether they are connected to Azure VPN.
diff --git a/.github/agents/sessions.md b/.github/agents/sessions.md
new file mode 100644
index 0000000000000..1bd1d3986c399
--- /dev/null
+++ b/.github/agents/sessions.md
@@ -0,0 +1,15 @@
+---
+name: Sessions Window Developer
+description: Specialist in developing the Agent Sessions Window
+---
+
+# Role and Objective
+
+You are a developer working on the 'sessions window'. Your goal is to make changes to the sessions window (`src/vs/sessions`), minimally editing outside of that directory.
+
+# Instructions
+
+1.  **Always read the `sessions` skill first.** This is your primary source of truth for the sessions architecture.
+    -   Invoke `skill: "sessions"`.
+2.  Focus your work on `src/vs/sessions/`.
+3.  Avoid making changes to core VS Code files (`src/vs/workbench/`, `src/vs/platform/`, etc.) unless absolutely necessary for the sessions window functionality.
diff --git a/.github/commands.json b/.github/commands.json
index 978a0960eabf6..c52e21eeb8dec 100644
--- a/.github/commands.json
+++ b/.github/commands.json
@@ -631,7 +631,7 @@
 		"addLabel": "capi",
 		"removeLabel": "~capi",
 		"assign": [
-			"samvantran",
+			"rheapatel",
 			"sharonlo"
 		],
 		"comment": "Thank you for creating this issue! Please provide one or more `requestIds` to help the platform team investigate. You can follow instructions [found here](https://github.com/microsoft/vscode/wiki/Copilot-Issues#language-model-requests-and-responses) to locate the `requestId` value.\n\nHappy Coding!"
diff --git a/.github/copilot-instructions.md b/.github/copilot-instructions.md
index 62d002fc4564b..8d56465c45a83 100644
--- a/.github/copilot-instructions.md
+++ b/.github/copilot-instructions.md
@@ -24,6 +24,7 @@ Visual Studio Code is built with a layered architecture using TypeScript, web AP
   - `workbench/api/` - Extension host and VS Code API implementation
 - `src/vs/code/` - Electron main process specific implementation
 - `src/vs/server/` - Server specific implementation
+- `src/vs/sessions/` - Agent sessions window, a dedicated workbench layer for agentic workflows (sits alongside `vs/workbench`, may import from it but not vice versa)
 
 The core architecture follows these principles:
 - **Layered architecture** - from `base`, `platform`, `editor`, to `workbench`
@@ -49,15 +50,16 @@ Each extension follows the standard VS Code extension structure with `package.js
 
 ## Validating TypeScript changes
 
-MANDATORY: Always check the `VS Code - Build` watch task output via #runTasks/getTaskOutput for compilation errors before running ANY script or declaring work complete, then fix all compilation errors before moving forward.
+MANDATORY: Always check for compilation errors before running any tests or validation scripts, or declaring work complete, then fix all compilation errors before moving forward.
 
 - NEVER run tests if there are compilation errors
-- NEVER use `npm run compile` to compile TypeScript files but call #runTasks/getTaskOutput instead
+- NEVER use `npm run compile` to compile TypeScript files
 
 ### TypeScript compilation steps
-- Monitor the `VS Code - Build` task outputs for real-time compilation errors as you make changes
-- This task runs `Core - Build` and `Ext - Build` to incrementally compile VS Code TypeScript sources and built-in extensions
-- Start the task if it's not already running in the background
+- If the `#runTasks/getTaskOutput` tool is available, check the `VS Code - Build` watch task output for compilation errors. This task runs `Core - Build` and `Ext - Build` to incrementally compile VS Code TypeScript sources and built-in extensions. Start the task if it's not already running in the background.
+- If the tool is not available (e.g. in CLI environments) and you only changed code under `src/`, run `npm run compile-check-ts-native` after making changes to type-check the main VS Code sources (it validates `./src/tsconfig.json`).
+- If you changed built-in extensions under `extensions/` and the tool is not available, run the corresponding gulp task `npm run gulp compile-extensions` instead so that TypeScript errors in extensions are also reported.
+- For TypeScript changes in the `build` folder, you can simply run `npm run typecheck` in the `build` folder.
 
 ### TypeScript validation steps
 - Use the run test tool if you need to run tests. If that tool is not available, then you can use `scripts/test.sh` (or `scripts\test.bat` on Windows) for unit tests (add `--grep <pattern>` to filter tests) or `scripts/test-integration.sh` (or `scripts\test-integration.bat` on Windows) for integration tests (integration tests end with .integrationTest.ts or are in /extensions/).
@@ -134,6 +136,7 @@ function f(x: number, y: string): void { }
 - Prefer regex capture groups with names over numbered capture groups.
 - If you create any temporary new files, scripts, or helper files for iteration, clean up these files by removing them at the end of the task
 - Never duplicate imports. Always reuse existing imports if they are present.
+- When removing an import, do not leave behind blank lines where the import was. Ensure the surrounding code remains compact.
 - Do not use `any` or `unknown` as the type for variables, parameters, or return values unless absolutely necessary. If they need type annotations, they should have proper types or interfaces defined.
 - When adding file watching, prefer correlated file watchers (via fileService.createWatcher) to shared ones.
 - When adding tooltips to UI elements, prefer the use of IHoverService service.
diff --git a/.github/hooks/hooks.json b/.github/hooks/hooks.json
new file mode 100644
index 0000000000000..4457634963e9e
--- /dev/null
+++ b/.github/hooks/hooks.json
@@ -0,0 +1,41 @@
+{
+	"version": 1,
+	"hooks": {
+		"sessionStart": [
+			{
+				"type": "command",
+				"bash": ""
+			}
+		],
+		"sessionEnd": [
+			{
+				"type": "command",
+				"bash": ""
+			}
+		],
+		"agentStop": [
+			{
+				"type": "command",
+				"bash": ""
+			}
+		],
+		"userPromptSubmitted": [
+			{
+				"type": "command",
+				"bash": ""
+			}
+		],
+		"preToolUse": [
+			{
+				"type": "command",
+				"bash": ""
+			}
+		],
+		"postToolUse": [
+			{
+				"type": "command",
+				"bash": ""
+			}
+		]
+	}
+}
diff --git a/.github/instructions/kusto.instructions.md b/.github/instructions/kusto.instructions.md
index 2c77e92555d6c..ac247c5772415 100644
--- a/.github/instructions/kusto.instructions.md
+++ b/.github/instructions/kusto.instructions.md
@@ -6,7 +6,7 @@ description: Kusto exploration and telemetry analysis instructions
 
 When performing Kusto queries, telemetry analysis, or data exploration tasks for VS Code, consult the comprehensive Kusto instructions located at:
 
-**[kusto-vscode-instructions.md](../../../vscode-internalbacklog/instructions/kusto/kusto-vscode-instructions.md)**
+**[kusto-vscode-instructions.md](../../../vscode-tools/.github/skills/kusto-telemetry/kusto-vscode.instructions.md)**
 
 These instructions contain valuable information about:
 - Available Kusto clusters and databases for VS Code telemetry
@@ -16,4 +16,4 @@ These instructions contain valuable information about:
 
 Reading these instructions before writing Kusto queries will help you write more accurate and efficient queries, avoid common pitfalls, and leverage existing knowledge about VS Code's telemetry infrastructure.
 
-(Make sure to have the main branch of vscode-internalbacklog up to date in case there are problems).
+(Make sure to have the main branch of vscode-tools up to date in case there are problems and the repository cloned from https://github.com/microsoft/vscode-tools).
diff --git a/.github/instructions/oss.instructions.md b/.github/instructions/oss.instructions.md
new file mode 100644
index 0000000000000..2e73cdbbbc20b
--- /dev/null
+++ b/.github/instructions/oss.instructions.md
@@ -0,0 +1,34 @@
+---
+applyTo: '{ThirdPartyNotices.txt,cli/ThirdPartyNotices.txt,cglicenses.json,cgmanifest.json}'
+---
+
+# OSS License Review
+
+When reviewing changes to these files, verify:
+
+## ThirdPartyNotices.txt
+
+- Every new entry has a license type header (e.g., "MIT License", "Apache License 2.0")
+- License text is present and non-empty for every entry
+- License text matches the declared license type (e.g., MIT-declared entry actually contains MIT license text, not Apache)
+- Removed entries are cleanly removed (no leftover fragments)
+- Entries are sorted alphabetically by package name
+
+## cglicenses.json
+
+- New overrides have a justification comment
+- No obviously stale entries for packages no longer in the dependency tree
+
+## cgmanifest.json
+
+- Package versions match what's actually installed
+- Repository URLs are valid and point to real source repositories
+- Newly added license identifiers should use SPDX format where possible
+- License identifiers match the corresponding ThirdPartyNotices.txt entries
+
+## Red Flags
+
+- Any **newly added** copyleft license (GPL, LGPL, AGPL) — flag immediately (existing copyleft entries like ffmpeg are pre-approved)
+- Any "UNKNOWN" or placeholder license text
+- License text that appears truncated or corrupted
+- A package declared as MIT but with Apache/BSD/other license text (or vice versa)
diff --git a/.github/skills/accessibility/SKILL.md b/.github/skills/accessibility/SKILL.md
index 1d141f0c09275..591e85ff8123c 100644
--- a/.github/skills/accessibility/SKILL.md
+++ b/.github/skills/accessibility/SKILL.md
@@ -1,8 +1,22 @@
 ---
 name: accessibility
-description: Accessibility guidelines for VS Code features — covers accessibility help dialogs, accessible views, verbosity settings, accessibility signals, ARIA alerts/status announcements, keyboard navigation, and ARIA labels/roles. Applies to both new interactive UI surfaces and updates to existing features. Use when creating new UI or updating existing UI features.
+description: Primary accessibility skill for VS Code. REQUIRED for new feature and contribution work, and also applies to updates of existing UI. Covers accessibility help dialogs, accessible views, verbosity settings, signals, ARIA announcements, keyboard navigation, and ARIA labels/roles.
 ---
 
+## When to Use This Skill
+
+Use this skill for any VS Code feature work that introduces or changes interactive UI.
+Use this skill by default for new features and contributions, including when the request does not explicitly mention accessibility.
+
+Trigger examples:
+- "add a new feature"
+- "implement a new panel/view/widget"
+- "add a new command or workflow"
+- "new contribution in workbench/editor/extensions"
+- "update existing UI interactions"
+
+Do not skip this skill just because accessibility is not named in the prompt.
+
 When adding a **new interactive UI surface** to VS Code — a panel, view, widget, editor overlay, dialog, or any rich focusable component the user interacts with — you **must** provide three accessibility components (if they do not already exist for the feature):
 
 1. **An Accessibility Help Dialog** — opened via the accessibility help keybinding when the feature has focus.
@@ -47,10 +61,7 @@ An accessibility help dialog tells the user what the feature does, which keyboar
 The simplest approach is to return an `AccessibleContentProvider` directly from `getProvider()`. This is the most common pattern in the codebase (used by chat, inline chat, quick chat, etc.):
 
 ```ts
-import { AccessibleViewType, AccessibleContentProvider, AccessibleViewProviderId } from '…/accessibleView.js';
-import { IAccessibleViewImplementation } from '…/accessibleViewRegistry.js';
-import { AccessibilityVerbositySettingId } from '…/accessibilityConfiguration.js';
-import { AccessibleViewType, AccessibleContentProvider, AccessibleViewProviderId, IAccessibleViewContentProvider, IAccessibleViewOptions } from '../../../../platform/accessibility/browser/accessibleView.js';
+import { AccessibleViewType, AccessibleContentProvider, AccessibleViewProviderId } from '../../../../platform/accessibility/browser/accessibleView.js';
 import { IAccessibleViewImplementation } from '../../../../platform/accessibility/browser/accessibleViewRegistry.js';
 import { AccessibilityVerbositySettingId } from '../../../../platform/accessibility/common/accessibilityConfiguration.js';
 
diff --git a/.github/skills/add-policy/SKILL.md b/.github/skills/add-policy/SKILL.md
new file mode 100644
index 0000000000000..64119b056bad3
--- /dev/null
+++ b/.github/skills/add-policy/SKILL.md
@@ -0,0 +1,139 @@
+---
+name: add-policy
+description: Use when adding, modifying, or reviewing VS Code configuration policies. Covers the full policy lifecycle from registration to export to platform-specific artifacts. Run on ANY change that adds a `policy:` field to a configuration property.
+---
+
+# Adding a Configuration Policy
+
+Policies allow enterprise administrators to lock configuration settings via OS-level mechanisms (Windows Group Policy, macOS managed preferences, Linux config files) or via Copilot account-level policy data. This skill covers the complete procedure.
+
+## When to Use
+
+- Adding a new `policy:` field to any configuration property
+- Modifying an existing policy (rename, category change, etc.)
+- Reviewing a PR that touches policy registration
+- Adding account-based policy support via `IPolicyData`
+
+## Architecture Overview
+
+### Policy Sources (layered, last writer wins)
+
+| Source | Implementation | How it reads policies |
+|--------|---------------|----------------------|
+| **OS-level** (Windows registry, macOS plist) | `NativePolicyService` via `@vscode/policy-watcher` | Watches `Software\Policies\Microsoft\{productName}` (Windows) or bundle identifier prefs (macOS) |
+| **Linux file** | `FilePolicyService` | Reads `/etc/vscode/policy.json` |
+| **Account/GitHub** | `AccountPolicyService` | Reads `IPolicyData` from `IDefaultAccountService.policyData`, applies `value()` function |
+| **Multiplex** | `MultiplexPolicyService` | Combines OS-level + account policy services; used in desktop main |
+
+### Key Files
+
+| File | Purpose |
+|------|---------|
+| `src/vs/base/common/policy.ts` | `PolicyCategory` enum, `IPolicy` interface |
+| `src/vs/platform/policy/common/policy.ts` | `IPolicyService`, `AbstractPolicyService`, `PolicyDefinition` |
+| `src/vs/platform/configuration/common/configurations.ts` | `PolicyConfiguration` — bridges policies to configuration values |
+| `src/vs/workbench/services/policies/common/accountPolicyService.ts` | Account/GitHub-based policy evaluation |
+| `src/vs/workbench/services/policies/common/multiplexPolicyService.ts` | Combines multiple policy services |
+| `src/vs/workbench/contrib/policyExport/electron-browser/policyExport.contribution.ts` | `--export-policy-data` CLI handler |
+| `src/vs/base/common/defaultAccount.ts` | `IPolicyData` interface for account-level policy fields |
+| `build/lib/policies/policyData.jsonc` | Auto-generated policy catalog (DO NOT edit manually) |
+| `build/lib/policies/policyGenerator.ts` | Generates ADMX/ADML (Windows), plist (macOS), JSON (Linux) |
+| `build/lib/test/policyConversion.test.ts` | Tests for policy artifact generation |
+
+## Procedure
+
+### Step 1 — Add the `policy` field to the configuration property
+
+Find the configuration registration (typically in a `*.contribution.ts` file) and add a `policy` object to the property schema.
+
+**Required fields:**
+
+**Determining `minimumVersion`:** Always read `version` from the root `package.json` and use the `major.minor` portion. For example, if `package.json` has `"version": "1.112.0"`, use `minimumVersion: '1.112'`. Never hardcode an old version like `'1.99'`.
+
+```typescript
+policy: {
+    name: 'MyPolicyName',                          // PascalCase, unique across all policies
+    category: PolicyCategory.InteractiveSession,    // From PolicyCategory enum
+    minimumVersion: '1.112',                        // Use major.minor from package.json version
+    localization: {
+        description: {
+            key: 'my.config.key',                   // NLS key for the description
+            value: nls.localize('my.config.key', "Human-readable description."),
+        }
+    }
+}
+```
+
+**Optional: `value` function for account-based policy:**
+
+If this policy should also be controllable via Copilot account policy data (from `IPolicyData`), add a `value` function:
+
+```typescript
+policy: {
+    name: 'MyPolicyName',
+    category: PolicyCategory.InteractiveSession,
+    minimumVersion: '1.112',                        // Use major.minor from package.json version
+    value: (policyData) => policyData.my_field === false ? false : undefined,
+    localization: { /* ... */ }
+}
+```
+
+The `value` function receives `IPolicyData` (from `src/vs/base/common/defaultAccount.ts`) and should:
+- Return a concrete value to **override** the user's setting
+- Return `undefined` to **not apply** any account-level override (falls through to OS policy or user setting)
+
+If you need a new field on `IPolicyData`, add it to the interface in `src/vs/base/common/defaultAccount.ts`.
+
+**Optional: `enumDescriptions` for enum/string policies:**
+
+```typescript
+localization: {
+    description: { key: '...', value: nls.localize('...', "...") },
+    enumDescriptions: [
+        { key: 'opt.none', value: nls.localize('opt.none', "No access.") },
+        { key: 'opt.all', value: nls.localize('opt.all', "Full access.") },
+    ]
+}
+```
+
+### Step 2 — Ensure `PolicyCategory` is imported
+
+```typescript
+import { PolicyCategory } from '../../../../base/common/policy.js';
+```
+
+Existing categories in the `PolicyCategory` enum:
+- `Extensions`
+- `IntegratedTerminal`
+- `InteractiveSession` (used for all chat/Copilot policies)
+- `Telemetry`
+- `Update`
+
+If you need a new category, add it to `PolicyCategory` in `src/vs/base/common/policy.ts` and add corresponding `PolicyCategoryData` localization.
+
+### Step 3 — Validate TypeScript compilation
+
+Check the `VS Code - Build` watch task output, or run:
+
+```bash
+npm run compile-check-ts-native
+```
+
+### Step 4 — Export the policy data
+
+Regenerate the auto-generated policy catalog:
+
+```bash
+npm run transpile-client && ./scripts/code.sh --export-policy-data
+```
+
+This updates `build/lib/policies/policyData.jsonc`. **Never edit this file manually.** Verify your new policy appears in the output.  You will need code review from a codeowner to merge the change to main.
+
+
+## Policy for extension-provided settings
+
+For an extension author to provide policies for their extension's settings, a change must be made in `vscode-distro` to the `product.json`.
+
+## Examples
+
+Search the codebase for `policy:` to find all the examples of different policy configurations.
diff --git a/.github/skills/agent-sessions-layout/SKILL.md b/.github/skills/agent-sessions-layout/SKILL.md
index a76794d9c7d8a..af4f03a3f6066 100644
--- a/.github/skills/agent-sessions-layout/SKILL.md
+++ b/.github/skills/agent-sessions-layout/SKILL.md
@@ -45,7 +45,7 @@ When proposing or implementing changes, follow these rules from the spec:
 4. **New parts go in the right section** — Any new parts should be added to the horizontal branch alongside Chat Bar and Auxiliary Bar
 5. **Preserve no-op methods** — Unsupported features (zen mode, centered layout, etc.) should remain as no-ops, not throw errors
 6. **Handle pane composite lifecycle** — When hiding/showing parts, manage the associated pane composites
-7. **Use agent session parts** — New part functionality goes in the agent session part classes (`SidebarPart`, `AuxiliaryBarPart`, `PanelPart`, `ChatBarPart`), not the standard workbench parts
+7. **Use agent session parts** — New part functionality goes in the agent session part classes (`SidebarPart`, `AuxiliaryBarPart`, `PanelPart`, `ChatBarPart`, `ProjectBarPart`), not the standard workbench parts
 8. **Use separate storage keys** — Agent session parts use their own storage keys (prefixed with `workbench.agentsession.` or `workbench.chatbar.`) to avoid conflicts with regular workbench state
 9. **Use agent session menu IDs** — Actions should use `Menus.*` menu IDs (from `sessions/browser/menus.ts`), not shared `MenuId.*` constants
 
@@ -53,20 +53,24 @@ When proposing or implementing changes, follow these rules from the spec:
 
 | File | Purpose |
 |------|---------|
-| `sessions/LAYOUT.md` | Authoritative specification |
+| `sessions/LAYOUT.md` | Authoritative layout specification |
 | `sessions/browser/workbench.ts` | Main layout implementation (`Workbench` class) |
 | `sessions/browser/menus.ts` | Agent sessions menu IDs (`Menus` export) |
 | `sessions/browser/layoutActions.ts` | Layout actions (toggle sidebar, panel, secondary sidebar) |
 | `sessions/browser/paneCompositePartService.ts` | `AgenticPaneCompositePartService` |
-| `sessions/browser/style.css` | Layout-specific styles |
-| `sessions/browser/parts/` | Agent session part implementations |
+| `sessions/browser/media/style.css` | Layout-specific styles |
+| `sessions/browser/parts/parts.ts` | `AgenticParts` enum |
 | `sessions/browser/parts/titlebarPart.ts` | Titlebar part, MainTitlebarPart, AuxiliaryTitlebarPart, TitleService |
-| `sessions/browser/parts/sidebarPart.ts` | Sidebar part (with footer) |
+| `sessions/browser/parts/sidebarPart.ts` | Sidebar part (with footer and macOS traffic light spacer) |
 | `sessions/browser/parts/chatBarPart.ts` | Chat Bar part |
-| `sessions/browser/widget/` | Agent sessions chat widget |
+| `sessions/browser/parts/auxiliaryBarPart.ts` | Auxiliary Bar part (with run script dropdown) |
+| `sessions/browser/parts/panelPart.ts` | Panel part |
+| `sessions/browser/parts/projectBarPart.ts` | Project Bar part (folder entries, icon customization) |
+| `sessions/contrib/configuration/browser/configuration.contribution.ts` | Sets `workbench.editor.useModal` to `'all'` for modal editor overlay |
 | `sessions/contrib/sessions/browser/sessionsTitleBarWidget.ts` | Title bar widget and session picker |
-| `sessions/contrib/chat/browser/runScriptAction.ts` | Run script contribution |
+| `sessions/contrib/chat/browser/runScriptAction.ts` | Run script split button for titlebar |
 | `sessions/contrib/accountMenu/browser/account.contribution.ts` | Account widget for sidebar footer |
+| `sessions/electron-browser/parts/titlebarPart.ts` | Desktop (Electron) titlebar part |
 
 ## 5. Testing Changes
 
diff --git a/.github/skills/azure-pipelines/SKILL.md b/.github/skills/azure-pipelines/SKILL.md
index b7b2e164e038d..9790401995258 100644
--- a/.github/skills/azure-pipelines/SKILL.md
+++ b/.github/skills/azure-pipelines/SKILL.md
@@ -66,21 +66,24 @@ Use the [queue command](./azure-pipeline.ts) to queue a validation build:
 
 ```bash
 # Queue a build on the current branch
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts queue
+node .github/skills/azure-pipelines/azure-pipeline.ts queue
 
 # Queue with a specific source branch
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts queue --branch my-feature-branch
+node .github/skills/azure-pipelines/azure-pipeline.ts queue --branch my-feature-branch
 
-# Queue with custom variables (e.g., to skip certain stages)
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts queue --variables "SKIP_TESTS=true"
+# Queue with custom parameters
+node .github/skills/azure-pipelines/azure-pipeline.ts queue --parameter "VSCODE_BUILD_WEB=false" --parameter "VSCODE_PUBLISH=false"
+
+# Parameter value with spaces
+node .github/skills/azure-pipelines/azure-pipeline.ts queue --parameter "VSCODE_BUILD_TYPE=Product Build"
 ```
 
 > **Important**: Before queueing a new build, cancel any previous builds on the same branch that you no longer need. This frees up build agents and reduces resource waste:
 > ```bash
 > # Find the build ID from status, then cancel it
-> node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status
-> node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id <id>
-> node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts queue
+> node .github/skills/azure-pipelines/azure-pipeline.ts status
+> node .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id <id>
+> node .github/skills/azure-pipelines/azure-pipeline.ts queue
 > ```
 
 ### Script Options
@@ -89,9 +92,43 @@ node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts
 |--------|-------------|
 | `--branch <name>` | Source branch to build (default: current git branch) |
 | `--definition <id>` | Pipeline definition ID (default: 111) |
-| `--variables <vars>` | Pipeline variables in `KEY=value` format, space-separated |
+| `--parameter <entry>` | Pipeline parameter in `KEY=value` format (repeatable) |
+| `--parameters <list>` | Space-separated parameters in `KEY=value KEY2=value2` format |
 | `--dry-run` | Print the command without executing |
 
+### Product Build Queue Parameters (`build/azure-pipelines/product-build.yml`)
+
+| Name | Type | Default | Allowed Values | Description |
+|------|------|---------|----------------|-------------|
+| `VSCODE_QUALITY` | string | `insider` | `exploration`, `insider`, `stable` | Build quality channel |
+| `VSCODE_BUILD_TYPE` | string | `Product Build` | `Product`, `CI` | Build mode for Product vs CI |
+| `NPM_REGISTRY` | string | `https://pkgs.dev.azure.com/monacotools/Monaco/_packaging/vscode/npm/registry/` | any URL | Custom npm registry |
+| `CARGO_REGISTRY` | string | `sparse+https://pkgs.dev.azure.com/monacotools/Monaco/_packaging/vscode/Cargo/index/` | any URL | Custom Cargo registry |
+| `VSCODE_BUILD_WIN32` | boolean | `true` | `true`, `false` | Build Windows x64 |
+| `VSCODE_BUILD_WIN32_ARM64` | boolean | `true` | `true`, `false` | Build Windows arm64 |
+| `VSCODE_BUILD_LINUX` | boolean | `true` | `true`, `false` | Build Linux x64 |
+| `VSCODE_BUILD_LINUX_SNAP` | boolean | `true` | `true`, `false` | Build Linux x64 Snap |
+| `VSCODE_BUILD_LINUX_ARM64` | boolean | `true` | `true`, `false` | Build Linux arm64 |
+| `VSCODE_BUILD_LINUX_ARMHF` | boolean | `true` | `true`, `false` | Build Linux armhf |
+| `VSCODE_BUILD_ALPINE` | boolean | `true` | `true`, `false` | Build Alpine x64 |
+| `VSCODE_BUILD_ALPINE_ARM64` | boolean | `true` | `true`, `false` | Build Alpine arm64 |
+| `VSCODE_BUILD_MACOS` | boolean | `true` | `true`, `false` | Build macOS x64 |
+| `VSCODE_BUILD_MACOS_ARM64` | boolean | `true` | `true`, `false` | Build macOS arm64 |
+| `VSCODE_BUILD_MACOS_UNIVERSAL` | boolean | `true` | `true`, `false` | Build macOS universal (requires both macOS arches) |
+| `VSCODE_BUILD_WEB` | boolean | `true` | `true`, `false` | Build Web artifacts |
+| `VSCODE_PUBLISH` | boolean | `true` | `true`, `false` | Publish to builds.code.visualstudio.com |
+| `VSCODE_RELEASE` | boolean | `false` | `true`, `false` | Trigger release flow if successful |
+| `VSCODE_STEP_ON_IT` | boolean | `false` | `true`, `false` | Skip tests |
+
+Example: run a quick CI-oriented validation with minimal publish/release side effects:
+
+```bash
+node .github/skills/azure-pipelines/azure-pipeline.ts queue \
+   --parameter "VSCODE_BUILD_TYPE=CI Build" \
+   --parameter "VSCODE_PUBLISH=false" \
+   --parameter "VSCODE_RELEASE=false"
+```
+
 ---
 
 ## Checking Build Status
@@ -99,17 +136,17 @@ node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts
 Use the [status command](./azure-pipeline.ts) to monitor a running build:
 
 ```bash
-# Get status of the most recent build on your branch
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status
+# Get status of the most recent builds
+node .github/skills/azure-pipelines/azure-pipeline.ts status
 
 # Get overview of a specific build by ID
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status --build-id 123456
+node .github/skills/azure-pipelines/azure-pipeline.ts status --build-id 123456
 
 # Watch build status (refreshes every 30 seconds)
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status --watch
+node .github/skills/azure-pipelines/azure-pipeline.ts status --watch
 
 # Watch with custom interval (60 seconds)
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status --watch 60
+node .github/skills/azure-pipelines/azure-pipeline.ts status --watch 60
 ```
 
 ### Script Options
@@ -133,10 +170,10 @@ Use the [cancel command](./azure-pipeline.ts) to stop a running build:
 
 ```bash
 # Cancel a build by ID (use status command to find IDs)
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id 123456
+node .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id 123456
 
 # Dry run (show what would be cancelled)
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id 123456 --dry-run
+node .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id 123456 --dry-run
 ```
 
 ### Script Options
@@ -149,6 +186,44 @@ node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts
 
 ---
 
+## Testing Pipeline Changes
+
+When the user asks to **test changes in an Azure Pipelines build**, follow this workflow:
+
+1. **Queue a new build** on the current branch
+2. **Poll for completion** by periodically checking the build status until it finishes
+
+### Polling for Build Completion
+
+Use a shell loop with `sleep` to poll the build status. The `sleep` command works on all major operating systems:
+
+```bash
+# Queue the build and note the build ID from output (e.g., 123456)
+node .github/skills/azure-pipelines/azure-pipeline.ts queue
+
+# Poll every 60 seconds until complete (works on macOS, Linux, and Windows with Git Bash/WSL)
+# Replace <BUILD_ID> with the actual build ID from the queue command
+while true; do
+  node .github/skills/azure-pipelines/azure-pipeline.ts status --build-id <BUILD_ID> --json 2>/dev/null | grep -q '"status": "completed"' && break
+  sleep 60
+done
+
+# Check final result
+node .github/skills/azure-pipelines/azure-pipeline.ts status --build-id <BUILD_ID>
+```
+
+Alternatively, use the built-in `--watch` flag which handles polling automatically:
+
+```bash
+node .github/skills/azure-pipelines/azure-pipeline.ts queue
+# Use the build ID returned by the queue command
+node .github/skills/azure-pipelines/azure-pipeline.ts status --build-id <BUILD_ID> --watch
+```
+
+> **Note**: The `--watch` flag polls every 30 seconds by default. Use `--watch 60` for a 60-second interval to reduce API calls.
+
+---
+
 ## Common Workflows
 
 ### 1. Quick Pipeline Validation
@@ -159,45 +234,50 @@ git add -A && git commit -m "test: pipeline changes"
 git push origin HEAD
 
 # Check for any previous builds on this branch and cancel if needed
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id <id>  # if there's an active build
+node .github/skills/azure-pipelines/azure-pipeline.ts status
+node .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id <id>  # if there's an active build
 
 # Queue and watch the new build
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts queue
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status --watch
+node .github/skills/azure-pipelines/azure-pipeline.ts queue
+node .github/skills/azure-pipelines/azure-pipeline.ts status --watch
 ```
 
 ### 2. Investigate a Build
 
 ```bash
 # Get overview of a build (shows stages, artifacts, and log IDs)
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status --build-id 123456
+node .github/skills/azure-pipelines/azure-pipeline.ts status --build-id 123456
 
 # Download a specific log for deeper inspection
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status --build-id 123456 --download-log 5
+node .github/skills/azure-pipelines/azure-pipeline.ts status --build-id 123456 --download-log 5
 
 # Download an artifact
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status --build-id 123456 --download-artifact unsigned_vscode_cli_win32_x64_cli
+node .github/skills/azure-pipelines/azure-pipeline.ts status --build-id 123456 --download-artifact unsigned_vscode_cli_win32_x64_cli
 ```
 
-### 3. Test with Modified Variables
+### 3. Test with Modified Parameters
 
 ```bash
-# Skip expensive stages during validation
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts queue --variables "VSCODE_BUILD_SKIP_INTEGRATION_TESTS=true"
+# Customize build matrix for quicker validation
+node .github/skills/azure-pipelines/azure-pipeline.ts queue \
+   --parameter "VSCODE_BUILD_TYPE=CI Build" \
+   --parameter "VSCODE_BUILD_WEB=false" \
+   --parameter "VSCODE_BUILD_ALPINE=false" \
+   --parameter "VSCODE_BUILD_ALPINE_ARM64=false" \
+   --parameter "VSCODE_PUBLISH=false"
 ```
 
 ### 4. Cancel a Running Build
 
 ```bash
 # First, find the build ID
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status
+node .github/skills/azure-pipelines/azure-pipeline.ts status
 
 # Cancel a specific build by ID
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id 123456
+node .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id 123456
 
 # Dry run to see what would be cancelled
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id 123456 --dry-run
+node .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id 123456 --dry-run
 ```
 
 ### 5. Iterate on Pipeline Changes
@@ -210,12 +290,12 @@ git add -A && git commit --amend --no-edit
 git push --force-with-lease origin HEAD
 
 # Find the outdated build ID and cancel it
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id <id>
+node .github/skills/azure-pipelines/azure-pipeline.ts status
+node .github/skills/azure-pipelines/azure-pipeline.ts cancel --build-id <id>
 
 # Queue a fresh build and monitor
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts queue
-node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status --watch
+node .github/skills/azure-pipelines/azure-pipeline.ts queue
+node .github/skills/azure-pipelines/azure-pipeline.ts status --watch
 ```
 
 ---
diff --git a/.github/skills/azure-pipelines/azure-pipeline.ts b/.github/skills/azure-pipelines/azure-pipeline.ts
index 7fad554050bb3..fbb74b5dd4aa0 100644
--- a/.github/skills/azure-pipelines/azure-pipeline.ts
+++ b/.github/skills/azure-pipelines/azure-pipeline.ts
@@ -9,7 +9,7 @@
  * A unified command-line tool for managing Azure Pipeline builds.
  *
  * Usage:
- *   node --experimental-strip-types azure-pipeline.ts <command> [options]
+ *   node azure-pipeline.ts <command> [options]
  *
  * Commands:
  *   queue   - Queue a new pipeline build
@@ -38,8 +38,8 @@ const NUMERIC_ID_PATTERN = /^\d+$/;
 const MAX_ID_LENGTH = 15;
 const BRANCH_PATTERN = /^[a-zA-Z0-9_\-./]+$/;
 const MAX_BRANCH_LENGTH = 256;
-const VARIABLE_PATTERN = /^[a-zA-Z_][a-zA-Z0-9_]*=[a-zA-Z0-9_\-./: ]*$/;
-const MAX_VARIABLE_LENGTH = 256;
+const PARAMETER_PATTERN = /^[a-zA-Z_][a-zA-Z0-9_]*=[a-zA-Z0-9_\-./: +]*$/;
+const MAX_PARAMETER_LENGTH = 256;
 const ARTIFACT_NAME_PATTERN = /^[a-zA-Z0-9_\-.]+$/;
 const MAX_ARTIFACT_NAME_LENGTH = 256;
 const MIN_WATCH_INTERVAL = 5;
@@ -88,7 +88,7 @@ interface Artifact {
 interface QueueArgs {
 	branch: string;
 	definitionId: string;
-	variables: string;
+	parameters: string[];
 	dryRun: boolean;
 	help: boolean;
 }
@@ -159,19 +159,18 @@ function validateBranch(value: string): void {
 	}
 }
 
-function validateVariables(value: string): void {
-	if (!value) {
+function validateParameters(values: string[]): void {
+	if (!values.length) {
 		return;
 	}
-	const vars = value.split(' ').filter(v => v.length > 0);
-	for (const v of vars) {
-		if (v.length > MAX_VARIABLE_LENGTH) {
-			console.error(colors.red(`Error: Variable '${v.substring(0, 20)}...' is too long (max ${MAX_VARIABLE_LENGTH} characters)`));
+	for (const parameter of values) {
+		if (parameter.length > MAX_PARAMETER_LENGTH) {
+			console.error(colors.red(`Error: Parameter '${parameter.substring(0, 20)}...' is too long (max ${MAX_PARAMETER_LENGTH} characters)`));
 			process.exit(1);
 		}
-		if (!VARIABLE_PATTERN.test(v)) {
-			console.error(colors.red(`Error: Invalid variable format '${v}'`));
-			console.log('Expected format: KEY=value (alphanumeric, underscores, hyphens, dots, slashes, colons, spaces in value)');
+		if (!PARAMETER_PATTERN.test(parameter)) {
+			console.error(colors.red(`Error: Invalid parameter format '${parameter}'`));
+			console.log('Expected format: KEY=value (alphanumeric, underscores, hyphens, dots, slashes, colons, plus signs, spaces in value)');
 			process.exit(1);
 		}
 	}
@@ -612,7 +611,7 @@ class AzureDevOpsClient {
 		return JSON.parse(result);
 	}
 
-	async queueBuild(definitionId: string, branch: string, variables?: string): Promise<Build> {
+	async queueBuild(definitionId: string, branch: string, parameters: string[] = []): Promise<Build> {
 		const args = [
 			'pipelines', 'run',
 			'--organization', this.organization,
@@ -621,8 +620,8 @@ class AzureDevOpsClient {
 			'--branch', branch,
 		];
 
-		if (variables) {
-			args.push('--variables', ...variables.split(' '));
+		if (parameters.length > 0) {
+			args.push('--parameters', ...parameters);
 		}
 
 		args.push('--output', 'json');
@@ -771,7 +770,7 @@ class AzureDevOpsClient {
 // ============================================================================
 
 function printQueueUsage(): void {
-	const scriptName = 'node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts queue';
+	const scriptName = 'node .github/skills/azure-pipelines/azure-pipeline.ts queue';
 	console.log(`Usage: ${scriptName} [options]`);
 	console.log('');
 	console.log('Queue an Azure DevOps pipeline build for VS Code.');
@@ -779,21 +778,23 @@ function printQueueUsage(): void {
 	console.log('Options:');
 	console.log('  --branch <name>       Source branch to build (default: current git branch)');
 	console.log('  --definition <id>     Pipeline definition ID (default: 111)');
-	console.log('  --variables <vars>    Pipeline variables in "KEY=value KEY2=value2" format');
+	console.log('  --parameter <entry>   Pipeline parameter in "KEY=value" format (repeatable)');
+	console.log('  --parameters <list>   Space-separated parameter list in "KEY=value KEY2=value2" format');
 	console.log('  --dry-run             Print the command without executing');
 	console.log('  --help                Show this help message');
 	console.log('');
 	console.log('Examples:');
 	console.log(`  ${scriptName}                                    # Queue build on current branch`);
 	console.log(`  ${scriptName} --branch my-feature                # Queue build on specific branch`);
-	console.log(`  ${scriptName} --variables "SKIP_TESTS=true"      # Queue with custom variables`);
+	console.log(`  ${scriptName} --parameter "VSCODE_BUILD_WEB=false" --parameter "VSCODE_PUBLISH=false"`);
+	console.log(`  ${scriptName} --parameter "VSCODE_BUILD_TYPE=Product Build"  # Parameter values with spaces`);
 }
 
 function parseQueueArgs(args: string[]): QueueArgs {
 	const result: QueueArgs = {
 		branch: '',
 		definitionId: DEFAULT_DEFINITION_ID,
-		variables: '',
+		parameters: [],
 		dryRun: false,
 		help: false,
 	};
@@ -807,8 +808,15 @@ function parseQueueArgs(args: string[]): QueueArgs {
 			case '--definition':
 				result.definitionId = args[++i] || DEFAULT_DEFINITION_ID;
 				break;
-			case '--variables':
-				result.variables = args[++i] || '';
+			case '--parameter': {
+				const parameter = args[++i] || '';
+				if (parameter) {
+					result.parameters.push(parameter);
+				}
+				break;
+			}
+			case '--parameters':
+				result.parameters.push(...(args[++i] || '').split(' ').filter(v => v.length > 0));
 				break;
 			case '--dry-run':
 				result.dryRun = true;
@@ -829,7 +837,7 @@ function parseQueueArgs(args: string[]): QueueArgs {
 function validateQueueArgs(args: QueueArgs): void {
 	validateNumericId(args.definitionId, '--definition');
 	validateBranch(args.branch);
-	validateVariables(args.variables);
+	validateParameters(args.parameters);
 }
 
 async function runQueueCommand(args: string[]): Promise<void> {
@@ -860,8 +868,8 @@ async function runQueueCommand(args: string[]): Promise<void> {
 	console.log(`Project:      ${colors.green(PROJECT)}`);
 	console.log(`Definition:   ${colors.green(parsedArgs.definitionId)}`);
 	console.log(`Branch:       ${colors.green(branch)}`);
-	if (parsedArgs.variables) {
-		console.log(`Variables:    ${colors.green(parsedArgs.variables)}`);
+	if (parsedArgs.parameters.length > 0) {
+		console.log(`Parameters:   ${colors.green(parsedArgs.parameters.join(' '))}`);
 	}
 	console.log('━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━');
 	console.log('');
@@ -875,8 +883,8 @@ async function runQueueCommand(args: string[]): Promise<void> {
 			'--id', parsedArgs.definitionId,
 			'--branch', branch,
 		];
-		if (parsedArgs.variables) {
-			cmdArgs.push('--variables', ...parsedArgs.variables.split(' '));
+		if (parsedArgs.parameters.length > 0) {
+			cmdArgs.push('--parameters', ...parsedArgs.parameters);
 		}
 		cmdArgs.push('--output', 'json');
 		console.log(`az ${cmdArgs.join(' ')}`);
@@ -887,7 +895,7 @@ async function runQueueCommand(args: string[]): Promise<void> {
 
 	try {
 		const client = new AzureDevOpsClient(ORGANIZATION, PROJECT);
-		const data = await client.queueBuild(parsedArgs.definitionId, branch, parsedArgs.variables);
+		const data = await client.queueBuild(parsedArgs.definitionId, branch, parsedArgs.parameters);
 
 		const buildId = data.id;
 		const buildNumber = data.buildNumber;
@@ -904,10 +912,10 @@ async function runQueueCommand(args: string[]): Promise<void> {
 		console.log('━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━━');
 		console.log('');
 		console.log('To check status, run:');
-		console.log(`  node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status --build-id ${buildId}`);
+		console.log(`  node .github/skills/azure-pipelines/azure-pipeline.ts status --build-id ${buildId}`);
 		console.log('');
 		console.log('To watch progress:');
-		console.log(`  node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status --build-id ${buildId} --watch`);
+		console.log(`  node .github/skills/azure-pipelines/azure-pipeline.ts status --build-id ${buildId} --watch`);
 	} catch (e) {
 		const error = e instanceof Error ? e : new Error(String(e));
 		console.error(colors.red('Error queuing build:'));
@@ -921,7 +929,7 @@ async function runQueueCommand(args: string[]): Promise<void> {
 // ============================================================================
 
 function printStatusUsage(): void {
-	const scriptName = 'node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status';
+	const scriptName = 'node .github/skills/azure-pipelines/azure-pipeline.ts status';
 	console.log(`Usage: ${scriptName} [options]`);
 	console.log('');
 	console.log('Get status and logs of an Azure DevOps pipeline build.');
@@ -1068,7 +1076,7 @@ async function runStatusCommand(args: string[]): Promise<void> {
 
 		if (!buildId) {
 			console.error(colors.red(`Error: No builds found for branch '${branch}'.`));
-			console.log('You can queue a new build with: node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts queue');
+			console.log('You can queue a new build with: node .github/skills/azure-pipelines/azure-pipeline.ts queue');
 			process.exit(1);
 		}
 	}
@@ -1162,7 +1170,7 @@ async function runStatusCommand(args: string[]): Promise<void> {
 // ============================================================================
 
 function printCancelUsage(): void {
-	const scriptName = 'node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts cancel';
+	const scriptName = 'node .github/skills/azure-pipelines/azure-pipeline.ts cancel';
 	console.log(`Usage: ${scriptName} --build-id <id> [options]`);
 	console.log('');
 	console.log('Cancel a running Azure DevOps pipeline build.');
@@ -1233,7 +1241,7 @@ async function runCancelCommand(args: string[]): Promise<void> {
 		console.error(colors.red('Error: --build-id is required.'));
 		console.log('');
 		console.log('To find build IDs, run:');
-		console.log('  node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status');
+		console.log('  node .github/skills/azure-pipelines/azure-pipeline.ts status');
 		process.exit(1);
 	}
 
@@ -1287,7 +1295,7 @@ async function runCancelCommand(args: string[]): Promise<void> {
 		console.log('');
 		console.log('The build will transition to "cancelling" state and then "canceled".');
 		console.log('Check status with:');
-		console.log(`  node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts status --build-id ${buildId}`);
+		console.log(`  node .github/skills/azure-pipelines/azure-pipeline.ts status --build-id ${buildId}`);
 	} catch (e) {
 		const error = e instanceof Error ? e : new Error(String(e));
 		console.error('');
@@ -1390,15 +1398,15 @@ async function runAllTests(): Promise<void> {
 			validateBranch('');
 		});
 
-		it('validateVariables accepts valid variable formats', () => {
-			validateVariables('KEY=value');
-			validateVariables('MY_VAR=some-value');
-			validateVariables('A=1 B=2 C=3');
-			validateVariables('PATH=/usr/bin:path');
+		it('validateParameters accepts valid parameter formats', () => {
+			validateParameters(['KEY=value']);
+			validateParameters(['MY_VAR=some-value']);
+			validateParameters(['A=1', 'B=2', 'C=3']);
+			validateParameters(['PATH=/usr/bin:path']);
 		});
 
-		it('validateVariables accepts empty string', () => {
-			validateVariables('');
+		it('validateParameters accepts empty list', () => {
+			validateParameters([]);
 		});
 
 		it('validateArtifactName accepts valid artifact names', () => {
@@ -1429,9 +1437,14 @@ async function runAllTests(): Promise<void> {
 			assert.strictEqual(args.definitionId, '222');
 		});
 
-		it('parseQueueArgs parses --variables correctly', () => {
-			const args = parseQueueArgs(['--variables', 'KEY=value']);
-			assert.strictEqual(args.variables, 'KEY=value');
+		it('parseQueueArgs parses --parameters correctly', () => {
+			const args = parseQueueArgs(['--parameters', 'KEY=value']);
+			assert.deepStrictEqual(args.parameters, ['KEY=value']);
+		});
+
+		it('parseQueueArgs parses repeated --parameter correctly', () => {
+			const args = parseQueueArgs(['--parameter', 'A=1', '--parameter', 'B=two words']);
+			assert.deepStrictEqual(args.parameters, ['A=1', 'B=two words']);
 		});
 
 		it('parseQueueArgs parses --dry-run correctly', () => {
@@ -1440,10 +1453,10 @@ async function runAllTests(): Promise<void> {
 		});
 
 		it('parseQueueArgs parses combined arguments', () => {
-			const args = parseQueueArgs(['--branch', 'main', '--definition', '333', '--variables', 'A=1 B=2', '--dry-run']);
+			const args = parseQueueArgs(['--branch', 'main', '--definition', '333', '--parameters', 'A=1 B=2', '--dry-run']);
 			assert.strictEqual(args.branch, 'main');
 			assert.strictEqual(args.definitionId, '333');
-			assert.strictEqual(args.variables, 'A=1 B=2');
+			assert.deepStrictEqual(args.parameters, ['A=1', 'B=2']);
 			assert.strictEqual(args.dryRun, true);
 		});
 
@@ -1516,12 +1529,12 @@ async function runAllTests(): Promise<void> {
 			assert.ok(cmd.includes('json'));
 		});
 
-		it('queueBuild includes variables when provided', async () => {
+		it('queueBuild includes parameters when provided', async () => {
 			const client = new TestableAzureDevOpsClient(ORGANIZATION, PROJECT);
-			await client.queueBuild('111', 'main', 'KEY=value OTHER=test');
+			await client.queueBuild('111', 'main', ['KEY=value', 'OTHER=test']);
 
 			const cmd = client.capturedCommands[0];
-			assert.ok(cmd.includes('--variables'));
+			assert.ok(cmd.includes('--parameters'));
 			assert.ok(cmd.includes('KEY=value'));
 			assert.ok(cmd.includes('OTHER=test'));
 		});
@@ -1718,7 +1731,7 @@ async function runAllTests(): Promise<void> {
 	describe('Integration Tests', () => {
 		it('full queue command flow constructs correct az commands', async () => {
 			const client = new TestableAzureDevOpsClient(ORGANIZATION, PROJECT);
-			await client.queueBuild('111', 'feature/test', 'DEBUG=true');
+			await client.queueBuild('111', 'feature/test', ['DEBUG=true']);
 
 			assert.strictEqual(client.capturedCommands.length, 1);
 			const cmd = client.capturedCommands[0];
@@ -1733,7 +1746,7 @@ async function runAllTests(): Promise<void> {
 			assert.ok(cmd.includes('111'));
 			assert.ok(cmd.includes('--branch'));
 			assert.ok(cmd.includes('feature/test'));
-			assert.ok(cmd.includes('--variables'));
+			assert.ok(cmd.includes('--parameters'));
 			assert.ok(cmd.includes('DEBUG=true'));
 		});
 
@@ -1797,7 +1810,7 @@ async function runAllTests(): Promise<void> {
 // ============================================================================
 
 function printMainUsage(): void {
-	const scriptName = 'node --experimental-strip-types .github/skills/azure-pipelines/azure-pipeline.ts';
+	const scriptName = 'node .github/skills/azure-pipelines/azure-pipeline.ts';
 	console.log(`Usage: ${scriptName} <command> [options]`);
 	console.log('');
 	console.log('Azure DevOps Pipeline CLI for VS Code builds.');
diff --git a/.github/skills/component-fixtures/SKILL.md b/.github/skills/component-fixtures/SKILL.md
new file mode 100644
index 0000000000000..6c7eb5a6059dc
--- /dev/null
+++ b/.github/skills/component-fixtures/SKILL.md
@@ -0,0 +1,343 @@
+---
+name: component-fixtures
+description: Use when creating or updating component fixtures for screenshot testing, or when designing UI components to be fixture-friendly. Covers fixture file structure, theming, service setup, CSS scoping, async rendering, and common pitfalls.
+---
+
+# Component Fixtures
+
+Component fixtures render isolated UI components for visual screenshot testing via the component explorer. Fixtures live in `src/vs/workbench/test/browser/componentFixtures/` and are auto-discovered by the Vite dev server using the glob `src/**/*.fixture.ts`.
+
+Use tools `mcp_component-exp_`* to list and screenshot fixtures. If you cannot see these tools, inform the user to them on.
+
+## Running Fixtures Locally
+
+1. Start the component explorer daemon: run the **Launch Component Explorer** task
+2. Use the `mcp_component-exp_list_fixtures` tool to see all available fixtures and their URLs
+3. Use the `mcp_component-exp_screenshot` tool to capture screenshots programmatically
+
+## File Structure
+
+Each fixture file exports a default `defineThemedFixtureGroup(...)`. The file must end with `.fixture.ts`.
+
+```
+src/vs/workbench/test/browser/componentFixtures/
+  fixtureUtils.ts              # Shared helpers (DO NOT import @vscode/component-explorer elsewhere)
+  myComponent.fixture.ts       # Your fixture file
+```
+
+## Basic Pattern
+
+```typescript
+import { ComponentFixtureContext, createEditorServices, defineComponentFixture, defineThemedFixtureGroup } from './fixtureUtils.js';
+
+export default defineThemedFixtureGroup({ path: 'myFeature/' }, {
+    Default: defineComponentFixture({ render: renderMyComponent }),
+    AnotherVariant: defineComponentFixture({ render: renderMyComponent }),
+});
+
+function renderMyComponent({ container, disposableStore, theme }: ComponentFixtureContext): void {
+    container.style.width = '400px';
+
+    const instantiationService = createEditorServices(disposableStore, {
+        colorTheme: theme,
+        additionalServices: (reg) => {
+            // Register additional services the component needs
+            reg.define(IMyService, MyServiceImpl);
+            reg.defineInstance(IMockService, mockInstance);
+        },
+    });
+
+    const widget = disposableStore.add(
+        instantiationService.createInstance(MyWidget, /* constructor args */)
+    );
+    container.appendChild(widget.domNode);
+}
+```
+
+Key points:
+- **`defineThemedFixtureGroup`** automatically creates Dark and Light variants for each fixture
+- **`defineComponentFixture`** wraps your render function with theme setup and shadow DOM isolation
+- **`createEditorServices`** provides a `TestInstantiationService` with base editor services pre-registered
+- Always register created widgets with `disposableStore.add(...)` to prevent leaks
+- Pass `colorTheme: theme` to `createEditorServices` so theme colors render correctly
+
+## Utilities from fixtureUtils.ts
+
+| Export | Purpose |
+|---|---|
+| `defineComponentFixture` | Creates Dark/Light themed fixture variants from a render function |
+| `defineThemedFixtureGroup` | Groups multiple themed fixtures into a named fixture group |
+| `createEditorServices` | Creates `TestInstantiationService` with all base editor services |
+| `registerWorkbenchServices` | Registers additional workbench services (context menu, label, etc.) |
+| `createTextModel` | Creates a text model via `ModelService` for editor fixtures |
+| `setupTheme` | Applies theme CSS to a container (called automatically by `defineComponentFixture`) |
+| `darkTheme` / `lightTheme` | Pre-loaded `ColorThemeData` instances |
+
+**Important:** Only `fixtureUtils.ts` may import from `@vscode/component-explorer`. All fixture files must go through the helpers in `fixtureUtils.ts`.
+
+## CSS Scoping
+
+Fixtures render inside shadow DOM. The component-explorer automatically adopts the global VS Code stylesheets and theme CSS.
+
+### Matching production CSS selectors
+
+Many VS Code components have CSS rules scoped to deep ancestor selectors (e.g., `.interactive-session .interactive-input-part > .widget-container .my-element`). In fixtures, you must recreate the required ancestor DOM structure for these selectors to match:
+
+```typescript
+function render({ container }: ComponentFixtureContext): void {
+    container.classList.add('interactive-session');
+
+    // Recreate ancestor structure that CSS selectors expect
+    const inputPart = dom.$('.interactive-input-part');
+    const widgetContainer = dom.$('.widget-container');
+    inputPart.appendChild(widgetContainer);
+    container.appendChild(inputPart);
+
+    widgetContainer.appendChild(myWidget.domNode);
+}
+```
+
+**Design recommendation for new components:** Avoid deeply nested CSS selectors that require specific ancestor elements. Use self-contained class names (e.g., `.my-widget .my-element` rather than `.parent-view .parent-part > .wrapper .my-element`). This makes components easier to fixture and reuse.
+
+## Services
+
+### Using createEditorServices
+
+`createEditorServices` pre-registers these services: `IAccessibilityService`, `IKeybindingService`, `IClipboardService`, `IOpenerService`, `INotificationService`, `IDialogService`, `IUndoRedoService`, `ILanguageService`, `IConfigurationService`, `IStorageService`, `IThemeService`, `IModelService`, `ICodeEditorService`, `IContextKeyService`, `ICommandService`, `ITelemetryService`, `IHoverService`, `IUserInteractionService`, and more.
+
+### Additional services
+
+Register extra services via `additionalServices`:
+
+```typescript
+createEditorServices(disposableStore, {
+    additionalServices: (reg) => {
+        // Class-based (instantiated by DI):
+        reg.define(IMyService, MyServiceImpl);
+        // Instance-based (pre-constructed):
+        reg.defineInstance(IMyService, myMockInstance);
+    },
+});
+```
+
+### Mocking services
+
+Use the `mock<T>()` helper from `base/test/common/mock.js` to create mock service instances:
+
+```typescript
+import { mock } from '../../../../base/test/common/mock.js';
+
+const myService = new class extends mock<IMyService>() {
+    override someMethod(): string { return 'test'; }
+    override onSomeEvent = Event.None;
+};
+reg.defineInstance(IMyService, myService);
+```
+
+For mock view models or data objects:
+```typescript
+const element = new class extends mock<IChatRequestViewModel>() { }();
+```
+
+## Async Rendering
+
+The component explorer waits **2 animation frames** after the synchronous render function returns. For most components, this is sufficient.
+
+If your render function returns a `Promise`, the component explorer waits for the promise to resolve.
+
+### Pitfall: DOM reparenting causes flickering
+
+Avoid moving rendered widgets between DOM parents after initial render. This causes:
+- Layout recalculation (the widget jumps as `position: absolute` coordinates become invalid)
+- Focus loss (blur events can trigger hide logic in widgets like QuickInput)
+- Screenshot instability (the component explorer may capture an intermediate layout state)
+
+**Bad pattern — reparenting a widget after async wait:**
+```typescript
+async function render({ container }: ComponentFixtureContext): Promise<void> {
+    const host = document.createElement('div');
+    container.appendChild(host);
+    // ... create widget inside host ...
+    await waitForWidget();
+    container.appendChild(widget);  // BAD: reparenting causes flicker
+    host.remove();
+}
+```
+
+**Better pattern — render in-place with the correct DOM structure from the start:**
+```typescript
+function render({ container }: ComponentFixtureContext): void {
+    // Set up the correct DOM structure first, then create the widget inside it
+    const widget = createWidget(container);
+    container.appendChild(widget.domNode);
+}
+```
+
+If the component absolutely requires async setup (e.g., QuickInput which renders internally), minimize DOM manipulation after the widget appears by structuring the host container to match the final layout from the beginning.
+
+## Adapting Existing Components for Fixtures
+
+Existing components often need small changes to become fixturable. When writing a fixture reveals friction, fix the component — don't work around it in the fixture. Common adaptations:
+
+### Decouple CSS from ancestor context
+
+If a component's CSS only works inside a deeply nested selector like `.workbench .sidebar .my-view .my-widget`, refactor the CSS to be self-contained. Move the styles so they're scoped to the component's own root class:
+
+```css
+/* Before: requires specific ancestors */
+.workbench .sidebar .my-view .my-widget .header { font-weight: bold; }
+
+/* After: self-contained */
+.my-widget .header { font-weight: bold; }
+```
+
+If the component shares styles with its parent (e.g., inheriting background color), use CSS custom properties rather than relying on ancestor selectors.
+
+### Extract hard-coded service dependencies
+
+If a component reaches into singletons or global state instead of using DI, refactor it to accept services through the constructor:
+
+```typescript
+// Before: hard to mock in fixtures
+class MyWidget {
+    private readonly config = getSomeGlobalConfig();
+}
+
+// After: injectable and testable
+class MyWidget {
+    constructor(@IConfigurationService private readonly configService: IConfigurationService) { }
+}
+```
+
+### Add options to control auto-focus and animation
+
+Components that auto-focus on creation or run animations cause flaky screenshots. Add an options parameter:
+
+```typescript
+interface IMyWidgetOptions {
+    shouldAutoFocus?: boolean;
+}
+```
+
+The fixture passes `shouldAutoFocus: false`. The production call site keeps the default behavior.
+
+### Expose internal state for "already completed" rendering
+
+Many components have lifecycle states (loading → active → completed). If the component can only reach the "completed" state through user interaction, add support for initializing directly into that state via constructor data:
+
+```typescript
+// The fixture can pass pre-filled data to render the summary/completed state
+// without simulating the full user interaction flow.
+const carousel: IChatQuestionCarousel = {
+    questions,
+    allowSkip: true,
+    kind: 'questionCarousel',
+    isUsed: true,           // Already completed
+    data: { 'q1': 'answer' }, // Pre-filled answers
+};
+```
+
+### Make DOM node accessible
+
+If a component builds its DOM internally and doesn't expose the root element, add a public `readonly domNode: HTMLElement` property so fixtures can append it to the container.
+
+## Writing Fixture-Friendly Components
+
+When designing new UI components, follow these practices to make them easy to fixture:
+
+### 1. Accept a container element in the constructor
+
+```typescript
+// Good: container is passed in
+class MyWidget {
+    constructor(container: HTMLElement, @IFoo foo: IFoo) {
+        this.domNode = dom.append(container, dom.$('.my-widget'));
+    }
+}
+
+// Also good: widget creates its own domNode for the caller to place
+class MyWidget {
+    readonly domNode: HTMLElement;
+    constructor(@IFoo foo: IFoo) {
+        this.domNode = dom.$('.my-widget');
+    }
+}
+```
+
+### 2. Use dependency injection for all services
+
+All external dependencies should come through DI so fixtures can provide test implementations:
+
+```typescript
+// Good: services injected
+constructor(@IThemeService private readonly themeService: IThemeService) { }
+
+// Bad: reaching into globals
+constructor() { this.theme = getGlobalTheme(); }
+```
+
+### 3. Keep CSS selectors shallow
+
+```css
+/* Good: self-contained, easy to fixture */
+.my-widget .my-header { ... }
+.my-widget .my-list-item { ... }
+
+/* Bad: requires deep ancestor chain */
+.workbench .sidebar .my-view .my-widget .my-header { ... }
+```
+
+### 4. Avoid reading from layout/window services during construction
+
+Components that measure the window or read layout dimensions during construction are hard to fixture because the shadow DOM container has different dimensions than the workbench:
+
+```typescript
+// Prefer: use CSS for sizing, or accept dimensions as parameters
+container.style.width = '400px';
+container.style.height = '300px';
+
+// Avoid: reading from layoutService during construction
+const width = this.layoutService.mainContainerDimension.width;
+```
+
+### 5. Support disabling auto-focus in fixtures
+
+Auto-focus can interfere with screenshot stability. Provide options to disable it:
+
+```typescript
+interface IMyWidgetOptions {
+    shouldAutoFocus?: boolean;  // Fixtures pass false
+}
+```
+
+### 6. Expose the DOM node
+
+The fixture needs to append the widget's DOM to the container. Expose it as a public `readonly domNode: HTMLElement`.
+
+## Multiple Fixture Variants
+
+Create variants to show different states of the same component:
+
+```typescript
+export default defineThemedFixtureGroup({
+    // Different data states
+    Empty: defineComponentFixture({ render: (ctx) => renderWidget(ctx, { items: [] }) }),
+    WithItems: defineComponentFixture({ render: (ctx) => renderWidget(ctx, { items: sampleItems }) }),
+
+    // Different configurations
+    ReadOnly: defineComponentFixture({ render: (ctx) => renderWidget(ctx, { readonly: true }) }),
+    Editable: defineComponentFixture({ render: (ctx) => renderWidget(ctx, { readonly: false }) }),
+
+    // Lifecycle states
+    Loading: defineComponentFixture({ render: (ctx) => renderWidget(ctx, { state: 'loading' }) }),
+    Completed: defineComponentFixture({ render: (ctx) => renderWidget(ctx, { state: 'done' }) }),
+});
+```
+
+## Learnings
+
+Update this section with insights from your fixture development experience!
+
+* Do not copy the component to the fixture and modify it there. Always adapt the original component to be fixture-friendly, then render it in the fixture. This ensures the fixture tests the real component code and lifecycle, rather than a modified version that may hide bugs.
+
+* **Don't recompose child widgets in fixtures.** Never manually instantiate and add a sub-widget (e.g., a toolbar content widget) that the parent component is supposed to create. Instead, configure the parent correctly (e.g., set the right editor option, register the right provider) so the child appears through the normal code path. Manually recomposing hides integration bugs and doesn't test the real widget lifecycle.
diff --git a/.github/skills/sessions/SKILL.md b/.github/skills/sessions/SKILL.md
index fc49548b7a384..e39957e5f66bc 100644
--- a/.github/skills/sessions/SKILL.md
+++ b/.github/skills/sessions/SKILL.md
@@ -15,8 +15,6 @@ The `src/vs/sessions/` directory contains authoritative specification documents.
 | Layout spec | `src/vs/sessions/LAYOUT.md` | Grid structure, part positions, sizing, CSS classes, API reference |
 | AI Customizations | `src/vs/sessions/AI_CUSTOMIZATIONS.md` | AI customization editor and tree view design |
 | Chat Widget | `src/vs/sessions/browser/widget/AGENTS_CHAT_WIDGET.md` | Chat widget wrapper architecture, deferred session creation, option delivery |
-| AI Customization Mgmt | `src/vs/sessions/contrib/aiCustomizationManagement/browser/SPEC.md` | Management editor specification |
-| AI Customization Tree | `src/vs/sessions/contrib/aiCustomizationTreeView/browser/SPEC.md` | Tree view specification |
 
 If you modify the implementation, you **must** update the corresponding spec to keep it in sync. Update the Revision History table at the bottom of `LAYOUT.md` with a dated entry.
 
@@ -62,44 +60,57 @@ src/vs/sessions/
 ├── AI_CUSTOMIZATIONS.md                    # AI customization design document
 ├── sessions.common.main.ts                 # Common (browser + desktop) entry point
 ├── sessions.desktop.main.ts                # Desktop entry point (imports all contributions)
-├── common/                                 # Shared types and context keys
-│   └── contextkeys.ts                      # ChatBar context keys
+├── common/                                 # Shared types, context keys, and theme
+│   ├── categories.ts                       # Command categories
+│   ├── contextkeys.ts                      # ChatBar and welcome context keys
+│   └── theme.ts                            # Theme contributions
 ├── browser/                                # Core workbench implementation
 │   ├── workbench.ts                        # Main Workbench class (implements IWorkbenchLayoutService)
 │   ├── menus.ts                            # Agent sessions menu IDs (Menus export)
 │   ├── layoutActions.ts                    # Layout toggle actions (sidebar, panel, auxiliary bar)
 │   ├── paneCompositePartService.ts         # AgenticPaneCompositePartService
-│   ├── style.css                           # Layout-specific styles
 │   ├── widget/                             # Agent sessions chat widget
-│   │   ├── AGENTS_CHAT_WIDGET.md           # Chat widget architecture doc
-│   │   ├── agentSessionsChatWidget.ts      # Main wrapper around ChatWidget
-│   │   ├── agentSessionsChatTargetConfig.ts # Observable target state
-│   │   ├── agentSessionsTargetPickerActionItem.ts # Target picker for input toolbar
-│   │   └── media/
-│   └── parts/                              # Workbench part implementations
-│       ├── parts.ts                        # AgenticParts enum
-│       ├── titlebarPart.ts                 # Titlebar (3-section toolbar layout)
-│       ├── sidebarPart.ts                  # Sidebar (with footer for account widget)
-│       ├── chatBarPart.ts                  # Chat Bar (primary chat surface)
-│       ├── auxiliaryBarPart.ts             # Auxiliary Bar (with run script dropdown)
-│       ├── panelPart.ts                    # Panel (terminal, output, etc.)
-│       ├── projectBarPart.ts              # Project bar (folder entries)
-│       ├── agentSessionsChatInputPart.ts   # Chat input part adapter
-│       ├── agentSessionsChatWelcomePart.ts # Welcome view (mascot + target buttons + pickers)
-│       └── media/                          # Part CSS files
+│   │   └── AGENTS_CHAT_WIDGET.md           # Chat widget architecture doc
+│   ├── parts/                              # Workbench part implementations
+│   │   ├── parts.ts                        # AgenticParts enum
+│   │   ├── titlebarPart.ts                 # Titlebar (3-section toolbar layout)
+│   │   ├── sidebarPart.ts                  # Sidebar (with footer for account widget)
+│   │   ├── chatBarPart.ts                  # Chat Bar (primary chat surface)
+│   │   ├── auxiliaryBarPart.ts             # Auxiliary Bar
+│   │   ├── panelPart.ts                    # Panel (terminal, output, etc.)
+│   │   ├── projectBarPart.ts               # Project bar (folder entries)
+│   │   └── media/                          # Part CSS files
+│   └── media/                              # Layout-specific styles
 ├── electron-browser/                       # Desktop-specific entry points
 │   ├── sessions.main.ts                    # Desktop main bootstrap
 │   ├── sessions.ts                         # Electron process entry
 │   ├── sessions.html                       # Production HTML shell
-│   └── sessions-dev.html                   # Development HTML shell
+│   ├── sessions-dev.html                   # Development HTML shell
+│   ├── titleService.ts                     # Desktop title service override
+│   └── parts/
+│       └── titlebarPart.ts                 # Desktop titlebar part
+├── services/                               # Service overrides
+│   ├── configuration/browser/              # Configuration service overrides
+│   └── workspace/browser/                  # Workspace service overrides
+├── test/                                   # Unit tests
+│   └── browser/
+│       └── layoutActions.test.ts
 └── contrib/                                # Feature contributions
     ├── accountMenu/browser/                # Account widget for sidebar footer
-    ├── aiCustomizationManagement/browser/  # AI customization management editor
+    ├── agentFeedback/browser/              # Agent feedback attachments, overlays, hover
     ├── aiCustomizationTreeView/browser/    # AI customization tree view sidebar
+    ├── applyToParentRepo/browser/          # Apply changes to parent repo
     ├── changesView/browser/                # File changes view
     ├── chat/browser/                       # Chat actions (run script, branch, prompts)
     ├── configuration/browser/              # Configuration overrides
-    └── sessions/browser/                   # Sessions view, title bar widget, active session service
+    ├── files/browser/                      # File-related contributions
+    ├── fileTreeView/browser/               # File tree view (filesystem provider)
+    ├── gitSync/browser/                    # Git sync contributions
+    ├── logs/browser/                       # Log contributions
+    ├── sessions/browser/                   # Sessions view, title bar widget, active session service
+    ├── terminal/browser/                   # Terminal contributions
+    ├── welcome/browser/                    # Welcome view contribution
+    └── workspace/browser/                  # Workspace contributions
 ```
 
 ## 4. Layout
@@ -165,18 +176,21 @@ The agent sessions window uses **its own menu IDs** defined in `browser/menus.ts
 
 | Menu ID | Purpose |
 |---------|---------|
-| `Menus.TitleBarLeft` | Left toolbar (toggle sidebar) |
-| `Menus.TitleBarCenter` | Not used directly (see CommandCenter) |
-| `Menus.TitleBarRight` | Right toolbar (run script, open, toggle auxiliary bar) |
+| `Menus.ChatBarTitle` | Chat bar title actions |
 | `Menus.CommandCenter` | Center toolbar with session picker widget |
-| `Menus.TitleBarControlMenu` | Submenu intercepted to render `SessionsTitleBarWidget` |
+| `Menus.CommandCenterCenter` | Center section of command center |
+| `Menus.TitleBarContext` | Titlebar context menu |
+| `Menus.TitleBarLeftLayout` | Left layout toolbar |
+| `Menus.TitleBarSessionTitle` | Session title in titlebar |
+| `Menus.TitleBarSessionMenu` | Session menu in titlebar |
+| `Menus.TitleBarRightLayout` | Right layout toolbar |
 | `Menus.PanelTitle` | Panel title bar actions |
 | `Menus.SidebarTitle` | Sidebar title bar actions |
 | `Menus.SidebarFooter` | Sidebar footer (account widget) |
+| `Menus.SidebarCustomizations` | Sidebar customizations menu |
 | `Menus.AuxiliaryBarTitle` | Auxiliary bar title actions |
 | `Menus.AuxiliaryBarTitleLeft` | Auxiliary bar left title actions |
-| `Menus.OpenSubMenu` | "Open..." split button (Open Terminal, Open in VS Code) |
-| `Menus.ChatBarTitle` | Chat bar title actions |
+| `Menus.AgentFeedbackEditorContent` | Agent feedback editor content menu |
 
 ## 7. Context Keys
 
@@ -187,7 +201,7 @@ Defined in `common/contextkeys.ts`:
 | `activeChatBar` | `string` | ID of the active chat bar panel |
 | `chatBarFocus` | `boolean` | Whether chat bar has keyboard focus |
 | `chatBarVisible` | `boolean` | Whether chat bar is visible |
-
+| `sessionsWelcomeVisible` | `boolean` | Whether the sessions welcome overlay is visible |
 ## 8. Contributions
 
 Feature contributions live under `contrib/<featureName>/browser/` and are registered via imports in `sessions.desktop.main.ts` (desktop) or `sessions.common.main.ts` (browser-compatible).
@@ -199,13 +213,18 @@ Feature contributions live under `contrib/<featureName>/browser/` and are regist
 | **Sessions View** | `contrib/sessions/browser/` | Sessions list in sidebar, session picker, active session service |
 | **Title Bar Widget** | `contrib/sessions/browser/sessionsTitleBarWidget.ts` | Session picker in titlebar center |
 | **Account Widget** | `contrib/accountMenu/browser/` | Account button in sidebar footer |
-| **Run Script** | `contrib/chat/browser/runScriptAction.ts` | Run configured script in terminal |
-| **Branch Chat Session** | `contrib/chat/browser/branchChatSessionAction.ts` | Branch a chat session |
-| **Open in VS Code / Terminal** | `contrib/chat/browser/chat.contribution.ts` | Open worktree in VS Code or terminal |
-| **Prompts Service** | `contrib/chat/browser/promptsService.ts` | Agentic prompts service override |
+| **Chat Actions** | `contrib/chat/browser/` | Chat actions (run script, branch, prompts, customizations debug log) |
 | **Changes View** | `contrib/changesView/browser/` | File changes in auxiliary bar |
-| **AI Customization Editor** | `contrib/aiCustomizationManagement/browser/` | Management editor for prompts, hooks, MCP, etc. |
+| **Agent Feedback** | `contrib/agentFeedback/browser/` | Agent feedback attachments, editor overlays, hover |
 | **AI Customization Tree** | `contrib/aiCustomizationTreeView/browser/` | Sidebar tree for AI customizations |
+| **Apply to Parent Repo** | `contrib/applyToParentRepo/browser/` | Apply changes to parent repo |
+| **Files** | `contrib/files/browser/` | File-related contributions |
+| **File Tree View** | `contrib/fileTreeView/browser/` | File tree view (filesystem provider) |
+| **Git Sync** | `contrib/gitSync/browser/` | Git sync contributions |
+| **Logs** | `contrib/logs/browser/` | Log contributions |
+| **Terminal** | `contrib/terminal/browser/` | Terminal contributions |
+| **Welcome** | `contrib/welcome/browser/` | Welcome view contribution |
+| **Workspace** | `contrib/workspace/browser/` | Workspace contributions |
 | **Configuration** | `contrib/configuration/browser/` | Configuration overrides |
 
 ### 8.2 Service Overrides
@@ -216,6 +235,10 @@ The agent sessions window registers its own implementations for:
 - `IPromptsService` → `AgenticPromptsService` (scopes prompt discovery to active session worktree)
 - `IActiveSessionService` → `ActiveSessionService` (tracks active session)
 
+Service overrides also live under `services/`:
+- `services/configuration/browser/` - configuration service overrides
+- `services/workspace/browser/` - workspace service overrides
+
 ### 8.3 `WindowVisibility.Sessions`
 
 Views and contributions that should only appear in the agent sessions window (not in regular VS Code) use `WindowVisibility.Sessions` in their registration.
@@ -224,12 +247,14 @@ Views and contributions that should only appear in the agent sessions window (no
 
 | File | Purpose |
 |------|---------|
-| `sessions.common.main.ts` | Common entry — imports browser-compatible services, workbench contributions |
-| `sessions.desktop.main.ts` | Desktop entry — imports desktop services, electron contributions, all `contrib/` modules |
+| `sessions.common.main.ts` | Common entry; imports browser-compatible services, workbench contributions |
+| `sessions.desktop.main.ts` | Desktop entry; imports desktop services, electron contributions, all `contrib/` modules |
 | `electron-browser/sessions.main.ts` | Desktop bootstrap |
 | `electron-browser/sessions.ts` | Electron process entry |
 | `electron-browser/sessions.html` | Production HTML shell |
 | `electron-browser/sessions-dev.html` | Development HTML shell |
+| `electron-browser/titleService.ts` | Desktop title service override |
+| `electron-browser/parts/titlebarPart.ts` | Desktop titlebar part |
 
 ## 10. Development Guidelines
 
@@ -243,7 +268,15 @@ Views and contributions that should only appear in the agent sessions window (no
 6. Use agent session part classes, not standard workbench parts
 7. Mark views with `WindowVisibility.Sessions` so they only appear in this window
 
-### 10.2 Layout Changes
+### 10.2 Validating Changes
+
+1. Run `npm run compile-check-ts-native` to run a repo-wide TypeScript compilation check (including `src/vs/sessions/`). This is a fast way to catch TypeScript errors introduced by your changes.
+2. Run `npm run valid-layers-check` to verify layering rules are not violated.
+3. Use `scripts/test.sh` (or `scripts\test.bat` on Windows) for unit tests (add `--grep <pattern>` to filter tests)
+
+**Important** do not run `tsc` to check for TypeScript errors always use above methods to validate TypeScript changes in `src/vs/**`.
+
+### 10.3 Layout Changes
 
 1. **Read `LAYOUT.md` first** — it's the authoritative spec
 2. Use the `agent-sessions-layout` skill for detailed implementation guidance
diff --git a/.github/skills/update-screenshots/SKILL.md b/.github/skills/update-screenshots/SKILL.md
index 46172cfee2d9b..294125273ef12 100644
--- a/.github/skills/update-screenshots/SKILL.md
+++ b/.github/skills/update-screenshots/SKILL.md
@@ -72,7 +72,16 @@ git add test/componentFixtures/.screenshots/baseline/
 git commit -m "update screenshot baselines from CI"
 ```
 
-### 7. Verify
+### 7. Push LFS objects before pushing
+
+Screenshot baselines are stored in Git LFS. The `git lfs pre-push` hook is not active in this repo (husky overwrites it), so LFS objects are NOT automatically uploaded on `git push`. You must push them manually before pushing the branch, otherwise the push will fail with `GH008: Your push referenced unknown Git LFS objects`.
+
+```bash
+git lfs push --all origin <branch-name>
+git push
+```
+
+### 8. Verify
 
 Confirm the baselines are updated by listing the files:
 
diff --git a/.github/workflows/api-proposal-version-check.yml b/.github/workflows/api-proposal-version-check.yml
new file mode 100644
index 0000000000000..ee082dee49f5b
--- /dev/null
+++ b/.github/workflows/api-proposal-version-check.yml
@@ -0,0 +1,298 @@
+name: API Proposal Version Check
+
+on:
+  pull_request:
+    branches:
+      - main
+      - 'release/*'
+    paths:
+      - 'src/vscode-dts/vscode.proposed.*.d.ts'
+  issue_comment:
+    types: [created]
+
+permissions:
+  contents: read
+  pull-requests: write
+  actions: write
+
+concurrency:
+  group: api-proposal-${{ github.event.pull_request.number || github.event.issue.number }}
+  cancel-in-progress: true
+
+jobs:
+  check-version-changes:
+    name: Check API Proposal Version Changes
+    # Run on PR events, or on issue_comment if it's on a PR and contains the override command
+    if: |
+      github.event_name == 'pull_request' ||
+      (github.event_name == 'issue_comment' &&
+       github.event.issue.pull_request &&
+       contains(github.event.comment.body, '/api-proposal-change-required') &&
+       (github.event.comment.author_association == 'OWNER' ||
+        github.event.comment.author_association == 'MEMBER' ||
+        github.event.comment.author_association == 'COLLABORATOR'))
+    runs-on: ubuntu-latest
+    steps:
+      - name: Get PR info
+        id: pr_info
+        uses: actions/github-script@v8
+        with:
+          script: |
+            let prNumber, headSha, baseSha;
+
+            if (context.eventName === 'pull_request') {
+              prNumber = context.payload.pull_request.number;
+              headSha = context.payload.pull_request.head.sha;
+              baseSha = context.payload.pull_request.base.sha;
+            } else {
+              // issue_comment event - need to fetch PR details
+              prNumber = context.payload.issue.number;
+              const { data: pr } = await github.rest.pulls.get({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                pull_number: prNumber
+              });
+              headSha = pr.head.sha;
+              baseSha = pr.base.sha;
+            }
+
+            core.setOutput('number', prNumber);
+            core.setOutput('head_sha', headSha);
+            core.setOutput('base_sha', baseSha);
+
+      - name: Check for override comment
+        id: check_override
+        uses: actions/github-script@v8
+        with:
+          script: |
+            const prNumber = ${{ steps.pr_info.outputs.number }};
+            const { data: comments } = await github.rest.issues.listComments({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              issue_number: prNumber
+            });
+
+            // Only accept overrides from trusted users (repo members/collaborators)
+            const trustedAssociations = ['OWNER', 'MEMBER', 'COLLABORATOR'];
+            let overrideComment = null;
+            const untrustedOverrides = [];
+
+            comments.forEach((comment, index) => {
+              const hasOverrideText = comment.body.includes('/api-proposal-change-required');
+              const isTrusted = trustedAssociations.includes(comment.author_association);
+              console.log(`Comment ${index + 1}:`);
+              console.log(`  Author: ${comment.user.login}`);
+              console.log(`  Author association: ${comment.author_association}`);
+              console.log(`  Created at: ${comment.created_at}`);
+              console.log(`  Contains override command: ${hasOverrideText}`);
+              console.log(`  Author is trusted: ${isTrusted}`);
+              console.log(`  Would be valid override: ${hasOverrideText && isTrusted}`);
+
+              if (hasOverrideText) {
+                if (isTrusted && !overrideComment) {
+                  overrideComment = comment;
+                } else if (!isTrusted) {
+                  untrustedOverrides.push(comment);
+                }
+              }
+            });
+
+            if (overrideComment) {
+              console.log(`✅ Override comment FOUND`);
+              console.log(`  Comment ID: ${overrideComment.id}`);
+              console.log(`  Author: ${overrideComment.user.login}`);
+              console.log(`  Association: ${overrideComment.author_association}`);
+              console.log(`  Created at: ${overrideComment.created_at}`);
+              core.setOutput('override_found', 'true');
+              core.setOutput('override_user', overrideComment.user.login);
+            } else {
+              if (untrustedOverrides.length > 0) {
+                console.log(`⚠️ Found ${untrustedOverrides.length} override comment(s) from UNTRUSTED user(s):`);
+                untrustedOverrides.forEach((comment, index) => {
+                  console.log(`  Untrusted override ${index + 1}:`);
+                  console.log(`    Author: ${comment.user.login}`);
+                  console.log(`    Association: ${comment.author_association}`);
+                  console.log(`    Created at: ${comment.created_at}`);
+                  console.log(`    Comment ID: ${comment.id}`);
+                });
+                console.log(`  Trusted associations are: ${trustedAssociations.join(', ')}`);
+              }
+              console.log('❌ No valid override comment found');
+              core.setOutput('override_found', 'false');
+            }
+
+      # If triggered by the override comment, re-run the failed workflow to update its status
+      # Only allow trusted users to trigger re-runs to prevent spam
+      - name: Re-run failed workflow on override
+        if: |
+          steps.check_override.outputs.override_found == 'true' &&
+          github.event_name == 'issue_comment' &&
+          (github.event.comment.author_association == 'OWNER' ||
+           github.event.comment.author_association == 'MEMBER' ||
+           github.event.comment.author_association == 'COLLABORATOR')
+        uses: actions/github-script@v8
+        with:
+          script: |
+            const headSha = '${{ steps.pr_info.outputs.head_sha }}';
+            console.log(`Override comment found by ${{ steps.check_override.outputs.override_user }}`);
+            console.log('API proposal version change has been acknowledged.');
+
+            // Find the failed workflow run for this PR's head SHA
+            const { data: runs } = await github.rest.actions.listWorkflowRuns({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              workflow_id: 'api-proposal-version-check.yml',
+              head_sha: headSha,
+              status: 'completed',
+              per_page: 10
+            });
+
+            // Find the most recent failed run
+            const failedRun = runs.workflow_runs.find(run =>
+              run.conclusion === 'failure' && run.event === 'pull_request'
+            );
+
+            if (failedRun) {
+              console.log(`Re-running failed workflow run ${failedRun.id}`);
+              await github.rest.actions.reRunWorkflow({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                run_id: failedRun.id
+              });
+              console.log('Workflow re-run triggered successfully');
+            } else {
+              console.log('No failed pull_request workflow run found to re-run');
+              // The check will pass on this run since override exists
+            }
+
+      - name: Pass on override comment
+        if: steps.check_override.outputs.override_found == 'true'
+        run: |
+          echo "Override comment found by ${{ steps.check_override.outputs.override_user }}"
+          echo "API proposal version change has been acknowledged."
+
+      # Only continue checking if no override found
+      - name: Checkout repository
+        if: steps.check_override.outputs.override_found != 'true'
+        uses: actions/checkout@v6
+        with:
+          fetch-depth: 0
+
+      - name: Check for version changes
+        if: steps.check_override.outputs.override_found != 'true'
+        id: version_check
+        env:
+          HEAD_SHA: ${{ steps.pr_info.outputs.head_sha }}
+          BASE_SHA: ${{ steps.pr_info.outputs.base_sha }}
+        run: |
+          set -e
+
+          # Use merge-base to get accurate diff of what the PR actually changes
+          MERGE_BASE=$(git merge-base "$BASE_SHA" "$HEAD_SHA")
+          echo "Merge base: $MERGE_BASE"
+
+          # Get the list of changed proposed API files (diff against merge-base)
+          CHANGED_FILES=$(git diff --name-only "$MERGE_BASE" "$HEAD_SHA" -- 'src/vscode-dts/vscode.proposed.*.d.ts' || true)
+
+          if [ -z "$CHANGED_FILES" ]; then
+            echo "No proposed API files changed"
+            echo "version_changed=false" >> $GITHUB_OUTPUT
+            exit 0
+          fi
+
+          echo "Changed proposed API files:"
+          echo "$CHANGED_FILES"
+
+          VERSION_CHANGED="false"
+          CHANGED_LIST=""
+
+          for FILE in $CHANGED_FILES; do
+            # Check if file exists in head
+            if ! git cat-file -e "$HEAD_SHA:$FILE" 2>/dev/null; then
+              echo "File $FILE was deleted, skipping version check"
+              continue
+            fi
+
+            # Get version from head (current PR)
+            HEAD_VERSION=$(git show "$HEAD_SHA:$FILE" | grep -E '^// version: [0-9]+' | sed 's/.*version: //' || echo "")
+
+            # Get version from merge-base (what the PR is based on)
+            BASE_VERSION=$(git show "$MERGE_BASE:$FILE" 2>/dev/null | grep -E '^// version: [0-9]+' | sed 's/.*version: //' || echo "")
+
+            echo "File: $FILE"
+            echo "  Base version: ${BASE_VERSION:-'(none)'}"
+            echo "  Head version: ${HEAD_VERSION:-'(none)'}"
+
+            # Check if version was added or changed
+            if [ -n "$HEAD_VERSION" ] && [ "$HEAD_VERSION" != "$BASE_VERSION" ]; then
+              echo "  -> Version changed!"
+              VERSION_CHANGED="true"
+              FILENAME=$(basename "$FILE")
+              if [ -n "$CHANGED_LIST" ]; then
+                CHANGED_LIST="$CHANGED_LIST, $FILENAME"
+              else
+                CHANGED_LIST="$FILENAME"
+              fi
+            fi
+          done
+
+          echo "version_changed=$VERSION_CHANGED" >> $GITHUB_OUTPUT
+          echo "changed_files=$CHANGED_LIST" >> $GITHUB_OUTPUT
+
+      - name: Post warning comment
+        if: steps.check_override.outputs.override_found != 'true' && steps.version_check.outputs.version_changed == 'true'
+        uses: actions/github-script@v8
+        with:
+          script: |
+            const prNumber = ${{ steps.pr_info.outputs.number }};
+            const changedFiles = '${{ steps.version_check.outputs.changed_files }}';
+
+            // Check if we already posted a warning comment
+            const { data: comments } = await github.rest.issues.listComments({
+              owner: context.repo.owner,
+              repo: context.repo.repo,
+              issue_number: prNumber
+            });
+
+            const marker = '<!-- api-proposal-version-warning -->';
+            const existingComment = comments.find(comment =>
+              comment.body.includes(marker)
+            );
+
+            const body = `${marker}
+            ## ⚠️ API Proposal Version Change Detected
+
+            The following proposed API files have version changes: **${changedFiles}**
+
+            API proposal version changes should only be used when maintaining compatibility is not possible. Consider keeping the version as is and maintaining backward compatibility.
+
+            **Any version changes must be adopted by the consuming extensions before the next insiders for the extension to work.**
+
+            ---
+
+            If the version change is required, comment \`/api-proposal-change-required\` to unblock this check and acknowledge that you will update any critical consuming extensions (Copilot Chat).`;
+
+            if (existingComment) {
+              await github.rest.issues.updateComment({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                comment_id: existingComment.id,
+                body: body
+              });
+              console.log('Updated existing warning comment');
+            } else {
+              await github.rest.issues.createComment({
+                owner: context.repo.owner,
+                repo: context.repo.repo,
+                issue_number: prNumber,
+                body: body
+              });
+              console.log('Posted new warning comment');
+            }
+
+      - name: Fail if version changed without override
+        if: steps.check_override.outputs.override_found != 'true' && steps.version_check.outputs.version_changed == 'true'
+        run: |
+          echo "::error::API proposal version changed in: ${{ steps.version_check.outputs.changed_files }}"
+          echo "To unblock, comment '/api-proposal-change-required' on the PR."
+          exit 1
diff --git a/.github/workflows/no-engineering-system-changes.yml b/.github/workflows/no-engineering-system-changes.yml
index 45d1ae55f623b..be9cf34d0777a 100644
--- a/.github/workflows/no-engineering-system-changes.yml
+++ b/.github/workflows/no-engineering-system-changes.yml
@@ -21,22 +21,52 @@ jobs:
             echo "engineering_systems_modified=false" >> $GITHUB_OUTPUT
             echo "No engineering systems were modified in this PR"
           fi
+      - name: Allow automated distro updates
+        id: distro_exception
+        if: ${{ steps.engineering_systems_check.outputs.engineering_systems_modified == 'true' && github.event.pull_request.user.login == 'vs-code-engineering[bot]' }}
+        run: |
+          # Allow the vs-code-engineering bot ONLY when package.json is the
+          # sole changed file and the diff exclusively touches the "distro" field.
+          ONLY_PKG=$(jq -e '. == ["package.json"]' "$HOME/files.json" > /dev/null 2>&1 && echo true || echo false)
+          if [[ "$ONLY_PKG" != "true" ]]; then
+            echo "Bot modified files beyond package.json — not allowed"
+            echo "allowed=false" >> $GITHUB_OUTPUT
+            exit 0
+          fi
+
+          DIFF=$(gh pr diff ${{ github.event.pull_request.number }} --repo ${{ github.repository }}) || {
+            echo "Failed to fetch PR diff — not allowed"
+            echo "allowed=false" >> $GITHUB_OUTPUT
+            exit 0
+          }
+          CHANGED_LINES=$(echo "$DIFF" | grep -E '^[+-]' | grep -vE '^(\+\+\+|---)' | wc -l)
+          DISTRO_LINES=$(echo "$DIFF" | grep -cE '^[+-][[:space:]]*"distro"[[:space:]]*:' || true)
+
+          if [[ "$CHANGED_LINES" -eq 2 && "$DISTRO_LINES" -eq 2 ]]; then
+            echo "Distro-only update by bot — allowing"
+            echo "allowed=true" >> $GITHUB_OUTPUT
+          else
+            echo "Bot changed more than the distro field — not allowed"
+            echo "allowed=false" >> $GITHUB_OUTPUT
+          fi
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
       - name: Prevent Copilot from modifying engineering systems
-        if: ${{ steps.engineering_systems_check.outputs.engineering_systems_modified == 'true' && github.event.pull_request.user.login == 'Copilot' }}
+        if: ${{ steps.engineering_systems_check.outputs.engineering_systems_modified == 'true' && steps.distro_exception.outputs.allowed != 'true' && github.event.pull_request.user.login == 'Copilot' }}
         run: |
           echo "Copilot is not allowed to modify .github/workflows, build folder files, or package.json files."
           echo "If you need to update engineering systems, please do so manually or through authorized means."
           exit 1
       - uses: octokit/request-action@dad4362715b7fb2ddedf9772c8670824af564f0d # v2.4.0
         id: get_permissions
-        if: ${{ steps.engineering_systems_check.outputs.engineering_systems_modified == 'true' && github.event.pull_request.user.login != 'Copilot' }}
+        if: ${{ steps.engineering_systems_check.outputs.engineering_systems_modified == 'true' && steps.distro_exception.outputs.allowed != 'true' && github.event.pull_request.user.login != 'Copilot' }}
         with:
           route: GET /repos/microsoft/vscode/collaborators/${{ github.event.pull_request.user.login }}/permission
         env:
           GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
       - name: Set control output variable
         id: control
-        if: ${{ steps.engineering_systems_check.outputs.engineering_systems_modified == 'true' && github.event.pull_request.user.login != 'Copilot' }}
+        if: ${{ steps.engineering_systems_check.outputs.engineering_systems_modified == 'true' && steps.distro_exception.outputs.allowed != 'true' && github.event.pull_request.user.login != 'Copilot' }}
         run: |
           echo "user: ${{ github.event.pull_request.user.login }}"
           echo "role: ${{ fromJson(steps.get_permissions.outputs.data).permission }}"
@@ -44,7 +74,7 @@ jobs:
           echo "should_run: ${{ !contains(fromJson('["admin", "maintain", "write"]'), fromJson(steps.get_permissions.outputs.data).permission) }}"
           echo "should_run=${{ !contains(fromJson('["admin", "maintain", "write"]'), fromJson(steps.get_permissions.outputs.data).permission) && github.event.pull_request.user.login != 'dependabot[bot]' }}" >> $GITHUB_OUTPUT
       - name: Check for engineering system changes
-        if: ${{ steps.engineering_systems_check.outputs.engineering_systems_modified == 'true' && steps.control.outputs.should_run == 'true' }}
+        if: ${{ steps.engineering_systems_check.outputs.engineering_systems_modified == 'true' && steps.distro_exception.outputs.allowed != 'true' && steps.control.outputs.should_run == 'true' }}
         run: |
           echo "Changes to .github/workflows/, build/ folder files, or package.json files aren't allowed in PRs."
           exit 1
diff --git a/.github/workflows/pr-darwin-test.yml b/.github/workflows/pr-darwin-test.yml
index c876d2a3782be..56cd6e6ba2eb4 100644
--- a/.github/workflows/pr-darwin-test.yml
+++ b/.github/workflows/pr-darwin-test.yml
@@ -212,7 +212,7 @@ jobs:
         if: always()
 
       - name: Publish Crash Reports
-        uses: actions/upload-artifact@v6
+        uses: actions/upload-artifact@v7
         if: failure()
         continue-on-error: true
         with:
@@ -223,7 +223,7 @@ jobs:
       # In order to properly symbolify above crash reports
       # (if any), we need the compiled native modules too
       - name: Publish Node Modules
-        uses: actions/upload-artifact@v6
+        uses: actions/upload-artifact@v7
         if: failure()
         continue-on-error: true
         with:
@@ -232,7 +232,7 @@ jobs:
           if-no-files-found: ignore
 
       - name: Publish Log Files
-        uses: actions/upload-artifact@v6
+        uses: actions/upload-artifact@v7
         if: always()
         continue-on-error: true
         with:
diff --git a/.github/workflows/pr-linux-test.yml b/.github/workflows/pr-linux-test.yml
index df6ab20e586b5..7922ec107f90a 100644
--- a/.github/workflows/pr-linux-test.yml
+++ b/.github/workflows/pr-linux-test.yml
@@ -258,7 +258,7 @@ jobs:
         if: always()
 
       - name: Publish Crash Reports
-        uses: actions/upload-artifact@v6
+        uses: actions/upload-artifact@v7
         if: failure()
         continue-on-error: true
         with:
@@ -269,7 +269,7 @@ jobs:
       # In order to properly symbolify above crash reports
       # (if any), we need the compiled native modules too
       - name: Publish Node Modules
-        uses: actions/upload-artifact@v6
+        uses: actions/upload-artifact@v7
         if: failure()
         continue-on-error: true
         with:
@@ -278,7 +278,7 @@ jobs:
           if-no-files-found: ignore
 
       - name: Publish Log Files
-        uses: actions/upload-artifact@v6
+        uses: actions/upload-artifact@v7
         if: always()
         continue-on-error: true
         with:
diff --git a/.github/workflows/pr-win32-test.yml b/.github/workflows/pr-win32-test.yml
index bd4a62d42fa26..2bde317b4806a 100644
--- a/.github/workflows/pr-win32-test.yml
+++ b/.github/workflows/pr-win32-test.yml
@@ -249,7 +249,7 @@ jobs:
         if: always()
 
       - name: Publish Crash Reports
-        uses: actions/upload-artifact@v6
+        uses: actions/upload-artifact@v7
         if: failure()
         continue-on-error: true
         with:
@@ -260,7 +260,7 @@ jobs:
       # In order to properly symbolify above crash reports
       # (if any), we need the compiled native modules too
       - name: Publish Node Modules
-        uses: actions/upload-artifact@v6
+        uses: actions/upload-artifact@v7
         if: failure()
         continue-on-error: true
         with:
@@ -269,7 +269,7 @@ jobs:
           if-no-files-found: ignore
 
       - name: Publish Log Files
-        uses: actions/upload-artifact@v6
+        uses: actions/upload-artifact@v7
         if: always()
         continue-on-error: true
         with:
diff --git a/.github/workflows/pr.yml b/.github/workflows/pr.yml
index b988d19f49ea6..bb87ac077bce2 100644
--- a/.github/workflows/pr.yml
+++ b/.github/workflows/pr.yml
@@ -77,7 +77,7 @@ jobs:
         working-directory: build
 
       - name: Compile & Hygiene
-        run: npm exec -- npm-run-all2 -lp core-ci extensions-ci hygiene eslint valid-layers-check define-class-fields-check vscode-dts-compile-check tsec-compile-check test-build-scripts
+        run: npm exec -- npm-run-all2 -lp core-ci hygiene eslint valid-layers-check define-class-fields-check vscode-dts-compile-check tsec-compile-check test-build-scripts
         env:
           GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
 
diff --git a/.github/workflows/screenshot-test.yml b/.github/workflows/screenshot-test.yml
index a45f8d38133bb..01f186a1c8146 100644
--- a/.github/workflows/screenshot-test.yml
+++ b/.github/workflows/screenshot-test.yml
@@ -1,4 +1,4 @@
-name: Screenshot Tests
+name: Checking Component Screenshots
 
 on:
   push:
@@ -10,8 +10,6 @@ on:
 
 permissions:
   contents: read
-  pull-requests: write
-  checks: write
   statuses: write
 
 concurrency:
@@ -20,15 +18,16 @@ concurrency:
 
 jobs:
   screenshots:
+    name: Checking Component Screenshots
     runs-on: ubuntu-latest
     steps:
       - name: Checkout
-        uses: actions/checkout@v4
+        uses: actions/checkout@v6
         with:
           lfs: true
 
       - name: Setup Node.js
-        uses: actions/setup-node@v4
+        uses: actions/setup-node@v6
         with:
           node-version-file: .nvmrc
 
@@ -55,12 +54,12 @@ jobs:
         run: npx playwright install chromium
 
       - name: Capture screenshots
-        run: npx component-explorer screenshot --project ./test/componentFixtures/component-explorer.json
+        run: ./node_modules/.bin/component-explorer screenshot --project ./test/componentFixtures/component-explorer.json
 
       - name: Compare screenshots
         id: compare
         run: |
-          npx component-explorer screenshot:compare \
+          ./node_modules/.bin/component-explorer screenshot:compare \
             --project ./test/componentFixtures \
             --report ./test/componentFixtures/.screenshots/report
         continue-on-error: true
@@ -74,14 +73,14 @@ jobs:
           fi
 
       - name: Upload explorer artifact
-        uses: actions/upload-artifact@v4
+        uses: actions/upload-artifact@v7
         with:
           name: component-explorer
           path: /tmp/explorer-artifact/
 
       - name: Upload screenshot report
         if: steps.compare.outcome == 'failure'
-        uses: actions/upload-artifact@v4
+        uses: actions/upload-artifact@v7
         with:
           name: screenshot-diff
           path: |
@@ -93,41 +92,35 @@ jobs:
           GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
         run: |
           REPORT="test/componentFixtures/.screenshots/report/report.json"
+          STATE="success"
           if [ -f "$REPORT" ]; then
             CHANGED=$(node -e "const r = require('./$REPORT'); console.log(r.summary.added + r.summary.removed + r.summary.changed)")
-            TITLE="${CHANGED} screenshots changed"
+            TITLE="⚠ ${CHANGED} screenshots changed"
+            BLOCKS_CI=$(node -e "
+              const r = require('./$REPORT');
+              const blocking = Object.entries(r.fixtures).filter(([, f]) =>
+                f.status !== 'unchanged' && (f.labels || []).includes('blocks-ci')
+              );
+              if (blocking.length > 0) {
+                console.log(blocking.map(([name]) => name).join(', '));
+              }
+            ")
+            if [ -n "$BLOCKS_CI" ]; then
+              STATE="failure"
+              TITLE="❌ ${CHANGED} screenshots changed (blocks CI: ${BLOCKS_CI})"
+            fi
           else
-            TITLE="Screenshots match"
+            TITLE="✅ Screenshots match"
           fi
 
           SHA="${{ github.event.pull_request.head.sha || github.sha }}"
-          CHECK_RUN_ID=$(gh api "repos/${{ github.repository }}/commits/$SHA/check-runs" \
-            --jq '.check_runs[] | select(.name == "screenshots") | .id')
+          DETAILS_URL="https://hediet-ghartifactpreview.azurewebsites.net/${{ github.repository }}/run/${{ github.run_id }}/component-explorer/___explorer.html?report=./screenshot-report/report.json&search=changed"
 
-          DETAILS_URL="https://hediet-ghartifactpreview.azurewebsites.net/${{ github.repository }}/run/${{ github.run_id }}/component-explorer/___explorer.html?report=./screenshot-report/report.json"
-
-          if [ -n "$CHECK_RUN_ID" ]; then
-            gh api "repos/${{ github.repository }}/check-runs/$CHECK_RUN_ID" \
-              -X PATCH --input - <<EOF || echo "::warning::Could not update check run (expected for fork PRs)"
-          {"details_url":"$DETAILS_URL","output":{"title":"$TITLE","summary":"$TITLE"}}
-          EOF
-          fi
-
-          DETAILS_URL="https://hediet-ghartifactpreview.azurewebsites.net/${{ github.repository }}/run/${{ github.run_id }}/component-explorer/___explorer.html?report=./screenshot-report/report.json"
           gh api "repos/${{ github.repository }}/statuses/$SHA" \
             --input - <<EOF || echo "::warning::Could not create commit status (expected for fork PRs)"
-          {"state":"success","target_url":"$DETAILS_URL","description":"$TITLE","context":"screenshots / explorer"}
+          {"state":"$STATE","target_url":"$DETAILS_URL","description":"$TITLE","context":"Component Screenshots"}
           EOF
 
-      - name: Post summary
-        run: |
-          if [ -f test/componentFixtures/.screenshots/report/report.md ]; then
-            cat test/componentFixtures/.screenshots/report/report.md >> $GITHUB_STEP_SUMMARY
-          else
-            echo "## Screenshots ✅" >> $GITHUB_STEP_SUMMARY
-            echo "No visual changes detected." >> $GITHUB_STEP_SUMMARY
-          fi
-
       # - name: Post PR comment
       #   if: github.event_name == 'pull_request'
       #   env:
diff --git a/.github/workflows/sessions-e2e.yml b/.github/workflows/sessions-e2e.yml
new file mode 100644
index 0000000000000..b7047a8e30a07
--- /dev/null
+++ b/.github/workflows/sessions-e2e.yml
@@ -0,0 +1,66 @@
+name: Sessions E2E Tests
+
+on:
+  pull_request:
+    branches:
+      - main
+      - 'release/*'
+    paths:
+      - 'src/vs/sessions/**'
+      - 'scripts/code-sessions-web.*'
+
+permissions:
+  contents: read
+
+concurrency:
+  group: sessions-e2e-${{ github.event.pull_request.number || github.sha }}
+  cancel-in-progress: true
+
+jobs:
+  sessions-e2e:
+    name: Sessions E2E Tests
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v6
+
+      - name: Setup Node.js
+        uses: actions/setup-node@v6
+        with:
+          node-version-file: .nvmrc
+
+      - name: Install build tools
+        run: sudo apt update -y && sudo apt install -y build-essential pkg-config libx11-dev libx11-xcb-dev libxkbfile-dev libnotify-bin libkrb5-dev xvfb
+
+      - name: Install dependencies
+        run: npm ci
+        env:
+          ELECTRON_SKIP_BINARY_DOWNLOAD: 1
+          PLAYWRIGHT_SKIP_BROWSER_DOWNLOAD: 1
+          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+
+      - name: Install build dependencies
+        run: npm ci
+        working-directory: build
+
+      - name: Transpile sources
+        run: npm run transpile-client
+
+      - name: Install E2E test dependencies
+        run: npm ci
+        working-directory: src/vs/sessions/test/e2e
+
+      - name: Install Playwright browsers
+        run: npx playwright install chromium
+
+      - name: Run Sessions E2E tests
+        run: xvfb-run npm test
+        working-directory: src/vs/sessions/test/e2e
+
+      - name: Upload failure screenshots
+        if: failure()
+        uses: actions/upload-artifact@v7
+        with:
+          name: sessions-e2e-failures
+          path: src/vs/sessions/test/e2e/out/failure-*.png
+          retention-days: 7
diff --git a/.gitignore b/.gitignore
index 9a9fdcadff97a..e5ca4dd32cc0b 100644
--- a/.gitignore
+++ b/.gitignore
@@ -29,3 +29,22 @@ test-output.json
 test/componentFixtures/.screenshots/*
 !test/componentFixtures/.screenshots/baseline/
 dist
+.playwright-cli
+.agents/agents/*.local.md
+.claude/agents/*.local.md
+.github/agents/*.local.md
+.agents/agents/*.local.agent.md
+.claude/agents/*.local.agent.md
+.github/agents/*.local.agent.md
+.agents/hooks/*.local.json
+.claude/hooks/*.local.json
+.github/hooks/*.local.json
+.agents/instructions/*.local.instructions.md
+.claude/instructions/*.local.instructions.md
+.github/instructions/*.local.instructions.md
+.agents/prompts/*.local.prompt.md
+.claude/prompts/*.local.prompt.md
+.github/prompts/*.local.prompt.md
+.agents/skills/.local/
+.claude/skills/.local/
+.github/skills/.local/
diff --git a/.npmrc b/.npmrc
index b07eade64d573..a275846ab5c04 100644
--- a/.npmrc
+++ b/.npmrc
@@ -1,6 +1,6 @@
 disturl="https://electronjs.org/headers"
-target="39.6.0"
-ms_build_id="13330601"
+target="39.8.0"
+ms_build_id="13470701"
 runtime="electron"
 ignore-scripts=false
 build_from_source="true"
diff --git a/.vscode/extensions/vscode-extras/package-lock.json b/.vscode/extensions/vscode-extras/package-lock.json
new file mode 100644
index 0000000000000..3268c74682804
--- /dev/null
+++ b/.vscode/extensions/vscode-extras/package-lock.json
@@ -0,0 +1,16 @@
+{
+	"name": "vscode-extras",
+	"version": "0.0.1",
+	"lockfileVersion": 3,
+	"requires": true,
+	"packages": {
+		"": {
+			"name": "vscode-extras",
+			"version": "0.0.1",
+			"license": "MIT",
+			"engines": {
+				"vscode": "^1.88.0"
+			}
+		}
+	}
+}
diff --git a/.vscode/extensions/vscode-extras/package.json b/.vscode/extensions/vscode-extras/package.json
new file mode 100644
index 0000000000000..c773d5923c322
--- /dev/null
+++ b/.vscode/extensions/vscode-extras/package.json
@@ -0,0 +1,38 @@
+{
+	"name": "vscode-extras",
+	"displayName": "VS Code Extras",
+	"description": "Extra utility features for the VS Code selfhost workspace",
+	"engines": {
+		"vscode": "^1.88.0"
+	},
+	"version": "0.0.1",
+	"publisher": "ms-vscode",
+	"categories": [
+		"Other"
+	],
+	"activationEvents": [
+		"workspaceContains:src/vscode-dts/vscode.d.ts"
+	],
+	"main": "./out/extension.js",
+	"repository": {
+		"type": "git",
+		"url": "https://github.com/microsoft/vscode.git"
+	},
+	"license": "MIT",
+	"scripts": {
+		"compile": "gulp compile-extension:vscode-extras",
+		"watch": "gulp watch-extension:vscode-extras"
+	},
+	"contributes": {
+		"configuration": {
+			"title": "VS Code Extras",
+			"properties": {
+				"vscode-extras.npmUpToDateFeature.enabled": {
+					"type": "boolean",
+					"default": true,
+					"description": "Show a status bar warning when npm dependencies are out of date."
+				}
+			}
+		}
+	}
+}
diff --git a/.vscode/extensions/vscode-extras/src/extension.ts b/.vscode/extensions/vscode-extras/src/extension.ts
new file mode 100644
index 0000000000000..675bfe9177549
--- /dev/null
+++ b/.vscode/extensions/vscode-extras/src/extension.ts
@@ -0,0 +1,51 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as vscode from 'vscode';
+import { NpmUpToDateFeature } from './npmUpToDateFeature';
+
+export class Extension extends vscode.Disposable {
+	private readonly _output: vscode.LogOutputChannel;
+	private _npmFeature: NpmUpToDateFeature | undefined;
+
+	constructor(_context: vscode.ExtensionContext) {
+		const disposables: vscode.Disposable[] = [];
+		super(() => disposables.forEach(d => d.dispose()));
+
+		this._output = vscode.window.createOutputChannel('VS Code Extras', { log: true });
+		disposables.push(this._output);
+
+		this._updateNpmFeature();
+
+		disposables.push(
+			vscode.workspace.onDidChangeConfiguration(e => {
+				if (e.affectsConfiguration('vscode-extras.npmUpToDateFeature.enabled')) {
+					this._updateNpmFeature();
+				}
+			})
+		);
+	}
+
+	private _updateNpmFeature(): void {
+		const enabled = vscode.workspace.getConfiguration('vscode-extras').get<boolean>('npmUpToDateFeature.enabled', true);
+		if (enabled && !this._npmFeature) {
+			this._npmFeature = new NpmUpToDateFeature(this._output);
+		} else if (!enabled && this._npmFeature) {
+			this._npmFeature.dispose();
+			this._npmFeature = undefined;
+		}
+	}
+}
+
+let extension: Extension | undefined;
+
+export function activate(context: vscode.ExtensionContext) {
+	extension = new Extension(context);
+	context.subscriptions.push(extension);
+}
+
+export function deactivate() {
+	extension = undefined;
+}
diff --git a/.vscode/extensions/vscode-extras/src/npmUpToDateFeature.ts b/.vscode/extensions/vscode-extras/src/npmUpToDateFeature.ts
new file mode 100644
index 0000000000000..8927b0b7064a9
--- /dev/null
+++ b/.vscode/extensions/vscode-extras/src/npmUpToDateFeature.ts
@@ -0,0 +1,251 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as cp from 'child_process';
+import * as fs from 'fs';
+import * as path from 'path';
+import * as vscode from 'vscode';
+
+interface FileHashes {
+	readonly [relativePath: string]: string;
+}
+
+interface PostinstallState {
+	readonly nodeVersion: string;
+	readonly fileHashes: FileHashes;
+}
+
+interface InstallState {
+	readonly root: string;
+	readonly stateContentsFile: string;
+	readonly current: PostinstallState;
+	readonly saved: PostinstallState | undefined;
+	readonly files: readonly string[];
+}
+
+export class NpmUpToDateFeature extends vscode.Disposable {
+	private readonly _statusBarItem: vscode.StatusBarItem;
+	private readonly _disposables: vscode.Disposable[] = [];
+	private _watchers: fs.FSWatcher[] = [];
+	private _terminal: vscode.Terminal | undefined;
+	private _stateContentsFile: string | undefined;
+	private _root: string | undefined;
+
+	private static readonly _scheme = 'npm-dep-state';
+
+	constructor(private readonly _output: vscode.LogOutputChannel) {
+		const disposables: vscode.Disposable[] = [];
+		super(() => {
+			disposables.forEach(d => d.dispose());
+			for (const w of this._watchers) {
+				w.close();
+			}
+		});
+		this._disposables = disposables;
+
+		this._statusBarItem = vscode.window.createStatusBarItem(vscode.StatusBarAlignment.Left, 10000);
+		this._statusBarItem.name = 'npm Install State';
+		this._statusBarItem.text = '$(warning) node_modules is stale - run npm i';
+		this._statusBarItem.tooltip = 'Dependencies are out of date. Click to run npm install.';
+		this._statusBarItem.command = 'vscode-extras.runNpmInstall';
+		this._statusBarItem.backgroundColor = new vscode.ThemeColor('statusBarItem.warningBackground');
+		this._disposables.push(this._statusBarItem);
+
+		this._disposables.push(
+			vscode.workspace.registerTextDocumentContentProvider(NpmUpToDateFeature._scheme, {
+				provideTextDocumentContent: (uri) => {
+					const params = new URLSearchParams(uri.query);
+					const source = params.get('source');
+					const file = uri.path.slice(1); // strip leading /
+					if (source === 'saved') {
+						return this._readSavedContent(file);
+					}
+					return this._readCurrentContent(file);
+				}
+			})
+		);
+
+		this._disposables.push(
+			vscode.commands.registerCommand('vscode-extras.runNpmInstall', () => this._runNpmInstall())
+		);
+
+		this._disposables.push(
+			vscode.commands.registerCommand('vscode-extras.showDependencyDiff', (file: string) => this._showDiff(file))
+		);
+
+		this._disposables.push(
+			vscode.window.onDidCloseTerminal(t => {
+				if (t === this._terminal) {
+					this._terminal = undefined;
+					this._check();
+				}
+			})
+		);
+
+		this._check();
+	}
+
+	private _runNpmInstall(): void {
+		if (this._terminal) {
+			this._terminal.dispose();
+		}
+		const workspaceRoot = vscode.workspace.workspaceFolders?.[0]?.uri;
+		if (!workspaceRoot) {
+			return;
+		}
+		this._terminal = vscode.window.createTerminal({ name: 'npm install', cwd: workspaceRoot });
+		this._terminal.sendText('node build/npm/fast-install.ts --force');
+		this._terminal.show();
+
+		this._statusBarItem.text = '$(loading~spin) npm i';
+		this._statusBarItem.tooltip = 'npm install is running...';
+		this._statusBarItem.backgroundColor = undefined;
+		this._statusBarItem.command = 'vscode-extras.runNpmInstall';
+	}
+
+	private _queryState(): InstallState | undefined {
+		const workspaceRoot = vscode.workspace.workspaceFolders?.[0]?.uri.fsPath;
+		if (!workspaceRoot) {
+			return undefined;
+		}
+		try {
+			const script = path.join(workspaceRoot, 'build', 'npm', 'installStateHash.ts');
+			const output = cp.execFileSync(process.execPath, [script], {
+				cwd: workspaceRoot,
+				timeout: 10_000,
+				encoding: 'utf8',
+			});
+			const parsed = JSON.parse(output.trim());
+			this._output.trace('raw output:', output.trim());
+			return parsed;
+		} catch (e) {
+			this._output.error('_queryState error:', e as any);
+			return undefined;
+		}
+	}
+
+	private _check(): void {
+		const state = this._queryState();
+		this._output.trace('state:', JSON.stringify(state, null, 2));
+		if (!state) {
+			this._output.trace('no state, hiding');
+			this._statusBarItem.hide();
+			return;
+		}
+
+		this._stateContentsFile = state.stateContentsFile;
+		this._root = state.root;
+		this._setupWatcher(state);
+
+		const changedFiles = this._getChangedFiles(state);
+		this._output.trace('changedFiles:', JSON.stringify(changedFiles));
+
+		if (changedFiles.length === 0) {
+			this._statusBarItem.hide();
+		} else {
+			this._statusBarItem.text = '$(warning) node_modules is stale - run npm i';
+			const tooltip = new vscode.MarkdownString();
+			tooltip.isTrusted = true;
+			tooltip.supportHtml = true;
+			tooltip.appendMarkdown('**Dependencies are out of date.** Click to run npm install.\n\nChanged files:\n\n');
+			for (const entry of changedFiles) {
+				if (entry.isFile) {
+					const args = encodeURIComponent(JSON.stringify(entry.label));
+					tooltip.appendMarkdown(`- [${entry.label}](command:vscode-extras.showDependencyDiff?${args})\n`);
+				} else {
+					tooltip.appendMarkdown(`- ${entry.label}\n`);
+				}
+			}
+			this._statusBarItem.tooltip = tooltip;
+			this._statusBarItem.backgroundColor = new vscode.ThemeColor('statusBarItem.warningBackground');
+			this._statusBarItem.show();
+		}
+	}
+
+	private _showDiff(file: string): void {
+		const cacheBuster = Date.now().toString();
+		const savedUri = vscode.Uri.from({
+			scheme: NpmUpToDateFeature._scheme,
+			path: `/${file}`,
+			query: new URLSearchParams({ source: 'saved', t: cacheBuster }).toString(),
+		});
+		const currentUri = vscode.Uri.from({
+			scheme: NpmUpToDateFeature._scheme,
+			path: `/${file}`,
+			query: new URLSearchParams({ source: 'current', t: cacheBuster }).toString(),
+		});
+
+		vscode.commands.executeCommand('vscode.diff', savedUri, currentUri, `${file} (last install ↔ current)`);
+	}
+
+	private _readSavedContent(file: string): string {
+		if (!this._stateContentsFile) {
+			return '';
+		}
+		try {
+			const contents: Record<string, string> = JSON.parse(fs.readFileSync(this._stateContentsFile, 'utf8'));
+			return contents[file] ?? '';
+		} catch {
+			return '';
+		}
+	}
+
+	private _readCurrentContent(file: string): string {
+		if (!this._root) {
+			return '';
+		}
+		try {
+			const script = path.join(this._root, 'build', 'npm', 'installStateHash.ts');
+			return cp.execFileSync(process.execPath, [script, '--normalize-file', path.join(this._root, file)], {
+				cwd: this._root,
+				timeout: 10_000,
+				encoding: 'utf8',
+			});
+		} catch {
+			return '';
+		}
+	}
+
+	private _getChangedFiles(state: InstallState): { readonly label: string; readonly isFile: boolean }[] {
+		if (!state.saved) {
+			return [{ label: '(no postinstall state found)', isFile: false }];
+		}
+		const changed: { readonly label: string; readonly isFile: boolean }[] = [];
+		if (state.saved.nodeVersion !== state.current.nodeVersion) {
+			changed.push({ label: `Node.js version (${state.saved.nodeVersion} → ${state.current.nodeVersion})`, isFile: false });
+		}
+		const allKeys = new Set([...Object.keys(state.current.fileHashes), ...Object.keys(state.saved.fileHashes)]);
+		for (const key of allKeys) {
+			if (state.current.fileHashes[key] !== state.saved.fileHashes[key]) {
+				changed.push({ label: key, isFile: true });
+			}
+		}
+		return changed;
+	}
+
+	private _setupWatcher(state: InstallState): void {
+		for (const w of this._watchers) {
+			w.close();
+		}
+		this._watchers = [];
+
+		let debounceTimer: ReturnType<typeof setTimeout> | undefined;
+		const scheduleCheck = () => {
+			if (debounceTimer) {
+				clearTimeout(debounceTimer);
+			}
+			debounceTimer = setTimeout(() => this._check(), 500);
+		};
+
+		for (const file of state.files) {
+			try {
+				const watcher = fs.watch(file, scheduleCheck);
+				this._watchers.push(watcher);
+			} catch {
+				// file may not exist yet
+			}
+		}
+	}
+}
diff --git a/.vscode/extensions/vscode-extras/tsconfig.json b/.vscode/extensions/vscode-extras/tsconfig.json
new file mode 100644
index 0000000000000..9133c3bbf4b87
--- /dev/null
+++ b/.vscode/extensions/vscode-extras/tsconfig.json
@@ -0,0 +1,14 @@
+{
+	"extends": "../../../extensions/tsconfig.base.json",
+	"compilerOptions": {
+		"rootDir": "./src",
+		"outDir": "./out",
+		"types": [
+			"node"
+		]
+	},
+	"include": [
+		"src/**/*",
+		"../../../src/vscode-dts/vscode.d.ts"
+	]
+}
diff --git a/.vscode/extensions/vscode-selfhost-test-provider/src/testOutputScanner.ts b/.vscode/extensions/vscode-selfhost-test-provider/src/testOutputScanner.ts
index 296ed1e9f12be..09e9a2af6d2b5 100644
--- a/.vscode/extensions/vscode-selfhost-test-provider/src/testOutputScanner.ts
+++ b/.vscode/extensions/vscode-selfhost-test-provider/src/testOutputScanner.ts
@@ -545,6 +545,9 @@ export class SourceMapStore {
 			}
 		}
 
+		if (/^[a-zA-Z]:/.test(source) || source.startsWith('/')) {
+			return vscode.Uri.file(source);
+		}
 		return vscode.Uri.parse(source);
 	}
 
diff --git a/.vscode/launch.json b/.vscode/launch.json
index d116d2c003389..47d901042e3a8 100644
--- a/.vscode/launch.json
+++ b/.vscode/launch.json
@@ -278,6 +278,51 @@
 				"hidden": true,
 			},
 		},
+		{
+			"type": "chrome",
+			"request": "launch",
+			"name": "Launch VS Sessions Internal",
+			"windows": {
+				"runtimeExecutable": "${workspaceFolder}/scripts/code.bat"
+			},
+			"osx": {
+				"runtimeExecutable": "${workspaceFolder}/scripts/code.sh"
+			},
+			"linux": {
+				"runtimeExecutable": "${workspaceFolder}/scripts/code.sh"
+			},
+			"port": 9222,
+			"timeout": 0,
+			"env": {
+				"VSCODE_EXTHOST_WILL_SEND_SOCKET": null,
+				"VSCODE_SKIP_PRELAUNCH": "1",
+				"VSCODE_DEV_DEBUG_OBSERVABLES": "1",
+			},
+			"cleanUp": "wholeBrowser",
+			"killBehavior": "polite",
+			"runtimeArgs": [
+				"--inspect-brk=5875",
+				"--no-cached-data",
+				"--crash-reporter-directory=${workspaceFolder}/.profile-oss/crashes",
+				// for general runtime freezes: https://github.com/microsoft/vscode/issues/127861#issuecomment-904144910
+				"--disable-features=CalculateNativeWinOcclusion",
+				"--disable-extension=vscode.vscode-api-tests",
+				"--sessions"
+			],
+			"userDataDir": "${userHome}/.vscode-oss-sessions-dev",
+			"webRoot": "${workspaceFolder}",
+			"cascadeTerminateToConfigurations": [
+				"Attach to Extension Host"
+			],
+			"pauseForSourceMap": false,
+			"outFiles": [
+				"${workspaceFolder}/out/**/*.js"
+			],
+			"browserLaunchLocation": "workspace",
+			"presentation": {
+				"hidden": true,
+			},
+		},
 		{
 			// To debug observables you also need the extension "ms-vscode.debug-value-editor"
 			"type": "chrome",
@@ -603,9 +648,19 @@
 			}
 		},
 		{
-			"name": "Component Explorer",
+			"name": "Component Explorer (Edge)",
 			"type": "msedge",
-			"port": 9230,
+			"request": "launch",
+			"url": "http://localhost:5337/___explorer",
+			"preLaunchTask": "Launch Component Explorer",
+			"presentation": {
+				"group": "1_component_explorer",
+				"order": 4
+			}
+		},
+		{
+			"name": "Component Explorer (Chrome)",
+			"type": "chrome",
 			"request": "launch",
 			"url": "http://localhost:5337/___explorer",
 			"preLaunchTask": "Launch Component Explorer",
@@ -653,6 +708,21 @@
 				"order": 1
 			}
 		},
+		{
+			"name": "VS Sessions",
+			"stopAll": true,
+			"configurations": [
+				"Launch VS Sessions Internal",
+				"Attach to Main Process",
+				"Attach to Extension Host",
+				"Attach to Shared Process",
+			],
+			"preLaunchTask": "Ensure Prelaunch Dependencies",
+			"presentation": {
+				"group": "0_vscode",
+				"order": 1
+			}
+		},
 		{
 			"name": "VS Code (Hot Reload)",
 			"stopAll": true,
diff --git a/.vscode/notebooks/endgame.github-issues b/.vscode/notebooks/endgame.github-issues
index d3f716f5749cb..96e5e5690d0ea 100644
--- a/.vscode/notebooks/endgame.github-issues
+++ b/.vscode/notebooks/endgame.github-issues
@@ -7,7 +7,7 @@
   {
     "kind": 2,
     "language": "github-issues",
-    "value": "$MILESTONE=milestone:\"February 2026\""
+    "value": "$MILESTONE=milestone:\"1.112.0\""
   },
   {
     "kind": 1,
diff --git a/.vscode/notebooks/my-endgame.github-issues b/.vscode/notebooks/my-endgame.github-issues
index b58910ad675e5..e3ddd3af411af 100644
--- a/.vscode/notebooks/my-endgame.github-issues
+++ b/.vscode/notebooks/my-endgame.github-issues
@@ -7,12 +7,12 @@
   {
     "kind": 2,
     "language": "github-issues",
-    "value": "$MILESTONE=milestone:\"February 2026\"\n\n$MINE=assignee:@me"
+    "value": "$MILESTONE=milestone:\"1.112.0\"\n\n$MINE=assignee:@me"
   },
   {
     "kind": 2,
     "language": "github-issues",
-    "value": "$NOT_TEAM_MEMBERS=-author:aeschli -author:alexdima -author:alexr00 -author:AmandaSilver -author:bamurtaugh -author:bpasero -author:chrmarti -author:Chuxel -author:claudiaregio -author:connor4312 -author:dbaeumer -author:deepak1556 -author:devinvalenciano -author:digitarald -author:DonJayamanne -author:egamma -author:fiveisprime -author:ntrogh -author:hediet -author:isidorn -author:joaomoreno -author:jrieken -author:kieferrm -author:lramos15 -author:lszomoru -author:meganrogge -author:misolori -author:mjbvz -author:rebornix -author:roblourens -author:rzhao271 -author:sandy081 -author:sbatten -author:stevencl -author:TylerLeonhardt -author:Tyriar -author:weinand -author:amunger -author:karthiknadig -author:eleanorjboyd -author:Yoyokrazy -author:ulugbekna -author:aiday-mar -author:bhavyaus -author:justschen -author:benibenj -author:luabud -author:anthonykim1 -author:joshspicer -author:osortega -author:hawkticehurst -author:pierceboggan -author:benvillalobos -author:dileepyavan -author:dineshc-msft -author:dmitrivMS -author:eli-w-king -author:jo-oikawa -author:jruales -author:jytjyt05 -author:kycutler -author:mrleemurray -author:pwang347 -author:vijayupadya -author:bryanchen-d -author:cwebster-99 -author:rwoll -author:lostintangent -author:jukasper -author:zhichli"
+    "value": "$NOT_TEAM_MEMBERS=-author:aeschli -author:alexdima -author:alexr00 -author:AmandaSilver -author:bamurtaugh -author:bpasero -author:chrmarti -author:Chuxel -author:claudiaregio -author:connor4312 -author:dbaeumer -author:deepak1556 -author:devinvalenciano -author:digitarald -author:DonJayamanne -author:egamma -author:fiveisprime -author:ntrogh -author:hediet -author:isidorn -author:joaomoreno -author:jrieken -author:kieferrm -author:lramos15 -author:lszomoru -author:meganrogge -author:mjbvz -author:rebornix -author:roblourens -author:rzhao271 -author:sandy081 -author:sbatten -author:stevencl -author:TylerLeonhardt -author:Tyriar -author:amunger -author:karthiknadig -author:eleanorjboyd -author:Yoyokrazy -author:ulugbekna -author:aiday-mar -author:bhavyaus -author:justschen -author:benibenj -author:luabud -author:anthonykim1 -author:joshspicer -author:osortega -author:hawkticehurst -author:pierceboggan -author:benvillalobos -author:dileepyavan -author:dmitrivMS -author:eli-w-king -author:jo-oikawa -author:jruales -author:jytjyt05 -author:kycutler -author:mrleemurray -author:pwang347 -author:vijayupadya -author:bryanchen-d -author:cwebster-99 -author:rwoll -author:lostintangent -author:jukasper -author:zhichli"
   },
   {
     "kind": 1,
diff --git a/.vscode/notebooks/my-work.github-issues b/.vscode/notebooks/my-work.github-issues
index b6c82fff3590b..c4bc569e9da31 100644
--- a/.vscode/notebooks/my-work.github-issues
+++ b/.vscode/notebooks/my-work.github-issues
@@ -7,7 +7,7 @@
   {
     "kind": 2,
     "language": "github-issues",
-    "value": "// list of repos we work in\n$REPOS=repo:microsoft/lsprotocol repo:microsoft/monaco-editor repo:microsoft/vscode repo:microsoft/vscode-anycode repo:microsoft/vscode-autopep8 repo:microsoft/vscode-black-formatter repo:microsoft/vscode-copilot repo:microsoft/vscode-copilot-release repo:microsoft/vscode-dev repo:microsoft/vscode-dev-chrome-launcher repo:microsoft/vscode-emmet-helper repo:microsoft/vscode-extension-telemetry repo:microsoft/vscode-flake8 repo:microsoft/vscode-github-issue-notebooks repo:microsoft/vscode-hexeditor repo:microsoft/vscode-internalbacklog repo:microsoft/vscode-isort repo:microsoft/vscode-js-debug repo:microsoft/vscode-jupyter repo:microsoft/vscode-jupyter-internal repo:microsoft/vscode-l10n repo:microsoft/vscode-livepreview repo:microsoft/vscode-markdown-languageservice repo:microsoft/vscode-markdown-tm-grammar repo:microsoft/vscode-mypy repo:microsoft/vscode-pull-request-github repo:microsoft/vscode-pylint repo:microsoft/vscode-python repo:microsoft/vscode-python-debugger repo:microsoft/vscode-python-tools-extension-template repo:microsoft/vscode-references-view repo:microsoft/vscode-remote-release repo:microsoft/vscode-remote-repositories-github repo:microsoft/vscode-remote-tunnels repo:microsoft/vscode-remotehub repo:microsoft/vscode-settings-sync-server repo:microsoft/vscode-unpkg repo:microsoft/vscode-vsce repo:microsoft/vscode-copilot-issues repo:microsoft/vscode-extension-samples\n\n// current milestone name\n$MILESTONE=milestone:\"February 2026\"\n"
+    "value": "// list of repos we work in\n$REPOS=repo:microsoft/lsprotocol repo:microsoft/monaco-editor repo:microsoft/vscode repo:microsoft/vscode-anycode repo:microsoft/vscode-autopep8 repo:microsoft/vscode-black-formatter repo:microsoft/vscode-copilot repo:microsoft/vscode-copilot-release repo:microsoft/vscode-dev repo:microsoft/vscode-dev-chrome-launcher repo:microsoft/vscode-emmet-helper repo:microsoft/vscode-extension-telemetry repo:microsoft/vscode-flake8 repo:microsoft/vscode-github-issue-notebooks repo:microsoft/vscode-hexeditor repo:microsoft/vscode-internalbacklog repo:microsoft/vscode-isort repo:microsoft/vscode-js-debug repo:microsoft/vscode-jupyter repo:microsoft/vscode-jupyter-internal repo:microsoft/vscode-l10n repo:microsoft/vscode-livepreview repo:microsoft/vscode-markdown-languageservice repo:microsoft/vscode-markdown-tm-grammar repo:microsoft/vscode-mypy repo:microsoft/vscode-pull-request-github repo:microsoft/vscode-pylint repo:microsoft/vscode-python repo:microsoft/vscode-python-debugger repo:microsoft/vscode-python-tools-extension-template repo:microsoft/vscode-references-view repo:microsoft/vscode-remote-release repo:microsoft/vscode-remote-repositories-github repo:microsoft/vscode-remote-tunnels repo:microsoft/vscode-remotehub repo:microsoft/vscode-settings-sync-server repo:microsoft/vscode-unpkg repo:microsoft/vscode-vsce repo:microsoft/vscode-copilot-issues repo:microsoft/vscode-extension-samples\n\n// current milestone name\n$MILESTONE=milestone:\"March 2026\"\n"
   },
   {
     "kind": 1,
diff --git a/.vscode/settings.json b/.vscode/settings.json
index 74343459e02ef..bd45f6441fa04 100644
--- a/.vscode/settings.json
+++ b/.vscode/settings.json
@@ -209,4 +209,9 @@
 	"azureMcp.serverMode": "all",
 	"azureMcp.readOnly": true,
 	"debug.breakpointsView.presentation": "tree",
+	"chat.agentSkillsLocations": {
+		".github/skills/.local": true,
+		".agents/skills/.local": true,
+		".claude/skills/.local": true,
+	}
 }
diff --git a/.vscode/tasks.json b/.vscode/tasks.json
index c330df2edecc9..687521f7e649c 100644
--- a/.vscode/tasks.json
+++ b/.vscode/tasks.json
@@ -225,8 +225,7 @@
 			"windows": {
 				"command": ".\\scripts\\code.bat"
 			},
-			"problemMatcher": [],
-			"inSessions": true
+			"problemMatcher": []
 		},
 		{
 			"label": "Run Dev Sessions",
@@ -238,6 +237,18 @@
 			"args": [
 				"--sessions"
 			],
+			"problemMatcher": []
+		},
+		{
+			"label": "Run and Compile Dev Sessions",
+			"type": "shell",
+			"command": "npm run transpile-client && ./scripts/code.sh",
+			"windows": {
+				"command": "npm run transpile-client && .\\scripts\\code.bat"
+			},
+			"args": [
+				"--sessions"
+			],
 			"inSessions": true,
 			"problemMatcher": []
 		},
@@ -375,9 +386,35 @@
 		{
 			"label": "Launch Component Explorer",
 			"type": "shell",
-			"command": "npx component-explorer serve -c ./test/componentFixtures/component-explorer.json",
+			"command": "npx component-explorer serve -c ./test/componentFixtures/component-explorer.json -vv --kill-if-running",
 			"isBackground": true,
-			"problemMatcher": []
+			"problemMatcher": {
+				"owner": "component-explorer",
+				"fileLocation": "absolute",
+				"pattern": {
+					"regexp": "^\\s*at\\s+(.+?):(\\d+):(\\d+)\\s*$",
+					"file": 1,
+					"line": 2,
+					"column": 3
+				},
+				"background": {
+					"activeOnStart": true,
+					"beginsPattern": ".*Setting up sessions.*",
+					"endsPattern": "Redirection server listening on.*"
+				}
+			}
+		},
+		{
+			"label": "Install & Watch",
+			"type": "shell",
+			"command": "npm install && npm run watch",
+			"windows": {
+				"command": "cmd /d /c \"npm install && npm run watch\""
+			},
+			"inSessions": true,
+			"runOptions": {
+				"runOn": "worktreeCreated"
+			}
 		}
 	]
 }
diff --git a/ThirdPartyNotices.txt b/ThirdPartyNotices.txt
index 896b59001d616..0a15b3ff5fc30 100644
--- a/ThirdPartyNotices.txt
+++ b/ThirdPartyNotices.txt
@@ -684,7 +684,7 @@ more details.
 
 ---------------------------------------------------------
 
-go-syntax 0.8.5 - MIT
+go-syntax 0.8.6 - MIT
 https://github.com/worlpaker/go-syntax
 
 MIT License
diff --git a/build/.npmrc b/build/.npmrc
index 551822f79cd63..f1c087f86b52c 100644
--- a/build/.npmrc
+++ b/build/.npmrc
@@ -4,3 +4,4 @@ build_from_source="true"
 legacy-peer-deps="true"
 force_process_config="true"
 timeout=180000
+min-release-age="1"
diff --git a/build/azure-pipelines/alpine/product-build-alpine.yml b/build/azure-pipelines/alpine/product-build-alpine.yml
index 5c5714e9d5b12..a9a1b0d1292ba 100644
--- a/build/azure-pipelines/alpine/product-build-alpine.yml
+++ b/build/azure-pipelines/alpine/product-build-alpine.yml
@@ -64,15 +64,6 @@ jobs:
           KeyVaultName: vscode-build-secrets
           SecretsFilter: "github-distro-mixin-password"
 
-      - task: DownloadPipelineArtifact@2
-        inputs:
-          artifact: Compilation
-          path: $(Build.ArtifactStagingDirectory)
-        displayName: Download compilation output
-
-      - script: tar -xzf $(Build.ArtifactStagingDirectory)/compilation.tar.gz
-        displayName: Extract compilation output
-
       - script: node build/setup-npm-registry.ts $NPM_REGISTRY
         condition: and(succeeded(), ne(variables['NPM_REGISTRY'], 'none'))
         displayName: Setup NPM Registry
@@ -173,6 +164,11 @@ jobs:
 
       - template: ../common/install-builtin-extensions.yml@self
 
+      - script: npm run gulp core-ci
+        env:
+          GITHUB_TOKEN: "$(github-distro-mixin-password)"
+        displayName: Compile
+
       - script: |
           set -e
           TARGET=$([ "$VSCODE_ARCH" == "x64" ] && echo "linux-alpine" || echo "alpine-arm64") # TODO@joaomoreno
diff --git a/build/azure-pipelines/common/extract-telemetry.sh b/build/azure-pipelines/common/extract-telemetry.sh
deleted file mode 100755
index 9cebe22bfd189..0000000000000
--- a/build/azure-pipelines/common/extract-telemetry.sh
+++ /dev/null
@@ -1,19 +0,0 @@
-#!/usr/bin/env bash
-set -e
-
-cd $BUILD_STAGINGDIRECTORY
-mkdir extraction
-cd extraction
-git clone --depth 1 https://github.com/microsoft/vscode-extension-telemetry.git
-git clone --depth 1 https://github.com/microsoft/vscode-chrome-debug-core.git
-git clone --depth 1 https://github.com/microsoft/vscode-node-debug2.git
-git clone --depth 1 https://github.com/microsoft/vscode-node-debug.git
-git clone --depth 1 https://github.com/microsoft/vscode-html-languageservice.git
-git clone --depth 1 https://github.com/microsoft/vscode-json-languageservice.git
-node $BUILD_SOURCESDIRECTORY/node_modules/.bin/vscode-telemetry-extractor --sourceDir $BUILD_SOURCESDIRECTORY --excludedDir $BUILD_SOURCESDIRECTORY/extensions --outputDir . --applyEndpoints
-node $BUILD_SOURCESDIRECTORY/node_modules/.bin/vscode-telemetry-extractor --config $BUILD_SOURCESDIRECTORY/build/azure-pipelines/common/telemetry-config.json -o .
-mkdir -p $BUILD_SOURCESDIRECTORY/.build/telemetry
-mv declarations-resolved.json $BUILD_SOURCESDIRECTORY/.build/telemetry/telemetry-core.json
-mv config-resolved.json $BUILD_SOURCESDIRECTORY/.build/telemetry/telemetry-extensions.json
-cd ..
-rm -rf extraction
diff --git a/build/azure-pipelines/common/extract-telemetry.ts b/build/azure-pipelines/common/extract-telemetry.ts
new file mode 100644
index 0000000000000..a5fafac71d5f8
--- /dev/null
+++ b/build/azure-pipelines/common/extract-telemetry.ts
@@ -0,0 +1,95 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import cp from 'child_process';
+import fs from 'fs';
+import os from 'os';
+import path from 'path';
+
+const BUILD_STAGINGDIRECTORY = process.env.BUILD_STAGINGDIRECTORY ?? fs.mkdtempSync(path.join(os.tmpdir(), 'vscode-telemetry-'));
+const BUILD_SOURCESDIRECTORY = process.env.BUILD_SOURCESDIRECTORY ?? path.resolve(import.meta.dirname, '..', '..', '..');
+
+const extractionDir = path.join(BUILD_STAGINGDIRECTORY, 'extraction');
+fs.mkdirSync(extractionDir, { recursive: true });
+
+const repos = [
+	'https://github.com/microsoft/vscode-extension-telemetry.git',
+	'https://github.com/microsoft/vscode-chrome-debug-core.git',
+	'https://github.com/microsoft/vscode-node-debug2.git',
+	'https://github.com/microsoft/vscode-node-debug.git',
+	'https://github.com/microsoft/vscode-html-languageservice.git',
+	'https://github.com/microsoft/vscode-json-languageservice.git',
+];
+
+for (const repo of repos) {
+	cp.execSync(`git clone --depth 1 ${repo}`, { cwd: extractionDir, stdio: 'inherit' });
+}
+
+const extractor = path.join(BUILD_SOURCESDIRECTORY, 'node_modules', '@vscode', 'telemetry-extractor', 'out', 'extractor.js');
+const telemetryConfig = path.join(BUILD_SOURCESDIRECTORY, 'build', 'azure-pipelines', 'common', 'telemetry-config.json');
+
+interface ITelemetryConfigEntry {
+	eventPrefix: string;
+	sourceDirs: string[];
+	excludedDirs: string[];
+	applyEndpoints: boolean;
+	patchDebugEvents?: boolean;
+}
+
+const pipelineExtensionsPathPrefix = '../../s/extensions/';
+
+const telemetryConfigEntries = JSON.parse(fs.readFileSync(telemetryConfig, 'utf8')) as ITelemetryConfigEntry[];
+let hasLocalConfigOverrides = false;
+
+const resolvedTelemetryConfigEntries = telemetryConfigEntries.map(entry => {
+	const sourceDirs = entry.sourceDirs.map(sourceDir => {
+		if (!sourceDir.startsWith(pipelineExtensionsPathPrefix)) {
+			return sourceDir;
+		}
+
+		const sourceDirInExtractionDir = path.resolve(extractionDir, sourceDir);
+		if (fs.existsSync(sourceDirInExtractionDir)) {
+			return sourceDir;
+		}
+
+		const extensionRelativePath = sourceDir.slice(pipelineExtensionsPathPrefix.length);
+		const sourceDirInWorkspace = path.join(BUILD_SOURCESDIRECTORY, 'extensions', extensionRelativePath);
+		if (fs.existsSync(sourceDirInWorkspace)) {
+			hasLocalConfigOverrides = true;
+			return sourceDirInWorkspace;
+		}
+
+		return sourceDir;
+	});
+
+	return {
+		...entry,
+		sourceDirs,
+	};
+});
+
+const telemetryConfigForExtraction = hasLocalConfigOverrides
+	? path.join(extractionDir, 'telemetry-config.local.json')
+	: telemetryConfig;
+
+if (hasLocalConfigOverrides) {
+	fs.writeFileSync(telemetryConfigForExtraction, JSON.stringify(resolvedTelemetryConfigEntries, null, '\t'));
+}
+
+try {
+	cp.execSync(`node "${extractor}" --sourceDir "${BUILD_SOURCESDIRECTORY}" --excludedDir "${path.join(BUILD_SOURCESDIRECTORY, 'extensions')}" --outputDir . --applyEndpoints`, { cwd: extractionDir, stdio: 'inherit' });
+	cp.execSync(`node "${extractor}" --config "${telemetryConfigForExtraction}" -o .`, { cwd: extractionDir, stdio: 'inherit' });
+} catch (error) {
+	const message = error instanceof Error ? error.message : String(error);
+	console.error(`Telemetry extraction failed: ${message}`);
+	process.exit(1);
+}
+
+const telemetryDir = path.join(BUILD_SOURCESDIRECTORY, '.build', 'telemetry');
+fs.mkdirSync(telemetryDir, { recursive: true });
+fs.renameSync(path.join(extractionDir, 'declarations-resolved.json'), path.join(telemetryDir, 'telemetry-core.json'));
+fs.renameSync(path.join(extractionDir, 'config-resolved.json'), path.join(telemetryDir, 'telemetry-extensions.json'));
+
+fs.rmSync(extractionDir, { recursive: true, force: true });
diff --git a/build/azure-pipelines/common/publish.ts b/build/azure-pipelines/common/publish.ts
index 572efa57bf998..fd621e4224021 100644
--- a/build/azure-pipelines/common/publish.ts
+++ b/build/azure-pipelines/common/publish.ts
@@ -970,15 +970,7 @@ async function main() {
 		console.log(`\u2705 ${name}`);
 	}
 
-	const stages = new Set<string>(['Compile']);
-
-	if (
-		e('VSCODE_BUILD_STAGE_LINUX') === 'True' ||
-		e('VSCODE_BUILD_STAGE_MACOS') === 'True' ||
-		e('VSCODE_BUILD_STAGE_WINDOWS') === 'True'
-	) {
-		stages.add('CompileCLI');
-	}
+	const stages = new Set<string>(['Quality']);
 
 	if (e('VSCODE_BUILD_STAGE_WINDOWS') === 'True') { stages.add('Windows'); }
 	if (e('VSCODE_BUILD_STAGE_LINUX') === 'True') { stages.add('Linux'); }
diff --git a/build/azure-pipelines/common/releaseBuild.ts b/build/azure-pipelines/common/releaseBuild.ts
index 3cd8082308e28..708978a130cad 100644
--- a/build/azure-pipelines/common/releaseBuild.ts
+++ b/build/azure-pipelines/common/releaseBuild.ts
@@ -66,15 +66,8 @@ async function main(force: boolean): Promise<void> {
 
 	console.log(`Releasing build ${commit}...`);
 
-	let rolloutDurationMs = undefined;
-
-	// If the build is insiders or exploration, start a rollout of 4 hours
-	if (quality === 'insider') {
-		rolloutDurationMs = 4 * 60 * 60 * 1000; // 4 hours
-	}
-
 	const scripts = client.database('builds').container(quality).scripts;
-	await retry(() => scripts.storedProcedure('releaseBuild').execute('', [commit, rolloutDurationMs]));
+	await retry(() => scripts.storedProcedure('releaseBuild').execute('', [commit]));
 }
 
 const [, , force] = process.argv;
diff --git a/build/azure-pipelines/common/sanity-tests.yml b/build/azure-pipelines/common/sanity-tests.yml
index 3606777f9a375..ce6d95dd7e59d 100644
--- a/build/azure-pipelines/common/sanity-tests.yml
+++ b/build/azure-pipelines/common/sanity-tests.yml
@@ -29,18 +29,36 @@ jobs:
       name: ${{ parameters.poolName }}
       os: ${{ parameters.os }}
     timeoutInMinutes: 30
+    templateContext:
+      outputs:
+        - output: pipelineArtifact
+          targetPath: $(SCREENSHOTS_DIR)
+          artifactName: screenshots-${{ parameters.name }}
+          displayName: Publish Screenshots
+          condition: succeededOrFailed()
+          continueOnError: true
+          sbomEnabled: false
     variables:
       TEST_DIR: $(Build.SourcesDirectory)/test/sanity
       LOG_FILE: $(TEST_DIR)/results.xml
+      SCREENSHOTS_DIR: $(TEST_DIR)/screenshots
       DOCKER_CACHE_DIR: $(Pipeline.Workspace)/docker-cache
       DOCKER_CACHE_FILE: $(DOCKER_CACHE_DIR)/${{ parameters.container }}.tar
     steps:
       - checkout: self
         fetchDepth: 1
         fetchTags: false
-        sparseCheckoutDirectories: test/sanity .nvmrc
+        sparseCheckoutDirectories: build/azure-pipelines/config test/sanity .nvmrc
         displayName: Checkout test/sanity
 
+      - ${{ if eq(parameters.os, 'windows') }}:
+        - script: mkdir "$(SCREENSHOTS_DIR)"
+          displayName: Create Screenshots Directory
+
+      - ${{ else }}:
+        - bash: mkdir -p "$(SCREENSHOTS_DIR)"
+          displayName: Create Screenshots Directory
+
       - ${{ if and(eq(parameters.os, 'windows'), eq(parameters.arch, 'arm64')) }}:
         - script: |
             @echo off
@@ -101,19 +119,19 @@ jobs:
 
       # Windows
       - ${{ if eq(parameters.os, 'windows') }}:
-        - script: $(TEST_DIR)/scripts/run-win32.cmd -c $(BUILD_COMMIT) -q $(BUILD_QUALITY) -t $(LOG_FILE) -v ${{ parameters.args }}
+        - script: $(TEST_DIR)/scripts/run-win32.cmd -c $(BUILD_COMMIT) -q $(BUILD_QUALITY) -t $(LOG_FILE) -s $(SCREENSHOTS_DIR) -v ${{ parameters.args }}
           workingDirectory: $(TEST_DIR)
           displayName: Run Sanity Tests
 
       # macOS
       - ${{ if eq(parameters.os, 'macOS') }}:
-        - bash: $(TEST_DIR)/scripts/run-macOS.sh -c $(BUILD_COMMIT) -q $(BUILD_QUALITY) -t $(LOG_FILE) -v ${{ parameters.args }}
+        - bash: $(TEST_DIR)/scripts/run-macOS.sh -c $(BUILD_COMMIT) -q $(BUILD_QUALITY) -t $(LOG_FILE) -s $(SCREENSHOTS_DIR) -v ${{ parameters.args }}
           workingDirectory: $(TEST_DIR)
           displayName: Run Sanity Tests
 
       # Native Linux host
       - ${{ if and(eq(parameters.container, ''), eq(parameters.os, 'linux')) }}:
-        - bash: $(TEST_DIR)/scripts/run-ubuntu.sh -c $(BUILD_COMMIT) -q $(BUILD_QUALITY) -t $(LOG_FILE) -v ${{ parameters.args }}
+        - bash: $(TEST_DIR)/scripts/run-ubuntu.sh -c $(BUILD_COMMIT) -q $(BUILD_QUALITY) -t $(LOG_FILE) -s $(SCREENSHOTS_DIR) -v ${{ parameters.args }}
           workingDirectory: $(TEST_DIR)
           displayName: Run Sanity Tests
 
@@ -141,6 +159,7 @@ jobs:
               --quality "$(BUILD_QUALITY)" \
               --commit "$(BUILD_COMMIT)" \
               --test-results "/root/results.xml" \
+              --screenshots-dir "/root/screenshots" \
               --verbose \
               ${{ parameters.args }}
           workingDirectory: $(TEST_DIR)
diff --git a/build/azure-pipelines/darwin/product-build-darwin-cli-sign.yml b/build/azure-pipelines/darwin/product-build-darwin-cli-sign.yml
deleted file mode 100644
index 94eee5e476c2a..0000000000000
--- a/build/azure-pipelines/darwin/product-build-darwin-cli-sign.yml
+++ /dev/null
@@ -1,86 +0,0 @@
-parameters:
-  - name: VSCODE_BUILD_MACOS
-    type: boolean
-  - name: VSCODE_BUILD_MACOS_ARM64
-    type: boolean
-
-jobs:
-  - job: macOSCLISign
-    timeoutInMinutes: 90
-    templateContext:
-      outputParentDirectory: $(Build.ArtifactStagingDirectory)/out
-      outputs:
-        - ${{ if eq(parameters.VSCODE_BUILD_MACOS, true) }}:
-          - output: pipelineArtifact
-            targetPath: $(Build.ArtifactStagingDirectory)/out/vscode_cli_darwin_x64_cli/vscode_cli_darwin_x64_cli.zip
-            artifactName: vscode_cli_darwin_x64_cli
-            displayName: Publish signed artifact with ID vscode_cli_darwin_x64_cli
-            sbomBuildDropPath: $(Build.ArtifactStagingDirectory)/sign/unsigned_vscode_cli_darwin_x64_cli
-            sbomPackageName: "VS Code macOS x64 CLI"
-            sbomPackageVersion: $(Build.SourceVersion)
-        - ${{ if eq(parameters.VSCODE_BUILD_MACOS_ARM64, true) }}:
-          - output: pipelineArtifact
-            targetPath: $(Build.ArtifactStagingDirectory)/out/vscode_cli_darwin_arm64_cli/vscode_cli_darwin_arm64_cli.zip
-            artifactName: vscode_cli_darwin_arm64_cli
-            displayName: Publish signed artifact with ID vscode_cli_darwin_arm64_cli
-            sbomBuildDropPath: $(Build.ArtifactStagingDirectory)/sign/unsigned_vscode_cli_darwin_arm64_cli
-            sbomPackageName: "VS Code macOS arm64 CLI"
-            sbomPackageVersion: $(Build.SourceVersion)
-    steps:
-      - template: ../common/checkout.yml@self
-
-      - task: NodeTool@0
-        inputs:
-          versionSource: fromFile
-          versionFilePath: .nvmrc
-
-      - task: AzureKeyVault@2
-        displayName: "Azure Key Vault: Get Secrets"
-        inputs:
-          azureSubscription: vscode
-          KeyVaultName: vscode-build-secrets
-          SecretsFilter: "github-distro-mixin-password"
-
-      - script: node build/setup-npm-registry.ts $NPM_REGISTRY build
-        condition: and(succeeded(), ne(variables['NPM_REGISTRY'], 'none'))
-        displayName: Setup NPM Registry
-
-      - script: |
-          set -e
-          # Set the private NPM registry to the global npmrc file
-          # so that authentication works for subfolders like build/, remote/, extensions/ etc
-          # which does not have their own .npmrc file
-          npm config set registry "$NPM_REGISTRY"
-          echo "##vso[task.setvariable variable=NPMRC_PATH]$(npm config get userconfig)"
-        condition: and(succeeded(), ne(variables['NPM_REGISTRY'], 'none'))
-        displayName: Setup NPM
-
-      - task: npmAuthenticate@0
-        inputs:
-          workingFile: $(NPMRC_PATH)
-        condition: and(succeeded(), ne(variables['NPM_REGISTRY'], 'none'))
-        displayName: Setup NPM Authentication
-
-      - script: |
-          set -e
-
-          for i in {1..5}; do # try 5 times
-            npm ci && break
-            if [ $i -eq 5 ]; then
-              echo "Npm install failed too many times" >&2
-              exit 1
-            fi
-            echo "Npm install failed $i, trying again..."
-          done
-        workingDirectory: build
-        env:
-          GITHUB_TOKEN: "$(github-distro-mixin-password)"
-        displayName: Install build dependencies
-
-      - template: ./steps/product-build-darwin-cli-sign.yml@self
-        parameters:
-          VSCODE_CLI_ARTIFACTS:
-            - ${{ if eq(parameters.VSCODE_BUILD_MACOS, true) }}:
-              - unsigned_vscode_cli_darwin_x64_cli
-            - ${{ if eq(parameters.VSCODE_BUILD_MACOS_ARM64, true) }}:
-              - unsigned_vscode_cli_darwin_arm64_cli
diff --git a/build/azure-pipelines/darwin/product-build-darwin-cli.yml b/build/azure-pipelines/darwin/product-build-darwin-cli.yml
index dc5a5d79c1457..1b6ea51bd146f 100644
--- a/build/azure-pipelines/darwin/product-build-darwin-cli.yml
+++ b/build/azure-pipelines/darwin/product-build-darwin-cli.yml
@@ -9,8 +9,8 @@ parameters:
 
 jobs:
 - job: macOSCLI_${{ parameters.VSCODE_ARCH }}
-  displayName: macOS (${{ upper(parameters.VSCODE_ARCH) }})
-  timeoutInMinutes: 60
+  displayName: macOS CLI (${{ upper(parameters.VSCODE_ARCH) }})
+  timeoutInMinutes: 90
   pool:
     name: AcesShared
     os: macOS
@@ -24,11 +24,12 @@ jobs:
     outputs:
       - ${{ if not(parameters.VSCODE_CHECK_ONLY) }}:
         - output: pipelineArtifact
-          targetPath: $(Build.ArtifactStagingDirectory)/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli.zip
-          artifactName: unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli
-          displayName: Publish unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli artifact
-          sbomEnabled: false
-          isProduction: false
+          targetPath: $(Build.ArtifactStagingDirectory)/out/vscode_cli_darwin_$(VSCODE_ARCH)_cli/vscode_cli_darwin_$(VSCODE_ARCH)_cli.zip
+          artifactName: vscode_cli_darwin_$(VSCODE_ARCH)_cli
+          displayName: Publish vscode_cli_darwin_$(VSCODE_ARCH)_cli artifact
+          sbomBuildDropPath: $(Build.ArtifactStagingDirectory)/sign/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli
+          sbomPackageName: "VS Code macOS $(VSCODE_ARCH) CLI"
+          sbomPackageVersion: $(Build.SourceVersion)
   steps:
     - template: ../common/checkout.yml@self
 
@@ -83,3 +84,55 @@ jobs:
           VSCODE_CLI_ENV:
             OPENSSL_LIB_DIR: $(Build.ArtifactStagingDirectory)/openssl/arm64-osx/lib
             OPENSSL_INCLUDE_DIR: $(Build.ArtifactStagingDirectory)/openssl/arm64-osx/include
+
+    - ${{ if not(parameters.VSCODE_CHECK_ONLY) }}:
+      - template: ../common/publish-artifact.yml@self
+        parameters:
+          targetPath: $(Build.ArtifactStagingDirectory)/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli.zip
+          artifactName: unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli
+          displayName: Publish unsigned CLI
+          sbomEnabled: false
+
+      - script: |
+          set -e
+          mkdir -p $(Build.ArtifactStagingDirectory)/pkg/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli
+          cp $(Build.ArtifactStagingDirectory)/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli.zip $(Build.ArtifactStagingDirectory)/pkg/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli.zip
+        displayName: Prepare CLI for signing
+
+      - task: ExtractFiles@1
+        displayName: Extract unsigned CLI (for SBOM)
+        inputs:
+          archiveFilePatterns: $(Build.ArtifactStagingDirectory)/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli.zip
+          destinationFolder: $(Build.ArtifactStagingDirectory)/sign/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli
+
+      - task: UseDotNet@2
+        inputs:
+          version: 6.x
+
+      - task: EsrpCodeSigning@5
+        inputs:
+          UseMSIAuthentication: true
+          ConnectedServiceName: vscode-esrp
+          AppRegistrationClientId: $(ESRP_CLIENT_ID)
+          AppRegistrationTenantId: $(ESRP_TENANT_ID)
+          AuthAKVName: vscode-esrp
+          AuthSignCertName: esrp-sign
+          FolderPath: .
+          Pattern: noop
+        displayName: 'Install ESRP Tooling'
+
+      - script: node build/azure-pipelines/common/sign.ts $(Agent.RootDirectory)/_tasks/EsrpCodeSigning_*/*/net6.0/esrpcli.dll sign-darwin $(Build.ArtifactStagingDirectory)/pkg/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli "*.zip"
+        env:
+          SYSTEM_ACCESSTOKEN: $(System.AccessToken)
+        displayName: ✍️ Codesign
+
+      - script: node build/azure-pipelines/common/sign.ts $(Agent.RootDirectory)/_tasks/EsrpCodeSigning_*/*/net6.0/esrpcli.dll notarize-darwin $(Build.ArtifactStagingDirectory)/pkg/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli "*.zip"
+        env:
+          SYSTEM_ACCESSTOKEN: $(System.AccessToken)
+        displayName: ✍️ Notarize
+
+      - script: |
+          set -e
+          mkdir -p $(Build.ArtifactStagingDirectory)/out/vscode_cli_darwin_$(VSCODE_ARCH)_cli
+          mv $(Build.ArtifactStagingDirectory)/pkg/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli/unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli.zip $(Build.ArtifactStagingDirectory)/out/vscode_cli_darwin_$(VSCODE_ARCH)_cli/vscode_cli_darwin_$(VSCODE_ARCH)_cli.zip
+        displayName: Rename signed artifact
diff --git a/build/azure-pipelines/darwin/steps/product-build-darwin-cli-sign.yml b/build/azure-pipelines/darwin/steps/product-build-darwin-cli-sign.yml
deleted file mode 100644
index 1cd0fe2a8245f..0000000000000
--- a/build/azure-pipelines/darwin/steps/product-build-darwin-cli-sign.yml
+++ /dev/null
@@ -1,53 +0,0 @@
-parameters:
-  - name: VSCODE_CLI_ARTIFACTS
-    type: object
-    default: []
-
-steps:
-  - task: UseDotNet@2
-    inputs:
-      version: 6.x
-
-  - task: EsrpCodeSigning@5
-    inputs:
-      UseMSIAuthentication: true
-      ConnectedServiceName: vscode-esrp
-      AppRegistrationClientId: $(ESRP_CLIENT_ID)
-      AppRegistrationTenantId: $(ESRP_TENANT_ID)
-      AuthAKVName: vscode-esrp
-      AuthSignCertName: esrp-sign
-      FolderPath: .
-      Pattern: noop
-    displayName: 'Install ESRP Tooling'
-
-  - ${{ each target in parameters.VSCODE_CLI_ARTIFACTS }}:
-    - task: DownloadPipelineArtifact@2
-      displayName: Download ${{ target }}
-      inputs:
-        artifact: ${{ target }}
-        path: $(Build.ArtifactStagingDirectory)/pkg/${{ target }}
-
-    - task: ExtractFiles@1
-      displayName: Extract artifact
-      inputs:
-        archiveFilePatterns: $(Build.ArtifactStagingDirectory)/pkg/${{ target }}/*.zip
-        destinationFolder: $(Build.ArtifactStagingDirectory)/sign/${{ target }}
-
-  - script: node build/azure-pipelines/common/sign.ts $(Agent.RootDirectory)/_tasks/EsrpCodeSigning_*/*/net6.0/esrpcli.dll sign-darwin $(Build.ArtifactStagingDirectory)/pkg "*.zip"
-    env:
-      SYSTEM_ACCESSTOKEN: $(System.AccessToken)
-    displayName: ✍️ Codesign
-
-  - script: node build/azure-pipelines/common/sign.ts $(Agent.RootDirectory)/_tasks/EsrpCodeSigning_*/*/net6.0/esrpcli.dll notarize-darwin $(Build.ArtifactStagingDirectory)/pkg "*.zip"
-    env:
-      SYSTEM_ACCESSTOKEN: $(System.AccessToken)
-    displayName: ✍️ Notarize
-
-  - ${{ each target in parameters.VSCODE_CLI_ARTIFACTS }}:
-    - script: |
-        set -e
-        ASSET_ID=$(echo "${{ target }}" | sed "s/unsigned_//")
-        mkdir -p $(Build.ArtifactStagingDirectory)/out/$ASSET_ID
-        mv $(Build.ArtifactStagingDirectory)/pkg/${{ target }}/${{ target }}.zip $(Build.ArtifactStagingDirectory)/out/$ASSET_ID/$ASSET_ID.zip
-        echo "##vso[task.setvariable variable=ASSET_ID]$ASSET_ID"
-      displayName: Set asset id variable
diff --git a/build/azure-pipelines/darwin/steps/product-build-darwin-compile.yml b/build/azure-pipelines/darwin/steps/product-build-darwin-compile.yml
index 64b91f714016f..cd5f6c287c01c 100644
--- a/build/azure-pipelines/darwin/steps/product-build-darwin-compile.yml
+++ b/build/azure-pipelines/darwin/steps/product-build-darwin-compile.yml
@@ -30,15 +30,6 @@ steps:
       KeyVaultName: vscode-build-secrets
       SecretsFilter: "github-distro-mixin-password,macos-developer-certificate,macos-developer-certificate-key"
 
-  - task: DownloadPipelineArtifact@2
-    inputs:
-      artifact: Compilation
-      path: $(Build.ArtifactStagingDirectory)
-    displayName: Download compilation output
-
-  - script: tar -xzf $(Build.ArtifactStagingDirectory)/compilation.tar.gz
-    displayName: Extract compilation output
-
   - script: node build/setup-npm-registry.ts $NPM_REGISTRY
     condition: and(succeeded(), ne(variables['NPM_REGISTRY'], 'none'))
     displayName: Setup NPM Registry
@@ -112,11 +103,33 @@ steps:
     condition: and(succeeded(), ne(variables.NODE_MODULES_RESTORED, 'true'))
     displayName: Create node_modules archive
 
+  - ${{ if ne(parameters.VSCODE_CIBUILD, true) }}:
+    - script: npx deemon --detach --wait -- node build/azure-pipelines/common/waitForArtifacts.ts unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli
+      env:
+        SYSTEM_ACCESSTOKEN: $(System.AccessToken)
+      displayName: Wait for CLI artifact (background)
+
   - script: node build/azure-pipelines/distro/mixin-quality.ts
     displayName: Mixin distro quality
 
   - template: ../../common/install-builtin-extensions.yml@self
 
+  - script: npm run gulp core-ci
+    env:
+      GITHUB_TOKEN: "$(github-distro-mixin-password)"
+    displayName: Compile
+
+  - script: node build/azure-pipelines/common/extract-telemetry.ts
+    displayName: Generate lists of telemetry events
+
+  - ${{ if or(eq(parameters.VSCODE_RUN_ELECTRON_TESTS, true), eq(parameters.VSCODE_RUN_BROWSER_TESTS, true), eq(parameters.VSCODE_RUN_REMOTE_TESTS, true)) }}:
+    - script: |
+        set -e
+        npm run compile --prefix test/smoke
+        npm run compile --prefix test/integration/browser
+      displayName: Compile test suites (non-OSS)
+      condition: and(succeeded(), eq(variables['VSCODE_STEP_ON_IT'], 'false'))
+
   - ${{ if ne(parameters.VSCODE_CIBUILD, true) }}:
     - script: npm run copy-policy-dto --prefix build && node build/lib/policies/policyGenerator.ts build/lib/policies/policyData.jsonc darwin
       displayName: Generate policy definitions
@@ -147,6 +160,11 @@ steps:
     displayName: Build server (web)
 
   - ${{ if ne(parameters.VSCODE_CIBUILD, true) }}:
+    - script: npx deemon --attach -- node build/azure-pipelines/common/waitForArtifacts.ts unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli
+      env:
+        SYSTEM_ACCESSTOKEN: $(System.AccessToken)
+      displayName: Wait for CLI artifact
+
     - task: DownloadPipelineArtifact@2
       inputs:
         artifact: unsigned_vscode_cli_darwin_$(VSCODE_ARCH)_cli
diff --git a/build/azure-pipelines/linux/product-build-linux-ci.yml b/build/azure-pipelines/linux/product-build-linux-ci.yml
index 6c6b102891a7e..619aff676407e 100644
--- a/build/azure-pipelines/linux/product-build-linux-ci.yml
+++ b/build/azure-pipelines/linux/product-build-linux-ci.yml
@@ -5,6 +5,9 @@ parameters:
     type: string
   - name: VSCODE_TEST_SUITE
     type: string
+  - name: VSCODE_RUN_CHECKS
+    type: boolean
+    default: false
 
 jobs:
   - job: Linux${{ parameters.VSCODE_TEST_SUITE }}
@@ -43,6 +46,7 @@ jobs:
           VSCODE_ARCH: x64
           VSCODE_CIBUILD: ${{ parameters.VSCODE_CIBUILD }}
           VSCODE_QUALITY: ${{ parameters.VSCODE_QUALITY }}
+          VSCODE_RUN_CHECKS: ${{ parameters.VSCODE_RUN_CHECKS }}
           ${{ if eq(parameters.VSCODE_TEST_SUITE, 'Electron') }}:
             VSCODE_RUN_ELECTRON_TESTS: true
           ${{ if eq(parameters.VSCODE_TEST_SUITE, 'Browser') }}:
diff --git a/build/azure-pipelines/linux/product-build-linux-cli.yml b/build/azure-pipelines/linux/product-build-linux-cli.yml
index ef160c2cc3849..a9107129b73b5 100644
--- a/build/azure-pipelines/linux/product-build-linux-cli.yml
+++ b/build/azure-pipelines/linux/product-build-linux-cli.yml
@@ -9,7 +9,7 @@ parameters:
 
 jobs:
   - job: LinuxCLI_${{ parameters.VSCODE_ARCH }}
-    displayName: Linux (${{ upper(parameters.VSCODE_ARCH) }})
+    displayName: Linux CLI (${{ upper(parameters.VSCODE_ARCH) }})
     timeoutInMinutes: 60
     pool:
       name: 1es-ubuntu-22.04-x64
diff --git a/build/azure-pipelines/linux/product-build-linux.yml b/build/azure-pipelines/linux/product-build-linux.yml
index 31eb7c3d46668..00ffd0aaab07e 100644
--- a/build/azure-pipelines/linux/product-build-linux.yml
+++ b/build/azure-pipelines/linux/product-build-linux.yml
@@ -19,6 +19,9 @@ parameters:
   - name: VSCODE_RUN_REMOTE_TESTS
     type: boolean
     default: false
+  - name: VSCODE_RUN_CHECKS
+    type: boolean
+    default: false
 
 jobs:
   - job: Linux_${{ parameters.VSCODE_ARCH }}
@@ -26,6 +29,7 @@ jobs:
     timeoutInMinutes: 90
     variables:
       DISPLAY: ":10"
+      BUILDS_API_URL: $(System.CollectionUri)$(System.TeamProject)/_apis/build/builds/$(Build.BuildId)/
       NPM_ARCH: ${{ parameters.NPM_ARCH }}
       VSCODE_ARCH: ${{ parameters.VSCODE_ARCH }}
     templateContext:
@@ -110,3 +114,4 @@ jobs:
           VSCODE_RUN_ELECTRON_TESTS: ${{ parameters.VSCODE_RUN_ELECTRON_TESTS }}
           VSCODE_RUN_BROWSER_TESTS: ${{ parameters.VSCODE_RUN_BROWSER_TESTS }}
           VSCODE_RUN_REMOTE_TESTS: ${{ parameters.VSCODE_RUN_REMOTE_TESTS }}
+          VSCODE_RUN_CHECKS: ${{ parameters.VSCODE_RUN_CHECKS }}
diff --git a/build/azure-pipelines/linux/steps/product-build-linux-compile.yml b/build/azure-pipelines/linux/steps/product-build-linux-compile.yml
index 89199ebbbb14c..a09758329cb61 100644
--- a/build/azure-pipelines/linux/steps/product-build-linux-compile.yml
+++ b/build/azure-pipelines/linux/steps/product-build-linux-compile.yml
@@ -17,6 +17,9 @@ parameters:
   - name: VSCODE_RUN_REMOTE_TESTS
     type: boolean
     default: false
+  - name: VSCODE_RUN_CHECKS
+    type: boolean
+    default: false
 
 steps:
   - template: ../../common/checkout.yml@self
@@ -35,15 +38,6 @@ steps:
       KeyVaultName: vscode-build-secrets
       SecretsFilter: "github-distro-mixin-password"
 
-  - task: DownloadPipelineArtifact@2
-    inputs:
-      artifact: Compilation
-      path: $(Build.ArtifactStagingDirectory)
-    displayName: Download compilation output
-
-  - script: tar -xzf $(Build.ArtifactStagingDirectory)/compilation.tar.gz
-    displayName: Extract compilation output
-
   - script: |
       set -e
       # Start X server
@@ -165,11 +159,34 @@ steps:
     condition: and(succeeded(), ne(variables.NODE_MODULES_RESTORED, 'true'))
     displayName: Create node_modules archive
 
+  - ${{ if ne(parameters.VSCODE_CIBUILD, true) }}:
+    - script: npx deemon --detach --wait -- node build/azure-pipelines/common/waitForArtifacts.ts $(ARTIFACT_PREFIX)vscode_cli_linux_$(VSCODE_ARCH)_cli
+      env:
+        SYSTEM_ACCESSTOKEN: $(System.AccessToken)
+      displayName: Wait for CLI artifact (background)
+
   - script: node build/azure-pipelines/distro/mixin-quality.ts
     displayName: Mixin distro quality
 
   - template: ../../common/install-builtin-extensions.yml@self
 
+  - script: npm run gulp core-ci
+    env:
+      GITHUB_TOKEN: "$(github-distro-mixin-password)"
+    displayName: Compile
+
+  - ${{ if eq(parameters.VSCODE_ARCH, 'x64') }}:
+    - script: node build/azure-pipelines/common/extract-telemetry.ts
+      displayName: Generate lists of telemetry events
+
+  - ${{ if or(eq(parameters.VSCODE_RUN_ELECTRON_TESTS, true), eq(parameters.VSCODE_RUN_BROWSER_TESTS, true), eq(parameters.VSCODE_RUN_REMOTE_TESTS, true)) }}:
+    - script: |
+        set -e
+        npm run compile --prefix test/smoke
+        npm run compile --prefix test/integration/browser
+      displayName: Compile test suites (non-OSS)
+      condition: and(succeeded(), eq(variables['VSCODE_STEP_ON_IT'], 'false'))
+
   - ${{ if ne(parameters.VSCODE_CIBUILD, true) }}:
     - script: npm run copy-policy-dto --prefix build && node build/lib/policies/policyGenerator.ts build/lib/policies/policyData.jsonc linux
       displayName: Generate policy definitions
@@ -187,6 +204,11 @@ steps:
     displayName: Build client
 
   - ${{ if ne(parameters.VSCODE_CIBUILD, true) }}:
+    - script: npx deemon --attach -- node build/azure-pipelines/common/waitForArtifacts.ts $(ARTIFACT_PREFIX)vscode_cli_linux_$(VSCODE_ARCH)_cli
+      env:
+        SYSTEM_ACCESSTOKEN: $(System.AccessToken)
+      displayName: Wait for CLI artifact
+
     - task: DownloadPipelineArtifact@2
       inputs:
         artifact: $(ARTIFACT_PREFIX)vscode_cli_linux_$(VSCODE_ARCH)_cli
@@ -323,7 +345,7 @@ steps:
         - script: |
             set -e
             npm run gulp "vscode-linux-$(VSCODE_ARCH)-prepare-snap"
-            sudo -E docker run -e VSCODE_ARCH -e VSCODE_QUALITY -v $(pwd):/work -w /work vscodehub.azurecr.io/vscode-linux-build-agent:snapcraft-x64 /bin/bash -c "./build/azure-pipelines/linux/build-snap.sh"
+            sudo -E docker run -e VSCODE_ARCH -e VSCODE_QUALITY -v $(pwd):/work -w /work vscodehub.azurecr.io/vscode-linux-build-agent:snapcraft-x64@sha256:ab4a88c4d85e0d7a85acabba59543f7143f575bab2c0b2b07f5b77d4a7e491ff /bin/bash -c "./build/azure-pipelines/linux/build-snap.sh"
 
             SNAP_ROOT="$(pwd)/.build/linux/snap/$(VSCODE_ARCH)"
             SNAP_EXTRACTED_PATH=$(find $SNAP_ROOT -maxdepth 1 -type d -name 'code-*')
diff --git a/build/azure-pipelines/product-build-macos.yml b/build/azure-pipelines/product-build-macos.yml
deleted file mode 100644
index cc563953b0071..0000000000000
--- a/build/azure-pipelines/product-build-macos.yml
+++ /dev/null
@@ -1,106 +0,0 @@
-pr: none
-
-trigger: none
-
-parameters:
-  - name: VSCODE_QUALITY
-    displayName: Quality
-    type: string
-    default: insider
-  - name: NPM_REGISTRY
-    displayName: "Custom NPM Registry"
-    type: string
-    default: 'https://pkgs.dev.azure.com/monacotools/Monaco/_packaging/vscode/npm/registry/'
-  - name: CARGO_REGISTRY
-    displayName: "Custom Cargo Registry"
-    type: string
-    default: 'sparse+https://pkgs.dev.azure.com/monacotools/Monaco/_packaging/vscode/Cargo/index/'
-
-variables:
-  - name: NPM_REGISTRY
-    ${{ if in(variables['Build.Reason'], 'IndividualCI', 'BatchedCI') }}: # disable terrapin when in VSCODE_CIBUILD
-      value: none
-    ${{ else }}:
-      value: ${{ parameters.NPM_REGISTRY }}
-  - name: CARGO_REGISTRY
-    value: ${{ parameters.CARGO_REGISTRY }}
-  - name: VSCODE_QUALITY
-    value: ${{ parameters.VSCODE_QUALITY }}
-  - name: VSCODE_CIBUILD
-    value: ${{ in(variables['Build.Reason'], 'IndividualCI', 'BatchedCI') }}
-  - name: VSCODE_STEP_ON_IT
-    value: false
-  - name: skipComponentGovernanceDetection
-    value: true
-  - name: ComponentDetection.Timeout
-    value: 600
-  - name: Codeql.SkipTaskAutoInjection
-    value: true
-  - name: ARTIFACT_PREFIX
-    value: ''
-
-name: "$(Date:yyyyMMdd).$(Rev:r) (${{ parameters.VSCODE_QUALITY }})"
-
-resources:
-  repositories:
-    - repository: 1esPipelines
-      type: git
-      name: 1ESPipelineTemplates/1ESPipelineTemplates
-      ref: refs/tags/release
-
-extends:
-  template: v1/1ES.Official.PipelineTemplate.yml@1esPipelines
-  parameters:
-    sdl:
-      tsa:
-        enabled: true
-        configFile: $(Build.SourcesDirectory)/build/azure-pipelines/config/tsaoptions.json
-      codeql:
-        runSourceLanguagesInSourceAnalysis: true
-        compiled:
-          enabled: false
-          justificationForDisabling: "CodeQL breaks ESRP CodeSign on macOS (ICM #520035761, githubcustomers/microsoft-codeql-support#198)"
-      credscan:
-        suppressionsFile: $(Build.SourcesDirectory)/build/azure-pipelines/config/CredScanSuppressions.json
-      eslint:
-        enabled: true
-        enableExclusions: true
-        exclusionsFilePath: $(Build.SourcesDirectory)/.eslint-ignore
-      sourceAnalysisPool: 1es-windows-2022-x64
-      createAdoIssuesForJustificationsForDisablement: false
-    containers:
-      ubuntu-2004-arm64:
-        image: onebranch.azurecr.io/linux/ubuntu-2004-arm64:latest
-    stages:
-      - stage: Compile
-        pool:
-          name: AcesShared
-          os: macOS
-          demands:
-            - ImageOverride -equals ACES_VM_SharedPool_Sequoia
-        jobs:
-          - template: build/azure-pipelines/product-compile.yml@self
-
-      - stage: macOS
-        dependsOn:
-          - Compile
-        pool:
-          name: AcesShared
-          os: macOS
-          demands:
-            - ImageOverride -equals ACES_VM_SharedPool_Sequoia
-        variables:
-          BUILDSECMON_OPT_IN: true
-        jobs:
-          - template: build/azure-pipelines/darwin/product-build-darwin-ci.yml@self
-            parameters:
-              VSCODE_CIBUILD: true
-              VSCODE_TEST_SUITE: Electron
-          - template: build/azure-pipelines/darwin/product-build-darwin-ci.yml@self
-            parameters:
-              VSCODE_CIBUILD: true
-              VSCODE_TEST_SUITE: Browser
-          - template: build/azure-pipelines/darwin/product-build-darwin-ci.yml@self
-            parameters:
-              VSCODE_CIBUILD: true
-              VSCODE_TEST_SUITE: Remote
diff --git a/build/azure-pipelines/product-build.yml b/build/azure-pipelines/product-build.yml
index 77c3dd0665f9e..e016db506862f 100644
--- a/build/azure-pipelines/product-build.yml
+++ b/build/azure-pipelines/product-build.yml
@@ -26,6 +26,13 @@ parameters:
       - exploration
       - insider
       - stable
+  - name: VSCODE_BUILD_TYPE
+    displayName: Build Type
+    type: string
+    default: Product
+    values:
+      - Product
+      - CI
   - name: NPM_REGISTRY
     displayName: "Custom NPM Registry"
     type: string
@@ -90,10 +97,6 @@ parameters:
     displayName: "Release build if successful"
     type: boolean
     default: false
-  - name: VSCODE_COMPILE_ONLY
-    displayName: "Run Compile stage exclusively"
-    type: boolean
-    default: false
   - name: VSCODE_STEP_ON_IT
     displayName: "Skip tests"
     type: boolean
@@ -119,9 +122,9 @@ variables:
   - name: VSCODE_BUILD_STAGE_WEB
     value: ${{ eq(parameters.VSCODE_BUILD_WEB, true) }}
   - name: VSCODE_CIBUILD
-    value: ${{ in(variables['Build.Reason'], 'IndividualCI', 'BatchedCI') }}
+    value: ${{ or(in(variables['Build.Reason'], 'IndividualCI', 'BatchedCI'), eq(parameters.VSCODE_BUILD_TYPE, 'CI')) }}
   - name: VSCODE_PUBLISH
-    value: ${{ and(eq(parameters.VSCODE_PUBLISH, true), eq(variables.VSCODE_CIBUILD, false), eq(parameters.VSCODE_COMPILE_ONLY, false)) }}
+    value: ${{ and(eq(parameters.VSCODE_PUBLISH, true), eq(variables.VSCODE_CIBUILD, false)) }}
   - name: VSCODE_SCHEDULEDBUILD
     value: ${{ eq(variables['Build.Reason'], 'Schedule') }}
   - name: VSCODE_STEP_ON_IT
@@ -190,27 +193,21 @@ extends:
       ubuntu-2004-arm64:
         image: onebranch.azurecr.io/linux/ubuntu-2004-arm64:latest
     stages:
-      - stage: Compile
+
+      - stage: Quality
+        dependsOn: []
         pool:
-          name: AcesShared
-          os: macOS
-          demands:
-            - ImageOverride -equals ACES_VM_SharedPool_Sequoia
+          name: 1es-ubuntu-22.04-x64
+          os: linux
         jobs:
-          - template: build/azure-pipelines/product-compile.yml@self
+          - template: build/azure-pipelines/product-quality-checks.yml@self
 
-      - ${{ if eq(variables['VSCODE_PUBLISH'], 'true') }}:
-        - stage: ValidationChecks
+      - ${{ if eq(variables['VSCODE_BUILD_STAGE_WINDOWS'], true) }}:
+        - stage: Windows
           dependsOn: []
           pool:
-            name: 1es-ubuntu-22.04-x64
-            os: linux
-          jobs:
-            - template: build/azure-pipelines/product-validation-checks.yml@self
-
-      - ${{ if or(eq(parameters.VSCODE_BUILD_LINUX, true),eq(parameters.VSCODE_BUILD_LINUX_ARMHF, true),eq(parameters.VSCODE_BUILD_LINUX_ARM64, true),eq(parameters.VSCODE_BUILD_MACOS, true),eq(parameters.VSCODE_BUILD_MACOS_ARM64, true),eq(parameters.VSCODE_BUILD_WIN32, true),eq(parameters.VSCODE_BUILD_WIN32_ARM64, true)) }}:
-        - stage: CompileCLI
-          dependsOn: []
+            name: 1es-windows-2022-x64
+            os: windows
           jobs:
             - ${{ if eq(parameters.VSCODE_BUILD_WIN32, true) }}:
               - template: build/azure-pipelines/win32/product-build-win32-cli.yml@self
@@ -225,88 +222,6 @@ extends:
                   VSCODE_ARCH: arm64
                   VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
 
-            - ${{ if eq(parameters.VSCODE_BUILD_LINUX, true) }}:
-              - template: build/azure-pipelines/linux/product-build-linux-cli.yml@self
-                parameters:
-                  VSCODE_ARCH: x64
-                  VSCODE_CHECK_ONLY: ${{ variables.VSCODE_CIBUILD }}
-                  VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
-
-            - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), eq(parameters.VSCODE_BUILD_LINUX_ARM64, true)) }}:
-              - template: build/azure-pipelines/linux/product-build-linux-cli.yml@self
-                parameters:
-                  VSCODE_ARCH: arm64
-                  VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
-
-            - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), eq(parameters.VSCODE_BUILD_LINUX_ARMHF, true)) }}:
-              - template: build/azure-pipelines/linux/product-build-linux-cli.yml@self
-                parameters:
-                  VSCODE_ARCH: armhf
-                  VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
-
-            - ${{ if eq(parameters.VSCODE_BUILD_MACOS, true) }}:
-              - template: build/azure-pipelines/darwin/product-build-darwin-cli.yml@self
-                parameters:
-                  VSCODE_ARCH: x64
-                  VSCODE_CHECK_ONLY: ${{ variables.VSCODE_CIBUILD }}
-                  VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
-
-            - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), eq(parameters.VSCODE_BUILD_MACOS_ARM64, true)) }}:
-              - template: build/azure-pipelines/darwin/product-build-darwin-cli.yml@self
-                parameters:
-                  VSCODE_ARCH: arm64
-                  VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
-
-      - ${{ if and(eq(variables['VSCODE_CIBUILD'], true), eq(parameters.VSCODE_COMPILE_ONLY, false)) }}:
-        - stage: node_modules
-          dependsOn: []
-          jobs:
-            - template: build/azure-pipelines/win32/product-build-win32-node-modules.yml@self
-              parameters:
-                VSCODE_ARCH: arm64
-            - template: build/azure-pipelines/linux/product-build-linux-node-modules.yml@self
-              parameters:
-                NPM_ARCH: arm64
-                VSCODE_ARCH: arm64
-            - template: build/azure-pipelines/linux/product-build-linux-node-modules.yml@self
-              parameters:
-                NPM_ARCH: arm
-                VSCODE_ARCH: armhf
-            - template: build/azure-pipelines/alpine/product-build-alpine-node-modules.yml@self
-              parameters:
-                VSCODE_ARCH: x64
-            - template: build/azure-pipelines/alpine/product-build-alpine-node-modules.yml@self
-              parameters:
-                VSCODE_ARCH: arm64
-            - template: build/azure-pipelines/darwin/product-build-darwin-node-modules.yml@self
-              parameters:
-                VSCODE_ARCH: x64
-            - template: build/azure-pipelines/web/product-build-web-node-modules.yml@self
-
-      - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), eq(parameters.VSCODE_COMPILE_ONLY, false)) }}:
-        - stage: APIScan
-          dependsOn: []
-          pool:
-            name: 1es-windows-2022-x64
-            os: windows
-          jobs:
-            - job: WindowsAPIScan
-              steps:
-                - template: build/azure-pipelines/win32/sdl-scan-win32.yml@self
-                  parameters:
-                    VSCODE_ARCH: x64
-                    VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
-
-      - ${{ if and(eq(parameters.VSCODE_COMPILE_ONLY, false), eq(variables['VSCODE_BUILD_STAGE_WINDOWS'], true)) }}:
-        - stage: Windows
-          dependsOn:
-            - Compile
-            - ${{ if or(eq(parameters.VSCODE_BUILD_LINUX, true),eq(parameters.VSCODE_BUILD_LINUX_ARMHF, true),eq(parameters.VSCODE_BUILD_LINUX_ARM64, true),eq(parameters.VSCODE_BUILD_MACOS, true),eq(parameters.VSCODE_BUILD_MACOS_ARM64, true),eq(parameters.VSCODE_BUILD_WIN32, true),eq(parameters.VSCODE_BUILD_WIN32_ARM64, true)) }}:
-              - CompileCLI
-          pool:
-            name: 1es-windows-2022-x64
-            os: windows
-          jobs:
             - ${{ if eq(variables['VSCODE_CIBUILD'], true) }}:
               - template: build/azure-pipelines/win32/product-build-win32-ci.yml@self
                 parameters:
@@ -341,22 +256,32 @@ extends:
                   VSCODE_CIBUILD: ${{ variables.VSCODE_CIBUILD }}
                   VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
 
-            - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), or(eq(parameters.VSCODE_BUILD_WIN32, true), eq(parameters.VSCODE_BUILD_WIN32_ARM64, true))) }}:
-              - template: build/azure-pipelines/win32/product-build-win32-cli-sign.yml@self
-                parameters:
-                  VSCODE_BUILD_WIN32: ${{ parameters.VSCODE_BUILD_WIN32 }}
-                  VSCODE_BUILD_WIN32_ARM64: ${{ parameters.VSCODE_BUILD_WIN32_ARM64 }}
-
-      - ${{ if and(eq(parameters.VSCODE_COMPILE_ONLY, false), eq(variables['VSCODE_BUILD_STAGE_LINUX'], true)) }}:
+      - ${{ if eq(variables['VSCODE_BUILD_STAGE_LINUX'], true) }}:
         - stage: Linux
-          dependsOn:
-            - Compile
-            - ${{ if or(eq(parameters.VSCODE_BUILD_LINUX, true),eq(parameters.VSCODE_BUILD_LINUX_ARMHF, true),eq(parameters.VSCODE_BUILD_LINUX_ARM64, true),eq(parameters.VSCODE_BUILD_MACOS, true),eq(parameters.VSCODE_BUILD_MACOS_ARM64, true),eq(parameters.VSCODE_BUILD_WIN32, true),eq(parameters.VSCODE_BUILD_WIN32_ARM64, true)) }}:
-              - CompileCLI
+          dependsOn: []
           pool:
             name: 1es-ubuntu-22.04-x64
             os: linux
           jobs:
+            - ${{ if eq(parameters.VSCODE_BUILD_LINUX, true) }}:
+              - template: build/azure-pipelines/linux/product-build-linux-cli.yml@self
+                parameters:
+                  VSCODE_ARCH: x64
+                  VSCODE_CHECK_ONLY: ${{ variables.VSCODE_CIBUILD }}
+                  VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
+
+            - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), eq(parameters.VSCODE_BUILD_LINUX_ARM64, true)) }}:
+              - template: build/azure-pipelines/linux/product-build-linux-cli.yml@self
+                parameters:
+                  VSCODE_ARCH: arm64
+                  VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
+
+            - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), eq(parameters.VSCODE_BUILD_LINUX_ARMHF, true)) }}:
+              - template: build/azure-pipelines/linux/product-build-linux-cli.yml@self
+                parameters:
+                  VSCODE_ARCH: armhf
+                  VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
+
             - ${{ if eq(variables['VSCODE_CIBUILD'], true) }}:
               - template: build/azure-pipelines/linux/product-build-linux-ci.yml@self
                 parameters:
@@ -402,10 +327,9 @@ extends:
                   VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
                   VSCODE_CIBUILD: ${{ variables.VSCODE_CIBUILD }}
 
-      - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), eq(parameters.VSCODE_COMPILE_ONLY, false), eq(variables['VSCODE_BUILD_STAGE_ALPINE'], true)) }}:
+      - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), eq(variables['VSCODE_BUILD_STAGE_ALPINE'], true)) }}:
         - stage: Alpine
-          dependsOn:
-            - Compile
+          dependsOn: []
           jobs:
             - ${{ if eq(parameters.VSCODE_BUILD_ALPINE, true) }}:
               - template: build/azure-pipelines/alpine/product-build-alpine.yml@self
@@ -424,12 +348,9 @@ extends:
                   VSCODE_ARCH: arm64
                   VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
 
-      - ${{ if and(eq(parameters.VSCODE_COMPILE_ONLY, false), eq(variables['VSCODE_BUILD_STAGE_MACOS'], true)) }}:
+      - ${{ if eq(variables['VSCODE_BUILD_STAGE_MACOS'], true) }}:
         - stage: macOS
-          dependsOn:
-            - Compile
-            - ${{ if or(eq(parameters.VSCODE_BUILD_LINUX, true),eq(parameters.VSCODE_BUILD_LINUX_ARMHF, true),eq(parameters.VSCODE_BUILD_LINUX_ARM64, true),eq(parameters.VSCODE_BUILD_MACOS, true),eq(parameters.VSCODE_BUILD_MACOS_ARM64, true),eq(parameters.VSCODE_BUILD_WIN32, true),eq(parameters.VSCODE_BUILD_WIN32_ARM64, true)) }}:
-              - CompileCLI
+          dependsOn: []
           pool:
             name: AcesShared
             os: macOS
@@ -438,6 +359,19 @@ extends:
           variables:
             BUILDSECMON_OPT_IN: true
           jobs:
+            - ${{ if eq(parameters.VSCODE_BUILD_MACOS, true) }}:
+              - template: build/azure-pipelines/darwin/product-build-darwin-cli.yml@self
+                parameters:
+                  VSCODE_ARCH: x64
+                  VSCODE_CHECK_ONLY: ${{ variables.VSCODE_CIBUILD }}
+                  VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
+
+            - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), eq(parameters.VSCODE_BUILD_MACOS_ARM64, true)) }}:
+              - template: build/azure-pipelines/darwin/product-build-darwin-cli.yml@self
+                parameters:
+                  VSCODE_ARCH: arm64
+                  VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
+
             - ${{ if eq(variables['VSCODE_CIBUILD'], true) }}:
               - template: build/azure-pipelines/darwin/product-build-darwin-ci.yml@self
                 parameters:
@@ -470,20 +404,13 @@ extends:
             - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), eq(variables['VSCODE_BUILD_MACOS_UNIVERSAL'], true)) }}:
               - template: build/azure-pipelines/darwin/product-build-darwin-universal.yml@self
 
-            - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), or(eq(parameters.VSCODE_BUILD_MACOS, true), eq(parameters.VSCODE_BUILD_MACOS_ARM64, true))) }}:
-              - template: build/azure-pipelines/darwin/product-build-darwin-cli-sign.yml@self
-                parameters:
-                  VSCODE_BUILD_MACOS: ${{ parameters.VSCODE_BUILD_MACOS }}
-                  VSCODE_BUILD_MACOS_ARM64: ${{ parameters.VSCODE_BUILD_MACOS_ARM64 }}
-
-      - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), eq(parameters.VSCODE_COMPILE_ONLY, false), eq(variables['VSCODE_BUILD_STAGE_WEB'], true)) }}:
+      - ${{ if and(eq(variables['VSCODE_CIBUILD'], false), eq(variables['VSCODE_BUILD_STAGE_WEB'], true)) }}:
         - stage: Web
-          dependsOn:
-            - Compile
+          dependsOn: []
           jobs:
             - template: build/azure-pipelines/web/product-build-web.yml@self
 
-      - ${{ if eq(variables['VSCODE_PUBLISH'], 'true') }}:
+      - ${{ if eq(variables['VSCODE_PUBLISH'], true) }}:
         - stage: Publish
           dependsOn: []
           jobs:
@@ -811,3 +738,43 @@ extends:
                   - template: build/azure-pipelines/product-release.yml@self
                     parameters:
                       VSCODE_RELEASE: ${{ parameters.VSCODE_RELEASE }}
+
+      - ${{ if eq(variables['VSCODE_CIBUILD'], true) }}:
+        - stage: node_modules
+          dependsOn: []
+          jobs:
+            - template: build/azure-pipelines/win32/product-build-win32-node-modules.yml@self
+              parameters:
+                VSCODE_ARCH: arm64
+            - template: build/azure-pipelines/linux/product-build-linux-node-modules.yml@self
+              parameters:
+                NPM_ARCH: arm64
+                VSCODE_ARCH: arm64
+            - template: build/azure-pipelines/linux/product-build-linux-node-modules.yml@self
+              parameters:
+                NPM_ARCH: arm
+                VSCODE_ARCH: armhf
+            - template: build/azure-pipelines/alpine/product-build-alpine-node-modules.yml@self
+              parameters:
+                VSCODE_ARCH: x64
+            - template: build/azure-pipelines/alpine/product-build-alpine-node-modules.yml@self
+              parameters:
+                VSCODE_ARCH: arm64
+            - template: build/azure-pipelines/darwin/product-build-darwin-node-modules.yml@self
+              parameters:
+                VSCODE_ARCH: x64
+            - template: build/azure-pipelines/web/product-build-web-node-modules.yml@self
+
+      - ${{ if eq(variables['VSCODE_CIBUILD'], false) }}:
+        - stage: APIScan
+          dependsOn: []
+          pool:
+            name: 1es-windows-2022-x64
+            os: windows
+          jobs:
+            - job: WindowsAPIScan
+              steps:
+                - template: build/azure-pipelines/win32/sdl-scan-win32.yml@self
+                  parameters:
+                    VSCODE_ARCH: x64
+                    VSCODE_QUALITY: ${{ variables.VSCODE_QUALITY }}
diff --git a/build/azure-pipelines/product-compile.yml b/build/azure-pipelines/product-quality-checks.yml
similarity index 64%
rename from build/azure-pipelines/product-compile.yml
rename to build/azure-pipelines/product-quality-checks.yml
index bc13d980df2dd..983a0a4b25aea 100644
--- a/build/azure-pipelines/product-compile.yml
+++ b/build/azure-pipelines/product-quality-checks.yml
@@ -1,14 +1,12 @@
 jobs:
-  - job: Compile
-    timeoutInMinutes: 60
-    templateContext:
-      outputs:
-        - output: pipelineArtifact
-          targetPath: $(Build.ArtifactStagingDirectory)/compilation.tar.gz
-          artifactName: Compilation
-          displayName: Publish compilation artifact
-          isProduction: false
-          sbomEnabled: false
+  - job: Quality
+    displayName: Quality Checks
+    timeoutInMinutes: 20
+    variables:
+      - name: skipComponentGovernanceDetection
+        value: true
+      - name: Codeql.SkipTaskAutoInjection
+        value: true
     steps:
       - template: ./common/checkout.yml@self
 
@@ -30,7 +28,7 @@ jobs:
         condition: and(succeeded(), ne(variables['NPM_REGISTRY'], 'none'))
         displayName: Setup NPM Registry
 
-      - script: mkdir -p .build && node build/azure-pipelines/common/computeNodeModulesCacheKey.ts compile $(node -p process.arch) > .build/packagelockhash
+      - script: mkdir -p .build && node build/azure-pipelines/common/computeNodeModulesCacheKey.ts quality $(node -p process.arch) > .build/packagelockhash
         displayName: Prepare node_modules cache key
 
       - task: Cache@2
@@ -46,9 +44,6 @@ jobs:
 
       - script: |
           set -e
-          # Set the private NPM registry to the global npmrc file
-          # so that authentication works for subfolders like build/, remote/, extensions/ etc
-          # which does not have their own .npmrc file
           npm config set registry "$NPM_REGISTRY"
           echo "##vso[task.setvariable variable=NPMRC_PATH]$(npm config get userconfig)"
         condition: and(succeeded(), ne(variables.NODE_MODULES_RESTORED, 'true'), ne(variables['NPM_REGISTRY'], 'none'))
@@ -71,7 +66,38 @@ jobs:
             fi
             echo "Npm install failed $i, trying again..."
           done
+        workingDirectory: build
         env:
+          GITHUB_TOKEN: "$(github-distro-mixin-password)"
+        displayName: Install build dependencies
+        condition: and(succeeded(), ne(variables.NODE_MODULES_RESTORED, 'true'))
+
+      - script: |
+          set -e
+          export VSCODE_SYSROOT_DIR=$(Build.SourcesDirectory)/.build/sysroots/glibc-2.28-gcc-8.5.0
+          SYSROOT_ARCH="amd64" VSCODE_SYSROOT_PREFIX="-glibc-2.28-gcc-8.5.0" node -e 'import { getVSCodeSysroot } from "./build/linux/debian/install-sysroot.ts"; (async () => { await getVSCodeSysroot(process.env["SYSROOT_ARCH"]); })()'
+        env:
+          VSCODE_ARCH: x64
+          GITHUB_TOKEN: "$(github-distro-mixin-password)"
+        displayName: Download vscode sysroots
+
+      - script: |
+          set -e
+
+          source ./build/azure-pipelines/linux/setup-env.sh
+          node build/npm/preinstall.ts
+
+          for i in {1..5}; do # try 5 times
+            npm ci && break
+            if [ $i -eq 5 ]; then
+              echo "Npm install failed too many times" >&2
+              exit 1
+            fi
+            echo "Npm install failed $i, trying again..."
+          done
+        env:
+          npm_config_arch: x64
+          VSCODE_ARCH: x64
           ELECTRON_SKIP_BINARY_DOWNLOAD: 1
           PLAYWRIGHT_SKIP_BROWSER_DOWNLOAD: 1
           GITHUB_TOKEN: "$(github-distro-mixin-password)"
@@ -93,43 +119,37 @@ jobs:
       - script: node build/azure-pipelines/distro/mixin-quality.ts
         displayName: Mixin distro quality
 
-      - template: common/install-builtin-extensions.yml@self
-
-      - script: npm exec -- npm-run-all2 -lp core-ci extensions-ci hygiene eslint valid-layers-check define-class-fields-check vscode-dts-compile-check tsec-compile-check test-build-scripts
+      - script: node build/azure-pipelines/common/checkDistroCommit.ts
+        displayName: Check distro commit
         env:
           GITHUB_TOKEN: "$(github-distro-mixin-password)"
-        displayName: Compile & Hygiene
-
-      - script: |
-          set -e
-
-          [ -d "out-build" ] || { echo "ERROR: out-build folder is missing" >&2; exit 1; }
-          [ -n "$(find out-build -mindepth 1 2>/dev/null | head -1)" ] || { echo "ERROR: out-build folder is empty" >&2; exit 1; }
-          echo "out-build exists and is not empty"
+          BUILD_SOURCEBRANCH: "$(Build.SourceBranch)"
+        continueOnError: true
+        condition: and(succeeded(), eq(lower(variables['VSCODE_PUBLISH']), 'true'))
 
-          ls -d out-vscode-* >/dev/null 2>&1 || { echo "ERROR: No out-vscode-* folders found" >&2; exit 1; }
-          for folder in out-vscode-*; do
-            [ -d "$folder" ] || { echo "ERROR: $folder is missing" >&2; exit 1; }
-            [ -n "$(find "$folder" -mindepth 1 2>/dev/null | head -1)" ] || { echo "ERROR: $folder is empty" >&2; exit 1; }
-            echo "$folder exists and is not empty"
-          done
+      - script: node build/azure-pipelines/common/checkCopilotChatCompatibility.ts --warn-only
+        displayName: Check Copilot Chat compatibility
+        continueOnError: true
+        condition: and(succeeded(), eq(lower(variables['VSCODE_PUBLISH']), 'true'))
 
-          echo "All required compilation folders checked."
-        displayName: Validate compilation folders
+      - script: npm exec -- npm-run-all2 -lp core-ci hygiene eslint valid-layers-check define-class-fields-check vscode-dts-compile-check tsec-compile-check test-build-scripts
+        env:
+          GITHUB_TOKEN: "$(github-distro-mixin-password)"
+        displayName: Compile & Hygiene
 
-      - script: |
-          set -e
-          npm run compile
-        displayName: Compile smoke test suites (non-OSS)
-        workingDirectory: test/smoke
-        condition: and(succeeded(), eq(variables['VSCODE_STEP_ON_IT'], 'false'))
+      - script: npm run download-builtin-extensions-cg
+        env:
+          GITHUB_TOKEN: "$(github-distro-mixin-password)"
+        displayName: Download component details of built-in extensions
+        condition: and(succeeded(), eq(lower(variables['VSCODE_PUBLISH']), 'true'))
 
-      - script: |
-          set -e
-          npm run compile
-        displayName: Compile integration test suites (non-OSS)
-        workingDirectory: test/integration/browser
-        condition: and(succeeded(), eq(variables['VSCODE_STEP_ON_IT'], 'false'))
+      - task: ms.vss-governance-buildtask.governance-build-task-component-detection.ComponentGovernanceComponentDetection@0
+        displayName: "Component Detection"
+        inputs:
+          sourceScanPath: $(Build.SourcesDirectory)
+          alertWarningLevel: Medium
+        continueOnError: true
+        condition: and(succeeded(), eq(lower(variables['VSCODE_PUBLISH']), 'true'))
 
       - task: AzureCLI@2
         displayName: Fetch secrets
@@ -142,6 +162,7 @@ jobs:
             Write-Host "##vso[task.setvariable variable=AZURE_TENANT_ID]$env:tenantId"
             Write-Host "##vso[task.setvariable variable=AZURE_CLIENT_ID]$env:servicePrincipalId"
             Write-Host "##vso[task.setvariable variable=AZURE_ID_TOKEN;issecret=true]$env:idToken"
+        condition: and(succeeded(), eq(lower(variables['VSCODE_PUBLISH']), 'true'))
 
       - script: |
           set -e
@@ -151,21 +172,4 @@ jobs:
           AZURE_ID_TOKEN="$(AZURE_ID_TOKEN)" \
             node build/azure-pipelines/upload-sourcemaps.ts
         displayName: Upload sourcemaps to Azure
-
-      - script: ./build/azure-pipelines/common/extract-telemetry.sh
-        displayName: Generate lists of telemetry events
-
-      - script: tar -cz --exclude='.build/node_modules_cache' --exclude='.build/node_modules_list.txt' --exclude='.build/distro' -f $(Build.ArtifactStagingDirectory)/compilation.tar.gz $(ls -d .build out-* test/integration/browser/out test/smoke/out test/automation/out 2>/dev/null)
-        displayName: Compress compilation artifact
-
-      - script: npm run download-builtin-extensions-cg
-        env:
-          GITHUB_TOKEN: "$(github-distro-mixin-password)"
-        displayName: Download component details of built-in extensions
-
-      - task: ms.vss-governance-buildtask.governance-build-task-component-detection.ComponentGovernanceComponentDetection@0
-        displayName: "Component Detection"
-        inputs:
-          sourceScanPath: $(Build.SourcesDirectory)
-          alertWarningLevel: Medium
-        continueOnError: true
+        condition: and(succeeded(), eq(lower(variables['VSCODE_PUBLISH']), 'true'))
diff --git a/build/azure-pipelines/product-validation-checks.yml b/build/azure-pipelines/product-validation-checks.yml
deleted file mode 100644
index adf61f33c428c..0000000000000
--- a/build/azure-pipelines/product-validation-checks.yml
+++ /dev/null
@@ -1,40 +0,0 @@
-jobs:
-  - job: ValidationChecks
-    displayName: Distro and Extension Validation
-    timeoutInMinutes: 15
-    steps:
-      - template: ./common/checkout.yml@self
-
-      - task: NodeTool@0
-        inputs:
-          versionSource: fromFile
-          versionFilePath: .nvmrc
-
-      - template: ./distro/download-distro.yml@self
-
-      - script: node build/azure-pipelines/distro/mixin-quality.ts
-        displayName: Mixin distro quality
-
-      - task: AzureKeyVault@2
-        displayName: "Azure Key Vault: Get Secrets"
-        inputs:
-          azureSubscription: vscode
-          KeyVaultName: vscode-build-secrets
-          SecretsFilter: "github-distro-mixin-password"
-
-      - script: npm ci
-        workingDirectory: build
-        env:
-          GITHUB_TOKEN: "$(github-distro-mixin-password)"
-        displayName: Install build dependencies
-
-      - script: node build/azure-pipelines/common/checkDistroCommit.ts
-        displayName: Check distro commit
-        env:
-          GITHUB_TOKEN: "$(github-distro-mixin-password)"
-          BUILD_SOURCEBRANCH: "$(Build.SourceBranch)"
-        continueOnError: true
-
-      - script: node build/azure-pipelines/common/checkCopilotChatCompatibility.ts --warn-only
-        displayName: Check Copilot Chat compatibility
-        continueOnError: true
diff --git a/build/azure-pipelines/web/product-build-web.yml b/build/azure-pipelines/web/product-build-web.yml
index 71932745be7fb..c9916acded34d 100644
--- a/build/azure-pipelines/web/product-build-web.yml
+++ b/build/azure-pipelines/web/product-build-web.yml
@@ -33,15 +33,6 @@ jobs:
           KeyVaultName: vscode-build-secrets
           SecretsFilter: "github-distro-mixin-password"
 
-      - task: DownloadPipelineArtifact@2
-        inputs:
-          artifact: Compilation
-          path: $(Build.ArtifactStagingDirectory)
-        displayName: Download compilation output
-
-      - script: tar -xzf $(Build.ArtifactStagingDirectory)/compilation.tar.gz
-        displayName: Extract compilation output
-
       - script: node build/setup-npm-registry.ts $NPM_REGISTRY
         condition: and(succeeded(), ne(variables['NPM_REGISTRY'], 'none'))
         displayName: Setup NPM Registry
@@ -118,6 +109,11 @@ jobs:
 
       - template: ../common/install-builtin-extensions.yml@self
 
+      - script: npm run gulp core-ci
+        env:
+          GITHUB_TOKEN: "$(github-distro-mixin-password)"
+        displayName: Compile
+
       - script: |
           set -e
           npm run gulp vscode-web-min-ci
diff --git a/build/azure-pipelines/win32/codesign.ts b/build/azure-pipelines/win32/codesign.ts
index dce5e55b84069..1d51cb08c622e 100644
--- a/build/azure-pipelines/win32/codesign.ts
+++ b/build/azure-pipelines/win32/codesign.ts
@@ -19,7 +19,7 @@ async function main() {
 	// 2. Codesign Powershell scripts
 	// 3. Codesign context menu appx package (insiders only)
 	const codesignTask1 = spawnCodesignProcess(esrpCliDLLPath, 'sign-windows', codeSigningFolderPath, '*.dll,*.exe,*.node');
-	const codesignTask2 = spawnCodesignProcess(esrpCliDLLPath, 'sign-windows-appx', codeSigningFolderPath, '*.ps1');
+	const codesignTask2 = spawnCodesignProcess(esrpCliDLLPath, 'sign-windows-appx', codeSigningFolderPath, '*.ps1,*.psm1,*.psd1,*.ps1xml');
 	const codesignTask3 = process.env['VSCODE_QUALITY'] !== 'exploration'
 		? spawnCodesignProcess(esrpCliDLLPath, 'sign-windows-appx', codeSigningFolderPath, '*.appx')
 		: undefined;
diff --git a/build/azure-pipelines/win32/product-build-win32-cli-sign.yml b/build/azure-pipelines/win32/product-build-win32-cli-sign.yml
deleted file mode 100644
index fa1328d99e27f..0000000000000
--- a/build/azure-pipelines/win32/product-build-win32-cli-sign.yml
+++ /dev/null
@@ -1,83 +0,0 @@
-parameters:
-  - name: VSCODE_BUILD_WIN32
-    type: boolean
-  - name: VSCODE_BUILD_WIN32_ARM64
-    type: boolean
-
-jobs:
-  - job: WindowsCLISign
-    timeoutInMinutes: 90
-    templateContext:
-      outputParentDirectory: $(Build.ArtifactStagingDirectory)/out
-      outputs:
-        - ${{ if eq(parameters.VSCODE_BUILD_WIN32, true) }}:
-          - output: pipelineArtifact
-            targetPath: $(Build.ArtifactStagingDirectory)/out/vscode_cli_win32_x64_cli.zip
-            artifactName: vscode_cli_win32_x64_cli
-            displayName: Publish signed artifact with ID vscode_cli_win32_x64_cli
-            sbomBuildDropPath: $(Build.BinariesDirectory)/sign/unsigned_vscode_cli_win32_x64_cli
-            sbomPackageName: "VS Code Windows x64 CLI"
-            sbomPackageVersion: $(Build.SourceVersion)
-        - ${{ if eq(parameters.VSCODE_BUILD_WIN32_ARM64, true) }}:
-          - output: pipelineArtifact
-            targetPath: $(Build.ArtifactStagingDirectory)/out/vscode_cli_win32_arm64_cli.zip
-            artifactName: vscode_cli_win32_arm64_cli
-            displayName: Publish signed artifact with ID vscode_cli_win32_arm64_cli
-            sbomBuildDropPath: $(Build.BinariesDirectory)/sign/unsigned_vscode_cli_win32_arm64_cli
-            sbomPackageName: "VS Code Windows arm64 CLI"
-            sbomPackageVersion: $(Build.SourceVersion)
-    steps:
-      - template: ../common/checkout.yml@self
-
-      - task: NodeTool@0
-        displayName: "Use Node.js"
-        inputs:
-          versionSource: fromFile
-          versionFilePath: .nvmrc
-
-      - task: AzureKeyVault@2
-        displayName: "Azure Key Vault: Get Secrets"
-        inputs:
-          azureSubscription: vscode
-          KeyVaultName: vscode-build-secrets
-          SecretsFilter: "github-distro-mixin-password"
-
-      - powershell: node build/setup-npm-registry.ts $env:NPM_REGISTRY build
-        condition: and(succeeded(), ne(variables['NPM_REGISTRY'], 'none'))
-        displayName: Setup NPM Registry
-
-      - powershell: |
-          . build/azure-pipelines/win32/exec.ps1
-          $ErrorActionPreference = "Stop"
-          # Set the private NPM registry to the global npmrc file
-          # so that authentication works for subfolders like build/, remote/, extensions/ etc
-          # which does not have their own .npmrc file
-          exec { npm config set registry "$env:NPM_REGISTRY" }
-          $NpmrcPath = (npm config get userconfig)
-          echo "##vso[task.setvariable variable=NPMRC_PATH]$NpmrcPath"
-        condition: and(succeeded(), ne(variables['NPM_REGISTRY'], 'none'))
-        displayName: Setup NPM
-
-      - task: npmAuthenticate@0
-        inputs:
-          workingFile: $(NPMRC_PATH)
-        condition: and(succeeded(), ne(variables['NPM_REGISTRY'], 'none'))
-        displayName: Setup NPM Authentication
-
-      - powershell: |
-          . azure-pipelines/win32/exec.ps1
-          $ErrorActionPreference = "Stop"
-          exec { npm ci }
-        workingDirectory: build
-        env:
-          GITHUB_TOKEN: "$(github-distro-mixin-password)"
-        retryCountOnTaskFailure: 5
-        displayName: Install build dependencies
-
-      - template: ./steps/product-build-win32-cli-sign.yml@self
-        parameters:
-          VSCODE_CLI_ARTIFACTS:
-            - ${{ if eq(parameters.VSCODE_BUILD_WIN32, true) }}:
-              - unsigned_vscode_cli_win32_x64_cli
-            - ${{ if eq(parameters.VSCODE_BUILD_WIN32_ARM64, true) }}:
-              - unsigned_vscode_cli_win32_arm64_cli
diff --git a/build/azure-pipelines/win32/product-build-win32-cli.yml b/build/azure-pipelines/win32/product-build-win32-cli.yml
index 5dd69c3b50de3..78461a959eda3 100644
--- a/build/azure-pipelines/win32/product-build-win32-cli.yml
+++ b/build/azure-pipelines/win32/product-build-win32-cli.yml
@@ -9,22 +9,23 @@ parameters:
 
 jobs:
   - job: WindowsCLI_${{ upper(parameters.VSCODE_ARCH) }}
-    displayName: Windows (${{ upper(parameters.VSCODE_ARCH) }})
+    displayName: Windows CLI (${{ upper(parameters.VSCODE_ARCH) }})
     pool:
       name: 1es-windows-2022-x64
       os: windows
-    timeoutInMinutes: 30
+    timeoutInMinutes: 90
     variables:
       VSCODE_ARCH: ${{ parameters.VSCODE_ARCH }}
     templateContext:
       outputs:
         - ${{ if not(parameters.VSCODE_CHECK_ONLY) }}:
           - output: pipelineArtifact
-            targetPath: $(Build.ArtifactStagingDirectory)/unsigned_vscode_cli_win32_$(VSCODE_ARCH)_cli.zip
-            artifactName: unsigned_vscode_cli_win32_$(VSCODE_ARCH)_cli
-            displayName: Publish unsigned_vscode_cli_win32_$(VSCODE_ARCH)_cli artifact
-            sbomEnabled: false
-            isProduction: false
+            targetPath: $(Build.ArtifactStagingDirectory)/out/vscode_cli_win32_$(VSCODE_ARCH)_cli.zip
+            artifactName: vscode_cli_win32_$(VSCODE_ARCH)_cli
+            displayName: Publish vscode_cli_win32_$(VSCODE_ARCH)_cli artifact
+            sbomBuildDropPath: $(Build.ArtifactStagingDirectory)/sign
+            sbomPackageName: "VS Code Windows $(VSCODE_ARCH) CLI"
+            sbomPackageVersion: $(Build.SourceVersion)
 
     steps:
       - template: ../common/checkout.yml@self
@@ -75,3 +76,54 @@ jobs:
             ${{ if eq(parameters.VSCODE_ARCH, 'arm64') }}:
               RUSTFLAGS: "-Ctarget-feature=+crt-static -Clink-args=/guard:cf -Clink-args=/CETCOMPAT:NO"
             CFLAGS: "/guard:cf /Qspectre"
+
+      - ${{ if not(parameters.VSCODE_CHECK_ONLY) }}:
+        - template: ../common/publish-artifact.yml@self
+          parameters:
+            targetPath: $(Build.ArtifactStagingDirectory)/unsigned_vscode_cli_win32_$(VSCODE_ARCH)_cli.zip
+            artifactName: unsigned_vscode_cli_win32_$(VSCODE_ARCH)_cli
+            displayName: Publish unsigned CLI
+            sbomEnabled: false
+
+        - task: ExtractFiles@1
+          displayName: Extract unsigned CLI
+          inputs:
+            archiveFilePatterns: $(Build.ArtifactStagingDirectory)/unsigned_vscode_cli_win32_$(VSCODE_ARCH)_cli.zip
+            destinationFolder: $(Build.ArtifactStagingDirectory)/sign
+
+        - task: UseDotNet@2
+          inputs:
+            version: 6.x
+
+        - task: EsrpCodeSigning@5
+          inputs:
+            UseMSIAuthentication: true
+            ConnectedServiceName: vscode-esrp
+            AppRegistrationClientId: $(ESRP_CLIENT_ID)
+            AppRegistrationTenantId: $(ESRP_TENANT_ID)
+            AuthAKVName: vscode-esrp
+            AuthSignCertName: esrp-sign
+            FolderPath: .
+            Pattern: noop
+          displayName: 'Install ESRP Tooling'
+
+        - powershell: |
+            . build/azure-pipelines/win32/exec.ps1
+            $ErrorActionPreference = "Stop"
+            $EsrpCodeSigningTool = (gci -directory -filter EsrpCodeSigning_* $(Agent.RootDirectory)\_tasks | Select-Object -last 1).FullName
+            $Version = (gci -directory $EsrpCodeSigningTool | Select-Object -last 1).FullName
+            echo "##vso[task.setvariable variable=EsrpCliDllPath]$Version\net6.0\esrpcli.dll"
+          displayName: Find ESRP CLI
+
+        - powershell: node build\azure-pipelines\common\sign.ts $env:EsrpCliDllPath sign-windows $(Build.ArtifactStagingDirectory)/sign "*.exe"
+          env:
+            SYSTEM_ACCESSTOKEN: $(System.AccessToken)
+          displayName: ✍️ Codesign
+
+        - task: ArchiveFiles@2
+          displayName: Archive signed CLI
+          inputs:
+            rootFolderOrFile: $(Build.ArtifactStagingDirectory)/sign
+            includeRootFolder: false
+            archiveType: zip
+            archiveFile: $(Build.ArtifactStagingDirectory)/out/vscode_cli_win32_$(VSCODE_ARCH)_cli.zip
diff --git a/build/azure-pipelines/win32/product-build-win32.yml b/build/azure-pipelines/win32/product-build-win32.yml
index 3a91d3cdd97db..9b4c4e27070ab 100644
--- a/build/azure-pipelines/win32/product-build-win32.yml
+++ b/build/azure-pipelines/win32/product-build-win32.yml
@@ -21,6 +21,7 @@ jobs:
     timeoutInMinutes: 90
     variables:
       VSCODE_ARCH: ${{ parameters.VSCODE_ARCH }}
+      BUILDS_API_URL: $(System.CollectionUri)$(System.TeamProject)/_apis/build/builds/$(Build.BuildId)/
     templateContext:
       outputParentDirectory: $(Build.ArtifactStagingDirectory)/out
       outputs:
diff --git a/build/azure-pipelines/win32/sdl-scan-win32.yml b/build/azure-pipelines/win32/sdl-scan-win32.yml
index e3356effa95a7..2580588a7433f 100644
--- a/build/azure-pipelines/win32/sdl-scan-win32.yml
+++ b/build/azure-pipelines/win32/sdl-scan-win32.yml
@@ -100,7 +100,11 @@ steps:
     env:
       VSCODE_QUALITY: ${{ parameters.VSCODE_QUALITY }}
 
-  - powershell: npm run compile
+  - template: ../common/install-builtin-extensions.yml@self
+
+  - powershell: npm run gulp core-ci
+    env:
+      GITHUB_TOKEN: "$(github-distro-mixin-password)"
     displayName: Compile
 
   - powershell: npm run gulp "vscode-symbols-win32-${{ parameters.VSCODE_ARCH }}"
diff --git a/build/azure-pipelines/win32/steps/product-build-win32-cli-sign.yml b/build/azure-pipelines/win32/steps/product-build-win32-cli-sign.yml
deleted file mode 100644
index 0caba3d1a2b88..0000000000000
--- a/build/azure-pipelines/win32/steps/product-build-win32-cli-sign.yml
+++ /dev/null
@@ -1,61 +0,0 @@
-parameters:
-  - name: VSCODE_CLI_ARTIFACTS
-    type: object
-    default: []
-
-steps:
-  - task: UseDotNet@2
-    inputs:
-      version: 6.x
-
-  - task: EsrpCodeSigning@5
-    inputs:
-      UseMSIAuthentication: true
-      ConnectedServiceName: vscode-esrp
-      AppRegistrationClientId: $(ESRP_CLIENT_ID)
-      AppRegistrationTenantId: $(ESRP_TENANT_ID)
-      AuthAKVName: vscode-esrp
-      AuthSignCertName: esrp-sign
-      FolderPath: .
-      Pattern: noop
-    displayName: 'Install ESRP Tooling'
-
-  - powershell: |
-      . build/azure-pipelines/win32/exec.ps1
-      $ErrorActionPreference = "Stop"
-      $EsrpCodeSigningTool = (gci -directory -filter EsrpCodeSigning_* $(Agent.RootDirectory)\_tasks | Select-Object -last 1).FullName
-      $Version = (gci -directory $EsrpCodeSigningTool | Select-Object -last 1).FullName
-      echo "##vso[task.setvariable variable=EsrpCliDllPath]$Version\net6.0\esrpcli.dll"
-    displayName: Find ESRP CLI
-
-  - ${{ each target in parameters.VSCODE_CLI_ARTIFACTS }}:
-      - task: DownloadPipelineArtifact@2
-        displayName: Download artifact
-        inputs:
-          artifact: ${{ target }}
-          path: $(Build.BinariesDirectory)/pkg/${{ target }}
-
-      - task: ExtractFiles@1
-        displayName: Extract artifact
-        inputs:
-          archiveFilePatterns: $(Build.BinariesDirectory)/pkg/${{ target }}/*.zip
-          destinationFolder: $(Build.BinariesDirectory)/sign/${{ target }}
-
-  - powershell: node build\azure-pipelines\common\sign.ts $env:EsrpCliDllPath sign-windows $(Build.BinariesDirectory)/sign "*.exe"
-    env:
-      SYSTEM_ACCESSTOKEN: $(System.AccessToken)
-    displayName: ✍️ Codesign
-
-  - ${{ each target in parameters.VSCODE_CLI_ARTIFACTS }}:
-      - powershell: |
-          $ASSET_ID = "${{ target }}".replace("unsigned_", "");
-          echo "##vso[task.setvariable variable=ASSET_ID]$ASSET_ID"
-        displayName: Set asset id variable
-
-      - task: ArchiveFiles@2
-        displayName: Archive signed files
-        inputs:
-          rootFolderOrFile: $(Build.BinariesDirectory)/sign/${{ target }}
-          includeRootFolder: false
-          archiveType: zip
-          archiveFile: $(Build.ArtifactStagingDirectory)/out/$(ASSET_ID).zip
diff --git a/build/azure-pipelines/win32/steps/product-build-win32-compile.yml b/build/azure-pipelines/win32/steps/product-build-win32-compile.yml
index d6412c2342090..3cb6413480af8 100644
--- a/build/azure-pipelines/win32/steps/product-build-win32-compile.yml
+++ b/build/azure-pipelines/win32/steps/product-build-win32-compile.yml
@@ -37,18 +37,6 @@ steps:
       KeyVaultName: vscode-build-secrets
       SecretsFilter: "github-distro-mixin-password"
 
-  - task: DownloadPipelineArtifact@2
-    inputs:
-      artifact: Compilation
-      path: $(Build.ArtifactStagingDirectory)
-    displayName: Download compilation output
-
-  - task: ExtractFiles@1
-    displayName: Extract compilation output
-    inputs:
-      archiveFilePatterns: "$(Build.ArtifactStagingDirectory)/compilation.tar.gz"
-      cleanDestinationFolder: false
-
   - powershell: node build/setup-npm-registry.ts $env:NPM_REGISTRY
     condition: and(succeeded(), ne(variables['NPM_REGISTRY'], 'none'))
     displayName: Setup NPM Registry
@@ -114,11 +102,34 @@ steps:
     condition: and(succeeded(), ne(variables.NODE_MODULES_RESTORED, 'true'))
     displayName: Create node_modules archive
 
+  - ${{ if ne(parameters.VSCODE_CIBUILD, true) }}:
+    - pwsh: npx deemon --detach --wait -- node build/azure-pipelines/common/waitForArtifacts.ts unsigned_vscode_cli_win32_$(VSCODE_ARCH)_cli
+      env:
+        SYSTEM_ACCESSTOKEN: $(System.AccessToken)
+      displayName: Wait for CLI artifact (background)
+
   - powershell: node build/azure-pipelines/distro/mixin-quality.ts
     displayName: Mixin distro quality
 
   - template: ../../common/install-builtin-extensions.yml@self
 
+  - powershell: npm run gulp core-ci
+    env:
+      GITHUB_TOKEN: "$(github-distro-mixin-password)"
+    displayName: Compile
+
+  - script: node build/azure-pipelines/common/extract-telemetry.ts
+    displayName: Generate lists of telemetry events
+
+  - ${{ if or(eq(parameters.VSCODE_RUN_ELECTRON_TESTS, true), eq(parameters.VSCODE_RUN_BROWSER_TESTS, true), eq(parameters.VSCODE_RUN_REMOTE_TESTS, true)) }}:
+    - powershell: |
+        . build/azure-pipelines/win32/exec.ps1
+        $ErrorActionPreference = "Stop"
+        exec { npm run compile --prefix test/smoke }
+        exec { npm run compile --prefix test/integration/browser }
+      displayName: Compile test suites (non-OSS)
+      condition: and(succeeded(), eq(variables['VSCODE_STEP_ON_IT'], 'false'))
+
   - ${{ if ne(parameters.VSCODE_CIBUILD, true) }}:
     - powershell: |
         npm run copy-policy-dto --prefix build
@@ -181,6 +192,11 @@ steps:
     displayName: Build server (web)
 
   - ${{ if ne(parameters.VSCODE_CIBUILD, true) }}:
+    - pwsh: npx deemon --attach -- node build/azure-pipelines/common/waitForArtifacts.ts unsigned_vscode_cli_win32_$(VSCODE_ARCH)_cli
+      env:
+        SYSTEM_ACCESSTOKEN: $(System.AccessToken)
+      displayName: Wait for CLI artifact
+
     - task: DownloadPipelineArtifact@2
       inputs:
         artifact: unsigned_vscode_cli_win32_$(VSCODE_ARCH)_cli
diff --git a/build/checksums/electron.txt b/build/checksums/electron.txt
index 3df57a48a97d2..5d8343f42a9cd 100644
--- a/build/checksums/electron.txt
+++ b/build/checksums/electron.txt
@@ -1,75 +1,75 @@
-1a1bb622d9788793310458b7bf9eedcea8347da9556dd1d7661b757c15ebfdd5 *chromedriver-v39.6.0-darwin-arm64.zip
-c84565c127adeca567ca69e85bbd8f387fff1f83c09e69f6f851528f5602dc4e *chromedriver-v39.6.0-darwin-x64.zip
-f50df11f99a2e3df84560d5331608cd0a9d7a147a1490f25edfd8a95531918a2 *chromedriver-v39.6.0-linux-arm64.zip
-a571fd25e33f3b3bded91506732a688319d93eb652e959bb19a09cd3f67f9e5f *chromedriver-v39.6.0-linux-armv7l.zip
-2a50751190bbfe07984f7d8cbf2f12c257a4c132a36922a78c4e320169b8f498 *chromedriver-v39.6.0-linux-x64.zip
-cf6034c20b727c48a6f44bb87b1ec89fd4189f56200a32cd39cedaab3f19e007 *chromedriver-v39.6.0-mas-arm64.zip
-d2107db701c41fa5f3aaa04c279275ac4dcffde4542c032c806939acd8c6cd6c *chromedriver-v39.6.0-mas-x64.zip
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+1bc0a3294d258a59846aa5c5359cd8b0f43831ebd7c3e1dde9a6cfaa39d845bf *mksnapshot-v39.8.0-linux-armv7l-x64.zip
+4e414dbe75f460cb34508608db984aa6f4d274f333fa327a3d631da4a516da8f *mksnapshot-v39.8.0-linux-x64.zip
+c51c86e3a11ad75fb4f7559798f6d64ec7def19583c96ce08de7ee5796568841 *mksnapshot-v39.8.0-mas-arm64.zip
+6544d1e93adea1e9a694f9b9f539d96f84df647d9c9319b29d4fc88751ff9075 *mksnapshot-v39.8.0-mas-x64.zip
+372b4685c53f19ccc72c33d78c1283d9389c72f42cd48224439fe4f89199caa0 *mksnapshot-v39.8.0-win32-arm64-x64.zip
+199e9244f4522a4a02aece09a6a33887b24d7ec837640d39c930170e4b3caa57 *mksnapshot-v39.8.0-win32-ia32.zip
+970e979e7a8b70f300f7854cb571756d9049bc42b44a6153a9ce3a18e1a83243 *mksnapshot-v39.8.0-win32-x64.zip
diff --git a/build/darwin/create-universal-app.ts b/build/darwin/create-universal-app.ts
index 26aead0ca19dd..9e90e31491f58 100644
--- a/build/darwin/create-universal-app.ts
+++ b/build/darwin/create-universal-app.ts
@@ -28,7 +28,7 @@ async function main(buildDir?: string) {
 	const filesToSkip = [
 		'**/CodeResources',
 		'**/Credits.rtf',
-		'**/policies/{*.mobileconfig,**/*.plist}',
+		'**/policies/{*.mobileconfig,**/*.plist}'
 	];
 
 	await makeUniversalApp({
diff --git a/build/darwin/dmg-settings.py.template b/build/darwin/dmg-settings.py.template
index 4a54a69ab0264..f471029f32a2a 100644
--- a/build/darwin/dmg-settings.py.template
+++ b/build/darwin/dmg-settings.py.template
@@ -6,8 +6,9 @@ format = 'ULMO'
 badge_icon = {{BADGE_ICON}}
 background = {{BACKGROUND}}
 
-# Volume size (None = auto-calculate)
-size = None
+# Volume size
+size = '1g'
+shrink = False
 
 # Files and symlinks
 files = [{{APP_PATH}}]
diff --git a/build/gulpfile.extensions.ts b/build/gulpfile.extensions.ts
index a2eb47535f4dd..e0137816c8c92 100644
--- a/build/gulpfile.extensions.ts
+++ b/build/gulpfile.extensions.ts
@@ -95,6 +95,7 @@ const compilations = [
 
 	'.vscode/extensions/vscode-selfhost-test-provider/tsconfig.json',
 	'.vscode/extensions/vscode-selfhost-import-aid/tsconfig.json',
+	'.vscode/extensions/vscode-extras/tsconfig.json',
 ];
 
 const getBaseUrl = (out: string) => `https://main.vscode-cdn.net/sourcemaps/${commit}/${out}`;
@@ -289,19 +290,7 @@ export const compileAllExtensionsBuildTask = task.define('compile-extensions-bui
 ));
 gulp.task(compileAllExtensionsBuildTask);
 
-// This task is run in the compilation stage of the CI pipeline. We only compile the non-native extensions since those can be fully built regardless of platform.
-// This defers the native extensions to the platform specific stage of the CI pipeline.
-gulp.task(task.define('extensions-ci', task.series(compileNonNativeExtensionsBuildTask, compileExtensionMediaBuildTask)));
 
-const compileExtensionsBuildPullRequestTask = task.define('compile-extensions-build-pr', task.series(
-	cleanExtensionsBuildTask,
-	bundleMarketplaceExtensionsBuildTask,
-	task.define('bundle-extensions-build-pr', () => ext.packageAllLocalExtensionsStream(false, true).pipe(gulp.dest('.build'))),
-));
-gulp.task(compileExtensionsBuildPullRequestTask);
-
-// This task is run in the compilation stage of the PR pipeline. We compile all extensions in it to verify compilation.
-gulp.task(task.define('extensions-ci-pr', task.series(compileExtensionsBuildPullRequestTask, compileExtensionMediaBuildTask)));
 
 //#endregion
 
@@ -320,13 +309,6 @@ async function buildWebExtensions(isWatch: boolean): Promise<void> {
 		{ ignore: ['**/node_modules'] }
 	);
 
-	// Find all webpack configs, excluding those that will be esbuilt
-	const esbuildExtensionDirs = new Set(esbuildConfigLocations.map(p => path.dirname(p)));
-	const webpackConfigLocations = (await nodeUtil.promisify(glob)(
-		path.join(extensionsPath, '**', 'extension-browser.webpack.config.js'),
-		{ ignore: ['**/node_modules'] }
-	)).filter(configPath => !esbuildExtensionDirs.has(path.dirname(configPath)));
-
 	const promises: Promise<unknown>[] = [];
 
 	// Esbuild for extensions
@@ -341,10 +323,5 @@ async function buildWebExtensions(isWatch: boolean): Promise<void> {
 		);
 	}
 
-	// Run webpack for remaining extensions
-	if (webpackConfigLocations.length > 0) {
-		promises.push(ext.webpackExtensions('packaging web extension', isWatch, webpackConfigLocations.map(configPath => ({ configPath }))));
-	}
-
 	await Promise.all(promises);
 }
diff --git a/build/gulpfile.reh.ts b/build/gulpfile.reh.ts
index 8e7f6bbbdca7e..0ad08ab6fbe98 100644
--- a/build/gulpfile.reh.ts
+++ b/build/gulpfile.reh.ts
@@ -83,6 +83,7 @@ const serverResourceIncludes = [
 	'out-build/vs/workbench/contrib/terminal/common/scripts/shellIntegration-rc.zsh',
 	'out-build/vs/workbench/contrib/terminal/common/scripts/shellIntegration-login.zsh',
 	'out-build/vs/workbench/contrib/terminal/common/scripts/shellIntegration.fish',
+	'out-build/vs/workbench/contrib/terminal/common/scripts/psreadline/**',
 
 ];
 
diff --git a/build/gulpfile.vscode.ts b/build/gulpfile.vscode.ts
index c50bdfcda3f7c..f60817b66d525 100644
--- a/build/gulpfile.vscode.ts
+++ b/build/gulpfile.vscode.ts
@@ -31,6 +31,7 @@ import minimist from 'minimist';
 import { compileBuildWithoutManglingTask, compileBuildWithManglingTask } from './gulpfile.compile.ts';
 import { compileNonNativeExtensionsBuildTask, compileNativeExtensionsBuildTask, compileAllExtensionsBuildTask, compileExtensionMediaBuildTask, cleanExtensionsBuildTask } from './gulpfile.extensions.ts';
 import { copyCodiconsTask } from './lib/compilation.ts';
+import type { EmbeddedProductInfo } from './lib/embeddedType.ts';
 import { useEsbuildTranspile } from './buildConfig.ts';
 import { promisify } from 'util';
 import globCallback from 'glob';
@@ -42,8 +43,6 @@ const glob = promisify(globCallback);
 const rcedit = promisify(rceditCallback);
 const root = path.dirname(import.meta.dirname);
 const commit = getVersion(root);
-const useVersionedUpdate = process.platform === 'win32' && (product as typeof product & { win32VersionedUpdate?: boolean })?.win32VersionedUpdate;
-const versionedResourcesFolder = useVersionedUpdate ? commit!.substring(0, 10) : '';
 
 // Build
 const vscodeEntryPoints = [
@@ -90,6 +89,7 @@ const vscodeResourceIncludes = [
 	'out-build/vs/workbench/contrib/terminal/common/scripts/*.psm1',
 	'out-build/vs/workbench/contrib/terminal/common/scripts/*.sh',
 	'out-build/vs/workbench/contrib/terminal/common/scripts/*.zsh',
+	'out-build/vs/workbench/contrib/terminal/common/scripts/psreadline/**',
 
 	// Accessibility Signals
 	'out-build/vs/platform/accessibilitySignal/browser/media/*.mp3',
@@ -99,6 +99,8 @@ const vscodeResourceIncludes = [
 
 	// Sessions
 	'out-build/vs/sessions/contrib/chat/browser/media/*.svg',
+	'out-build/vs/sessions/prompts/*.prompt.md',
+	'out-build/vs/sessions/skills/**/SKILL.md',
 
 	// Extensions
 	'out-build/vs/workbench/contrib/extensions/browser/media/{theme-icon.png,language-icon.svg}',
@@ -236,6 +238,9 @@ function runTsGoTypeCheck(): Promise<void> {
 }
 
 const sourceMappingURLBase = `https://main.vscode-cdn.net/sourcemaps/${commit}`;
+const isCI = !!process.env['CI'] || !!process.env['BUILD_ARTIFACTSTAGINGDIRECTORY'] || !!process.env['GITHUB_WORKSPACE'];
+const useCdnSourceMapsForPackagingTasks = isCI;
+const stripSourceMapsInPackagingTasks = isCI;
 const minifyVSCodeTask = task.define('minify-vscode', task.series(
 	bundleVSCodeTask,
 	util.rimraf('out-vscode-min'),
@@ -243,19 +248,17 @@ const minifyVSCodeTask = task.define('minify-vscode', task.series(
 ));
 gulp.task(minifyVSCodeTask);
 
-const coreCIOld = task.define('core-ci-old', task.series(
+gulp.task(task.define('core-ci-old', task.series(
 	gulp.task('compile-build-with-mangling') as task.Task,
 	task.parallel(
 		gulp.task('minify-vscode') as task.Task,
 		gulp.task('minify-vscode-reh') as task.Task,
 		gulp.task('minify-vscode-reh-web') as task.Task,
 	)
-));
-gulp.task(coreCIOld);
+)));
 
-const coreCIEsbuild = task.define('core-ci-esbuild', task.series(
+gulp.task(task.define('core-ci', task.series(
 	copyCodiconsTask,
-	cleanExtensionsBuildTask,
 	compileNonNativeExtensionsBuildTask,
 	compileExtensionMediaBuildTask,
 	writeISODate('out-build'),
@@ -269,10 +272,7 @@ const coreCIEsbuild = task.define('core-ci-esbuild', task.series(
 		task.define('esbuild-vscode-reh-min', () => runEsbuildBundle('out-vscode-reh-min', true, true, 'server', `${sourceMappingURLBase}/core`)),
 		task.define('esbuild-vscode-reh-web-min', () => runEsbuildBundle('out-vscode-reh-web-min', true, true, 'server-web', `${sourceMappingURLBase}/core`)),
 	)
-));
-gulp.task(coreCIEsbuild);
-
-gulp.task(task.define('core-ci', useEsbuildTranspile ? coreCIEsbuild : coreCIOld));
+)));
 
 const coreCIPR = task.define('core-ci-pr', task.series(
 	gulp.task('compile-build-without-mangling') as task.Task,
@@ -324,6 +324,7 @@ function packageTask(platform: string, arch: string, sourceFolderName: string, d
 
 	const task = () => {
 		const out = sourceFolderName;
+		const versionedResourcesFolder = util.getVersionedResourcesFolder(platform, commit!);
 
 		const checksums = computeChecksums(out, [
 			'vs/base/parts/sandbox/electron-browser/preload.js',
@@ -353,8 +354,11 @@ function packageTask(platform: string, arch: string, sourceFolderName: string, d
 
 		const extensions = gulp.src(['.build/extensions/**', ...platformSpecificBuiltInExtensionsExclusions], { base: '.build', dot: true });
 
+		const sourceFilterPattern = stripSourceMapsInPackagingTasks
+			? ['**', '!**/*.{js,css}.map']
+			: ['**'];
 		const sources = es.merge(src, extensions)
-			.pipe(filter(['**', '!**/*.{js,css}.map'], { dot: true }));
+			.pipe(filter(sourceFilterPattern, { dot: true }));
 
 		let version = packageJson.version;
 		const quality = (product as { quality?: string }).quality;
@@ -389,7 +393,7 @@ function packageTask(platform: string, arch: string, sourceFolderName: string, d
 
 		const isInsiderOrExploration = quality === 'insider' || quality === 'exploration';
 		const embedded = isInsiderOrExploration
-			? (product as typeof product & { embedded?: { nameShort: string; nameLong: string; applicationName: string; dataFolderName: string; darwinBundleIdentifier: string; urlProtocol: string } }).embedded
+			? (product as typeof product & { embedded?: EmbeddedProductInfo }).embedded
 			: undefined;
 
 		const packageSubJsonStream = isInsiderOrExploration
@@ -404,12 +408,9 @@ function packageTask(platform: string, arch: string, sourceFolderName: string, d
 		const productSubJsonStream = embedded
 			? gulp.src(['product.json'], { base: '.' })
 				.pipe(jsonEditor((json: Record<string, unknown>) => {
-					json.nameShort = embedded.nameShort;
-					json.nameLong = embedded.nameLong;
-					json.applicationName = embedded.applicationName;
-					json.dataFolderName = embedded.dataFolderName;
-					json.darwinBundleIdentifier = embedded.darwinBundleIdentifier;
-					json.urlProtocol = embedded.urlProtocol;
+					Object.keys(embedded).forEach(key => {
+						json[key] = embedded[key as keyof EmbeddedProductInfo];
+					});
 					return json;
 				}))
 				.pipe(rename('product.sub.json'))
@@ -427,8 +428,13 @@ function packageTask(platform: string, arch: string, sourceFolderName: string, d
 		const productionDependencies = getProductionDependencies(root);
 		const dependenciesSrc = productionDependencies.map(d => path.relative(root, d)).map(d => [`${d}/**`, `!${d}/**/{test,tests}/**`]).flat().concat('!**/*.mk');
 
+		const depFilterPattern = ['**', `!**/${config.version}/**`, '!**/bin/darwin-arm64-87/**', '!**/package-lock.json', '!**/yarn.lock'];
+		if (stripSourceMapsInPackagingTasks) {
+			depFilterPattern.push('!**/*.{js,css}.map');
+		}
+
 		const deps = gulp.src(dependenciesSrc, { base: '.', dot: true })
-			.pipe(filter(['**', `!**/${config.version}/**`, '!**/bin/darwin-arm64-87/**', '!**/package-lock.json', '!**/yarn.lock', '!**/*.{js,css}.map']))
+			.pipe(filter(depFilterPattern))
 			.pipe(util.cleanNodeModules(path.join(import.meta.dirname, '.moduleignore')))
 			.pipe(util.cleanNodeModules(path.join(import.meta.dirname, `.moduleignore.${process.platform}`)))
 			.pipe(jsFilter)
@@ -500,6 +506,9 @@ function packageTask(platform: string, arch: string, sourceFolderName: string, d
 				'resources/win32/code_70x70.png',
 				'resources/win32/code_150x150.png'
 			], { base: '.' }));
+			if (embedded) {
+				all = es.merge(all, gulp.src('resources/win32/sessions.ico', { base: '.' }));
+			}
 		} else if (platform === 'linux') {
 			const policyDest = gulp.src('.build/policies/linux/**', { base: '.build/policies/linux' })
 				.pipe(rename(f => f.dirname = `policies/${f.dirname}`));
@@ -519,10 +528,19 @@ function packageTask(platform: string, arch: string, sourceFolderName: string, d
 			platform,
 			arch: arch === 'armhf' ? 'arm' : arch,
 			ffmpegChromium: false,
+			darwinAssetsCar: 'resources/darwin/code.car',
 			...(embedded ? {
 				darwinMiniAppName: embedded.nameShort,
 				darwinMiniAppBundleIdentifier: embedded.darwinBundleIdentifier,
 				darwinMiniAppIcon: 'resources/darwin/sessions.icns',
+				darwinMiniAppAssetsCar: 'resources/darwin/sessions.car',
+				darwinMiniAppBundleURLTypes: [{
+					role: 'Viewer',
+					name: embedded.nameLong,
+					urlSchemes: [embedded.urlProtocol]
+				}],
+				win32ProxyAppName: embedded.nameShort,
+				win32ProxyIcon: 'resources/win32/sessions.ico',
 			} : {})
 		};
 
@@ -531,7 +549,13 @@ function packageTask(platform: string, arch: string, sourceFolderName: string, d
 			.pipe(util.fixWin32DirectoryPermissions())
 			.pipe(filter(['**', '!**/.github/**'], { dot: true })) // https://github.com/microsoft/vscode/issues/116523
 			.pipe(electron(electronConfig))
-			.pipe(filter(['**', '!LICENSE', '!version'], { dot: true }));
+			.pipe(filter([
+				'**',
+				'!LICENSE',
+				'!version',
+				...(platform === 'darwin' && !isInsiderOrExploration ? ['!**/Contents/Applications', '!**/Contents/Applications/**'] : []),
+				...(platform === 'win32' && !isInsiderOrExploration ? ['!**/electron_proxy.exe'] : []),
+			], { dot: true }));
 
 		if (platform === 'linux') {
 			result = es.merge(result, gulp.src('resources/completions/bash/code', { base: '.' })
@@ -546,7 +570,7 @@ function packageTask(platform: string, arch: string, sourceFolderName: string, d
 		if (platform === 'win32') {
 			result = es.merge(result, gulp.src('resources/win32/bin/code.js', { base: 'resources/win32', allowEmpty: true }));
 
-			if (useVersionedUpdate) {
+			if (versionedResourcesFolder) {
 				result = es.merge(result, gulp.src('resources/win32/versioned/bin/code.cmd', { base: 'resources/win32/versioned' })
 					.pipe(replace('@@NAME@@', product.nameShort))
 					.pipe(replace('@@VERSIONFOLDER@@', versionedResourcesFolder))
@@ -579,6 +603,7 @@ function packageTask(platform: string, arch: string, sourceFolderName: string, d
 			}
 
 			result = es.merge(result, gulp.src('resources/win32/VisualElementsManifest.xml', { base: 'resources/win32' })
+				.pipe(replace('@@VERSIONFOLDER@@', versionedResourcesFolder ? `${versionedResourcesFolder}\\` : ''))
 				.pipe(rename(product.nameShort + '.VisualElementsManifest.xml')));
 
 			result = es.merge(result, gulp.src('.build/policies/win32/**', { base: '.build/policies/win32' })
@@ -623,6 +648,7 @@ function patchWin32DependenciesTask(destinationFolderName: string) {
 	const cwd = path.join(path.dirname(root), destinationFolderName);
 
 	return async () => {
+		const versionedResourcesFolder = util.getVersionedResourcesFolder('win32', commit!);
 		const deps = (await Promise.all([
 			glob('**/*.node', { cwd, ignore: 'extensions/node_modules/@parcel/watcher/**' }),
 			glob('**/rg.exe', { cwd }),
@@ -692,7 +718,13 @@ BUILD_TARGETS.forEach(buildTarget => {
 		if (useEsbuildTranspile) {
 			const esbuildBundleTask = task.define(
 				`esbuild-bundle${dashed(platform)}${dashed(arch)}${dashed(minified)}`,
-				() => runEsbuildBundle(sourceFolderName, !!minified, true, 'desktop', minified ? `${sourceMappingURLBase}/core` : undefined)
+				() => runEsbuildBundle(
+					sourceFolderName,
+					!!minified,
+					true,
+					'desktop',
+					minified && useCdnSourceMapsForPackagingTasks ? `${sourceMappingURLBase}/core` : undefined
+				)
 			);
 			vscodeTask = task.define(`vscode${dashed(platform)}${dashed(arch)}${dashed(minified)}`, task.series(
 				copyCodiconsTask,
diff --git a/build/gulpfile.vscode.web.ts b/build/gulpfile.vscode.web.ts
index e9cc3720fcf7f..3e6b29adfe9fa 100644
--- a/build/gulpfile.vscode.web.ts
+++ b/build/gulpfile.vscode.web.ts
@@ -33,7 +33,7 @@ const quality = (product as { quality?: string }).quality;
 const version = (quality && quality !== 'stable') ? `${packageJson.version}-${quality}` : packageJson.version;
 
 // esbuild-based bundle for standalone web
-function runEsbuildBundle(outDir: string, minify: boolean, nls: boolean): Promise<void> {
+function runEsbuildBundle(outDir: string, minify: boolean, nls: boolean, sourceMapBaseUrl?: string): Promise<void> {
 	return new Promise((resolve, reject) => {
 		const scriptPath = path.join(REPO_ROOT, 'build/next/index.ts');
 		const args = [scriptPath, 'bundle', '--out', outDir, '--target', 'web'];
@@ -44,6 +44,9 @@ function runEsbuildBundle(outDir: string, minify: boolean, nls: boolean): Promis
 		if (nls) {
 			args.push('--nls');
 		}
+		if (sourceMapBaseUrl) {
+			args.push('--source-map-base-url', sourceMapBaseUrl);
+		}
 
 		const proc = cp.spawn(process.execPath, args, {
 			cwd: REPO_ROOT,
@@ -164,8 +167,9 @@ const minifyVSCodeWebTask = task.define('minify-vscode-web-OLD', task.series(
 gulp.task(minifyVSCodeWebTask);
 
 // esbuild-based tasks (new)
+const sourceMappingURLBase = `https://main.vscode-cdn.net/sourcemaps/${commit}`;
 const esbuildBundleVSCodeWebTask = task.define('esbuild-vscode-web', () => runEsbuildBundle('out-vscode-web', false, true));
-const esbuildBundleVSCodeWebMinTask = task.define('esbuild-vscode-web-min', () => runEsbuildBundle('out-vscode-web-min', true, true));
+const esbuildBundleVSCodeWebMinTask = task.define('esbuild-vscode-web-min', () => runEsbuildBundle('out-vscode-web-min', true, true, `${sourceMappingURLBase}/core`));
 
 function packageTask(sourceFolderName: string, destinationFolderName: string) {
 	const destination = path.join(BUILD_ROOT, destinationFolderName);
diff --git a/build/gulpfile.vscode.win32.ts b/build/gulpfile.vscode.win32.ts
index d04e7f1f0e7d3..0f81323c98db2 100644
--- a/build/gulpfile.vscode.win32.ts
+++ b/build/gulpfile.vscode.win32.ts
@@ -14,6 +14,7 @@ import product from '../product.json' with { type: 'json' };
 import { getVersion } from './lib/getVersion.ts';
 import * as task from './lib/task.ts';
 import * as util from './lib/util.ts';
+import type { EmbeddedProductInfo } from './lib/embeddedType.ts';
 
 import { createRequire } from 'module';
 const require = createRequire(import.meta.url);
@@ -112,6 +113,17 @@ function buildWin32Setup(arch: string, target: string): task.CallbackTask {
 			Quality: quality
 		};
 
+		const isInsiderOrExploration = quality === 'insider' || quality === 'exploration';
+		const embedded = isInsiderOrExploration
+			? (product as typeof product & { embedded?: EmbeddedProductInfo }).embedded
+			: undefined;
+
+		if (embedded) {
+			definitions['ProxyExeBasename'] = embedded.nameShort;
+			definitions['ProxyAppUserId'] = embedded.win32AppUserModelId;
+			definitions['ProxyNameLong'] = embedded.nameLong;
+		}
+
 		if (quality === 'stable' || quality === 'insider') {
 			definitions['AppxPackage'] = `${quality === 'stable' ? 'code' : 'code_insider'}_${arch}.appx`;
 			definitions['AppxPackageDll'] = `${quality === 'stable' ? 'code' : 'code_insider'}_explorer_command_${arch}.dll`;
diff --git a/build/lib/date.ts b/build/lib/date.ts
index 68d52521349ed..99ba91a5282df 100644
--- a/build/lib/date.ts
+++ b/build/lib/date.ts
@@ -5,9 +5,23 @@
 
 import path from 'path';
 import fs from 'fs';
+import { execSync } from 'child_process';
 
 const root = path.join(import.meta.dirname, '..', '..');
 
+/**
+ * Get the ISO date for the build. Uses the git commit date of HEAD
+ * so that independent builds on different machines produce the same
+ * timestamp (required for deterministic builds, e.g. macOS Universal).
+ */
+export function getGitCommitDate(): string {
+	try {
+		return execSync('git log -1 --format=%cI HEAD', { cwd: root, encoding: 'utf8' }).trim();
+	} catch {
+		return new Date().toISOString();
+	}
+}
+
 /**
  * Writes a `outDir/date` file with the contents of the build
  * so that other tasks during the build process can use it and
@@ -18,7 +32,7 @@ export function writeISODate(outDir: string) {
 		const outDirectory = path.join(root, outDir);
 		fs.mkdirSync(outDirectory, { recursive: true });
 
-		const date = new Date().toISOString();
+		const date = getGitCommitDate();
 		fs.writeFileSync(path.join(outDirectory, 'date'), date, 'utf8');
 
 		resolve();
diff --git a/build/lib/embeddedType.ts b/build/lib/embeddedType.ts
new file mode 100644
index 0000000000000..4b3075f4a7165
--- /dev/null
+++ b/build/lib/embeddedType.ts
@@ -0,0 +1,18 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+export type EmbeddedProductInfo = {
+	nameShort: string;
+	nameLong: string;
+	applicationName: string;
+	dataFolderName: string;
+	darwinBundleIdentifier: string;
+	urlProtocol: string;
+	win32AppUserModelId: string;
+	win32MutexName: string;
+	win32RegValueName: string;
+	win32NameVersion: string;
+	win32VersionedUpdate: boolean;
+};
diff --git a/build/lib/extensions.ts b/build/lib/extensions.ts
index 5710f4d6919fd..aacf25cbbc131 100644
--- a/build/lib/extensions.ts
+++ b/build/lib/extensions.ts
@@ -20,10 +20,8 @@ import fancyLog from 'fancy-log';
 import ansiColors from 'ansi-colors';
 import buffer from 'gulp-buffer';
 import * as jsoncParser from 'jsonc-parser';
-import webpack from 'webpack';
 import { getProductionDependencies } from './dependencies.ts';
 import { type IExtensionDefinition, getExtensionStream } from './builtInExtensions.ts';
-import { getVersion } from './getVersion.ts';
 import { fetchUrls, fetchGithub } from './fetch.ts';
 import { createTsgoStream, spawnTsgo } from './tsgo.ts';
 import vzip from 'gulp-vinyl-zip';
@@ -32,8 +30,8 @@ import { createRequire } from 'module';
 const require = createRequire(import.meta.url);
 
 const root = path.dirname(path.dirname(import.meta.dirname));
-const commit = getVersion(root);
-const sourceMappingURLBase = `https://main.vscode-cdn.net/sourcemaps/${commit}`;
+// const commit = getVersion(root);
+// const sourceMappingURLBase = `https://main.vscode-cdn.net/sourcemaps/${commit}`;
 
 function minifyExtensionResources(input: Stream): Stream {
 	const jsonFilter = filter(['**/*.json', '**/*.code-snippets'], { restore: true });
@@ -65,32 +63,24 @@ function updateExtensionPackageJSON(input: Stream, update: (data: any) => any):
 		.pipe(packageJsonFilter.restore);
 }
 
-function fromLocal(extensionPath: string, forWeb: boolean, disableMangle: boolean): Stream {
+function fromLocal(extensionPath: string, forWeb: boolean, _disableMangle: boolean): Stream {
 
 	const esbuildConfigFileName = forWeb
 		? 'esbuild.browser.mts'
 		: 'esbuild.mts';
 
-	const webpackConfigFileName = forWeb
-		? `extension-browser.webpack.config.js`
-		: `extension.webpack.config.js`;
-
 	const hasEsbuild = fs.existsSync(path.join(extensionPath, esbuildConfigFileName));
-	const hasWebpack = fs.existsSync(path.join(extensionPath, webpackConfigFileName));
 
 	let input: Stream;
 	let isBundled = false;
 
 	if (hasEsbuild) {
-		// Unlike webpack, esbuild only does bundling so we still want to run a separate type check step
+		// Esbuild only does bundling so we still want to run a separate type check step
 		input = es.merge(
 			fromLocalEsbuild(extensionPath, esbuildConfigFileName),
 			...getBuildRootsForExtension(extensionPath).map(root => typeCheckExtensionStream(root, forWeb)),
 		);
 		isBundled = true;
-	} else if (hasWebpack) {
-		input = fromLocalWebpack(extensionPath, webpackConfigFileName, disableMangle);
-		isBundled = true;
 	} else {
 		input = fromLocalNormal(extensionPath);
 	}
@@ -122,132 +112,6 @@ export function typeCheckExtensionStream(extensionPath: string, forWeb: boolean)
 	return createTsgoStream(tsconfigPath, { taskName: 'typechecking extension (tsgo)', noEmit: true });
 }
 
-function fromLocalWebpack(extensionPath: string, webpackConfigFileName: string, disableMangle: boolean): Stream {
-	const vsce = require('@vscode/vsce') as typeof import('@vscode/vsce');
-	const webpack = require('webpack');
-	const webpackGulp = require('webpack-stream');
-	const result = es.through();
-
-	const packagedDependencies: string[] = [];
-	const stripOutSourceMaps: string[] = [];
-	const packageJsonConfig = require(path.join(extensionPath, 'package.json'));
-	if (packageJsonConfig.dependencies) {
-		const webpackConfig = require(path.join(extensionPath, webpackConfigFileName));
-		const webpackRootConfig = webpackConfig.default;
-		for (const key in webpackRootConfig.externals) {
-			if (key in packageJsonConfig.dependencies) {
-				packagedDependencies.push(key);
-			}
-		}
-
-		if (webpackConfig.StripOutSourceMaps) {
-			for (const filePath of webpackConfig.StripOutSourceMaps) {
-				stripOutSourceMaps.push(filePath);
-			}
-		}
-	}
-
-	// TODO: add prune support based on packagedDependencies to vsce.PackageManager.Npm similar
-	// to vsce.PackageManager.Yarn.
-	// A static analysis showed there are no webpack externals that are dependencies of the current
-	// local extensions so we can use the vsce.PackageManager.None config to ignore dependencies list
-	// as a temporary workaround.
-	vsce.listFiles({ cwd: extensionPath, packageManager: vsce.PackageManager.None, packagedDependencies }).then(fileNames => {
-		const files = fileNames
-			.map(fileName => path.join(extensionPath, fileName))
-			.map(filePath => new File({
-				path: filePath,
-				stat: fs.statSync(filePath),
-				base: extensionPath,
-				contents: fs.createReadStream(filePath)
-			}));
-
-		// check for a webpack configuration files, then invoke webpack
-		// and merge its output with the files stream.
-		const webpackConfigLocations = (glob.sync(
-			path.join(extensionPath, '**', webpackConfigFileName),
-			{ ignore: ['**/node_modules'] }
-		) as string[]);
-		const webpackStreams = webpackConfigLocations.flatMap(webpackConfigPath => {
-
-			const webpackDone = (err: Error | undefined, stats: any) => {
-				fancyLog(`Bundled extension: ${ansiColors.yellow(path.join(path.basename(extensionPath), path.relative(extensionPath, webpackConfigPath)))}...`);
-				if (err) {
-					result.emit('error', err);
-				}
-				const { compilation } = stats;
-				if (compilation.errors.length > 0) {
-					result.emit('error', compilation.errors.join('\n'));
-				}
-				if (compilation.warnings.length > 0) {
-					result.emit('error', compilation.warnings.join('\n'));
-				}
-			};
-
-			const exportedConfig = require(webpackConfigPath).default;
-			return (Array.isArray(exportedConfig) ? exportedConfig : [exportedConfig]).map(config => {
-				const webpackConfig = {
-					...config,
-					...{ mode: 'production' }
-				};
-				if (disableMangle) {
-					if (Array.isArray(config.module.rules)) {
-						for (const rule of config.module.rules) {
-							if (Array.isArray(rule.use)) {
-								for (const use of rule.use) {
-									if (String(use.loader).endsWith('mangle-loader.js')) {
-										use.options.disabled = true;
-									}
-								}
-							}
-						}
-					}
-				}
-				const relativeOutputPath = path.relative(extensionPath, webpackConfig.output.path);
-
-				return webpackGulp(webpackConfig, webpack, webpackDone)
-					.pipe(es.through(function (data) {
-						data.stat = data.stat || {};
-						data.base = extensionPath;
-						this.emit('data', data);
-					}))
-					.pipe(es.through(function (data: File) {
-						// source map handling:
-						// * rewrite sourceMappingURL
-						// * save to disk so that upload-task picks this up
-						if (path.extname(data.basename) === '.js') {
-							if (stripOutSourceMaps.indexOf(data.relative) >= 0) { // remove source map
-								const contents = (data.contents as Buffer).toString('utf8');
-								data.contents = Buffer.from(contents.replace(/\n\/\/# sourceMappingURL=(.*)$/gm, ''), 'utf8');
-							} else {
-								const contents = (data.contents as Buffer).toString('utf8');
-								data.contents = Buffer.from(contents.replace(/\n\/\/# sourceMappingURL=(.*)$/gm, function (_m, g1) {
-									return `\n//# sourceMappingURL=${sourceMappingURLBase}/extensions/${path.basename(extensionPath)}/${relativeOutputPath}/${g1}`;
-								}), 'utf8');
-							}
-						}
-
-						this.emit('data', data);
-					}));
-			});
-		});
-
-		es.merge(...webpackStreams, es.readArray(files))
-			// .pipe(es.through(function (data) {
-			// 	// debug
-			// 	console.log('out', data.path, data.contents.length);
-			// 	this.emit('data', data);
-			// }))
-			.pipe(result);
-
-	}).catch(err => {
-		console.error(extensionPath);
-		console.error(packagedDependencies);
-		result.emit('error', err);
-	});
-
-	return result.pipe(createStatsStream(path.basename(extensionPath)));
-}
 
 function fromLocalNormal(extensionPath: string): Stream {
 	const vsce = require('@vscode/vsce') as typeof import('@vscode/vsce');
@@ -649,70 +513,6 @@ export function translatePackageJSON(packageJSON: string, packageNLSPath: string
 
 const extensionsPath = path.join(root, 'extensions');
 
-export async function webpackExtensions(taskName: string, isWatch: boolean, webpackConfigLocations: { configPath: string; outputRoot?: string }[]) {
-	const webpack = require('webpack') as typeof import('webpack');
-
-	const webpackConfigs: webpack.Configuration[] = [];
-
-	for (const { configPath, outputRoot } of webpackConfigLocations) {
-		const configOrFnOrArray = require(configPath).default;
-		function addConfig(configOrFnOrArray: webpack.Configuration | ((env: unknown, args: unknown) => webpack.Configuration) | webpack.Configuration[]) {
-			for (const configOrFn of Array.isArray(configOrFnOrArray) ? configOrFnOrArray : [configOrFnOrArray]) {
-				const config = typeof configOrFn === 'function' ? configOrFn({}, {}) : configOrFn;
-				if (outputRoot) {
-					config.output!.path = path.join(outputRoot, path.relative(path.dirname(configPath), config.output!.path!));
-				}
-				webpackConfigs.push(config);
-			}
-		}
-		addConfig(configOrFnOrArray);
-	}
-
-	function reporter(fullStats: any) {
-		if (Array.isArray(fullStats.children)) {
-			for (const stats of fullStats.children) {
-				const outputPath = stats.outputPath;
-				if (outputPath) {
-					const relativePath = path.relative(extensionsPath, outputPath).replace(/\\/g, '/');
-					const match = relativePath.match(/[^\/]+(\/server|\/client)?/);
-					fancyLog(`Finished ${ansiColors.green(taskName)} ${ansiColors.cyan(match![0])} with ${stats.errors.length} errors.`);
-				}
-				if (Array.isArray(stats.errors)) {
-					stats.errors.forEach((error: any) => {
-						fancyLog.error(error);
-					});
-				}
-				if (Array.isArray(stats.warnings)) {
-					stats.warnings.forEach((warning: any) => {
-						fancyLog.warn(warning);
-					});
-				}
-			}
-		}
-	}
-	return new Promise<void>((resolve, reject) => {
-		if (isWatch) {
-			webpack(webpackConfigs).watch({}, (err, stats) => {
-				if (err) {
-					reject();
-				} else {
-					reporter(stats?.toJson());
-				}
-			});
-		} else {
-			webpack(webpackConfigs).run((err, stats) => {
-				if (err) {
-					fancyLog.error(err);
-					reject();
-				} else {
-					reporter(stats?.toJson());
-					resolve();
-				}
-			});
-		}
-	});
-}
-
 export async function esbuildExtensions(taskName: string, isWatch: boolean, scripts: { script: string; outputRoot?: string }[]): Promise<void> {
 	function reporter(stdError: string, script: string) {
 		const matches = (stdError || '').match(/\> (.+): error: (.+)?/g);
diff --git a/build/lib/i18n.resources.json b/build/lib/i18n.resources.json
index 921137824ee3c..26e1e27302743 100644
--- a/build/lib/i18n.resources.json
+++ b/build/lib/i18n.resources.json
@@ -170,6 +170,10 @@
 			"name": "vs/workbench/contrib/inlineChat",
 			"project": "vscode-workbench"
 		},
+		{
+			"name": "vs/workbench/contrib/imageCarousel",
+			"project": "vscode-workbench"
+		},
 		{
 			"name": "vs/workbench/contrib/chat",
 			"project": "vscode-workbench"
@@ -561,6 +565,120 @@
 		{
 			"name": "vs/workbench/contrib/list",
 			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/contrib/browserView",
+			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/contrib/dropOrPasteInto",
+			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/contrib/editTelemetry",
+			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/contrib/inlineCompletions",
+			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/contrib/mcp",
+			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/contrib/meteredConnection",
+			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/contrib/processExplorer",
+			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/contrib/remoteCodingAgents",
+			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/contrib/telemetry",
+			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/contrib/welcomeAgentSessions",
+			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/services/accounts",
+			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/services/chat",
+			"project": "vscode-workbench"
+		},
+		{
+			"name": "vs/workbench/services/request",
+			"project": "vscode-workbench"
+		}
+	],
+	"sessions": [
+		{
+			"name": "vs/sessions",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/accountMenu",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/agentFeedback",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/aiCustomizationTreeView",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/applyCommitsToParentRepo",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/changes",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/chat",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/codeReview",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/fileTreeView",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/files",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/git",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/logs",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/sessions",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/terminal",
+			"project": "vscode-sessions"
+		},
+		{
+			"name": "vs/sessions/contrib/welcome",
+			"project": "vscode-sessions"
 		}
 	]
 }
diff --git a/build/lib/i18n.ts b/build/lib/i18n.ts
index 8ebcb1f177b06..61ed524f35bf8 100644
--- a/build/lib/i18n.ts
+++ b/build/lib/i18n.ts
@@ -391,7 +391,8 @@ const editorProject: string = 'vscode-editor',
 	workbenchProject: string = 'vscode-workbench',
 	extensionsProject: string = 'vscode-extensions',
 	setupProject: string = 'vscode-setup',
-	serverProject: string = 'vscode-server';
+	serverProject: string = 'vscode-server',
+	sessionsProject: string = 'vscode-sessions';
 
 export function getResource(sourceFile: string): Resource {
 	let resource: string;
@@ -416,6 +417,11 @@ export function getResource(sourceFile: string): Resource {
 		return { name: resource, project: workbenchProject };
 	} else if (/^vs\/workbench/.test(sourceFile)) {
 		return { name: 'vs/workbench', project: workbenchProject };
+	} else if (/^vs\/sessions\/contrib/.test(sourceFile)) {
+		resource = sourceFile.split('/', 4).join('/');
+		return { name: resource, project: sessionsProject };
+	} else if (/^vs\/sessions/.test(sourceFile)) {
+		return { name: 'vs/sessions', project: sessionsProject };
 	}
 
 	throw new Error(`Could not identify the XLF bundle for ${sourceFile}`);
@@ -737,6 +743,10 @@ export function prepareI18nPackFiles(resultingTranslationPaths: TranslationPath[
 		if (EXTERNAL_EXTENSIONS.find(e => e === resource)) {
 			project = extensionsProject;
 		}
+		// vscode-setup has its own import path via prepareIslFiles
+		if (project === setupProject) {
+			return;
+		}
 		const contents = xlf.contents!.toString();
 		log(`Found ${project}: ${resource}`);
 		const parsePromise = getL10nFilesFromXlf(contents);
diff --git a/build/lib/policies/policyData.jsonc b/build/lib/policies/policyData.jsonc
index 9c1e1e0e87a8f..f58dda70afad4 100644
--- a/build/lib/policies/policyData.jsonc
+++ b/build/lib/policies/policyData.jsonc
@@ -39,28 +39,28 @@
     ],
     "policies": [
         {
-            "key": "chat.mcp.gallery.serviceUrl",
-            "name": "McpGalleryServiceUrl",
-            "category": "InteractiveSession",
-            "minimumVersion": "1.101",
+            "key": "extensions.gallery.serviceUrl",
+            "name": "ExtensionGalleryServiceUrl",
+            "category": "Extensions",
+            "minimumVersion": "1.99",
             "localization": {
                 "description": {
-                    "key": "mcp.gallery.serviceUrl",
-                    "value": "Configure the MCP Gallery service URL to connect to"
+                    "key": "extensions.gallery.serviceUrl",
+                    "value": "Configure the Marketplace service URL to connect to"
                 }
             },
             "type": "string",
             "default": ""
         },
         {
-            "key": "extensions.gallery.serviceUrl",
-            "name": "ExtensionGalleryServiceUrl",
-            "category": "Extensions",
-            "minimumVersion": "1.99",
+            "key": "chat.mcp.gallery.serviceUrl",
+            "name": "McpGalleryServiceUrl",
+            "category": "InteractiveSession",
+            "minimumVersion": "1.101",
             "localization": {
                 "description": {
-                    "key": "extensions.gallery.serviceUrl",
-                    "value": "Configure the Marketplace service URL to connect to"
+                    "key": "mcp.gallery.serviceUrl",
+                    "value": "Configure the MCP Gallery service URL to connect to"
                 }
             },
             "type": "string",
@@ -169,6 +169,20 @@
             "type": "boolean",
             "default": true
         },
+        {
+            "key": "chat.editMode.hidden",
+            "name": "DeprecatedEditModeHidden",
+            "category": "InteractiveSession",
+            "minimumVersion": "1.112",
+            "localization": {
+                "description": {
+                    "key": "chat.editMode.hidden",
+                    "value": "When enabled, hides the Edit mode from the chat mode picker."
+                }
+            },
+            "type": "boolean",
+            "default": true
+        },
         {
             "key": "chat.useHooks",
             "name": "ChatHooks",
@@ -286,6 +300,20 @@
             },
             "type": "boolean",
             "default": true
+        },
+        {
+            "key": "workbench.browser.enableChatTools",
+            "name": "BrowserChatTools",
+            "category": "InteractiveSession",
+            "minimumVersion": "1.110",
+            "localization": {
+                "description": {
+                    "key": "browser.enableChatTools",
+                    "value": "When enabled, chat agents can use browser tools to open and interact with pages in the Integrated Browser."
+                }
+            },
+            "type": "boolean",
+            "default": false
         }
     ]
 }
diff --git a/build/lib/stylelint/vscode-known-variables.json b/build/lib/stylelint/vscode-known-variables.json
index a913a9534fcfc..5b0fc9b6ad5b4 100644
--- a/build/lib/stylelint/vscode-known-variables.json
+++ b/build/lib/stylelint/vscode-known-variables.json
@@ -21,6 +21,7 @@
 		"--vscode-activityErrorBadge-foreground",
 		"--vscode-activityWarningBadge-background",
 		"--vscode-activityWarningBadge-foreground",
+		"--vscode-agentFeedbackInputWidget-border",
 		"--vscode-agentSessionReadIndicator-foreground",
 		"--vscode-agentSessionSelectedBadge-border",
 		"--vscode-agentSessionSelectedUnfocusedBadge-border",
@@ -35,6 +36,7 @@
 		"--vscode-breadcrumb-focusForeground",
 		"--vscode-breadcrumb-foreground",
 		"--vscode-breadcrumbPicker-background",
+		"--vscode-browser-border",
 		"--vscode-button-background",
 		"--vscode-button-border",
 		"--vscode-button-foreground",
@@ -644,6 +646,8 @@
 		"--vscode-searchEditor-findMatchBorder",
 		"--vscode-searchEditor-textInputBorder",
 		"--vscode-selection-background",
+		"--vscode-sessionsUpdateButton-downloadedBackground",
+		"--vscode-sessionsUpdateButton-downloadingBackground",
 		"--vscode-settings-checkboxBackground",
 		"--vscode-settings-checkboxBorder",
 		"--vscode-settings-checkboxForeground",
@@ -945,6 +949,7 @@
 		"--testMessageDecorationFontSize",
 		"--title-border-bottom-color",
 		"--title-wco-width",
+		"--update-progress",
 		"--reveal-button-size",
 		"--part-background",
 		"--part-border-color",
@@ -968,6 +973,14 @@
 		"--vscode-repl-line-height",
 		"--vscode-sash-hover-size",
 		"--vscode-sash-size",
+		"--vscode-shadow-active-tab",
+		"--vscode-shadow-depth-x",
+		"--vscode-shadow-depth-y",
+		"--vscode-shadow-hover",
+		"--vscode-shadow-lg",
+		"--vscode-shadow-md",
+		"--vscode-shadow-sm",
+		"--vscode-shadow-xl",
 		"--vscode-testing-coverage-lineHeight",
 		"--vscode-editorStickyScroll-scrollableWidth",
 		"--vscode-editorStickyScroll-foldingOpacityTransition",
@@ -998,6 +1011,7 @@
 		"--text-link-decoration",
 		"--vscode-action-item-auto-timeout",
 		"--monaco-editor-warning-decoration",
+		"--animation-angle",
 		"--animation-opacity",
 		"--chat-setup-dialog-glow-angle",
 		"--vscode-chat-font-family",
diff --git a/build/lib/test/i18n.test.ts b/build/lib/test/i18n.test.ts
index 7d5bb0433feed..6c9409bcb4a34 100644
--- a/build/lib/test/i18n.test.ts
+++ b/build/lib/test/i18n.test.ts
@@ -31,7 +31,8 @@ suite('XLF Parser Tests', () => {
 
 	test('JSON file source path to Transifex resource match', () => {
 		const editorProject: string = 'vscode-editor',
-			workbenchProject: string = 'vscode-workbench';
+			workbenchProject: string = 'vscode-workbench',
+			sessionsProject: string = 'vscode-sessions';
 
 		const platform: i18n.Resource = { name: 'vs/platform', project: editorProject },
 			editorContrib = { name: 'vs/editor/contrib', project: editorProject },
@@ -40,7 +41,9 @@ suite('XLF Parser Tests', () => {
 			code = { name: 'vs/code', project: workbenchProject },
 			workbenchParts = { name: 'vs/workbench/contrib/html', project: workbenchProject },
 			workbenchServices = { name: 'vs/workbench/services/textfile', project: workbenchProject },
-			workbench = { name: 'vs/workbench', project: workbenchProject };
+			workbench = { name: 'vs/workbench', project: workbenchProject },
+			sessionsContrib = { name: 'vs/sessions/contrib/chat', project: sessionsProject },
+			sessions = { name: 'vs/sessions', project: sessionsProject };
 
 		assert.deepStrictEqual(i18n.getResource('vs/platform/actions/browser/menusExtensionPoint'), platform);
 		assert.deepStrictEqual(i18n.getResource('vs/editor/contrib/clipboard/browser/clipboard'), editorContrib);
@@ -50,5 +53,7 @@ suite('XLF Parser Tests', () => {
 		assert.deepStrictEqual(i18n.getResource('vs/workbench/contrib/html/browser/webview'), workbenchParts);
 		assert.deepStrictEqual(i18n.getResource('vs/workbench/services/textfile/node/testFileService'), workbenchServices);
 		assert.deepStrictEqual(i18n.getResource('vs/workbench/browser/parts/panel/panelActions'), workbench);
+		assert.deepStrictEqual(i18n.getResource('vs/sessions/contrib/chat/browser/chatWidget'), sessionsContrib);
+		assert.deepStrictEqual(i18n.getResource('vs/sessions/browser/layoutActions'), sessions);
 	});
 });
diff --git a/build/lib/util.ts b/build/lib/util.ts
index e4d01e143c93b..4203e6e653041 100644
--- a/build/lib/util.ts
+++ b/build/lib/util.ts
@@ -381,6 +381,12 @@ export function getElectronVersion(): Record<string, string> {
 	return { electronVersion, msBuildId };
 }
 
+export function getVersionedResourcesFolder(platform: string, commit: string): string {
+	const productJson = JSON.parse(fs.readFileSync(path.join(root, 'product.json'), 'utf8'));
+	const useVersionedUpdate = platform === 'win32' && productJson.win32VersionedUpdate;
+	return useVersionedUpdate ? commit.substring(0, 10) : '';
+}
+
 export class VinylStat implements fs.Stats {
 
 	readonly dev: number;
diff --git a/build/next/index.ts b/build/next/index.ts
index b0120837efa26..a5bb0796da00d 100644
--- a/build/next/index.ts
+++ b/build/next/index.ts
@@ -7,11 +7,13 @@ import * as esbuild from 'esbuild';
 import * as fs from 'fs';
 import * as path from 'path';
 import { promisify } from 'util';
+
 import glob from 'glob';
 import gulpWatch from '../lib/watch/index.ts';
 import { nlsPlugin, createNLSCollector, finalizeNLS, postProcessNLS } from './nls-plugin.ts';
 import { convertPrivateFields, adjustSourceMap, type ConvertPrivateFieldsResult } from './private-to-property.ts';
 import { getVersion } from '../lib/getVersion.ts';
+import { getGitCommitDate } from '../lib/date.ts';
 import product from '../../product.json' with { type: 'json' };
 import packageJson from '../../package.json' with { type: 'json' };
 import { useEsbuildTranspile } from '../buildConfig.ts';
@@ -72,7 +74,8 @@ const extensionHostEntryPoints = [
 ];
 
 function isExtensionHostBundle(filePath: string): boolean {
-	return extensionHostEntryPoints.some(ep => filePath.endsWith(`${ep}.js`));
+	const normalized = filePath.replaceAll('\\', '/');
+	return extensionHostEntryPoints.some(ep => normalized.endsWith(`${ep}.js`));
 }
 
 // Workers - shared between targets
@@ -257,6 +260,12 @@ const desktopResourcePatterns = [
 	'vs/workbench/contrib/terminal/common/scripts/*.psm1',
 	'vs/workbench/contrib/terminal/common/scripts/*.fish',
 	'vs/workbench/contrib/terminal/common/scripts/*.zsh',
+	'vs/workbench/contrib/terminal/common/scripts/psreadline/*.psd1',
+	'vs/workbench/contrib/terminal/common/scripts/psreadline/*.psm1',
+	'vs/workbench/contrib/terminal/common/scripts/psreadline/*.dll',
+	'vs/workbench/contrib/terminal/common/scripts/psreadline/*.ps1xml',
+	'vs/workbench/contrib/terminal/common/scripts/psreadline/net6plus/*.dll',
+	'vs/workbench/contrib/terminal/common/scripts/psreadline/netstd/*.dll',
 	'vs/workbench/contrib/externalTerminal/**/*.scpt',
 
 	// Media - audio
@@ -270,6 +279,9 @@ const desktopResourcePatterns = [
 	'vs/workbench/services/extensionManagement/common/media/*.png',
 	'vs/workbench/browser/parts/editor/media/*.png',
 	'vs/workbench/contrib/debug/browser/media/*.png',
+
+	// Sessions - built-in prompts
+	'vs/sessions/prompts/*.prompt.md',
 ];
 
 // Resources for server target (minimal - no UI)
@@ -291,6 +303,12 @@ const serverResourcePatterns = [
 	'vs/workbench/contrib/terminal/common/scripts/shellIntegration-rc.zsh',
 	'vs/workbench/contrib/terminal/common/scripts/shellIntegration-login.zsh',
 	'vs/workbench/contrib/terminal/common/scripts/shellIntegration.fish',
+	'vs/workbench/contrib/terminal/common/scripts/psreadline/*.psd1',
+	'vs/workbench/contrib/terminal/common/scripts/psreadline/*.psm1',
+	'vs/workbench/contrib/terminal/common/scripts/psreadline/*.dll',
+	'vs/workbench/contrib/terminal/common/scripts/psreadline/*.ps1xml',
+	'vs/workbench/contrib/terminal/common/scripts/psreadline/net6plus/*.dll',
+	'vs/workbench/contrib/terminal/common/scripts/psreadline/netstd/*.dll',
 ];
 
 // Resources for server-web target (server + web UI)
@@ -419,13 +437,13 @@ function scanBuiltinExtensions(extensionsRoot: string): Array<IScannedBuiltinExt
 }
 
 /**
- * Get the date from the out directory date file, or return current date.
+ * Get the date from the out directory date file, or return the git commit date.
  */
 function readISODate(outDir: string): string {
 	try {
 		return fs.readFileSync(path.join(REPO_ROOT, outDir, 'date'), 'utf8');
 	} catch {
-		return new Date().toISOString();
+		return getGitCommitDate();
 	}
 }
 
@@ -723,10 +741,19 @@ async function transpile(outDir: string, excludeTests: boolean): Promise<void> {
 async function bundle(outDir: string, doMinify: boolean, doNls: boolean, doManglePrivates: boolean, target: BuildTarget, sourceMapBaseUrl?: string): Promise<void> {
 	await cleanDir(outDir);
 
-	// Write build date file (used by packaging to embed in product.json)
+	// Write build date file (used by packaging to embed in product.json).
+	// Reuse the date from out-build/date if it exists (written by the gulp
+	// writeISODate task) so that all parallel bundle outputs share the same
+	// timestamp - this is required for deterministic builds (e.g. macOS Universal).
 	const outDirPath = path.join(REPO_ROOT, outDir);
 	await fs.promises.mkdir(outDirPath, { recursive: true });
-	await fs.promises.writeFile(path.join(outDirPath, 'date'), new Date().toISOString(), 'utf8');
+	let buildDate: string;
+	try {
+		buildDate = await fs.promises.readFile(path.join(REPO_ROOT, 'out-build', 'date'), 'utf8');
+	} catch {
+		buildDate = getGitCommitDate();
+	}
+	await fs.promises.writeFile(path.join(outDirPath, 'date'), buildDate, 'utf8');
 
 	console.log(`[bundle] ${SRC_DIR} → ${outDir} (target: ${target})${doMinify ? ' (minify)' : ''}${doNls ? ' (nls)' : ''}${doManglePrivates ? ' (mangle-privates)' : ''}`);
 	const t1 = Date.now();
@@ -885,6 +912,13 @@ ${tslib}`,
 	const mangleStats: { file: string; result: ConvertPrivateFieldsResult }[] = [];
 	// Map from JS file path to pre-mangle content + edits, for source map adjustment
 	const mangleEdits = new Map<string, { preMangleCode: string; edits: readonly import('./private-to-property.ts').TextEdit[] }>();
+	// Map from JS file path to pre-NLS content + edits, for source map adjustment
+	const nlsEdits = new Map<string, { preNLSCode: string; edits: readonly import('./private-to-property.ts').TextEdit[] }>();
+	// Defer .map files until all .js files are processed, because esbuild may
+	// emit the .map file in a different build result than the .js file (e.g.
+	// code-split chunks), and we need the NLS/mangle edits from the .js pass
+	// to be available when adjusting the .map.
+	const deferredMaps: { path: string; text: string; contents: Uint8Array }[] = [];
 	for (const { result } of buildResults) {
 		if (!result.outputFiles) {
 			continue;
@@ -913,7 +947,12 @@ ${tslib}`,
 
 				// Apply NLS post-processing if enabled (JS only)
 				if (file.path.endsWith('.js') && doNls && indexMap.size > 0) {
-					content = postProcessNLS(content, indexMap, preserveEnglish);
+					const preNLSCode = content;
+					const nlsResult = postProcessNLS(content, indexMap, preserveEnglish);
+					content = nlsResult.code;
+					if (nlsResult.edits.length > 0) {
+						nlsEdits.set(file.path, { preNLSCode, edits: nlsResult.edits });
+					}
 				}
 
 				// Rewrite sourceMappingURL to CDN URL if configured
@@ -931,16 +970,8 @@ ${tslib}`,
 
 				await fs.promises.writeFile(file.path, content);
 			} else if (file.path.endsWith('.map')) {
-				// Source maps may need adjustment if private fields were mangled
-				const jsPath = file.path.replace(/\.map$/, '');
-				const editInfo = mangleEdits.get(jsPath);
-				if (editInfo) {
-					const mapJson = JSON.parse(file.text);
-					const adjusted = adjustSourceMap(mapJson, editInfo.preMangleCode, editInfo.edits);
-					await fs.promises.writeFile(file.path, JSON.stringify(adjusted));
-				} else {
-					await fs.promises.writeFile(file.path, file.contents);
-				}
+				// Defer .map processing until all .js files have been handled
+				deferredMaps.push({ path: file.path, text: file.text, contents: file.contents });
 			} else {
 				// Write other files (assets, etc.) as-is
 				await fs.promises.writeFile(file.path, file.contents);
@@ -949,6 +980,27 @@ ${tslib}`,
 		bundled++;
 	}
 
+	// Second pass: process deferred .map files now that all mangle/NLS edits
+	// have been collected from .js processing above.
+	for (const mapFile of deferredMaps) {
+		const jsPath = mapFile.path.replace(/\.map$/, '');
+		const mangle = mangleEdits.get(jsPath);
+		const nls = nlsEdits.get(jsPath);
+
+		if (mangle || nls) {
+			let mapJson = JSON.parse(mapFile.text);
+			if (mangle) {
+				mapJson = adjustSourceMap(mapJson, mangle.preMangleCode, mangle.edits);
+			}
+			if (nls) {
+				mapJson = adjustSourceMap(mapJson, nls.preNLSCode, nls.edits);
+			}
+			await fs.promises.writeFile(mapFile.path, JSON.stringify(mapJson));
+		} else {
+			await fs.promises.writeFile(mapFile.path, mapFile.contents);
+		}
+	}
+
 	// Log mangle-privates stats
 	if (doManglePrivates && mangleStats.length > 0) {
 		let totalClasses = 0, totalFields = 0, totalEdits = 0, totalElapsed = 0;
@@ -1128,7 +1180,7 @@ async function main(): Promise<void> {
 					// Write build date file (used by packaging to embed in product.json)
 					const outDirPath = path.join(REPO_ROOT, outDir);
 					await fs.promises.mkdir(outDirPath, { recursive: true });
-					await fs.promises.writeFile(path.join(outDirPath, 'date'), new Date().toISOString(), 'utf8');
+					await fs.promises.writeFile(path.join(outDirPath, 'date'), getGitCommitDate(), 'utf8');
 
 					console.log(`[transpile] ${SRC_DIR} → ${outDir}${options.excludeTests ? ' (excluding tests)' : ''}`);
 					const t1 = Date.now();
diff --git a/build/next/nls-plugin.ts b/build/next/nls-plugin.ts
index 7be3faccf2439..e2b19f7d7f13d 100644
--- a/build/next/nls-plugin.ts
+++ b/build/next/nls-plugin.ts
@@ -12,6 +12,7 @@ import {
 	analyzeLocalizeCalls,
 	parseLocalizeKeyOrValue
 } from '../lib/nls-analysis.ts';
+import type { TextEdit } from './private-to-property.ts';
 
 // ============================================================================
 // Types
@@ -148,12 +149,13 @@ export async function finalizeNLS(
 
 /**
  * Post-processes a JavaScript file to replace NLS placeholders with indices.
+ * Returns the transformed code and the edits applied (for source map adjustment).
  */
 export function postProcessNLS(
 	content: string,
 	indexMap: Map<string, number>,
 	preserveEnglish: boolean
-): string {
+): { code: string; edits: readonly TextEdit[] } {
 	return replaceInOutput(content, indexMap, preserveEnglish);
 }
 
@@ -244,7 +246,7 @@ function generateNLSSourceMap(
 	const generator = new SourceMapGenerator();
 	generator.setSourceContent(filePath, originalSource);
 
-	const lineCount = originalSource.split('\n').length;
+	const lines = originalSource.split('\n');
 
 	// Group edits by line
 	const editsByLine = new Map<number, NLSEdit[]>();
@@ -257,7 +259,7 @@ function generateNLSSourceMap(
 		arr.push(edit);
 	}
 
-	for (let line = 0; line < lineCount; line++) {
+	for (let line = 0; line < lines.length; line++) {
 		const smLine = line + 1; // source maps use 1-based lines
 
 		// Always map start of line
@@ -273,7 +275,8 @@ function generateNLSSourceMap(
 
 			let cumulativeShift = 0;
 
-			for (const edit of lineEdits) {
+			for (let i = 0; i < lineEdits.length; i++) {
+				const edit = lineEdits[i];
 				const origLen = edit.endCol - edit.startCol;
 
 				// Map start of edit: the replacement begins at the same original position
@@ -285,12 +288,20 @@ function generateNLSSourceMap(
 
 				cumulativeShift += edit.newLength - origLen;
 
-				// Map content after edit: columns resume with the shift applied
-				generator.addMapping({
-					generated: { line: smLine, column: edit.endCol + cumulativeShift },
-					original: { line: smLine, column: edit.endCol },
-					source: filePath,
-				});
+				// Source maps don't interpolate columns — each query resolves to the
+				// last segment with generatedColumn <= queryColumn. A single mapping
+				// at edit-end would cause every subsequent column on this line to
+				// collapse to that one original position. Add per-column identity
+				// mappings from edit-end to the next edit (or end of line) so that
+				// esbuild's source-map composition preserves fine-grained accuracy.
+				const nextBound = i + 1 < lineEdits.length ? lineEdits[i + 1].startCol : lines[line].length;
+				for (let origCol = edit.endCol; origCol < nextBound; origCol++) {
+					generator.addMapping({
+						generated: { line: smLine, column: origCol + cumulativeShift },
+						original: { line: smLine, column: origCol },
+						source: filePath,
+					});
+				}
 			}
 		}
 	}
@@ -302,17 +313,19 @@ function replaceInOutput(
 	content: string,
 	indexMap: Map<string, number>,
 	preserveEnglish: boolean
-): string {
-	// Replace all placeholders in a single pass using regex
-	// Two types of placeholders:
-	// - %%NLS:moduleId#key%% for localize() - message replaced with null
-	// - %%NLS2:moduleId#key%% for localize2() - message preserved
-	// Note: esbuild may use single or double quotes, so we handle both
+): { code: string; edits: readonly TextEdit[] } {
+	// Collect all matches first, then apply from back to front so that byte
+	// offsets remain valid. Each match becomes a TextEdit in terms of the
+	// ORIGINAL content offsets, which is what adjustSourceMap expects.
+
+	interface PendingEdit { start: number; end: number; replacement: string }
+	const pending: PendingEdit[] = [];
 
 	if (preserveEnglish) {
-		// Just replace the placeholder with the index (both NLS and NLS2)
-		return content.replace(/["']%%NLS2?:([^%]+)%%["']/g, (match, inner) => {
-			// Try NLS first, then NLS2
+		const re = /["']%%NLS2?:([^%]+)%%["']/g;
+		let m: RegExpExecArray | null;
+		while ((m = re.exec(content)) !== null) {
+			const inner = m[1];
 			let placeholder = `%%NLS:${inner}%%`;
 			let index = indexMap.get(placeholder);
 			if (index === undefined) {
@@ -320,45 +333,60 @@ function replaceInOutput(
 				index = indexMap.get(placeholder);
 			}
 			if (index !== undefined) {
-				return String(index);
+				pending.push({ start: m.index, end: m.index + m[0].length, replacement: String(index) });
 			}
-			// Placeholder not found in map, leave as-is (shouldn't happen)
-			return match;
-		});
+		}
 	} else {
-		// For NLS (localize): replace placeholder with index AND replace message with null
-		// For NLS2 (localize2): replace placeholder with index, keep message
-		// Note: Use (?:[^"\\]|\\.)* to properly handle escaped quotes like \" or \\
-		// Note: esbuild may use single or double quotes, so we handle both
-
-		// First handle NLS (localize) - replace both key and message
-		content = content.replace(
-			/["']%%NLS:([^%]+)%%["'](\s*,\s*)(?:"(?:[^"\\]|\\.)*"|'(?:[^'\\]|\\.)*'|`(?:[^`\\]|\\.)*`)/g,
-			(match, inner, comma) => {
-				const placeholder = `%%NLS:${inner}%%`;
-				const index = indexMap.get(placeholder);
-				if (index !== undefined) {
-					return `${index}${comma}null`;
-				}
-				return match;
+		// NLS (localize): replace placeholder with index AND replace message with null
+		const reNLS = /["']%%NLS:([^%]+)%%["'](\s*,\s*)(?:"(?:[^"\\]|\\.)*"|'(?:[^'\\]|\\.)*'|`(?:[^`\\]|\\.)*`)/g;
+		let m: RegExpExecArray | null;
+		while ((m = reNLS.exec(content)) !== null) {
+			const inner = m[1];
+			const comma = m[2];
+			const placeholder = `%%NLS:${inner}%%`;
+			const index = indexMap.get(placeholder);
+			if (index !== undefined) {
+				pending.push({ start: m.index, end: m.index + m[0].length, replacement: `${index}${comma}null` });
 			}
-		);
-
-		// Then handle NLS2 (localize2) - replace only key, keep message
-		content = content.replace(
-			/["']%%NLS2:([^%]+)%%["']/g,
-			(match, inner) => {
-				const placeholder = `%%NLS2:${inner}%%`;
-				const index = indexMap.get(placeholder);
-				if (index !== undefined) {
-					return String(index);
-				}
-				return match;
+		}
+
+		// NLS2 (localize2): replace only key, keep message
+		const reNLS2 = /["']%%NLS2:([^%]+)%%["']/g;
+		while ((m = reNLS2.exec(content)) !== null) {
+			const inner = m[1];
+			const placeholder = `%%NLS2:${inner}%%`;
+			const index = indexMap.get(placeholder);
+			if (index !== undefined) {
+				pending.push({ start: m.index, end: m.index + m[0].length, replacement: String(index) });
 			}
-		);
+		}
+	}
 
-		return content;
+	if (pending.length === 0) {
+		return { code: content, edits: [] };
 	}
+
+	// Sort by offset ascending, then apply back-to-front to keep offsets valid
+	pending.sort((a, b) => a.start - b.start);
+
+	// Build TextEdit[] (in original-content coordinates) and apply edits
+	const edits: TextEdit[] = [];
+	for (const p of pending) {
+		edits.push({ start: p.start, end: p.end, newText: p.replacement });
+	}
+
+	// Apply edits using forward-scanning parts array — O(N+K) instead of
+	// O(N*K) from repeated substring concatenation on large strings.
+	const parts: string[] = [];
+	let lastEnd = 0;
+	for (const p of pending) {
+		parts.push(content.substring(lastEnd, p.start));
+		parts.push(p.replacement);
+		lastEnd = p.end;
+	}
+	parts.push(content.substring(lastEnd));
+
+	return { code: parts.join(''), edits };
 }
 
 // ============================================================================
@@ -399,7 +427,11 @@ export function nlsPlugin(options: NLSPluginOptions): esbuild.Plugin {
 					// back to the original. Embed it inline so esbuild composes it
 					// with its own bundle source map, making the final map point to
 					// the original TS source.
-					const sourceName = relativePath.replace(/\\/g, '/');
+					// This inline source map is resolved relative to esbuild's sourcefile
+					// for args.path. Using the full repo-relative path here makes esbuild
+					// resolve it against the file's own directory, which duplicates the
+					// directory segments in the final bundled source map.
+					const sourceName = path.basename(args.path);
 					const sourcemap = generateNLSSourceMap(source, sourceName, edits);
 					const encodedMap = Buffer.from(sourcemap).toString('base64');
 					const contentsWithMap = code + `\n//# sourceMappingURL=data:application/json;base64,${encodedMap}\n`;
diff --git a/build/next/private-to-property.ts b/build/next/private-to-property.ts
index 11f977774a5fd..98ff98a64408a 100644
--- a/build/next/private-to-property.ts
+++ b/build/next/private-to-property.ts
@@ -220,15 +220,53 @@ export function adjustSourceMap(
 		return sourceMapJson;
 	}
 
-	// Build a line-offset table for the original code to convert byte offsets to line/column
-	const lineStarts: number[] = [0];
-	for (let i = 0; i < originalCode.length; i++) {
-		if (originalCode.charCodeAt(i) === 10 /* \n */) {
-			lineStarts.push(i + 1);
+	// Build line-offset tables for the original code and the code after edits.
+	// When edits span newlines (e.g. NLS replacing a multi-line template literal
+	// with `null`), subsequent lines shift up and columns change. We handle this
+	// by converting each mapping's old generated (line, col) to a byte offset,
+	// adjusting the offset for the edits, then converting back to (line, col) in
+	// the post-edit coordinate system.
+
+	const oldLineStarts = buildLineStarts(originalCode);
+	const newLineStarts = buildLineStartsAfterEdits(originalCode, edits);
+
+	// Precompute cumulative byte-shift after each edit for binary search
+	const n = edits.length;
+	const editStarts: number[] = new Array(n);
+	const editEnds: number[] = new Array(n);
+	const cumShifts: number[] = new Array(n); // cumulative shift *after* edit[i]
+	let cumShift = 0;
+	for (let i = 0; i < n; i++) {
+		editStarts[i] = edits[i].start;
+		editEnds[i] = edits[i].end;
+		cumShift += edits[i].newText.length - (edits[i].end - edits[i].start);
+		cumShifts[i] = cumShift;
+	}
+
+	function adjustOffset(oldOff: number): number {
+		// Binary search: find last edit with start <= oldOff
+		let lo = 0, hi = n - 1;
+		while (lo <= hi) {
+			const mid = (lo + hi) >> 1;
+			if (editStarts[mid] <= oldOff) {
+				lo = mid + 1;
+			} else {
+				hi = mid - 1;
+			}
+		}
+		// hi = index of last edit where start <= oldOff, or -1 if none
+		if (hi < 0) {
+			return oldOff;
 		}
+		if (oldOff < editEnds[hi]) {
+			// Inside edit range — clamp to edit start in new coordinates
+			const prevShift = hi > 0 ? cumShifts[hi - 1] : 0;
+			return editStarts[hi] + prevShift;
+		}
+		return oldOff + cumShifts[hi];
 	}
 
-	function offsetToLineCol(offset: number): { line: number; col: number } {
+	function offsetToLineCol(lineStarts: readonly number[], offset: number): { line: number; col: number } {
 		let lo = 0, hi = lineStarts.length - 1;
 		while (lo < hi) {
 			const mid = (lo + hi + 1) >> 1;
@@ -241,23 +279,9 @@ export function adjustSourceMap(
 		return { line: lo, col: offset - lineStarts[lo] };
 	}
 
-	// Convert edits from byte offsets to per-line column shifts
-	interface LineEdit { col: number; origLen: number; newLen: number }
-	const editsByLine = new Map<number, LineEdit[]>();
-	for (const edit of edits) {
-		const pos = offsetToLineCol(edit.start);
-		const origLen = edit.end - edit.start;
-		let arr = editsByLine.get(pos.line);
-		if (!arr) {
-			arr = [];
-			editsByLine.set(pos.line, arr);
-		}
-		arr.push({ col: pos.col, origLen, newLen: edit.newText.length });
-	}
-
 	// Use source-map library to read, adjust, and write
 	const consumer = new SourceMapConsumer(sourceMapJson);
-	const generator = new SourceMapGenerator({ file: sourceMapJson.file });
+	const generator = new SourceMapGenerator({ file: sourceMapJson.file, sourceRoot: sourceMapJson.sourceRoot });
 
 	// Copy sourcesContent
 	for (let i = 0; i < sourceMapJson.sources.length; i++) {
@@ -267,15 +291,19 @@ export function adjustSourceMap(
 		}
 	}
 
-	// Walk every mapping, adjust the generated column, and add to the new generator
+	// Walk every mapping, convert old generated position → byte offset → adjust → new position
 	consumer.eachMapping(mapping => {
-		const lineEdits = editsByLine.get(mapping.generatedLine - 1); // 0-based for our data
-		const adjustedCol = adjustColumn(mapping.generatedColumn, lineEdits);
+		const oldLine0 = mapping.generatedLine - 1; // 0-based
+		const oldOff = (oldLine0 < oldLineStarts.length
+			? oldLineStarts[oldLine0]
+			: oldLineStarts[oldLineStarts.length - 1]) + mapping.generatedColumn;
+
+		const newOff = adjustOffset(oldOff);
+		const newPos = offsetToLineCol(newLineStarts, newOff);
 
-		// Some mappings may be unmapped (no original position/source) - skip those.
 		if (mapping.source !== null && mapping.originalLine !== null && mapping.originalColumn !== null) {
 			const newMapping: Mapping = {
-				generated: { line: mapping.generatedLine, column: adjustedCol },
+				generated: { line: newPos.line + 1, column: newPos.col },
 				original: { line: mapping.originalLine, column: mapping.originalColumn },
 				source: mapping.source,
 			};
@@ -283,25 +311,82 @@ export function adjustSourceMap(
 				newMapping.name = mapping.name;
 			}
 			generator.addMapping(newMapping);
+		} else {
+			// Preserve unmapped segments (generated-only mappings with no original
+			// position). These create essential "gaps" that prevent
+			// originalPositionFor() from wrongly interpolating between distant
+			// valid mappings on the same line in minified output.
+			// eslint-disable-next-line local/code-no-dangerous-type-assertions
+			generator.addMapping({
+				generated: { line: newPos.line + 1, column: newPos.col },
+			} as Mapping);
 		}
 	});
 
 	return JSON.parse(generator.toString());
 }
 
-function adjustColumn(col: number, lineEdits: { col: number; origLen: number; newLen: number }[] | undefined): number {
-	if (!lineEdits) {
-		return col;
+function buildLineStarts(text: string): number[] {
+	const starts: number[] = [0];
+	let pos = 0;
+	while (true) {
+		const nl = text.indexOf('\n', pos);
+		if (nl === -1) {
+			break;
+		}
+		starts.push(nl + 1);
+		pos = nl + 1;
+	}
+	return starts;
+}
+
+/**
+ * Compute line starts for the code that results from applying `edits` to
+ * `originalCode`, without materialising the full new string.
+ */
+function buildLineStartsAfterEdits(originalCode: string, edits: readonly TextEdit[]): number[] {
+	const starts: number[] = [0];
+	let oldPos = 0;
+	let newPos = 0;
+
+	for (const edit of edits) {
+		// Scan unchanged region [oldPos, edit.start) for newlines
+		let from = oldPos;
+		while (true) {
+			const nl = originalCode.indexOf('\n', from);
+			if (nl === -1 || nl >= edit.start) {
+				break;
+			}
+			starts.push(newPos + (nl - oldPos) + 1);
+			from = nl + 1;
+		}
+		newPos += edit.start - oldPos;
+
+		// Scan replacement text for newlines
+		let replFrom = 0;
+		while (true) {
+			const nl = edit.newText.indexOf('\n', replFrom);
+			if (nl === -1) {
+				break;
+			}
+			starts.push(newPos + nl + 1);
+			replFrom = nl + 1;
+		}
+		newPos += edit.newText.length;
+
+		oldPos = edit.end;
 	}
-	let shift = 0;
-	for (const edit of lineEdits) {
-		if (edit.col + edit.origLen <= col) {
-			shift += edit.newLen - edit.origLen;
-		} else if (edit.col < col) {
-			return edit.col + shift;
-		} else {
+
+	// Scan remaining unchanged text after last edit
+	let from = oldPos;
+	while (true) {
+		const nl = originalCode.indexOf('\n', from);
+		if (nl === -1) {
 			break;
 		}
+		starts.push(newPos + (nl - oldPos) + 1);
+		from = nl + 1;
 	}
-	return col + shift;
+
+	return starts;
 }
diff --git a/build/next/test/nls-sourcemap.test.ts b/build/next/test/nls-sourcemap.test.ts
index fd732b8680217..c3aad2c80dcdc 100644
--- a/build/next/test/nls-sourcemap.test.ts
+++ b/build/next/test/nls-sourcemap.test.ts
@@ -10,6 +10,7 @@ import * as fs from 'fs';
 import * as os from 'os';
 import { type RawSourceMap, SourceMapConsumer } from 'source-map';
 import { nlsPlugin, createNLSCollector, finalizeNLS, postProcessNLS } from '../nls-plugin.ts';
+import { adjustSourceMap } from '../private-to-property.ts';
 
 // analyzeLocalizeCalls requires the import path to end with `/nls`
 const NLS_STUB = [
@@ -36,7 +37,7 @@ interface BundleResult {
 async function bundleWithNLS(
 	files: Record<string, string>,
 	entryPoint: string,
-	opts?: { postProcess?: boolean }
+	opts?: { postProcess?: boolean; minify?: boolean }
 ): Promise<BundleResult> {
 	const tmpDir = await fs.promises.mkdtemp(path.join(os.tmpdir(), 'nls-sm-test-'));
 	const srcDir = path.join(tmpDir, 'src');
@@ -64,6 +65,7 @@ async function bundleWithNLS(
 		packages: 'external',
 		sourcemap: 'linked',
 		sourcesContent: true,
+		minify: opts?.minify ?? false,
 		write: false,
 		plugins: [
 			nlsPlugin({ baseDir: srcDir, collector }),
@@ -91,7 +93,16 @@ async function bundleWithNLS(
 	// Optionally apply NLS post-processing (replaces placeholders with indices)
 	if (opts?.postProcess) {
 		const nlsResult = await finalizeNLS(collector, outDir);
-		jsContent = postProcessNLS(jsContent, nlsResult.indexMap, false);
+		const preNLSCode = jsContent;
+		const nlsProcessed = postProcessNLS(jsContent, nlsResult.indexMap, false);
+		jsContent = nlsProcessed.code;
+
+		// Adjust source map for NLS edits
+		if (nlsProcessed.edits.length > 0) {
+			const mapJson = JSON.parse(mapContent);
+			const adjusted = adjustSourceMap(mapJson, preNLSCode, nlsProcessed.edits);
+			mapContent = JSON.stringify(adjusted);
+		}
 	}
 
 	assert.ok(jsContent, 'Expected JS output');
@@ -209,6 +220,28 @@ suite('NLS plugin source maps', () => {
 		}
 	});
 
+	test('NLS-affected nested file keeps a non-duplicated source path', async () => {
+		const source = [
+			'import { localize } from "../../vs/nls";',
+			'export const msg = localize("myKey", "Hello World");',
+		].join('\n');
+
+		const { mapJson, cleanup } = await bundleWithNLS(
+			{ 'nested/deep/file.ts': source },
+			'nested/deep/file.ts',
+		);
+
+		try {
+			const sources: string[] = mapJson.sources ?? [];
+			const nestedSource = sources.find((s: string) => s.endsWith('/nested/deep/file.ts'));
+			assert.ok(nestedSource, 'Should find nested/deep/file.ts in sources');
+			assert.ok(!nestedSource.includes('/nested/deep/nested/deep/file.ts'),
+				`Source path should not duplicate directory segments. Actual: ${nestedSource}`);
+		} finally {
+			cleanup();
+		}
+	});
+
 	test('line mapping correct for code after localize calls', async () => {
 		const source = [
 			'import { localize } from "../vs/nls";',                         // 1
@@ -370,4 +403,82 @@ suite('NLS plugin source maps', () => {
 			cleanup();
 		}
 	});
+
+	test('post-processed NLS - column mappings correct after placeholder replacement', async () => {
+		// NLS placeholders like "%%NLS:test/drift#k%%" are much longer than their
+		// replacements (e.g. "0"). Without source map adjustment the columns for
+		// tokens AFTER the replacement drift by the cumulative length delta.
+		const source = [
+			'import { localize } from "../vs/nls";',                                   // 1
+			'export const a = localize("k1", "Alpha"); export const MARKER = "FINDME";',   // 2
+		].join('\n');
+
+		const { js, map, cleanup } = await bundleWithNLS(
+			{ 'test/drift.ts': source },
+			'test/drift.ts',
+			{ postProcess: true }
+		);
+
+		try {
+			assert.ok(!js.includes('%%NLS:'), 'Placeholders should be replaced');
+
+			const bundleLine = findLine(js, 'FINDME');
+			const bundleCol = findColumn(js, '"FINDME"');
+			const pos = map.originalPositionFor({ line: bundleLine, column: bundleCol });
+
+			assert.ok(pos.source, 'Should have source');
+			assert.strictEqual(pos.line, 2, 'Should map to line 2');
+
+			const originalCol = findColumn(source, '"FINDME"');
+			const columnDrift = Math.abs(pos.column! - originalCol);
+			assert.ok(columnDrift <= 20,
+				`Column drift after NLS post-processing should be small. ` +
+				`Expected ~${originalCol}, got ${pos.column} (drift: ${columnDrift}). ` +
+				`Large drift means postProcessNLS edits were not applied to the source map.`);
+		} finally {
+			cleanup();
+		}
+	});
+
+	test('minified bundle with NLS - end-to-end column mapping', async () => {
+		// With minification, the entire output is (roughly) on one line.
+		// Multiple NLS replacements compound their column shifts. A function
+		// defined after several localize() calls must still map correctly.
+		const source = [
+			'import { localize } from "../vs/nls";',                               // 1
+			'',                                                                     // 2
+			'export const a = localize("k1", "Alpha message");',                   // 3
+			'export const b = localize("k2", "Bravo message that is quite long");', // 4
+			'export const c = localize("k3", "Charlie");',                         // 5
+			'export const d = localize("k4", "Delta is the fourth letter");',      // 6
+			'',                                                                     // 7
+			'export function computeResult(x: number): number {',                  // 8
+			'\treturn x * 42;',                                                     // 9
+			'}',                                                                    // 10
+		].join('\n');
+
+		const { js, map, cleanup } = await bundleWithNLS(
+			{ 'test/minified.ts': source },
+			'test/minified.ts',
+			{ postProcess: true, minify: true }
+		);
+
+		try {
+			assert.ok(!js.includes('%%NLS:'), 'Placeholders should be replaced');
+
+			// Find the computeResult function in the minified output.
+			// esbuild minifies `x * 42` and may rename the parameter, so
+			// search for `*42` which survives both minification and renaming.
+			const needle = '*42';
+			const bundleLine = findLine(js, needle);
+			const bundleCol = findColumn(js, needle);
+			const pos = map.originalPositionFor({ line: bundleLine, column: bundleCol });
+
+			assert.ok(pos.source, 'Should have source for minified mapping');
+			assert.strictEqual(pos.line, 9,
+				`Should map "*42" back to line 9. Got line ${pos.line}.`);
+		} finally {
+			cleanup();
+		}
+	});
 });
diff --git a/build/next/test/private-to-property.test.ts b/build/next/test/private-to-property.test.ts
index aa9da72ce9a51..9b97679767933 100644
--- a/build/next/test/private-to-property.test.ts
+++ b/build/next/test/private-to-property.test.ts
@@ -439,6 +439,41 @@ suite('adjustSourceMap', () => {
 		assert.strictEqual(pos.column, origGetValueCol, 'getValue column should match original');
 	});
 
+	test('multi-line edit: removing newlines shifts subsequent lines up', () => {
+		// Simulates the NLS scenario: a template literal with embedded newlines
+		// is replaced with `null`, collapsing 3 lines into 1.
+		const code = [
+			'var a = "hello";',          // line 0 (0-based)
+			'var b = `line1',             // line 1
+			'line2',                      // line 2
+			'line3`;',                    // line 3
+			'var c = "world";',           // line 4
+		].join('\n');
+		const map = createIdentitySourceMap(code, 'test.js');
+
+		// Replace the template literal `line1\nline2\nline3` with `null`
+		// (keeps `var b = ` and `;` intact)
+		const tplStart = code.indexOf('`line1');
+		const tplEnd = code.indexOf('line3`') + 'line3`'.length;
+		const edits = [{ start: tplStart, end: tplEnd, newText: 'null' }];
+
+		const result = adjustSourceMap(map, code, edits);
+		const consumer = new SourceMapConsumer(result);
+
+		// After edit, code is:
+		// "var a = \"hello\";\nvar b = null;\nvar c = \"world\";"
+		// "var c" was on line 5 (1-based), now on line 3 (1-based) since 2 newlines removed
+
+		// 'var c' at original line 5, col 0 should now map at generated line 3
+		const pos = consumer.originalPositionFor({ line: 3, column: 0 });
+		assert.strictEqual(pos.line, 5, 'var c should map to original line 5');
+		assert.strictEqual(pos.column, 0, 'var c column should be 0');
+
+		// 'var a' on line 1 should be unaffected
+		const posA = consumer.originalPositionFor({ line: 1, column: 0 });
+		assert.strictEqual(posA.line, 1, 'var a should still map to original line 1');
+	});
+
 	test('brand check: #field in obj -> string replacement adjusts map', () => {
 		const code = 'class C { #x; check(o) { return #x in o; } }';
 		const map = createIdentitySourceMap(code, 'test.js');
diff --git a/build/next/working.md b/build/next/working.md
index b59b347611dbd..a7ea64db8b648 100644
--- a/build/next/working.md
+++ b/build/next/working.md
@@ -37,7 +37,7 @@ In [gulpfile.vscode.ts](../gulpfile.vscode.ts#L228-L242), the `core-ci` task use
 - `runEsbuildTranspile()` → transpile command
 - `runEsbuildBundle()` → bundle command
 
-Old gulp-based bundling renamed to `core-ci-OLD`.
+Old gulp-based bundling renamed to `core-ci-old`.
 
 ---
 
@@ -134,7 +134,7 @@ npm run gulp vscode-reh-web-darwin-arm64-min
 
 1. **`BUILD_INSERT_PACKAGE_CONFIGURATION`** - Server bootstrap files ([bootstrap-meta.ts](../../src/bootstrap-meta.ts)) have this marker for package.json injection. Currently handled by [inlineMeta.ts](../lib/inlineMeta.ts) in the old build's packaging step.
 
-2. **Mangling** - The new build doesn't do TypeScript-based mangling yet. Old `core-ci` with mangling is now `core-ci-OLD`.
+2. **Mangling** - The new build doesn't do TypeScript-based mangling yet. Old `core-ci` with mangling is now `core-ci-old`.
 
 3. **Entry point duplication** - Entry points are duplicated between [buildfile.ts](../buildfile.ts) and [index.ts](index.ts). Consider consolidating.
 
@@ -222,13 +222,13 @@ Two categories of corruption:
 
 2. **`--source-map-base-url` option** - Rewrites `sourceMappingURL` comments to point to CDN URLs.
 
-3. **NLS plugin inline source maps** (`nls-plugin.ts`) - The `onLoad` handler now generates an inline source map (`//# sourceMappingURL=data:...`) mapping from NLS-transformed source back to original. esbuild composes this with its own bundle source map. `SourceMapGenerator.setSourceContent` embeds the original source so `sourcesContent` in the final `.map` has the real TypeScript. Tests in `test/nls-sourcemap.test.ts`.
+3. **NLS plugin inline source maps** (`nls-plugin.ts`) - The `onLoad` handler generates an inline source map (`//# sourceMappingURL=data:...`) mapping from NLS-transformed source back to original. esbuild composes this with its own bundle source map. `SourceMapGenerator.setSourceContent` embeds the original source so `sourcesContent` in the final `.map` has the real TypeScript. `generateNLSSourceMap` adds per-column identity mappings after each edit on a line so that esbuild's source-map composition preserves fine-grained column accuracy (source maps don't interpolate columns — they use binary search, so a single boundary mapping would collapse all subsequent columns to the edit-end position). Tests in `test/nls-sourcemap.test.ts`.
 
 4. **`convertPrivateFields` source map adjustment** (`private-to-property.ts`) - `convertPrivateFields` returns its sorted edits as `TextEdit[]`. `adjustSourceMap()` uses `SourceMapConsumer` to walk every mapping, adjusts generated columns based on cumulative edit shifts per line, and rebuilds with `SourceMapGenerator`. The post-processing loop in `index.ts` saves pre-mangle content + edits per JS file, then applies `adjustSourceMap` to the corresponding `.map`. Tests in `test/private-to-property.test.ts`.
 
-### Not Yet Fixed
+5. **`postProcessNLS` source map adjustment** (`nls-plugin.ts`, `index.ts`) — `postProcessNLS` now returns `{ code, edits }` where `edits` is a `TextEdit[]` tracking each replacement's byte offset. The bundle loop in `index.ts` chains `adjustSourceMap` calls: first for mangle edits, then for NLS edits, so both transforms are accurately reflected in the final `.map` file. Tests in `test/nls-sourcemap.test.ts`.
 
-**`postProcessNLS` column drift** - Replaces NLS placeholders with short indices in bundled output without updating `.map` files. Shifts columns but never lines, so line-level debugging and crash reporting work correctly. Fixing would require tracking replacement offsets through regex matches and adjusting the source map, similar to `adjustSourceMap`.
+6. **`adjustSourceMap` unmapped segment preservation** (`private-to-property.ts`) — Previously, `adjustSourceMap()` silently dropped mappings where `source === null`. These unmapped segments create essential "gaps" that prevent `originalPositionFor()` from wrongly interpolating between distant valid mappings on the same minified line. Now emits them as generated-only mappings. Also preserves `sourceRoot` from the input map.
 
 ### Key Technical Details
 
@@ -241,6 +241,71 @@ Two categories of corruption:
 
 **Plugin interaction:** Both the NLS plugin and `fileContentMapperPlugin` register `onLoad({ filter: /\.ts$/ })`. In esbuild, the first `onLoad` to return non-`undefined` wins. The NLS plugin is `unshift`ed (runs first), so files with NLS calls skip `fileContentMapperPlugin`. This is safe in practice since `product.ts` (which has `BUILD->INSERT_PRODUCT_CONFIGURATION`) has no localize calls.
 
+### Still Broken — Full Production Build (`npm run gulp vscode-min`)
+
+**Symptom:** Source maps are totally broken in the minified production build. E.g. a breakpoint at `src/vs/editor/browser/editorExtensions.ts` line 308 resolves to `src/vs/editor/common/cursor/cursorMoveCommands.ts` line 732 — a completely different file. This is **cross-file** mapping corruption, not just column drift.
+
+**Status of unit tests:** The fixes above pass in isolated unit tests (small 1–2 file bundles via `esbuild.build` with `minify: true`). The tests verify column drift ≤ 20 and correct line mapping for single-file bundles with NLS. **183 tests pass, 0 failing.** But the full production build bundles hundreds of files into huge minified outputs (e.g. `workbench.desktop.main.js` at ~15 MB) and the source maps break at that scale.
+
+**Suspected root causes (need investigation):**
+
+1. **`generateNLSSourceMap` per-column identity mappings may overwhelm esbuild's source-map composition.** The fix added one mapping per column from edit-end to end-of-line (or next edit). For a long TypeScript line with a `localize()` call near the beginning, this generates hundreds of identity mappings per line. Across hundreds of files, the inline source maps embedded in `onLoad` responses may be extremely large. esbuild must compose these with its own source maps during bundling — it may hit limits, silently drop mappings, or produce incorrect composed maps at this scale. **Mitigation to try:** Instead of per-column mappings, use sparser "checkpoint" mappings (e.g., every N characters) or rely only on boundary mappings and accept some column drift within the NLS-transformed region. The old boundary-only approach was wrong (collapsed all downstream columns), but per-column may be the other extreme.
+
+2. **`adjustSourceMap` may corrupt source indices in large minified bundles.** In a minified bundle, the entire output is on one or very few lines. `adjustSourceMap()` walks every mapping via `SourceMapConsumer.eachMapping()` and adjusts `generatedColumn` using `adjustColumn()`. But when thousands of mappings all share `generatedLine: 1` and there are hundreds of NLS edits on that same line, there may be sorting/ordering bugs: `eachMapping()` returns mappings in generated order by default, but `adjustColumn()` binary-searches through edits sorted by column. If edits cover regions that interleave with mappings from different source files, the cumulative shift calculation might produce wrong columns that then resolve to wrong source files.
+
+3. **Chained `adjustSourceMap` calls (mangle → NLS) may compound errors.** After the first `adjustSourceMap` for mangle edits, the source map's generated columns are updated. The second call for NLS edits uses `nlsEdits` which were computed against `preNLSCode` — but `preNLSCode` is the post-mangle JS, which is what the first `adjustSourceMap` maps from. This chaining _should_ be correct, but needs verification at scale with a real minified bundle.
+
+4. **The `source-map` v0.6.1 library may have precision issues with very large VLQ-encoded maps.** The bundled outputs have source maps with hundreds of thousands of mappings. The library is old (2017) and there may be numerical precision or sorting issues with very large maps. Consider testing with `source-map` v0.7+ or the Rust-based `@aspect-build/source-map`.
+
+5. **Alternative approach: skip per-column NLS plugin mappings, fix only `postProcessNLS`.** The NLS plugin `onLoad` replaces `"key"` with `"%%NLS:longPlaceholder%%"` — a length change that only affects columns on affected lines. The subsequent `postProcessNLS` then replaces the long placeholder with a short index. If the `adjustSourceMap` for `postProcessNLS` is correct, it should compensate for both expansions (plugin expansion + post-process contraction). We might not need per-column mappings in `generateNLSSourceMap` at all — just the boundary mapping. The column will drift in the intermediate representation but `adjustSourceMap` for NLS should fix it. **This hypothesis needs testing.**
+
+6. **Alternative approach: do NLS replacement purely in post-processing.** Skip the `onLoad` two-phase approach (placeholder insertion + post-processing replacement) entirely. Instead, run `postProcessNLS` as a single post-processing step that directly replaces `localize("key", "message")` → `localize(0, null)` in the bundled JS output, with proper source-map adjustment via `adjustSourceMap`. This avoids both the inline source map composition complexity and the two-step replacement. The downside is that post-processing must parse/regex-match real `localize()` calls (not easy placeholders), which is more fragile.
+
+**Summary of fixes applied vs status:**
+
+| Bug | Fix | Unit test | Production |
+|-----|-----|-----------|------------|
+| `generateNLSSourceMap` only had boundary mappings → columns collapsed | Added per-column identity mappings after each edit | Pass (drift: 0) | **Broken** — may overwhelm esbuild composition at scale |
+| `postProcessNLS` didn't track edits for source map adjustment | Returns `{ code, edits }`, chained in `index.ts` | Pass | **Broken** — `adjustSourceMap` may corrupt source indices on huge single-line minified output |
+| `adjustSourceMap` dropped unmapped segments | Preserves generated-only mappings + `sourceRoot` | Pass (no regressions) | **Broken** — same cross-file mapping issue |
+
+**Files involved:**
+- `build/next/nls-plugin.ts` — `generateNLSSourceMap()` (per-column mappings), `postProcessNLS()` (returns edits), `replaceInOutput()` (regex replacement)
+- `build/next/private-to-property.ts` — `adjustSourceMap()` (column adjustment)
+- `build/next/index.ts` — bundle post-processing loop (lines ~899–975), chains adjustSourceMap calls
+- `build/next/test/nls-sourcemap.test.ts` — unit tests (pass but don't cover production-scale bundles)
+
+**How to reproduce:**
+```bash
+npm run gulp vscode-min
+# Open out-vscode-min/ in a debugger, set breakpoints in editor files
+# Observe breakpoints resolve to wrong files
+```
+
+**How to debug further:**
+```bash
+# 1. Build with just --nls (no mangle) to isolate NLS from mangle issues
+npx tsx build/next/index.ts bundle --nls --minify --target desktop --out out-debug
+
+# 2. Build with just --mangle-privates (no NLS) to isolate mangle issues
+npx tsx build/next/index.ts bundle --mangle-privates --minify --target desktop --out out-debug
+
+# 3. Build with neither (baseline — does esbuild's own map work?)
+npx tsx build/next/index.ts bundle --minify --target desktop --out out-debug
+
+# 4. Compare .map files across the three builds to find where mappings diverge
+
+# 5. Validate a specific mapping in the large bundle:
+node -e "
+const {SourceMapConsumer} = require('source-map');
+const fs = require('fs');
+const map = JSON.parse(fs.readFileSync('./out-debug/vs/workbench/workbench.desktop.main.js.map','utf8'));
+const c = new SourceMapConsumer(map);
+// Look up a known position and see which source file it resolves to
+console.log(c.originalPositionFor({line: 1, column: XXXX}));
+"
+```
+
 ---
 
 ## Self-hosting Setup
diff --git a/build/npm/dirs.ts b/build/npm/dirs.ts
index 48d76e2731a6e..b56884af25c52 100644
--- a/build/npm/dirs.ts
+++ b/build/npm/dirs.ts
@@ -60,6 +60,7 @@ export const dirs = [
 	'test/mcp',
 	'.vscode/extensions/vscode-selfhost-import-aid',
 	'.vscode/extensions/vscode-selfhost-test-provider',
+	'.vscode/extensions/vscode-extras',
 ];
 
 if (existsSync(`${import.meta.dirname}/../../.build/distro/npm`)) {
diff --git a/build/npm/fast-install.ts b/build/npm/fast-install.ts
new file mode 100644
index 0000000000000..ff9a7d2097cf2
--- /dev/null
+++ b/build/npm/fast-install.ts
@@ -0,0 +1,22 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as child_process from 'child_process';
+import { root, isUpToDate, forceInstallMessage } from './installStateHash.ts';
+
+if (!process.argv.includes('--force') && isUpToDate()) {
+	console.log(`\x1b[32mAll dependencies up to date.\x1b[0m ${forceInstallMessage}`);
+	process.exit(0);
+}
+
+const npm = process.platform === 'win32' ? 'npm.cmd' : 'npm';
+const result = child_process.spawnSync(npm, ['install'], {
+	cwd: root,
+	stdio: 'inherit',
+	shell: true,
+	env: { ...process.env, VSCODE_FORCE_INSTALL: '1' },
+});
+
+process.exit(result.status ?? 1);
diff --git a/build/npm/gyp/package-lock.json b/build/npm/gyp/package-lock.json
index 6e28e550f4699..8c499c6740fa9 100644
--- a/build/npm/gyp/package-lock.json
+++ b/build/npm/gyp/package-lock.json
@@ -526,13 +526,13 @@
       }
     },
     "node_modules/minimatch": {
-      "version": "9.0.5",
-      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-9.0.5.tgz",
-      "integrity": "sha512-G6T0ZX48xgozx7587koeX9Ys2NYy6Gmv//P89sEte9V9whIapMNF4idKxnW2QtCcLiTWlb/wfCabAtAFWhhBow==",
+      "version": "9.0.9",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-9.0.9.tgz",
+      "integrity": "sha512-OBwBN9AL4dqmETlpS2zasx+vTeWclWzkblfZk7KTA5j3jeOONz/tRCnZomUyvNg83wL5Zv9Ss6HMJXAgL8R2Yg==",
       "dev": true,
       "license": "ISC",
       "dependencies": {
-        "brace-expansion": "^2.0.1"
+        "brace-expansion": "^2.0.2"
       },
       "engines": {
         "node": ">=16 || 14 >=14.17"
@@ -1069,9 +1069,9 @@
       }
     },
     "node_modules/tar": {
-      "version": "7.5.9",
-      "resolved": "https://registry.npmjs.org/tar/-/tar-7.5.9.tgz",
-      "integrity": "sha512-BTLcK0xsDh2+PUe9F6c2TlRp4zOOBMTkoQHQIWSIzI0R7KG46uEwq4OPk2W7bZcprBMsuaeFsqwYr7pjh6CuHg==",
+      "version": "7.5.11",
+      "resolved": "https://registry.npmjs.org/tar/-/tar-7.5.11.tgz",
+      "integrity": "sha512-ChjMH33/KetonMTAtpYdgUFr0tbz69Fp2v7zWxQfYZX4g5ZN2nOBXm1R2xyA+lMIKrLKIoKAwFj93jE/avX9cQ==",
       "dev": true,
       "license": "BlueOak-1.0.0",
       "dependencies": {
diff --git a/build/npm/installStateHash.ts b/build/npm/installStateHash.ts
new file mode 100644
index 0000000000000..f52c0a4696d4f
--- /dev/null
+++ b/build/npm/installStateHash.ts
@@ -0,0 +1,159 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as crypto from 'crypto';
+import * as fs from 'fs';
+import path from 'path';
+import { dirs } from './dirs.ts';
+
+export const root = fs.realpathSync.native(path.dirname(path.dirname(import.meta.dirname)));
+export const stateFile = path.join(root, 'node_modules', '.postinstall-state');
+export const stateContentsFile = path.join(root, 'node_modules', '.postinstall-state-contents');
+export const forceInstallMessage = 'Run \x1b[36mnode build/npm/fast-install.ts --force\x1b[0m to force a full install.';
+
+export function collectInputFiles(): string[] {
+	const files: string[] = [];
+
+	for (const dir of dirs) {
+		const base = dir === '' ? root : path.join(root, dir);
+		for (const file of ['package.json', 'package-lock.json', '.npmrc']) {
+			const filePath = path.join(base, file);
+			if (fs.existsSync(filePath)) {
+				files.push(filePath);
+			}
+		}
+	}
+
+	files.push(path.join(root, '.nvmrc'));
+
+	return files;
+}
+
+export interface PostinstallState {
+	readonly nodeVersion: string;
+	readonly fileHashes: Record<string, string>;
+}
+
+const packageJsonRelevantKeys = new Set([
+	'name',
+	'dependencies',
+	'devDependencies',
+	'optionalDependencies',
+	'peerDependencies',
+	'peerDependenciesMeta',
+	'overrides',
+	'engines',
+	'workspaces',
+	'bundledDependencies',
+	'bundleDependencies',
+]);
+
+const packageLockJsonIgnoredKeys = new Set(['version']);
+
+function normalizeFileContent(filePath: string): string {
+	const raw = fs.readFileSync(filePath, 'utf8');
+	const basename = path.basename(filePath);
+	if (basename === 'package.json') {
+		const json = JSON.parse(raw);
+		const filtered: Record<string, unknown> = {};
+		for (const key of packageJsonRelevantKeys) {
+			// eslint-disable-next-line local/code-no-in-operator
+			if (key in json) {
+				filtered[key] = json[key];
+			}
+		}
+		return JSON.stringify(filtered, null, '\t') + '\n';
+	}
+	if (basename === 'package-lock.json') {
+		const json = JSON.parse(raw);
+		for (const key of packageLockJsonIgnoredKeys) {
+			delete json[key];
+		}
+		if (json.packages?.['']) {
+			for (const key of packageLockJsonIgnoredKeys) {
+				delete json.packages[''][key];
+			}
+		}
+		return JSON.stringify(json, null, '\t') + '\n';
+	}
+	return raw;
+}
+
+function hashContent(content: string): string {
+	const hash = crypto.createHash('sha256');
+	hash.update(content);
+	return hash.digest('hex');
+}
+
+export function computeState(): PostinstallState {
+	const fileHashes: Record<string, string> = {};
+	for (const filePath of collectInputFiles()) {
+		const key = path.relative(root, filePath);
+		try {
+			fileHashes[key] = hashContent(normalizeFileContent(filePath));
+		} catch {
+			// file may not be readable
+		}
+	}
+	return { nodeVersion: process.versions.node, fileHashes };
+}
+
+export function computeContents(): Record<string, string> {
+	const fileContents: Record<string, string> = {};
+	for (const filePath of collectInputFiles()) {
+		try {
+			fileContents[path.relative(root, filePath)] = normalizeFileContent(filePath);
+		} catch {
+			// file may not be readable
+		}
+	}
+	return fileContents;
+}
+
+export function readSavedState(): PostinstallState | undefined {
+	try {
+		const { nodeVersion, fileHashes } = JSON.parse(fs.readFileSync(stateFile, 'utf8'));
+		return { nodeVersion, fileHashes };
+	} catch {
+		return undefined;
+	}
+}
+
+export function isUpToDate(): boolean {
+	const saved = readSavedState();
+	if (!saved) {
+		return false;
+	}
+	const current = computeState();
+	return saved.nodeVersion === current.nodeVersion
+		&& JSON.stringify(saved.fileHashes) === JSON.stringify(current.fileHashes);
+}
+
+export function readSavedContents(): Record<string, string> | undefined {
+	try {
+		return JSON.parse(fs.readFileSync(stateContentsFile, 'utf8'));
+	} catch {
+		return undefined;
+	}
+}
+
+// When run directly, output state as JSON for tooling (e.g. the vscode-extras extension).
+if (import.meta.filename === process.argv[1]) {
+	if (process.argv[2] === '--normalize-file') {
+		const filePath = process.argv[3];
+		if (!filePath) {
+			process.exit(1);
+		}
+		process.stdout.write(normalizeFileContent(filePath));
+	} else {
+		console.log(JSON.stringify({
+			root,
+			stateContentsFile,
+			current: computeState(),
+			saved: readSavedState(),
+			files: [...collectInputFiles(), stateFile],
+		}));
+	}
+}
diff --git a/build/npm/postinstall.ts b/build/npm/postinstall.ts
index b6a934f74b3eb..ae2651cd188a1 100644
--- a/build/npm/postinstall.ts
+++ b/build/npm/postinstall.ts
@@ -8,9 +8,9 @@ import path from 'path';
 import * as os from 'os';
 import * as child_process from 'child_process';
 import { dirs } from './dirs.ts';
+import { root, stateFile, stateContentsFile, computeState, computeContents, isUpToDate } from './installStateHash.ts';
 
 const npm = process.platform === 'win32' ? 'npm.cmd' : 'npm';
-const root = path.dirname(path.dirname(import.meta.dirname));
 const rootNpmrcConfigKeys = getNpmrcConfigKeys(path.join(root, '.npmrc'));
 
 function log(dir: string, message: string) {
@@ -35,24 +35,45 @@ function run(command: string, args: string[], opts: child_process.SpawnSyncOptio
 	}
 }
 
-function npmInstall(dir: string, opts?: child_process.SpawnSyncOptions) {
-	opts = {
+function spawnAsync(command: string, args: string[], opts: child_process.SpawnOptions): Promise<string> {
+	return new Promise((resolve, reject) => {
+		const child = child_process.spawn(command, args, { ...opts, stdio: ['ignore', 'pipe', 'pipe'] });
+		let output = '';
+		child.stdout?.on('data', (data: Buffer) => { output += data.toString(); });
+		child.stderr?.on('data', (data: Buffer) => { output += data.toString(); });
+		child.on('error', reject);
+		child.on('close', (code) => {
+			if (code !== 0) {
+				reject(new Error(`Process exited with code: ${code}\n${output}`));
+			} else {
+				resolve(output);
+			}
+		});
+	});
+}
+
+async function npmInstallAsync(dir: string, opts?: child_process.SpawnOptions): Promise<void> {
+	const finalOpts: child_process.SpawnOptions = {
 		env: { ...process.env },
 		...(opts ?? {}),
-		cwd: dir,
-		stdio: 'inherit',
-		shell: true
+		cwd: path.join(root, dir),
+		shell: true,
 	};
 
 	const command = process.env['npm_command'] || 'install';
 
 	if (process.env['VSCODE_REMOTE_DEPENDENCIES_CONTAINER_NAME'] && /^(.build\/distro\/npm\/)?remote$/.test(dir)) {
+		const syncOpts: child_process.SpawnSyncOptions = {
+			env: finalOpts.env,
+			cwd: root,
+			stdio: 'inherit',
+			shell: true,
+		};
 		const userinfo = os.userInfo();
 		log(dir, `Installing dependencies inside container ${process.env['VSCODE_REMOTE_DEPENDENCIES_CONTAINER_NAME']}...`);
 
-		opts.cwd = root;
 		if (process.env['npm_config_arch'] === 'arm64') {
-			run('sudo', ['docker', 'run', '--rm', '--privileged', 'multiarch/qemu-user-static', '--reset', '-p', 'yes'], opts);
+			run('sudo', ['docker', 'run', '--rm', '--privileged', 'multiarch/qemu-user-static', '--reset', '-p', 'yes'], syncOpts);
 		}
 		run('sudo', [
 			'docker', 'run',
@@ -63,11 +84,16 @@ function npmInstall(dir: string, opts?: child_process.SpawnSyncOptions) {
 			'-w', path.resolve('/root/vscode', dir),
 			process.env['VSCODE_REMOTE_DEPENDENCIES_CONTAINER_NAME'],
 			'sh', '-c', `\"chown -R root:root ${path.resolve('/root/vscode', dir)} && export PATH="/root/vscode/.build/nodejs-musl/usr/local/bin:$PATH" && npm i -g node-gyp-build && npm ci\"`
-		], opts);
-		run('sudo', ['chown', '-R', `${userinfo.uid}:${userinfo.gid}`, `${path.resolve(root, dir)}`], opts);
+		], syncOpts);
+		run('sudo', ['chown', '-R', `${userinfo.uid}:${userinfo.gid}`, `${path.resolve(root, dir)}`], syncOpts);
 	} else {
 		log(dir, 'Installing dependencies...');
-		run(npm, command.split(' '), opts);
+		const output = await spawnAsync(npm, command.split(' '), finalOpts);
+		if (output.trim()) {
+			for (const line of output.trim().split('\n')) {
+				log(dir, line);
+			}
+		}
 	}
 	removeParcelWatcherPrebuild(dir);
 }
@@ -156,65 +182,115 @@ function clearInheritedNpmrcConfig(dir: string, env: NodeJS.ProcessEnv): void {
 	}
 }
 
-for (const dir of dirs) {
+async function runWithConcurrency(tasks: (() => Promise<void>)[], concurrency: number): Promise<void> {
+	const errors: Error[] = [];
+	let index = 0;
 
-	if (dir === '') {
-		removeParcelWatcherPrebuild(dir);
-		continue; // already executed in root
+	async function worker() {
+		while (index < tasks.length) {
+			const i = index++;
+			try {
+				await tasks[i]();
+			} catch (err) {
+				errors.push(err as Error);
+			}
+		}
 	}
 
-	let opts: child_process.SpawnSyncOptions | undefined;
+	await Promise.all(Array.from({ length: Math.min(concurrency, tasks.length) }, () => worker()));
 
-	if (dir === 'build') {
-		opts = {
-			env: {
-				...process.env
-			},
-		};
-		if (process.env['CC']) { opts.env!['CC'] = 'gcc'; }
-		if (process.env['CXX']) { opts.env!['CXX'] = 'g++'; }
-		if (process.env['CXXFLAGS']) { opts.env!['CXXFLAGS'] = ''; }
-		if (process.env['LDFLAGS']) { opts.env!['LDFLAGS'] = ''; }
-
-		setNpmrcConfig('build', opts.env!);
-		npmInstall('build', opts);
-		continue;
-	}
-
-	if (/^(.build\/distro\/npm\/)?remote$/.test(dir)) {
-		// node modules used by vscode server
-		opts = {
-			env: {
-				...process.env
-			},
-		};
-		if (process.env['VSCODE_REMOTE_CC']) {
-			opts.env!['CC'] = process.env['VSCODE_REMOTE_CC'];
-		} else {
-			delete opts.env!['CC'];
+	if (errors.length > 0) {
+		for (const err of errors) {
+			console.error(err.message);
 		}
-		if (process.env['VSCODE_REMOTE_CXX']) {
-			opts.env!['CXX'] = process.env['VSCODE_REMOTE_CXX'];
-		} else {
-			delete opts.env!['CXX'];
+		process.exit(1);
+	}
+}
+
+async function main() {
+	if (!process.env['VSCODE_FORCE_INSTALL'] && isUpToDate()) {
+		log('.', 'All dependencies up to date, skipping postinstall.');
+		child_process.execSync('git config pull.rebase merges');
+		child_process.execSync('git config blame.ignoreRevsFile .git-blame-ignore-revs');
+		return;
+	}
+
+	const _state = computeState();
+
+	const nativeTasks: (() => Promise<void>)[] = [];
+	const parallelTasks: (() => Promise<void>)[] = [];
+
+	for (const dir of dirs) {
+		if (dir === '') {
+			removeParcelWatcherPrebuild(dir);
+			continue; // already executed in root
+		}
+
+		if (dir === 'build') {
+			nativeTasks.push(() => {
+				const env: NodeJS.ProcessEnv = { ...process.env };
+				if (process.env['CC']) { env['CC'] = 'gcc'; }
+				if (process.env['CXX']) { env['CXX'] = 'g++'; }
+				if (process.env['CXXFLAGS']) { env['CXXFLAGS'] = ''; }
+				if (process.env['LDFLAGS']) { env['LDFLAGS'] = ''; }
+				setNpmrcConfig('build', env);
+				return npmInstallAsync('build', { env });
+			});
+			continue;
+		}
+
+		if (/^(.build\/distro\/npm\/)?remote$/.test(dir)) {
+			const remoteDir = dir;
+			nativeTasks.push(() => {
+				const env: NodeJS.ProcessEnv = { ...process.env };
+				if (process.env['VSCODE_REMOTE_CC']) {
+					env['CC'] = process.env['VSCODE_REMOTE_CC'];
+				} else {
+					delete env['CC'];
+				}
+				if (process.env['VSCODE_REMOTE_CXX']) {
+					env['CXX'] = process.env['VSCODE_REMOTE_CXX'];
+				} else {
+					delete env['CXX'];
+				}
+				if (process.env['CXXFLAGS']) { delete env['CXXFLAGS']; }
+				if (process.env['CFLAGS']) { delete env['CFLAGS']; }
+				if (process.env['LDFLAGS']) { delete env['LDFLAGS']; }
+				if (process.env['VSCODE_REMOTE_CXXFLAGS']) { env['CXXFLAGS'] = process.env['VSCODE_REMOTE_CXXFLAGS']; }
+				if (process.env['VSCODE_REMOTE_LDFLAGS']) { env['LDFLAGS'] = process.env['VSCODE_REMOTE_LDFLAGS']; }
+				if (process.env['VSCODE_REMOTE_NODE_GYP']) { env['npm_config_node_gyp'] = process.env['VSCODE_REMOTE_NODE_GYP']; }
+				setNpmrcConfig('remote', env);
+				return npmInstallAsync(remoteDir, { env });
+			});
+			continue;
 		}
-		if (process.env['CXXFLAGS']) { delete opts.env!['CXXFLAGS']; }
-		if (process.env['CFLAGS']) { delete opts.env!['CFLAGS']; }
-		if (process.env['LDFLAGS']) { delete opts.env!['LDFLAGS']; }
-		if (process.env['VSCODE_REMOTE_CXXFLAGS']) { opts.env!['CXXFLAGS'] = process.env['VSCODE_REMOTE_CXXFLAGS']; }
-		if (process.env['VSCODE_REMOTE_LDFLAGS']) { opts.env!['LDFLAGS'] = process.env['VSCODE_REMOTE_LDFLAGS']; }
-		if (process.env['VSCODE_REMOTE_NODE_GYP']) { opts.env!['npm_config_node_gyp'] = process.env['VSCODE_REMOTE_NODE_GYP']; }
-
-		setNpmrcConfig('remote', opts.env!);
-		npmInstall(dir, opts);
-		continue;
-	}
-
-	// For directories that don't define their own .npmrc, clear inherited config
-	const env = { ...process.env };
-	clearInheritedNpmrcConfig(dir, env);
-	npmInstall(dir, { env });
+
+		const taskDir = dir;
+		parallelTasks.push(() => {
+			const env = { ...process.env };
+			clearInheritedNpmrcConfig(taskDir, env);
+			return npmInstallAsync(taskDir, { env });
+		});
+	}
+
+	// Native dirs (build, remote) run sequentially to avoid node-gyp conflicts
+	for (const task of nativeTasks) {
+		await task();
+	}
+
+	// JS-only dirs run in parallel
+	const concurrency = Math.min(os.cpus().length, 8);
+	log('.', `Running ${parallelTasks.length} npm installs with concurrency ${concurrency}...`);
+	await runWithConcurrency(parallelTasks, concurrency);
+
+	child_process.execSync('git config pull.rebase merges');
+	child_process.execSync('git config blame.ignoreRevsFile .git-blame-ignore-revs');
+
+	fs.writeFileSync(stateFile, JSON.stringify(_state));
+	fs.writeFileSync(stateContentsFile, JSON.stringify(computeContents()));
 }
 
-child_process.execSync('git config pull.rebase merges');
-child_process.execSync('git config blame.ignoreRevsFile .git-blame-ignore-revs');
+main().catch(err => {
+	console.error(err);
+	process.exit(1);
+});
diff --git a/build/npm/preinstall.ts b/build/npm/preinstall.ts
index 3476fcabb5009..dd53ff4467123 100644
--- a/build/npm/preinstall.ts
+++ b/build/npm/preinstall.ts
@@ -6,6 +6,7 @@ import path from 'path';
 import * as fs from 'fs';
 import * as child_process from 'child_process';
 import * as os from 'os';
+import { isUpToDate, forceInstallMessage } from './installStateHash.ts';
 
 if (!process.env['VSCODE_SKIP_NODE_VERSION_CHECK']) {
 	// Get the running Node.js version
@@ -41,6 +42,13 @@ if (process.env.npm_execpath?.includes('yarn')) {
 	throw new Error();
 }
 
+// Fast path: if nothing changed since last successful install, skip everything.
+// This makes `npm i` near-instant when dependencies haven't changed.
+if (!process.env['VSCODE_FORCE_INSTALL'] && isUpToDate()) {
+	console.log(`\x1b[32mAll dependencies up to date.\x1b[0m ${forceInstallMessage}`);
+	process.exit(0);
+}
+
 if (process.platform === 'win32') {
 	if (!hasSupportedVisualStudioVersion()) {
 		console.error('\x1b[1;31m*** Invalid C/C++ Compiler Toolchain. Please check https://github.com/microsoft/vscode/wiki/How-to-Contribute#prerequisites.\x1b[0;0m');
diff --git a/build/package-lock.json b/build/package-lock.json
index b78c4c8389ac5..644e16f901b77 100644
--- a/build/package-lock.json
+++ b/build/package-lock.json
@@ -48,7 +48,7 @@
         "@types/workerpool": "^6.4.0",
         "@types/xml2js": "0.0.33",
         "@vscode/iconv-lite-umd": "0.7.1",
-        "@vscode/ripgrep": "^1.15.13",
+        "@vscode/ripgrep": "^1.17.1",
         "@vscode/vsce": "3.6.1",
         "ansi-colors": "^3.2.3",
         "byline": "^5.0.0",
@@ -1027,29 +1027,6 @@
         "node": ">=18"
       }
     },
-    "node_modules/@isaacs/balanced-match": {
-      "version": "4.0.1",
-      "resolved": "https://registry.npmjs.org/@isaacs/balanced-match/-/balanced-match-4.0.1.tgz",
-      "integrity": "sha512-yzMTt9lEb8Gv7zRioUilSglI0c0smZ9k5D65677DLWLtWJaXIS3CqcGyUFByYKlnUj6TkjLVs54fBl6+TiGQDQ==",
-      "dev": true,
-      "license": "MIT",
-      "engines": {
-        "node": "20 || >=22"
-      }
-    },
-    "node_modules/@isaacs/brace-expansion": {
-      "version": "5.0.0",
-      "resolved": "https://registry.npmjs.org/@isaacs/brace-expansion/-/brace-expansion-5.0.0.tgz",
-      "integrity": "sha512-ZT55BDLV0yv0RBm2czMiZ+SqCGO7AvmOM3G/w2xhVPH+te0aKgFjmBvGlL1dH+ql2tgGO3MVrbb3jCKyvpgnxA==",
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@@ -2170,6 +2147,29 @@
         "url": "https://github.com/chalk/ansi-styles?sponsor=1"
       }
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+      "resolved": "https://registry.npmjs.org/balanced-match/-/balanced-match-4.0.4.tgz",
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+      "license": "MIT",
+      "engines": {
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+    "node_modules/@vscode/vsce/node_modules/brace-expansion": {
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+      "resolved": "https://registry.npmjs.org/brace-expansion/-/brace-expansion-5.0.4.tgz",
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+      "license": "MIT",
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@@ -2232,16 +2232,16 @@
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+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.2.4.tgz",
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       "dev": true,
       "license": "BlueOak-1.0.0",
       "dependencies": {
-        "@isaacs/brace-expansion": "^5.0.0"
+        "brace-expansion": "^5.0.2"
       },
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-        "node": "20 || >=22"
+        "node": "18 || 20 || >=22"
       },
       "funding": {
         "url": "https://github.com/sponsors/isaacs"
@@ -2318,9 +2318,9 @@
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+      "version": "8.18.0",
+      "resolved": "https://registry.npmjs.org/ajv/-/ajv-8.18.0.tgz",
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@@ -3493,10 +3493,23 @@
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       "license": "BSD-3-Clause"
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+      "version": "1.0.0",
+      "resolved": "https://registry.npmjs.org/fast-xml-builder/-/fast-xml-builder-1.0.0.tgz",
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+      "dev": true,
+      "funding": [
+        {
+          "type": "github",
+          "url": "https://github.com/sponsors/NaturalIntelligence"
+        }
+      ],
+      "license": "MIT"
+    },
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-      "version": "5.3.6",
-      "resolved": "https://registry.npmjs.org/fast-xml-parser/-/fast-xml-parser-5.3.6.tgz",
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+      "version": "5.4.1",
+      "resolved": "https://registry.npmjs.org/fast-xml-parser/-/fast-xml-parser-5.4.1.tgz",
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       "dev": true,
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@@ -3506,6 +3519,7 @@
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       "license": "MIT",
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         "strnum": "^2.1.2"
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@@ -4512,9 +4526,9 @@
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@@ -6743,12 +6758,13 @@
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+      "version": "9.0.9",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-9.0.9.tgz",
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+        "brace-expansion": "^2.0.2"
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diff --git a/build/package.json b/build/package.json
index 785f04f3b22e3..8a65120c4d60e 100644
--- a/build/package.json
+++ b/build/package.json
@@ -42,7 +42,7 @@
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     "@types/xml2js": "0.0.33",
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-    "@vscode/ripgrep": "^1.15.13",
+    "@vscode/ripgrep": "^1.17.1",
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     "ansi-colors": "^3.2.3",
     "byline": "^5.0.0",
diff --git a/build/vite/package-lock.json b/build/vite/package-lock.json
index 4179138e714c7..72f036bc0dfbd 100644
--- a/build/vite/package-lock.json
+++ b/build/vite/package-lock.json
@@ -8,13 +8,166 @@
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-        "@vscode/component-explorer-vite-plugin": "^0.1.1-12",
+        "@vscode/component-explorer": "^0.1.1-24",
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         "rollup": "*",
         "vite": "npm:rolldown-vite@latest"
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+      "resolved": "https://registry.npmjs.org/@actions/exec/-/exec-1.1.1.tgz",
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+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
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+      "license": "MIT",
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+      "resolved": "https://registry.npmjs.org/@babel/code-frame/-/code-frame-7.12.11.tgz",
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+      "license": "MIT",
+      "engines": {
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+      }
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+    "node_modules/@babel/highlight/node_modules/has-flag": {
+      "version": "3.0.0",
+      "resolved": "https://registry.npmjs.org/has-flag/-/has-flag-3.0.0.tgz",
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+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=4"
+      }
+    },
+    "node_modules/@babel/highlight/node_modules/supports-color": {
+      "version": "5.5.0",
+      "resolved": "https://registry.npmjs.org/supports-color/-/supports-color-5.5.0.tgz",
+      "integrity": "sha512-QjVjwdXIt408MIiAqCX4oUKsgU2EqAGzs2Ppkm4aQYbjm+ZEWEcW4SfFNTr4uMNZma0ey4f5lgLrkB0aX0QMow==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
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     "node_modules/@emnapi/core": {
       "version": "1.8.1",
       "resolved": "https://registry.npmjs.org/@emnapi/core/-/core-1.8.1.tgz",
@@ -49,6 +202,65 @@
         "tslib": "^2.4.0"
       }
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+      "version": "0.4.3",
+      "resolved": "https://registry.npmjs.org/@eslint/eslintrc/-/eslintrc-0.4.3.tgz",
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+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "ajv": "^6.12.4",
+        "debug": "^4.1.1",
+        "espree": "^7.3.0",
+        "globals": "^13.9.0",
+        "ignore": "^4.0.6",
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+        "js-yaml": "^3.13.1",
+        "minimatch": "^3.0.4",
+        "strip-json-comments": "^3.1.1"
+      },
+      "engines": {
+        "node": "^10.12.0 || >=12.0.0"
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+    "node_modules/@hediet/semver": {
+      "version": "0.2.2",
+      "resolved": "https://registry.npmjs.org/@hediet/semver/-/semver-0.2.2.tgz",
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+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@actions/exec": "^1.0.4",
+        "@actions/github": "^2.2.0",
+        "@typescript-eslint/eslint-plugin": "^3.0.1",
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+      "version": "0.5.0",
+      "resolved": "https://registry.npmjs.org/@humanwhocodes/config-array/-/config-array-0.5.0.tgz",
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+      "deprecated": "Use @eslint/config-array instead",
+      "dev": true,
+      "license": "Apache-2.0",
+      "dependencies": {
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+        "debug": "^4.1.1",
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+      "deprecated": "Use @eslint/object-schema instead",
+      "dev": true,
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+      "dev": true,
+      "license": "MIT",
+      "engines": {
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+      }
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+      "resolved": "https://registry.npmjs.org/strip-json-comments/-/strip-json-comments-3.1.1.tgz",
+      "integrity": "sha512-6fPc+R4ihwqP6N/aIv2f1gMH8lOVtWQHoqC4yK6oSDVVocumAsfCqjkXnqiYMhmMwS/mEHLp7Vehlt3ql6lEig==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=8"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
+      }
+    },
+    "node_modules/supports-color": {
+      "version": "7.2.0",
+      "resolved": "https://registry.npmjs.org/supports-color/-/supports-color-7.2.0.tgz",
+      "integrity": "sha512-qpCAvRl9stuOHveKsn7HncJRvv501qIacKzQlO/+Lwxc9+0q2wLyv4Dfvt80/DPn2pqOBsJdDiogXGR9+OvwRw==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "has-flag": "^4.0.0"
+      },
+      "engines": {
+        "node": ">=8"
+      }
+    },
+    "node_modules/table": {
+      "version": "6.9.0",
+      "resolved": "https://registry.npmjs.org/table/-/table-6.9.0.tgz",
+      "integrity": "sha512-9kY+CygyYM6j02t5YFHbNz2FN5QmYGv9zAjVp4lCDjlCw7amdckXlEt/bjMhUIfj4ThGRE4gCUH5+yGnNuPo5A==",
+      "dev": true,
+      "license": "BSD-3-Clause",
+      "dependencies": {
+        "ajv": "^8.0.1",
+        "lodash.truncate": "^4.4.2",
+        "slice-ansi": "^4.0.0",
+        "string-width": "^4.2.3",
+        "strip-ansi": "^6.0.1"
+      },
+      "engines": {
+        "node": ">=10.0.0"
+      }
+    },
+    "node_modules/table/node_modules/ajv": {
+      "version": "8.18.0",
+      "resolved": "https://registry.npmjs.org/ajv/-/ajv-8.18.0.tgz",
+      "integrity": "sha512-PlXPeEWMXMZ7sPYOHqmDyCJzcfNrUr3fGNKtezX14ykXOEIvyK81d+qydx89KY5O71FKMPaQ2vBfBFI5NHR63A==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "fast-deep-equal": "^3.1.3",
+        "fast-uri": "^3.0.1",
+        "json-schema-traverse": "^1.0.0",
+        "require-from-string": "^2.0.2"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/epoberezkin"
+      }
+    },
+    "node_modules/table/node_modules/json-schema-traverse": {
+      "version": "1.0.0",
+      "resolved": "https://registry.npmjs.org/json-schema-traverse/-/json-schema-traverse-1.0.0.tgz",
+      "integrity": "sha512-NM8/P9n3XjXhIZn1lLhkFaACTOURQXjWhV4BA/RnOv8xvgqtqpAX9IO4mRQxSx1Rlo4tqzeqb0sOlruaOy3dug==",
+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/text-table": {
+      "version": "0.2.0",
+      "resolved": "https://registry.npmjs.org/text-table/-/text-table-0.2.0.tgz",
+      "integrity": "sha512-N+8UisAXDGk8PFXP4HAzVR9nbfmVJ3zYLAWiTIoqC5v5isinhr+r5uaO8+7r3BMfuNIufIsA7RdpVgacC2cSpw==",
+      "dev": true,
+      "license": "MIT"
+    },
     "node_modules/tinyglobby": {
       "version": "0.2.15",
       "resolved": "https://registry.npmjs.org/tinyglobby/-/tinyglobby-0.2.15.tgz",
@@ -1248,6 +3396,13 @@
         "url": "https://github.com/sponsors/SuperchupuDev"
       }
     },
+    "node_modules/tr46": {
+      "version": "0.0.3",
+      "resolved": "https://registry.npmjs.org/tr46/-/tr46-0.0.3.tgz",
+      "integrity": "sha512-N3WMsuqV66lT30CrXNbEjx4GEwlow3v6rr4mCcv6prnfwhS01rkgyFdjPNBYd9br7LpXV1+Emh01fHnq2Gdgrw==",
+      "dev": true,
+      "license": "MIT"
+    },
     "node_modules/tslib": {
       "version": "2.8.1",
       "resolved": "https://registry.npmjs.org/tslib/-/tslib-2.8.1.tgz",
@@ -1256,6 +3411,111 @@
       "license": "0BSD",
       "optional": true
     },
+    "node_modules/tsutils": {
+      "version": "3.21.0",
+      "resolved": "https://registry.npmjs.org/tsutils/-/tsutils-3.21.0.tgz",
+      "integrity": "sha512-mHKK3iUXL+3UF6xL5k0PEhKRUBKPBCv/+RkEOpjRWxxx27KKRBmmA60A9pgOUvMi8GKhRMPEmjBRPzs2W7O1OA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "tslib": "^1.8.1"
+      },
+      "engines": {
+        "node": ">= 6"
+      },
+      "peerDependencies": {
+        "typescript": ">=2.8.0 || >= 3.2.0-dev || >= 3.3.0-dev || >= 3.4.0-dev || >= 3.5.0-dev || >= 3.6.0-dev || >= 3.6.0-beta || >= 3.7.0-dev || >= 3.7.0-beta"
+      }
+    },
+    "node_modules/tsutils/node_modules/tslib": {
+      "version": "1.14.1",
+      "resolved": "https://registry.npmjs.org/tslib/-/tslib-1.14.1.tgz",
+      "integrity": "sha512-Xni35NKzjgMrwevysHTCArtLDpPvye8zV/0E4EyYn43P7/7qvQwPh9BGkHewbMulVntbigmcT7rdX3BNo9wRJg==",
+      "dev": true,
+      "license": "0BSD"
+    },
+    "node_modules/tunnel": {
+      "version": "0.0.6",
+      "resolved": "https://registry.npmjs.org/tunnel/-/tunnel-0.0.6.tgz",
+      "integrity": "sha512-1h/Lnq9yajKY2PEbBadPXj3VxsDDu844OnaAo52UVmIzIvwwtBPIuNvkjuzBlTWpfJyUbG3ez0KSBibQkj4ojg==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=0.6.11 <=0.7.0 || >=0.7.3"
+      }
+    },
+    "node_modules/type-check": {
+      "version": "0.4.0",
+      "resolved": "https://registry.npmjs.org/type-check/-/type-check-0.4.0.tgz",
+      "integrity": "sha512-XleUoc9uwGXqjWwXaUTZAmzMcFZ5858QA2vvx1Ur5xIcixXIP+8LnFDgRplU30us6teqdlskFfu+ae4K79Ooew==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "prelude-ls": "^1.2.1"
+      },
+      "engines": {
+        "node": ">= 0.8.0"
+      }
+    },
+    "node_modules/type-fest": {
+      "version": "0.20.2",
+      "resolved": "https://registry.npmjs.org/type-fest/-/type-fest-0.20.2.tgz",
+      "integrity": "sha512-Ne+eE4r0/iWnpAxD852z3A+N0Bt5RN//NjJwRd2VFHEmrywxf5vsZlh4R6lixl6B+wz/8d+maTSAkN1FIkI3LQ==",
+      "dev": true,
+      "license": "(MIT OR CC0-1.0)",
+      "engines": {
+        "node": ">=10"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
+      }
+    },
+    "node_modules/typescript": {
+      "version": "5.9.3",
+      "resolved": "https://registry.npmjs.org/typescript/-/typescript-5.9.3.tgz",
+      "integrity": "sha512-jl1vZzPDinLr9eUt3J/t7V6FgNEw9QjvBPdysz9KfQDD41fQrC2Y4vKQdiaUpFT4bXlb1RHhLpp8wtm6M5TgSw==",
+      "dev": true,
+      "license": "Apache-2.0",
+      "peer": true,
+      "bin": {
+        "tsc": "bin/tsc",
+        "tsserver": "bin/tsserver"
+      },
+      "engines": {
+        "node": ">=14.17"
+      }
+    },
+    "node_modules/undici-types": {
+      "version": "7.18.2",
+      "resolved": "https://registry.npmjs.org/undici-types/-/undici-types-7.18.2.tgz",
+      "integrity": "sha512-AsuCzffGHJybSaRrmr5eHr81mwJU3kjw6M+uprWvCXiNeN9SOGwQ3Jn8jb8m3Z6izVgknn1R0FTCEAP2QrLY/w==",
+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/universal-user-agent": {
+      "version": "6.0.1",
+      "resolved": "https://registry.npmjs.org/universal-user-agent/-/universal-user-agent-6.0.1.tgz",
+      "integrity": "sha512-yCzhz6FN2wU1NiiQRogkTQszlQSlpWaw8SvVegAc+bDxbzHgh1vX8uIe8OYyMH6DwH+sdTJsgMl36+mSMdRJIQ==",
+      "dev": true,
+      "license": "ISC"
+    },
+    "node_modules/uri-js": {
+      "version": "4.4.1",
+      "resolved": "https://registry.npmjs.org/uri-js/-/uri-js-4.4.1.tgz",
+      "integrity": "sha512-7rKUyy33Q1yc98pQ1DAmLtwX109F7TIfWlW1Ydo8Wl1ii1SeHieeh0HHfPeL2fMXK6z0s8ecKs9frCuLJvndBg==",
+      "dev": true,
+      "license": "BSD-2-Clause",
+      "dependencies": {
+        "punycode": "^2.1.0"
+      }
+    },
+    "node_modules/v8-compile-cache": {
+      "version": "2.4.0",
+      "resolved": "https://registry.npmjs.org/v8-compile-cache/-/v8-compile-cache-2.4.0.tgz",
+      "integrity": "sha512-ocyWc3bAHBB/guyqJQVI5o4BZkPhznPYUG2ea80Gond/BgNWpap8TOmLSeeQG7bnh2KMISxskdADG59j7zruhw==",
+      "dev": true,
+      "license": "MIT"
+    },
     "node_modules/vite": {
       "name": "rolldown-vite",
       "version": "7.3.1",
@@ -1332,6 +3592,73 @@
           "optional": true
         }
       }
+    },
+    "node_modules/webidl-conversions": {
+      "version": "3.0.1",
+      "resolved": "https://registry.npmjs.org/webidl-conversions/-/webidl-conversions-3.0.1.tgz",
+      "integrity": "sha512-2JAn3z8AR6rjK8Sm8orRC0h/bcl/DqL7tRPdGZ4I1CjdF+EaMLmYxBHyXuKL849eucPFhvBoxMsflfOb8kxaeQ==",
+      "dev": true,
+      "license": "BSD-2-Clause"
+    },
+    "node_modules/whatwg-url": {
+      "version": "5.0.0",
+      "resolved": "https://registry.npmjs.org/whatwg-url/-/whatwg-url-5.0.0.tgz",
+      "integrity": "sha512-saE57nupxk6v3HY35+jzBwYa0rKSy0XR8JSxZPwgLr7ys0IBzhGviA1/TUGJLmSVqs8pb9AnvICXEuOHLprYTw==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "tr46": "~0.0.3",
+        "webidl-conversions": "^3.0.0"
+      }
+    },
+    "node_modules/which": {
+      "version": "2.0.2",
+      "resolved": "https://registry.npmjs.org/which/-/which-2.0.2.tgz",
+      "integrity": "sha512-BLI3Tl1TW3Pvl70l3yq3Y64i+awpwXqsGBYWkkqMtnbXgrMD+yj7rhW0kuEDxzJaYXGjEW5ogapKNMEKNMjibA==",
+      "dev": true,
+      "license": "ISC",
+      "dependencies": {
+        "isexe": "^2.0.0"
+      },
+      "bin": {
+        "node-which": "bin/node-which"
+      },
+      "engines": {
+        "node": ">= 8"
+      }
+    },
+    "node_modules/windows-release": {
+      "version": "3.3.3",
+      "resolved": "https://registry.npmjs.org/windows-release/-/windows-release-3.3.3.tgz",
+      "integrity": "sha512-OSOGH1QYiW5yVor9TtmXKQvt2vjQqbYS+DqmsZw+r7xDwLXEeT3JGW0ZppFmHx4diyXmxt238KFR3N9jzevBRg==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "execa": "^1.0.0"
+      },
+      "engines": {
+        "node": ">=6"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
+      }
+    },
+    "node_modules/word-wrap": {
+      "version": "1.2.5",
+      "resolved": "https://registry.npmjs.org/word-wrap/-/word-wrap-1.2.5.tgz",
+      "integrity": "sha512-BN22B5eaMMI9UMtjrGd5g5eCYPpCPDUy0FJXbYsaT5zYxjFOckS53SQDE3pWkVoWpHXVb3BrYcEN4Twa55B5cA==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=0.10.0"
+      }
+    },
+    "node_modules/wrappy": {
+      "version": "1.0.2",
+      "resolved": "https://registry.npmjs.org/wrappy/-/wrappy-1.0.2.tgz",
+      "integrity": "sha512-l4Sp/DRseor9wL6EvV2+TuQn63dMkPjZ/sp9XkghTEbV9KlPS1xUsZ3u7/IQO4wxtcFB4bgpQPRcR3QCvezPcQ==",
+      "dev": true,
+      "license": "ISC"
     }
   }
 }
diff --git a/build/vite/package.json b/build/vite/package.json
index 245bf4fc8001a..05a96fa1ffd84 100644
--- a/build/vite/package.json
+++ b/build/vite/package.json
@@ -9,8 +9,8 @@
     "preview": "vite preview"
   },
   "devDependencies": {
-    "@vscode/component-explorer": "^0.1.1-12",
-    "@vscode/component-explorer-vite-plugin": "^0.1.1-12",
+    "@vscode/component-explorer": "^0.1.1-24",
+    "@vscode/component-explorer-vite-plugin": "^0.1.1-24",
     "@vscode/rollup-plugin-esm-url": "^1.0.1-1",
     "rollup": "*",
     "vite": "npm:rolldown-vite@latest"
diff --git a/build/vite/vite.config.ts b/build/vite/vite.config.ts
index cdae205f030df..24aaa12c02655 100644
--- a/build/vite/vite.config.ts
+++ b/build/vite/vite.config.ts
@@ -143,11 +143,8 @@ const logger = createLogger();
 const loggerWarn = logger.warn;
 
 logger.warn = (msg, options) => {
-	// amdX and the baseUrl code cannot be analyzed by vite.
-	// However, they are not needed, so it is okay to silence the warning.
-	if (msg.indexOf('vs/amdX.ts') !== -1) {
-		return;
-	}
+	// the baseUrl code cannot be analyzed by vite.
+	// However, it is not needed, so it is okay to silence the warning.
 	if (msg.indexOf('await import(new URL(`vs/workbench/workbench.desktop.main.js`, baseUrl).href)') !== -1) {
 		return;
 	}
diff --git a/build/win32/Cargo.lock b/build/win32/Cargo.lock
index d35c41e4098f9..bc102802568e8 100644
--- a/build/win32/Cargo.lock
+++ b/build/win32/Cargo.lock
@@ -3,93 +3,141 @@
 version = 4
 
 [[package]]
-name = "bitflags"
-version = "1.3.2"
+name = "android_system_properties"
+version = "0.1.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "bef38d45163c2f1dde094a7dfd33ccf595c92905c8f8f4fdc18d06fb1037718a"
+checksum = "819e7219dbd41043ac279b19830f2efc897156490d7fd6ea916720117ee66311"
+dependencies = [
+ "libc",
+]
+
+[[package]]
+name = "anyhow"
+version = "1.0.101"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5f0e0fee31ef5ed1ba1316088939cea399010ed7731dba877ed44aeb407a75ea"
+
+[[package]]
+name = "autocfg"
+version = "1.5.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "c08606f8c3cbf4ce6ec8e28fb0014a2c086708fe954eaa885384a6165172e7e8"
 
 [[package]]
 name = "bitflags"
-version = "2.9.1"
+version = "2.10.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "812e12b5285cc515a9c72a5c1d3b6d46a19dac5acfef5265968c166106e31dd3"
+
+[[package]]
+name = "bumpalo"
+version = "3.19.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "1b8e56985ec62d17e9c1001dc89c88ecd7dc08e47eba5ec7c29c7b5eeecde967"
+checksum = "5dd9dc738b7a8311c7ade152424974d8115f2cdad61e8dab8dac9f2362298510"
 
 [[package]]
 name = "byteorder"
-version = "1.4.3"
+version = "1.5.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "14c189c53d098945499cdfa7ecc63567cf3886b3332b312a5b4585d8d3a6a610"
+checksum = "1fd0f2584146f6f2ef48085050886acf353beff7305ebd1ae69500e27c67f64b"
+
+[[package]]
+name = "cc"
+version = "1.2.55"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "47b26a0954ae34af09b50f0de26458fa95369a0d478d8236d3f93082b219bd29"
+dependencies = [
+ "find-msvc-tools",
+ "shlex",
+]
 
 [[package]]
 name = "cfg-if"
-version = "1.0.0"
+version = "1.0.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9330f8b2ff13f34540b44e946ef35111825727b38d33286ef986142615121801"
+
+[[package]]
+name = "chrono"
+version = "0.4.43"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "fac4744fb15ae8337dc853fee7fb3f4e48c0fbaa23d0afe49c447b4fab126118"
+dependencies = [
+ "iana-time-zone",
+ "js-sys",
+ "num-traits",
+ "wasm-bindgen",
+ "windows-link",
+]
+
+[[package]]
+name = "core-foundation-sys"
+version = "0.8.7"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "baf1de4339761588bc0619e3cbc0120ee582ebb74b53b4efbf79117bd2da40fd"
+checksum = "773648b94d0e5d620f64f280777445740e61fe701025087ec8b57f45c791888b"
 
 [[package]]
 name = "crc"
-version = "3.0.1"
+version = "3.4.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "86ec7a15cbe22e59248fc7eadb1907dab5ba09372595da4d73dd805ed4417dfe"
+checksum = "5eb8a2a1cd12ab0d987a5d5e825195d372001a4094a0376319d5a0ad71c1ba0d"
 dependencies = [
  "crc-catalog",
 ]
 
 [[package]]
 name = "crc-catalog"
-version = "2.2.0"
+version = "2.4.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9cace84e55f07e7301bae1c519df89cdad8cc3cd868413d3fdbdeca9ff3db484"
+checksum = "19d374276b40fb8bbdee95aef7c7fa6b5316ec764510eb64b8dd0e2ed0d7e7f5"
 
 [[package]]
 name = "crossbeam-channel"
-version = "0.5.5"
+version = "0.5.15"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4c02a4d71819009c192cf4872265391563fd6a84c81ff2c0f2a7026ca4c1d85c"
+checksum = "82b8f8f868b36967f9606790d1903570de9ceaf870a7bf9fbbd3016d636a2cb2"
 dependencies = [
- "cfg-if",
  "crossbeam-utils",
 ]
 
 [[package]]
 name = "crossbeam-utils"
-version = "0.8.10"
+version = "0.8.21"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7d82ee10ce34d7bc12c2122495e7593a9c41347ecdd64185af4ecf72cb1a7f83"
-dependencies = [
- "cfg-if",
- "once_cell",
-]
+checksum = "d0a5c400df2834b80a4c3327b3aad3a4c4cd4de0629063962b03235697506a28"
 
 [[package]]
-name = "dirs-next"
-version = "2.0.0"
+name = "deranged"
+version = "0.5.6"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b98cf8ebf19c3d1b223e151f99a4f9f0690dca41414773390fc824184ac833e1"
+checksum = "cc3dc5ad92c2e2d1c193bbbbdf2ea477cb81331de4f3103f267ca18368b988c4"
 dependencies = [
- "cfg-if",
- "dirs-sys-next",
+ "powerfmt",
 ]
 
 [[package]]
-name = "dirs-sys-next"
-version = "0.1.2"
+name = "equivalent"
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-checksum = "4ebda144c4fe02d1f7ea1a7d9641b6fc6b580adcfa024ae48797ecdeb6825b4d"
+checksum = "877a4ace8713b0bcf2a4e7eec82529c029f1d0619886d18145fea96c3ffe5c0f"
+
+[[package]]
+name = "erased-serde"
+version = "0.3.31"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "6c138974f9d5e7fe373eb04df7cae98833802ae4b11c24ac7039a21d5af4b26c"
 dependencies = [
- "libc",
- "redox_users",
- "winapi",
+ "serde",
 ]
 
 [[package]]
 name = "errno"
-version = "0.3.13"
+version = "0.3.14"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "778e2ac28f6c47af28e4907f13ffd1e1ddbd400980a9abd7c8df189bf578a5ad"
+checksum = "39cab71617ae0d63f51a36d69f866391735b51691dbda63cf6f96d042b63efeb"
 dependencies = [
  "libc",
- "windows-sys 0.52.0",
+ "windows-sys 0.61.2",
 ]
 
 [[package]]
@@ -98,38 +146,103 @@ version = "2.3.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "37909eebbb50d72f9059c3b6d82c0463f2ff062c9e95845c43a6c9c0355411be"
 
+[[package]]
+name = "find-msvc-tools"
+version = "0.1.9"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5baebc0774151f905a1a2cc41989300b1e6fbb29aff0ceffa1064fdd3088d582"
+
+[[package]]
+name = "foldhash"
+version = "0.1.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d9c4f5dac5e15c24eb999c26181a6ca40b39fe946cbe4c263c7209467bc83af2"
+
 [[package]]
 name = "getrandom"
-version = "0.2.7"
+version = "0.4.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4eb1a864a501629691edf6c15a593b7a51eebaa1e8468e9ddc623de7c9b58ec6"
+checksum = "139ef39800118c7683f2fd3c98c1b23c09ae076556b435f8e9064ae108aaeeec"
 dependencies = [
  "cfg-if",
  "libc",
- "wasi 0.11.0+wasi-snapshot-preview1",
+ "r-efi",
+ "wasip2",
+ "wasip3",
 ]
 
 [[package]]
-name = "getrandom"
-version = "0.3.3"
+name = "hashbrown"
+version = "0.15.5"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "26145e563e54f2cadc477553f1ec5ee650b00862f0a58bcd12cbdc5f0ea2d2f4"
+checksum = "9229cfe53dfd69f0609a49f65461bd93001ea1ef889cd5529dd176593f5338a1"
 dependencies = [
- "cfg-if",
- "libc",
- "r-efi",
- "wasi 0.14.2+wasi-0.2.4",
+ "foldhash",
 ]
 
+[[package]]
+name = "hashbrown"
+version = "0.16.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "841d1cc9bed7f9236f321df977030373f4a4163ae1a7dbfe1a51a2c1a51d9100"
+
+[[package]]
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+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "2304e00983f87ffb38b55b444b5e3b60a884b5d30c0fca7d82fe33449bbe55ea"
+
 [[package]]
 name = "hermit-abi"
-version = "0.3.9"
+version = "0.5.2"
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-checksum = "d231dfb89cfffdbc30e7fc41579ed6066ad03abda9e567ccafae602b97ec5024"
+checksum = "fc0fef456e4baa96da950455cd02c081ca953b141298e41db3fc7e36b1da849c"
+
+[[package]]
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+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e31bc9ad994ba00e440a8aa5c9ef0ec67d5cb5e5cb0cc7f8b744a35b389cc470"
+dependencies = [
+ "android_system_properties",
+ "core-foundation-sys",
+ "iana-time-zone-haiku",
+ "js-sys",
+ "log",
+ "wasm-bindgen",
+ "windows-core",
+]
+
+[[package]]
+name = "iana-time-zone-haiku"
+version = "0.1.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f31827a206f56af32e590ba56d5d2d085f558508192593743f16b2306495269f"
+dependencies = [
+ "cc",
+]
+
+[[package]]
+name = "id-arena"
+version = "2.3.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3d3067d79b975e8844ca9eb072e16b31c3c1c36928edf9c6789548c524d0d954"
+
+[[package]]
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+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7714e70437a7dc3ac8eb7e6f8df75fd8eb422675fc7678aff7364301092b1017"
+dependencies = [
+ "equivalent",
+ "hashbrown 0.16.1",
+ "serde",
+ "serde_core",
+]
 
 [[package]]
 name = "inno_updater"
-version = "0.18.2"
+version = "0.19.0"
 dependencies = [
  "byteorder",
  "crc",
@@ -142,40 +255,74 @@ dependencies = [
 
 [[package]]
 name = "is-terminal"
-version = "0.4.12"
+version = "0.4.17"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "f23ff5ef2b80d608d61efee834934d862cd92461afc0560dedf493e4c033738b"
+checksum = "3640c1c38b8e4e43584d8df18be5fc6b0aa314ce6ebf51b53313d4306cca8e46"
 dependencies = [
  "hermit-abi",
  "libc",
- "windows-sys 0.52.0",
+ "windows-sys 0.61.2",
 ]
 
 [[package]]
 name = "itoa"
-version = "1.0.2"
+version = "1.0.17"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "92ecc6618181def0457392ccd0ee51198e065e016d1d527a7ac1b6dc7c1f09d2"
+
+[[package]]
+name = "js-sys"
+version = "0.3.85"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8c942ebf8e95485ca0d52d97da7c5a2c387d0e7f0ba4c35e93bfcaee045955b3"
+dependencies = [
+ "once_cell",
+ "wasm-bindgen",
+]
+
+[[package]]
+name = "leb128fmt"
+version = "0.1.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "112c678d4050afce233f4f2852bb2eb519230b3cf12f33585275537d7e41578d"
+checksum = "09edd9e8b54e49e587e4f6295a7d29c3ea94d469cb40ab8ca70b288248a81db2"
 
 [[package]]
 name = "libc"
-version = "0.2.174"
+version = "0.2.181"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "1171693293099992e19cddea4e8b849964e9846f4acee11b3948bcc337be8776"
+checksum = "459427e2af2b9c839b132acb702a1c654d95e10f8c326bfc2ad11310e458b1c5"
 
 [[package]]
 name = "linux-raw-sys"
-version = "0.9.4"
+version = "0.11.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "cd945864f07fe9f5371a27ad7b52a172b4b499999f1d97574c9fa68373937e12"
+checksum = "df1d3c3b53da64cf5760482273a98e575c651a67eec7f77df96b5b642de8f039"
 
 [[package]]
-name = "num_threads"
-version = "0.1.6"
+name = "log"
+version = "0.4.29"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "2819ce041d2ee131036f4fc9d6ae7ae125a3a40e97ba64d04fe799ad9dabbb44"
+checksum = "5e5032e24019045c762d3c0f28f5b6b8bbf38563a65908389bf7978758920897"
+
+[[package]]
+name = "memchr"
+version = "2.8.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f8ca58f447f06ed17d5fc4043ce1b10dd205e060fb3ce5b979b8ed8e59ff3f79"
+
+[[package]]
+name = "num-conv"
+version = "0.2.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "cf97ec579c3c42f953ef76dbf8d55ac91fb219dde70e49aa4a6b7d74e9919050"
+
+[[package]]
+name = "num-traits"
+version = "0.2.19"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "071dfc062690e90b734c0b2273ce72ad0ffa95f0c74596bc250dcfd960262841"
 dependencies = [
- "libc",
+ "autocfg",
 ]
 
 [[package]]
@@ -184,20 +331,36 @@ version = "1.21.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "42f5e15c9953c5e4ccceeb2e7382a716482c34515315f7b03532b8b4e8393d2d"
 
+[[package]]
+name = "powerfmt"
+version = "0.2.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "439ee305def115ba05938db6eb1644ff94165c5ab5e9420d1c1bcedbba909391"
+
+[[package]]
+name = "prettyplease"
+version = "0.2.37"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "479ca8adacdd7ce8f1fb39ce9ecccbfe93a3f1344b3d0d97f20bc0196208f62b"
+dependencies = [
+ "proc-macro2",
+ "syn",
+]
+
 [[package]]
 name = "proc-macro2"
-version = "1.0.40"
+version = "1.0.106"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "dd96a1e8ed2596c337f8eae5f24924ec83f5ad5ab21ea8e455d3566c69fbcaf7"
+checksum = "8fd00f0bb2e90d81d1044c2b32617f68fcb9fa3bb7640c23e9c748e53fb30934"
 dependencies = [
  "unicode-ident",
 ]
 
 [[package]]
 name = "quote"
-version = "1.0.20"
+version = "1.0.44"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "3bcdf212e9776fbcb2d23ab029360416bb1706b1aea2d1a5ba002727cbcab804"
+checksum = "21b2ebcf727b7760c461f091f9f0f539b77b8e87f2fd88131e7f1b433b3cece4"
 dependencies = [
  "proc-macro2",
 ]
@@ -209,55 +372,95 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "69cdb34c158ceb288df11e18b4bd39de994f6657d83847bdffdbd7f346754b0f"
 
 [[package]]
-name = "redox_syscall"
-version = "0.2.13"
+name = "rustix"
+version = "1.1.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "62f25bc4c7e55e0b0b7a1d43fb893f4fa1361d0abe38b9ce4f323c2adfe6ef42"
+checksum = "146c9e247ccc180c1f61615433868c99f3de3ae256a30a43b49f67c2d9171f34"
 dependencies = [
- "bitflags 1.3.2",
+ "bitflags",
+ "errno",
+ "libc",
+ "linux-raw-sys",
+ "windows-sys 0.61.2",
 ]
 
 [[package]]
-name = "redox_users"
-version = "0.4.3"
+name = "rustversion"
+version = "1.0.22"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b033d837a7cf162d7993aded9304e30a83213c648b6e389db233191f891e5c2b"
+checksum = "b39cdef0fa800fc44525c84ccb54a029961a8215f9619753635a9c0d2538d46d"
+
+[[package]]
+name = "semver"
+version = "1.0.27"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d767eb0aabc880b29956c35734170f26ed551a859dbd361d140cdbeca61ab1e2"
+
+[[package]]
+name = "serde"
+version = "1.0.228"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9a8e94ea7f378bd32cbbd37198a4a91436180c5bb472411e48b5ec2e2124ae9e"
 dependencies = [
- "getrandom 0.2.7",
- "redox_syscall",
- "thiserror",
+ "serde_core",
 ]
 
 [[package]]
-name = "rustix"
-version = "1.0.7"
+name = "serde_core"
+version = "1.0.228"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c71e83d6afe7ff64890ec6b71d6a69bb8a610ab78ce364b3352876bb4c801266"
+checksum = "41d385c7d4ca58e59fc732af25c3983b67ac852c1a25000afe1175de458b67ad"
 dependencies = [
- "bitflags 2.9.1",
- "errno",
- "libc",
- "linux-raw-sys",
- "windows-sys 0.52.0",
+ "serde_derive",
 ]
 
 [[package]]
-name = "rustversion"
-version = "1.0.7"
+name = "serde_derive"
+version = "1.0.228"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d540f220d3187173da220f885ab66608367b6574e925011a9353e4badda91d79"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn",
+]
+
+[[package]]
+name = "serde_json"
+version = "1.0.149"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "83fc039473c5595ace860d8c4fafa220ff474b3fc6bfdb4293327f1a37e94d86"
+dependencies = [
+ "itoa",
+ "memchr",
+ "serde",
+ "serde_core",
+ "zmij",
+]
+
+[[package]]
+name = "shlex"
+version = "1.3.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "a0a5f7c728f5d284929a1cccb5bc19884422bfe6ef4d6c409da2c41838983fcf"
+checksum = "0fda2ff0d084019ba4d7c6f371c95d8fd75ce3524c3cb8fb653a3023f6323e64"
 
 [[package]]
 name = "slog"
-version = "2.7.0"
+version = "2.8.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8347046d4ebd943127157b94d63abb990fcf729dc4e9978927fdf4ac3c998d06"
+checksum = "9b3b8565691b22d2bdfc066426ed48f837fc0c5f2c8cad8d9718f7f99d6995c1"
+dependencies = [
+ "anyhow",
+ "erased-serde",
+ "rustversion",
+ "serde_core",
+]
 
 [[package]]
 name = "slog-async"
-version = "2.7.0"
+version = "2.8.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "766c59b252e62a34651412870ff55d8c4e6d04df19b43eecb2703e417b097ffe"
+checksum = "72c8038f898a2c79507940990f05386455b3a317d8f18d4caea7cbc3d5096b84"
 dependencies = [
  "crossbeam-channel",
  "slog",
@@ -267,10 +470,11 @@ dependencies = [
 
 [[package]]
 name = "slog-term"
-version = "2.9.1"
+version = "2.9.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "b6e022d0b998abfe5c3782c1f03551a596269450ccd677ea51c56f8b214610e8"
+checksum = "5cb1fc680b38eed6fad4c02b3871c09d2c81db8c96aa4e9c0a34904c830f09b5"
 dependencies = [
+ "chrono",
  "is-terminal",
  "slog",
  "term",
@@ -280,9 +484,9 @@ dependencies = [
 
 [[package]]
 name = "syn"
-version = "1.0.98"
+version = "2.0.115"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c50aef8a904de4c23c788f104b7dddc7d6f79c647c7c8ce4cc8f73eb0ca773dd"
+checksum = "6e614ed320ac28113fa64972c4262d5dbc89deacdfd00c34a3e4cea073243c12"
 dependencies = [
  "proc-macro2",
  "quote",
@@ -297,156 +501,256 @@ checksum = "f764005d11ee5f36500a149ace24e00e3da98b0158b3e2d53a7495660d3f4d60"
 
 [[package]]
 name = "tempfile"
-version = "3.20.0"
+version = "3.25.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "e8a64e3985349f2441a1a9ef0b853f869006c3855f2cda6862a94d26ebb9d6a1"
+checksum = "0136791f7c95b1f6dd99f9cc786b91bb81c3800b639b3478e561ddb7be95e5f1"
 dependencies = [
  "fastrand",
- "getrandom 0.3.3",
+ "getrandom",
  "once_cell",
  "rustix",
- "windows-sys 0.52.0",
+ "windows-sys 0.61.2",
 ]
 
 [[package]]
 name = "term"
-version = "0.7.0"
+version = "1.2.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d8c27177b12a6399ffc08b98f76f7c9a1f4fe9fc967c784c5a071fa8d93cf7e1"
+dependencies = [
+ "windows-sys 0.61.2",
+]
+
+[[package]]
+name = "thread_local"
+version = "1.1.9"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f60246a4944f24f6e018aa17cdeffb7818b76356965d03b07d6a9886e8962185"
+dependencies = [
+ "cfg-if",
+]
+
+[[package]]
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+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "743bd48c283afc0388f9b8827b976905fb217ad9e647fae3a379a9283c4def2c"
+dependencies = [
+ "deranged",
+ "itoa",
+ "num-conv",
+ "powerfmt",
+ "serde_core",
+ "time-core",
+ "time-macros",
+]
+
+[[package]]
+name = "time-core"
+version = "0.1.8"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "c59df8ac95d96ff9bede18eb7300b0fda5e5d8d90960e76f8e14ae765eedbf1f"
+checksum = "7694e1cfe791f8d31026952abf09c69ca6f6fa4e1a1229e18988f06a04a12dca"
+
+[[package]]
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+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "2e70e4c5a0e0a8a4823ad65dfe1a6930e4f4d756dcd9dd7939022b5e8c501215"
 dependencies = [
- "dirs-next",
+ "num-conv",
+ "time-core",
+]
+
+[[package]]
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+source = "registry+https://github.com/rust-lang/crates.io-index"
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+
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+
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+checksum = "9517f9239f02c069db75e65f174b3da828fe5f5b945c4dd26bd25d89c03ebcf5"
+dependencies = [
+ "wit-bindgen",
+]
+
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+checksum = "5428f8bf88ea5ddc08faddef2ac4a67e390b88186c703ce6dbd955e1c145aca5"
+dependencies = [
+ "wit-bindgen",
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+
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+dependencies = [
+ "cfg-if",
+ "once_cell",
  "rustversion",
- "winapi",
+ "wasm-bindgen-macro",
+ "wasm-bindgen-shared",
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 [[package]]
-name = "thiserror"
-version = "1.0.31"
+name = "wasm-bindgen-macro"
+version = "0.2.108"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "bd829fe32373d27f76265620b5309d0340cb8550f523c1dda251d6298069069a"
+checksum = "008b239d9c740232e71bd39e8ef6429d27097518b6b30bdf9086833bd5b6d608"
 dependencies = [
- "thiserror-impl",
+ "quote",
+ "wasm-bindgen-macro-support",
 ]
 
 [[package]]
-name = "thiserror-impl"
-version = "1.0.31"
+name = "wasm-bindgen-macro-support"
+version = "0.2.108"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "0396bc89e626244658bef819e22d0cc459e795a5ebe878e6ec336d1674a8d79a"
+checksum = "5256bae2d58f54820e6490f9839c49780dff84c65aeab9e772f15d5f0e913a55"
 dependencies = [
+ "bumpalo",
  "proc-macro2",
  "quote",
  "syn",
+ "wasm-bindgen-shared",
 ]
 
 [[package]]
-name = "thread_local"
-version = "1.1.4"
+name = "wasm-bindgen-shared"
+version = "0.2.108"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5516c27b78311c50bf42c071425c560ac799b11c30b31f87e3081965fe5e0180"
+checksum = "1f01b580c9ac74c8d8f0c0e4afb04eeef2acf145458e52c03845ee9cd23e3d12"
 dependencies = [
- "once_cell",
+ "unicode-ident",
 ]
 
 [[package]]
-name = "time"
-version = "0.3.11"
+name = "wasm-encoder"
+version = "0.244.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "72c91f41dcb2f096c05f0873d667dceec1087ce5bcf984ec8ffb19acddbb3217"
+checksum = "990065f2fe63003fe337b932cfb5e3b80e0b4d0f5ff650e6985b1048f62c8319"
 dependencies = [
- "itoa",
- "libc",
- "num_threads",
- "time-macros",
+ "leb128fmt",
+ "wasmparser",
 ]
 
 [[package]]
-name = "time-macros"
-version = "0.2.4"
+name = "wasm-metadata"
+version = "0.244.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "42657b1a6f4d817cda8e7a0ace261fe0cc946cf3a80314390b22cc61ae080792"
+checksum = "bb0e353e6a2fbdc176932bbaab493762eb1255a7900fe0fea1a2f96c296cc909"
+dependencies = [
+ "anyhow",
+ "indexmap",
+ "wasm-encoder",
+ "wasmparser",
+]
 
 [[package]]
-name = "unicode-ident"
-version = "1.0.1"
+name = "wasmparser"
+version = "0.244.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5bd2fe26506023ed7b5e1e315add59d6f584c621d037f9368fea9cfb988f368c"
+checksum = "47b807c72e1bac69382b3a6fb3dbe8ea4c0ed87ff5629b8685ae6b9a611028fe"
+dependencies = [
+ "bitflags",
+ "hashbrown 0.15.5",
+ "indexmap",
+ "semver",
+]
 
 [[package]]
-name = "wasi"
-version = "0.11.0+wasi-snapshot-preview1"
+name = "windows-core"
+version = "0.62.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9c8d87e72b64a3b4db28d11ce29237c246188f4f51057d65a7eab63b7987e423"
+checksum = "b8e83a14d34d0623b51dce9581199302a221863196a1dde71a7663a4c2be9deb"
+dependencies = [
+ "windows-implement",
+ "windows-interface",
+ "windows-link",
+ "windows-result",
+ "windows-strings",
+]
 
 [[package]]
-name = "wasi"
-version = "0.14.2+wasi-0.2.4"
+name = "windows-implement"
+version = "0.60.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9683f9a5a998d873c0d21fcbe3c083009670149a8fab228644b8bd36b2c48cb3"
+checksum = "053e2e040ab57b9dc951b72c264860db7eb3b0200ba345b4e4c3b14f67855ddf"
 dependencies = [
- "wit-bindgen-rt",
+ "proc-macro2",
+ "quote",
+ "syn",
 ]
 
 [[package]]
-name = "winapi"
-version = "0.3.9"
+name = "windows-interface"
+version = "0.59.3"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5c839a674fcd7a98952e593242ea400abe93992746761e38641405d28b00f419"
+checksum = "3f316c4a2570ba26bbec722032c4099d8c8bc095efccdc15688708623367e358"
 dependencies = [
- "winapi-i686-pc-windows-gnu",
- "winapi-x86_64-pc-windows-gnu",
+ "proc-macro2",
+ "quote",
+ "syn",
 ]
 
 [[package]]
-name = "winapi-i686-pc-windows-gnu"
-version = "0.4.0"
+name = "windows-link"
+version = "0.2.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "ac3b87c63620426dd9b991e5ce0329eff545bccbbb34f3be09ff6fb6ab51b7b6"
+checksum = "f0805222e57f7521d6a62e36fa9163bc891acd422f971defe97d64e70d0a4fe5"
 
 [[package]]
-name = "winapi-x86_64-pc-windows-gnu"
-version = "0.4.0"
+name = "windows-result"
+version = "0.4.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "712e227841d057c1ee1cd2fb22fa7e5a5461ae8e48fa2ca79ec42cfc1931183f"
+checksum = "7781fa89eaf60850ac3d2da7af8e5242a5ea78d1a11c49bf2910bb5a73853eb5"
+dependencies = [
+ "windows-link",
+]
 
 [[package]]
-name = "windows-sys"
-version = "0.42.0"
+name = "windows-strings"
+version = "0.5.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "5a3e1820f08b8513f676f7ab6c1f99ff312fb97b553d30ff4dd86f9f15728aa7"
+checksum = "7837d08f69c77cf6b07689544538e017c1bfcf57e34b4c0ff58e6c2cd3b37091"
 dependencies = [
- "windows_aarch64_gnullvm 0.42.2",
- "windows_aarch64_msvc 0.42.2",
- "windows_i686_gnu 0.42.2",
- "windows_i686_msvc 0.42.2",
- "windows_x86_64_gnu 0.42.2",
- "windows_x86_64_gnullvm 0.42.2",
- "windows_x86_64_msvc 0.42.2",
+ "windows-link",
 ]
 
 [[package]]
 name = "windows-sys"
-version = "0.52.0"
+version = "0.42.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "282be5f36a8ce781fad8c8ae18fa3f9beff57ec1b52cb3de0789201425d9a33d"
+checksum = "5a3e1820f08b8513f676f7ab6c1f99ff312fb97b553d30ff4dd86f9f15728aa7"
 dependencies = [
- "windows-targets",
+ "windows_aarch64_gnullvm",
+ "windows_aarch64_msvc",
+ "windows_i686_gnu",
+ "windows_i686_msvc",
+ "windows_x86_64_gnu",
+ "windows_x86_64_gnullvm",
+ "windows_x86_64_msvc",
 ]
 
 [[package]]
-name = "windows-targets"
-version = "0.52.5"
+name = "windows-sys"
+version = "0.61.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6f0713a46559409d202e70e28227288446bf7841d3211583a4b53e3f6d96e7eb"
+checksum = "ae137229bcbd6cdf0f7b80a31df61766145077ddf49416a728b02cb3921ff3fc"
 dependencies = [
- "windows_aarch64_gnullvm 0.52.5",
- "windows_aarch64_msvc 0.52.5",
- "windows_i686_gnu 0.52.5",
- "windows_i686_gnullvm",
- "windows_i686_msvc 0.52.5",
- "windows_x86_64_gnu 0.52.5",
- "windows_x86_64_gnullvm 0.52.5",
- "windows_x86_64_msvc 0.52.5",
+ "windows-link",
 ]
 
 [[package]]
@@ -455,24 +759,12 @@ version = "0.42.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "597a5118570b68bc08d8d59125332c54f1ba9d9adeedeef5b99b02ba2b0698f8"
 
-[[package]]
-name = "windows_aarch64_gnullvm"
-version = "0.52.5"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "7088eed71e8b8dda258ecc8bac5fb1153c5cffaf2578fc8ff5d61e23578d3263"
-
 [[package]]
 name = "windows_aarch64_msvc"
 version = "0.42.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "e08e8864a60f06ef0d0ff4ba04124db8b0fb3be5776a5cd47641e942e58c4d43"
 
-[[package]]
-name = "windows_aarch64_msvc"
-version = "0.52.5"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9985fd1504e250c615ca5f281c3f7a6da76213ebd5ccc9561496568a2752afb6"
-
 [[package]]
 name = "windows_i686_gnu"
 version = "0.42.2"
@@ -480,70 +772,119 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "c61d927d8da41da96a81f029489353e68739737d3beca43145c8afec9a31a84f"
 
 [[package]]
-name = "windows_i686_gnu"
-version = "0.52.5"
-source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "88ba073cf16d5372720ec942a8ccbf61626074c6d4dd2e745299726ce8b89670"
-
-[[package]]
-name = "windows_i686_gnullvm"
-version = "0.52.5"
+name = "windows_i686_msvc"
+version = "0.42.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "87f4261229030a858f36b459e748ae97545d6f1ec60e5e0d6a3d32e0dc232ee9"
+checksum = "44d840b6ec649f480a41c8d80f9c65108b92d89345dd94027bfe06ac444d1060"
 
 [[package]]
-name = "windows_i686_msvc"
+name = "windows_x86_64_gnu"
 version = "0.42.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "44d840b6ec649f480a41c8d80f9c65108b92d89345dd94027bfe06ac444d1060"
+checksum = "8de912b8b8feb55c064867cf047dda097f92d51efad5b491dfb98f6bbb70cb36"
 
 [[package]]
-name = "windows_i686_msvc"
-version = "0.52.5"
+name = "windows_x86_64_gnullvm"
+version = "0.42.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "db3c2bf3d13d5b658be73463284eaf12830ac9a26a90c717b7f771dfe97487bf"
+checksum = "26d41b46a36d453748aedef1486d5c7a85db22e56aff34643984ea85514e94a3"
 
 [[package]]
-name = "windows_x86_64_gnu"
+name = "windows_x86_64_msvc"
 version = "0.42.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "8de912b8b8feb55c064867cf047dda097f92d51efad5b491dfb98f6bbb70cb36"
+checksum = "9aec5da331524158c6d1a4ac0ab1541149c0b9505fde06423b02f5ef0106b9f0"
 
 [[package]]
-name = "windows_x86_64_gnu"
-version = "0.52.5"
+name = "wit-bindgen"
+version = "0.51.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "4e4246f76bdeff09eb48875a0fd3e2af6aada79d409d33011886d3e1581517d9"
+checksum = "d7249219f66ced02969388cf2bb044a09756a083d0fab1e566056b04d9fbcaa5"
+dependencies = [
+ "wit-bindgen-rust-macro",
+]
 
 [[package]]
-name = "windows_x86_64_gnullvm"
-version = "0.42.2"
+name = "wit-bindgen-core"
+version = "0.51.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "26d41b46a36d453748aedef1486d5c7a85db22e56aff34643984ea85514e94a3"
+checksum = "ea61de684c3ea68cb082b7a88508a8b27fcc8b797d738bfc99a82facf1d752dc"
+dependencies = [
+ "anyhow",
+ "heck",
+ "wit-parser",
+]
 
 [[package]]
-name = "windows_x86_64_gnullvm"
-version = "0.52.5"
+name = "wit-bindgen-rust"
+version = "0.51.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "852298e482cd67c356ddd9570386e2862b5673c85bd5f88df9ab6802b334c596"
+checksum = "b7c566e0f4b284dd6561c786d9cb0142da491f46a9fbed79ea69cdad5db17f21"
+dependencies = [
+ "anyhow",
+ "heck",
+ "indexmap",
+ "prettyplease",
+ "syn",
+ "wasm-metadata",
+ "wit-bindgen-core",
+ "wit-component",
+]
 
 [[package]]
-name = "windows_x86_64_msvc"
-version = "0.42.2"
+name = "wit-bindgen-rust-macro"
+version = "0.51.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "9aec5da331524158c6d1a4ac0ab1541149c0b9505fde06423b02f5ef0106b9f0"
+checksum = "0c0f9bfd77e6a48eccf51359e3ae77140a7f50b1e2ebfe62422d8afdaffab17a"
+dependencies = [
+ "anyhow",
+ "prettyplease",
+ "proc-macro2",
+ "quote",
+ "syn",
+ "wit-bindgen-core",
+ "wit-bindgen-rust",
+]
 
 [[package]]
-name = "windows_x86_64_msvc"
-version = "0.52.5"
+name = "wit-component"
+version = "0.244.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "bec47e5bfd1bff0eeaf6d8b485cc1074891a197ab4225d504cb7a1ab88b02bf0"
+checksum = "9d66ea20e9553b30172b5e831994e35fbde2d165325bec84fc43dbf6f4eb9cb2"
+dependencies = [
+ "anyhow",
+ "bitflags",
+ "indexmap",
+ "log",
+ "serde",
+ "serde_derive",
+ "serde_json",
+ "wasm-encoder",
+ "wasm-metadata",
+ "wasmparser",
+ "wit-parser",
+]
 
 [[package]]
-name = "wit-bindgen-rt"
-version = "0.39.0"
+name = "wit-parser"
+version = "0.244.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
-checksum = "6f42320e61fe2cfd34354ecb597f86f413484a798ba44a8ca1165c58d42da6c1"
+checksum = "ecc8ac4bc1dc3381b7f59c34f00b67e18f910c2c0f50015669dde7def656a736"
 dependencies = [
- "bitflags 2.9.1",
+ "anyhow",
+ "id-arena",
+ "indexmap",
+ "log",
+ "semver",
+ "serde",
+ "serde_derive",
+ "serde_json",
+ "unicode-xid",
+ "wasmparser",
 ]
+
+[[package]]
+name = "zmij"
+version = "1.0.21"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b8848ee67ecc8aedbaf3e4122217aff892639231befc6a1b58d29fff4c2cabaa"
diff --git a/build/win32/Cargo.toml b/build/win32/Cargo.toml
index 40e1a7a60fddc..3e400552cc07d 100644
--- a/build/win32/Cargo.toml
+++ b/build/win32/Cargo.toml
@@ -1,6 +1,6 @@
 [package]
 name = "inno_updater"
-version = "0.18.2"
+version = "0.19.0"
 authors = ["Microsoft <monacotools@microsoft.com>"]
 build = "build.rs"
 
@@ -9,7 +9,7 @@ byteorder = "1.4.3"
 crc = "3.0.1"
 slog = "2.7.0"
 slog-async = "2.7.0"
-slog-term = "2.9.1"
+slog-term = "2.9.2"
 tempfile = "3.5.0"
 
 [target.'cfg(windows)'.dependencies.windows-sys]
diff --git a/build/win32/code.iss b/build/win32/code.iss
index f7091b28e5597..a61eef9c066e7 100644
--- a/build/win32/code.iss
+++ b/build/win32/code.iss
@@ -86,7 +86,7 @@ Type: files; Name: "{app}\updating_version"
 Name: "desktopicon"; Description: "{cm:CreateDesktopIcon}"; GroupDescription: "{cm:AdditionalIcons}"; Flags: unchecked
 Name: "quicklaunchicon"; Description: "{cm:CreateQuickLaunchIcon}"; GroupDescription: "{cm:AdditionalIcons}"; Flags: unchecked; OnlyBelowVersion: 0,6.1
 Name: "addcontextmenufiles"; Description: "{cm:AddContextMenuFiles,{#NameShort}}"; GroupDescription: "{cm:Other}"; Flags: unchecked
-Name: "addcontextmenufolders"; Description: "{cm:AddContextMenuFolders,{#NameShort}}"; GroupDescription: "{cm:Other}"; Flags: unchecked; Check: not ShouldUseWindows11ContextMenu
+Name: "addcontextmenufolders"; Description: "{cm:AddContextMenuFolders,{#NameShort}}"; GroupDescription: "{cm:Other}"; Flags: unchecked
 Name: "associatewithfiles"; Description: "{cm:AssociateWithFiles,{#NameShort}}"; GroupDescription: "{cm:Other}"
 Name: "addtopath"; Description: "{cm:AddToPath}"; GroupDescription: "{cm:Other}"
 Name: "runcode"; Description: "{cm:RunAfter,{#NameShort}}"; GroupDescription: "{cm:Other}"; Check: WizardSilent
@@ -95,9 +95,12 @@ Name: "runcode"; Description: "{cm:RunAfter,{#NameShort}}"; GroupDescription: "{
 Name: "{app}"; AfterInstall: DisableAppDirInheritance
 
 [Files]
-Source: "*"; Excludes: "\CodeSignSummary*.md,\tools,\tools\*,\policies,\policies\*,\appx,\appx\*,\resources\app\product.json,\{#ExeBasename}.exe,\{#ExeBasename}.VisualElementsManifest.xml,\bin,\bin\*"; DestDir: "{code:GetDestDir}"; Flags: ignoreversion recursesubdirs createallsubdirs
+Source: "*"; Excludes: "\CodeSignSummary*.md,\tools,\tools\*,\policies,\policies\*,\appx,\appx\*,\resources\app\product.json,\{#ExeBasename}.exe,{#ifdef ProxyExeBasename}\{#ProxyExeBasename}.exe,{#endif}\{#ExeBasename}.VisualElementsManifest.xml,\bin,\bin\*"; DestDir: "{code:GetDestDir}"; Flags: ignoreversion recursesubdirs createallsubdirs
 Source: "{#ExeBasename}.exe"; DestDir: "{code:GetDestDir}"; DestName: "{code:GetExeBasename}"; Flags: ignoreversion
 Source: "{#ExeBasename}.VisualElementsManifest.xml"; DestDir: "{code:GetDestDir}"; DestName: "{code:GetVisualElementsManifest}"; Flags: ignoreversion
+#ifdef ProxyExeBasename
+Source: "{#ProxyExeBasename}.exe"; DestDir: "{code:GetDestDir}"; DestName: "{code:GetProxyExeBasename}"; Flags: ignoreversion
+#endif
 Source: "tools\*"; DestDir: "{app}\{#VersionedResourcesFolder}\tools"; Flags: ignoreversion
 Source: "policies\*"; DestDir: "{code:GetDestDir}\{#VersionedResourcesFolder}\policies"; Flags: ignoreversion skipifsourcedoesntexist
 Source: "bin\{#TunnelApplicationName}.exe"; DestDir: "{code:GetDestDir}\bin"; DestName: "{code:GetBinDirTunnelApplicationFilename}"; Flags: ignoreversion skipifsourcedoesntexist
@@ -113,6 +116,11 @@ Source: "appx\{#AppxPackageDll}"; DestDir: "{code:GetDestDir}\{#VersionedResourc
 Name: "{group}\{#NameLong}"; Filename: "{app}\{#ExeBasename}.exe"; AppUserModelID: "{#AppUserId}"; Check: ShouldUpdateShortcut(ExpandConstant('{group}\{#NameLong}.lnk'))
 Name: "{autodesktop}\{#NameLong}"; Filename: "{app}\{#ExeBasename}.exe"; Tasks: desktopicon; AppUserModelID: "{#AppUserId}"; Check: ShouldUpdateShortcut(ExpandConstant('{autodesktop}\{#NameLong}.lnk'))
 Name: "{userappdata}\Microsoft\Internet Explorer\Quick Launch\{#NameLong}"; Filename: "{app}\{#ExeBasename}.exe"; Tasks: quicklaunchicon; AppUserModelID: "{#AppUserId}"; Check: ShouldUpdateShortcut(ExpandConstant('{userappdata}\Microsoft\Internet Explorer\Quick Launch\{#NameLong}.lnk'))
+#ifdef ProxyExeBasename
+Name: "{group}\{#ProxyExeBasename}"; Filename: "{app}\{#ProxyExeBasename}.exe"; AppUserModelID: "{#ProxyAppUserId}"; Check: ShouldUpdateShortcut(ExpandConstant('{group}\{#ProxyExeBasename}.lnk'))
+Name: "{autodesktop}\{#ProxyNameLong}"; Filename: "{app}\{#ProxyExeBasename}.exe"; Tasks: desktopicon; AppUserModelID: "{#ProxyAppUserId}"; Check: ShouldUpdateShortcut(ExpandConstant('{autodesktop}\{#ProxyNameLong}.lnk'))
+Name: "{userappdata}\Microsoft\Internet Explorer\Quick Launch\{#ProxyNameLong}"; Filename: "{app}\{#ProxyExeBasename}.exe"; Tasks: quicklaunchicon; AppUserModelID: "{#ProxyAppUserId}"; Check: ShouldUpdateShortcut(ExpandConstant('{userappdata}\Microsoft\Internet Explorer\Quick Launch\{#ProxyNameLong}.lnk'))
+#endif
 
 [Run]
 Filename: "{app}\{#ExeBasename}.exe"; Description: "{cm:LaunchProgram,{#NameLong}}"; Tasks: runcode; Flags: nowait postinstall; Check: ShouldRunAfterUpdate
@@ -1276,15 +1284,15 @@ Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\{#RegValueName}Contex
 Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\*\shell\{#RegValueName}"; ValueType: expandsz; ValueName: ""; ValueData: "{cm:OpenWithCodeContextMenu,{#ShellNameShort}}"; Tasks: addcontextmenufiles; Flags: uninsdeletekey; Check: not ShouldUseWindows11ContextMenu
 Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\*\shell\{#RegValueName}"; ValueType: expandsz; ValueName: "Icon"; ValueData: "{app}\{#ExeBasename}.exe"; Tasks: addcontextmenufiles; Check: not ShouldUseWindows11ContextMenu
 Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\*\shell\{#RegValueName}\command"; ValueType: expandsz; ValueName: ""; ValueData: """{app}\{#ExeBasename}.exe"" ""%1"""; Tasks: addcontextmenufiles; Check: not ShouldUseWindows11ContextMenu
-Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\directory\shell\{#RegValueName}"; ValueType: expandsz; ValueName: ""; ValueData: "{cm:OpenWithCodeContextMenu,{#ShellNameShort}}"; Tasks: addcontextmenufolders; Flags: uninsdeletekey; Check: not ShouldUseWindows11ContextMenu
-Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\directory\shell\{#RegValueName}"; ValueType: expandsz; ValueName: "Icon"; ValueData: "{app}\{#ExeBasename}.exe"; Tasks: addcontextmenufolders; Check: not ShouldUseWindows11ContextMenu
-Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\directory\shell\{#RegValueName}\command"; ValueType: expandsz; ValueName: ""; ValueData: """{app}\{#ExeBasename}.exe"" ""%V"""; Tasks: addcontextmenufolders; Check: not ShouldUseWindows11ContextMenu
-Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\directory\background\shell\{#RegValueName}"; ValueType: expandsz; ValueName: ""; ValueData: "{cm:OpenWithCodeContextMenu,{#ShellNameShort}}"; Tasks: addcontextmenufolders; Flags: uninsdeletekey; Check: not ShouldUseWindows11ContextMenu
-Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\directory\background\shell\{#RegValueName}"; ValueType: expandsz; ValueName: "Icon"; ValueData: "{app}\{#ExeBasename}.exe"; Tasks: addcontextmenufolders; Check: not ShouldUseWindows11ContextMenu
-Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\directory\background\shell\{#RegValueName}\command"; ValueType: expandsz; ValueName: ""; ValueData: """{app}\{#ExeBasename}.exe"" ""%V"""; Tasks: addcontextmenufolders; Check: not ShouldUseWindows11ContextMenu
-Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\Drive\shell\{#RegValueName}"; ValueType: expandsz; ValueName: ""; ValueData: "{cm:OpenWithCodeContextMenu,{#ShellNameShort}}"; Tasks: addcontextmenufolders; Flags: uninsdeletekey; Check: not ShouldUseWindows11ContextMenu
-Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\Drive\shell\{#RegValueName}"; ValueType: expandsz; ValueName: "Icon"; ValueData: "{app}\{#ExeBasename}.exe"; Tasks: addcontextmenufolders; Check: not ShouldUseWindows11ContextMenu
-Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\Drive\shell\{#RegValueName}\command"; ValueType: expandsz; ValueName: ""; ValueData: """{app}\{#ExeBasename}.exe"" ""%V"""; Tasks: addcontextmenufolders; Check: not ShouldUseWindows11ContextMenu
+Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\directory\shell\{#RegValueName}"; ValueType: expandsz; ValueName: ""; ValueData: "{cm:OpenWithCodeContextMenu,{#ShellNameShort}}"; Flags: uninsdeletekey; Check: ShouldInstallLegacyFolderContextMenu
+Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\directory\shell\{#RegValueName}"; ValueType: expandsz; ValueName: "Icon"; ValueData: "{app}\{#ExeBasename}.exe"; Check: ShouldInstallLegacyFolderContextMenu
+Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\directory\shell\{#RegValueName}\command"; ValueType: expandsz; ValueName: ""; ValueData: """{app}\{#ExeBasename}.exe"" ""%V"""; Check: ShouldInstallLegacyFolderContextMenu
+Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\directory\background\shell\{#RegValueName}"; ValueType: expandsz; ValueName: ""; ValueData: "{cm:OpenWithCodeContextMenu,{#ShellNameShort}}"; Flags: uninsdeletekey; Check: ShouldInstallLegacyFolderContextMenu
+Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\directory\background\shell\{#RegValueName}"; ValueType: expandsz; ValueName: "Icon"; ValueData: "{app}\{#ExeBasename}.exe"; Check: ShouldInstallLegacyFolderContextMenu
+Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\directory\background\shell\{#RegValueName}\command"; ValueType: expandsz; ValueName: ""; ValueData: """{app}\{#ExeBasename}.exe"" ""%V"""; Check: ShouldInstallLegacyFolderContextMenu
+Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\Drive\shell\{#RegValueName}"; ValueType: expandsz; ValueName: ""; ValueData: "{cm:OpenWithCodeContextMenu,{#ShellNameShort}}"; Flags: uninsdeletekey; Check: ShouldInstallLegacyFolderContextMenu
+Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\Drive\shell\{#RegValueName}"; ValueType: expandsz; ValueName: "Icon"; ValueData: "{app}\{#ExeBasename}.exe"; Check: ShouldInstallLegacyFolderContextMenu
+Root: {#SoftwareClassesRootKey}; Subkey: "Software\Classes\Drive\shell\{#RegValueName}\command"; ValueType: expandsz; ValueName: ""; ValueData: """{app}\{#ExeBasename}.exe"" ""%V"""; Check: ShouldInstallLegacyFolderContextMenu
 
 ; Environment
 #if "user" == InstallTarget
@@ -1519,6 +1527,68 @@ begin
   Result := IsWindows11OrLater() and not IsWindows10ContextMenuForced();
 end;
 
+function HasLegacyFileContextMenu(): Boolean;
+begin
+  Result := RegKeyExists({#EnvironmentRootKey}, 'Software\Classes\*\shell\{#RegValueName}\command');
+end;
+
+function HasLegacyFolderContextMenu(): Boolean;
+begin
+  Result := RegKeyExists({#EnvironmentRootKey}, 'Software\Classes\directory\shell\{#RegValueName}\command');
+end;
+
+function ShouldRepairFolderContextMenu(): Boolean;
+begin
+  // Repair folder context menu during updates if:
+  // 1. This is a background update (not a fresh install or manual re-install)
+  // 2. Windows 11+ with forced classic context menu
+  // 3. Legacy file context menu exists (user previously selected it)
+  // 4. Legacy folder context menu is MISSING
+  Result := IsBackgroundUpdate()
+    and IsWindows11OrLater()
+    and IsWindows10ContextMenuForced()
+    and HasLegacyFileContextMenu()
+    and not HasLegacyFolderContextMenu();
+end;
+
+function ShouldInstallLegacyFolderContextMenu(): Boolean;
+begin
+  Result := (WizardIsTaskSelected('addcontextmenufolders') and not ShouldUseWindows11ContextMenu()) or ShouldRepairFolderContextMenu();
+end;
+
+function BoolToStr(Value: Boolean): String;
+begin
+  if Value then
+    Result := 'true'
+  else
+    Result := 'false';
+end;
+
+procedure LogContextMenuInstallState();
+begin
+  Log(
+    'Context menu state: '
+    + 'isBackgroundUpdate=' + BoolToStr(IsBackgroundUpdate())
+    + ', isWindows11OrLater=' + BoolToStr(IsWindows11OrLater())
+    + ', isWindows10ContextMenuForced=' + BoolToStr(IsWindows10ContextMenuForced())
+    + ', shouldUseWindows11ContextMenu=' + BoolToStr(ShouldUseWindows11ContextMenu())
+    + ', hasLegacyFileContextMenu=' + BoolToStr(HasLegacyFileContextMenu())
+    + ', hasLegacyFolderContextMenu=' + BoolToStr(HasLegacyFolderContextMenu())
+    + ', shouldRepairFolderContextMenu=' + BoolToStr(ShouldRepairFolderContextMenu())
+    + ', shouldInstallLegacyFolderContextMenu=' + BoolToStr(ShouldInstallLegacyFolderContextMenu())
+    + ', addcontextmenufiles=' + BoolToStr(WizardIsTaskSelected('addcontextmenufiles'))
+    + ', addcontextmenufolders=' + BoolToStr(WizardIsTaskSelected('addcontextmenufolders'))
+  );
+end;
+
+procedure DeleteLegacyContextMenuRegistryKeys();
+begin
+  RegDeleteKeyIncludingSubkeys({#EnvironmentRootKey}, 'Software\Classes\*\shell\{#RegValueName}');
+  RegDeleteKeyIncludingSubkeys({#EnvironmentRootKey}, 'Software\Classes\directory\shell\{#RegValueName}');
+  RegDeleteKeyIncludingSubkeys({#EnvironmentRootKey}, 'Software\Classes\directory\background\shell\{#RegValueName}');
+  RegDeleteKeyIncludingSubkeys({#EnvironmentRootKey}, 'Software\Classes\Drive\shell\{#RegValueName}');
+end;
+
 function GetAppMutex(Value: string): string;
 begin
   if IsBackgroundUpdate() then
@@ -1562,6 +1632,16 @@ begin
     Result := ExpandConstant('{#ExeBasename}.exe');
 end;
 
+#ifdef ProxyExeBasename
+function GetProxyExeBasename(Value: string): string;
+begin
+  if IsBackgroundUpdate() and IsVersionedUpdate() then
+    Result := ExpandConstant('new_{#ProxyExeBasename}.exe')
+  else
+    Result := ExpandConstant('{#ProxyExeBasename}.exe');
+end;
+#endif
+
 function GetBinDirTunnelApplicationFilename(Value: string): string;
 begin
   if IsBackgroundUpdate() and IsVersionedUpdate() then
@@ -1586,14 +1666,6 @@ begin
     Result := ExpandConstant('{#ApplicationName}.cmd');
 end;
 
-function BoolToStr(Value: Boolean): String;
-begin
-  if Value then
-    Result := 'true'
-  else
-    Result := 'false';
-end;
-
 function QualityIsInsiders(): boolean;
 begin
   if '{#Quality}' = 'insider' then
@@ -1616,30 +1688,43 @@ end;
 function AppxPackageInstalled(const name: String; var ResultCode: Integer): Boolean;
 begin
   AppxPackageFullname := '';
+  ResultCode := -1;
   try
     Log('Get-AppxPackage for package with name: ' + name);
     ExecAndLogOutput('powershell.exe', '-NoLogo -NoProfile -NonInteractive -WindowStyle Hidden -ExecutionPolicy Bypass -Command ' + AddQuotes('Get-AppxPackage -Name ''' + name + ''' | Select-Object -ExpandProperty PackageFullName'), '', SW_HIDE, ewWaitUntilTerminated, ResultCode, @ExecAndGetFirstLineLog);
   except
     Log(GetExceptionMessage);
+    ResultCode := -1;
   end;
   if (AppxPackageFullname <> '') then
     Result := True
   else
-    Result := False
+    Result := False;
+
+  Log('Get-AppxPackage result: name=' + name + ', installed=' + BoolToStr(Result) + ', resultCode=' + IntToStr(ResultCode) + ', packageFullName=' + AppxPackageFullname);
 end;
 
 procedure AddAppxPackage();
 var
   AddAppxPackageResultCode: Integer;
+  IsCurrentAppxInstalled: Boolean;
 begin
-  if not SessionEndFileExists() and not AppxPackageInstalled(ExpandConstant('{#AppxPackageName}'), AddAppxPackageResultCode) then begin
+  if SessionEndFileExists() then begin
+    Log('Skipping Add-AppxPackage because session end was detected.');
+    exit;
+  end;
+
+  IsCurrentAppxInstalled := AppxPackageInstalled(ExpandConstant('{#AppxPackageName}'), AddAppxPackageResultCode);
+  if not IsCurrentAppxInstalled then begin
     Log('Installing appx ' + AppxPackageFullname + ' ...');
 #if "user" == InstallTarget
     ShellExec('', 'powershell.exe', '-NoLogo -NoProfile -NonInteractive -WindowStyle Hidden -ExecutionPolicy Bypass -Command ' + AddQuotes('Add-AppxPackage -Path ''' + ExpandConstant('{app}\{#VersionedResourcesFolder}\appx\{#AppxPackage}') + ''' -ExternalLocation ''' + ExpandConstant('{app}\{#VersionedResourcesFolder}\appx') + ''''), '', SW_HIDE, ewWaitUntilTerminated, AddAppxPackageResultCode);
 #else
     ShellExec('', 'powershell.exe', '-NoLogo -NoProfile -NonInteractive -WindowStyle Hidden -ExecutionPolicy Bypass -Command ' + AddQuotes('Add-AppxPackage -Stage ''' + ExpandConstant('{app}\{#VersionedResourcesFolder}\appx\{#AppxPackage}') + ''' -ExternalLocation ''' + ExpandConstant('{app}\{#VersionedResourcesFolder}\appx') + '''; Add-AppxProvisionedPackage -Online -SkipLicense -PackagePath ''' + ExpandConstant('{app}\{#VersionedResourcesFolder}\appx\{#AppxPackage}') + ''''), '', SW_HIDE, ewWaitUntilTerminated, AddAppxPackageResultCode);
 #endif
-    Log('Add-AppxPackage complete.');
+    Log('Add-AppxPackage complete with result code ' + IntToStr(AddAppxPackageResultCode) + '.');
+  end else begin
+    Log('Skipping Add-AppxPackage because package is already installed.');
   end;
 end;
 
@@ -1652,6 +1737,7 @@ begin
   if QualityIsInsiders() and not SessionEndFileExists() and AppxPackageInstalled('Microsoft.VSCodeInsiders', RemoveAppxPackageResultCode) then begin
     Log('Deleting old appx ' + AppxPackageFullname + ' installation...');
     ShellExec('', 'powershell.exe', '-NoLogo -NoProfile -NonInteractive -WindowStyle Hidden -ExecutionPolicy Bypass -Command ' + AddQuotes('Remove-AppxPackage -Package ''' + AppxPackageFullname + ''''), '', SW_HIDE, ewWaitUntilTerminated, RemoveAppxPackageResultCode);
+    Log('Remove-AppxPackage for old appx completed with result code ' + IntToStr(RemoveAppxPackageResultCode) + '.');
     DeleteFile(ExpandConstant('{app}\appx\code_insiders_explorer_{#Arch}.appx'));
     DeleteFile(ExpandConstant('{app}\appx\code_insiders_explorer_command.dll'));
   end;
@@ -1662,7 +1748,9 @@ begin
 #else
     ShellExec('', 'powershell.exe', '-NoLogo -NoProfile -NonInteractive -WindowStyle Hidden -ExecutionPolicy Bypass -Command ' + AddQuotes('$packages = Get-AppxPackage ''' + ExpandConstant('{#AppxPackageName}') + '''; foreach ($package in $packages) { Remove-AppxProvisionedPackage -PackageName $package.PackageFullName -Online }; foreach ($package in $packages) { Remove-AppxPackage -Package $package.PackageFullName -AllUsers }'), '', SW_HIDE, ewWaitUntilTerminated, RemoveAppxPackageResultCode);
 #endif
-    Log('Remove-AppxPackage for current appx installation complete.');
+    Log('Remove-AppxPackage for current appx installation complete with result code ' + IntToStr(RemoveAppxPackageResultCode) + '.');
+  end else if not SessionEndFileExists() then begin
+    Log('Skipping Remove-AppxPackage for current appx because package is not installed.');
   end;
 end;
 #endif
@@ -1674,6 +1762,8 @@ var
 begin
   if CurStep = ssPostInstall then
   begin
+    LogContextMenuInstallState();
+
 #ifdef AppxPackageName
     // Remove the appx package when user has forced Windows 10 context menus via
     // registry. This handles the case where the user previously had the appx
@@ -1683,10 +1773,7 @@ begin
     end;
     // Remove the old context menu registry keys
     if ShouldUseWindows11ContextMenu() then begin
-      RegDeleteKeyIncludingSubkeys({#EnvironmentRootKey}, 'Software\Classes\*\shell\{#RegValueName}');
-      RegDeleteKeyIncludingSubkeys({#EnvironmentRootKey}, 'Software\Classes\directory\shell\{#RegValueName}');
-      RegDeleteKeyIncludingSubkeys({#EnvironmentRootKey}, 'Software\Classes\directory\background\shell\{#RegValueName}');
-      RegDeleteKeyIncludingSubkeys({#EnvironmentRootKey}, 'Software\Classes\Drive\shell\{#RegValueName}');
+      DeleteLegacyContextMenuRegistryKeys();
     end;
 #endif
 
@@ -1799,6 +1886,7 @@ begin
   if not CurUninstallStep = usUninstall then begin
     exit;
   end;
+
 #ifdef AppxPackageName
   RemoveAppxPackage();
 #endif
diff --git a/build/win32/inno_updater.exe b/build/win32/inno_updater.exe
index c3c4a0cd2bcb8..424e997bde5b9 100644
Binary files a/build/win32/inno_updater.exe and b/build/win32/inno_updater.exe differ
diff --git a/cglicenses.json b/cglicenses.json
index 2b1bc6fece5b6..48d2c3b093c9c 100644
--- a/cglicenses.json
+++ b/cglicenses.json
@@ -306,11 +306,6 @@
 		"name": "russh-keys",
 		"fullLicenseTextUri": "https://raw.githubusercontent.com/warp-tech/russh/1da80d0d599b6ee2d257c544c0d6af4f649c9029/LICENSE-2.0.txt"
 	},
-	{
-		// Reason: license is in a subdirectory in repo
-		"name": "dirs-next",
-		"fullLicenseTextUri": "https://raw.githubusercontent.com/xdg-rs/dirs/af4aa39daba0ac68e222962a5aca17360158b7cc/dirs/LICENSE-MIT"
-	},
 	{
 		// Reason: license is in a subdirectory in repo
 		"name": "openssl",
@@ -361,10 +356,6 @@
 		"name": "toml_datetime",
 		"fullLicenseTextUri": "https://raw.githubusercontent.com/toml-rs/toml/main/crates/toml_datetime/LICENSE-MIT"
 	},
-	{ // License is MIT/Apache and tool doesn't look in subfolders
-		"name": "dirs-sys-next",
-		"fullLicenseTextUri": "https://raw.githubusercontent.com/xdg-rs/dirs/master/dirs-sys/LICENSE-MIT"
-	},
 	{ // License is MIT/Apache and gitlab API doesn't find the project
 		"name": "libredox",
 		"fullLicenseTextUri": "https://gitlab.redox-os.org/redox-os/libredox/-/raw/master/LICENSE"
@@ -707,64 +698,6 @@
 			"For more information, please refer to <http://unlicense.org>"
 		]
 	},
-	{
-		"name": "@isaacs/balanced-match",
-		"fullLicenseText": [
-			"MIT License",
-			"",
-			"Copyright Isaac Z. Schlueter <i@izs.me>",
-			"",
-			"Original code Copyright Julian Gruber <julian@juliangruber.com>",
-			"",
-			"Port to TypeScript Copyright Isaac Z. Schlueter <i@izs.me>",
-			"",
-			"Permission is hereby granted, free of charge, to any person obtaining a copy of",
-			"this software and associated documentation files (the \"Software\"), to deal in",
-			"the Software without restriction, including without limitation the rights to",
-			"use, copy, modify, merge, publish, distribute, sublicense, and/or sell copies",
-			"of the Software, and to permit persons to whom the Software is furnished to do",
-			"so, subject to the following conditions:",
-			"",
-			"The above copyright notice and this permission notice shall be included in all",
-			"copies or substantial portions of the Software.",
-			"",
-			"THE SOFTWARE IS PROVIDED \"AS IS\", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR",
-			"IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,",
-			"FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE",
-			"AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER",
-			"LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,",
-			"OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE",
-			"SOFTWARE.",
-			""
-		]
-	},
-	{
-		"name": "@isaacs/brace-expansion",
-		"fullLicenseText": [
-			"MIT License",
-			"",
-			"Copyright (c) 2013 Julian Gruber <julian@juliangruber.com>",
-			"",
-			"Permission is hereby granted, free of charge, to any person obtaining a copy",
-			"of this software and associated documentation files (the \"Software\"), to deal",
-			"in the Software without restriction, including without limitation the rights",
-			"to use, copy, modify, merge, publish, distribute, sublicense, and/or sell",
-			"copies of the Software, and to permit persons to whom the Software is",
-			"furnished to do so, subject to the following conditions:",
-			"",
-			"The above copyright notice and this permission notice shall be included in all",
-			"copies or substantial portions of the Software.",
-			"",
-			"THE SOFTWARE IS PROVIDED \"AS IS\", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR",
-			"IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,",
-			"FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE",
-			"AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER",
-			"LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,",
-			"OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE",
-			"SOFTWARE.",
-			""
-		]
-	},
 	{
 		// Reason: License file starts with (MIT) before the copyright, tool can't parse it
 		"name": "balanced-match",
diff --git a/cgmanifest.json b/cgmanifest.json
index 21554434500a7..1b1e1711ccfd8 100644
--- a/cgmanifest.json
+++ b/cgmanifest.json
@@ -529,13 +529,13 @@
 				"git": {
 					"name": "electron",
 					"repositoryUrl": "https://github.com/electron/electron",
-					"commitHash": "a229dbf7a56336b847b34dfff1bac79afc311eee",
-					"tag": "39.6.0"
+					"commitHash": "69c8cbf259da0f84e9c1db04958516a68f7170aa",
+					"tag": "39.8.0"
 				}
 			},
 			"isOnlyProductionDependency": true,
 			"license": "MIT",
-			"version": "39.6.0"
+			"version": "39.8.0"
 		},
 		{
 			"component": {
diff --git a/cli/Cargo.lock b/cli/Cargo.lock
index cd9b8de6afba6..afe353213b1b5 100644
--- a/cli/Cargo.lock
+++ b/cli/Cargo.lock
@@ -447,6 +447,7 @@ dependencies = [
  "uuid",
  "winapi",
  "winreg 0.50.0",
+ "winresource",
  "zbus",
  "zip",
 ]
@@ -2645,6 +2646,15 @@ dependencies = [
  "syn 2.0.115",
 ]
 
+[[package]]
+name = "serde_spanned"
+version = "1.0.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "f8bbf91e5a4d6315eee45e704372590b30e260ee83af6639d64557f51b067776"
+dependencies = [
+ "serde_core",
+]
+
 [[package]]
 name = "serde_urlencoded"
 version = "0.7.1"
@@ -3004,12 +3014,36 @@ dependencies = [
  "tokio",
 ]
 
+[[package]]
+name = "toml"
+version = "0.9.12+spec-1.1.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "cf92845e79fc2e2def6a5d828f0801e29a2f8acc037becc5ab08595c7d5e9863"
+dependencies = [
+ "indexmap 2.13.0",
+ "serde_core",
+ "serde_spanned",
+ "toml_datetime 0.7.5+spec-1.1.0",
+ "toml_parser",
+ "toml_writer",
+ "winnow 0.7.14",
+]
+
 [[package]]
 name = "toml_datetime"
 version = "0.6.11"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "22cddaf88f4fbc13c51aebbf5f8eceb5c7c5a9da2ac40a13519eb5b0a0e8f11c"
 
+[[package]]
+name = "toml_datetime"
+version = "0.7.5+spec-1.1.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "92e1cfed4a3038bc5a127e35a2d360f145e1f4b971b551a2ba5fd7aedf7e1347"
+dependencies = [
+ "serde_core",
+]
+
 [[package]]
 name = "toml_edit"
 version = "0.19.15"
@@ -3017,10 +3051,25 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "1b5bb770da30e5cbfde35a2d7b9b8a2c4b8ef89548a7a6aeab5c9a576e3e7421"
 dependencies = [
  "indexmap 2.13.0",
- "toml_datetime",
- "winnow",
+ "toml_datetime 0.6.11",
+ "winnow 0.5.40",
+]
+
+[[package]]
+name = "toml_parser"
+version = "1.0.9+spec-1.1.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "702d4415e08923e7e1ef96cd5727c0dfed80b4d2fa25db9647fe5eb6f7c5a4c4"
+dependencies = [
+ "winnow 0.7.14",
 ]
 
+[[package]]
+name = "toml_writer"
+version = "1.0.6+spec-1.1.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "ab16f14aed21ee8bfd8ec22513f7287cd4a91aa92e44edfe2c17ddd004e92607"
+
 [[package]]
 name = "tower-service"
 version = "0.3.3"
@@ -3699,6 +3748,12 @@ dependencies = [
  "memchr",
 ]
 
+[[package]]
+name = "winnow"
+version = "0.7.14"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5a5364e9d77fcdeeaa6062ced926ee3381faa2ee02d3eb83a5c27a8825540829"
+
 [[package]]
 name = "winreg"
 version = "0.8.0"
@@ -3718,6 +3773,16 @@ dependencies = [
  "windows-sys 0.48.0",
 ]
 
+[[package]]
+name = "winresource"
+version = "0.1.30"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e287ced0f21cd11f4035fe946fd3af145f068d1acb708afd248100f89ec7432d"
+dependencies = [
+ "toml",
+ "version_check",
+]
+
 [[package]]
 name = "wit-bindgen"
 version = "0.51.0"
diff --git a/cli/ThirdPartyNotices.txt b/cli/ThirdPartyNotices.txt
index 61cacaea79978..6e21ddb37297a 100644
--- a/cli/ThirdPartyNotices.txt
+++ b/cli/ThirdPartyNotices.txt
@@ -1666,7 +1666,6 @@ Unless you explicitly state otherwise, any contribution intentionally submitted
 [//]: # (crates)
 
 [`aead`]: ./aead
-[`async‑signature`]: ./signature/async
 [`cipher`]: ./cipher
 [`crypto‑common`]: ./crypto-common
 [`crypto`]: ./crypto
@@ -1828,7 +1827,6 @@ Unless you explicitly state otherwise, any contribution intentionally submitted
 [//]: # (crates)
 
 [`aead`]: ./aead
-[`async‑signature`]: ./signature/async
 [`cipher`]: ./cipher
 [`crypto‑common`]: ./crypto-common
 [`crypto`]: ./crypto
@@ -9189,6 +9187,32 @@ DEALINGS IN THE SOFTWARE.
 
 ---------------------------------------------------------
 
+serde_spanned 1.0.4 - MIT OR Apache-2.0
+https://github.com/toml-rs/toml
+
+Copyright (c) Individual contributors
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.
+---------------------------------------------------------
+
+---------------------------------------------------------
+
 serde_urlencoded 0.7.1 - MIT/Apache-2.0
 https://github.com/nox/serde_urlencoded
 
@@ -10517,7 +10541,34 @@ SOFTWARE.
 
 ---------------------------------------------------------
 
+toml 0.9.12+spec-1.1.0 - MIT OR Apache-2.0
+https://github.com/toml-rs/toml
+
+Copyright (c) Individual contributors
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.
+---------------------------------------------------------
+
+---------------------------------------------------------
+
 toml_datetime 0.6.11 - MIT OR Apache-2.0
+toml_datetime 0.7.5+spec-1.1.0 - MIT OR Apache-2.0
 https://github.com/toml-rs/toml
 
 ../../LICENSE-MIT
@@ -10533,6 +10584,58 @@ https://github.com/toml-rs/toml
 
 ---------------------------------------------------------
 
+toml_parser 1.0.9+spec-1.1.0 - MIT OR Apache-2.0
+https://github.com/toml-rs/toml
+
+Copyright (c) Individual contributors
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.
+---------------------------------------------------------
+
+---------------------------------------------------------
+
+toml_writer 1.0.6+spec-1.1.0 - MIT OR Apache-2.0
+https://github.com/toml-rs/toml
+
+Copyright (c) Individual contributors
+
+Permission is hereby granted, free of charge, to any person obtaining a copy
+of this software and associated documentation files (the "Software"), to deal
+in the Software without restriction, including without limitation the rights
+to use, copy, modify, merge, publish, distribute, sublicense, and/or sell
+copies of the Software, and to permit persons to whom the Software is
+furnished to do so, subject to the following conditions:
+
+The above copyright notice and this permission notice shall be included in all
+copies or substantial portions of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF ANY KIND, EXPRESS OR
+IMPLIED, INCLUDING BUT NOT LIMITED TO THE WARRANTIES OF MERCHANTABILITY,
+FITNESS FOR A PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT SHALL THE
+AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY CLAIM, DAMAGES OR OTHER
+LIABILITY, WHETHER IN AN ACTION OF CONTRACT, TORT OR OTHERWISE, ARISING FROM,
+OUT OF OR IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE
+SOFTWARE.
+---------------------------------------------------------
+
+---------------------------------------------------------
+
 tower-service 0.3.3 - MIT
 https://github.com/tower-rs/tower
 
@@ -12700,6 +12803,7 @@ MIT License
 ---------------------------------------------------------
 
 winnow 0.5.40 - MIT
+winnow 0.7.14 - MIT
 https://github.com/winnow-rs/winnow
 
 The MIT License (MIT)
@@ -12755,6 +12859,40 @@ THE SOFTWARE.
 
 ---------------------------------------------------------
 
+winresource 0.1.30 - MIT
+https://github.com/BenjaminRi/winresource
+
+The MIT License (MIT)
+
+Copyright 2016 Max Resch
+
+Permission is hereby granted, free of charge, to any
+person obtaining a copy of this software and associated
+documentation files (the "Software"), to deal in the
+Software without restriction, including without
+limitation the rights to use, copy, modify, merge,
+publish, distribute, sublicense, and/or sell copies of
+the Software, and to permit persons to whom the Software
+is furnished to do so, subject to the following
+conditions:
+
+The above copyright notice and this permission notice
+shall be included in all copies or substantial portions
+of the Software.
+
+THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF
+ANY KIND, EXPRESS OR IMPLIED, INCLUDING BUT NOT LIMITED
+TO THE WARRANTIES OF MERCHANTABILITY, FITNESS FOR A
+PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT
+SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY
+CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION
+OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR
+IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER
+DEALINGS IN THE SOFTWARE.
+---------------------------------------------------------
+
+---------------------------------------------------------
+
 wit-bindgen 0.51.0 - Apache-2.0 WITH LLVM-exception OR Apache-2.0 OR MIT
 https://github.com/bytecodealliance/wit-bindgen
 
@@ -13531,33 +13669,7 @@ ICU 1.8.1 to ICU 57.1 © 1995-2016 International Business Machines Corporation a
 zbus 3.15.2 - MIT
 https://github.com/z-galaxy/zbus/
 
-The MIT License (MIT)
-
-Copyright (c) 2024 Zeeshan Ali Khan & zbus contributors
-
-Permission is hereby granted, free of charge, to any
-person obtaining a copy of this software and associated
-documentation files (the "Software"), to deal in the
-Software without restriction, including without
-limitation the rights to use, copy, modify, merge,
-publish, distribute, sublicense, and/or sell copies of
-the Software, and to permit persons to whom the Software
-is furnished to do so, subject to the following
-conditions:
-
-The above copyright notice and this permission notice
-shall be included in all copies or substantial portions
-of the Software.
-
-THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF
-ANY KIND, EXPRESS OR IMPLIED, INCLUDING BUT NOT LIMITED
-TO THE WARRANTIES OF MERCHANTABILITY, FITNESS FOR A
-PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT
-SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY
-CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION
-OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR
-IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER
-DEALINGS IN THE SOFTWARE.
+LICENSE-MIT
 ---------------------------------------------------------
 
 ---------------------------------------------------------
@@ -13565,33 +13677,7 @@ DEALINGS IN THE SOFTWARE.
 zbus_macros 3.15.2 - MIT
 https://github.com/z-galaxy/zbus/
 
-The MIT License (MIT)
-
-Copyright (c) 2024 Zeeshan Ali Khan & zbus contributors
-
-Permission is hereby granted, free of charge, to any
-person obtaining a copy of this software and associated
-documentation files (the "Software"), to deal in the
-Software without restriction, including without
-limitation the rights to use, copy, modify, merge,
-publish, distribute, sublicense, and/or sell copies of
-the Software, and to permit persons to whom the Software
-is furnished to do so, subject to the following
-conditions:
-
-The above copyright notice and this permission notice
-shall be included in all copies or substantial portions
-of the Software.
-
-THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF
-ANY KIND, EXPRESS OR IMPLIED, INCLUDING BUT NOT LIMITED
-TO THE WARRANTIES OF MERCHANTABILITY, FITNESS FOR A
-PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT
-SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY
-CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION
-OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR
-IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER
-DEALINGS IN THE SOFTWARE.
+LICENSE-MIT
 ---------------------------------------------------------
 
 ---------------------------------------------------------
@@ -13599,33 +13685,7 @@ DEALINGS IN THE SOFTWARE.
 zbus_names 2.6.1 - MIT
 https://github.com/z-galaxy/zbus/
 
-The MIT License (MIT)
-
-Copyright (c) 2024 Zeeshan Ali Khan & zbus contributors
-
-Permission is hereby granted, free of charge, to any
-person obtaining a copy of this software and associated
-documentation files (the "Software"), to deal in the
-Software without restriction, including without
-limitation the rights to use, copy, modify, merge,
-publish, distribute, sublicense, and/or sell copies of
-the Software, and to permit persons to whom the Software
-is furnished to do so, subject to the following
-conditions:
-
-The above copyright notice and this permission notice
-shall be included in all copies or substantial portions
-of the Software.
-
-THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF
-ANY KIND, EXPRESS OR IMPLIED, INCLUDING BUT NOT LIMITED
-TO THE WARRANTIES OF MERCHANTABILITY, FITNESS FOR A
-PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT
-SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY
-CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION
-OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR
-IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER
-DEALINGS IN THE SOFTWARE.
+LICENSE-MIT
 ---------------------------------------------------------
 
 ---------------------------------------------------------
@@ -14071,33 +14131,7 @@ DEALINGS IN THE SOFTWARE.
 zvariant 3.15.2 - MIT
 https://github.com/z-galaxy/zbus/
 
-The MIT License (MIT)
-
-Copyright (c) 2024 Zeeshan Ali Khan & zbus contributors
-
-Permission is hereby granted, free of charge, to any
-person obtaining a copy of this software and associated
-documentation files (the "Software"), to deal in the
-Software without restriction, including without
-limitation the rights to use, copy, modify, merge,
-publish, distribute, sublicense, and/or sell copies of
-the Software, and to permit persons to whom the Software
-is furnished to do so, subject to the following
-conditions:
-
-The above copyright notice and this permission notice
-shall be included in all copies or substantial portions
-of the Software.
-
-THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF
-ANY KIND, EXPRESS OR IMPLIED, INCLUDING BUT NOT LIMITED
-TO THE WARRANTIES OF MERCHANTABILITY, FITNESS FOR A
-PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT
-SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY
-CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION
-OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR
-IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER
-DEALINGS IN THE SOFTWARE.
+LICENSE-MIT
 ---------------------------------------------------------
 
 ---------------------------------------------------------
@@ -14105,33 +14139,7 @@ DEALINGS IN THE SOFTWARE.
 zvariant_derive 3.15.2 - MIT
 https://github.com/z-galaxy/zbus/
 
-The MIT License (MIT)
-
-Copyright (c) 2024 Zeeshan Ali Khan & zbus contributors
-
-Permission is hereby granted, free of charge, to any
-person obtaining a copy of this software and associated
-documentation files (the "Software"), to deal in the
-Software without restriction, including without
-limitation the rights to use, copy, modify, merge,
-publish, distribute, sublicense, and/or sell copies of
-the Software, and to permit persons to whom the Software
-is furnished to do so, subject to the following
-conditions:
-
-The above copyright notice and this permission notice
-shall be included in all copies or substantial portions
-of the Software.
-
-THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF
-ANY KIND, EXPRESS OR IMPLIED, INCLUDING BUT NOT LIMITED
-TO THE WARRANTIES OF MERCHANTABILITY, FITNESS FOR A
-PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT
-SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY
-CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION
-OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR
-IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER
-DEALINGS IN THE SOFTWARE.
+LICENSE-MIT
 ---------------------------------------------------------
 
 ---------------------------------------------------------
@@ -14139,31 +14147,5 @@ DEALINGS IN THE SOFTWARE.
 zvariant_utils 1.0.1 - MIT
 https://github.com/z-galaxy/zbus/
 
-The MIT License (MIT)
-
-Copyright (c) 2024 Zeeshan Ali Khan & zbus contributors
-
-Permission is hereby granted, free of charge, to any
-person obtaining a copy of this software and associated
-documentation files (the "Software"), to deal in the
-Software without restriction, including without
-limitation the rights to use, copy, modify, merge,
-publish, distribute, sublicense, and/or sell copies of
-the Software, and to permit persons to whom the Software
-is furnished to do so, subject to the following
-conditions:
-
-The above copyright notice and this permission notice
-shall be included in all copies or substantial portions
-of the Software.
-
-THE SOFTWARE IS PROVIDED "AS IS", WITHOUT WARRANTY OF
-ANY KIND, EXPRESS OR IMPLIED, INCLUDING BUT NOT LIMITED
-TO THE WARRANTIES OF MERCHANTABILITY, FITNESS FOR A
-PARTICULAR PURPOSE AND NONINFRINGEMENT. IN NO EVENT
-SHALL THE AUTHORS OR COPYRIGHT HOLDERS BE LIABLE FOR ANY
-CLAIM, DAMAGES OR OTHER LIABILITY, WHETHER IN AN ACTION
-OF CONTRACT, TORT OR OTHERWISE, ARISING FROM, OUT OF OR
-IN CONNECTION WITH THE SOFTWARE OR THE USE OR OTHER
-DEALINGS IN THE SOFTWARE.
+LICENSE-MIT
 ---------------------------------------------------------
\ No newline at end of file
diff --git a/eslint.config.js b/eslint.config.js
index 93a8a1b7b4396..5dadd67e26ec6 100644
--- a/eslint.config.js
+++ b/eslint.config.js
@@ -828,6 +828,36 @@ export default tseslint.config(
 			]
 		}
 	},
+	// git extension - ban non-type imports from git.d.ts (use git.constants for runtime values)
+	{
+		files: [
+			'extensions/git/src/**/*.ts',
+		],
+		ignores: [
+			'extensions/git/src/api/git.constants.ts',
+		],
+		languageOptions: {
+			parser: tseslint.parser,
+		},
+		plugins: {
+			'@typescript-eslint': tseslint.plugin,
+		},
+		rules: {
+			'no-restricted-imports': 'off',
+			'@typescript-eslint/no-restricted-imports': [
+				'warn',
+				{
+					'patterns': [
+						{
+							'group': ['*/api/git'],
+							'allowTypeImports': true,
+							'message': 'Use \'import type\' for types from git.d.ts and import runtime const enum values from git.constants instead'
+						},
+					]
+				}
+			]
+		}
+	},
 	// vscode API
 	{
 		files: [
@@ -1426,6 +1456,7 @@ export default tseslint.config(
 					// - electron-main
 					'when': 'hasNode',
 					'allow': [
+						'@anthropic-ai/sandbox-runtime',
 						'@parcel/watcher',
 						'@vscode/sqlite3',
 						'@vscode/vscode-languagedetection',
@@ -1935,6 +1966,7 @@ export default tseslint.config(
 						'vs/editor/contrib/*/~',
 						'vs/editor/editor.all.js',
 						'vs/sessions/~',
+						'vs/sessions/services/*/~',
 						'vs/sessions/contrib/*/~',
 						'vs/workbench/~',
 						'vs/workbench/api/~',
@@ -1943,6 +1975,75 @@ export default tseslint.config(
 						'vs/sessions/sessions.common.main.js'
 					]
 				},
+				{
+					'target': 'src/vs/sessions/sessions.web.main.ts',
+					'layer': 'browser',
+					'restrictions': [
+						'vs/base/*/~',
+						'vs/base/parts/*/~',
+						'vs/platform/*/~',
+						'vs/editor/~',
+						'vs/editor/contrib/*/~',
+						'vs/editor/editor.all.js',
+						'vs/sessions/~',
+						'vs/sessions/services/*/~',
+						'vs/sessions/contrib/*/~',
+						'vs/workbench/~',
+						'vs/workbench/api/~',
+						'vs/workbench/services/*/~',
+						'vs/workbench/contrib/*/~',
+						'vs/sessions/sessions.common.main.js'
+					]
+				},
+				{
+					'target': 'src/vs/sessions/sessions.web.main.internal.ts',
+					'layer': 'browser',
+					'restrictions': [
+						'vs/base/~',
+						'vs/base/parts/*/~',
+						'vs/platform/*/~',
+						'vs/sessions/~',
+						'vs/sessions/contrib/*/~',
+						'vs/workbench/~',
+						'vs/workbench/browser/**',
+						'vs/workbench/services/*/~',
+						'vs/workbench/contrib/*/~',
+						'vs/sessions/sessions.web.main.js'
+					]
+				},
+				{
+					'target': 'src/vs/sessions/test/sessions.web.test.internal.ts',
+					'layer': 'browser',
+					'restrictions': [
+						'vs/base/~',
+						'vs/base/parts/*/~',
+						'vs/platform/*/~',
+						'vs/sessions/~',
+						'vs/sessions/test/**',
+						'vs/sessions/contrib/*/~',
+						'vs/workbench/~',
+						'vs/workbench/browser/**',
+						'vs/workbench/services/*/~',
+						'vs/workbench/contrib/*/~',
+						'vs/sessions/sessions.web.main.js'
+					]
+				},
+				{
+					'target': 'src/vs/sessions/test/{web.test.ts,web.test.factory.ts}',
+					'layer': 'browser',
+					'restrictions': [
+						'vs/base/~',
+						'vs/base/parts/*/~',
+						'vs/platform/*/~',
+						'vs/sessions/~',
+						'vs/sessions/test/**',
+						'vs/sessions/contrib/*/~',
+						'vs/workbench/~',
+						'vs/workbench/browser/**',
+						'vs/workbench/services/*/~',
+						'vs/workbench/contrib/*/~'
+					]
+				},
 				{
 					'target': 'src/vs/sessions/~',
 					'restrictions': [
@@ -1955,7 +2056,8 @@ export default tseslint.config(
 						'vs/workbench/browser/**',
 						'vs/workbench/contrib/**',
 						'vs/workbench/services/*/~',
-						'vs/sessions/~'
+						'vs/sessions/~',
+						'vs/sessions/services/*/~'
 					]
 				},
 				{
@@ -1974,6 +2076,32 @@ export default tseslint.config(
 						'vs/sessions/contrib/*/~'
 					]
 				},
+				{
+					'target': 'src/vs/sessions/services/*/~',
+					'restrictions': [
+						'vs/base/~',
+						'vs/base/parts/*/~',
+						'vs/platform/*/~',
+						'vs/editor/~',
+						'vs/editor/contrib/*/~',
+						'vs/workbench/~',
+						'vs/workbench/services/*/~',
+						'vs/sessions/~',
+						'vs/sessions/services/*/~',
+						{
+							'when': 'test',
+							'pattern': 'vs/workbench/contrib/*/~'
+						}, // TODO@layers
+						'tas-client', // node module allowed even in /common/
+						'vscode-textmate', // node module allowed even in /common/
+						'@vscode/vscode-languagedetection', // node module allowed even in /common/
+						'@vscode/tree-sitter-wasm', // type import
+						{
+							'when': 'hasBrowser',
+							'pattern': '@xterm/xterm'
+						} // node module allowed even in /browser/
+					]
+				},
 			]
 		}
 	},
@@ -2147,21 +2275,13 @@ export default tseslint.config(
 			'@typescript-eslint': tseslint.plugin,
 		},
 		rules: {
-			'@typescript-eslint/naming-convention': [
+			'no-restricted-syntax': [
 				'warn',
 				{
-					'selector': 'default',
-					'modifiers': ['private'],
-					'format': null,
-					'leadingUnderscore': 'require'
+					selector: ':matches(PropertyDefinition, TSParameterProperty, MethodDefinition[key.name!="constructor"])[accessibility="private"]',
+					message: 'Use #private instead',
 				},
-				{
-					'selector': 'default',
-					'modifiers': ['public'],
-					'format': null,
-					'leadingUnderscore': 'forbid'
-				}
-			]
+			],
 		}
 	},
 	// Additional extension strictness rules
@@ -2227,5 +2347,4 @@ export default tseslint.config(
 				},
 			],
 		}
-	},
-);
+	});
diff --git a/extensions/CONTRIBUTING.md b/extensions/CONTRIBUTING.md
new file mode 100644
index 0000000000000..cfaf6b0ca8dc1
--- /dev/null
+++ b/extensions/CONTRIBUTING.md
@@ -0,0 +1,32 @@
+# Contributing to Built-In Extensions
+
+This directory contains built-in extensions that ship with VS Code.
+
+## Basic Structure
+
+A typical TypeScript-based built-in extension has the following structure:
+
+- `package.json`: extension manifest.
+- `src/`: Main directory for TypeScript source code.
+- `tsconfig.json`: primary TypeScript config. This should inherit from `tsconfig.base.json`.
+- `esbuild.mts`: esbuild build script used for production builds.
+- `.vscodeignore`: Ignore file list. You can copy this from an existing extension.
+
+TypeScript-based extensions have the following output structure:
+
+- `out`: Output directory for development builds
+- `dist`: Output directory for production builds.
+
+
+## Enabling an Extension in the Browser
+
+By default extensions will only target desktop. To enable an extension in browsers as well:
+
+- Add a `"browser"` entry in `package.json` pointing to the browser bundle (for example `"./dist/browser/extension"`).
+- Add `tsconfig.browser.json` that typechecks only browser-safe sources.
+- Add an `esbuild.browser.mts` file. This should set `platform: 'browser'`.
+
+Make sure the browser build of the extension only uses browser-safe APIs. If an extension needs different behavior between desktop and web, you can create distinct entrypoints for each target:
+
+- `src/extension.ts`: Desktop entrypoint.
+- `src/extension.browser.ts`: Browser entrypoint. Make sure `esbuild.browser.mts` builds this and that `tsconfig.browser.json` targets it.
diff --git a/extensions/css-language-features/package-lock.json b/extensions/css-language-features/package-lock.json
index 231eda54dba77..e5cf7c26d199e 100644
--- a/extensions/css-language-features/package-lock.json
+++ b/extensions/css-language-features/package-lock.json
@@ -51,9 +51,9 @@
       }
     },
     "node_modules/minimatch": {
-      "version": "10.2.2",
-      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.2.2.tgz",
-      "integrity": "sha512-+G4CpNBxa5MprY+04MbgOw1v7So6n5JY166pFi9KfYwT78fxScCeSNQSNzp6dpPSW2rONOps6Ocam1wFhCgoVw==",
+      "version": "10.2.4",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.2.4.tgz",
+      "integrity": "sha512-oRjTw/97aTBN0RHbYCdtF1MQfvusSIBQM0IZEgzl6426+8jSC0nF1a/GmnVLpfB9yyr6g6FTqWqiZVbxrtaCIg==",
       "license": "BlueOak-1.0.0",
       "dependencies": {
         "brace-expansion": "^5.0.2"
diff --git a/extensions/css-language-features/package.json b/extensions/css-language-features/package.json
index 1fd31eeae793b..0abce3a2cfb48 100644
--- a/extensions/css-language-features/package.json
+++ b/extensions/css-language-features/package.json
@@ -218,7 +218,7 @@
             },
             "scope": "resource",
             "default": [],
-            "description": "%css.lint.validProperties.desc%"
+            "markdownDescription": "%css.lint.validProperties.desc%"
           },
           "css.lint.ieHack": {
             "type": "string",
@@ -534,7 +534,7 @@
             },
             "scope": "resource",
             "default": [],
-            "description": "%scss.lint.validProperties.desc%"
+            "markdownDescription": "%scss.lint.validProperties.desc%"
           },
           "scss.lint.ieHack": {
             "type": "string",
@@ -840,7 +840,7 @@
             },
             "scope": "resource",
             "default": [],
-            "description": "%less.lint.validProperties.desc%"
+            "markdownDescription": "%less.lint.validProperties.desc%"
           },
           "less.lint.ieHack": {
             "type": "string",
diff --git a/extensions/css-language-features/package.nls.json b/extensions/css-language-features/package.nls.json
index 057ec214bc2f8..d3de22412c286 100644
--- a/extensions/css-language-features/package.nls.json
+++ b/extensions/css-language-features/package.nls.json
@@ -33,7 +33,7 @@
 	"css.format.enable.desc": "Enable/disable default CSS formatter.",
 	"css.format.newlineBetweenSelectors.desc": "Separate selectors with a new line.",
 	"css.format.newlineBetweenRules.desc": "Separate rulesets by a blank line.",
-	"css.format.spaceAroundSelectorSeparator.desc": "Ensure a space character around selector separators '>', '+', '~' (e.g. `a > b`).",
+	"css.format.spaceAroundSelectorSeparator.desc": "Ensure a space character around selector separators `>`, `+`, `~` (e.g. `a > b`).",
 	"css.format.braceStyle.desc": "Put braces on the same line as rules (`collapse`) or put braces on own line (`expand`).",
 	"css.format.preserveNewLines.desc": "Whether existing line breaks before rules and declarations should be preserved.",
 	"css.format.maxPreserveNewLines.desc": "Maximum number of line breaks to be preserved in one chunk, when `#css.format.preserveNewLines#` is enabled.",
@@ -67,7 +67,7 @@
 	"less.format.enable.desc": "Enable/disable default LESS formatter.",
 	"less.format.newlineBetweenSelectors.desc": "Separate selectors with a new line.",
 	"less.format.newlineBetweenRules.desc": "Separate rulesets by a blank line.",
-	"less.format.spaceAroundSelectorSeparator.desc": "Ensure a space character around selector separators '>', '+', '~' (e.g. `a > b`).",
+	"less.format.spaceAroundSelectorSeparator.desc": "Ensure a space character around selector separators `>`, `+`, `~` (e.g. `a > b`).",
 	"less.format.braceStyle.desc": "Put braces on the same line as rules (`collapse`) or put braces on own line (`expand`).",
 	"less.format.preserveNewLines.desc": "Whether existing line breaks before rules and declarations should be preserved.",
 	"less.format.maxPreserveNewLines.desc": "Maximum number of line breaks to be preserved in one chunk, when `#less.format.preserveNewLines#` is enabled.",
@@ -101,7 +101,7 @@
 	"scss.format.enable.desc": "Enable/disable default SCSS formatter.",
 	"scss.format.newlineBetweenSelectors.desc": "Separate selectors with a new line.",
 	"scss.format.newlineBetweenRules.desc": "Separate rulesets by a blank line.",
-	"scss.format.spaceAroundSelectorSeparator.desc": "Ensure a space character around selector separators '>', '+', '~' (e.g. `a > b`).",
+	"scss.format.spaceAroundSelectorSeparator.desc": "Ensure a space character around selector separators `>`, `+`, `~` (e.g. `a > b`).",
 	"scss.format.braceStyle.desc": "Put braces on the same line as rules (`collapse`) or put braces on own line (`expand`).",
 	"scss.format.preserveNewLines.desc": "Whether existing line breaks before rules and declarations should be preserved.",
 	"scss.format.maxPreserveNewLines.desc": "Maximum number of line breaks to be preserved in one chunk, when `#scss.format.preserveNewLines#` is enabled.",
diff --git a/extensions/css/cgmanifest.json b/extensions/css/cgmanifest.json
index 7b85089b6b91a..93bd8ba0f3109 100644
--- a/extensions/css/cgmanifest.json
+++ b/extensions/css/cgmanifest.json
@@ -6,7 +6,7 @@
 				"git": {
 					"name": "microsoft/vscode-css",
 					"repositoryUrl": "https://github.com/microsoft/vscode-css",
-					"commitHash": "a927fe2f73927bf5c25d0b0c4dd0e63d69fd8887"
+					"commitHash": "9a07d76cb0e7a56f9bfc76328a57227751e4adb4"
 				}
 			},
 			"licenseDetail": [
diff --git a/extensions/css/syntaxes/css.tmLanguage.json b/extensions/css/syntaxes/css.tmLanguage.json
index 5ba8bc90b7381..484af027c195c 100644
--- a/extensions/css/syntaxes/css.tmLanguage.json
+++ b/extensions/css/syntaxes/css.tmLanguage.json
@@ -4,7 +4,7 @@
 		"If you want to provide a fix or improvement, please create a pull request against the original repository.",
 		"Once accepted there, we are happy to receive an update request."
 	],
-	"version": "https://github.com/microsoft/vscode-css/commit/a927fe2f73927bf5c25d0b0c4dd0e63d69fd8887",
+	"version": "https://github.com/microsoft/vscode-css/commit/9a07d76cb0e7a56f9bfc76328a57227751e4adb4",
 	"name": "CSS",
 	"scopeName": "source.css",
 	"patterns": [
@@ -1401,7 +1401,7 @@
 		"property-keywords": {
 			"patterns": [
 				{
-					"match": "(?xi) (?<![\\w-])\n(above|absolute|active|add|additive|after-edge|alias|all|all-petite-caps|all-scroll|all-small-caps|alpha|alphabetic|alternate|alternate-reverse\n|always|antialiased|auto|auto-fill|auto-fit|auto-pos|available|avoid|avoid-column|avoid-page|avoid-region|backwards|balance|baseline|before-edge|below|bevel\n|bidi-override|blink|block|block-axis|block-start|block-end|bold|bolder|border|border-box|both|bottom|bottom-outside|break-all|break-word|bullets\n|butt|capitalize|caption|cell|center|central|char|circle|clip|clone|close-quote|closest-corner|closest-side|col-resize|collapse|color|color-burn\n|color-dodge|column|column-reverse|common-ligatures|compact|condensed|contain|content|content-box|contents|context-menu|contextual|copy|cover\n|crisp-edges|crispEdges|crosshair|cyclic|dark|darken|dashed|decimal|default|dense|diagonal-fractions|difference|digits|disabled|disc|discretionary-ligatures\n|distribute|distribute-all-lines|distribute-letter|distribute-space|dot|dotted|double|double-circle|downleft|downright|e-resize|each-line|ease|ease-in\n|ease-in-out|ease-out|economy|ellipse|ellipsis|embed|end|evenodd|ew-resize|exact|exclude|exclusion|expanded|extends|extra-condensed|extra-expanded\n|fallback|farthest-corner|farthest-side|fill|fill-available|fill-box|filled|fit-content|fixed|flat|flex|flex-end|flex-start|flip|flow-root|forwards|freeze\n|from-image|full-width|geometricPrecision|georgian|grab|grabbing|grayscale|grid|groove|hand|hanging|hard-light|help|hidden|hide\n|historical-forms|historical-ligatures|horizontal|horizontal-tb|hue|icon|ideograph-alpha|ideograph-numeric|ideograph-parenthesis|ideograph-space\n|ideographic|inactive|infinite|inherit|initial|inline|inline-axis|inline-block|inline-end|inline-flex|inline-grid|inline-list-item|inline-start\n|inline-table|inset|inside|inter-character|inter-ideograph|inter-word|intersect|invert|isolate|isolate-override|italic|jis04|jis78|jis83\n|jis90|justify|justify-all|kannada|keep-all|landscape|large|larger|left|light|lighten|lighter|line|line-edge|line-through|linear|linearRGB\n|lining-nums|list-item|local|loose|lowercase|lr|lr-tb|ltr|luminance|luminosity|main-size|mandatory|manipulation|manual|margin-box|match-parent\n|match-source|mathematical|max-content|medium|menu|message-box|middle|min-content|miter|mixed|move|multiply|n-resize|narrower|ne-resize\n|nearest-neighbor|nesw-resize|newspaper|no-change|no-clip|no-close-quote|no-common-ligatures|no-contextual|no-discretionary-ligatures\n|no-drop|no-historical-ligatures|no-open-quote|no-repeat|none|nonzero|normal|not-allowed|nowrap|ns-resize|numbers|numeric|nw-resize|nwse-resize\n|oblique|oldstyle-nums|open|open-quote|optimizeLegibility|optimizeQuality|optimizeSpeed|optional|ordinal|outset|outside|over|overlay|overline|padding\n|padding-box|page|painted|pan-down|pan-left|pan-right|pan-up|pan-x|pan-y|paused|petite-caps|pixelated|plaintext|pointer|portrait|pre|pre-line\n|pre-wrap|preserve-3d|progress|progressive|proportional-nums|proportional-width|proximity|radial|recto|region|relative|remove|repeat|repeat-[xy]\n|reset-size|reverse|revert|ridge|right|rl|rl-tb|round|row|row-resize|row-reverse|row-severse|rtl|ruby|ruby-base|ruby-base-container|ruby-text\n|ruby-text-container|run-in|running|s-resize|saturation|scale-down|screen|scroll|scroll-position|se-resize|semi-condensed|semi-expanded|separate\n|sesame|show|sideways|sideways-left|sideways-lr|sideways-right|sideways-rl|simplified|slashed-zero|slice|small|small-caps|small-caption|smaller\n|smooth|soft-light|solid|space|space-around|space-between|space-evenly|spell-out|square|sRGB|stacked-fractions|start|static|status-bar|swap\n|step-end|step-start|sticky|stretch|strict|stroke|stroke-box|style|sub|subgrid|subpixel-antialiased|subtract|super|sw-resize|symbolic|table\n|table-caption|table-cell|table-column|table-column-group|table-footer-group|table-header-group|table-row|table-row-group|tabular-nums|tb|tb-rl\n|text|text-after-edge|text-before-edge|text-bottom|text-top|thick|thin|titling-caps|top|top-outside|touch|traditional|transparent|triangle\n|ultra-condensed|ultra-expanded|under|underline|unicase|unset|upleft|uppercase|upright|use-glyph-orientation|use-script|verso|vertical\n|vertical-ideographic|vertical-lr|vertical-rl|vertical-text|view-box|visible|visibleFill|visiblePainted|visibleStroke|w-resize|wait|wavy\n|weight|whitespace|wider|words|wrap|wrap-reverse|x|x-large|x-small|xx-large|xx-small|y|zero|zoom-in|zoom-out)\n(?![\\w-])",
+					"match": "(?xi) (?<![\\w-])\n(above|absolute|active|add|additive|after-edge|alias|all|all-petite-caps|all-scroll|all-small-caps|alpha|alphabetic|alternate|alternate-reverse\n|always|antialiased|auto|auto-fill|auto-fit|auto-pos|available|avoid|avoid-column|avoid-page|avoid-region|backwards|balance|baseline|before-edge|below|bevel\n|bidi-override|blink|block|block-axis|block-start|block-end|bold|bolder|border|border-box|both|bottom|bottom-outside|break-all|break-word|bullets\n|butt|capitalize|caption|cell|center|central|char|circle|clip|clone|close-quote|closest-corner|closest-side|col-resize|collapse|color|color-burn\n|color-dodge|column|column-reverse|common-ligatures|compact|condensed|contain|content|content-box|contents|context-menu|contextual|copy|cover\n|crisp-edges|crispEdges|crosshair|cyclic|dark|darken|dashed|decimal|default|dense|diagonal-fractions|difference|digits|disabled|disc|discretionary-ligatures\n|distribute|distribute-all-lines|distribute-letter|distribute-space|dot|dotted|double|double-circle|downleft|downright|e-resize|each-line|ease|ease-in\n|ease-in-out|ease-out|economy|ellipse|ellipsis|embed|end|evenodd|ew-resize|exact|exclude|exclusion|expanded|extends|extra-condensed|extra-expanded\n|fallback|farthest-corner|farthest-side|fill|fill-available|fill-box|filled|fit-content|fixed|flat|flex|flex-end|flex-start|flip|flow|flow-root|forwards|freeze\n|from-image|full-width|geometricPrecision|georgian|grab|grabbing|grayscale|grid|groove|hand|hanging|hard-light|help|hidden|hide\n|historical-forms|historical-ligatures|horizontal|horizontal-tb|hue|icon|ideograph-alpha|ideograph-numeric|ideograph-parenthesis|ideograph-space\n|ideographic|inactive|infinite|inherit|initial|inline|inline-axis|inline-block|inline-end|inline-flex|inline-grid|inline-list-item|inline-start\n|inline-table|inset|inside|inter-character|inter-ideograph|inter-word|intersect|invert|isolate|isolate-override|italic|jis04|jis78|jis83\n|jis90|justify|justify-all|kannada|keep-all|landscape|large|larger|left|light|lighten|lighter|line|line-edge|line-through|linear|linearRGB\n|lining-nums|list-item|local|loose|lowercase|lr|lr-tb|ltr|luminance|luminosity|main-size|mandatory|manipulation|manual|margin-box|match-parent\n|match-source|mathematical|max-content|medium|menu|message-box|middle|min-content|miter|mixed|move|multiply|n-resize|narrower|ne-resize\n|nearest-neighbor|nesw-resize|newspaper|no-change|no-clip|no-close-quote|no-common-ligatures|no-contextual|no-discretionary-ligatures\n|no-drop|no-historical-ligatures|no-open-quote|no-repeat|none|nonzero|normal|not-allowed|nowrap|ns-resize|numbers|numeric|nw-resize|nwse-resize\n|oblique|oldstyle-nums|open|open-quote|optimizeLegibility|optimizeQuality|optimizeSpeed|optional|ordinal|outset|outside|over|overlay|overline|padding\n|padding-box|page|painted|pan-down|pan-left|pan-right|pan-up|pan-x|pan-y|paused|petite-caps|pixelated|plaintext|pointer|portrait|pre|pre-line\n|pre-wrap|preserve-3d|progress|progressive|proportional-nums|proportional-width|proximity|radial|recto|region|relative|remove|repeat|repeat-[xy]\n|reset-size|reverse|revert|revert-layer|ridge|right|rl|rl-tb|round|row|row-resize|row-reverse|row-severse|rtl|ruby|ruby-base|ruby-base-container|ruby-text\n|ruby-text-container|run-in|running|s-resize|saturation|scale-down|screen|scroll|scroll-position|se-resize|semi-condensed|semi-expanded|separate\n|sesame|show|sideways|sideways-left|sideways-lr|sideways-right|sideways-rl|simplified|slashed-zero|slice|small|small-caps|small-caption|smaller\n|smooth|soft-light|solid|space|space-around|space-between|space-evenly|spell-out|square|sRGB|stacked-fractions|start|static|status-bar|swap\n|step-end|step-start|sticky|stretch|strict|stroke|stroke-box|style|sub|subgrid|subpixel-antialiased|subtract|super|sw-resize|symbolic|table\n|table-caption|table-cell|table-column|table-column-group|table-footer-group|table-header-group|table-row|table-row-group|tabular-nums|tb|tb-rl\n|text|text-after-edge|text-before-edge|text-bottom|text-top|thick|thin|titling-caps|top|top-outside|touch|traditional|transparent|triangle\n|ultra-condensed|ultra-expanded|under|underline|unicase|unset|upleft|uppercase|upright|use-glyph-orientation|use-script|verso|vertical\n|vertical-ideographic|vertical-lr|vertical-rl|vertical-text|view-box|visible|visibleFill|visiblePainted|visibleStroke|w-resize|wait|wavy\n|weight|whitespace|wider|words|wrap|wrap-reverse|x|x-large|x-small|xx-large|xx-small|y|zero|zoom-in|zoom-out)\n(?![\\w-])",
 					"name": "support.constant.property-value.css"
 				},
 				{
diff --git a/extensions/dart/cgmanifest.json b/extensions/dart/cgmanifest.json
index 5558b78af1d9b..9bd59135d851e 100644
--- a/extensions/dart/cgmanifest.json
+++ b/extensions/dart/cgmanifest.json
@@ -6,7 +6,7 @@
 				"git": {
 					"name": "dart-lang/dart-syntax-highlight",
 					"repositoryUrl": "https://github.com/dart-lang/dart-syntax-highlight",
-					"commitHash": "e1ac5c446c2531343393adbe8fff9d45d8a7c412"
+					"commitHash": "b2e04fbe2334bfe56940106b652f4c5799affbb1"
 				}
 			},
 			"licenseDetail": [
diff --git a/extensions/dart/syntaxes/dart.tmLanguage.json b/extensions/dart/syntaxes/dart.tmLanguage.json
index b4f80b680bd8f..30bce5e30219c 100644
--- a/extensions/dart/syntaxes/dart.tmLanguage.json
+++ b/extensions/dart/syntaxes/dart.tmLanguage.json
@@ -4,7 +4,7 @@
 		"If you want to provide a fix or improvement, please create a pull request against the original repository.",
 		"Once accepted there, we are happy to receive an update request."
 	],
-	"version": "https://github.com/dart-lang/dart-syntax-highlight/commit/e1ac5c446c2531343393adbe8fff9d45d8a7c412",
+	"version": "https://github.com/dart-lang/dart-syntax-highlight/commit/b2e04fbe2334bfe56940106b652f4c5799affbb1",
 	"name": "Dart",
 	"scopeName": "source.dart",
 	"patterns": [
@@ -58,6 +58,12 @@
 		{
 			"include": "#constants-and-special-vars"
 		},
+		{
+			"include": "#class-identifier-with-optional-factory-method"
+		},
+		{
+			"include": "#function-identifier"
+		},
 		{
 			"include": "#operators"
 		},
@@ -224,12 +230,49 @@
 				{
 					"name": "constant.numeric.dart",
 					"match": "(?<!\\$)\\b((0(x|X)[0-9a-fA-F][0-9a-fA-F_]*)|(([0-9][0-9_]*\\.?[0-9_]*)|(\\.[0-9][0-9_]*))((e|E)(\\+|-)?[0-9][0-9_]*)?)\\b(?!\\$)"
+				}
+			]
+		},
+		"class-identifier-with-optional-factory-method": {
+			"patterns": [
+				{
+					"match": "(?<!\\$)\\b(bool|num|int|double|dynamic)\\b(?!\\$)\\s*(factory\\b)?",
+					"captures": {
+						"1": {
+							"name": "support.class.dart"
+						},
+						"2": {
+							"name": "entity.name.function.dart"
+						}
+					}
 				},
 				{
-					"include": "#class-identifier"
+					"match": "(?<!\\$)\\b(void)\\b(?!\\$)\\s*(factory\\b)?",
+					"captures": {
+						"1": {
+							"name": "storage.type.primitive.dart"
+						},
+						"2": {
+							"name": "entity.name.function.dart"
+						}
+					}
 				},
 				{
-					"include": "#function-identifier"
+					"begin": "(?<![a-zA-Z0-9_$])([_$]*[A-Z][a-zA-Z0-9_$]*)\\b\\s*(factory\\b)?",
+					"end": "(?!<)",
+					"beginCaptures": {
+						"1": {
+							"name": "support.class.dart"
+						},
+						"2": {
+							"name": "entity.name.function.dart"
+						}
+					},
+					"patterns": [
+						{
+							"include": "#type-args"
+						}
+					]
 				}
 			]
 		},
@@ -275,6 +318,10 @@
 							]
 						}
 					}
+				},
+				{
+					"match": "(?<=\\.)new\\b",
+					"name": "entity.name.function.dart"
 				}
 			]
 		},
@@ -330,8 +377,8 @@
 					"match": "(?<!\\$)\\bassert\\b(?!\\$)"
 				},
 				{
-					"name": "keyword.control.new.dart",
-					"match": "(?<!\\$)\\b(new)\\b(?!\\$)"
+					"name": "keyword.new.dart",
+					"match": "(?<![\\$\\.])\\b(new)\\b(?!\\$)"
 				},
 				{
 					"name": "keyword.control.return.dart",
@@ -347,7 +394,7 @@
 				},
 				{
 					"name": "storage.type.primitive.dart",
-					"match": "(?<!\\$)\\b(?:void|var)\\b(?!\\$)"
+					"match": "(?<!\\$)\\b(?:var)\\b(?!\\$)"
 				}
 			]
 		},
@@ -404,6 +451,12 @@
 				{
 					"include": "#constants-and-special-vars"
 				},
+				{
+					"include": "#class-identifier-with-optional-factory-method"
+				},
+				{
+					"include": "#function-identifier"
+				},
 				{
 					"include": "#strings"
 				},
diff --git a/extensions/emmet/package.nls.json b/extensions/emmet/package.nls.json
index 2a58c39641d52..683bcc7f307e2 100644
--- a/extensions/emmet/package.nls.json
+++ b/extensions/emmet/package.nls.json
@@ -50,10 +50,10 @@
 	"emmetPreferencesFormatNoIndentTags": "An array of tag names that should never get inner indentation.",
 	"emmetPreferencesFormatForceIndentTags": "An array of tag names that should always get inner indentation.",
 	"emmetPreferencesAllowCompactBoolean": "If `true`, compact notation of boolean attributes are produced.",
-	"emmetPreferencesCssWebkitProperties": "Comma separated CSS properties that get the 'webkit' vendor prefix when used in Emmet abbreviation that starts with `-`. Set to empty string to always avoid the 'webkit' prefix.",
-	"emmetPreferencesCssMozProperties": "Comma separated CSS properties that get the 'moz' vendor prefix when used in Emmet abbreviation that starts with `-`. Set to empty string to always avoid the 'moz' prefix.",
-	"emmetPreferencesCssOProperties": "Comma separated CSS properties that get the 'o' vendor prefix when used in Emmet abbreviation that starts with `-`. Set to empty string to always avoid the 'o' prefix.",
-	"emmetPreferencesCssMsProperties": "Comma separated CSS properties that get the 'ms' vendor prefix when used in Emmet abbreviation that starts with `-`. Set to empty string to always avoid the 'ms' prefix.",
+	"emmetPreferencesCssWebkitProperties": "Comma separated CSS properties that get the `webkit` vendor prefix when used in Emmet abbreviation that starts with `-`. Set to empty string to always avoid the `webkit` prefix.",
+	"emmetPreferencesCssMozProperties": "Comma separated CSS properties that get the `moz` vendor prefix when used in Emmet abbreviation that starts with `-`. Set to empty string to always avoid the `moz` prefix.",
+	"emmetPreferencesCssOProperties": "Comma separated CSS properties that get the `o` vendor prefix when used in Emmet abbreviation that starts with `-`. Set to empty string to always avoid the `o` prefix.",
+	"emmetPreferencesCssMsProperties": "Comma separated CSS properties that get the `ms` vendor prefix when used in Emmet abbreviation that starts with `-`. Set to empty string to always avoid the `ms` prefix.",
 	"emmetPreferencesCssFuzzySearchMinScore": "The minimum score (from 0 to 1) that fuzzy-matched abbreviation should achieve. Lower values may produce many false-positive matches, higher values may reduce possible matches.",
 	"emmetOptimizeStylesheetParsing": "When set to `false`, the whole file is parsed to determine if current position is valid for expanding Emmet abbreviations. When set to `true`, only the content around the current position in CSS/SCSS/Less files is parsed.",
 	"emmetPreferencesOutputInlineBreak": "The number of sibling inline elements needed for line breaks to be placed between those elements. If `0`, inline elements are always expanded onto a single line.",
diff --git a/extensions/esbuild-extension-common.mts b/extensions/esbuild-extension-common.mts
index 1c458e4bfe172..cc716f2ca6aa8 100644
--- a/extensions/esbuild-extension-common.mts
+++ b/extensions/esbuild-extension-common.mts
@@ -33,6 +33,7 @@ async function tryBuild(options: BuildOptions, didBuild?: (outDir: string) => un
 
 interface RunConfig {
 	readonly platform: 'node' | 'browser';
+	readonly format?: 'cjs' | 'esm';
 	readonly srcDir: string;
 	readonly outdir: string;
 	readonly entryPoints: string[] | Record<string, string> | { in: string; out: string }[];
@@ -48,6 +49,7 @@ function resolveOptions(config: RunConfig, outdir: string): BuildOptions {
 		sourcemap: true,
 		target: ['es2024'],
 		external: ['vscode'],
+		format: config.format ?? 'cjs',
 		entryPoints: config.entryPoints,
 		outdir,
 		logOverride: {
@@ -57,10 +59,8 @@ function resolveOptions(config: RunConfig, outdir: string): BuildOptions {
 	};
 
 	if (config.platform === 'node') {
-		options.format = 'cjs';
 		options.mainFields = ['module', 'main'];
 	} else if (config.platform === 'browser') {
-		options.format = 'cjs';
 		options.mainFields = ['browser', 'module', 'main'];
 		options.alias = {
 			'path': 'path-browserify',
diff --git a/extensions/extension-editing/esbuild.browser.mts b/extensions/extension-editing/esbuild.browser.mts
index 170f3cda31380..58b5fb7d6d5fa 100644
--- a/extensions/extension-editing/esbuild.browser.mts
+++ b/extensions/extension-editing/esbuild.browser.mts
@@ -15,4 +15,7 @@ run({
 	},
 	srcDir,
 	outdir: outDir,
+	additionalOptions: {
+		tsconfig: path.join(import.meta.dirname, 'tsconfig.browser.json'),
+	},
 }, process.argv);
diff --git a/extensions/extension-editing/package-lock.json b/extensions/extension-editing/package-lock.json
index be1aa96eea6cb..d96f9a2bccacf 100644
--- a/extensions/extension-editing/package-lock.json
+++ b/extensions/extension-editing/package-lock.json
@@ -14,18 +14,37 @@
         "parse5": "^3.0.2"
       },
       "devDependencies": {
-        "@types/markdown-it": "0.0.2",
+        "@types/markdown-it": "^14",
         "@types/node": "22.x"
       },
       "engines": {
         "vscode": "^1.4.0"
       }
     },
+    "node_modules/@types/linkify-it": {
+      "version": "5.0.0",
+      "resolved": "https://registry.npmjs.org/@types/linkify-it/-/linkify-it-5.0.0.tgz",
+      "integrity": "sha512-sVDA58zAw4eWAffKOaQH5/5j3XeayukzDk+ewSsnv3p4yJEZHCCzMDiZM8e0OUrRvmpGZ85jf4yDHkHsgBNr9Q==",
+      "dev": true,
+      "license": "MIT"
+    },
     "node_modules/@types/markdown-it": {
-      "version": "0.0.2",
-      "resolved": "https://registry.npmjs.org/@types/markdown-it/-/markdown-it-0.0.2.tgz",
-      "integrity": "sha1-XZrRnm5lCM3S8llt+G/Qqt5ZhmA= sha512-A2seE+zJYSjGHy7L/v0EN/xRfgv2A60TuXOwI8tt5aZxF4UeoYIkM2jERnNH8w4VFr7oFEm0lElGOao7fZgygQ==",
-      "dev": true
+      "version": "14.1.2",
+      "resolved": "https://registry.npmjs.org/@types/markdown-it/-/markdown-it-14.1.2.tgz",
+      "integrity": "sha512-promo4eFwuiW+TfGxhi+0x3czqTYJkG8qB17ZUJiVF10Xm7NLVRSLUsfRTU/6h1e24VvRnXCx+hG7li58lkzog==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@types/linkify-it": "^5",
+        "@types/mdurl": "^2"
+      }
+    },
+    "node_modules/@types/mdurl": {
+      "version": "2.0.0",
+      "resolved": "https://registry.npmjs.org/@types/mdurl/-/mdurl-2.0.0.tgz",
+      "integrity": "sha512-RGdgjQUZba5p6QEFAVx2OGb8rQDL/cPRG7GiedRzMcJ1tYnUANBncjbSB1NRGwbvjcPeikRABz2nshyPk1bhWg==",
+      "dev": true,
+      "license": "MIT"
     },
     "node_modules/@types/node": {
       "version": "22.13.10",
diff --git a/extensions/extension-editing/package.json b/extensions/extension-editing/package.json
index 3e277dbbfd385..c491fbedca2f5 100644
--- a/extensions/extension-editing/package.json
+++ b/extensions/extension-editing/package.json
@@ -66,7 +66,7 @@
     ]
   },
   "devDependencies": {
-    "@types/markdown-it": "0.0.2",
+    "@types/markdown-it": "^14",
     "@types/node": "22.x"
   },
   "repository": {
diff --git a/extensions/extension-editing/src/extensionEditingBrowserMain.ts b/extensions/extension-editing/src/extensionEditingBrowserMain.ts
index f9d6885c6223c..57c969d017020 100644
--- a/extensions/extension-editing/src/extensionEditingBrowserMain.ts
+++ b/extensions/extension-editing/src/extensionEditingBrowserMain.ts
@@ -5,11 +5,14 @@
 
 import * as vscode from 'vscode';
 import { PackageDocument } from './packageDocumentHelper';
+import { PackageDocumentL10nSupport } from './packageDocumentL10nSupport';
 
 export function activate(context: vscode.ExtensionContext) {
 	//package.json suggestions
 	context.subscriptions.push(registerPackageDocumentCompletions());
 
+	//package.json go to definition for NLS strings
+	context.subscriptions.push(new PackageDocumentL10nSupport());
 }
 
 function registerPackageDocumentCompletions(): vscode.Disposable {
@@ -18,5 +21,4 @@ function registerPackageDocumentCompletions(): vscode.Disposable {
 			return new PackageDocument(document).provideCompletionItems(position, token);
 		}
 	});
-
 }
diff --git a/extensions/extension-editing/src/extensionEditingMain.ts b/extensions/extension-editing/src/extensionEditingMain.ts
index c056fbfa975ae..c620b3039541f 100644
--- a/extensions/extension-editing/src/extensionEditingMain.ts
+++ b/extensions/extension-editing/src/extensionEditingMain.ts
@@ -5,6 +5,7 @@
 
 import * as vscode from 'vscode';
 import { PackageDocument } from './packageDocumentHelper';
+import { PackageDocumentL10nSupport } from './packageDocumentL10nSupport';
 import { ExtensionLinter } from './extensionLinter';
 
 export function activate(context: vscode.ExtensionContext) {
@@ -15,6 +16,9 @@ export function activate(context: vscode.ExtensionContext) {
 	//package.json code actions for lint warnings
 	context.subscriptions.push(registerCodeActionsProvider());
 
+	// package.json l10n support
+	context.subscriptions.push(new PackageDocumentL10nSupport());
+
 	context.subscriptions.push(new ExtensionLinter());
 }
 
diff --git a/extensions/extension-editing/src/extensionLinter.ts b/extensions/extension-editing/src/extensionLinter.ts
index 5c73304b4d891..6249500e2d171 100644
--- a/extensions/extension-editing/src/extensionLinter.ts
+++ b/extensions/extension-editing/src/extensionLinter.ts
@@ -8,7 +8,7 @@ import * as fs from 'fs';
 import { URL } from 'url';
 
 import { parseTree, findNodeAtLocation, Node as JsonNode, getNodeValue } from 'jsonc-parser';
-import * as MarkdownItType from 'markdown-it';
+import type MarkdownIt from 'markdown-it';
 
 import { commands, languages, workspace, Disposable, TextDocument, Uri, Diagnostic, Range, DiagnosticSeverity, Position, env, l10n } from 'vscode';
 import { INormalizedVersion, normalizeVersion, parseVersion } from './extensionEngineValidation';
@@ -44,7 +44,7 @@ enum Context {
 }
 
 interface TokenAndPosition {
-	token: MarkdownItType.Token;
+	token: MarkdownIt.Token;
 	begin: number;
 	end: number;
 }
@@ -67,7 +67,7 @@ export class ExtensionLinter {
 	private packageJsonQ = new Set<TextDocument>();
 	private readmeQ = new Set<TextDocument>();
 	private timer: NodeJS.Timeout | undefined;
-	private markdownIt: MarkdownItType.MarkdownIt | undefined;
+	private markdownIt: MarkdownIt | undefined;
 	private parse5: typeof import('parse5') | undefined;
 
 	constructor() {
@@ -292,7 +292,7 @@ export class ExtensionLinter {
 				this.markdownIt = new ((await import('markdown-it')).default);
 			}
 			const tokens = this.markdownIt.parse(text, {});
-			const tokensAndPositions: TokenAndPosition[] = (function toTokensAndPositions(this: ExtensionLinter, tokens: MarkdownItType.Token[], begin = 0, end = text.length): TokenAndPosition[] {
+			const tokensAndPositions: TokenAndPosition[] = (function toTokensAndPositions(this: ExtensionLinter, tokens: MarkdownIt.Token[], begin = 0, end = text.length): TokenAndPosition[] {
 				const tokensAndPositions = tokens.map<TokenAndPosition>(token => {
 					if (token.map) {
 						const tokenBegin = document.offsetAt(new Position(token.map[0], 0));
@@ -313,7 +313,7 @@ export class ExtensionLinter {
 				});
 				return tokensAndPositions.concat(
 					...tokensAndPositions.filter(tnp => tnp.token.children && tnp.token.children.length)
-						.map(tnp => toTokensAndPositions.call(this, tnp.token.children, tnp.begin, tnp.end))
+						.map(tnp => toTokensAndPositions.call(this, tnp.token.children ?? [], tnp.begin, tnp.end))
 				);
 			}).call(this, tokens);
 
@@ -373,7 +373,7 @@ export class ExtensionLinter {
 		}
 	}
 
-	private locateToken(text: string, begin: number, end: number, token: MarkdownItType.Token, content: string | null) {
+	private locateToken(text: string, begin: number, end: number, token: MarkdownIt.Token, content: string | null) {
 		if (content) {
 			const tokenBegin = text.indexOf(content, begin);
 			if (tokenBegin !== -1) {
diff --git a/extensions/extension-editing/src/packageDocumentL10nSupport.ts b/extensions/extension-editing/src/packageDocumentL10nSupport.ts
new file mode 100644
index 0000000000000..4d844e98d5f71
--- /dev/null
+++ b/extensions/extension-editing/src/packageDocumentL10nSupport.ts
@@ -0,0 +1,204 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as vscode from 'vscode';
+import { getLocation, getNodeValue, parseTree, findNodeAtLocation, visit } from 'jsonc-parser';
+
+
+const packageJsonSelector: vscode.DocumentSelector = { language: 'json', pattern: '**/package.json' };
+const packageNlsJsonSelector: vscode.DocumentSelector = { language: 'json', pattern: '**/package.nls.json' };
+
+export class PackageDocumentL10nSupport implements vscode.DefinitionProvider, vscode.ReferenceProvider, vscode.Disposable {
+
+	private readonly _disposables: vscode.Disposable[] = [];
+
+	constructor() {
+		this._disposables.push(vscode.languages.registerDefinitionProvider(packageJsonSelector, this));
+		this._disposables.push(vscode.languages.registerDefinitionProvider(packageNlsJsonSelector, this));
+
+		this._disposables.push(vscode.languages.registerReferenceProvider(packageNlsJsonSelector, this));
+		this._disposables.push(vscode.languages.registerReferenceProvider(packageJsonSelector, this));
+	}
+
+	dispose(): void {
+		for (const d of this._disposables) {
+			d.dispose();
+		}
+	}
+
+	public async provideDefinition(document: vscode.TextDocument, position: vscode.Position, _token: vscode.CancellationToken): Promise<vscode.DefinitionLink[] | undefined> {
+		const basename = document.uri.path.split('/').pop()?.toLowerCase();
+		if (basename === 'package.json') {
+			return this.provideNlsValueDefinition(document, position);
+		}
+
+		if (basename === 'package.nls.json') {
+			return this.provideNlsKeyDefinition(document, position);
+		}
+
+		return undefined;
+	}
+
+	private async provideNlsValueDefinition(packageJsonDoc: vscode.TextDocument, position: vscode.Position): Promise<vscode.DefinitionLink[] | undefined> {
+		const nlsRef = this.getNlsReferenceAtPosition(packageJsonDoc, position);
+		if (!nlsRef) {
+			return undefined;
+		}
+
+		const nlsUri = vscode.Uri.joinPath(packageJsonDoc.uri, '..', 'package.nls.json');
+		return this.resolveNlsDefinition(nlsRef, nlsUri);
+	}
+
+	private async provideNlsKeyDefinition(nlsDoc: vscode.TextDocument, position: vscode.Position): Promise<vscode.DefinitionLink[] | undefined> {
+		const nlsKey = this.getNlsKeyDefinitionAtPosition(nlsDoc, position);
+		if (!nlsKey) {
+			return undefined;
+		}
+		return this.resolveNlsDefinition(nlsKey, nlsDoc.uri);
+	}
+
+	private async resolveNlsDefinition(origin: { key: string; range: vscode.Range }, nlsUri: vscode.Uri): Promise<vscode.DefinitionLink[] | undefined> {
+		const target = await this.findNlsKeyDeclaration(origin.key, nlsUri);
+		if (!target) {
+			return undefined;
+		}
+
+		return [{
+			originSelectionRange: origin.range,
+			targetUri: target.uri,
+			targetRange: target.range,
+		}];
+	}
+
+	private getNlsReferenceAtPosition(packageJsonDoc: vscode.TextDocument, position: vscode.Position): { key: string; range: vscode.Range } | undefined {
+		const location = getLocation(packageJsonDoc.getText(), packageJsonDoc.offsetAt(position));
+		if (!location.previousNode || location.previousNode.type !== 'string') {
+			return undefined;
+		}
+
+		const value = getNodeValue(location.previousNode);
+		if (typeof value !== 'string') {
+			return undefined;
+		}
+
+		const match = value.match(/^%(.+)%$/);
+		if (!match) {
+			return undefined;
+		}
+
+		const nodeStart = packageJsonDoc.positionAt(location.previousNode.offset);
+		const nodeEnd = packageJsonDoc.positionAt(location.previousNode.offset + location.previousNode.length);
+		return { key: match[1], range: new vscode.Range(nodeStart, nodeEnd) };
+	}
+
+	public async provideReferences(document: vscode.TextDocument, position: vscode.Position, context: vscode.ReferenceContext, _token: vscode.CancellationToken): Promise<vscode.Location[] | undefined> {
+		const basename = document.uri.path.split('/').pop()?.toLowerCase();
+		if (basename === 'package.nls.json') {
+			return this.provideNlsKeyReferences(document, position, context);
+		}
+		if (basename === 'package.json') {
+			return this.provideNlsValueReferences(document, position, context);
+		}
+		return undefined;
+	}
+
+	private async provideNlsKeyReferences(nlsDoc: vscode.TextDocument, position: vscode.Position, context: vscode.ReferenceContext): Promise<vscode.Location[] | undefined> {
+		const nlsKey = this.getNlsKeyDefinitionAtPosition(nlsDoc, position);
+		if (!nlsKey) {
+			return undefined;
+		}
+
+		const packageJsonUri = vscode.Uri.joinPath(nlsDoc.uri, '..', 'package.json');
+		return this.findAllNlsReferences(nlsKey.key, packageJsonUri, nlsDoc.uri, context);
+	}
+
+	private async provideNlsValueReferences(packageJsonDoc: vscode.TextDocument, position: vscode.Position, context: vscode.ReferenceContext): Promise<vscode.Location[] | undefined> {
+		const nlsRef = this.getNlsReferenceAtPosition(packageJsonDoc, position);
+		if (!nlsRef) {
+			return undefined;
+		}
+
+		const nlsUri = vscode.Uri.joinPath(packageJsonDoc.uri, '..', 'package.nls.json');
+		return this.findAllNlsReferences(nlsRef.key, packageJsonDoc.uri, nlsUri, context);
+	}
+
+	private async findAllNlsReferences(nlsKey: string, packageJsonUri: vscode.Uri, nlsUri: vscode.Uri, context: vscode.ReferenceContext): Promise<vscode.Location[]> {
+		const locations = await this.findNlsReferencesInPackageJson(nlsKey, packageJsonUri);
+
+		if (context.includeDeclaration) {
+			const decl = await this.findNlsKeyDeclaration(nlsKey, nlsUri);
+			if (decl) {
+				locations.push(decl);
+			}
+		}
+
+		return locations;
+	}
+
+	private async findNlsKeyDeclaration(nlsKey: string, nlsUri: vscode.Uri): Promise<vscode.Location | undefined> {
+		try {
+			const nlsDoc = await vscode.workspace.openTextDocument(nlsUri);
+			const nlsTree = parseTree(nlsDoc.getText());
+			if (!nlsTree) {
+				return undefined;
+			}
+
+			const node = findNodeAtLocation(nlsTree, [nlsKey]);
+			if (!node?.parent) {
+				return undefined;
+			}
+
+			const keyNode = node.parent.children?.[0];
+			if (!keyNode) {
+				return undefined;
+			}
+
+			const start = nlsDoc.positionAt(keyNode.offset);
+			const end = nlsDoc.positionAt(keyNode.offset + keyNode.length);
+			return new vscode.Location(nlsUri, new vscode.Range(start, end));
+		} catch {
+			return undefined;
+		}
+	}
+
+	private async findNlsReferencesInPackageJson(nlsKey: string, packageJsonUri: vscode.Uri): Promise<vscode.Location[]> {
+		let packageJsonDoc: vscode.TextDocument;
+		try {
+			packageJsonDoc = await vscode.workspace.openTextDocument(packageJsonUri);
+		} catch {
+			return [];
+		}
+
+		const text = packageJsonDoc.getText();
+		const needle = `%${nlsKey}%`;
+		const locations: vscode.Location[] = [];
+
+		visit(text, {
+			onLiteralValue(value, offset, length) {
+				if (value === needle) {
+					const start = packageJsonDoc.positionAt(offset);
+					const end = packageJsonDoc.positionAt(offset + length);
+					locations.push(new vscode.Location(packageJsonUri, new vscode.Range(start, end)));
+				}
+			}
+		});
+
+		return locations;
+	}
+
+	private getNlsKeyDefinitionAtPosition(nlsDoc: vscode.TextDocument, position: vscode.Position): { key: string; range: vscode.Range } | undefined {
+		const location = getLocation(nlsDoc.getText(), nlsDoc.offsetAt(position));
+
+		// Must be on a top-level property key
+		if (location.path.length !== 1 || !location.isAtPropertyKey || !location.previousNode) {
+			return undefined;
+		}
+
+		const key = location.path[0] as string;
+		const start = nlsDoc.positionAt(location.previousNode.offset);
+		const end = nlsDoc.positionAt(location.previousNode.offset + location.previousNode.length);
+		return { key, range: new vscode.Range(start, end) };
+	}
+}
diff --git a/extensions/git/.vscodeignore b/extensions/git/.vscodeignore
index a1fc5df7d26b8..9de840770944a 100644
--- a/extensions/git/.vscodeignore
+++ b/extensions/git/.vscodeignore
@@ -3,5 +3,5 @@ test/**
 out/**
 tsconfig*.json
 build/**
-extension.webpack.config.js
+esbuild*.mts
 package-lock.json
diff --git a/extensions/git/esbuild.mts b/extensions/git/esbuild.mts
new file mode 100644
index 0000000000000..1b397880bc6ca
--- /dev/null
+++ b/extensions/git/esbuild.mts
@@ -0,0 +1,35 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+import * as fs from 'node:fs/promises';
+import * as path from 'node:path';
+import { run } from '../esbuild-extension-common.mts';
+
+const srcDir = path.join(import.meta.dirname, 'src');
+const outDir = path.join(import.meta.dirname, 'dist');
+
+async function copyNonTsFiles(outDir: string): Promise<void> {
+	const entries = await fs.readdir(srcDir, { withFileTypes: true, recursive: true });
+	for (const entry of entries) {
+		if (!entry.isFile() || entry.name.endsWith('.ts')) {
+			continue;
+		}
+		const srcPath = path.join(entry.parentPath, entry.name);
+		const relativePath = path.relative(srcDir, srcPath);
+		const destPath = path.join(outDir, relativePath);
+		await fs.mkdir(path.dirname(destPath), { recursive: true });
+		await fs.copyFile(srcPath, destPath);
+	}
+}
+
+run({
+	platform: 'node',
+	entryPoints: {
+		'main': path.join(srcDir, 'main.ts'),
+		'askpass-main': path.join(srcDir, 'askpass-main.ts'),
+		'git-editor-main': path.join(srcDir, 'git-editor-main.ts'),
+	},
+	srcDir,
+	outdir: outDir,
+}, process.argv, copyNonTsFiles);
diff --git a/extensions/git/package-lock.json b/extensions/git/package-lock.json
index b552ce9fa5b3f..9d6f684de6102 100644
--- a/extensions/git/package-lock.json
+++ b/extensions/git/package-lock.json
@@ -12,7 +12,7 @@
         "@joaomoreno/unique-names-generator": "^5.2.0",
         "@vscode/extension-telemetry": "^0.9.8",
         "byline": "^5.0.0",
-        "file-type": "16.5.4",
+        "file-type": "21.3.1",
         "picomatch": "2.3.1",
         "vscode-uri": "^2.0.0",
         "which": "4.0.0"
@@ -28,6 +28,16 @@
         "vscode": "^1.5.0"
       }
     },
+    "node_modules/@borewit/text-codec": {
+      "version": "0.2.1",
+      "resolved": "https://registry.npmjs.org/@borewit/text-codec/-/text-codec-0.2.1.tgz",
+      "integrity": "sha512-k7vvKPbf7J2fZ5klGRD9AeKfUvojuZIQ3BT5u7Jfv+puwXkUBUT5PVyMDfJZpy30CBDXGMgw7fguK/lpOMBvgw==",
+      "license": "MIT",
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/Borewit"
+      }
+    },
     "node_modules/@joaomoreno/unique-names-generator": {
       "version": "5.2.0",
       "resolved": "https://registry.npmjs.org/@joaomoreno/unique-names-generator/-/unique-names-generator-5.2.0.tgz",
@@ -161,10 +171,28 @@
       "integrity": "sha512-OUUJTh3fnaUSzg9DEHgv3d7jC+DnPL65mIO7RaR+jWve7+MmcgIvF79gY97DPQ4frH+IpNR78YAYd/dW4gK3kg==",
       "license": "MIT"
     },
+    "node_modules/@tokenizer/inflate": {
+      "version": "0.4.1",
+      "resolved": "https://registry.npmjs.org/@tokenizer/inflate/-/inflate-0.4.1.tgz",
+      "integrity": "sha512-2mAv+8pkG6GIZiF1kNg1jAjh27IDxEPKwdGul3snfztFerfPGI1LjDezZp3i7BElXompqEtPmoPx6c2wgtWsOA==",
+      "license": "MIT",
+      "dependencies": {
+        "debug": "^4.4.3",
+        "token-types": "^6.1.1"
+      },
+      "engines": {
+        "node": ">=18"
+      },
+      "funding": {
+        "type": "github",
+        "url": "https://github.com/sponsors/Borewit"
+      }
+    },
     "node_modules/@tokenizer/token": {
       "version": "0.3.0",
       "resolved": "https://registry.npmjs.org/@tokenizer/token/-/token-0.3.0.tgz",
-      "integrity": "sha512-OvjF+z51L3ov0OyAU0duzsYuvO01PH7x4t6DJx+guahgTnBHkhJdG7soQeTSFLWN3efnHyibZ4Z8l2EuWwJN3A=="
+      "integrity": "sha512-OvjF+z51L3ov0OyAU0duzsYuvO01PH7x4t6DJx+guahgTnBHkhJdG7soQeTSFLWN3efnHyibZ4Z8l2EuWwJN3A==",
+      "license": "MIT"
     },
     "node_modules/@types/byline": {
       "version": "4.2.31",
@@ -226,17 +254,36 @@
         "node": ">=0.10.0"
       }
     },
+    "node_modules/debug": {
+      "version": "4.4.3",
+      "resolved": "https://registry.npmjs.org/debug/-/debug-4.4.3.tgz",
+      "integrity": "sha512-RGwwWnwQvkVfavKVt22FGLw+xYSdzARwm0ru6DhTVA3umU5hZc28V3kO4stgYryrTlLpuvgI9GiijltAjNbcqA==",
+      "license": "MIT",
+      "dependencies": {
+        "ms": "^2.1.3"
+      },
+      "engines": {
+        "node": ">=6.0"
+      },
+      "peerDependenciesMeta": {
+        "supports-color": {
+          "optional": true
+        }
+      }
+    },
     "node_modules/file-type": {
-      "version": "16.5.4",
-      "resolved": "https://registry.npmjs.org/file-type/-/file-type-16.5.4.tgz",
-      "integrity": "sha512-/yFHK0aGjFEgDJjEKP0pWCplsPFPhwyfwevf/pVxiN0tmE4L9LmwWxWukdJSHdoCli4VgQLehjJtwQBnqmsKcw==",
+      "version": "21.3.1",
+      "resolved": "https://registry.npmjs.org/file-type/-/file-type-21.3.1.tgz",
+      "integrity": "sha512-SrzXX46I/zsRDjTb82eucsGg0ODq2NpGDp4HcsFKApPy8P8vACjpJRDoGGMfEzhFC0ry61ajd7f72J3603anBA==",
+      "license": "MIT",
       "dependencies": {
-        "readable-web-to-node-stream": "^3.0.0",
-        "strtok3": "^6.2.4",
-        "token-types": "^4.1.1"
+        "@tokenizer/inflate": "^0.4.1",
+        "strtok3": "^10.3.4",
+        "token-types": "^6.1.1",
+        "uint8array-extras": "^1.4.0"
       },
       "engines": {
-        "node": ">=10"
+        "node": ">=20"
       },
       "funding": {
         "url": "https://github.com/sindresorhus/file-type?sponsor=1"
@@ -259,12 +306,8 @@
           "type": "consulting",
           "url": "https://feross.org/support"
         }
-      ]
-    },
-    "node_modules/inherits": {
-      "version": "2.0.4",
-      "resolved": "https://registry.npmjs.org/inherits/-/inherits-2.0.4.tgz",
-      "integrity": "sha512-k/vGaX4/Yla3WzyMCvTQOXYeIHvqOKtnqBduzTHpzpQZzAskKMhZ2K+EnBiSM9zGSoIFeMpXKxa4dYeZIQqewQ=="
+      ],
+      "license": "BSD-3-Clause"
     },
     "node_modules/isexe": {
       "version": "3.1.1",
@@ -274,17 +317,11 @@
         "node": ">=16"
       }
     },
-    "node_modules/peek-readable": {
-      "version": "4.1.0",
-      "resolved": "https://registry.npmjs.org/peek-readable/-/peek-readable-4.1.0.tgz",
-      "integrity": "sha512-ZI3LnwUv5nOGbQzD9c2iDG6toheuXSZP5esSHBjopsXH4dg19soufvpUGA3uohi5anFtGb2lhAVdHzH6R/Evvg==",
-      "engines": {
-        "node": ">=8"
-      },
-      "funding": {
-        "type": "github",
-        "url": "https://github.com/sponsors/Borewit"
-      }
+    "node_modules/ms": {
+      "version": "2.1.3",
+      "resolved": "https://registry.npmjs.org/ms/-/ms-2.1.3.tgz",
+      "integrity": "sha512-6FlzubTLZG3J2a/NVCAleEhjzq5oxgHyaCU9yYXvcLsvoVaHJq/s5xXI6/XXP6tz7R9xAOtHnSO/tXtF3WRTlA==",
+      "license": "MIT"
     },
     "node_modules/picomatch": {
       "version": "2.3.1",
@@ -297,91 +334,50 @@
         "url": "https://github.com/sponsors/jonschlinkert"
       }
     },
-    "node_modules/readable-stream": {
-      "version": "3.6.0",
-      "resolved": "https://registry.npmjs.org/readable-stream/-/readable-stream-3.6.0.tgz",
-      "integrity": "sha512-BViHy7LKeTz4oNnkcLJ+lVSL6vpiFeX6/d3oSH8zCW7UxP2onchk+vTGB143xuFjHS3deTgkKoXXymXqymiIdA==",
-      "dependencies": {
-        "inherits": "^2.0.3",
-        "string_decoder": "^1.1.1",
-        "util-deprecate": "^1.0.1"
-      },
-      "engines": {
-        "node": ">= 6"
-      }
-    },
-    "node_modules/readable-web-to-node-stream": {
-      "version": "3.0.2",
-      "resolved": "https://registry.npmjs.org/readable-web-to-node-stream/-/readable-web-to-node-stream-3.0.2.tgz",
-      "integrity": "sha512-ePeK6cc1EcKLEhJFt/AebMCLL+GgSKhuygrZ/GLaKZYEecIgIECf4UaUuaByiGtzckwR4ain9VzUh95T1exYGw==",
+    "node_modules/strtok3": {
+      "version": "10.3.4",
+      "resolved": "https://registry.npmjs.org/strtok3/-/strtok3-10.3.4.tgz",
+      "integrity": "sha512-KIy5nylvC5le1OdaaoCJ07L+8iQzJHGH6pWDuzS+d07Cu7n1MZ2x26P8ZKIWfbK02+XIL8Mp4RkWeqdUCrDMfg==",
+      "license": "MIT",
       "dependencies": {
-        "readable-stream": "^3.6.0"
+        "@tokenizer/token": "^0.3.0"
       },
       "engines": {
-        "node": ">=8"
+        "node": ">=18"
       },
       "funding": {
         "type": "github",
         "url": "https://github.com/sponsors/Borewit"
       }
     },
-    "node_modules/safe-buffer": {
-      "version": "5.2.1",
-      "resolved": "https://registry.npmjs.org/safe-buffer/-/safe-buffer-5.2.1.tgz",
-      "integrity": "sha512-rp3So07KcdmmKbGvgaNxQSJr7bGVSVk5S9Eq1F+ppbRo70+YeaDxkw5Dd8NPN+GD6bjnYm2VuPuCXmpuYvmCXQ==",
-      "funding": [
-        {
-          "type": "github",
-          "url": "https://github.com/sponsors/feross"
-        },
-        {
-          "type": "patreon",
-          "url": "https://www.patreon.com/feross"
-        },
-        {
-          "type": "consulting",
-          "url": "https://feross.org/support"
-        }
-      ]
-    },
-    "node_modules/string_decoder": {
-      "version": "1.3.0",
-      "resolved": "https://registry.npmjs.org/string_decoder/-/string_decoder-1.3.0.tgz",
-      "integrity": "sha512-hkRX8U1WjJFd8LsDJ2yQ/wWWxaopEsABU1XfkM8A+j0+85JAGppt16cr1Whg6KIbb4okU6Mql6BOj+uup/wKeA==",
-      "dependencies": {
-        "safe-buffer": "~5.2.0"
-      }
-    },
-    "node_modules/strtok3": {
-      "version": "6.3.0",
-      "resolved": "https://registry.npmjs.org/strtok3/-/strtok3-6.3.0.tgz",
-      "integrity": "sha512-fZtbhtvI9I48xDSywd/somNqgUHl2L2cstmXCCif0itOf96jeW18MBSyrLuNicYQVkvpOxkZtkzujiTJ9LW5Jw==",
+    "node_modules/token-types": {
+      "version": "6.1.2",
+      "resolved": "https://registry.npmjs.org/token-types/-/token-types-6.1.2.tgz",
+      "integrity": "sha512-dRXchy+C0IgK8WPC6xvCHFRIWYUbqqdEIKPaKo/AcTUNzwLTK6AH7RjdLWsEZcAN/TBdtfUw3PYEgPr5VPr6ww==",
+      "license": "MIT",
       "dependencies": {
+        "@borewit/text-codec": "^0.2.1",
         "@tokenizer/token": "^0.3.0",
-        "peek-readable": "^4.1.0"
+        "ieee754": "^1.2.1"
       },
       "engines": {
-        "node": ">=10"
+        "node": ">=14.16"
       },
       "funding": {
         "type": "github",
         "url": "https://github.com/sponsors/Borewit"
       }
     },
-    "node_modules/token-types": {
-      "version": "4.2.0",
-      "resolved": "https://registry.npmjs.org/token-types/-/token-types-4.2.0.tgz",
-      "integrity": "sha512-P0rrp4wUpefLncNamWIef62J0v0kQR/GfDVji9WKY7GDCWy5YbVSrKUTam07iWPZQGy0zWNOfstYTykMmPNR7w==",
-      "dependencies": {
-        "@tokenizer/token": "^0.3.0",
-        "ieee754": "^1.2.1"
-      },
+    "node_modules/uint8array-extras": {
+      "version": "1.5.0",
+      "resolved": "https://registry.npmjs.org/uint8array-extras/-/uint8array-extras-1.5.0.tgz",
+      "integrity": "sha512-rvKSBiC5zqCCiDZ9kAOszZcDvdAHwwIKJG33Ykj43OKcWsnmcBRL09YTU4nOeHZ8Y2a7l1MgTd08SBe9A8Qj6A==",
+      "license": "MIT",
       "engines": {
-        "node": ">=10"
+        "node": ">=18"
       },
       "funding": {
-        "type": "github",
-        "url": "https://github.com/sponsors/Borewit"
+        "url": "https://github.com/sponsors/sindresorhus"
       }
     },
     "node_modules/undici-types": {
@@ -391,11 +387,6 @@
       "dev": true,
       "license": "MIT"
     },
-    "node_modules/util-deprecate": {
-      "version": "1.0.2",
-      "resolved": "https://registry.npmjs.org/util-deprecate/-/util-deprecate-1.0.2.tgz",
-      "integrity": "sha512-EPD5q1uXyFxJpCrLnCc1nHnq3gOa6DZBocAIiI2TaSCA7VCJ1UJDMagCzIkXNsUYfD1daK//LTEQ8xiIbrHtcw=="
-    },
     "node_modules/vscode-uri": {
       "version": "2.0.0",
       "resolved": "https://registry.npmjs.org/vscode-uri/-/vscode-uri-2.0.0.tgz",
diff --git a/extensions/git/package.json b/extensions/git/package.json
index 39017ca4e1eed..8ff55b2a41576 100644
--- a/extensions/git/package.json
+++ b/extensions/git/package.json
@@ -38,6 +38,7 @@
     "scmTextDocument",
     "scmValidation",
     "statusBarItemTooltip",
+    "taskRunOptions",
     "tabInputMultiDiff",
     "tabInputTextMerge",
     "textEditorDiffInformation",
@@ -1147,6 +1148,46 @@
         "title": "%command.deleteRef%",
         "category": "Git",
         "enablement": "!operationInProgress"
+      },
+      {
+        "command": "git.repositories.worktreeCopyBranchName",
+        "title": "%command.artifactCopyBranchName%",
+        "category": "Git"
+      },
+      {
+        "command": "git.repositories.worktreeCopyCommitHash",
+        "title": "%command.artifactCopyCommitHash%",
+        "category": "Git"
+      },
+      {
+        "command": "git.repositories.worktreeCopyPath",
+        "title": "%command.artifactCopyWorktreePath%",
+        "category": "Git"
+      },
+      {
+        "command": "git.repositories.copyCommitHash",
+        "title": "%command.artifactCopyCommitHash%",
+        "category": "Git"
+      },
+      {
+        "command": "git.repositories.copyBranchName",
+        "title": "%command.artifactCopyBranchName%",
+        "category": "Git"
+      },
+      {
+        "command": "git.repositories.copyTagName",
+        "title": "%command.artifactCopyTagName%",
+        "category": "Git"
+      },
+      {
+        "command": "git.repositories.copyStashName",
+        "title": "%command.artifactCopyStashName%",
+        "category": "Git"
+      },
+      {
+        "command": "git.repositories.stashCopyBranchName",
+        "title": "%command.artifactCopyBranchName%",
+        "category": "Git"
       }
     ],
     "continueEditSession": [
@@ -1846,6 +1887,38 @@
         {
           "command": "git.repositories.deleteWorktree",
           "when": "false"
+        },
+        {
+          "command": "git.repositories.worktreeCopyBranchName",
+          "when": "false"
+        },
+        {
+          "command": "git.repositories.worktreeCopyCommitHash",
+          "when": "false"
+        },
+        {
+          "command": "git.repositories.worktreeCopyPath",
+          "when": "false"
+        },
+        {
+          "command": "git.repositories.copyCommitHash",
+          "when": "false"
+        },
+        {
+          "command": "git.repositories.copyBranchName",
+          "when": "false"
+        },
+        {
+          "command": "git.repositories.copyTagName",
+          "when": "false"
+        },
+        {
+          "command": "git.repositories.copyStashName",
+          "when": "false"
+        },
+        {
+          "command": "git.repositories.stashCopyBranchName",
+          "when": "false"
         }
       ],
       "scm/title": [
@@ -2090,6 +2163,16 @@
           "group": "3_drop@3",
           "when": "scmProvider == git && scmArtifactGroupId == stashes"
         },
+        {
+          "command": "git.repositories.stashCopyBranchName",
+          "group": "4_copy@1",
+          "when": "scmProvider == git && scmArtifactGroupId == stashes"
+        },
+        {
+          "command": "git.repositories.copyStashName",
+          "group": "4_copy@2",
+          "when": "scmProvider == git && scmArtifactGroupId == stashes"
+        },
         {
           "command": "git.repositories.checkout",
           "group": "1_checkout@1",
@@ -2130,6 +2213,21 @@
           "group": "4_compare@1",
           "when": "scmProvider == git && (scmArtifactGroupId == branches || scmArtifactGroupId == tags)"
         },
+        {
+          "command": "git.repositories.copyCommitHash",
+          "group": "5_copy@2",
+          "when": "scmProvider == git && (scmArtifactGroupId == branches || scmArtifactGroupId == tags)"
+        },
+        {
+          "command": "git.repositories.copyBranchName",
+          "group": "5_copy@1",
+          "when": "scmProvider == git && scmArtifactGroupId == branches"
+        },
+        {
+          "command": "git.repositories.copyTagName",
+          "group": "5_copy@2",
+          "when": "scmProvider == git && scmArtifactGroupId == tags"
+        },
         {
           "command": "git.repositories.openWorktreeInNewWindow",
           "group": "inline@1",
@@ -2149,6 +2247,21 @@
           "command": "git.repositories.deleteWorktree",
           "group": "2_modify@1",
           "when": "scmProvider == git && scmArtifactGroupId == worktrees"
+        },
+        {
+          "command": "git.repositories.worktreeCopyCommitHash",
+          "group": "3_copy@2",
+          "when": "scmProvider == git && scmArtifactGroupId == worktrees"
+        },
+        {
+          "command": "git.repositories.worktreeCopyBranchName",
+          "group": "3_copy@1",
+          "when": "scmProvider == git && scmArtifactGroupId == worktrees"
+        },
+        {
+          "command": "git.repositories.worktreeCopyPath",
+          "group": "3_copy@3",
+          "when": "scmProvider == git && scmArtifactGroupId == worktrees"
         }
       ],
       "scm/resourceGroup/context": [
@@ -4235,7 +4348,7 @@
     "@joaomoreno/unique-names-generator": "^5.2.0",
     "@vscode/extension-telemetry": "^0.9.8",
     "byline": "^5.0.0",
-    "file-type": "16.5.4",
+    "file-type": "21.3.1",
     "picomatch": "2.3.1",
     "vscode-uri": "^2.0.0",
     "which": "4.0.0"
diff --git a/extensions/git/package.nls.json b/extensions/git/package.nls.json
index 9d469e33c84e9..147a75f9b7024 100644
--- a/extensions/git/package.nls.json
+++ b/extensions/git/package.nls.json
@@ -129,7 +129,7 @@
 	"command.stashView": "View Stash...",
 	"command.stashView2": "View Stash",
 	"command.timelineOpenDiff": "Open Changes",
-	"command.timelineCopyCommitId": "Copy Commit ID",
+	"command.timelineCopyCommitId": "Copy Commit Hash",
 	"command.timelineCopyCommitMessage": "Copy Commit Message",
 	"command.timelineSelectForCompare": "Select for Compare",
 	"command.timelineCompareWithSelected": "Compare with Selected",
@@ -148,6 +148,11 @@
 	"command.graphCompareWithMergeBase": "Compare with Merge Base",
 	"command.graphCompareWithRemote": "Compare with Remote",
 	"command.deleteRef": "Delete",
+	"command.artifactCopyCommitHash": "Copy Commit Hash",
+	"command.artifactCopyBranchName": "Copy Branch Name",
+	"command.artifactCopyTagName": "Copy Tag Name",
+	"command.artifactCopyStashName": "Copy Stash Name",
+	"command.artifactCopyWorktreePath": "Copy Worktree Path",
 	"command.blameToggleEditorDecoration": "Toggle Git Blame Editor Decoration",
 	"command.blameToggleStatusBarItem": "Toggle Git Blame Status Bar Item",
 	"command.api.getRepositories": "Get Repositories",
diff --git a/extensions/git/src/actionButton.ts b/extensions/git/src/actionButton.ts
index 63eefb1de028a..5804c23f69755 100644
--- a/extensions/git/src/actionButton.ts
+++ b/extensions/git/src/actionButton.ts
@@ -4,7 +4,8 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Command, Disposable, Event, EventEmitter, SourceControlActionButton, Uri, workspace, l10n, LogOutputChannel } from 'vscode';
-import { Branch, RefType, Status } from './api/git';
+import type { Branch } from './api/git';
+import { RefType, Status } from './api/git.constants';
 import { OperationKind } from './operation';
 import { CommitCommandsCenter } from './postCommitCommands';
 import { Repository } from './repository';
diff --git a/extensions/git/src/api/api1.ts b/extensions/git/src/api/api1.ts
index 0791401665ec0..b97337596d1bd 100644
--- a/extensions/git/src/api/api1.ts
+++ b/extensions/git/src/api/api1.ts
@@ -5,7 +5,8 @@
 
 import { Model } from '../model';
 import { Repository as BaseRepository, Resource } from '../repository';
-import { InputBox, Git, API, Repository, Remote, RepositoryState, Branch, ForcePushMode, Ref, Submodule, Commit, Change, RepositoryUIState, Status, LogOptions, APIState, CommitOptions, RefType, CredentialsProvider, BranchQuery, PushErrorHandler, PublishEvent, FetchOptions, RemoteSourceProvider, RemoteSourcePublisher, PostCommitCommandsProvider, RefQuery, BranchProtectionProvider, InitOptions, SourceControlHistoryItemDetailsProvider, GitErrorCodes, CloneOptions, CommitShortStat, DiffChange, Worktree, RepositoryKind, RepositoryAccessDetails } from './git';
+import type { InputBox, Git, API, Repository, Remote, RepositoryState, Branch, Ref, Submodule, Commit, Change, RepositoryUIState, LogOptions, APIState, CommitOptions, CredentialsProvider, BranchQuery, PushErrorHandler, PublishEvent, FetchOptions, RemoteSourceProvider, RemoteSourcePublisher, PostCommitCommandsProvider, RefQuery, BranchProtectionProvider, InitOptions, SourceControlHistoryItemDetailsProvider, CloneOptions, CommitShortStat, DiffChange, Worktree, RepositoryKind, RepositoryAccessDetails } from './git';
+import { ForcePushMode, GitErrorCodes, RefType, Status } from './git.constants';
 import { Event, SourceControlInputBox, Uri, SourceControl, Disposable, commands, CancellationToken } from 'vscode';
 import { combinedDisposable, filterEvent, mapEvent } from '../util';
 import { toGitUri } from '../uri';
@@ -319,6 +320,10 @@ export class ApiRepository implements Repository {
 		return this.#repository.mergeAbort();
 	}
 
+	rebase(branch: string): Promise<void> {
+		return this.#repository.rebase(branch);
+	}
+
 	createStash(options?: { message?: string; includeUntracked?: boolean; staged?: boolean }): Promise<void> {
 		return this.#repository.createStash(options?.message, options?.includeUntracked, options?.staged);
 	}
@@ -346,6 +351,14 @@ export class ApiRepository implements Repository {
 	migrateChanges(sourceRepositoryPath: string, options?: { confirmation?: boolean; deleteFromSource?: boolean; untracked?: boolean }): Promise<void> {
 		return this.#repository.migrateChanges(sourceRepositoryPath, options);
 	}
+
+	generateRandomBranchName(): Promise<string | undefined> {
+		return this.#repository.generateRandomBranchName();
+	}
+
+	isBranchProtected(branch?: Branch): boolean {
+		return this.#repository.isBranchProtected(branch);
+	}
 }
 
 export class ApiGit implements Git {
diff --git a/extensions/git/src/api/extension.ts b/extensions/git/src/api/extension.ts
index 7b0313b6c26e6..a4c6af087ce1b 100644
--- a/extensions/git/src/api/extension.ts
+++ b/extensions/git/src/api/extension.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Model } from '../model';
-import { GitExtension, Repository, API } from './git';
+import type { GitExtension, Repository, API } from './git';
 import { ApiRepository, ApiImpl } from './api1';
 import { Event, EventEmitter } from 'vscode';
 import { CloneManager } from '../cloneManager';
diff --git a/extensions/git/src/api/git.constants.ts b/extensions/git/src/api/git.constants.ts
new file mode 100644
index 0000000000000..5847e21d5d0da
--- /dev/null
+++ b/extensions/git/src/api/git.constants.ts
@@ -0,0 +1,98 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import type * as git from './git';
+
+export type ForcePushMode = git.ForcePushMode;
+export type RefType = git.RefType;
+export type Status = git.Status;
+export type GitErrorCodes = git.GitErrorCodes;
+
+export const ForcePushMode = Object.freeze({
+	Force: 0,
+	ForceWithLease: 1,
+	ForceWithLeaseIfIncludes: 2,
+}) satisfies typeof git.ForcePushMode;
+
+export const RefType = Object.freeze({
+	Head: 0,
+	RemoteHead: 1,
+	Tag: 2,
+}) satisfies typeof git.RefType;
+
+export const Status = Object.freeze({
+	INDEX_MODIFIED: 0,
+	INDEX_ADDED: 1,
+	INDEX_DELETED: 2,
+	INDEX_RENAMED: 3,
+	INDEX_COPIED: 4,
+
+	MODIFIED: 5,
+	DELETED: 6,
+	UNTRACKED: 7,
+	IGNORED: 8,
+	INTENT_TO_ADD: 9,
+	INTENT_TO_RENAME: 10,
+	TYPE_CHANGED: 11,
+
+	ADDED_BY_US: 12,
+	ADDED_BY_THEM: 13,
+	DELETED_BY_US: 14,
+	DELETED_BY_THEM: 15,
+	BOTH_ADDED: 16,
+	BOTH_DELETED: 17,
+	BOTH_MODIFIED: 18,
+}) satisfies typeof git.Status;
+
+export const GitErrorCodes = Object.freeze({
+	BadConfigFile: 'BadConfigFile',
+	BadRevision: 'BadRevision',
+	AuthenticationFailed: 'AuthenticationFailed',
+	NoUserNameConfigured: 'NoUserNameConfigured',
+	NoUserEmailConfigured: 'NoUserEmailConfigured',
+	NoRemoteRepositorySpecified: 'NoRemoteRepositorySpecified',
+	NotAGitRepository: 'NotAGitRepository',
+	NotASafeGitRepository: 'NotASafeGitRepository',
+	NotAtRepositoryRoot: 'NotAtRepositoryRoot',
+	Conflict: 'Conflict',
+	StashConflict: 'StashConflict',
+	UnmergedChanges: 'UnmergedChanges',
+	PushRejected: 'PushRejected',
+	ForcePushWithLeaseRejected: 'ForcePushWithLeaseRejected',
+	ForcePushWithLeaseIfIncludesRejected: 'ForcePushWithLeaseIfIncludesRejected',
+	RemoteConnectionError: 'RemoteConnectionError',
+	DirtyWorkTree: 'DirtyWorkTree',
+	CantOpenResource: 'CantOpenResource',
+	GitNotFound: 'GitNotFound',
+	CantCreatePipe: 'CantCreatePipe',
+	PermissionDenied: 'PermissionDenied',
+	CantAccessRemote: 'CantAccessRemote',
+	RepositoryNotFound: 'RepositoryNotFound',
+	RepositoryIsLocked: 'RepositoryIsLocked',
+	BranchNotFullyMerged: 'BranchNotFullyMerged',
+	NoRemoteReference: 'NoRemoteReference',
+	InvalidBranchName: 'InvalidBranchName',
+	BranchAlreadyExists: 'BranchAlreadyExists',
+	NoLocalChanges: 'NoLocalChanges',
+	NoStashFound: 'NoStashFound',
+	LocalChangesOverwritten: 'LocalChangesOverwritten',
+	NoUpstreamBranch: 'NoUpstreamBranch',
+	IsInSubmodule: 'IsInSubmodule',
+	WrongCase: 'WrongCase',
+	CantLockRef: 'CantLockRef',
+	CantRebaseMultipleBranches: 'CantRebaseMultipleBranches',
+	PatchDoesNotApply: 'PatchDoesNotApply',
+	NoPathFound: 'NoPathFound',
+	UnknownPath: 'UnknownPath',
+	EmptyCommitMessage: 'EmptyCommitMessage',
+	BranchFastForwardRejected: 'BranchFastForwardRejected',
+	BranchNotYetBorn: 'BranchNotYetBorn',
+	TagConflict: 'TagConflict',
+	CherryPickEmpty: 'CherryPickEmpty',
+	CherryPickConflict: 'CherryPickConflict',
+	WorktreeContainsChanges: 'WorktreeContainsChanges',
+	WorktreeAlreadyExists: 'WorktreeAlreadyExists',
+	WorktreeBranchAlreadyUsed: 'WorktreeBranchAlreadyUsed',
+}) satisfies Record<keyof typeof git.GitErrorCodes, string>;
diff --git a/extensions/git/src/api/git.d.ts b/extensions/git/src/api/git.d.ts
index 287dd4399bf2c..8a258ba5741ff 100644
--- a/extensions/git/src/api/git.d.ts
+++ b/extensions/git/src/api/git.d.ts
@@ -315,6 +315,7 @@ export interface Repository {
 	commit(message: string, opts?: CommitOptions): Promise<void>;
 	merge(ref: string): Promise<void>;
 	mergeAbort(): Promise<void>;
+	rebase(branch: string): Promise<void>;
 
 	createStash(options?: { message?: string; includeUntracked?: boolean; staged?: boolean }): Promise<void>;
 	applyStash(index?: number): Promise<void>;
@@ -325,6 +326,10 @@ export interface Repository {
 	deleteWorktree(path: string, options?: { force?: boolean }): Promise<void>;
 
 	migrateChanges(sourceRepositoryPath: string, options?: { confirmation?: boolean; deleteFromSource?: boolean; untracked?: boolean }): Promise<void>;
+
+	generateRandomBranchName(): Promise<string | undefined>;
+
+	isBranchProtected(branch?: Branch): boolean;
 }
 
 export interface RemoteSource {
diff --git a/extensions/git/src/artifactProvider.ts b/extensions/git/src/artifactProvider.ts
index f63899efa3edb..f9e2d99087fd6 100644
--- a/extensions/git/src/artifactProvider.ts
+++ b/extensions/git/src/artifactProvider.ts
@@ -4,9 +4,10 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { LogOutputChannel, SourceControlArtifactProvider, SourceControlArtifactGroup, SourceControlArtifact, Event, EventEmitter, ThemeIcon, l10n, workspace, Uri, Disposable, Command } from 'vscode';
-import { coalesce, dispose, filterEvent, IDisposable, isCopilotWorktree } from './util';
+import { coalesce, dispose, filterEvent, IDisposable, isCopilotWorktreeFolder } from './util';
 import { Repository } from './repository';
-import { Ref, RefType, Worktree } from './api/git';
+import type { Ref, Worktree } from './api/git';
+import { RefType } from './api/git.constants';
 import { OperationKind } from './operation';
 
 /**
@@ -177,7 +178,7 @@ export class GitArtifactProvider implements SourceControlArtifactProvider, IDisp
 					]).join(' \u2022 '),
 					icon: w.main
 						? new ThemeIcon('repo')
-						: isCopilotWorktree(w.path)
+						: isCopilotWorktreeFolder(w.path)
 							? new ThemeIcon('chat-sparkle')
 							: new ThemeIcon('worktree')
 				}));
diff --git a/extensions/git/src/askpass.ts b/extensions/git/src/askpass.ts
index 1cb1890e24245..cc9e607f08f48 100644
--- a/extensions/git/src/askpass.ts
+++ b/extensions/git/src/askpass.ts
@@ -6,7 +6,7 @@
 import { window, InputBoxOptions, Uri, Disposable, workspace, QuickPickOptions, l10n, LogOutputChannel } from 'vscode';
 import { IDisposable, EmptyDisposable, toDisposable, extractFilePathFromArgs } from './util';
 import { IIPCHandler, IIPCServer } from './ipc/ipcServer';
-import { CredentialsProvider, Credentials } from './api/git';
+import type { CredentialsProvider, Credentials } from './api/git';
 import { ITerminalEnvironmentProvider } from './terminal';
 import { AskpassPaths } from './askpassManager';
 
diff --git a/extensions/git/src/autofetch.ts b/extensions/git/src/autofetch.ts
index 00d6450b3baf8..201bf647f1a11 100644
--- a/extensions/git/src/autofetch.ts
+++ b/extensions/git/src/autofetch.ts
@@ -6,7 +6,7 @@
 import { workspace, Disposable, EventEmitter, Memento, window, MessageItem, ConfigurationTarget, Uri, ConfigurationChangeEvent, l10n, env } from 'vscode';
 import { Repository } from './repository';
 import { eventToPromise, filterEvent, onceEvent } from './util';
-import { GitErrorCodes } from './api/git';
+import { GitErrorCodes } from './api/git.constants';
 
 export class AutoFetcher {
 
diff --git a/extensions/git/src/blame.ts b/extensions/git/src/blame.ts
index 8773264eb70f2..83a60ec9e1879 100644
--- a/extensions/git/src/blame.ts
+++ b/extensions/git/src/blame.ts
@@ -13,7 +13,7 @@ import { fromGitUri, isGitUri, toGitUri } from './uri';
 import { emojify, ensureEmojis } from './emoji';
 import { getWorkingTreeAndIndexDiffInformation, getWorkingTreeDiffInformation } from './staging';
 import { provideSourceControlHistoryItemAvatar, provideSourceControlHistoryItemHoverCommands, provideSourceControlHistoryItemMessageLinks } from './historyItemDetailsProvider';
-import { AvatarQuery, AvatarQueryCommit } from './api/git';
+import type { AvatarQuery, AvatarQueryCommit } from './api/git';
 import { LRUCache } from './cache';
 import { AVATAR_SIZE, getCommitHover, getHoverCommitHashCommands, processHoverRemoteCommands } from './hover';
 
diff --git a/extensions/git/src/branchProtection.ts b/extensions/git/src/branchProtection.ts
index 0fbb3b7d4b166..b142a333b24a1 100644
--- a/extensions/git/src/branchProtection.ts
+++ b/extensions/git/src/branchProtection.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Disposable, Event, EventEmitter, Uri, workspace } from 'vscode';
-import { BranchProtection, BranchProtectionProvider } from './api/git';
+import type { BranchProtection, BranchProtectionProvider } from './api/git';
 import { dispose, filterEvent } from './util';
 
 export interface IBranchProtectionProviderRegistry {
diff --git a/extensions/git/src/cloneManager.ts b/extensions/git/src/cloneManager.ts
index 49d57d8763c63..cee231dda779c 100644
--- a/extensions/git/src/cloneManager.ts
+++ b/extensions/git/src/cloneManager.ts
@@ -39,7 +39,8 @@ export class CloneManager {
 			/* __GDPR__
 				"clone" : {
 					"owner": "lszomoru",
-					"outcome" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "comment": "The outcome of the git operation" }
+					"outcome" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "comment": "The outcome of the git operation" },
+					"openFolder": { "classification": "SystemMetaData", "purpose": "PerformanceAndHealth", "isMeasurement": true, "comment": "Indicates whether the folder is opened following the clone operation" }
 				}
 			*/
 			this.telemetryReporter.sendTelemetryEvent('clone', { outcome: 'no_URL' });
@@ -74,7 +75,8 @@ export class CloneManager {
 				/* __GDPR__
 					"clone" : {
 						"owner": "lszomoru",
-						"outcome" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "comment": "The outcome of the git operation" }
+						"outcome" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "comment": "The outcome of the git operation" },
+						"openFolder": { "classification": "SystemMetaData", "purpose": "PerformanceAndHealth", "isMeasurement": true, "comment": "Indicates whether the folder is opened following the clone operation" }
 					}
 				*/
 				this.telemetryReporter.sendTelemetryEvent('clone', { outcome: 'no_directory' });
@@ -105,7 +107,8 @@ export class CloneManager {
 				/* __GDPR__
 					"clone" : {
 						"owner": "lszomoru",
-						"outcome" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "comment": "The outcome of the git operation" }
+						"outcome" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "comment": "The outcome of the git operation" },
+						"openFolder": { "classification": "SystemMetaData", "purpose": "PerformanceAndHealth", "isMeasurement": true, "comment": "Indicates whether the folder is opened following the clone operation" }
 					}
 				*/
 				this.telemetryReporter.sendTelemetryEvent('clone', { outcome: 'directory_not_empty' });
@@ -115,7 +118,8 @@ export class CloneManager {
 				/* __GDPR__
 					"clone" : {
 						"owner": "lszomoru",
-						"outcome" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "comment": "The outcome of the git operation" }
+						"outcome" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "comment": "The outcome of the git operation" },
+						"openFolder": { "classification": "SystemMetaData", "purpose": "PerformanceAndHealth", "isMeasurement": true, "comment": "Indicates whether the folder is opened following the clone operation" }
 					}
 				*/
 				this.telemetryReporter.sendTelemetryEvent('clone', { outcome: 'error' });
diff --git a/extensions/git/src/commands.ts b/extensions/git/src/commands.ts
index f1456675f2e61..51cbef08d2e68 100644
--- a/extensions/git/src/commands.ts
+++ b/extensions/git/src/commands.ts
@@ -7,8 +7,8 @@ import * as os from 'os';
 import * as path from 'path';
 import { Command, commands, Disposable, MessageOptions, Position, QuickPickItem, Range, SourceControlResourceState, TextDocumentShowOptions, TextEditor, Uri, ViewColumn, window, workspace, WorkspaceEdit, WorkspaceFolder, TimelineItem, env, Selection, TextDocumentContentProvider, InputBoxValidationSeverity, TabInputText, TabInputTextMerge, QuickPickItemKind, TextDocument, LogOutputChannel, l10n, Memento, UIKind, QuickInputButton, ThemeIcon, SourceControlHistoryItem, SourceControl, InputBoxValidationMessage, Tab, TabInputNotebook, QuickInputButtonLocation, languages, SourceControlArtifact, ProgressLocation } from 'vscode';
 import TelemetryReporter from '@vscode/extension-telemetry';
-import { uniqueNamesGenerator, adjectives, animals, colors, NumberDictionary } from '@joaomoreno/unique-names-generator';
-import { ForcePushMode, GitErrorCodes, RefType, Status, CommitOptions, RemoteSourcePublisher, Remote, Branch, Ref } from './api/git';
+import type { CommitOptions, RemoteSourcePublisher, Remote, Branch, Ref } from './api/git';
+import { ForcePushMode, GitErrorCodes, RefType, Status } from './api/git.constants';
 import { Git, GitError, Repository as GitRepository, Stash, Worktree } from './git';
 import { Model } from './model';
 import { GitResourceGroup, Repository, Resource, ResourceGroupType } from './repository';
@@ -106,6 +106,8 @@ class RefItem implements QuickPickItem {
 				return `refs/remotes/${this.ref.name}`;
 			case RefType.Tag:
 				return `refs/tags/${this.ref.name}`;
+			default:
+				throw new Error('Unknown ref type');
 		}
 	}
 	get refName(): string | undefined { return this.ref.name; }
@@ -1028,8 +1030,8 @@ export class CommandCenter {
 	}
 
 	@command('git.clone')
-	async clone(url?: string, parentPath?: string, options?: { ref?: string }): Promise<void> {
-		await this.cloneManager.clone(url, { parentPath, ...options });
+	async clone(url?: string, parentPath?: string, options?: { ref?: string; postCloneAction?: 'none' }): Promise<string | undefined> {
+		return this.cloneManager.clone(url, { parentPath, ...options });
 	}
 
 	@command('git.cloneRecursive')
@@ -1038,24 +1040,73 @@ export class CommandCenter {
 	}
 
 	@command('_git.cloneRepository')
-	async cloneRepository(url: string, parentPath: string): Promise<void> {
+	async cloneRepository(url: string, localPath: string, ref?: string): Promise<void> {
 		const opts = {
 			location: ProgressLocation.Notification,
 			title: l10n.t('Cloning git repository "{0}"...', url),
 			cancellable: true
 		};
 
+		const parentPath = path.dirname(localPath);
+		const targetName = path.basename(localPath);
+
 		await window.withProgress(
 			opts,
-			(progress, token) => this.model.git.clone(url, { parentPath, progress }, token)
+			(progress, token) => this.model.git.clone(url, { parentPath, targetName, progress, ref }, token)
 		);
 	}
 
+	@command('_git.checkout')
+	async checkoutRepository(repositoryPath: string, treeish: string, detached?: boolean): Promise<void> {
+		const dotGit = await this.git.getRepositoryDotGit(repositoryPath);
+		const repo = new GitRepository(this.git, repositoryPath, undefined, dotGit, this.logger);
+		await repo.checkout(treeish, [], detached ? { detached: true } : {});
+	}
+
 	@command('_git.pull')
-	async pullRepository(repositoryPath: string): Promise<void> {
+	async pullRepository(repositoryPath: string): Promise<boolean> {
+		const dotGit = await this.git.getRepositoryDotGit(repositoryPath);
+		const repo = new GitRepository(this.git, repositoryPath, undefined, dotGit, this.logger);
+		return repo.pull();
+	}
+
+	@command('_git.fetchRepository')
+	async fetchRepository(repositoryPath: string): Promise<void> {
+		const dotGit = await this.git.getRepositoryDotGit(repositoryPath);
+		const repo = new GitRepository(this.git, repositoryPath, undefined, dotGit, this.logger);
+		await repo.fetch();
+	}
+
+	@command('_git.revParse')
+	async revParse(repositoryPath: string, ref: string): Promise<string> {
+		const dotGit = await this.git.getRepositoryDotGit(repositoryPath);
+		const repo = new GitRepository(this.git, repositoryPath, undefined, dotGit, this.logger);
+		const result = await repo.exec(['rev-parse', ref]);
+		return result.stdout.trim();
+	}
+
+	@command('_git.revListCount')
+	async revListCount(repositoryPath: string, fromRef: string, toRef: string): Promise<number> {
+		const dotGit = await this.git.getRepositoryDotGit(repositoryPath);
+		const repo = new GitRepository(this.git, repositoryPath, undefined, dotGit, this.logger);
+		const result = await repo.exec(['rev-list', '--count', `${fromRef}..${toRef}`]);
+		return Number(result.stdout.trim()) || 0;
+	}
+
+	@command('_git.revParseAbbrevRef')
+	async revParseAbbrevRef(repositoryPath: string): Promise<string> {
+		const dotGit = await this.git.getRepositoryDotGit(repositoryPath);
+		const repo = new GitRepository(this.git, repositoryPath, undefined, dotGit, this.logger);
+		const result = await repo.exec(['rev-parse', '--abbrev-ref', 'HEAD']);
+		return result.stdout.trim();
+	}
+
+	@command('_git.mergeBranch')
+	async mergeBranch(repositoryPath: string, branch: string): Promise<string> {
 		const dotGit = await this.git.getRepositoryDotGit(repositoryPath);
 		const repo = new GitRepository(this.git, repositoryPath, undefined, dotGit, this.logger);
-		await repo.pull();
+		const result = await repo.exec(['merge', branch, '--no-edit']);
+		return result.stdout.trim();
 	}
 
 	@command('git.init')
@@ -2940,48 +2991,6 @@ export class CommandCenter {
 		await this._branch(repository, undefined, true);
 	}
 
-	private async generateRandomBranchName(repository: Repository, separator: string): Promise<string> {
-		const config = workspace.getConfiguration('git');
-		const branchRandomNameDictionary = config.get<string[]>('branchRandomName.dictionary')!;
-
-		const dictionaries: string[][] = [];
-		for (const dictionary of branchRandomNameDictionary) {
-			if (dictionary.toLowerCase() === 'adjectives') {
-				dictionaries.push(adjectives);
-			}
-			if (dictionary.toLowerCase() === 'animals') {
-				dictionaries.push(animals);
-			}
-			if (dictionary.toLowerCase() === 'colors') {
-				dictionaries.push(colors);
-			}
-			if (dictionary.toLowerCase() === 'numbers') {
-				dictionaries.push(NumberDictionary.generate({ length: 3 }));
-			}
-		}
-
-		if (dictionaries.length === 0) {
-			return '';
-		}
-
-		// 5 attempts to generate a random branch name
-		for (let index = 0; index < 5; index++) {
-			const randomName = uniqueNamesGenerator({
-				dictionaries,
-				length: dictionaries.length,
-				separator
-			});
-
-			// Check for local ref conflict
-			const refs = await repository.getRefs({ pattern: `refs/heads/${randomName}` });
-			if (refs.length === 0) {
-				return randomName;
-			}
-		}
-
-		return '';
-	}
-
 	private async promptForBranchName(repository: Repository, defaultName?: string, initialValue?: string): Promise<string> {
 		const config = workspace.getConfiguration('git');
 		const branchPrefix = config.get<string>('branchPrefix')!;
@@ -2995,8 +3004,7 @@ export class CommandCenter {
 		}
 
 		const getBranchName = async (): Promise<string> => {
-			const branchName = branchRandomNameEnabled ? await this.generateRandomBranchName(repository, branchWhitespaceChar) : '';
-			return `${branchPrefix}${branchName}`;
+			return await repository.generateRandomBranchName() ?? branchPrefix;
 		};
 
 		const getValueSelection = (value: string): [number, number] | undefined => {
@@ -5415,6 +5423,97 @@ export class CommandCenter {
 		await repository.deleteWorktree(artifact.id);
 	}
 
+	@command('git.repositories.worktreeCopyBranchName', { repository: true })
+	async artifactWorktreeCopyBranchName(repository: Repository, artifact: SourceControlArtifact): Promise<void> {
+		if (!repository || !artifact) {
+			return;
+		}
+
+		const worktrees = await repository.getWorktreeDetails();
+		const worktree = worktrees.find(w => w.path === artifact.id);
+		if (!worktree || worktree.detached) {
+			return;
+		}
+
+		env.clipboard.writeText(worktree.ref.substring(11));
+	}
+
+	@command('git.repositories.worktreeCopyCommitHash', { repository: true })
+	async artifactWorktreeCopyCommitHash(repository: Repository, artifact: SourceControlArtifact): Promise<void> {
+		if (!repository || !artifact) {
+			return;
+		}
+
+		const worktrees = await repository.getWorktreeDetails();
+		const worktree = worktrees.find(w => w.path === artifact.id);
+		if (!worktree?.commitDetails) {
+			return;
+		}
+
+		env.clipboard.writeText(worktree.commitDetails.hash);
+	}
+
+	@command('git.repositories.worktreeCopyPath', { repository: true })
+	async artifactWorktreeCopyPath(repository: Repository, artifact: SourceControlArtifact): Promise<void> {
+		if (!repository || !artifact) {
+			return;
+		}
+
+		env.clipboard.writeText(artifact.id);
+	}
+
+	@command('git.repositories.copyCommitHash', { repository: true })
+	async artifactCopyCommitHash(repository: Repository, artifact: SourceControlArtifact): Promise<void> {
+		if (!repository || !artifact) {
+			return;
+		}
+
+		const commit = await repository.getCommit(artifact.id);
+		env.clipboard.writeText(commit.hash);
+	}
+
+	@command('git.repositories.copyBranchName', { repository: true })
+	async artifactCopyBranchName(repository: Repository, artifact: SourceControlArtifact): Promise<void> {
+		if (!repository || !artifact) {
+			return;
+		}
+
+		env.clipboard.writeText(artifact.name);
+	}
+
+	@command('git.repositories.copyTagName', { repository: true })
+	async artifactCopyTagName(repository: Repository, artifact: SourceControlArtifact): Promise<void> {
+		if (!repository || !artifact) {
+			return;
+		}
+
+		env.clipboard.writeText(artifact.name);
+	}
+
+	@command('git.repositories.copyStashName', { repository: true })
+	async artifactCopyStashName(repository: Repository, artifact: SourceControlArtifact): Promise<void> {
+		if (!repository || !artifact) {
+			return;
+		}
+
+		env.clipboard.writeText(artifact.name);
+	}
+
+	@command('git.repositories.stashCopyBranchName', { repository: true })
+	async artifactStashCopyBranchName(repository: Repository, artifact: SourceControlArtifact): Promise<void> {
+		if (!repository || !artifact?.description) {
+			return;
+		}
+
+		const stashes = await repository.getStashes();
+		const stash = stashes.find(s => artifact.id === `stash@{${s.index}}`);
+		if (!stash?.branchName) {
+			return;
+		}
+
+		env.clipboard.writeText(stash.branchName);
+	}
+
 	private createCommand(id: string, key: string, method: Function, options: ScmCommandOptions): (...args: any[]) => any {
 		const result = (...args: any[]) => {
 			let result: Promise<any>;
@@ -5545,15 +5644,14 @@ export class CommandCenter {
 						options.modal = false;
 						break;
 					default: {
-						const hint = (err.stderr || err.message || String(err))
+						const hintLines = (err.stderr || err.stdout || err.message || String(err))
 							.replace(/^error: /mi, '')
 							.replace(/^> husky.*$/mi, '')
 							.split(/[\r\n]/)
-							.filter((line: string) => !!line)
-						[0];
+							.filter((line: string) => !!line);
 
-						message = hint
-							? l10n.t('Git: {0}', hint)
+						message = hintLines.length > 0
+							? l10n.t('Git: {0}', err.stdout ? hintLines[hintLines.length - 1] : hintLines[0])
 							: l10n.t('Git error');
 
 						break;
diff --git a/extensions/git/src/decorationProvider.ts b/extensions/git/src/decorationProvider.ts
index fb895d5aff2b3..11778f7f8f582 100644
--- a/extensions/git/src/decorationProvider.ts
+++ b/extensions/git/src/decorationProvider.ts
@@ -9,7 +9,8 @@ import { Repository, GitResourceGroup } from './repository';
 import { Model } from './model';
 import { debounce } from './decorators';
 import { filterEvent, dispose, anyEvent, PromiseSource, combinedDisposable, runAndSubscribeEvent } from './util';
-import { Change, GitErrorCodes, Status } from './api/git';
+import type { Change } from './api/git';
+import { GitErrorCodes, Status } from './api/git.constants';
 
 function equalSourceControlHistoryItemRefs(ref1?: SourceControlHistoryItemRef, ref2?: SourceControlHistoryItemRef): boolean {
 	if (ref1 === ref2) {
diff --git a/extensions/git/src/editSessionIdentityProvider.ts b/extensions/git/src/editSessionIdentityProvider.ts
index 8380f03ecfd94..a3336d441743d 100644
--- a/extensions/git/src/editSessionIdentityProvider.ts
+++ b/extensions/git/src/editSessionIdentityProvider.ts
@@ -5,7 +5,7 @@
 
 import * as path from 'path';
 import * as vscode from 'vscode';
-import { RefType } from './api/git';
+import { RefType } from './api/git.constants';
 import { Model } from './model';
 
 export class GitEditSessionIdentityProvider implements vscode.EditSessionIdentityProvider, vscode.Disposable {
diff --git a/extensions/git/src/fileSystemProvider.ts b/extensions/git/src/fileSystemProvider.ts
index 19928863832a5..a09d00bfc2268 100644
--- a/extensions/git/src/fileSystemProvider.ts
+++ b/extensions/git/src/fileSystemProvider.ts
@@ -131,6 +131,26 @@ export class GitFileSystemProvider implements FileSystemProvider {
 		this.cache = cache;
 	}
 
+	private async getOrOpenRepository(uri: string | Uri): Promise<Repository | undefined> {
+		let repository = this.model.getRepository(uri);
+		if (repository) {
+			return repository;
+		}
+
+		// In case of the empty window, or the agent sessions window, no repositories are open
+		// so we need to explicitly open a repository before we can serve git content for the
+		// given git resource.
+		if (workspace.workspaceFolders === undefined || workspace.isAgentSessionsWorkspace) {
+			const fsPath = typeof uri === 'string' ? uri : fromGitUri(uri).path;
+			this.logger.info(`[GitFileSystemProvider][getOrOpenRepository] Opening repository for ${fsPath}`);
+
+			await this.model.openRepository(fsPath, true, true);
+			repository = this.model.getRepository(uri);
+		}
+
+		return repository;
+	}
+
 	watch(): Disposable {
 		return EmptyDisposable;
 	}
@@ -139,7 +159,11 @@ export class GitFileSystemProvider implements FileSystemProvider {
 		await this.model.isInitialized;
 
 		const { submoduleOf, path, ref } = fromGitUri(uri);
-		const repository = submoduleOf ? this.model.getRepository(submoduleOf) : this.model.getRepository(uri);
+
+		const repository = submoduleOf
+			? await this.getOrOpenRepository(submoduleOf)
+			: await this.getOrOpenRepository(uri);
+
 		if (!repository) {
 			this.logger.warn(`[GitFileSystemProvider][stat] Repository not found - ${uri.toString()}`);
 			throw FileSystemError.FileNotFound();
@@ -175,7 +199,7 @@ export class GitFileSystemProvider implements FileSystemProvider {
 		const { path, ref, submoduleOf } = fromGitUri(uri);
 
 		if (submoduleOf) {
-			const repository = this.model.getRepository(submoduleOf);
+			const repository = await this.getOrOpenRepository(submoduleOf);
 
 			if (!repository) {
 				throw FileSystemError.FileNotFound();
@@ -190,7 +214,7 @@ export class GitFileSystemProvider implements FileSystemProvider {
 			}
 		}
 
-		const repository = this.model.getRepository(uri);
+		const repository = await this.getOrOpenRepository(uri);
 
 		if (!repository) {
 			this.logger.warn(`[GitFileSystemProvider][readFile] Repository not found - ${uri.toString()}`);
diff --git a/extensions/git/src/git.ts b/extensions/git/src/git.ts
index 5127ae0fbb95f..14e61bc3f8b70 100644
--- a/extensions/git/src/git.ts
+++ b/extensions/git/src/git.ts
@@ -10,10 +10,11 @@ import * as cp from 'child_process';
 import { fileURLToPath } from 'url';
 import which from 'which';
 import { EventEmitter } from 'events';
-import * as filetype from 'file-type';
+import { fileTypeFromBuffer } from 'file-type';
 import { assign, groupBy, IDisposable, toDisposable, dispose, mkdirp, readBytes, detectUnicodeEncoding, Encoding, onceEvent, splitInChunks, Limiter, Versions, isWindows, pathEquals, isMacintosh, isDescendant, relativePathWithNoFallback, Mutable } from './util';
 import { CancellationError, CancellationToken, ConfigurationChangeEvent, LogOutputChannel, Progress, Uri, workspace } from 'vscode';
-import { Commit as ApiCommit, Ref, RefType, Branch, Remote, ForcePushMode, GitErrorCodes, LogOptions, Change, Status, CommitOptions, RefQuery as ApiRefQuery, InitOptions, DiffChange, Worktree as ApiWorktree } from './api/git';
+import type { Commit as ApiCommit, Ref, Branch, Remote, LogOptions, Change, CommitOptions, RefQuery as ApiRefQuery, InitOptions, DiffChange, Worktree as ApiWorktree } from './api/git';
+import { RefType, ForcePushMode, GitErrorCodes, Status } from './api/git.constants';
 import * as byline from 'byline';
 import { StringDecoder } from 'string_decoder';
 
@@ -377,6 +378,7 @@ const STASH_FORMAT = '%H%n%P%n%gd%n%gs%n%at%n%ct';
 
 export interface ICloneOptions {
 	readonly parentPath: string;
+	readonly targetName?: string;
 	readonly progress: Progress<{ increment: number }>;
 	readonly recursive?: boolean;
 	readonly ref?: string;
@@ -432,14 +434,16 @@ export class Git {
 	}
 
 	async clone(url: string, options: ICloneOptions, cancellationToken?: CancellationToken): Promise<string> {
-		const baseFolderName = decodeURI(url).replace(/[\/]+$/, '').replace(/^.*[\/\\]/, '').replace(/\.git$/, '') || 'repository';
+		const baseFolderName = options.targetName || decodeURI(url).replace(/[\/]+$/, '').replace(/^.*[\/\\]/, '').replace(/\.git$/, '') || 'repository';
 		let folderName = baseFolderName;
 		let folderPath = path.join(options.parentPath, folderName);
 		let count = 1;
 
-		while (count < 20 && await new Promise(c => exists(folderPath, c))) {
-			folderName = `${baseFolderName}-${count++}`;
-			folderPath = path.join(options.parentPath, folderName);
+		if (!options.targetName) {
+			while (count < 20 && await new Promise(c => exists(folderPath, c))) {
+				folderName = `${baseFolderName}-${count++}`;
+				folderPath = path.join(options.parentPath, folderName);
+			}
 		}
 
 		await mkdirp(options.parentPath);
@@ -1073,7 +1077,7 @@ function parseGitChanges(repositoryRoot: string, raw: string): Change[] {
 
 		let uri = originalUri;
 		let renameUri = originalUri;
-		let status = Status.UNTRACKED;
+		let status: Status = Status.UNTRACKED;
 
 		// Copy or Rename status comes with a number (ex: 'R100').
 		// We don't need the number, we use only first character of the status.
@@ -1138,7 +1142,7 @@ function parseGitChangesRaw(repositoryRoot: string, raw: string): DiffChange[] {
 
 			let uri = originalUri;
 			let renameUri = originalUri;
-			let status = Status.UNTRACKED;
+			let status: Status = Status.UNTRACKED;
 
 			switch (change[0]) {
 				case 'A':
@@ -1687,7 +1691,7 @@ export class Repository {
 		}
 
 		if (!isText) {
-			const result = await filetype.fromBuffer(buffer);
+			const result = await fileTypeFromBuffer(buffer);
 
 			if (!result) {
 				return { mimetype: 'application/octet-stream' };
@@ -2420,7 +2424,7 @@ export class Repository {
 		await this.exec(args, spawnOptions);
 	}
 
-	async pull(rebase?: boolean, remote?: string, branch?: string, options: PullOptions = {}): Promise<void> {
+	async pull(rebase?: boolean, remote?: string, branch?: string, options: PullOptions = {}): Promise<boolean> {
 		const args = ['pull'];
 
 		if (options.tags) {
@@ -2446,10 +2450,11 @@ export class Repository {
 		}
 
 		try {
-			await this.exec(args, {
+			const result = await this.exec(args, {
 				cancellationToken: options.cancellationToken,
 				env: { 'GIT_HTTP_USER_AGENT': this.git.userAgent }
 			});
+			return !/Already up to date/i.test(result.stdout);
 		} catch (err) {
 			if (/^CONFLICT \([^)]+\): \b/m.test(err.stdout || '')) {
 				err.gitErrorCode = GitErrorCodes.Conflict;
diff --git a/extensions/git/src/historyItemDetailsProvider.ts b/extensions/git/src/historyItemDetailsProvider.ts
index be0e2b337f8f6..cccdf508fe3a8 100644
--- a/extensions/git/src/historyItemDetailsProvider.ts
+++ b/extensions/git/src/historyItemDetailsProvider.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Command, Disposable } from 'vscode';
-import { AvatarQuery, SourceControlHistoryItemDetailsProvider } from './api/git';
+import type { AvatarQuery, SourceControlHistoryItemDetailsProvider } from './api/git';
 import { Repository } from './repository';
 import { ApiRepository } from './api/api1';
 
diff --git a/extensions/git/src/historyProvider.ts b/extensions/git/src/historyProvider.ts
index 29e8705e04b35..c658b4c005eec 100644
--- a/extensions/git/src/historyProvider.ts
+++ b/extensions/git/src/historyProvider.ts
@@ -8,7 +8,8 @@ import { CancellationToken, Disposable, Event, EventEmitter, FileDecoration, Fil
 import { Repository, Resource } from './repository';
 import { IDisposable, deltaHistoryItemRefs, dispose, filterEvent, subject, truncate } from './util';
 import { toMultiFileDiffEditorUris } from './uri';
-import { AvatarQuery, AvatarQueryCommit, Branch, LogOptions, Ref, RefType } from './api/git';
+import type { AvatarQuery, AvatarQueryCommit, Branch, LogOptions, Ref } from './api/git';
+import { RefType } from './api/git.constants';
 import { emojify, ensureEmojis } from './emoji';
 import { Commit } from './git';
 import { OperationKind, OperationResult } from './operation';
diff --git a/extensions/git/src/main.ts b/extensions/git/src/main.ts
index b37ae9c79c5b7..b2690b24a7cdd 100644
--- a/extensions/git/src/main.ts
+++ b/extensions/git/src/main.ts
@@ -12,7 +12,7 @@ import { GitDecorations } from './decorationProvider';
 import { Askpass } from './askpass';
 import { toDisposable, filterEvent, eventToPromise } from './util';
 import TelemetryReporter from '@vscode/extension-telemetry';
-import { GitExtension } from './api/git';
+import type { GitExtension } from './api/git';
 import { GitProtocolHandler } from './protocolHandler';
 import { GitExtensionImpl } from './api/extension';
 import * as path from 'path';
diff --git a/extensions/git/src/model.ts b/extensions/git/src/model.ts
index 1d65d3dc2d755..deecc7c28629a 100644
--- a/extensions/git/src/model.ts
+++ b/extensions/git/src/model.ts
@@ -12,7 +12,7 @@ import { Git } from './git';
 import * as path from 'path';
 import * as fs from 'fs';
 import { fromGitUri } from './uri';
-import { APIState as State, CredentialsProvider, PushErrorHandler, PublishEvent, RemoteSourcePublisher, PostCommitCommandsProvider, BranchProtectionProvider, SourceControlHistoryItemDetailsProvider } from './api/git';
+import type { APIState as State, CredentialsProvider, PushErrorHandler, PublishEvent, RemoteSourcePublisher, PostCommitCommandsProvider, BranchProtectionProvider, SourceControlHistoryItemDetailsProvider } from './api/git';
 import { Askpass } from './askpass';
 import { IPushErrorHandlerRegistry } from './pushError';
 import { ApiRepository } from './api/api1';
diff --git a/extensions/git/src/postCommitCommands.ts b/extensions/git/src/postCommitCommands.ts
index 69a18114a41e2..50658d14202ba 100644
--- a/extensions/git/src/postCommitCommands.ts
+++ b/extensions/git/src/postCommitCommands.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Command, commands, Disposable, Event, EventEmitter, Memento, Uri, workspace, l10n } from 'vscode';
-import { PostCommitCommandsProvider } from './api/git';
+import type { PostCommitCommandsProvider } from './api/git';
 import { IRepositoryResolver, Repository } from './repository';
 import { ApiRepository } from './api/api1';
 import { dispose } from './util';
diff --git a/extensions/git/src/pushError.ts b/extensions/git/src/pushError.ts
index 6222923ff6864..71f564e8fa255 100644
--- a/extensions/git/src/pushError.ts
+++ b/extensions/git/src/pushError.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Disposable } from 'vscode';
-import { PushErrorHandler } from './api/git';
+import type { PushErrorHandler } from './api/git';
 
 export interface IPushErrorHandlerRegistry {
 	registerPushErrorHandler(provider: PushErrorHandler): Disposable;
diff --git a/extensions/git/src/quickDiffProvider.ts b/extensions/git/src/quickDiffProvider.ts
index 3b1aa64c8faae..961f5387555fd 100644
--- a/extensions/git/src/quickDiffProvider.ts
+++ b/extensions/git/src/quickDiffProvider.ts
@@ -7,7 +7,7 @@ import { FileType, l10n, LogOutputChannel, QuickDiffProvider, Uri, workspace } f
 import { IRepositoryResolver, Repository } from './repository';
 import { isDescendant, pathEquals } from './util';
 import { toGitUri } from './uri';
-import { Status } from './api/git';
+import { Status } from './api/git.constants';
 
 export class GitQuickDiffProvider implements QuickDiffProvider {
 	readonly label = l10n.t('Git Local Changes (Working Tree)');
diff --git a/extensions/git/src/remotePublisher.ts b/extensions/git/src/remotePublisher.ts
index 1326776cde4a0..eb8ec7b8e19bb 100644
--- a/extensions/git/src/remotePublisher.ts
+++ b/extensions/git/src/remotePublisher.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Disposable, Event } from 'vscode';
-import { RemoteSourcePublisher } from './api/git';
+import type { RemoteSourcePublisher } from './api/git';
 
 export interface IRemoteSourcePublisherRegistry {
 	readonly onDidAddRemoteSourcePublisher: Event<RemoteSourcePublisher>;
diff --git a/extensions/git/src/repository.ts b/extensions/git/src/repository.ts
index f3b1afb4689e0..446384bc3dbb0 100644
--- a/extensions/git/src/repository.ts
+++ b/extensions/git/src/repository.ts
@@ -4,14 +4,16 @@
  *--------------------------------------------------------------------------------------------*/
 
 import TelemetryReporter from '@vscode/extension-telemetry';
+import { uniqueNamesGenerator, adjectives, animals, colors, NumberDictionary } from '@joaomoreno/unique-names-generator';
 import * as fs from 'fs';
 import * as fsPromises from 'fs/promises';
 import * as path from 'path';
 import picomatch from 'picomatch';
-import { CancellationError, CancellationToken, CancellationTokenSource, Command, commands, Disposable, Event, EventEmitter, ExcludeSettingOptions, FileDecoration, l10n, LogLevel, LogOutputChannel, Memento, ProgressLocation, ProgressOptions, RelativePattern, scm, SourceControl, SourceControlInputBox, SourceControlInputBoxValidation, SourceControlInputBoxValidationType, SourceControlResourceDecorations, SourceControlResourceGroup, SourceControlResourceState, TabInputNotebookDiff, TabInputTextDiff, TabInputTextMultiDiff, ThemeColor, ThemeIcon, Uri, window, workspace, WorkspaceEdit } from 'vscode';
+import { CancellationError, CancellationToken, CancellationTokenSource, Command, commands, CustomExecution, Disposable, Event, EventEmitter, ExcludeSettingOptions, FileDecoration, l10n, LogLevel, LogOutputChannel, Memento, ProcessExecution, ProgressLocation, ProgressOptions, RelativePattern, scm, ShellExecution, SourceControl, SourceControlInputBox, SourceControlInputBoxValidation, SourceControlInputBoxValidationType, SourceControlResourceDecorations, SourceControlResourceGroup, SourceControlResourceState, TabInputNotebookDiff, TabInputTextDiff, TabInputTextMultiDiff, Task, TaskRunOn, tasks, ThemeColor, ThemeIcon, Uri, window, workspace, WorkspaceEdit, WorkspaceFolder } from 'vscode';
 import { ActionButton } from './actionButton';
 import { ApiRepository } from './api/api1';
-import { Branch, BranchQuery, Change, CommitOptions, DiffChange, FetchOptions, ForcePushMode, GitErrorCodes, LogOptions, Ref, RefType, Remote, RepositoryKind, Status } from './api/git';
+import type { Branch, BranchQuery, Change, CommitOptions, DiffChange, FetchOptions, LogOptions, Ref, Remote, RepositoryKind } from './api/git';
+import { ForcePushMode, GitErrorCodes, RefType, Status } from './api/git.constants';
 import { AutoFetcher } from './autofetch';
 import { GitBranchProtectionProvider, IBranchProtectionProviderRegistry } from './branchProtection';
 import { debounce, memoize, sequentialize, throttle } from './decorators';
@@ -23,7 +25,7 @@ import { IPushErrorHandlerRegistry } from './pushError';
 import { IRemoteSourcePublisherRegistry } from './remotePublisher';
 import { StatusBarCommands } from './statusbar';
 import { toGitUri } from './uri';
-import { anyEvent, combinedDisposable, debounceEvent, dispose, EmptyDisposable, eventToPromise, filterEvent, find, getCommitShortHash, IDisposable, isCopilotWorktree, isDescendant, isLinuxSnap, isRemote, isWindows, Limiter, onceEvent, pathEquals, relativePath } from './util';
+import { anyEvent, combinedDisposable, debounceEvent, dispose, EmptyDisposable, eventToPromise, filterEvent, find, getCommitShortHash, IDisposable, isCopilotWorktreeFolder, isDescendant, isLinuxSnap, isRemote, isWindows, Limiter, onceEvent, pathEquals, relativePath } from './util';
 import { IFileWatcher, watch } from './watch';
 import { ISourceControlHistoryItemDetailsProviderRegistry } from './historyItemDetailsProvider';
 import { GitArtifactProvider } from './artifactProvider';
@@ -952,7 +954,7 @@ export class Repository implements Disposable {
 		const icon = repository.kind === 'submodule'
 			? new ThemeIcon('archive')
 			: repository.kind === 'worktree'
-				? isCopilotWorktree(repository.root)
+				? isCopilotWorktreeFolder(repository.root)
 					? new ThemeIcon('chat-sparkle')
 					: new ThemeIcon('worktree')
 				: new ThemeIcon('repo');
@@ -965,7 +967,7 @@ export class Repository implements Disposable {
 		//   from the Repositories view.
 		this._isHidden = workspace.workspaceFolders === undefined ||
 			(repository.kind === 'worktree' &&
-				isCopilotWorktree(repository.root) && parent !== undefined);
+				isCopilotWorktreeFolder(repository.root) && parent !== undefined);
 
 		const root = Uri.file(repository.root);
 		this._sourceControl = scm.createSourceControl('git', 'Git', root, icon, this._isHidden, parent);
@@ -1890,15 +1892,41 @@ export class Repository implements Disposable {
 				this.globalState.update(`${Repository.WORKTREE_ROOT_STORAGE_KEY}:${this.root}`, newWorktreeRoot);
 			}
 
-			// Copy worktree include files. We explicitly do not await this
-			// since we don't want to block the worktree creation on the
-			// copy operation.
-			this._copyWorktreeIncludeFiles(worktreePath!);
+			this._setupWorktree(worktreePath!);
 
 			return worktreePath!;
 		});
 	}
 
+	private async _setupWorktree(worktreePath: string): Promise<void> {
+		// Copy worktree include files and wait for the copy to complete
+		// before running any worktree-created tasks.
+		await this._copyWorktreeIncludeFiles(worktreePath);
+
+		await this._runWorktreeCreatedTasks(worktreePath);
+	}
+
+	private async _runWorktreeCreatedTasks(worktreePath: string): Promise<void> {
+		try {
+			const allTasks = await tasks.fetchTasks();
+			const worktreeTasks = allTasks.filter(task => task.runOptions.runOn === TaskRunOn.WorktreeCreated);
+
+			for (const task of worktreeTasks) {
+				const worktreeTask = retargetTaskToWorktree(task, worktreePath);
+				if (!worktreeTask) {
+					this.logger.warn(`[Repository][_runWorktreeCreatedTasks] Skipped task '${task.name}' because it could not be retargeted to worktree '${worktreePath}'.`);
+					continue;
+				}
+
+				tasks.executeTask(worktreeTask).then(undefined, err => {
+					this.logger.warn(`[Repository][_runWorktreeCreatedTasks] Failed to execute worktree-created task '${task.name}' for '${worktreePath}': ${err}`);
+				});
+			}
+		} catch (err) {
+			this.logger.warn(`[Repository][_runWorktreeCreatedTasks] Failed to execute worktree-created tasks for '${worktreePath}': ${err}`);
+		}
+	}
+
 	private async _getWorktreeIncludePaths(): Promise<Set<string>> {
 		const config = workspace.getConfiguration('git', Uri.file(this.root));
 		const worktreeIncludeFiles = config.get<string[]>('worktreeIncludeFiles', []);
@@ -3293,7 +3321,110 @@ export class Repository implements Disposable {
 		return this.unpublishedCommits;
 	}
 
+	async generateRandomBranchName(): Promise<string | undefined> {
+		const config = workspace.getConfiguration('git', Uri.file(this.root));
+		const branchRandomNameEnabled = config.get<boolean>('branchRandomName.enable', false);
+
+		if (!branchRandomNameEnabled) {
+			return undefined;
+		}
+
+		const branchPrefix = config.get<string>('branchPrefix', '');
+		const branchWhitespaceChar = config.get<string>('branchWhitespaceChar', '-');
+		const branchRandomNameDictionary = config.get<string[]>('branchRandomName.dictionary', ['adjectives', 'animals']);
+
+		const dictionaries: string[][] = [];
+		for (const dictionary of branchRandomNameDictionary) {
+			if (dictionary.toLowerCase() === 'adjectives') {
+				dictionaries.push(adjectives);
+			}
+			if (dictionary.toLowerCase() === 'animals') {
+				dictionaries.push(animals);
+			}
+			if (dictionary.toLowerCase() === 'colors') {
+				dictionaries.push(colors);
+			}
+			if (dictionary.toLowerCase() === 'numbers') {
+				dictionaries.push(NumberDictionary.generate({ length: 3 }));
+			}
+		}
+
+		if (dictionaries.length === 0) {
+			return undefined;
+		}
+
+		// 5 attempts to generate a random branch name
+		for (let index = 0; index < 5; index++) {
+			const randomName = uniqueNamesGenerator({
+				dictionaries,
+				length: dictionaries.length,
+				separator: branchWhitespaceChar
+			});
+
+			// Check for local ref conflict
+			const refs = await this.getRefs({ pattern: `refs/heads/${branchPrefix}${randomName}` });
+			if (refs.length === 0) {
+				return `${branchPrefix}${randomName}`;
+			}
+		}
+
+		return undefined;
+	}
+
 	dispose(): void {
 		this.disposables = dispose(this.disposables);
 	}
 }
+
+function retargetTaskToWorktree(task: Task, worktreePath: string): Task | undefined {
+	const execution = retargetTaskExecution(task.execution, worktreePath);
+	if (!execution) {
+		return undefined;
+	}
+
+	const worktreeFolder: WorkspaceFolder = {
+		uri: Uri.file(worktreePath),
+		name: path.basename(worktreePath),
+		index: workspace.workspaceFolders?.length ?? 0
+	};
+
+	const worktreeTask = new Task({ ...task.definition }, worktreeFolder, task.name, task.source, execution, task.problemMatchers);
+	worktreeTask.detail = task.detail;
+	worktreeTask.group = task.group;
+	worktreeTask.isBackground = task.isBackground;
+	worktreeTask.presentationOptions = { ...task.presentationOptions };
+	worktreeTask.runOptions = { ...task.runOptions };
+
+	return worktreeTask;
+}
+
+function retargetTaskExecution(execution: ProcessExecution | ShellExecution | CustomExecution | undefined, worktreePath: string): ProcessExecution | ShellExecution | CustomExecution | undefined {
+	if (!execution) {
+		return undefined;
+	}
+
+	if (execution instanceof ProcessExecution) {
+		return new ProcessExecution(execution.process, execution.args, {
+			...execution.options,
+			cwd: worktreePath
+		});
+	}
+
+	if (execution instanceof ShellExecution) {
+		if (execution.commandLine !== undefined) {
+			return new ShellExecution(execution.commandLine, {
+				...execution.options,
+				cwd: worktreePath
+			});
+		}
+
+		if (execution.command !== undefined) {
+			return new ShellExecution(execution.command, execution.args ?? [], {
+				...execution.options,
+				cwd: worktreePath
+			});
+		}
+	}
+
+	return execution;
+}
diff --git a/extensions/git/src/repositoryCache.ts b/extensions/git/src/repositoryCache.ts
index 6aa998b7679bb..8f03d8998c771 100644
--- a/extensions/git/src/repositoryCache.ts
+++ b/extensions/git/src/repositoryCache.ts
@@ -5,7 +5,7 @@
 
 import { LogOutputChannel, Memento, Uri, workspace } from 'vscode';
 import { LRUCache } from './cache';
-import { Remote, RepositoryAccessDetails } from './api/git';
+import type { Remote, RepositoryAccessDetails } from './api/git';
 import { isDescendant } from './util';
 
 export interface RepositoryCacheInfo {
diff --git a/extensions/git/src/statusbar.ts b/extensions/git/src/statusbar.ts
index d5cbe86ee7c88..32fb1f588642b 100644
--- a/extensions/git/src/statusbar.ts
+++ b/extensions/git/src/statusbar.ts
@@ -6,7 +6,8 @@
 import { Disposable, Command, EventEmitter, Event, workspace, Uri, l10n } from 'vscode';
 import { Repository } from './repository';
 import { anyEvent, dispose, filterEvent } from './util';
-import { Branch, RefType, RemoteSourcePublisher } from './api/git';
+import type { Branch, RemoteSourcePublisher } from './api/git';
+import { RefType } from './api/git.constants';
 import { IRemoteSourcePublisherRegistry } from './remotePublisher';
 import { CheckoutOperation, CheckoutTrackingOperation, OperationKind } from './operation';
 
diff --git a/extensions/git/src/test/smoke.test.ts b/extensions/git/src/test/smoke.test.ts
index d9a5776824b2e..c2870a2631ee3 100644
--- a/extensions/git/src/test/smoke.test.ts
+++ b/extensions/git/src/test/smoke.test.ts
@@ -9,7 +9,8 @@ import { workspace, commands, window, Uri, WorkspaceEdit, Range, TextDocument, e
 import * as cp from 'child_process';
 import * as fs from 'fs';
 import * as path from 'path';
-import { GitExtension, API, Repository, Status } from '../api/git';
+import type { GitExtension, API, Repository } from '../api/git';
+import { Status } from '../api/git.constants';
 import { eventToPromise } from '../util';
 
 suite('git smoke test', function () {
diff --git a/extensions/git/src/timelineProvider.ts b/extensions/git/src/timelineProvider.ts
index 1ccf04a423d8d..a07eb4bfba78e 100644
--- a/extensions/git/src/timelineProvider.ts
+++ b/extensions/git/src/timelineProvider.ts
@@ -12,7 +12,7 @@ import { CommandCenter } from './commands';
 import { OperationKind, OperationResult } from './operation';
 import { truncate } from './util';
 import { provideSourceControlHistoryItemAvatar, provideSourceControlHistoryItemHoverCommands, provideSourceControlHistoryItemMessageLinks } from './historyItemDetailsProvider';
-import { AvatarQuery, AvatarQueryCommit } from './api/git';
+import type { AvatarQuery, AvatarQueryCommit } from './api/git';
 import { getCommitHover, getHoverCommitHashCommands, processHoverRemoteCommands } from './hover';
 
 export class GitTimelineItem extends TimelineItem {
diff --git a/extensions/git/src/uri.ts b/extensions/git/src/uri.ts
index 8b04fabe583eb..1d79e67e8e67b 100644
--- a/extensions/git/src/uri.ts
+++ b/extensions/git/src/uri.ts
@@ -4,7 +4,8 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Uri } from 'vscode';
-import { Change, Status } from './api/git';
+import type { Change } from './api/git';
+import { Status } from './api/git.constants';
 
 export interface GitUriParams {
 	path: string;
diff --git a/extensions/git/src/util.ts b/extensions/git/src/util.ts
index c6ec6ece45c69..58a6d06419a78 100644
--- a/extensions/git/src/util.ts
+++ b/extensions/git/src/util.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Event, Disposable, EventEmitter, SourceControlHistoryItemRef, l10n, workspace, Uri, DiagnosticSeverity, env, SourceControlHistoryItem } from 'vscode';
-import { dirname, normalize, sep, relative } from 'path';
+import { basename, dirname, normalize, sep, relative } from 'path';
 import { Readable } from 'stream';
 import { promises as fs, createReadStream } from 'fs';
 import byline from 'byline';
@@ -867,10 +867,6 @@ export function getStashDescription(stash: Stash): string | undefined {
 	return descriptionSegments.join(' \u2022 ');
 }
 
-export function isCopilotWorktree(path: string): boolean {
-	const lastSepIndex = path.lastIndexOf(sep);
-
-	return lastSepIndex !== -1
-		? path.substring(lastSepIndex + 1).startsWith('copilot-worktree-')
-		: path.startsWith('copilot-worktree-');
+export function isCopilotWorktreeFolder(path: string): boolean {
+	return basename(path).startsWith('copilot-');
 }
diff --git a/extensions/git/tsconfig.json b/extensions/git/tsconfig.json
index 2a7ad5259acca..a34d12aaa4838 100644
--- a/extensions/git/tsconfig.json
+++ b/extensions/git/tsconfig.json
@@ -27,6 +27,7 @@
 		"../../src/vscode-dts/vscode.proposed.scmMultiDiffEditor.d.ts",
 		"../../src/vscode-dts/vscode.proposed.scmTextDocument.d.ts",
 		"../../src/vscode-dts/vscode.proposed.statusBarItemTooltip.d.ts",
+		"../../src/vscode-dts/vscode.proposed.taskRunOptions.d.ts",
 		"../../src/vscode-dts/vscode.proposed.tabInputMultiDiff.d.ts",
 		"../../src/vscode-dts/vscode.proposed.tabInputTextMerge.d.ts",
 		"../../src/vscode-dts/vscode.proposed.textEditorDiffInformation.d.ts",
diff --git a/extensions/github-authentication/.vscodeignore b/extensions/github-authentication/.vscodeignore
index 0f1797efe9561..fd8583ab8d125 100644
--- a/extensions/github-authentication/.vscodeignore
+++ b/extensions/github-authentication/.vscodeignore
@@ -3,7 +3,7 @@ src/**
 !src/common/config.json
 out/**
 build/**
-extension.webpack.config.js
-extension-browser.webpack.config.js
+esbuild.mts
+esbuild.browser.mts
 tsconfig*.json
 package-lock.json
diff --git a/extensions/github-authentication/esbuild.browser.mts b/extensions/github-authentication/esbuild.browser.mts
new file mode 100644
index 0000000000000..20745e1d0870e
--- /dev/null
+++ b/extensions/github-authentication/esbuild.browser.mts
@@ -0,0 +1,40 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+import * as path from 'node:path';
+import type { Plugin } from 'esbuild';
+import { run } from '../esbuild-extension-common.mts';
+
+const srcDir = path.join(import.meta.dirname, 'src');
+const outDir = path.join(import.meta.dirname, 'dist', 'browser');
+
+/**
+ * Plugin that rewrites `./node/*` imports to `./browser/*` for the web build,
+ * replacing the platform-specific implementations with their browser equivalents.
+ */
+const platformModulesPlugin: Plugin = {
+	name: 'platform-modules',
+	setup(build) {
+		build.onResolve({ filter: /\/node\// }, args => {
+			if (args.kind !== 'import-statement' || !args.resolveDir) {
+				return;
+			}
+			const remapped = args.path.replace('/node/', '/browser/');
+			return build.resolve(remapped, { resolveDir: args.resolveDir, kind: args.kind });
+		});
+	},
+};
+
+run({
+	platform: 'browser',
+	entryPoints: {
+		'extension': path.join(srcDir, 'extension.ts'),
+	},
+	srcDir,
+	outdir: outDir,
+	additionalOptions: {
+		plugins: [platformModulesPlugin],
+		tsconfig: path.join(import.meta.dirname, 'tsconfig.browser.json'),
+	},
+}, process.argv);
diff --git a/extensions/github/extension.webpack.config.js b/extensions/github-authentication/esbuild.mts
similarity index 51%
rename from extensions/github/extension.webpack.config.js
rename to extensions/github-authentication/esbuild.mts
index 9e2b191a389d4..2b75ca703da06 100644
--- a/extensions/github/extension.webpack.config.js
+++ b/extensions/github-authentication/esbuild.mts
@@ -2,22 +2,17 @@
  *  Copyright (c) Microsoft Corporation. All rights reserved.
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
-// @ts-check
-import withDefaults from '../shared.webpack.config.mjs';
+import * as path from 'node:path';
+import { run } from '../esbuild-extension-common.mts';
 
-export default withDefaults({
-	context: import.meta.dirname,
-	entry: {
-		extension: './src/extension.ts'
-	},
-	output: {
-		libraryTarget: 'module',
-		chunkFormat: 'module',
-	},
-	externals: {
-		'vscode': 'module vscode',
+const srcDir = path.join(import.meta.dirname, 'src');
+const outDir = path.join(import.meta.dirname, 'dist');
+
+run({
+	platform: 'node',
+	entryPoints: {
+		'extension': path.join(srcDir, 'extension.ts'),
 	},
-	experiments: {
-		outputModule: true
-	}
-});
+	srcDir,
+	outdir: outDir,
+}, process.argv);
diff --git a/extensions/github-authentication/extension-browser.webpack.config.js b/extensions/github-authentication/extension-browser.webpack.config.js
deleted file mode 100644
index 70a7fd87cf4a3..0000000000000
--- a/extensions/github-authentication/extension-browser.webpack.config.js
+++ /dev/null
@@ -1,24 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-// @ts-check
-import path from 'path';
-import { browser as withBrowserDefaults } from '../shared.webpack.config.mjs';
-
-export default withBrowserDefaults({
-	context: import.meta.dirname,
-	node: false,
-	entry: {
-		extension: './src/extension.ts',
-	},
-	resolve: {
-		alias: {
-			'uuid': path.resolve(import.meta.dirname, 'node_modules/uuid/dist/esm-browser/index.js'),
-			'./node/authServer': path.resolve(import.meta.dirname, 'src/browser/authServer'),
-			'./node/crypto': path.resolve(import.meta.dirname, 'src/browser/crypto'),
-			'./node/fetch': path.resolve(import.meta.dirname, 'src/browser/fetch'),
-			'./node/buffer': path.resolve(import.meta.dirname, 'src/browser/buffer'),
-		}
-	}
-});
diff --git a/extensions/github-authentication/media/index.html b/extensions/github-authentication/media/index.html
index 3292e2a08fc9f..2df45293528fa 100644
--- a/extensions/github-authentication/media/index.html
+++ b/extensions/github-authentication/media/index.html
@@ -30,9 +30,17 @@ <h1 class="title">Launching <span class="app-name"></span></h1>
 	</div>
 	<script>
 		const urlParams = new URLSearchParams(window.location.search);
+
 		const appName = urlParams.get('app_name');
 		document.querySelectorAll('.app-name').forEach(e => e.innerText = appName);
 
+		if (urlParams.get('app_is_sessions') === 'true') {
+			const iconImg = document.querySelector('.icon-container img');
+			if (iconImg) {
+				iconImg.src = 'sessions-icon.svg';
+			}
+		}
+
 		// if name contains 'insiders', update filter CSS variables
 		if (appName.toLowerCase().includes('insiders')) {
 			document.documentElement.style.setProperty('--vscode-filter-0', 'var(--vscode-insiders-filter-0)');
diff --git a/extensions/github-authentication/media/sessions-icon.svg b/extensions/github-authentication/media/sessions-icon.svg
new file mode 100644
index 0000000000000..d1eb57cf32618
--- /dev/null
+++ b/extensions/github-authentication/media/sessions-icon.svg
@@ -0,0 +1,24 @@
+<svg width="1024" height="1024" viewBox="0 0 1024 1024" fill="none" xmlns="http://www.w3.org/2000/svg">
+<path d="M64 302.719C64 333.652 80.64 361.599 106.667 376.532L469.333 585.812V930.772C469.333 945.919 461.227 959.999 448 967.679C434.773 975.359 418.56 975.359 405.333 967.679L85.3333 782.932C72.1067 775.252 64 761.172 64 746.025V302.719Z" fill="url(#paint0_linear_608_6009)"/>
+<path d="M448 56.3225C461.227 64.0025 469.333 78.0825 469.333 93.2292V585.816L106.667 376.536C80.64 361.603 64 333.656 64 302.723C64 272.216 80.2133 244.056 106.667 228.696L405.333 56.3225C418.56 48.6425 434.773 48.6425 448 56.3225Z" fill="url(#paint1_linear_608_6009)"/>
+<path d="M618.667 56.3225L938.667 241.069C951.893 248.749 960 262.829 960 277.976V721.283C960 690.349 943.36 662.403 917.333 647.469L554.667 437.976V93.2292C554.667 78.0825 562.773 64.0025 576 56.3225C589.227 48.6425 605.44 48.6425 618.667 56.3225Z" fill="url(#paint2_linear_608_6009)"/>
+<path d="M554.667 437.974L917.333 647.467C943.36 662.401 960 690.347 960 721.281C960 752.214 943.787 779.947 917.333 795.307L618.667 967.681C605.44 975.361 589.227 975.361 576 967.681C562.773 960.001 554.667 945.921 554.667 930.774V437.974Z" fill="url(#paint3_linear_608_6009)"/>
+<defs>
+<linearGradient id="paint0_linear_608_6009" x1="469.333" y1="586.667" x2="64" y2="586.667" gradientUnits="userSpaceOnUse">
+<stop stop-color="#1797D9"/>
+<stop offset="1" stop-color="#087CBF"/>
+</linearGradient>
+<linearGradient id="paint1_linear_608_6009" x1="181.333" y1="405.333" x2="394.667" y2="53.3333" gradientUnits="userSpaceOnUse">
+<stop stop-color="#005B9E"/>
+<stop offset="1" stop-color="#087CBF"/>
+</linearGradient>
+<linearGradient id="paint2_linear_608_6009" x1="970.667" y1="166.975" x2="554.667" y2="166.975" gradientUnits="userSpaceOnUse">
+<stop offset="0.0211942" stop-color="#26B2F3"/>
+<stop offset="1" stop-color="#3AC6FF"/>
+</linearGradient>
+<linearGradient id="paint3_linear_608_6009" x1="570.2" y1="973.443" x2="810.667" y2="581.333" gradientUnits="userSpaceOnUse">
+<stop stop-color="#1EA5E6"/>
+<stop offset="1" stop-color="#087CBF"/>
+</linearGradient>
+</defs>
+</svg>
diff --git a/extensions/github-authentication/package.json b/extensions/github-authentication/package.json
index 91f2d1b57dbcb..28877821ed171 100644
--- a/extensions/github-authentication/package.json
+++ b/extensions/github-authentication/package.json
@@ -19,7 +19,8 @@
   ],
   "enabledApiProposals": [
     "authIssuers",
-    "authProviderSpecific"
+    "authProviderSpecific",
+    "agentSessionsWorkspace"
   ],
   "activationEvents": [],
   "capabilities": {
@@ -78,9 +79,9 @@
   "browser": "./dist/browser/extension.js",
   "scripts": {
     "compile": "gulp compile-extension:github-authentication",
-    "compile-web": "npx webpack-cli --config extension-browser.webpack.config --mode none",
+    "compile-web": "node esbuild.browser.mts",
     "watch": "gulp watch-extension:github-authentication",
-    "watch-web": "npx webpack-cli --config extension-browser.webpack.config --mode none --watch --info-verbosity verbose",
+    "watch-web": "node esbuild.browser.mts --watch",
     "vscode:prepublish": "npm run compile"
   },
   "dependencies": {
diff --git a/extensions/github-authentication/src/browser/authServer.ts b/extensions/github-authentication/src/browser/authServer.ts
index 60b53c713a85e..b53642ee74a18 100644
--- a/extensions/github-authentication/src/browser/authServer.ts
+++ b/extensions/github-authentication/src/browser/authServer.ts
@@ -10,3 +10,9 @@ export function startServer(_: any): any {
 export function createServer(_: any): any {
 	throw new Error('Not implemented');
 }
+
+export class LoopbackAuthServer {
+	constructor(..._args: any[]) {
+		throw new Error('Not implemented');
+	}
+}
diff --git a/extensions/github-authentication/src/common/env.ts b/extensions/github-authentication/src/common/env.ts
index ebc474936aa40..5456fb864ee4c 100644
--- a/extensions/github-authentication/src/common/env.ts
+++ b/extensions/github-authentication/src/common/env.ts
@@ -8,12 +8,15 @@ import { AuthProviderType } from '../github';
 const VALID_DESKTOP_CALLBACK_SCHEMES = [
 	'vscode',
 	'vscode-insiders',
+	'vscode-exploration',
+	'vscode-sessions',
+	'vscode-sessions-insiders',
+	'vscode-sessions-exploration',
 	// On Windows, some browsers don't seem to redirect back to OSS properly.
 	// As a result, you get stuck in the auth flow. We exclude this from the
 	// list until we can figure out a way to fix this behavior in browsers.
 	// 'code-oss',
 	'vscode-wsl',
-	'vscode-exploration'
 ];
 
 export function isSupportedClient(uri: Uri): boolean {
diff --git a/extensions/github-authentication/src/node/authServer.ts b/extensions/github-authentication/src/node/authServer.ts
index 45dca93e2d0a6..76b7fe61084d0 100644
--- a/extensions/github-authentication/src/node/authServer.ts
+++ b/extensions/github-authentication/src/node/authServer.ts
@@ -7,7 +7,7 @@ import { URL } from 'url';
 import * as fs from 'fs';
 import * as path from 'path';
 import { randomBytes } from 'crypto';
-import { env } from 'vscode';
+import { env, workspace } from 'vscode';
 
 function sendFile(res: http.ServerResponse, filepath: string) {
 	const isSvg = filepath.endsWith('.svg');
@@ -99,13 +99,14 @@ export class LoopbackAuthServer implements ILoopbackServer {
 		this._resultPromise = new Promise<IOAuthResult>((resolve, reject) => deferred = { resolve, reject });
 
 		const appNameQueryParam = `&app_name=${encodeURIComponent(env.appName)}`;
+		const appIsSessionsQueryParam = workspace.isAgentSessionsWorkspace ? '&app_is_sessions=true' : '';
 		this._server = http.createServer((req, res) => {
 			const reqUrl = new URL(req.url!, `http://${req.headers.host}`);
 			switch (reqUrl.pathname) {
 				case '/signin': {
 					const receivedNonce = (reqUrl.searchParams.get('nonce') ?? '').replace(/ /g, '+');
 					if (receivedNonce !== this.nonce) {
-						res.writeHead(302, { location: `/?error=${encodeURIComponent('Nonce does not match.')}${appNameQueryParam}` });
+						res.writeHead(302, { location: `/?error=${encodeURIComponent('Nonce does not match.')}${appNameQueryParam}${appIsSessionsQueryParam}` });
 						res.end();
 					}
 					res.writeHead(302, { location: this._startingRedirect.toString() });
@@ -122,20 +123,20 @@ export class LoopbackAuthServer implements ILoopbackServer {
 						return;
 					}
 					if (this.state !== state) {
-						res.writeHead(302, { location: `/?error=${encodeURIComponent('State does not match.')}${appNameQueryParam}` });
+						res.writeHead(302, { location: `/?error=${encodeURIComponent('State does not match.')}${appNameQueryParam}${appIsSessionsQueryParam}` });
 						res.end();
 						throw new Error('State does not match.');
 					}
 					if (this.nonce !== nonce) {
-						res.writeHead(302, { location: `/?error=${encodeURIComponent('Nonce does not match.')}${appNameQueryParam}` });
+						res.writeHead(302, { location: `/?error=${encodeURIComponent('Nonce does not match.')}${appNameQueryParam}${appIsSessionsQueryParam}` });
 						res.end();
 						throw new Error('Nonce does not match.');
 					}
 					deferred.resolve({ code, state });
 					if (isPortable) {
-						res.writeHead(302, { location: `/?app_name=${encodeURIComponent(env.appName)}` });
+						res.writeHead(302, { location: `/?app_name=${encodeURIComponent(env.appName)}${appIsSessionsQueryParam}` });
 					} else {
-						res.writeHead(302, { location: `/?redirect_uri=${encodeURIComponent(callbackUri)}${appNameQueryParam}` });
+						res.writeHead(302, { location: `/?redirect_uri=${encodeURIComponent(callbackUri)}${appNameQueryParam}${appIsSessionsQueryParam}` });
 					}
 					res.end();
 					break;
diff --git a/extensions/github-authentication/tsconfig.browser.json b/extensions/github-authentication/tsconfig.browser.json
new file mode 100644
index 0000000000000..233289b8bd578
--- /dev/null
+++ b/extensions/github-authentication/tsconfig.browser.json
@@ -0,0 +1,8 @@
+{
+	"extends": "./tsconfig.json",
+	"compilerOptions": {},
+	"exclude": [
+		"./src/node/**",
+		"./src/test/**"
+	]
+}
diff --git a/extensions/github-authentication/tsconfig.json b/extensions/github-authentication/tsconfig.json
index df8791cdebcd4..eac554232a0a5 100644
--- a/extensions/github-authentication/tsconfig.json
+++ b/extensions/github-authentication/tsconfig.json
@@ -14,6 +14,7 @@
 		"src/**/*",
 		"../../src/vscode-dts/vscode.d.ts",
 		"../../src/vscode-dts/vscode.proposed.authIssuers.d.ts",
-		"../../src/vscode-dts/vscode.proposed.authProviderSpecific.d.ts"
+		"../../src/vscode-dts/vscode.proposed.authProviderSpecific.d.ts",
+		"../../src/vscode-dts/vscode.proposed.agentSessionsWorkspace.d.ts"
 	]
 }
diff --git a/extensions/github/.vscodeignore b/extensions/github/.vscodeignore
index 77ec048a6daff..a6590bd39343c 100644
--- a/extensions/github/.vscodeignore
+++ b/extensions/github/.vscodeignore
@@ -2,7 +2,7 @@ src/**
 !src/common/config.json
 out/**
 build/**
-extension.webpack.config.js
+esbuild*.mts
 tsconfig*.json
 package-lock.json
 testWorkspace/**
diff --git a/extensions/github/esbuild.mts b/extensions/github/esbuild.mts
new file mode 100644
index 0000000000000..51494c329a5d1
--- /dev/null
+++ b/extensions/github/esbuild.mts
@@ -0,0 +1,25 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+import * as path from 'node:path';
+import { run } from '../esbuild-extension-common.mts';
+
+const srcDir = path.join(import.meta.dirname, 'src');
+const outDir = path.join(import.meta.dirname, 'dist');
+
+run({
+	platform: 'node',
+	format: 'esm',
+	entryPoints: {
+		'extension': path.join(srcDir, 'extension.ts'),
+	},
+	srcDir,
+	outdir: outDir,
+	additionalOptions: {
+		banner: {
+			// The tunnel package uses `require` and needs this shim to work in an ESM environment
+			js: `import { createRequire } from 'module'; const require = createRequire(import.meta.url);`,
+		},
+	},
+}, process.argv);
diff --git a/extensions/github/package.json b/extensions/github/package.json
index a9ba2e87d3087..a122a856488ae 100644
--- a/extensions/github/package.json
+++ b/extensions/github/package.json
@@ -19,10 +19,10 @@
   "extensionDependencies": [
     "vscode.git-base"
   ],
-  "main": "./out/extension.js",
   "type": "module",
+  "main": "./out/extension.js",
   "capabilities": {
-    "virtualWorkspaces": false,
+    "virtualWorkspaces": true,
     "untrustedWorkspaces": {
       "supported": true
     }
@@ -74,6 +74,11 @@
         "command": "github.createPullRequest",
         "title": "%command.createPullRequest%",
         "icon": "$(git-pull-request)"
+      },
+      {
+        "command": "github.openPullRequest",
+        "title": "%command.openPullRequest%",
+        "icon": "$(git-pull-request)"
       }
     ],
     "continueEditSession": [
@@ -95,6 +100,10 @@
           "command": "github.createPullRequest",
           "when": "false"
         },
+        {
+          "command": "github.openPullRequest",
+          "when": "false"
+        },
         {
           "command": "github.graph.openOnGitHub",
           "when": "false"
@@ -174,14 +183,7 @@
           "when": "github.hasGitHubRepo && timelineItem =~ /git:file:commit\\b/"
         }
       ],
-      "chat/input/editing/sessionToolbar": [
-        {
-          "command": "github.createPullRequest",
-          "group": "navigation",
-          "order": 1,
-          "when": "isSessionsWindow && agentSessionHasChanges && chatSessionType == copilotcli"
-        }
-      ]
+      "chat/input/editing/sessionApplyActions": []
     },
     "configuration": [
       {
diff --git a/extensions/github/package.nls.json b/extensions/github/package.nls.json
index ced536e4bd7c6..04497595eb6d2 100644
--- a/extensions/github/package.nls.json
+++ b/extensions/github/package.nls.json
@@ -5,7 +5,8 @@
 	"command.publish": "Publish to GitHub",
 	"command.openOnGitHub": "Open on GitHub",
 	"command.openOnVscodeDev": "Open in vscode.dev",
-	"command.createPullRequest": "Create Pull Request",
+	"command.createPullRequest": "Create PR",
+	"command.openPullRequest": "Open PR",
 	"config.branchProtection": "Controls whether to query repository rules for GitHub repositories",
 	"config.gitAuthentication": "Controls whether to enable automatic GitHub authentication for git commands within VS Code.",
 	"config.gitProtocol": "Controls which protocol is used to clone a GitHub repository",
diff --git a/extensions/github/src/branchProtection.ts b/extensions/github/src/branchProtection.ts
index 040df24942a60..0c616d33905ea 100644
--- a/extensions/github/src/branchProtection.ts
+++ b/extensions/github/src/branchProtection.ts
@@ -6,7 +6,7 @@
 import { EventEmitter, LogOutputChannel, Memento, Uri, workspace } from 'vscode';
 import { Repository as GitHubRepository, RepositoryRuleset } from '@octokit/graphql-schema';
 import { AuthenticationError, OctokitService } from './auth.js';
-import { API, BranchProtection, BranchProtectionProvider, BranchProtectionRule, Repository } from './typings/git.js';
+import type { API, BranchProtection, BranchProtectionProvider, BranchProtectionRule, Repository } from './typings/git.d.ts';
 import { DisposableStore, getRepositoryFromUrl } from './util.js';
 import { TelemetryReporter } from '@vscode/extension-telemetry';
 
diff --git a/extensions/github/src/canonicalUriProvider.ts b/extensions/github/src/canonicalUriProvider.ts
index 0838c7377dd63..9218707ed2605 100644
--- a/extensions/github/src/canonicalUriProvider.ts
+++ b/extensions/github/src/canonicalUriProvider.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { CancellationToken, CanonicalUriProvider, CanonicalUriRequestOptions, Disposable, ProviderResult, Uri, workspace } from 'vscode';
-import { API } from './typings/git.js';
+import type { API } from './typings/git.d.ts';
 
 const SUPPORTED_SCHEMES = ['ssh', 'https', 'file'];
 
diff --git a/extensions/github/src/commands.ts b/extensions/github/src/commands.ts
index 496772ededf82..a8b69f1093616 100644
--- a/extensions/github/src/commands.ts
+++ b/extensions/github/src/commands.ts
@@ -4,10 +4,12 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as vscode from 'vscode';
-import { API as GitAPI, RefType, Repository } from './typings/git.js';
+import { RefType } from './typings/git.constants.js';
+import type { API as GitAPI, Repository } from './typings/git.d.ts';
 import { publishRepository } from './publish.js';
 import { DisposableStore, getRepositoryFromUrl } from './util.js';
 import { LinkContext, getCommitLink, getLink, getVscodeDevHost } from './links.js';
+import { getOctokit } from './auth.js';
 
 async function copyVscodeDevLink(gitAPI: GitAPI, useSelection: boolean, context: LinkContext, includeRange = true) {
 	try {
@@ -34,46 +36,73 @@ async function openVscodeDevLink(gitAPI: GitAPI): Promise<vscode.Uri | undefined
 	}
 }
 
-async function createPullRequest(gitAPI: GitAPI, sessionResource: vscode.Uri | undefined, sessionMetadata: { worktreePath?: string } | undefined): Promise<void> {
-	if (!sessionResource || !sessionMetadata?.worktreePath) {
-		return;
+interface ResolvedSessionRepo {
+	repository: Repository;
+	remoteInfo: { owner: string; repo: string };
+	gitRemote: { name: string; fetchUrl: string };
+	head: { name: string; upstream?: { name: string; remote: string; commit: string } };
+}
+
+function resolveSessionRepo(gitAPI: GitAPI, sessionMetadata: { worktreePath?: string } | undefined, showErrors: boolean): ResolvedSessionRepo | undefined {
+	if (!sessionMetadata?.worktreePath) {
+		return undefined;
 	}
 
 	const worktreeUri = vscode.Uri.file(sessionMetadata.worktreePath);
 	const repository = gitAPI.getRepository(worktreeUri);
 
 	if (!repository) {
-		vscode.window.showErrorMessage(vscode.l10n.t('Could not find a git repository for the session worktree.'));
-		return;
+		if (showErrors) {
+			vscode.window.showErrorMessage(vscode.l10n.t('Could not find a git repository for the session worktree.'));
+		}
+		return undefined;
 	}
 
-	// Find the GitHub remote
 	const remotes = repository.state.remotes
 		.filter(remote => remote.fetchUrl && getRepositoryFromUrl(remote.fetchUrl));
 
 	if (remotes.length === 0) {
-		vscode.window.showErrorMessage(vscode.l10n.t('Could not find a GitHub remote for this repository.'));
-		return;
+		if (showErrors) {
+			vscode.window.showErrorMessage(vscode.l10n.t('Could not find a GitHub remote for this repository.'));
+		}
+		return undefined;
 	}
 
-	// Prefer upstream -> origin -> first
 	const gitRemote = remotes.find(r => r.name === 'upstream')
 		?? remotes.find(r => r.name === 'origin')
 		?? remotes[0];
 
 	const remoteInfo = getRepositoryFromUrl(gitRemote.fetchUrl!);
 	if (!remoteInfo) {
-		vscode.window.showErrorMessage(vscode.l10n.t('Could not parse GitHub remote URL.'));
-		return;
+		if (showErrors) {
+			vscode.window.showErrorMessage(vscode.l10n.t('Could not parse GitHub remote URL.'));
+		}
+		return undefined;
 	}
 
-	// Get the current branch (the worktree branch)
 	const head = repository.state.HEAD;
 	if (!head?.name) {
-		vscode.window.showErrorMessage(vscode.l10n.t('Could not determine the current branch.'));
+		if (showErrors) {
+			vscode.window.showErrorMessage(vscode.l10n.t('Could not determine the current branch.'));
+		}
+		return undefined;
+	}
+
+	return { repository, remoteInfo, gitRemote: { name: gitRemote.name, fetchUrl: gitRemote.fetchUrl! }, head: head as ResolvedSessionRepo['head'] };
+}
+
+async function createPullRequest(gitAPI: GitAPI, sessionResource: vscode.Uri | undefined, sessionMetadata: { worktreePath?: string } | undefined): Promise<void> {
+	if (!sessionResource) {
+		return;
+	}
+
+	const resolved = resolveSessionRepo(gitAPI, sessionMetadata, true);
+	if (!resolved) {
 		return;
 	}
 
+	const { repository, remoteInfo, gitRemote, head } = resolved;
+
 	// Ensure the branch is published to the remote
 	if (!head.upstream) {
 		try {
@@ -96,6 +125,34 @@ async function createPullRequest(gitAPI: GitAPI, sessionResource: vscode.Uri | u
 	vscode.env.openExternal(vscode.Uri.parse(prUrl));
 }
 
+async function openPullRequest(gitAPI: GitAPI, _sessionResource: vscode.Uri | undefined, sessionMetadata: { worktreePath?: string } | undefined): Promise<void> {
+	const resolved = resolveSessionRepo(gitAPI, sessionMetadata, true);
+	if (!resolved) {
+		return;
+	}
+
+	try {
+		const octokit = await getOctokit();
+		const { data: pullRequests } = await octokit.pulls.list({
+			owner: resolved.remoteInfo.owner,
+			repo: resolved.remoteInfo.repo,
+			head: `${resolved.remoteInfo.owner}:${resolved.head.name}`,
+			state: 'all',
+		});
+
+		if (pullRequests.length > 0) {
+			vscode.env.openExternal(vscode.Uri.parse(pullRequests[0].html_url));
+			return;
+		}
+	} catch {
+		// If the API call fails, fall through to open the repo page
+	}
+
+	// Fallback: open the repository page
+	const { remoteInfo } = resolved;
+	vscode.env.openExternal(vscode.Uri.parse(`https://github.com/${remoteInfo.owner}/${remoteInfo.repo}`));
+}
+
 async function openOnGitHub(repository: Repository, commit: string): Promise<void> {
 	// Get the unique remotes that contain the commit
 	const branches = await repository.getBranches({ contains: commit, remote: true });
@@ -181,5 +238,9 @@ export function registerCommands(gitAPI: GitAPI): vscode.Disposable {
 		return createPullRequest(gitAPI, sessionResource, sessionMetadata);
 	}));
 
+	disposables.add(vscode.commands.registerCommand('github.openPullRequest', async (sessionResource: vscode.Uri | undefined, sessionMetadata: { worktreePath?: string } | undefined) => {
+		return openPullRequest(gitAPI, sessionResource, sessionMetadata);
+	}));
+
 	return disposables;
 }
diff --git a/extensions/github/src/credentialProvider.ts b/extensions/github/src/credentialProvider.ts
index d184960c23bbb..4964724eed6b9 100644
--- a/extensions/github/src/credentialProvider.ts
+++ b/extensions/github/src/credentialProvider.ts
@@ -3,7 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { CredentialsProvider, Credentials, API as GitAPI } from './typings/git.js';
+import type { CredentialsProvider, Credentials, API as GitAPI } from './typings/git.d.ts';
 import { workspace, Uri, Disposable } from 'vscode';
 import { getSession } from './auth.js';
 
diff --git a/extensions/github/src/extension.ts b/extensions/github/src/extension.ts
index 17906c57d44f2..e6a44f516ac1d 100644
--- a/extensions/github/src/extension.ts
+++ b/extensions/github/src/extension.ts
@@ -6,7 +6,7 @@
 import { commands, Disposable, ExtensionContext, extensions, l10n, LogLevel, LogOutputChannel, window } from 'vscode';
 import { TelemetryReporter } from '@vscode/extension-telemetry';
 import { GithubRemoteSourceProvider } from './remoteSourceProvider.js';
-import { API, GitExtension } from './typings/git.js';
+import type { API, GitExtension } from './typings/git.d.ts';
 import { registerCommands } from './commands.js';
 import { GithubCredentialProviderManager } from './credentialProvider.js';
 import { DisposableStore, repositoryHasGitHubRemote } from './util.js';
diff --git a/extensions/github/src/historyItemDetailsProvider.ts b/extensions/github/src/historyItemDetailsProvider.ts
index 9a267b9e8443b..d0a145ec9f23b 100644
--- a/extensions/github/src/historyItemDetailsProvider.ts
+++ b/extensions/github/src/historyItemDetailsProvider.ts
@@ -5,7 +5,7 @@
 
 import { Command, l10n, LogOutputChannel, workspace } from 'vscode';
 import { Commit, Repository as GitHubRepository, Maybe } from '@octokit/graphql-schema';
-import { API, AvatarQuery, AvatarQueryCommit, Repository, SourceControlHistoryItemDetailsProvider } from './typings/git.js';
+import type { API, AvatarQuery, AvatarQueryCommit, Repository, SourceControlHistoryItemDetailsProvider } from './typings/git.d.ts';
 import { DisposableStore, getRepositoryDefaultRemote, getRepositoryDefaultRemoteUrl, getRepositoryFromUrl, groupBy, sequentialize } from './util.js';
 import { AuthenticationError, OctokitService } from './auth.js';
 import { getAvatarLink } from './links.js';
diff --git a/extensions/github/src/links.ts b/extensions/github/src/links.ts
index b4f8379e5f79e..fbdde106149cd 100644
--- a/extensions/github/src/links.ts
+++ b/extensions/github/src/links.ts
@@ -4,7 +4,8 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as vscode from 'vscode';
-import { API as GitAPI, RefType, Repository } from './typings/git.js';
+import { RefType } from './typings/git.constants.js';
+import type { API as GitAPI, Repository } from './typings/git.d.ts';
 import { getRepositoryFromUrl, repositoryHasGitHubRemote } from './util.js';
 
 export function isFileInRepo(repository: Repository, file: vscode.Uri): boolean {
diff --git a/extensions/github/src/publish.ts b/extensions/github/src/publish.ts
index 618f752745020..dab81037d5924 100644
--- a/extensions/github/src/publish.ts
+++ b/extensions/github/src/publish.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as vscode from 'vscode';
-import { API as GitAPI, Repository } from './typings/git.js';
+import type { API as GitAPI, Repository } from './typings/git.d.ts';
 import { getOctokit } from './auth.js';
 import { TextEncoder } from 'util';
 import { basename } from 'path';
diff --git a/extensions/github/src/pushErrorHandler.ts b/extensions/github/src/pushErrorHandler.ts
index f7b0b9ef8696d..751654515f982 100644
--- a/extensions/github/src/pushErrorHandler.ts
+++ b/extensions/github/src/pushErrorHandler.ts
@@ -6,7 +6,8 @@
 import { TextDecoder } from 'util';
 import { commands, env, ProgressLocation, Uri, window, workspace, QuickPickOptions, FileType, l10n, Disposable, TextDocumentContentProvider } from 'vscode';
 import { getOctokit } from './auth.js';
-import { GitErrorCodes, PushErrorHandler, Remote, Repository } from './typings/git.js';
+import { GitErrorCodes } from './typings/git.constants.js';
+import type { PushErrorHandler, Remote, Repository } from './typings/git.d.ts';
 import * as path from 'path';
 import { TelemetryReporter } from '@vscode/extension-telemetry';
 
diff --git a/extensions/github/src/remoteSourcePublisher.ts b/extensions/github/src/remoteSourcePublisher.ts
index 97ce05a835cf8..67c1e567e3687 100644
--- a/extensions/github/src/remoteSourcePublisher.ts
+++ b/extensions/github/src/remoteSourcePublisher.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { publishRepository } from './publish.js';
-import { API as GitAPI, RemoteSourcePublisher, Repository } from './typings/git.js';
+import type { API as GitAPI, RemoteSourcePublisher, Repository } from './typings/git.d.ts';
 
 export class GithubRemoteSourcePublisher implements RemoteSourcePublisher {
 	readonly name = 'GitHub';
diff --git a/extensions/github/src/shareProviders.ts b/extensions/github/src/shareProviders.ts
index d2e94a471477d..a52cf84d7044a 100644
--- a/extensions/github/src/shareProviders.ts
+++ b/extensions/github/src/shareProviders.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as vscode from 'vscode';
-import { API } from './typings/git.js';
+import type { API } from './typings/git.d.ts';
 import { getRepositoryFromUrl, repositoryHasGitHubRemote } from './util.js';
 import { encodeURIComponentExceptSlashes, ensurePublished, getRepositoryForFile, notebookCellRangeString, rangeString } from './links.js';
 
diff --git a/extensions/github/src/typings/git.constants.ts b/extensions/github/src/typings/git.constants.ts
new file mode 100644
index 0000000000000..e39a3fb03b327
--- /dev/null
+++ b/extensions/github/src/typings/git.constants.ts
@@ -0,0 +1,98 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import type * as git from './git.d.ts';
+
+export type ForcePushMode = git.ForcePushMode;
+export type RefType = git.RefType;
+export type Status = git.Status;
+export type GitErrorCodes = git.GitErrorCodes;
+
+export const ForcePushMode = Object.freeze({
+	Force: 0,
+	ForceWithLease: 1,
+	ForceWithLeaseIfIncludes: 2,
+}) satisfies typeof git.ForcePushMode;
+
+export const RefType = Object.freeze({
+	Head: 0,
+	RemoteHead: 1,
+	Tag: 2,
+}) satisfies typeof git.RefType;
+
+export const Status = Object.freeze({
+	INDEX_MODIFIED: 0,
+	INDEX_ADDED: 1,
+	INDEX_DELETED: 2,
+	INDEX_RENAMED: 3,
+	INDEX_COPIED: 4,
+
+	MODIFIED: 5,
+	DELETED: 6,
+	UNTRACKED: 7,
+	IGNORED: 8,
+	INTENT_TO_ADD: 9,
+	INTENT_TO_RENAME: 10,
+	TYPE_CHANGED: 11,
+
+	ADDED_BY_US: 12,
+	ADDED_BY_THEM: 13,
+	DELETED_BY_US: 14,
+	DELETED_BY_THEM: 15,
+	BOTH_ADDED: 16,
+	BOTH_DELETED: 17,
+	BOTH_MODIFIED: 18,
+}) satisfies typeof git.Status;
+
+export const GitErrorCodes = Object.freeze({
+	BadConfigFile: 'BadConfigFile',
+	BadRevision: 'BadRevision',
+	AuthenticationFailed: 'AuthenticationFailed',
+	NoUserNameConfigured: 'NoUserNameConfigured',
+	NoUserEmailConfigured: 'NoUserEmailConfigured',
+	NoRemoteRepositorySpecified: 'NoRemoteRepositorySpecified',
+	NotAGitRepository: 'NotAGitRepository',
+	NotASafeGitRepository: 'NotASafeGitRepository',
+	NotAtRepositoryRoot: 'NotAtRepositoryRoot',
+	Conflict: 'Conflict',
+	StashConflict: 'StashConflict',
+	UnmergedChanges: 'UnmergedChanges',
+	PushRejected: 'PushRejected',
+	ForcePushWithLeaseRejected: 'ForcePushWithLeaseRejected',
+	ForcePushWithLeaseIfIncludesRejected: 'ForcePushWithLeaseIfIncludesRejected',
+	RemoteConnectionError: 'RemoteConnectionError',
+	DirtyWorkTree: 'DirtyWorkTree',
+	CantOpenResource: 'CantOpenResource',
+	GitNotFound: 'GitNotFound',
+	CantCreatePipe: 'CantCreatePipe',
+	PermissionDenied: 'PermissionDenied',
+	CantAccessRemote: 'CantAccessRemote',
+	RepositoryNotFound: 'RepositoryNotFound',
+	RepositoryIsLocked: 'RepositoryIsLocked',
+	BranchNotFullyMerged: 'BranchNotFullyMerged',
+	NoRemoteReference: 'NoRemoteReference',
+	InvalidBranchName: 'InvalidBranchName',
+	BranchAlreadyExists: 'BranchAlreadyExists',
+	NoLocalChanges: 'NoLocalChanges',
+	NoStashFound: 'NoStashFound',
+	LocalChangesOverwritten: 'LocalChangesOverwritten',
+	NoUpstreamBranch: 'NoUpstreamBranch',
+	IsInSubmodule: 'IsInSubmodule',
+	WrongCase: 'WrongCase',
+	CantLockRef: 'CantLockRef',
+	CantRebaseMultipleBranches: 'CantRebaseMultipleBranches',
+	PatchDoesNotApply: 'PatchDoesNotApply',
+	NoPathFound: 'NoPathFound',
+	UnknownPath: 'UnknownPath',
+	EmptyCommitMessage: 'EmptyCommitMessage',
+	BranchFastForwardRejected: 'BranchFastForwardRejected',
+	BranchNotYetBorn: 'BranchNotYetBorn',
+	TagConflict: 'TagConflict',
+	CherryPickEmpty: 'CherryPickEmpty',
+	CherryPickConflict: 'CherryPickConflict',
+	WorktreeContainsChanges: 'WorktreeContainsChanges',
+	WorktreeAlreadyExists: 'WorktreeAlreadyExists',
+	WorktreeBranchAlreadyUsed: 'WorktreeBranchAlreadyUsed',
+}) satisfies Record<keyof typeof git.GitErrorCodes, string>;
diff --git a/extensions/github/src/util.ts b/extensions/github/src/util.ts
index 2247292dd93ba..bcdddaed6e5e7 100644
--- a/extensions/github/src/util.ts
+++ b/extensions/github/src/util.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as vscode from 'vscode';
-import { Repository } from './typings/git.js';
+import type { Repository } from './typings/git.d.ts';
 
 export class DisposableStore {
 
diff --git a/extensions/go/cgmanifest.json b/extensions/go/cgmanifest.json
index b697426969b2a..bdad000b91991 100644
--- a/extensions/go/cgmanifest.json
+++ b/extensions/go/cgmanifest.json
@@ -6,12 +6,12 @@
 				"git": {
 					"name": "go-syntax",
 					"repositoryUrl": "https://github.com/worlpaker/go-syntax",
-					"commitHash": "6e8421faf8f1445512825f63925e54a62106bcf1"
+					"commitHash": "c74e22eb9ef32958e3edd130ea750ce78d8b8241"
 				}
 			},
 			"license": "MIT",
 			"description": "The file syntaxes/go.tmLanguage.json is from https://github.com/worlpaker/go-syntax, which in turn was derived from https://github.com/jeff-hykin/better-go-syntax.",
-			"version": "0.8.5"
+			"version": "0.8.6"
 		}
 	],
 	"version": 1
diff --git a/extensions/go/syntaxes/go.tmLanguage.json b/extensions/go/syntaxes/go.tmLanguage.json
index 72d7df0cb4045..b2aec3c4e14d4 100644
--- a/extensions/go/syntaxes/go.tmLanguage.json
+++ b/extensions/go/syntaxes/go.tmLanguage.json
@@ -4,7 +4,7 @@
 		"If you want to provide a fix or improvement, please create a pull request against the original repository.",
 		"Once accepted there, we are happy to receive an update request."
 	],
-	"version": "https://github.com/worlpaker/go-syntax/commit/6e8421faf8f1445512825f63925e54a62106bcf1",
+	"version": "https://github.com/worlpaker/go-syntax/commit/c74e22eb9ef32958e3edd130ea750ce78d8b8241",
 	"name": "Go",
 	"scopeName": "source.go",
 	"patterns": [
@@ -1929,12 +1929,12 @@
 				},
 				{
 					"comment": "one line with semicolon(;) without formatting gofmt - single type | property variables and types",
-					"match": "(?:(?<=\\{)((?:\\s*(?:(?:(?:\\w+\\,\\s*)+)?(?:\\w+\\s+))?(?:(?:(?:\\s*(?:[\\*\\[\\]]+)?(?:\\<\\-\\s*)?\\bchan\\b(?:\\s*\\<\\-)?\\s*)+)?(?:[^\\s/]+)(?:\\;)?))+)\\s*(?=\\}))",
+					"match": "(?:(?<=\\{)((?:\\s*(?:(?:(?:\\w+\\,\\s*)+)?(?:\\w+\\s+))?(?:(?:(?:\\s*(?:[\\*\\[\\]]+)?(?:\\<\\-\\s*)?\\bchan\\b(?:\\s*\\<\\-)?\\s*)+)?(?:[^\\s/\\`\"]+)(?:\\;)?))+)\\s*(?=\\}))",
 					"captures": {
 						"1": {
 							"patterns": [
 								{
-									"match": "(?:((?:(?:\\w+\\,\\s*)+)?(?:\\w+\\s+))?((?:(?:\\s*(?:[\\*\\[\\]]+)?(?:\\<\\-\\s*)?\\bchan\\b(?:\\s*\\<\\-)?\\s*)+)?(?:[^\\s/]+)(?:\\;)?))",
+									"match": "(?:((?:(?:\\w+\\,\\s*)+)?(?:\\w+\\s+))?((?:(?:\\s*(?:[\\*\\[\\]]+)?(?:\\<\\-\\s*)?\\bchan\\b(?:\\s*\\<\\-)?\\s*)+)?(?:[^\\s/\\`\"]+)(?:\\;)?))",
 									"captures": {
 										"1": {
 											"patterns": [
diff --git a/extensions/html-language-features/package-lock.json b/extensions/html-language-features/package-lock.json
index 1e97c143679e7..ef75469b9646a 100644
--- a/extensions/html-language-features/package-lock.json
+++ b/extensions/html-language-features/package-lock.json
@@ -20,27 +20,6 @@
         "vscode": "^1.77.0"
       }
     },
-    "node_modules/@isaacs/balanced-match": {
-      "version": "4.0.1",
-      "resolved": "https://registry.npmjs.org/@isaacs/balanced-match/-/balanced-match-4.0.1.tgz",
-      "integrity": "sha512-yzMTt9lEb8Gv7zRioUilSglI0c0smZ9k5D65677DLWLtWJaXIS3CqcGyUFByYKlnUj6TkjLVs54fBl6+TiGQDQ==",
-      "license": "MIT",
-      "engines": {
-        "node": "20 || >=22"
-      }
-    },
-    "node_modules/@isaacs/brace-expansion": {
-      "version": "5.0.1",
-      "resolved": "https://registry.npmjs.org/@isaacs/brace-expansion/-/brace-expansion-5.0.1.tgz",
-      "integrity": "sha512-WMz71T1JS624nWj2n2fnYAuPovhv7EUhk69R6i9dsVyzxt5eM3bjwvgk9L+APE1TRscGysAVMANkB0jh0LQZrQ==",
-      "license": "MIT",
-      "dependencies": {
-        "@isaacs/balanced-match": "^4.0.1"
-      },
-      "engines": {
-        "node": "20 || >=22"
-      }
-    },
     "node_modules/@microsoft/1ds-core-js": {
       "version": "4.3.4",
       "resolved": "https://registry.npmjs.org/@microsoft/1ds-core-js/-/1ds-core-js-4.3.4.tgz",
@@ -189,16 +168,37 @@
         "vscode": "^1.75.0"
       }
     },
+    "node_modules/balanced-match": {
+      "version": "4.0.4",
+      "resolved": "https://registry.npmjs.org/balanced-match/-/balanced-match-4.0.4.tgz",
+      "integrity": "sha512-BLrgEcRTwX2o6gGxGOCNyMvGSp35YofuYzw9h1IMTRmKqttAZZVU67bdb9Pr2vUHA8+j3i2tJfjO6C6+4myGTA==",
+      "license": "MIT",
+      "engines": {
+        "node": "18 || 20 || >=22"
+      }
+    },
+    "node_modules/brace-expansion": {
+      "version": "5.0.3",
+      "resolved": "https://registry.npmjs.org/brace-expansion/-/brace-expansion-5.0.3.tgz",
+      "integrity": "sha512-fy6KJm2RawA5RcHkLa1z/ScpBeA762UF9KmZQxwIbDtRJrgLzM10depAiEQ+CXYcoiqW1/m96OAAoke2nE9EeA==",
+      "license": "MIT",
+      "dependencies": {
+        "balanced-match": "^4.0.2"
+      },
+      "engines": {
+        "node": "18 || 20 || >=22"
+      }
+    },
     "node_modules/minimatch": {
-      "version": "10.0.3",
-      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.0.3.tgz",
-      "integrity": "sha512-IPZ167aShDZZUMdRk66cyQAW3qr0WzbHkPdMYa8bzZhlHhO3jALbKdxcaak7W9FfT2rZNpQuUu4Od7ILEpXSaw==",
-      "license": "ISC",
+      "version": "10.2.4",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.2.4.tgz",
+      "integrity": "sha512-oRjTw/97aTBN0RHbYCdtF1MQfvusSIBQM0IZEgzl6426+8jSC0nF1a/GmnVLpfB9yyr6g6FTqWqiZVbxrtaCIg==",
+      "license": "BlueOak-1.0.0",
       "dependencies": {
-        "@isaacs/brace-expansion": "^5.0.0"
+        "brace-expansion": "^5.0.2"
       },
       "engines": {
-        "node": "20 || >=22"
+        "node": "18 || 20 || >=22"
       },
       "funding": {
         "url": "https://github.com/sponsors/isaacs"
diff --git a/extensions/html-language-features/server/build/javaScriptLibraryLoader.js b/extensions/html-language-features/server/build/javaScriptLibraryLoader.js
deleted file mode 100644
index b8b0f8c4eb64a..0000000000000
--- a/extensions/html-language-features/server/build/javaScriptLibraryLoader.js
+++ /dev/null
@@ -1,132 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-// a webpack loader that bundles all library definitions (d.ts) for the embedded JavaScript engine.
-
-const path = require('path');
-const fs = require('fs');
-
-const TYPESCRIPT_LIB_SOURCE = path.join(__dirname, '../../../node_modules/typescript/lib');
-const JQUERY_DTS = path.join(__dirname, '../lib/jquery.d.ts');
-
-module.exports = function () {
-	function getFileName(name) {
-		return (name === '' ? 'lib.d.ts' : `lib.${name}.d.ts`);
-	}
-	function readLibFile(name) {
-		var srcPath = path.join(TYPESCRIPT_LIB_SOURCE, getFileName(name));
-		return fs.readFileSync(srcPath).toString();
-	}
-
-	var queue = [];
-	var in_queue = {};
-
-	var enqueue = function (name) {
-		if (in_queue[name]) {
-			return;
-		}
-		in_queue[name] = true;
-		queue.push(name);
-	};
-
-	enqueue('es2020.full');
-
-	var result = [];
-	while (queue.length > 0) {
-		var name = queue.shift();
-		var contents = readLibFile(name);
-		var lines = contents.split(/\r\n|\r|\n/);
-
-		var outputLines = [];
-		for (let i = 0; i < lines.length; i++) {
-			let m = lines[i].match(/\/\/\/\s*<reference\s*lib="([^"]+)"/);
-			if (m) {
-				enqueue(m[1]);
-			}
-			outputLines.push(lines[i]);
-		}
-
-		result.push({
-			name: getFileName(name),
-			output: `"${escapeText(outputLines.join('\n'))}"`
-		});
-	}
-
-	const jquerySource = fs.readFileSync(JQUERY_DTS).toString();
-	var lines = jquerySource.split(/\r\n|\r|\n/);
-	result.push({
-		name: 'jquery',
-		output: `"${escapeText(lines.join('\n'))}"`
-	});
-
-	let strResult = `\nconst libs : { [name:string]: string; } = {\n`
-	for (let i = result.length - 1; i >= 0; i--) {
-		strResult += `"${result[i].name}": ${result[i].output},\n`;
-	}
-	strResult += `\n};`
-
-	strResult += `export function loadLibrary(name: string) : string {\n return libs[name] || ''; \n}`;
-
-	return strResult;
-}
-
-/**
- * Escape text such that it can be used in a javascript string enclosed by double quotes (")
- */
-function escapeText(text) {
-	// See http://www.javascriptkit.com/jsref/escapesequence.shtml
-	var _backspace = '\b'.charCodeAt(0);
-	var _formFeed = '\f'.charCodeAt(0);
-	var _newLine = '\n'.charCodeAt(0);
-	var _nullChar = 0;
-	var _carriageReturn = '\r'.charCodeAt(0);
-	var _tab = '\t'.charCodeAt(0);
-	var _verticalTab = '\v'.charCodeAt(0);
-	var _backslash = '\\'.charCodeAt(0);
-	var _doubleQuote = '"'.charCodeAt(0);
-
-	var startPos = 0, chrCode, replaceWith = null, resultPieces = [];
-
-	for (var i = 0, len = text.length; i < len; i++) {
-		chrCode = text.charCodeAt(i);
-		switch (chrCode) {
-			case _backspace:
-				replaceWith = '\\b';
-				break;
-			case _formFeed:
-				replaceWith = '\\f';
-				break;
-			case _newLine:
-				replaceWith = '\\n';
-				break;
-			case _nullChar:
-				replaceWith = '\\0';
-				break;
-			case _carriageReturn:
-				replaceWith = '\\r';
-				break;
-			case _tab:
-				replaceWith = '\\t';
-				break;
-			case _verticalTab:
-				replaceWith = '\\v';
-				break;
-			case _backslash:
-				replaceWith = '\\\\';
-				break;
-			case _doubleQuote:
-				replaceWith = '\\"';
-				break;
-		}
-		if (replaceWith !== null) {
-			resultPieces.push(text.substring(startPos, i));
-			resultPieces.push(replaceWith);
-			startPos = i + 1;
-			replaceWith = null;
-		}
-	}
-	resultPieces.push(text.substring(startPos, len));
-	return resultPieces.join('');
-}
diff --git a/extensions/json-language-features/client/src/jsonClient.ts b/extensions/json-language-features/client/src/jsonClient.ts
index eb336e8f89bc5..06dfa8efe48db 100644
--- a/extensions/json-language-features/client/src/jsonClient.ts
+++ b/extensions/json-language-features/client/src/jsonClient.ts
@@ -690,6 +690,23 @@ async function startClientWithParticipants(_context: ExtensionContext, languageP
 			execute: () => Promise<void>;
 		}
 
+		const normalizeTrustedDomains = (domains: Record<string, boolean>): Record<string, boolean> => {
+			return Object.fromEntries(Object.entries(domains).sort(([a], [b]) => a.localeCompare(b)));
+		};
+
+		const updateTrustedDomains = async (updateDomain: string): Promise<void> => {
+			const config = workspace.getConfiguration();
+			const currentDomains = config.get<Record<string, boolean>>(SettingIds.trustedDomains, {});
+			if (currentDomains[updateDomain] === true) {
+				return;
+			}
+			const nextDomains = normalizeTrustedDomains({
+				...currentDomains,
+				[updateDomain]: true
+			});
+			await config.update(SettingIds.trustedDomains, nextDomains, true);
+		};
+
 		const items: QuickPickItemWithAction[] = [];
 
 		try {
@@ -701,10 +718,7 @@ async function startClientWithParticipants(_context: ExtensionContext, languageP
 				label: l10n.t('Trust Domain: {0}', domain),
 				description: l10n.t('Allow all schemas from this domain'),
 				execute: async () => {
-					const config = workspace.getConfiguration();
-					const currentDomains = config.get<Record<string, boolean>>(SettingIds.trustedDomains, {});
-					currentDomains[domain] = true;
-					await config.update(SettingIds.trustedDomains, currentDomains, true);
+					await updateTrustedDomains(domain);
 					await commands.executeCommand(CommandIds.workbenchActionOpenSettings, SettingIds.trustedDomains);
 				}
 			});
@@ -714,10 +728,7 @@ async function startClientWithParticipants(_context: ExtensionContext, languageP
 				label: l10n.t('Trust URI: {0}', schemaUri),
 				description: l10n.t('Allow only this specific schema'),
 				execute: async () => {
-					const config = workspace.getConfiguration();
-					const currentDomains = config.get<Record<string, boolean>>(SettingIds.trustedDomains, {});
-					currentDomains[schemaUri] = true;
-					await config.update(SettingIds.trustedDomains, currentDomains, true);
+					await updateTrustedDomains(schemaUri);
 					await commands.executeCommand(CommandIds.workbenchActionOpenSettings, SettingIds.trustedDomains);
 				}
 			});
@@ -926,4 +937,3 @@ export function isSchemaResolveError(d: Diagnostic) {
 	return typeof d.code === 'number' && d.code >= ErrorCodes.SchemaResolveError;
 }
 
-
diff --git a/extensions/json-language-features/package-lock.json b/extensions/json-language-features/package-lock.json
index e5e1b9c133204..9ceade066818b 100644
--- a/extensions/json-language-features/package-lock.json
+++ b/extensions/json-language-features/package-lock.json
@@ -190,9 +190,9 @@
       }
     },
     "node_modules/minimatch": {
-      "version": "10.2.2",
-      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.2.2.tgz",
-      "integrity": "sha512-+G4CpNBxa5MprY+04MbgOw1v7So6n5JY166pFi9KfYwT78fxScCeSNQSNzp6dpPSW2rONOps6Ocam1wFhCgoVw==",
+      "version": "10.2.4",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-10.2.4.tgz",
+      "integrity": "sha512-oRjTw/97aTBN0RHbYCdtF1MQfvusSIBQM0IZEgzl6426+8jSC0nF1a/GmnVLpfB9yyr6g6FTqWqiZVbxrtaCIg==",
       "license": "BlueOak-1.0.0",
       "dependencies": {
         "brace-expansion": "^5.0.2"
diff --git a/extensions/json-language-features/package.json b/extensions/json-language-features/package.json
index fe0a23cb59101..1368b6cda477a 100644
--- a/extensions/json-language-features/package.json
+++ b/extensions/json-language-features/package.json
@@ -59,17 +59,17 @@
               "url": {
                 "type": "string",
                 "default": "/user.schema.json",
-                "description": "%json.schemas.url.desc%"
+                "markdownDescription": "%json.schemas.url.desc%"
               },
               "fileMatch": {
                 "type": "array",
                 "items": {
                   "type": "string",
                   "default": "MyFile.json",
-                  "description": "%json.schemas.fileMatch.item.desc%"
+                  "markdownDescription": "%json.schemas.fileMatch.item.desc%"
                 },
                 "minItems": 1,
-                "description": "%json.schemas.fileMatch.desc%"
+                "markdownDescription": "%json.schemas.fileMatch.desc%"
               },
               "schema": {
                 "$ref": "http://json-schema.org/draft-07/schema#",
@@ -141,7 +141,7 @@
           "additionalProperties": {
             "type": "boolean"
           },
-          "description": "%json.schemaDownload.trustedDomains.desc%",
+          "markdownDescription": "%json.schemaDownload.trustedDomains.desc%",
           "tags": [
             "usesOnlineServices"
           ]
diff --git a/extensions/json-language-features/package.nls.json b/extensions/json-language-features/package.nls.json
index 9052d3781c9ce..30199b2bb33f3 100644
--- a/extensions/json-language-features/package.nls.json
+++ b/extensions/json-language-features/package.nls.json
@@ -2,12 +2,12 @@
 	"displayName": "JSON Language Features",
 	"description": "Provides rich language support for JSON files.",
 	"json.schemas.desc": "Associate schemas to JSON files in the current project.",
-	"json.schemas.url.desc": "A URL or absolute file path to a schema. Can be a relative path (starting with './') in workspace and workspace folder settings.",
-	"json.schemas.fileMatch.desc": "An array of file patterns to match against when resolving JSON files to schemas. `*` and '**' can be used as a wildcard. Exclusion patterns can also be defined and start with '!'. A file matches when there is at least one matching pattern and the last matching pattern is not an exclusion pattern.",
-	"json.schemas.fileMatch.item.desc": "A file pattern that can contain '*' and '**' to match against when resolving JSON files to schemas. When beginning with '!', it defines an exclusion pattern.",
+	"json.schemas.url.desc": "A URL or absolute file path to a schema. Can be a relative path (starting with `./`) in workspace and workspace folder settings.",
+	"json.schemas.fileMatch.desc": "An array of file patterns to match against when resolving JSON files to schemas. `*` and `**` can be used as a wildcard. Exclusion patterns can also be defined and start with `!`. A file matches when there is at least one matching pattern and the last matching pattern is not an exclusion pattern.",
+	"json.schemas.fileMatch.item.desc": "A file pattern that can contain `*` and `**` to match against when resolving JSON files to schemas. When beginning with `!`, it defines an exclusion pattern.",
 	"json.schemas.schema.desc": "The schema definition for the given URL. The schema only needs to be provided to avoid accesses to the schema URL.",
 	"json.format.enable.desc": "Enable/disable default JSON formatter",
-	"json.format.keepLines.desc" : "Keep all existing new lines when formatting.",
+	"json.format.keepLines.desc": "Keep all existing new lines when formatting.",
 	"json.validate.enable.desc": "Enable/disable JSON validation.",
 	"json.tracing.desc": "Traces the communication between VS Code and the JSON language server.",
 	"json.colorDecorators.enable.desc": "Enables or disables color decorators",
@@ -20,5 +20,5 @@
 	"json.command.clearCache": "Clear Schema Cache",
 	"json.command.sort": "Sort Document",
 	"json.workspaceTrust": "The extension requires workspace trust to load schemas from http and https.",
-	"json.schemaDownload.trustedDomains.desc": "List of trusted domains for downloading JSON schemas over http(s). Use '*' to trust all domains. '*' can also be used as a wildcard in domain names."
+	"json.schemaDownload.trustedDomains.desc": "List of trusted domains for downloading JSON schemas over http(s). Use `*` to trust all domains. `*` can also be used as a wildcard in domain names."
 }
diff --git a/extensions/json-language-features/server/.npmignore b/extensions/json-language-features/server/.npmignore
index 960a01cc7b5da..f85ce05804aed 100644
--- a/extensions/json-language-features/server/.npmignore
+++ b/extensions/json-language-features/server/.npmignore
@@ -6,5 +6,4 @@ test/
 tsconfig.json
 .gitignore
 package-lock.json
-extension.webpack.config.js
 vscode-json-languageserver-*.tgz
diff --git a/extensions/mangle-loader.js b/extensions/mangle-loader.js
deleted file mode 100644
index ed32a85e633f3..0000000000000
--- a/extensions/mangle-loader.js
+++ /dev/null
@@ -1,66 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-// @ts-check
-
-const fs = require('fs');
-const webpack = require('webpack');
-const fancyLog = require('fancy-log');
-const ansiColors = require('ansi-colors');
-const { Mangler } = require('../build/lib/mangle/index.js');
-
-/**
- * Map of project paths to mangled file contents
- *
- * @type {Map<string, Promise<Map<string, { out: string; sourceMap?: string }>>>}
- */
-const mangleMap = new Map();
-
-/**
- * @param {string} projectPath
- */
-function getMangledFileContents(projectPath) {
-	let entry = mangleMap.get(projectPath);
-	if (!entry) {
-		const log = (...data) => fancyLog(ansiColors.blue('[mangler]'), ...data);
-		log(`Mangling ${projectPath}`);
-		const ts2tsMangler = new Mangler(projectPath, log, { mangleExports: true, manglePrivateFields: true });
-		entry = ts2tsMangler.computeNewFileContents();
-		mangleMap.set(projectPath, entry);
-	}
-
-	return entry;
-}
-
-/**
- * @type {webpack.LoaderDefinitionFunction}
- */
-module.exports = async function (source, sourceMap, meta) {
-	if (this.mode !== 'production') {
-		// Only enable mangling in production builds
-		return source;
-	}
-	if (true) {
-		// disable mangling for now, SEE https://github.com/microsoft/vscode/issues/204692
-		return source;
-	}
-	const options = this.getOptions();
-	if (options.disabled) {
-		// Dynamically disabled
-		return source;
-	}
-
-	if (source !== fs.readFileSync(this.resourcePath).toString()) {
-		// File content has changed by previous webpack steps.
-		// Skip mangling.
-		return source;
-	}
-
-	const callback = this.async();
-
-	const fileContentsMap = await getMangledFileContents(options.configFile);
-
-	const newContents = fileContentsMap.get(this.resourcePath);
-	callback(null, newContents?.out ?? source, sourceMap, meta);
-};
diff --git a/extensions/markdown-basics/package.json b/extensions/markdown-basics/package.json
index c77aad6a30149..58cc459ce3f2d 100644
--- a/extensions/markdown-basics/package.json
+++ b/extensions/markdown-basics/package.json
@@ -8,7 +8,9 @@
   "engines": {
     "vscode": "^1.20.0"
   },
-  "categories": ["Programming Languages"],
+  "categories": [
+    "Programming Languages"
+  ],
   "contributes": {
     "languages": [
       {
@@ -20,12 +22,16 @@
         "extensions": [
           ".md",
           ".mkd",
+          ".mkdn",
           ".mdwn",
           ".mdown",
           ".markdown",
           ".markdn",
           ".mdtxt",
           ".mdtext",
+          ".litcoffee",
+          ".ron",
+          ".ronn",
           ".workbook"
         ],
         "filenamePatterns": [
diff --git a/extensions/markdown-language-features/package-lock.json b/extensions/markdown-language-features/package-lock.json
index b7180c307306d..162ff688b0a54 100644
--- a/extensions/markdown-language-features/package-lock.json
+++ b/extensions/markdown-language-features/package-lock.json
@@ -10,7 +10,7 @@
       "license": "MIT",
       "dependencies": {
         "@vscode/extension-telemetry": "^0.9.8",
-        "dompurify": "^3.2.7",
+        "dompurify": "^3.3.2",
         "highlight.js": "^11.8.0",
         "markdown-it": "^12.3.2",
         "markdown-it-front-matter": "^0.2.4",
@@ -386,10 +386,13 @@
       }
     },
     "node_modules/dompurify": {
-      "version": "3.2.7",
-      "resolved": "https://registry.npmjs.org/dompurify/-/dompurify-3.2.7.tgz",
-      "integrity": "sha512-WhL/YuveyGXJaerVlMYGWhvQswa7myDG17P7Vu65EWC05o8vfeNbvNf4d/BOvH99+ZW+LlQsc1GDKMa1vNK6dw==",
+      "version": "3.3.2",
+      "resolved": "https://registry.npmjs.org/dompurify/-/dompurify-3.3.2.tgz",
+      "integrity": "sha512-6obghkliLdmKa56xdbLOpUZ43pAR6xFy1uOrxBaIDjT+yaRuuybLjGS9eVBoSR/UPU5fq3OXClEHLJNGvbxKpQ==",
       "license": "(MPL-2.0 OR Apache-2.0)",
+      "engines": {
+        "node": ">=20"
+      },
       "optionalDependencies": {
         "@types/trusted-types": "^2.0.7"
       }
@@ -513,9 +516,10 @@
       "integrity": "sha512-/sKlQJCBYVY9Ers9hqzKou4H6V5UWc/M59TH2dvkt+84itfnq7uFOMLpOiOS4ujvHP4etln18fmIxA5R5fll0g=="
     },
     "node_modules/minimatch": {
-      "version": "3.1.2",
-      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-3.1.2.tgz",
-      "integrity": "sha512-J7p63hRiAjw1NDEww1W7i37+ByIrOWO5XQQAzZ3VOcL0PNybwpfmV/N05zFAzwQ9USyEcX6t3UO+K5aqBQOIHw==",
+      "version": "3.1.5",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-3.1.5.tgz",
+      "integrity": "sha512-VgjWUsnnT6n+NUk6eZq77zeFdpW2LWDzP6zFGrCbHXiYNul5Dzqk2HHQ5uFH2DNW5Xbp8+jVzaeNt94ssEEl4w==",
+      "license": "ISC",
       "dependencies": {
         "brace-expansion": "^1.1.7"
       },
diff --git a/extensions/markdown-language-features/package.json b/extensions/markdown-language-features/package.json
index 745ba66b56c5e..b4141d80bf5df 100644
--- a/extensions/markdown-language-features/package.json
+++ b/extensions/markdown-language-features/package.json
@@ -230,6 +230,14 @@
           "group": "1_markdown"
         }
       ],
+      "modalEditor/editorTitle": [
+        {
+          "command": "markdown.showPreviewToSide",
+          "when": "editorLangId =~ /^(markdown|prompt|instructions|chatagent|skill)$/ && !notebookEditorFocused && !hasCustomMarkdownPreview",
+          "alt": "markdown.showPreview",
+          "group": "navigation"
+        }
+      ],
       "explorer/context": [
         {
           "command": "markdown.showPreview",
@@ -774,7 +782,7 @@
   },
   "dependencies": {
     "@vscode/extension-telemetry": "^0.9.8",
-    "dompurify": "^3.2.7",
+    "dompurify": "^3.3.2",
     "highlight.js": "^11.8.0",
     "markdown-it": "^12.3.2",
     "markdown-it-front-matter": "^0.2.4",
diff --git a/extensions/markdown-language-features/preview-src/activeLineMarker.ts b/extensions/markdown-language-features/preview-src/activeLineMarker.ts
index 75c1ed7cbc962..0e63dad4599df 100644
--- a/extensions/markdown-language-features/preview-src/activeLineMarker.ts
+++ b/extensions/markdown-language-features/preview-src/activeLineMarker.ts
@@ -5,27 +5,27 @@
 import { getElementsForSourceLine } from './scroll-sync';
 
 export class ActiveLineMarker {
-	private _current: any;
+	#current: HTMLElement | undefined;
 
 	onDidChangeTextEditorSelection(line: number, documentVersion: number) {
 		const { previous } = getElementsForSourceLine(line, documentVersion);
-		this._update(previous && (previous.codeElement || previous.element));
+		this.#update(previous && (previous.codeElement || previous.element));
 	}
 
-	private _update(before: HTMLElement | undefined) {
-		this._unmarkActiveElement(this._current);
-		this._markActiveElement(before);
-		this._current = before;
+	#update(before: HTMLElement | undefined) {
+		this.#unmarkActiveElement(this.#current);
+		this.#markActiveElement(before);
+		this.#current = before;
 	}
 
-	private _unmarkActiveElement(element: HTMLElement | undefined) {
+	#unmarkActiveElement(element: HTMLElement | undefined) {
 		if (!element) {
 			return;
 		}
 		element.classList.toggle('code-active-line', false);
 	}
 
-	private _markActiveElement(element: HTMLElement | undefined) {
+	#markActiveElement(element: HTMLElement | undefined) {
 		if (!element) {
 			return;
 		}
diff --git a/extensions/markdown-language-features/preview-src/csp.ts b/extensions/markdown-language-features/preview-src/csp.ts
index fcc38352da880..4db9d7b116fb4 100644
--- a/extensions/markdown-language-features/preview-src/csp.ts
+++ b/extensions/markdown-language-features/preview-src/csp.ts
@@ -11,45 +11,49 @@ import { getStrings } from './strings';
  * Shows an alert when there is a content security policy violation.
  */
 export class CspAlerter {
-	private _didShow = false;
-	private _didHaveCspWarning = false;
+	#didShow = false;
+	#didHaveCspWarning = false;
 
-	private _messaging?: MessagePoster;
+	#messaging?: MessagePoster;
+
+	readonly #settingsManager: SettingsManager;
 
 	constructor(
-		private readonly _settingsManager: SettingsManager,
+		settingsManager: SettingsManager,
 	) {
+		this.#settingsManager = settingsManager;
+
 		document.addEventListener('securitypolicyviolation', () => {
-			this._onCspWarning();
+			this.#onCspWarning();
 		});
 
 		window.addEventListener('message', (event) => {
 			if (event?.data && event.data.name === 'vscode-did-block-svg') {
-				this._onCspWarning();
+				this.#onCspWarning();
 			}
 		});
 	}
 
 	public setPoster(poster: MessagePoster) {
-		this._messaging = poster;
-		if (this._didHaveCspWarning) {
-			this._showCspWarning();
+		this.#messaging = poster;
+		if (this.#didHaveCspWarning) {
+			this.#showCspWarning();
 		}
 	}
 
-	private _onCspWarning() {
-		this._didHaveCspWarning = true;
-		this._showCspWarning();
+	#onCspWarning() {
+		this.#didHaveCspWarning = true;
+		this.#showCspWarning();
 	}
 
-	private _showCspWarning() {
+	#showCspWarning() {
 		const strings = getStrings();
-		const settings = this._settingsManager.settings;
+		const settings = this.#settingsManager.settings;
 
-		if (this._didShow || settings.disableSecurityWarnings || !this._messaging) {
+		if (this.#didShow || settings.disableSecurityWarnings || !this.#messaging) {
 			return;
 		}
-		this._didShow = true;
+		this.#didShow = true;
 
 		const notification = document.createElement('a');
 		notification.innerText = strings.cspAlertMessageText;
@@ -59,7 +63,7 @@ export class CspAlerter {
 		notification.setAttribute('role', 'button');
 		notification.setAttribute('aria-label', strings.cspAlertMessageLabel);
 		notification.onclick = () => {
-			this._messaging!.postMessage('showPreviewSecuritySelector', { source: settings.source });
+			this.#messaging!.postMessage('showPreviewSecuritySelector', { source: settings.source });
 		};
 		document.body.appendChild(notification);
 	}
diff --git a/extensions/markdown-language-features/preview-src/index.ts b/extensions/markdown-language-features/preview-src/index.ts
index 08475ad7fa4be..95ec3211b581b 100644
--- a/extensions/markdown-language-features/preview-src/index.ts
+++ b/extensions/markdown-language-features/preview-src/index.ts
@@ -26,12 +26,14 @@ const vscode = acquireVsCodeApi();
 interface State {
 	scrollProgress?: number;
 	resource?: string;
+	line?: number;
+	fragment?: string;
 }
 
 const originalState: State = vscode.getState() ?? {};
-const state = {
+const state: State = {
 	...originalState,
-	...getData<any>('data-state')
+	...getData<Partial<State>>('data-state')
 };
 
 if (typeof originalState.scrollProgress !== 'undefined' && originalState?.resource !== state.resource) {
@@ -335,10 +337,10 @@ document.addEventListener('click', event => {
 		return;
 	}
 
-	let node: any = event.target;
+	let node = event.target as Element | null;
 	while (node) {
-		if (node.tagName && node.tagName === 'A' && node.href) {
-			if (node.getAttribute('href').startsWith('#')) {
+		if (node.tagName && node.tagName === 'A' && (node as HTMLAnchorElement).href) {
+			if (node.getAttribute('href')?.startsWith('#')) {
 				return;
 			}
 
@@ -346,13 +348,13 @@ document.addEventListener('click', event => {
 			if (!hrefText) {
 				hrefText = node.getAttribute('href');
 				// Pass through known schemes
-				if (passThroughLinkSchemes.some(scheme => hrefText.startsWith(scheme))) {
+				if (hrefText && passThroughLinkSchemes.some(scheme => hrefText!.startsWith(scheme))) {
 					return;
 				}
 			}
 
 			// If original link doesn't look like a url, delegate back to VS Code to resolve
-			if (!/^[a-z\-]+:/i.test(hrefText)) {
+			if (hrefText && !/^[a-z\-]+:/i.test(hrefText)) {
 				messaging.postMessage('openLink', { href: hrefText });
 				event.preventDefault();
 				event.stopPropagation();
@@ -361,7 +363,7 @@ document.addEventListener('click', event => {
 
 			return;
 		}
-		node = node.parentNode;
+		node = node.parentElement;
 	}
 }, true);
 
diff --git a/extensions/markdown-language-features/preview-src/loading.ts b/extensions/markdown-language-features/preview-src/loading.ts
index c6e6d27acd904..f3270b22214e2 100644
--- a/extensions/markdown-language-features/preview-src/loading.ts
+++ b/extensions/markdown-language-features/preview-src/loading.ts
@@ -5,15 +5,20 @@
 import { MessagePoster } from './messaging';
 
 export class StyleLoadingMonitor {
-	private readonly _unloadedStyles: string[] = [];
-	private _finishedLoading: boolean = false;
+	readonly #unloadedStyles: string[] = [];
+	#finishedLoading: boolean = false;
 
-	private _poster?: MessagePoster;
+	#poster?: MessagePoster;
 
 	constructor() {
-		const onStyleLoadError = (event: any) => {
-			const source = event.target.dataset.source;
-			this._unloadedStyles.push(source);
+		const onStyleLoadError = (event: Event | string) => {
+			if (!(event instanceof Event)) {
+				return;
+			}
+			const source = (event.target as HTMLElement | null)?.dataset.source;
+			if (source) {
+				this.#unloadedStyles.push(source);
+			}
 		};
 
 		window.addEventListener('DOMContentLoaded', () => {
@@ -25,18 +30,18 @@ export class StyleLoadingMonitor {
 		});
 
 		window.addEventListener('load', () => {
-			if (!this._unloadedStyles.length) {
+			if (!this.#unloadedStyles.length) {
 				return;
 			}
-			this._finishedLoading = true;
-			this._poster?.postMessage('previewStyleLoadError', { unloadedStyles: this._unloadedStyles });
+			this.#finishedLoading = true;
+			this.#poster?.postMessage('previewStyleLoadError', { unloadedStyles: this.#unloadedStyles });
 		});
 	}
 
 	public setPoster(poster: MessagePoster): void {
-		this._poster = poster;
-		if (this._finishedLoading) {
-			poster.postMessage('previewStyleLoadError', { unloadedStyles: this._unloadedStyles });
+		this.#poster = poster;
+		if (this.#finishedLoading) {
+			poster.postMessage('previewStyleLoadError', { unloadedStyles: this.#unloadedStyles });
 		}
 	}
 }
diff --git a/extensions/markdown-language-features/preview-src/messaging.ts b/extensions/markdown-language-features/preview-src/messaging.ts
index 1fb29f0b55b94..0458cac997c5e 100644
--- a/extensions/markdown-language-features/preview-src/messaging.ts
+++ b/extensions/markdown-language-features/preview-src/messaging.ts
@@ -3,8 +3,9 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { SettingsManager } from './settings';
+import type { WebviewApi } from 'vscode-webview';
 import type { FromWebviewMessage } from '../types/previewMessaging';
+import { SettingsManager } from './settings';
 
 export interface MessagePoster {
 	/**
@@ -16,7 +17,7 @@ export interface MessagePoster {
 	): void;
 }
 
-export const createPosterForVsCode = (vscode: any, settingsManager: SettingsManager): MessagePoster => {
+export const createPosterForVsCode = (vscode: WebviewApi<unknown>, settingsManager: SettingsManager): MessagePoster => {
 	return {
 		postMessage<T extends FromWebviewMessage.Type>(
 			type: T['type'],
diff --git a/extensions/markdown-language-features/preview-src/scroll-sync.ts b/extensions/markdown-language-features/preview-src/scroll-sync.ts
index 33d81094cb59f..14aa18d54908c 100644
--- a/extensions/markdown-language-features/preview-src/scroll-sync.ts
+++ b/extensions/markdown-language-features/preview-src/scroll-sync.ts
@@ -9,18 +9,18 @@ const codeLineClass = 'code-line';
 
 
 export class CodeLineElement {
-	private readonly _detailParentElements: readonly HTMLDetailsElement[];
+	readonly #detailParentElements: readonly HTMLDetailsElement[];
 
 	constructor(
 		readonly element: HTMLElement,
 		readonly line: number,
 		readonly codeElement?: HTMLElement,
 	) {
-		this._detailParentElements = Array.from(getParentsWithTagName<HTMLDetailsElement>(element, 'DETAILS'));
+		this.#detailParentElements = Array.from(getParentsWithTagName<HTMLDetailsElement>(element, 'DETAILS'));
 	}
 
 	get isVisible(): boolean {
-		if (this._detailParentElements.some(x => !x.open)) {
+		if (this.#detailParentElements.some(x => !x.open)) {
 			return false;
 		}
 
diff --git a/extensions/markdown-language-features/preview-src/settings.ts b/extensions/markdown-language-features/preview-src/settings.ts
index 0fb5d0c2686cc..6d642b58c64e3 100644
--- a/extensions/markdown-language-features/preview-src/settings.ts
+++ b/extensions/markdown-language-features/preview-src/settings.ts
@@ -33,13 +33,13 @@ export function getData<T = {}>(key: string): T {
 }
 
 export class SettingsManager {
-	private _settings: PreviewSettings = getData('data-settings');
+	#settings: PreviewSettings = getData('data-settings');
 
 	public get settings(): PreviewSettings {
-		return this._settings;
+		return this.#settings;
 	}
 
 	public updateSettings(newSettings: PreviewSettings) {
-		this._settings = newSettings;
+		this.#settings = newSettings;
 	}
 }
diff --git a/extensions/markdown-language-features/src/client/client.ts b/extensions/markdown-language-features/src/client/client.ts
index bf7be3f32064c..dc279f02d84ec 100644
--- a/extensions/markdown-language-features/src/client/client.ts
+++ b/extensions/markdown-language-features/src/client/client.ts
@@ -17,37 +17,43 @@ export type LanguageClientConstructor = (name: string, description: string, clie
 
 export class MdLanguageClient implements IDisposable {
 
+	readonly #client: BaseLanguageClient;
+	readonly #workspace: VsCodeMdWorkspace;
+
 	constructor(
-		private readonly _client: BaseLanguageClient,
-		private readonly _workspace: VsCodeMdWorkspace,
-	) { }
+		client: BaseLanguageClient,
+		workspace: VsCodeMdWorkspace,
+	) {
+		this.#client = client;
+		this.#workspace = workspace;
+	}
 
 	dispose(): void {
-		this._client.stop();
-		this._workspace.dispose();
+		this.#client.stop();
+		this.#workspace.dispose();
 	}
 
 	resolveLinkTarget(linkText: string, uri: vscode.Uri): Promise<proto.ResolvedDocumentLinkTarget> {
-		return this._client.sendRequest(proto.resolveLinkTarget, { linkText, uri: uri.toString() });
+		return this.#client.sendRequest(proto.resolveLinkTarget, { linkText, uri: uri.toString() });
 	}
 
 	getEditForFileRenames(files: ReadonlyArray<{ oldUri: string; newUri: string }>, token: vscode.CancellationToken) {
-		return this._client.sendRequest(proto.getEditForFileRenames, files, token);
+		return this.#client.sendRequest(proto.getEditForFileRenames, files, token);
 	}
 
 	getReferencesToFileInWorkspace(resource: vscode.Uri, token: vscode.CancellationToken) {
-		return this._client.sendRequest(proto.getReferencesToFileInWorkspace, { uri: resource.toString() }, token);
+		return this.#client.sendRequest(proto.getReferencesToFileInWorkspace, { uri: resource.toString() }, token);
 	}
 
 	prepareUpdatePastedLinks(doc: vscode.Uri, ranges: readonly vscode.Range[], token: vscode.CancellationToken) {
-		return this._client.sendRequest(proto.prepareUpdatePastedLinks, {
+		return this.#client.sendRequest(proto.prepareUpdatePastedLinks, {
 			uri: doc.toString(),
 			ranges: ranges.map(range => Range.create(range.start.line, range.start.character, range.end.line, range.end.character)),
 		}, token);
 	}
 
 	getUpdatePastedLinksEdit(pastingIntoDoc: vscode.Uri, edits: readonly vscode.TextEdit[], metadata: string, token: vscode.CancellationToken) {
-		return this._client.sendRequest(proto.getUpdatePastedLinksEdit, {
+		return this.#client.sendRequest(proto.getUpdatePastedLinksEdit, {
 			metadata,
 			pasteIntoDoc: pastingIntoDoc.toString(),
 			edits: edits.map(edit => TextEdit.replace(edit.range, edit.newText)),
diff --git a/extensions/markdown-language-features/src/client/fileWatchingManager.ts b/extensions/markdown-language-features/src/client/fileWatchingManager.ts
index e2010edda8a45..c617a73634df7 100644
--- a/extensions/markdown-language-features/src/client/fileWatchingManager.ts
+++ b/extensions/markdown-language-features/src/client/fileWatchingManager.ts
@@ -17,12 +17,12 @@ type DirWatcherEntry = {
 
 export class FileWatcherManager {
 
-	private readonly _fileWatchers = new Map<number, {
+	readonly #fileWatchers = new Map<number, {
 		readonly watcher: vscode.FileSystemWatcher;
 		readonly dirWatchers: DirWatcherEntry[];
 	}>();
 
-	private readonly _dirWatchers = new ResourceMap<{
+	readonly #dirWatchers = new ResourceMap<{
 		readonly watcher: vscode.FileSystemWatcher;
 		refCount: number;
 	}>();
@@ -35,7 +35,7 @@ export class FileWatcherManager {
 
 		const watcher = vscode.workspace.createFileSystemWatcher(new vscode.RelativePattern(uri, '*'), !listeners.create, !listeners.change, !listeners.delete);
 		const parentDirWatchers: DirWatcherEntry[] = [];
-		this._fileWatchers.set(id, { watcher, dirWatchers: parentDirWatchers });
+		this.#fileWatchers.set(id, { watcher, dirWatchers: parentDirWatchers });
 
 		if (listeners.create) { watcher.onDidCreate(listeners.create); }
 		if (listeners.change) { watcher.onDidChange(listeners.change); }
@@ -46,12 +46,12 @@ export class FileWatcherManager {
 			for (let dirUri = Utils.dirname(uri); dirUri.path.length > 1; dirUri = Utils.dirname(dirUri)) {
 				const disposables: IDisposable[] = [];
 
-				let parentDirWatcher = this._dirWatchers.get(dirUri);
+				let parentDirWatcher = this.#dirWatchers.get(dirUri);
 				if (!parentDirWatcher) {
 					const glob = new vscode.RelativePattern(Utils.dirname(dirUri), Utils.basename(dirUri));
 					const parentWatcher = vscode.workspace.createFileSystemWatcher(glob, !listeners.create, true, !listeners.delete);
 					parentDirWatcher = { refCount: 0, watcher: parentWatcher };
-					this._dirWatchers.set(dirUri, parentDirWatcher);
+					this.#dirWatchers.set(dirUri, parentDirWatcher);
 				}
 				parentDirWatcher.refCount++;
 
@@ -81,16 +81,16 @@ export class FileWatcherManager {
 	}
 
 	delete(id: number): void {
-		const entry = this._fileWatchers.get(id);
+		const entry = this.#fileWatchers.get(id);
 		if (entry) {
 			for (const dirWatcher of entry.dirWatchers) {
 				disposeAll(dirWatcher.disposables);
 
-				const dirWatcherEntry = this._dirWatchers.get(dirWatcher.uri);
+				const dirWatcherEntry = this.#dirWatchers.get(dirWatcher.uri);
 				if (dirWatcherEntry) {
 					if (--dirWatcherEntry.refCount <= 0) {
 						dirWatcherEntry.watcher.dispose();
-						this._dirWatchers.delete(dirWatcher.uri);
+						this.#dirWatchers.delete(dirWatcher.uri);
 					}
 				}
 			}
@@ -98,6 +98,6 @@ export class FileWatcherManager {
 			entry.watcher.dispose();
 		}
 
-		this._fileWatchers.delete(id);
+		this.#fileWatchers.delete(id);
 	}
 }
diff --git a/extensions/markdown-language-features/src/client/inMemoryDocument.ts b/extensions/markdown-language-features/src/client/inMemoryDocument.ts
index 953f0da7c898a..2726adb6de16f 100644
--- a/extensions/markdown-language-features/src/client/inMemoryDocument.ts
+++ b/extensions/markdown-language-features/src/client/inMemoryDocument.ts
@@ -9,7 +9,7 @@ import { ITextDocument } from '../types/textDocument';
 
 export class InMemoryDocument implements ITextDocument {
 
-	private readonly _doc: TextDocument;
+	readonly #doc: TextDocument;
 
 	public readonly uri: vscode.Uri;
 	public readonly version: number;
@@ -21,15 +21,15 @@ export class InMemoryDocument implements ITextDocument {
 	) {
 		this.uri = uri;
 		this.version = version;
-		this._doc = TextDocument.create(this.uri.toString(), 'markdown', 0, contents);
+		this.#doc = TextDocument.create(this.uri.toString(), 'markdown', 0, contents);
 	}
 
 	getText(range?: vscode.Range): string {
-		return this._doc.getText(range);
+		return this.#doc.getText(range);
 	}
 
 	positionAt(offset: number): vscode.Position {
-		const pos = this._doc.positionAt(offset);
+		const pos = this.#doc.positionAt(offset);
 		return new vscode.Position(pos.line, pos.character);
 	}
 }
diff --git a/extensions/markdown-language-features/src/client/workspace.ts b/extensions/markdown-language-features/src/client/workspace.ts
index 9ea3173c9cc1e..b07a93ade7856 100644
--- a/extensions/markdown-language-features/src/client/workspace.ts
+++ b/extensions/markdown-language-features/src/client/workspace.ts
@@ -17,47 +17,47 @@ import { ResourceMap } from '../util/resourceMap';
  */
 export class VsCodeMdWorkspace extends Disposable {
 
-	private readonly _watcher: vscode.FileSystemWatcher | undefined;
+	readonly #watcher: vscode.FileSystemWatcher | undefined;
 
-	private readonly _documentCache = new ResourceMap<ITextDocument>();
+	readonly #documentCache = new ResourceMap<ITextDocument>();
 
-	private readonly _utf8Decoder = new TextDecoder('utf-8');
+	readonly #utf8Decoder = new TextDecoder('utf-8');
 
 	constructor() {
 		super();
 
-		this._watcher = this._register(vscode.workspace.createFileSystemWatcher('**/*.md'));
+		this.#watcher = this._register(vscode.workspace.createFileSystemWatcher('**/*.md'));
 
-		this._register(this._watcher.onDidChange(async resource => {
-			this._documentCache.delete(resource);
+		this._register(this.#watcher.onDidChange(async resource => {
+			this.#documentCache.delete(resource);
 		}));
 
-		this._register(this._watcher.onDidDelete(resource => {
-			this._documentCache.delete(resource);
+		this._register(this.#watcher.onDidDelete(resource => {
+			this.#documentCache.delete(resource);
 		}));
 
 		this._register(vscode.workspace.onDidOpenTextDocument(e => {
-			this._documentCache.delete(e.uri);
+			this.#documentCache.delete(e.uri);
 		}));
 
 		this._register(vscode.workspace.onDidCloseTextDocument(e => {
-			this._documentCache.delete(e.uri);
+			this.#documentCache.delete(e.uri);
 		}));
 	}
 
-	private _isRelevantMarkdownDocument(doc: vscode.TextDocument) {
+	#isRelevantMarkdownDocument(doc: vscode.TextDocument) {
 		return isMarkdownFile(doc) && doc.uri.scheme !== 'vscode-bulkeditpreview';
 	}
 
 	public async getOrLoadMarkdownDocument(resource: vscode.Uri): Promise<ITextDocument | undefined> {
-		const existing = this._documentCache.get(resource);
+		const existing = this.#documentCache.get(resource);
 		if (existing) {
 			return existing;
 		}
 
-		const matchingDocument = vscode.workspace.textDocuments.find((doc) => this._isRelevantMarkdownDocument(doc) && doc.uri.toString() === resource.toString());
+		const matchingDocument = vscode.workspace.textDocuments.find((doc) => this.#isRelevantMarkdownDocument(doc) && doc.uri.toString() === resource.toString());
 		if (matchingDocument) {
-			this._documentCache.set(resource, matchingDocument);
+			this.#documentCache.set(resource, matchingDocument);
 			return matchingDocument;
 		}
 
@@ -69,9 +69,9 @@ export class VsCodeMdWorkspace extends Disposable {
 			const bytes = await vscode.workspace.fs.readFile(resource);
 
 			// We assume that markdown is in UTF-8
-			const text = this._utf8Decoder.decode(bytes);
+			const text = this.#utf8Decoder.decode(bytes);
 			const doc = new InMemoryDocument(resource, text, 0);
-			this._documentCache.set(resource, doc);
+			this.#documentCache.set(resource, doc);
 			return doc;
 		} catch {
 			return undefined;
diff --git a/extensions/markdown-language-features/src/commandManager.ts b/extensions/markdown-language-features/src/commandManager.ts
index ae2c4985066d0..0563db020c7df 100644
--- a/extensions/markdown-language-features/src/commandManager.ts
+++ b/extensions/markdown-language-features/src/commandManager.ts
@@ -12,27 +12,27 @@ export interface Command {
 }
 
 export class CommandManager {
-	private readonly _commands = new Map<string, vscode.Disposable>();
+	readonly #commands = new Map<string, vscode.Disposable>();
 
 	public dispose() {
-		for (const registration of this._commands.values()) {
+		for (const registration of this.#commands.values()) {
 			registration.dispose();
 		}
-		this._commands.clear();
+		this.#commands.clear();
 	}
 
 	public register<T extends Command>(command: T): vscode.Disposable {
-		this._registerCommand(command.id, command.execute, command);
+		this.#registerCommand(command.id, command.execute, command);
 		return new vscode.Disposable(() => {
-			this._commands.delete(command.id);
+			this.#commands.delete(command.id);
 		});
 	}
 
-	private _registerCommand(id: string, impl: (...args: any[]) => void, thisArg?: any) {
-		if (this._commands.has(id)) {
+	#registerCommand(id: string, impl: (...args: any[]) => void, thisArg?: any) {
+		if (this.#commands.has(id)) {
 			return;
 		}
 
-		this._commands.set(id, vscode.commands.registerCommand(id, impl, thisArg));
+		this.#commands.set(id, vscode.commands.registerCommand(id, impl, thisArg));
 	}
 }
diff --git a/extensions/markdown-language-features/src/commands/copyImage.ts b/extensions/markdown-language-features/src/commands/copyImage.ts
index 86fd349c730fa..09a683ecfb234 100644
--- a/extensions/markdown-language-features/src/commands/copyImage.ts
+++ b/extensions/markdown-language-features/src/commands/copyImage.ts
@@ -10,12 +10,16 @@ import { MarkdownPreviewManager } from '../preview/previewManager';
 export class CopyImageCommand implements Command {
 	public readonly id = '_markdown.copyImage';
 
+	readonly #webviewManager: MarkdownPreviewManager;
+
 	public constructor(
-		private readonly _webviewManager: MarkdownPreviewManager,
-	) { }
+		webviewManager: MarkdownPreviewManager,
+	) {
+		this.#webviewManager = webviewManager;
+	}
 
 	public execute(args: { id: string; resource: string }) {
 		const source = vscode.Uri.parse(args.resource);
-		this._webviewManager.findPreview(source)?.copyImage(args.id);
+		this.#webviewManager.findPreview(source)?.copyImage(args.id);
 	}
 }
diff --git a/extensions/markdown-language-features/src/commands/openImage.ts b/extensions/markdown-language-features/src/commands/openImage.ts
index 64b1831df0d98..4a121fd6989ca 100644
--- a/extensions/markdown-language-features/src/commands/openImage.ts
+++ b/extensions/markdown-language-features/src/commands/openImage.ts
@@ -10,12 +10,16 @@ import { MarkdownPreviewManager } from '../preview/previewManager';
 export class OpenImageCommand implements Command {
 	public readonly id = '_markdown.openImage';
 
+	readonly #webviewManager: MarkdownPreviewManager;
+
 	public constructor(
-		private readonly _webviewManager: MarkdownPreviewManager,
-	) { }
+		webviewManager: MarkdownPreviewManager,
+	) {
+		this.#webviewManager = webviewManager;
+	}
 
 	public execute(args: { resource: string; imageSource: string }) {
 		const source = vscode.Uri.parse(args.resource);
-		this._webviewManager.openDocumentLink(args.imageSource, source);
+		this.#webviewManager.openDocumentLink(args.imageSource, source);
 	}
 }
diff --git a/extensions/markdown-language-features/src/commands/refreshPreview.ts b/extensions/markdown-language-features/src/commands/refreshPreview.ts
index a94fa7974625e..52f320098b746 100644
--- a/extensions/markdown-language-features/src/commands/refreshPreview.ts
+++ b/extensions/markdown-language-features/src/commands/refreshPreview.ts
@@ -10,13 +10,19 @@ import { MarkdownPreviewManager } from '../preview/previewManager';
 export class RefreshPreviewCommand implements Command {
 	public readonly id = 'markdown.preview.refresh';
 
+	readonly #webviewManager: MarkdownPreviewManager;
+	readonly #engine: MarkdownItEngine;
+
 	public constructor(
-		private readonly _webviewManager: MarkdownPreviewManager,
-		private readonly _engine: MarkdownItEngine
-	) { }
+		webviewManager: MarkdownPreviewManager,
+		engine: MarkdownItEngine
+	) {
+		this.#webviewManager = webviewManager;
+		this.#engine = engine;
+	}
 
 	public execute() {
-		this._engine.cleanCache();
-		this._webviewManager.refresh();
+		this.#engine.cleanCache();
+		this.#webviewManager.refresh();
 	}
 }
diff --git a/extensions/markdown-language-features/src/commands/reloadPlugins.ts b/extensions/markdown-language-features/src/commands/reloadPlugins.ts
index 16be408bbef8d..5d410780a2bb5 100644
--- a/extensions/markdown-language-features/src/commands/reloadPlugins.ts
+++ b/extensions/markdown-language-features/src/commands/reloadPlugins.ts
@@ -10,14 +10,20 @@ import { MarkdownPreviewManager } from '../preview/previewManager';
 export class ReloadPlugins implements Command {
 	public readonly id = 'markdown.api.reloadPlugins';
 
+	readonly #webviewManager: MarkdownPreviewManager;
+	readonly #engine: MarkdownItEngine;
+
 	public constructor(
-		private readonly _webviewManager: MarkdownPreviewManager,
-		private readonly _engine: MarkdownItEngine,
-	) { }
+		webviewManager: MarkdownPreviewManager,
+		engine: MarkdownItEngine,
+	) {
+		this.#webviewManager = webviewManager;
+		this.#engine = engine;
+	}
 
 	public execute(): void {
-		this._engine.reloadPlugins();
-		this._engine.cleanCache();
-		this._webviewManager.refresh();
+		this.#engine.reloadPlugins();
+		this.#engine.cleanCache();
+		this.#webviewManager.refresh();
 	}
 }
diff --git a/extensions/markdown-language-features/src/commands/renderDocument.ts b/extensions/markdown-language-features/src/commands/renderDocument.ts
index ccefddedbd2ec..ffcbab6d41a62 100644
--- a/extensions/markdown-language-features/src/commands/renderDocument.ts
+++ b/extensions/markdown-language-features/src/commands/renderDocument.ts
@@ -10,11 +10,15 @@ import { ITextDocument } from '../types/textDocument';
 export class RenderDocument implements Command {
 	public readonly id = 'markdown.api.render';
 
+	readonly #engine: MarkdownItEngine;
+
 	public constructor(
-		private readonly _engine: MarkdownItEngine
-	) { }
+		engine: MarkdownItEngine
+	) {
+		this.#engine = engine;
+	}
 
 	public async execute(document: ITextDocument | string): Promise<string> {
-		return (await (this._engine.render(document))).html;
+		return (await (this.#engine.render(document))).html;
 	}
 }
diff --git a/extensions/markdown-language-features/src/commands/showPreview.ts b/extensions/markdown-language-features/src/commands/showPreview.ts
index d5d430ade0ee6..4d59062c1a117 100644
--- a/extensions/markdown-language-features/src/commands/showPreview.ts
+++ b/extensions/markdown-language-features/src/commands/showPreview.ts
@@ -53,14 +53,20 @@ async function showPreview(
 export class ShowPreviewCommand implements Command {
 	public readonly id = 'markdown.showPreview';
 
+	readonly #webviewManager: MarkdownPreviewManager;
+	readonly #telemetryReporter: TelemetryReporter;
+
 	public constructor(
-		private readonly _webviewManager: MarkdownPreviewManager,
-		private readonly _telemetryReporter: TelemetryReporter
-	) { }
+		webviewManager: MarkdownPreviewManager,
+		telemetryReporter: TelemetryReporter
+	) {
+		this.#webviewManager = webviewManager;
+		this.#telemetryReporter = telemetryReporter;
+	}
 
 	public execute(mainUri?: vscode.Uri, allUris?: vscode.Uri[], previewSettings?: DynamicPreviewSettings) {
 		for (const uri of Array.isArray(allUris) ? allUris : [mainUri]) {
-			showPreview(this._webviewManager, this._telemetryReporter, uri, {
+			showPreview(this.#webviewManager, this.#telemetryReporter, uri, {
 				sideBySide: false,
 				locked: previewSettings?.locked
 			});
@@ -71,13 +77,19 @@ export class ShowPreviewCommand implements Command {
 export class ShowPreviewToSideCommand implements Command {
 	public readonly id = 'markdown.showPreviewToSide';
 
+	readonly #webviewManager: MarkdownPreviewManager;
+	readonly #telemetryReporter: TelemetryReporter;
+
 	public constructor(
-		private readonly _webviewManager: MarkdownPreviewManager,
-		private readonly _telemetryReporter: TelemetryReporter
-	) { }
+		webviewManager: MarkdownPreviewManager,
+		telemetryReporter: TelemetryReporter
+	) {
+		this.#webviewManager = webviewManager;
+		this.#telemetryReporter = telemetryReporter;
+	}
 
 	public execute(uri?: vscode.Uri, previewSettings?: DynamicPreviewSettings) {
-		showPreview(this._webviewManager, this._telemetryReporter, uri, {
+		showPreview(this.#webviewManager, this.#telemetryReporter, uri, {
 			sideBySide: true,
 			locked: previewSettings?.locked
 		});
@@ -88,13 +100,19 @@ export class ShowPreviewToSideCommand implements Command {
 export class ShowLockedPreviewToSideCommand implements Command {
 	public readonly id = 'markdown.showLockedPreviewToSide';
 
+	readonly #webviewManager: MarkdownPreviewManager;
+	readonly #telemetryReporter: TelemetryReporter;
+
 	public constructor(
-		private readonly _webviewManager: MarkdownPreviewManager,
-		private readonly _telemetryReporter: TelemetryReporter
-	) { }
+		webviewManager: MarkdownPreviewManager,
+		telemetryReporter: TelemetryReporter
+	) {
+		this.#webviewManager = webviewManager;
+		this.#telemetryReporter = telemetryReporter;
+	}
 
 	public execute(uri?: vscode.Uri) {
-		showPreview(this._webviewManager, this._telemetryReporter, uri, {
+		showPreview(this.#webviewManager, this.#telemetryReporter, uri, {
 			sideBySide: true,
 			locked: true
 		});
diff --git a/extensions/markdown-language-features/src/commands/showPreviewSecuritySelector.ts b/extensions/markdown-language-features/src/commands/showPreviewSecuritySelector.ts
index 7ea5a4079ed40..fb6cd9ce9e729 100644
--- a/extensions/markdown-language-features/src/commands/showPreviewSecuritySelector.ts
+++ b/extensions/markdown-language-features/src/commands/showPreviewSecuritySelector.ts
@@ -12,19 +12,25 @@ import { isMarkdownFile } from '../util/file';
 export class ShowPreviewSecuritySelectorCommand implements Command {
 	public readonly id = 'markdown.showPreviewSecuritySelector';
 
+	readonly #previewSecuritySelector: PreviewSecuritySelector;
+	readonly #previewManager: MarkdownPreviewManager;
+
 	public constructor(
-		private readonly _previewSecuritySelector: PreviewSecuritySelector,
-		private readonly _previewManager: MarkdownPreviewManager
-	) { }
+		previewSecuritySelector: PreviewSecuritySelector,
+		previewManager: MarkdownPreviewManager
+	) {
+		this.#previewSecuritySelector = previewSecuritySelector;
+		this.#previewManager = previewManager;
+	}
 
 	public execute(resource: string | undefined) {
-		if (this._previewManager.activePreviewResource) {
-			this._previewSecuritySelector.showSecuritySelectorForResource(this._previewManager.activePreviewResource);
+		if (this.#previewManager.activePreviewResource) {
+			this.#previewSecuritySelector.showSecuritySelectorForResource(this.#previewManager.activePreviewResource);
 		} else if (resource) {
 			const source = vscode.Uri.parse(resource);
-			this._previewSecuritySelector.showSecuritySelectorForResource(source.query ? vscode.Uri.parse(source.query) : source);
+			this.#previewSecuritySelector.showSecuritySelectorForResource(source.query ? vscode.Uri.parse(source.query) : source);
 		} else if (vscode.window.activeTextEditor && isMarkdownFile(vscode.window.activeTextEditor.document)) {
-			this._previewSecuritySelector.showSecuritySelectorForResource(vscode.window.activeTextEditor.document.uri);
+			this.#previewSecuritySelector.showSecuritySelectorForResource(vscode.window.activeTextEditor.document.uri);
 		}
 	}
 }
diff --git a/extensions/markdown-language-features/src/commands/showSource.ts b/extensions/markdown-language-features/src/commands/showSource.ts
index 87d6b21ec68e7..3a6bb3e0e202b 100644
--- a/extensions/markdown-language-features/src/commands/showSource.ts
+++ b/extensions/markdown-language-features/src/commands/showSource.ts
@@ -10,12 +10,16 @@ import { MarkdownPreviewManager } from '../preview/previewManager';
 export class ShowSourceCommand implements Command {
 	public readonly id = 'markdown.showSource';
 
+	readonly #previewManager: MarkdownPreviewManager;
+
 	public constructor(
-		private readonly _previewManager: MarkdownPreviewManager
-	) { }
+		previewManager: MarkdownPreviewManager
+	) {
+		this.#previewManager = previewManager;
+	}
 
 	public execute() {
-		const { activePreviewResource, activePreviewResourceColumn } = this._previewManager;
+		const { activePreviewResource, activePreviewResourceColumn } = this.#previewManager;
 		if (activePreviewResource && activePreviewResourceColumn) {
 			return vscode.workspace.openTextDocument(activePreviewResource).then(document => {
 				return vscode.window.showTextDocument(document, activePreviewResourceColumn);
diff --git a/extensions/markdown-language-features/src/commands/toggleLock.ts b/extensions/markdown-language-features/src/commands/toggleLock.ts
index 9975d4872bbf2..0bc4656d08f7e 100644
--- a/extensions/markdown-language-features/src/commands/toggleLock.ts
+++ b/extensions/markdown-language-features/src/commands/toggleLock.ts
@@ -9,11 +9,15 @@ import { MarkdownPreviewManager } from '../preview/previewManager';
 export class ToggleLockCommand implements Command {
 	public readonly id = 'markdown.preview.toggleLock';
 
+	readonly #previewManager: MarkdownPreviewManager;
+
 	public constructor(
-		private readonly _previewManager: MarkdownPreviewManager
-	) { }
+		previewManager: MarkdownPreviewManager
+	) {
+		this.#previewManager = previewManager;
+	}
 
 	public execute() {
-		this._previewManager.toggleLock();
+		this.#previewManager.toggleLock();
 	}
 }
diff --git a/extensions/markdown-language-features/src/languageFeatures/copyFiles/dropOrPasteResource.ts b/extensions/markdown-language-features/src/languageFeatures/copyFiles/dropOrPasteResource.ts
index 7791d6b19e42f..e59a207487d8f 100644
--- a/extensions/markdown-language-features/src/languageFeatures/copyFiles/dropOrPasteResource.ts
+++ b/extensions/markdown-language-features/src/languageFeatures/copyFiles/dropOrPasteResource.ts
@@ -36,14 +36,18 @@ class ResourcePasteOrDropProvider implements vscode.DocumentPasteEditProvider, v
 		...Object.values(rootMediaMimesTypes).map(type => `${type}/*`),
 	];
 
-	private readonly _yieldTo = [
+	readonly #yieldTo = [
 		vscode.DocumentDropOrPasteEditKind.Text,
 		vscode.DocumentDropOrPasteEditKind.Empty.append('markdown', 'link', 'image', 'attachment'), // Prefer notebook attachments
 	];
 
+	readonly #parser: IMdParser;
+
 	constructor(
-		private readonly _parser: IMdParser,
-	) { }
+		parser: IMdParser,
+	) {
+		this.#parser = parser;
+	}
 
 	public async provideDocumentDropEdits(
 		document: vscode.TextDocument,
@@ -51,8 +55,8 @@ class ResourcePasteOrDropProvider implements vscode.DocumentPasteEditProvider, v
 		dataTransfer: vscode.DataTransfer,
 		token: vscode.CancellationToken,
 	): Promise<vscode.DocumentDropEdit | undefined> {
-		const edit = await this._createEdit(document, [new vscode.Range(position, position)], dataTransfer, {
-			insert: this._getEnabled(document, 'editor.drop.enabled'),
+		const edit = await this.#createEdit(document, [new vscode.Range(position, position)], dataTransfer, {
+			insert: this.#getEnabled(document, 'editor.drop.enabled'),
 			copyIntoWorkspace: vscode.workspace.getConfiguration('markdown', document).get<CopyFilesSettings>('editor.drop.copyIntoWorkspace', CopyFilesSettings.MediaFiles)
 		}, undefined, token);
 
@@ -64,7 +68,7 @@ class ResourcePasteOrDropProvider implements vscode.DocumentPasteEditProvider, v
 		dropEdit.title = edit.label;
 		dropEdit.kind = edit.kind;
 		dropEdit.additionalEdit = edit.additionalEdits;
-		dropEdit.yieldTo = [...this._yieldTo, ...edit.yieldTo];
+		dropEdit.yieldTo = [...this.#yieldTo, ...edit.yieldTo];
 		return dropEdit;
 	}
 
@@ -75,8 +79,8 @@ class ResourcePasteOrDropProvider implements vscode.DocumentPasteEditProvider, v
 		context: vscode.DocumentPasteEditContext,
 		token: vscode.CancellationToken,
 	): Promise<vscode.DocumentPasteEdit[] | undefined> {
-		const edit = await this._createEdit(document, ranges, dataTransfer, {
-			insert: this._getEnabled(document, 'editor.paste.enabled'),
+		const edit = await this.#createEdit(document, ranges, dataTransfer, {
+			insert: this.#getEnabled(document, 'editor.paste.enabled'),
 			copyIntoWorkspace: vscode.workspace.getConfiguration('markdown', document).get<CopyFilesSettings>('editor.paste.copyIntoWorkspace', CopyFilesSettings.MediaFiles)
 		}, context, token);
 
@@ -86,11 +90,11 @@ class ResourcePasteOrDropProvider implements vscode.DocumentPasteEditProvider, v
 
 		const pasteEdit = new vscode.DocumentPasteEdit(edit.snippet, edit.label, edit.kind);
 		pasteEdit.additionalEdit = edit.additionalEdits;
-		pasteEdit.yieldTo = [...this._yieldTo, ...edit.yieldTo];
+		pasteEdit.yieldTo = [...this.#yieldTo, ...edit.yieldTo];
 		return [pasteEdit];
 	}
 
-	private _getEnabled(document: vscode.TextDocument, settingName: string): InsertMarkdownLink {
+	#getEnabled(document: vscode.TextDocument, settingName: string): InsertMarkdownLink {
 		const setting = vscode.workspace.getConfiguration('markdown', document).get<boolean | InsertMarkdownLink>(settingName, true);
 		// Convert old boolean values to new enum setting
 		if (setting === false) {
@@ -102,7 +106,7 @@ class ResourcePasteOrDropProvider implements vscode.DocumentPasteEditProvider, v
 		}
 	}
 
-	private async _createEdit(
+	async #createEdit(
 		document: vscode.TextDocument,
 		ranges: readonly vscode.Range[],
 		dataTransfer: vscode.DataTransfer,
@@ -117,27 +121,27 @@ class ResourcePasteOrDropProvider implements vscode.DocumentPasteEditProvider, v
 			return;
 		}
 
-		let edit = await this._createEditForMediaFiles(document, dataTransfer, settings.copyIntoWorkspace, token);
+		let edit = await this.#createEditForMediaFiles(document, dataTransfer, settings.copyIntoWorkspace, token);
 		if (token.isCancellationRequested) {
 			return;
 		}
 
 		if (!edit) {
-			edit = await this._createEditFromUriListData(document, ranges, dataTransfer, context, token);
+			edit = await this.#createEditFromUriListData(document, ranges, dataTransfer, context, token);
 		}
 
 		if (!edit || token.isCancellationRequested) {
 			return;
 		}
 
-		if (!(await shouldInsertMarkdownLinkByDefault(this._parser, document, settings.insert, ranges, token))) {
+		if (!(await shouldInsertMarkdownLinkByDefault(this.#parser, document, settings.insert, ranges, token))) {
 			edit.yieldTo.push(vscode.DocumentDropOrPasteEditKind.Empty.append('uri'));
 		}
 
 		return edit;
 	}
 
-	private async _createEditFromUriListData(
+	async #createEditFromUriListData(
 		document: vscode.TextDocument,
 		ranges: readonly vscode.Range[],
 		dataTransfer: vscode.DataTransfer,
@@ -194,7 +198,7 @@ class ResourcePasteOrDropProvider implements vscode.DocumentPasteEditProvider, v
 	 *
 	 * This tries copying files outside of the workspace into the workspace.
 	 */
-	private async _createEditForMediaFiles(
+	async #createEditForMediaFiles(
 		document: vscode.TextDocument,
 		dataTransfer: vscode.DataTransfer,
 		copyIntoWorkspace: CopyFilesSettings,
diff --git a/extensions/markdown-language-features/src/languageFeatures/copyFiles/newFilePathGenerator.ts b/extensions/markdown-language-features/src/languageFeatures/copyFiles/newFilePathGenerator.ts
index 1625977a72cb8..fe9030704c117 100644
--- a/extensions/markdown-language-features/src/languageFeatures/copyFiles/newFilePathGenerator.ts
+++ b/extensions/markdown-language-features/src/languageFeatures/copyFiles/newFilePathGenerator.ts
@@ -12,7 +12,7 @@ import { CopyFileConfiguration, getCopyFileConfiguration, parseGlob, resolveCopy
 
 export class NewFilePathGenerator {
 
-	private readonly _usedPaths = new Set<string>();
+	readonly #usedPaths = new Set<string>();
 
 	async getNewFilePath(
 		document: vscode.TextDocument,
@@ -33,13 +33,13 @@ export class NewFilePathGenerator {
 
 			const name = i === 0 ? baseName : `${baseName}-${i}`;
 			const uri = vscode.Uri.joinPath(root, name + ext);
-			if (this._wasPathAlreadyUsed(uri)) {
+			if (this.#wasPathAlreadyUsed(uri)) {
 				continue;
 			}
 
 			// Try overwriting if it already exists
 			if (config.overwriteBehavior === 'overwrite') {
-				this._usedPaths.add(uri.toString());
+				this.#usedPaths.add(uri.toString());
 				return { uri, overwrite: true };
 			}
 
@@ -47,17 +47,17 @@ export class NewFilePathGenerator {
 			try {
 				await vscode.workspace.fs.stat(uri);
 			} catch {
-				if (!this._wasPathAlreadyUsed(uri)) {
+				if (!this.#wasPathAlreadyUsed(uri)) {
 					// Does not exist
-					this._usedPaths.add(uri.toString());
+					this.#usedPaths.add(uri.toString());
 					return { uri, overwrite: false };
 				}
 			}
 		}
 	}
 
-	private _wasPathAlreadyUsed(uri: vscode.Uri) {
-		return this._usedPaths.has(uri.toString());
+	#wasPathAlreadyUsed(uri: vscode.Uri) {
+		return this.#usedPaths.has(uri.toString());
 	}
 }
 
diff --git a/extensions/markdown-language-features/src/languageFeatures/copyFiles/pasteUrlProvider.ts b/extensions/markdown-language-features/src/languageFeatures/copyFiles/pasteUrlProvider.ts
index a947216fe3272..faad54e10c342 100644
--- a/extensions/markdown-language-features/src/languageFeatures/copyFiles/pasteUrlProvider.ts
+++ b/extensions/markdown-language-features/src/languageFeatures/copyFiles/pasteUrlProvider.ts
@@ -21,9 +21,13 @@ class PasteUrlEditProvider implements vscode.DocumentPasteEditProvider {
 
 	public static readonly pasteMimeTypes = [Mime.textPlain];
 
+	readonly #parser: IMdParser;
+
 	constructor(
-		private readonly _parser: IMdParser,
-	) { }
+		parser: IMdParser,
+	) {
+		this.#parser = parser;
+	}
 
 	async provideDocumentPasteEdits(
 		document: vscode.TextDocument,
@@ -64,7 +68,7 @@ class PasteUrlEditProvider implements vscode.DocumentPasteEditProvider {
 		workspaceEdit.set(document.uri, edit.edits);
 		pasteEdit.additionalEdit = workspaceEdit;
 
-		if (!(await shouldInsertMarkdownLinkByDefault(this._parser, document, pasteUrlSetting, ranges, token))) {
+		if (!(await shouldInsertMarkdownLinkByDefault(this.#parser, document, pasteUrlSetting, ranges, token))) {
 			pasteEdit.yieldTo = [
 				vscode.DocumentDropOrPasteEditKind.Text,
 				vscode.DocumentDropOrPasteEditKind.Empty.append('uri')
diff --git a/extensions/markdown-language-features/src/languageFeatures/diagnostics.ts b/extensions/markdown-language-features/src/languageFeatures/diagnostics.ts
index 8df16f4dcc6f7..871333cf4a422 100644
--- a/extensions/markdown-language-features/src/languageFeatures/diagnostics.ts
+++ b/extensions/markdown-language-features/src/languageFeatures/diagnostics.ts
@@ -19,18 +19,18 @@ export enum DiagnosticCode {
 
 class AddToIgnoreLinksQuickFixProvider implements vscode.CodeActionProvider {
 
-	private static readonly _addToIgnoreLinksCommandId = '_markdown.addToIgnoreLinks';
+	static readonly #addToIgnoreLinksCommandId = '_markdown.addToIgnoreLinks';
 
-	private static readonly _metadata: vscode.CodeActionProviderMetadata = {
+	static readonly #metadata: vscode.CodeActionProviderMetadata = {
 		providedCodeActionKinds: [
 			vscode.CodeActionKind.QuickFix
 		],
 	};
 
 	public static register(selector: vscode.DocumentSelector, commandManager: CommandManager): vscode.Disposable {
-		const reg = vscode.languages.registerCodeActionsProvider(selector, new AddToIgnoreLinksQuickFixProvider(), AddToIgnoreLinksQuickFixProvider._metadata);
+		const reg = vscode.languages.registerCodeActionsProvider(selector, new AddToIgnoreLinksQuickFixProvider(), AddToIgnoreLinksQuickFixProvider.#metadata);
 		const commandReg = commandManager.register({
-			id: AddToIgnoreLinksQuickFixProvider._addToIgnoreLinksCommandId,
+			id: AddToIgnoreLinksQuickFixProvider.#addToIgnoreLinksCommandId,
 			execute(resource: vscode.Uri, path: string) {
 				const settingId = 'validate.ignoredLinks';
 				const config = vscode.workspace.getConfiguration('markdown', resource);
@@ -58,7 +58,7 @@ class AddToIgnoreLinksQuickFixProvider implements vscode.CodeActionProvider {
 							vscode.CodeActionKind.QuickFix);
 
 						fix.command = {
-							command: AddToIgnoreLinksQuickFixProvider._addToIgnoreLinksCommandId,
+							command: AddToIgnoreLinksQuickFixProvider.#addToIgnoreLinksCommandId,
 							title: '',
 							arguments: [document.uri, hrefText],
 						};
diff --git a/extensions/markdown-language-features/src/languageFeatures/fileReferences.ts b/extensions/markdown-language-features/src/languageFeatures/fileReferences.ts
index bda8b721e8bca..23a2ed9e7703a 100644
--- a/extensions/markdown-language-features/src/languageFeatures/fileReferences.ts
+++ b/extensions/markdown-language-features/src/languageFeatures/fileReferences.ts
@@ -13,9 +13,13 @@ export class FindFileReferencesCommand implements Command {
 
 	public readonly id = 'markdown.findAllFileReferences';
 
+	readonly #client: MdLanguageClient;
+
 	constructor(
-		private readonly _client: MdLanguageClient,
-	) { }
+		client: MdLanguageClient,
+	) {
+		this.#client = client;
+	}
 
 	public async execute(resource?: vscode.Uri) {
 		resource ??= vscode.window.activeTextEditor?.document.uri;
@@ -28,7 +32,7 @@ export class FindFileReferencesCommand implements Command {
 			location: vscode.ProgressLocation.Window,
 			title: vscode.l10n.t("Finding file references")
 		}, async (_progress, token) => {
-			const locations = (await this._client.getReferencesToFileInWorkspace(resource, token)).map(loc => {
+			const locations = (await this.#client.getReferencesToFileInWorkspace(resource, token)).map(loc => {
 				return new vscode.Location(vscode.Uri.parse(loc.uri), convertRange(loc.range));
 			});
 
diff --git a/extensions/markdown-language-features/src/languageFeatures/linkUpdater.ts b/extensions/markdown-language-features/src/languageFeatures/linkUpdater.ts
index 5d42a033842c0..d912caa906009 100644
--- a/extensions/markdown-language-features/src/languageFeatures/linkUpdater.ts
+++ b/extensions/markdown-language-features/src/languageFeatures/linkUpdater.ts
@@ -33,46 +33,48 @@ interface RenameAction {
 
 class UpdateLinksOnFileRenameHandler extends Disposable {
 
-	private readonly _delayer = new Delayer(50);
-	private readonly _pendingRenames = new Set<RenameAction>();
+	readonly #delayer = new Delayer(50);
+	readonly #pendingRenames = new Set<RenameAction>();
+	readonly #client: MdLanguageClient;
 
 	public constructor(
-		private readonly _client: MdLanguageClient,
+		client: MdLanguageClient,
 	) {
 		super();
+		this.#client = client;
 
 		this._register(vscode.workspace.onDidRenameFiles(async (e) => {
 			await Promise.all(e.files.map(async (rename) => {
-				if (await this._shouldParticipateInLinkUpdate(rename.newUri)) {
-					this._pendingRenames.add(rename);
+				if (await this.#shouldParticipateInLinkUpdate(rename.newUri)) {
+					this.#pendingRenames.add(rename);
 				}
 			}));
 
-			if (this._pendingRenames.size) {
-				this._delayer.trigger(() => {
+			if (this.#pendingRenames.size) {
+				this.#delayer.trigger(() => {
 					vscode.window.withProgress({
 						location: vscode.ProgressLocation.Window,
 						title: vscode.l10n.t("Checking for Markdown links to update")
-					}, () => this._flushRenames());
+					}, () => this.#flushRenames());
 				});
 			}
 		}));
 	}
 
-	private async _flushRenames(): Promise<void> {
-		const renames = Array.from(this._pendingRenames);
-		this._pendingRenames.clear();
+	async #flushRenames(): Promise<void> {
+		const renames = Array.from(this.#pendingRenames);
+		this.#pendingRenames.clear();
 
-		const result = await this._getEditsForFileRename(renames, noopToken);
+		const result = await this.#getEditsForFileRename(renames, noopToken);
 
 		if (result?.edit.size) {
-			if (await this._confirmActionWithUser(result.resourcesBeingRenamed)) {
+			if (await this.#confirmActionWithUser(result.resourcesBeingRenamed)) {
 				await vscode.workspace.applyEdit(result.edit);
 			}
 		}
 	}
 
-	private async _confirmActionWithUser(newResources: readonly vscode.Uri[]): Promise<boolean> {
+	async #confirmActionWithUser(newResources: readonly vscode.Uri[]): Promise<boolean> {
 		if (!newResources.length) {
 			return false;
 		}
@@ -81,7 +83,7 @@ class UpdateLinksOnFileRenameHandler extends Disposable {
 		const setting = config.get<UpdateLinksOnFileMoveSetting>(settingNames.enabled);
 		switch (setting) {
 			case UpdateLinksOnFileMoveSetting.Prompt:
-				return this._promptUser(newResources);
+				return this.#promptUser(newResources);
 			case UpdateLinksOnFileMoveSetting.Always:
 				return true;
 			case UpdateLinksOnFileMoveSetting.Never:
@@ -89,7 +91,7 @@ class UpdateLinksOnFileRenameHandler extends Disposable {
 				return false;
 		}
 	}
-	private async _shouldParticipateInLinkUpdate(newUri: vscode.Uri): Promise<boolean> {
+	async #shouldParticipateInLinkUpdate(newUri: vscode.Uri): Promise<boolean> {
 		const config = vscode.workspace.getConfiguration('markdown', newUri);
 		const setting = config.get<UpdateLinksOnFileMoveSetting>(settingNames.enabled);
 		if (setting === UpdateLinksOnFileMoveSetting.Never) {
@@ -113,7 +115,7 @@ class UpdateLinksOnFileRenameHandler extends Disposable {
 		return false;
 	}
 
-	private async _promptUser(newResources: readonly vscode.Uri[]): Promise<boolean> {
+	async #promptUser(newResources: readonly vscode.Uri[]): Promise<boolean> {
 		if (!newResources.length) {
 			return false;
 		}
@@ -138,7 +140,7 @@ class UpdateLinksOnFileRenameHandler extends Disposable {
 		const choice = await vscode.window.showInformationMessage(
 			newResources.length === 1
 				? vscode.l10n.t("Update Markdown links for '{0}'?", Utils.basename(newResources[0]))
-				: this._getConfirmMessage(vscode.l10n.t("Update Markdown links for the following {0} files?", newResources.length), newResources), {
+				: this.#getConfirmMessage(vscode.l10n.t("Update Markdown links for the following {0} files?", newResources.length), newResources), {
 			modal: true,
 		}, rejectItem, acceptItem, alwaysItem, neverItem);
 
@@ -154,7 +156,7 @@ class UpdateLinksOnFileRenameHandler extends Disposable {
 				config.update(
 					settingNames.enabled,
 					UpdateLinksOnFileMoveSetting.Always,
-					this._getConfigTargetScope(config, settingNames.enabled));
+					this.#getConfigTargetScope(config, settingNames.enabled));
 				return true;
 			}
 			case neverItem: {
@@ -162,7 +164,7 @@ class UpdateLinksOnFileRenameHandler extends Disposable {
 				config.update(
 					settingNames.enabled,
 					UpdateLinksOnFileMoveSetting.Never,
-					this._getConfigTargetScope(config, settingNames.enabled));
+					this.#getConfigTargetScope(config, settingNames.enabled));
 				return false;
 			}
 			default: {
@@ -171,8 +173,8 @@ class UpdateLinksOnFileRenameHandler extends Disposable {
 		}
 	}
 
-	private async _getEditsForFileRename(renames: readonly RenameAction[], token: vscode.CancellationToken): Promise<{ edit: vscode.WorkspaceEdit; resourcesBeingRenamed: vscode.Uri[] } | undefined> {
-		const result = await this._client.getEditForFileRenames(renames.map(rename => ({ oldUri: rename.oldUri.toString(), newUri: rename.newUri.toString() })), token);
+	async #getEditsForFileRename(renames: readonly RenameAction[], token: vscode.CancellationToken): Promise<{ edit: vscode.WorkspaceEdit; resourcesBeingRenamed: vscode.Uri[] } | undefined> {
+		const result = await this.#client.getEditForFileRenames(renames.map(rename => ({ oldUri: rename.oldUri.toString(), newUri: rename.newUri.toString() })), token);
 		if (!result?.edit.documentChanges?.length) {
 			return undefined;
 		}
@@ -192,7 +194,7 @@ class UpdateLinksOnFileRenameHandler extends Disposable {
 		};
 	}
 
-	private _getConfirmMessage(start: string, resourcesToConfirm: readonly vscode.Uri[]): string {
+	#getConfirmMessage(start: string, resourcesToConfirm: readonly vscode.Uri[]): string {
 		const MAX_CONFIRM_FILES = 10;
 
 		const paths = [start];
@@ -211,7 +213,7 @@ class UpdateLinksOnFileRenameHandler extends Disposable {
 		return paths.join('\n');
 	}
 
-	private _getConfigTargetScope(config: vscode.WorkspaceConfiguration, settingsName: string): vscode.ConfigurationTarget {
+	#getConfigTargetScope(config: vscode.WorkspaceConfiguration, settingsName: string): vscode.ConfigurationTarget {
 		const inspected = config.inspect(settingsName);
 		if (inspected?.workspaceFolderValue) {
 			return vscode.ConfigurationTarget.WorkspaceFolder;
diff --git a/extensions/markdown-language-features/src/languageFeatures/updateLinksOnPaste.ts b/extensions/markdown-language-features/src/languageFeatures/updateLinksOnPaste.ts
index f8a7128eb05fe..b27a869db0edc 100644
--- a/extensions/markdown-language-features/src/languageFeatures/updateLinksOnPaste.ts
+++ b/extensions/markdown-language-features/src/languageFeatures/updateLinksOnPaste.ts
@@ -13,16 +13,20 @@ class UpdatePastedLinksEditProvider implements vscode.DocumentPasteEditProvider
 
 	public static readonly metadataMime = 'application/vnd.vscode.markdown.updatelinks.metadata';
 
+	readonly #client: MdLanguageClient;
+
 	constructor(
-		private readonly _client: MdLanguageClient,
-	) { }
+		client: MdLanguageClient,
+	) {
+		this.#client = client;
+	}
 
 	async prepareDocumentPaste(document: vscode.TextDocument, ranges: readonly vscode.Range[], dataTransfer: vscode.DataTransfer, token: vscode.CancellationToken): Promise<void> {
-		if (!this._isEnabled(document)) {
+		if (!this.#isEnabled(document)) {
 			return;
 		}
 
-		const metadata = await this._client.prepareUpdatePastedLinks(document.uri, ranges, token);
+		const metadata = await this.#client.prepareUpdatePastedLinks(document.uri, ranges, token);
 		if (token.isCancellationRequested) {
 			return;
 		}
@@ -37,7 +41,7 @@ class UpdatePastedLinksEditProvider implements vscode.DocumentPasteEditProvider
 		context: vscode.DocumentPasteEditContext,
 		token: vscode.CancellationToken,
 	): Promise<vscode.DocumentPasteEdit[] | undefined> {
-		if (!this._isEnabled(document)) {
+		if (!this.#isEnabled(document)) {
 			return;
 		}
 
@@ -56,7 +60,7 @@ class UpdatePastedLinksEditProvider implements vscode.DocumentPasteEditProvider
 		// - copy empty line
 		// - Copy with multiple cursors and paste into multiple locations
 		// - ...
-		const edits = await this._client.getUpdatePastedLinksEdit(document.uri, ranges.map(x => new vscode.TextEdit(x, text)), metadata, token);
+		const edits = await this.#client.getUpdatePastedLinksEdit(document.uri, ranges.map(x => new vscode.TextEdit(x, text)), metadata, token);
 		if (!edits?.length || token.isCancellationRequested) {
 			return;
 		}
@@ -73,7 +77,7 @@ class UpdatePastedLinksEditProvider implements vscode.DocumentPasteEditProvider
 		return [pasteEdit];
 	}
 
-	private _isEnabled(document: vscode.TextDocument): boolean {
+	#isEnabled(document: vscode.TextDocument): boolean {
 		return vscode.workspace.getConfiguration('markdown', document.uri).get<boolean>('editor.updateLinksOnPaste.enabled', true);
 	}
 }
diff --git a/extensions/markdown-language-features/src/logging.ts b/extensions/markdown-language-features/src/logging.ts
index b5ea76f360816..30839d8c756c1 100644
--- a/extensions/markdown-language-features/src/logging.ts
+++ b/extensions/markdown-language-features/src/logging.ts
@@ -12,11 +12,11 @@ export interface ILogger {
 }
 
 export class VsCodeOutputLogger extends Disposable implements ILogger {
-	private _outputChannelValue?: vscode.LogOutputChannel;
+	#outputChannelValue?: vscode.LogOutputChannel;
 
-	private get _outputChannel() {
-		this._outputChannelValue ??= this._register(vscode.window.createOutputChannel('Markdown', { log: true }));
-		return this._outputChannelValue;
+	get #outputChannel() {
+		this.#outputChannelValue ??= this._register(vscode.window.createOutputChannel('Markdown', { log: true }));
+		return this.#outputChannelValue;
 	}
 
 	constructor() {
@@ -24,6 +24,6 @@ export class VsCodeOutputLogger extends Disposable implements ILogger {
 	}
 
 	public trace(title: string, message: string, data?: any): void {
-		this._outputChannel.trace(`${title}: ${message}`, ...(data ? [JSON.stringify(data, null, 4)] : []));
+		this.#outputChannel.trace(`${title}: ${message}`, ...(data ? [JSON.stringify(data, null, 4)] : []));
 	}
 }
diff --git a/extensions/markdown-language-features/src/markdownEngine.ts b/extensions/markdown-language-features/src/markdownEngine.ts
index 0f4c7eb671792..4ed3186c3807d 100644
--- a/extensions/markdown-language-features/src/markdownEngine.ts
+++ b/extensions/markdown-language-features/src/markdownEngine.ts
@@ -44,37 +44,37 @@ const pluginSourceMap: MarkdownIt.PluginSimple = (md): void => {
 type MarkdownItConfig = Readonly<Required<Pick<MarkdownIt.Options, 'breaks' | 'linkify' | 'typographer'>>>;
 
 class TokenCache {
-	private _cachedDocument?: {
+	#cachedDocument?: {
 		readonly uri: vscode.Uri;
 		readonly version: number;
 		readonly config: MarkdownItConfig;
 	};
-	private _tokens?: MarkdownIt.Token[];
+	#tokens?: MarkdownIt.Token[];
 
 	public tryGetCached(document: ITextDocument, config: MarkdownItConfig): MarkdownIt.Token[] | undefined {
-		if (this._cachedDocument
-			&& this._cachedDocument.uri.toString() === document.uri.toString()
-			&& document.version >= 0 && this._cachedDocument.version === document.version
-			&& this._cachedDocument.config.breaks === config.breaks
-			&& this._cachedDocument.config.linkify === config.linkify
+		if (this.#cachedDocument
+			&& this.#cachedDocument.uri.toString() === document.uri.toString()
+			&& document.version >= 0 && this.#cachedDocument.version === document.version
+			&& this.#cachedDocument.config.breaks === config.breaks
+			&& this.#cachedDocument.config.linkify === config.linkify
 		) {
-			return this._tokens;
+			return this.#tokens;
 		}
 		return undefined;
 	}
 
 	public update(document: ITextDocument, config: MarkdownItConfig, tokens: MarkdownIt.Token[]) {
-		this._cachedDocument = {
+		this.#cachedDocument = {
 			uri: document.uri,
 			version: document.version,
 			config,
 		};
-		this._tokens = tokens;
+		this.#tokens = tokens;
 	}
 
 	public clean(): void {
-		this._cachedDocument = undefined;
-		this._tokens = undefined;
+		this.#cachedDocument = undefined;
+		this.#tokens = undefined;
 	}
 }
 
@@ -98,40 +98,45 @@ export interface IMdParser {
 
 export class MarkdownItEngine implements IMdParser {
 
-	private _md?: Promise<MarkdownIt>;
+	#md?: Promise<MarkdownIt>;
 
-	private readonly _tokenCache = new TokenCache();
+	readonly #tokenCache = new TokenCache();
 
 	public readonly slugifier: ISlugifier;
 
+	readonly #contributionProvider: MarkdownContributionProvider;
+	readonly #logger: ILogger;
+
 	public constructor(
-		private readonly _contributionProvider: MarkdownContributionProvider,
+		contributionProvider: MarkdownContributionProvider,
 		slugifier: ISlugifier,
-		private readonly _logger: ILogger,
+		logger: ILogger,
 	) {
+		this.#contributionProvider = contributionProvider;
 		this.slugifier = slugifier;
+		this.#logger = logger;
 
-		_contributionProvider.onContributionsChanged(() => {
+		contributionProvider.onContributionsChanged(() => {
 			// Markdown plugin contributions may have changed
-			this._md = undefined;
-			this._tokenCache.clean();
+			this.#md = undefined;
+			this.#tokenCache.clean();
 		});
 	}
 
 
 	public async getEngine(resource: vscode.Uri | undefined): Promise<MarkdownIt> {
-		const config = this._getConfig(resource);
-		return this._getEngine(config);
+		const config = this.#getConfig(resource);
+		return this.#getEngine(config);
 	}
 
-	private async _getEngine(config: MarkdownItConfig): Promise<MarkdownIt> {
-		if (!this._md) {
-			this._md = (async () => {
+	async #getEngine(config: MarkdownItConfig): Promise<MarkdownIt> {
+		if (!this.#md) {
+			this.#md = (async () => {
 				const markdownIt = await import('markdown-it');
 				let md: MarkdownIt = markdownIt.default(await getMarkdownOptions(() => md));
 				md.linkify.set({ fuzzyLink: false });
 
-				for (const plugin of this._contributionProvider.contributions.markdownItPlugins.values()) {
+				for (const plugin of this.#contributionProvider.contributions.markdownItPlugins.values()) {
 					try {
 						md = (await plugin)(md);
 					} catch (e) {
@@ -154,43 +159,43 @@ export class MarkdownItEngine implements IMdParser {
 					alt: ['paragraph', 'reference', 'blockquote', 'list']
 				});
 
-				this._addImageRenderer(md);
-				this._addFencedRenderer(md);
-				this._addLinkNormalizer(md);
-				this._addLinkValidator(md);
-				this._addNamedHeaders(md);
-				this._addLinkRenderer(md);
+				this.#addImageRenderer(md);
+				this.#addFencedRenderer(md);
+				this.#addLinkNormalizer(md);
+				this.#addLinkValidator(md);
+				this.#addNamedHeaders(md);
+				this.#addLinkRenderer(md);
 				md.use(pluginSourceMap);
 				return md;
 			})();
 		}
 
-		const md = await this._md!;
+		const md = await this.#md!;
 		md.set(config);
 		return md;
 	}
 
 	public reloadPlugins() {
-		this._md = undefined;
+		this.#md = undefined;
 	}
 
-	private _tokenizeDocument(
+	#tokenizeDocument(
 		document: ITextDocument,
 		config: MarkdownItConfig,
 		engine: MarkdownIt
 	): MarkdownIt.Token[] {
-		const cached = this._tokenCache.tryGetCached(document, config);
+		const cached = this.#tokenCache.tryGetCached(document, config);
 		if (cached) {
 			return cached;
 		}
 
-		this._logger.trace('MarkdownItEngine', `tokenizeDocument - ${document.uri}`);
-		const tokens = this._tokenizeString(document.getText(), engine);
-		this._tokenCache.update(document, config, tokens);
+		this.#logger.trace('MarkdownItEngine', `tokenizeDocument - ${document.uri}`);
+		const tokens = this.#tokenizeString(document.getText(), engine);
+		this.#tokenCache.update(document, config, tokens);
 		return tokens;
 	}
 
-	private _tokenizeString(text: string, engine: MarkdownIt) {
+	#tokenizeString(text: string, engine: MarkdownIt) {
 		const env: RenderEnv = {
 			currentDocument: undefined,
 			containingImages: new Set<string>(),
@@ -201,12 +206,12 @@ export class MarkdownItEngine implements IMdParser {
 	}
 
 	public async render(input: ITextDocument | string, resourceProvider?: WebviewResourceProvider): Promise<RenderOutput> {
-		const config = this._getConfig(typeof input === 'string' ? undefined : input.uri);
-		const engine = await this._getEngine(config);
+		const config = this.#getConfig(typeof input === 'string' ? undefined : input.uri);
+		const engine = await this.#getEngine(config);
 
 		const tokens = typeof input === 'string'
-			? this._tokenizeString(input, engine)
-			: this._tokenizeDocument(input, config, engine);
+			? this.#tokenizeString(input, engine)
+			: this.#tokenizeDocument(input, config, engine);
 
 		const env: RenderEnv = {
 			containingImages: new Set<string>(),
@@ -227,16 +232,16 @@ export class MarkdownItEngine implements IMdParser {
 	}
 
 	public async tokenize(document: ITextDocument): Promise<MarkdownIt.Token[]> {
-		const config = this._getConfig(document.uri);
-		const engine = await this._getEngine(config);
-		return this._tokenizeDocument(document, config, engine);
+		const config = this.#getConfig(document.uri);
+		const engine = await this.#getEngine(config);
+		return this.#tokenizeDocument(document, config, engine);
 	}
 
 	public cleanCache(): void {
-		this._tokenCache.clean();
+		this.#tokenCache.clean();
 	}
 
-	private _getConfig(resource?: vscode.Uri): MarkdownItConfig {
+	#getConfig(resource?: vscode.Uri): MarkdownItConfig {
 		const config = MarkdownPreviewConfiguration.getForResource(resource ?? null);
 		return {
 			breaks: config.previewLineBreaks,
@@ -245,7 +250,7 @@ export class MarkdownItEngine implements IMdParser {
 		};
 	}
 
-	private _addImageRenderer(md: MarkdownIt): void {
+	#addImageRenderer(md: MarkdownIt): void {
 		const original = md.renderer.rules.image;
 		md.renderer.rules.image = (tokens: MarkdownIt.Token[], idx: number, options, env: RenderEnv, self) => {
 			const token = tokens[idx];
@@ -254,7 +259,7 @@ export class MarkdownItEngine implements IMdParser {
 				env.containingImages?.add(src);
 
 				if (!token.attrGet('data-src')) {
-					token.attrSet('src', this._toResourceUri(src, env.currentDocument, env.resourceProvider));
+					token.attrSet('src', this.#toResourceUri(src, env.currentDocument, env.resourceProvider));
 					token.attrSet('data-src', src);
 				}
 			}
@@ -267,7 +272,7 @@ export class MarkdownItEngine implements IMdParser {
 		};
 	}
 
-	private _addFencedRenderer(md: MarkdownIt): void {
+	#addFencedRenderer(md: MarkdownIt): void {
 		const original = md.renderer.rules['fenced'];
 		md.renderer.rules['fenced'] = (tokens: MarkdownIt.Token[], idx: number, options, env, self) => {
 			const token = tokens[idx];
@@ -283,7 +288,7 @@ export class MarkdownItEngine implements IMdParser {
 		};
 	}
 
-	private _addLinkNormalizer(md: MarkdownIt): void {
+	#addLinkNormalizer(md: MarkdownIt): void {
 		const normalizeLink = md.normalizeLink;
 		md.normalizeLink = (link: string) => {
 			try {
@@ -299,7 +304,7 @@ export class MarkdownItEngine implements IMdParser {
 		};
 	}
 
-	private _addLinkValidator(md: MarkdownIt): void {
+	#addLinkValidator(md: MarkdownIt): void {
 		const validateLink = md.validateLink;
 		md.validateLink = (link: string) => {
 			return validateLink(link)
@@ -309,10 +314,10 @@ export class MarkdownItEngine implements IMdParser {
 		};
 	}
 
-	private _addNamedHeaders(md: MarkdownIt): void {
+	#addNamedHeaders(md: MarkdownIt): void {
 		const original = md.renderer.rules.heading_open;
 		md.renderer.rules.heading_open = (tokens: MarkdownIt.Token[], idx: number, options, env: unknown, self) => {
-			const title = this._tokenToPlainText(tokens[idx + 1]);
+			const title = this.#tokenToPlainText(tokens[idx + 1]);
 			const slug = (env as RenderEnv).slugifier ? (env as RenderEnv).slugifier.add(title) : this.slugifier.fromHeading(title);
 			tokens[idx].attrSet('id', slug.value);
 
@@ -324,9 +329,9 @@ export class MarkdownItEngine implements IMdParser {
 		};
 	}
 
-	private _tokenToPlainText(token: MarkdownIt.Token): string {
+	#tokenToPlainText(token: MarkdownIt.Token): string {
 		if (token.children) {
-			return token.children.map(x => this._tokenToPlainText(x)).join('');
+			return token.children.map(x => this.#tokenToPlainText(x)).join('');
 		}
 
 		switch (token.type) {
@@ -339,7 +344,7 @@ export class MarkdownItEngine implements IMdParser {
 		}
 	}
 
-	private _addLinkRenderer(md: MarkdownIt): void {
+	#addLinkRenderer(md: MarkdownIt): void {
 		const original = md.renderer.rules.link_open;
 
 		md.renderer.rules.link_open = (tokens: MarkdownIt.Token[], idx: number, options, env, self) => {
@@ -357,7 +362,7 @@ export class MarkdownItEngine implements IMdParser {
 		};
 	}
 
-	private _toResourceUri(href: string, currentDocument: vscode.Uri | undefined, resourceProvider: WebviewResourceProvider | undefined): string {
+	#toResourceUri(href: string, currentDocument: vscode.Uri | undefined, resourceProvider: WebviewResourceProvider | undefined): string {
 		try {
 			// Support file:// links
 			if (isOfScheme(Schemes.file, href)) {
diff --git a/extensions/markdown-language-features/src/markdownExtensions.ts b/extensions/markdown-language-features/src/markdownExtensions.ts
index 1357b03d1de80..568a0f0b6386d 100644
--- a/extensions/markdown-language-features/src/markdownExtensions.ts
+++ b/extensions/markdown-language-features/src/markdownExtensions.ts
@@ -119,36 +119,38 @@ export interface MarkdownContributionProvider {
 
 class VSCodeExtensionMarkdownContributionProvider extends Disposable implements MarkdownContributionProvider {
 
-	private _contributions?: MarkdownContributions;
+	#contributions?: MarkdownContributions;
+	readonly #extensionContext: vscode.ExtensionContext;
 
 	public constructor(
-		private readonly _extensionContext: vscode.ExtensionContext,
+		extensionContext: vscode.ExtensionContext,
 	) {
 		super();
+		this.#extensionContext = extensionContext;
 
 		this._register(vscode.extensions.onDidChange(() => {
-			const currentContributions = this._getCurrentContributions();
-			const existingContributions = this._contributions || MarkdownContributions.Empty;
+			const currentContributions = this.#getCurrentContributions();
+			const existingContributions = this.#contributions || MarkdownContributions.Empty;
 			if (!MarkdownContributions.equal(existingContributions, currentContributions)) {
-				this._contributions = currentContributions;
-				this._onContributionsChanged.fire(this);
+				this.#contributions = currentContributions;
+				this.#onContributionsChanged.fire(this);
 			}
 		}));
 	}
 
 	public get extensionUri() {
-		return this._extensionContext.extensionUri;
+		return this.#extensionContext.extensionUri;
 	}
 
-	private readonly _onContributionsChanged = this._register(new vscode.EventEmitter<this>());
-	public readonly onContributionsChanged = this._onContributionsChanged.event;
+	readonly #onContributionsChanged = this._register(new vscode.EventEmitter<this>());
+	public readonly onContributionsChanged = this.#onContributionsChanged.event;
 
 	public get contributions(): MarkdownContributions {
-		this._contributions ??= this._getCurrentContributions();
-		return this._contributions;
+		this.#contributions ??= this.#getCurrentContributions();
+		return this.#contributions;
 	}
 
-	private _getCurrentContributions(): MarkdownContributions {
+	#getCurrentContributions(): MarkdownContributions {
 		return vscode.extensions.all
 			.map(MarkdownContributions.fromExtension)
 			.reduce(MarkdownContributions.merge, MarkdownContributions.Empty);
diff --git a/extensions/markdown-language-features/src/preview/documentRenderer.ts b/extensions/markdown-language-features/src/preview/documentRenderer.ts
index 61182a2443684..f96fce9b745a6 100644
--- a/extensions/markdown-language-features/src/preview/documentRenderer.ts
+++ b/extensions/markdown-language-features/src/preview/documentRenderer.ts
@@ -41,16 +41,28 @@ export interface ImageInfo {
 }
 
 export class MdDocumentRenderer {
+
+	readonly #engine: MarkdownItEngine;
+	readonly #context: vscode.ExtensionContext;
+	readonly #cspArbiter: ContentSecurityPolicyArbiter;
+	readonly #contributionProvider: MarkdownContributionProvider;
+	readonly #logger: ILogger;
+
 	constructor(
-		private readonly _engine: MarkdownItEngine,
-		private readonly _context: vscode.ExtensionContext,
-		private readonly _cspArbiter: ContentSecurityPolicyArbiter,
-		private readonly _contributionProvider: MarkdownContributionProvider,
-		private readonly _logger: ILogger
+		engine: MarkdownItEngine,
+		context: vscode.ExtensionContext,
+		cspArbiter: ContentSecurityPolicyArbiter,
+		contributionProvider: MarkdownContributionProvider,
+		logger: ILogger
 	) {
+		this.#engine = engine;
+		this.#context = context;
+		this.#cspArbiter = cspArbiter;
+		this.#contributionProvider = contributionProvider;
+		this.#logger = logger;
 		this.iconPath = {
-			dark: vscode.Uri.joinPath(this._context.extensionUri, 'media', 'preview-dark.svg'),
-			light: vscode.Uri.joinPath(this._context.extensionUri, 'media', 'preview-light.svg'),
+			dark: vscode.Uri.joinPath(this.#context.extensionUri, 'media', 'preview-dark.svg'),
+			light: vscode.Uri.joinPath(this.#context.extensionUri, 'media', 'preview-light.svg'),
 		};
 	}
 
@@ -76,15 +88,15 @@ export class MdDocumentRenderer {
 			scrollPreviewWithEditor: config.scrollPreviewWithEditor,
 			scrollEditorWithPreview: config.scrollEditorWithPreview,
 			doubleClickToSwitchToEditor: config.doubleClickToSwitchToEditor,
-			disableSecurityWarnings: this._cspArbiter.shouldDisableSecurityWarnings(),
+			disableSecurityWarnings: this.#cspArbiter.shouldDisableSecurityWarnings(),
 			webviewResourceRoot: resourceProvider.asWebviewUri(markdownDocument.uri).toString(),
 		};
 
-		this._logger.trace('DocumentRenderer', `provideTextDocumentContent - ${markdownDocument.uri}`, initialData);
+		this.#logger.trace('DocumentRenderer', `provideTextDocumentContent - ${markdownDocument.uri}`, initialData);
 
 		// Content Security Policy
 		const nonce = generateUuid();
-		const csp = this._getCsp(resourceProvider, sourceUri, nonce);
+		const csp = this.#getCsp(resourceProvider, sourceUri, nonce);
 
 		const body = await this.renderBody(markdownDocument, resourceProvider);
 		if (token.isCancellationRequested) {
@@ -92,7 +104,7 @@ export class MdDocumentRenderer {
 		}
 
 		const html = `<!DOCTYPE html>
-			<html style="${escapeAttribute(this._getSettingsOverrideStyles(config))}">
+			<html style="${escapeAttribute(this.#getSettingsOverrideStyles(config))}">
 			<head>
 				<meta http-equiv="Content-type" content="text/html;charset=UTF-8">
 				<meta http-equiv="Content-Security-Policy" content="${escapeAttribute(csp)}">
@@ -101,12 +113,12 @@ export class MdDocumentRenderer {
 					data-strings="${escapeAttribute(JSON.stringify(previewStrings))}"
 					data-state="${escapeAttribute(JSON.stringify(state || {}))}"
 					data-initial-md-content="${escapeAttribute(body.html)}">
-				<script src="${this._extensionResourcePath(resourceProvider, 'pre.js')}" nonce="${nonce}"></script>
-				${this._getStyles(resourceProvider, sourceUri, config, imageInfo)}
+				<script src="${this.#extensionResourcePath(resourceProvider, 'pre.js')}" nonce="${nonce}"></script>
+				${this.#getStyles(resourceProvider, sourceUri, config, imageInfo)}
 				<base href="${resourceProvider.asWebviewUri(markdownDocument.uri)}">
 			</head>
 			<body class="vscode-body ${config.scrollBeyondLastLine ? 'scrollBeyondLastLine' : ''} ${config.wordWrap ? 'wordWrap' : ''} ${config.markEditorSelection ? 'showEditorSelection' : ''}">
-				${this._getScripts(resourceProvider, nonce)}
+				${this.#getScripts(resourceProvider, nonce)}
 			</body>
 			</html>`;
 		return {
@@ -119,7 +131,7 @@ export class MdDocumentRenderer {
 		markdownDocument: vscode.TextDocument,
 		resourceProvider: WebviewResourceProvider,
 	): Promise<MarkdownContentProviderOutput> {
-		const rendered = await this._engine.render(markdownDocument, resourceProvider);
+		const rendered = await this.#engine.render(markdownDocument, resourceProvider);
 		const html = `<div class="markdown-body" dir="auto">${rendered.html}<div class="code-line" data-line="${markdownDocument.lineCount}"></div></div>`;
 		return {
 			html,
@@ -138,13 +150,13 @@ export class MdDocumentRenderer {
 			</html>`;
 	}
 
-	private _extensionResourcePath(resourceProvider: WebviewResourceProvider, mediaFile: string): string {
+	#extensionResourcePath(resourceProvider: WebviewResourceProvider, mediaFile: string): string {
 		const webviewResource = resourceProvider.asWebviewUri(
-			vscode.Uri.joinPath(this._context.extensionUri, 'media', mediaFile));
+			vscode.Uri.joinPath(this.#context.extensionUri, 'media', mediaFile));
 		return webviewResource.toString();
 	}
 
-	private _fixHref(resourceProvider: WebviewResourceProvider, resource: vscode.Uri, href: string): string {
+	#fixHref(resourceProvider: WebviewResourceProvider, resource: vscode.Uri, href: string): string {
 		if (!href) {
 			return href;
 		}
@@ -168,18 +180,18 @@ export class MdDocumentRenderer {
 		return resourceProvider.asWebviewUri(vscode.Uri.joinPath(uri.Utils.dirname(resource), href)).toString();
 	}
 
-	private _computeCustomStyleSheetIncludes(resourceProvider: WebviewResourceProvider, resource: vscode.Uri, config: MarkdownPreviewConfiguration): string {
+	#computeCustomStyleSheetIncludes(resourceProvider: WebviewResourceProvider, resource: vscode.Uri, config: MarkdownPreviewConfiguration): string {
 		if (!Array.isArray(config.styles)) {
 			return '';
 		}
 		const out: string[] = [];
 		for (const style of config.styles) {
-			out.push(`<link rel="stylesheet" class="code-user-style" data-source="${escapeAttribute(style)}" href="${escapeAttribute(this._fixHref(resourceProvider, resource, style))}" type="text/css" media="screen">`);
+			out.push(`<link rel="stylesheet" class="code-user-style" data-source="${escapeAttribute(style)}" href="${escapeAttribute(this.#fixHref(resourceProvider, resource, style))}" type="text/css" media="screen">`);
 		}
 		return out.join('\n');
 	}
 
-	private _getSettingsOverrideStyles(config: MarkdownPreviewConfiguration): string {
+	#getSettingsOverrideStyles(config: MarkdownPreviewConfiguration): string {
 		return [
 			config.fontFamily ? `--markdown-font-family: ${config.fontFamily};` : '',
 			isNaN(config.fontSize) ? '' : `--markdown-font-size: ${config.fontSize}px;`,
@@ -187,7 +199,7 @@ export class MdDocumentRenderer {
 		].join(' ');
 	}
 
-	private _getImageStabilizerStyles(imageInfo: readonly ImageInfo[]): string {
+	#getImageStabilizerStyles(imageInfo: readonly ImageInfo[]): string {
 		if (!imageInfo.length) {
 			return '';
 		}
@@ -204,20 +216,20 @@ export class MdDocumentRenderer {
 		return ret;
 	}
 
-	private _getStyles(resourceProvider: WebviewResourceProvider, resource: vscode.Uri, config: MarkdownPreviewConfiguration, imageInfo: readonly ImageInfo[]): string {
+	#getStyles(resourceProvider: WebviewResourceProvider, resource: vscode.Uri, config: MarkdownPreviewConfiguration, imageInfo: readonly ImageInfo[]): string {
 		const baseStyles: string[] = [];
-		for (const resource of this._contributionProvider.contributions.previewStyles) {
+		for (const resource of this.#contributionProvider.contributions.previewStyles) {
 			baseStyles.push(`<link rel="stylesheet" type="text/css" href="${escapeAttribute(resourceProvider.asWebviewUri(resource))}">`);
 		}
 
 		return `${baseStyles.join('\n')}
-			${this._computeCustomStyleSheetIncludes(resourceProvider, resource, config)}
-			${this._getImageStabilizerStyles(imageInfo)}`;
+			${this.#computeCustomStyleSheetIncludes(resourceProvider, resource, config)}
+			${this.#getImageStabilizerStyles(imageInfo)}`;
 	}
 
-	private _getScripts(resourceProvider: WebviewResourceProvider, nonce: string): string {
+	#getScripts(resourceProvider: WebviewResourceProvider, nonce: string): string {
 		const out: string[] = [];
-		for (const resource of this._contributionProvider.contributions.previewScripts) {
+		for (const resource of this.#contributionProvider.contributions.previewScripts) {
 			out.push(`<script async
 				src="${escapeAttribute(resourceProvider.asWebviewUri(resource))}"
 				nonce="${nonce}"
@@ -226,13 +238,13 @@ export class MdDocumentRenderer {
 		return out.join('\n');
 	}
 
-	private _getCsp(
+	#getCsp(
 		provider: WebviewResourceProvider,
 		resource: vscode.Uri,
 		nonce: string
 	): string {
 		const rule = provider.cspSource.split(';')[0];
-		switch (this._cspArbiter.getSecurityLevelForResource(resource)) {
+		switch (this.#cspArbiter.getSecurityLevelForResource(resource)) {
 			case MarkdownPreviewSecurityLevel.AllowInsecureContent:
 				return `default-src 'none'; img-src 'self' ${rule} http: https: data:; media-src 'self' ${rule} http: https: data:; script-src 'nonce-${nonce}'; style-src 'self' ${rule} 'unsafe-inline' http: https: data:; font-src 'self' ${rule} http: https: data:;`;
 
diff --git a/extensions/markdown-language-features/src/preview/preview.ts b/extensions/markdown-language-features/src/preview/preview.ts
index 19d1755e7eb4f..9932db7d1b2d2 100644
--- a/extensions/markdown-language-features/src/preview/preview.ts
+++ b/extensions/markdown-language-features/src/preview/preview.ts
@@ -10,7 +10,7 @@ import { MarkdownContributionProvider } from '../markdownExtensions';
 import { Disposable } from '../util/dispose';
 import { isMarkdownFile } from '../util/file';
 import { MdLinkOpener } from '../util/openDocumentLink';
-import { WebviewResourceProvider } from '../util/resources';
+import { areUrisEqual, WebviewResourceProvider } from '../util/resources';
 import { urlToUri } from '../util/url';
 import { ImageInfo, MdDocumentRenderer } from './documentRenderer';
 import { MarkdownPreviewConfigurationManager } from './previewConfig';
@@ -21,16 +21,16 @@ import type { FromWebviewMessage, ToWebviewMessage } from '../../types/previewMe
 export class PreviewDocumentVersion {
 
 	public readonly resource: vscode.Uri;
-	private readonly _version: number;
+	readonly #version: number;
 
 	public constructor(document: vscode.TextDocument) {
 		this.resource = document.uri;
-		this._version = document.version;
+		this.#version = document.version;
 	}
 
 	public equals(other: PreviewDocumentVersion): boolean {
-		return this.resource.fsPath === other.resource.fsPath
-			&& this._version === other._version;
+		return areUrisEqual(this.resource, other.resource)
+			&& this.#version === other.#version;
 	}
 }
 
@@ -42,59 +42,73 @@ interface MarkdownPreviewDelegate {
 
 class MarkdownPreview extends Disposable implements WebviewResourceProvider {
 
-	private static readonly _unwatchedImageSchemes = new Set(['https', 'http', 'data']);
+	static readonly #unwatchedImageSchemes = new Set(['https', 'http', 'data']);
 
-	private _disposed: boolean = false;
+	#disposed: boolean = false;
 
-	private readonly _delay = 300;
-	private _throttleTimer: any;
+	readonly #delay = 300;
+	#throttleTimer: any;
 
-	private readonly _resource: vscode.Uri;
-	private readonly _webviewPanel: vscode.WebviewPanel;
+	readonly #resource: vscode.Uri;
+	readonly #webviewPanel: vscode.WebviewPanel;
 
-	private _line: number | undefined;
-	private readonly _scrollToFragment: string | undefined;
-	private _firstUpdate = true;
-	private _currentVersion?: PreviewDocumentVersion;
-	private _isScrolling = false;
+	#line: number | undefined;
+	readonly #scrollToFragment: string | undefined;
+	#firstUpdate = true;
+	#currentVersion?: PreviewDocumentVersion;
+	#isScrolling = false;
 
-	private _imageInfo: readonly ImageInfo[] = [];
-	private readonly _fileWatchersBySrc = new Map</* src: */ string, vscode.FileSystemWatcher>();
+	#imageInfo: readonly ImageInfo[] = [];
+	readonly #fileWatchersBySrc = new Map</* src: */ string, vscode.FileSystemWatcher>();
 
-	private readonly _onScrollEmitter = this._register(new vscode.EventEmitter<LastScrollLocation>());
-	public readonly onScroll = this._onScrollEmitter.event;
+	readonly #onScrollEmitter = this._register(new vscode.EventEmitter<LastScrollLocation>());
+	public readonly onScroll = this.#onScrollEmitter.event;
 
-	private readonly _disposeCts = this._register(new vscode.CancellationTokenSource());
+	readonly #disposeCts = this._register(new vscode.CancellationTokenSource());
+
+	readonly #delegate: MarkdownPreviewDelegate;
+	readonly #contentProvider: MdDocumentRenderer;
+	readonly #previewConfigurations: MarkdownPreviewConfigurationManager;
+	readonly #logger: ILogger;
+	readonly #contributionProvider: MarkdownContributionProvider;
+	readonly #opener: MdLinkOpener;
 
 	constructor(
 		webview: vscode.WebviewPanel,
 		resource: vscode.Uri,
 		startingScroll: StartingScrollLocation | undefined,
-		private readonly _delegate: MarkdownPreviewDelegate,
-		private readonly _contentProvider: MdDocumentRenderer,
-		private readonly _previewConfigurations: MarkdownPreviewConfigurationManager,
-		private readonly _logger: ILogger,
-		private readonly _contributionProvider: MarkdownContributionProvider,
-		private readonly _opener: MdLinkOpener,
+		delegate: MarkdownPreviewDelegate,
+		contentProvider: MdDocumentRenderer,
+		previewConfigurations: MarkdownPreviewConfigurationManager,
+		logger: ILogger,
+		contributionProvider: MarkdownContributionProvider,
+		opener: MdLinkOpener,
 	) {
 		super();
 
-		this._webviewPanel = webview;
-		this._resource = resource;
+		this.#delegate = delegate;
+		this.#contentProvider = contentProvider;
+		this.#previewConfigurations = previewConfigurations;
+		this.#logger = logger;
+		this.#contributionProvider = contributionProvider;
+		this.#opener = opener;
+
+		this.#webviewPanel = webview;
+		this.#resource = resource;
 
 		switch (startingScroll?.type) {
 			case 'line':
 				if (!isNaN(startingScroll.line!)) {
-					this._line = startingScroll.line;
+					this.#line = startingScroll.line;
 				}
 				break;
 
 			case 'fragment':
-				this._scrollToFragment = startingScroll.fragment;
+				this.#scrollToFragment = startingScroll.fragment;
 				break;
 		}
 
-		this._register(_contributionProvider.onContributionsChanged(() => {
+		this._register(contributionProvider.onContributionsChanged(() => {
 			setTimeout(() => this.refresh(true), 0);
 		}));
 
@@ -122,26 +136,26 @@ class MarkdownPreview extends Disposable implements WebviewResourceProvider {
 			}));
 		}
 
-		this._register(this._webviewPanel.webview.onDidReceiveMessage((e: FromWebviewMessage.Type) => {
-			if (e.source !== this._resource.toString()) {
+		this._register(this.#webviewPanel.webview.onDidReceiveMessage((e: FromWebviewMessage.Type) => {
+			if (e.source !== this.#resource.toString()) {
 				return;
 			}
 
 			switch (e.type) {
 				case 'cacheImageSizes':
-					this._imageInfo = e.imageData;
+					this.#imageInfo = e.imageData;
 					break;
 
 				case 'revealLine':
-					this._onDidScrollPreview(e.line);
+					this.#onDidScrollPreview(e.line);
 					break;
 
 				case 'didClick':
-					this._onDidClickPreview(e.line);
+					this.#onDidClickPreview(e.line);
 					break;
 
 				case 'openLink':
-					this._onDidClickPreviewLink(e.href);
+					this.#onDidClickPreviewLink(e.href);
 					break;
 
 				case 'showPreviewSecuritySelector':
@@ -159,29 +173,29 @@ class MarkdownPreview extends Disposable implements WebviewResourceProvider {
 	}
 
 	override dispose() {
-		this._disposeCts.cancel();
+		this.#disposeCts.cancel();
 
 		super.dispose();
 
-		this._disposed = true;
+		this.#disposed = true;
 
-		clearTimeout(this._throttleTimer);
-		for (const entry of this._fileWatchersBySrc.values()) {
+		clearTimeout(this.#throttleTimer);
+		for (const entry of this.#fileWatchersBySrc.values()) {
 			entry.dispose();
 		}
-		this._fileWatchersBySrc.clear();
+		this.#fileWatchersBySrc.clear();
 	}
 
 	public get resource(): vscode.Uri {
-		return this._resource;
+		return this.#resource;
 	}
 
 	public get state() {
 		return {
-			resource: this._resource.toString(),
-			line: this._line,
-			fragment: this._scrollToFragment,
-			...this._delegate.getAdditionalState(),
+			resource: this.#resource.toString(),
+			line: this.#line,
+			fragment: this.#scrollToFragment,
+			...this.#delegate.getAdditionalState(),
 		};
 	}
 
@@ -191,79 +205,79 @@ class MarkdownPreview extends Disposable implements WebviewResourceProvider {
 	*/
 	public refresh(forceUpdate: boolean = false) {
 		// Schedule update if none is pending
-		if (!this._throttleTimer) {
-			if (this._firstUpdate) {
-				this._updatePreview(true);
+		if (!this.#throttleTimer) {
+			if (this.#firstUpdate) {
+				this.#updatePreview(true);
 			} else {
-				this._throttleTimer = setTimeout(() => this._updatePreview(forceUpdate), this._delay);
+				this.#throttleTimer = setTimeout(() => this.#updatePreview(forceUpdate), this.#delay);
 			}
 		}
 
-		this._firstUpdate = false;
+		this.#firstUpdate = false;
 	}
 
 
 	public isPreviewOf(resource: vscode.Uri): boolean {
-		return this._resource.fsPath === resource.fsPath;
+		return areUrisEqual(this.#resource, resource);
 	}
 
 	public postMessage(msg: ToWebviewMessage.Type) {
-		if (!this._disposed) {
-			this._webviewPanel.webview.postMessage(msg);
+		if (!this.#disposed) {
+			this.#webviewPanel.webview.postMessage(msg);
 		}
 	}
 
 	public scrollTo(topLine: number) {
-		if (this._disposed) {
+		if (this.#disposed) {
 			return;
 		}
 
-		if (this._isScrolling) {
-			this._isScrolling = false;
+		if (this.#isScrolling) {
+			this.#isScrolling = false;
 			return;
 		}
 
-		this._logger.trace('MarkdownPreview', 'updateForView', { markdownFile: this._resource });
-		this._line = topLine;
+		this.#logger.trace('MarkdownPreview', 'updateForView', { markdownFile: this.#resource });
+		this.#line = topLine;
 		this.postMessage({
 			type: 'updateView',
 			line: topLine,
-			source: this._resource.toString()
+			source: this.#resource.toString()
 		});
 	}
 
-	private async _updatePreview(forceUpdate?: boolean): Promise<void> {
-		clearTimeout(this._throttleTimer);
-		this._throttleTimer = undefined;
+	async #updatePreview(forceUpdate?: boolean): Promise<void> {
+		clearTimeout(this.#throttleTimer);
+		this.#throttleTimer = undefined;
 
-		if (this._disposed) {
+		if (this.#disposed) {
 			return;
 		}
 
 		let document: vscode.TextDocument;
 		try {
-			document = await vscode.workspace.openTextDocument(this._resource);
+			document = await vscode.workspace.openTextDocument(this.#resource);
 		} catch {
-			if (!this._disposed) {
-				await this._showFileNotFoundError();
+			if (!this.#disposed) {
+				await this.#showFileNotFoundError();
 			}
 			return;
 		}
 
-		if (this._disposed) {
+		if (this.#disposed) {
 			return;
 		}
 
 		const pendingVersion = new PreviewDocumentVersion(document);
-		if (!forceUpdate && this._currentVersion?.equals(pendingVersion)) {
-			if (this._line) {
-				this.scrollTo(this._line);
+		if (!forceUpdate && this.#currentVersion?.equals(pendingVersion)) {
+			if (this.#line) {
+				this.scrollTo(this.#line);
 			}
 			return;
 		}
 
-		const shouldReloadPage = forceUpdate || !this._currentVersion || this._currentVersion.resource.toString() !== pendingVersion.resource.toString() || !this._webviewPanel.visible;
-		this._currentVersion = pendingVersion;
+		const shouldReloadPage = forceUpdate || !this.#currentVersion || this.#currentVersion.resource.toString() !== pendingVersion.resource.toString() || !this.#webviewPanel.visible;
+		this.#currentVersion = pendingVersion;
 
 		let selectedLine: number | undefined = undefined;
 		for (const editor of vscode.window.visibleTextEditors) {
@@ -274,21 +288,21 @@ class MarkdownPreview extends Disposable implements WebviewResourceProvider {
 		}
 
 		const content = await (shouldReloadPage
-			? this._contentProvider.renderDocument(document, this, this._previewConfigurations, this._line, selectedLine, this.state, this._imageInfo, this._disposeCts.token)
-			: this._contentProvider.renderBody(document, this));
+			? this.#contentProvider.renderDocument(document, this, this.#previewConfigurations, this.#line, selectedLine, this.state, this.#imageInfo, this.#disposeCts.token)
+			: this.#contentProvider.renderBody(document, this));
 
 		// Another call to `doUpdate` may have happened.
 		// Make sure we are still updating for the correct document
-		if (this._currentVersion?.equals(pendingVersion)) {
-			this._updateWebviewContent(content.html, shouldReloadPage);
-			this._updateImageWatchers(content.containingImages);
+		if (this.#currentVersion?.equals(pendingVersion)) {
+			this.#updateWebviewContent(content.html, shouldReloadPage);
+			this.#updateImageWatchers(content.containingImages);
 		}
 	}
 
-	private _onDidScrollPreview(line: number) {
-		this._line = line;
-		this._onScrollEmitter.fire({ line: this._line, uri: this._resource });
-		const config = this._previewConfigurations.loadAndCacheConfiguration(this._resource);
+	#onDidScrollPreview(line: number) {
+		this.#line = line;
+		this.#onScrollEmitter.fire({ line: this.#line, uri: this.#resource });
+		const config = this.#previewConfigurations.loadAndCacheConfiguration(this.#resource);
 		if (!config.scrollEditorWithPreview) {
 			return;
 		}
@@ -298,12 +312,12 @@ class MarkdownPreview extends Disposable implements WebviewResourceProvider {
 				continue;
 			}
 
-			this._isScrolling = true;
+			this.#isScrolling = true;
 			scrollEditorToLine(line, editor);
 		}
 	}
 
-	private async _onDidClickPreview(line: number): Promise<void> {
+	async #onDidClickPreview(line: number): Promise<void> {
 		// fix #82457, find currently opened but unfocused source tab
 		await vscode.commands.executeCommand('markdown.showSource');
 
@@ -322,97 +336,97 @@ class MarkdownPreview extends Disposable implements WebviewResourceProvider {
 			}
 		}
 
-		await vscode.workspace.openTextDocument(this._resource)
+		await vscode.workspace.openTextDocument(this.#resource)
 			.then(vscode.window.showTextDocument)
 			.then((editor) => {
 				revealLineInEditor(editor);
 			}, () => {
-				vscode.window.showErrorMessage(vscode.l10n.t('Could not open {0}', this._resource.toString()));
+				vscode.window.showErrorMessage(vscode.l10n.t('Could not open {0}', this.#resource.toString()));
 			});
 	}
 
-	private async _showFileNotFoundError() {
-		this._webviewPanel.webview.html = this._contentProvider.renderFileNotFoundDocument(this._resource);
+	async #showFileNotFoundError() {
+		this.#webviewPanel.webview.html = this.#contentProvider.renderFileNotFoundDocument(this.#resource);
 	}
 
-	private _updateWebviewContent(html: string, reloadPage: boolean): void {
-		if (this._disposed) {
+	#updateWebviewContent(html: string, reloadPage: boolean): void {
+		if (this.#disposed) {
 			return;
 		}
 
-		if (this._delegate.getTitle) {
-			this._webviewPanel.title = this._delegate.getTitle(this._resource);
+		if (this.#delegate.getTitle) {
+			this.#webviewPanel.title = this.#delegate.getTitle(this.#resource);
 		}
-		this._webviewPanel.webview.options = this._getWebviewOptions();
+		this.#webviewPanel.webview.options = this.#getWebviewOptions();
 
 		if (reloadPage) {
-			this._webviewPanel.webview.html = html;
+			this.#webviewPanel.webview.html = html;
 		} else {
 			this.postMessage({
 				type: 'updateContent',
 				content: html,
-				source: this._resource.toString(),
+				source: this.#resource.toString(),
 			});
 		}
 	}
 
-	private _updateImageWatchers(srcs: Set<string>) {
+	#updateImageWatchers(srcs: Set<string>) {
 		// Delete stale file watchers.
-		for (const [src, watcher] of this._fileWatchersBySrc) {
+		for (const [src, watcher] of this.#fileWatchersBySrc) {
 			if (!srcs.has(src)) {
 				watcher.dispose();
-				this._fileWatchersBySrc.delete(src);
+				this.#fileWatchersBySrc.delete(src);
 			}
 		}
 
 		// Create new file watchers.
-		const root = vscode.Uri.joinPath(this._resource, '../');
+		const root = vscode.Uri.joinPath(this.#resource, '../');
 		for (const src of srcs) {
 			const uri = urlToUri(src, root);
-			if (uri && !MarkdownPreview._unwatchedImageSchemes.has(uri.scheme) && !this._fileWatchersBySrc.has(src)) {
+			if (uri && !MarkdownPreview.#unwatchedImageSchemes.has(uri.scheme) && !this.#fileWatchersBySrc.has(src)) {
 				const watcher = vscode.workspace.createFileSystemWatcher(new vscode.RelativePattern(uri, '*'));
 				watcher.onDidChange(() => {
 					this.refresh(true);
 				});
-				this._fileWatchersBySrc.set(src, watcher);
+				this.#fileWatchersBySrc.set(src, watcher);
 			}
 		}
 	}
 
-	private _getWebviewOptions(): vscode.WebviewOptions {
+	#getWebviewOptions(): vscode.WebviewOptions {
 		return {
 			enableScripts: true,
 			enableForms: false,
-			localResourceRoots: this._getLocalResourceRoots()
+			localResourceRoots: this.#getLocalResourceRoots()
 		};
 	}
 
-	private _getLocalResourceRoots(): ReadonlyArray<vscode.Uri> {
-		const baseRoots = Array.from(this._contributionProvider.contributions.previewResourceRoots);
+	#getLocalResourceRoots(): ReadonlyArray<vscode.Uri> {
+		const baseRoots = Array.from(this.#contributionProvider.contributions.previewResourceRoots);
 
-		const folder = vscode.workspace.getWorkspaceFolder(this._resource);
+		const folder = vscode.workspace.getWorkspaceFolder(this.#resource);
 		if (folder) {
 			const workspaceRoots = vscode.workspace.workspaceFolders?.map(folder => folder.uri);
 			if (workspaceRoots) {
 				baseRoots.push(...workspaceRoots);
 			}
 		} else {
-			baseRoots.push(uri.Utils.dirname(this._resource));
+			baseRoots.push(uri.Utils.dirname(this.#resource));
 		}
 
 		return baseRoots;
 	}
 
-	private async _onDidClickPreviewLink(href: string) {
+	async #onDidClickPreviewLink(href: string) {
 		const config = vscode.workspace.getConfiguration('markdown', this.resource);
 		const openLinks = config.get<string>('preview.openMarkdownLinks', 'inPreview');
 		if (openLinks === 'inPreview') {
-			const resolved = await this._opener.resolveDocumentLink(href, this.resource);
+			const resolved = await this.#opener.resolveDocumentLink(href, this.resource);
 			if (resolved.kind === 'file') {
 				try {
 					const doc = await vscode.workspace.openTextDocument(vscode.Uri.from(resolved.uri));
 					if (isMarkdownFile(doc)) {
-						return this._delegate.openPreviewLinkToMarkdownFile(doc.uri, resolved.fragment ? decodeURIComponent(resolved.fragment) : undefined);
+						return this.#delegate.openPreviewLinkToMarkdownFile(doc.uri, resolved.fragment ? decodeURIComponent(resolved.fragment) : undefined);
 					}
 				} catch {
 					// Noop
@@ -420,21 +434,21 @@ class MarkdownPreview extends Disposable implements WebviewResourceProvider {
 			}
 		}
 
-		return this._opener.openDocumentLink(href, this.resource);
+		return this.#opener.openDocumentLink(href, this.resource);
 	}
 
 	//#region WebviewResourceProvider
 
 	asWebviewUri(resource: vscode.Uri) {
-		return this._webviewPanel.webview.asWebviewUri(resource);
+		return this.#webviewPanel.webview.asWebviewUri(resource);
 	}
 
 	get cspSource() {
 		return [
-			this._webviewPanel.webview.cspSource,
+			this.#webviewPanel.webview.cspSource,
 
 			// On web, we also need to allow loading of resources from contributed extensions
-			...this._contributionProvider.contributions.previewResourceRoots
+			...this.#contributionProvider.contributions.previewResourceRoots
 				.filter(root => root.scheme === 'http' || root.scheme === 'https')
 				.map(root => {
 					const dirRoot = root.path.endsWith('/') ? root : root.with({ path: root.path + '/' });
@@ -484,13 +498,16 @@ export class StaticMarkdownPreview extends Disposable implements IManagedMarkdow
 		return new StaticMarkdownPreview(webview, resource, contentProvider, previewConfigurations, topmostLineMonitor, logger, contributionProvider, opener, scrollLine);
 	}
 
-	private readonly _preview: MarkdownPreview;
+	readonly #preview: MarkdownPreview;
+
+	readonly #webviewPanel: vscode.WebviewPanel;
+	readonly #previewConfigurations: MarkdownPreviewConfigurationManager;
 
 	private constructor(
-		private readonly _webviewPanel: vscode.WebviewPanel,
+		webviewPanel: vscode.WebviewPanel,
 		resource: vscode.Uri,
 		contentProvider: MdDocumentRenderer,
-		private readonly _previewConfigurations: MarkdownPreviewConfigurationManager,
+		previewConfigurations: MarkdownPreviewConfigurationManager,
 		topmostLineMonitor: TopmostLineMonitor,
 		logger: ILogger,
 		contributionProvider: MarkdownContributionProvider,
@@ -498,52 +515,56 @@ export class StaticMarkdownPreview extends Disposable implements IManagedMarkdow
 		scrollLine?: number,
 	) {
 		super();
+
+		this.#webviewPanel = webviewPanel;
+		this.#previewConfigurations = previewConfigurations;
+
 		const topScrollLocation = scrollLine ? new StartingScrollLine(scrollLine) : undefined;
-		this._preview = this._register(new MarkdownPreview(this._webviewPanel, resource, topScrollLocation, {
+		this.#preview = this._register(new MarkdownPreview(this.#webviewPanel, resource, topScrollLocation, {
 			getAdditionalState: () => { return {}; },
 			openPreviewLinkToMarkdownFile: (markdownLink, fragment) => {
 				return vscode.commands.executeCommand('vscode.openWith', markdownLink.with({
 					fragment
-				}), StaticMarkdownPreview.customEditorViewType, this._webviewPanel.viewColumn);
+				}), StaticMarkdownPreview.customEditorViewType, this.#webviewPanel.viewColumn);
 			}
-		}, contentProvider, _previewConfigurations, logger, contributionProvider, opener));
+		}, contentProvider, previewConfigurations, logger, contributionProvider, opener));
 
-		this._register(this._webviewPanel.onDidDispose(() => {
+		this._register(this.#webviewPanel.onDidDispose(() => {
 			this.dispose();
 		}));
 
-		this._register(this._webviewPanel.onDidChangeViewState(e => {
-			this._onDidChangeViewState.fire(e);
+		this._register(this.#webviewPanel.onDidChangeViewState(e => {
+			this.#onDidChangeViewState.fire(e);
 		}));
 
-		this._register(this._preview.onScroll((scrollInfo) => {
+		this._register(this.#preview.onScroll((scrollInfo) => {
 			topmostLineMonitor.setPreviousStaticEditorLine(scrollInfo);
 		}));
 
 		this._register(topmostLineMonitor.onDidChanged(event => {
-			if (this._preview.isPreviewOf(event.resource)) {
-				this._preview.scrollTo(event.line);
+			if (this.#preview.isPreviewOf(event.resource)) {
+				this.#preview.scrollTo(event.line);
 			}
 		}));
 	}
 
 	copyImage(id: string) {
-		this._webviewPanel.reveal();
-		this._preview.postMessage({
+		this.#webviewPanel.reveal();
+		this.#preview.postMessage({
 			type: 'copyImage',
 			source: this.resource.toString(),
 			id: id
 		});
 	}
 
-	private readonly _onDispose = this._register(new vscode.EventEmitter<void>());
-	public readonly onDispose = this._onDispose.event;
+	readonly #onDispose = this._register(new vscode.EventEmitter<void>());
+	public readonly onDispose = this.#onDispose.event;
 
-	private readonly _onDidChangeViewState = this._register(new vscode.EventEmitter<vscode.WebviewPanelOnDidChangeViewStateEvent>());
-	public readonly onDidChangeViewState = this._onDidChangeViewState.event;
+	readonly #onDidChangeViewState = this._register(new vscode.EventEmitter<vscode.WebviewPanelOnDidChangeViewStateEvent>());
+	public readonly onDidChangeViewState = this.#onDidChangeViewState.event;
 
 	override dispose() {
-		this._onDispose.fire();
+		this.#onDispose.fire();
 		super.dispose();
 	}
 
@@ -556,21 +577,21 @@ export class StaticMarkdownPreview extends Disposable implements IManagedMarkdow
 	}
 
 	public refresh() {
-		this._preview.refresh(true);
+		this.#preview.refresh(true);
 	}
 
 	public updateConfiguration() {
-		if (this._previewConfigurations.hasConfigurationChanged(this._preview.resource)) {
+		if (this.#previewConfigurations.hasConfigurationChanged(this.#preview.resource)) {
 			this.refresh();
 		}
 	}
 
 	public get resource() {
-		return this._preview.resource;
+		return this.#preview.resource;
 	}
 
 	public get resourceColumn() {
-		return this._webviewPanel.viewColumn || vscode.ViewColumn.One;
+		return this.#webviewPanel.viewColumn || vscode.ViewColumn.One;
 	}
 }
 
@@ -585,11 +606,11 @@ export class DynamicMarkdownPreview extends Disposable implements IManagedMarkdo
 
 	public static readonly viewType = 'markdown.preview';
 
-	private readonly _resourceColumn: vscode.ViewColumn;
-	private _locked: boolean;
+	readonly #resourceColumn: vscode.ViewColumn;
+	#locked: boolean;
 
-	private readonly _webviewPanel: vscode.WebviewPanel;
-	private _preview: MarkdownPreview;
+	readonly #webviewPanel: vscode.WebviewPanel;
+	#preview: MarkdownPreview;
 
 	public static revive(
 		input: DynamicPreviewInput,
@@ -619,7 +640,7 @@ export class DynamicMarkdownPreview extends Disposable implements IManagedMarkdo
 	): DynamicMarkdownPreview {
 		const webview = vscode.window.createWebviewPanel(
 			DynamicMarkdownPreview.viewType,
-			DynamicMarkdownPreview._getPreviewTitle(input.resource, input.locked),
+			DynamicMarkdownPreview.#getPreviewTitle(input.resource, input.locked),
 			previewColumn, { enableFindWidget: true, });
 
 		webview.iconPath = contentProvider.iconPath;
@@ -628,43 +649,57 @@ export class DynamicMarkdownPreview extends Disposable implements IManagedMarkdo
 			contentProvider, previewConfigurations, logger, topmostLineMonitor, contributionProvider, opener);
 	}
 
+	readonly #contentProvider: MdDocumentRenderer;
+	readonly #previewConfigurations: MarkdownPreviewConfigurationManager;
+	readonly #logger: ILogger;
+	readonly #topmostLineMonitor: TopmostLineMonitor;
+	readonly #contributionProvider: MarkdownContributionProvider;
+	readonly #opener: MdLinkOpener;
+
 	private constructor(
 		webview: vscode.WebviewPanel,
 		input: DynamicPreviewInput,
-		private readonly _contentProvider: MdDocumentRenderer,
-		private readonly _previewConfigurations: MarkdownPreviewConfigurationManager,
-		private readonly _logger: ILogger,
-		private readonly _topmostLineMonitor: TopmostLineMonitor,
-		private readonly _contributionProvider: MarkdownContributionProvider,
-		private readonly _opener: MdLinkOpener,
+		contentProvider: MdDocumentRenderer,
+		previewConfigurations: MarkdownPreviewConfigurationManager,
+		logger: ILogger,
+		topmostLineMonitor: TopmostLineMonitor,
+		contributionProvider: MarkdownContributionProvider,
+		opener: MdLinkOpener,
 	) {
 		super();
 
-		this._webviewPanel = webview;
+		this.#contentProvider = contentProvider;
+		this.#previewConfigurations = previewConfigurations;
+		this.#logger = logger;
+		this.#topmostLineMonitor = topmostLineMonitor;
+		this.#contributionProvider = contributionProvider;
+		this.#opener = opener;
+
+		this.#webviewPanel = webview;
 
-		this._resourceColumn = input.resourceColumn;
-		this._locked = input.locked;
+		this.#resourceColumn = input.resourceColumn;
+		this.#locked = input.locked;
 
-		this._preview = this._createPreview(input.resource, typeof input.line === 'number' ? new StartingScrollLine(input.line) : undefined);
+		this.#preview = this.#createPreview(input.resource, typeof input.line === 'number' ? new StartingScrollLine(input.line) : undefined);
 
 		this._register(webview.onDidDispose(() => { this.dispose(); }));
 
-		this._register(this._webviewPanel.onDidChangeViewState(e => {
-			this._onDidChangeViewStateEmitter.fire(e);
+		this._register(this.#webviewPanel.onDidChangeViewState(e => {
+			this.#onDidChangeViewStateEmitter.fire(e);
 		}));
 
-		this._register(this._topmostLineMonitor.onDidChanged(event => {
-			if (this._preview.isPreviewOf(event.resource)) {
-				this._preview.scrollTo(event.line);
+		this._register(this.#topmostLineMonitor.onDidChanged(event => {
+			if (this.#preview.isPreviewOf(event.resource)) {
+				this.#preview.scrollTo(event.line);
 			}
 		}));
 
 		this._register(vscode.window.onDidChangeTextEditorSelection(event => {
-			if (this._preview.isPreviewOf(event.textEditor.document.uri)) {
-				this._preview.postMessage({
+			if (this.#preview.isPreviewOf(event.textEditor.document.uri)) {
+				this.#preview.postMessage({
 					type: 'onDidChangeTextEditorSelection',
 					line: event.selections[0].active.line,
-					source: this._preview.resource.toString()
+					source: this.#preview.resource.toString()
 				});
 			}
 		}));
@@ -675,7 +710,7 @@ export class DynamicMarkdownPreview extends Disposable implements IManagedMarkdo
 				return;
 			}
 
-			if (isMarkdownFile(editor.document) && !this._locked && !this._preview.isPreviewOf(editor.document.uri)) {
+			if (isMarkdownFile(editor.document) && !this.#locked && !this.#preview.isPreviewOf(editor.document.uri)) {
 				const line = getVisibleLine(editor);
 				this.update(editor.document.uri, line ? new StartingScrollLine(line) : undefined);
 			}
@@ -683,56 +718,56 @@ export class DynamicMarkdownPreview extends Disposable implements IManagedMarkdo
 	}
 
 	copyImage(id: string) {
-		this._webviewPanel.reveal();
-		this._preview.postMessage({
+		this.#webviewPanel.reveal();
+		this.#preview.postMessage({
 			type: 'copyImage',
 			source: this.resource.toString(),
 			id: id
 		});
 	}
 
-	private readonly _onDisposeEmitter = this._register(new vscode.EventEmitter<void>());
-	public readonly onDispose = this._onDisposeEmitter.event;
+	readonly #onDisposeEmitter = this._register(new vscode.EventEmitter<void>());
+	public readonly onDispose = this.#onDisposeEmitter.event;
 
-	private readonly _onDidChangeViewStateEmitter = this._register(new vscode.EventEmitter<vscode.WebviewPanelOnDidChangeViewStateEvent>());
-	public readonly onDidChangeViewState = this._onDidChangeViewStateEmitter.event;
+	readonly #onDidChangeViewStateEmitter = this._register(new vscode.EventEmitter<vscode.WebviewPanelOnDidChangeViewStateEvent>());
+	public readonly onDidChangeViewState = this.#onDidChangeViewStateEmitter.event;
 
 	override dispose() {
-		this._preview.dispose();
-		this._webviewPanel.dispose();
+		this.#preview.dispose();
+		this.#webviewPanel.dispose();
 
-		this._onDisposeEmitter.fire();
-		this._onDisposeEmitter.dispose();
+		this.#onDisposeEmitter.fire();
+		this.#onDisposeEmitter.dispose();
 		super.dispose();
 	}
 
 	public get resource() {
-		return this._preview.resource;
+		return this.#preview.resource;
 	}
 
 	public get resourceColumn() {
-		return this._resourceColumn;
+		return this.#resourceColumn;
 	}
 
 	public reveal(viewColumn: vscode.ViewColumn) {
-		this._webviewPanel.reveal(viewColumn);
+		this.#webviewPanel.reveal(viewColumn);
 	}
 
 	public refresh() {
-		this._preview.refresh(true);
+		this.#preview.refresh(true);
 	}
 
 	public updateConfiguration() {
-		if (this._previewConfigurations.hasConfigurationChanged(this._preview.resource)) {
+		if (this.#previewConfigurations.hasConfigurationChanged(this.#preview.resource)) {
 			this.refresh();
 		}
 	}
 
 	public update(newResource: vscode.Uri, scrollLocation?: StartingScrollLocation) {
-		if (this._preview.isPreviewOf(newResource)) {
+		if (this.#preview.isPreviewOf(newResource)) {
 			switch (scrollLocation?.type) {
 				case 'line':
-					this._preview.scrollTo(scrollLocation.line);
+					this.#preview.scrollTo(scrollLocation.line);
 					return;
 
 				case 'fragment':
@@ -744,16 +779,16 @@ export class DynamicMarkdownPreview extends Disposable implements IManagedMarkdo
 			}
 		}
 
-		this._preview.dispose();
-		this._preview = this._createPreview(newResource, scrollLocation);
+		this.#preview.dispose();
+		this.#preview = this.#createPreview(newResource, scrollLocation);
 	}
 
 	public toggleLock() {
-		this._locked = !this._locked;
-		this._webviewPanel.title = DynamicMarkdownPreview._getPreviewTitle(this._preview.resource, this._locked);
+		this.#locked = !this.#locked;
+		this.#webviewPanel.title = DynamicMarkdownPreview.#getPreviewTitle(this.#preview.resource, this.#locked);
 	}
 
-	private static _getPreviewTitle(resource: vscode.Uri, locked: boolean): string {
+	static #getPreviewTitle(resource: vscode.Uri, locked: boolean): string {
 		const resourceLabel = uri.Utils.basename(resource);
 		return locked
 			? vscode.l10n.t('[Preview] {0}', resourceLabel)
@@ -761,7 +796,7 @@ export class DynamicMarkdownPreview extends Disposable implements IManagedMarkdo
 	}
 
 	public get position(): vscode.ViewColumn | undefined {
-		return this._webviewPanel.viewColumn;
+		return this.#webviewPanel.viewColumn;
 	}
 
 	public matchesResource(
@@ -773,34 +808,34 @@ export class DynamicMarkdownPreview extends Disposable implements IManagedMarkdo
 			return false;
 		}
 
-		if (this._locked) {
-			return otherLocked && this._preview.isPreviewOf(otherResource);
+		if (this.#locked) {
+			return otherLocked && this.#preview.isPreviewOf(otherResource);
 		} else {
 			return !otherLocked;
 		}
 	}
 
 	public matches(otherPreview: DynamicMarkdownPreview): boolean {
-		return this.matchesResource(otherPreview._preview.resource, otherPreview.position, otherPreview._locked);
+		return this.matchesResource(otherPreview.#preview.resource, otherPreview.position, otherPreview.#locked);
 	}
 
-	private _createPreview(resource: vscode.Uri, startingScroll?: StartingScrollLocation): MarkdownPreview {
-		return new MarkdownPreview(this._webviewPanel, resource, startingScroll, {
-			getTitle: (resource) => DynamicMarkdownPreview._getPreviewTitle(resource, this._locked),
+	#createPreview(resource: vscode.Uri, startingScroll?: StartingScrollLocation): MarkdownPreview {
+		return new MarkdownPreview(this.#webviewPanel, resource, startingScroll, {
+			getTitle: (resource) => DynamicMarkdownPreview.#getPreviewTitle(resource, this.#locked),
 			getAdditionalState: () => {
 				return {
 					resourceColumn: this.resourceColumn,
-					locked: this._locked,
+					locked: this.#locked,
 				};
 			},
 			openPreviewLinkToMarkdownFile: (link: vscode.Uri, fragment?: string) => {
 				this.update(link, fragment ? new StartingScrollFragment(fragment) : undefined);
 			}
 		},
-			this._contentProvider,
-			this._previewConfigurations,
-			this._logger,
-			this._contributionProvider,
-			this._opener);
+			this.#contentProvider,
+			this.#previewConfigurations,
+			this.#logger,
+			this.#contributionProvider,
+			this.#opener);
 	}
 }
diff --git a/extensions/markdown-language-features/src/preview/previewConfig.ts b/extensions/markdown-language-features/src/preview/previewConfig.ts
index 01d6340337763..ac240b97eb71c 100644
--- a/extensions/markdown-language-features/src/preview/previewConfig.ts
+++ b/extensions/markdown-language-features/src/preview/previewConfig.ts
@@ -73,24 +73,24 @@ export class MarkdownPreviewConfiguration {
 }
 
 export class MarkdownPreviewConfigurationManager {
-	private readonly _previewConfigurationsForWorkspaces = new Map<string, MarkdownPreviewConfiguration>();
+	readonly #previewConfigurationsForWorkspaces = new Map<string, MarkdownPreviewConfiguration>();
 
 	public loadAndCacheConfiguration(
 		resource: vscode.Uri
 	): MarkdownPreviewConfiguration {
 		const config = MarkdownPreviewConfiguration.getForResource(resource);
-		this._previewConfigurationsForWorkspaces.set(this._getKey(resource), config);
+		this.#previewConfigurationsForWorkspaces.set(this.#getKey(resource), config);
 		return config;
 	}
 
 	public hasConfigurationChanged(resource: vscode.Uri): boolean {
-		const key = this._getKey(resource);
-		const currentConfig = this._previewConfigurationsForWorkspaces.get(key);
+		const key = this.#getKey(resource);
+		const currentConfig = this.#previewConfigurationsForWorkspaces.get(key);
 		const newConfig = MarkdownPreviewConfiguration.getForResource(resource);
 		return !currentConfig?.isEqualTo(newConfig);
 	}
 
-	private _getKey(
+	#getKey(
 		resource: vscode.Uri
 	): string {
 		const folder = vscode.workspace.getWorkspaceFolder(resource);
diff --git a/extensions/markdown-language-features/src/preview/previewManager.ts b/extensions/markdown-language-features/src/preview/previewManager.ts
index 3aa126da063d6..cc1f7fda40b63 100644
--- a/extensions/markdown-language-features/src/preview/previewManager.ts
+++ b/extensions/markdown-language-features/src/preview/previewManager.ts
@@ -24,23 +24,23 @@ export interface DynamicPreviewSettings {
 
 class PreviewStore<T extends IManagedMarkdownPreview> extends Disposable {
 
-	private readonly _previews = new Set<T>();
+	readonly #previews = new Set<T>();
 
 	public override dispose(): void {
 		super.dispose();
-		for (const preview of this._previews) {
+		for (const preview of this.#previews) {
 			preview.dispose();
 		}
-		this._previews.clear();
+		this.#previews.clear();
 	}
 
 	[Symbol.iterator](): Iterator<T> {
-		return this._previews[Symbol.iterator]();
+		return this.#previews[Symbol.iterator]();
 	}
 
 	public get(resource: vscode.Uri, previewSettings: DynamicPreviewSettings): T | undefined {
-		const previewColumn = this._resolvePreviewColumn(previewSettings);
-		for (const preview of this._previews) {
+		const previewColumn = this.#resolvePreviewColumn(previewSettings);
+		for (const preview of this.#previews) {
 			if (preview.matchesResource(resource, previewColumn, previewSettings.locked)) {
 				return preview;
 			}
@@ -49,14 +49,14 @@ class PreviewStore<T extends IManagedMarkdownPreview> extends Disposable {
 	}
 
 	public add(preview: T) {
-		this._previews.add(preview);
+		this.#previews.add(preview);
 	}
 
 	public delete(preview: T) {
-		this._previews.delete(preview);
+		this.#previews.delete(preview);
 	}
 
-	private _resolvePreviewColumn(previewSettings: DynamicPreviewSettings): vscode.ViewColumn | undefined {
+	#resolvePreviewColumn(previewSettings: DynamicPreviewSettings): vscode.ViewColumn | undefined {
 		if (previewSettings.previewColumn === vscode.ViewColumn.Active) {
 			return vscode.window.tabGroups.activeTabGroup.viewColumn;
 		}
@@ -71,22 +71,32 @@ class PreviewStore<T extends IManagedMarkdownPreview> extends Disposable {
 
 export class MarkdownPreviewManager extends Disposable implements vscode.WebviewPanelSerializer, vscode.CustomTextEditorProvider {
 
-	private readonly _topmostLineMonitor = new TopmostLineMonitor();
-	private readonly _previewConfigurations = new MarkdownPreviewConfigurationManager();
+	readonly #topmostLineMonitor = new TopmostLineMonitor();
+	readonly #previewConfigurations = new MarkdownPreviewConfigurationManager();
 
-	private readonly _dynamicPreviews = this._register(new PreviewStore<DynamicMarkdownPreview>());
-	private readonly _staticPreviews = this._register(new PreviewStore<StaticMarkdownPreview>());
+	readonly #dynamicPreviews = this._register(new PreviewStore<DynamicMarkdownPreview>());
+	readonly #staticPreviews = this._register(new PreviewStore<StaticMarkdownPreview>());
 
-	private _activePreview: IManagedMarkdownPreview | undefined = undefined;
+	#activePreview: IManagedMarkdownPreview | undefined = undefined;
+
+	readonly #contentProvider: MdDocumentRenderer;
+	readonly #logger: ILogger;
+	readonly #contributions: MarkdownContributionProvider;
+	readonly #opener: MdLinkOpener;
 
 	public constructor(
-		private readonly _contentProvider: MdDocumentRenderer,
-		private readonly _logger: ILogger,
-		private readonly _contributions: MarkdownContributionProvider,
-		private readonly _opener: MdLinkOpener,
+		contentProvider: MdDocumentRenderer,
+		logger: ILogger,
+		contributions: MarkdownContributionProvider,
+		opener: MdLinkOpener,
 	) {
 		super();
 
+		this.#contentProvider = contentProvider;
+		this.#logger = logger;
+		this.#contributions = contributions;
+		this.#opener = opener;
+
 		this._register(vscode.window.registerWebviewPanelSerializer(DynamicMarkdownPreview.viewType, this));
 
 		this._register(vscode.window.registerCustomEditorProvider(StaticMarkdownPreview.customEditorViewType, this, {
@@ -96,7 +106,7 @@ export class MarkdownPreviewManager extends Disposable implements vscode.Webview
 		this._register(vscode.window.onDidChangeActiveTextEditor(textEditor => {
 			// When at a markdown file, apply existing scroll settings
 			if (textEditor?.document && isMarkdownFile(textEditor.document)) {
-				const line = this._topmostLineMonitor.getPreviousStaticEditorLineByUri(textEditor.document.uri);
+				const line = this.#topmostLineMonitor.getPreviousStaticEditorLineByUri(textEditor.document.uri);
 				if (typeof line === 'number') {
 					scrollEditorToLine(line, textEditor);
 				}
@@ -105,19 +115,19 @@ export class MarkdownPreviewManager extends Disposable implements vscode.Webview
 	}
 
 	public refresh() {
-		for (const preview of this._dynamicPreviews) {
+		for (const preview of this.#dynamicPreviews) {
 			preview.refresh();
 		}
-		for (const preview of this._staticPreviews) {
+		for (const preview of this.#staticPreviews) {
 			preview.refresh();
 		}
 	}
 
 	public updateConfiguration() {
-		for (const preview of this._dynamicPreviews) {
+		for (const preview of this.#dynamicPreviews) {
 			preview.updateConfiguration();
 		}
-		for (const preview of this._staticPreviews) {
+		for (const preview of this.#staticPreviews) {
 			preview.updateConfiguration();
 		}
 	}
@@ -126,11 +136,11 @@ export class MarkdownPreviewManager extends Disposable implements vscode.Webview
 		resource: vscode.Uri,
 		settings: DynamicPreviewSettings
 	): void {
-		let preview = this._dynamicPreviews.get(resource, settings);
+		let preview = this.#dynamicPreviews.get(resource, settings);
 		if (preview) {
 			preview.reveal(settings.previewColumn);
 		} else {
-			preview = this._createNewDynamicPreview(resource, settings);
+			preview = this.#createNewDynamicPreview(resource, settings);
 		}
 
 		preview.update(
@@ -140,15 +150,15 @@ export class MarkdownPreviewManager extends Disposable implements vscode.Webview
 	}
 
 	public get activePreviewResource() {
-		return this._activePreview?.resource;
+		return this.#activePreview?.resource;
 	}
 
 	public get activePreviewResourceColumn() {
-		return this._activePreview?.resourceColumn;
+		return this.#activePreview?.resourceColumn;
 	}
 
 	public findPreview(resource: vscode.Uri): IManagedMarkdownPreview | undefined {
-		for (const preview of [...this._dynamicPreviews, ...this._staticPreviews]) {
+		for (const preview of [...this.#dynamicPreviews, ...this.#staticPreviews]) {
 			if (preview.resource.fsPath === resource.fsPath) {
 				return preview;
 			}
@@ -157,12 +167,12 @@ export class MarkdownPreviewManager extends Disposable implements vscode.Webview
 	}
 
 	public toggleLock() {
-		const preview = this._activePreview;
+		const preview = this.#activePreview;
 		if (preview instanceof DynamicMarkdownPreview) {
 			preview.toggleLock();
 
 			// Close any previews that are now redundant, such as having two dynamic previews in the same editor group
-			for (const otherPreview of this._dynamicPreviews) {
+			for (const otherPreview of this.#dynamicPreviews) {
 				if (otherPreview !== preview && preview.matches(otherPreview)) {
 					otherPreview.dispose();
 				}
@@ -172,7 +182,7 @@ export class MarkdownPreviewManager extends Disposable implements vscode.Webview
 
 	public openDocumentLink(linkText: string, fromResource: vscode.Uri) {
 		const viewColumn = this.findPreview(fromResource)?.resourceColumn;
-		return this._opener.openDocumentLink(linkText, fromResource, viewColumn);
+		return this.#opener.openDocumentLink(linkText, fromResource, viewColumn);
 	}
 
 	public async deserializeWebviewPanel(
@@ -188,14 +198,14 @@ export class MarkdownPreviewManager extends Disposable implements vscode.Webview
 			const preview = DynamicMarkdownPreview.revive(
 				{ resource, locked, line, resourceColumn },
 				webview,
-				this._contentProvider,
-				this._previewConfigurations,
-				this._logger,
-				this._topmostLineMonitor,
-				this._contributions,
-				this._opener);
-
-			this._registerDynamicPreview(preview);
+				this.#contentProvider,
+				this.#previewConfigurations,
+				this.#logger,
+				this.#topmostLineMonitor,
+				this.#contributions,
+				this.#opener);
+
+			this.#registerDynamicPreview(preview);
 		} catch (e) {
 			console.error(e);
 
@@ -237,23 +247,23 @@ export class MarkdownPreviewManager extends Disposable implements vscode.Webview
 		document: vscode.TextDocument,
 		webview: vscode.WebviewPanel
 	): Promise<void> {
-		const lineNumber = this._topmostLineMonitor.getPreviousStaticTextEditorLineByUri(document.uri);
+		const lineNumber = this.#topmostLineMonitor.getPreviousStaticTextEditorLineByUri(document.uri);
 		const preview = StaticMarkdownPreview.revive(
 			document.uri,
 			webview,
-			this._contentProvider,
-			this._previewConfigurations,
-			this._topmostLineMonitor,
-			this._logger,
-			this._contributions,
-			this._opener,
+			this.#contentProvider,
+			this.#previewConfigurations,
+			this.#topmostLineMonitor,
+			this.#logger,
+			this.#contributions,
+			this.#opener,
 			lineNumber
 		);
-		this._registerStaticPreview(preview);
-		this._activePreview = preview;
+		this.#registerStaticPreview(preview);
+		this.#activePreview = preview;
 	}
 
-	private _createNewDynamicPreview(
+	#createNewDynamicPreview(
 		resource: vscode.Uri,
 		previewSettings: DynamicPreviewSettings
 	): DynamicMarkdownPreview {
@@ -267,52 +277,52 @@ export class MarkdownPreviewManager extends Disposable implements vscode.Webview
 				line: scrollLine,
 			},
 			previewSettings.previewColumn,
-			this._contentProvider,
-			this._previewConfigurations,
-			this._logger,
-			this._topmostLineMonitor,
-			this._contributions,
-			this._opener);
-
-		this._activePreview = preview;
-		return this._registerDynamicPreview(preview);
+			this.#contentProvider,
+			this.#previewConfigurations,
+			this.#logger,
+			this.#topmostLineMonitor,
+			this.#contributions,
+			this.#opener);
+
+		this.#activePreview = preview;
+		return this.#registerDynamicPreview(preview);
 	}
 
-	private _registerDynamicPreview(preview: DynamicMarkdownPreview): DynamicMarkdownPreview {
-		this._dynamicPreviews.add(preview);
+	#registerDynamicPreview(preview: DynamicMarkdownPreview): DynamicMarkdownPreview {
+		this.#dynamicPreviews.add(preview);
 
 		preview.onDispose(() => {
-			this._dynamicPreviews.delete(preview);
+			this.#dynamicPreviews.delete(preview);
 		});
 
-		this._trackActive(preview);
+		this.#trackActive(preview);
 
 		preview.onDidChangeViewState(() => {
 			// Remove other dynamic previews in our column
-			disposeAll(Array.from(this._dynamicPreviews).filter(otherPreview => preview !== otherPreview && preview.matches(otherPreview)));
+			disposeAll(Array.from(this.#dynamicPreviews).filter(otherPreview => preview !== otherPreview && preview.matches(otherPreview)));
 		});
 		return preview;
 	}
 
-	private _registerStaticPreview(preview: StaticMarkdownPreview): StaticMarkdownPreview {
-		this._staticPreviews.add(preview);
+	#registerStaticPreview(preview: StaticMarkdownPreview): StaticMarkdownPreview {
+		this.#staticPreviews.add(preview);
 
 		preview.onDispose(() => {
-			this._staticPreviews.delete(preview);
+			this.#staticPreviews.delete(preview);
 		});
 
-		this._trackActive(preview);
+		this.#trackActive(preview);
 		return preview;
 	}
 
-	private _trackActive(preview: IManagedMarkdownPreview): void {
+	#trackActive(preview: IManagedMarkdownPreview): void {
 		preview.onDidChangeViewState(({ webviewPanel }) => {
-			this._activePreview = webviewPanel.active ? preview : undefined;
+			this.#activePreview = webviewPanel.active ? preview : undefined;
 		});
 
 		preview.onDispose(() => {
-			if (this._activePreview === preview) {
-				this._activePreview = undefined;
+			if (this.#activePreview === preview) {
+				this.#activePreview = undefined;
 			}
 		});
 	}
diff --git a/extensions/markdown-language-features/src/preview/security.ts b/extensions/markdown-language-features/src/preview/security.ts
index 0ba1a9f61f087..292e19563c90f 100644
--- a/extensions/markdown-language-features/src/preview/security.ts
+++ b/extensions/markdown-language-features/src/preview/security.ts
@@ -27,31 +27,37 @@ export interface ContentSecurityPolicyArbiter {
 }
 
 export class ExtensionContentSecurityPolicyArbiter implements ContentSecurityPolicyArbiter {
-	private readonly _old_trusted_workspace_key = 'trusted_preview_workspace:';
-	private readonly _security_level_key = 'preview_security_level:';
-	private readonly _should_disable_security_warning_key = 'preview_should_show_security_warning:';
+	readonly #old_trusted_workspace_key = 'trusted_preview_workspace:';
+	readonly #security_level_key = 'preview_security_level:';
+	readonly #should_disable_security_warning_key = 'preview_should_show_security_warning:';
+
+	readonly #globalState: vscode.Memento;
+	readonly #workspaceState: vscode.Memento;
 
 	constructor(
-		private readonly _globalState: vscode.Memento,
-		private readonly _workspaceState: vscode.Memento
-	) { }
+		globalState: vscode.Memento,
+		workspaceState: vscode.Memento
+	) {
+		this.#globalState = globalState;
+		this.#workspaceState = workspaceState;
+	}
 
 	public getSecurityLevelForResource(resource: vscode.Uri): MarkdownPreviewSecurityLevel {
 		// Use new security level setting first
-		const level = this._globalState.get<MarkdownPreviewSecurityLevel | undefined>(this._security_level_key + this._getRoot(resource), undefined);
+		const level = this.#globalState.get<MarkdownPreviewSecurityLevel | undefined>(this.#security_level_key + this.#getRoot(resource), undefined);
 		if (typeof level !== 'undefined') {
 			return level;
 		}
 
 		// Fallback to old trusted workspace setting
-		if (this._globalState.get<boolean>(this._old_trusted_workspace_key + this._getRoot(resource), false)) {
+		if (this.#globalState.get<boolean>(this.#old_trusted_workspace_key + this.#getRoot(resource), false)) {
 			return MarkdownPreviewSecurityLevel.AllowScriptsAndAllContent;
 		}
 		return MarkdownPreviewSecurityLevel.Strict;
 	}
 
 	public setSecurityLevelForResource(resource: vscode.Uri, level: MarkdownPreviewSecurityLevel): Thenable<void> {
-		return this._globalState.update(this._security_level_key + this._getRoot(resource), level);
+		return this.#globalState.update(this.#security_level_key + this.#getRoot(resource), level);
 	}
 
 	public shouldAllowSvgsForResource(resource: vscode.Uri) {
@@ -60,14 +66,14 @@ export class ExtensionContentSecurityPolicyArbiter implements ContentSecurityPol
 	}
 
 	public shouldDisableSecurityWarnings(): boolean {
-		return this._workspaceState.get<boolean>(this._should_disable_security_warning_key, false);
+		return this.#workspaceState.get<boolean>(this.#should_disable_security_warning_key, false);
 	}
 
 	public setShouldDisableSecurityWarning(disabled: boolean): Thenable<void> {
-		return this._workspaceState.update(this._should_disable_security_warning_key, disabled);
+		return this.#workspaceState.update(this.#should_disable_security_warning_key, disabled);
 	}
 
-	private _getRoot(resource: vscode.Uri): vscode.Uri {
+	#getRoot(resource: vscode.Uri): vscode.Uri {
 		if (vscode.workspace.workspaceFolders) {
 			const folderForResource = vscode.workspace.getWorkspaceFolder(resource);
 			if (folderForResource) {
@@ -85,10 +91,16 @@ export class ExtensionContentSecurityPolicyArbiter implements ContentSecurityPol
 
 export class PreviewSecuritySelector {
 
+	readonly #cspArbiter: ContentSecurityPolicyArbiter;
+	readonly #webviewManager: MarkdownPreviewManager;
+
 	public constructor(
-		private readonly _cspArbiter: ContentSecurityPolicyArbiter,
-		private readonly _webviewManager: MarkdownPreviewManager
-	) { }
+		cspArbiter: ContentSecurityPolicyArbiter,
+		webviewManager: MarkdownPreviewManager
+	) {
+		this.#cspArbiter = cspArbiter;
+		this.#webviewManager = webviewManager;
+	}
 
 	public async showSecuritySelectorForResource(resource: vscode.Uri): Promise<void> {
 		interface PreviewSecurityPickItem extends vscode.QuickPickItem {
@@ -99,7 +111,7 @@ export class PreviewSecuritySelector {
 			return when ? '• ' : '';
 		}
 
-		const currentSecurityLevel = this._cspArbiter.getSecurityLevelForResource(resource);
+		const currentSecurityLevel = this.#cspArbiter.getSecurityLevelForResource(resource);
 		const selection = await vscode.window.showQuickPick<PreviewSecurityPickItem>(
 			[
 				{
@@ -124,7 +136,7 @@ export class PreviewSecuritySelector {
 					description: ''
 				}, {
 					type: 'toggle',
-					label: this._cspArbiter.shouldDisableSecurityWarnings()
+					label: this.#cspArbiter.shouldDisableSecurityWarnings()
 						? vscode.l10n.t("Enable preview security warnings in this workspace")
 						: vscode.l10n.t("Disable preview security warning in this workspace"),
 					description: vscode.l10n.t("Does not affect the content security level")
@@ -142,12 +154,12 @@ export class PreviewSecuritySelector {
 		}
 
 		if (selection.type === 'toggle') {
-			this._cspArbiter.setShouldDisableSecurityWarning(!this._cspArbiter.shouldDisableSecurityWarnings());
-			this._webviewManager.refresh();
+			this.#cspArbiter.setShouldDisableSecurityWarning(!this.#cspArbiter.shouldDisableSecurityWarnings());
+			this.#webviewManager.refresh();
 			return;
 		} else {
-			await this._cspArbiter.setSecurityLevelForResource(resource, selection.type);
+			await this.#cspArbiter.setSecurityLevelForResource(resource, selection.type);
 		}
-		this._webviewManager.refresh();
+		this.#webviewManager.refresh();
 	}
 }
diff --git a/extensions/markdown-language-features/src/preview/topmostLineMonitor.ts b/extensions/markdown-language-features/src/preview/topmostLineMonitor.ts
index d676fa9ffbcfa..59fdbb13cfd9b 100644
--- a/extensions/markdown-language-features/src/preview/topmostLineMonitor.ts
+++ b/extensions/markdown-language-features/src/preview/topmostLineMonitor.ts
@@ -15,10 +15,10 @@ export interface LastScrollLocation {
 
 export class TopmostLineMonitor extends Disposable {
 
-	private readonly _pendingUpdates = new ResourceMap<number>();
-	private readonly _throttle = 50;
-	private readonly _previousTextEditorInfo = new ResourceMap<LastScrollLocation>();
-	private readonly _previousStaticEditorInfo = new ResourceMap<LastScrollLocation>();
+	readonly #pendingUpdates = new ResourceMap<number>();
+	readonly #throttle = 50;
+	readonly #previousTextEditorInfo = new ResourceMap<LastScrollLocation>();
+	readonly #previousStaticEditorInfo = new ResourceMap<LastScrollLocation>();
 
 	constructor() {
 		super();
@@ -39,32 +39,32 @@ export class TopmostLineMonitor extends Disposable {
 		}));
 	}
 
-	private readonly _onChanged = this._register(new vscode.EventEmitter<{ readonly resource: vscode.Uri; readonly line: number }>());
-	public readonly onDidChanged = this._onChanged.event;
+	readonly #onChanged = this._register(new vscode.EventEmitter<{ readonly resource: vscode.Uri; readonly line: number }>());
+	public readonly onDidChanged = this.#onChanged.event;
 
 	public setPreviousStaticEditorLine(scrollLocation: LastScrollLocation): void {
-		this._previousStaticEditorInfo.set(scrollLocation.uri, scrollLocation);
+		this.#previousStaticEditorInfo.set(scrollLocation.uri, scrollLocation);
 	}
 
 	public getPreviousStaticEditorLineByUri(resource: vscode.Uri): number | undefined {
-		const scrollLoc = this._previousStaticEditorInfo.get(resource);
-		this._previousStaticEditorInfo.delete(resource);
+		const scrollLoc = this.#previousStaticEditorInfo.get(resource);
+		this.#previousStaticEditorInfo.delete(resource);
 		return scrollLoc?.line;
 	}
 
 
 	public setPreviousTextEditorLine(scrollLocation: LastScrollLocation): void {
-		this._previousTextEditorInfo.set(scrollLocation.uri, scrollLocation);
+		this.#previousTextEditorInfo.set(scrollLocation.uri, scrollLocation);
 	}
 
 	public getPreviousTextEditorLineByUri(resource: vscode.Uri): number | undefined {
-		const scrollLoc = this._previousTextEditorInfo.get(resource);
-		this._previousTextEditorInfo.delete(resource);
+		const scrollLoc = this.#previousTextEditorInfo.get(resource);
+		this.#previousTextEditorInfo.delete(resource);
 		return scrollLoc?.line;
 	}
 
 	public getPreviousStaticTextEditorLineByUri(resource: vscode.Uri): number | undefined {
-		const state = this._previousStaticEditorInfo.get(resource);
+		const state = this.#previousStaticEditorInfo.get(resource);
 		return state?.line;
 	}
 
@@ -72,20 +72,20 @@ export class TopmostLineMonitor extends Disposable {
 		resource: vscode.Uri,
 		line: number
 	) {
-		if (!this._pendingUpdates.has(resource)) {
+		if (!this.#pendingUpdates.has(resource)) {
 			// schedule update
 			setTimeout(() => {
-				if (this._pendingUpdates.has(resource)) {
-					this._onChanged.fire({
+				if (this.#pendingUpdates.has(resource)) {
+					this.#onChanged.fire({
 						resource,
-						line: this._pendingUpdates.get(resource) as number
+						line: this.#pendingUpdates.get(resource) as number
 					});
-					this._pendingUpdates.delete(resource);
+					this.#pendingUpdates.delete(resource);
 				}
-			}, this._throttle);
+			}, this.#throttle);
 		}
 
-		this._pendingUpdates.set(resource, line);
+		this.#pendingUpdates.set(resource, line);
 	}
 }
 
diff --git a/extensions/markdown-language-features/src/telemetryReporter.ts b/extensions/markdown-language-features/src/telemetryReporter.ts
index 808acc4ceab99..059e468aa546b 100644
--- a/extensions/markdown-language-features/src/telemetryReporter.ts
+++ b/extensions/markdown-language-features/src/telemetryReporter.ts
@@ -24,21 +24,21 @@ const nullReporter = new class NullTelemetryReporter implements TelemetryReporte
 };
 
 class ExtensionReporter implements TelemetryReporter {
-	private readonly _reporter: VSCodeTelemetryReporter;
+	readonly #reporter: VSCodeTelemetryReporter;
 
 	constructor(
 		packageInfo: IPackageInfo
 	) {
-		this._reporter = new VSCodeTelemetryReporter(packageInfo.aiKey);
+		this.#reporter = new VSCodeTelemetryReporter(packageInfo.aiKey);
 	}
 	sendTelemetryEvent(eventName: string, properties?: {
 		[key: string]: string;
 	}) {
-		this._reporter.sendTelemetryEvent(eventName, properties);
+		this.#reporter.sendTelemetryEvent(eventName, properties);
 	}
 
 	dispose() {
-		this._reporter.dispose();
+		this.#reporter.dispose();
 	}
 }
 
diff --git a/extensions/markdown-language-features/src/test/engine.ts b/extensions/markdown-language-features/src/test/engine.ts
index 31d780850b5fb..7778ab7b05ff2 100644
--- a/extensions/markdown-language-features/src/test/engine.ts
+++ b/extensions/markdown-language-features/src/test/engine.ts
@@ -13,11 +13,11 @@ const emptyContributions = new class implements MarkdownContributionProvider {
 	readonly extensionUri = vscode.Uri.file('/');
 	readonly contributions = MarkdownContributions.Empty;
 
-	private readonly _onContributionsChanged = new vscode.EventEmitter<this>();
-	readonly onContributionsChanged = this._onContributionsChanged.event;
+	readonly #onContributionsChanged = new vscode.EventEmitter<this>();
+	readonly onContributionsChanged = this.#onContributionsChanged.event;
 
 	dispose() {
-		this._onContributionsChanged.dispose();
+		this.#onContributionsChanged.dispose();
 	}
 };
 
diff --git a/extensions/markdown-language-features/src/util/async.ts b/extensions/markdown-language-features/src/util/async.ts
index 49bcbe6402bd0..90b2a40ed2cbf 100644
--- a/extensions/markdown-language-features/src/util/async.ts
+++ b/extensions/markdown-language-features/src/util/async.ts
@@ -10,55 +10,55 @@ export interface ITask<T> {
 export class Delayer<T> {
 
 	public defaultDelay: number;
-	private _timeout: any; // Timer
-	private _cancelTimeout: Promise<T | null> | null;
-	private _onSuccess: ((value: T | PromiseLike<T> | undefined) => void) | null;
-	private _task: ITask<T> | null;
+	#timeout: any; // Timer
+	#cancelTimeout: Promise<T | null> | null;
+	#onSuccess: ((value: T | PromiseLike<T> | undefined) => void) | null;
+	#task: ITask<T> | null;
 
 	constructor(defaultDelay: number) {
 		this.defaultDelay = defaultDelay;
-		this._timeout = null;
-		this._cancelTimeout = null;
-		this._onSuccess = null;
-		this._task = null;
+		this.#timeout = null;
+		this.#cancelTimeout = null;
+		this.#onSuccess = null;
+		this.#task = null;
 	}
 
 	dispose() {
-		this._doCancelTimeout();
+		this.#doCancelTimeout();
 	}
 
 	public trigger(task: ITask<T>, delay: number = this.defaultDelay): Promise<T | null> {
-		this._task = task;
+		this.#task = task;
 		if (delay >= 0) {
-			this._doCancelTimeout();
+			this.#doCancelTimeout();
 		}
 
-		if (!this._cancelTimeout) {
-			this._cancelTimeout = new Promise<T | undefined>((resolve) => {
-				this._onSuccess = resolve;
+		if (!this.#cancelTimeout) {
+			this.#cancelTimeout = new Promise<T | undefined>((resolve) => {
+				this.#onSuccess = resolve;
 			}).then(() => {
-				this._cancelTimeout = null;
-				this._onSuccess = null;
-				const result = this._task?.() ?? null;
-				this._task = null;
+				this.#cancelTimeout = null;
+				this.#onSuccess = null;
+				const result = this.#task?.() ?? null;
+				this.#task = null;
 				return result;
 			});
 		}
 
-		if (delay >= 0 || this._timeout === null) {
-			this._timeout = setTimeout(() => {
-				this._timeout = null;
-				this._onSuccess?.(undefined);
+		if (delay >= 0 || this.#timeout === null) {
+			this.#timeout = setTimeout(() => {
+				this.#timeout = null;
+				this.#onSuccess?.(undefined);
 			}, delay >= 0 ? delay : this.defaultDelay);
 		}
 
-		return this._cancelTimeout;
+		return this.#cancelTimeout;
 	}
 
-	private _doCancelTimeout(): void {
-		if (this._timeout !== null) {
-			clearTimeout(this._timeout);
-			this._timeout = null;
+	#doCancelTimeout(): void {
+		if (this.#timeout !== null) {
+			clearTimeout(this.#timeout);
+			this.#timeout = null;
 		}
 	}
 }
diff --git a/extensions/markdown-language-features/src/util/cancellation.ts b/extensions/markdown-language-features/src/util/cancellation.ts
index 45556cb6f1d4a..a0aa6583864e0 100644
--- a/extensions/markdown-language-features/src/util/cancellation.ts
+++ b/extensions/markdown-language-features/src/util/cancellation.ts
@@ -6,8 +6,8 @@
 import * as vscode from 'vscode';
 
 export const noopToken: vscode.CancellationToken = new class implements vscode.CancellationToken {
-	private readonly _onCancellationRequestedEmitter = new vscode.EventEmitter<void>();
-	onCancellationRequested = this._onCancellationRequestedEmitter.event;
+	readonly #onCancellationRequestedEmitter = new vscode.EventEmitter<void>();
+	onCancellationRequested = this.#onCancellationRequestedEmitter.event;
 
 	get isCancellationRequested() { return false; }
 };
diff --git a/extensions/markdown-language-features/src/util/dispose.ts b/extensions/markdown-language-features/src/util/dispose.ts
index f222642908e1f..064302623fd1e 100644
--- a/extensions/markdown-language-features/src/util/dispose.ts
+++ b/extensions/markdown-language-features/src/util/dispose.ts
@@ -28,20 +28,20 @@ export interface IDisposable {
 }
 
 export abstract class Disposable {
-	private _isDisposed = false;
+	#isDisposed = false;
 
 	protected _disposables: vscode.Disposable[] = [];
 
 	public dispose(): any {
-		if (this._isDisposed) {
+		if (this.#isDisposed) {
 			return;
 		}
-		this._isDisposed = true;
+		this.#isDisposed = true;
 		disposeAll(this._disposables);
 	}
 
 	protected _register<T extends IDisposable>(value: T): T {
-		if (this._isDisposed) {
+		if (this.#isDisposed) {
 			value.dispose();
 		} else {
 			this._disposables.push(value);
@@ -50,6 +50,6 @@ export abstract class Disposable {
 	}
 
 	protected get isDisposed() {
-		return this._isDisposed;
+		return this.#isDisposed;
 	}
 }
diff --git a/extensions/markdown-language-features/src/util/openDocumentLink.ts b/extensions/markdown-language-features/src/util/openDocumentLink.ts
index 285dd91029b44..20c0343171fad 100644
--- a/extensions/markdown-language-features/src/util/openDocumentLink.ts
+++ b/extensions/markdown-language-features/src/util/openDocumentLink.ts
@@ -14,21 +14,38 @@ enum OpenMarkdownLinks {
 
 export class MdLinkOpener {
 
+	readonly #client: MdLanguageClient;
+
 	constructor(
-		private readonly _client: MdLanguageClient,
-	) { }
+		client: MdLanguageClient,
+	) {
+		this.#client = client;
+	}
 
 	public async resolveDocumentLink(linkText: string, fromResource: vscode.Uri): Promise<proto.ResolvedDocumentLinkTarget> {
-		return this._client.resolveLinkTarget(linkText, fromResource);
+		return this.#client.resolveLinkTarget(linkText, fromResource);
 	}
 
 	public async openDocumentLink(linkText: string, fromResource: vscode.Uri, viewColumn?: vscode.ViewColumn): Promise<void> {
-		const resolved = await this._client.resolveLinkTarget(linkText, fromResource);
+		const resolved = await this.#client.resolveLinkTarget(linkText, fromResource);
 		if (!resolved) {
 			return;
 		}
 
-		const uri = vscode.Uri.from(resolved.uri);
+		let uri = vscode.Uri.from(resolved.uri);
+		let rangeSelection: vscode.Range | undefined;
+		if (resolved.kind === 'file' && !resolved.position) {
+			if (uri.fragment) {
+				rangeSelection = getSelectionFromLocationFragment(uri.fragment);
+			} else {
+				const locationFragment = getLocationFragmentFromLinkText(linkText);
+				if (locationFragment) {
+					uri = uri.with({ fragment: locationFragment });
+					rangeSelection = getSelectionFromLocationFragment(locationFragment);
+				}
+			}
+		}
+
 		switch (resolved.kind) {
 			case 'external':
 				return vscode.commands.executeCommand('vscode.open', uri);
@@ -50,7 +67,9 @@ export class MdLinkOpener {
 				}
 
 				return vscode.commands.executeCommand('vscode.open', uri, {
-					selection: resolved.position ? new vscode.Range(resolved.position.line, resolved.position.character, resolved.position.line, resolved.position.character) : undefined,
+					selection: resolved.position
+						? new vscode.Range(resolved.position.line, resolved.position.character, resolved.position.line, resolved.position.character)
+						: rangeSelection,
 					viewColumn: viewColumn ?? getViewColumn(fromResource),
 				} satisfies vscode.TextDocumentShowOptions);
 			}
@@ -58,6 +77,72 @@ export class MdLinkOpener {
 	}
 }
 
+function getSelectionFromLocationFragment(fragment: string): vscode.Range | undefined {
+	const match = /^L?(\d+)(?:,(\d+))?(?:-L?(\d+)(?:,(\d+))?)?$/i.exec(fragment);
+	if (!match) {
+		return undefined;
+	}
+
+	const startLineNumber = parseInt(match[1], 10);
+	if (isNaN(startLineNumber) || startLineNumber <= 0) {
+		return undefined;
+	}
+
+	const startColumn = match[2] ? parseInt(match[2], 10) : 1;
+	const endLineNumberRaw = match[3] ? parseInt(match[3], 10) : undefined;
+	if (typeof endLineNumberRaw !== 'undefined' && endLineNumberRaw <= 0) {
+		return undefined;
+	}
+	const endLineNumber = endLineNumberRaw;
+	const endColumn = match[3] ? (match[4] ? parseInt(match[4], 10) : 1) : undefined;
+
+	let normalizedStartLine = startLineNumber;
+	let normalizedStartColumn = startColumn;
+	let normalizedEndLine = endLineNumber;
+	let normalizedEndColumn = endColumn ?? 1;
+
+	if (typeof normalizedEndLine === 'number') {
+		if (normalizedEndLine < normalizedStartLine || (normalizedEndLine === normalizedStartLine && normalizedEndColumn < normalizedStartColumn)) {
+			const tmpLine = normalizedStartLine;
+			const tmpColumn = normalizedStartColumn;
+			normalizedStartLine = normalizedEndLine;
+			normalizedStartColumn = normalizedEndColumn;
+			normalizedEndLine = tmpLine;
+			normalizedEndColumn = tmpColumn;
+		}
+	}
+
+	const start = new vscode.Position(normalizedStartLine - 1, Math.max(0, normalizedStartColumn - 1));
+	const end = typeof normalizedEndLine === 'number'
+		? new vscode.Position(normalizedEndLine - 1, Math.max(0, normalizedEndColumn - 1))
+		: start;
+
+	return new vscode.Range(start, end);
+}
+
+function getLocationFragmentFromLinkText(linkText: string): string | undefined {
+	const fragmentStart = linkText.indexOf('#');
+	if (fragmentStart < 0) {
+		return undefined;
+	}
+
+	let fragment: string;
+	try {
+		fragment = decodeURIComponent(linkText.slice(fragmentStart + 1));
+	} catch {
+		return undefined;
+	}
+	if (!fragment) {
+		return undefined;
+	}
+
+	if (/^L?\d+(?:,\d+)?(?:-L?\d+(?:,\d+)?)?$/i.test(fragment)) {
+		return fragment;
+	}
+
+	return undefined;
+}
+
 function getViewColumn(resource: vscode.Uri): vscode.ViewColumn {
 	const config = vscode.workspace.getConfiguration('markdown', resource);
 	const openLinks = config.get<OpenMarkdownLinks>('links.openLocation', OpenMarkdownLinks.currentGroup);
diff --git a/extensions/markdown-language-features/src/util/resourceMap.ts b/extensions/markdown-language-features/src/util/resourceMap.ts
index 99dd71a8718b9..10eb8e2289041 100644
--- a/extensions/markdown-language-features/src/util/resourceMap.ts
+++ b/extensions/markdown-language-features/src/util/resourceMap.ts
@@ -11,53 +11,53 @@ const defaultResourceToKey = (resource: vscode.Uri): string => resource.toString
 
 export class ResourceMap<T> {
 
-	private readonly _map = new Map<string, { readonly uri: vscode.Uri; readonly value: T }>();
+	readonly #map = new Map<string, { readonly uri: vscode.Uri; readonly value: T }>();
 
-	private readonly _toKey: ResourceToKey;
+	readonly #toKey: ResourceToKey;
 
 	constructor(toKey: ResourceToKey = defaultResourceToKey) {
-		this._toKey = toKey;
+		this.#toKey = toKey;
 	}
 
 	public set(uri: vscode.Uri, value: T): this {
-		this._map.set(this._toKey(uri), { uri, value });
+		this.#map.set(this.#toKey(uri), { uri, value });
 		return this;
 	}
 
 	public get(resource: vscode.Uri): T | undefined {
-		return this._map.get(this._toKey(resource))?.value;
+		return this.#map.get(this.#toKey(resource))?.value;
 	}
 
 	public has(resource: vscode.Uri): boolean {
-		return this._map.has(this._toKey(resource));
+		return this.#map.has(this.#toKey(resource));
 	}
 
 	public get size(): number {
-		return this._map.size;
+		return this.#map.size;
 	}
 
 	public clear(): void {
-		this._map.clear();
+		this.#map.clear();
 	}
 
 	public delete(resource: vscode.Uri): boolean {
-		return this._map.delete(this._toKey(resource));
+		return this.#map.delete(this.#toKey(resource));
 	}
 
 	public *values(): IterableIterator<T> {
-		for (const entry of this._map.values()) {
+		for (const entry of this.#map.values()) {
 			yield entry.value;
 		}
 	}
 
 	public *keys(): IterableIterator<vscode.Uri> {
-		for (const entry of this._map.values()) {
+		for (const entry of this.#map.values()) {
 			yield entry.uri;
 		}
 	}
 
 	public *entries(): IterableIterator<[vscode.Uri, T]> {
-		for (const entry of this._map.values()) {
+		for (const entry of this.#map.values()) {
 			yield [entry.uri, entry.value];
 		}
 	}
diff --git a/extensions/markdown-language-features/src/util/resources.ts b/extensions/markdown-language-features/src/util/resources.ts
index f1f2d0886ab23..3edb0bdf48ff4 100644
--- a/extensions/markdown-language-features/src/util/resources.ts
+++ b/extensions/markdown-language-features/src/util/resources.ts
@@ -11,3 +11,22 @@ export interface WebviewResourceProvider {
 	readonly cspSource: string;
 }
 
+export function areUrisEqual(uri1: vscode.Uri, uri2: vscode.Uri): boolean {
+	if (uri1.scheme !== uri2.scheme) {
+		return false;
+	}
+
+	if (uri1.authority !== uri2.authority) {
+		return false;
+	}
+
+	if (uri1.scheme === 'file') {
+		if (process.platform === 'win32') {
+			return uri1.fsPath.toLowerCase() === uri2.fsPath.toLowerCase();
+		}
+
+		return uri1.fsPath === uri2.fsPath;
+	}
+
+	return uri1.toString() === uri2.toString();
+}
diff --git a/extensions/markdown-math/.npmrc b/extensions/markdown-math/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/markdown-math/.npmrc
+++ b/extensions/markdown-math/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/media-preview/.npmrc b/extensions/media-preview/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/media-preview/.npmrc
+++ b/extensions/media-preview/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/media-preview/.vscodeignore b/extensions/media-preview/.vscodeignore
index 8621eb9e9f489..ca6d6ff79d724 100644
--- a/extensions/media-preview/.vscodeignore
+++ b/extensions/media-preview/.vscodeignore
@@ -7,4 +7,3 @@ out/**
 cgmanifest.json
 package-lock.json
 preview-src/**
-webpack.config.js
diff --git a/extensions/merge-conflict/.npmrc b/extensions/merge-conflict/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/merge-conflict/.npmrc
+++ b/extensions/merge-conflict/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/mermaid-chat-features/.npmrc b/extensions/mermaid-chat-features/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/mermaid-chat-features/.npmrc
+++ b/extensions/mermaid-chat-features/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/mermaid-chat-features/.vscodeignore b/extensions/mermaid-chat-features/.vscodeignore
index 4722e5869901e..485bbd8df38c0 100644
--- a/extensions/mermaid-chat-features/.vscodeignore
+++ b/extensions/mermaid-chat-features/.vscodeignore
@@ -1,8 +1,6 @@
 src/**
-extension.webpack.config.js
 esbuild.*
 cgmanifest.json
 package-lock.json
-webpack.config.js
 tsconfig*.json
 .gitignore
diff --git a/extensions/mermaid-chat-features/package-lock.json b/extensions/mermaid-chat-features/package-lock.json
index 0d0bb2a582beb..23436bd9f005c 100644
--- a/extensions/mermaid-chat-features/package-lock.json
+++ b/extensions/mermaid-chat-features/package-lock.json
@@ -9,7 +9,7 @@
       "version": "10.0.0",
       "license": "MIT",
       "dependencies": {
-        "dompurify": "^3.2.7",
+        "dompurify": "^3.3.2",
         "mermaid": "^11.12.3"
       },
       "devDependencies": {
@@ -1016,10 +1016,13 @@
       }
     },
     "node_modules/dompurify": {
-      "version": "3.2.7",
-      "resolved": "https://registry.npmjs.org/dompurify/-/dompurify-3.2.7.tgz",
-      "integrity": "sha512-WhL/YuveyGXJaerVlMYGWhvQswa7myDG17P7Vu65EWC05o8vfeNbvNf4d/BOvH99+ZW+LlQsc1GDKMa1vNK6dw==",
+      "version": "3.3.2",
+      "resolved": "https://registry.npmjs.org/dompurify/-/dompurify-3.3.2.tgz",
+      "integrity": "sha512-6obghkliLdmKa56xdbLOpUZ43pAR6xFy1uOrxBaIDjT+yaRuuybLjGS9eVBoSR/UPU5fq3OXClEHLJNGvbxKpQ==",
       "license": "(MPL-2.0 OR Apache-2.0)",
+      "engines": {
+        "node": ">=20"
+      },
       "optionalDependencies": {
         "@types/trusted-types": "^2.0.7"
       }
diff --git a/extensions/mermaid-chat-features/package.json b/extensions/mermaid-chat-features/package.json
index 811bff8076d1f..68f5271fef668 100644
--- a/extensions/mermaid-chat-features/package.json
+++ b/extensions/mermaid-chat-features/package.json
@@ -130,7 +130,7 @@
     "@vscode/codicons": "^0.0.36"
   },
   "dependencies": {
-    "dompurify": "^3.2.7",
+    "dompurify": "^3.3.2",
     "mermaid": "^11.12.3"
   }
 }
diff --git a/extensions/microsoft-authentication/.npmrc b/extensions/microsoft-authentication/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/microsoft-authentication/.npmrc
+++ b/extensions/microsoft-authentication/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/microsoft-authentication/src/common/env.ts b/extensions/microsoft-authentication/src/common/env.ts
index 9460a27d2fea9..b63c94195a9e9 100644
--- a/extensions/microsoft-authentication/src/common/env.ts
+++ b/extensions/microsoft-authentication/src/common/env.ts
@@ -9,12 +9,15 @@ export const DEFAULT_REDIRECT_URI = 'https://vscode.dev/redirect';
 const VALID_DESKTOP_CALLBACK_SCHEMES = [
 	'vscode',
 	'vscode-insiders',
+	'vscode-exploration',
+	'vscode-sessions',
+	'vscode-sessions-insiders',
+	'vscode-sessions-exploration',
 	// On Windows, some browsers don't seem to redirect back to OSS properly.
 	// As a result, you get stuck in the auth flow. We exclude this from the
 	// list until we can figure out a way to fix this behavior in browsers.
 	// 'code-oss',
 	'vscode-wsl',
-	'vscode-exploration'
 ];
 
 export function isSupportedClient(uri: Uri): boolean {
diff --git a/extensions/notebook-renderers/.npmrc b/extensions/notebook-renderers/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/notebook-renderers/.npmrc
+++ b/extensions/notebook-renderers/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/notebook-renderers/package-lock.json b/extensions/notebook-renderers/package-lock.json
index beacde5ae213c..7908a9bf049b6 100644
--- a/extensions/notebook-renderers/package-lock.json
+++ b/extensions/notebook-renderers/package-lock.json
@@ -12,518 +12,393 @@
 				"@types/jsdom": "^21.1.0",
 				"@types/node": "^22.18.10",
 				"@types/vscode-notebook-renderer": "^1.60.0",
-				"jsdom": "^21.1.1"
+				"jsdom": "^28.1.0"
 			},
 			"engines": {
 				"vscode": "^1.57.0"
 			}
 		},
-		"node_modules/@tootallnate/once": {
-			"version": "2.0.0",
-			"resolved": "https://registry.npmjs.org/@tootallnate/once/-/once-2.0.0.tgz",
-			"integrity": "sha512-XCuKFP5PS55gnMVu3dty8KPatLqUoy/ZYzDzAGCQ8JNFCkLXzmI7vNHCR+XpbZaMWQK/vQubr7PkYq8g470J/A==",
+		"node_modules/@acemir/cssom": {
+			"version": "0.9.31",
+			"resolved": "https://registry.npmjs.org/@acemir/cssom/-/cssom-0.9.31.tgz",
+			"integrity": "sha512-ZnR3GSaH+/vJ0YlHau21FjfLYjMpYVIzTD8M8vIEQvIGxeOXyXdzCI140rrCY862p/C/BbzWsjc1dgnM9mkoTA==",
 			"dev": true,
-			"engines": {
-				"node": ">= 10"
-			}
+			"license": "MIT"
 		},
-		"node_modules/@types/jsdom": {
-			"version": "21.1.0",
-			"resolved": "https://registry.npmjs.org/@types/jsdom/-/jsdom-21.1.0.tgz",
-			"integrity": "sha512-leWreJOdnuIxq9Y70tBVm/bvTuh31DSlF/r4l7Cfi4uhVQqLHD0Q4v301GMisEMwwbMgF7ZKxuZ+Jbd4NcdmRw==",
+		"node_modules/@asamuzakjp/css-color": {
+			"version": "5.0.1",
+			"resolved": "https://registry.npmjs.org/@asamuzakjp/css-color/-/css-color-5.0.1.tgz",
+			"integrity": "sha512-2SZFvqMyvboVV1d15lMf7XiI3m7SDqXUuKaTymJYLN6dSGadqp+fVojqJlVoMlbZnlTmu3S0TLwLTJpvBMO1Aw==",
 			"dev": true,
+			"license": "MIT",
 			"dependencies": {
-				"@types/node": "*",
-				"@types/tough-cookie": "*",
-				"parse5": "^7.0.0"
+				"@csstools/css-calc": "^3.1.1",
+				"@csstools/css-color-parser": "^4.0.2",
+				"@csstools/css-parser-algorithms": "^4.0.0",
+				"@csstools/css-tokenizer": "^4.0.0",
+				"lru-cache": "^11.2.6"
+			},
+			"engines": {
+				"node": "^20.19.0 || ^22.12.0 || >=24.0.0"
 			}
 		},
-		"node_modules/@types/node": {
-			"version": "22.18.10",
-			"resolved": "https://registry.npmjs.org/@types/node/-/node-22.18.10.tgz",
-			"integrity": "sha512-anNG/V/Efn/YZY4pRzbACnKxNKoBng2VTFydVu8RRs5hQjikP8CQfaeAV59VFSCzKNp90mXiVXW2QzV56rwMrg==",
+		"node_modules/@asamuzakjp/dom-selector": {
+			"version": "6.8.1",
+			"resolved": "https://registry.npmjs.org/@asamuzakjp/dom-selector/-/dom-selector-6.8.1.tgz",
+			"integrity": "sha512-MvRz1nCqW0fsy8Qz4dnLIvhOlMzqDVBabZx6lH+YywFDdjXhMY37SmpV1XFX3JzG5GWHn63j6HX6QPr3lZXHvQ==",
 			"dev": true,
 			"license": "MIT",
 			"dependencies": {
-				"undici-types": "~6.21.0"
+				"@asamuzakjp/nwsapi": "^2.3.9",
+				"bidi-js": "^1.0.3",
+				"css-tree": "^3.1.0",
+				"is-potential-custom-element-name": "^1.0.1",
+				"lru-cache": "^11.2.6"
 			}
 		},
-		"node_modules/@types/tough-cookie": {
-			"version": "4.0.2",
-			"resolved": "https://registry.npmjs.org/@types/tough-cookie/-/tough-cookie-4.0.2.tgz",
-			"integrity": "sha512-Q5vtl1W5ue16D+nIaW8JWebSSraJVlK+EthKn7e7UcD4KWsaSJ8BqGPXNaPghgtcn/fhvrN17Tv8ksUsQpiplw==",
-			"dev": true
-		},
-		"node_modules/@types/vscode-notebook-renderer": {
-			"version": "1.60.0",
-			"resolved": "https://registry.npmjs.org/@types/vscode-notebook-renderer/-/vscode-notebook-renderer-1.60.0.tgz",
-			"integrity": "sha512-u7TD2uuEZTVuitx0iijOJdKI0JLiQP6PsSBSRy2XmHXUOXcp5p1S56NrjOEDoF+PIHd3NL3eO6KTRSf5nukDqQ==",
-			"dev": true
-		},
-		"node_modules/abab": {
-			"version": "2.0.6",
-			"resolved": "https://registry.npmjs.org/abab/-/abab-2.0.6.tgz",
-			"integrity": "sha512-j2afSsaIENvHZN2B8GOpF566vZ5WVk5opAiMTvWgaQT8DkbOqsTfvNAvHoRGU2zzP8cPoqys+xHTRDWW8L+/BA==",
-			"deprecated": "Use your platform's native atob() and btoa() methods instead",
-			"dev": true
-		},
-		"node_modules/acorn": {
-			"version": "8.8.2",
-			"resolved": "https://registry.npmjs.org/acorn/-/acorn-8.8.2.tgz",
-			"integrity": "sha512-xjIYgE8HBrkpd/sJqOGNspf8uHG+NOHGOw6a/Urj8taM2EXfdNAH2oFcPeIFfsv3+kz/mJrS5VuMqbNLjCa2vw==",
+		"node_modules/@asamuzakjp/nwsapi": {
+			"version": "2.3.9",
+			"resolved": "https://registry.npmjs.org/@asamuzakjp/nwsapi/-/nwsapi-2.3.9.tgz",
+			"integrity": "sha512-n8GuYSrI9bF7FFZ/SjhwevlHc8xaVlb/7HmHelnc/PZXBD2ZR49NnN9sMMuDdEGPeeRQ5d0hqlSlEpgCX3Wl0Q==",
 			"dev": true,
-			"bin": {
-				"acorn": "bin/acorn"
-			},
-			"engines": {
-				"node": ">=0.4.0"
-			}
+			"license": "MIT"
 		},
-		"node_modules/acorn-globals": {
-			"version": "7.0.1",
-			"resolved": "https://registry.npmjs.org/acorn-globals/-/acorn-globals-7.0.1.tgz",
-			"integrity": "sha512-umOSDSDrfHbTNPuNpC2NSnnA3LUrqpevPb4T9jRx4MagXNS0rs+gwiTcAvqCRmsD6utzsrzNt+ebm00SNWiC3Q==",
+		"node_modules/@bramus/specificity": {
+			"version": "2.4.2",
+			"resolved": "https://registry.npmjs.org/@bramus/specificity/-/specificity-2.4.2.tgz",
+			"integrity": "sha512-ctxtJ/eA+t+6q2++vj5j7FYX3nRu311q1wfYH3xjlLOsczhlhxAg2FWNUXhpGvAw3BWo1xBcvOV6/YLc2r5FJw==",
 			"dev": true,
+			"license": "MIT",
 			"dependencies": {
-				"acorn": "^8.1.0",
-				"acorn-walk": "^8.0.2"
+				"css-tree": "^3.0.0"
+			},
+			"bin": {
+				"specificity": "bin/cli.js"
 			}
 		},
-		"node_modules/acorn-walk": {
-			"version": "8.2.0",
-			"resolved": "https://registry.npmjs.org/acorn-walk/-/acorn-walk-8.2.0.tgz",
-			"integrity": "sha512-k+iyHEuPgSw6SbuDpGQM+06HQUa04DZ3o+F6CSzXMvvI5KMvnaEqXe+YVe555R9nn6GPt404fos4wcgpw12SDA==",
+		"node_modules/@csstools/color-helpers": {
+			"version": "6.0.2",
+			"resolved": "https://registry.npmjs.org/@csstools/color-helpers/-/color-helpers-6.0.2.tgz",
+			"integrity": "sha512-LMGQLS9EuADloEFkcTBR3BwV/CGHV7zyDxVRtVDTwdI2Ca4it0CCVTT9wCkxSgokjE5Ho41hEPgb8OEUwoXr6Q==",
 			"dev": true,
+			"funding": [
+				{
+					"type": "github",
+					"url": "https://github.com/sponsors/csstools"
+				},
+				{
+					"type": "opencollective",
+					"url": "https://opencollective.com/csstools"
+				}
+			],
+			"license": "MIT-0",
 			"engines": {
-				"node": ">=0.4.0"
+				"node": ">=20.19.0"
 			}
 		},
-		"node_modules/agent-base": {
-			"version": "6.0.2",
-			"resolved": "https://registry.npmjs.org/agent-base/-/agent-base-6.0.2.tgz",
-			"integrity": "sha512-RZNwNclF7+MS/8bDg70amg32dyeZGZxiDuQmZxKLAlQjr3jGyLx+4Kkk58UO7D2QdgFIQCovuSuZESne6RG6XQ==",
+		"node_modules/@csstools/css-calc": {
+			"version": "3.1.1",
+			"resolved": "https://registry.npmjs.org/@csstools/css-calc/-/css-calc-3.1.1.tgz",
+			"integrity": "sha512-HJ26Z/vmsZQqs/o3a6bgKslXGFAungXGbinULZO3eMsOyNJHeBBZfup5FiZInOghgoM4Hwnmw+OgbJCNg1wwUQ==",
 			"dev": true,
-			"dependencies": {
-				"debug": "4"
-			},
+			"funding": [
+				{
+					"type": "github",
+					"url": "https://github.com/sponsors/csstools"
+				},
+				{
+					"type": "opencollective",
+					"url": "https://opencollective.com/csstools"
+				}
+			],
+			"license": "MIT",
 			"engines": {
-				"node": ">= 6.0.0"
+				"node": ">=20.19.0"
+			},
+			"peerDependencies": {
+				"@csstools/css-parser-algorithms": "^4.0.0",
+				"@csstools/css-tokenizer": "^4.0.0"
 			}
 		},
-		"node_modules/asynckit": {
-			"version": "0.4.0",
-			"resolved": "https://registry.npmjs.org/asynckit/-/asynckit-0.4.0.tgz",
-			"integrity": "sha512-Oei9OH4tRh0YqU3GxhX79dM/mwVgvbZJaSNaRk+bshkj0S5cfHcgYakreBjrHwatXKbz+IoIdYLxrKim2MjW0Q==",
-			"dev": true
-		},
-		"node_modules/call-bind-apply-helpers": {
-			"version": "1.0.2",
-			"resolved": "https://registry.npmjs.org/call-bind-apply-helpers/-/call-bind-apply-helpers-1.0.2.tgz",
-			"integrity": "sha512-Sp1ablJ0ivDkSzjcaJdxEunN5/XvksFJ2sMBFfq6x0ryhQV/2b/KwFe21cMpmHtPOSij8K99/wSfoEuTObmuMQ==",
+		"node_modules/@csstools/css-color-parser": {
+			"version": "4.0.2",
+			"resolved": "https://registry.npmjs.org/@csstools/css-color-parser/-/css-color-parser-4.0.2.tgz",
+			"integrity": "sha512-0GEfbBLmTFf0dJlpsNU7zwxRIH0/BGEMuXLTCvFYxuL1tNhqzTbtnFICyJLTNK4a+RechKP75e7w42ClXSnJQw==",
 			"dev": true,
+			"funding": [
+				{
+					"type": "github",
+					"url": "https://github.com/sponsors/csstools"
+				},
+				{
+					"type": "opencollective",
+					"url": "https://opencollective.com/csstools"
+				}
+			],
 			"license": "MIT",
 			"dependencies": {
-				"es-errors": "^1.3.0",
-				"function-bind": "^1.1.2"
+				"@csstools/color-helpers": "^6.0.2",
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-			"dev": true
-		},
-		"node_modules/rrweb-cssom": {
-			"version": "0.6.0",
-			"resolved": "https://registry.npmjs.org/rrweb-cssom/-/rrweb-cssom-0.6.0.tgz",
-			"integrity": "sha512-APM0Gt1KoXBz0iIkkdB/kfvGOwC4UuJFeG/c+yV7wSc7q96cG/kJ0HiYCnzivD9SB53cLV1MlHFNfOuPaadYSw==",
-			"dev": true
-		},
-		"node_modules/safer-buffer": {
-			"version": "2.1.2",
-			"resolved": "https://registry.npmjs.org/safer-buffer/-/safer-buffer-2.1.2.tgz",
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-			"dev": true
-		},
 		"node_modules/saxes": {
 			"version": "6.0.0",
 			"resolved": "https://registry.npmjs.org/saxes/-/saxes-6.0.0.tgz",
@@ -722,12 +542,12 @@
 				"node": ">=v12.22.7"
 			}
 		},
-		"node_modules/source-map": {
-			"version": "0.6.1",
-			"resolved": "https://registry.npmjs.org/source-map/-/source-map-0.6.1.tgz",
-			"integrity": "sha512-UjgapumWlbMhkBgzT7Ykc5YXUT46F0iKu8SGXq0bcwP5dz/h0Plj6enJqjz1Zbq2l5WaqYnrVbwWOWMyF3F47g==",
+		"node_modules/source-map-js": {
+			"version": "1.2.1",
+			"resolved": "https://registry.npmjs.org/source-map-js/-/source-map-js-1.2.1.tgz",
+			"integrity": "sha512-UXWMKhLOwVKb728IUtQPXxfYU+usdybtUrK/8uGE8CQMvrhOpwvzDBwj0QhSL7MQc7vIsISBG8VQ8+IDQxpfQA==",
 			"dev": true,
-			"optional": true,
+			"license": "BSD-3-Clause",
 			"engines": {
 				"node": ">=0.10.0"
 			}
@@ -738,43 +558,60 @@
 			"integrity": "sha512-9QNk5KwDF+Bvz+PyObkmSYjI5ksVUYtjW7AU22r2NKcfLJcXp96hkDWU3+XndOsUb+AQ9QhfzfCT2O+CNWT5Tw==",
 			"dev": true
 		},
+		"node_modules/tldts": {
+			"version": "7.0.24",
+			"resolved": "https://registry.npmjs.org/tldts/-/tldts-7.0.24.tgz",
+			"integrity": "sha512-1r6vQTTt1rUiJkI5vX7KG8PR342Ru/5Oh13kEQP2SMbRSZpOey9SrBe27IDxkoWulx8ShWu4K6C0BkctP8Z1bQ==",
+			"dev": true,
+			"license": "MIT",
+			"dependencies": {
+				"tldts-core": "^7.0.24"
+			},
+			"bin": {
+				"tldts": "bin/cli.js"
+			}
+		},
+		"node_modules/tldts-core": {
+			"version": "7.0.24",
+			"resolved": "https://registry.npmjs.org/tldts-core/-/tldts-core-7.0.24.tgz",
+			"integrity": "sha512-pj7yygNMoMRqG7ML2SDQ0xNIOfN3IBDUcPVM2Sg6hP96oFNN2nqnzHreT3z9xLq85IWJyNTvD38O002DdOrPMw==",
+			"dev": true,
+			"license": "MIT"
+		},
 		"node_modules/tough-cookie": {
-			"version": "4.1.3",
-			"resolved": "https://registry.npmjs.org/tough-cookie/-/tough-cookie-4.1.3.tgz",
-			"integrity": "sha512-aX/y5pVRkfRnfmuX+OdbSdXvPe6ieKX/G2s7e98f4poJHnqH3281gDPm/metm6E/WRamfx7WC4HUqkWHfQHprw==",
+			"version": "6.0.0",
+			"resolved": "https://registry.npmjs.org/tough-cookie/-/tough-cookie-6.0.0.tgz",
+			"integrity": "sha512-kXuRi1mtaKMrsLUxz3sQYvVl37B0Ns6MzfrtV5DvJceE9bPyspOqk9xxv7XbZWcfLWbFmm997vl83qUWVJA64w==",
 			"dev": true,
+			"license": "BSD-3-Clause",
 			"dependencies": {
-				"psl": "^1.1.33",
-				"punycode": "^2.1.1",
-				"universalify": "^0.2.0",
-				"url-parse": "^1.5.3"
+				"tldts": "^7.0.5"
 			},
 			"engines": {
-				"node": ">=6"
+				"node": ">=16"
 			}
 		},
 		"node_modules/tr46": {
-			"version": "4.1.1",
-			"resolved": "https://registry.npmjs.org/tr46/-/tr46-4.1.1.tgz",
-			"integrity": "sha512-2lv/66T7e5yNyhAAC4NaKe5nVavzuGJQVVtRYLyQ2OI8tsJ61PMLlelehb0wi2Hx6+hT/OJUWZcw8MjlSRnxvw==",
+			"version": "6.0.0",
+			"resolved": "https://registry.npmjs.org/tr46/-/tr46-6.0.0.tgz",
+			"integrity": "sha512-bLVMLPtstlZ4iMQHpFHTR7GAGj2jxi8Dg0s2h2MafAE4uSWF98FC/3MomU51iQAMf8/qDUbKWf5GxuvvVcXEhw==",
 			"dev": true,
+			"license": "MIT",
 			"dependencies": {
-				"punycode": "^2.3.0"
+				"punycode": "^2.3.1"
 			},
 			"engines": {
-				"node": ">=14"
+				"node": ">=20"
 			}
 		},
-		"node_modules/type-check": {
-			"version": "0.3.2",
-			"resolved": "https://registry.npmjs.org/type-check/-/type-check-0.3.2.tgz",
-			"integrity": "sha512-ZCmOJdvOWDBYJlzAoFkC+Q0+bUyEOS1ltgp1MGU03fqHG+dbi9tBFU2Rd9QKiDZFAYrhPh2JUf7rZRIuHRKtOg==",
+		"node_modules/undici": {
+			"version": "7.22.0",
+			"resolved": "https://registry.npmjs.org/undici/-/undici-7.22.0.tgz",
+			"integrity": "sha512-RqslV2Us5BrllB+JeiZnK4peryVTndy9Dnqq62S3yYRRTj0tFQCwEniUy2167skdGOy3vqRzEvl1Dm4sV2ReDg==",
 			"dev": true,
-			"dependencies": {
-				"prelude-ls": "~1.1.2"
-			},
+			"license": "MIT",
 			"engines": {
-				"node": ">= 0.8.0"
+				"node": ">=20.18.1"
 			}
 		},
 		"node_modules/undici-types": {
@@ -784,117 +621,62 @@
 			"dev": true,
 			"license": "MIT"
 		},
-		"node_modules/universalify": {
-			"version": "0.2.0",
-			"resolved": "https://registry.npmjs.org/universalify/-/universalify-0.2.0.tgz",
-			"integrity": "sha512-CJ1QgKmNg3CwvAv/kOFmtnEN05f0D/cn9QntgNOQlQF9dgvVTHj3t+8JPdjqawCHk7V/KA+fbUqzZ9XWhcqPUg==",
-			"dev": true,
-			"engines": {
-				"node": ">= 4.0.0"
-			}
-		},
-		"node_modules/url-parse": {
-			"version": "1.5.10",
-			"resolved": "https://registry.npmjs.org/url-parse/-/url-parse-1.5.10.tgz",
-			"integrity": "sha512-WypcfiRhfeUP9vvF0j6rw0J3hrWrw6iZv3+22h6iRMJ/8z1Tj6XfLP4DsUix5MhMPnXpiHDoKyoZ/bdCkwBCiQ==",
-			"dev": true,
-			"dependencies": {
-				"querystringify": "^2.1.1",
-				"requires-port": "^1.0.0"
-			}
-		},
 		"node_modules/w3c-xmlserializer": {
-			"version": "4.0.0",
-			"resolved": "https://registry.npmjs.org/w3c-xmlserializer/-/w3c-xmlserializer-4.0.0.tgz",
-			"integrity": "sha512-d+BFHzbiCx6zGfz0HyQ6Rg69w9k19nviJspaj4yNscGjrHu94sVP+aRm75yEbCh+r2/yR+7q6hux9LVtbuTGBw==",
+			"version": "5.0.0",
+			"resolved": "https://registry.npmjs.org/w3c-xmlserializer/-/w3c-xmlserializer-5.0.0.tgz",
+			"integrity": "sha512-o8qghlI8NZHU1lLPrpi2+Uq7abh4GGPpYANlalzWxyWteJOCsr/P+oPBA49TOLu5FTZO4d3F9MnWJfiMo4BkmA==",
 			"dev": true,
+			"license": "MIT",
 			"dependencies": {
-				"xml-name-validator": "^4.0.0"
+				"xml-name-validator": "^5.0.0"
 			},
 			"engines": {
-				"node": ">=14"
+				"node": ">=18"
 			}
 		},
 		"node_modules/webidl-conversions": {
-			"version": "7.0.0",
-			"resolved": "https://registry.npmjs.org/webidl-conversions/-/webidl-conversions-7.0.0.tgz",
-			"integrity": "sha512-VwddBukDzu71offAQR975unBIGqfKZpM+8ZX6ySk8nYhVoo5CYaZyzt3YBvYtRtO+aoGlqxPg/B87NGVZ/fu6g==",
-			"dev": true,
-			"engines": {
-				"node": ">=12"
-			}
-		},
-		"node_modules/whatwg-encoding": {
-			"version": "2.0.0",
-			"resolved": "https://registry.npmjs.org/whatwg-encoding/-/whatwg-encoding-2.0.0.tgz",
-			"integrity": "sha512-p41ogyeMUrw3jWclHWTQg1k05DSVXPLcVxRTYsXUk+ZooOCZLcoYgPZ/HL/D/N+uQPOtcp1me1WhBEaX02mhWg==",
+			"version": "8.0.1",
+			"resolved": "https://registry.npmjs.org/webidl-conversions/-/webidl-conversions-8.0.1.tgz",
+			"integrity": "sha512-BMhLD/Sw+GbJC21C/UgyaZX41nPt8bUTg+jWyDeg7e7YN4xOM05YPSIXceACnXVtqyEw/LMClUQMtMZ+PGGpqQ==",
 			"dev": true,
-			"dependencies": {
-				"iconv-lite": "0.6.3"
-			},
+			"license": "BSD-2-Clause",
 			"engines": {
-				"node": ">=12"
+				"node": ">=20"
 			}
 		},
 		"node_modules/whatwg-mimetype": {
-			"version": "3.0.0",
-			"resolved": "https://registry.npmjs.org/whatwg-mimetype/-/whatwg-mimetype-3.0.0.tgz",
-			"integrity": "sha512-nt+N2dzIutVRxARx1nghPKGv1xHikU7HKdfafKkLNLindmPU/ch3U31NOCGGA/dmPcmb1VlofO0vnKAcsm0o/Q==",
+			"version": "5.0.0",
+			"resolved": "https://registry.npmjs.org/whatwg-mimetype/-/whatwg-mimetype-5.0.0.tgz",
+			"integrity": "sha512-sXcNcHOC51uPGF0P/D4NVtrkjSU2fNsm9iog4ZvZJsL3rjoDAzXZhkm2MWt1y+PUdggKAYVoMAIYcs78wJ51Cw==",
 			"dev": true,
+			"license": "MIT",
 			"engines": {
-				"node": ">=12"
+				"node": ">=20"
 			}
 		},
 		"node_modules/whatwg-url": {
-			"version": "12.0.1",
-			"resolved": "https://registry.npmjs.org/whatwg-url/-/whatwg-url-12.0.1.tgz",
-			"integrity": "sha512-Ed/LrqB8EPlGxjS+TrsXcpUond1mhccS3pchLhzSgPCnTimUCKj3IZE75pAs5m6heB2U2TMerKFUXheyHY+VDQ==",
+			"version": "16.0.1",
+			"resolved": "https://registry.npmjs.org/whatwg-url/-/whatwg-url-16.0.1.tgz",
+			"integrity": "sha512-1to4zXBxmXHV3IiSSEInrreIlu02vUOvrhxJJH5vcxYTBDAx51cqZiKdyTxlecdKNSjj8EcxGBxNf6Vg+945gw==",
 			"dev": true,
+			"license": "MIT",
 			"dependencies": {
-				"tr46": "^4.1.1",
-				"webidl-conversions": "^7.0.0"
+				"@exodus/bytes": "^1.11.0",
+				"tr46": "^6.0.0",
+				"webidl-conversions": "^8.0.1"
 			},
 			"engines": {
-				"node": ">=14"
-			}
-		},
-		"node_modules/word-wrap": {
-			"version": "1.2.4",
-			"resolved": "https://registry.npmjs.org/word-wrap/-/word-wrap-1.2.4.tgz",
-			"integrity": "sha512-2V81OA4ugVo5pRo46hAoD2ivUJx8jXmWXfUkY4KFNw0hEptvN0QfH3K4nHiwzGeKl5rFKedV48QVoqYavy4YpA==",
-			"dev": true,
-			"engines": {
-				"node": ">=0.10.0"
-			}
-		},
-		"node_modules/ws": {
-			"version": "8.17.1",
-			"resolved": "https://registry.npmjs.org/ws/-/ws-8.17.1.tgz",
-			"integrity": "sha512-6XQFvXTkbfUOZOKKILFG1PDK2NDQs4azKQl26T0YS5CxqWLgXajbPZ+h4gZekJyRqFU8pvnbAbbs/3TgRPy+GQ==",
-			"dev": true,
-			"engines": {
-				"node": ">=10.0.0"
-			},
-			"peerDependencies": {
-				"bufferutil": "^4.0.1",
-				"utf-8-validate": ">=5.0.2"
-			},
-			"peerDependenciesMeta": {
-				"bufferutil": {
-					"optional": true
-				},
-				"utf-8-validate": {
-					"optional": true
-				}
+				"node": "^20.19.0 || ^22.12.0 || >=24.0.0"
 			}
 		},
 		"node_modules/xml-name-validator": {
-			"version": "4.0.0",
-			"resolved": "https://registry.npmjs.org/xml-name-validator/-/xml-name-validator-4.0.0.tgz",
-			"integrity": "sha512-ICP2e+jsHvAj2E2lIHxa5tjXRlKDJo4IdvPvCXbXQGdzSfmSpNVyIKMvoZHjDY9DP0zV17iI85o90vRFXNccRw==",
+			"version": "5.0.0",
+			"resolved": "https://registry.npmjs.org/xml-name-validator/-/xml-name-validator-5.0.0.tgz",
+			"integrity": "sha512-EvGK8EJ3DhaHfbRlETOWAS5pO9MZITeauHKJyb8wyajUfQUenkIg2MvLDTZ4T/TgIcm3HU0TFBgWWboAZ30UHg==",
 			"dev": true,
+			"license": "Apache-2.0",
 			"engines": {
-				"node": ">=12"
+				"node": ">=18"
 			}
 		},
 		"node_modules/xmlchars": {
diff --git a/extensions/notebook-renderers/package.json b/extensions/notebook-renderers/package.json
index e9890cad8991d..fad11bc9e3005 100644
--- a/extensions/notebook-renderers/package.json
+++ b/extensions/notebook-renderers/package.json
@@ -50,7 +50,7 @@
 		"@types/jsdom": "^21.1.0",
 		"@types/node": "^22.18.10",
 		"@types/vscode-notebook-renderer": "^1.60.0",
-		"jsdom": "^21.1.1"
+		"jsdom": "^28.1.0"
 	},
 	"repository": {
 		"type": "git",
diff --git a/extensions/npm/.npmrc b/extensions/npm/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/npm/.npmrc
+++ b/extensions/npm/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/npm/package-lock.json b/extensions/npm/package-lock.json
index 694e98b5e1213..d3bf11daf09c5 100644
--- a/extensions/npm/package-lock.json
+++ b/extensions/npm/package-lock.json
@@ -12,7 +12,7 @@
         "find-up": "^5.0.0",
         "find-yarn-workspace-root": "^2.0.0",
         "jsonc-parser": "^3.2.0",
-        "minimatch": "^5.1.6",
+        "minimatch": "^5.1.8",
         "request-light": "^0.7.0",
         "vscode-uri": "^3.0.8",
         "which": "^4.0.0",
@@ -209,9 +209,10 @@
       }
     },
     "node_modules/minimatch": {
-      "version": "5.1.6",
-      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-5.1.6.tgz",
-      "integrity": "sha512-lKwV/1brpG6mBUFHtb7NUmtABCb2WZZmm2wNiOA5hAb8VdCS4B3dtMWyvcoViccwAW/COERjXLt0zP1zXUN26g==",
+      "version": "5.1.8",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-5.1.8.tgz",
+      "integrity": "sha512-7RN35vit8DeBclkofOVmBY0eDAZZQd1HzmukRdSyz95CRh8FT54eqnbj0krQr3mrHR6sfRyYkyhwBWjoV5uqlQ==",
+      "license": "ISC",
       "dependencies": {
         "brace-expansion": "^2.0.1"
       },
diff --git a/extensions/npm/package.json b/extensions/npm/package.json
index bba6a23b8ac99..81985c8b29461 100644
--- a/extensions/npm/package.json
+++ b/extensions/npm/package.json
@@ -30,7 +30,7 @@
     "find-up": "^5.0.0",
     "find-yarn-workspace-root": "^2.0.0",
     "jsonc-parser": "^3.2.0",
-    "minimatch": "^5.1.6",
+    "minimatch": "^5.1.8",
     "request-light": "^0.7.0",
     "which": "^4.0.0",
     "which-pm": "^2.1.1",
@@ -295,7 +295,7 @@
           "default": false,
           "scope": "resource",
           "deprecationMessage": "The NPM Script Explorer is now available in 'Views' menu in the Explorer in all folders.",
-          "description": "%config.npm.enableScriptExplorer%"
+          "markdownDescription": "%config.npm.enableScriptExplorer%"
         },
         "npm.enableRunFromFolder": {
           "type": "boolean",
@@ -333,7 +333,7 @@
         },
         "npm.scriptHover": {
           "type": "boolean",
-          "description": "%config.npm.scriptHover%",
+          "markdownDescription": "%config.npm.scriptHover%",
           "default": true,
           "scope": "window"
         }
diff --git a/extensions/npm/package.nls.json b/extensions/npm/package.nls.json
index 56a77ff4f822d..1235a5519c1e7 100644
--- a/extensions/npm/package.nls.json
+++ b/extensions/npm/package.nls.json
@@ -19,12 +19,12 @@
 	"config.npm.scriptRunner.node": "Use Node.js as the script runner.",
 	"config.npm.scriptRunner.auto": "Auto-detect which script runner to use based on lock files and installed package managers.",
 	"config.npm.exclude": "Configure glob patterns for folders that should be excluded from automatic script detection.",
-	"config.npm.enableScriptExplorer": "Enable an explorer view for npm scripts when there is no top-level 'package.json' file.",
+	"config.npm.enableScriptExplorer": "Enable an explorer view for npm scripts when there is no top-level `package.json` file.",
 	"config.npm.scriptExplorerAction": "The default click action used in the NPM Scripts Explorer: `open` or `run`, the default is `open`.",
 	"config.npm.scriptExplorerExclude": "An array of regular expressions that indicate which scripts should be excluded from the NPM Scripts view.",
 	"config.npm.enableRunFromFolder": "Enable running npm scripts contained in a folder from the Explorer context menu.",
 	"config.npm.fetchOnlinePackageInfo": "Fetch data from https://registry.npmjs.org and https://registry.bower.io to provide auto-completion and information on hover features on npm dependencies.",
-	"config.npm.scriptHover": "Display hover with 'Run' and 'Debug' commands for scripts.",
+	"config.npm.scriptHover": "Display hover with `Run` and `Debug` commands for scripts.",
 	"npm.parseError": "Npm task detection: failed to parse the file {0}",
 	"taskdef.script": "The npm script to customize.",
 	"taskdef.path": "The path to the folder of the package.json file that provides the script. Can be omitted.",
diff --git a/extensions/php-language-features/.npmrc b/extensions/php-language-features/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/php-language-features/.npmrc
+++ b/extensions/php-language-features/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/php/cgmanifest.json b/extensions/php/cgmanifest.json
index 090bdf642f9ac..1fe92816e2cce 100644
--- a/extensions/php/cgmanifest.json
+++ b/extensions/php/cgmanifest.json
@@ -6,7 +6,7 @@
 				"git": {
 					"name": "language-php",
 					"repositoryUrl": "https://github.com/KapitanOczywisty/language-php",
-					"commitHash": "6941b924add3b2587a5be789248176edf5f14595"
+					"commitHash": "a0f3d9a3b0d017181455ed515e48a36607a90e3b"
 				}
 			},
 			"license": "MIT",
diff --git a/extensions/php/syntaxes/php.tmLanguage.json b/extensions/php/syntaxes/php.tmLanguage.json
index efb122c98d30b..afa1a5bbb6773 100644
--- a/extensions/php/syntaxes/php.tmLanguage.json
+++ b/extensions/php/syntaxes/php.tmLanguage.json
@@ -4,7 +4,7 @@
 		"If you want to provide a fix or improvement, please create a pull request against the original repository.",
 		"Once accepted there, we are happy to receive an update request."
 	],
-	"version": "https://github.com/KapitanOczywisty/language-php/commit/6941b924add3b2587a5be789248176edf5f14595",
+	"version": "https://github.com/KapitanOczywisty/language-php/commit/a0f3d9a3b0d017181455ed515e48a36607a90e3b",
 	"scopeName": "source.php",
 	"patterns": [
 		{
@@ -2464,7 +2464,7 @@
 							"name": "punctuation.definition.arguments.begin.bracket.round.php"
 						}
 					},
-					"end": "\\)",
+					"end": "\\)|(?=\\?>)",
 					"endCaptures": {
 						"0": {
 							"name": "punctuation.definition.arguments.end.bracket.round.php"
@@ -2536,16 +2536,33 @@
 			]
 		},
 		"invoke-call": {
-			"captures": {
+			"begin": "(?i)((\\$+)[a-z_\\x{7f}-\\x{10ffff}][a-z0-9_\\x{7f}-\\x{10ffff}]*)\\s*(\\()",
+			"beginCaptures": {
 				"1": {
 					"name": "variable.other.php"
 				},
 				"2": {
 					"name": "punctuation.definition.variable.php"
+				},
+				"3": {
+					"name": "punctuation.definition.arguments.begin.bracket.round.php"
+				}
+			},
+			"end": "\\)|(?=\\?>)",
+			"endCaptures": {
+				"0": {
+					"name": "punctuation.definition.arguments.end.bracket.round.php"
 				}
 			},
-			"match": "(?i)((\\$+)[a-z_\\x{7f}-\\x{10ffff}][a-z0-9_\\x{7f}-\\x{10ffff}]*)(?=\\s*\\()",
-			"name": "meta.function-call.invoke.php"
+			"name": "meta.function-call.invoke.php",
+			"patterns": [
+				{
+					"include": "#named-arguments"
+				},
+				{
+					"include": "$self"
+				}
+			]
 		},
 		"namespace": {
 			"begin": "(?i)(?:(namespace)|[a-z_\\x{7f}-\\x{10ffff}][a-z0-9_\\x{7f}-\\x{10ffff}]*)?(\\\\)",
diff --git a/extensions/references-view/.npmrc b/extensions/references-view/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/references-view/.npmrc
+++ b/extensions/references-view/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/ruby/cgmanifest.json b/extensions/ruby/cgmanifest.json
index 5d7a966206122..0fb779250dd30 100644
--- a/extensions/ruby/cgmanifest.json
+++ b/extensions/ruby/cgmanifest.json
@@ -6,7 +6,7 @@
 				"git": {
 					"name": "Shopify/ruby-lsp",
 					"repositoryUrl": "https://github.com/Shopify/ruby-lsp",
-					"commitHash": "59da6a0ae3409437474b85d0daa5535f1878699d"
+					"commitHash": "ba41f8b4f9677fb14c1ecbe15d73ebe12a0d3859"
 				}
 			},
 			"licenseDetail": [
diff --git a/extensions/ruby/syntaxes/ruby.tmLanguage.json b/extensions/ruby/syntaxes/ruby.tmLanguage.json
index f5e3f2b0c0d27..8cda18871b5ce 100644
--- a/extensions/ruby/syntaxes/ruby.tmLanguage.json
+++ b/extensions/ruby/syntaxes/ruby.tmLanguage.json
@@ -4,7 +4,7 @@
 		"If you want to provide a fix or improvement, please create a pull request against the original repository.",
 		"Once accepted there, we are happy to receive an update request."
 	],
-	"version": "https://github.com/Shopify/ruby-lsp/commit/59da6a0ae3409437474b85d0daa5535f1878699d",
+	"version": "https://github.com/Shopify/ruby-lsp/commit/ba41f8b4f9677fb14c1ecbe15d73ebe12a0d3859",
 	"name": "Ruby",
 	"scopeName": "source.ruby",
 	"patterns": [
@@ -1583,7 +1583,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)HTML)\\b\\1))",
 			"comment": "Heredoc with embedded HTML",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)HTML)$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.html",
 			"patterns": [
 				{
@@ -1594,12 +1599,7 @@
 						}
 					},
 					"contentName": "text.html",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)HTML)\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -1620,7 +1620,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)HAML)\\b\\1))",
 			"comment": "Heredoc with embedded HAML",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)HAML)$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.haml",
 			"patterns": [
 				{
@@ -1631,12 +1636,7 @@
 						}
 					},
 					"contentName": "text.haml",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)HAML)\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -1657,7 +1657,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)XML)\\b\\1))",
 			"comment": "Heredoc with embedded XML",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)XML)$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.xml",
 			"patterns": [
 				{
@@ -1668,12 +1673,7 @@
 						}
 					},
 					"contentName": "text.xml",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)XML)\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -1694,7 +1694,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)SQL)\\b\\1))",
 			"comment": "Heredoc with embedded SQL",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)SQL)$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.sql",
 			"patterns": [
 				{
@@ -1705,12 +1710,7 @@
 						}
 					},
 					"contentName": "source.sql",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)SQL)\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -1731,7 +1731,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)(?:GRAPHQL|GQL))\\b\\1))",
 			"comment": "Heredoc with embedded GraphQL",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)(?:GRAPHQL|GQL))$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.graphql",
 			"patterns": [
 				{
@@ -1742,12 +1747,7 @@
 						}
 					},
 					"contentName": "source.graphql",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)(?:GRAPHQL|GQL))\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -1768,7 +1768,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)CSS)\\b\\1))",
 			"comment": "Heredoc with embedded CSS",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)CSS)$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.css",
 			"patterns": [
 				{
@@ -1779,12 +1784,7 @@
 						}
 					},
 					"contentName": "source.css",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)CSS)\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -1805,7 +1805,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)CPP)\\b\\1))",
 			"comment": "Heredoc with embedded C++",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)CPP)$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.cpp",
 			"patterns": [
 				{
@@ -1816,12 +1821,7 @@
 						}
 					},
 					"contentName": "source.cpp",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)CPP)\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -1842,7 +1842,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)C)\\b\\1))",
 			"comment": "Heredoc with embedded C",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)C)$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.c",
 			"patterns": [
 				{
@@ -1853,12 +1858,7 @@
 						}
 					},
 					"contentName": "source.c",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)C)\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -1879,7 +1879,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)(?:JS|JAVASCRIPT))\\b\\1))",
 			"comment": "Heredoc with embedded Javascript",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)(?:JS|JAVASCRIPT))$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.js",
 			"patterns": [
 				{
@@ -1890,12 +1895,7 @@
 						}
 					},
 					"contentName": "source.js",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)(?:JS|JAVASCRIPT))\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -1916,7 +1916,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)JQUERY)\\b\\1))",
 			"comment": "Heredoc with embedded jQuery Javascript",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)JQUERY)$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.js.jquery",
 			"patterns": [
 				{
@@ -1927,12 +1932,7 @@
 						}
 					},
 					"contentName": "source.js.jquery",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)JQUERY)\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -1953,7 +1953,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)(?:SH|SHELL))\\b\\1))",
 			"comment": "Heredoc with embedded Shell",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)(?:SH|SHELL))$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.shell",
 			"patterns": [
 				{
@@ -1964,12 +1969,7 @@
 						}
 					},
 					"contentName": "source.shell",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)(?:SH|SHELL))\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -1990,7 +1990,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)LUA)\\b\\1))",
 			"comment": "Heredoc with embedded Lua",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)LUA)$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.lua",
 			"patterns": [
 				{
@@ -2001,12 +2006,7 @@
 						}
 					},
 					"contentName": "source.lua",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)LUA)\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -2027,7 +2027,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)RUBY)\\b\\1))",
 			"comment": "Heredoc with embedded Ruby",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)RUBY)$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.ruby",
 			"patterns": [
 				{
@@ -2038,12 +2043,7 @@
 						}
 					},
 					"contentName": "source.ruby",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)RUBY)\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -2064,7 +2064,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)(?:YAML|YML))\\b\\1))",
 			"comment": "Heredoc with embedded YAML",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)(?:YAML|YML))$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.yaml",
 			"patterns": [
 				{
@@ -2075,12 +2080,7 @@
 						}
 					},
 					"contentName": "source.yaml",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)(?:YAML|YML))\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
@@ -2101,7 +2101,12 @@
 		{
 			"begin": "(?=(?><<[-~]?([\"'`]?)((?:[_\\w]+_|)SLIM)\\b\\1))",
 			"comment": "Heredoc with embedded Slim",
-			"end": "(?!\\G)",
+			"end": "^\\s*((?:[_\\w]+_|)SLIM)$\\n?",
+			"endCaptures": {
+				"0": {
+					"name": "string.definition.end.ruby"
+				}
+			},
 			"name": "meta.embedded.block.slim",
 			"patterns": [
 				{
@@ -2112,12 +2117,7 @@
 						}
 					},
 					"contentName": "text.slim",
-					"end": "^\\s*\\2$\\n?",
-					"endCaptures": {
-						"0": {
-							"name": "string.definition.end.ruby"
-						}
-					},
+					"while": "^(?!\\s*((?:[_\\w]+_|)SLIM)\\s*$)",
 					"patterns": [
 						{
 							"include": "#heredoc"
diff --git a/extensions/shared.webpack.config.mjs b/extensions/shared.webpack.config.mjs
deleted file mode 100644
index 12b1ea522a4ad..0000000000000
--- a/extensions/shared.webpack.config.mjs
+++ /dev/null
@@ -1,209 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-// @ts-check
-import path from 'node:path';
-import fs from 'node:fs';
-import merge from 'merge-options';
-import CopyWebpackPlugin from 'copy-webpack-plugin';
-import webpack from 'webpack';
-import { createRequire } from 'node:module';
-
-/** @typedef {import('webpack').Configuration} WebpackConfig **/
-
-const require = createRequire(import.meta.url);
-
-const tsLoaderOptions = {
-	compilerOptions: {
-		'sourceMap': true,
-	},
-	onlyCompileBundledFiles: true,
-};
-
-function withNodeDefaults(/**@type WebpackConfig & { context: string }*/extConfig) {
-	const defaultConfig = {
-		mode: 'none', // this leaves the source code as close as possible to the original (when packaging we set this to 'production')
-		target: 'node', // extensions run in a node context
-		node: {
-			__dirname: false // leave the __dirname-behaviour intact
-		},
-
-		resolve: {
-			conditionNames: ['import', 'require', 'node-addons', 'node'],
-			mainFields: ['module', 'main'],
-			extensions: ['.ts', '.js'], // support ts-files and js-files
-			extensionAlias: {
-				// this is needed to resolve dynamic imports that now require the .js extension
-				'.js': ['.js', '.ts'],
-			}
-		},
-		module: {
-			rules: [{
-				test: /\.ts$/,
-				exclude: /node_modules/,
-				use: [
-					{
-						// configure TypeScript loader:
-						// * enable sources maps for end-to-end source maps
-						loader: 'ts-loader',
-						options: tsLoaderOptions
-					},
-					// disable mangling for now, SEE https://github.com/microsoft/vscode/issues/204692
-					// {
-					// 	loader: path.resolve(import.meta.dirname, 'mangle-loader.js'),
-					// 	options: {
-					// 		configFile: path.join(extConfig.context, 'tsconfig.json')
-					// 	},
-					// },
-				]
-			}]
-		},
-		externals: {
-			'electron': 'commonjs electron', // ignored to avoid bundling from node_modules
-			'vscode': 'commonjs vscode', // ignored because it doesn't exist,
-			'applicationinsights-native-metrics': 'commonjs applicationinsights-native-metrics', // ignored because we don't ship native module
-			'@azure/functions-core': 'commonjs azure/functions-core', // optional dependency of appinsights that we don't use
-			'@opentelemetry/tracing': 'commonjs @opentelemetry/tracing', // ignored because we don't ship this module
-			'@opentelemetry/instrumentation': 'commonjs @opentelemetry/instrumentation', // ignored because we don't ship this module
-			'@azure/opentelemetry-instrumentation-azure-sdk': 'commonjs @azure/opentelemetry-instrumentation-azure-sdk', // ignored because we don't ship this module
-		},
-		output: {
-			// all output goes into `dist`.
-			// packaging depends on that and this must always be like it
-			filename: '[name].js',
-			path: path.join(extConfig.context, 'dist'),
-			libraryTarget: 'commonjs',
-		},
-		// yes, really source maps
-		devtool: 'source-map',
-		plugins: nodePlugins(extConfig.context),
-	};
-
-	return merge(defaultConfig, extConfig);
-}
-
-/**
- *
- * @param {string} context
- */
-function nodePlugins(context) {
-	// Need to find the top-most `package.json` file
-	const folderName = path.relative(import.meta.dirname, context).split(/[\\\/]/)[0];
-	const pkgPath = path.join(import.meta.dirname, folderName, 'package.json');
-	const pkg = JSON.parse(fs.readFileSync(pkgPath, 'utf8'));
-	const id = `${pkg.publisher}.${pkg.name}`;
-	return [
-		new CopyWebpackPlugin({
-			patterns: [
-				{ from: 'src', to: '.', globOptions: { ignore: ['**/test/**', '**/*.ts'] }, noErrorOnMissing: true }
-			]
-		})
-	];
-}
-/**
- * @typedef {{
- * 	configFile?: string
- * }} AdditionalBrowserConfig
- */
-
-function withBrowserDefaults(/**@type WebpackConfig & { context: string }*/extConfig, /** @type AdditionalBrowserConfig */ additionalOptions = {}) {
-	/** @type WebpackConfig */
-	const defaultConfig = {
-		mode: 'none', // this leaves the source code as close as possible to the original (when packaging we set this to 'production')
-		target: 'webworker', // extensions run in a webworker context
-		resolve: {
-			mainFields: ['browser', 'module', 'main'],
-			extensions: ['.ts', '.js'], // support ts-files and js-files
-			fallback: {
-				'path': require.resolve('path-browserify'),
-				'os': require.resolve('os-browserify'),
-				'util': require.resolve('util')
-			},
-			extensionAlias: {
-				// this is needed to resolve dynamic imports that now require the .js extension
-				'.js': ['.js', '.ts'],
-			},
-		},
-		module: {
-			rules: [{
-				test: /\.ts$/,
-				exclude: /node_modules/,
-				use: [
-					{
-						// configure TypeScript loader:
-						// * enable sources maps for end-to-end source maps
-						loader: 'ts-loader',
-						options: {
-							...tsLoaderOptions,
-							//							...(additionalOptions ? {} : { configFile: additionalOptions.configFile }),
-						}
-					},
-					// disable mangling for now, SEE https://github.com/microsoft/vscode/issues/204692
-					// {
-					// 	loader: path.resolve(import.meta.dirname, 'mangle-loader.js'),
-					// 	options: {
-					// 		configFile: path.join(extConfig.context, additionalOptions?.configFile ?? 'tsconfig.json')
-					// 	},
-					// },
-				]
-			}, {
-				test: /\.wasm$/,
-				type: 'asset/inline'
-			}]
-		},
-		externals: {
-			'vscode': 'commonjs vscode', // ignored because it doesn't exist,
-			'applicationinsights-native-metrics': 'commonjs applicationinsights-native-metrics', // ignored because we don't ship native module
-			'@azure/functions-core': 'commonjs azure/functions-core', // optional dependency of appinsights that we don't use
-			'@opentelemetry/tracing': 'commonjs @opentelemetry/tracing', // ignored because we don't ship this module
-			'@opentelemetry/instrumentation': 'commonjs @opentelemetry/instrumentation', // ignored because we don't ship this module
-			'@azure/opentelemetry-instrumentation-azure-sdk': 'commonjs @azure/opentelemetry-instrumentation-azure-sdk', // ignored because we don't ship this module
-		},
-		performance: {
-			hints: false
-		},
-		output: {
-			// all output goes into `dist`.
-			// packaging depends on that and this must always be like it
-			filename: '[name].js',
-			path: path.join(extConfig.context, 'dist', 'browser'),
-			libraryTarget: 'commonjs',
-		},
-		// yes, really source maps
-		devtool: 'source-map',
-		plugins: browserPlugins(extConfig.context)
-	};
-
-	return merge(defaultConfig, extConfig);
-}
-
-/**
- *
- * @param {string} context
- */
-function browserPlugins(context) {
-	// Need to find the top-most `package.json` file
-	// const folderName = path.relative(__dirname, context).split(/[\\\/]/)[0];
-	// const pkgPath = path.join(__dirname, folderName, 'package.json');
-	// const pkg = JSON.parse(fs.readFileSync(pkgPath, 'utf8'));
-	// const id = `${pkg.publisher}.${pkg.name}`;
-	return [
-		new webpack.optimize.LimitChunkCountPlugin({
-			maxChunks: 1
-		}),
-		new CopyWebpackPlugin({
-			patterns: [
-				{ from: 'src', to: '.', globOptions: { ignore: ['**/test/**', '**/*.ts'] }, noErrorOnMissing: true }
-			]
-		}),
-		new webpack.DefinePlugin({
-			'process.platform': JSON.stringify('web'),
-			'process.env': JSON.stringify({}),
-			'process.env.BROWSER_ENV': JSON.stringify('true')
-		})
-	];
-}
-
-export default withNodeDefaults;
-export { withNodeDefaults as node, withBrowserDefaults as browser, nodePlugins, browserPlugins };
diff --git a/extensions/simple-browser/.npmrc b/extensions/simple-browser/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/simple-browser/.npmrc
+++ b/extensions/simple-browser/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/swift/cgmanifest.json b/extensions/swift/cgmanifest.json
index ecd2705da2a90..02ea0744ecd2c 100644
--- a/extensions/swift/cgmanifest.json
+++ b/extensions/swift/cgmanifest.json
@@ -6,7 +6,7 @@
 				"git": {
 					"name": "jtbandes/swift-tmlanguage",
 					"repositoryUrl": "https://github.com/jtbandes/swift-tmlanguage",
-					"commitHash": "45ac01d47c6d63402570c2c36bcfbadbd1c7bca6"
+					"commitHash": "3fca2fa10f7dc962d19ee617b17844d6eecfa2cb"
 				}
 			},
 			"license": "MIT"
diff --git a/extensions/swift/syntaxes/swift.tmLanguage.json b/extensions/swift/syntaxes/swift.tmLanguage.json
index a8bbe5d00b479..d52cabb836ba4 100644
--- a/extensions/swift/syntaxes/swift.tmLanguage.json
+++ b/extensions/swift/syntaxes/swift.tmLanguage.json
@@ -4,7 +4,7 @@
 		"If you want to provide a fix or improvement, please create a pull request against the original repository.",
 		"Once accepted there, we are happy to receive an update request."
 	],
-	"version": "https://github.com/jtbandes/swift-tmlanguage/commit/45ac01d47c6d63402570c2c36bcfbadbd1c7bca6",
+	"version": "https://github.com/jtbandes/swift-tmlanguage/commit/3fca2fa10f7dc962d19ee617b17844d6eecfa2cb",
 	"name": "Swift",
 	"scopeName": "source.swift",
 	"comment": "See swift.tmbundle/grammar-test.swift for test cases.",
@@ -3848,7 +3848,7 @@
 				},
 				{
 					"name": "string.quoted.double.block.raw.swift",
-					"begin": "#\"\"\"",
+					"begin": "#\"\"\"(?!#)(?=(?:[^\"]|\"(?!#))*$)",
 					"end": "\"\"\"#(#*)",
 					"beginCaptures": {
 						"0": {
@@ -3884,7 +3884,7 @@
 				},
 				{
 					"name": "string.quoted.double.block.raw.swift",
-					"begin": "(##+)\"\"\"",
+					"begin": "(?<!#)(##+)\"\"\"(?!\\1)(?=(?:[^\"]|\"(?!\\1))*$)",
 					"end": "\"\"\"\\1(#*)",
 					"beginCaptures": {
 						"0": {
@@ -3936,7 +3936,7 @@
 				{
 					"comment": "SE-0168: raw string literals (more than one #, grammar limitations prevent us from supporting escapes)",
 					"name": "string.quoted.double.single-line.raw.swift",
-					"begin": "(##+)\"",
+					"begin": "(?<!#)(##+)\"",
 					"end": "\"\\1(#*)",
 					"beginCaptures": {
 						"0": {
diff --git a/extensions/terminal-suggest/.npmrc b/extensions/terminal-suggest/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/terminal-suggest/.npmrc
+++ b/extensions/terminal-suggest/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/terminal-suggest/src/media/icon.png b/extensions/terminal-suggest/media/icon.png
similarity index 100%
rename from extensions/terminal-suggest/src/media/icon.png
rename to extensions/terminal-suggest/media/icon.png
diff --git a/extensions/terminal-suggest/package.json b/extensions/terminal-suggest/package.json
index 734e3e91c82a5..5eea60ebf7bdc 100644
--- a/extensions/terminal-suggest/package.json
+++ b/extensions/terminal-suggest/package.json
@@ -6,7 +6,7 @@
   "version": "1.0.1",
   "private": true,
   "license": "MIT",
-  "icon": "./src/media/icon.png",
+  "icon": "./media/icon.png",
   "engines": {
     "vscode": "^1.95.0"
   },
diff --git a/extensions/terminal-suggest/src/completions/azd.ts b/extensions/terminal-suggest/src/completions/azd.ts
index 6a4cf535ee793..97c9fc661910e 100644
--- a/extensions/terminal-suggest/src/completions/azd.ts
+++ b/extensions/terminal-suggest/src/completions/azd.ts
@@ -278,6 +278,121 @@ const completionSpec: Fig.Spec = {
 								},
 							],
 						},
+						{
+							name: ['monitor'],
+							description: 'Monitor logs from a hosted agent container.',
+							options: [
+								{
+									name: ['--account-name', '-a'],
+									description: 'Cognitive Services account name',
+									args: [
+										{
+											name: 'account-name',
+										},
+									],
+								},
+								{
+									name: ['--follow', '-f'],
+									description: 'Stream logs in real-time',
+								},
+								{
+									name: ['--name', '-n'],
+									description: 'Name of the hosted agent (required)',
+									args: [
+										{
+											name: 'name',
+										},
+									],
+								},
+								{
+									name: ['--project-name', '-p'],
+									description: 'AI Foundry project name',
+									args: [
+										{
+											name: 'project-name',
+										},
+									],
+								},
+								{
+									name: ['--tail', '-l'],
+									description: 'Number of trailing log lines to fetch (1-300)',
+									args: [
+										{
+											name: 'tail',
+										},
+									],
+								},
+								{
+									name: ['--type', '-t'],
+									description: 'Type of logs: \'console\' (stdout/stderr) or \'system\' (container events)',
+									args: [
+										{
+											name: 'type',
+										},
+									],
+								},
+								{
+									name: ['--version', '-v'],
+									description: 'Version of the hosted agent (required)',
+									args: [
+										{
+											name: 'version',
+										},
+									],
+								},
+							],
+						},
+						{
+							name: ['show'],
+							description: 'Show the status of a hosted agent deployment.',
+							options: [
+								{
+									name: ['--account-name', '-a'],
+									description: 'Cognitive Services account name',
+									args: [
+										{
+											name: 'account-name',
+										},
+									],
+								},
+								{
+									name: ['--name', '-n'],
+									description: 'Name of the hosted agent (required)',
+									args: [
+										{
+											name: 'name',
+										},
+									],
+								},
+								{
+									name: ['--output', '-o'],
+									description: 'Output format (json or table)',
+									args: [
+										{
+											name: 'output',
+										},
+									],
+								},
+								{
+									name: ['--project-name', '-p'],
+									description: 'AI Foundry project name',
+									args: [
+										{
+											name: 'project-name',
+										},
+									],
+								},
+								{
+									name: ['--version', '-v'],
+									description: 'Version of the hosted agent (required)',
+									args: [
+										{
+											name: 'version',
+										},
+									],
+								},
+							],
+						},
 						{
 							name: ['version'],
 							description: 'Prints the version of the application',
@@ -750,6 +865,363 @@ const completionSpec: Fig.Spec = {
 						},
 					],
 				},
+				{
+					name: ['models'],
+					description: 'Extension for managing custom models in Azure AI Foundry. (Preview)',
+					subcommands: [
+						{
+							name: ['custom'],
+							description: 'Manage custom models in Azure AI Foundry',
+							subcommands: [
+								{
+									name: ['create'],
+									description: 'Upload and register a custom model',
+									options: [
+										{
+											name: ['--azcopy-path'],
+											description: 'Path to azcopy binary (auto-detected if not provided)',
+											args: [
+												{
+													name: 'azcopy-path',
+												},
+											],
+										},
+										{
+											name: ['--base-model'],
+											description: 'Base model identifier (e.g., FW-GPT-OSS-120B or full azureml:// URI)',
+											args: [
+												{
+													name: 'base-model',
+												},
+											],
+										},
+										{
+											name: ['--blob-uri'],
+											description: 'Already-uploaded blob URI (skips upload, registers directly)',
+											args: [
+												{
+													name: 'blob-uri',
+												},
+											],
+										},
+										{
+											name: ['--description'],
+											description: 'Model description',
+											args: [
+												{
+													name: 'description',
+												},
+											],
+										},
+										{
+											name: ['--name', '-n'],
+											description: 'Model name (required)',
+											args: [
+												{
+													name: 'name',
+												},
+											],
+										},
+										{
+											name: ['--project-endpoint', '-e'],
+											description: 'Azure AI Foundry project endpoint URL (e.g., https://account.services.ai.azure.com/api/projects/project-name)',
+											args: [
+												{
+													name: 'project-endpoint',
+												},
+											],
+										},
+										{
+											name: ['--publisher'],
+											description: 'Model publisher ID for catalog info',
+											args: [
+												{
+													name: 'publisher',
+												},
+											],
+										},
+										{
+											name: ['--source'],
+											description: 'Local path or remote URL to model files',
+											args: [
+												{
+													name: 'source',
+												},
+											],
+										},
+										{
+											name: ['--source-file'],
+											description: 'Path to a file containing the source URL (useful for URLs with special characters)',
+											args: [
+												{
+													name: 'source-file',
+												},
+											],
+										},
+										{
+											name: ['--subscription', '-s'],
+											description: 'Azure subscription ID',
+											args: [
+												{
+													name: 'subscription',
+												},
+											],
+										},
+										{
+											name: ['--version'],
+											description: 'Model version',
+											args: [
+												{
+													name: 'version',
+												},
+											],
+										},
+									],
+								},
+								{
+									name: ['delete'],
+									description: 'Delete a custom model',
+									options: [
+										{
+											name: ['--force', '-f'],
+											description: 'Skip confirmation prompt',
+											isDangerous: true,
+										},
+										{
+											name: ['--name', '-n'],
+											description: 'Model name (required)',
+											args: [
+												{
+													name: 'name',
+												},
+											],
+										},
+										{
+											name: ['--project-endpoint', '-e'],
+											description: 'Azure AI Foundry project endpoint URL (e.g., https://account.services.ai.azure.com/api/projects/project-name)',
+											args: [
+												{
+													name: 'project-endpoint',
+												},
+											],
+										},
+										{
+											name: ['--subscription', '-s'],
+											description: 'Azure subscription ID',
+											args: [
+												{
+													name: 'subscription',
+												},
+											],
+										},
+										{
+											name: ['--version'],
+											description: 'Model version',
+											args: [
+												{
+													name: 'version',
+												},
+											],
+										},
+									],
+								},
+								{
+									name: ['list'],
+									description: 'List all custom models',
+									options: [
+										{
+											name: ['--output', '-o'],
+											description: 'Output format (table, json)',
+											args: [
+												{
+													name: 'output',
+												},
+											],
+										},
+										{
+											name: ['--project-endpoint', '-e'],
+											description: 'Azure AI Foundry project endpoint URL (e.g., https://account.services.ai.azure.com/api/projects/project-name)',
+											args: [
+												{
+													name: 'project-endpoint',
+												},
+											],
+										},
+										{
+											name: ['--subscription', '-s'],
+											description: 'Azure subscription ID',
+											args: [
+												{
+													name: 'subscription',
+												},
+											],
+										},
+									],
+								},
+								{
+									name: ['show'],
+									description: 'Show details of a custom model',
+									options: [
+										{
+											name: ['--name', '-n'],
+											description: 'Model name (required)',
+											args: [
+												{
+													name: 'name',
+												},
+											],
+										},
+										{
+											name: ['--output', '-o'],
+											description: 'Output format (table, json)',
+											args: [
+												{
+													name: 'output',
+												},
+											],
+										},
+										{
+											name: ['--project-endpoint', '-e'],
+											description: 'Azure AI Foundry project endpoint URL (e.g., https://account.services.ai.azure.com/api/projects/project-name)',
+											args: [
+												{
+													name: 'project-endpoint',
+												},
+											],
+										},
+										{
+											name: ['--subscription', '-s'],
+											description: 'Azure subscription ID',
+											args: [
+												{
+													name: 'subscription',
+												},
+											],
+										},
+										{
+											name: ['--version'],
+											description: 'Model version',
+											args: [
+												{
+													name: 'version',
+												},
+											],
+										},
+									],
+								},
+							],
+							options: [
+								{
+									name: ['--project-endpoint', '-e'],
+									description: 'Azure AI Foundry project endpoint URL (e.g., https://account.services.ai.azure.com/api/projects/project-name)',
+									args: [
+										{
+											name: 'project-endpoint',
+										},
+									],
+								},
+								{
+									name: ['--subscription', '-s'],
+									description: 'Azure subscription ID',
+									args: [
+										{
+											name: 'subscription',
+										},
+									],
+								},
+							],
+						},
+						{
+							name: ['init'],
+							description: 'Initialize a new AI models project. (Preview)',
+							options: [
+								{
+									name: ['--environment', '-n'],
+									description: 'The name of the azd environment to use',
+									args: [
+										{
+											name: 'environment',
+										},
+									],
+								},
+								{
+									name: ['--project-endpoint', '-e'],
+									description: 'Azure AI Foundry project endpoint URL (e.g., https://account.services.ai.azure.com/api/projects/project-name)',
+									args: [
+										{
+											name: 'project-endpoint',
+										},
+									],
+								},
+								{
+									name: ['--project-resource-id', '-p'],
+									description: 'ARM resource ID of the Foundry project',
+									args: [
+										{
+											name: 'project-resource-id',
+										},
+									],
+								},
+								{
+									name: ['--subscription', '-s'],
+									description: 'Azure subscription ID',
+									args: [
+										{
+											name: 'subscription',
+										},
+									],
+								},
+							],
+						},
+						{
+							name: ['version'],
+							description: 'Prints the version of the application',
+						},
+					],
+				},
+			],
+		},
+		{
+			name: ['appservice'],
+			description: 'Extension for managing Azure App Service resources.',
+			subcommands: [
+				{
+					name: ['swap'],
+					description: 'Swap deployment slots for an App Service.',
+					options: [
+						{
+							name: ['--dst'],
+							description: 'The destination slot name. Use @main for production.',
+							args: [
+								{
+									name: 'dst',
+								},
+							],
+						},
+						{
+							name: ['--service'],
+							description: 'The name of the service to swap slots for.',
+							args: [
+								{
+									name: 'service',
+								},
+							],
+						},
+						{
+							name: ['--src'],
+							description: 'The source slot name. Use @main for production.',
+							args: [
+								{
+									name: 'src',
+								},
+							],
+						},
+					],
+				},
+				{
+					name: ['version'],
+					description: 'Display the version of the extension.',
+				},
 			],
 		},
 		{
@@ -1001,8 +1473,26 @@ const completionSpec: Fig.Spec = {
 		},
 		{
 			name: ['demo'],
-			description: 'This extension provides examples of the AZD extension framework.',
+			description: 'This extension provides examples of the azd extension framework.',
 			subcommands: [
+				{
+					name: ['ai'],
+					description: 'Interactive AI model discovery, deployment, and quota demos.',
+					subcommands: [
+						{
+							name: ['deployment'],
+							description: 'Select model/version/SKU/capacity and resolve a valid deployment configuration.',
+						},
+						{
+							name: ['models'],
+							description: 'Browse available AI models interactively.',
+						},
+						{
+							name: ['quota'],
+							description: 'View usage meters and limits for a selected location.',
+						},
+					],
+				},
 				{
 					name: ['colors', 'colours'],
 					description: 'Displays all ASCII colors with their standard and high-intensity variants.',
@@ -1013,7 +1503,7 @@ const completionSpec: Fig.Spec = {
 				},
 				{
 					name: ['context'],
-					description: 'Get the context of the AZD project & environment.',
+					description: 'Get the context of the azd project & environment.',
 				},
 				{
 					name: ['gh-url-parse'],
@@ -1226,7 +1716,7 @@ const completionSpec: Fig.Spec = {
 						},
 						{
 							name: ['--subscription'],
-							description: 'Name or ID of an Azure subscription to use for the new environment',
+							description: 'ID of an Azure subscription to use for the new environment',
 							args: [
 								{
 									name: 'subscription',
@@ -1493,6 +1983,19 @@ const completionSpec: Fig.Spec = {
 								name: 'name',
 							},
 						},
+						{
+							name: ['validate'],
+							description: 'Validate an extension source\'s registry.json file.',
+							options: [
+								{
+									name: ['--strict'],
+									description: 'Enable strict validation (require checksums)',
+								},
+							],
+							args: {
+								name: 'name-or-path-or-url',
+							},
+						},
 					],
 				},
 				{
@@ -1683,7 +2186,7 @@ const completionSpec: Fig.Spec = {
 				},
 				{
 					name: ['--subscription', '-s'],
-					description: 'Name or ID of an Azure subscription to use for the new environment',
+					description: 'ID of an Azure subscription to use for the new environment',
 					args: [
 						{
 							name: 'subscription',
@@ -1692,7 +2195,7 @@ const completionSpec: Fig.Spec = {
 				},
 				{
 					name: ['--template', '-t'],
-					description: 'Initializes a new application from a template. You can use Full URI, <owner>/<repository>, or <repository> if it\'s part of the azure-samples organization.',
+					description: 'Initializes a new application from a template. You can use a Full URI, <owner>/<repository>, <repository> if it\'s part of the azure-samples organization, or a local directory path (./dir, ../dir, or absolute path).',
 					args: [
 						{
 							name: 'template',
@@ -2059,6 +2562,15 @@ const completionSpec: Fig.Spec = {
 						},
 					],
 				},
+				{
+					name: ['--location', '-l'],
+					description: 'Azure location for the new environment',
+					args: [
+						{
+							name: 'location',
+						},
+					],
+				},
 				{
 					name: ['--no-state'],
 					description: '(Bicep only) Forces a fresh deployment based on current Bicep template files, ignoring any stored deployment state.',
@@ -2067,6 +2579,15 @@ const completionSpec: Fig.Spec = {
 					name: ['--preview'],
 					description: 'Preview changes to Azure resources.',
 				},
+				{
+					name: ['--subscription'],
+					description: 'ID of an Azure subscription to use for the new environment',
+					args: [
+						{
+							name: 'subscription',
+						},
+					],
+				},
 			],
 			args: {
 				name: 'layer',
@@ -2267,6 +2788,24 @@ const completionSpec: Fig.Spec = {
 						},
 					],
 				},
+				{
+					name: ['--location', '-l'],
+					description: 'Azure location for the new environment',
+					args: [
+						{
+							name: 'location',
+						},
+					],
+				},
+				{
+					name: ['--subscription'],
+					description: 'ID of an Azure subscription to use for the new environment',
+					args: [
+						{
+							name: 'subscription',
+						},
+					],
+				},
 			],
 		},
 		{
@@ -2275,7 +2814,7 @@ const completionSpec: Fig.Spec = {
 		},
 		{
 			name: ['x'],
-			description: 'This extension provides a set of tools for AZD extension developers to test and debug their extensions.',
+			description: 'This extension provides a set of tools for azd extension developers to test and debug their extensions.',
 			subcommands: [
 				{
 					name: ['build'],
@@ -2302,7 +2841,7 @@ const completionSpec: Fig.Spec = {
 				},
 				{
 					name: ['init'],
-					description: 'Initialize a new AZD extension project',
+					description: 'Initialize a new azd extension project',
 					options: [
 						{
 							name: ['--capabilities'],
@@ -2506,7 +3045,7 @@ const completionSpec: Fig.Spec = {
 				},
 				{
 					name: ['watch'],
-					description: 'Watches the AZD extension project for file changes and rebuilds it.',
+					description: 'Watches the azd extension project for file changes and rebuilds it.',
 				},
 			],
 		},
@@ -2530,6 +3069,14 @@ const completionSpec: Fig.Spec = {
 									name: ['init'],
 									description: 'Initialize a new AI agent project. (Preview)',
 								},
+								{
+									name: ['monitor'],
+									description: 'Monitor logs from a hosted agent container.',
+								},
+								{
+									name: ['show'],
+									description: 'Show the status of a hosted agent deployment.',
+								},
 								{
 									name: ['version'],
 									description: 'Prints the version of the application',
@@ -2584,6 +3131,56 @@ const completionSpec: Fig.Spec = {
 								},
 							],
 						},
+						{
+							name: ['models'],
+							description: 'Extension for managing custom models in Azure AI Foundry. (Preview)',
+							subcommands: [
+								{
+									name: ['custom'],
+									description: 'Manage custom models in Azure AI Foundry',
+									subcommands: [
+										{
+											name: ['create'],
+											description: 'Upload and register a custom model',
+										},
+										{
+											name: ['delete'],
+											description: 'Delete a custom model',
+										},
+										{
+											name: ['list'],
+											description: 'List all custom models',
+										},
+										{
+											name: ['show'],
+											description: 'Show details of a custom model',
+										},
+									],
+								},
+								{
+									name: ['init'],
+									description: 'Initialize a new AI models project. (Preview)',
+								},
+								{
+									name: ['version'],
+									description: 'Prints the version of the application',
+								},
+							],
+						},
+					],
+				},
+				{
+					name: ['appservice'],
+					description: 'Extension for managing Azure App Service resources.',
+					subcommands: [
+						{
+							name: ['swap'],
+							description: 'Swap deployment slots for an App Service.',
+						},
+						{
+							name: ['version'],
+							description: 'Display the version of the extension.',
+						},
 					],
 				},
 				{
@@ -2694,8 +3291,26 @@ const completionSpec: Fig.Spec = {
 				},
 				{
 					name: ['demo'],
-					description: 'This extension provides examples of the AZD extension framework.',
+					description: 'This extension provides examples of the azd extension framework.',
 					subcommands: [
+						{
+							name: ['ai'],
+							description: 'Interactive AI model discovery, deployment, and quota demos.',
+							subcommands: [
+								{
+									name: ['deployment'],
+									description: 'Select model/version/SKU/capacity and resolve a valid deployment configuration.',
+								},
+								{
+									name: ['models'],
+									description: 'Browse available AI models interactively.',
+								},
+								{
+									name: ['quota'],
+									description: 'View usage meters and limits for a selected location.',
+								},
+							],
+						},
 						{
 							name: ['colors', 'colours'],
 							description: 'Displays all ASCII colors with their standard and high-intensity variants.',
@@ -2706,7 +3321,7 @@ const completionSpec: Fig.Spec = {
 						},
 						{
 							name: ['context'],
-							description: 'Get the context of the AZD project & environment.',
+							description: 'Get the context of the azd project & environment.',
 						},
 						{
 							name: ['gh-url-parse'],
@@ -2836,6 +3451,10 @@ const completionSpec: Fig.Spec = {
 									name: ['remove'],
 									description: 'Remove an extension source with the specified name',
 								},
+								{
+									name: ['validate'],
+									description: 'Validate an extension source\'s registry.json file.',
+								},
 							],
 						},
 						{
@@ -2976,7 +3595,7 @@ const completionSpec: Fig.Spec = {
 				},
 				{
 					name: ['x'],
-					description: 'This extension provides a set of tools for AZD extension developers to test and debug their extensions.',
+					description: 'This extension provides a set of tools for azd extension developers to test and debug their extensions.',
 					subcommands: [
 						{
 							name: ['build'],
@@ -2984,7 +3603,7 @@ const completionSpec: Fig.Spec = {
 						},
 						{
 							name: ['init'],
-							description: 'Initialize a new AZD extension project',
+							description: 'Initialize a new azd extension project',
 						},
 						{
 							name: ['pack'],
@@ -3004,7 +3623,7 @@ const completionSpec: Fig.Spec = {
 						},
 						{
 							name: ['watch'],
-							description: 'Watches the AZD extension project for file changes and rebuilds it.',
+							description: 'Watches the azd extension project for file changes and rebuilds it.',
 						},
 					],
 				},
diff --git a/extensions/theme-2026/package.json b/extensions/theme-2026/package.json
index 305cc066c89f1..8360afdac5ca7 100644
--- a/extensions/theme-2026/package.json
+++ b/extensions/theme-2026/package.json
@@ -8,9 +8,6 @@
 	"engines": {
 		"vscode": "^1.85.0"
 	},
-    "enabledApiProposals": [
-      "css"
-  ],
 	"categories": [
 		"Themes"
 	],
@@ -28,11 +25,6 @@
 				"uiTheme": "vs-dark",
 				"path": "./themes/2026-dark.json"
 			}
-		],
-    "css": [
-      {
-        "path": "./themes/styles.css"
-      }
-    ]
+		]
 	}
 }
diff --git a/extensions/theme-2026/themes/2026-dark.json b/extensions/theme-2026/themes/2026-dark.json
index ee51bb61214e2..d204a5506b093 100644
--- a/extensions/theme-2026/themes/2026-dark.json
+++ b/extensions/theme-2026/themes/2026-dark.json
@@ -5,7 +5,7 @@
 	"type": "dark",
 	"colors": {
 		"foreground": "#bfbfbf",
-		"disabledForeground": "#666666",
+		"disabledForeground": "#555555",
 		"errorForeground": "#f48771",
 		"descriptionForeground": "#8C8C8C",
 		"icon.foreground": "#8C8C8C",
@@ -25,7 +25,7 @@
 		"button.secondaryHoverBackground": "#FFFFFF10",
 		"checkbox.background": "#242526",
 		"checkbox.border": "#333536",
-		"checkbox.foreground": "#bfbfbf",
+		"checkbox.foreground": "#8C8C8C",
 		"dropdown.background": "#191A1B",
 		"dropdown.border": "#333536",
 		"dropdown.foreground": "#bfbfbf",
@@ -33,7 +33,7 @@
 		"input.background": "#191A1B",
 		"input.border": "#333536FF",
 		"input.foreground": "#bfbfbf",
-		"input.placeholderForeground": "#777777",
+		"input.placeholderForeground": "#555555",
 		"inputOption.activeBackground": "#3994BC33",
 		"inputOption.activeForeground": "#bfbfbf",
 		"inputOption.activeBorder": "#2A2B2CFF",
@@ -60,6 +60,7 @@
 		"list.hoverBackground": "#262728",
 		"list.hoverForeground": "#bfbfbf",
 		"list.dropBackground": "#3994BC1A",
+		"toolbar.hoverBackground": "#FFFFFF18",
 		"list.focusBackground": "#3994BC26",
 		"list.focusForeground": "#bfbfbf",
 		"list.focusOutline": "#3994BCB3",
@@ -84,7 +85,7 @@
 		"sideBarSectionHeader.foreground": "#bfbfbf",
 		"sideBarSectionHeader.border": "#2A2B2CFF",
 		"titleBar.activeBackground": "#191A1B",
-		"titleBar.activeForeground": "#bfbfbf",
+		"titleBar.activeForeground": "#8C8C8C",
 		"titleBar.inactiveBackground": "#191A1B",
 		"titleBar.inactiveForeground": "#8C8C8C",
 		"titleBar.border": "#2A2B2CFF",
@@ -99,22 +100,23 @@
 		"commandCenter.foreground": "#bfbfbf",
 		"commandCenter.activeForeground": "#bfbfbf",
 		"commandCenter.background": "#191A1B",
-		"commandCenter.activeBackground": "#252627",
+		"commandCenter.activeBackground": "#FFFFFF0F",
 		"commandCenter.border": "#2E3031",
 		"editor.background": "#121314",
 		"editor.foreground": "#BBBEBF",
 		"editorStickyScroll.background": "#121314",
 		"editorStickyScrollHover.background": "#202122",
+		"editorStickyScroll.border": "#2A2B2CFF",
 		"editorLineNumber.foreground": "#858889",
 		"editorLineNumber.activeForeground": "#BBBEBF",
 		"editorCursor.foreground": "#BBBEBF",
-		"editor.selectionBackground": "#27678280",
+		"editor.selectionBackground": "#276782dd",
 		"editor.inactiveSelectionBackground": "#27678260",
-        "editor.selectionHighlightBackground": "#27678260",
-        "editor.wordHighlightBackground": "#27678250",
-        "editor.wordHighlightStrongBackground": "#27678280",
-        "editor.findMatchBackground": "#27678290",
-        "editor.findMatchHighlightBackground": "#27678280",
+		"editor.selectionHighlightBackground": "#27678260",
+		"editor.wordHighlightBackground": "#27678250",
+		"editor.wordHighlightStrongBackground": "#27678280",
+		"editor.findMatchBackground": "#27678290",
+		"editor.findMatchHighlightBackground": "#27678280",
 		"editor.findRangeHighlightBackground": "#242526",
 		"editor.hoverHighlightBackground": "#242526",
 		"editor.lineHighlightBackground": "#242526",
@@ -153,8 +155,10 @@
 		"editorGutter.background": "#121314",
 		"editorGutter.addedBackground": "#72C892",
 		"editorGutter.deletedBackground": "#F28772",
-		"diffEditor.insertedTextBackground": "#72C89233",
-		"diffEditor.removedTextBackground": "#F2877233",
+		"diffEditor.insertedLineBackground": "#347d3926",
+		"diffEditor.insertedTextBackground": "#57ab5a4d",
+		"diffEditor.removedLineBackground": "#c93c3726",
+		"diffEditor.removedTextBackground": "#f470674d",
 		"editorOverviewRuler.border": "#2A2B2CFF",
 		"editorOverviewRuler.findMatchForeground": "#3a94bc99",
 		"editorOverviewRuler.modifiedForeground": "#6ab890",
@@ -187,15 +191,15 @@
 		"tab.inactiveForeground": "#8C8C8C",
 		"tab.border": "#2A2B2CFF",
 		"tab.lastPinnedBorder": "#2A2B2CFF",
-		"tab.activeBorder": "#121314",
 		"tab.activeBorderTop": "#3994BC",
-		"tab.hoverBackground": "#262728",
+		"tab.hoverBackground": "#121314",
 		"tab.hoverForeground": "#bfbfbf",
 		"tab.unfocusedActiveBackground": "#121314",
 		"tab.unfocusedActiveForeground": "#8C8C8C",
 		"tab.unfocusedInactiveBackground": "#191A1B",
 		"tab.unfocusedInactiveForeground": "#444444",
 		"editorGroupHeader.tabsBackground": "#191A1B",
+		"tab.activeBorder": "#121314",
 		"editorGroupHeader.tabsBorder": "#2A2B2CFF",
 		"breadcrumb.foreground": "#8C8C8C",
 		"breadcrumb.background": "#121314",
@@ -227,7 +231,7 @@
 		"quickInputList.focusBackground": "#3994BC26",
 		"quickInputList.focusForeground": "#bfbfbf",
 		"quickInputList.focusIconForeground": "#bfbfbf",
-		"quickInputList.hoverBackground": "#515253",
+		"quickInputList.hoverBackground": "#262728",
 		"terminal.selectionBackground": "#3994BC33",
 		"terminal.background": "#191A1B",
 		"terminal.border": "#2A2B2CFF",
@@ -263,374 +267,428 @@
 		"charts.yellow": "#E0B97F",
 		"charts.orange": "#CD861A",
 		"charts.green": "#86CF86",
-		"charts.purple": "#AD80D7"
+		"charts.purple": "#AD80D7",
+		"inlineChat.border": "#00000000",
+		"minimapSlider.background": "#83848533",
+		"minimapSlider.hoverBackground": "#83848566",
+		"minimapSlider.activeBackground": "#83848599",
 	},
 	"tokenColors": [
 		{
 			"scope": [
-				"comment"
+				"comment",
+				"punctuation.definition.comment",
+				"string.comment"
 			],
 			"settings": {
-				"foreground": "#6F9B60"
+				"foreground": "#768390"
 			}
 		},
 		{
 			"scope": [
-				"keyword",
-				"storage.modifier",
-				"storage.type",
-				"keyword.operator.new",
-				"keyword.operator.expression",
-				"keyword.operator.cast",
-				"keyword.operator.sizeof",
-				"keyword.operator.instanceof"
+				"constant.other.placeholder",
+				"constant.character"
 			],
 			"settings": {
-				"foreground": "#4F8FDD"
+				"foreground": "#F47067"
 			}
 		},
 		{
 			"scope": [
-				"string"
+				"constant",
+				"entity.name.constant",
+				"variable.other.constant",
+				"variable.other.enummember",
+				"variable.language",
+				"entity"
 			],
 			"settings": {
-				"foreground": "#C48081"
+				"foreground": "#6CB6FF"
 			}
 		},
 		{
-			"name": "Language constants",
 			"scope": [
-				"constant.language"
+				"entity.name",
+				"meta.export.default",
+				"meta.definition.variable"
 			],
 			"settings": {
-				"foreground": "#4F8FDD"
+				"foreground": "#F69D50"
 			}
 		},
 		{
-			"name": "HTML/XML tags",
 			"scope": [
-				"entity.name.tag",
-				"meta.tag.sgml",
-				"markup.deleted.git_gutter"
+				"variable.parameter.function",
+				"meta.jsx.children",
+				"meta.block",
+				"meta.tag.attributes",
+				"entity.name.constant",
+				"meta.object.member",
+				"meta.embedded.expression"
 			],
 			"settings": {
-				"foreground": "#4F9BDD"
+				"foreground": "#ADBAC7"
 			}
 		},
 		{
-			"name": "HTML/XML tag punctuation",
-			"scope": [
-				"punctuation.definition.tag.html",
-				"punctuation.definition.tag.begin.html",
-				"punctuation.definition.tag.end.html"
-			],
+			"scope": "entity.name.function",
 			"settings": {
-				"foreground": "#7A828B"
+				"foreground": "#DCBDFB"
 			}
 		},
 		{
-			"name": "HTML/XML attribute names",
 			"scope": [
-				"entity.other.attribute-name"
+				"entity.name.tag",
+				"support.class.component"
 			],
 			"settings": {
-				"foreground": "#90D5FF"
+				"foreground": "#8DDB8C"
 			}
 		},
 		{
-			"name": "Operators",
-			"scope": [
-				"keyword.operator"
-			],
+			"scope": "keyword",
 			"settings": {
-				"foreground": "#C5CCD6"
+				"foreground": "#F47067"
 			}
 		},
 		{
-			"name": "Function declarations",
 			"scope": [
-				"entity.name.function",
-				"support.function",
-				"support.constant.handlebars",
-				"source.powershell variable.other.member",
-				"entity.name.operator.custom-literal"
+				"storage",
+				"storage.type"
 			],
 			"settings": {
-				"foreground": "#D1D6AE"
+				"foreground": "#F47067"
 			}
 		},
 		{
-			"name": "Types declaration and references",
 			"scope": [
-				"support.class",
-				"support.type",
-				"entity.name.type",
-				"entity.name.namespace",
-				"entity.other.attribute",
-				"entity.name.scope-resolution",
-				"entity.name.class",
-				"storage.type.numeric.go",
-				"storage.type.byte.go",
-				"storage.type.boolean.go",
-				"storage.type.string.go",
-				"storage.type.uintptr.go",
-				"storage.type.error.go",
-				"storage.type.rune.go",
-				"storage.type.cs",
-				"storage.type.generic.cs",
-				"storage.type.modifier.cs",
-				"storage.type.variable.cs",
-				"storage.type.annotation.java",
-				"storage.type.generic.java",
-				"storage.type.java",
-				"storage.type.object.array.java",
-				"storage.type.primitive.array.java",
-				"storage.type.primitive.java",
-				"storage.type.token.java",
-				"storage.type.groovy",
-				"storage.type.annotation.groovy",
-				"storage.type.parameters.groovy",
-				"storage.type.generic.groovy",
-				"storage.type.object.array.groovy",
-				"storage.type.primitive.array.groovy",
-				"storage.type.primitive.groovy"
+				"storage.modifier.package",
+				"storage.modifier.import",
+				"storage.type.java"
 			],
 			"settings": {
-				"foreground": "#48C9C4"
+				"foreground": "#ADBAC7"
 			}
 		},
 		{
-			"name": "Types declaration and references, TS grammar specific",
 			"scope": [
-				"meta.type.cast.expr",
-				"meta.type.new.expr",
-				"support.constant.math",
-				"support.constant.dom",
-				"support.constant.json",
-				"entity.other.inherited-class",
-				"punctuation.separator.namespace.ruby"
+				"string",
+				"string punctuation.section.embedded source"
 			],
 			"settings": {
-				"foreground": "#48C9B9"
+				"foreground": "#96D0FF"
 			}
 		},
 		{
-			"name": "Control flow / Special keywords",
-			"scope": [
-				"keyword.control",
-				"source.cpp keyword.operator.new",
-				"keyword.operator.delete",
-				"keyword.other.using",
-				"keyword.other.directive.using",
-				"keyword.other.operator",
-				"entity.name.operator"
-			],
+			"scope": "support",
 			"settings": {
-				"foreground": "#C184C6"
+				"foreground": "#6CB6FF"
 			}
 		},
 		{
-			"name": "Variable and parameter name",
-			"scope": [
-				"variable",
-				"meta.definition.variable.name",
-				"support.variable",
-				"entity.name.variable",
-				"constant.other.placeholder"
-			],
+			"scope": "meta.property-name",
 			"settings": {
-				"foreground": "#90D5FF"
+				"foreground": "#6CB6FF"
 			}
 		},
 		{
-			"name": "Constants and enums",
-			"scope": [
-				"variable.other.constant",
-				"variable.other.enummember"
-			],
+			"scope": "variable",
+			"settings": {
+				"foreground": "#F69D50"
+			}
+		},
+		{
+			"scope": "variable.other",
+			"settings": {
+				"foreground": "#ADBAC7"
+			}
+		},
+		{
+			"scope": "invalid.broken",
+			"settings": {
+				"foreground": "#FF938A",
+				"fontStyle": "italic"
+			}
+		},
+		{
+			"scope": "invalid.deprecated",
+			"settings": {
+				"foreground": "#FF938A",
+				"fontStyle": "italic"
+			}
+		},
+		{
+			"scope": "invalid.illegal",
+			"settings": {
+				"foreground": "#FF938A",
+				"fontStyle": "italic"
+			}
+		},
+		{
+			"scope": "invalid.unimplemented",
+			"settings": {
+				"foreground": "#FF938A",
+				"fontStyle": "italic"
+			}
+		},
+		{
+			"scope": "carriage-return",
+			"settings": {
+				"foreground": "#CDD9E5",
+				"background": "#F47067",
+				"fontStyle": "italic underline",
+				"content": "^M"
+			}
+		},
+		{
+			"scope": "message.error",
 			"settings": {
-				"foreground": "#4CBDFF"
+				"foreground": "#FF938A"
+			}
+		},
+		{
+			"scope": "string variable",
+			"settings": {
+				"foreground": "#6CB6FF"
 			}
 		},
 		{
-			"name": "Object keys, TS grammar specific",
 			"scope": [
-				"meta.object-literal.key"
+				"source.regexp",
+				"string.regexp"
 			],
 			"settings": {
-				"foreground": "#90D5FF"
+				"foreground": "#96D0FF"
 			}
 		},
 		{
-			"name": "CSS property value",
 			"scope": [
-				"support.constant.property-value",
-				"support.constant.font-name",
-				"support.constant.media-type",
-				"support.constant.media",
-				"constant.other.color.rgb-value",
-				"constant.other.rgb-value",
-				"support.constant.color"
+				"string.regexp.character-class",
+				"string.regexp constant.character.escape",
+				"string.regexp source.ruby.embedded",
+				"string.regexp string.regexp.arbitrary-repitition"
 			],
 			"settings": {
-				"foreground": "#C48F80"
+				"foreground": "#96D0FF"
+			}
+		},
+		{
+			"scope": "string.regexp constant.character.escape",
+			"settings": {
+				"foreground": "#8DDB8C",
+				"fontStyle": "bold"
+			}
+		},
+		{
+			"scope": "support.constant",
+			"settings": {
+				"foreground": "#6CB6FF"
+			}
+		},
+		{
+			"scope": "support.variable",
+			"settings": {
+				"foreground": "#6CB6FF"
+			}
+		},
+		{
+			"scope": "support.type.property-name.json",
+			"settings": {
+				"foreground": "#8DDB8C"
+			}
+		},
+		{
+			"scope": "meta.module-reference",
+			"settings": {
+				"foreground": "#6CB6FF"
+			}
+		},
+		{
+			"scope": "punctuation.definition.list.begin.markdown",
+			"settings": {
+				"foreground": "#F69D50"
 			}
 		},
 		{
-			"name": "Regular expression groups",
 			"scope": [
-				"punctuation.definition.group.regexp",
-				"punctuation.definition.group.assertion.regexp",
-				"punctuation.definition.character-class.regexp",
-				"punctuation.character.set.begin.regexp",
-				"punctuation.character.set.end.regexp",
-				"keyword.operator.negation.regexp",
-				"support.other.parenthesis.regexp"
+				"markup.heading",
+				"markup.heading entity.name"
 			],
 			"settings": {
-				"foreground": "#C49580"
+				"foreground": "#6CB6FF",
+				"fontStyle": "bold"
+			}
+		},
+		{
+			"scope": "markup.quote",
+			"settings": {
+				"foreground": "#8DDB8C"
+			}
+		},
+		{
+			"scope": "markup.italic",
+			"settings": {
+				"foreground": "#ADBAC7",
+				"fontStyle": "italic"
+			}
+		},
+		{
+			"scope": "markup.bold",
+			"settings": {
+				"foreground": "#ADBAC7",
+				"fontStyle": "bold"
 			}
 		},
 		{
 			"scope": [
-				"constant.character.character-class.regexp",
-				"constant.other.character-class.set.regexp",
-				"constant.other.character-class.regexp",
-				"constant.character.set.regexp"
+				"markup.underline"
 			],
 			"settings": {
-				"foreground": "#C86971"
+				"fontStyle": "underline"
 			}
 		},
 		{
 			"scope": [
-				"keyword.operator.or.regexp",
-				"keyword.control.anchor.regexp"
+				"markup.strikethrough"
 			],
 			"settings": {
-				"foreground": "#CBD6AE"
+				"fontStyle": "strikethrough"
+			}
+		},
+		{
+			"scope": "markup.inline.raw",
+			"settings": {
+				"foreground": "#6CB6FF"
 			}
 		},
 		{
-			"scope": "keyword.operator.quantifier.regexp",
+			"scope": [
+				"markup.deleted",
+				"meta.diff.header.from-file",
+				"punctuation.definition.deleted"
+			],
 			"settings": {
-				"foreground": "#CCBD84"
+				"foreground": "#FF938A",
+				"background": "#5D0F12"
 			}
 		},
 		{
 			"scope": [
-				"constant.character",
-				"constant.other.option"
+				"punctuation.section.embedded"
 			],
 			"settings": {
-				"foreground": "#4F9BDD"
+				"foreground": "#F47067"
 			}
 		},
 		{
-			"scope": "constant.character.escape",
+			"scope": [
+				"markup.inserted",
+				"meta.diff.header.to-file",
+				"punctuation.definition.inserted"
+			],
 			"settings": {
-				"foreground": "#CCB784"
+				"foreground": "#8DDB8C",
+				"background": "#113417"
 			}
 		},
 		{
-			"scope": "entity.name.label",
+			"scope": [
+				"markup.changed",
+				"punctuation.definition.changed"
+			],
 			"settings": {
-				"foreground": "#BAC2CC"
+				"foreground": "#F69D50",
+				"background": "#682D0F"
 			}
 		},
 		{
-			"name": "Numbers",
 			"scope": [
-				"constant.numeric"
+				"markup.ignored",
+				"markup.untracked"
 			],
 			"settings": {
-				"foreground": "#A8CAAD"
+				"foreground": "#2D333B",
+				"background": "#6CB6FF"
 			}
 		},
 		{
-			"name": "Markup Heading",
-			"scope": "markup.heading",
+			"scope": "meta.diff.range",
 			"settings": {
-				"foreground": "#64b0df",
+				"foreground": "#DCBDFB",
 				"fontStyle": "bold"
 			}
 		},
 		{
-			"name": "Markup Bold",
-			"scope": "markup.bold",
+			"scope": "meta.diff.header",
 			"settings": {
-				"foreground": "#C48081",
+				"foreground": "#6CB6FF"
+			}
+		},
+		{
+			"scope": "meta.separator",
+			"settings": {
+				"foreground": "#6CB6FF",
 				"fontStyle": "bold"
 			}
 		},
 		{
-			"name": "Markup Italic",
-			"scope": "markup.italic",
+			"scope": "meta.output",
 			"settings": {
-				"fontStyle": "italic"
+				"foreground": "#6CB6FF"
 			}
 		},
 		{
-			"name": "Markup Strikethrough",
-			"scope": "markup.strikethrough",
+			"scope": [
+				"brackethighlighter.tag",
+				"brackethighlighter.curly",
+				"brackethighlighter.round",
+				"brackethighlighter.square",
+				"brackethighlighter.angle",
+				"brackethighlighter.quote"
+			],
 			"settings": {
-				"fontStyle": "strikethrough"
+				"foreground": "#768390"
 			}
 		},
 		{
-			"name": "Markup Underline",
-			"scope": "markup.underline",
+			"scope": "brackethighlighter.unmatched",
 			"settings": {
-				"fontStyle": "underline"
+				"foreground": "#FF938A"
 			}
 		},
 		{
-			"name": "Markup Quote",
-			"scope": "markup.quote",
+			"scope": [
+				"constant.other.reference.link",
+				"string.other.link"
+			],
 			"settings": {
-				"foreground": "#C184C6"
+				"foreground": "#96D0FF"
 			}
 		},
 		{
-			"name": "Markup List",
-			"scope": "markup.list",
+			"scope": "token.info-token",
 			"settings": {
-				"foreground": "#48C9C4"
+				"foreground": "#6796E6"
 			}
 		},
 		{
-			"name": "Markup Inline Raw",
-			"scope": "markup.inline.raw",
+			"scope": "token.warn-token",
 			"settings": {
-				"foreground": "#D1D6AE"
+				"foreground": "#CD9731"
 			}
 		},
 		{
-			"name": "Markup Raw/Fenced Code Block",
-			"scope": [
-				"markup.raw",
-				"markup.fenced_code"
-			],
+			"scope": "token.error-token",
 			"settings": {
-				"foreground": "#8C8C8C"
+				"foreground": "#F44747"
 			}
 		},
 		{
-			"name": "Markup Link",
-			"scope": [
-				"meta.link",
-				"markup.underline.link"
-			],
+			"scope": "token.debug-token",
 			"settings": {
-				"foreground": "#48A0C7"
+				"foreground": "#B267E6"
 			}
 		}
 	],
-	"semanticHighlighting": true,
-	"semanticTokenColors": {
-		"newOperator": "#C586C0",
-		"stringLiteral": "#ce9178",
-		"customLiteral": "#DCDCAA",
-		"numberLiteral": "#b5cea8"
-	}
+	"semanticHighlighting": true
 }
diff --git a/extensions/theme-2026/themes/2026-light.json b/extensions/theme-2026/themes/2026-light.json
index b86ef612b20c3..6df7171b0d29a 100644
--- a/extensions/theme-2026/themes/2026-light.json
+++ b/extensions/theme-2026/themes/2026-light.json
@@ -11,7 +11,7 @@
 		"icon.foreground": "#606060",
 		"focusBorder": "#0069CCFF",
 		"textBlockQuote.background": "#EAEAEA",
-		"textBlockQuote.border": "#F2F3F4FF",
+		"textBlockQuote.border": "#F0F1F2FF",
 		"textCodeBlock.background": "#EAEAEA",
 		"textLink.foreground": "#0069CC",
 		"textLink.activeForeground": "#0069CC",
@@ -27,7 +27,7 @@
 		"button.secondaryHoverBackground": "#F2F3F4",
 		"checkbox.background": "#EAEAEA",
 		"checkbox.border": "#D8D8D8",
-		"checkbox.foreground": "#202020",
+		"checkbox.foreground": "#606060",
 		"dropdown.background": "#FFFFFF",
 		"dropdown.border": "#D8D8D8",
 		"dropdown.foreground": "#202020",
@@ -38,7 +38,7 @@
 		"input.placeholderForeground": "#999999",
 		"inputOption.activeBackground": "#0069CC26",
 		"inputOption.activeForeground": "#202020",
-		"inputOption.activeBorder": "#F2F3F4FF",
+		"inputOption.activeBorder": "#F0F1F2FF",
 		"inputValidation.infoBackground": "#E6F2FA",
 		"inputValidation.infoBorder": "#0069CC",
 		"inputValidation.infoForeground": "#202020",
@@ -50,9 +50,10 @@
 		"inputValidation.errorForeground": "#202020",
 		"scrollbar.shadow": "#00000000",
 		"widget.shadow": "#00000000",
-		"widget.border": "#EEEEF1",
+		"widget.border": "#E2E2E5",
 		"editorStickyScroll.shadow": "#00000000",
 		"editorStickyScrollHover.background": "#F0F0F3",
+		"editorStickyScroll.border": "#F0F1F2FF",
 		"sideBarStickyScroll.shadow": "#00000000",
 		"panelStickyScroll.shadow": "#00000000",
 		"listFilterWidget.shadow": "#00000000",
@@ -79,7 +80,7 @@
 		"activityBar.background": "#FAFAFD",
 		"activityBar.foreground": "#202020",
 		"activityBar.inactiveForeground": "#606060",
-		"activityBar.border": "#F2F3F4FF",
+		"activityBar.border": "#F0F1F2FF",
 		"activityBar.activeBorder": "#000000",
 		"activityBar.activeFocusBorder": "#0069CCFF",
 		"activityBarBadge.background": "#0069CC",
@@ -87,16 +88,16 @@
 		"activityBarTop.activeBorder": "#000000",
 		"sideBar.background": "#FAFAFD",
 		"sideBar.foreground": "#202020",
-		"sideBar.border": "#F2F3F4FF",
+		"sideBar.border": "#F0F1F2FF",
 		"sideBarTitle.foreground": "#202020",
 		"sideBarSectionHeader.background": "#FAFAFD",
 		"sideBarSectionHeader.foreground": "#202020",
-		"sideBarSectionHeader.border": "#F2F3F4FF",
+		"sideBarSectionHeader.border": "#F0F1F2FF",
 		"titleBar.activeBackground": "#FAFAFD",
-		"titleBar.activeForeground": "#424242",
+		"titleBar.activeForeground": "#606060",
 		"titleBar.inactiveBackground": "#FAFAFD",
 		"titleBar.inactiveForeground": "#606060",
-		"titleBar.border": "#F2F3F4FF",
+		"titleBar.border": "#F0F1F2FF",
 		"menubar.selectionBackground": "#EAEAEA",
 		"menubar.selectionForeground": "#202020",
 		"menu.background": "#FAFAFD",
@@ -104,7 +105,7 @@
 		"menu.selectionBackground": "#0069CC1A",
 		"menu.selectionForeground": "#202020",
 		"menu.separatorBackground": "#EEEEF1",
-		"menu.border": "#F2F3F4FF",
+		"menu.border": "#E4E5E6FF",
 		"commandCenter.foreground": "#202020",
 		"commandCenter.activeForeground": "#202020",
 		"commandCenter.background": "#FAFAFD",
@@ -115,7 +116,7 @@
 		"editorLineNumber.foreground": "#606060",
 		"editorLineNumber.activeForeground": "#202020",
 		"editorCursor.foreground": "#202020",
-		"editor.selectionBackground": "#0069CC1A",
+		"editor.selectionBackground": "#0069CC40",
 		"editor.inactiveSelectionBackground": "#0069CC1A",
 		"editor.selectionHighlightBackground": "#0069CC15",
 		"editor.wordHighlightBackground": "#0069CC26",
@@ -133,34 +134,34 @@
 		"editorRuler.foreground": "#F7F7F7",
 		"editorCodeLens.foreground": "#606060",
 		"editorBracketMatch.background": "#0069CC40",
-		"editorBracketMatch.border": "#F2F3F4FF",
-		"editorWidget.background": "#F0F0F3",
-		"editorWidget.border": "#EEEEF1",
+		"editorBracketMatch.border": "#F0F1F2FF",
+		"editorWidget.background": "#FAFAFD",
+		"editorWidget.border": "#E4E5E6FF",
 		"editorWidget.foreground": "#202020",
-		"editorSuggestWidget.background": "#F0F0F3",
-		"editorSuggestWidget.border": "#EEEEF1",
+		"editorSuggestWidget.background": "#FAFAFD",
+		"editorSuggestWidget.border": "#E4E5E6FF",
 		"editorSuggestWidget.foreground": "#202020",
 		"editorSuggestWidget.highlightForeground": "#0069CC",
 		"editorSuggestWidget.selectedBackground": "#0069CC26",
-		"editorHoverWidget.background": "#F0F0F3",
-		"editorHoverWidget.border": "#EEEEF1",
+		"editorHoverWidget.background": "#FAFAFD",
+		"editorHoverWidget.border": "#E4E5E6FF",
 		"peekView.border": "#0069CC",
-		"peekViewEditor.background": "#F0F0F3",
+		"peekViewEditor.background": "#FAFAFD",
 		"peekViewEditor.matchHighlightBackground": "#0069CC33",
-		"peekViewResult.background": "#F0F0F3",
+		"peekViewResult.background": "#FAFAFD",
 		"peekViewResult.fileForeground": "#202020",
 		"peekViewResult.lineForeground": "#606060",
 		"peekViewResult.matchHighlightBackground": "#0069CC33",
 		"peekViewResult.selectionBackground": "#0069CC26",
 		"peekViewResult.selectionForeground": "#202020",
-		"peekViewTitle.background": "#F0F0F3",
+		"peekViewTitle.background": "#FAFAFD",
 		"peekViewTitleDescription.foreground": "#606060",
 		"peekViewTitleLabel.foreground": "#202020",
 		"editorGutter.addedBackground": "#587c0c",
 		"editorGutter.deletedBackground": "#ad0707",
 		"diffEditor.insertedTextBackground": "#587c0c26",
 		"diffEditor.removedTextBackground": "#ad070726",
-		"editorOverviewRuler.border": "#F2F3F4FF",
+		"editorOverviewRuler.border": "#F0F1F2FF",
 		"editorOverviewRuler.findMatchForeground": "#0069CC99",
 		"editorOverviewRuler.modifiedForeground": "#0069CC",
 		"editorOverviewRuler.addedForeground": "#587c0c",
@@ -169,13 +170,13 @@
 		"editorOverviewRuler.warningForeground": "#667309",
 		"editorGutter.background": "#FFFFFF",
 		"panel.background": "#FAFAFD",
-		"panel.border": "#F2F3F4FF",
+		"panel.border": "#F0F1F2FF",
 		"panelTitle.activeBorder": "#000000",
 		"panelTitle.activeForeground": "#202020",
 		"panelTitle.inactiveForeground": "#606060",
 		"statusBar.background": "#FAFAFD",
 		"statusBar.foreground": "#606060",
-		"statusBar.border": "#F2F3F4FF",
+		"statusBar.border": "#F0F1F2FF",
 		"statusBar.focusBorder": "#0069CCFF",
 		"statusBar.debuggingBackground": "#0069CC",
 		"statusBar.debuggingForeground": "#FFFFFF",
@@ -187,35 +188,35 @@
 		"statusBarItem.prominentBackground": "#0069CCDD",
 		"statusBarItem.prominentForeground": "#FFFFFF",
 		"statusBarItem.prominentHoverBackground": "#0069CC",
-		"toolbar.hoverBackground": "#DADADA4f",
+		"toolbar.hoverBackground": "#00000010",
 		"tab.activeBackground": "#FFFFFF",
 		"tab.activeForeground": "#202020",
 		"tab.inactiveBackground": "#FAFAFD",
 		"tab.inactiveForeground": "#606060",
-		"tab.border": "#F2F3F4FF",
-		"tab.lastPinnedBorder": "#F2F3F4FF",
-		"tab.activeBorder": "#FAFAFD",
+		"tab.border": "#F0F1F2FF",
+		"tab.lastPinnedBorder": "#F0F1F2FF",
 		"tab.activeBorderTop": "#000000",
-		"tab.hoverBackground": "#DADADA4f",
+		"tab.hoverBackground": "#FFFFFF",
 		"tab.hoverForeground": "#202020",
 		"tab.unfocusedActiveBackground": "#FAFAFD",
 		"tab.unfocusedActiveForeground": "#606060",
 		"tab.unfocusedInactiveBackground": "#FAFAFD",
 		"tab.unfocusedInactiveForeground": "#BBBBBB",
 		"editorGroupHeader.tabsBackground": "#FAFAFD",
-		"editorGroupHeader.tabsBorder": "#F2F3F4FF",
+		"tab.activeBorder": "#FFFFFF",
+		"editorGroupHeader.tabsBorder": "#F0F1F2FF",
 		"breadcrumb.foreground": "#606060",
 		"breadcrumb.background": "#FFFFFF",
 		"breadcrumb.focusForeground": "#202020",
 		"breadcrumb.activeSelectionForeground": "#202020",
-		"breadcrumbPicker.background": "#F0F0F3",
-		"notificationCenter.border": "#F2F3F4FF",
+		"breadcrumbPicker.background": "#FAFAFD",
+		"notificationCenter.border": "#F0F1F2FF",
 		"notificationCenterHeader.foreground": "#202020",
 		"notificationCenterHeader.background": "#FAFAFD",
-		"notificationToast.border": "#F2F3F4FF",
+		"notificationToast.border": "#F0F1F2FF",
 		"notifications.foreground": "#202020",
 		"notifications.background": "#FAFAFD",
-		"notifications.border": "#F2F3F4FF",
+		"notifications.border": "#F0F1F2FF",
 		"notificationLink.foreground": "#0069CC",
 		"notificationsWarningIcon.foreground": "#B69500",
 		"notificationsErrorIcon.foreground": "#ad0707",
@@ -229,7 +230,7 @@
 		"extensionButton.prominentHoverBackground": "#0064CC",
 		"pickerGroup.border": "#EEEEF1",
 		"pickerGroup.foreground": "#202020",
-		"quickInput.background": "#F0F0F3",
+		"quickInput.background": "#FAFAFD",
 		"quickInput.foreground": "#202020",
 		"quickInputList.focusBackground": "#0069CC1A",
 		"quickInputList.focusForeground": "#202020",
@@ -250,13 +251,13 @@
 		"quickInput.border": "#D8D8D8",
 		"gauge.foreground": "#0069CC",
 		"gauge.background": "#0069CC40",
-		"gauge.border": "#F2F3F4FF",
+		"gauge.border": "#F0F1F2FF",
 		"gauge.warningForeground": "#B69500",
 		"gauge.warningBackground": "#B6950040",
 		"gauge.errorForeground": "#ad0707",
 		"gauge.errorBackground": "#ad070740",
 		"statusBarItem.prominentHoverForeground": "#FFFFFF",
-		"quickInputTitle.background": "#F0F0F3",
+		"quickInputTitle.background": "#FAFAFD",
 		"chat.requestBubbleBackground": "#EEF4FB",
 		"chat.requestBubbleHoverBackground": "#E6EDFA",
 		"chat.thinkingShimmer": "#999999",
@@ -271,373 +272,403 @@
 		"charts.green": "#388A34",
 		"charts.purple": "#652D90",
 		"agentStatusIndicator.background": "#FFFFFF",
+		"inlineChat.border": "#00000000",
+		"minimapSlider.background": "#99999926",
+		"minimapSlider.hoverBackground": "#99999940",
+		"minimapSlider.activeBackground": "#99999955",
 	},
 	"tokenColors": [
 		{
 			"scope": [
-				"comment"
+				"comment",
+				"punctuation.definition.comment",
+				"string.comment"
 			],
 			"settings": {
-				"foreground": "#60984D"
+				"foreground": "#6e7781"
 			}
 		},
 		{
 			"scope": [
-				"keyword",
-				"storage.modifier",
-				"storage.type",
-				"keyword.operator.new",
-				"keyword.operator.expression",
-				"keyword.operator.cast",
-				"keyword.operator.sizeof",
-				"keyword.operator.instanceof"
+				"constant.other.placeholder",
+				"constant.character"
 			],
 			"settings": {
-				"foreground": "#5460C1"
+				"foreground": "#cf222e"
 			}
 		},
 		{
 			"scope": [
-				"string"
+				"constant",
+				"entity.name.constant",
+				"variable.other.constant",
+				"variable.other.enummember",
+				"variable.language",
+				"entity"
 			],
 			"settings": {
-				"foreground": "#B86855"
+				"foreground": "#0550ae"
 			}
 		},
 		{
-			"name": "Language constants",
 			"scope": [
-				"constant.language"
+				"entity.name",
+				"meta.export.default",
+				"meta.definition.variable"
 			],
 			"settings": {
-				"foreground": "#5460C1"
+				"foreground": "#953800"
 			}
 		},
 		{
-			"name": "HTML/XML tags",
 			"scope": [
-				"entity.name.tag",
-				"meta.tag.sgml",
-				"markup.deleted.git_gutter"
+				"variable.parameter.function",
+				"meta.jsx.children",
+				"meta.block",
+				"meta.tag.attributes",
+				"entity.name.constant",
+				"meta.object.member",
+				"meta.embedded.expression"
 			],
 			"settings": {
-				"foreground": "#5751DE"
+				"foreground": "#1f2328"
 			}
 		},
 		{
-			"name": "HTML/XML tag punctuation",
-			"scope": [
-				"punctuation.definition.tag.html",
-				"punctuation.definition.tag.begin.html",
-				"punctuation.definition.tag.end.html"
-			],
+			"scope": "entity.name.function",
 			"settings": {
-				"foreground": "#93201A"
+				"foreground": "#8250df"
 			}
 		},
 		{
-			"name": "HTML/XML attribute names",
 			"scope": [
-				"entity.other.attribute-name"
+				"entity.name.tag",
+				"support.class.component"
 			],
 			"settings": {
-				"foreground": "#E75854"
+				"foreground": "#116329"
 			}
 		},
 		{
-			"name": "Operators",
-			"scope": [
-				"keyword.operator"
-			],
+			"scope": "keyword",
 			"settings": {
-				"foreground": "#573F35"
+				"foreground": "#cf222e"
 			}
 		},
 		{
-			"name": "Function declarations",
 			"scope": [
-				"entity.name.function",
-				"support.function",
-				"support.constant.handlebars",
-				"source.powershell variable.other.member",
-				"entity.name.operator.custom-literal"
+				"storage",
+				"storage.type"
 			],
 			"settings": {
-				"foreground": "#98863B"
+				"foreground": "#cf222e"
 			}
 		},
 		{
-			"name": "Types declaration and references",
 			"scope": [
-				"support.class",
-				"support.type",
-				"entity.name.type",
-				"entity.name.namespace",
-				"entity.other.attribute",
-				"entity.name.scope-resolution",
-				"entity.name.class",
-				"storage.type.numeric.go",
-				"storage.type.byte.go",
-				"storage.type.boolean.go",
-				"storage.type.string.go",
-				"storage.type.uintptr.go",
-				"storage.type.error.go",
-				"storage.type.rune.go",
-				"storage.type.cs",
-				"storage.type.generic.cs",
-				"storage.type.modifier.cs",
-				"storage.type.variable.cs",
-				"storage.type.annotation.java",
-				"storage.type.generic.java",
-				"storage.type.java",
-				"storage.type.object.array.java",
-				"storage.type.primitive.array.java",
-				"storage.type.primitive.java",
-				"storage.type.token.java",
-				"storage.type.groovy",
-				"storage.type.annotation.groovy",
-				"storage.type.parameters.groovy",
-				"storage.type.generic.groovy",
-				"storage.type.object.array.groovy",
-				"storage.type.primitive.array.groovy",
-				"storage.type.primitive.groovy"
+				"storage.modifier.package",
+				"storage.modifier.import",
+				"storage.type.java"
 			],
 			"settings": {
-				"foreground": "#46969A"
+				"foreground": "#1f2328"
 			}
 		},
 		{
-			"name": "Types declaration and references, TS grammar specific",
 			"scope": [
-				"meta.type.cast.expr",
-				"meta.type.new.expr",
-				"support.constant.math",
-				"support.constant.dom",
-				"support.constant.json",
-				"entity.other.inherited-class",
-				"punctuation.separator.namespace.ruby"
+				"string",
+				"string punctuation.section.embedded source"
 			],
 			"settings": {
-				"foreground": "#419BB3"
+				"foreground": "#0a3069"
 			}
 		},
 		{
-			"name": "Control flow / Special keywords",
-			"scope": [
-				"keyword.control",
-				"source.cpp keyword.operator.new",
-				"source.cpp keyword.operator.delete",
-				"keyword.other.using",
-				"keyword.other.directive.using",
-				"keyword.other.operator",
-				"entity.name.operator"
-			],
+			"scope": "support",
 			"settings": {
-				"foreground": "#8F41AD"
+				"foreground": "#0550ae"
 			}
 		},
 		{
-			"name": "Variable and parameter name",
-			"scope": [
-				"variable",
-				"meta.definition.variable.name",
-				"support.variable",
-				"entity.name.variable",
-				"constant.other.placeholder"
-			],
+			"scope": "meta.property-name",
 			"settings": {
-				"foreground": "#282D85"
+				"foreground": "#0550ae"
 			}
 		},
 		{
-			"name": "Constants and enums",
-			"scope": [
-				"variable.other.constant",
-				"variable.other.enummember"
-			],
+			"scope": "variable",
 			"settings": {
-				"foreground": "#3086C5"
+				"foreground": "#953800"
 			}
 		},
 		{
-			"name": "Object keys, TS grammar specific",
-			"scope": [
-				"meta.object-literal.key"
-			],
+			"scope": "variable.other",
 			"settings": {
-				"foreground": "#282D85"
+				"foreground": "#1f2328"
 			}
 		},
 		{
-			"name": "CSS property value",
-			"scope": [
-				"support.constant.property-value",
-				"support.constant.font-name",
-				"support.constant.media-type",
-				"support.constant.media",
-				"constant.other.color.rgb-value",
-				"constant.other.rgb-value",
-				"support.constant.color"
-			],
+			"scope": "invalid.broken",
+			"settings": {
+				"fontStyle": "italic",
+				"foreground": "#82071e"
+			}
+		},
+		{
+			"scope": "invalid.deprecated",
+			"settings": {
+				"fontStyle": "italic",
+				"foreground": "#82071e"
+			}
+		},
+		{
+			"scope": "invalid.illegal",
 			"settings": {
-				"foreground": "#2D6AAE"
+				"fontStyle": "italic",
+				"foreground": "#82071e"
+			}
+		},
+		{
+			"scope": "invalid.unimplemented",
+			"settings": {
+				"fontStyle": "italic",
+				"foreground": "#82071e"
+			}
+		},
+		{
+			"scope": "carriage-return",
+			"settings": {
+				"fontStyle": "italic underline",
+				"background": "#cf222e",
+				"foreground": "#f6f8fa",
+				"content": "^M"
+			}
+		},
+		{
+			"scope": "message.error",
+			"settings": {
+				"foreground": "#82071e"
+			}
+		},
+		{
+			"scope": "string variable",
+			"settings": {
+				"foreground": "#0550ae"
 			}
 		},
 		{
-			"name": "Regular expression groups",
 			"scope": [
-				"punctuation.definition.group.regexp",
-				"punctuation.definition.group.assertion.regexp",
-				"punctuation.definition.character-class.regexp",
-				"punctuation.character.set.begin.regexp",
-				"punctuation.character.set.end.regexp",
-				"keyword.operator.negation.regexp",
-				"support.other.parenthesis.regexp"
+				"source.regexp",
+				"string.regexp"
 			],
 			"settings": {
-				"foreground": "#D68490"
+				"foreground": "#0a3069"
 			}
 		},
 		{
 			"scope": [
-				"constant.character.character-class.regexp",
-				"constant.other.character-class.set.regexp",
-				"constant.other.character-class.regexp",
-				"constant.character.set.regexp"
+				"string.regexp.character-class",
+				"string.regexp constant.character.escape",
+				"string.regexp source.ruby.embedded",
+				"string.regexp string.regexp.arbitrary-repitition"
 			],
 			"settings": {
-				"foreground": "#A63350"
+				"foreground": "#0a3069"
+			}
+		},
+		{
+			"scope": "string.regexp constant.character.escape",
+			"settings": {
+				"fontStyle": "bold",
+				"foreground": "#116329"
 			}
 		},
 		{
-			"scope": "keyword.operator.quantifier.regexp",
+			"scope": "support.constant",
 			"settings": {
-				"foreground": "#573F35"
+				"foreground": "#0550ae"
+			}
+		},
+		{
+			"scope": "support.variable",
+			"settings": {
+				"foreground": "#0550ae"
+			}
+		},
+		{
+			"scope": "support.type.property-name.json",
+			"settings": {
+				"foreground": "#116329"
+			}
+		},
+		{
+			"scope": "meta.module-reference",
+			"settings": {
+				"foreground": "#0550ae"
+			}
+		},
+		{
+			"scope": "punctuation.definition.list.begin.markdown",
+			"settings": {
+				"foreground": "#953800"
 			}
 		},
 		{
 			"scope": [
-				"keyword.operator.or.regexp",
-				"keyword.control.anchor.regexp"
+				"markup.heading",
+				"markup.heading entity.name"
 			],
 			"settings": {
-				"foreground": "#C54C5B"
+				"fontStyle": "bold",
+				"foreground": "#0550ae"
+			}
+		},
+		{
+			"scope": "markup.quote",
+			"settings": {
+				"foreground": "#116329"
+			}
+		},
+		{
+			"scope": "markup.italic",
+			"settings": {
+				"fontStyle": "italic",
+				"foreground": "#1f2328"
+			}
+		},
+		{
+			"scope": "markup.bold",
+			"settings": {
+				"fontStyle": "bold",
+				"foreground": "#1f2328"
 			}
 		},
 		{
 			"scope": [
-				"constant.character",
-				"constant.other.option"
+				"markup.underline"
 			],
 			"settings": {
-				"foreground": "#5751DE"
+				"fontStyle": "underline"
 			}
 		},
 		{
-			"scope": "constant.character.escape",
+			"scope": [
+				"markup.strikethrough"
+			],
 			"settings": {
-				"foreground": "#E14A46"
+				"fontStyle": "strikethrough"
 			}
 		},
 		{
-			"scope": "entity.name.label",
+			"scope": "markup.inline.raw",
 			"settings": {
-				"foreground": "#5C3923"
+				"foreground": "#0550ae"
 			}
 		},
 		{
-			"name": "Numbers",
 			"scope": [
-				"constant.numeric"
+				"markup.deleted",
+				"meta.diff.header.from-file",
+				"punctuation.definition.deleted"
 			],
 			"settings": {
-				"foreground": "#2B9A69"
+				"background": "#ffebe9",
+				"foreground": "#82071e"
 			}
 		},
 		{
-			"name": "Markup Heading",
-			"scope": "markup.heading",
+			"scope": [
+				"punctuation.section.embedded"
+			],
 			"settings": {
-				"foreground": "#5460C1",
-				"fontStyle": "bold"
+				"foreground": "#cf222e"
 			}
 		},
 		{
-			"name": "Markup Bold",
-			"scope": "markup.bold",
+			"scope": [
+				"markup.inserted",
+				"meta.diff.header.to-file",
+				"punctuation.definition.inserted"
+			],
 			"settings": {
-				"foreground": "#B86855",
-				"fontStyle": "bold"
+				"background": "#dafbe1",
+				"foreground": "#116329"
 			}
 		},
 		{
-			"name": "Markup Italic",
-			"scope": "markup.italic",
+			"scope": [
+				"markup.changed",
+				"punctuation.definition.changed"
+			],
 			"settings": {
-				"fontStyle": "italic"
+				"background": "#ffd8b5",
+				"foreground": "#953800"
 			}
 		},
 		{
-			"name": "Markup Strikethrough",
-			"scope": "markup.strikethrough",
+			"scope": [
+				"markup.ignored",
+				"markup.untracked"
+			],
 			"settings": {
-				"fontStyle": "strikethrough"
+				"foreground": "#eaeef2",
+				"background": "#0550ae"
 			}
 		},
 		{
-			"name": "Markup Underline",
-			"scope": "markup.underline",
+			"scope": "meta.diff.range",
 			"settings": {
-				"fontStyle": "underline"
+				"foreground": "#8250df",
+				"fontStyle": "bold"
 			}
 		},
 		{
-			"name": "Markup Quote",
-			"scope": "markup.quote",
+			"scope": "meta.diff.header",
 			"settings": {
-				"foreground": "#8F41AD"
+				"foreground": "#0550ae"
 			}
 		},
 		{
-			"name": "Markup List",
-			"scope": "markup.list",
+			"scope": "meta.separator",
 			"settings": {
-				"foreground": "#46969A"
+				"fontStyle": "bold",
+				"foreground": "#0550ae"
 			}
 		},
 		{
-			"name": "Markup Inline Raw",
-			"scope": "markup.inline.raw",
+			"scope": "meta.output",
 			"settings": {
-				"foreground": "#98863B"
+				"foreground": "#0550ae"
 			}
 		},
 		{
-			"name": "Markup Raw/Fenced Code Block",
 			"scope": [
-				"markup.raw",
-				"markup.fenced_code"
+				"brackethighlighter.tag",
+				"brackethighlighter.curly",
+				"brackethighlighter.round",
+				"brackethighlighter.square",
+				"brackethighlighter.angle",
+				"brackethighlighter.quote"
 			],
 			"settings": {
-				"foreground": "#606060"
+				"foreground": "#57606a"
+			}
+		},
+		{
+			"scope": "brackethighlighter.unmatched",
+			"settings": {
+				"foreground": "#82071e"
 			}
 		},
 		{
-			"name": "Markup Link",
 			"scope": [
-				"meta.link",
-				"markup.underline.link"
+				"constant.other.reference.link",
+				"string.other.link"
 			],
 			"settings": {
-				"foreground": "#0069CC"
+				"foreground": "#0a3069"
 			}
 		}
 	],
-	"semanticHighlighting": true,
-	"semanticTokenColors": {
-		"newOperator": "#AF00DB",
-		"stringLiteral": "#a31515",
-		"customLiteral": "#795E26",
-		"numberLiteral": "#098658"
-	}
+	"semanticHighlighting": true
 }
diff --git a/extensions/theme-2026/themes/styles.css b/extensions/theme-2026/themes/styles.css
deleted file mode 100644
index c1bc21f212125..0000000000000
--- a/extensions/theme-2026/themes/styles.css
+++ /dev/null
@@ -1,878 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-:root {
-	--radius-sm: 4px;
-	--radius-md: 6px;
-	--radius-lg: 8px;
-
-	--shadow-sm: 0 0 4px rgba(0, 0, 0, 0.08);
-	--shadow-md: 0 0 6px rgba(0, 0, 0, 0.08);
-	--shadow-lg: 0 0 12px rgba(0, 0, 0, 0.14);
-	--shadow-xl: 0 0 20px rgba(0, 0, 0, 0.15);
-	--shadow-hover: 0 0 8px rgba(0, 0, 0, 0.12);
-	--shadow-sm-strong: 0 0 4px rgba(0, 0, 0, 0.18);
-	--shadow-button-active: inset 0 1px 2px rgba(0, 0, 0, 0.1);
-	--shadow-active-tab: 0 8px 12px rgba(0, 0, 0, 0.02);
-
-	--backdrop-blur-md: blur(20px) saturate(180%);
-	--backdrop-blur-lg: blur(40px) saturate(180%);
-}
-
-/* Dark theme: add brightness reduction for contrast-safe luminosity blending over bright backgrounds */
-.monaco-workbench.vs-dark {
-	--backdrop-blur-md: blur(20px) saturate(180%) brightness(0.55);
-	--backdrop-blur-lg: blur(40px) saturate(180%) brightness(0.55);
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-/* Stealth Shadows - shadow-based depth for UI elements, controlled by workbench.stealthShadows.enabled */
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-/* Activity Bar */
-.monaco-workbench.vs .part.activitybar {
-	z-index: 50;
-	position: relative;
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-.monaco-workbench.nosidebar .part.activitybar {
-	box-shadow: var(--shadow-md);
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-.monaco-workbench.activitybar-right .part.activitybar {
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-/* Sidebar */
-.monaco-workbench.vs .part.sidebar {
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-.monaco-workbench.vs .part.auxiliarybar {
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-.monaco-workbench.panel-position-left.vs .part.panel {
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-.monaco-workbench.panel-position-right.vs .part.panel {
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-.monaco-pane-view .split-view-view:first-of-type > .pane > .pane-header {
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-.monaco-workbench.vs .monaco-sash.vertical {
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-.monaco-workbench.vs .monaco-sash.vertical:nth-child(2) {
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-.monaco-workbench.vs .monaco-sash.horizontal {
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-.monaco-workbench.vs .part.editor > .content .editor-group-container > .title .tabs-container > .tab.active {
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-.monaco-workbench.vs .part.editor > .content .editor-group-container > .title .tabs-container > .tab:hover:not(.active) {
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-
-/* Quick Input (Command Palette) */
-.monaco-workbench.monaco-reduce-transparency .quick-input-widget {
-	background-color: var(--vscode-quickInput-background) !important;
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-}
-
-/* Notifications */
-.monaco-workbench.monaco-reduce-transparency .notification-toast-container {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-	background: var(--vscode-notifications-background) !important;
-}
-
-.monaco-workbench.monaco-reduce-transparency .notifications-center {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-	background: var(--vscode-notifications-background) !important;
-}
-
-/* Context Menu / Action Widget */
-.monaco-workbench.monaco-reduce-transparency .action-widget {
-	background: var(--vscode-menu-background) !important;
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-}
-
-/* Suggest Widget */
-.monaco-workbench.monaco-reduce-transparency .monaco-editor .suggest-widget {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-	background: var(--vscode-editorSuggestWidget-background) !important;
-}
-
-/* Find Widget */
-.monaco-workbench.monaco-reduce-transparency .monaco-editor .find-widget {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-}
-
-.monaco-workbench.monaco-reduce-transparency .inline-chat-gutter-menu {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-}
-
-/* Dialog */
-.monaco-workbench.monaco-reduce-transparency .monaco-dialog-box {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-	background: var(--vscode-editor-background) !important;
-}
-
-/* Peek View */
-.monaco-workbench.monaco-reduce-transparency .monaco-editor .peekview-widget {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-	background: var(--vscode-peekViewEditor-background) !important;
-}
-
-/* Hover */
-.monaco-reduce-transparency .monaco-hover {
-	background-color: var(--vscode-editorHoverWidget-background) !important;
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-}
-
-.monaco-reduce-transparency .monaco-hover.workbench-hover,
-.monaco-reduce-transparency .workbench-hover {
-	background-color: var(--vscode-editorHoverWidget-background) !important;
-	-webkit-backdrop-filter: none !important;
-	backdrop-filter: none !important;
-}
-
-/* Keybinding Widget */
-.monaco-workbench.monaco-reduce-transparency .defineKeybindingWidget {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-}
-
-/* Chat Editor Overlay */
-.monaco-workbench.monaco-reduce-transparency .chat-editor-overlay-widget,
-.monaco-workbench.monaco-reduce-transparency .chat-diff-change-content-widget {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-}
-
-/* Debug Toolbar */
-.monaco-workbench.monaco-reduce-transparency .debug-toolbar {
-	-webkit-backdrop-filter: none !important;
-	backdrop-filter: none !important;
-}
-
-.monaco-workbench.monaco-reduce-transparency .debug-hover-widget {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-}
-
-/* Parameter Hints */
-.monaco-workbench.monaco-reduce-transparency .monaco-editor .parameter-hints-widget {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-	background: var(--vscode-editorWidget-background) !important;
-}
-
-/* Sticky Scroll */
-.monaco-workbench.monaco-reduce-transparency .monaco-editor .sticky-widget {
-	-webkit-backdrop-filter: none !important;
-	backdrop-filter: none !important;
-	background: var(--vscode-editor-background) !important;
-}
-
-.monaco-workbench.monaco-reduce-transparency .monaco-editor .sticky-widget .sticky-widget-line-numbers,
-.monaco-workbench.monaco-reduce-transparency .monaco-editor .sticky-widget .sticky-widget-lines,
-.monaco-workbench.monaco-reduce-transparency .monaco-editor .sticky-widget .sticky-line-content {
-	-webkit-backdrop-filter: none !important;
-	backdrop-filter: none !important;
-	background: var(--vscode-editor-background) !important;
-}
-
-/* Rename Box */
-.monaco-reduce-transparency .monaco-editor .rename-box.preview {
-	-webkit-backdrop-filter: none !important;
-	backdrop-filter: none !important;
-}
-
-/* Notebook */
-.monaco-workbench.monaco-reduce-transparency .notebookOverlay .monaco-list-row .cell-title-toolbar {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-}
-
-/* Command Center */
-.monaco-workbench.monaco-reduce-transparency .part.titlebar > .titlebar-container > .titlebar-center > .window-title > .command-center .action-item.command-center-center {
-	background: var(--vscode-commandCenter-background) !important;
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-}
-
-.monaco-workbench.monaco-reduce-transparency .part.titlebar > .titlebar-container > .titlebar-center > .window-title > .command-center .action-item.command-center-center:hover {
-	background: var(--vscode-commandCenter-activeBackground) !important;
-}
-
-/* Breadcrumbs */
-.monaco-workbench.monaco-reduce-transparency .breadcrumbs-picker-widget {
-	-webkit-backdrop-filter: none;
-	backdrop-filter: none;
-	background: var(--vscode-breadcrumbPicker-background) !important;
-}
-
-/* Quick Input filter input */
-.monaco-workbench.monaco-reduce-transparency .quick-input-widget .quick-input-filter .monaco-inputbox {
-	background: var(--vscode-input-background) !important;
-}
diff --git a/extensions/theme-seti/build/update-icon-theme.js b/extensions/theme-seti/build/update-icon-theme.js
index 366e7f37dd673..d4da96611081b 100644
--- a/extensions/theme-seti/build/update-icon-theme.js
+++ b/extensions/theme-seti/build/update-icon-theme.js
@@ -47,7 +47,11 @@ const inheritIconFromLanguage = {
 	"jsonl": 'json',
 	"postcss": 'css',
 	"django-html": 'html',
-	"blade": 'php'
+	"blade": 'php',
+	"prompt": 'markdown',
+	"instructions": 'markdown',
+	"chatagent": 'markdown',
+	"skill": 'markdown'
 };
 
 const ignoreExtAssociation = {
diff --git a/extensions/tunnel-forwarding/.npmrc b/extensions/tunnel-forwarding/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/tunnel-forwarding/.npmrc
+++ b/extensions/tunnel-forwarding/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/typescript-language-features/.npmrc b/extensions/typescript-language-features/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/typescript-language-features/.npmrc
+++ b/extensions/typescript-language-features/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/typescript-language-features/package.json b/extensions/typescript-language-features/package.json
index 51446da2325b6..879be480493bb 100644
--- a/extensions/typescript-language-features/package.json
+++ b/extensions/typescript-language-features/package.json
@@ -30,7 +30,9 @@
         "typescript.npm",
         "js/ts.tsserver.npm.path",
         "typescript.tsserver.nodePath",
-        "js/ts.tsserver.node.path"
+        "js/ts.tsserver.node.path",
+        "js/ts.tsserver.diagnosticDir",
+        "js/ts.tsserver.heapProfile"
       ]
     }
   },
@@ -1919,10 +1921,10 @@
             "markdownDeprecationMessage": "%configuration.suggest.paths.unifiedDeprecationMessage%",
             "scope": "resource"
           },
-          "js/ts.suggest.completeJSDocs": {
+          "js/ts.suggest.jsdoc.enabled": {
             "type": "boolean",
             "default": true,
-            "description": "%configuration.suggest.completeJSDocs%",
+            "description": "%configuration.suggest.jsdoc.enabled%",
             "scope": "language-overridable",
             "keywords": [
               "JavaScript",
@@ -1932,14 +1934,14 @@
           "javascript.suggest.completeJSDocs": {
             "type": "boolean",
             "default": true,
-            "description": "%configuration.suggest.completeJSDocs%",
+            "description": "%configuration.suggest.jsdoc.enabled%",
             "markdownDeprecationMessage": "%configuration.suggest.completeJSDocs.unifiedDeprecationMessage%",
             "scope": "language-overridable"
           },
           "typescript.suggest.completeJSDocs": {
             "type": "boolean",
             "default": true,
-            "description": "%configuration.suggest.completeJSDocs%",
+            "description": "%configuration.suggest.jsdoc.enabled%",
             "markdownDeprecationMessage": "%configuration.suggest.completeJSDocs.unifiedDeprecationMessage%",
             "scope": "language-overridable"
           },
@@ -2421,7 +2423,7 @@
           },
           "js/ts.tsserver.node.path": {
             "type": "string",
-            "description": "%configuration.tsserver.nodePath%",
+            "markdownDescription": "%configuration.tsserver.nodePath%",
             "scope": "window",
             "keywords": [
               "TypeScript"
@@ -2429,7 +2431,7 @@
           },
           "typescript.tsserver.nodePath": {
             "type": "string",
-            "description": "%configuration.tsserver.nodePath%",
+            "markdownDescription": "%configuration.tsserver.nodePath%",
             "markdownDeprecationMessage": "%configuration.tsserver.nodePath.unifiedDeprecationMessage%",
             "scope": "window"
           },
@@ -2556,6 +2558,16 @@
               "TypeScript"
             ]
           },
+          "js/ts.tsserver.diagnosticDir": {
+            "type": "string",
+            "markdownDescription": "%configuration.tsserver.diagnosticDir%",
+            "scope": "machine",
+            "keywords": [
+              "TypeScript",
+              "diagnostic",
+              "memory"
+            ]
+          },
           "typescript.tsserver.maxTsServerMemory": {
             "type": "number",
             "default": 3072,
@@ -2563,6 +2575,48 @@
             "markdownDeprecationMessage": "%configuration.tsserver.maxTsServerMemory.unifiedDeprecationMessage%",
             "scope": "window"
           },
+          "js/ts.tsserver.heapSnapshot": {
+            "type": "number",
+            "default": 0,
+            "minimum": 0,
+            "markdownDescription": "%configuration.tsserver.heapSnapshot%",
+            "scope": "window",
+            "keywords": [
+              "TypeScript",
+              "memory",
+              "diagnostics"
+            ]
+          },
+          "js/ts.tsserver.heapProfile": {
+            "type": "object",
+            "default": {
+              "enabled": false
+            },
+            "markdownDescription": "%configuration.tsserver.heapProfile%",
+            "scope": "machine",
+            "properties": {
+              "enabled": {
+                "type": "boolean",
+                "default": false,
+                "description": "%configuration.tsserver.heapProfile.enabled%"
+              },
+              "dir": {
+                "type": "string",
+                "description": "%configuration.tsserver.heapProfile.dir%"
+              },
+              "interval": {
+                "type": "number",
+                "minimum": 1,
+                "description": "%configuration.tsserver.heapProfile.interval%"
+              }
+            },
+            "keywords": [
+              "TypeScript",
+              "memory",
+              "heap",
+              "profile"
+            ]
+          },
           "js/ts.tsserver.watchOptions": {
             "description": "%configuration.tsserver.watchOptions%",
             "scope": "window",
@@ -2856,13 +2910,13 @@
         "command": "typescript.experimental.enableTsgo",
         "title": "Use TypeScript Go (Experimental)",
         "category": "TypeScript",
-        "enablement": "!config.typescript.experimental.useTsgo && config.typescript-go.executablePath"
+        "enablement": "!config.js/ts.experimental.useTsgo && !config.typescript.experimental.useTsgo && config.typescript-go.executablePath"
       },
       {
         "command": "typescript.experimental.disableTsgo",
         "title": "Stop using TypeScript Go (Experimental)",
         "category": "TypeScript",
-        "enablement": "config.typescript.experimental.useTsgo"
+        "enablement": "config.js/ts.experimental.useTsgo || config.typescript.experimental.useTsgo"
       }
     ],
     "menus": {
@@ -2939,7 +2993,7 @@
       "editor/context": [
         {
           "command": "typescript.goToSourceDefinition",
-          "when": "!config.typescript.experimental.useTsgo && tsSupportsSourceDefinition && (resourceLangId == typescript || resourceLangId == typescriptreact || resourceLangId == javascript || resourceLangId == javascriptreact)",
+          "when": "!config.js/ts.experimental.useTsgo && !config.typescript.experimental.useTsgo && tsSupportsSourceDefinition && (resourceLangId == typescript || resourceLangId == typescriptreact || resourceLangId == javascript || resourceLangId == javascriptreact)",
           "group": "navigation@1.41"
         }
       ],
diff --git a/extensions/typescript-language-features/package.nls.json b/extensions/typescript-language-features/package.nls.json
index 7cd88f9bf609b..48955c38552a0 100644
--- a/extensions/typescript-language-features/package.nls.json
+++ b/extensions/typescript-language-features/package.nls.json
@@ -1,5 +1,5 @@
 {
-	"displayName": "TypeScript and JavaScript Language Features",
+	"displayName": "JavaScript and TypeScript Language Features",
 	"description": "Provides rich language support for JavaScript and TypeScript.",
 	"workspaceTrust": "The extension requires workspace trust when the workspace version is used because it executes code specified by the workspace.",
 	"virtualWorkspaces": "In virtual workspaces, resolving and finding references across files is not supported.",
@@ -64,7 +64,7 @@
 	"format.semicolons.remove": "Remove unnecessary semicolons.",
 	"format.indentSwitchCase": "Indent case clauses in switch statements. Requires using TypeScript 5.1+ in the workspace.",
 	"format.enable": "Enable/disable the default JavaScript and TypeScript formatter.",
-	"configuration.format.enable.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.format.enable#` instead.",
+	"configuration.format.enable.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.format.enabled#` instead.",
 	"configuration.format.insertSpaceAfterCommaDelimiter.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.format.insertSpaceAfterCommaDelimiter#` instead.",
 	"configuration.format.insertSpaceAfterConstructor.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.format.insertSpaceAfterConstructor#` instead.",
 	"configuration.format.insertSpaceAfterSemicolonInForStatements.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.format.insertSpaceAfterSemicolonInForStatements#` instead.",
@@ -126,6 +126,12 @@
 	"configuration.tsserver.maxTsServerMemory": "The maximum amount of memory (in MB) to allocate to the TypeScript server process. To use a memory limit greater than 4 GB, use `#js/ts.tsserver.node.path#` to run TS Server with a custom Node installation.",
 	"configuration.tsserver.maxTsServerMemory.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.tsserver.maxMemory#` instead.",
 	"configuration.tsserver.maxMemory": "The maximum amount of memory (in MB) to allocate to the TypeScript server process. To use a memory limit greater than 4 GB, use `#js/ts.tsserver.node.path#` to run TS Server with a custom Node installation.",
+	"configuration.tsserver.diagnosticDir": "Directory where TypeScript server writes Node diagnostic output by passing `--diagnostic-dir`.",
+	"configuration.tsserver.heapSnapshot": "Controls how many near-heap-limit snapshots TypeScript server writes by passing `--heapsnapshot-near-heap-limit`. Set to `0` to disable.",
+	"configuration.tsserver.heapProfile": "Configures heap profiling for TypeScript server.",
+	"configuration.tsserver.heapProfile.enabled": "Enable heap profiling for TypeScript server by passing `--heap-prof`.",
+	"configuration.tsserver.heapProfile.dir": "Directory where TypeScript server writes heap profiles by passing `--heap-prof-dir`.",
+	"configuration.tsserver.heapProfile.interval": "Sampling interval in bytes for TypeScript server heap profiling by passing `--heap-prof-interval`.",
 	"configuration.tsserver.experimental.enableProjectDiagnostics": "Enables project wide error reporting.",
 	"configuration.tsserver.experimental.enableProjectDiagnostics.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.tsserver.experimental.enableProjectDiagnostics#` instead.",
 	"typescript.locale": "Sets the locale used to report JavaScript and TypeScript errors. Defaults to use VS Code's locale.",
@@ -248,8 +254,8 @@
 	"configuration.autoClosingTags.enabled.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.autoClosingTags.enabled#` instead.",
 	"typescript.suggest.enabled": "Enable/disable autocomplete suggestions.",
 	"configuration.suggest.enabled.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.suggest.enabled#` instead.",
-	"configuration.suggest.completeJSDocs": "Enable/disable suggestion to complete JSDoc comments.",
-	"configuration.suggest.completeJSDocs.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.suggest.completeJSDocs#` instead.",
+	"configuration.suggest.jsdoc.enabled": "Enable/disable suggestion to complete JSDoc comments.",
+	"configuration.suggest.completeJSDocs.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.suggest.jsdoc.enabled#` instead.",
 	"configuration.tsserver.useVsCodeWatcher": "Use VS Code's file watchers instead of TypeScript's. Requires using TypeScript 5.4+ in the workspace.",
 	"configuration.tsserver.watchOptions": "Configure which watching strategies should be used to keep track of files and directories.",
 	"configuration.tsserver.watchOptions.vscode": "Use VS Code's file watchers instead of TypeScript's. Requires using TypeScript 5.4+ in the workspace.",
@@ -311,7 +317,7 @@
 	"configuration.tsserver.web.projectWideIntellisense.suppressSemanticErrors.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.tsserver.web.projectWideIntellisense.suppressSemanticErrors#` instead.",
 	"configuration.tsserver.web.typeAcquisition.enabled": "Enable/disable package acquisition on the web. This enables IntelliSense for imported packages. Requires `#js/ts.tsserver.web.projectWideIntellisense.enabled#`. Currently not supported for Safari.",
 	"configuration.tsserver.web.typeAcquisition.enabled.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.tsserver.web.typeAcquisition.enabled#` instead.",
-	"configuration.tsserver.nodePath": "Run TS Server on a custom Node installation. This can be a path to a Node executable, or 'node' if you want VS Code to detect a Node installation.",
+	"configuration.tsserver.nodePath": "Run TS Server on a custom Node installation. This can be a path to a Node executable, or `node` if you want VS Code to detect a Node installation.",
 	"configuration.tsserver.nodePath.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.tsserver.node.path#` instead.",
 	"configuration.tsserver.watchOptions.unifiedDeprecationMessage": "This setting is deprecated. Use `#js/ts.tsserver.watchOptions#` instead.",
 	"configuration.updateImportsOnPaste": "Automatically update imports when pasting code. Requires TypeScript 5.6+.",
diff --git a/extensions/typescript-language-features/src/configuration/configuration.ts b/extensions/typescript-language-features/src/configuration/configuration.ts
index a557f08c0246b..ae43fda659eda 100644
--- a/extensions/typescript-language-features/src/configuration/configuration.ts
+++ b/extensions/typescript-language-features/src/configuration/configuration.ts
@@ -110,6 +110,12 @@ export class ImplicitProjectConfiguration {
 	}
 }
 
+export interface TsServerHeapProfileConfiguration {
+	readonly enabled: boolean;
+	readonly dir: string | undefined;
+	readonly interval: number | undefined;
+}
+
 export interface TypeScriptServiceConfiguration {
 	readonly locale: string | null;
 	readonly globalTsdk: string | null;
@@ -126,6 +132,9 @@ export interface TypeScriptServiceConfiguration {
 	readonly enableDiagnosticsTelemetry: boolean;
 	readonly enableProjectDiagnostics: boolean;
 	readonly maxTsServerMemory: number;
+	readonly diagnosticDir: string | undefined;
+	readonly heapSnapshot: number;
+	readonly heapProfile: TsServerHeapProfileConfiguration;
 	readonly enablePromptUseWorkspaceTsdk: boolean;
 	readonly useVsCodeWatcher: boolean;
 	readonly watchOptions: Proto.WatchOptions | undefined;
@@ -168,6 +177,9 @@ export abstract class BaseServiceConfigurationProvider implements ServiceConfigu
 			enableDiagnosticsTelemetry: this.readEnableDiagnosticsTelemetry(),
 			enableProjectDiagnostics: this.readEnableProjectDiagnostics(),
 			maxTsServerMemory: this.readMaxTsServerMemory(),
+			diagnosticDir: this.readDiagnosticDir(),
+			heapSnapshot: this.readHeapSnapshot(),
+			heapProfile: this.readHeapProfileConfiguration(),
 			enablePromptUseWorkspaceTsdk: this.readEnablePromptUseWorkspaceTsdk(),
 			useVsCodeWatcher: this.readUseVsCodeWatcher(configuration),
 			watchOptions: this.readWatchOptions(),
@@ -288,6 +300,42 @@ export abstract class BaseServiceConfigurationProvider implements ServiceConfigu
 		return Math.max(memoryInMB, minimumMaxMemory);
 	}
 
+	protected readDiagnosticDir(): string | undefined {
+		const diagnosticDir = readUnifiedConfig<string | undefined>('tsserver.diagnosticDir', undefined, { fallbackSection: 'typescript' });
+		return typeof diagnosticDir === 'string' && diagnosticDir.length > 0 ? diagnosticDir : undefined;
+	}
+
+	protected readHeapSnapshot(): number {
+		const defaultNearHeapLimitSnapshotCount = 0;
+		const nearHeapLimitSnapshotCount = readUnifiedConfig<number>('tsserver.heapSnapshot', defaultNearHeapLimitSnapshotCount, { fallbackSection: 'typescript' });
+		if (!Number.isSafeInteger(nearHeapLimitSnapshotCount)) {
+			return defaultNearHeapLimitSnapshotCount;
+		}
+		return Math.max(nearHeapLimitSnapshotCount, 0);
+	}
+
+	private readHeapProfileConfiguration(): TsServerHeapProfileConfiguration {
+		const defaultHeapProfileConfiguration: TsServerHeapProfileConfiguration = {
+			enabled: false,
+			dir: undefined,
+			interval: undefined,
+		};
+
+		const rawConfig = readUnifiedConfig<{ enabled?: unknown; dir?: unknown; interval?: unknown }>('tsserver.heapProfile', defaultHeapProfileConfiguration, { fallbackSection: 'typescript' });
+
+		const enabled = typeof rawConfig.enabled === 'boolean' ? rawConfig.enabled : false;
+		const dir = typeof rawConfig.dir === 'string' && rawConfig.dir.length > 0 ? rawConfig.dir : undefined;
+		const interval = typeof rawConfig.interval === 'number' && Number.isSafeInteger(rawConfig.interval) && rawConfig.interval > 0
+			? rawConfig.interval
+			: undefined;
+
+		return {
+			enabled,
+			dir,
+			interval,
+		};
+	}
+
 	protected readEnablePromptUseWorkspaceTsdk(): boolean {
 		return readUnifiedConfig<boolean>('tsdk.promptToUseWorkspaceVersion', false, { fallbackSection: 'typescript', fallbackSubSectionNameOverride: 'enablePromptUseWorkspaceTsdk' });
 	}
diff --git a/extensions/typescript-language-features/src/languageFeatures/jsDocCompletions.ts b/extensions/typescript-language-features/src/languageFeatures/jsDocCompletions.ts
index 9e1c3c7cf9dcb..a060d7600147f 100644
--- a/extensions/typescript-language-features/src/languageFeatures/jsDocCompletions.ts
+++ b/extensions/typescript-language-features/src/languageFeatures/jsDocCompletions.ts
@@ -46,7 +46,7 @@ class JsDocCompletionProvider implements vscode.CompletionItemProvider {
 		position: vscode.Position,
 		token: vscode.CancellationToken
 	): Promise<vscode.CompletionItem[] | undefined> {
-		if (!readUnifiedConfig<boolean>('suggest.completeJSDocs', true, { scope: document, fallbackSection: this.language.id })) {
+		if (!readUnifiedConfig<boolean>('suggest.jsdoc.enabled', true, { scope: document, fallbackSection: this.language.id, fallbackSubSectionNameOverride: 'suggest.completeJSDocs' })) {
 			return undefined;
 		}
 
diff --git a/extensions/typescript-language-features/src/tsServer/serverProcess.electron.ts b/extensions/typescript-language-features/src/tsServer/serverProcess.electron.ts
index 7dbde90f7924c..a356fd7817bd4 100644
--- a/extensions/typescript-language-features/src/tsServer/serverProcess.electron.ts
+++ b/extensions/typescript-language-features/src/tsServer/serverProcess.electron.ts
@@ -24,6 +24,12 @@ const contentLengthSize: number = Buffer.byteLength(contentLength, 'utf8');
 const blank: number = Buffer.from(' ', 'utf8')[0];
 const backslashR: number = Buffer.from('\r', 'utf8')[0];
 const backslashN: number = Buffer.from('\n', 'utf8')[0];
+const gracefulExitTimeout = 5000;
+const tsServerExitRequest: Proto.Request = {
+	seq: 0,
+	type: 'request',
+	command: 'exit',
+};
 
 class ProtocolBuffer {
 
@@ -162,6 +168,24 @@ function getExecArgv(kind: TsServerProcessKind, configuration: TypeScriptService
 		args.push(`--max-old-space-size=${configuration.maxTsServerMemory}`);
 	}
 
+	if (configuration.diagnosticDir) {
+		args.push(`--diagnostic-dir=${configuration.diagnosticDir}`);
+	}
+
+	if (configuration.heapSnapshot > 0) {
+		args.push(`--heapsnapshot-near-heap-limit=${configuration.heapSnapshot}`);
+	}
+
+	if (configuration.heapProfile.enabled) {
+		args.push('--heap-prof');
+		if (configuration.heapProfile.dir) {
+			args.push(`--heap-prof-dir=${configuration.heapProfile.dir}`);
+		}
+		if (configuration.heapProfile.interval) {
+			args.push(`--heap-prof-interval=${configuration.heapProfile.interval}`);
+		}
+	}
+
 	return args;
 }
 
@@ -189,10 +213,15 @@ function getTssDebugBrk(): string | undefined {
 }
 
 class IpcChildServerProcess extends Disposable implements TsServerProcess {
+	private _killTimeout: NodeJS.Timeout | undefined;
+	private _isShuttingDown = false;
+
 	constructor(
 		private readonly _process: child_process.ChildProcess,
+		private readonly _useGracefulShutdown: boolean,
 	) {
 		super();
+		this._process.once('exit', () => this.clearKillTimeout());
 	}
 
 	write(serverRequest: Proto.Request): void {
@@ -212,18 +241,47 @@ class IpcChildServerProcess extends Disposable implements TsServerProcess {
 	}
 
 	kill(): void {
-		this._process.kill();
+		if (!this._useGracefulShutdown) {
+			this._process.kill();
+			return;
+		}
+
+		if (this._isShuttingDown) {
+			return;
+		}
+		this._isShuttingDown = true;
+
+		try {
+			this._process.send(tsServerExitRequest);
+		} catch {
+			this._process.kill();
+			return;
+		}
+
+		this._killTimeout = setTimeout(() => this._process.kill(), gracefulExitTimeout);
+		this._killTimeout.unref?.();
+	}
+
+	private clearKillTimeout(): void {
+		if (this._killTimeout) {
+			clearTimeout(this._killTimeout);
+			this._killTimeout = undefined;
+		}
 	}
 }
 
 class StdioChildServerProcess extends Disposable implements TsServerProcess {
 	private readonly _reader: Reader<Proto.Response>;
+	private _killTimeout: NodeJS.Timeout | undefined;
+	private _isShuttingDown = false;
 
 	constructor(
 		private readonly _process: child_process.ChildProcess,
+		private readonly _useGracefulShutdown: boolean,
 	) {
 		super();
 		this._reader = this._register(new Reader<Proto.Response>(this._process.stdout!));
+		this._process.once('exit', () => this.clearKillTimeout());
 	}
 
 	write(serverRequest: Proto.Request): void {
@@ -244,7 +302,39 @@ class StdioChildServerProcess extends Disposable implements TsServerProcess {
 	}
 
 	kill(): void {
-		this._process.kill();
+		if (!this._useGracefulShutdown) {
+			this._process.kill();
+			this._reader.dispose();
+			return;
+		}
+
+		if (this._isShuttingDown) {
+			return;
+		}
+		this._isShuttingDown = true;
+
+		try {
+			this._process.stdin?.write(JSON.stringify(tsServerExitRequest) + '\r\n', 'utf8');
+			this._process.stdin?.end();
+		} catch {
+			this._process.kill();
+			this._reader.dispose();
+			return;
+		}
+
+		this._killTimeout = setTimeout(() => {
+			this._process.kill();
+			this._reader.dispose();
+		}, gracefulExitTimeout);
+		this._killTimeout.unref?.();
+	}
+
+	private clearKillTimeout(): void {
+		if (this._killTimeout) {
+			clearTimeout(this._killTimeout);
+			this._killTimeout = undefined;
+		}
+
 		this._reader.dispose();
 	}
 }
@@ -272,6 +362,7 @@ export class ElectronServiceProcessFactory implements TsServerProcessFactory {
 		const env = generatePatchedEnv(process.env, tsServerPath, !!execPath);
 		const runtimeArgs = [...args];
 		const execArgv = getExecArgv(kind, configuration);
+		const useGracefulShutdown = configuration.heapProfile.enabled;
 		const useIpc = !execPath && version.apiVersion?.gte(API.v460);
 		if (useIpc) {
 			runtimeArgs.push('--useNodeIpc');
@@ -291,6 +382,6 @@ export class ElectronServiceProcessFactory implements TsServerProcessFactory {
 				stdio: useIpc ? ['pipe', 'pipe', 'pipe', 'ipc'] : undefined,
 			});
 
-		return useIpc ? new IpcChildServerProcess(childProcess) : new StdioChildServerProcess(childProcess);
+		return useIpc ? new IpcChildServerProcess(childProcess, useGracefulShutdown) : new StdioChildServerProcess(childProcess, useGracefulShutdown);
 	}
 }
diff --git a/extensions/vscode-api-tests/.npmrc b/extensions/vscode-api-tests/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/vscode-api-tests/.npmrc
+++ b/extensions/vscode-api-tests/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/vscode-api-tests/package.json b/extensions/vscode-api-tests/package.json
index 58ec85b1450d0..0ba8a2d299954 100644
--- a/extensions/vscode-api-tests/package.json
+++ b/extensions/vscode-api-tests/package.json
@@ -7,8 +7,10 @@
   "enabledApiProposals": [
     "activeComment",
     "authSession",
+    "browser",
     "environmentPower",
     "chatParticipantPrivate",
+    "chatPromptFiles",
     "chatProvider",
     "contribStatusBarItems",
     "contribViewsRemote",
@@ -70,6 +72,10 @@
       {
         "vendor": "test-lm-vendor",
         "displayName": "Test LM Vendor"
+      },
+      {
+        "vendor": "copilot",
+        "displayName": "Test Copilot LM Vendor"
       }
     ],
     "chatParticipants": [
@@ -146,6 +152,11 @@
           "id": "test.treeId",
           "name": "test-tree",
           "when": "never"
+        },
+        {
+          "id": "test.treeSwitchUpdate",
+          "name": "test-tree-switch-update",
+          "when": "never"
         }
       ]
     },
diff --git a/extensions/vscode-api-tests/src/singlefolder-tests/browser.test.ts b/extensions/vscode-api-tests/src/singlefolder-tests/browser.test.ts
new file mode 100644
index 0000000000000..fc0bcbb66bfb7
--- /dev/null
+++ b/extensions/vscode-api-tests/src/singlefolder-tests/browser.test.ts
@@ -0,0 +1,190 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as assert from 'assert';
+import * as vscode from 'vscode';
+import { window, ViewColumn } from 'vscode';
+import { assertNoRpc, closeAllEditors } from '../utils';
+
+(vscode.env.uiKind === vscode.UIKind.Web ? suite.skip : suite)('vscode API - browser', () => {
+
+	teardown(async function () {
+		assertNoRpc();
+		await closeAllEditors();
+	});
+
+	// #region window.browserTabs / activeBrowserTab
+
+	test('browserTabs is an array', () => {
+		assert.ok(Array.isArray(window.browserTabs));
+	});
+
+	test('activeBrowserTab is undefined when no browser tab is open', () => {
+		assert.strictEqual(window.activeBrowserTab, undefined);
+	});
+
+	// #endregion
+
+	// #region openBrowserTab
+
+	test('openBrowserTab returns a BrowserTab with url, title, and icon', async () => {
+		const tab = await window.openBrowserTab('about:blank');
+
+		assert.ok(tab);
+		assert.strictEqual(tab.url, 'about:blank');
+		assert.ok(tab.title);
+		assert.ok(tab.icon);
+	});
+
+	test('openBrowserTab adds tab to browserTabs', async () => {
+		const before = window.browserTabs.length;
+		await window.openBrowserTab('about:blank');
+		assert.strictEqual(window.browserTabs.length, before + 1);
+	});
+
+	test('openBrowserTab with viewColumn.Beside', async () => {
+		const tab = await window.openBrowserTab('about:blank', { viewColumn: ViewColumn.Beside });
+		assert.ok(tab);
+		assert.strictEqual(tab.url, 'about:blank');
+	});
+
+	test('openBrowserTab with preserveFocus', async () => {
+		const tab = await window.openBrowserTab('about:blank', { preserveFocus: true });
+		assert.ok(tab);
+	});
+
+	test('openBrowserTab with background', async () => {
+		const tab = await window.openBrowserTab('about:blank', { background: true });
+		assert.ok(tab);
+	});
+
+	// #endregion
+
+	// #region BrowserTab.close
+
+	test('BrowserTab.close removes the tab from browserTabs', async () => {
+		const tab = await window.openBrowserTab('about:blank');
+		const countBefore = window.browserTabs.length;
+
+		await tab.close();
+
+		assert.strictEqual(window.browserTabs.length, countBefore - 1);
+	});
+
+	// #endregion
+
+	// #region onDidOpenBrowserTab
+
+	test('onDidOpenBrowserTab fires when a tab is opened', async () => {
+		const opened = new Promise<vscode.BrowserTab>(resolve => {
+			const disposable = window.onDidOpenBrowserTab(tab => {
+				disposable.dispose();
+				resolve(tab);
+			});
+		});
+
+		const tab = await window.openBrowserTab('about:blank');
+		const firedTab = await opened;
+		assert.strictEqual(firedTab.url, tab.url);
+	});
+
+	// #endregion
+
+	// #region onDidCloseBrowserTab
+
+	test('onDidCloseBrowserTab fires when a tab is closed', async () => {
+		const tab = await window.openBrowserTab('about:blank');
+
+		const closed = new Promise<vscode.BrowserTab>(resolve => {
+			const disposable = window.onDidCloseBrowserTab(t => {
+				disposable.dispose();
+				resolve(t);
+			});
+		});
+
+		await tab.close();
+		const firedTab = await closed;
+		assert.ok(firedTab);
+	});
+
+	// #endregion
+
+	// #region activeBrowserTab / onDidChangeActiveBrowserTab
+
+	test('activeBrowserTab is set after opening a tab', async () => {
+		await window.openBrowserTab('about:blank');
+		assert.ok(window.activeBrowserTab);
+	});
+
+	test('onDidChangeActiveBrowserTab fires when active tab changes', async () => {
+		const changed = new Promise<vscode.BrowserTab | undefined>(resolve => {
+			const disposable = window.onDidChangeActiveBrowserTab(tab => {
+				disposable.dispose();
+				resolve(tab);
+			});
+		});
+
+		await window.openBrowserTab('about:blank');
+		const activeTab = await changed;
+		assert.ok(activeTab);
+	});
+
+	// #endregion
+
+	// #region CDP sessions
+
+	test('startCDPSession returns a session with expected API', async () => {
+		const tab = await window.openBrowserTab('about:blank');
+		const session = await tab.startCDPSession();
+
+		assert.ok(session);
+		assert.ok(session.onDidReceiveMessage);
+		assert.ok(session.onDidClose);
+		assert.ok(typeof session.sendMessage === 'function');
+		assert.ok(typeof session.close === 'function');
+
+		await session.close();
+	});
+
+	test('CDP sendMessage and onDidReceiveMessage round-trip', async () => {
+		const tab = await window.openBrowserTab('about:blank');
+		const session = await tab.startCDPSession();
+
+		const response = new Promise<any>(resolve => {
+			const disposable = session.onDidReceiveMessage((msg: any) => {
+				if (msg.id === 1) {
+					disposable.dispose();
+					resolve(msg);
+				}
+			});
+		});
+
+		await session.sendMessage({ id: 1, method: 'Target.getTargets' });
+		const msg = await response;
+		assert.ok(msg.result);
+		const targets: any[] = msg.result.targetInfos;
+		assert.equal(targets.length, 1);
+		assert.equal(targets[0].url, 'about:blank');
+
+		await session.close();
+	});
+
+	test('CDP session.close fires onDidClose', async () => {
+		const tab = await window.openBrowserTab('about:blank');
+		const session = await tab.startCDPSession();
+
+		const closed = new Promise<void>(resolve => {
+			const disposable = session.onDidClose(() => {
+				disposable.dispose();
+				resolve();
+			});
+		});
+
+		await session.close();
+		await closed;
+	});
+
+	// #endregion
+});
diff --git a/extensions/vscode-api-tests/src/singlefolder-tests/chat.test.ts b/extensions/vscode-api-tests/src/singlefolder-tests/chat.test.ts
index ff5b49d9b69a1..6ed6c91171878 100644
--- a/extensions/vscode-api-tests/src/singlefolder-tests/chat.test.ts
+++ b/extensions/vscode-api-tests/src/singlefolder-tests/chat.test.ts
@@ -17,7 +17,7 @@ suite('chat', () => {
 		disposables = [];
 
 		// Register a dummy default model which is required for a participant request to go through
-		disposables.push(lm.registerLanguageModelChatProvider('test-lm-vendor', {
+		disposables.push(lm.registerLanguageModelChatProvider('copilot', {
 			async provideLanguageModelChatInformation(_options, _token) {
 				return [{
 					id: 'test-lm',
diff --git a/extensions/vscode-api-tests/src/singlefolder-tests/tree.test.ts b/extensions/vscode-api-tests/src/singlefolder-tests/tree.test.ts
index a9d9bc5aa345a..02259dc98c274 100644
--- a/extensions/vscode-api-tests/src/singlefolder-tests/tree.test.ts
+++ b/extensions/vscode-api-tests/src/singlefolder-tests/tree.test.ts
@@ -98,10 +98,11 @@ suite('vscode API - tree', () => {
 		await provider.resolveNextRequest();
 
 		const [firstResult, secondResult] = await Promise.all([revealFirst, revealSecond]);
-		const error = firstResult.error ?? secondResult.error;
-		if (error && /Element with id .+ is already registered/.test(error.message)) {
-			assert.fail(error.message);
-		}
+		// Two concurrent root fetches race: the stale one gets invalidated and
+		// its reveal fails with "Cannot resolve". The other succeeds.
+		const errors = [firstResult.error, secondResult.error].filter((e): e is Error => !!e);
+		assert.strictEqual(errors.length, 1, 'Exactly one reveal should fail from the stale fetch');
+		assert.ok(/Cannot resolve tree item/.test(errors[0].message), `Expected "Cannot resolve" error but got: ${errors[0].message}`);
 	});
 
 	test('TreeView - element already registered after rapid root refresh', async function () {
@@ -206,10 +207,113 @@ suite('vscode API - tree', () => {
 		provider.resolveRequestWithElement(1, provider.getElement2());
 
 		const [firstResult, secondResult] = await Promise.all([firstReveal, secondReveal]);
-		const error = firstResult.error ?? secondResult.error;
-		if (error && /Element with id .+ is already registered/.test(error.message)) {
-			assert.fail(error.message);
+		const errors = [firstResult.error, secondResult.error].filter((e): e is Error => !!e);
+		assert.strictEqual(errors.length, 1, 'Exactly one reveal should fail from the stale fetch');
+		assert.ok(/Cannot resolve tree item/.test(errors[0].message), `Expected "Cannot resolve" error but got: ${errors[0].message}`);
+	});
+
+	test('TreeView - element already registered during switch and update', async function () {
+		this.timeout(60_000);
+
+		// This test reproduces a race condition where the tree is being "switched to"
+		// (via reveal, which triggers getChildren) while simultaneously the tree data
+		// is being updated with a new element being added. Both operations trigger
+		// concurrent getChildren calls. The first resolves with the old set of elements,
+		// the second resolves with a new set that includes a new element. If both try
+		// to register elements with the same ID, the error is thrown.
+
+		type TreeElement = { readonly kind: 'leaf'; readonly instance: number };
+
+		class SwitchAndUpdateTreeDataProvider implements vscode.TreeDataProvider<TreeElement> {
+			private readonly changeEmitter = new vscode.EventEmitter<TreeElement | undefined>();
+			private readonly requestEmitter = new vscode.EventEmitter<number>();
+			private readonly pendingRequests: DeferredPromise<TreeElement[]>[] = [];
+			private readonly existingOld: TreeElement = { kind: 'leaf', instance: 1 };
+			private readonly existingNew: TreeElement = { kind: 'leaf', instance: 2 };
+			private readonly addedElement: TreeElement = { kind: 'leaf', instance: 3 };
+
+			readonly onDidChangeTreeData = this.changeEmitter.event;
+
+			getChildren(element?: TreeElement): Thenable<TreeElement[]> {
+				if (!element) {
+					const deferred = new DeferredPromise<TreeElement[]>();
+					this.pendingRequests.push(deferred);
+					this.requestEmitter.fire(this.pendingRequests.length);
+					return deferred.p;
+				}
+				return Promise.resolve([]);
+			}
+
+			getTreeItem(element: TreeElement): vscode.TreeItem {
+				if (element === this.addedElement) {
+					const item = new vscode.TreeItem('added', vscode.TreeItemCollapsibleState.None);
+					item.id = 'added-elem';
+					return item;
+				}
+				const item = new vscode.TreeItem('existing', vscode.TreeItemCollapsibleState.None);
+				item.id = 'existing-elem';
+				return item;
+			}
+
+			getParent(): TreeElement | undefined {
+				return undefined;
+			}
+
+			async waitForRequestCount(count: number): Promise<void> {
+				while (this.pendingRequests.length < count) {
+					await asPromise(this.requestEmitter.event);
+				}
+			}
+
+			resolveRequestAt(index: number, elements: TreeElement[]): void {
+				const request = this.pendingRequests[index];
+				if (request) {
+					request.complete(elements);
+				}
+			}
+
+			getExistingOld(): TreeElement { return this.existingOld; }
+			getExistingNew(): TreeElement { return this.existingNew; }
+			getAddedElement(): TreeElement { return this.addedElement; }
+
+			dispose(): void {
+				this.changeEmitter.dispose();
+				this.requestEmitter.dispose();
+				while (this.pendingRequests.length) {
+					this.pendingRequests.shift()!.complete([]);
+				}
+			}
 		}
+
+		const provider = new SwitchAndUpdateTreeDataProvider();
+		disposables.push(provider);
+
+		const treeView = vscode.window.createTreeView('test.treeSwitchUpdate', { treeDataProvider: provider });
+		disposables.push(treeView);
+
+		// Two concurrent reveals simulate the tree being "switched to" while also
+		// being updated: both trigger getChildren calls on the ext host directly.
+		const revealFirst = (treeView.reveal(provider.getExistingOld(), { expand: true })
+			.then(() => ({ error: undefined as Error | undefined })) as Promise<{ error: Error | undefined }>)
+			.catch(error => ({ error }));
+		const revealSecond = (treeView.reveal(provider.getExistingNew(), { expand: true })
+			.then(() => ({ error: undefined as Error | undefined })) as Promise<{ error: Error | undefined }>)
+			.catch(error => ({ error }));
+
+		// Wait for both getChildren calls to be pending
+		await provider.waitForRequestCount(2);
+
+		// Resolve first request with old data (just the existing element, old instance)
+		provider.resolveRequestAt(0, [provider.getExistingOld()]);
+		await delay(0);
+
+		// Resolve second request with new data: different instance of existing + added element
+		provider.resolveRequestAt(1, [provider.getExistingNew(), provider.getAddedElement()]);
+
+		const [firstResult, secondResult] = await Promise.all([revealFirst, revealSecond]);
+		const errors = [firstResult.error, secondResult.error].filter((e): e is Error => !!e);
+		assert.strictEqual(errors.length, 1, 'Exactly one reveal should fail from the stale fetch');
+		assert.ok(/Cannot resolve tree item/.test(errors[0].message), `Expected "Cannot resolve" error but got: ${errors[0].message}`);
 	});
 
 	test('TreeView - element already registered after refresh', async function () {
@@ -345,9 +449,7 @@ suite('vscode API - tree', () => {
 		await provider.resolveChildRequestAt(0, [staleChild]);
 
 		const [firstResult, secondResult] = await Promise.all([firstReveal, secondReveal]);
-		const error = firstResult.error ?? secondResult.error;
-		if (error && /Element with id .+ is already registered/.test(error.message)) {
-			assert.fail(error.message);
-		}
+		assert.strictEqual(firstResult.error, undefined, `First reveal should not fail: ${firstResult.error?.message}`);
+		assert.strictEqual(secondResult.error, undefined, `Second reveal should not fail: ${secondResult.error?.message}`);
 	});
 });
diff --git a/extensions/vscode-colorize-perf-tests/.npmrc b/extensions/vscode-colorize-perf-tests/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/vscode-colorize-perf-tests/.npmrc
+++ b/extensions/vscode-colorize-perf-tests/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/vscode-colorize-tests/.npmrc b/extensions/vscode-colorize-tests/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/vscode-colorize-tests/.npmrc
+++ b/extensions/vscode-colorize-tests/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/vscode-test-resolver/.npmrc b/extensions/vscode-test-resolver/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/extensions/vscode-test-resolver/.npmrc
+++ b/extensions/vscode-test-resolver/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/extensions/vscode-test-resolver/src/extension.browser.ts b/extensions/vscode-test-resolver/src/extension.browser.ts
index 93703fde4df50..e93a414a79a4e 100644
--- a/extensions/vscode-test-resolver/src/extension.browser.ts
+++ b/extensions/vscode-test-resolver/src/extension.browser.ts
@@ -24,7 +24,7 @@ export function activate(_context: vscode.ExtensionContext) {
  * actual WebSocket.
  */
 class InitialManagedMessagePassing implements vscode.ManagedMessagePassing {
-	private readonly dataEmitter = new vscode.EventEmitter<Uint8Array>();
+	private readonly dataEmitter = new vscode.EventEmitter<Uint8Array<ArrayBuffer>>();
 	private readonly closeEmitter = new vscode.EventEmitter<Error | undefined>();
 	private readonly endEmitter = new vscode.EventEmitter<void>();
 
@@ -38,7 +38,7 @@ class InitialManagedMessagePassing implements vscode.ManagedMessagePassing {
 	public send(d: Uint8Array): void {
 		if (this._actual) {
 			// we already got the HTTP headers
-			this._actual.send(d);
+			this._actual.send(d as Uint8Array<ArrayBuffer>);
 			return;
 		}
 
@@ -80,7 +80,7 @@ class OpeningManagedMessagePassing {
 
 	private readonly socket: WebSocket;
 	private isOpen = false;
-	private bufferedData: Uint8Array[] = [];
+	private bufferedData: Uint8Array<ArrayBuffer>[] = [];
 
 	constructor(
 		url: URL,
@@ -119,7 +119,7 @@ class OpeningManagedMessagePassing {
 		});
 	}
 
-	public send(d: Uint8Array): void {
+	public send(d: Uint8Array<ArrayBuffer>): void {
 		if (!this.isOpen) {
 			this.bufferedData.push(d);
 			return;
diff --git a/extensions/vscode-test-resolver/src/extension.ts b/extensions/vscode-test-resolver/src/extension.ts
index 3e6c9f0ad4955..c342647e672f2 100644
--- a/extensions/vscode-test-resolver/src/extension.ts
+++ b/extensions/vscode-test-resolver/src/extension.ts
@@ -211,12 +211,12 @@ export function activate(context: vscode.ExtensionContext) {
 				console.log('Connecting via a managed authority');
 				return Promise.resolve(new vscode.ManagedResolvedAuthority(async () => {
 					const remoteSocket = net.createConnection({ port: serverAddr.port });
-					const dataEmitter = new vscode.EventEmitter<Uint8Array>();
+					const dataEmitter = new vscode.EventEmitter<Uint8Array<ArrayBuffer>>();
 					const closeEmitter = new vscode.EventEmitter<Error | undefined>();
 					const endEmitter = new vscode.EventEmitter<void>();
 
 					await new Promise((res, rej) => {
-						remoteSocket.on('data', d => dataEmitter.fire(d))
+						remoteSocket.on('data', d => dataEmitter.fire(d as Uint8Array<ArrayBuffer>))
 							.on('error', err => { rej(); closeEmitter.fire(err); })
 							.on('close', () => endEmitter.fire())
 							.on('end', () => endEmitter.fire())
diff --git a/package-lock.json b/package-lock.json
index bf94454e49551..3795213a01de3 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -1,12 +1,12 @@
 {
   "name": "code-oss-dev",
-  "version": "1.110.0",
+  "version": "1.112.0",
   "lockfileVersion": 3,
   "requires": true,
   "packages": {
     "": {
       "name": "code-oss-dev",
-      "version": "1.110.0",
+      "version": "1.112.0",
       "hasInstallScript": true,
       "license": "MIT",
       "dependencies": {
@@ -15,13 +15,13 @@
         "@microsoft/1ds-post-js": "^3.2.13",
         "@parcel/watcher": "^2.5.6",
         "@types/semver": "^7.5.8",
-        "@vscode/codicons": "^0.0.45-10",
+        "@vscode/codicons": "^0.0.45-14",
         "@vscode/deviceid": "^0.1.1",
         "@vscode/iconv-lite-umd": "0.7.1",
         "@vscode/native-watchdog": "^1.4.6",
         "@vscode/policy-watcher": "^1.3.2",
-        "@vscode/proxy-agent": "^0.38.0",
-        "@vscode/ripgrep": "^1.15.13",
+        "@vscode/proxy-agent": "^0.39.1",
+        "@vscode/ripgrep": "^1.17.1",
         "@vscode/spdlog": "^0.15.7",
         "@vscode/sqlite3": "5.1.12-vscode",
         "@vscode/sudo-prompt": "9.3.2",
@@ -30,16 +30,16 @@
         "@vscode/windows-mutex": "^0.5.0",
         "@vscode/windows-process-tree": "^0.6.0",
         "@vscode/windows-registry": "^1.2.0",
-        "@xterm/addon-clipboard": "^0.3.0-beta.167",
-        "@xterm/addon-image": "^0.10.0-beta.167",
-        "@xterm/addon-ligatures": "^0.11.0-beta.167",
-        "@xterm/addon-progress": "^0.3.0-beta.167",
-        "@xterm/addon-search": "^0.17.0-beta.167",
-        "@xterm/addon-serialize": "^0.15.0-beta.167",
-        "@xterm/addon-unicode11": "^0.10.0-beta.167",
-        "@xterm/addon-webgl": "^0.20.0-beta.166",
-        "@xterm/headless": "^6.1.0-beta.167",
-        "@xterm/xterm": "^6.1.0-beta.167",
+        "@xterm/addon-clipboard": "^0.3.0-beta.191",
+        "@xterm/addon-image": "^0.10.0-beta.191",
+        "@xterm/addon-ligatures": "^0.11.0-beta.191",
+        "@xterm/addon-progress": "^0.3.0-beta.191",
+        "@xterm/addon-search": "^0.17.0-beta.191",
+        "@xterm/addon-serialize": "^0.15.0-beta.191",
+        "@xterm/addon-unicode11": "^0.10.0-beta.191",
+        "@xterm/addon-webgl": "^0.20.0-beta.190",
+        "@xterm/headless": "^6.1.0-beta.191",
+        "@xterm/xterm": "^6.1.0-beta.191",
         "http-proxy-agent": "^7.0.0",
         "https-proxy-agent": "^7.0.2",
         "jschardet": "3.1.4",
@@ -52,7 +52,7 @@
         "open": "^10.1.2",
         "playwright-core": "1.59.0-alpha-2026-02-20",
         "tas-client": "0.3.1",
-        "undici": "^7.18.2",
+        "undici": "^7.24.0",
         "v8-inspect-profiler": "^0.1.1",
         "vscode-oniguruma": "1.7.0",
         "vscode-regexpp": "^3.1.0",
@@ -61,6 +61,7 @@
         "yazl": "^2.4.3"
       },
       "devDependencies": {
+        "@playwright/cli": "^0.1.1",
         "@playwright/test": "^1.56.1",
         "@stylistic/eslint-plugin-ts": "^2.8.0",
         "@types/cookie": "^0.3.3",
@@ -76,41 +77,38 @@
         "@types/sinon-test": "^2.4.2",
         "@types/trusted-types": "^2.0.7",
         "@types/vscode-notebook-renderer": "^1.72.0",
-        "@types/webpack": "^5.28.5",
         "@types/wicg-file-system-access": "^2023.10.7",
         "@types/windows-foreground-love": "^0.3.0",
         "@types/winreg": "^1.2.30",
         "@types/yauzl": "^2.10.0",
         "@types/yazl": "^2.4.2",
         "@typescript-eslint/utils": "^8.45.0",
-        "@typescript/native-preview": "^7.0.0-dev.20260130",
-        "@vscode/component-explorer": "^0.1.1-12",
-        "@vscode/component-explorer-cli": "^0.1.1-8",
-        "@vscode/gulp-electron": "https://github.com/microsoft/vscode-gulp-electron.git#405e3df0e4e9c37fcf549cbe6f5cef8d5ba5ddff",
+        "@typescript/native-preview": "^7.0.0-dev.20260306",
+        "@vscode/component-explorer": "^0.1.1-24",
+        "@vscode/component-explorer-cli": "^0.1.1-20",
+        "@vscode/gulp-electron": "1.41.0",
         "@vscode/l10n-dev": "0.0.35",
-        "@vscode/telemetry-extractor": "^1.10.2",
+        "@vscode/telemetry-extractor": "^1.20.2",
         "@vscode/test-cli": "^0.0.6",
         "@vscode/test-electron": "^2.4.0",
         "@vscode/test-web": "^0.0.76",
         "@vscode/v8-heap-parser": "^0.1.0",
         "@vscode/vscode-perf": "^0.0.19",
         "@webgpu/types": "^0.1.66",
+        "agent-browser": "^0.16.3",
         "ansi-colors": "^3.2.3",
         "asar": "^3.0.3",
         "chromium-pickle-js": "^0.2.0",
         "cookie": "^0.7.2",
-        "copy-webpack-plugin": "^11.0.0",
-        "css-loader": "^6.9.1",
         "debounce": "^1.0.0",
         "deemon": "^1.13.6",
-        "electron": "39.6.0",
+        "electron": "39.8.0",
         "eslint": "^9.36.0",
         "eslint-formatter-compact": "^8.40.0",
         "eslint-plugin-header": "3.1.1",
         "eslint-plugin-jsdoc": "^50.3.1",
         "event-stream": "3.3.4",
         "fancy-log": "^1.3.3",
-        "file-loader": "^6.2.0",
         "glob": "^5.0.13",
         "gulp": "^4.0.0",
         "gulp-azure-storage": "^0.12.1",
@@ -136,7 +134,7 @@
         "lazy.js": "^0.4.2",
         "merge-options": "^1.0.1",
         "mime": "^1.4.1",
-        "minimatch": "^3.0.4",
+        "minimatch": "^3.1.5",
         "mocha": "^10.8.2",
         "mocha-junit-reporter": "^2.2.1",
         "mocha-multi-reporters": "^1.5.1",
@@ -151,17 +149,12 @@
         "sinon-test": "^3.1.3",
         "source-map": "0.6.1",
         "source-map-support": "^0.3.2",
-        "style-loader": "^3.3.2",
         "tar": "^7.5.9",
-        "ts-loader": "^9.5.1",
         "tsec": "0.2.7",
         "tslib": "^2.6.3",
-        "typescript": "^6.0.0-dev.20260130",
+        "typescript": "^6.0.0-dev.20260306",
         "typescript-eslint": "^8.45.0",
         "util": "^0.12.4",
-        "webpack": "^5.105.0",
-        "webpack-cli": "^5.1.4",
-        "webpack-stream": "^7.0.0",
         "xml2js": "^0.5.0",
         "yaserver": "^0.4.0"
       },
@@ -169,6 +162,245 @@
         "windows-foreground-love": "0.6.1"
       }
     },
+    "node_modules/@actions/exec": {
+      "version": "1.1.1",
+      "resolved": "https://registry.npmjs.org/@actions/exec/-/exec-1.1.1.tgz",
+      "integrity": "sha512-+sCcHHbVdk93a0XT19ECtO/gIXoxvdsgQLzb2fE2/5sIZmWQuluYyjPQtrtTHdU1YzTZ7bAPN4sITq2xi1679w==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@actions/io": "^1.0.1"
+      }
+    },
+    "node_modules/@actions/github": {
+      "version": "2.2.0",
+      "resolved": "https://registry.npmjs.org/@actions/github/-/github-2.2.0.tgz",
+      "integrity": "sha512-9UAZqn8ywdR70n3GwVle4N8ALosQs4z50N7XMXrSTUVOmVpaBC5kE3TRTT7qQdi3OaQV24mjGuJZsHUmhD+ZXw==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@actions/http-client": "^1.0.3",
+        "@octokit/graphql": "^4.3.1",
+        "@octokit/rest": "^16.43.1"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/auth-token": {
+      "version": "2.5.0",
+      "resolved": "https://registry.npmjs.org/@octokit/auth-token/-/auth-token-2.5.0.tgz",
+      "integrity": "sha512-r5FVUJCOLl19AxiuZD2VRZ/ORjp/4IN98Of6YJoJOkY75CIBuYfmiNHGrDwXr+aLGG55igl9QrxX3hbiXlLb+g==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@octokit/types": "^6.0.3"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/endpoint": {
+      "version": "6.0.12",
+      "resolved": "https://registry.npmjs.org/@octokit/endpoint/-/endpoint-6.0.12.tgz",
+      "integrity": "sha512-lF3puPwkQWGfkMClXb4k/eUT/nZKQfxinRWJrdZaJO85Dqwo/G0yOC434Jr2ojwafWJMYqFGFa5ms4jJUgujdA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@octokit/types": "^6.0.3",
+        "is-plain-object": "^5.0.0",
+        "universal-user-agent": "^6.0.0"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/graphql": {
+      "version": "4.8.0",
+      "resolved": "https://registry.npmjs.org/@octokit/graphql/-/graphql-4.8.0.tgz",
+      "integrity": "sha512-0gv+qLSBLKF0z8TKaSKTsS39scVKF9dbMxJpj3U0vC7wjNWFuIpL/z76Qe2fiuCbDRcJSavkXsVtMS6/dtQQsg==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@octokit/request": "^5.6.0",
+        "@octokit/types": "^6.0.3",
+        "universal-user-agent": "^6.0.0"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/openapi-types": {
+      "version": "12.11.0",
+      "resolved": "https://registry.npmjs.org/@octokit/openapi-types/-/openapi-types-12.11.0.tgz",
+      "integrity": "sha512-VsXyi8peyRq9PqIz/tpqiL2w3w80OgVMwBHltTml3LmVvXiphgeqmY9mvBw9Wu7e0QWk/fqD37ux8yP5uVekyQ==",
+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/@actions/github/node_modules/@octokit/plugin-paginate-rest": {
+      "version": "1.1.2",
+      "resolved": "https://registry.npmjs.org/@octokit/plugin-paginate-rest/-/plugin-paginate-rest-1.1.2.tgz",
+      "integrity": "sha512-jbsSoi5Q1pj63sC16XIUboklNw+8tL9VOnJsWycWYR78TKss5PVpIPb1TUUcMQ+bBh7cY579cVAWmf5qG+dw+Q==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@octokit/types": "^2.0.1"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/plugin-paginate-rest/node_modules/@octokit/types": {
+      "version": "2.16.2",
+      "resolved": "https://registry.npmjs.org/@octokit/types/-/types-2.16.2.tgz",
+      "integrity": "sha512-O75k56TYvJ8WpAakWwYRN8Bgu60KrmX0z1KqFp1kNiFNkgW+JW+9EBKZ+S33PU6SLvbihqd+3drvPxKK68Ee8Q==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@types/node": ">= 8"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/plugin-request-log": {
+      "version": "1.0.4",
+      "resolved": "https://registry.npmjs.org/@octokit/plugin-request-log/-/plugin-request-log-1.0.4.tgz",
+      "integrity": "sha512-mLUsMkgP7K/cnFEw07kWqXGF5LKrOkD+lhCrKvPHXWDywAwuDUeDwWBpc69XK3pNX0uKiVt8g5z96PJ6z9xCFA==",
+      "dev": true,
+      "license": "MIT",
+      "peerDependencies": {
+        "@octokit/core": ">=3"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/plugin-rest-endpoint-methods": {
+      "version": "2.4.0",
+      "resolved": "https://registry.npmjs.org/@octokit/plugin-rest-endpoint-methods/-/plugin-rest-endpoint-methods-2.4.0.tgz",
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+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@octokit/types": "^2.0.1",
+        "deprecation": "^2.3.1"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/plugin-rest-endpoint-methods/node_modules/@octokit/types": {
+      "version": "2.16.2",
+      "resolved": "https://registry.npmjs.org/@octokit/types/-/types-2.16.2.tgz",
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+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@types/node": ">= 8"
+      }
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+    "node_modules/@actions/github/node_modules/@octokit/request": {
+      "version": "5.6.3",
+      "resolved": "https://registry.npmjs.org/@octokit/request/-/request-5.6.3.tgz",
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+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@octokit/endpoint": "^6.0.1",
+        "@octokit/request-error": "^2.1.0",
+        "@octokit/types": "^6.16.1",
+        "is-plain-object": "^5.0.0",
+        "node-fetch": "^2.6.7",
+        "universal-user-agent": "^6.0.0"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/request-error": {
+      "version": "2.1.0",
+      "resolved": "https://registry.npmjs.org/@octokit/request-error/-/request-error-2.1.0.tgz",
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+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@octokit/types": "^6.0.3",
+        "deprecation": "^2.0.0",
+        "once": "^1.4.0"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/rest": {
+      "version": "16.43.2",
+      "resolved": "https://registry.npmjs.org/@octokit/rest/-/rest-16.43.2.tgz",
+      "integrity": "sha512-ngDBevLbBTFfrHZeiS7SAMAZ6ssuVmXuya+F/7RaVvlysgGa1JKJkKWY+jV6TCJYcW0OALfJ7nTIGXcBXzycfQ==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@octokit/auth-token": "^2.4.0",
+        "@octokit/plugin-paginate-rest": "^1.1.1",
+        "@octokit/plugin-request-log": "^1.0.0",
+        "@octokit/plugin-rest-endpoint-methods": "2.4.0",
+        "@octokit/request": "^5.2.0",
+        "@octokit/request-error": "^1.0.2",
+        "atob-lite": "^2.0.0",
+        "before-after-hook": "^2.0.0",
+        "btoa-lite": "^1.0.0",
+        "deprecation": "^2.0.0",
+        "lodash.get": "^4.4.2",
+        "lodash.set": "^4.3.2",
+        "lodash.uniq": "^4.5.0",
+        "octokit-pagination-methods": "^1.1.0",
+        "once": "^1.4.0",
+        "universal-user-agent": "^4.0.0"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/rest/node_modules/@octokit/request-error": {
+      "version": "1.2.1",
+      "resolved": "https://registry.npmjs.org/@octokit/request-error/-/request-error-1.2.1.tgz",
+      "integrity": "sha512-+6yDyk1EES6WK+l3viRDElw96MvwfJxCt45GvmjDUKWjYIb3PJZQkq3i46TwGwoPD4h8NmTrENmtyA1FwbmhRA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@octokit/types": "^2.0.0",
+        "deprecation": "^2.0.0",
+        "once": "^1.4.0"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/rest/node_modules/@octokit/types": {
+      "version": "2.16.2",
+      "resolved": "https://registry.npmjs.org/@octokit/types/-/types-2.16.2.tgz",
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+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@types/node": ">= 8"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/rest/node_modules/universal-user-agent": {
+      "version": "4.0.1",
+      "resolved": "https://registry.npmjs.org/universal-user-agent/-/universal-user-agent-4.0.1.tgz",
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+      "dev": true,
+      "license": "ISC",
+      "dependencies": {
+        "os-name": "^3.1.0"
+      }
+    },
+    "node_modules/@actions/github/node_modules/@octokit/types": {
+      "version": "6.41.0",
+      "resolved": "https://registry.npmjs.org/@octokit/types/-/types-6.41.0.tgz",
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+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@octokit/openapi-types": "^12.11.0"
+      }
+    },
+    "node_modules/@actions/github/node_modules/before-after-hook": {
+      "version": "2.2.3",
+      "resolved": "https://registry.npmjs.org/before-after-hook/-/before-after-hook-2.2.3.tgz",
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+      "dev": true,
+      "license": "Apache-2.0"
+    },
+    "node_modules/@actions/github/node_modules/universal-user-agent": {
+      "version": "6.0.1",
+      "resolved": "https://registry.npmjs.org/universal-user-agent/-/universal-user-agent-6.0.1.tgz",
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+      "dev": true,
+      "license": "ISC"
+    },
+    "node_modules/@actions/http-client": {
+      "version": "1.0.11",
+      "resolved": "https://registry.npmjs.org/@actions/http-client/-/http-client-1.0.11.tgz",
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+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "tunnel": "0.0.6"
+      }
+    },
+    "node_modules/@actions/io": {
+      "version": "1.1.3",
+      "resolved": "https://registry.npmjs.org/@actions/io/-/io-1.1.3.tgz",
+      "integrity": "sha512-wi9JjgKLYS7U/z8PPbco+PvTb/nRWjeoFlJ1Qer83k/3C5PHQi28hiVdeE2kHXmIL99mQFawx8qt/JPjZilJ8Q==",
+      "dev": true,
+      "license": "MIT"
+    },
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-      },
-      "peerDependencies": {
-        "webpack": "^5.21.2"
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       }
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       "dev": true,
+      "license": "MIT",
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+        "node": ">=12"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
       }
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+    "node_modules/webdriverio/node_modules/serialize-error": {
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+      "resolved": "https://registry.npmjs.org/serialize-error/-/serialize-error-12.0.0.tgz",
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+        "type-fest": "^4.31.0"
       },
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-        "node": ">=10"
+        "node": ">=18"
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       "funding": {
-        "url": "https://github.com/chalk/supports-color?sponsor=1"
+        "url": "https://github.com/sponsors/sindresorhus"
       }
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+    "node_modules/webidl-conversions": {
+      "version": "3.0.1",
+      "resolved": "https://registry.npmjs.org/webidl-conversions/-/webidl-conversions-3.0.1.tgz",
+      "integrity": "sha1-JFNCdeKnvGvnvIZhHMFq4KVlSHE= sha512-2JAn3z8AR6rjK8Sm8orRC0h/bcl/DqL7tRPdGZ4I1CjdF+EaMLmYxBHyXuKL849eucPFhvBoxMsflfOb8kxaeQ==",
+      "dev": true
+    },
+    "node_modules/whatwg-encoding": {
+      "version": "3.1.1",
+      "resolved": "https://registry.npmjs.org/whatwg-encoding/-/whatwg-encoding-3.1.1.tgz",
+      "integrity": "sha512-6qN4hJdMwfYBtE3YBTTHhoeuUrDBPZmbQaxWAqSALV/MeEnR5z1xd8UKud2RAkFoPkmB+hli1TZSnyi84xz1vQ==",
+      "deprecated": "Use @exodus/bytes instead for a more spec-conformant and faster implementation",
       "dev": true,
+      "license": "MIT",
       "dependencies": {
-        "clone": "^2.1.1",
-        "clone-buffer": "^1.0.0",
-        "clone-stats": "^1.0.0",
-        "cloneable-readable": "^1.0.0",
-        "remove-trailing-separator": "^1.0.1",
-        "replace-ext": "^1.0.0"
+        "iconv-lite": "0.6.3"
       },
       "engines": {
-        "node": ">= 0.10"
+        "node": ">=18"
       }
     },
-    "node_modules/webpack/node_modules/es-module-lexer": {
-      "version": "2.0.0",
-      "resolved": "https://registry.npmjs.org/es-module-lexer/-/es-module-lexer-2.0.0.tgz",
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-      "dev": true,
-      "license": "MIT"
-    },
-    "node_modules/webpack/node_modules/eslint-scope": {
-      "version": "5.1.1",
-      "resolved": "https://registry.npmjs.org/eslint-scope/-/eslint-scope-5.1.1.tgz",
-      "integrity": "sha512-2NxwbF/hZ0KpepYN0cNbo+FN6XoK7GaHlQhgx/hIZl6Va0bF45RQOOwhLIy8lQDbuCiadSLCBnH2CFYquit5bw==",
+    "node_modules/whatwg-encoding/node_modules/iconv-lite": {
+      "version": "0.6.3",
+      "resolved": "https://registry.npmjs.org/iconv-lite/-/iconv-lite-0.6.3.tgz",
+      "integrity": "sha512-4fCk79wshMdzMp2rH06qWrJE4iolqLhCUH+OiuIgU++RB0+94NlDL81atO7GX55uUKueo0txHNtvEyI6D7WdMw==",
       "dev": true,
+      "license": "MIT",
       "dependencies": {
-        "esrecurse": "^4.3.0",
-        "estraverse": "^4.1.1"
+        "safer-buffer": ">= 2.1.2 < 3.0.0"
       },
       "engines": {
-        "node": ">=8.0.0"
+        "node": ">=0.10.0"
       }
     },
-    "node_modules/webpack/node_modules/estraverse": {
-      "version": "4.3.0",
-      "resolved": "https://registry.npmjs.org/estraverse/-/estraverse-4.3.0.tgz",
-      "integrity": "sha512-39nnKffWz8xN1BU/2c79n9nB9HDzo0niYUqx6xyqUnyoAnQyyWpOTdZEeiCch8BBu515t4wp9ZmgVfVhn9EBpw==",
+    "node_modules/whatwg-mimetype": {
+      "version": "4.0.0",
+      "resolved": "https://registry.npmjs.org/whatwg-mimetype/-/whatwg-mimetype-4.0.0.tgz",
+      "integrity": "sha512-QaKxh0eNIi2mE9p2vEdzfagOKHCcj1pJ56EEHGQOVxp8r9/iszLUUV7v89x9O1p/T+NlTM5W7jW6+cz4Fq1YVg==",
       "dev": true,
+      "license": "MIT",
       "engines": {
-        "node": ">=4.0"
+        "node": ">=18"
       }
     },
     "node_modules/whatwg-url": {
@@ -18841,12 +20842,6 @@
         "url": "https://github.com/sponsors/ljharb"
       }
     },
-    "node_modules/wildcard": {
-      "version": "2.0.0",
-      "resolved": "https://registry.npmjs.org/wildcard/-/wildcard-2.0.0.tgz",
-      "integrity": "sha512-JcKqAHLPxcdb9KM49dufGXn2x3ssnfjbcaQdLlfZsL9rH9wgDQjUtDxbo8NE0F6SFvydeu1VhZe7hZuHsB2/pw==",
-      "dev": true
-    },
     "node_modules/windows-foreground-love": {
       "version": "0.6.1",
       "resolved": "https://registry.npmjs.org/windows-foreground-love/-/windows-foreground-love-0.6.1.tgz",
@@ -18855,6 +20850,22 @@
       "license": "MIT",
       "optional": true
     },
+    "node_modules/windows-release": {
+      "version": "3.3.3",
+      "resolved": "https://registry.npmjs.org/windows-release/-/windows-release-3.3.3.tgz",
+      "integrity": "sha512-OSOGH1QYiW5yVor9TtmXKQvt2vjQqbYS+DqmsZw+r7xDwLXEeT3JGW0ZppFmHx4diyXmxt238KFR3N9jzevBRg==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "execa": "^1.0.0"
+      },
+      "engines": {
+        "node": ">=6"
+      },
+      "funding": {
+        "url": "https://github.com/sponsors/sindresorhus"
+      }
+    },
     "node_modules/word-wrap": {
       "version": "1.2.5",
       "resolved": "https://registry.npmjs.org/word-wrap/-/word-wrap-1.2.5.tgz",
@@ -18954,6 +20965,28 @@
       "resolved": "https://registry.npmjs.org/wrappy/-/wrappy-1.0.2.tgz",
       "integrity": "sha1-tSQ9jz7BqjXxNkYFvA0QNuMKtp8= sha512-l4Sp/DRseor9wL6EvV2+TuQn63dMkPjZ/sp9XkghTEbV9KlPS1xUsZ3u7/IQO4wxtcFB4bgpQPRcR3QCvezPcQ=="
     },
+    "node_modules/ws": {
+      "version": "8.19.0",
+      "resolved": "https://registry.npmjs.org/ws/-/ws-8.19.0.tgz",
+      "integrity": "sha512-blAT2mjOEIi0ZzruJfIhb3nps74PRWTCz1IjglWEEpQl5XS/UNama6u2/rjFkDDouqr4L67ry+1aGIALViWjDg==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=10.0.0"
+      },
+      "peerDependencies": {
+        "bufferutil": "^4.0.1",
+        "utf-8-validate": ">=5.0.2"
+      },
+      "peerDependenciesMeta": {
+        "bufferutil": {
+          "optional": true
+        },
+        "utf-8-validate": {
+          "optional": true
+        }
+      }
+    },
     "node_modules/xml": {
       "version": "1.0.1",
       "resolved": "https://registry.npmjs.org/xml/-/xml-1.0.1.tgz",
@@ -19128,6 +21161,94 @@
         "url": "https://github.com/sponsors/sindresorhus"
       }
     },
+    "node_modules/zip-stream": {
+      "version": "6.0.1",
+      "resolved": "https://registry.npmjs.org/zip-stream/-/zip-stream-6.0.1.tgz",
+      "integrity": "sha512-zK7YHHz4ZXpW89AHXUPbQVGKI7uvkd3hzusTdotCg1UxyaVtg0zFJSTfW/Dq5f7OBBVnq6cZIaC8Ti4hb6dtCA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "archiver-utils": "^5.0.0",
+        "compress-commons": "^6.0.2",
+        "readable-stream": "^4.0.0"
+      },
+      "engines": {
+        "node": ">= 14"
+      }
+    },
+    "node_modules/zip-stream/node_modules/buffer": {
+      "version": "6.0.3",
+      "resolved": "https://registry.npmjs.org/buffer/-/buffer-6.0.3.tgz",
+      "integrity": "sha512-FTiCpNxtwiZZHEZbcbTIcZjERVICn9yq/pDFkTl95/AxzD1naBctN7YO68riM/gLSDY7sdrMby8hofADYuuqOA==",
+      "dev": true,
+      "funding": [
+        {
+          "type": "github",
+          "url": "https://github.com/sponsors/feross"
+        },
+        {
+          "type": "patreon",
+          "url": "https://www.patreon.com/feross"
+        },
+        {
+          "type": "consulting",
+          "url": "https://feross.org/support"
+        }
+      ],
+      "license": "MIT",
+      "dependencies": {
+        "base64-js": "^1.3.1",
+        "ieee754": "^1.2.1"
+      }
+    },
+    "node_modules/zip-stream/node_modules/readable-stream": {
+      "version": "4.7.0",
+      "resolved": "https://registry.npmjs.org/readable-stream/-/readable-stream-4.7.0.tgz",
+      "integrity": "sha512-oIGGmcpTLwPga8Bn6/Z75SVaH1z5dUut2ibSyAMVhmUggWpmDn2dapB0n7f8nwaSiRtepAsfJyfXIO5DCVAODg==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "abort-controller": "^3.0.0",
+        "buffer": "^6.0.3",
+        "events": "^3.3.0",
+        "process": "^0.11.10",
+        "string_decoder": "^1.3.0"
+      },
+      "engines": {
+        "node": "^12.22.0 || ^14.17.0 || >=16.0.0"
+      }
+    },
+    "node_modules/zip-stream/node_modules/safe-buffer": {
+      "version": "5.2.1",
+      "resolved": "https://registry.npmjs.org/safe-buffer/-/safe-buffer-5.2.1.tgz",
+      "integrity": "sha512-rp3So07KcdmmKbGvgaNxQSJr7bGVSVk5S9Eq1F+ppbRo70+YeaDxkw5Dd8NPN+GD6bjnYm2VuPuCXmpuYvmCXQ==",
+      "dev": true,
+      "funding": [
+        {
+          "type": "github",
+          "url": "https://github.com/sponsors/feross"
+        },
+        {
+          "type": "patreon",
+          "url": "https://www.patreon.com/feross"
+        },
+        {
+          "type": "consulting",
+          "url": "https://feross.org/support"
+        }
+      ],
+      "license": "MIT"
+    },
+    "node_modules/zip-stream/node_modules/string_decoder": {
+      "version": "1.3.0",
+      "resolved": "https://registry.npmjs.org/string_decoder/-/string_decoder-1.3.0.tgz",
+      "integrity": "sha512-hkRX8U1WjJFd8LsDJ2yQ/wWWxaopEsABU1XfkM8A+j0+85JAGppt16cr1Whg6KIbb4okU6Mql6BOj+uup/wKeA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "safe-buffer": "~5.2.0"
+      }
+    },
     "node_modules/zod": {
       "version": "3.25.76",
       "resolved": "https://registry.npmjs.org/zod/-/zod-3.25.76.tgz",
diff --git a/package.json b/package.json
index f8a9d07778bbb..c0ee0cd0c823f 100644
--- a/package.json
+++ b/package.json
@@ -1,7 +1,7 @@
 {
   "name": "code-oss-dev",
-  "version": "1.110.0",
-  "distro": "1b8e5b3448f8be12228bc9bee56b42a5f95158e7",
+  "version": "1.112.0",
+  "distro": "2e74305a6fb0a094a3797324d58940dda3d161ff",
   "author": {
     "name": "Microsoft Corporation"
   },
@@ -31,6 +31,7 @@
     "watch-client": "npm run gulp watch-client",
     "watch-clientd": "deemon npm run watch-client",
     "kill-watch-clientd": "deemon --kill npm run watch-client",
+    "transpile-client": "node build/next/index.ts transpile",
     "watch-client-transpile": "node build/next/index.ts transpile --watch",
     "watch-client-transpiled": "deemon npm run watch-client-transpile",
     "kill-watch-client-transpiled": "deemon --kill npm run watch-client-transpile",
@@ -75,6 +76,7 @@
     "perf": "node scripts/code-perf.js",
     "update-build-ts-version": "npm install -D typescript@next && npm install -D @typescript/native-preview && (cd build && npm run typecheck)",
     "install-local-component-explorer": "npm install ../vscode-packages/js-component-explorer/dist/vscode-component-explorer-0.1.0.tgz ../vscode-packages/js-component-explorer/dist/vscode-component-explorer-cli-0.1.0.tgz --no-save && cd build/vite && npm install ../../../vscode-packages/js-component-explorer/dist/vscode-component-explorer-vite-plugin-0.1.0.tgz --no-save",
+    "symlink-local-component-explorer": "npm install ../vscode-packages/js-component-explorer/packages/explorer ../vscode-packages/js-component-explorer/packages/cli --no-save && cd build/vite && npm install ../../../vscode-packages/js-component-explorer/packages/vite-plugin ../../../vscode-packages/js-component-explorer/packages/explorer --no-save",
     "install-latest-component-explorer": "npm install @vscode/component-explorer@next @vscode/component-explorer-cli@next && cd build/vite && npm install @vscode/component-explorer-vite-plugin@next && npm install @vscode/component-explorer@next"
   },
   "dependencies": {
@@ -83,13 +85,13 @@
     "@microsoft/1ds-post-js": "^3.2.13",
     "@parcel/watcher": "^2.5.6",
     "@types/semver": "^7.5.8",
-    "@vscode/codicons": "^0.0.45-10",
+    "@vscode/codicons": "^0.0.45-14",
     "@vscode/deviceid": "^0.1.1",
     "@vscode/iconv-lite-umd": "0.7.1",
     "@vscode/native-watchdog": "^1.4.6",
     "@vscode/policy-watcher": "^1.3.2",
-    "@vscode/proxy-agent": "^0.38.0",
-    "@vscode/ripgrep": "^1.15.13",
+    "@vscode/proxy-agent": "^0.39.1",
+    "@vscode/ripgrep": "^1.17.1",
     "@vscode/spdlog": "^0.15.7",
     "@vscode/sqlite3": "5.1.12-vscode",
     "@vscode/sudo-prompt": "9.3.2",
@@ -98,16 +100,16 @@
     "@vscode/windows-mutex": "^0.5.0",
     "@vscode/windows-process-tree": "^0.6.0",
     "@vscode/windows-registry": "^1.2.0",
-    "@xterm/addon-clipboard": "^0.3.0-beta.167",
-    "@xterm/addon-image": "^0.10.0-beta.167",
-    "@xterm/addon-ligatures": "^0.11.0-beta.167",
-    "@xterm/addon-progress": "^0.3.0-beta.167",
-    "@xterm/addon-search": "^0.17.0-beta.167",
-    "@xterm/addon-serialize": "^0.15.0-beta.167",
-    "@xterm/addon-unicode11": "^0.10.0-beta.167",
-    "@xterm/addon-webgl": "^0.20.0-beta.166",
-    "@xterm/headless": "^6.1.0-beta.167",
-    "@xterm/xterm": "^6.1.0-beta.167",
+    "@xterm/addon-clipboard": "^0.3.0-beta.191",
+    "@xterm/addon-image": "^0.10.0-beta.191",
+    "@xterm/addon-ligatures": "^0.11.0-beta.191",
+    "@xterm/addon-progress": "^0.3.0-beta.191",
+    "@xterm/addon-search": "^0.17.0-beta.191",
+    "@xterm/addon-serialize": "^0.15.0-beta.191",
+    "@xterm/addon-unicode11": "^0.10.0-beta.191",
+    "@xterm/addon-webgl": "^0.20.0-beta.190",
+    "@xterm/headless": "^6.1.0-beta.191",
+    "@xterm/xterm": "^6.1.0-beta.191",
     "http-proxy-agent": "^7.0.0",
     "https-proxy-agent": "^7.0.2",
     "jschardet": "3.1.4",
@@ -120,7 +122,7 @@
     "open": "^10.1.2",
     "playwright-core": "1.59.0-alpha-2026-02-20",
     "tas-client": "0.3.1",
-    "undici": "^7.18.2",
+    "undici": "^7.24.0",
     "v8-inspect-profiler": "^0.1.1",
     "vscode-oniguruma": "1.7.0",
     "vscode-regexpp": "^3.1.0",
@@ -129,6 +131,7 @@
     "yazl": "^2.4.3"
   },
   "devDependencies": {
+    "@playwright/cli": "^0.1.1",
     "@playwright/test": "^1.56.1",
     "@stylistic/eslint-plugin-ts": "^2.8.0",
     "@types/cookie": "^0.3.3",
@@ -144,41 +147,38 @@
     "@types/sinon-test": "^2.4.2",
     "@types/trusted-types": "^2.0.7",
     "@types/vscode-notebook-renderer": "^1.72.0",
-    "@types/webpack": "^5.28.5",
     "@types/wicg-file-system-access": "^2023.10.7",
     "@types/windows-foreground-love": "^0.3.0",
     "@types/winreg": "^1.2.30",
     "@types/yauzl": "^2.10.0",
     "@types/yazl": "^2.4.2",
     "@typescript-eslint/utils": "^8.45.0",
-    "@typescript/native-preview": "^7.0.0-dev.20260130",
-    "@vscode/component-explorer": "^0.1.1-12",
-    "@vscode/component-explorer-cli": "^0.1.1-8",
-    "@vscode/gulp-electron": "https://github.com/microsoft/vscode-gulp-electron.git#405e3df0e4e9c37fcf549cbe6f5cef8d5ba5ddff",
+    "@typescript/native-preview": "^7.0.0-dev.20260306",
+    "@vscode/component-explorer": "^0.1.1-24",
+    "@vscode/component-explorer-cli": "^0.1.1-20",
+    "@vscode/gulp-electron": "1.41.0",
     "@vscode/l10n-dev": "0.0.35",
-    "@vscode/telemetry-extractor": "^1.10.2",
+    "@vscode/telemetry-extractor": "^1.20.2",
     "@vscode/test-cli": "^0.0.6",
     "@vscode/test-electron": "^2.4.0",
     "@vscode/test-web": "^0.0.76",
     "@vscode/v8-heap-parser": "^0.1.0",
     "@vscode/vscode-perf": "^0.0.19",
     "@webgpu/types": "^0.1.66",
+    "agent-browser": "^0.16.3",
     "ansi-colors": "^3.2.3",
     "asar": "^3.0.3",
     "chromium-pickle-js": "^0.2.0",
     "cookie": "^0.7.2",
-    "copy-webpack-plugin": "^11.0.0",
-    "css-loader": "^6.9.1",
     "debounce": "^1.0.0",
     "deemon": "^1.13.6",
-    "electron": "39.6.0",
+    "electron": "39.8.0",
     "eslint": "^9.36.0",
     "eslint-formatter-compact": "^8.40.0",
     "eslint-plugin-header": "3.1.1",
     "eslint-plugin-jsdoc": "^50.3.1",
     "event-stream": "3.3.4",
     "fancy-log": "^1.3.3",
-    "file-loader": "^6.2.0",
     "glob": "^5.0.13",
     "gulp": "^4.0.0",
     "gulp-azure-storage": "^0.12.1",
@@ -204,7 +204,7 @@
     "lazy.js": "^0.4.2",
     "merge-options": "^1.0.1",
     "mime": "^1.4.1",
-    "minimatch": "^3.0.4",
+    "minimatch": "^3.1.5",
     "mocha": "^10.8.2",
     "mocha-junit-reporter": "^2.2.1",
     "mocha-multi-reporters": "^1.5.1",
@@ -219,17 +219,12 @@
     "sinon-test": "^3.1.3",
     "source-map": "0.6.1",
     "source-map-support": "^0.3.2",
-    "style-loader": "^3.3.2",
     "tar": "^7.5.9",
-    "ts-loader": "^9.5.1",
     "tsec": "0.2.7",
     "tslib": "^2.6.3",
-    "typescript": "^6.0.0-dev.20260130",
+    "typescript": "^6.0.0-dev.20260306",
     "typescript-eslint": "^8.45.0",
     "util": "^0.12.4",
-    "webpack": "^5.105.0",
-    "webpack-cli": "^5.1.4",
-    "webpack-stream": "^7.0.0",
     "xml2js": "^0.5.0",
     "yaserver": "^0.4.0"
   },
@@ -237,7 +232,8 @@
     "node-gyp-build": "4.8.1",
     "kerberos@2.1.1": {
       "node-addon-api": "7.1.0"
-    }
+    },
+    "serialize-javascript": "^7.0.3"
   },
   "repository": {
     "type": "git",
diff --git a/product.json b/product.json
index af053a48660fd..48804f152268f 100644
--- a/product.json
+++ b/product.json
@@ -52,8 +52,8 @@
 		},
 		{
 			"name": "ms-vscode.js-debug",
-			"version": "1.105.0",
-			"sha256": "0c45b90342e8aafd4ff2963b4006de64208ca58c2fd01fea7a710fe61dcfd12a",
+			"version": "1.112.0",
+			"sha256": "c24322931434940938f8cf76ebc3dac1e95a5539b9625b165b6672d7f7eafea8",
 			"repo": "https://github.com/microsoft/vscode-js-debug",
 			"metadata": {
 				"id": "25629058-ddac-4e17-abba-74678e126c5d",
diff --git a/remote/.npmrc b/remote/.npmrc
index 666ce9aaa8cf9..b0fee29a02ca8 100644
--- a/remote/.npmrc
+++ b/remote/.npmrc
@@ -5,3 +5,4 @@ runtime="node"
 build_from_source="true"
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/remote/package-lock.json b/remote/package-lock.json
index 49b97cb47d00d..fd94c9d768c87 100644
--- a/remote/package-lock.json
+++ b/remote/package-lock.json
@@ -15,23 +15,23 @@
         "@vscode/deviceid": "^0.1.1",
         "@vscode/iconv-lite-umd": "0.7.1",
         "@vscode/native-watchdog": "^1.4.6",
-        "@vscode/proxy-agent": "^0.38.0",
-        "@vscode/ripgrep": "^1.15.13",
+        "@vscode/proxy-agent": "^0.39.1",
+        "@vscode/ripgrep": "^1.17.1",
         "@vscode/spdlog": "^0.15.7",
         "@vscode/tree-sitter-wasm": "^0.3.0",
         "@vscode/vscode-languagedetection": "1.0.23",
         "@vscode/windows-process-tree": "^0.6.0",
         "@vscode/windows-registry": "^1.2.0",
-        "@xterm/addon-clipboard": "^0.3.0-beta.167",
-        "@xterm/addon-image": "^0.10.0-beta.167",
-        "@xterm/addon-ligatures": "^0.11.0-beta.167",
-        "@xterm/addon-progress": "^0.3.0-beta.167",
-        "@xterm/addon-search": "^0.17.0-beta.167",
-        "@xterm/addon-serialize": "^0.15.0-beta.167",
-        "@xterm/addon-unicode11": "^0.10.0-beta.167",
-        "@xterm/addon-webgl": "^0.20.0-beta.166",
-        "@xterm/headless": "^6.1.0-beta.167",
-        "@xterm/xterm": "^6.1.0-beta.167",
+        "@xterm/addon-clipboard": "^0.3.0-beta.191",
+        "@xterm/addon-image": "^0.10.0-beta.191",
+        "@xterm/addon-ligatures": "^0.11.0-beta.191",
+        "@xterm/addon-progress": "^0.3.0-beta.191",
+        "@xterm/addon-search": "^0.17.0-beta.191",
+        "@xterm/addon-serialize": "^0.15.0-beta.191",
+        "@xterm/addon-unicode11": "^0.10.0-beta.191",
+        "@xterm/addon-webgl": "^0.20.0-beta.190",
+        "@xterm/headless": "^6.1.0-beta.191",
+        "@xterm/xterm": "^6.1.0-beta.191",
         "cookie": "^0.7.0",
         "http-proxy-agent": "^7.0.0",
         "https-proxy-agent": "^7.0.2",
@@ -421,9 +421,10 @@
       "license": "MIT"
     },
     "node_modules/@tootallnate/once": {
-      "version": "3.0.0",
-      "resolved": "https://registry.npmjs.org/@tootallnate/once/-/once-3.0.0.tgz",
-      "integrity": "sha512-OAdBVB7rlwvLD+DiecSAyVKzKVmSfXbouCyM5I6wHGi4MGXIyFqErg1IvyJ7PI1e+GYZuZh7cCHV/c4LA8SKMw==",
+      "version": "3.0.1",
+      "resolved": "https://registry.npmjs.org/@tootallnate/once/-/once-3.0.1.tgz",
+      "integrity": "sha512-VyMVKRrpHTT8PnotUeV8L/mDaMwD5DaAKCFLP73zAqAtvF0FCqky+Ki7BYbFCYQmqFyTe9316Ed5zS70QUR9eg==",
+      "license": "MIT",
       "engines": {
         "node": ">= 10"
       }
@@ -468,9 +469,9 @@
       "license": "MIT"
     },
     "node_modules/@vscode/proxy-agent": {
-      "version": "0.38.0",
-      "resolved": "https://registry.npmjs.org/@vscode/proxy-agent/-/proxy-agent-0.38.0.tgz",
-      "integrity": "sha512-f8fOGbYhCVG9FUbtVcL/90yjCyo6ZuuKQpA7hs7iIEMD8kesnoo04TUI3/29vifCZ2DCiyUN12CFgA+ktc2RTw==",
+      "version": "0.39.1",
+      "resolved": "https://registry.npmjs.org/@vscode/proxy-agent/-/proxy-agent-0.39.1.tgz",
+      "integrity": "sha512-Au6ra1oVBNlxgroyr58VuaO2mVH02xidPfN6o0znYr/NQ8OvXNm4CVM44iwyCP1sOzhLKjMoPEeWIbKDpLgtFg==",
       "license": "MIT",
       "dependencies": {
         "@tootallnate/once": "^3.0.0",
@@ -489,9 +490,9 @@
       }
     },
     "node_modules/@vscode/ripgrep": {
-      "version": "1.17.0",
-      "resolved": "https://registry.npmjs.org/@vscode/ripgrep/-/ripgrep-1.17.0.tgz",
-      "integrity": "sha512-mBRKm+ASPkUcw4o9aAgfbusIu6H4Sdhw09bjeP1YOBFTJEZAnrnk6WZwzv8NEjgC82f7ILvhmb1WIElSugea6g==",
+      "version": "1.17.1",
+      "resolved": "https://registry.npmjs.org/@vscode/ripgrep/-/ripgrep-1.17.1.tgz",
+      "integrity": "sha512-xTs7DGyAO3IsJYOCTBP8LnTvPiYVKEuyv8s0xyJDBXfs8rhBfqnZPvb6xDT+RnwWzcXqW27xLS/aGrkjX7lNWw==",
       "hasInstallScript": true,
       "license": "MIT",
       "dependencies": {
@@ -578,30 +579,30 @@
       "license": "MIT"
     },
     "node_modules/@xterm/addon-clipboard": {
-      "version": "0.3.0-beta.167",
-      "resolved": "https://registry.npmjs.org/@xterm/addon-clipboard/-/addon-clipboard-0.3.0-beta.167.tgz",
-      "integrity": "sha512-+JSjagAk6okCaGVYFwkKl8qIBfy+W+h7p/qULIi9cC8QyeswOLaE4GOqY5yuGNQYU+zMlrpgR1ttyp0o6y9LHg==",
+      "version": "0.3.0-beta.191",
+      "resolved": "https://registry.npmjs.org/@xterm/addon-clipboard/-/addon-clipboard-0.3.0-beta.191.tgz",
+      "integrity": "sha512-u+0smTVylu9IAntE2OPfD1ZqZ5TNIcSWM1fA/tu1tryGIscax9cn6V2U7T4kkTEFf3A4a3PKgCrKufBclXebjQ==",
       "license": "MIT",
       "dependencies": {
         "js-base64": "^3.7.5"
       },
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/addon-image": {
-      "version": "0.10.0-beta.167",
-      "resolved": "https://registry.npmjs.org/@xterm/addon-image/-/addon-image-0.10.0-beta.167.tgz",
-      "integrity": "sha512-Bxi2oTaX7YM1gup0OSv02n9+tA3P1Ozlu5zyB/ZwSVkepB9FOxCODWD0l3DhWyLGMBqQ+OY/COw5SRxrKyvkNg==",
+      "version": "0.10.0-beta.191",
+      "resolved": "https://registry.npmjs.org/@xterm/addon-image/-/addon-image-0.10.0-beta.191.tgz",
+      "integrity": "sha512-gX2WEQV2N7A9fx5VpzXK9GIqazUJKBreqEOuUcQPnY2ECJqVsC0uaoK9A/rhm2JuSkHRcqBt/pRVlT4Ki5KsZg==",
       "license": "MIT",
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/addon-ligatures": {
-      "version": "0.11.0-beta.167",
-      "resolved": "https://registry.npmjs.org/@xterm/addon-ligatures/-/addon-ligatures-0.11.0-beta.167.tgz",
-      "integrity": "sha512-d+9ANnoz6D4J06CjronVolcG+J0jqUWQXbzciRqQkHq0or5k8PYuIj2DuuyBx/0rOaN7JYN347KQ9iylk+++xA==",
+      "version": "0.11.0-beta.191",
+      "resolved": "https://registry.npmjs.org/@xterm/addon-ligatures/-/addon-ligatures-0.11.0-beta.191.tgz",
+      "integrity": "sha512-LFAPEUna5o7nZSJrlV8rrhU6WIC30btdqPf4PNAo5pxWjCWPBqlD1XkTmeYWGpsxk2OaXec/MGjG03k6Rg2z2w==",
       "license": "MIT",
       "dependencies": {
         "lru-cache": "^6.0.0",
@@ -611,67 +612,67 @@
         "node": ">8.0.0"
       },
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/addon-progress": {
-      "version": "0.3.0-beta.167",
-      "resolved": "https://registry.npmjs.org/@xterm/addon-progress/-/addon-progress-0.3.0-beta.167.tgz",
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+      "version": "0.3.0-beta.191",
+      "resolved": "https://registry.npmjs.org/@xterm/addon-progress/-/addon-progress-0.3.0-beta.191.tgz",
+      "integrity": "sha512-aImBOklbz37LqF4JsXe6cSTyFIpV5hxU4G/DS1IaFqbYPPMwWGdOUIB3L+TWwcMJh9hv1iwx5PbxNNi0KaylVw==",
       "license": "MIT",
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/addon-search": {
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-      "resolved": "https://registry.npmjs.org/@xterm/addon-search/-/addon-search-0.17.0-beta.167.tgz",
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+      "version": "0.17.0-beta.191",
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       "license": "MIT",
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/addon-serialize": {
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       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
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       "workspaces": [
         "addons/*"
diff --git a/remote/package.json b/remote/package.json
index 2de8217e16d43..ec73a84fff08b 100644
--- a/remote/package.json
+++ b/remote/package.json
@@ -10,23 +10,23 @@
     "@vscode/deviceid": "^0.1.1",
     "@vscode/iconv-lite-umd": "0.7.1",
     "@vscode/native-watchdog": "^1.4.6",
-    "@vscode/proxy-agent": "^0.38.0",
-    "@vscode/ripgrep": "^1.15.13",
+    "@vscode/proxy-agent": "^0.39.1",
+    "@vscode/ripgrep": "^1.17.1",
     "@vscode/spdlog": "^0.15.7",
     "@vscode/tree-sitter-wasm": "^0.3.0",
     "@vscode/vscode-languagedetection": "1.0.23",
     "@vscode/windows-process-tree": "^0.6.0",
     "@vscode/windows-registry": "^1.2.0",
-    "@xterm/addon-clipboard": "^0.3.0-beta.167",
-    "@xterm/addon-image": "^0.10.0-beta.167",
-    "@xterm/addon-ligatures": "^0.11.0-beta.167",
-    "@xterm/addon-progress": "^0.3.0-beta.167",
-    "@xterm/addon-search": "^0.17.0-beta.167",
-    "@xterm/addon-serialize": "^0.15.0-beta.167",
-    "@xterm/addon-unicode11": "^0.10.0-beta.167",
-    "@xterm/addon-webgl": "^0.20.0-beta.166",
-    "@xterm/headless": "^6.1.0-beta.167",
-    "@xterm/xterm": "^6.1.0-beta.167",
+    "@xterm/addon-clipboard": "^0.3.0-beta.191",
+    "@xterm/addon-image": "^0.10.0-beta.191",
+    "@xterm/addon-ligatures": "^0.11.0-beta.191",
+    "@xterm/addon-progress": "^0.3.0-beta.191",
+    "@xterm/addon-search": "^0.17.0-beta.191",
+    "@xterm/addon-serialize": "^0.15.0-beta.191",
+    "@xterm/addon-unicode11": "^0.10.0-beta.191",
+    "@xterm/addon-webgl": "^0.20.0-beta.190",
+    "@xterm/headless": "^6.1.0-beta.191",
+    "@xterm/xterm": "^6.1.0-beta.191",
     "cookie": "^0.7.0",
     "http-proxy-agent": "^7.0.0",
     "https-proxy-agent": "^7.0.2",
diff --git a/remote/web/.npmrc b/remote/web/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/remote/web/.npmrc
+++ b/remote/web/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/remote/web/package-lock.json b/remote/web/package-lock.json
index 1b80d4aedeac4..3e36911e4dc08 100644
--- a/remote/web/package-lock.json
+++ b/remote/web/package-lock.json
@@ -10,19 +10,19 @@
       "dependencies": {
         "@microsoft/1ds-core-js": "^3.2.13",
         "@microsoft/1ds-post-js": "^3.2.13",
-        "@vscode/codicons": "^0.0.45-10",
+        "@vscode/codicons": "^0.0.45-14",
         "@vscode/iconv-lite-umd": "0.7.1",
         "@vscode/tree-sitter-wasm": "^0.3.0",
         "@vscode/vscode-languagedetection": "1.0.23",
-        "@xterm/addon-clipboard": "^0.3.0-beta.167",
-        "@xterm/addon-image": "^0.10.0-beta.167",
-        "@xterm/addon-ligatures": "^0.11.0-beta.167",
-        "@xterm/addon-progress": "^0.3.0-beta.167",
-        "@xterm/addon-search": "^0.17.0-beta.167",
-        "@xterm/addon-serialize": "^0.15.0-beta.167",
-        "@xterm/addon-unicode11": "^0.10.0-beta.167",
-        "@xterm/addon-webgl": "^0.20.0-beta.166",
-        "@xterm/xterm": "^6.1.0-beta.167",
+        "@xterm/addon-clipboard": "^0.3.0-beta.191",
+        "@xterm/addon-image": "^0.10.0-beta.191",
+        "@xterm/addon-ligatures": "^0.11.0-beta.191",
+        "@xterm/addon-progress": "^0.3.0-beta.191",
+        "@xterm/addon-search": "^0.17.0-beta.191",
+        "@xterm/addon-serialize": "^0.15.0-beta.191",
+        "@xterm/addon-unicode11": "^0.10.0-beta.191",
+        "@xterm/addon-webgl": "^0.20.0-beta.190",
+        "@xterm/xterm": "^6.1.0-beta.191",
         "jschardet": "3.1.4",
         "katex": "^0.16.22",
         "tas-client": "0.3.1",
@@ -73,9 +73,9 @@
       "integrity": "sha512-n1VPsljTSkthsAFYdiWfC+DKzK2WwcRp83Y1YAqdX552BstvsDjft9YXppjUzp11BPsapDoO1LDgrDB0XVsfNQ=="
     },
     "node_modules/@vscode/codicons": {
-      "version": "0.0.45-10",
-      "resolved": "https://registry.npmjs.org/@vscode/codicons/-/codicons-0.0.45-10.tgz",
-      "integrity": "sha512-05CYIpwSYKEQN0qBnfmLC/5VcasOwmeLsl3SGj944UyJ1/vJQpqL153A+0xh4geYEeqcOtIc42emmCizsCzf0Q==",
+      "version": "0.0.45-14",
+      "resolved": "https://registry.npmjs.org/@vscode/codicons/-/codicons-0.0.45-14.tgz",
+      "integrity": "sha512-EdrK2NnxNGluUm9ZlU1C5VTLfG1cpO4C0CCXloS+8bDuTbidE1qtwaF5lHPcoDE102WBqBzWA09nVKFoN8RSOA==",
       "license": "CC-BY-4.0"
     },
     "node_modules/@vscode/iconv-lite-umd": {
@@ -100,30 +100,30 @@
       }
     },
     "node_modules/@xterm/addon-clipboard": {
-      "version": "0.3.0-beta.167",
-      "resolved": "https://registry.npmjs.org/@xterm/addon-clipboard/-/addon-clipboard-0.3.0-beta.167.tgz",
-      "integrity": "sha512-+JSjagAk6okCaGVYFwkKl8qIBfy+W+h7p/qULIi9cC8QyeswOLaE4GOqY5yuGNQYU+zMlrpgR1ttyp0o6y9LHg==",
+      "version": "0.3.0-beta.191",
+      "resolved": "https://registry.npmjs.org/@xterm/addon-clipboard/-/addon-clipboard-0.3.0-beta.191.tgz",
+      "integrity": "sha512-u+0smTVylu9IAntE2OPfD1ZqZ5TNIcSWM1fA/tu1tryGIscax9cn6V2U7T4kkTEFf3A4a3PKgCrKufBclXebjQ==",
       "license": "MIT",
       "dependencies": {
         "js-base64": "^3.7.5"
       },
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/addon-image": {
-      "version": "0.10.0-beta.167",
-      "resolved": "https://registry.npmjs.org/@xterm/addon-image/-/addon-image-0.10.0-beta.167.tgz",
-      "integrity": "sha512-Bxi2oTaX7YM1gup0OSv02n9+tA3P1Ozlu5zyB/ZwSVkepB9FOxCODWD0l3DhWyLGMBqQ+OY/COw5SRxrKyvkNg==",
+      "version": "0.10.0-beta.191",
+      "resolved": "https://registry.npmjs.org/@xterm/addon-image/-/addon-image-0.10.0-beta.191.tgz",
+      "integrity": "sha512-gX2WEQV2N7A9fx5VpzXK9GIqazUJKBreqEOuUcQPnY2ECJqVsC0uaoK9A/rhm2JuSkHRcqBt/pRVlT4Ki5KsZg==",
       "license": "MIT",
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/addon-ligatures": {
-      "version": "0.11.0-beta.167",
-      "resolved": "https://registry.npmjs.org/@xterm/addon-ligatures/-/addon-ligatures-0.11.0-beta.167.tgz",
-      "integrity": "sha512-d+9ANnoz6D4J06CjronVolcG+J0jqUWQXbzciRqQkHq0or5k8PYuIj2DuuyBx/0rOaN7JYN347KQ9iylk+++xA==",
+      "version": "0.11.0-beta.191",
+      "resolved": "https://registry.npmjs.org/@xterm/addon-ligatures/-/addon-ligatures-0.11.0-beta.191.tgz",
+      "integrity": "sha512-LFAPEUna5o7nZSJrlV8rrhU6WIC30btdqPf4PNAo5pxWjCWPBqlD1XkTmeYWGpsxk2OaXec/MGjG03k6Rg2z2w==",
       "license": "MIT",
       "dependencies": {
         "lru-cache": "^6.0.0",
@@ -133,58 +133,58 @@
         "node": ">8.0.0"
       },
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/addon-progress": {
-      "version": "0.3.0-beta.167",
-      "resolved": "https://registry.npmjs.org/@xterm/addon-progress/-/addon-progress-0.3.0-beta.167.tgz",
-      "integrity": "sha512-8eeaWnp0pnjYaKtOLsXVCE0hTFXS0A2kZCciWp52l6CbNGQsnky4VNWJXKaJrGbS+RHGxT6qWgcB+Mx5ETzZfg==",
+      "version": "0.3.0-beta.191",
+      "resolved": "https://registry.npmjs.org/@xterm/addon-progress/-/addon-progress-0.3.0-beta.191.tgz",
+      "integrity": "sha512-aImBOklbz37LqF4JsXe6cSTyFIpV5hxU4G/DS1IaFqbYPPMwWGdOUIB3L+TWwcMJh9hv1iwx5PbxNNi0KaylVw==",
       "license": "MIT",
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/addon-search": {
-      "version": "0.17.0-beta.167",
-      "resolved": "https://registry.npmjs.org/@xterm/addon-search/-/addon-search-0.17.0-beta.167.tgz",
-      "integrity": "sha512-1K6POdu0iCdjtW0Bs2z3IGWpMU4gJypbYxGnecbGnsH86rNRGwAKS0bKwWlHAiUQLlOxSGxTiNbazbrDln03FQ==",
+      "version": "0.17.0-beta.191",
+      "resolved": "https://registry.npmjs.org/@xterm/addon-search/-/addon-search-0.17.0-beta.191.tgz",
+      "integrity": "sha512-fv+TQkhDXYxAeJ31Mi4C4BPFLcffFOHl/vDceMlzaqHB+XHTBo6BDRcXAWBAgA0rvChZrYYTQ/JCPq9R506JSw==",
       "license": "MIT",
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/addon-serialize": {
-      "version": "0.15.0-beta.167",
-      "resolved": "https://registry.npmjs.org/@xterm/addon-serialize/-/addon-serialize-0.15.0-beta.167.tgz",
-      "integrity": "sha512-7EK/PN7QaUZcNE+bHmt7ELSNK3OBR2UZEuqNkE/0ooha7KqqI9mxZQG53Yn6wYcmRip34OFW9YF49kbTCkFuBg==",
+      "version": "0.15.0-beta.191",
+      "resolved": "https://registry.npmjs.org/@xterm/addon-serialize/-/addon-serialize-0.15.0-beta.191.tgz",
+      "integrity": "sha512-Kzj/J52MEH8B1p84CZ0XEY3/engNDO1sJKmpZDLr0WP+EKvh5uwZe0bD5X5tNLNM5ZEFpMWailwTrGF9tSAd2g==",
       "license": "MIT",
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/addon-unicode11": {
-      "version": "0.10.0-beta.167",
-      "resolved": "https://registry.npmjs.org/@xterm/addon-unicode11/-/addon-unicode11-0.10.0-beta.167.tgz",
-      "integrity": "sha512-uOJCfsMhML8GTesUKqCC4CH2cPH9yCIFnixiwgpcE5eLVrLszXW3tny25S/bu6EM+rfvE4nwIvLNTMrQYYnMFA==",
+      "version": "0.10.0-beta.191",
+      "resolved": "https://registry.npmjs.org/@xterm/addon-unicode11/-/addon-unicode11-0.10.0-beta.191.tgz",
+      "integrity": "sha512-6FR4CjI0te0bLWF7jr7ujpjVOW1kGFl+rKWbblFRNhENuN6gT1phIm4V1L4N9Rr6seTku272YRnO0nAHWZNe6g==",
       "license": "MIT",
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/addon-webgl": {
-      "version": "0.20.0-beta.166",
-      "resolved": "https://registry.npmjs.org/@xterm/addon-webgl/-/addon-webgl-0.20.0-beta.166.tgz",
-      "integrity": "sha512-SZmz7HDeSMc4O0++x14ma/UWbK/0Ea8AikHw6V5ex/shjrjwbik7Uf2n8FfG2zMYNgBakvCy/SbwDPtQN+IbRQ==",
+      "version": "0.20.0-beta.190",
+      "resolved": "https://registry.npmjs.org/@xterm/addon-webgl/-/addon-webgl-0.20.0-beta.190.tgz",
+      "integrity": "sha512-9ABzdVhovpseQuD7v5sDz/4UZXvX7y8CH+EaF+LiP/HK6JwdWzVo9OftyWGNdHrOqo43PO7RTeC3eUQq9qqQGw==",
       "license": "MIT",
       "peerDependencies": {
-        "@xterm/xterm": "^6.1.0-beta.167"
+        "@xterm/xterm": "^6.1.0-beta.191"
       }
     },
     "node_modules/@xterm/xterm": {
-      "version": "6.1.0-beta.167",
-      "resolved": "https://registry.npmjs.org/@xterm/xterm/-/xterm-6.1.0-beta.167.tgz",
-      "integrity": "sha512-OOG2gcH9OhEjY+KW3X2s30e1KzaRlynhkF9/oKfb2PNUJBYUdXeww4YAugrz7+nLP8KxCeOdSJrq7VvRzyZrwA==",
+      "version": "6.1.0-beta.191",
+      "resolved": "https://registry.npmjs.org/@xterm/xterm/-/xterm-6.1.0-beta.191.tgz",
+      "integrity": "sha512-c50KmCnftJRZa3cXVBxcixTyeq4Brs603DHxYGZ0z0a58LkhKdfzOfKwYKxHfiZlsOlX58Xk21BJ4d1UrCuCAA==",
       "license": "MIT",
       "workspaces": [
         "addons/*"
diff --git a/remote/web/package.json b/remote/web/package.json
index 69493c7779ade..b358e1e32674a 100644
--- a/remote/web/package.json
+++ b/remote/web/package.json
@@ -5,19 +5,19 @@
   "dependencies": {
     "@microsoft/1ds-core-js": "^3.2.13",
     "@microsoft/1ds-post-js": "^3.2.13",
-    "@vscode/codicons": "^0.0.45-10",
+    "@vscode/codicons": "^0.0.45-14",
     "@vscode/iconv-lite-umd": "0.7.1",
     "@vscode/tree-sitter-wasm": "^0.3.0",
     "@vscode/vscode-languagedetection": "1.0.23",
-    "@xterm/addon-clipboard": "^0.3.0-beta.167",
-    "@xterm/addon-image": "^0.10.0-beta.167",
-    "@xterm/addon-ligatures": "^0.11.0-beta.167",
-    "@xterm/addon-progress": "^0.3.0-beta.167",
-    "@xterm/addon-search": "^0.17.0-beta.167",
-    "@xterm/addon-serialize": "^0.15.0-beta.167",
-    "@xterm/addon-unicode11": "^0.10.0-beta.167",
-    "@xterm/addon-webgl": "^0.20.0-beta.166",
-    "@xterm/xterm": "^6.1.0-beta.167",
+    "@xterm/addon-clipboard": "^0.3.0-beta.191",
+    "@xterm/addon-image": "^0.10.0-beta.191",
+    "@xterm/addon-ligatures": "^0.11.0-beta.191",
+    "@xterm/addon-progress": "^0.3.0-beta.191",
+    "@xterm/addon-search": "^0.17.0-beta.191",
+    "@xterm/addon-serialize": "^0.15.0-beta.191",
+    "@xterm/addon-unicode11": "^0.10.0-beta.191",
+    "@xterm/addon-webgl": "^0.20.0-beta.190",
+    "@xterm/xterm": "^6.1.0-beta.191",
     "jschardet": "3.1.4",
     "katex": "^0.16.22",
     "tas-client": "0.3.1",
diff --git a/resources/win32/VisualElementsManifest.xml b/resources/win32/VisualElementsManifest.xml
index 40efd0a396e87..5ad1283cd7e10 100644
--- a/resources/win32/VisualElementsManifest.xml
+++ b/resources/win32/VisualElementsManifest.xml
@@ -2,8 +2,8 @@
 		<VisualElements
 				BackgroundColor="#2D2D30"
 				ShowNameOnSquare150x150Logo="on"
-				Square150x150Logo="resources\app\resources\win32\code_150x150.png"
-				Square70x70Logo="resources\app\resources\win32\code_70x70.png"
-				ForegroundText="light" 
+				Square150x150Logo="@@VERSIONFOLDER@@resources\app\resources\win32\code_150x150.png"
+				Square70x70Logo="@@VERSIONFOLDER@@resources\app\resources\win32\code_70x70.png"
+				ForegroundText="light"
 				ShortDisplayName="Code - OSS" />
 </Application>
diff --git a/scripts/code-sessions-web.js b/scripts/code-sessions-web.js
new file mode 100644
index 0000000000000..c652b32e79eec
--- /dev/null
+++ b/scripts/code-sessions-web.js
@@ -0,0 +1,176 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+// @ts-check
+
+const http = require('http');
+const fs = require('fs');
+const path = require('path');
+const open = require('open');
+const minimist = require('minimist');
+
+const APP_ROOT = path.join(__dirname, '..');
+
+async function main() {
+	const args = minimist(process.argv.slice(2), {
+		boolean: ['help', 'no-open', 'skip-welcome', 'mock'],
+		string: ['host', 'port'],
+	});
+
+	if (args.help) {
+		console.log(
+			'./scripts/code-sessions-web.sh [options]\n' +
+			'  --host <host>   Host to bind to (default: localhost)\n' +
+			'  --port <port>   Port to bind to (default: 8081)\n' +
+			'  --no-open       Do not open browser automatically\n' +
+			'  --skip-welcome  Skip the sessions welcome overlay\n' +
+			'  --mock          Load mock extension for E2E testing\n'
+		);
+		return;
+	}
+
+	const HOST = args['host'] ?? 'localhost';
+	const PORT = parseInt(args['port'] ?? '8081', 10);
+
+	// Collect CSS module paths from the compiled output (same as @vscode/test-web does).
+	// These are turned into an import map so the browser can load `import './foo.css'`
+	// statements as JavaScript shims that inject the CSS via `_VSCODE_CSS_LOAD`.
+	let cssModules = [];
+	try {
+		const { glob } = require('tinyglobby');
+		cssModules = await glob('**/*.css', { cwd: path.join(APP_ROOT, 'out') });
+	} catch {
+		// tinyglobby may not be installed; fall back to a recursive fs walk
+		cssModules = collectCssFiles(path.join(APP_ROOT, 'out'), '');
+	}
+
+	const server = http.createServer((req, res) => {
+		const url = new URL(req.url, `http://${HOST}:${PORT}`);
+
+		// Serve the sessions workbench HTML at the root
+		if (url.pathname === '/' || url.pathname === '/index.html') {
+			res.writeHead(200, { 'Content-Type': 'text/html' });
+			res.end(getSessionsHTML(HOST, PORT, cssModules, args['mock']));
+			return;
+		}
+
+		// Serve static files from the repo root (out/, src/, node_modules/, etc.)
+		const filePath = path.join(APP_ROOT, url.pathname);
+		if (fs.existsSync(filePath) && fs.statSync(filePath).isFile()) {
+			const ext = path.extname(filePath);
+			const contentType = {
+				'.js': 'application/javascript',
+				'.mjs': 'application/javascript',
+				'.css': 'text/css',
+				'.html': 'text/html',
+				'.json': 'application/json',
+				'.svg': 'image/svg+xml',
+				'.png': 'image/png',
+				'.ttf': 'font/ttf',
+				'.woff': 'font/woff',
+				'.woff2': 'font/woff2',
+			}[ext] || 'application/octet-stream';
+
+			res.writeHead(200, {
+				'Content-Type': contentType,
+				'Access-Control-Allow-Origin': '*',
+			});
+			fs.createReadStream(filePath).pipe(res);
+			return;
+		}
+
+		res.writeHead(404);
+		res.end('Not found');
+	});
+
+	server.listen(PORT, HOST, () => {
+		console.log(`\n  Sessions Web running at: http://${HOST}:${PORT}/\n`);
+		if (!args['no-open'] && args.open !== false) {
+			const query = args['skip-welcome'] ? '?skip-sessions-welcome' : '';
+			open.default(`http://${HOST}:${PORT}/${query}`);
+		}
+	});
+
+	process.on('SIGINT', () => { server.close(); process.exit(0); });
+	process.on('SIGTERM', () => { server.close(); process.exit(0); });
+}
+
+function getSessionsHTML(host, port, cssModules, useMock) {
+	const baseUrl = `http://${host}:${port}`;
+	const fileRoot = `${baseUrl}/out`;
+
+	// Build the import map server-side. Each CSS file gets mapped to a
+	// data: URI containing a JS module that injects the stylesheet via
+	// a global helper function. This must be a static <script type="importmap">
+	// declared before any <script type="module"> tags.
+	const imports = {};
+	for (const cssModule of cssModules) {
+		const cssUrl = `${fileRoot}/${cssModule}`;
+		const jsSrc = `globalThis._VSCODE_CSS_LOAD('${cssUrl}');\n`;
+		const encoded = Buffer.from(jsSrc).toString('base64');
+		imports[cssUrl] = `data:application/javascript;base64,${encoded}`;
+	}
+	const importMapJson = JSON.stringify({ imports }, null, 2);
+
+	// When --mock is passed, load the E2E mock extension
+	const additionalBuiltinExtensions = useMock
+		? `additionalBuiltinExtensions: [{ scheme: 'http', authority: '${host}:${port}', path: '/src/vs/sessions/test/e2e/extensions/sessions-e2e-mock' }],`
+		: '';
+
+	return `<!DOCTYPE html>
+<html>
+<head>
+	<meta charset="utf-8" />
+	<meta name="viewport" content="width=device-width, initial-scale=1" />
+	<title>Sessions</title>
+	<style id="vscode-css-modules"></style>
+	<script>
+		globalThis._VSCODE_FILE_ROOT = '${fileRoot}';
+		const sheet = document.getElementById('vscode-css-modules').sheet;
+		globalThis._VSCODE_CSS_LOAD = function (url) { sheet.insertRule(\`@import url(\${url});\`); };
+	</script>
+	<script type="importmap">
+${importMapJson}
+	</script>
+</head>
+<body aria-label="">
+	<script type="module">
+		import { create, URI } from '${fileRoot}/vs/sessions/${useMock ? 'test/sessions.web.test.internal' : 'sessions.web.main.internal'}.js';
+		create(document.body, {
+			productConfiguration: {
+				nameShort: 'Sessions (Web)',
+				nameLong: 'Sessions (Web)',
+				enableTelemetry: false,
+			},
+			${additionalBuiltinExtensions}
+			workspaceProvider: {
+				workspace: ${useMock
+			? `{ folderUri: URI.parse('mock-fs://mock-repo/mock-repo') }`
+			: 'undefined'},
+				open: async () => false,
+				payload: [['isSessionsWindow', 'true']],
+			},
+		});
+	</script>
+</body>
+</html>`;
+}
+
+/** Recursively collect *.css paths relative to `dir`. */
+function collectCssFiles(dir, prefix) {
+	let results = [];
+	for (const entry of fs.readdirSync(dir, { withFileTypes: true })) {
+		const rel = prefix ? prefix + '/' + entry.name : entry.name;
+		if (entry.isDirectory()) {
+			results = results.concat(collectCssFiles(path.join(dir, entry.name), rel));
+		} else if (entry.name.endsWith('.css')) {
+			results.push(rel);
+		}
+	}
+	return results;
+}
+
+main();
+
diff --git a/scripts/code-sessions-web.sh b/scripts/code-sessions-web.sh
new file mode 100755
index 0000000000000..be62921a05f28
--- /dev/null
+++ b/scripts/code-sessions-web.sh
@@ -0,0 +1,27 @@
+#!/usr/bin/env bash
+
+if [[ "$OSTYPE" == "darwin"* ]]; then
+	realpath() { [[ $1 = /* ]] && echo "$1" || echo "$PWD/${1#./}"; }
+	ROOT=$(dirname $(dirname $(realpath "$0")))
+else
+	ROOT=$(dirname $(dirname $(readlink -f $0)))
+fi
+
+function code() {
+	cd $ROOT
+
+	# Sync built-in extensions
+	npm run download-builtin-extensions
+
+	NODE=$(node build/lib/node.ts)
+	if [ ! -e $NODE ];then
+		# Load remote node
+		npm run gulp node
+	fi
+
+	NODE=$(node build/lib/node.ts)
+
+	$NODE ./scripts/code-sessions-web.js "$@"
+}
+
+code "$@"
diff --git a/src/bootstrap-import.ts b/src/bootstrap-import.ts
index 3bd5c73a0af64..70c5525a274b5 100644
--- a/src/bootstrap-import.ts
+++ b/src/bootstrap-import.ts
@@ -52,7 +52,6 @@ export async function resolve(specifier: string | number, context: unknown, next
 	const newSpecifier = _specifierToUrl[specifier];
 	if (newSpecifier !== undefined) {
 		return {
-			format: 'commonjs',
 			shortCircuit: true,
 			url: newSpecifier
 		};
diff --git a/src/main.ts b/src/main.ts
index ec2e45c31d255..42f599c9b3785 100644
--- a/src/main.ts
+++ b/src/main.ts
@@ -342,7 +342,7 @@ function configureCommandlineSwitchesSync(cliArgs: NativeParsedArgs) {
 	app.commandLine.appendSwitch('disable-blink-features', blinkFeaturesToDisable);
 
 	// Support JS Flags
-	const jsFlags = getJSFlags(cliArgs);
+	const jsFlags = getJSFlags(cliArgs, argvConfig);
 	if (jsFlags) {
 		app.commandLine.appendSwitch('js-flags', jsFlags);
 	}
@@ -374,6 +374,7 @@ interface IArgvConfig {
 	readonly 'use-inmemory-secretstorage'?: boolean;
 	readonly 'enable-rdp-display-tracking'?: boolean;
 	readonly 'remote-debugging-port'?: string;
+	readonly 'js-flags'?: string;
 }
 
 function readArgvConfigSync(): IArgvConfig {
@@ -537,7 +538,7 @@ function configureCrashReporter(): void {
 	});
 }
 
-function getJSFlags(cliArgs: NativeParsedArgs): string | null {
+function getJSFlags(cliArgs: NativeParsedArgs, argvConfig: IArgvConfig): string | null {
 	const jsFlags: string[] = [];
 
 	// Add any existing JS flags we already got from the command line
@@ -545,6 +546,11 @@ function getJSFlags(cliArgs: NativeParsedArgs): string | null {
 		jsFlags.push(cliArgs['js-flags']);
 	}
 
+	// Add JS flags from runtime arguments (argv.json)
+	if (typeof argvConfig['js-flags'] === 'string' && argvConfig['js-flags']) {
+		jsFlags.push(argvConfig['js-flags']);
+	}
+
 	if (process.platform === 'linux') {
 		// Fix cppgc crash on Linux with 16KB page size.
 		// Refs https://issues.chromium.org/issues/378017037
diff --git a/src/tsconfig.vscode-dts.json b/src/tsconfig.vscode-dts.json
index b83f686e4f3d3..fae0ce15c38f1 100644
--- a/src/tsconfig.vscode-dts.json
+++ b/src/tsconfig.vscode-dts.json
@@ -1,7 +1,7 @@
 {
 	"compilerOptions": {
 		"noEmit": true,
-		"module": "None",
+		"module": "preserve",
 		"experimentalDecorators": false,
 		"noImplicitReturns": true,
 		"noImplicitOverride": true,
diff --git a/src/typings/base-common.d.ts b/src/typings/base-common.d.ts
index 56e9a6a799d7e..9028abb2975b5 100644
--- a/src/typings/base-common.d.ts
+++ b/src/typings/base-common.d.ts
@@ -25,7 +25,7 @@ declare global {
 	function setTimeout(handler: string | Function, timeout?: number, ...arguments: any[]): Timeout;
 	function clearTimeout(timeout: Timeout | undefined): void;
 
-	function setInterval(callback: (...args: any[]) => void, delay?: number, ...args: any[]): Timeout;
+	function setInterval(callback: (...args: unknown[]) => void, delay?: number, ...args: unknown[]): Timeout;
 	function clearInterval(timeout: Timeout | undefined): void;
 
 
diff --git a/src/vs/amdX.ts b/src/vs/amdX.ts
index 374d4f19faf13..98290fdc2b421 100644
--- a/src/vs/amdX.ts
+++ b/src/vs/amdX.ts
@@ -171,15 +171,15 @@ class AMDModuleImporter {
 		if (this._amdPolicy) {
 			scriptSrc = this._amdPolicy.createScriptURL(scriptSrc) as unknown as string;
 		}
-		await import(scriptSrc);
+		await import(/* @vite-ignore */ scriptSrc);
 		return this._defineCalls.pop();
 	}
 
 	private async _nodeJSLoadScript(scriptSrc: string): Promise<DefineCall | undefined> {
 		try {
-			const fs = (await import(`${'fs'}`)).default;
-			const vm = (await import(`${'vm'}`)).default;
-			const module = (await import(`${'module'}`)).default;
+			const fs = (await import(/* @vite-ignore */ `${'fs'}`)).default;
+			const vm = (await import(/* @vite-ignore */ `${'vm'}`)).default;
+			const module = (await import(/* @vite-ignore */ `${'module'}`)).default;
 
 			const filePath = URI.parse(scriptSrc).fsPath;
 			const content = fs.readFileSync(filePath).toString();
diff --git a/src/vs/base/browser/markdownRenderer.ts b/src/vs/base/browser/markdownRenderer.ts
index e3f20d96726b4..52f99538b1144 100644
--- a/src/vs/base/browser/markdownRenderer.ts
+++ b/src/vs/base/browser/markdownRenderer.ts
@@ -66,6 +66,25 @@ export interface MarkdownSanitizerConfig {
 	readonly remoteImageIsAllowed?: (uri: URI) => boolean;
 }
 
+/**
+ * Returns a human-readable tooltip string for a link href.
+ * For file:// URIs, converts to a decoded OS file system path to avoid
+ * showing raw URL-encoded paths (e.g. "C:\Users\..." instead of "file:///c%3A/Users/...").
+ */
+function getLinkTitle(href: string): string {
+	try {
+		const parsed = URI.parse(href);
+		if (parsed.scheme === Schemas.file) {
+			const path = parsed.fsPath;
+			const fragment = parsed.fragment;
+			return escapeDoubleQuotes(fragment ? `${path}#${fragment}` : path);
+		}
+	} catch {
+		// fall through
+	}
+	return '';
+}
+
 const defaultMarkedRenderers = Object.freeze({
 	image: ({ href, title, text }: marked.Tokens.Image): string => {
 		let dimensions: string[] = [];
@@ -104,6 +123,12 @@ const defaultMarkedRenderers = Object.freeze({
 		title = typeof title === 'string' ? escapeDoubleQuotes(removeMarkdownEscapes(title)) : '';
 		href = removeMarkdownEscapes(href);
 
+		// For file:// URIs without an explicit title, show the decoded OS path instead of
+		// the raw URL-encoded URI (e.g. display "C:\Users\..." instead of "file:///c%3A/Users/...")
+		if (!title && href.startsWith(`${Schemas.file}:`)) {
+			title = getLinkTitle(href);
+		}
+
 		// HTML Encode href
 		href = href.replace(/&/g, '&amp;')
 			.replace(/</g, '&lt;')
diff --git a/src/vs/base/browser/ui/actionbar/actionbar.css b/src/vs/base/browser/ui/actionbar/actionbar.css
index 467b1ff6efa32..e9e55ad9b269c 100644
--- a/src/vs/base/browser/ui/actionbar/actionbar.css
+++ b/src/vs/base/browser/ui/actionbar/actionbar.css
@@ -50,7 +50,7 @@
 	display: flex;
 	font-size: 11px;
 	padding: 3px;
-	border-radius: 5px;
+	border-radius: var(--vscode-cornerRadius-medium);
 }
 
 .monaco-action-bar .action-item.disabled .action-label:not(.icon) ,
diff --git a/src/vs/base/browser/ui/dialog/dialog.css b/src/vs/base/browser/ui/dialog/dialog.css
index c484fa86dbd94..cf35f8126c68d 100644
--- a/src/vs/base/browser/ui/dialog/dialog.css
+++ b/src/vs/base/browser/ui/dialog/dialog.css
@@ -25,12 +25,14 @@
 	display: flex;
 	flex-direction: column-reverse;
 	width: min-content;
-	min-width: 500px;
+	min-width: 480px;
 	max-width: 90vw;
+	max-height: 90vh;
 	min-height: 75px;
-	padding: 10px;
+	padding: 8px;
 	transform: translate3d(0px, 0px, 0px);
-	border-radius: 3px;
+	border-radius: var(--vscode-cornerRadius-xLarge);
+	box-shadow: var(--vscode-shadow-xl);
 }
 
 .monaco-dialog-box.align-vertical {
@@ -39,7 +41,7 @@
 
 /** Dialog: Title Actions Row */
 .monaco-dialog-box .dialog-toolbar-row {
-	height: 22px;
+	height: 20px;
 	padding-bottom: 4px;
 }
 
@@ -53,17 +55,23 @@
 	display: flex;
 	flex-grow: 1;
 	align-items: center;
-	padding: 0 10px;
+	padding: 0 8px 0 12px;
+	min-height: 0; /* allow flex item to shrink below content size */
+	overflow: hidden;
 }
 
 .monaco-dialog-box.align-vertical .dialog-message-row {
 	flex-direction: column;
 }
 
+.monaco-dialog-box.align-vertical .dialog-message-row .dialog-message-container {
+	min-height: 0; /* allow flex item to shrink below content size in column layout */
+}
+
 .monaco-dialog-box .dialog-message-row > .dialog-icon.codicon {
-	flex: 0 0 48px;
-	height: 48px;
-	font-size: 48px;
+	flex: 0 0 24px;
+	height: 24px;
+	font-size: 24px;
 }
 
 .monaco-dialog-box.align-vertical .dialog-message-row > .dialog-icon.codicon {
@@ -76,12 +84,17 @@
 	align-self: baseline;
 }
 
+.monaco-dialog-box:not(.align-vertical) .dialog-message-row .dialog-message-container {
+	align-self: stretch; /* fill row height so overflow-y scrolling works */
+}
+
 /** Dialog: Message/Footer Container */
 .monaco-dialog-box .dialog-message-row .dialog-message-container,
 .monaco-dialog-box .dialog-footer-row {
 	display: flex;
 	flex-direction: column;
-	overflow: hidden;
+	overflow-y: auto;
+	overflow-x: hidden;
 	text-overflow: ellipsis;
 	user-select: text;
 	-webkit-user-select: text;
@@ -95,7 +108,7 @@
 
 .monaco-dialog-box:not(.align-vertical) .dialog-message-row .dialog-message-container,
 .monaco-dialog-box:not(.align-vertical) .dialog-footer-row {
-	padding-left: 24px;
+	padding-left: 12px;
 }
 
 .monaco-dialog-box.align-vertical .dialog-message-row .dialog-message-container,
@@ -111,20 +124,20 @@
 
 /** Dialog: Message */
 .monaco-dialog-box .dialog-message-row .dialog-message-container .dialog-message {
-	line-height: 22px;
-	font-size: 18px;
+	font-size: 14px;
+	font-weight: 600;
 	flex: 1; /* let the message always grow */
 	white-space: normal;
 	word-wrap: break-word; /* never overflow long words, but break to next line */
-	min-height: 48px; /* matches icon height */
-	margin-bottom: 8px;
+	min-height: 22px;
+	margin-bottom: 4px;
 	display: flex;
 	align-items: center;
 }
 
 /** Dialog: Details */
 .monaco-dialog-box .dialog-message-row .dialog-message-container .dialog-message-detail {
-	line-height: 22px;
+	line-height: 20px;
 	flex: 1; /* let the message always grow */
 }
 
@@ -167,12 +180,8 @@
 	align-items: center;
 	padding-right: 1px;
 	overflow: hidden; /* buttons row should never overflow */
-}
-
-.monaco-dialog-box > .dialog-buttons-row {
-	display: flex;
 	white-space: nowrap;
-	padding: 20px 10px 10px;
+	padding: 20px 0px 0px;
 }
 
 /** Dialog: Buttons */
@@ -196,8 +205,8 @@
 .monaco-dialog-box > .dialog-buttons-row > .dialog-buttons > .monaco-button {
 	overflow: hidden;
 	text-overflow: ellipsis;
-	margin: 4px 5px; /* allows button focus outline to be visible */
-	outline-offset: 2px !important;
+	margin: 4px; /* allows button focus outline to be visible */
+	outline-offset: 1px !important;
 }
 
 .monaco-dialog-box.align-vertical > .dialog-buttons-row > .dialog-buttons > .monaco-button {
@@ -238,3 +247,7 @@
 .monaco-dialog-box > .dialog-buttons-row > .dialog-buttons > .monaco-button-dropdown > .monaco-dropdown-button {
 	padding: 0 4px;
 }
+
+.monaco-dialog-modal-block .dialog-shadow {
+	border-radius: var(--vscode-cornerRadius-xLarge);
+}
diff --git a/src/vs/base/browser/ui/dropdown/dropdown.css b/src/vs/base/browser/ui/dropdown/dropdown.css
index bfcaee41f98ad..7c70f376b1491 100644
--- a/src/vs/base/browser/ui/dropdown/dropdown.css
+++ b/src/vs/base/browser/ui/dropdown/dropdown.css
@@ -20,6 +20,11 @@
 	cursor: default;
 }
 
+.monaco-dropdown .dropdown-menu {
+	border-radius: var(--vscode-cornerRadius-large);
+	box-shadow: var(--vscode-shadow-lg);
+}
+
 .monaco-dropdown-with-primary {
 	display: flex !important;
 	flex-direction: row;
diff --git a/src/vs/base/browser/ui/iconLabel/iconLabel.ts b/src/vs/base/browser/ui/iconLabel/iconLabel.ts
index 468667aabc013..034c650442a04 100644
--- a/src/vs/base/browser/ui/iconLabel/iconLabel.ts
+++ b/src/vs/base/browser/ui/iconLabel/iconLabel.ts
@@ -9,7 +9,7 @@ import * as css from '../../cssValue.js';
 import { HighlightedLabel } from '../highlightedlabel/highlightedLabel.js';
 import { IHoverDelegate } from '../hover/hoverDelegate.js';
 import { IMatch } from '../../../common/filters.js';
-import { Disposable, IDisposable } from '../../../common/lifecycle.js';
+import { Disposable, DisposableStore, IDisposable } from '../../../common/lifecycle.js';
 import { equals } from '../../../common/objects.js';
 import { Range } from '../../../common/range.js';
 import { getDefaultHoverDelegate } from '../hover/hoverDelegateFactory.js';
@@ -340,6 +340,7 @@ class LabelWithHighlights extends Disposable {
 	private label: string | string[] | undefined = undefined;
 	private singleLabel: HighlightedLabel | undefined = undefined;
 	private options: IIconLabelValueOptions | undefined;
+	private readonly _labelDisposables = this._register(new DisposableStore());
 
 	constructor(private container: HTMLElement, private supportIcons: boolean) {
 		super();
@@ -358,13 +359,15 @@ class LabelWithHighlights extends Disposable {
 
 		if (typeof label === 'string') {
 			if (!this.singleLabel) {
+				this._labelDisposables.clear();
 				this.container.textContent = '';
 				this.container.classList.remove('multiple');
-				this.singleLabel = this._register(new HighlightedLabel(dom.append(this.container, dom.$('a.label-name', { id: options?.domId }))));
+				this.singleLabel = this._labelDisposables.add(new HighlightedLabel(dom.append(this.container, dom.$('a.label-name', { id: options?.domId }))));
 			}
 
 			this.singleLabel.set(label, options?.matches, undefined, options?.labelEscapeNewLines, supportIcons);
 		} else {
+			this._labelDisposables.clear();
 			this.container.textContent = '';
 			this.container.classList.add('multiple');
 			this.singleLabel = undefined;
@@ -378,7 +381,7 @@ class LabelWithHighlights extends Disposable {
 				const id = options?.domId && `${options?.domId}_${i}`;
 
 				const name = dom.$('a.label-name', { id, 'data-icon-label-count': label.length, 'data-icon-label-index': i, 'role': 'treeitem' });
-				const highlightedLabel = this._register(new HighlightedLabel(dom.append(this.container, name)));
+				const highlightedLabel = this._labelDisposables.add(new HighlightedLabel(dom.append(this.container, name)));
 				highlightedLabel.set(l, m, undefined, options?.labelEscapeNewLines, supportIcons);
 
 				if (i < label.length - 1) {
diff --git a/src/vs/base/browser/ui/inputbox/inputBox.css b/src/vs/base/browser/ui/inputbox/inputBox.css
index 827a19f29b487..dc5e637f6ee56 100644
--- a/src/vs/base/browser/ui/inputbox/inputBox.css
+++ b/src/vs/base/browser/ui/inputbox/inputBox.css
@@ -103,4 +103,5 @@
 	background-repeat: no-repeat;
 	width: 16px;
 	height: 16px;
+	color: var(--vscode-icon-foreground);
 }
diff --git a/src/vs/base/browser/ui/list/listView.ts b/src/vs/base/browser/ui/list/listView.ts
index 6e29b67c503a5..5c62e99faf886 100644
--- a/src/vs/base/browser/ui/list/listView.ts
+++ b/src/vs/base/browser/ui/list/listView.ts
@@ -152,8 +152,8 @@ export class ExternalElementsDragAndDropData<T> implements IDragAndDropData {
 
 export class NativeDragAndDropData implements IDragAndDropData {
 
-	readonly types: any[];
-	readonly files: any[];
+	readonly types: unknown[];
+	readonly files: unknown[];
 
 	constructor() {
 		this.types = [];
diff --git a/src/vs/base/browser/ui/menu/menu.ts b/src/vs/base/browser/ui/menu/menu.ts
index c747ea1cd87da..500b0614adeaf 100644
--- a/src/vs/base/browser/ui/menu/menu.ts
+++ b/src/vs/base/browser/ui/menu/menu.ts
@@ -321,14 +321,12 @@ export class Menu extends ActionBar {
 		const fgColor = style.foregroundColor ?? '';
 		const bgColor = style.backgroundColor ?? '';
 		const border = style.borderColor ? `1px solid ${style.borderColor}` : '';
-		const borderRadius = '5px';
-		const shadow = style.shadowColor ? `0 2px 8px ${style.shadowColor}` : '';
+		const borderRadius = 'var(--vscode-cornerRadius-large)';
 
 		scrollElement.style.outline = border;
 		scrollElement.style.borderRadius = borderRadius;
 		scrollElement.style.color = fgColor;
 		scrollElement.style.backgroundColor = bgColor;
-		scrollElement.style.boxShadow = shadow;
 	}
 
 	override getContainer(): HTMLElement {
@@ -1022,7 +1020,7 @@ export function getMenuWidgetCSS(style: IMenuStyles, isForShadowDom: boolean): s
 	let result = /* css */`
 .monaco-menu {
 	font-size: 13px;
-	border-radius: 5px;
+	border-radius: var(--vscode-cornerRadius-large);
 	min-width: 160px;
 }
 
@@ -1137,11 +1135,11 @@ ${formatRule(Codicon.menuSubmenu)}
 .monaco-menu .monaco-action-bar.vertical .action-menu-item {
 	flex: 1 1 auto;
 	display: flex;
-	height: 2em;
+	height: 24px;
 	align-items: center;
 	position: relative;
 	margin: 0 4px;
-	border-radius: 4px;
+	border-radius: var(--vscode-cornerRadius-medium);
 }
 
 .monaco-menu .monaco-action-bar.vertical .action-menu-item:hover .keybinding,
@@ -1241,6 +1239,9 @@ ${formatRule(Codicon.menuSubmenu)}
 	border: none;
 	animation: fadeIn 0.083s linear;
 	-webkit-app-region: no-drag;
+	box-shadow: var(--vscode-shadow-lg${style.shadowColor ? `, 0 0 12px ${style.shadowColor}` : ''});
+	border-radius: var(--vscode-cornerRadius-large);
+	overflow: hidden;
 }
 
 .context-view.monaco-menu-container :focus,
@@ -1270,7 +1271,7 @@ ${formatRule(Codicon.menuSubmenu)}
 }
 
 .monaco-menu .monaco-action-bar.vertical .action-menu-item {
-	height: 2em;
+	height: 24px;
 }
 
 .monaco-menu .monaco-action-bar.vertical .action-label:not(.separator),
diff --git a/src/vs/base/browser/ui/selectBox/selectBox.ts b/src/vs/base/browser/ui/selectBox/selectBox.ts
index 335c2c9c09bdc..e70edcbac5f57 100644
--- a/src/vs/base/browser/ui/selectBox/selectBox.ts
+++ b/src/vs/base/browser/ui/selectBox/selectBox.ts
@@ -51,11 +51,13 @@ export interface ISelectOptionItem {
 	descriptionIsMarkdown?: boolean;
 	readonly descriptionMarkdownActionHandler?: MarkdownActionHandler;
 	isDisabled?: boolean;
+	isSeparator?: boolean;
 }
 
 export const SeparatorSelectOption: Readonly<ISelectOptionItem> = Object.freeze({
 	text: '\u2500\u2500\u2500\u2500\u2500\u2500\u2500\u2500\u2500',
 	isDisabled: true,
+	isSeparator: true,
 });
 
 export interface ISelectBoxStyles extends IListStyles {
diff --git a/src/vs/base/browser/ui/selectBox/selectBoxCustom.css b/src/vs/base/browser/ui/selectBox/selectBoxCustom.css
index b2665393270ab..769ba3a08aa26 100644
--- a/src/vs/base/browser/ui/selectBox/selectBoxCustom.css
+++ b/src/vs/base/browser/ui/selectBox/selectBoxCustom.css
@@ -6,8 +6,8 @@
 .monaco-select-box-dropdown-container {
 	display: none;
 	box-sizing: border-box;
-	border-radius: var(--vscode-cornerRadius-small);
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	border-radius: var(--vscode-cornerRadius-large);
+	box-shadow: var(--vscode-shadow-lg);
 }
 
 .monaco-select-box-dropdown-container > .select-box-details-pane > .select-box-description-markdown * {
@@ -45,6 +45,11 @@
 	padding: 5px 6px;
 }
 
+/* Remove list-level focus ring — individual rows show their own focus indicators */
+.monaco-select-box-dropdown-container > .select-box-dropdown-list-container .monaco-list:focus::before {
+	outline: 0 !important;
+}
+
 .monaco-select-box-dropdown-container > .select-box-dropdown-list-container .monaco-list .monaco-list-row {
 	cursor: pointer;
 	padding-left: 2px;
@@ -76,6 +81,38 @@
 }
 
 
+/* Separator styling */
+.monaco-select-box-dropdown-container > .select-box-dropdown-list-container .monaco-list .monaco-list-row.option-separator {
+	cursor: default;
+	border-radius: 0;
+	padding: 0;
+}
+
+.monaco-select-box-dropdown-container > .select-box-dropdown-list-container .monaco-list .monaco-list-row.option-separator > .option-text {
+	visibility: hidden;
+	width: 0;
+	float: none;
+}
+
+.monaco-select-box-dropdown-container > .select-box-dropdown-list-container .monaco-list .monaco-list-row.option-separator > .option-detail {
+	display: none;
+}
+
+.monaco-select-box-dropdown-container > .select-box-dropdown-list-container .monaco-list .monaco-list-row.option-separator > .option-decorator-right {
+	color: var(--vscode-descriptionForeground);
+	font-size: 12px;
+}
+
+.monaco-select-box-dropdown-container > .select-box-dropdown-list-container .monaco-list .monaco-list-row.option-separator::after {
+	content: '';
+	position: absolute;
+	left: 0;
+	right: 0;
+	top: 50%;
+	height: 1px;
+	background-color: var(--vscode-menu-separatorBackground);
+}
+
 /* Accepted CSS hiding technique for accessibility reader text  */
 /* https://webaim.org/techniques/css/invisiblecontent/ */
 
diff --git a/src/vs/base/browser/ui/selectBox/selectBoxCustom.ts b/src/vs/base/browser/ui/selectBox/selectBoxCustom.ts
index f6c2ff1cb4fec..b7cbca1525069 100644
--- a/src/vs/base/browser/ui/selectBox/selectBoxCustom.ts
+++ b/src/vs/base/browser/ui/selectBox/selectBoxCustom.ts
@@ -71,6 +71,14 @@ class SelectListRenderer implements IListRenderer<ISelectOptionItem, ISelectList
 			// Make sure we do class removal from prior template rendering
 			data.root.classList.remove('option-disabled');
 		}
+
+		// Separator option - show a CSS border instead of text characters
+		if (element.isSeparator) {
+			data.root.classList.add('option-separator');
+			data.root.classList.add('option-disabled');
+		} else {
+			data.root.classList.remove('option-separator');
+		}
 	}
 
 	disposeTemplate(_templateData: ISelectListTemplateData): void {
@@ -395,13 +403,13 @@ export class SelectBoxList extends Disposable implements ISelectBoxDelegate, ILi
 			content.push(`.monaco-select-box-dropdown-container > .select-box-dropdown-list-container .monaco-list .monaco-list-row:not(.option-disabled):not(.focused):hover { background-color: ${this.styles.listHoverBackground} !important; }`);
 		}
 
-		// Match quick input outline styles - ignore for disabled options
+		// Match action widget outline styles - ignore for disabled options
 		if (this.styles.listFocusOutline) {
-			content.push(`.monaco-select-box-dropdown-container > .select-box-dropdown-list-container .monaco-list .monaco-list-row.focused { outline: 1.6px dotted ${this.styles.listFocusOutline} !important; outline-offset: -1.6px !important; }`);
+			content.push(`.monaco-select-box-dropdown-container > .select-box-dropdown-list-container .monaco-list .monaco-list-row.focused { outline: 1px solid ${this.styles.listFocusOutline} !important; outline-offset: -1px !important; }`);
 		}
 
 		if (this.styles.listHoverOutline) {
-			content.push(`.monaco-select-box-dropdown-container > .select-box-dropdown-list-container .monaco-list .monaco-list-row:not(.option-disabled):not(.focused):hover { outline: 1.6px dashed ${this.styles.listHoverOutline} !important; outline-offset: -1.6px !important; }`);
+			content.push(`.monaco-select-box-dropdown-container > .select-box-dropdown-list-container .monaco-list .monaco-list-row:not(.option-disabled):not(.focused):hover { outline: 1px solid ${this.styles.listHoverOutline} !important; outline-offset: -1px !important; }`);
 		}
 
 		// Clear list styles on focus and on hover for disabled options
@@ -425,11 +433,9 @@ export class SelectBoxList extends Disposable implements ISelectBoxDelegate, ILi
 		const background = this.styles.selectBackground ?? '';
 
 		const listBackground = cssJs.asCssValueWithDefault(this.styles.selectListBackground, background);
+		this.selectDropDownContainer.style.backgroundColor = listBackground;
 		this.selectDropDownListContainer.style.backgroundColor = listBackground;
 		this.selectionDetailsPane.style.backgroundColor = listBackground;
-		const optionsBorder = this.styles.focusBorder ?? '';
-		this.selectDropDownContainer.style.outlineColor = optionsBorder;
-		this.selectDropDownContainer.style.outlineOffset = '-1px';
 
 		this.selectList.style(this.styles);
 	}
@@ -510,6 +516,12 @@ export class SelectBoxList extends Disposable implements ISelectBoxDelegate, ILi
 	private renderSelectDropDown(container: HTMLElement, preLayoutPosition?: boolean): IDisposable {
 		container.appendChild(this.selectDropDownContainer);
 
+		// Inherit font-size from the select button so the dropdown matches
+		const computedFontSize = dom.getWindow(this.selectElement).getComputedStyle(this.selectElement).fontSize;
+		if (computedFontSize) {
+			this.selectDropDownContainer.style.fontSize = computedFontSize;
+		}
+
 		// Pre-Layout allows us to change position
 		this.layoutSelectDropDown(preLayoutPosition);
 
@@ -727,6 +739,10 @@ export class SelectBoxList extends Disposable implements ISelectBoxDelegate, ILi
 			mouseSupport: false,
 			accessibilityProvider: {
 				getAriaLabel: element => {
+					if (element.isSeparator) {
+						return localize('selectBoxSeparator', "separator");
+					}
+
 					let label = element.text;
 					if (element.detail) {
 						label += `. ${element.detail}`;
@@ -772,7 +788,7 @@ export class SelectBoxList extends Disposable implements ISelectBoxDelegate, ILi
 		// SetUp list mouse controller - control navigation, disabled items, focus
 		this._register(dom.addDisposableListener(this.selectList.getHTMLElement(), dom.EventType.POINTER_UP, e => this.onPointerUp(e)));
 
-		this._register(this.selectList.onMouseOver(e => typeof e.index !== 'undefined' && this.selectList.setFocus([e.index])));
+		this._register(this.selectList.onMouseOver(e => typeof e.index !== 'undefined' && !this.options[e.index]?.isDisabled && this.selectList.setFocus([e.index])));
 		this._register(this.selectList.onDidChangeFocus(e => this.onListFocus(e)));
 
 		this._register(dom.addDisposableListener(this.selectDropDownContainer, dom.EventType.FOCUS_OUT, e => {
@@ -932,6 +948,12 @@ export class SelectBoxList extends Disposable implements ISelectBoxDelegate, ILi
 	private onEnter(e: StandardKeyboardEvent): void {
 		dom.EventHelper.stop(e);
 
+		// Ignore if current selection is disabled (e.g. separator)
+		if (this.options[this.selected]?.isDisabled) {
+			this.hideSelectDropDown(true);
+			return;
+		}
+
 		// Only fire if selection change
 		if (this.selected !== this._currentSelection) {
 			this._currentSelection = this.selected;
@@ -947,22 +969,23 @@ export class SelectBoxList extends Disposable implements ISelectBoxDelegate, ILi
 		this.hideSelectDropDown(true);
 	}
 
-	// List navigation - have to handle a disabled option (jump over)
+	// List navigation - have to handle disabled options (jump over)
 	private onDownArrow(e: StandardKeyboardEvent): void {
 		if (this.selected < this.options.length - 1) {
 			dom.EventHelper.stop(e, true);
 
-			// Skip disabled options
-			const nextOptionDisabled = this.options[this.selected + 1].isDisabled;
+			// Skip over all contiguous disabled options
+			let next = this.selected + 1;
+			while (next < this.options.length && this.options[next].isDisabled) {
+				next++;
+			}
 
-			if (nextOptionDisabled && this.options.length > this.selected + 2) {
-				this.selected += 2;
-			} else if (nextOptionDisabled) {
+			if (next >= this.options.length) {
 				return;
-			} else {
-				this.selected++;
 			}
 
+			this.selected = next;
+
 			// Set focus/selection - only fire event when closing drop-down or on blur
 			this.select(this.selected);
 			this.selectList.setFocus([this.selected]);
@@ -973,13 +996,19 @@ export class SelectBoxList extends Disposable implements ISelectBoxDelegate, ILi
 	private onUpArrow(e: StandardKeyboardEvent): void {
 		if (this.selected > 0) {
 			dom.EventHelper.stop(e, true);
-			// Skip disabled options
-			const previousOptionDisabled = this.options[this.selected - 1].isDisabled;
-			if (previousOptionDisabled && this.selected > 1) {
-				this.selected -= 2;
-			} else {
-				this.selected--;
+
+			// Skip over all contiguous disabled options
+			let prev = this.selected - 1;
+			while (prev >= 0 && this.options[prev].isDisabled) {
+				prev--;
+			}
+
+			if (prev < 0) {
+				return;
 			}
+
+			this.selected = prev;
+
 			// Set focus/selection - only fire event when closing drop-down or on blur
 			this.select(this.selected);
 			this.selectList.setFocus([this.selected]);
@@ -994,13 +1023,17 @@ export class SelectBoxList extends Disposable implements ISelectBoxDelegate, ILi
 
 		// Allow scrolling to settle
 		setTimeout(() => {
-			this.selected = this.selectList.getFocus()[0];
+			let candidate = this.selectList.getFocus()[0];
 
-			// Shift selection down if we land on a disabled option
-			if (this.options[this.selected].isDisabled && this.selected < this.options.length - 1) {
-				this.selected++;
-				this.selectList.setFocus([this.selected]);
+			// Shift selection up if we land on a disabled option
+			while (candidate > 0 && this.options[candidate].isDisabled) {
+				candidate--;
+			}
+			if (this.options[candidate].isDisabled) {
+				return;
 			}
+			this.selected = candidate;
+			this.selectList.setFocus([this.selected]);
 			this.selectList.reveal(this.selected);
 			this.select(this.selected);
 		}, 1);
@@ -1013,13 +1046,17 @@ export class SelectBoxList extends Disposable implements ISelectBoxDelegate, ILi
 
 		// Allow scrolling to settle
 		setTimeout(() => {
-			this.selected = this.selectList.getFocus()[0];
+			let candidate = this.selectList.getFocus()[0];
 
-			// Shift selection up if we land on a disabled option
-			if (this.options[this.selected].isDisabled && this.selected > 0) {
-				this.selected--;
-				this.selectList.setFocus([this.selected]);
+			// Shift selection down if we land on a disabled option
+			while (candidate < this.options.length - 1 && this.options[candidate].isDisabled) {
+				candidate++;
 			}
+			if (this.options[candidate].isDisabled) {
+				return;
+			}
+			this.selected = candidate;
+			this.selectList.setFocus([this.selected]);
 			this.selectList.reveal(this.selected);
 			this.select(this.selected);
 		}, 1);
@@ -1031,10 +1068,14 @@ export class SelectBoxList extends Disposable implements ISelectBoxDelegate, ILi
 		if (this.options.length < 2) {
 			return;
 		}
-		this.selected = 0;
-		if (this.options[this.selected].isDisabled && this.selected > 1) {
-			this.selected++;
+		let candidate = 0;
+		while (candidate < this.options.length - 1 && this.options[candidate].isDisabled) {
+			candidate++;
 		}
+		if (this.options[candidate].isDisabled) {
+			return;
+		}
+		this.selected = candidate;
 		this.selectList.setFocus([this.selected]);
 		this.selectList.reveal(this.selected);
 		this.select(this.selected);
@@ -1046,10 +1087,14 @@ export class SelectBoxList extends Disposable implements ISelectBoxDelegate, ILi
 		if (this.options.length < 2) {
 			return;
 		}
-		this.selected = this.options.length - 1;
-		if (this.options[this.selected].isDisabled && this.selected > 1) {
-			this.selected--;
+		let candidate = this.options.length - 1;
+		while (candidate > 0 && this.options[candidate].isDisabled) {
+			candidate--;
+		}
+		if (this.options[candidate].isDisabled) {
+			return;
 		}
+		this.selected = candidate;
 		this.selectList.setFocus([this.selected]);
 		this.selectList.reveal(this.selected);
 		this.select(this.selected);
diff --git a/src/vs/base/browser/ui/selectBox/selectBoxNative.ts b/src/vs/base/browser/ui/selectBox/selectBoxNative.ts
index 9eebae7dbb138..0c7ac5bcb35a3 100644
--- a/src/vs/base/browser/ui/selectBox/selectBoxNative.ts
+++ b/src/vs/base/browser/ui/selectBox/selectBoxNative.ts
@@ -98,7 +98,7 @@ export class SelectBoxNative extends Disposable implements ISelectBoxDelegate {
 			this.selectElement.options.length = 0;
 
 			this.options.forEach((option, index) => {
-				this.selectElement.add(this.createOption(option.text, index, option.isDisabled));
+				this.selectElement.add(this.createOption(option.text, index, option.isDisabled, option.isSeparator));
 			});
 
 		}
@@ -179,11 +179,15 @@ export class SelectBoxNative extends Disposable implements ISelectBoxDelegate {
 
 	}
 
-	private createOption(value: string, index: number, disabled?: boolean): HTMLOptionElement {
+	private createOption(value: string, index: number, disabled?: boolean, isSeparator?: boolean): HTMLOptionElement {
 		const option = document.createElement('option');
 		option.value = value;
 		option.text = value;
-		option.disabled = !!disabled;
+		option.disabled = !!disabled || !!isSeparator;
+
+		if (isSeparator) {
+			option.setAttribute('role', 'separator');
+		}
 
 		return option;
 	}
diff --git a/src/vs/base/common/actions.ts b/src/vs/base/common/actions.ts
index 6d3e3f2b3db58..18641db33f93e 100644
--- a/src/vs/base/common/actions.ts
+++ b/src/vs/base/common/actions.ts
@@ -220,6 +220,24 @@ export class Separator implements IAction {
 		return out;
 	}
 
+	/**
+	 * Removes leading, trailing, and consecutive duplicate separators in-place and returns the actions.
+	 */
+	public static clean(actions: IAction[]): IAction[] {
+		while (actions.length > 0 && actions[0].id === Separator.ID) {
+			actions.shift();
+		}
+		while (actions.length > 0 && actions[actions.length - 1].id === Separator.ID) {
+			actions.pop();
+		}
+		for (let i = actions.length - 2; i >= 0; i--) {
+			if (actions[i].id === Separator.ID && actions[i + 1].id === Separator.ID) {
+				actions.splice(i + 1, 1);
+			}
+		}
+		return actions;
+	}
+
 	static readonly ID = 'vs.actions.separator';
 
 	readonly id: string = Separator.ID;
diff --git a/src/vs/base/common/async.ts b/src/vs/base/common/async.ts
index 3dcfa0c513087..e5aaa42487681 100644
--- a/src/vs/base/common/async.ts
+++ b/src/vs/base/common/async.ts
@@ -1098,15 +1098,15 @@ export class IntervalTimer implements IDisposable {
 	}
 }
 
-export class RunOnceScheduler implements IDisposable {
+export class RunOnceScheduler<Runner extends (...args: any[]) => any = () => any> implements IDisposable {
 
-	protected runner: ((...args: unknown[]) => void) | null;
+	protected runner: Runner | null;
 
 	private timeoutToken: Timeout | undefined;
 	private timeout: number;
 	private timeoutHandler: () => void;
 
-	constructor(runner: (...args: any[]) => void, delay: number) {
+	constructor(runner: Runner, delay: number) {
 		this.timeoutToken = undefined;
 		this.runner = runner;
 		this.timeout = delay;
@@ -1246,7 +1246,7 @@ export class ProcessTimeRunOnceScheduler {
 	}
 }
 
-export class RunOnceWorker<T> extends RunOnceScheduler {
+export class RunOnceWorker<T> extends RunOnceScheduler<(units: T[]) => void> {
 
 	private units: T[] = [];
 
diff --git a/src/vs/base/common/codiconsLibrary.ts b/src/vs/base/common/codiconsLibrary.ts
index f541d4face8e6..1a2d78bcd70ef 100644
--- a/src/vs/base/common/codiconsLibrary.ts
+++ b/src/vs/base/common/codiconsLibrary.ts
@@ -655,4 +655,5 @@ export const codiconsLibrary = {
 	openai: register('openai', 0xec81),
 	claude: register('claude', 0xec82),
 	openInWindow: register('open-in-window', 0xec83),
+	newSession: register('new-session', 0xec84),
 } as const;
diff --git a/src/vs/base/common/decorators.ts b/src/vs/base/common/decorators.ts
index 7510ffcec1f4f..74d2e56f51e12 100644
--- a/src/vs/base/common/decorators.ts
+++ b/src/vs/base/common/decorators.ts
@@ -45,7 +45,7 @@ export function memoize(_target: Object, key: string, descriptor: PropertyDescri
 	}
 
 	const memoizeKey = `$memoize$${key}`;
-	descriptor[fnKey!] = function (...args: any[]) {
+	descriptor[fnKey!] = function (this: any, ...args: unknown[]) {
 		if (!this.hasOwnProperty(memoizeKey)) {
 			Object.defineProperty(this, memoizeKey, {
 				configurable: false,
@@ -54,8 +54,7 @@ export function memoize(_target: Object, key: string, descriptor: PropertyDescri
 				value: fn.apply(this, args)
 			});
 		}
-		// eslint-disable-next-line local/code-no-any-casts
-		return (this as any)[memoizeKey];
+		return this[memoizeKey];
 	};
 }
 
diff --git a/src/vs/base/common/defaultAccount.ts b/src/vs/base/common/defaultAccount.ts
index 2d10cedc84d9d..3c53a69862215 100644
--- a/src/vs/base/common/defaultAccount.ts
+++ b/src/vs/base/common/defaultAccount.ts
@@ -48,6 +48,11 @@ export interface IPolicyData {
 	readonly mcpAccess?: 'allow_all' | 'registry_only';
 }
 
+export interface ICopilotTokenInfo {
+	readonly sn?: string;
+	readonly fcv1?: string;
+}
+
 export interface IDefaultAccountAuthenticationProvider {
 	readonly id: string;
 	readonly name: string;
diff --git a/src/vs/base/common/event.ts b/src/vs/base/common/event.ts
index de0fce1d4fdd0..a9d495ab6b090 100644
--- a/src/vs/base/common/event.ts
+++ b/src/vs/base/common/event.ts
@@ -11,6 +11,7 @@ import { createSingleCallFunction } from './functional.js';
 import { combinedDisposable, Disposable, DisposableMap, DisposableStore, IDisposable, toDisposable } from './lifecycle.js';
 import { LinkedList } from './linkedList.js';
 import { IObservable, IObservableWithChange, IObserver } from './observable.js';
+import { env } from './process.js';
 import { StopWatch } from './stopwatch.js';
 import { MicrotaskDelay } from './symbols.js';
 
@@ -31,6 +32,14 @@ const _enableSnapshotPotentialLeakWarning = false
 	// || Boolean("TRUE") // causes a linter warning so that it cannot be pushed
 	;
 
+
+const _bufferLeakWarnCountThreshold = 100;
+const _bufferLeakWarnTimeThreshold = 60_000; // 1 minute
+
+function _isBufferLeakWarningEnabled(): boolean {
+	return !!env['VSCODE_DEV'];
+}
+
 /**
  * An event with zero or one parameters that can be subscribed to. The event is a function itself.
  */
@@ -490,6 +499,7 @@ export namespace Event {
 	 * returned event causes this utility to leak a listener on the original event.
 	 *
 	 * @param event The event source for the new event.
+	 * @param debugName A name for this buffer, used in leak detection warnings.
 	 * @param flushAfterTimeout Determines whether to flush the buffer after a timeout immediately or after a
 	 * `setTimeout` when the first event listener is added.
 	 * @param _buffer Internal: A source event array used for tests.
@@ -499,15 +509,46 @@ export namespace Event {
 	 * // Start accumulating events, when the first listener is attached, flush
 	 * // the event after a timeout such that multiple listeners attached before
 	 * // the timeout would receive the event
-	 * this.onInstallExtension = Event.buffer(service.onInstallExtension, true);
+	 * this.onInstallExtension = Event.buffer(service.onInstallExtension, 'onInstallExtension', true);
 	 * ```
 	 */
-	export function buffer<T>(event: Event<T>, flushAfterTimeout = false, _buffer: T[] = [], disposable?: DisposableStore): Event<T> {
+	export function buffer<T>(event: Event<T>, debugName: string, flushAfterTimeout = false, _buffer: T[] = [], disposable?: DisposableStore): Event<T> {
 		let buffer: T[] | null = _buffer.slice();
 
+		// Dev-only leak detection: track when buffer was created and warn
+		// if events accumulate without ever being consumed.
+		let bufferLeakWarningData: { stack: Stacktrace; timerId: ReturnType<typeof setTimeout>; warned: boolean } | undefined;
+		if (_isBufferLeakWarningEnabled()) {
+			bufferLeakWarningData = {
+				stack: Stacktrace.create(),
+				timerId: setTimeout(() => {
+					if (buffer && buffer.length > 0 && bufferLeakWarningData && !bufferLeakWarningData.warned) {
+						bufferLeakWarningData.warned = true;
+						console.warn(`[Event.buffer][${debugName}] potential LEAK detected: ${buffer.length} events buffered for ${_bufferLeakWarnTimeThreshold / 1000}s without being consumed. Buffered here:`);
+						bufferLeakWarningData.stack.print();
+					}
+				}, _bufferLeakWarnTimeThreshold),
+				warned: false
+			};
+			if (disposable) {
+				disposable.add(toDisposable(() => clearTimeout(bufferLeakWarningData!.timerId)));
+			}
+		}
+
+		const clearLeakWarningTimer = () => {
+			if (bufferLeakWarningData) {
+				clearTimeout(bufferLeakWarningData.timerId);
+			}
+		};
+
 		let listener: IDisposable | null = event(e => {
 			if (buffer) {
 				buffer.push(e);
+				if (_isBufferLeakWarningEnabled() && bufferLeakWarningData && !bufferLeakWarningData.warned && buffer.length >= _bufferLeakWarnCountThreshold) {
+					bufferLeakWarningData.warned = true;
+					console.warn(`[Event.buffer][${debugName}] potential LEAK detected: ${buffer.length} events buffered without being consumed. Buffered here:`);
+					bufferLeakWarningData.stack.print();
+				}
 			} else {
 				emitter.fire(e);
 			}
@@ -520,6 +561,7 @@ export namespace Event {
 		const flush = () => {
 			buffer?.forEach(e => emitter.fire(e));
 			buffer = null;
+			clearLeakWarningTimer();
 		};
 
 		const emitter = new Emitter<T>({
@@ -547,6 +589,7 @@ export namespace Event {
 					listener.dispose();
 				}
 				listener = null;
+				clearLeakWarningTimer();
 			}
 		});
 
@@ -664,7 +707,7 @@ export namespace Event {
 	 * Creates an {@link Event} from a node event emitter.
 	 */
 	export function fromNodeEventEmitter<T>(emitter: NodeEventEmitter, eventName: string, map: (...args: any[]) => T = id => id): Event<T> {
-		const fn = (...args: any[]) => result.fire(map(...args));
+		const fn = (...args: unknown[]) => result.fire(map(...args));
 		const onFirstListenerAdd = () => emitter.on(eventName, fn);
 		const onLastListenerRemove = () => emitter.removeListener(eventName, fn);
 		const result = new Emitter<T>({ onWillAddFirstListener: onFirstListenerAdd, onDidRemoveLastListener: onLastListenerRemove });
@@ -681,7 +724,7 @@ export namespace Event {
 	 * Creates an {@link Event} from a DOM event emitter.
 	 */
 	export function fromDOMEventEmitter<T>(emitter: DOMEventEmitter, eventName: string, map: (...args: any[]) => T = id => id): Event<T> {
-		const fn = (...args: any[]) => result.fire(map(...args));
+		const fn = (...args: unknown[]) => result.fire(map(...args));
 		const onFirstListenerAdd = () => emitter.addEventListener(eventName, fn);
 		const onLastListenerRemove = () => emitter.removeEventListener(eventName, fn);
 		const result = new Emitter<T>({ onWillAddFirstListener: onFirstListenerAdd, onDidRemoveLastListener: onLastListenerRemove });
diff --git a/src/vs/base/common/htmlContent.ts b/src/vs/base/common/htmlContent.ts
index 070279f045ae7..16049d7e6f731 100644
--- a/src/vs/base/common/htmlContent.ts
+++ b/src/vs/base/common/htmlContent.ts
@@ -210,9 +210,9 @@ export function createMarkdownLink(text: string, href: string, title?: string, e
 	return `[${escapeTokens ? escapeMarkdownSyntaxTokens(text) : text}](${href}${title ? ` "${escapeMarkdownSyntaxTokens(title)}"` : ''})`;
 }
 
-export function createMarkdownCommandLink(command: { title: string; id: string; arguments?: unknown[]; tooltip?: string }, escapeTokens = true): string {
+export function createMarkdownCommandLink(command: { text: string; id: string; arguments?: unknown[]; tooltip: string }, escapeTokens = true): string {
 	const uri = createCommandUri(command.id, ...(command.arguments || [])).toString();
-	return createMarkdownLink(command.title, uri, command.tooltip, escapeTokens);
+	return createMarkdownLink(command.text, uri, command.tooltip, escapeTokens);
 }
 
 export function createCommandUri(commandId: string, ...commandArgs: unknown[]): URI {
diff --git a/src/vs/base/common/jsonRpcProtocol.ts b/src/vs/base/common/jsonRpcProtocol.ts
index 67c4ed4fc4d82..35d7144ba82bf 100644
--- a/src/vs/base/common/jsonRpcProtocol.ts
+++ b/src/vs/base/common/jsonRpcProtocol.ts
@@ -43,6 +43,7 @@ export interface IJsonRpcErrorResponse {
 }
 
 export type JsonRpcMessage = IJsonRpcRequest | IJsonRpcNotification | IJsonRpcSuccessResponse | IJsonRpcErrorResponse;
+export type JsonRpcResponse = IJsonRpcSuccessResponse | IJsonRpcErrorResponse;
 
 interface IPendingRequest {
 	promise: DeferredPromise<unknown>;
@@ -122,15 +123,31 @@ export class JsonRpcProtocol extends Disposable {
 		}) as Promise<T>;
 	}
 
-	public async handleMessage(message: JsonRpcMessage | JsonRpcMessage[]): Promise<void> {
+	/**
+	 * Handles one or more incoming JSON-RPC messages.
+	 *
+	 * Returns an array of JSON-RPC response objects generated for any incoming
+	 * requests in the message(s). Notifications and responses to our own
+	 * outgoing requests do not produce return values. For batch inputs, the
+	 * returned responses are in the same order as the corresponding requests.
+	 *
+	 * Note: responses are also emitted via the `_send` callback, so callers
+	 * that rely on the return value should not re-send them.
+	 */
+	public async handleMessage(message: JsonRpcMessage | JsonRpcMessage[]): Promise<JsonRpcResponse[]> {
 		if (Array.isArray(message)) {
+			const replies: JsonRpcResponse[] = [];
 			for (const single of message) {
-				await this._handleMessage(single);
+				const reply = await this._handleMessage(single);
+				if (reply) {
+					replies.push(reply);
+				}
 			}
-			return;
+			return replies;
 		}
 
-		await this._handleMessage(message);
+		const reply = await this._handleMessage(message);
+		return reply ? [reply] : [];
 	}
 
 	public cancelPendingRequest(id: JsonRpcId): void {
@@ -152,22 +169,25 @@ export class JsonRpcProtocol extends Disposable {
 		}
 	}
 
-	private async _handleMessage(message: JsonRpcMessage): Promise<void> {
+	private async _handleMessage(message: JsonRpcMessage): Promise<JsonRpcResponse | undefined> {
 		if (isJsonRpcResponse(message)) {
 			if (hasKey(message, { result: true })) {
 				this._handleResult(message);
 			} else {
 				this._handleError(message);
 			}
+			return undefined;
 		}
 
 		if (isJsonRpcRequest(message)) {
-			await this._handleRequest(message);
+			return this._handleRequest(message);
 		}
 
 		if (isJsonRpcNotification(message)) {
 			this._handlers.handleNotification?.(message);
 		}
+
+		return undefined;
 	}
 
 	private _handleResult(response: IJsonRpcSuccessResponse): void {
@@ -192,17 +212,18 @@ export class JsonRpcProtocol extends Disposable {
 		}
 	}
 
-	private async _handleRequest(request: IJsonRpcRequest): Promise<void> {
+	private async _handleRequest(request: IJsonRpcRequest): Promise<JsonRpcResponse> {
 		if (!this._handlers.handleRequest) {
-			this._send({
+			const response: IJsonRpcErrorResponse = {
 				jsonrpc: '2.0',
 				id: request.id,
 				error: {
 					code: JsonRpcProtocol.MethodNotFound,
 					message: `Method not found: ${request.method}`,
 				}
-			});
-			return;
+			};
+			this._send(response);
+			return response;
 		}
 
 		const cts = new CancellationTokenSource();
@@ -211,14 +232,17 @@ export class JsonRpcProtocol extends Disposable {
 		try {
 			const resultOrThenable = this._handlers.handleRequest(request, cts.token);
 			const result = isThenable(resultOrThenable) ? await resultOrThenable : resultOrThenable;
-			this._send({
+			const response: IJsonRpcSuccessResponse = {
 				jsonrpc: '2.0',
 				id: request.id,
 				result,
-			});
+			};
+			this._send(response);
+			return response;
 		} catch (error) {
+			let response: IJsonRpcErrorResponse;
 			if (error instanceof JsonRpcError) {
-				this._send({
+				response = {
 					jsonrpc: '2.0',
 					id: request.id,
 					error: {
@@ -226,17 +250,19 @@ export class JsonRpcProtocol extends Disposable {
 						message: error.message,
 						data: error.data,
 					}
-				});
+				};
 			} else {
-				this._send({
+				response = {
 					jsonrpc: '2.0',
 					id: request.id,
 					error: {
 						code: JsonRpcProtocol.InternalError,
 						message: error instanceof Error ? error.message : 'Internal error',
 					}
-				});
+				};
 			}
+			this._send(response);
+			return response;
 		} finally {
 			cts.dispose(true);
 		}
diff --git a/src/vs/base/common/lifecycle.ts b/src/vs/base/common/lifecycle.ts
index 630edb097f250..a75cbb1cce309 100644
--- a/src/vs/base/common/lifecycle.ts
+++ b/src/vs/base/common/lifecycle.ts
@@ -720,7 +720,7 @@ export class AsyncReferenceCollection<T> {
 
 	constructor(private referenceCollection: ReferenceCollection<Promise<T>>) { }
 
-	async acquire(key: string, ...args: any[]): Promise<IReference<T>> {
+	async acquire(key: string, ...args: unknown[]): Promise<IReference<T>> {
 		const ref = this.referenceCollection.acquire(key, ...args);
 
 		try {
diff --git a/src/vs/base/common/network.ts b/src/vs/base/common/network.ts
index 74cb106fd3cef..c2efd167054a8 100644
--- a/src/vs/base/common/network.ts
+++ b/src/vs/base/common/network.ts
@@ -75,6 +75,9 @@ export namespace Schemas {
 
 	export const vscodeTerminal = 'vscode-terminal';
 
+	/** Scheme used for the image carousel editor. */
+	export const vscodeImageCarousel = 'vscode-image-carousel';
+
 	/** Scheme used for code blocks in chat. */
 	export const vscodeChatCodeBlock = 'vscode-chat-code-block';
 
diff --git a/src/vs/base/common/observableInternal/index.ts b/src/vs/base/common/observableInternal/index.ts
index af010d118c3b6..95347c3088b3e 100644
--- a/src/vs/base/common/observableInternal/index.ts
+++ b/src/vs/base/common/observableInternal/index.ts
@@ -7,7 +7,7 @@
 
 export { observableValueOpts } from './observables/observableValueOpts.js';
 export { autorun, autorunDelta, autorunHandleChanges, autorunOpts, autorunWithStore, autorunWithStoreHandleChanges, autorunIterableDelta, autorunSelfDisposable } from './reactions/autorun.js';
-export { type IObservable, type IObservableWithChange, type IObserver, type IReader, type ISettable, type ISettableObservable, type ITransaction } from './base.js';
+export { type IObservable, type IObservableWithChange, type IObserver, type IReader, type ISettable, type IReaderWithStore, type ISettableObservable, type ITransaction } from './base.js';
 export { disposableObservableValue } from './observables/observableValue.js';
 export { derived, derivedDisposable, derivedHandleChanges, derivedOpts, derivedWithSetter, derivedWithStore } from './observables/derived.js';
 export { type IDerivedReader } from './observables/derivedImpl.js';
diff --git a/src/vs/base/common/observableInternal/logging/debugger/rpc.ts b/src/vs/base/common/observableInternal/logging/debugger/rpc.ts
index d19da1fe15970..c4d392bca69fd 100644
--- a/src/vs/base/common/observableInternal/logging/debugger/rpc.ts
+++ b/src/vs/base/common/observableInternal/logging/debugger/rpc.ts
@@ -72,7 +72,7 @@ export class SimpleTypedRpcConnection<T extends Side> {
 
 		const requests = new Proxy({}, {
 			get: (target, key: string) => {
-				return async (...args: any[]) => {
+				return async (...args: unknown[]) => {
 					const result = await this._channel.sendRequest([key, args] satisfies OutgoingMessage);
 					if (result.type === 'error') {
 						throw result.value;
@@ -85,7 +85,7 @@ export class SimpleTypedRpcConnection<T extends Side> {
 
 		const notifications = new Proxy({}, {
 			get: (target, key: string) => {
-				return (...args: any[]) => {
+				return (...args: unknown[]) => {
 					this._channel.sendNotification([key, args] satisfies OutgoingMessage);
 				};
 			}
diff --git a/src/vs/base/parts/ipc/common/ipc.ts b/src/vs/base/parts/ipc/common/ipc.ts
index 8e061681e5c51..663b7f541ee68 100644
--- a/src/vs/base/parts/ipc/common/ipc.ts
+++ b/src/vs/base/parts/ipc/common/ipc.ts
@@ -1118,7 +1118,7 @@ export namespace ProxyChannel {
 		const mapEventNameToEvent = new Map<string, Event<unknown>>();
 		for (const key in handler) {
 			if (propertyIsEvent(key)) {
-				mapEventNameToEvent.set(key, Event.buffer(handler[key] as Event<unknown>, true, undefined, disposables));
+				mapEventNameToEvent.set(key, Event.buffer(handler[key] as Event<unknown>, key, true, undefined, disposables));
 			}
 		}
 
@@ -1137,7 +1137,7 @@ export namespace ProxyChannel {
 					}
 
 					if (propertyIsEvent(event)) {
-						mapEventNameToEvent.set(event, Event.buffer(handler[event] as Event<unknown>, true, undefined, disposables));
+						mapEventNameToEvent.set(event, Event.buffer(handler[event] as Event<unknown>, event, true, undefined, disposables));
 
 						return mapEventNameToEvent.get(event) as Event<T>;
 					}
@@ -1209,10 +1209,10 @@ export namespace ProxyChannel {
 					}
 
 					// Function
-					return async function (...args: any[]) {
+					return async function (...args: unknown[]) {
 
 						// Add context if any
-						let methodArgs: any[];
+						let methodArgs: unknown[];
 						if (options && !isUndefinedOrNull(options.context)) {
 							methodArgs = [options.context, ...args];
 						} else {
diff --git a/src/vs/base/parts/ipc/electron-main/ipcMain.ts b/src/vs/base/parts/ipc/electron-main/ipcMain.ts
index 0137b8924eb47..267c15b7125b2 100644
--- a/src/vs/base/parts/ipc/electron-main/ipcMain.ts
+++ b/src/vs/base/parts/ipc/electron-main/ipcMain.ts
@@ -25,7 +25,7 @@ class ValidatedIpcMain implements Event.NodeEventEmitter {
 
 		// Remember the wrapped listener so that later we can
 		// properly implement `removeListener`.
-		const wrappedListener = (event: electron.IpcMainEvent, ...args: any[]) => {
+		const wrappedListener = (event: electron.IpcMainEvent, ...args: unknown[]) => {
 			if (this.validateEvent(channel, event)) {
 				listener(event, ...args);
 			}
@@ -43,7 +43,7 @@ class ValidatedIpcMain implements Event.NodeEventEmitter {
 	 * only the next time a message is sent to `channel`, after which it is removed.
 	 */
 	once(channel: string, listener: ipcMainListener): this {
-		electron.ipcMain.once(channel, (event: electron.IpcMainEvent, ...args: any[]) => {
+		electron.ipcMain.once(channel, (event: electron.IpcMainEvent, ...args: unknown[]) => {
 			if (this.validateEvent(channel, event)) {
 				listener(event, ...args);
 			}
@@ -69,7 +69,7 @@ class ValidatedIpcMain implements Event.NodeEventEmitter {
 	 * provided to the renderer process. Please refer to #24427 for details.
 	 */
 	handle(channel: string, listener: (event: electron.IpcMainInvokeEvent, ...args: any[]) => Promise<unknown>): this {
-		electron.ipcMain.handle(channel, (event: electron.IpcMainInvokeEvent, ...args: any[]) => {
+		electron.ipcMain.handle(channel, (event: electron.IpcMainInvokeEvent, ...args: unknown[]) => {
 			if (this.validateEvent(channel, event)) {
 				return listener(event, ...args);
 			}
diff --git a/src/vs/base/parts/request/common/request.ts b/src/vs/base/parts/request/common/request.ts
index 1e2a8ead2fdb0..b649cff368f72 100644
--- a/src/vs/base/parts/request/common/request.ts
+++ b/src/vs/base/parts/request/common/request.ts
@@ -50,6 +50,11 @@ export interface IRequestOptions {
 	 * be supported in all implementations.
 	 */
 	disableCache?: boolean;
+	/**
+	 * Identifies the call site making this request, used for telemetry.
+	 * Use "NO_FETCH_TELEMETRY" to opt out of request telemetry.
+	 */
+	callSite: string;
 }
 
 export interface IRequestContext {
diff --git a/src/vs/base/parts/request/test/electron-main/request.test.ts b/src/vs/base/parts/request/test/electron-main/request.test.ts
index 895b5dc6899fd..1b51cbf42893b 100644
--- a/src/vs/base/parts/request/test/electron-main/request.test.ts
+++ b/src/vs/base/parts/request/test/electron-main/request.test.ts
@@ -58,7 +58,8 @@ suite('Request', () => {
 			url: `http://127.0.0.1:${port}`,
 			headers: {
 				'echo-header': 'echo-value'
-			}
+			},
+			callSite: 'request.test.GET'
 		}, CancellationToken.None);
 		assert.strictEqual(context.res.statusCode, 200);
 		assert.strictEqual(context.res.headers['content-type'], 'application/json');
@@ -74,6 +75,7 @@ suite('Request', () => {
 			type: 'POST',
 			url: `http://127.0.0.1:${port}/postpath`,
 			data: 'Some data',
+			callSite: 'request.test.POST'
 		}, CancellationToken.None);
 		assert.strictEqual(context.res.statusCode, 200);
 		assert.strictEqual(context.res.headers['content-type'], 'application/json');
@@ -91,6 +93,7 @@ suite('Request', () => {
 					type: 'GET',
 					url: `http://127.0.0.1:${port}/noreply`,
 					timeout: 123,
+					callSite: 'request.test.timeout'
 				}, CancellationToken.None);
 				assert.fail('Should fail with timeout');
 			} catch (err) {
@@ -106,6 +109,7 @@ suite('Request', () => {
 				const res = request({
 					type: 'GET',
 					url: `http://127.0.0.1:${port}/noreply`,
+					callSite: 'request.test.cancel'
 				}, source.token);
 				await new Promise(resolve => setTimeout(resolve, 100));
 				source.cancel();
diff --git a/src/vs/base/test/browser/markdownRenderer.test.ts b/src/vs/base/test/browser/markdownRenderer.test.ts
index cdfbe914fa929..16373be210102 100644
--- a/src/vs/base/test/browser/markdownRenderer.test.ts
+++ b/src/vs/base/test/browser/markdownRenderer.test.ts
@@ -307,6 +307,36 @@ suite('MarkdownRenderer', () => {
 		assert.strictEqual(result.innerHTML, `<p><a href="" title="./foo" draggable="false" data-href="https://example.com/path/foo">text</a> <a href="" data-href="https://example.com/path/bar">bar</a> <img src="https://example.com/path/cat.gif"></p>`);
 	});
 
+	test('Should use decoded file path as title for file:// links', () => {
+		const fileUri = URI.file('/home/user/project/lib.d.ts');
+		const md = new MarkdownString(`[log](${fileUri.toString()})`, {});
+
+		const result = store.add(renderMarkdown(md)).element;
+		const anchor = result.querySelector('a')!;
+		assert.ok(anchor);
+		assert.strictEqual(anchor.title, fileUri.fsPath);
+	});
+
+	test('Should include fragment in title for file:// links with line numbers', () => {
+		const fileUri = URI.file('/home/user/project/lib.d.ts');
+		const md = new MarkdownString(`[log](${fileUri.toString()}#L42)`, {});
+
+		const result = store.add(renderMarkdown(md)).element;
+		const anchor = result.querySelector('a')!;
+		assert.ok(anchor);
+		assert.strictEqual(anchor.title, `${fileUri.fsPath}#L42`);
+	});
+
+	test('Should not override explicit title for file:// links', () => {
+		const fileUri = URI.file('/home/user/project/lib.d.ts');
+		const md = new MarkdownString(`[log](${fileUri.toString()} "Go to definition")`, {});
+
+		const result = store.add(renderMarkdown(md)).element;
+		const anchor = result.querySelector('a')!;
+		assert.ok(anchor);
+		assert.strictEqual(anchor.title, 'Go to definition');
+	});
+
 	suite('PlaintextMarkdownRender', () => {
 
 		test('test code, blockquote, heading, list, listitem, paragraph, table, tablerow, tablecell, strong, em, br, del, text are rendered plaintext', () => {
diff --git a/src/vs/base/test/common/event.test.ts b/src/vs/base/test/common/event.test.ts
index 4f0369b28b979..cf3c252b90902 100644
--- a/src/vs/base/test/common/event.test.ts
+++ b/src/vs/base/test/common/event.test.ts
@@ -1006,7 +1006,7 @@ suite('Event utils', () => {
 			const result: number[] = [];
 			const emitter = ds.add(new Emitter<number>());
 			const event = emitter.event;
-			const bufferedEvent = Event.buffer(event);
+			const bufferedEvent = Event.buffer(event, 'test');
 
 			emitter.fire(1);
 			emitter.fire(2);
@@ -1028,7 +1028,7 @@ suite('Event utils', () => {
 			const result: number[] = [];
 			const emitter = ds.add(new Emitter<number>());
 			const event = emitter.event;
-			const bufferedEvent = Event.buffer(event, true);
+			const bufferedEvent = Event.buffer(event, 'test', true);
 
 			emitter.fire(1);
 			emitter.fire(2);
@@ -1050,7 +1050,7 @@ suite('Event utils', () => {
 			const result: number[] = [];
 			const emitter = ds.add(new Emitter<number>());
 			const event = emitter.event;
-			const bufferedEvent = Event.buffer(event, false, [-2, -1, 0]);
+			const bufferedEvent = Event.buffer(event, 'test', false, [-2, -1, 0]);
 
 			emitter.fire(1);
 			emitter.fire(2);
diff --git a/src/vs/base/test/common/jsonRpcProtocol.test.ts b/src/vs/base/test/common/jsonRpcProtocol.test.ts
index 4a167d2cc8a2c..9a000e35f48d2 100644
--- a/src/vs/base/test/common/jsonRpcProtocol.test.ts
+++ b/src/vs/base/test/common/jsonRpcProtocol.test.ts
@@ -39,7 +39,7 @@ suite('JsonRpcProtocol', () => {
 		const requestPromise = protocol.sendRequest<string>({ method: 'echo', params: { value: 'ok' } });
 		const outgoingRequest = sentMessages[0] as IJsonRpcRequest;
 
-		await protocol.handleMessage({
+		const replies = await protocol.handleMessage({
 			jsonrpc: '2.0',
 			id: outgoingRequest.id,
 			result: 'done'
@@ -47,6 +47,7 @@ suite('JsonRpcProtocol', () => {
 
 		const result = await requestPromise;
 		assert.strictEqual(result, 'done');
+		assert.deepStrictEqual(replies, []);
 	});
 
 	test('sendRequest rejects on error response', async () => {
@@ -107,20 +108,22 @@ suite('JsonRpcProtocol', () => {
 	test('handleRequest responds with method not found without handler', async () => {
 		const { protocol, sentMessages } = createProtocol();
 
-		await protocol.handleMessage({
+		const replies = await protocol.handleMessage({
 			jsonrpc: '2.0',
 			id: 7,
 			method: 'unknown'
 		});
 
-		assert.deepStrictEqual(sentMessages, [{
+		const expected = [{
 			jsonrpc: '2.0',
 			id: 7,
 			error: {
 				code: -32601,
 				message: 'Method not found: unknown'
 			}
-		}]);
+		}];
+		assert.deepStrictEqual(sentMessages, expected);
+		assert.deepStrictEqual(replies, expected);
 	});
 
 	test('handleRequest responds with result and passes cancellation token', async () => {
@@ -134,7 +137,7 @@ suite('JsonRpcProtocol', () => {
 			}
 		});
 
-		await protocol.handleMessage({
+		const replies = await protocol.handleMessage({
 			jsonrpc: '2.0',
 			id: 9,
 			method: 'compute'
@@ -142,27 +145,29 @@ suite('JsonRpcProtocol', () => {
 
 		assert.ok(receivedToken);
 		assert.strictEqual(wasCanceledDuringHandler, false);
-		assert.deepStrictEqual(sentMessages, [{
+		const expected = [{
 			jsonrpc: '2.0',
 			id: 9,
 			result: 'compute:ok'
-		}]);
+		}];
+		assert.deepStrictEqual(sentMessages, expected);
+		assert.deepStrictEqual(replies, expected);
 	});
 
-	test('handleRequest serializes JsonRpcError', async () => {
+	test('handleRequest serializes JsonRpcError and returns it', async () => {
 		const { protocol, sentMessages } = createProtocol({
 			handleRequest: () => {
 				throw new JsonRpcError(88, 'bad request', { detail: true });
 			}
 		});
 
-		await protocol.handleMessage({
+		const replies = await protocol.handleMessage({
 			jsonrpc: '2.0',
 			id: 'a',
 			method: 'boom'
 		});
 
-		assert.deepStrictEqual(sentMessages, [{
+		const expected = [{
 			jsonrpc: '2.0',
 			id: 'a',
 			error: {
@@ -170,30 +175,34 @@ suite('JsonRpcProtocol', () => {
 				message: 'bad request',
 				data: { detail: true }
 			}
-		}]);
+		}];
+		assert.deepStrictEqual(sentMessages, expected);
+		assert.deepStrictEqual(replies, expected);
 	});
 
-	test('handleRequest maps unknown errors to internal error', async () => {
+	test('handleRequest maps unknown errors to internal error and returns it', async () => {
 		const { protocol, sentMessages } = createProtocol({
 			handleRequest: () => {
 				throw new Error('unexpected');
 			}
 		});
 
-		await protocol.handleMessage({
+		const replies = await protocol.handleMessage({
 			jsonrpc: '2.0',
 			id: 'b',
 			method: 'explode'
 		});
 
-		assert.deepStrictEqual(sentMessages, [{
+		const expected = [{
 			jsonrpc: '2.0',
 			id: 'b',
 			error: {
 				code: -32603,
 				message: 'unexpected'
 			}
-		}]);
+		}];
+		assert.deepStrictEqual(sentMessages, expected);
+		assert.deepStrictEqual(replies, expected);
 	});
 
 	test('handleMessage processes batch sequentially', async () => {
@@ -225,8 +234,9 @@ suite('JsonRpcProtocol', () => {
 		assert.deepStrictEqual(sequence, ['request:start']);
 
 		gate.complete();
-		await handlingPromise;
+		const replies = await handlingPromise;
 
 		assert.deepStrictEqual(sequence, ['request:start', 'request:end', 'notification']);
+		assert.deepStrictEqual(replies, [{ jsonrpc: '2.0', id: 1, result: true }]);
 	});
 });
diff --git a/src/vs/code/electron-browser/workbench/workbench-dev.html b/src/vs/code/electron-browser/workbench/workbench-dev.html
index 13ff778a58cdf..8ccafe7816e1f 100644
--- a/src/vs/code/electron-browser/workbench/workbench-dev.html
+++ b/src/vs/code/electron-browser/workbench/workbench-dev.html
@@ -65,6 +65,7 @@
 					tokenizeToString
 					notebookChatEditController
 					richScreenReaderContent
+					chatDebugTokenizer
 				;
 		"/>
 	</head>
diff --git a/src/vs/code/electron-browser/workbench/workbench.html b/src/vs/code/electron-browser/workbench/workbench.html
index dda0dd75b77e4..ce51984cd542d 100644
--- a/src/vs/code/electron-browser/workbench/workbench.html
+++ b/src/vs/code/electron-browser/workbench/workbench.html
@@ -63,6 +63,7 @@
 					tokenizeToString
 					notebookChatEditController
 					richScreenReaderContent
+					chatDebugTokenizer
 				;
 		"/>
 
diff --git a/src/vs/code/electron-main/app.ts b/src/vs/code/electron-main/app.ts
index 7881f739531cc..c2c70d3930304 100644
--- a/src/vs/code/electron-main/app.ts
+++ b/src/vs/code/electron-main/app.ts
@@ -41,7 +41,6 @@ import { ipcBrowserViewChannelName } from '../../platform/browserView/common/bro
 import { ipcBrowserViewGroupChannelName } from '../../platform/browserView/common/browserViewGroup.js';
 import { BrowserViewMainService, IBrowserViewMainService } from '../../platform/browserView/electron-main/browserViewMainService.js';
 import { BrowserViewGroupMainService, IBrowserViewGroupMainService } from '../../platform/browserView/electron-main/browserViewGroupMainService.js';
-import { BrowserViewCDPProxyServer, IBrowserViewCDPProxyServer } from '../../platform/browserView/electron-main/browserViewCDPProxyServer.js';
 import { NativeParsedArgs } from '../../platform/environment/common/argv.js';
 import { IEnvironmentMainService } from '../../platform/environment/electron-main/environmentMainService.js';
 import { isLaunchedFromCli } from '../../platform/environment/node/argvHelper.js';
@@ -133,6 +132,9 @@ import { NativeMcpDiscoveryHelperService } from '../../platform/mcp/node/nativeM
 import { IMcpGatewayService, McpGatewayChannelName } from '../../platform/mcp/common/mcpGateway.js';
 import { McpGatewayService } from '../../platform/mcp/node/mcpGatewayService.js';
 import { McpGatewayChannel } from '../../platform/mcp/node/mcpGatewayChannel.js';
+import { SandboxHelperChannelName } from '../../platform/sandbox/common/sandboxHelperIpc.js';
+import { ISandboxHelperService } from '../../platform/sandbox/common/sandboxHelperService.js';
+import { SandboxHelperService } from '../../platform/sandbox/node/sandboxHelperService.js';
 import { IWebContentExtractorService } from '../../platform/webContentExtractor/common/webContentExtractor.js';
 import { NativeWebContentExtractorService } from '../../platform/webContentExtractor/electron-main/webContentExtractorService.js';
 import ErrorTelemetry from '../../platform/telemetry/electron-main/errorTelemetry.js';
@@ -408,7 +410,11 @@ export class CodeApplication extends Disposable {
 
 			// Mac only event: open new window when we get activated
 			if (!hasVisibleWindows) {
-				await this.windowsMainService?.openEmptyWindow({ context: OpenContext.DOCK });
+				if ((process as INodeProcess).isEmbeddedApp || (this.environmentMainService.args['sessions'] && this.productService.quality !== 'stable')) {
+					await this.windowsMainService?.openSessionsWindow({ context: OpenContext.DOCK });
+				} else {
+					await this.windowsMainService?.openEmptyWindow({ context: OpenContext.DOCK });
+				}
 			}
 		});
 
@@ -1059,7 +1065,6 @@ export class CodeApplication extends Disposable {
 		services.set(INativeBrowserElementsMainService, new SyncDescriptor(NativeBrowserElementsMainService, undefined, false /* proxied to other processes */));
 
 		// Browser View
-		services.set(IBrowserViewCDPProxyServer, new SyncDescriptor(BrowserViewCDPProxyServer, undefined, true));
 		services.set(IBrowserViewMainService, new SyncDescriptor(BrowserViewMainService, undefined, false /* proxied to other processes */));
 		services.set(IBrowserViewGroupMainService, new SyncDescriptor(BrowserViewGroupMainService, undefined, false /* proxied to other processes */));
 
@@ -1149,6 +1154,9 @@ export class CodeApplication extends Disposable {
 		// Proxy Auth
 		services.set(IProxyAuthService, new SyncDescriptor(ProxyAuthService));
 
+		// Sandbox
+		services.set(ISandboxHelperService, new SyncDescriptor(SandboxHelperService));
+
 		// MCP
 		services.set(INativeMcpDiscoveryHelperService, new SyncDescriptor(NativeMcpDiscoveryHelperService));
 		services.set(IMcpGatewayService, new SyncDescriptor(McpGatewayService));
@@ -1281,10 +1289,14 @@ export class CodeApplication extends Disposable {
 		const externalTerminalChannel = ProxyChannel.fromService(accessor.get(IExternalTerminalMainService), disposables);
 		mainProcessElectronServer.registerChannel('externalTerminal', externalTerminalChannel);
 
+		// Sandbox
+		const sandboxHelperChannel = ProxyChannel.fromService(accessor.get(ISandboxHelperService), disposables);
+		mainProcessElectronServer.registerChannel(SandboxHelperChannelName, sandboxHelperChannel);
+
 		// MCP
 		const mcpDiscoveryChannel = ProxyChannel.fromService(accessor.get(INativeMcpDiscoveryHelperService), disposables);
 		mainProcessElectronServer.registerChannel(NativeMcpDiscoveryHelperChannelName, mcpDiscoveryChannel);
-		const mcpGatewayChannel = this._register(new McpGatewayChannel(mainProcessElectronServer, accessor.get(IMcpGatewayService)));
+		const mcpGatewayChannel = this._register(new McpGatewayChannel(mainProcessElectronServer, accessor.get(IMcpGatewayService), accessor.get(ILoggerMainService)));
 		mainProcessElectronServer.registerChannel(McpGatewayChannelName, mcpGatewayChannel);
 
 		// Logger
diff --git a/src/vs/code/electron-utility/sharedProcess/sharedProcessMain.ts b/src/vs/code/electron-utility/sharedProcess/sharedProcessMain.ts
index e112b958d730e..7f5cd7c26e9b4 100644
--- a/src/vs/code/electron-utility/sharedProcess/sharedProcessMain.ts
+++ b/src/vs/code/electron-utility/sharedProcess/sharedProcessMain.ts
@@ -134,9 +134,7 @@ import { IMcpGalleryManifestService } from '../../../platform/mcp/common/mcpGall
 import { McpGalleryManifestIPCService } from '../../../platform/mcp/common/mcpGalleryManifestServiceIpc.js';
 import { IMeteredConnectionService } from '../../../platform/meteredConnection/common/meteredConnection.js';
 import { MeteredConnectionChannelClient, METERED_CONNECTION_CHANNEL } from '../../../platform/meteredConnection/common/meteredConnectionIpc.js';
-import { IPlaywrightService } from '../../../platform/browserView/common/playwrightService.js';
-import { PlaywrightService } from '../../../platform/browserView/node/playwrightService.js';
-import { IBrowserViewGroupRemoteService, BrowserViewGroupRemoteService } from '../../../platform/browserView/node/browserViewGroupRemoteService.js';
+import { PlaywrightChannel } from '../../../platform/browserView/node/playwrightChannel.js';
 
 class SharedProcessMain extends Disposable implements IClientConnectionFilter {
 
@@ -404,10 +402,6 @@ class SharedProcessMain extends Disposable implements IClientConnectionFilter {
 		// Web Content Extractor
 		services.set(ISharedWebContentExtractorService, new SyncDescriptor(SharedWebContentExtractorService));
 
-		// Playwright
-		services.set(IBrowserViewGroupRemoteService, new SyncDescriptor(BrowserViewGroupRemoteService));
-		services.set(IPlaywrightService, new SyncDescriptor(PlaywrightService));
-
 		return new InstantiationService(services);
 	}
 
@@ -476,7 +470,7 @@ class SharedProcessMain extends Disposable implements IClientConnectionFilter {
 		this.server.registerChannel('sharedWebContentExtractor', webContentExtractorChannel);
 
 		// Playwright
-		const playwrightChannel = ProxyChannel.fromService(accessor.get(IPlaywrightService), this._store);
+		const playwrightChannel = this._register(new PlaywrightChannel(this.server, accessor.get(IMainProcessService), accessor.get(ILogService)));
 		this.server.registerChannel('playwright', playwrightChannel);
 	}
 
diff --git a/src/vs/code/node/cli.ts b/src/vs/code/node/cli.ts
index 8e29f4924766b..5f50659ff46c2 100644
--- a/src/vs/code/node/cli.ts
+++ b/src/vs/code/node/cli.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { ChildProcess, spawn, SpawnOptions, StdioOptions } from 'child_process';
-import { chmodSync, existsSync, readFileSync, statSync, truncateSync, unlinkSync } from 'fs';
+import { chmodSync, existsSync, readFileSync, statSync, truncateSync, unlinkSync, promises } from 'fs';
 import { homedir, tmpdir } from 'os';
 import type { ProfilingSession, Target } from 'v8-inspect-profiler';
 import { Event } from '../../base/common/event.js';
@@ -499,8 +499,26 @@ export async function main(argv: string[]): Promise<void> {
 			//    This way, Mac does not automatically try to foreground the new instance, which causes
 			//    focusing issues when the new instance only sends data to a previous instance and then closes.
 			const spawnArgs = ['-n', '-g'];
-			// -a opens the given application.
-			spawnArgs.push('-a', process.execPath); // -a: opens a specific application
+
+			// Figure out the app to launch: with --sessions we try to launch the embedded app
+			let appToLaunch = process.execPath;
+			if (args.sessions) {
+				// process.execPath is e.g. /Applications/Code.app/Contents/MacOS/Electron
+				// Embedded app is at /Applications/Code.app/Contents/Applications/<EmbeddedApp>.app
+				const contentsPath = dirname(dirname(process.execPath));
+				const applicationsPath = join(contentsPath, 'Applications');
+				try {
+					const files = await promises.readdir(applicationsPath);
+					const embeddedApp = files.find(file => file.endsWith('.app'));
+					if (embeddedApp) {
+						appToLaunch = join(applicationsPath, embeddedApp);
+						argv = argv.filter(arg => arg !== '--sessions');
+					}
+				} catch (error) {
+					/* may not exist on disk */
+				}
+			}
+			spawnArgs.push('-a', appToLaunch); // -a opens the given application.
 
 			if (args.verbose || args.status) {
 				spawnArgs.push('--wait-apps'); // `open --wait-apps`: blocks until the launched app is closed (even if they were already running)
diff --git a/src/vs/editor/browser/controller/editContext/native/nativeEditContext.ts b/src/vs/editor/browser/controller/editContext/native/nativeEditContext.ts
index 88d97714e7ce2..528a8e0f590fc 100644
--- a/src/vs/editor/browser/controller/editContext/native/nativeEditContext.ts
+++ b/src/vs/editor/browser/controller/editContext/native/nativeEditContext.ts
@@ -58,6 +58,7 @@ export class NativeEditContext extends AbstractEditContext {
 	private readonly _editContext: EditContext;
 	private readonly _screenReaderSupport: ScreenReaderSupport;
 	private _previousEditContextSelection: OffsetRange = new OffsetRange(0, 0);
+	private _previousEditContextText: string = '';
 	private _editContextPrimarySelection: Selection = new Selection(1, 1, 1, 1);
 
 	// Overflow guard container
@@ -247,6 +248,19 @@ export class NativeEditContext extends AbstractEditContext {
 			}
 		}));
 		this._register(NativeEditContextRegistry.register(ownerID, this));
+		this._register(context.viewModel.model.onDidChangeContent((e) => {
+			let doChange = false;
+			for (const change of e.changes) {
+				if (change.range.startLineNumber <= this._editContextPrimarySelection.endLineNumber
+					&& change.range.endLineNumber >= this._editContextPrimarySelection.startLineNumber) {
+					doChange = true;
+					break;
+				}
+			}
+			if (doChange) {
+				this._updateEditContext();
+			}
+		}));
 	}
 
 	// --- Public methods ---
@@ -310,27 +324,17 @@ export class NativeEditContext extends AbstractEditContext {
 	}
 
 	public override onLinesChanged(e: ViewLinesChangedEvent): boolean {
-		this._updateEditContextOnLineChange(e.fromLineNumber, e.fromLineNumber + e.count - 1);
 		return true;
 	}
 
 	public override onLinesDeleted(e: ViewLinesDeletedEvent): boolean {
-		this._updateEditContextOnLineChange(e.fromLineNumber, e.toLineNumber);
 		return true;
 	}
 
 	public override onLinesInserted(e: ViewLinesInsertedEvent): boolean {
-		this._updateEditContextOnLineChange(e.fromLineNumber, e.toLineNumber);
 		return true;
 	}
 
-	private _updateEditContextOnLineChange(fromLineNumber: number, toLineNumber: number): void {
-		if (this._editContextPrimarySelection.endLineNumber < fromLineNumber || this._editContextPrimarySelection.startLineNumber > toLineNumber) {
-			return;
-		}
-		this._updateEditContext();
-	}
-
 	public override onScrollChanged(e: ViewScrollChangedEvent): boolean {
 		this._scrollLeft = e.scrollLeft;
 		this._scrollTop = e.scrollTop;
@@ -412,8 +416,15 @@ export class NativeEditContext extends AbstractEditContext {
 		if (!editContextState) {
 			return;
 		}
-		this._editContext.updateText(0, Number.MAX_SAFE_INTEGER, editContextState.text ?? ' ');
-		this._editContext.updateSelection(editContextState.selectionStartOffset, editContextState.selectionEndOffset);
+		const newText = editContextState.text ?? ' ';
+		if (newText !== this._previousEditContextText) {
+			this._editContext.updateText(0, this._previousEditContextText.length, newText);
+			this._previousEditContextText = newText;
+		}
+		if (editContextState.selectionStartOffset !== this._previousEditContextSelection.start ||
+			editContextState.selectionEndOffset !== this._previousEditContextSelection.endExclusive) {
+			this._editContext.updateSelection(editContextState.selectionStartOffset, editContextState.selectionEndOffset);
+		}
 		this._editContextPrimarySelection = editContextState.editContextPrimarySelection;
 		this._previousEditContextSelection = new OffsetRange(editContextState.selectionStartOffset, editContextState.selectionEndOffset);
 	}
diff --git a/src/vs/editor/browser/view/domLineBreaksComputer.ts b/src/vs/editor/browser/view/domLineBreaksComputer.ts
index 881275f34af4a..cdd1923cbe6c6 100644
--- a/src/vs/editor/browser/view/domLineBreaksComputer.ts
+++ b/src/vs/editor/browser/view/domLineBreaksComputer.ts
@@ -8,11 +8,10 @@ import { CharCode } from '../../../base/common/charCode.js';
 import * as strings from '../../../base/common/strings.js';
 import { assertReturnsDefined } from '../../../base/common/types.js';
 import { applyFontInfo } from '../config/domFontInfo.js';
-import { WrappingIndent } from '../../common/config/editorOptions.js';
-import { FontInfo } from '../../common/config/fontInfo.js';
+import { EditorOption, IComputedEditorOptions, WrappingIndent } from '../../common/config/editorOptions.js';
 import { StringBuilder } from '../../common/core/stringBuilder.js';
 import { InjectedTextOptions } from '../../common/model.js';
-import { ILineBreaksComputer, ILineBreaksComputerFactory, ModelLineProjectionData } from '../../common/modelLineProjectionData.js';
+import { ILineBreaksComputer, ILineBreaksComputerContext, ILineBreaksComputerFactory, ModelLineProjectionData } from '../../common/modelLineProjectionData.js';
 import { LineInjectedText } from '../../common/textModelEvents.js';
 
 const ttPolicy = createTrustedTypesPolicy('domLineBreaksComputer', { createHTML: value => value });
@@ -26,26 +25,25 @@ export class DOMLineBreaksComputerFactory implements ILineBreaksComputerFactory
 	constructor(private targetWindow: WeakRef<Window>) {
 	}
 
-	public createLineBreaksComputer(fontInfo: FontInfo, tabSize: number, wrappingColumn: number, wrappingIndent: WrappingIndent, wordBreak: 'normal' | 'keepAll', wrapOnEscapedLineFeeds: boolean): ILineBreaksComputer {
-		const requests: string[] = [];
-		const injectedTexts: (LineInjectedText[] | null)[] = [];
+	public createLineBreaksComputer(context: ILineBreaksComputerContext, options: IComputedEditorOptions, tabSize: number): ILineBreaksComputer {
+		const lineNumbers: number[] = [];
 		return {
-			addRequest: (lineText: string, injectedText: LineInjectedText[] | null, previousLineBreakData: ModelLineProjectionData | null) => {
-				requests.push(lineText);
-				injectedTexts.push(injectedText);
+			addRequest: (lineNumber: number, previousLineBreakData: ModelLineProjectionData | null) => {
+				lineNumbers.push(lineNumber);
 			},
 			finalize: () => {
-				return createLineBreaks(assertReturnsDefined(this.targetWindow.deref()), requests, fontInfo, tabSize, wrappingColumn, wrappingIndent, wordBreak, injectedTexts);
+				return createLineBreaks(assertReturnsDefined(this.targetWindow.deref()), context, lineNumbers, options, tabSize);
 			}
 		};
 	}
 }
 
-function createLineBreaks(targetWindow: Window, requests: string[], fontInfo: FontInfo, tabSize: number, firstLineBreakColumn: number, wrappingIndent: WrappingIndent, wordBreak: 'normal' | 'keepAll', injectedTextsPerLine: (LineInjectedText[] | null)[]): (ModelLineProjectionData | null)[] {
-	function createEmptyLineBreakWithPossiblyInjectedText(requestIdx: number): ModelLineProjectionData | null {
-		const injectedTexts = injectedTextsPerLine[requestIdx];
+function createLineBreaks(targetWindow: Window, context: ILineBreaksComputerContext, lineNumbers: number[], options: IComputedEditorOptions, tabSize: number): (ModelLineProjectionData | null)[] {
+	function createEmptyLineBreakWithPossiblyInjectedText(lineNumber: number): ModelLineProjectionData | null {
+		const injectedTexts = context.getLineInjectedText(lineNumber);
 		if (injectedTexts) {
-			const lineText = LineInjectedText.applyInjectedText(requests[requestIdx], injectedTexts);
+			const lineContent = context.getLineContent(lineNumber);
+			const lineText = LineInjectedText.applyInjectedText(lineContent, injectedTexts);
 
 			const injectionOptions = injectedTexts.map(t => t.options);
 			const injectionOffsets = injectedTexts.map(text => text.column - 1);
@@ -57,11 +55,14 @@ function createLineBreaks(targetWindow: Window, requests: string[], fontInfo: Fo
 			return null;
 		}
 	}
-
+	const wrappingIndent = options.get(EditorOption.wrappingIndent);
+	const fontInfo = options.get(EditorOption.fontInfo);
+	const wordBreak = options.get(EditorOption.wordBreak);
+	const firstLineBreakColumn = options.get(EditorOption.wrappingInfo).wrappingColumn;
 	if (firstLineBreakColumn === -1) {
 		const result: (ModelLineProjectionData | null)[] = [];
-		for (let i = 0, len = requests.length; i < len; i++) {
-			result[i] = createEmptyLineBreakWithPossiblyInjectedText(i);
+		for (let i = 0, len = lineNumbers.length; i < len; i++) {
+			result[i] = createEmptyLineBreakWithPossiblyInjectedText(lineNumbers[i]);
 		}
 		return result;
 	}
@@ -80,8 +81,9 @@ function createLineBreaks(targetWindow: Window, requests: string[], fontInfo: Fo
 	const renderLineContents: string[] = [];
 	const allCharOffsets: number[][] = [];
 	const allVisibleColumns: number[][] = [];
-	for (let i = 0; i < requests.length; i++) {
-		const lineContent = LineInjectedText.applyInjectedText(requests[i], injectedTextsPerLine[i]);
+	for (let i = 0; i < lineNumbers.length; i++) {
+		const lineNumber = lineNumbers[i];
+		const lineContent = LineInjectedText.applyInjectedText(context.getLineContent(lineNumber), context.getLineInjectedText(lineNumber));
 
 		let firstNonWhitespaceIndex = 0;
 		let wrappedTextIndentLength = 0;
@@ -146,11 +148,12 @@ function createLineBreaks(targetWindow: Window, requests: string[], fontInfo: Fo
 	const lineDomNodes = Array.prototype.slice.call(containerDomNode.children, 0);
 
 	const result: (ModelLineProjectionData | null)[] = [];
-	for (let i = 0; i < requests.length; i++) {
+	for (let i = 0; i < lineNumbers.length; i++) {
+		const lineNumber = lineNumbers[i];
 		const lineDomNode = lineDomNodes[i];
 		const breakOffsets: number[] | null = readLineBreaks(range, lineDomNode, renderLineContents[i], allCharOffsets[i]);
 		if (breakOffsets === null) {
-			result[i] = createEmptyLineBreakWithPossiblyInjectedText(i);
+			result[i] = createEmptyLineBreakWithPossiblyInjectedText(lineNumber);
 			continue;
 		}
 
@@ -172,7 +175,7 @@ function createLineBreaks(targetWindow: Window, requests: string[], fontInfo: Fo
 
 		let injectionOptions: InjectedTextOptions[] | null;
 		let injectionOffsets: number[] | null;
-		const curInjectedTexts = injectedTextsPerLine[i];
+		const curInjectedTexts = context.getLineInjectedText(lineNumber);
 		if (curInjectedTexts) {
 			injectionOptions = curInjectedTexts.map(t => t.options);
 			injectionOffsets = curInjectedTexts.map(text => text.column - 1);
diff --git a/src/vs/editor/browser/viewParts/minimap/minimap.css b/src/vs/editor/browser/viewParts/minimap/minimap.css
index 35bb6e3b7178b..e6ced7d3dc851 100644
--- a/src/vs/editor/browser/viewParts/minimap/minimap.css
+++ b/src/vs/editor/browser/viewParts/minimap/minimap.css
@@ -25,7 +25,7 @@
 	background: var(--vscode-minimapSlider-activeBackground);
 }
 .monaco-editor .minimap-shadow-visible {
-	box-shadow: var(--vscode-scrollbar-shadow) -6px 0 6px -6px inset;
+	box-shadow: var(--vscode-shadow-md);
 }
 .monaco-editor .minimap-shadow-hidden {
 	position: absolute;
@@ -61,3 +61,7 @@
 .monaco-editor .minimap {
 	z-index: 5;
 }
+
+.monaco-editor .minimap canvas {
+	opacity: 0.9;
+}
diff --git a/src/vs/editor/browser/viewParts/viewLines/viewLine.ts b/src/vs/editor/browser/viewParts/viewLines/viewLine.ts
index 4aaa9200561a9..3bf79d8b67925 100644
--- a/src/vs/editor/browser/viewParts/viewLines/viewLine.ts
+++ b/src/vs/editor/browser/viewParts/viewLines/viewLine.ts
@@ -116,7 +116,7 @@ export class ViewLine implements IVisibleLine {
 		const lineData = viewportData.getViewLineRenderingData(lineNumber);
 		const options = this._options;
 		const actualInlineDecorations = LineDecoration.filter(lineData.inlineDecorations, lineNumber, lineData.minColumn, lineData.maxColumn);
-		const renderWhitespace = (lineData.hasVariableFonts || options.experimentalWhitespaceRendering === 'off') ? options.renderWhitespace : 'none';
+		const renderWhitespace = options.experimentalWhitespaceRendering === 'off' ? options.renderWhitespace : 'none';
 		const allowFastRendering = !lineData.hasVariableFonts;
 
 		// Only send selection information when needed for rendering whitespace
diff --git a/src/vs/editor/browser/viewParts/whitespace/whitespace.ts b/src/vs/editor/browser/viewParts/whitespace/whitespace.ts
index 546d268130c31..42ee0e30dade4 100644
--- a/src/vs/editor/browser/viewParts/whitespace/whitespace.ts
+++ b/src/vs/editor/browser/viewParts/whitespace/whitespace.ts
@@ -122,9 +122,6 @@ export class WhitespaceOverlay extends DynamicViewOverlay {
 	}
 
 	private _applyRenderWhitespace(ctx: RenderingContext, lineNumber: number, selections: OffsetRange[] | null, lineData: ViewLineRenderingData): string {
-		if (lineData.hasVariableFonts) {
-			return '';
-		}
 		if (this._options.renderWhitespace === 'selection' && !selections) {
 			return '';
 		}
diff --git a/src/vs/editor/browser/widget/codeEditor/editor.css b/src/vs/editor/browser/widget/codeEditor/editor.css
index d33122122dedf..638055a055d57 100644
--- a/src/vs/editor/browser/widget/codeEditor/editor.css
+++ b/src/vs/editor/browser/widget/codeEditor/editor.css
@@ -21,6 +21,7 @@
 	position: relative;
 	overflow: visible;
 	-webkit-text-size-adjust: 100%;
+	text-spacing-trim: space-all;
 	color: var(--vscode-editor-foreground);
 	background-color: var(--vscode-editor-background);
 	overflow-wrap: initial;
diff --git a/src/vs/editor/browser/widget/diffEditor/components/diffEditorViewZones/diffEditorViewZones.ts b/src/vs/editor/browser/widget/diffEditor/components/diffEditorViewZones/diffEditorViewZones.ts
index 62bf7ece01a52..56d3850c945ef 100644
--- a/src/vs/editor/browser/widget/diffEditor/components/diffEditorViewZones/diffEditorViewZones.ts
+++ b/src/vs/editor/browser/widget/diffEditor/components/diffEditorViewZones/diffEditorViewZones.ts
@@ -31,6 +31,7 @@ import { IContextMenuService } from '../../../../../../platform/contextview/brow
 import { DiffEditorOptions } from '../../diffEditorOptions.js';
 import { Range } from '../../../../../common/core/range.js';
 import { InlineDecoration, InlineDecorationType } from '../../../../../common/viewModel/inlineDecorations.js';
+import { ILineBreaksComputerContext } from '../../../../../common/modelLineProjectionData.js';
 
 /**
  * Ensures both editors have the same height by aligning unchanged lines.
@@ -163,8 +164,15 @@ export class DiffEditorViewZones extends Disposable {
 			}
 
 			const renderSideBySide = this._options.renderSideBySide.read(reader);
-
-			const deletedCodeLineBreaksComputer = !renderSideBySide ? this._editors.modified._getViewModel()?.createLineBreaksComputer() : undefined;
+			const context: ILineBreaksComputerContext = {
+				getLineContent: (lineNumber: number): string => {
+					return this._editors.original.getModel()!.getLineContent(lineNumber);
+				},
+				getLineInjectedText: (lineNumber: number) => {
+					return null;
+				}
+			};
+			const deletedCodeLineBreaksComputer = !renderSideBySide ? this._editors.modified._getViewModel()?.createLineBreaksComputer(context) : undefined;
 			if (deletedCodeLineBreaksComputer) {
 				const originalModel = this._editors.original.getModel()!;
 				for (const a of alignmentsVal) {
@@ -176,7 +184,7 @@ export class DiffEditorViewZones extends Disposable {
 							if (i > originalModel.getLineCount()) {
 								return { orig: origViewZones, mod: modViewZones };
 							}
-							deletedCodeLineBreaksComputer?.addRequest(originalModel.getLineContent(i), null, null);
+							deletedCodeLineBreaksComputer?.addRequest(i, null);
 						}
 					}
 				}
diff --git a/src/vs/editor/common/config/editorOptions.ts b/src/vs/editor/common/config/editorOptions.ts
index 34cdd09c350c4..313793845dd64 100644
--- a/src/vs/editor/common/config/editorOptions.ts
+++ b/src/vs/editor/common/config/editorOptions.ts
@@ -1744,6 +1744,10 @@ export interface IEditorFindOptions {
 	 * Controls whether the search result and diff result automatically restarts from the beginning (or the end) when no further matches can be found
 	 */
 	loop?: boolean;
+	/**
+	 * Controls whether to close the Find Widget after an explicit find navigation command lands on a match.
+	 */
+	closeOnResult?: boolean;
 	/**
 	 * @internal
 	 * Controls how the find widget search history should be stored
@@ -1772,6 +1776,7 @@ class EditorFind extends BaseEditorOption<EditorOption.find, IEditorFindOptions,
 			globalFindClipboard: false,
 			addExtraSpaceOnTop: true,
 			loop: true,
+			closeOnResult: false,
 			history: 'workspace',
 			replaceHistory: 'workspace',
 		};
@@ -1821,6 +1826,11 @@ class EditorFind extends BaseEditorOption<EditorOption.find, IEditorFindOptions,
 					default: defaults.loop,
 					description: nls.localize('find.loop', "Controls whether the search automatically restarts from the beginning (or the end) when no further matches can be found.")
 				},
+				'editor.find.closeOnResult': {
+					type: 'boolean',
+					default: defaults.closeOnResult,
+					description: nls.localize('find.closeOnResult', "Controls whether the Find Widget closes after an explicit find navigation command lands on a result.")
+				},
 				'editor.find.history': {
 					type: 'string',
 					enum: ['never', 'workspace'],
@@ -1867,6 +1877,7 @@ class EditorFind extends BaseEditorOption<EditorOption.find, IEditorFindOptions,
 			globalFindClipboard: boolean(input.globalFindClipboard, this.defaultValue.globalFindClipboard),
 			addExtraSpaceOnTop: boolean(input.addExtraSpaceOnTop, this.defaultValue.addExtraSpaceOnTop),
 			loop: boolean(input.loop, this.defaultValue.loop),
+			closeOnResult: boolean(input.closeOnResult, this.defaultValue.closeOnResult),
 			history: stringSet<'never' | 'workspace'>(input.history, this.defaultValue.history, ['never', 'workspace']),
 			replaceHistory: stringSet<'never' | 'workspace'>(input.replaceHistory, this.defaultValue.replaceHistory, ['never', 'workspace']),
 		};
@@ -2322,6 +2333,11 @@ export interface IEditorHoverOptions {
 	 * Defaults to false.
 	 */
 	above?: boolean;
+	/**
+	 * Should long line warning hovers be shown (tokenization skipped, rendering paused)?
+	 * Defaults to true.
+	 */
+	showLongLineWarning?: boolean;
 }
 
 /**
@@ -2338,6 +2354,7 @@ class EditorHover extends BaseEditorOption<EditorOption.hover, IEditorHoverOptio
 			hidingDelay: 300,
 			sticky: true,
 			above: true,
+			showLongLineWarning: true,
 		};
 		super(
 			EditorOption.hover, 'hover', defaults,
@@ -2376,6 +2393,11 @@ class EditorHover extends BaseEditorOption<EditorOption.hover, IEditorHoverOptio
 					default: defaults.above,
 					description: nls.localize('hover.above', "Prefer showing hovers above the line, if there's space.")
 				},
+				'editor.hover.showLongLineWarning': {
+					type: 'boolean',
+					default: defaults.showLongLineWarning,
+					description: nls.localize('hover.showLongLineWarning', "Controls whether long line warning hovers are shown, such as when tokenization is skipped or rendering is paused.")
+				},
 			}
 		);
 	}
@@ -2391,6 +2413,7 @@ class EditorHover extends BaseEditorOption<EditorOption.hover, IEditorHoverOptio
 			sticky: boolean(input.sticky, this.defaultValue.sticky),
 			hidingDelay: EditorIntOption.clampedInt(input.hidingDelay, this.defaultValue.hidingDelay, 0, 600000),
 			above: boolean(input.above, this.defaultValue.above),
+			showLongLineWarning: boolean(input.showLongLineWarning, this.defaultValue.showLongLineWarning),
 		};
 	}
 }
@@ -3749,7 +3772,7 @@ class EditorQuickSuggestions extends BaseEditorOption<EditorOption.quickSuggesti
 			{
 				type: 'string',
 				enum: ['on', 'inline', 'off', 'offWhenInlineCompletions'],
-				enumDescriptions: [nls.localize('on', "Quick suggestions show inside the suggest widget"), nls.localize('inline', "Quick suggestions show as ghost text"), nls.localize('off', "Quick suggestions are disabled"), nls.localize('offWhenInlineCompletions', "Quick suggestions are disabled when an inline completion provider is available")]
+				enumDescriptions: [nls.localize('on', "Quick suggestions show inside the suggest widget"), nls.localize('inline', "Quick suggestions show as ghost text"), nls.localize('off', "Quick suggestions are disabled"), nls.localize('offWhenInlineCompletions', "Quick suggestions are disabled when inline completions are showing")]
 			}
 		];
 		super(EditorOption.quickSuggestions, 'quickSuggestions', defaults, {
@@ -3758,7 +3781,7 @@ class EditorQuickSuggestions extends BaseEditorOption<EditorOption.quickSuggesti
 				{
 					type: 'string',
 					enum: ['on', 'inline', 'off', 'offWhenInlineCompletions'],
-					enumDescriptions: [nls.localize('quickSuggestions.topLevel.on', "Quick suggestions are enabled for all token types"), nls.localize('quickSuggestions.topLevel.inline', "Quick suggestions show as ghost text for all token types"), nls.localize('quickSuggestions.topLevel.off', "Quick suggestions are disabled for all token types"), nls.localize('quickSuggestions.topLevel.offWhenInlineCompletions', "Quick suggestions are disabled for all token types when an inline completion provider is available")]
+					enumDescriptions: [nls.localize('quickSuggestions.topLevel.on', "Quick suggestions are enabled for all token types"), nls.localize('quickSuggestions.topLevel.inline', "Quick suggestions show as ghost text for all token types"), nls.localize('quickSuggestions.topLevel.off', "Quick suggestions are disabled for all token types"), nls.localize('quickSuggestions.topLevel.offWhenInlineCompletions', "Quick suggestions are disabled for all token types when inline completions are showing")]
 				},
 				{
 					type: 'object',
diff --git a/src/vs/editor/common/cursor/cursorMoveCommands.ts b/src/vs/editor/common/cursor/cursorMoveCommands.ts
index a447e3a8f7598..d3183d48af57c 100644
--- a/src/vs/editor/common/cursor/cursorMoveCommands.ts
+++ b/src/vs/editor/common/cursor/cursorMoveCommands.ts
@@ -294,6 +294,9 @@ export class CursorMoveCommands {
 				if (unit === CursorMove.Unit.WrappedLine) {
 					// Move up by view lines
 					return this._moveUpByViewLines(viewModel, cursors, inSelectionMode, value);
+				} else if (unit === CursorMove.Unit.FoldedLine) {
+					// Move up by model lines, skipping over folded regions
+					return this._moveUpByFoldedLines(viewModel, cursors, inSelectionMode, value);
 				} else {
 					// Move up by model lines
 					return this._moveUpByModelLines(viewModel, cursors, inSelectionMode, value);
@@ -303,6 +306,9 @@ export class CursorMoveCommands {
 				if (unit === CursorMove.Unit.WrappedLine) {
 					// Move down by view lines
 					return this._moveDownByViewLines(viewModel, cursors, inSelectionMode, value);
+				} else if (unit === CursorMove.Unit.FoldedLine) {
+					// Move down by model lines, skipping over folded regions
+					return this._moveDownByFoldedLines(viewModel, cursors, inSelectionMode, value);
 				} else {
 					// Move down by model lines
 					return this._moveDownByModelLines(viewModel, cursors, inSelectionMode, value);
@@ -515,6 +521,113 @@ export class CursorMoveCommands {
 		return result;
 	}
 
+	private static _moveDownByFoldedLines(viewModel: IViewModel, cursors: CursorState[], inSelectionMode: boolean, count: number): PartialCursorState[] {
+		const model = viewModel.model;
+		const lineCount = model.getLineCount();
+		const hiddenAreas = viewModel.getHiddenAreas();
+
+		return cursors.map(cursor => {
+			const startLine = cursor.modelState.hasSelection() && !inSelectionMode
+				? cursor.modelState.selection.endLineNumber
+				: cursor.modelState.position.lineNumber;
+
+			const targetLine = CursorMoveCommands._targetFoldedDown(startLine, count, hiddenAreas, lineCount);
+			const delta = targetLine - startLine;
+			if (delta === 0) {
+				return CursorState.fromModelState(cursor.modelState);
+			}
+			return CursorState.fromModelState(MoveOperations.moveDown(viewModel.cursorConfig, model, cursor.modelState, inSelectionMode, delta));
+		});
+	}
+
+	private static _moveUpByFoldedLines(viewModel: IViewModel, cursors: CursorState[], inSelectionMode: boolean, count: number): PartialCursorState[] {
+		const model = viewModel.model;
+		const hiddenAreas = viewModel.getHiddenAreas();
+
+		return cursors.map(cursor => {
+			const startLine = cursor.modelState.hasSelection() && !inSelectionMode
+				? cursor.modelState.selection.startLineNumber
+				: cursor.modelState.position.lineNumber;
+
+			const targetLine = CursorMoveCommands._targetFoldedUp(startLine, count, hiddenAreas);
+			const delta = startLine - targetLine;
+			if (delta === 0) {
+				return CursorState.fromModelState(cursor.modelState);
+			}
+			return CursorState.fromModelState(MoveOperations.moveUp(viewModel.cursorConfig, model, cursor.modelState, inSelectionMode, delta));
+		});
+	}
+
+	// Compute the target line after moving `count` steps downward from `startLine`,
+	// treating each folded region as a single step.
+	private static _targetFoldedDown(startLine: number, count: number, hiddenAreas: Range[], lineCount: number): number {
+		let line = startLine;
+		let i = 0;
+
+		while (i < hiddenAreas.length && hiddenAreas[i].endLineNumber < line + 1) {
+			i++;
+		}
+
+		for (let step = 0; step < count; step++) {
+			if (line >= lineCount) {
+				return lineCount;
+			}
+
+			let candidate = line + 1;
+			while (i < hiddenAreas.length && hiddenAreas[i].endLineNumber < candidate) {
+				i++;
+			}
+
+			if (i < hiddenAreas.length && hiddenAreas[i].startLineNumber <= candidate) {
+				candidate = hiddenAreas[i].endLineNumber + 1;
+			}
+
+			if (candidate > lineCount) {
+				// The next visible line does not exist (e.g. a fold reaches EOF).
+				return line;
+			}
+
+			line = candidate;
+		}
+
+		return line;
+	}
+
+	// Compute the target line after moving `count` steps upward from `startLine`,
+	// treating each folded region as a single step.
+	private static _targetFoldedUp(startLine: number, count: number, hiddenAreas: Range[]): number {
+		let line = startLine;
+		let i = hiddenAreas.length - 1;
+
+		while (i >= 0 && hiddenAreas[i].startLineNumber > line - 1) {
+			i--;
+		}
+
+		for (let step = 0; step < count; step++) {
+			if (line <= 1) {
+				return 1;
+			}
+
+			let candidate = line - 1;
+			while (i >= 0 && hiddenAreas[i].startLineNumber > candidate) {
+				i--;
+			}
+
+			if (i >= 0 && hiddenAreas[i].endLineNumber >= candidate) {
+				candidate = hiddenAreas[i].startLineNumber - 1;
+			}
+
+			if (candidate < 1) {
+				// The previous visible line does not exist (e.g. a fold reaches BOF).
+				return line;
+			}
+
+			line = candidate;
+		}
+
+		return line;
+	}
+
 	private static _moveToViewPosition(viewModel: IViewModel, cursor: CursorState, inSelectionMode: boolean, toViewLineNumber: number, toViewColumn: number): PartialCursorState {
 		return CursorState.fromViewState(cursor.viewState.move(inSelectionMode, toViewLineNumber, toViewColumn, 0));
 	}
@@ -626,8 +739,10 @@ export namespace CursorMove {
 						\`\`\`
 					* 'by': Unit to move. Default is computed based on 'to' value.
 						\`\`\`
-						'line', 'wrappedLine', 'character', 'halfLine'
+						'line', 'wrappedLine', 'character', 'halfLine', 'foldedLine'
 						\`\`\`
+						Use 'foldedLine' with 'up'/'down' to move by logical lines while treating each
+						folded region as a single step.
 					* 'value': Number of units to move. Default is '1'.
 					* 'select': If 'true' makes the selection. Default is 'false'.
 					* 'noHistory': If 'true' does not add the movement to navigation history. Default is 'false'.
@@ -643,7 +758,7 @@ export namespace CursorMove {
 						},
 						'by': {
 							'type': 'string',
-							'enum': ['line', 'wrappedLine', 'character', 'halfLine']
+							'enum': ['line', 'wrappedLine', 'character', 'halfLine', 'foldedLine']
 						},
 						'value': {
 							'type': 'number',
@@ -695,7 +810,8 @@ export namespace CursorMove {
 		Line: 'line',
 		WrappedLine: 'wrappedLine',
 		Character: 'character',
-		HalfLine: 'halfLine'
+		HalfLine: 'halfLine',
+		FoldedLine: 'foldedLine'
 	};
 
 	/**
@@ -781,6 +897,9 @@ export namespace CursorMove {
 			case RawUnit.HalfLine:
 				unit = Unit.HalfLine;
 				break;
+			case RawUnit.FoldedLine:
+				unit = Unit.FoldedLine;
+				break;
 		}
 
 		return {
@@ -855,6 +974,7 @@ export namespace CursorMove {
 		WrappedLine,
 		Character,
 		HalfLine,
+		FoldedLine,
 	}
 
 }
diff --git a/src/vs/editor/common/languages.ts b/src/vs/editor/common/languages.ts
index f141c78d98eaa..33e90ab7f7572 100644
--- a/src/vs/editor/common/languages.ts
+++ b/src/vs/editor/common/languages.ts
@@ -826,7 +826,7 @@ export class SelectedSuggestionInfo {
 	) {
 	}
 
-	public equals(other: SelectedSuggestionInfo) {
+	public equals(other: SelectedSuggestionInfo): boolean {
 		return Range.lift(this.range).equalsRange(other.range)
 			&& this.text === other.text
 			&& this.completionKind === other.completionKind
diff --git a/src/vs/editor/common/model.ts b/src/vs/editor/common/model.ts
index 5195e0b635374..2fc027b34a231 100644
--- a/src/vs/editor/common/model.ts
+++ b/src/vs/editor/common/model.ts
@@ -19,7 +19,7 @@ import { IWordAtPosition } from './core/wordHelper.js';
 import { FormattingOptions } from './languages.js';
 import { ILanguageSelection } from './languages/language.js';
 import { IBracketPairsTextModelPart } from './textModelBracketPairs.js';
-import { IModelContentChangedEvent, IModelDecorationsChangedEvent, IModelLanguageChangedEvent, IModelLanguageConfigurationChangedEvent, IModelOptionsChangedEvent, IModelTokensChangedEvent, ModelFontChangedEvent, ModelLineHeightChangedEvent } from './textModelEvents.js';
+import { IModelContentChangedEvent, IModelDecorationsChangedEvent, IModelLanguageChangedEvent, IModelLanguageConfigurationChangedEvent, IModelOptionsChangedEvent, IModelTokensChangedEvent, LineInjectedText, ModelFontChangedEvent, ModelLineHeightChangedEvent } from './textModelEvents.js';
 import { IModelContentChange } from './model/mirrorTextModel.js';
 import { IGuidesTextModelPart } from './textModelGuides.js';
 import { ITokenizationTextModelPart } from './tokenizationTextModelPart.js';
@@ -856,6 +856,12 @@ export interface ITextModel {
 	 */
 	getLineContent(lineNumber: number): string;
 
+	/**
+	 * Get the line injected text for a certain line.
+	 * @internal
+	 */
+	getLineInjectedText(lineNumber: number, ownerId?: number): LineInjectedText[];
+
 	/**
 	 * Get the text length for a certain line.
 	 */
diff --git a/src/vs/editor/common/model/textModel.ts b/src/vs/editor/common/model/textModel.ts
index 4d3ae947ad6e5..6d7e5a6be5503 100644
--- a/src/vs/editor/common/model/textModel.ts
+++ b/src/vs/editor/common/model/textModel.ts
@@ -3,7 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { ArrayQueue, pushMany } from '../../../base/common/arrays.js';
+import { pushMany } from '../../../base/common/arrays.js';
 import { VSBuffer, VSBufferReadableStream } from '../../../base/common/buffer.js';
 import { CharCode } from '../../../base/common/charCode.js';
 import { SetWithKey } from '../../../base/common/collections.js';
@@ -1539,65 +1539,36 @@ export class TextModel extends Disposable implements model.ITextModel, IDecorati
 				const changeLineCountDelta = (insertingLinesCnt - deletingLinesCnt);
 
 				const currentEditStartLineNumber = newLineCount - lineCount - changeLineCountDelta + startLineNumber;
-				const firstEditLineNumber = currentEditStartLineNumber;
-				const lastInsertedLineNumber = currentEditStartLineNumber + insertingLinesCnt;
-
-				const decorationsWithInjectedTextInEditedRange = this._decorationsTree.getInjectedTextInInterval(
-					this,
-					this.getOffsetAt(new Position(firstEditLineNumber, 1)),
-					this.getOffsetAt(new Position(lastInsertedLineNumber, this.getLineMaxColumn(lastInsertedLineNumber))),
-					0
-				);
-
-
-				const injectedTextInEditedRange = LineInjectedText.fromDecorations(decorationsWithInjectedTextInEditedRange);
-				const injectedTextInEditedRangeQueue = new ArrayQueue(injectedTextInEditedRange);
 
 				for (let j = editingLinesCnt; j >= 0; j--) {
 					const editLineNumber = startLineNumber + j;
 					const currentEditLineNumber = currentEditStartLineNumber + j;
 
-					injectedTextInEditedRangeQueue.takeFromEndWhile(r => r.lineNumber > currentEditLineNumber);
-					const decorationsInCurrentLine = injectedTextInEditedRangeQueue.takeFromEndWhile(r => r.lineNumber === currentEditLineNumber);
-
 					rawContentChanges.push(
 						new ModelRawLineChanged(
 							editLineNumber,
-							currentEditLineNumber,
-							this.getLineContent(currentEditLineNumber),
-							decorationsInCurrentLine
+							currentEditLineNumber
 						));
 				}
 
 				if (editingLinesCnt < deletingLinesCnt) {
 					// Must delete some lines
 					const spliceStartLineNumber = startLineNumber + editingLinesCnt;
-					rawContentChanges.push(new ModelRawLinesDeleted(spliceStartLineNumber + 1, endLineNumber));
+					const cnt = insertingLinesCnt - deletingLinesCnt;
+					const lastUntouchedLinePostEdit = newLineCount - lineCount - cnt + spliceStartLineNumber;
+					rawContentChanges.push(new ModelRawLinesDeleted(spliceStartLineNumber + 1, endLineNumber, lastUntouchedLinePostEdit));
 				}
 
 				if (editingLinesCnt < insertingLinesCnt) {
-					const injectedTextInEditedRangeQueue = new ArrayQueue(injectedTextInEditedRange);
 					// Must insert some lines
 					const spliceLineNumber = startLineNumber + editingLinesCnt;
 					const cnt = insertingLinesCnt - editingLinesCnt;
 					const fromLineNumber = newLineCount - lineCount - cnt + spliceLineNumber + 1;
-					const injectedTexts: (LineInjectedText[] | null)[] = [];
-					const newLines: string[] = [];
-					for (let i = 0; i < cnt; i++) {
-						const lineNumber = fromLineNumber + i;
-						newLines[i] = this.getLineContent(lineNumber);
-
-						injectedTextInEditedRangeQueue.takeWhile(r => r.lineNumber < lineNumber);
-						injectedTexts[i] = injectedTextInEditedRangeQueue.takeWhile(r => r.lineNumber === lineNumber);
-					}
-
 					rawContentChanges.push(
 						new ModelRawLinesInserted(
 							spliceLineNumber + 1,
 							fromLineNumber,
-							cnt,
-							newLines,
-							injectedTexts
+							cnt
 						)
 					);
 				}
@@ -1655,7 +1626,7 @@ export class TextModel extends Disposable implements model.ITextModel, IDecorati
 
 		if (affectedInjectedTextLines && affectedInjectedTextLines.size > 0) {
 			const affectedLines = Array.from(affectedInjectedTextLines);
-			const lineChangeEvents = affectedLines.map(lineNumber => new ModelRawLineChanged(lineNumber, lineNumber, this.getLineContent(lineNumber), this._getInjectedTextInLine(lineNumber)));
+			const lineChangeEvents = affectedLines.map(lineNumber => new ModelRawLineChanged(lineNumber, lineNumber));
 			this._onDidChangeContentOrInjectedText(new ModelInjectedTextChangedEvent(lineChangeEvents));
 		}
 		this._fireOnDidChangeLineHeight(affectedLineHeights);
@@ -1881,11 +1852,11 @@ export class TextModel extends Disposable implements model.ITextModel, IDecorati
 		return decs;
 	}
 
-	private _getInjectedTextInLine(lineNumber: number): LineInjectedText[] {
+	public getLineInjectedText(lineNumber: number, ownerId: number = 0): LineInjectedText[] {
 		const startOffset = this._buffer.getOffsetAt(lineNumber, 1);
 		const endOffset = startOffset + this._buffer.getLineLength(lineNumber);
 
-		const result = this._decorationsTree.getInjectedTextInInterval(this, startOffset, endOffset, 0);
+		const result = this._decorationsTree.getInjectedTextInInterval(this, startOffset, endOffset, ownerId);
 		return LineInjectedText.fromDecorations(result).filter(t => t.lineNumber === lineNumber);
 	}
 
diff --git a/src/vs/editor/common/modelLineProjectionData.ts b/src/vs/editor/common/modelLineProjectionData.ts
index aac6ae4642d68..dc661c4b25a46 100644
--- a/src/vs/editor/common/modelLineProjectionData.ts
+++ b/src/vs/editor/common/modelLineProjectionData.ts
@@ -4,8 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { assertNever } from '../../base/common/assert.js';
-import { WrappingIndent } from './config/editorOptions.js';
-import { FontInfo } from './config/fontInfo.js';
+import { IComputedEditorOptions } from './config/editorOptions.js';
 import { Position } from './core/position.js';
 import { InjectedTextCursorStops, InjectedTextOptions, PositionAffinity } from './model.js';
 import { LineInjectedText } from './textModelEvents.js';
@@ -328,14 +327,19 @@ export class OutputPosition {
 	}
 }
 
+export interface ILineBreaksComputerContext {
+	getLineContent(lineNumber: number): string;
+	getLineInjectedText(lineNumber: number): LineInjectedText[] | null;
+}
+
 export interface ILineBreaksComputerFactory {
-	createLineBreaksComputer(fontInfo: FontInfo, tabSize: number, wrappingColumn: number, wrappingIndent: WrappingIndent, wordBreak: 'normal' | 'keepAll', wrapOnEscapedLineFeeds: boolean): ILineBreaksComputer;
+	createLineBreaksComputer(context: ILineBreaksComputerContext, options: IComputedEditorOptions, tabSize: number): ILineBreaksComputer;
 }
 
 export interface ILineBreaksComputer {
 	/**
 	 * Pass in `previousLineBreakData` if the only difference is in breaking columns!!!
 	 */
-	addRequest(lineText: string, injectedText: LineInjectedText[] | null, previousLineBreakData: ModelLineProjectionData | null): void;
+	addRequest(lineNumber: number, previousLineBreakData: ModelLineProjectionData | null): void;
 	finalize(): (ModelLineProjectionData | null)[];
 }
diff --git a/src/vs/editor/common/textModelEvents.ts b/src/vs/editor/common/textModelEvents.ts
index 4fa24afd2c1b0..1f504db5852e6 100644
--- a/src/vs/editor/common/textModelEvents.ts
+++ b/src/vs/editor/common/textModelEvents.ts
@@ -315,20 +315,10 @@ export class ModelRawLineChanged {
 	 * The new line number the old one is mapped to (after the change was applied).
 	 */
 	public readonly lineNumberPostEdit: number;
-	/**
-	 * The new value of the line.
-	 */
-	public readonly detail: string;
-	/**
-	 * The injected text on the line.
-	 */
-	public readonly injectedText: LineInjectedText[] | null;
 
-	constructor(lineNumber: number, lineNumberPostEdit: number, detail: string, injectedText: LineInjectedText[] | null) {
+	constructor(lineNumber: number, lineNumberPostEdit: number) {
 		this.lineNumber = lineNumber;
 		this.lineNumberPostEdit = lineNumberPostEdit;
-		this.detail = detail;
-		this.injectedText = injectedText;
 	}
 }
 
@@ -397,10 +387,15 @@ export class ModelRawLinesDeleted {
 	 * At what line the deletion stopped (inclusive).
 	 */
 	public readonly toLineNumber: number;
+	/**
+	 * The last unmodified line in the updated buffer after the deletion is made.
+	 */
+	public readonly lastUntouchedLinePostEdit: number;
 
-	constructor(fromLineNumber: number, toLineNumber: number) {
+	constructor(fromLineNumber: number, toLineNumber: number, lastUntouchedLinePostEdit: number) {
 		this.fromLineNumber = fromLineNumber;
 		this.toLineNumber = toLineNumber;
+		this.lastUntouchedLinePostEdit = lastUntouchedLinePostEdit;
 	}
 }
 
@@ -434,21 +429,11 @@ export class ModelRawLinesInserted {
 	public get toLineNumberPostEdit(): number {
 		return this.fromLineNumberPostEdit + this.count - 1;
 	}
-	/**
-	 * The text that was inserted
-	 */
-	public readonly detail: string[];
-	/**
-	 * The injected texts for every inserted line.
-	 */
-	public readonly injectedTexts: (LineInjectedText[] | null)[];
 
-	constructor(fromLineNumber: number, fromLineNumberPostEdit: number, count: number, detail: string[], injectedTexts: (LineInjectedText[] | null)[]) {
-		this.injectedTexts = injectedTexts;
+	constructor(fromLineNumber: number, fromLineNumberPostEdit: number, count: number) {
 		this.fromLineNumber = fromLineNumber;
 		this.fromLineNumberPostEdit = fromLineNumberPostEdit;
 		this.count = count;
-		this.detail = detail;
 	}
 }
 
diff --git a/src/vs/editor/common/viewLayout/lineHeights.ts b/src/vs/editor/common/viewLayout/lineHeights.ts
index 215d210f9fda1..3c5ab572d66a6 100644
--- a/src/vs/editor/common/viewLayout/lineHeights.ts
+++ b/src/vs/editor/common/viewLayout/lineHeights.ts
@@ -21,7 +21,7 @@ type PendingChange =
 	| { readonly kind: PendingChangeKind.InsertOrChange; readonly decorationId: string; readonly startLineNumber: number; readonly endLineNumber: number; readonly lineHeight: number }
 	| { readonly kind: PendingChangeKind.Remove; readonly decorationId: string }
 	| { readonly kind: PendingChangeKind.LinesDeleted; readonly fromLineNumber: number; readonly toLineNumber: number }
-	| { readonly kind: PendingChangeKind.LinesInserted; readonly fromLineNumber: number; readonly toLineNumber: number; readonly lineHeightsAdded: CustomLineHeightData[] };
+	| { readonly kind: PendingChangeKind.LinesInserted; readonly fromLineNumber: number; readonly toLineNumber: number };
 
 export class CustomLine {
 
@@ -132,8 +132,8 @@ export class LineHeightsManager {
 		this._hasPending = true;
 	}
 
-	public onLinesInserted(fromLineNumber: number, toLineNumber: number, lineHeightsAdded: CustomLineHeightData[]): void {
-		this._pendingChanges.push({ kind: PendingChangeKind.LinesInserted, fromLineNumber, toLineNumber, lineHeightsAdded });
+	public onLinesInserted(fromLineNumber: number, toLineNumber: number): void {
+		this._pendingChanges.push({ kind: PendingChangeKind.LinesInserted, fromLineNumber, toLineNumber });
 		this._hasPending = true;
 	}
 
@@ -146,28 +146,29 @@ export class LineHeightsManager {
 		this._hasPending = false;
 
 		const stagedInserts: CustomLine[] = [];
+		const stagedIdMap = new ArrayMap<string, CustomLine>();
 		for (const change of changes) {
 			switch (change.kind) {
 				case PendingChangeKind.Remove:
-					this._doRemoveCustomLineHeight(change.decorationId, stagedInserts);
+					this._doRemoveCustomLineHeight(change.decorationId, stagedIdMap);
 					break;
 				case PendingChangeKind.InsertOrChange:
-					this._doInsertOrChangeCustomLineHeight(change.decorationId, change.startLineNumber, change.endLineNumber, change.lineHeight, stagedInserts);
+					this._doInsertOrChangeCustomLineHeight(change.decorationId, change.startLineNumber, change.endLineNumber, change.lineHeight, stagedInserts, stagedIdMap);
 					break;
 				case PendingChangeKind.LinesDeleted:
-					this._flushStagedDecorationChanges(stagedInserts);
+					this._flushStagedDecorationChanges(stagedInserts, stagedIdMap);
 					this._doLinesDeleted(change.fromLineNumber, change.toLineNumber);
 					break;
 				case PendingChangeKind.LinesInserted:
-					this._flushStagedDecorationChanges(stagedInserts);
-					this._doLinesInserted(change.fromLineNumber, change.toLineNumber, change.lineHeightsAdded, stagedInserts);
+					this._flushStagedDecorationChanges(stagedInserts, stagedIdMap);
+					this._doLinesInserted(change.fromLineNumber, change.toLineNumber, stagedInserts, stagedIdMap);
 					break;
 			}
 		}
-		this._flushStagedDecorationChanges(stagedInserts);
+		this._flushStagedDecorationChanges(stagedInserts, stagedIdMap);
 	}
 
-	private _doRemoveCustomLineHeight(decorationID: string, stagedInserts: CustomLine[]): void {
+	private _doRemoveCustomLineHeight(decorationID: string, stagedIdMap: ArrayMap<string, CustomLine>): void {
 		const customLines = this._decorationIDToCustomLine.get(decorationID);
 		if (customLines) {
 			this._decorationIDToCustomLine.delete(decorationID);
@@ -176,32 +177,42 @@ export class LineHeightsManager {
 				this._invalidIndex = Math.min(this._invalidIndex, customLine.index);
 			}
 		}
-		for (let i = stagedInserts.length - 1; i >= 0; i--) {
-			if (stagedInserts[i].decorationId === decorationID) {
-				stagedInserts.splice(i, 1);
+		const stagedLines = stagedIdMap.get(decorationID);
+		if (stagedLines) {
+			stagedIdMap.delete(decorationID);
+			for (const line of stagedLines) {
+				line.deleted = true;
 			}
 		}
 	}
 
-	private _doInsertOrChangeCustomLineHeight(decorationId: string, startLineNumber: number, endLineNumber: number, lineHeight: number, stagedInserts: CustomLine[]): void {
-		this._doRemoveCustomLineHeight(decorationId, stagedInserts);
+	private _doInsertOrChangeCustomLineHeight(decorationId: string, startLineNumber: number, endLineNumber: number, lineHeight: number, stagedInserts: CustomLine[], stagedIdMap: ArrayMap<string, CustomLine>): void {
+		this._doRemoveCustomLineHeight(decorationId, stagedIdMap);
 		for (let lineNumber = startLineNumber; lineNumber <= endLineNumber; lineNumber++) {
 			const customLine = new CustomLine(decorationId, -1, lineNumber, lineHeight, 0);
 			stagedInserts.push(customLine);
+			stagedIdMap.add(decorationId, customLine);
 		}
 	}
 
-	private _flushStagedDecorationChanges(stagedInserts: CustomLine[]): void {
+	private _flushStagedDecorationChanges(stagedInserts: CustomLine[], stagedIdMap: ArrayMap<string, CustomLine>): void {
 		if (stagedInserts.length === 0 && this._invalidIndex === Infinity) {
 			return;
 		}
 		for (const pendingChange of stagedInserts) {
+			if (pendingChange.deleted) {
+				continue;
+			}
 			const candidateInsertionIndex = this._binarySearchOverOrderedCustomLinesArray(pendingChange.lineNumber);
 			const insertionIndex = candidateInsertionIndex >= 0 ? candidateInsertionIndex : -(candidateInsertionIndex + 1);
 			this._orderedCustomLines.splice(insertionIndex, 0, pendingChange);
 			this._invalidIndex = Math.min(this._invalidIndex, insertionIndex);
 		}
 		stagedInserts.length = 0;
+		stagedIdMap.clear();
+		if (this._invalidIndex === Infinity) {
+			return;
+		}
 		const newDecorationIDToSpecialLine = new ArrayMap<string, CustomLine>();
 		const newOrderedSpecialLines: CustomLine[] = [];
 
@@ -358,7 +369,7 @@ export class LineHeightsManager {
 		}
 	}
 
-	private _doLinesInserted(fromLineNumber: number, toLineNumber: number, lineHeightsAdded: CustomLineHeightData[], stagedInserts: CustomLine[]): void {
+	private _doLinesInserted(fromLineNumber: number, toLineNumber: number, stagedInserts: CustomLine[], stagedIdMap: ArrayMap<string, CustomLine>): void {
 		const insertCount = toLineNumber - fromLineNumber + 1;
 		const candidateStartIndexOfInsertion = this._binarySearchOverOrderedCustomLinesArray(fromLineNumber);
 		let startIndexOfInsertion: number;
@@ -374,22 +385,6 @@ export class LineHeightsManager {
 		} else {
 			startIndexOfInsertion = -(candidateStartIndexOfInsertion + 1);
 		}
-		const maxLineHeightPerLine = new Map<number, number>();
-		for (const lineHeightAdded of lineHeightsAdded) {
-			for (let lineNumber = lineHeightAdded.startLineNumber; lineNumber <= lineHeightAdded.endLineNumber; lineNumber++) {
-				if (lineNumber >= fromLineNumber && lineNumber <= toLineNumber) {
-					const currentMax = maxLineHeightPerLine.get(lineNumber) ?? this._defaultLineHeight;
-					maxLineHeightPerLine.set(lineNumber, Math.max(currentMax, lineHeightAdded.lineHeight));
-				}
-			}
-			this._doInsertOrChangeCustomLineHeight(
-				lineHeightAdded.decorationId,
-				lineHeightAdded.startLineNumber,
-				lineHeightAdded.endLineNumber,
-				lineHeightAdded.lineHeight,
-				stagedInserts
-			);
-		}
 		const toReAdd: CustomLineHeightData[] = [];
 		const decorationsImmediatelyAfter = new Set<string>();
 		for (let i = startIndexOfInsertion; i < this._orderedCustomLines.length; i++) {
@@ -404,9 +399,7 @@ export class LineHeightsManager {
 			}
 		}
 		const decorationsWithGaps = intersection(decorationsImmediatelyBefore, decorationsImmediatelyAfter);
-		const specialHeightToAdd = Array.from(maxLineHeightPerLine.values()).reduce((acc, height) => acc + height, 0);
-		const defaultHeightToAdd = (insertCount - maxLineHeightPerLine.size) * this._defaultLineHeight;
-		const prefixSumToAdd = specialHeightToAdd + defaultHeightToAdd;
+		const prefixSumToAdd = insertCount * this._defaultLineHeight;
 		for (let i = startIndexOfInsertion; i < this._orderedCustomLines.length; i++) {
 			this._orderedCustomLines[i].lineNumber += insertCount;
 			this._orderedCustomLines[i].prefixSum += prefixSumToAdd;
@@ -429,7 +422,7 @@ export class LineHeightsManager {
 			}
 
 			for (const dec of toReAdd) {
-				this._doInsertOrChangeCustomLineHeight(dec.decorationId, dec.startLineNumber, dec.endLineNumber, dec.lineHeight, stagedInserts);
+				this._doInsertOrChangeCustomLineHeight(dec.decorationId, dec.startLineNumber, dec.endLineNumber, dec.lineHeight, stagedInserts, stagedIdMap);
 			}
 		}
 	}
@@ -493,4 +486,8 @@ class ArrayMap<K, T> {
 	delete(key: K): void {
 		this._map.delete(key);
 	}
+
+	clear(): void {
+		this._map.clear();
+	}
 }
diff --git a/src/vs/editor/common/viewLayout/linesLayout.ts b/src/vs/editor/common/viewLayout/linesLayout.ts
index cd69d95877d8f..033b7423db4c2 100644
--- a/src/vs/editor/common/viewLayout/linesLayout.ts
+++ b/src/vs/editor/common/viewLayout/linesLayout.ts
@@ -349,9 +349,8 @@ export class LinesLayout {
 	 *
 	 * @param fromLineNumber The line number at which the insertion started, inclusive
 	 * @param toLineNumber The line number at which the insertion ended, inclusive.
-	 * @param lineHeightsAdded The custom line height data for the inserted lines.
 	 */
-	public onLinesInserted(fromLineNumber: number, toLineNumber: number, lineHeightsAdded: CustomLineHeightData[]): void {
+	public onLinesInserted(fromLineNumber: number, toLineNumber: number): void {
 		fromLineNumber = fromLineNumber | 0;
 		toLineNumber = toLineNumber | 0;
 
@@ -363,7 +362,7 @@ export class LinesLayout {
 				this._arr[i].afterLineNumber += (toLineNumber - fromLineNumber + 1);
 			}
 		}
-		this._lineHeightsManager.onLinesInserted(fromLineNumber, toLineNumber, lineHeightsAdded);
+		this._lineHeightsManager.onLinesInserted(fromLineNumber, toLineNumber);
 	}
 
 	/**
diff --git a/src/vs/editor/common/viewLayout/viewLayout.ts b/src/vs/editor/common/viewLayout/viewLayout.ts
index 048dc241eae7d..202187a4aadb2 100644
--- a/src/vs/editor/common/viewLayout/viewLayout.ts
+++ b/src/vs/editor/common/viewLayout/viewLayout.ts
@@ -243,8 +243,8 @@ export class ViewLayout extends Disposable implements IViewLayout {
 	public onLinesDeleted(fromLineNumber: number, toLineNumber: number): void {
 		this._linesLayout.onLinesDeleted(fromLineNumber, toLineNumber);
 	}
-	public onLinesInserted(fromLineNumber: number, toLineNumber: number, lineHeightsAdded: CustomLineHeightData[]): void {
-		this._linesLayout.onLinesInserted(fromLineNumber, toLineNumber, lineHeightsAdded);
+	public onLinesInserted(fromLineNumber: number, toLineNumber: number): void {
+		this._linesLayout.onLinesInserted(fromLineNumber, toLineNumber);
 	}
 
 	// ---- end view event handlers
diff --git a/src/vs/editor/common/viewModel.ts b/src/vs/editor/common/viewModel.ts
index 37ccca993c4f6..94d4488ec9b28 100644
--- a/src/vs/editor/common/viewModel.ts
+++ b/src/vs/editor/common/viewModel.ts
@@ -15,7 +15,7 @@ import { CursorChangeReason } from './cursorEvents.js';
 import { INewScrollPosition, ScrollType } from './editorCommon.js';
 import { EditorTheme } from './editorTheme.js';
 import { EndOfLinePreference, IGlyphMarginLanesModel, IModelDecorationOptions, ITextModel, TextDirection } from './model.js';
-import { ILineBreaksComputer, InjectedText } from './modelLineProjectionData.js';
+import { ILineBreaksComputer, ILineBreaksComputerContext, InjectedText } from './modelLineProjectionData.js';
 import { InternalModelContentChangeEvent, ModelInjectedTextChangedEvent } from './textModelEvents.js';
 import { BracketGuideOptions, IActiveIndentGuideInfo, IndentGuide } from './textModelGuides.js';
 import { IViewLineTokens } from './tokens/lineTokens.js';
@@ -89,7 +89,7 @@ export interface IViewModel extends ICursorSimpleModel, ISimpleModel {
 	onDidChangeContentOrInjectedText(e: InternalModelContentChangeEvent | ModelInjectedTextChangedEvent): void;
 	emitContentChangeEvent(e: InternalModelContentChangeEvent | ModelInjectedTextChangedEvent): void;
 
-	createLineBreaksComputer(): ILineBreaksComputer;
+	createLineBreaksComputer(context?: ILineBreaksComputerContext): ILineBreaksComputer;
 
 	//#region cursor
 	getPrimaryCursorState(): CursorState;
diff --git a/src/vs/editor/common/viewModel/minimapTokensColorTracker.ts b/src/vs/editor/common/viewModel/minimapTokensColorTracker.ts
index 45473f77c4dec..72ea2bcd16bcc 100644
--- a/src/vs/editor/common/viewModel/minimapTokensColorTracker.ts
+++ b/src/vs/editor/common/viewModel/minimapTokensColorTracker.ts
@@ -38,7 +38,10 @@ export class MinimapTokensColorTracker extends Disposable {
 	private _updateColorMap(): void {
 		const colorMap = TokenizationRegistry.getColorMap();
 		if (!colorMap) {
-			this._colors = [RGBA8.Empty];
+			this._colors = [];
+			for (let i = 0; i <= ColorId.DefaultBackground; i++) {
+				this._colors[i] = RGBA8.Empty;
+			}
 			this._backgroundIsLight = true;
 			return;
 		}
diff --git a/src/vs/editor/common/viewModel/monospaceLineBreaksComputer.ts b/src/vs/editor/common/viewModel/monospaceLineBreaksComputer.ts
index 37fba22662555..58d52910d2e2c 100644
--- a/src/vs/editor/common/viewModel/monospaceLineBreaksComputer.ts
+++ b/src/vs/editor/common/viewModel/monospaceLineBreaksComputer.ts
@@ -7,10 +7,9 @@ import { CharCode } from '../../../base/common/charCode.js';
 import * as strings from '../../../base/common/strings.js';
 import { WrappingIndent, IComputedEditorOptions, EditorOption } from '../config/editorOptions.js';
 import { CharacterClassifier } from '../core/characterClassifier.js';
-import { FontInfo } from '../config/fontInfo.js';
 import { LineInjectedText } from '../textModelEvents.js';
 import { InjectedTextOptions } from '../model.js';
-import { ILineBreaksComputerFactory, ILineBreaksComputer, ModelLineProjectionData } from '../modelLineProjectionData.js';
+import { ILineBreaksComputerFactory, ILineBreaksComputer, ModelLineProjectionData, ILineBreaksComputerContext } from '../modelLineProjectionData.js';
 
 export class MonospaceLineBreaksComputerFactory implements ILineBreaksComputerFactory {
 	public static create(options: IComputedEditorOptions): MonospaceLineBreaksComputerFactory {
@@ -26,23 +25,27 @@ export class MonospaceLineBreaksComputerFactory implements ILineBreaksComputerFa
 		this.classifier = new WrappingCharacterClassifier(breakBeforeChars, breakAfterChars);
 	}
 
-	public createLineBreaksComputer(fontInfo: FontInfo, tabSize: number, wrappingColumn: number, wrappingIndent: WrappingIndent, wordBreak: 'normal' | 'keepAll', wrapOnEscapedLineFeeds: boolean): ILineBreaksComputer {
-		const requests: string[] = [];
-		const injectedTexts: (LineInjectedText[] | null)[] = [];
+	public createLineBreaksComputer(context: ILineBreaksComputerContext, options: IComputedEditorOptions, tabSize: number): ILineBreaksComputer {
+		const lineNumbers: number[] = [];
 		const previousBreakingData: (ModelLineProjectionData | null)[] = [];
 		return {
-			addRequest: (lineText: string, injectedText: LineInjectedText[] | null, previousLineBreakData: ModelLineProjectionData | null) => {
-				requests.push(lineText);
-				injectedTexts.push(injectedText);
+			addRequest: (lineNumber: number, previousLineBreakData: ModelLineProjectionData | null) => {
+				lineNumbers.push(lineNumber);
 				previousBreakingData.push(previousLineBreakData);
 			},
 			finalize: () => {
+				const fontInfo = options.get(EditorOption.fontInfo);
+				const wrappingColumn = options.get(EditorOption.wrappingInfo).wrappingColumn;
+				const wrappingIndent = options.get(EditorOption.wrappingIndent);
+				const wordBreak = options.get(EditorOption.wordBreak);
+				const wrapOnEscapedLineFeeds = options.get(EditorOption.wrapOnEscapedLineFeeds);
 				const columnsForFullWidthChar = fontInfo.typicalFullwidthCharacterWidth / fontInfo.typicalHalfwidthCharacterWidth;
 				const result: (ModelLineProjectionData | null)[] = [];
-				for (let i = 0, len = requests.length; i < len; i++) {
-					const injectedText = injectedTexts[i];
+				for (let i = 0, len = lineNumbers.length; i < len; i++) {
+					const lineNumber = lineNumbers[i];
+					const injectedText = context.getLineInjectedText(lineNumber);
+					const lineText = context.getLineContent(lineNumber);
 					const previousLineBreakData = previousBreakingData[i];
-					const lineText = requests[i];
 					const isLineFeedWrappingEnabled = wrapOnEscapedLineFeeds && lineText.includes('"') && lineText.includes('\\n');
 					if (previousLineBreakData && !previousLineBreakData.injectionOptions && !injectedText && !isLineFeedWrappingEnabled) {
 						result[i] = createLineBreaksFromPreviousLineBreaks(this.classifier, previousLineBreakData, lineText, tabSize, wrappingColumn, columnsForFullWidthChar, wrappingIndent, wordBreak);
diff --git a/src/vs/editor/common/viewModel/viewModelImpl.ts b/src/vs/editor/common/viewModel/viewModelImpl.ts
index 299fb151446f4..569ab17725338 100644
--- a/src/vs/editor/common/viewModel/viewModelImpl.ts
+++ b/src/vs/editor/common/viewModel/viewModelImpl.ts
@@ -33,7 +33,7 @@ import { EditorTheme } from '../editorTheme.js';
 import * as viewEvents from '../viewEvents.js';
 import { ViewLayout } from '../viewLayout/viewLayout.js';
 import { MinimapTokensColorTracker } from './minimapTokensColorTracker.js';
-import { ILineBreaksComputer, ILineBreaksComputerFactory, InjectedText } from '../modelLineProjectionData.js';
+import { ILineBreaksComputer, ILineBreaksComputerContext, ILineBreaksComputerFactory, InjectedText } from '../modelLineProjectionData.js';
 import { ViewEventHandler } from '../viewEventHandler.js';
 import { ILineHeightChangeAccessor, IViewModel, IWhitespaceChangeAccessor, MinimapLinesRenderingData, OverviewRulerDecorationsGroup, ViewLineData, ViewLineRenderingData, ViewModelDecoration } from '../viewModel.js';
 import { ViewModelDecorations } from './viewModelDecorations.js';
@@ -97,25 +97,13 @@ export class ViewModel extends Disposable implements IViewModel {
 
 		} else {
 			const options = this._configuration.options;
-			const fontInfo = options.get(EditorOption.fontInfo);
-			const wrappingStrategy = options.get(EditorOption.wrappingStrategy);
-			const wrappingInfo = options.get(EditorOption.wrappingInfo);
-			const wrappingIndent = options.get(EditorOption.wrappingIndent);
-			const wordBreak = options.get(EditorOption.wordBreak);
-			const wrapOnEscapedLineFeeds = options.get(EditorOption.wrapOnEscapedLineFeeds);
-
 			this._lines = new ViewModelLinesFromProjectedModel(
 				this._editorId,
 				this.model,
 				domLineBreaksComputerFactory,
 				monospaceLineBreaksComputerFactory,
-				fontInfo,
-				this.model.getOptions().tabSize,
-				wrappingStrategy,
-				wrappingInfo.wrappingColumn,
-				wrappingIndent,
-				wordBreak,
-				wrapOnEscapedLineFeeds
+				options,
+				this.model.getOptions().tabSize
 			);
 		}
 
@@ -184,8 +172,8 @@ export class ViewModel extends Disposable implements IViewModel {
 		return this._configuration.options.get(id);
 	}
 
-	public createLineBreaksComputer(): ILineBreaksComputer {
-		return this._lines.createLineBreaksComputer();
+	public createLineBreaksComputer(context?: ILineBreaksComputerContext): ILineBreaksComputer {
+		return this._lines.createLineBreaksComputer(context);
 	}
 
 	public addViewEventHandler(eventHandler: ViewEventHandler): void {
@@ -274,13 +262,8 @@ export class ViewModel extends Disposable implements IViewModel {
 	private _onConfigurationChanged(eventsCollector: ViewModelEventsCollector, e: ConfigurationChangedEvent): void {
 		const stableViewport = this._captureStableViewport();
 		const options = this._configuration.options;
-		const fontInfo = options.get(EditorOption.fontInfo);
-		const wrappingStrategy = options.get(EditorOption.wrappingStrategy);
-		const wrappingInfo = options.get(EditorOption.wrappingInfo);
-		const wrappingIndent = options.get(EditorOption.wrappingIndent);
-		const wordBreak = options.get(EditorOption.wordBreak);
 
-		if (this._lines.setWrappingSettings(fontInfo, wrappingStrategy, wrappingInfo.wrappingColumn, wrappingIndent, wordBreak)) {
+		if (this._lines.setWrappingSettings(options)) {
 			eventsCollector.emitViewEvent(new viewEvents.ViewFlushedEvent());
 			eventsCollector.emitViewEvent(new viewEvents.ViewLineMappingChangedEvent());
 			eventsCollector.emitViewEvent(new viewEvents.ViewDecorationsChangedEvent(null));
@@ -332,22 +315,13 @@ export class ViewModel extends Disposable implements IViewModel {
 			for (const change of changes) {
 				switch (change.changeType) {
 					case textModelEvents.RawContentChangedType.LinesInserted: {
-						for (let lineIdx = 0; lineIdx < change.detail.length; lineIdx++) {
-							const line = change.detail[lineIdx];
-							let injectedText = change.injectedTexts[lineIdx];
-							if (injectedText) {
-								injectedText = injectedText.filter(element => (!element.ownerId || element.ownerId === this._editorId));
-							}
-							lineBreaksComputer.addRequest(line, injectedText, null);
+						for (let i = 0; i < change.count; i++) {
+							lineBreaksComputer.addRequest(change.fromLineNumberPostEdit + i, null);
 						}
 						break;
 					}
 					case textModelEvents.RawContentChangedType.LineChanged: {
-						let injectedText: textModelEvents.LineInjectedText[] | null = null;
-						if (change.injectedText) {
-							injectedText = change.injectedText.filter(element => (!element.ownerId || element.ownerId === this._editorId));
-						}
-						lineBreaksComputer.addRequest(change.detail, injectedText, null);
+						lineBreaksComputer.addRequest(change.lineNumberPostEdit, null);
 						break;
 					}
 				}
@@ -355,6 +329,11 @@ export class ViewModel extends Disposable implements IViewModel {
 			const lineBreaks = lineBreaksComputer.finalize();
 			const lineBreakQueue = new ArrayQueue(lineBreaks);
 
+			// Collect model line ranges that need custom line height computation.
+			// We defer this until after the loop because the coordinatesConverter
+			// relies on projections that may not yet reflect all changes in the batch.
+			const customLineHeightRangesToInsert: { fromLineNumber: number; toLineNumber: number }[] = [];
+
 			for (const change of changes) {
 				switch (change.changeType) {
 					case textModelEvents.RawContentChangedType.Flush: {
@@ -370,16 +349,18 @@ export class ViewModel extends Disposable implements IViewModel {
 						if (linesDeletedEvent !== null) {
 							eventsCollector.emitViewEvent(linesDeletedEvent);
 							this.viewLayout.onLinesDeleted(linesDeletedEvent.fromLineNumber, linesDeletedEvent.toLineNumber);
+							customLineHeightRangesToInsert.push({ fromLineNumber: change.lastUntouchedLinePostEdit, toLineNumber: change.lastUntouchedLinePostEdit });
 						}
 						hadOtherModelChange = true;
 						break;
 					}
 					case textModelEvents.RawContentChangedType.LinesInserted: {
-						const insertedLineBreaks = lineBreakQueue.takeCount(change.detail.length);
+						const insertedLineBreaks = lineBreakQueue.takeCount(change.count);
 						const linesInsertedEvent = this._lines.onModelLinesInserted(versionId, change.fromLineNumber, change.toLineNumber, insertedLineBreaks);
 						if (linesInsertedEvent !== null) {
 							eventsCollector.emitViewEvent(linesInsertedEvent);
-							this.viewLayout.onLinesInserted(linesInsertedEvent.fromLineNumber, linesInsertedEvent.toLineNumber, this._getCustomLineHeightsForLines(change.fromLineNumberPostEdit, change.toLineNumberPostEdit));
+							this.viewLayout.onLinesInserted(linesInsertedEvent.fromLineNumber, linesInsertedEvent.toLineNumber);
+							customLineHeightRangesToInsert.push({ fromLineNumber: change.fromLineNumberPostEdit, toLineNumber: change.toLineNumberPostEdit });
 						}
 						hadOtherModelChange = true;
 						break;
@@ -394,11 +375,13 @@ export class ViewModel extends Disposable implements IViewModel {
 						}
 						if (linesInsertedEvent) {
 							eventsCollector.emitViewEvent(linesInsertedEvent);
-							this.viewLayout.onLinesInserted(linesInsertedEvent.fromLineNumber, linesInsertedEvent.toLineNumber, this._getCustomLineHeightsForLines(change.lineNumberPostEdit, change.lineNumberPostEdit));
+							this.viewLayout.onLinesInserted(linesInsertedEvent.fromLineNumber, linesInsertedEvent.toLineNumber);
+							customLineHeightRangesToInsert.push({ fromLineNumber: change.lineNumberPostEdit, toLineNumber: change.lineNumberPostEdit });
 						}
 						if (linesDeletedEvent) {
 							eventsCollector.emitViewEvent(linesDeletedEvent);
 							this.viewLayout.onLinesDeleted(linesDeletedEvent.fromLineNumber, linesDeletedEvent.toLineNumber);
+							customLineHeightRangesToInsert.push({ fromLineNumber: change.lineNumberPostEdit, toLineNumber: change.lineNumberPostEdit });
 						}
 						break;
 					}
@@ -412,6 +395,19 @@ export class ViewModel extends Disposable implements IViewModel {
 			if (versionId !== null) {
 				this._lines.acceptVersionId(versionId);
 			}
+
+			// Apply deferred custom line heights now that projections are stable
+			if (customLineHeightRangesToInsert.length > 0) {
+				this.viewLayout.changeSpecialLineHeights((accessor: ILineHeightChangeAccessor) => {
+					for (const range of customLineHeightRangesToInsert) {
+						const customLineHeights = this._getCustomLineHeightsForLines(range.fromLineNumber, range.toLineNumber);
+						for (const data of customLineHeights) {
+							accessor.insertOrChangeCustomLineHeight(data.decorationId, data.startLineNumber, data.endLineNumber, data.lineHeight);
+						}
+					}
+				});
+			}
+
 			this.viewLayout.onHeightMaybeChanged();
 
 			if (!hadOtherModelChange && hadModelLineChangeThatChangedLineMapping) {
diff --git a/src/vs/editor/common/viewModel/viewModelLines.ts b/src/vs/editor/common/viewModel/viewModelLines.ts
index b3721760c9d4e..cc0490d815870 100644
--- a/src/vs/editor/common/viewModel/viewModelLines.ts
+++ b/src/vs/editor/common/viewModel/viewModelLines.ts
@@ -3,32 +3,30 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import * as arrays from '../../../base/common/arrays.js';
 import { IDisposable } from '../../../base/common/lifecycle.js';
-import { WrappingIndent } from '../config/editorOptions.js';
-import { FontInfo } from '../config/fontInfo.js';
+import { EditorOption, IComputedEditorOptions } from '../config/editorOptions.js';
 import { IPosition, Position } from '../core/position.js';
 import { Range } from '../core/range.js';
 import { IModelDecoration, IModelDeltaDecoration, ITextModel, PositionAffinity } from '../model.js';
 import { IActiveIndentGuideInfo, BracketGuideOptions, IndentGuide, IndentGuideHorizontalLine } from '../textModelGuides.js';
 import { ModelDecorationOptions } from '../model/textModel.js';
-import { LineInjectedText } from '../textModelEvents.js';
 import * as viewEvents from '../viewEvents.js';
 import { createModelLineProjection, IModelLineProjection } from './modelLineProjection.js';
-import { ILineBreaksComputer, ModelLineProjectionData, InjectedText, ILineBreaksComputerFactory } from '../modelLineProjectionData.js';
+import { ILineBreaksComputer, ModelLineProjectionData, InjectedText, ILineBreaksComputerFactory, ILineBreaksComputerContext } from '../modelLineProjectionData.js';
 import { ConstantTimePrefixSumComputer } from '../model/prefixSumComputer.js';
 import { ViewLineData } from '../viewModel.js';
 import { ICoordinatesConverter, IdentityCoordinatesConverter } from '../coordinatesConverter.js';
+import { LineInjectedText } from '../textModelEvents.js';
 
 export interface IViewModelLines extends IDisposable {
 	createCoordinatesConverter(): ICoordinatesConverter;
 
-	setWrappingSettings(fontInfo: FontInfo, wrappingStrategy: 'simple' | 'advanced', wrappingColumn: number, wrappingIndent: WrappingIndent, wordBreak: 'normal' | 'keepAll'): boolean;
+	setWrappingSettings(options: IComputedEditorOptions): boolean;
 	setTabSize(newTabSize: number): boolean;
 	getHiddenAreas(): Range[];
 	setHiddenAreas(_ranges: readonly Range[]): boolean;
 
-	createLineBreaksComputer(): ILineBreaksComputer;
+	createLineBreaksComputer(context?: ILineBreaksComputerContext): ILineBreaksComputer;
 	onModelFlushed(): void;
 	onModelLinesDeleted(versionId: number | null, fromLineNumber: number, toLineNumber: number): viewEvents.ViewLinesDeletedEvent | null;
 	onModelLinesInserted(versionId: number | null, fromLineNumber: number, toLineNumber: number, lineBreaks: (ModelLineProjectionData | null)[]): viewEvents.ViewLinesInsertedEvent | null;
@@ -66,13 +64,8 @@ export class ViewModelLinesFromProjectedModel implements IViewModelLines {
 	private readonly _domLineBreaksComputerFactory: ILineBreaksComputerFactory;
 	private readonly _monospaceLineBreaksComputerFactory: ILineBreaksComputerFactory;
 
-	private fontInfo: FontInfo;
+	private options: IComputedEditorOptions;
 	private tabSize: number;
-	private wrappingColumn: number;
-	private wrappingIndent: WrappingIndent;
-	private wordBreak: 'normal' | 'keepAll';
-	private wrappingStrategy: 'simple' | 'advanced';
-	private wrapOnEscapedLineFeeds: boolean;
 
 	private modelLineProjections!: IModelLineProjection[];
 
@@ -88,26 +81,16 @@ export class ViewModelLinesFromProjectedModel implements IViewModelLines {
 		model: ITextModel,
 		domLineBreaksComputerFactory: ILineBreaksComputerFactory,
 		monospaceLineBreaksComputerFactory: ILineBreaksComputerFactory,
-		fontInfo: FontInfo,
+		options: IComputedEditorOptions,
 		tabSize: number,
-		wrappingStrategy: 'simple' | 'advanced',
-		wrappingColumn: number,
-		wrappingIndent: WrappingIndent,
-		wordBreak: 'normal' | 'keepAll',
-		wrapOnEscapedLineFeeds: boolean
 	) {
 		this._editorId = editorId;
 		this.model = model;
 		this._validModelVersionId = -1;
 		this._domLineBreaksComputerFactory = domLineBreaksComputerFactory;
 		this._monospaceLineBreaksComputerFactory = monospaceLineBreaksComputerFactory;
-		this.fontInfo = fontInfo;
+		this.options = options;
 		this.tabSize = tabSize;
-		this.wrappingStrategy = wrappingStrategy;
-		this.wrappingColumn = wrappingColumn;
-		this.wrappingIndent = wrappingIndent;
-		this.wordBreak = wordBreak;
-		this.wrapOnEscapedLineFeeds = wrapOnEscapedLineFeeds;
 
 		this._constructLines(/*resetHiddenAreas*/true, null);
 	}
@@ -128,14 +111,11 @@ export class ViewModelLinesFromProjectedModel implements IViewModelLines {
 		}
 
 		const linesContent = this.model.getLinesContent();
-		const injectedTextDecorations = this.model.getInjectedTextDecorations(this._editorId);
 		const lineCount = linesContent.length;
 		const lineBreaksComputer = this.createLineBreaksComputer();
 
-		const injectedTextQueue = new arrays.ArrayQueue(LineInjectedText.fromDecorations(injectedTextDecorations));
 		for (let i = 0; i < lineCount; i++) {
-			const lineInjectedText = injectedTextQueue.takeWhile(t => t.lineNumber === i + 1);
-			lineBreaksComputer.addRequest(linesContent[i], lineInjectedText, previousLineBreaks ? previousLineBreaks[i] : null);
+			lineBreaksComputer.addRequest(i + 1, previousLineBreaks ? previousLineBreaks[i] : null);
 		}
 		const linesBreaks = lineBreaksComputer.finalize();
 
@@ -278,23 +258,19 @@ export class ViewModelLinesFromProjectedModel implements IViewModelLines {
 		return true;
 	}
 
-	public setWrappingSettings(fontInfo: FontInfo, wrappingStrategy: 'simple' | 'advanced', wrappingColumn: number, wrappingIndent: WrappingIndent, wordBreak: 'normal' | 'keepAll'): boolean {
-		const equalFontInfo = this.fontInfo.equals(fontInfo);
-		const equalWrappingStrategy = (this.wrappingStrategy === wrappingStrategy);
-		const equalWrappingColumn = (this.wrappingColumn === wrappingColumn);
-		const equalWrappingIndent = (this.wrappingIndent === wrappingIndent);
-		const equalWordBreak = (this.wordBreak === wordBreak);
-		if (equalFontInfo && equalWrappingStrategy && equalWrappingColumn && equalWrappingIndent && equalWordBreak) {
+	public setWrappingSettings(options: IComputedEditorOptions): boolean {
+		const equalFontInfo = this.options.get(EditorOption.fontInfo).equals(options.get(EditorOption.fontInfo));
+		const equalWrappingStrategy = this.options.get(EditorOption.wrappingStrategy) === options.get(EditorOption.wrappingStrategy);
+		const equalWrappingInfo = this.options.get(EditorOption.wrappingInfo) === options.get(EditorOption.wrappingInfo);
+		const equalWrappingIndent = this.options.get(EditorOption.wrappingIndent) === options.get(EditorOption.wrappingIndent);
+		const equalWordBreak = this.options.get(EditorOption.wordBreak) === options.get(EditorOption.wordBreak);
+		if (equalFontInfo && equalWrappingStrategy && equalWrappingInfo && equalWrappingIndent && equalWordBreak) {
 			return false;
 		}
 
-		const onlyWrappingColumnChanged = (equalFontInfo && equalWrappingStrategy && !equalWrappingColumn && equalWrappingIndent && equalWordBreak);
+		const onlyWrappingColumnChanged = (equalFontInfo && equalWrappingStrategy && !equalWrappingInfo && equalWrappingIndent && equalWordBreak);
 
-		this.fontInfo = fontInfo;
-		this.wrappingStrategy = wrappingStrategy;
-		this.wrappingColumn = wrappingColumn;
-		this.wrappingIndent = wrappingIndent;
-		this.wordBreak = wordBreak;
+		this.options = options;
 
 		let previousLineBreaks: ((ModelLineProjectionData | null)[]) | null = null;
 		if (onlyWrappingColumnChanged) {
@@ -309,13 +285,21 @@ export class ViewModelLinesFromProjectedModel implements IViewModelLines {
 		return true;
 	}
 
-	public createLineBreaksComputer(): ILineBreaksComputer {
+	public createLineBreaksComputer(_context?: ILineBreaksComputerContext): ILineBreaksComputer {
 		const lineBreaksComputerFactory = (
-			this.wrappingStrategy === 'advanced'
+			this.options.get(EditorOption.wrappingStrategy) === 'advanced'
 				? this._domLineBreaksComputerFactory
 				: this._monospaceLineBreaksComputerFactory
 		);
-		return lineBreaksComputerFactory.createLineBreaksComputer(this.fontInfo, this.tabSize, this.wrappingColumn, this.wrappingIndent, this.wordBreak, this.wrapOnEscapedLineFeeds);
+		const context: ILineBreaksComputerContext = _context ?? {
+			getLineContent: (lineNumber: number): string => {
+				return this.model.getLineContent(lineNumber);
+			},
+			getLineInjectedText: (lineNumber: number): LineInjectedText[] => {
+				return this.model.getLineInjectedText(lineNumber, this._editorId);
+			}
+		};
+		return lineBreaksComputerFactory.createLineBreaksComputer(context, this.options, this.tabSize);
 	}
 
 	public onModelFlushed(): void {
@@ -1146,14 +1130,14 @@ export class ViewModelLinesFromModelAsIs implements IViewModelLines {
 		return false;
 	}
 
-	public setWrappingSettings(_fontInfo: FontInfo, _wrappingStrategy: 'simple' | 'advanced', _wrappingColumn: number, _wrappingIndent: WrappingIndent): boolean {
+	public setWrappingSettings(options: IComputedEditorOptions): boolean {
 		return false;
 	}
 
 	public createLineBreaksComputer(): ILineBreaksComputer {
 		const result: null[] = [];
 		return {
-			addRequest: (lineText: string, injectedText: LineInjectedText[] | null, previousLineBreakData: ModelLineProjectionData | null) => {
+			addRequest: (lineNumber: number, previousLineBreakData: ModelLineProjectionData | null) => {
 				result.push(null);
 			},
 			finalize: () => {
diff --git a/src/vs/editor/contrib/contextmenu/browser/contextmenu.ts b/src/vs/editor/contrib/contextmenu/browser/contextmenu.ts
index a1b8b00bd48b3..6bcb8223428ab 100644
--- a/src/vs/editor/contrib/contextmenu/browser/contextmenu.ts
+++ b/src/vs/editor/contrib/contextmenu/browser/contextmenu.ts
@@ -348,6 +348,19 @@ export class ContextMenuController implements IEditorContribution {
 				value: 'always'
 			}]
 		));
+		actions.push(createEnumAction<'right' | 'left'>(
+			nls.localize('context.minimap.side', "Side"),
+			minimapOptions.enabled,
+			'editor.minimap.side',
+			minimapOptions.side,
+			[{
+				label: nls.localize('context.minimap.side.right', "Right"),
+				value: 'right'
+			}, {
+				label: nls.localize('context.minimap.side.left', "Left"),
+				value: 'left'
+			}]
+		));
 
 		const useShadowDOM = this._editor.getOption(EditorOption.useShadowDOM) && !isIOS; // Do not use shadow dom on IOS #122035
 		this._contextMenuIsBeingShownCount++;
diff --git a/src/vs/editor/contrib/dropOrPasteInto/browser/postEditWidget.css b/src/vs/editor/contrib/dropOrPasteInto/browser/postEditWidget.css
index 496b989268e8f..cce094ae6dc5f 100644
--- a/src/vs/editor/contrib/dropOrPasteInto/browser/postEditWidget.css
+++ b/src/vs/editor/contrib/dropOrPasteInto/browser/postEditWidget.css
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 .post-edit-widget {
-	box-shadow: 0 0 8px 2px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	border: 1px solid var(--vscode-widget-border, transparent);
 	border-radius: 4px;
 	color: var(--vscode-button-foreground);
diff --git a/src/vs/editor/contrib/find/browser/findController.ts b/src/vs/editor/contrib/find/browser/findController.ts
index ec2ee490e1980..c504148633d2e 100644
--- a/src/vs/editor/contrib/find/browser/findController.ts
+++ b/src/vs/editor/contrib/find/browser/findController.ts
@@ -3,6 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { alert as alertFn } from '../../../../base/browser/ui/aria/aria.js';
 import { Delayer } from '../../../../base/common/async.js';
 import { KeyCode, KeyMod } from '../../../../base/common/keyCodes.js';
 import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
@@ -18,7 +19,7 @@ import { OverviewRulerLane } from '../../../common/model.js';
 import { CONTEXT_FIND_INPUT_FOCUSED, CONTEXT_FIND_WIDGET_VISIBLE, CONTEXT_REPLACE_INPUT_FOCUSED, FindModelBoundToEditorModel, FIND_IDS, ToggleCaseSensitiveKeybinding, TogglePreserveCaseKeybinding, ToggleRegexKeybinding, ToggleSearchScopeKeybinding, ToggleWholeWordKeybinding } from './findModel.js';
 import { FindOptionsWidget } from './findOptionsWidget.js';
 import { FindReplaceState, FindReplaceStateChangedEvent, INewFindReplaceState } from './findState.js';
-import { FindWidget, IFindController } from './findWidget.js';
+import { FindWidget, IFindController, NLS_NO_RESULTS } from './findWidget.js';
 import * as nls from '../../../../nls.js';
 import { MenuId } from '../../../../platform/actions/common/actions.js';
 import { IClipboardService } from '../../../../platform/clipboard/common/clipboardService.js';
@@ -725,11 +726,28 @@ async function matchFindAction(editor: ICodeEditor, next: boolean): Promise<void
 	if (!controller) {
 		return;
 	}
+	const shouldCloseOnResult = editor.getOption(EditorOption.find).closeOnResult;
+	const wasFindWidgetVisible = controller.getState().isRevealed;
 
 	const runMatch = (): boolean => {
+		const previousSelection = controller.editor.getSelection();
 		const result = next ? controller.moveToNextMatch() : controller.moveToPrevMatch();
+
+		let landedOnMatch = false;
 		if (result) {
+			const currentSelection = controller.editor.getSelection();
+			if (!previousSelection && currentSelection) {
+				landedOnMatch = true;
+			} else if (previousSelection && currentSelection && !previousSelection.equalsSelection(currentSelection)) {
+				landedOnMatch = true;
+			}
+		}
+
+		if (landedOnMatch) {
 			controller.editor.pushUndoStop();
+			if (shouldCloseOnResult && wasFindWidgetVisible && controller.isFindInputFocused()) {
+				controller.closeFindWidget();
+			}
 			return true;
 		}
 		return false;
@@ -746,7 +764,13 @@ async function matchFindAction(editor: ICodeEditor, next: boolean): Promise<void
 			updateSearchScope: false,
 			loop: editor.getOption(EditorOption.find).loop
 		});
-		runMatch();
+		if (!runMatch()) {
+			// Re-announce "no results" for screen readers on explicit navigation (#301126)
+			const state = controller.getState();
+			if (wasFindWidgetVisible && state.matchesCount === 0 && state.searchString) {
+				alertFn(nls.localize('ariaSearchNoResult', "{0} found for '{1}'", NLS_NO_RESULTS, state.searchString));
+			}
+		}
 	}
 }
 
diff --git a/src/vs/editor/contrib/find/browser/findDecorations.ts b/src/vs/editor/contrib/find/browser/findDecorations.ts
index 1940e2a315262..6ce266c699eae 100644
--- a/src/vs/editor/contrib/find/browser/findDecorations.ts
+++ b/src/vs/editor/contrib/find/browser/findDecorations.ts
@@ -103,7 +103,7 @@ export class FindDecorations implements IDisposable {
 		const candidates = this._editor.getModel().getDecorationsInRange(desiredRange);
 		for (const candidate of candidates) {
 			const candidateOpts = candidate.options;
-			if (candidateOpts === FindDecorations._FIND_MATCH_DECORATION || candidateOpts === FindDecorations._CURRENT_FIND_MATCH_DECORATION) {
+			if (candidateOpts === FindDecorations._FIND_MATCH_DECORATION || candidateOpts === FindDecorations._FIND_MATCH_NO_OVERVIEW_DECORATION || candidateOpts === FindDecorations._CURRENT_FIND_MATCH_DECORATION) {
 				return this._getDecorationIndex(candidate.id);
 			}
 		}
diff --git a/src/vs/editor/contrib/find/browser/findOptionsWidget.css b/src/vs/editor/contrib/find/browser/findOptionsWidget.css
index 2188fa9fa9db1..ac9f95c4e34ae 100644
--- a/src/vs/editor/contrib/find/browser/findOptionsWidget.css
+++ b/src/vs/editor/contrib/find/browser/findOptionsWidget.css
@@ -6,6 +6,6 @@
 .monaco-editor .findOptionsWidget {
 	background-color: var(--vscode-editorWidget-background);
 	color: var(--vscode-editorWidget-foreground);
-	box-shadow: 0 0 8px 2px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	border: 2px solid var(--vscode-contrastBorder);
 }
diff --git a/src/vs/editor/contrib/find/browser/findWidget.css b/src/vs/editor/contrib/find/browser/findWidget.css
index f1dd6191b9580..62c6056c1d98d 100644
--- a/src/vs/editor/contrib/find/browser/findWidget.css
+++ b/src/vs/editor/contrib/find/browser/findWidget.css
@@ -7,20 +7,18 @@
 .monaco-editor .find-widget {
 	position: absolute;
 	z-index: 35;
-	height: 33px;
+	height: 34px;
 	overflow: hidden;
 	line-height: 19px;
 	transition: transform 200ms linear;
 	padding: 0 4px 0 9px;
+	margin-top: 4px;
 	box-sizing: border-box;
 	transform: translateY(calc(-100% - 10px)); /* shadow (10px) */
-	box-shadow: 0 0 8px 2px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	color: var(--vscode-editorWidget-foreground);
-	border-left: 1px solid var(--vscode-widget-border);
-	border-right: 1px solid var(--vscode-widget-border);
-	border-bottom: 1px solid var(--vscode-widget-border);
-	border-bottom-left-radius: 4px;
-	border-bottom-right-radius: 4px;
+	border: 1px solid var(--vscode-widget-border);
+	border-radius: var(--vscode-cornerRadius-large);
 	background-color: var(--vscode-editorWidget-background);
 }
 
diff --git a/src/vs/editor/contrib/find/test/browser/findController.test.ts b/src/vs/editor/contrib/find/test/browser/findController.test.ts
index ed0383148f97e..1823dd31e1ab9 100644
--- a/src/vs/editor/contrib/find/test/browser/findController.test.ts
+++ b/src/vs/editor/contrib/find/test/browser/findController.test.ts
@@ -292,6 +292,67 @@ suite('FindController', () => {
 		});
 	});
 
+	test('editor.find.closeOnResult: closes find widget when a match is found from explicit navigation', async () => {
+		await withAsyncTestCodeEditor([
+			'ABC',
+			'ABC',
+			'XYZ',
+		], { serviceCollection: serviceCollection, find: { closeOnResult: true } }, async (editor, _, instantiationService) => {
+			const findController = editor.registerAndInstantiateContribution(TestFindController.ID, TestFindController);
+			const findState = findController.getState();
+
+			await executeAction(instantiationService, editor, StartFindAction);
+			assert.strictEqual(findState.isRevealed, true);
+
+			findState.change({ searchString: 'ABC' }, true);
+			await editor.runAction(NextMatchFindAction);
+
+			assert.strictEqual(findState.isRevealed, false);
+			findController.dispose();
+		});
+	});
+
+	test('editor.find.closeOnResult: keeps find widget open when no match is found', async () => {
+		await withAsyncTestCodeEditor([
+			'ABC',
+			'DEF',
+			'XYZ',
+		], { serviceCollection: serviceCollection, find: { closeOnResult: true } }, async (editor, _, instantiationService) => {
+			const findController = editor.registerAndInstantiateContribution(TestFindController.ID, TestFindController);
+			const findState = findController.getState();
+
+			await executeAction(instantiationService, editor, StartFindAction);
+			assert.strictEqual(findState.isRevealed, true);
+
+			findState.change({ searchString: 'NO_MATCH' }, true);
+			await editor.runAction(NextMatchFindAction);
+
+			assert.strictEqual(findState.matchesCount, 0);
+			assert.strictEqual(findState.isRevealed, true);
+			findController.dispose();
+		});
+	});
+
+	test('editor.find.closeOnResult: disabled keeps find widget open after navigation', async () => {
+		await withAsyncTestCodeEditor([
+			'ABC',
+			'ABC',
+			'XYZ',
+		], { serviceCollection: serviceCollection, find: { closeOnResult: false } }, async (editor, _, instantiationService) => {
+			const findController = editor.registerAndInstantiateContribution(TestFindController.ID, TestFindController);
+			const findState = findController.getState();
+
+			await executeAction(instantiationService, editor, StartFindAction);
+			assert.strictEqual(findState.isRevealed, true);
+
+			findState.change({ searchString: 'ABC' }, true);
+			await editor.runAction(NextMatchFindAction);
+
+			assert.strictEqual(findState.isRevealed, true);
+			findController.dispose();
+		});
+	});
+
 	test('issue #9043: Clear search scope when find widget is hidden', async () => {
 		await withAsyncTestCodeEditor([
 			'var x = (3 * 5)',
diff --git a/src/vs/editor/contrib/find/test/browser/findModel.test.ts b/src/vs/editor/contrib/find/test/browser/findModel.test.ts
index 09a0de5a7ae5f..8e2bbc3ccd362 100644
--- a/src/vs/editor/contrib/find/test/browser/findModel.test.ts
+++ b/src/vs/editor/contrib/find/test/browser/findModel.test.ts
@@ -2383,4 +2383,23 @@ suite('FindModel', () => {
 
 	});
 
+	test('issue #288515: Wrong current index in find widget if matches > 1000', () => {
+		// Create 1001 lines of 'hello'
+		const textArr = Array(1001).fill('hello');
+		withTestCodeEditor(textArr, {}, (_editor) => {
+			const editor = _editor as IActiveCodeEditor;
+
+			// Place cursor at line 900, selecting 'hello'
+			editor.setSelection(new Selection(900, 1, 900, 6));
+
+			const findState = disposables.add(new FindReplaceState());
+			findState.change({ searchString: 'hello' }, false);
+			disposables.add(new FindModelBoundToEditorModel(editor, findState));
+
+			assert.strictEqual(findState.matchesCount, 1001);
+			// With cursor selecting 'hello' at line 900, matchesPosition should be 900
+			assert.strictEqual(findState.matchesPosition, 900);
+		});
+	});
+
 });
diff --git a/src/vs/editor/contrib/floatingMenu/browser/floatingMenu.css b/src/vs/editor/contrib/floatingMenu/browser/floatingMenu.css
index 422e073e5e739..2182ed732e6df 100644
--- a/src/vs/editor/contrib/floatingMenu/browser/floatingMenu.css
+++ b/src/vs/editor/contrib/floatingMenu/browser/floatingMenu.css
@@ -7,16 +7,39 @@
 	padding: 2px 4px;
 	color: var(--vscode-foreground);
 	background-color: var(--vscode-editorWidget-background);
-	border-radius: 6px;
+	border-radius: var(--vscode-cornerRadius-medium);
 	border: 1px solid var(--vscode-contrastBorder);
 	display: flex;
 	align-items: center;
 	justify-content: center;
 	gap: 4px;
 	z-index: 10;
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	overflow: hidden;
 
+	&.single-button {
+		background-color: transparent;
+		border-width: 0;
+		padding: 0;
+		overflow: visible;
+
+		.action-item > .action-label,
+		.action-item > .action-label.codicon:not(.separator) {
+			height: 28px;
+			line-height: 28px;
+			border-radius: var(--vscode-cornerRadius-medium);
+			box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+		}
+
+		.action-item > .action-label {
+			padding: 0 8px;
+		}
+
+		.action-item > .action-label.codicon:not(.separator) {
+			width: 28px;
+		}
+	}
+
 	.actions-container {
 		gap: 4px;
 	}
@@ -25,7 +48,7 @@
 		padding: 4px 6px;
 		font-size: 11px;
 		line-height: 14px;
-		border-radius: 4px;
+		border-radius: var(--vscode-cornerRadius-small);
 	}
 
 	.action-item > .action-label.codicon:not(.separator) {
@@ -50,3 +73,16 @@
 		background-color: var(--vscode-button-hoverBackground) !important;
 	}
 }
+
+.hc-black .floating-menu-overlay-widget.single-button,
+.hc-light .floating-menu-overlay-widget.single-button {
+	border-width: 1px;
+	border-style: solid;
+	border-color: var(--vscode-contrastBorder);
+	background-color: var(--vscode-editorWidget-background);
+	padding: 0;
+	.action-item > .action-label,
+	.action-item > .action-label.codicon:not(.separator) {
+		box-shadow: none;
+	}
+}
diff --git a/src/vs/editor/contrib/floatingMenu/browser/floatingMenu.ts b/src/vs/editor/contrib/floatingMenu/browser/floatingMenu.ts
index 1a530186e669f..5e7be22f374a7 100644
--- a/src/vs/editor/contrib/floatingMenu/browser/floatingMenu.ts
+++ b/src/vs/editor/contrib/floatingMenu/browser/floatingMenu.ts
@@ -3,11 +3,12 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { Separator } from '../../../../base/common/actions.js';
 import { h } from '../../../../base/browser/dom.js';
 import { Disposable, toDisposable } from '../../../../base/common/lifecycle.js';
-import { getActionBarActions, MenuEntryActionViewItem } from '../../../../platform/actions/browser/menuEntryActionViewItem.js';
 import { autorun, constObservable, derived, IObservable, observableFromEvent } from '../../../../base/common/observable.js';
 import { URI } from '../../../../base/common/uri.js';
+import { getActionBarActions, MenuEntryActionViewItem } from '../../../../platform/actions/browser/menuEntryActionViewItem.js';
 import { HiddenItemStrategy, MenuWorkbenchToolBar } from '../../../../platform/actions/browser/toolbar.js';
 import { IMenuService, MenuId, MenuItemAction } from '../../../../platform/actions/common/actions.js';
 import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
@@ -75,25 +76,27 @@ export class FloatingEditorToolbarWidget extends Disposable {
 		const menu = this._register(menuService.createMenu(_menuId, _scopedContextKeyService));
 		const menuGroupsObs = observableFromEvent(this, menu.onDidChange, () => menu.getActions());
 
-		const menuPrimaryActionIdObs = derived(reader => {
+		const menuPrimaryActionsObs = derived(reader => {
 			const menuGroups = menuGroupsObs.read(reader);
-
 			const { primary } = getActionBarActions(menuGroups, () => true);
-			return primary.length > 0 ? primary[0].id : undefined;
+			return primary.filter(a => a.id !== Separator.ID);
 		});
 
-		this.hasActions = derived(reader => menuGroupsObs.read(reader).length > 0);
+		this.hasActions = derived(reader => menuPrimaryActionsObs.read(reader).length > 0);
 
 		this.element = h('div.floating-menu-overlay-widget').root;
 		this._register(toDisposable(() => this.element.remove()));
 
-		// Set height explicitly to ensure that the floating menu element
-		// is rendered in the lower right corner at the correct position.
-		this.element.style.height = '26px';
-
 		this._register(autorun(reader => {
-			const hasActions = this.hasActions.read(reader);
-			const menuPrimaryActionId = menuPrimaryActionIdObs.read(reader);
+			const primaryActions = menuPrimaryActionsObs.read(reader);
+			const hasActions = primaryActions.length > 0;
+			const menuPrimaryActionId = hasActions ? primaryActions[0].id : undefined;
+
+			const isSingleButton = primaryActions.length === 1;
+			this.element.classList.toggle('single-button', isSingleButton);
+			// Set height explicitly to ensure that the floating menu element
+			// is rendered in the lower right corner at the correct position.
+			this.element.style.height = isSingleButton ? '28px' : '26px';
 
 			if (!hasActions) {
 				return;
diff --git a/src/vs/editor/contrib/hover/browser/hover.css b/src/vs/editor/contrib/hover/browser/hover.css
index aedcb6944b324..269ee853c7ec2 100644
--- a/src/vs/editor/contrib/hover/browser/hover.css
+++ b/src/vs/editor/contrib/hover/browser/hover.css
@@ -9,20 +9,23 @@
 
 .monaco-editor .monaco-resizable-hover {
 	border: 1px solid var(--vscode-editorHoverWidget-border);
-	border-radius: 3px;
+	border-radius: var(--vscode-cornerRadius-large);
 	box-sizing: content-box;
+	background-color: var(--vscode-editorHoverWidget-background);
 }
 
 .monaco-editor .monaco-resizable-hover > .monaco-hover {
 	border: none;
-	border-radius: unset;
+	border-radius: inherit;
+	overflow: hidden;
 }
 
 .monaco-editor .monaco-hover {
 	border: 1px solid var(--vscode-editorHoverWidget-border);
-	border-radius: 3px;
+	border-radius: var(--vscode-cornerRadius-large);
 	color: var(--vscode-editorHoverWidget-foreground);
 	background-color: var(--vscode-editorHoverWidget-background);
+	box-shadow: var(--vscode-shadow-hover);
 }
 
 .monaco-editor .monaco-hover a {
@@ -34,6 +37,7 @@
 }
 
 .monaco-editor .monaco-hover .hover-row {
+	border-radius: var(--vscode-cornerRadius-large);
 	display: flex;
 }
 
diff --git a/src/vs/editor/contrib/hover/browser/hoverActionIds.ts b/src/vs/editor/contrib/hover/browser/hoverActionIds.ts
index 75b3930c79171..26eb23b7bb969 100644
--- a/src/vs/editor/contrib/hover/browser/hoverActionIds.ts
+++ b/src/vs/editor/contrib/hover/browser/hoverActionIds.ts
@@ -21,3 +21,4 @@ export const INCREASE_HOVER_VERBOSITY_ACTION_LABEL = nls.localize({ key: 'increa
 export const DECREASE_HOVER_VERBOSITY_ACTION_ID = 'editor.action.decreaseHoverVerbosityLevel';
 export const DECREASE_HOVER_VERBOSITY_ACCESSIBLE_ACTION_ID = 'editor.action.decreaseHoverVerbosityLevelFromAccessibleView';
 export const DECREASE_HOVER_VERBOSITY_ACTION_LABEL = nls.localize({ key: 'decreaseHoverVerbosityLevel', comment: ['Label for action that will decrease the hover verbosity level.'] }, "Decrease Hover Verbosity Level");
+export const HIDE_LONG_LINE_WARNING_HOVER_ACTION_ID = 'editor.action.hideLongLineWarningHover';
diff --git a/src/vs/editor/contrib/hover/browser/hoverContribution.ts b/src/vs/editor/contrib/hover/browser/hoverContribution.ts
index 9e4168a1be08b..678ffe4908d95 100644
--- a/src/vs/editor/contrib/hover/browser/hoverContribution.ts
+++ b/src/vs/editor/contrib/hover/browser/hoverContribution.ts
@@ -7,6 +7,9 @@ import { DecreaseHoverVerbosityLevel, GoToBottomHoverAction, GoToTopHoverAction,
 import { EditorContributionInstantiation, registerEditorAction, registerEditorContribution } from '../../../browser/editorExtensions.js';
 import { editorHoverBorder } from '../../../../platform/theme/common/colorRegistry.js';
 import { registerThemingParticipant } from '../../../../platform/theme/common/themeService.js';
+import { CommandsRegistry } from '../../../../platform/commands/common/commands.js';
+import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
+import { HIDE_LONG_LINE_WARNING_HOVER_ACTION_ID } from './hoverActionIds.js';
 import { HoverParticipantRegistry } from './hoverTypes.js';
 import { MarkdownHoverParticipant } from './markdownHoverParticipant.js';
 import { MarkerHoverParticipant } from './markerHoverParticipant.js';
@@ -33,6 +36,9 @@ registerEditorAction(IncreaseHoverVerbosityLevel);
 registerEditorAction(DecreaseHoverVerbosityLevel);
 HoverParticipantRegistry.register(MarkdownHoverParticipant);
 HoverParticipantRegistry.register(MarkerHoverParticipant);
+CommandsRegistry.registerCommand(HIDE_LONG_LINE_WARNING_HOVER_ACTION_ID, (accessor) => {
+	accessor.get(IConfigurationService).updateValue('editor.hover.showLongLineWarning', false);
+});
 
 // theming
 registerThemingParticipant((theme, collector) => {
diff --git a/src/vs/editor/contrib/hover/browser/markdownHoverParticipant.ts b/src/vs/editor/contrib/hover/browser/markdownHoverParticipant.ts
index ba261eaa4a44a..9cd72e14497e4 100644
--- a/src/vs/editor/contrib/hover/browser/markdownHoverParticipant.ts
+++ b/src/vs/editor/contrib/hover/browser/markdownHoverParticipant.ts
@@ -9,7 +9,7 @@ import { CancellationToken, CancellationTokenSource } from '../../../../base/com
 import { IMarkdownString, isEmptyMarkdownString, MarkdownString } from '../../../../base/common/htmlContent.js';
 import { DisposableStore, toDisposable } from '../../../../base/common/lifecycle.js';
 import { IMarkdownRendererService } from '../../../../platform/markdown/browser/markdownRenderer.js';
-import { DECREASE_HOVER_VERBOSITY_ACTION_ID, INCREASE_HOVER_VERBOSITY_ACTION_ID } from './hoverActionIds.js';
+import { DECREASE_HOVER_VERBOSITY_ACTION_ID, INCREASE_HOVER_VERBOSITY_ACTION_ID, HIDE_LONG_LINE_WARNING_HOVER_ACTION_ID } from './hoverActionIds.js';
 import { ICodeEditor } from '../../../browser/editorBrowser.js';
 import { Position } from '../../../common/core/position.js';
 import { Range } from '../../../common/core/range.js';
@@ -115,17 +115,32 @@ export class MarkdownHoverParticipant implements IEditorHoverParticipant<Markdow
 		const maxTokenizationLineLength = this._configurationService.getValue<number>('editor.maxTokenizationLineLength', {
 			overrideIdentifier: languageId
 		});
+		const showLongLineWarning = this._editor.getOption(EditorOption.hover).showLongLineWarning;
 		let stopRenderingMessage = false;
 		if (stopRenderingLineAfter >= 0 && lineLength > stopRenderingLineAfter && anchor.range.startColumn >= stopRenderingLineAfter) {
 			stopRenderingMessage = true;
-			result.push(new MarkdownHover(this, anchor.range, [{
-				value: nls.localize('stopped rendering', "Rendering paused for long line for performance reasons. This can be configured via `editor.stopRenderingLineAfter`.")
-			}], false, index++));
+			if (showLongLineWarning) {
+				result.push(new MarkdownHover(this, anchor.range, [{
+					value: nls.localize(
+						{ key: 'stopped rendering', comment: ['Please do not translate the word "command", it is part of our internal syntax which must not change', '{Locked="](command:{0})"}'] },
+						"Rendering paused for long line for performance reasons. This can be configured via `editor.stopRenderingLineAfter`. [Don't Show Again](command:{0})",
+						HIDE_LONG_LINE_WARNING_HOVER_ACTION_ID
+					),
+					isTrusted: true
+				}], false, index++));
+			}
 		}
 		if (!stopRenderingMessage && typeof maxTokenizationLineLength === 'number' && lineLength >= maxTokenizationLineLength) {
-			result.push(new MarkdownHover(this, anchor.range, [{
-				value: nls.localize('too many characters', "Tokenization is skipped for long lines for performance reasons. This can be configured via `editor.maxTokenizationLineLength`.")
-			}], false, index++));
+			if (showLongLineWarning) {
+				result.push(new MarkdownHover(this, anchor.range, [{
+					value: nls.localize(
+						{ key: 'too many characters', comment: ['Please do not translate the word "command", it is part of our internal syntax which must not change', '{Locked="](command:{0})"}'] },
+						"Tokenization is skipped for long lines for performance reasons. This can be configured via `editor.maxTokenizationLineLength`. [Don't Show Again](command:{0})",
+						HIDE_LONG_LINE_WARNING_HOVER_ACTION_ID
+					),
+					isTrusted: true
+				}], false, index++));
+			}
 		}
 
 		let isBeforeContent = false;
diff --git a/src/vs/editor/contrib/inlineCompletions/browser/model/suggestWidgetAdapter.ts b/src/vs/editor/contrib/inlineCompletions/browser/model/suggestWidgetAdapter.ts
index dcd8adce63d10..549865663123b 100644
--- a/src/vs/editor/contrib/inlineCompletions/browser/model/suggestWidgetAdapter.ts
+++ b/src/vs/editor/contrib/inlineCompletions/browser/model/suggestWidgetAdapter.ts
@@ -20,6 +20,7 @@ import { CompletionItem } from '../../../suggest/browser/suggest.js';
 import { SuggestController } from '../../../suggest/browser/suggestController.js';
 import { ObservableCodeEditor } from '../../../../browser/observableCodeEditor.js';
 import { observableFromEvent } from '../../../../../base/common/observable.js';
+import { EditorOption } from '../../../../common/config/editorOptions.js';
 
 export class SuggestWidgetAdaptor extends Disposable {
 	private isSuggestWidgetVisible: boolean = false;
@@ -149,6 +150,17 @@ export class SuggestWidgetAdaptor extends Disposable {
 			return undefined;
 		}
 
+		// When offWhenInlineCompletions is active, don't expose the selected
+		// suggest item to the inline completions model so that it does not
+		// trigger an inline completion request while the suggest widget is open
+		const quickSuggestions = this.editor.getOption(EditorOption.quickSuggestions);
+		if (typeof quickSuggestions === 'object'
+			&& (quickSuggestions.other === 'offWhenInlineCompletions'
+				|| quickSuggestions.comments === 'offWhenInlineCompletions'
+				|| quickSuggestions.strings === 'offWhenInlineCompletions')) {
+			return undefined;
+		}
+
 		const focusedItem = suggestController.widget.value.getFocusedItem();
 		const position = this.editor.getPosition();
 		const model = this.editor.getModel();
diff --git a/src/vs/editor/contrib/inlineCompletions/test/browser/utils.ts b/src/vs/editor/contrib/inlineCompletions/test/browser/utils.ts
index f4b3115a52ad7..3f5c6ba28ceff 100644
--- a/src/vs/editor/contrib/inlineCompletions/test/browser/utils.ts
+++ b/src/vs/editor/contrib/inlineCompletions/test/browser/utils.ts
@@ -5,34 +5,34 @@
 
 import { timeout } from '../../../../../base/common/async.js';
 import { CancellationToken } from '../../../../../base/common/cancellation.js';
+import { BugIndicatingError } from '../../../../../base/common/errors.js';
+import { Emitter, Event } from '../../../../../base/common/event.js';
 import { Disposable, DisposableStore, IReference } from '../../../../../base/common/lifecycle.js';
-import { CoreEditingCommands, CoreNavigationCommands } from '../../../../browser/coreCommands.js';
-import { Position } from '../../../../common/core/position.js';
-import { ITextModel } from '../../../../common/model.js';
-import { IInlineCompletionChangeHint, InlineCompletion, InlineCompletionContext, InlineCompletions, InlineCompletionsProvider } from '../../../../common/languages.js';
-import { ITestCodeEditor, TestCodeEditorInstantiationOptions, withAsyncTestCodeEditor } from '../../../../test/browser/testCodeEditor.js';
-import { InlineCompletionsModel } from '../../browser/model/inlineCompletionsModel.js';
 import { autorun, derived } from '../../../../../base/common/observable.js';
+import { URI } from '../../../../../base/common/uri.js';
 import { runWithFakedTimers } from '../../../../../base/test/common/timeTravelScheduler.js';
 import { IAccessibilitySignalService } from '../../../../../platform/accessibilitySignal/browser/accessibilitySignalService.js';
+import { IDefaultAccountService } from '../../../../../platform/defaultAccount/common/defaultAccount.js';
+import { SyncDescriptor } from '../../../../../platform/instantiation/common/descriptors.js';
 import { ServiceCollection } from '../../../../../platform/instantiation/common/serviceCollection.js';
+import { CoreEditingCommands, CoreNavigationCommands } from '../../../../browser/coreCommands.js';
+import { IBulkEditService } from '../../../../browser/services/bulkEditService.js';
+import { IRenameSymbolTrackerService, NullRenameSymbolTrackerService } from '../../../../browser/services/renameSymbolTrackerService.js';
+import { TextEdit } from '../../../../common/core/edits/textEdit.js';
+import { Position } from '../../../../common/core/position.js';
+import { Range } from '../../../../common/core/range.js';
+import { PositionOffsetTransformer } from '../../../../common/core/text/positionToOffset.js';
+import { IInlineCompletionChangeHint, InlineCompletion, InlineCompletionContext, InlineCompletions, InlineCompletionsProvider } from '../../../../common/languages.js';
+import { ITextModel } from '../../../../common/model.js';
 import { ILanguageFeaturesService } from '../../../../common/services/languageFeatures.js';
 import { LanguageFeaturesService } from '../../../../common/services/languageFeaturesService.js';
+import { IModelService } from '../../../../common/services/model.js';
+import { IResolvedTextEditorModel, ITextModelService } from '../../../../common/services/resolverService.js';
 import { ViewModel } from '../../../../common/viewModel/viewModelImpl.js';
+import { ITestCodeEditor, TestCodeEditorInstantiationOptions, withAsyncTestCodeEditor } from '../../../../test/browser/testCodeEditor.js';
 import { InlineCompletionsController } from '../../browser/controller/inlineCompletionsController.js';
-import { Range } from '../../../../common/core/range.js';
-import { TextEdit } from '../../../../common/core/edits/textEdit.js';
-import { BugIndicatingError } from '../../../../../base/common/errors.js';
-import { PositionOffsetTransformer } from '../../../../common/core/text/positionToOffset.js';
+import { InlineCompletionsModel } from '../../browser/model/inlineCompletionsModel.js';
 import { InlineSuggestionsView } from '../../browser/view/inlineSuggestionsView.js';
-import { IBulkEditService } from '../../../../browser/services/bulkEditService.js';
-import { IDefaultAccountService } from '../../../../../platform/defaultAccount/common/defaultAccount.js';
-import { Emitter, Event } from '../../../../../base/common/event.js';
-import { IRenameSymbolTrackerService, NullRenameSymbolTrackerService } from '../../../../browser/services/renameSymbolTrackerService.js';
-import { ITextModelService, IResolvedTextEditorModel } from '../../../../common/services/resolverService.js';
-import { IModelService } from '../../../../common/services/model.js';
-import { URI } from '../../../../../base/common/uri.js';
-import { SyncDescriptor } from '../../../../../platform/instantiation/common/descriptors.js';
 
 export class MockInlineCompletionsProvider implements InlineCompletionsProvider {
 	private returnValue: InlineCompletion[] = [];
@@ -274,6 +274,8 @@ export async function withAsyncTestCodeEditorAndInlineCompletionsModel<T>(
 					onDidChangeDefaultAccount: Event.None,
 					onDidChangePolicyData: Event.None,
 					policyData: null,
+					copilotTokenInfo: null,
+					onDidChangeCopilotTokenInfo: Event.None,
 					getDefaultAccount: async () => null,
 					setDefaultAccountProvider: () => { },
 					getDefaultAccountAuthenticationProvider: () => { return { id: 'mockProvider', name: 'Mock Provider', enterprise: false }; },
diff --git a/src/vs/editor/contrib/parameterHints/browser/parameterHints.css b/src/vs/editor/contrib/parameterHints/browser/parameterHints.css
index 3efac6c122caa..31dcb1d38a9d5 100644
--- a/src/vs/editor/contrib/parameterHints/browser/parameterHints.css
+++ b/src/vs/editor/contrib/parameterHints/browser/parameterHints.css
@@ -13,6 +13,8 @@
 	color: var(--vscode-editorHoverWidget-foreground);
 	background-color: var(--vscode-editorHoverWidget-background);
 	border: 1px solid var(--vscode-editorHoverWidget-border);
+	border-radius: var(--vscode-cornerRadius-large);
+	box-shadow: var(--vscode-shadow-lg);
 }
 
 .hc-black .monaco-editor .parameter-hints-widget,
@@ -76,6 +78,9 @@
 .monaco-editor .parameter-hints-widget .docs {
 	padding: 0 10px 0 5px;
 	white-space: pre-wrap;
+	overflow-wrap: break-word;
+	word-break: break-word;
+	min-width: 0;
 }
 
 .monaco-editor .parameter-hints-widget .docs.empty {
@@ -93,6 +98,9 @@
 
 .monaco-editor .parameter-hints-widget .docs .markdown-docs {
 	white-space: initial;
+	overflow-wrap: break-word;
+	word-break: break-word;
+	max-width: 100%;
 }
 
 .monaco-editor .parameter-hints-widget .docs code {
diff --git a/src/vs/editor/contrib/peekView/browser/media/peekViewWidget.css b/src/vs/editor/contrib/peekView/browser/media/peekViewWidget.css
index f49973bfea3fe..eb777d9ac7f42 100644
--- a/src/vs/editor/contrib/peekView/browser/media/peekViewWidget.css
+++ b/src/vs/editor/contrib/peekView/browser/media/peekViewWidget.css
@@ -3,6 +3,10 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+.monaco-editor .peekview-widget {
+	box-shadow: var(--vscode-shadow-hover);
+}
+
 .monaco-editor .peekview-widget .head {
 	box-sizing: border-box;
 	display: flex;
diff --git a/src/vs/editor/contrib/rename/browser/renameWidget.css b/src/vs/editor/contrib/rename/browser/renameWidget.css
index acd375f2afb7e..730bf8895b8fc 100644
--- a/src/vs/editor/contrib/rename/browser/renameWidget.css
+++ b/src/vs/editor/contrib/rename/browser/renameWidget.css
@@ -7,6 +7,7 @@
 	z-index: 100;
 	color: inherit;
 	border-radius: 4px;
+	box-shadow: var(--vscode-shadow-hover);
 }
 
 .monaco-editor .rename-box.preview {
diff --git a/src/vs/editor/contrib/semanticTokens/browser/documentSemanticTokens.ts b/src/vs/editor/contrib/semanticTokens/browser/documentSemanticTokens.ts
index 2bc7cab868a76..95348d44230af 100644
--- a/src/vs/editor/contrib/semanticTokens/browser/documentSemanticTokens.ts
+++ b/src/vs/editor/contrib/semanticTokens/browser/documentSemanticTokens.ts
@@ -6,7 +6,7 @@
 import { RunOnceScheduler } from '../../../../base/common/async.js';
 import { CancellationTokenSource } from '../../../../base/common/cancellation.js';
 import * as errors from '../../../../base/common/errors.js';
-import { Disposable, IDisposable, dispose } from '../../../../base/common/lifecycle.js';
+import { Disposable, DisposableStore, dispose } from '../../../../base/common/lifecycle.js';
 import { ResourceMap } from '../../../../base/common/map.js';
 import { StopWatch } from '../../../../base/common/stopwatch.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
@@ -27,6 +27,7 @@ import { SEMANTIC_HIGHLIGHTING_SETTING_ID, isSemanticColoringEnabled } from '../
 export class DocumentSemanticTokensFeature extends Disposable {
 
 	private readonly _watchers = new ResourceMap<ModelSemanticColoring>();
+	private readonly _providerChangeListeners = this._register(new DisposableStore());
 
 	constructor(
 		@ISemanticTokensStylingService semanticTokensStylingService: ISemanticTokensStylingService,
@@ -38,6 +39,8 @@ export class DocumentSemanticTokensFeature extends Disposable {
 	) {
 		super();
 
+		const provider = languageFeaturesService.documentSemanticTokensProvider;
+
 		const register = (model: ITextModel) => {
 			this._watchers.get(model.uri)?.dispose();
 			this._watchers.set(model.uri, new ModelSemanticColoring(model, semanticTokensStylingService, themeService, languageFeatureDebounceService, languageFeaturesService));
@@ -60,6 +63,20 @@ export class DocumentSemanticTokensFeature extends Disposable {
 				}
 			}
 		};
+
+		const bindProviderChangeListeners = () => {
+			this._providerChangeListeners.clear();
+			for (const p of provider.allNoModel()) {
+				if (typeof p.onDidChange === 'function') {
+					this._providerChangeListeners.add(p.onDidChange(() => {
+						for (const watcher of this._watchers.values()) {
+							watcher.handleProviderDidChange(p);
+						}
+					}));
+				}
+			}
+		};
+
 		modelService.getModels().forEach(model => {
 			if (isSemanticColoringEnabled(model, themeService, configurationService)) {
 				register(model);
@@ -82,6 +99,13 @@ export class DocumentSemanticTokensFeature extends Disposable {
 			}
 		}));
 		this._register(themeService.onDidColorThemeChange(handleSettingOrThemeChange));
+		bindProviderChangeListeners();
+		this._register(provider.onDidChange(() => {
+			bindProviderChangeListeners();
+			for (const watcher of this._watchers.values()) {
+				watcher.handleRegistryChange();
+			}
+		}));
 	}
 
 	override dispose(): void {
@@ -104,7 +128,7 @@ class ModelSemanticColoring extends Disposable {
 	private readonly _fetchDocumentSemanticTokens: RunOnceScheduler;
 	private _currentDocumentResponse: SemanticTokensResponse | null;
 	private _currentDocumentRequestCancellationTokenSource: CancellationTokenSource | null;
-	private _documentProvidersChangeListeners: IDisposable[];
+	private _relevantProviders = new Set<DocumentSemanticTokensProvider>();
 	private _providersChangedDuringRequest: boolean;
 
 	constructor(
@@ -123,8 +147,8 @@ class ModelSemanticColoring extends Disposable {
 		this._fetchDocumentSemanticTokens = this._register(new RunOnceScheduler(() => this._fetchDocumentSemanticTokensNow(), ModelSemanticColoring.REQUEST_MIN_DELAY));
 		this._currentDocumentResponse = null;
 		this._currentDocumentRequestCancellationTokenSource = null;
-		this._documentProvidersChangeListeners = [];
 		this._providersChangedDuringRequest = false;
+		this._updateRelevantProviders();
 
 		this._register(this._model.onDidChangeContent(() => {
 			if (!this._fetchDocumentSemanticTokens.isScheduled()) {
@@ -147,31 +171,10 @@ class ModelSemanticColoring extends Disposable {
 				this._currentDocumentRequestCancellationTokenSource = null;
 			}
 			this._setDocumentSemanticTokens(null, null, null, []);
+			this._updateRelevantProviders();
 			this._fetchDocumentSemanticTokens.schedule(0);
 		}));
 
-		const bindDocumentChangeListeners = () => {
-			dispose(this._documentProvidersChangeListeners);
-			this._documentProvidersChangeListeners = [];
-			for (const provider of this._provider.all(model)) {
-				if (typeof provider.onDidChange === 'function') {
-					this._documentProvidersChangeListeners.push(provider.onDidChange(() => {
-						if (this._currentDocumentRequestCancellationTokenSource) {
-							// there is already a request running,
-							this._providersChangedDuringRequest = true;
-							return;
-						}
-						this._fetchDocumentSemanticTokens.schedule(0);
-					}));
-				}
-			}
-		};
-		bindDocumentChangeListeners();
-		this._register(this._provider.onDidChange(() => {
-			bindDocumentChangeListeners();
-			this._fetchDocumentSemanticTokens.schedule(this._debounceInformation.get(this._model));
-		}));
-
 		this._register(themeService.onDidColorThemeChange(_ => {
 			// clear out existing tokens
 			this._setDocumentSemanticTokens(null, null, null, []);
@@ -181,6 +184,27 @@ class ModelSemanticColoring extends Disposable {
 		this._fetchDocumentSemanticTokens.schedule(0);
 	}
 
+	public handleRegistryChange(): void {
+		this._updateRelevantProviders();
+		this._fetchDocumentSemanticTokens.schedule(this._debounceInformation.get(this._model));
+	}
+
+	public handleProviderDidChange(provider: DocumentSemanticTokensProvider): void {
+		if (!this._relevantProviders.has(provider)) {
+			return;
+		}
+		if (this._currentDocumentRequestCancellationTokenSource) {
+			// there is already a request running,
+			this._providersChangedDuringRequest = true;
+			return;
+		}
+		this._fetchDocumentSemanticTokens.schedule(0);
+	}
+
+	private _updateRelevantProviders(): void {
+		this._relevantProviders = new Set(this._provider.all(this._model));
+	}
+
 	public override dispose(): void {
 		if (this._currentDocumentResponse) {
 			this._currentDocumentResponse.dispose();
@@ -190,8 +214,6 @@ class ModelSemanticColoring extends Disposable {
 			this._currentDocumentRequestCancellationTokenSource.cancel();
 			this._currentDocumentRequestCancellationTokenSource = null;
 		}
-		dispose(this._documentProvidersChangeListeners);
-		this._documentProvidersChangeListeners = [];
 		this._setDocumentSemanticTokens(null, null, null, []);
 		this._isDisposed = true;
 
diff --git a/src/vs/editor/contrib/snippet/test/browser/snippetVariables.test.ts b/src/vs/editor/contrib/snippet/test/browser/snippetVariables.test.ts
index 93ec32ae65e28..89c480c64c4e1 100644
--- a/src/vs/editor/contrib/snippet/test/browser/snippetVariables.test.ts
+++ b/src/vs/editor/contrib/snippet/test/browser/snippetVariables.test.ts
@@ -371,6 +371,7 @@ suite('Snippet Variables Resolver', function () {
 			getCompleteWorkspace = this._throw;
 			getWorkspace(): IWorkspace { return workspace; }
 			getWorkbenchState = this._throw;
+			hasWorkspaceData = this._throw;
 			getWorkspaceFolder = this._throw;
 			isCurrentWorkspace = this._throw;
 			isInsideWorkspace = this._throw;
diff --git a/src/vs/editor/contrib/stickyScroll/browser/stickyScroll.css b/src/vs/editor/contrib/stickyScroll/browser/stickyScroll.css
index ecc59245decf8..1cd84683e709c 100644
--- a/src/vs/editor/contrib/stickyScroll/browser/stickyScroll.css
+++ b/src/vs/editor/contrib/stickyScroll/browser/stickyScroll.css
@@ -7,7 +7,7 @@
 	overflow: hidden;
 	border-bottom: 1px solid var(--vscode-editorStickyScroll-border);
 	width: 100%;
-	box-shadow: var(--vscode-editorStickyScroll-shadow) 0 4px 2px -2px;
+	box-shadow: var(--vscode-shadow-md);
 	z-index: 4;
 	right: initial !important;
 	margin-left: '0px';
diff --git a/src/vs/editor/contrib/suggest/browser/media/suggest.css b/src/vs/editor/contrib/suggest/browser/media/suggest.css
index 755c457fc20bd..70f27a8fa869a 100644
--- a/src/vs/editor/contrib/suggest/browser/media/suggest.css
+++ b/src/vs/editor/contrib/suggest/browser/media/suggest.css
@@ -10,7 +10,8 @@
 	z-index: 40;
 	display: flex;
 	flex-direction: column;
-	border-radius: 3px;
+	border-radius: var(--vscode-cornerRadius-large);
+	box-shadow: var(--vscode-shadow-lg);
 }
 
 .monaco-editor .suggest-widget.message {
@@ -96,6 +97,7 @@
 .monaco-editor .suggest-widget .monaco-list {
 	user-select: none;
 	-webkit-user-select: none;
+	border-radius: var(--vscode-cornerRadius-large);
 }
 
 /** Styles for each row in the list element **/
diff --git a/src/vs/editor/contrib/suggest/browser/suggestModel.ts b/src/vs/editor/contrib/suggest/browser/suggestModel.ts
index 30c1276d5c4fd..595b7ef51c9f3 100644
--- a/src/vs/editor/contrib/suggest/browser/suggestModel.ts
+++ b/src/vs/editor/contrib/suggest/browser/suggestModel.ts
@@ -3,7 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { TimeoutTimer } from '../../../../base/common/async.js';
+import { TimeoutTimer, disposableTimeout } from '../../../../base/common/async.js';
 import { CancellationTokenSource } from '../../../../base/common/cancellation.js';
 import { onUnexpectedError } from '../../../../base/common/errors.js';
 import { Emitter, Event } from '../../../../base/common/event.js';
@@ -30,8 +30,10 @@ import { ILanguageFeaturesService } from '../../../common/services/languageFeatu
 import { FuzzyScoreOptions } from '../../../../base/common/filters.js';
 import { assertType } from '../../../../base/common/types.js';
 import { InlineCompletionContextKeys } from '../../inlineCompletions/browser/controller/inlineCompletionContextKeys.js';
+import { getInlineCompletionsController } from '../../inlineCompletions/browser/controller/common.js';
 import { SnippetController2 } from '../../snippet/browser/snippetController2.js';
 import { IEnvironmentService } from '../../../../platform/environment/common/environment.js';
+import { autorun } from '../../../../base/common/observable.js';
 
 export interface ICancelEvent {
 	readonly retrigger: boolean;
@@ -134,6 +136,7 @@ export class SuggestModel implements IDisposable {
 	private readonly _toDispose = new DisposableStore();
 	private readonly _triggerCharacterListener = new DisposableStore();
 	private readonly _triggerQuickSuggest = new TimeoutTimer();
+	private _waitForInlineCompletions: DisposableStore | undefined;
 
 	private _triggerState: SuggestTriggerOptions | undefined = undefined;
 	private _requestToken?: CancellationTokenSource;
@@ -209,6 +212,7 @@ export class SuggestModel implements IDisposable {
 	dispose(): void {
 		dispose(this._triggerCharacterListener);
 		dispose([this._onDidCancel, this._onDidSuggest, this._onDidTrigger, this._triggerQuickSuggest]);
+		this._waitForInlineCompletions?.dispose();
 		this._toDispose.dispose();
 		this._completionDisposables.dispose();
 		this.cancel();
@@ -310,8 +314,11 @@ export class SuggestModel implements IDisposable {
 	}
 
 	cancel(retrigger: boolean = false): void {
+		this._triggerQuickSuggest.cancel();
+		this._waitForInlineCompletions?.dispose();
+		this._waitForInlineCompletions = undefined;
+
 		if (this._triggerState !== undefined) {
-			this._triggerQuickSuggest.cancel();
 			this._requestToken?.cancel();
 			this._requestToken = undefined;
 			this._triggerState = undefined;
@@ -391,6 +398,10 @@ export class SuggestModel implements IDisposable {
 
 		this.cancel();
 
+		// Cancel any in-flight wait for inline completions from a previous cycle
+		this._waitForInlineCompletions?.dispose();
+		this._waitForInlineCompletions = undefined;
+
 		this._triggerQuickSuggest.cancelAndSet(() => {
 			if (this._triggerState !== undefined) {
 				return;
@@ -409,16 +420,19 @@ export class SuggestModel implements IDisposable {
 				return;
 			}
 
+			let waitForInlineCompletions = false;
 			if (!QuickSuggestionsOptions.isAllOn(config)) {
 				// Check the type of the token that triggered this
 				model.tokenization.tokenizeIfCheap(pos.lineNumber);
 				const lineTokens = model.tokenization.getLineTokens(pos.lineNumber);
 				const tokenType = lineTokens.getStandardTokenType(lineTokens.findTokenIndexAtOffset(Math.max(pos.column - 1 - 1, 0)));
-				if (QuickSuggestionsOptions.valueFor(config, tokenType) !== 'on') {
-					if (QuickSuggestionsOptions.valueFor(config, tokenType) !== 'offWhenInlineCompletions'
-						|| (this._languageFeaturesService.inlineCompletionsProvider.has(model) && this._editor.getOption(EditorOption.inlineSuggest).enabled)) {
-						return;
-					}
+				const value = QuickSuggestionsOptions.valueFor(config, tokenType);
+				if (value === 'off' || value === 'inline') {
+					return;
+				}
+				if (value === 'offWhenInlineCompletions') {
+					waitForInlineCompletions = this._languageFeaturesService.inlineCompletionsProvider.has(model)
+						&& this._editor.getOption(EditorOption.inlineSuggest).enabled;
 				}
 			}
 
@@ -431,12 +445,73 @@ export class SuggestModel implements IDisposable {
 				return;
 			}
 
-			// we made it till here -> trigger now
-			this.trigger({ auto: true });
+			if (waitForInlineCompletions) {
+				// Wait for inline completions to resolve before deciding
+				this._waitForInlineCompletionsAndTrigger(model, pos);
+			} else {
+				this.trigger({ auto: true });
+			}
 
 		}, this._editor.getOption(EditorOption.quickSuggestionsDelay));
 	}
 
+	private _waitForInlineCompletionsAndTrigger(initialModel: ITextModel, initialPosition: Position): void {
+		const initialModelVersion = initialModel.getVersionId();
+		const inlineController = getInlineCompletionsController(this._editor);
+		const inlineModel = inlineController?.model.get();
+		if (!inlineModel) {
+			this.trigger({ auto: true });
+			return;
+		}
+
+		const state = inlineModel.state.get();
+		if (state?.inlineSuggestion) {
+			// Inline completions are already showing - suppress
+			return;
+		}
+
+		const store = new DisposableStore();
+		this._waitForInlineCompletions = store;
+
+		const triggerAndCleanUp = (doTrigger: boolean) => {
+			store.dispose();
+			if (this._waitForInlineCompletions === store) {
+				this._waitForInlineCompletions = undefined;
+			}
+			if (this._triggerState !== undefined) {
+				return;
+			}
+			if (!doTrigger) {
+				return;
+			}
+			const currentModel = this._editor.getModel();
+			const currentPosition = this._editor.getPosition();
+			if (currentModel === initialModel
+				&& currentModel.getVersionId() === initialModelVersion
+				&& currentPosition?.equals(initialPosition)
+				&& this._editor.hasWidgetFocus()
+			) {
+				this.trigger({ auto: true });
+			}
+		};
+
+		// Race: observe inline completions state vs 750ms timeout
+		disposableTimeout(() => {
+			triggerAndCleanUp(true);
+			inlineModel.stop('automatic');
+		}, 750, store);
+
+		store.add(autorun(reader => {
+			const status = inlineModel.status.read(reader);
+			const currentState = inlineModel.state.read(reader);
+			if (!currentState && status === 'loading') {
+				// Still loading
+				return;
+			}
+			triggerAndCleanUp(!currentState);
+		}));
+	}
+
 	private _refilterCompletionItems(): void {
 		assertType(this._editor.hasModel());
 		assertType(this._triggerState !== undefined);
diff --git a/src/vs/editor/contrib/suggest/test/browser/suggestModel.test.ts b/src/vs/editor/contrib/suggest/test/browser/suggestModel.test.ts
index ff465706c0c28..d99d63f7c9836 100644
--- a/src/vs/editor/contrib/suggest/test/browser/suggestModel.test.ts
+++ b/src/vs/editor/contrib/suggest/test/browser/suggestModel.test.ts
@@ -25,7 +25,7 @@ import { SuggestController } from '../../browser/suggestController.js';
 import { ISuggestMemoryService } from '../../browser/suggestMemory.js';
 import { LineContext, SuggestModel } from '../../browser/suggestModel.js';
 import { ISelectedSuggestion } from '../../browser/suggestWidget.js';
-import { createTestCodeEditor, ITestCodeEditor } from '../../../../test/browser/testCodeEditor.js';
+import { createTestCodeEditor, ITestCodeEditor, withAsyncTestCodeEditor } from '../../../../test/browser/testCodeEditor.js';
 import { createModelServices, createTextModel, instantiateTextModel } from '../../../../test/common/testTextModel.js';
 import { ServiceCollection } from '../../../../../platform/instantiation/common/serviceCollection.js';
 import { IKeybindingService } from '../../../../../platform/keybinding/common/keybinding.js';
@@ -42,6 +42,15 @@ import { getSnippetSuggestSupport, setSnippetSuggestSupport } from '../../browse
 import { IEnvironmentService } from '../../../../../platform/environment/common/environment.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
 import { runWithFakedTimers } from '../../../../../base/test/common/timeTravelScheduler.js';
+import { timeout } from '../../../../../base/common/async.js';
+import { InlineCompletionsController } from '../../../inlineCompletions/browser/controller/inlineCompletionsController.js';
+import { InlineSuggestionsView } from '../../../inlineCompletions/browser/view/inlineSuggestionsView.js';
+import { IAccessibilitySignalService } from '../../../../../platform/accessibilitySignal/browser/accessibilitySignalService.js';
+import { IMenuService, IMenu } from '../../../../../platform/actions/common/actions.js';
+import { ILogService, NullLogService } from '../../../../../platform/log/common/log.js';
+import { IEditorWorkerService } from '../../../../common/services/editorWorker.js';
+import { IDefaultAccountService } from '../../../../../platform/defaultAccount/common/defaultAccount.js';
+import { ModifierKeyEmitter } from '../../../../../base/browser/dom.js';
 
 
 function createMockEditor(model: TextModel, languageFeaturesService: ILanguageFeaturesService): ITestCodeEditor {
@@ -1230,11 +1239,11 @@ suite('SuggestModel - TriggerAndCancelOracle', function () {
 		});
 	});
 
-	test('offWhenInlineCompletions - suppresses quick suggest when inline provider exists', function () {
+	test('offWhenInlineCompletions - allows quick suggest when inline provider returns empty results', function () {
 
 		disposables.add(registry.register({ scheme: 'test' }, alwaysSomethingSupport));
 
-		// Register a dummy inline completions provider
+		// Register a dummy inline completions provider that returns no items
 		const inlineProvider: InlineCompletionsProvider = {
 			provideInlineCompletions: () => ({ items: [] }),
 			disposeInlineCompletions: () => { }
@@ -1244,20 +1253,12 @@ suite('SuggestModel - TriggerAndCancelOracle', function () {
 		return withOracle((suggestOracle, editor) => {
 			editor.updateOptions({ quickSuggestions: { comments: 'off', strings: 'off', other: 'offWhenInlineCompletions' } });
 
-			return new Promise<void>((resolve, reject) => {
-				const unexpectedSuggestSub = suggestOracle.onDidSuggest(() => {
-					unexpectedSuggestSub.dispose();
-					reject(new Error('Quick suggestions should not have been triggered'));
-				});
-
+			// Without an InlineCompletionsController, the fallback triggers immediately
+			return assertEvent(suggestOracle.onDidSuggest, () => {
 				editor.setPosition({ lineNumber: 1, column: 4 });
 				editor.trigger('keyboard', Handler.Type, { text: 'd' });
-
-				// Wait for the quick suggest delay to pass without triggering
-				setTimeout(() => {
-					unexpectedSuggestSub.dispose();
-					resolve();
-				}, 200);
+			}, suggestEvent => {
+				assert.strictEqual(suggestEvent.triggerOptions.auto, true);
 			});
 		});
 	});
@@ -1336,7 +1337,7 @@ suite('SuggestModel - TriggerAndCancelOracle', function () {
 		});
 	});
 
-	test('string shorthand - "offWhenInlineCompletions" suppresses when inline provider exists', function () {
+	test('string shorthand - "offWhenInlineCompletions" allows quick suggest when inline provider returns empty', function () {
 		return runWithFakedTimers({ useFakeTimers: true }, () => {
 			disposables.add(registry.register({ scheme: 'test' }, alwaysSomethingSupport));
 
@@ -1347,24 +1348,202 @@ suite('SuggestModel - TriggerAndCancelOracle', function () {
 			disposables.add(languageFeaturesService.inlineCompletionsProvider.register({ scheme: 'test' }, inlineProvider));
 
 			return withOracle((suggestOracle, editor) => {
-				// Use string shorthand — applies to all token types
+				// Use string shorthand - applies to all token types
 				editor.updateOptions({ quickSuggestions: 'offWhenInlineCompletions' });
 
-				return new Promise<void>((resolve, reject) => {
-					const sub = suggestOracle.onDidSuggest(() => {
-						sub.dispose();
-						reject(new Error('Quick suggestions should have been suppressed by offWhenInlineCompletions shorthand'));
-					});
-
+				// Without InlineCompletionsController, the fallback triggers immediately
+				return assertEvent(suggestOracle.onDidSuggest, () => {
 					editor.setPosition({ lineNumber: 1, column: 4 });
 					editor.trigger('keyboard', Handler.Type, { text: 'd' });
+				}, suggestEvent => {
+					assert.strictEqual(suggestEvent.triggerOptions.auto, true);
+				});
+			});
+		});
+	});
+});
 
-					setTimeout(() => {
-						sub.dispose();
-						resolve();
-					}, 200);
+suite('SuggestModel - offWhenInlineCompletions with InlineCompletionsController', function () {
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	const completionProvider: CompletionItemProvider = {
+		_debugDisplayName: 'test',
+		provideCompletionItems(doc, pos): CompletionList {
+			const wordUntil = doc.getWordUntilPosition(pos);
+			return {
+				incomplete: false,
+				suggestions: [{
+					label: doc.getWordUntilPosition(pos).word,
+					kind: CompletionItemKind.Property,
+					insertText: 'foofoo',
+					range: new Range(pos.lineNumber, wordUntil.startColumn, pos.lineNumber, wordUntil.endColumn)
+				}]
+			};
+		}
+	};
+
+	async function withSuggestModelAndInlineCompletions(
+		text: string,
+		inlineProvider: InlineCompletionsProvider,
+		callback: (suggestModel: SuggestModel, editor: ITestCodeEditor) => Promise<void>,
+	): Promise<void> {
+		await runWithFakedTimers({ useFakeTimers: true }, async () => {
+			const disposableStore = new DisposableStore();
+			try {
+				const languageFeaturesService = new LanguageFeaturesService();
+				disposableStore.add(languageFeaturesService.completionProvider.register({ pattern: '**' }, completionProvider));
+				disposableStore.add(languageFeaturesService.inlineCompletionsProvider.register({ pattern: '**' }, inlineProvider));
+
+				const serviceCollection = new ServiceCollection(
+					[ILanguageFeaturesService, languageFeaturesService],
+					[ITelemetryService, NullTelemetryService],
+					[ILogService, new NullLogService()],
+					[IStorageService, disposableStore.add(new InMemoryStorageService())],
+					[IKeybindingService, new MockKeybindingService()],
+					[IEditorWorkerService, new class extends mock<IEditorWorkerService>() {
+						override computeWordRanges() {
+							return Promise.resolve({});
+						}
+					}],
+					[ISuggestMemoryService, new class extends mock<ISuggestMemoryService>() {
+						override memorize(): void { }
+						override select(): number { return 0; }
+					}],
+					[IMenuService, new class extends mock<IMenuService>() {
+						override createMenu() {
+							return new class extends mock<IMenu>() {
+								override onDidChange = Event.None;
+								override dispose() { }
+							};
+						}
+					}],
+					[ILabelService, new class extends mock<ILabelService>() { }],
+					[IWorkspaceContextService, new class extends mock<IWorkspaceContextService>() { }],
+					[IEnvironmentService, new class extends mock<IEnvironmentService>() {
+						override isBuilt: boolean = true;
+						override isExtensionDevelopment: boolean = false;
+					}],
+					[IAccessibilitySignalService, new class extends mock<IAccessibilitySignalService>() {
+						override async playSignal() { }
+						override isSoundEnabled() { return false; }
+					}],
+					[IDefaultAccountService, new class extends mock<IDefaultAccountService>() {
+						override onDidChangeDefaultAccount = Event.None;
+						override getDefaultAccount = async () => null;
+						override setDefaultAccountProvider = () => { };
+					}],
+				);
+
+				await withAsyncTestCodeEditor(text, { serviceCollection }, async (editor, _editorViewModel, instantiationService) => {
+					instantiationService.stubInstance(InlineSuggestionsView, {
+						dispose: () => { }
+					});
+					editor.registerAndInstantiateContribution(SnippetController2.ID, SnippetController2);
+					editor.registerAndInstantiateContribution(InlineCompletionsController.ID, InlineCompletionsController);
+
+					editor.hasWidgetFocus = () => true;
+					editor.updateOptions({
+						quickSuggestions: { comments: 'off', strings: 'off', other: 'offWhenInlineCompletions' },
+					});
+
+					const suggestModel = disposableStore.add(
+						editor.invokeWithinContext(accessor => accessor.get(IInstantiationService).createInstance(SuggestModel, editor))
+					);
+
+					await callback(suggestModel, editor);
 				});
+			} finally {
+				disposableStore.dispose();
+				ModifierKeyEmitter.disposeInstance();
+			}
+		});
+	}
+
+	test('suppresses quick suggest when inline completions are showing ghost text', async function () {
+		const inlineProvider: InlineCompletionsProvider = {
+			provideInlineCompletions: (model, pos) => {
+				// Return a completion that extends the current word - must be visible at cursor
+				const word = model.getWordAtPosition(pos);
+				if (!word) { return { items: [] }; }
+				return {
+					items: [{
+						insertText: word.word + 'Suffix',
+						range: new Range(pos.lineNumber, word.startColumn, pos.lineNumber, word.endColumn),
+					}]
+				};
+			},
+			disposeInlineCompletions: () => { }
+		};
+
+		await withSuggestModelAndInlineCompletions('abc def', inlineProvider, async (suggestModel, editor) => {
+			let didSuggest = false;
+			const sub = suggestModel.onDidSuggest(() => { didSuggest = true; });
+
+			editor.setPosition({ lineNumber: 1, column: 4 });
+			editor.trigger('keyboard', Handler.Type, { text: 'd' });
+
+			await timeout(200);
+
+			sub.dispose();
+			assert.strictEqual(didSuggest, false, 'Quick suggestions should have been suppressed when inline completions are showing');
+		});
+	});
+
+	test('allows quick suggest when inline completions resolve with no results', async function () {
+		const inlineProvider: InlineCompletionsProvider = {
+			provideInlineCompletions: () => ({ items: [] }),
+			disposeInlineCompletions: () => { }
+		};
+
+		await withSuggestModelAndInlineCompletions('abc def', inlineProvider, async (suggestModel, editor) => {
+			let didSuggest = false;
+			const sub = suggestModel.onDidSuggest(e => {
+				didSuggest = true;
+				assert.strictEqual(e.triggerOptions.auto, true);
+			});
+
+			editor.setPosition({ lineNumber: 1, column: 4 });
+			editor.trigger('keyboard', Handler.Type, { text: 'd' });
+
+			await timeout(200);
+
+			sub.dispose();
+			assert.strictEqual(didSuggest, true, 'Quick suggestions should have been triggered after inline completions resolved empty');
+		});
+	});
+
+	test('allows quick suggest when inlineSuggest is disabled even with provider', async function () {
+		const inlineProvider: InlineCompletionsProvider = {
+			provideInlineCompletions: (model, pos) => {
+				const word = model.getWordAtPosition(pos);
+				if (!word) { return { items: [] }; }
+				return {
+					items: [{
+						insertText: word.word + 'Suffix',
+						range: new Range(pos.lineNumber, word.startColumn, pos.lineNumber, word.endColumn),
+					}]
+				};
+			},
+			disposeInlineCompletions: () => { }
+		};
+
+		await withSuggestModelAndInlineCompletions('abc def', inlineProvider, async (suggestModel, editor) => {
+			editor.updateOptions({ inlineSuggest: { enabled: false } });
+
+			let didSuggest = false;
+			const sub = suggestModel.onDidSuggest(e => {
+				didSuggest = true;
+				assert.strictEqual(e.triggerOptions.auto, true);
 			});
+
+			editor.setPosition({ lineNumber: 1, column: 4 });
+			editor.trigger('keyboard', Handler.Type, { text: 'd' });
+
+			await timeout(200);
+
+			sub.dispose();
+			assert.strictEqual(didSuggest, true, 'Quick suggestions should have been triggered when inlineSuggest is disabled');
 		});
 	});
 });
diff --git a/src/vs/editor/standalone/browser/standaloneServices.ts b/src/vs/editor/standalone/browser/standaloneServices.ts
index 0824dfbb53337..e12a15076e4f9 100644
--- a/src/vs/editor/standalone/browser/standaloneServices.ts
+++ b/src/vs/editor/standalone/browser/standaloneServices.ts
@@ -3,106 +3,106 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import './standaloneCodeEditorService.js';
-import './standaloneLayoutService.js';
+import '../../../platform/hover/browser/hoverService.js';
 import '../../../platform/undoRedo/common/undoRedoService.js';
+import '../../browser/services/inlineCompletionsService.js';
 import '../../common/services/languageFeatureDebounce.js';
-import '../../common/services/semanticTokensStylingService.js';
 import '../../common/services/languageFeaturesService.js';
-import '../../../platform/hover/browser/hoverService.js';
-import '../../browser/services/inlineCompletionsService.js';
+import '../../common/services/semanticTokensStylingService.js';
+import './standaloneCodeEditorService.js';
+import './standaloneLayoutService.js';
 
-import * as strings from '../../../base/common/strings.js';
 import * as dom from '../../../base/browser/dom.js';
 import { StandardKeyboardEvent } from '../../../base/browser/keyboardEvent.js';
+import { mainWindow } from '../../../base/browser/window.js';
+import { IDefaultAccount, IDefaultAccountAuthenticationProvider, IPolicyData } from '../../../base/common/defaultAccount.js';
+import { onUnexpectedError } from '../../../base/common/errors.js';
 import { Emitter, Event, IValueWithChangeEvent, ValueWithChangeEvent } from '../../../base/common/event.js';
-import { ResolvedKeybinding, KeyCodeChord, Keybinding, decodeKeybinding } from '../../../base/common/keybindings.js';
-import { IDisposable, IReference, ImmortalReference, toDisposable, DisposableStore, Disposable, combinedDisposable } from '../../../base/common/lifecycle.js';
+import { KeyCodeChord, Keybinding, ResolvedKeybinding, decodeKeybinding } from '../../../base/common/keybindings.js';
+import { Disposable, DisposableStore, IDisposable, IReference, ImmortalReference, combinedDisposable, toDisposable } from '../../../base/common/lifecycle.js';
+import { ResourceMap } from '../../../base/common/map.js';
 import { OS, isLinux, isMacintosh } from '../../../base/common/platform.js';
+import { basename } from '../../../base/common/resources.js';
 import Severity from '../../../base/common/severity.js';
+import * as strings from '../../../base/common/strings.js';
 import { URI } from '../../../base/common/uri.js';
-import { IRenameSymbolTrackerService, NullRenameSymbolTrackerService } from '../../browser/services/renameSymbolTrackerService.js';
-import { IBulkEditOptions, IBulkEditResult, IBulkEditService, ResourceEdit, ResourceTextEdit } from '../../browser/services/bulkEditService.js';
-import { isDiffEditorConfigurationKey, isEditorConfigurationKey } from '../../common/config/editorConfigurationSchema.js';
-import { EditOperation, ISingleEditOperation } from '../../common/core/editOperation.js';
-import { IPosition, Position as Pos } from '../../common/core/position.js';
-import { Range } from '../../common/core/range.js';
-import { ITextModel, ITextSnapshot } from '../../common/model.js';
-import { IModelService } from '../../common/services/model.js';
-import { IResolvedTextEditorModel, ITextModelContentProvider, ITextModelService } from '../../common/services/resolverService.js';
-import { ITextResourceConfigurationService, ITextResourcePropertiesService, ITextResourceConfigurationChangeEvent } from '../../common/services/textResourceConfiguration.js';
-import { CommandsRegistry, ICommandEvent, ICommandHandler, ICommandService } from '../../../platform/commands/common/commands.js';
-import { IConfigurationChangeEvent, IConfigurationData, IConfigurationOverrides, IConfigurationService, IConfigurationModel, IConfigurationValue, ConfigurationTarget } from '../../../platform/configuration/common/configuration.js';
-import { Configuration, ConfigurationModel, ConfigurationChangeEvent } from '../../../platform/configuration/common/configurationModels.js';
-import { IContextKeyService, ContextKeyExpression } from '../../../platform/contextkey/common/contextkey.js';
-import { IConfirmation, IConfirmationResult, IDialogService, IInputResult, IPrompt, IPromptResult, IPromptWithCustomCancel, IPromptResultWithCancel, IPromptWithDefaultCancel, IPromptBaseButton } from '../../../platform/dialogs/common/dialogs.js';
-import { createDecorator, IInstantiationService, ServiceIdentifier } from '../../../platform/instantiation/common/instantiation.js';
-import { AbstractKeybindingService } from '../../../platform/keybinding/common/abstractKeybindingService.js';
-import { IKeybindingService, IKeyboardEvent, KeybindingsSchemaContribution } from '../../../platform/keybinding/common/keybinding.js';
-import { KeybindingResolver } from '../../../platform/keybinding/common/keybindingResolver.js';
-import { IKeybindingItem, KeybindingsRegistry } from '../../../platform/keybinding/common/keybindingsRegistry.js';
-import { ResolvedKeybindingItem } from '../../../platform/keybinding/common/resolvedKeybindingItem.js';
-import { USLayoutResolvedKeybinding } from '../../../platform/keybinding/common/usLayoutResolvedKeybinding.js';
-import { ILabelService, ResourceLabelFormatter, IFormatterChangeEvent, Verbosity } from '../../../platform/label/common/label.js';
-import { INotification, INotificationHandle, INotificationService, IPromptChoice, IPromptOptions, NoOpNotification, IStatusMessageOptions, INotificationSource, INotificationSourceFilter, NotificationsFilter, IStatusHandle } from '../../../platform/notification/common/notification.js';
-import { IProgressRunner, IEditorProgressService, IProgressService, IProgress, IProgressCompositeOptions, IProgressDialogOptions, IProgressNotificationOptions, IProgressOptions, IProgressStep, IProgressWindowOptions } from '../../../platform/progress/common/progress.js';
-import { ITelemetryService, TelemetryLevel } from '../../../platform/telemetry/common/telemetry.js';
-import { ISingleFolderWorkspaceIdentifier, IWorkspaceIdentifier, IWorkspace, IWorkspaceContextService, IWorkspaceFolder, IWorkspaceFoldersChangeEvent, IWorkspaceFoldersWillChangeEvent, WorkbenchState, WorkspaceFolder, STANDALONE_EDITOR_WORKSPACE_ID } from '../../../platform/workspace/common/workspace.js';
-import { ILayoutService } from '../../../platform/layout/browser/layoutService.js';
-import { StandaloneServicesNLS } from '../../common/standaloneStrings.js';
-import { basename } from '../../../base/common/resources.js';
-import { ICodeEditorService } from '../../browser/services/codeEditorService.js';
-import { ConsoleLogger, ILoggerService, ILogService, NullLoggerService } from '../../../platform/log/common/log.js';
-import { IWorkspaceTrustManagementService, IWorkspaceTrustTransitionParticipant, IWorkspaceTrustUriInfo } from '../../../platform/workspace/common/workspaceTrust.js';
-import { EditorOption } from '../../common/config/editorOptions.js';
-import { ICodeEditor, IDiffEditor } from '../../browser/editorBrowser.js';
-import { IContextMenuService, IContextViewDelegate, IContextViewService, IOpenContextView } from '../../../platform/contextview/browser/contextView.js';
-import { ContextViewService } from '../../../platform/contextview/browser/contextViewService.js';
-import { LanguageService } from '../../common/services/languageService.js';
-import { ContextMenuService } from '../../../platform/contextview/browser/contextMenuService.js';
-import { getSingletonServiceDescriptors, InstantiationType, registerSingleton } from '../../../platform/instantiation/common/extensions.js';
-import { OpenerService } from '../../browser/services/openerService.js';
-import { ILanguageService } from '../../common/languages/language.js';
-import { MarkerDecorationsService } from '../../common/services/markerDecorationsService.js';
-import { IMarkerDecorationsService } from '../../common/services/markerDecorations.js';
-import { ModelService } from '../../common/services/modelService.js';
-import { StandaloneQuickInputService } from './quickInput/standaloneQuickInputService.js';
-import { StandaloneThemeService } from './standaloneThemeService.js';
-import { IStandaloneThemeService } from '../common/standaloneTheme.js';
 import { AccessibilityService } from '../../../platform/accessibility/browser/accessibilityService.js';
 import { IAccessibilityService } from '../../../platform/accessibility/common/accessibility.js';
+import { AccessibilityModality, AccessibilitySignal, IAccessibilitySignalService, Sound } from '../../../platform/accessibilitySignal/browser/accessibilitySignalService.js';
 import { IMenuService } from '../../../platform/actions/common/actions.js';
 import { MenuService } from '../../../platform/actions/common/menuService.js';
 import { BrowserClipboardService } from '../../../platform/clipboard/browser/clipboardService.js';
 import { IClipboardService } from '../../../platform/clipboard/common/clipboardService.js';
+import { CommandsRegistry, ICommandEvent, ICommandHandler, ICommandService } from '../../../platform/commands/common/commands.js';
+import { ConfigurationTarget, IConfigurationChangeEvent, IConfigurationData, IConfigurationModel, IConfigurationOverrides, IConfigurationService, IConfigurationValue } from '../../../platform/configuration/common/configuration.js';
+import { Configuration, ConfigurationChangeEvent, ConfigurationModel } from '../../../platform/configuration/common/configurationModels.js';
+import { DefaultConfiguration } from '../../../platform/configuration/common/configurations.js';
 import { ContextKeyService } from '../../../platform/contextkey/browser/contextKeyService.js';
+import { ContextKeyExpression, IContextKeyService } from '../../../platform/contextkey/common/contextkey.js';
+import { ContextMenuService } from '../../../platform/contextview/browser/contextMenuService.js';
+import { IContextMenuService, IContextViewDelegate, IContextViewService, IOpenContextView } from '../../../platform/contextview/browser/contextView.js';
+import { ContextViewService } from '../../../platform/contextview/browser/contextViewService.js';
+import { IDataChannelService, NullDataChannelService } from '../../../platform/dataChannel/common/dataChannel.js';
+import { IDefaultAccountService } from '../../../platform/defaultAccount/common/defaultAccount.js';
+import { IConfirmation, IConfirmationResult, IDialogService, IInputResult, IPrompt, IPromptBaseButton, IPromptResult, IPromptResultWithCancel, IPromptWithCustomCancel, IPromptWithDefaultCancel } from '../../../platform/dialogs/common/dialogs.js';
+import { ExtensionKind, IEnvironmentService, IExtensionHostDebugParams } from '../../../platform/environment/common/environment.js';
 import { SyncDescriptor } from '../../../platform/instantiation/common/descriptors.js';
+import { InstantiationType, getSingletonServiceDescriptors, registerSingleton } from '../../../platform/instantiation/common/extensions.js';
+import { IInstantiationService, ServiceIdentifier, createDecorator } from '../../../platform/instantiation/common/instantiation.js';
 import { InstantiationService } from '../../../platform/instantiation/common/instantiationService.js';
 import { ServiceCollection } from '../../../platform/instantiation/common/serviceCollection.js';
+import { AbstractKeybindingService } from '../../../platform/keybinding/common/abstractKeybindingService.js';
+import { IKeybindingService, IKeyboardEvent, KeybindingsSchemaContribution } from '../../../platform/keybinding/common/keybinding.js';
+import { KeybindingResolver } from '../../../platform/keybinding/common/keybindingResolver.js';
+import { IKeybindingItem, KeybindingsRegistry } from '../../../platform/keybinding/common/keybindingsRegistry.js';
+import { ResolvedKeybindingItem } from '../../../platform/keybinding/common/resolvedKeybindingItem.js';
+import { USLayoutResolvedKeybinding } from '../../../platform/keybinding/common/usLayoutResolvedKeybinding.js';
+import { IFormatterChangeEvent, ILabelService, ResourceLabelFormatter, Verbosity } from '../../../platform/label/common/label.js';
+import { ILayoutService } from '../../../platform/layout/browser/layoutService.js';
 import { IListService, ListService } from '../../../platform/list/browser/listService.js';
+import { ConsoleLogger, ILogService, ILoggerService, NullLoggerService } from '../../../platform/log/common/log.js';
+import { LogService } from '../../../platform/log/common/logService.js';
 import { IMarkerService } from '../../../platform/markers/common/markers.js';
 import { MarkerService } from '../../../platform/markers/common/markerService.js';
+import { INotification, INotificationHandle, INotificationService, INotificationSource, INotificationSourceFilter, IPromptChoice, IPromptOptions, IStatusHandle, IStatusMessageOptions, NoOpNotification, NotificationsFilter } from '../../../platform/notification/common/notification.js';
 import { IOpenerService } from '../../../platform/opener/common/opener.js';
+import { IEditorProgressService, IProgress, IProgressCompositeOptions, IProgressDialogOptions, IProgressNotificationOptions, IProgressOptions, IProgressRunner, IProgressService, IProgressStep, IProgressWindowOptions } from '../../../platform/progress/common/progress.js';
 import { IQuickInputService } from '../../../platform/quickinput/common/quickInput.js';
 import { IStorageService, InMemoryStorageService } from '../../../platform/storage/common/storage.js';
-import { DefaultConfiguration } from '../../../platform/configuration/common/configurations.js';
-import { WorkspaceEdit } from '../../common/languages.js';
-import { AccessibilitySignal, AccessibilityModality, IAccessibilitySignalService, Sound } from '../../../platform/accessibilitySignal/browser/accessibilitySignalService.js';
-import { LogService } from '../../../platform/log/common/logService.js';
+import { ITelemetryService, TelemetryLevel } from '../../../platform/telemetry/common/telemetry.js';
+import { IUserInteractionService } from '../../../platform/userInteraction/browser/userInteractionService.js';
+import { UserInteractionService } from '../../../platform/userInteraction/browser/userInteractionServiceImpl.js';
+import { IWebWorkerService } from '../../../platform/webWorker/browser/webWorkerService.js';
+import { ISingleFolderWorkspaceIdentifier, IWorkspace, IWorkspaceContextService, IWorkspaceFolder, IWorkspaceFoldersChangeEvent, IWorkspaceFoldersWillChangeEvent, IWorkspaceIdentifier, STANDALONE_EDITOR_WORKSPACE_ID, WorkbenchState, WorkspaceFolder } from '../../../platform/workspace/common/workspace.js';
+import { IWorkspaceTrustManagementService, IWorkspaceTrustTransitionParticipant, IWorkspaceTrustUriInfo } from '../../../platform/workspace/common/workspaceTrust.js';
+import { ICodeEditor, IDiffEditor } from '../../browser/editorBrowser.js';
+import { IBulkEditOptions, IBulkEditResult, IBulkEditService, ResourceEdit, ResourceTextEdit } from '../../browser/services/bulkEditService.js';
+import { ICodeEditorService } from '../../browser/services/codeEditorService.js';
+import { OpenerService } from '../../browser/services/openerService.js';
+import { IRenameSymbolTrackerService, NullRenameSymbolTrackerService } from '../../browser/services/renameSymbolTrackerService.js';
+import { isDiffEditorConfigurationKey, isEditorConfigurationKey } from '../../common/config/editorConfigurationSchema.js';
+import { EditorOption } from '../../common/config/editorOptions.js';
+import { EditOperation, ISingleEditOperation } from '../../common/core/editOperation.js';
+import { IPosition, Position as Pos } from '../../common/core/position.js';
+import { Range } from '../../common/core/range.js';
 import { getEditorFeatures } from '../../common/editorFeatures.js';
-import { onUnexpectedError } from '../../../base/common/errors.js';
-import { ExtensionKind, IEnvironmentService, IExtensionHostDebugParams } from '../../../platform/environment/common/environment.js';
-import { mainWindow } from '../../../base/browser/window.js';
-import { ResourceMap } from '../../../base/common/map.js';
+import { WorkspaceEdit } from '../../common/languages.js';
+import { ILanguageService } from '../../common/languages/language.js';
+import { ITextModel, ITextSnapshot } from '../../common/model.js';
+import { LanguageService } from '../../common/services/languageService.js';
+import { IMarkerDecorationsService } from '../../common/services/markerDecorations.js';
+import { MarkerDecorationsService } from '../../common/services/markerDecorationsService.js';
+import { IModelService } from '../../common/services/model.js';
+import { ModelService } from '../../common/services/modelService.js';
+import { IResolvedTextEditorModel, ITextModelContentProvider, ITextModelService } from '../../common/services/resolverService.js';
+import { ITextResourceConfigurationChangeEvent, ITextResourceConfigurationService, ITextResourcePropertiesService } from '../../common/services/textResourceConfiguration.js';
 import { ITreeSitterLibraryService } from '../../common/services/treeSitter/treeSitterLibraryService.js';
-import { StandaloneTreeSitterLibraryService } from './standaloneTreeSitterLibraryService.js';
-import { IDataChannelService, NullDataChannelService } from '../../../platform/dataChannel/common/dataChannel.js';
-import { IWebWorkerService } from '../../../platform/webWorker/browser/webWorkerService.js';
+import { StandaloneServicesNLS } from '../../common/standaloneStrings.js';
+import { IStandaloneThemeService } from '../common/standaloneTheme.js';
+import { StandaloneQuickInputService } from './quickInput/standaloneQuickInputService.js';
 import { StandaloneWebWorkerService } from './services/standaloneWebWorkerService.js';
-import { IDefaultAccountService } from '../../../platform/defaultAccount/common/defaultAccount.js';
-import { IDefaultAccount, IDefaultAccountAuthenticationProvider, IPolicyData } from '../../../base/common/defaultAccount.js';
-import { IUserInteractionService } from '../../../platform/userInteraction/browser/userInteractionService.js';
-import { UserInteractionService } from '../../../platform/userInteraction/browser/userInteractionServiceImpl.js';
+import { StandaloneThemeService } from './standaloneThemeService.js';
+import { StandaloneTreeSitterLibraryService } from './standaloneTreeSitterLibraryService.js';
 
 class SimpleModel implements IResolvedTextEditorModel {
 
@@ -852,6 +852,10 @@ class StandaloneWorkspaceContextService implements IWorkspaceContextService {
 		return WorkbenchState.EMPTY;
 	}
 
+	public hasWorkspaceData(): boolean {
+		return this.getWorkbenchState() !== WorkbenchState.EMPTY;
+	}
+
 	public getWorkspaceFolder(resource: URI): IWorkspaceFolder | null {
 		return resource && resource.scheme === StandaloneWorkspaceContextService.SCHEME ? this.workspace.folders[0] : null;
 	}
@@ -1119,6 +1123,8 @@ class StandaloneDefaultAccountService implements IDefaultAccountService {
 	readonly onDidChangeDefaultAccount: Event<IDefaultAccount | null> = Event.None;
 	readonly onDidChangePolicyData: Event<IPolicyData | null> = Event.None;
 	readonly policyData: IPolicyData | null = null;
+	readonly copilotTokenInfo = null;
+	readonly onDidChangeCopilotTokenInfo: Event<null> = Event.None;
 
 	async getDefaultAccount(): Promise<IDefaultAccount | null> {
 		return null;
diff --git a/src/vs/editor/test/browser/controller/cursorMoveCommand.test.ts b/src/vs/editor/test/browser/controller/cursorMoveCommand.test.ts
index 511842715693f..f0f79d731d105 100644
--- a/src/vs/editor/test/browser/controller/cursorMoveCommand.test.ts
+++ b/src/vs/editor/test/browser/controller/cursorMoveCommand.test.ts
@@ -506,6 +506,114 @@ suite('Cursor move by blankline test', () => {
 	});
 });
 
+// Tests for 'foldedLine' unit: moves by model lines but treats each fold as a single step.
+// This is the semantics required by vim's j/k: move through visible lines, skip hidden ones.
+
+suite('Cursor move command - foldedLine unit', () => {
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	function executeFoldTest(callback: (editor: ITestCodeEditor, viewModel: ViewModel) => void): void {
+		withTestCodeEditor([
+			'line1',
+			'line2',
+			'line3',
+			'line4',
+			'line5',
+		].join('\n'), {}, (editor, viewModel) => {
+			callback(editor, viewModel);
+		});
+	}
+
+	test('move down by foldedLine skips a fold below the cursor', () => {
+		executeFoldTest((editor, viewModel) => {
+			// Line 4 is hidden (folded under line 3 as header)
+			viewModel.setHiddenAreas([new Range(4, 1, 4, 1)]);
+			moveTo(viewModel, 2, 1);
+			// j from line 2 → line 3 (visible fold header)
+			moveDownByFoldedLine(viewModel);
+			cursorEqual(viewModel, 3, 1);
+			// j from line 3 (fold header) → line 4 is hidden, lands on line 5
+			moveDownByFoldedLine(viewModel);
+			cursorEqual(viewModel, 5, 1);
+		});
+	});
+
+	test('move up by foldedLine skips a fold above the cursor', () => {
+		executeFoldTest((editor, viewModel) => {
+			// Line 3 is hidden (folded under line 2 as header)
+			viewModel.setHiddenAreas([new Range(3, 1, 3, 1)]);
+			moveTo(viewModel, 4, 1);
+			// k from line 4: line 3 is hidden, lands on line 2 (fold header)
+			moveUpByFoldedLine(viewModel);
+			cursorEqual(viewModel, 2, 1);
+			// k from line 2 → line 1
+			moveUpByFoldedLine(viewModel);
+			cursorEqual(viewModel, 1, 1);
+		});
+	});
+
+	test('move down by foldedLine with count treats each fold as one step', () => {
+		executeFoldTest((editor, viewModel) => {
+			// Line 3 is hidden
+			viewModel.setHiddenAreas([new Range(3, 1, 3, 1)]);
+			moveTo(viewModel, 1, 1);
+			// 3j from line 1: step1→2, step2→3(hidden)→4, step3→5
+			moveDownByFoldedLine(viewModel, 3);
+			cursorEqual(viewModel, 5, 1);
+		});
+	});
+
+	test('move down by foldedLine skips a multi-line fold as one step', () => {
+		executeFoldTest((editor, viewModel) => {
+			// Lines 2-4 are hidden (folded under line 1 as header)
+			viewModel.setHiddenAreas([new Range(2, 1, 4, 1)]);
+			moveTo(viewModel, 1, 1);
+			// j from line 1: lines 2-4 are all hidden, lands directly on line 5
+			moveDownByFoldedLine(viewModel);
+			cursorEqual(viewModel, 5, 1);
+		});
+	});
+
+	test('move down by foldedLine at last line stays at last line', () => {
+		executeFoldTest((editor, viewModel) => {
+			moveTo(viewModel, 5, 1);
+			moveDownByFoldedLine(viewModel);
+			cursorEqual(viewModel, 5, 1);
+		});
+	});
+
+	test('move up by foldedLine at first line stays at first line', () => {
+		executeFoldTest((editor, viewModel) => {
+			moveTo(viewModel, 1, 1);
+			moveUpByFoldedLine(viewModel);
+			cursorEqual(viewModel, 1, 1);
+		});
+	});
+
+	test('move down by foldedLine with count clamps to last visible line after fold', () => {
+		executeFoldTest((editor, viewModel) => {
+			// Lines 2-4 are hidden. Visible lines are 1 and 5.
+			viewModel.setHiddenAreas([new Range(2, 1, 4, 1)]);
+			moveTo(viewModel, 1, 1);
+			// 2j should land on line 5 and clamp there.
+			moveDownByFoldedLine(viewModel, 2);
+			cursorEqual(viewModel, 5, 1);
+		});
+	});
+
+	test('move up by foldedLine with count clamps to first visible line before fold', () => {
+		executeFoldTest((editor, viewModel) => {
+			// Lines 2-4 are hidden. Visible lines are 1 and 5.
+			viewModel.setHiddenAreas([new Range(2, 1, 4, 1)]);
+			moveTo(viewModel, 5, 1);
+			// 2k should land on line 1 and clamp there.
+			moveUpByFoldedLine(viewModel, 2);
+			cursorEqual(viewModel, 1, 1);
+		});
+	});
+});
+
 // Move command
 
 function move(viewModel: ViewModel, args: any) {
@@ -564,6 +672,14 @@ function moveDownByModelLine(viewModel: ViewModel, noOfLines: number = 1, select
 	move(viewModel, { to: CursorMove.RawDirection.Down, value: noOfLines, select: select });
 }
 
+function moveDownByFoldedLine(viewModel: ViewModel, noOfLines: number = 1, select?: boolean) {
+	move(viewModel, { to: CursorMove.RawDirection.Down, by: CursorMove.RawUnit.FoldedLine, value: noOfLines, select: select });
+}
+
+function moveUpByFoldedLine(viewModel: ViewModel, noOfLines: number = 1, select?: boolean) {
+	move(viewModel, { to: CursorMove.RawDirection.Up, by: CursorMove.RawUnit.FoldedLine, value: noOfLines, select: select });
+}
+
 function moveToTop(viewModel: ViewModel, noOfLines: number = 1, select?: boolean) {
 	move(viewModel, { to: CursorMove.RawDirection.ViewPortTop, value: noOfLines, select: select });
 }
diff --git a/src/vs/editor/test/browser/viewModel/modelLineProjection.test.ts b/src/vs/editor/test/browser/viewModel/modelLineProjection.test.ts
index 05f1deb2aa098..dfe7d94313598 100644
--- a/src/vs/editor/test/browser/viewModel/modelLineProjection.test.ts
+++ b/src/vs/editor/test/browser/viewModel/modelLineProjection.test.ts
@@ -94,14 +94,9 @@ suite('Editor ViewModel - SplitLinesCollection', () => {
 	});
 
 	function withSplitLinesCollection(text: string, callback: (model: TextModel, linesCollection: ViewModelLinesFromProjectedModel) => void): void {
-		const config = new TestConfiguration({});
-		const wrappingInfo = config.options.get(EditorOption.wrappingInfo);
-		const fontInfo = config.options.get(EditorOption.fontInfo);
+		const config = new TestConfiguration({ wrappingStrategy: 'simple' });
 		const wordWrapBreakAfterCharacters = config.options.get(EditorOption.wordWrapBreakAfterCharacters);
 		const wordWrapBreakBeforeCharacters = config.options.get(EditorOption.wordWrapBreakBeforeCharacters);
-		const wrappingIndent = config.options.get(EditorOption.wrappingIndent);
-		const wordBreak = config.options.get(EditorOption.wordBreak);
-		const wrapOnEscapedLineFeeds = config.options.get(EditorOption.wrapOnEscapedLineFeeds);
 		const lineBreaksComputerFactory = new MonospaceLineBreaksComputerFactory(wordWrapBreakBeforeCharacters, wordWrapBreakAfterCharacters);
 
 		const model = createTextModel(text);
@@ -111,13 +106,8 @@ suite('Editor ViewModel - SplitLinesCollection', () => {
 			model,
 			lineBreaksComputerFactory,
 			lineBreaksComputerFactory,
-			fontInfo,
-			model.getOptions().tabSize,
-			'simple',
-			wrappingInfo.wrappingColumn,
-			wrappingIndent,
-			wordBreak,
-			wrapOnEscapedLineFeeds
+			config.options,
+			model.getOptions().tabSize
 		);
 
 		callback(model, linesCollection);
@@ -943,14 +933,11 @@ suite('SplitLinesCollection', () => {
 		const configuration = new TestConfiguration({
 			wordWrap: wordWrap,
 			wordWrapColumn: wordWrapColumn,
-			wrappingIndent: 'indent'
+			wrappingIndent: 'indent',
+			wrappingStrategy: 'simple'
 		});
-		const wrappingInfo = configuration.options.get(EditorOption.wrappingInfo);
-		const fontInfo = configuration.options.get(EditorOption.fontInfo);
 		const wordWrapBreakAfterCharacters = configuration.options.get(EditorOption.wordWrapBreakAfterCharacters);
 		const wordWrapBreakBeforeCharacters = configuration.options.get(EditorOption.wordWrapBreakBeforeCharacters);
-		const wrappingIndent = configuration.options.get(EditorOption.wrappingIndent);
-		const wordBreak = configuration.options.get(EditorOption.wordBreak);
 
 		const lineBreaksComputerFactory = new MonospaceLineBreaksComputerFactory(wordWrapBreakBeforeCharacters, wordWrapBreakAfterCharacters);
 
@@ -959,13 +946,8 @@ suite('SplitLinesCollection', () => {
 			model,
 			lineBreaksComputerFactory,
 			lineBreaksComputerFactory,
-			fontInfo,
-			model.getOptions().tabSize,
-			'simple',
-			wrappingInfo.wrappingColumn,
-			wrappingIndent,
-			wordBreak,
-			wrapOnEscapedLineFeeds
+			configuration.options,
+			model.getOptions().tabSize
 		);
 
 		callback(linesCollection);
diff --git a/src/vs/editor/test/common/viewModel/monospaceLineBreaksComputer.test.ts b/src/vs/editor/test/browser/viewModel/monospaceLineBreaksComputer.test.ts
similarity index 94%
rename from src/vs/editor/test/common/viewModel/monospaceLineBreaksComputer.test.ts
rename to src/vs/editor/test/browser/viewModel/monospaceLineBreaksComputer.test.ts
index bed861e44a1bf..7934cc6867461 100644
--- a/src/vs/editor/test/common/viewModel/monospaceLineBreaksComputer.test.ts
+++ b/src/vs/editor/test/browser/viewModel/monospaceLineBreaksComputer.test.ts
@@ -4,10 +4,11 @@
  *--------------------------------------------------------------------------------------------*/
 import assert from 'assert';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../base/test/common/utils.js';
-import { EditorOptions, WrappingIndent } from '../../../common/config/editorOptions.js';
+import { EditorOption, EditorOptions, WrappingIndent } from '../../../common/config/editorOptions.js';
 import { FontInfo } from '../../../common/config/fontInfo.js';
-import { ILineBreaksComputerFactory, ModelLineProjectionData } from '../../../common/modelLineProjectionData.js';
+import { ILineBreaksComputerContext, ILineBreaksComputerFactory, ModelLineProjectionData } from '../../../common/modelLineProjectionData.js';
 import { MonospaceLineBreaksComputerFactory } from '../../../common/viewModel/monospaceLineBreaksComputer.js';
+import { ComputedEditorOptions } from '../../../browser/config/editorConfiguration.js';
 
 function parseAnnotatedText(annotatedText: string): { text: string; indices: number[] } {
 	let text = '';
@@ -63,9 +64,29 @@ function getLineBreakData(factory: ILineBreaksComputerFactory, tabSize: number,
 		wsmiddotWidth: 7,
 		maxDigitWidth: 7
 	}, false);
-	const lineBreaksComputer = factory.createLineBreaksComputer(fontInfo, tabSize, breakAfter, wrappingIndent, wordBreak, wrapOnEscapedLineFeeds);
+	const context: ILineBreaksComputerContext = {
+		getLineContent(lineNumber: number) {
+			return text;
+		},
+		getLineInjectedText(lineNumber) {
+			return null;
+		}
+	};
+	const options = new ComputedEditorOptions();
+	options._write(EditorOption.fontInfo, fontInfo);
+	options._write(EditorOption.wrappingIndent, wrappingIndent);
+	options._write(EditorOption.wordWrapColumn, breakAfter);
+	options._write(EditorOption.wordBreak, wordBreak);
+	options._write(EditorOption.wrapOnEscapedLineFeeds, wrapOnEscapedLineFeeds);
+	options._write(EditorOption.wrappingInfo, {
+		isDominatedByLongLines: false,
+		isWordWrapMinified: false,
+		isViewportWrapping: false,
+		wrappingColumn: breakAfter,
+	});
+	const lineBreaksComputer = factory.createLineBreaksComputer(context, options, tabSize);
 	const previousLineBreakDataClone = previousLineBreakData ? new ModelLineProjectionData(null, null, previousLineBreakData.breakOffsets.slice(0), previousLineBreakData.breakOffsetsVisibleColumn.slice(0), previousLineBreakData.wrappedTextIndentLength) : null;
-	lineBreaksComputer.addRequest(text, null, previousLineBreakDataClone);
+	lineBreaksComputer.addRequest(1, previousLineBreakDataClone);
 	return lineBreaksComputer.finalize()[0];
 }
 
diff --git a/src/vs/editor/test/common/model/model.test.ts b/src/vs/editor/test/common/model/model.test.ts
index 72140c2636000..953e761c4085d 100644
--- a/src/vs/editor/test/common/model/model.test.ts
+++ b/src/vs/editor/test/common/model/model.test.ts
@@ -130,7 +130,7 @@ suite('Editor Model - Model', () => {
 		});
 		assert.deepStrictEqual(e, new ModelRawContentChangedEvent(
 			[
-				new ModelRawLineChanged(1, 1, 'foo My First Line', null)
+				new ModelRawLineChanged(1, 1)
 			],
 			2,
 			false,
@@ -144,8 +144,8 @@ suite('Editor Model - Model', () => {
 		});
 		assert.deepStrictEqual(e, new ModelRawContentChangedEvent(
 			[
-				new ModelRawLineChanged(1, 1, 'My new line', null),
-				new ModelRawLinesInserted(2, 2, 1, ['No longer First Line'], [null]),
+				new ModelRawLineChanged(1, 1),
+				new ModelRawLinesInserted(2, 2, 1),
 			],
 			2,
 			false,
@@ -216,7 +216,7 @@ suite('Editor Model - Model', () => {
 		});
 		assert.deepStrictEqual(e, new ModelRawContentChangedEvent(
 			[
-				new ModelRawLineChanged(1, 1, 'y First Line', null),
+				new ModelRawLineChanged(1, 1),
 			],
 			2,
 			false,
@@ -230,7 +230,7 @@ suite('Editor Model - Model', () => {
 		});
 		assert.deepStrictEqual(e, new ModelRawContentChangedEvent(
 			[
-				new ModelRawLineChanged(1, 1, '', null),
+				new ModelRawLineChanged(1, 1),
 			],
 			2,
 			false,
@@ -244,8 +244,8 @@ suite('Editor Model - Model', () => {
 		});
 		assert.deepStrictEqual(e, new ModelRawContentChangedEvent(
 			[
-				new ModelRawLineChanged(1, 1, 'My Second Line', null),
-				new ModelRawLinesDeleted(2, 2),
+				new ModelRawLineChanged(1, 1),
+				new ModelRawLinesDeleted(2, 2, 1),
 			],
 			2,
 			false,
@@ -259,8 +259,8 @@ suite('Editor Model - Model', () => {
 		});
 		assert.deepStrictEqual(e, new ModelRawContentChangedEvent(
 			[
-				new ModelRawLineChanged(1, 1, 'My Third Line', null),
-				new ModelRawLinesDeleted(2, 3),
+				new ModelRawLineChanged(1, 1),
+				new ModelRawLinesDeleted(2, 3, 1),
 			],
 			2,
 			false,
diff --git a/src/vs/editor/test/common/model/modelInjectedText.test.ts b/src/vs/editor/test/common/model/modelInjectedText.test.ts
index d01509f642110..f67efe5677f91 100644
--- a/src/vs/editor/test/common/model/modelInjectedText.test.ts
+++ b/src/vs/editor/test/common/model/modelInjectedText.test.ts
@@ -8,7 +8,7 @@ import { mock } from '../../../../base/test/common/mock.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../base/test/common/utils.js';
 import { EditOperation } from '../../../common/core/editOperation.js';
 import { Range } from '../../../common/core/range.js';
-import { InternalModelContentChangeEvent, LineInjectedText, ModelInjectedTextChangedEvent, ModelRawChange, RawContentChangedType } from '../../../common/textModelEvents.js';
+import { InternalModelContentChangeEvent, ModelInjectedTextChangedEvent, ModelRawChange, RawContentChangedType } from '../../../common/textModelEvents.js';
 import { IViewModel } from '../../../common/viewModel.js';
 import { createTextModel } from '../testTextModel.js';
 
@@ -43,8 +43,8 @@ suite('Editor Model - Injected Text Events', () => {
 		assert.deepStrictEqual(recordedChanges.splice(0), [
 			{
 				kind: 'lineChanged',
-				line: '[injected1]First Line',
 				lineNumber: 1,
+				lineNumberPostEdit: 1,
 			}
 		]);
 
@@ -67,13 +67,13 @@ suite('Editor Model - Injected Text Events', () => {
 		assert.deepStrictEqual(recordedChanges.splice(0), [
 			{
 				kind: 'lineChanged',
-				line: 'First Line',
 				lineNumber: 1,
+				lineNumberPostEdit: 1,
 			},
 			{
 				kind: 'lineChanged',
-				line: '[injected1]S[injected2]econd Line',
 				lineNumber: 2,
+				lineNumberPostEdit: 2,
 			}
 		]);
 
@@ -82,8 +82,8 @@ suite('Editor Model - Injected Text Events', () => {
 		assert.deepStrictEqual(recordedChanges.splice(0), [
 			{
 				kind: 'lineChanged',
-				line: '[injected1]SHello[injected2]econd Line',
 				lineNumber: 2,
+				lineNumberPostEdit: 2,
 			}
 		]);
 
@@ -100,17 +100,13 @@ suite('Editor Model - Injected Text Events', () => {
 		assert.deepStrictEqual(recordedChanges.splice(0), [
 			{
 				kind: 'lineChanged',
-				line: '[injected1]S',
 				lineNumber: 2,
+				lineNumberPostEdit: 2,
 			},
 			{
-				fromLineNumber: 3,
 				kind: 'linesInserted',
-				lines: [
-					'',
-					'',
-					'Hello[injected2]econd Line',
-				]
+				fromLineNumber: 3,
+				count: 3,
 			}
 		]);
 
@@ -119,36 +115,24 @@ suite('Editor Model - Injected Text Events', () => {
 		thisModel.pushEditOperations(null, [EditOperation.replace(new Range(3, 1, 5, 1), '\n\n\n\n\n\n\n\n\n\n\n\n\n')], null);
 		assert.deepStrictEqual(recordedChanges.splice(0), [
 			{
-				'kind': 'lineChanged',
-				'line': '',
-				'lineNumber': 5,
+				kind: 'lineChanged',
+				lineNumber: 5,
+				lineNumberPostEdit: 5,
 			},
 			{
-				'kind': 'lineChanged',
-				'line': '',
-				'lineNumber': 4,
+				kind: 'lineChanged',
+				lineNumber: 4,
+				lineNumberPostEdit: 4,
 			},
 			{
-				'kind': 'lineChanged',
-				'line': '',
-				'lineNumber': 3,
+				kind: 'lineChanged',
+				lineNumber: 3,
+				lineNumberPostEdit: 3,
 			},
 			{
-				'fromLineNumber': 6,
-				'kind': 'linesInserted',
-				'lines': [
-					'',
-					'',
-					'',
-					'',
-					'',
-					'',
-					'',
-					'',
-					'',
-					'',
-					'Hello[injected2]econd Line',
-				]
+				kind: 'linesInserted',
+				fromLineNumber: 6,
+				count: 11,
 			}
 		]);
 
@@ -157,8 +141,8 @@ suite('Editor Model - Injected Text Events', () => {
 		assert.deepStrictEqual(recordedChanges.splice(0), [
 			{
 				kind: 'lineChanged',
-				line: '[injected1]SHello[injected2]econd Line',
 				lineNumber: 2,
+				lineNumberPostEdit: 2,
 			},
 			{
 				kind: 'linesDeleted',
@@ -171,20 +155,16 @@ suite('Editor Model - Injected Text Events', () => {
 
 function mapChange(change: ModelRawChange): unknown {
 	if (change.changeType === RawContentChangedType.LineChanged) {
-		(change.injectedText || []).every(e => {
-			assert.deepStrictEqual(e.lineNumber, change.lineNumber);
-		});
-
 		return {
 			kind: 'lineChanged',
-			line: getDetail(change.detail, change.injectedText),
 			lineNumber: change.lineNumber,
+			lineNumberPostEdit: change.lineNumberPostEdit,
 		};
 	} else if (change.changeType === RawContentChangedType.LinesInserted) {
 		return {
 			kind: 'linesInserted',
-			lines: change.detail.map((e, idx) => getDetail(e, change.injectedTexts[idx])),
-			fromLineNumber: change.fromLineNumber
+			fromLineNumber: change.fromLineNumber,
+			count: change.count,
 		};
 	} else if (change.changeType === RawContentChangedType.LinesDeleted) {
 		return {
@@ -201,7 +181,3 @@ function mapChange(change: ModelRawChange): unknown {
 	}
 	return { kind: 'unknown' };
 }
-
-function getDetail(line: string, injectedTexts: LineInjectedText[] | null): string {
-	return LineInjectedText.applyInjectedText(line, (injectedTexts || []).map(t => t.withText(`[${t.options.content}]`)));
-}
diff --git a/src/vs/editor/test/common/viewLayout/lineHeights.test.ts b/src/vs/editor/test/common/viewLayout/lineHeights.test.ts
index 48b50f306162a..695650dd8a355 100644
--- a/src/vs/editor/test/common/viewLayout/lineHeights.test.ts
+++ b/src/vs/editor/test/common/viewLayout/lineHeights.test.ts
@@ -182,7 +182,7 @@ suite('Editor ViewLayout - LineHeightsManager', () => {
 		const manager = new LineHeightsManager(10, []);
 		manager.insertOrChangeCustomLineHeight('dec1', 5, 7, 20);
 
-		manager.onLinesInserted(3, 4, []); // Insert 2 lines at line 3
+		manager.onLinesInserted(3, 4); // Insert 2 lines at line 3
 
 		assert.strictEqual(manager.heightForLineNumber(5), 10);
 		assert.strictEqual(manager.heightForLineNumber(6), 10);
@@ -195,7 +195,7 @@ suite('Editor ViewLayout - LineHeightsManager', () => {
 		const manager = new LineHeightsManager(10, []);
 		manager.insertOrChangeCustomLineHeight('dec1', 5, 7, 20);
 
-		manager.onLinesInserted(6, 7, []); // Insert 2 lines at line 6
+		manager.onLinesInserted(6, 7); // Insert 2 lines at line 6
 
 		assert.strictEqual(manager.heightForLineNumber(5), 20);
 		assert.strictEqual(manager.heightForLineNumber(6), 20);
@@ -267,9 +267,8 @@ suite('Editor ViewLayout - LineHeightsManager', () => {
 		assert.strictEqual(manager.heightForLineNumber(2), 10);
 
 		// Insert line 2 to line 2, with the same decoration ID 'decA' covering line 2
-		manager.onLinesInserted(2, 2, [
-			new CustomLineHeightData('decA', 2, 2, 30)
-		]);
+		manager.onLinesInserted(2, 2);
+		manager.insertOrChangeCustomLineHeight('decA', 2, 2, 30);
 
 		// After insertion, the decoration 'decA' now covers line 2
 		// Since insertOrChangeCustomLineHeight removes the old decoration first,
@@ -349,7 +348,7 @@ suite('Editor ViewLayout - LineHeightsManager (auto-commit on read)', () => {
 		// Caller A removes its decoration before any flush occurs.
 		manager.removeCustomLineHeight('decA');
 		// Caller B triggers a structural change that causes queue flush in the middle of commit.
-		manager.onLinesInserted(1, 1, []);
+		manager.onLinesInserted(1, 1);
 
 		// decA must stay removed. If queued inserts are not canceled on remove, decA incorrectly survives.
 		assert.strictEqual(manager.heightForLineNumber(4), 10);
@@ -381,7 +380,7 @@ suite('Editor ViewLayout - LineHeightsManager (auto-commit on read)', () => {
 		manager.insertOrChangeCustomLineHeight('dec1', 2, 2, 20);
 		manager.insertOrChangeCustomLineHeight('dec2', 5, 5, 30);
 		// Step 3: insert 2 lines at line 3 (shifts dec2 from line 5 → 7)
-		manager.onLinesInserted(3, 4, []);
+		manager.onLinesInserted(3, 4);
 		// Step 4: delete line 1 (shifts dec1 from line 2 → 1, dec2 from line 7 → 6)
 		manager.onLinesDeleted(1, 1);
 		// Step 5-6: remove the two decorations
@@ -402,7 +401,7 @@ suite('Editor ViewLayout - LineHeightsManager (auto-commit on read)', () => {
 		const manager = new LineHeightsManager(10, []);
 		manager.insertOrChangeCustomLineHeight('dec1', 3, 3, 20);
 		// Insert 1 line at line 1 → dec1 shifts from 3 → 4
-		manager.onLinesInserted(1, 1, []);
+		manager.onLinesInserted(1, 1);
 		manager.removeCustomLineHeight('dec1');
 		// Read — no explicit commit
 		assert.strictEqual(manager.heightForLineNumber(3), 10);
@@ -442,7 +441,7 @@ suite('Editor ViewLayout - LineHeightsManager (auto-commit on read)', () => {
 		const manager = new LineHeightsManager(10, []);
 		manager.insertOrChangeCustomLineHeight('dec1', 3, 3, 20);
 		// Insert 2 lines at line 1 → dec1 moves from 3 → 5
-		manager.onLinesInserted(1, 2, []);
+		manager.onLinesInserted(1, 2);
 		// Delete line 1 → dec1 moves from 5 → 4
 		manager.onLinesDeleted(1, 1);
 		// Read
@@ -455,9 +454,9 @@ suite('Editor ViewLayout - LineHeightsManager (auto-commit on read)', () => {
 		const manager = new LineHeightsManager(10, []);
 		manager.insertOrChangeCustomLineHeight('dec1', 3, 3, 20);
 		// Insert 1 line at line 1 → dec1 at 3 → 4
-		manager.onLinesInserted(1, 1, []);
+		manager.onLinesInserted(1, 1);
 		// Insert 1 line at line 1 → dec1 at 4 → 5
-		manager.onLinesInserted(1, 1, []);
+		manager.onLinesInserted(1, 1);
 		// Read
 		assert.strictEqual(manager.heightForLineNumber(5), 20);
 		assert.strictEqual(manager.heightForLineNumber(3), 10);
@@ -492,7 +491,7 @@ suite('Editor ViewLayout - LineHeightsManager (auto-commit on read)', () => {
 		// Insert a decoration at line 3 (pending, not committed)
 		manager.insertOrChangeCustomLineHeight('dec1', 3, 3, 20);
 		// Insert 2 lines before it at line 1 → should shift dec1 from 3 → 5
-		manager.onLinesInserted(1, 2, []);
+		manager.onLinesInserted(1, 2);
 		// Read
 		assert.strictEqual(manager.heightForLineNumber(3), 10);
 		assert.strictEqual(manager.heightForLineNumber(5), 20);
@@ -524,4 +523,13 @@ suite('Editor ViewLayout - LineHeightsManager (auto-commit on read)', () => {
 		assert.strictEqual(manager.heightForLineNumber(6), 30);
 		assert.strictEqual(manager.getAccumulatedLineHeightsIncludingLineNumber(6), 110);
 	});
+
+	test('deleting line 2 with lineHeightsRemoved re-adding at line 1 moves special line to line 1', () => {
+		const manager = new LineHeightsManager(10, []);
+		manager.insertOrChangeCustomLineHeight('dec1', 2, 2, 20);
+		assert.strictEqual(manager.heightForLineNumber(2), 20);
+		manager.onLinesDeleted(2, 2);
+		manager.insertOrChangeCustomLineHeight('dec1', 1, 1, 20);
+		assert.strictEqual(manager.heightForLineNumber(1), 20);
+	});
 });
diff --git a/src/vs/editor/test/common/viewLayout/linesLayout.test.ts b/src/vs/editor/test/common/viewLayout/linesLayout.test.ts
index ceb624ac2740e..7bf20a78d8457 100644
--- a/src/vs/editor/test/common/viewLayout/linesLayout.test.ts
+++ b/src/vs/editor/test/common/viewLayout/linesLayout.test.ts
@@ -208,7 +208,7 @@ suite('Editor ViewLayout - LinesLayout', () => {
 		// Insert two lines at the beginning
 		// 10 lines
 		// whitespace: - a(6,10)
-		linesLayout.onLinesInserted(1, 2, []);
+		linesLayout.onLinesInserted(1, 2);
 		assert.strictEqual(linesLayout.getLinesTotalHeight(), 20);
 		assert.strictEqual(linesLayout.getVerticalOffsetForLineNumber(1), 0);
 		assert.strictEqual(linesLayout.getVerticalOffsetForLineNumber(2), 1);
@@ -909,7 +909,7 @@ suite('Editor ViewLayout - LinesLayout', () => {
 		assert.strictEqual(linesLayout.getWhitespaceAccumulatedHeightBeforeLineNumber(5), 50);
 
 		// Insert a line before line 1
-		linesLayout.onLinesInserted(1, 1, []);
+		linesLayout.onLinesInserted(1, 1);
 		// whitespaces: d(3, 30), c(4, 20)
 		assert.strictEqual(linesLayout.getWhitespacesCount(), 2);
 		assert.strictEqual(linesLayout.getAfterLineNumberForWhitespaceIndex(0), 3);
diff --git a/src/vs/monaco.d.ts b/src/vs/monaco.d.ts
index ce6731adeb770..5b0047e74a3f2 100644
--- a/src/vs/monaco.d.ts
+++ b/src/vs/monaco.d.ts
@@ -4255,6 +4255,10 @@ declare namespace monaco.editor {
 		 * Controls whether the search result and diff result automatically restarts from the beginning (or the end) when no further matches can be found
 		 */
 		loop?: boolean;
+		/**
+		 * Controls whether to close the Find Widget after an explicit find navigation command lands on a match.
+		 */
+		closeOnResult?: boolean;
 	}
 
 	export type GoToLocationValues = 'peek' | 'gotoAndPeek' | 'goto';
@@ -4307,6 +4311,11 @@ declare namespace monaco.editor {
 		 * Defaults to false.
 		 */
 		above?: boolean;
+		/**
+		 * Should long line warning hovers be shown (tokenization skipped, rendering paused)?
+		 * Defaults to true.
+		 */
+		showLongLineWarning?: boolean;
 	}
 
 	/**
@@ -5254,7 +5263,7 @@ declare namespace monaco.editor {
 	export const EditorOptions: {
 		acceptSuggestionOnCommitCharacter: IEditorOption<EditorOption.acceptSuggestionOnCommitCharacter, boolean>;
 		acceptSuggestionOnEnter: IEditorOption<EditorOption.acceptSuggestionOnEnter, 'on' | 'off' | 'smart'>;
-		accessibilitySupport: IEditorOption<EditorOption.accessibilitySupport, AccessibilitySupport>;
+		accessibilitySupport: IEditorOption<EditorOption.accessibilitySupport, any>;
 		accessibilityPageSize: IEditorOption<EditorOption.accessibilityPageSize, number>;
 		allowOverflow: IEditorOption<EditorOption.allowOverflow, boolean>;
 		allowVariableLineHeights: IEditorOption<EditorOption.allowVariableLineHeights, boolean>;
@@ -5317,7 +5326,7 @@ declare namespace monaco.editor {
 		foldingMaximumRegions: IEditorOption<EditorOption.foldingMaximumRegions, number>;
 		unfoldOnClickAfterEndOfLine: IEditorOption<EditorOption.unfoldOnClickAfterEndOfLine, boolean>;
 		fontFamily: IEditorOption<EditorOption.fontFamily, string>;
-		fontInfo: IEditorOption<EditorOption.fontInfo, FontInfo>;
+		fontInfo: IEditorOption<EditorOption.fontInfo, any>;
 		fontLigatures2: IEditorOption<EditorOption.fontLigatures, string>;
 		fontSize: IEditorOption<EditorOption.fontSize, number>;
 		fontWeight: IEditorOption<EditorOption.fontWeight, string>;
@@ -5357,7 +5366,7 @@ declare namespace monaco.editor {
 		pasteAs: IEditorOption<EditorOption.pasteAs, Readonly<Required<IPasteAsOptions>>>;
 		parameterHints: IEditorOption<EditorOption.parameterHints, Readonly<Required<IEditorParameterHintOptions>>>;
 		peekWidgetDefaultFocus: IEditorOption<EditorOption.peekWidgetDefaultFocus, 'tree' | 'editor'>;
-		placeholder: IEditorOption<EditorOption.placeholder, string>;
+		placeholder: IEditorOption<EditorOption.placeholder, string | undefined>;
 		definitionLinkOpensInPeek: IEditorOption<EditorOption.definitionLinkOpensInPeek, boolean>;
 		quickSuggestions: IEditorOption<EditorOption.quickSuggestions, InternalQuickSuggestionsOptions>;
 		quickSuggestionsDelay: IEditorOption<EditorOption.quickSuggestionsDelay, number>;
diff --git a/src/vs/platform/actionWidget/browser/actionList.ts b/src/vs/platform/actionWidget/browser/actionList.ts
index 6d2cfda35684d..5a6cf722cccfb 100644
--- a/src/vs/platform/actionWidget/browser/actionList.ts
+++ b/src/vs/platform/actionWidget/browser/actionList.ts
@@ -10,7 +10,7 @@ import { getAnchorRect, IAnchor } from '../../../base/browser/ui/contextview/con
 import { KeybindingLabel } from '../../../base/browser/ui/keybindingLabel/keybindingLabel.js';
 import { IListEvent, IListMouseEvent, IListRenderer, IListVirtualDelegate } from '../../../base/browser/ui/list/list.js';
 import { IListAccessibilityProvider, List } from '../../../base/browser/ui/list/listWidget.js';
-import { IAction } from '../../../base/common/actions.js';
+import { IAction, toAction } from '../../../base/common/actions.js';
 import { CancellationToken, CancellationTokenSource } from '../../../base/common/cancellation.js';
 import { Codicon } from '../../../base/common/codicons.js';
 import { IMarkdownString, MarkdownString } from '../../../base/common/htmlContent.js';
@@ -96,6 +96,11 @@ export interface IActionListItem<T> {
 	 * When true, this item is always shown when filtering produces no other results.
 	 */
 	readonly showAlways?: boolean;
+	/**
+	 * Optional callback invoked when the item is removed via the built-in remove button.
+	 * When set, a close button is automatically added to the item toolbar.
+	 */
+	readonly onRemove?: () => void;
 }
 
 interface IActionMenuTemplateData {
@@ -176,6 +181,7 @@ class ActionItemRenderer<T> implements IListRenderer<IActionListItem<T>, IAction
 
 	constructor(
 		private readonly _supportsPreview: boolean,
+		private readonly _onRemoveItem: ((item: IActionListItem<T>) => void) | undefined,
 		@IKeybindingService private readonly _keybindingService: IKeybindingService,
 		@IOpenerService private readonly _openerService: IOpenerService,
 	) { }
@@ -297,11 +303,23 @@ class ActionItemRenderer<T> implements IListRenderer<IActionListItem<T>, IAction
 
 		// Clear and render toolbar actions
 		dom.clearNode(data.toolbar);
-		data.container.classList.toggle('has-toolbar', !!element.toolbarActions?.length);
-		if (element.toolbarActions?.length) {
+		const toolbarActions = [...(element.toolbarActions ?? [])];
+		if (element.onRemove) {
+			toolbarActions.push(toAction({
+				id: 'actionList.remove',
+				label: localize('actionList.remove', "Remove"),
+				class: ThemeIcon.asClassName(Codicon.close),
+				run: () => {
+					element.onRemove!();
+					this._onRemoveItem?.(element);
+				},
+			}));
+		}
+		data.container.classList.toggle('has-toolbar', toolbarActions.length > 0);
+		if (toolbarActions.length > 0) {
 			const actionBar = new ActionBar(data.toolbar);
 			data.elementDisposables.add(actionBar);
-			actionBar.push(element.toolbarActions, { icon: true, label: false });
+			actionBar.push(toolbarActions, { icon: true, label: false });
 		}
 	}
 
@@ -341,6 +359,11 @@ export interface IActionListOptions {
 	 */
 	readonly filterPlaceholder?: string;
 
+	/**
+	 * Optional actions shown in the filter row, to the right of the input.
+	 */
+	readonly filterActions?: readonly IAction[];
+
 	/**
 	 * Section IDs that should be collapsed by default.
 	 */
@@ -351,6 +374,12 @@ export interface IActionListOptions {
 	 */
 	readonly minWidth?: number;
 
+	/**
+	 * When true, descriptions are rendered as subtext below the title
+	 * instead of inline to the right.
+	 */
+	readonly descriptionBelow?: boolean;
+
 
 
 	/**
@@ -365,11 +394,11 @@ export class ActionList<T> extends Disposable {
 
 	private readonly _list: List<IActionListItem<T>>;
 
-	private readonly _actionLineHeight = 24;
+	private readonly _actionLineHeight: number;
 	private readonly _headerLineHeight = 24;
 	private readonly _separatorLineHeight = 8;
 
-	private readonly _allMenuItems: readonly IActionListItem<T>[];
+	private _allMenuItems: IActionListItem<T>[];
 
 	private readonly cts = this._register(new CancellationTokenSource());
 
@@ -413,6 +442,10 @@ export class ActionList<T> extends Disposable {
 		super();
 		this.domNode = document.createElement('div');
 		this.domNode.classList.add('actionList');
+		if (this._options?.descriptionBelow) {
+			this.domNode.classList.add('description-below');
+		}
+		this._actionLineHeight = this._options?.descriptionBelow ? 48 : 24;
 
 		// Initialize collapsed sections
 		if (this._options?.collapsedByDefault) {
@@ -437,7 +470,7 @@ export class ActionList<T> extends Disposable {
 
 
 		this._list = this._register(new List(user, this.domNode, virtualDelegate, [
-			new ActionItemRenderer<IActionListItem<T>>(preview, this._keybindingService, this._openerService),
+			new ActionItemRenderer<T>(preview, (item) => this._removeItem(item), this._keybindingService, this._openerService),
 			new HeaderRenderer(),
 			new SeparatorRenderer(),
 		], {
@@ -482,19 +515,27 @@ export class ActionList<T> extends Disposable {
 		this._register(this._list.onDidChangeFocus(() => this.onFocus()));
 		this._register(this._list.onDidChangeSelection(e => this.onListSelection(e)));
 
-		this._allMenuItems = items;
+		this._allMenuItems = [...items];
 
 		// Create filter input
 		if (this._options?.showFilter) {
 			this._filterContainer = document.createElement('div');
 			this._filterContainer.className = 'action-list-filter';
+			const filterRow = dom.append(this._filterContainer, dom.$('.action-list-filter-row'));
 
 			this._filterInput = document.createElement('input');
 			this._filterInput.type = 'text';
 			this._filterInput.className = 'action-list-filter-input';
 			this._filterInput.placeholder = this._options?.filterPlaceholder ?? localize('actionList.filter.placeholder', "Search...");
 			this._filterInput.setAttribute('aria-label', localize('actionList.filter.ariaLabel', "Filter items"));
-			this._filterContainer.appendChild(this._filterInput);
+			filterRow.appendChild(this._filterInput);
+
+			const filterActions = this._options?.filterActions ?? [];
+			if (filterActions.length > 0) {
+				const filterActionsContainer = dom.append(filterRow, dom.$('.action-list-filter-actions'));
+				const filterActionBar = this._register(new ActionBar(filterActionsContainer));
+				filterActionBar.push(filterActions, { icon: true, label: false });
+			}
 
 			this._register(dom.addDisposableListener(this._filterInput, 'input', () => {
 				this._filterText = this._filterInput!.value;
@@ -769,7 +810,8 @@ export class ActionList<T> extends Disposable {
 			availableHeight = widgetTop > 0 ? windowHeight - widgetTop - padding : windowHeight * 0.7;
 		}
 
-		const maxHeight = Math.max(availableHeight, this._actionLineHeight * 3 + filterHeight);
+		const viewportMaxHeight = Math.floor(targetWindow.innerHeight * 0.6);
+		const maxHeight = Math.min(Math.max(availableHeight, this._actionLineHeight * 3 + filterHeight), viewportMaxHeight);
 		const height = Math.min(listHeight + filterHeight, maxHeight);
 		return height - filterHeight;
 	}
@@ -815,7 +857,7 @@ export class ActionList<T> extends Disposable {
 					element.style.width = 'auto';
 					const width = element.getBoundingClientRect().width;
 					element.style.width = '';
-					itemWidths.push(width);
+					itemWidths.push(width + this._computeToolbarWidth(allItems[i]));
 				}
 			}
 
@@ -834,7 +876,7 @@ export class ActionList<T> extends Disposable {
 				element.style.width = 'auto';
 				const width = element.getBoundingClientRect().width;
 				element.style.width = '';
-				itemWidths.push(width);
+				itemWidths.push(width + this._computeToolbarWidth(this._list.element(i)));
 			}
 		}
 		return Math.max(...itemWidths, effectiveMinWidth);
@@ -1017,6 +1059,27 @@ export class ActionList<T> extends Disposable {
 		}
 	}
 
+	private _removeItem(item: IActionListItem<T>): void {
+		const index = this._allMenuItems.indexOf(item);
+		if (index >= 0) {
+			this._allMenuItems.splice(index, 1);
+			this._applyFilter();
+		}
+	}
+
+	private _computeToolbarWidth(item: IActionListItem<T>): number {
+		let actionCount = item.toolbarActions?.length ?? 0;
+		if (item.onRemove) {
+			actionCount++;
+		}
+		if (actionCount === 0) {
+			return 0;
+		}
+		// Each toolbar action button is ~22px (16px icon + padding) plus 6px row gap
+		const actionButtonWidth = 22;
+		return actionCount * actionButtonWidth + 6;
+	}
+
 	private _getRowElement(index: number): HTMLElement | null {
 		// eslint-disable-next-line no-restricted-syntax
 		return this.domNode.ownerDocument.getElementById(this._list.getElementID(index));
diff --git a/src/vs/platform/actionWidget/browser/actionWidget.css b/src/vs/platform/actionWidget/browser/actionWidget.css
index 96fc6cbf50661..8957a85b01f88 100644
--- a/src/vs/platform/actionWidget/browser/actionWidget.css
+++ b/src/vs/platform/actionWidget/browser/actionWidget.css
@@ -15,7 +15,7 @@
 	background-color: var(--vscode-menu-background);
 	color: var(--vscode-menu-foreground);
 	padding: 4px;
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 }
 
 .context-view-block {
@@ -119,7 +119,7 @@
 
 .action-widget .monaco-list-row.action {
 	display: flex;
-	gap: 6px;
+	gap: 8px;
 	align-items: center;
 }
 
@@ -217,6 +217,31 @@
 	font-size: 12px;
 }
 
+/* Description below mode — shows descriptions as subtext under the title */
+.action-widget .description-below .monaco-list .monaco-list-row.action {
+	flex-wrap: wrap;
+	align-content: center;
+	padding-top: 6px;
+	padding-right: 2px;
+
+	.title {
+		line-height: 14px;
+	}
+
+	.description {
+		display: block !important;
+		width: 100%;
+		margin-left: 0;
+		padding-left: 20px;
+		font-size: 11px;
+		line-height: 14px;
+		opacity: 0.8;
+		overflow: hidden;
+		text-overflow: ellipsis;
+		white-space: nowrap;
+	}
+}
+
 /* Item toolbar - shows on hover/focus */
 .action-widget .monaco-list-row.action .action-list-item-toolbar {
 	display: none;
@@ -240,7 +265,13 @@
 
 /* Filter input */
 .action-widget .action-list-filter {
-	padding: 2px 2px 4px 2px
+	padding: 2px 2px 4px 2px;
+}
+
+.action-widget .action-list-filter-row {
+	display: flex;
+	align-items: center;
+	gap: 4px;
 }
 
 .action-widget .action-list-filter:first-child {
@@ -253,6 +284,7 @@
 
 .action-widget .action-list-filter-input {
 	width: 100%;
+	flex: 1;
 	box-sizing: border-box;
 	padding: 4px 8px;
 	border: 1px solid var(--vscode-input-border, transparent);
@@ -269,3 +301,12 @@
 .action-widget .action-list-filter-input::placeholder {
 	color: var(--vscode-input-placeholderForeground);
 }
+
+.action-widget .action-list-filter-actions .action-label {
+	padding: 3px;
+	border-radius: 3px;
+}
+
+.action-widget .action-list-filter-actions .action-label:hover {
+	background-color: var(--vscode-toolbar-hoverBackground);
+}
diff --git a/src/vs/platform/actionWidget/browser/actionWidgetDropdown.ts b/src/vs/platform/actionWidget/browser/actionWidgetDropdown.ts
index 2b2022fb43572..82e6ff581bad9 100644
--- a/src/vs/platform/actionWidget/browser/actionWidgetDropdown.ts
+++ b/src/vs/platform/actionWidget/browser/actionWidgetDropdown.ts
@@ -170,6 +170,7 @@ export class ActionWidgetDropdown extends BaseDropdown {
 				action.run();
 			},
 			onHide: () => {
+				this.hide();
 				if (isHTMLElement(previouslyFocusedElement)) {
 					previouslyFocusedElement.focus();
 				}
@@ -221,6 +222,8 @@ export class ActionWidgetDropdown extends BaseDropdown {
 			getWidgetRole: () => 'menu',
 		};
 
+		super.show();
+
 		this.actionWidgetService.show<IActionWidgetDropdownAction>(
 			this._options.label ?? '',
 			false,
diff --git a/src/vs/platform/actions/browser/toolbar.ts b/src/vs/platform/actions/browser/toolbar.ts
index a167319371ca0..e44cdb4eae07e 100644
--- a/src/vs/platform/actions/browser/toolbar.ts
+++ b/src/vs/platform/actions/browser/toolbar.ts
@@ -15,7 +15,7 @@ import { Iterable } from '../../../base/common/iterator.js';
 import { DisposableStore } from '../../../base/common/lifecycle.js';
 import { localize } from '../../../nls.js';
 import { createActionViewItem, getActionBarActions } from './menuEntryActionViewItem.js';
-import { IMenuActionOptions, IMenuService, MenuId, MenuItemAction, SubmenuItemAction } from '../common/actions.js';
+import { IMenu, IMenuActionOptions, IMenuService, MenuId, MenuItemAction, SubmenuItemAction } from '../common/actions.js';
 import { createConfigureKeybindingAction } from '../common/menuService.js';
 import { ICommandService } from '../../commands/common/commands.js';
 import { IContextKeyService } from '../../contextkey/common/contextkey.js';
@@ -184,7 +184,8 @@ export class WorkbenchToolBar extends ToolBar {
 		// coalesce turns Array<IAction|undefined> into IAction[]
 		coalesceInPlace(primary);
 		coalesceInPlace(extraSecondary);
-		super.setActions(primary, Separator.join(extraSecondary, secondary));
+
+		super.setActions(Separator.clean(primary), Separator.join(extraSecondary, secondary));
 
 		// add context menu for toggle and configure keybinding actions
 		if (toggleActions.length > 0 || primary.length > 0) {
@@ -332,6 +333,11 @@ export class MenuWorkbenchToolBar extends WorkbenchToolBar {
 	private readonly _onDidChangeMenuItems = this._store.add(new Emitter<this>());
 	get onDidChangeMenuItems() { return this._onDidChangeMenuItems.event; }
 
+	private readonly _menu: IMenu;
+	private readonly _menuOptions: IMenuActionOptions | undefined;
+	private readonly _toolbarOptions: IToolBarRenderOptions | undefined;
+	private readonly _container: HTMLElement;
+
 	constructor(
 		container: HTMLElement,
 		menuId: MenuId,
@@ -361,30 +367,44 @@ export class MenuWorkbenchToolBar extends WorkbenchToolBar {
 			}
 		}, menuService, contextKeyService, contextMenuService, keybindingService, commandService, telemetryService);
 
+		this._container = container;
+		this._menuOptions = options?.menuOptions;
+		this._toolbarOptions = options?.toolbarOptions;
+
 		// update logic
-		const menu = this._store.add(menuService.createMenu(menuId, contextKeyService, { emitEventsForSubmenuChanges: true, eventDebounceDelay: options?.eventDebounceDelay }));
-		const updateToolbar = () => {
-			const { primary, secondary } = getActionBarActions(
-				menu.getActions(options?.menuOptions),
-				options?.toolbarOptions?.primaryGroup,
-				options?.toolbarOptions?.shouldInlineSubmenu,
-				options?.toolbarOptions?.useSeparatorsInPrimaryActions
-			);
-			container.classList.toggle('has-no-actions', primary.length === 0 && secondary.length === 0);
-			super.setActions(primary, secondary);
-		};
-
-		this._store.add(menu.onDidChange(() => {
-			updateToolbar();
+		this._menu = this._store.add(menuService.createMenu(menuId, contextKeyService, { emitEventsForSubmenuChanges: true, eventDebounceDelay: options?.eventDebounceDelay }));
+
+		this._store.add(this._menu.onDidChange(() => {
+			this._updateToolbar();
 			this._onDidChangeMenuItems.fire(this);
 		}));
 
 		this._store.add(actionViewService.onDidChange(e => {
 			if (e === menuId) {
-				updateToolbar();
+				this._updateToolbar();
 			}
 		}));
-		updateToolbar();
+		this._updateToolbar();
+	}
+
+	private _updateToolbar(): void {
+		const { primary, secondary } = getActionBarActions(
+			this._menu.getActions(this._menuOptions),
+			this._toolbarOptions?.primaryGroup,
+			this._toolbarOptions?.shouldInlineSubmenu,
+			this._toolbarOptions?.useSeparatorsInPrimaryActions
+		);
+		this._container.classList.toggle('has-no-actions', primary.length === 0 && secondary.length === 0);
+		super.setActions(primary, secondary);
+	}
+
+	/**
+	 * Force the toolbar to immediately re-evaluate its menu actions.
+	 * Use this after synchronously updating context keys to avoid
+	 * layout shifts caused by the debounced menu change event.
+	 */
+	refresh(): void {
+		this._updateToolbar();
 	}
 
 	/**
diff --git a/src/vs/platform/actions/common/actions.ts b/src/vs/platform/actions/common/actions.ts
index 1b3e9d595c887..5c1cf404a4c3a 100644
--- a/src/vs/platform/actions/common/actions.ts
+++ b/src/vs/platform/actions/common/actions.ts
@@ -89,6 +89,7 @@ export class MenuId {
 	static readonly EditorContextShare = new MenuId('EditorContextShare');
 	static readonly EditorTitle = new MenuId('EditorTitle');
 	static readonly ModalEditorTitle = new MenuId('ModalEditorTitle');
+	static readonly ModalEditorEditorTitle = new MenuId('ModalEditorEditorTitle');
 	static readonly CompactWindowEditorTitle = new MenuId('CompactWindowEditorTitle');
 	static readonly EditorTitleRun = new MenuId('EditorTitleRun');
 	static readonly EditorTitleContext = new MenuId('EditorTitleContext');
@@ -255,10 +256,13 @@ export class MenuId {
 	static readonly ChatExecute = new MenuId('ChatExecute');
 	static readonly ChatExecuteQueue = new MenuId('ChatExecuteQueue');
 	static readonly ChatInput = new MenuId('ChatInput');
+	static readonly ChatInputSecondary = new MenuId('ChatInputSecondary');
 	static readonly ChatInputSide = new MenuId('ChatInputSide');
 	static readonly ChatModePicker = new MenuId('ChatModePicker');
 	static readonly ChatEditingWidgetToolbar = new MenuId('ChatEditingWidgetToolbar');
 	static readonly ChatEditingSessionChangesToolbar = new MenuId('ChatEditingSessionChangesToolbar');
+	static readonly ChatEditingSessionApplySubmenu = new MenuId('ChatEditingSessionApplySubmenu');
+	static readonly ChatEditingSessionChangesVersionsSubmenu = new MenuId('ChatEditingSessionChangesVersionsSubmenu');
 	static readonly ChatEditingEditorContent = new MenuId('ChatEditingEditorContent');
 	static readonly ChatEditingEditorHunk = new MenuId('ChatEditingEditorHunk');
 	static readonly ChatEditingDeletedNotebookCell = new MenuId('ChatEditingDeletedNotebookCell');
diff --git a/src/vs/platform/assignment/common/assignment.ts b/src/vs/platform/assignment/common/assignment.ts
index 293eaee739ac1..584bef3b1fdf5 100644
--- a/src/vs/platform/assignment/common/assignment.ts
+++ b/src/vs/platform/assignment/common/assignment.ts
@@ -177,3 +177,10 @@ export class AssignmentFilterProvider implements IExperimentationFilterProvider
 		return filters;
 	}
 }
+
+export function getInternalOrg(organisations: string[] | undefined): 'vscode' | 'github' | 'microsoft' | undefined {
+	const isVSCodeInternal = organisations?.includes('Visual-Studio-Code');
+	const isGitHubInternal = organisations?.includes('github');
+	const isMicrosoftInternal = organisations?.includes('microsoft') || organisations?.includes('ms-copilot') || organisations?.includes('MicrosoftCopilot');
+	return isVSCodeInternal ? 'vscode' : isGitHubInternal ? 'github' : isMicrosoftInternal ? 'microsoft' : undefined;
+}
diff --git a/src/vs/platform/browserElements/common/browserElements.ts b/src/vs/platform/browserElements/common/browserElements.ts
index 2973d9db93918..2973512713422 100644
--- a/src/vs/platform/browserElements/common/browserElements.ts
+++ b/src/vs/platform/browserElements/common/browserElements.ts
@@ -56,6 +56,8 @@ export interface INativeBrowserElementsService {
 
 	getElementData(rect: IRectangle, token: CancellationToken, locator: IBrowserTargetLocator, cancellationId?: number): Promise<IElementData | undefined>;
 
+	getFocusedElementData(rect: IRectangle, token: CancellationToken, locator: IBrowserTargetLocator, cancellationId?: number): Promise<IElementData | undefined>;
+
 	startDebugSession(token: CancellationToken, locator: IBrowserTargetLocator, cancelAndDetachId?: number): Promise<void>;
 
 	startConsoleSession(token: CancellationToken, locator: IBrowserTargetLocator, cancelAndDetachId?: number): Promise<void>;
diff --git a/src/vs/platform/browserElements/electron-main/nativeBrowserElementsMainService.ts b/src/vs/platform/browserElements/electron-main/nativeBrowserElementsMainService.ts
index 5e018a6d718a2..84a64f6d43bfc 100644
--- a/src/vs/platform/browserElements/electron-main/nativeBrowserElementsMainService.ts
+++ b/src/vs/platform/browserElements/electron-main/nativeBrowserElementsMainService.ts
@@ -431,6 +431,121 @@ export class NativeBrowserElementsMainService extends Disposable implements INat
 		};
 	}
 
+	async getFocusedElementData(windowId: number | undefined, rect: IRectangle, _token: CancellationToken, locator: IBrowserTargetLocator, _cancellationId?: number): Promise<IElementData | undefined> {
+		const window = this.windowById(windowId);
+		if (!window?.win) {
+			return undefined;
+		}
+
+		const allWebContents = webContents.getAllWebContents();
+		const simpleBrowserWebview = allWebContents.find(webContent => webContent.id === window.id);
+		if (!simpleBrowserWebview) {
+			return undefined;
+		}
+
+		const debuggers = simpleBrowserWebview.debugger;
+		if (!debuggers.isAttached()) {
+			debuggers.attach();
+		}
+
+		let sessionId: string | undefined;
+		try {
+			const targetId = await this.findWebviewTarget(debuggers, locator);
+			if (!targetId) {
+				return undefined;
+			}
+
+			const attach = await debuggers.sendCommand('Target.attachToTarget', { targetId, flatten: true });
+			sessionId = attach.sessionId;
+			await debuggers.sendCommand('Runtime.enable', {}, sessionId);
+
+			const { result } = await debuggers.sendCommand('Runtime.evaluate', {
+				expression: `(() => {
+					const el = document.activeElement;
+					if (!el || el.nodeType !== 1) {
+						return undefined;
+					}
+					const r = el.getBoundingClientRect();
+					const attrs = {};
+					for (let i = 0; i < el.attributes.length; i++) {
+						attrs[el.attributes[i].name] = el.attributes[i].value;
+					}
+					const ancestors = [];
+					let n = el;
+					while (n && n.nodeType === 1) {
+						const entry = { tagName: n.tagName.toLowerCase() };
+						if (n.id) {
+							entry.id = n.id;
+						}
+						if (typeof n.className === 'string' && n.className.trim().length > 0) {
+							entry.classNames = n.className.trim().split(/\\s+/).filter(Boolean);
+						}
+						ancestors.unshift(entry);
+						n = n.parentElement;
+					}
+					const css = getComputedStyle(el);
+					const computedStyles = {};
+					for (let i = 0; i < css.length; i++) {
+						const name = css[i];
+						computedStyles[name] = css.getPropertyValue(name);
+					}
+					const text = (el.innerText || '').trim();
+					return {
+						outerHTML: el.outerHTML,
+						computedStyle: '',
+						bounds: { x: r.x, y: r.y, width: r.width, height: r.height },
+						ancestors,
+						attributes: attrs,
+						computedStyles,
+						dimensions: { top: r.top, left: r.left, width: r.width, height: r.height },
+						innerText: text.length > 100 ? text.slice(0, 100) + '\\u2026' : text
+					};
+				})();`,
+				returnByValue: true
+			}, sessionId);
+
+			const focusedData = result?.value as NodeDataResponse | undefined;
+			if (!focusedData) {
+				return undefined;
+			}
+
+			const zoomFactor = simpleBrowserWebview.getZoomFactor();
+			const absoluteBounds = {
+				x: rect.x + focusedData.bounds.x,
+				y: rect.y + focusedData.bounds.y,
+				width: focusedData.bounds.width,
+				height: focusedData.bounds.height
+			};
+
+			const clippedBounds = {
+				x: Math.max(absoluteBounds.x, rect.x),
+				y: Math.max(absoluteBounds.y, rect.y),
+				width: Math.max(0, Math.min(absoluteBounds.x + absoluteBounds.width, rect.x + rect.width) - Math.max(absoluteBounds.x, rect.x)),
+				height: Math.max(0, Math.min(absoluteBounds.y + absoluteBounds.height, rect.y + rect.height) - Math.max(absoluteBounds.y, rect.y))
+			};
+
+			return {
+				outerHTML: focusedData.outerHTML,
+				computedStyle: focusedData.computedStyle,
+				bounds: {
+					x: clippedBounds.x * zoomFactor,
+					y: clippedBounds.y * zoomFactor,
+					width: clippedBounds.width * zoomFactor,
+					height: clippedBounds.height * zoomFactor
+				},
+				ancestors: focusedData.ancestors,
+				attributes: focusedData.attributes,
+				computedStyles: focusedData.computedStyles,
+				dimensions: focusedData.dimensions,
+				innerText: focusedData.innerText,
+			};
+		} finally {
+			if (debuggers.isAttached()) {
+				debuggers.detach();
+			}
+		}
+	}
+
 	async getNodeData(sessionId: string, debuggers: Electron.Debugger, window: BrowserWindow, cancellationId?: number): Promise<NodeDataResponse> {
 		return new Promise((resolve, reject) => {
 			const onMessage = async (event: Electron.Event, method: string, params: { backendNodeId: number }) => {
diff --git a/src/vs/platform/browserView/common/browserView.ts b/src/vs/platform/browserView/common/browserView.ts
index 28161016f83a3..a11d7b88e4802 100644
--- a/src/vs/platform/browserView/common/browserView.ts
+++ b/src/vs/platform/browserView/common/browserView.ts
@@ -6,6 +6,30 @@
 import { Event } from '../../../base/common/event.js';
 import { VSBuffer } from '../../../base/common/buffer.js';
 import { URI } from '../../../base/common/uri.js';
+import { localize } from '../../../nls.js';
+
+const commandPrefix = 'workbench.action.browser';
+export enum BrowserViewCommandId {
+	Open = `${commandPrefix}.open`,
+	NewTab = `${commandPrefix}.newTab`,
+	GoBack = `${commandPrefix}.goBack`,
+	GoForward = `${commandPrefix}.goForward`,
+	Reload = `${commandPrefix}.reload`,
+	HardReload = `${commandPrefix}.hardReload`,
+	FocusUrlInput = `${commandPrefix}.focusUrlInput`,
+	AddElementToChat = `${commandPrefix}.addElementToChat`,
+	AddConsoleLogsToChat = `${commandPrefix}.addConsoleLogsToChat`,
+	ToggleDevTools = `${commandPrefix}.toggleDevTools`,
+	OpenExternal = `${commandPrefix}.openExternal`,
+	ClearGlobalStorage = `${commandPrefix}.clearGlobalStorage`,
+	ClearWorkspaceStorage = `${commandPrefix}.clearWorkspaceStorage`,
+	ClearEphemeralStorage = `${commandPrefix}.clearEphemeralStorage`,
+	OpenSettings = `${commandPrefix}.openSettings`,
+	ShowFind = `${commandPrefix}.showFind`,
+	HideFind = `${commandPrefix}.hideFind`,
+	FindNext = `${commandPrefix}.findNext`,
+	FindPrevious = `${commandPrefix}.findPrevious`,
+}
 
 export interface IBrowserViewBounds {
 	windowId: number;
@@ -14,6 +38,7 @@ export interface IBrowserViewBounds {
 	width: number;
 	height: number;
 	zoomFactor: number;
+	cornerRadius: number;
 }
 
 export interface IBrowserViewCaptureScreenshotOptions {
@@ -34,6 +59,7 @@ export interface IBrowserViewState {
 	lastFavicon: string | undefined;
 	lastError: IBrowserViewLoadError | undefined;
 	storageScope: BrowserViewStorageScope;
+	browserZoomIndex: number;
 }
 
 export interface IBrowserViewNavigationEvent {
@@ -118,6 +144,19 @@ export enum BrowserViewStorageScope {
 
 export const ipcBrowserViewChannelName = 'browserView';
 
+/**
+ * Discrete zoom levels matching Edge/Chrome.
+ * Note: When those browsers say "33%" and "67%" zoom, they really mean 33.33...% and 66.66...%
+ */
+export const browserZoomFactors = [0.25, 1 / 3, 0.5, 2 / 3, 0.75, 0.8, 0.9, 1, 1.1, 1.25, 1.5, 1.75, 2, 2.5, 3, 4, 5] as const;
+export const browserZoomDefaultIndex = browserZoomFactors.indexOf(1);
+export function browserZoomLabel(zoomFactor: number): string {
+	return localize('browserZoomPercent', "{0}%", Math.round(zoomFactor * 100));
+}
+export function browserZoomAccessibilityLabel(zoomFactor: number): string {
+	return localize('browserZoomAccessibilityLabel', "Page Zoom: {0}%", Math.round(zoomFactor * 100));
+}
+
 /**
  * This should match the isolated world ID defined in `preload-browserView.ts`.
  */
@@ -153,6 +192,14 @@ export interface IBrowserViewService {
 	 */
 	destroyBrowserView(id: string): Promise<void>;
 
+	/**
+	 * Get the state of an existing browser view by ID, or throw if it doesn't exist
+	 * @param id The browser view identifier
+	 * @return The state of the browser view for the given ID
+	 * @throws If no browser view exists for the given ID
+	 */
+	getState(id: string): Promise<IBrowserViewState>;
+
 	/**
 	 * Update the bounds of a browser view
 	 * @param id The browser view identifier
@@ -195,8 +242,9 @@ export interface IBrowserViewService {
 	/**
 	 * Reload the current page
 	 * @param id The browser view identifier
+	 * @param hard Whether to do a hard reload (bypassing cache)
 	 */
-	reload(id: string): Promise<void>;
+	reload(id: string, hard?: boolean): Promise<void>;
 
 	/**
 	 * Toggle developer tools for the browser view.
@@ -276,4 +324,13 @@ export interface IBrowserViewService {
 	 * @param id The browser view identifier
 	 */
 	clearStorage(id: string): Promise<void>;
+
+	/** Set the browser zoom index (independent from VS Code zoom). */
+	setBrowserZoomIndex(id: string, zoomIndex: number): Promise<void>;
+
+	/**
+	 * Update the keybinding accelerators used in browser view context menus.
+	 * @param keybindings A map of command ID to accelerator label
+	 */
+	updateKeybindings(keybindings: { [commandId: string]: string }): Promise<void>;
 }
diff --git a/src/vs/platform/browserView/common/browserViewGroup.ts b/src/vs/platform/browserView/common/browserViewGroup.ts
index 0f43b98c8b080..0851ac7ffe4ab 100644
--- a/src/vs/platform/browserView/common/browserViewGroup.ts
+++ b/src/vs/platform/browserView/common/browserViewGroup.ts
@@ -5,6 +5,7 @@
 
 import { Event } from '../../../base/common/event.js';
 import { IDisposable } from '../../../base/common/lifecycle.js';
+import { CDPEvent, CDPRequest, CDPResponse } from './cdp/types.js';
 
 export const ipcBrowserViewGroupChannelName = 'browserViewGroup';
 
@@ -27,10 +28,11 @@ export interface IBrowserViewGroup extends IDisposable {
 	readonly onDidAddView: Event<IBrowserViewGroupViewEvent>;
 	readonly onDidRemoveView: Event<IBrowserViewGroupViewEvent>;
 	readonly onDidDestroy: Event<void>;
+	readonly onCDPMessage: Event<CDPResponse | CDPEvent>;
 
 	addView(viewId: string): Promise<void>;
 	removeView(viewId: string): Promise<void>;
-	getDebugWebSocketEndpoint(): Promise<string>;
+	sendCDPMessage(msg: CDPRequest): Promise<void>;
 }
 
 /**
@@ -48,12 +50,14 @@ export interface IBrowserViewGroupService {
 	onDynamicDidAddView(groupId: string): Event<IBrowserViewGroupViewEvent>;
 	onDynamicDidRemoveView(groupId: string): Event<IBrowserViewGroupViewEvent>;
 	onDynamicDidDestroy(groupId: string): Event<void>;
+	onDynamicCDPMessage(groupId: string): Event<CDPResponse | CDPEvent>;
 
 	/**
 	 * Create a new browser view group.
+	 * @param windowId The ID of the primary window the group should be associated with.
 	 * @returns The id of the newly created group.
 	 */
-	createGroup(): Promise<string>;
+	createGroup(windowId: number): Promise<string>;
 
 	/**
 	 * Destroy a browser view group.
@@ -78,9 +82,9 @@ export interface IBrowserViewGroupService {
 	removeViewFromGroup(groupId: string, viewId: string): Promise<void>;
 
 	/**
-	 * Get a short-lived CDP WebSocket endpoint URL for a specific group.
-	 * The returned URL contains a single-use token.
+	 * Send a CDP message to a group's browser proxy.
 	 * @param groupId The group identifier.
+	 * @param message The CDP request.
 	 */
-	getDebugWebSocketEndpoint(groupId: string): Promise<string>;
+	sendCDPMessage(groupId: string, message: CDPRequest): Promise<void>;
 }
diff --git a/src/vs/platform/browserView/common/browserViewTelemetry.ts b/src/vs/platform/browserView/common/browserViewTelemetry.ts
index f261d0261a20b..66853e50999a2 100644
--- a/src/vs/platform/browserView/common/browserViewTelemetry.ts
+++ b/src/vs/platform/browserView/common/browserViewTelemetry.ts
@@ -9,6 +9,8 @@ import { ITelemetryService } from '../../telemetry/common/telemetry.js';
 export type IntegratedBrowserOpenSource =
 	/** Created via CDP, such as by the agent using Playwright tools. */
 	| 'cdpCreated'
+	/** Opened via a (non-agentic) chat tool invocation. */
+	| 'chatTool'
 	/** Opened via the "Open Integrated Browser" command without a URL argument.
 	 * This typically means the user ran the command manually from the Command Palette. */
 	| 'commandWithoutUrl'
diff --git a/src/vs/platform/browserView/common/cdp/proxy.ts b/src/vs/platform/browserView/common/cdp/proxy.ts
index 85dc5f6d52d84..86b3f4af1a50d 100644
--- a/src/vs/platform/browserView/common/cdp/proxy.ts
+++ b/src/vs/platform/browserView/common/cdp/proxy.ts
@@ -6,7 +6,7 @@
 import { Disposable, DisposableMap } from '../../../../base/common/lifecycle.js';
 import { Emitter, Event } from '../../../../base/common/event.js';
 import { generateUuid } from '../../../../base/common/uuid.js';
-import { ICDPTarget, CDPEvent, CDPError, CDPServerError, CDPMethodNotFoundError, CDPInvalidParamsError, ICDPConnection, CDPTargetInfo, ICDPBrowserTarget } from './types.js';
+import { ICDPTarget, CDPRequest, CDPResponse, CDPEvent, CDPError, CDPErrorCode, CDPServerError, CDPMethodNotFoundError, CDPInvalidParamsError, ICDPConnection, CDPTargetInfo, ICDPBrowserTarget } from './types.js';
 
 /**
  * CDP protocol handler for browser-level connections.
@@ -95,22 +95,29 @@ export class CDPBrowserProxy extends Disposable implements ICDPConnection {
 		for (const target of this.browserTarget.getTargets()) {
 			void this._targets.register(target);
 		}
+
+		// Mirror typed events to the onMessage channel
+		this._register(this._onEvent.event(event => {
+			this._onMessage.fire(event);
+		}));
 	}
 
 	// #region Public API
 
-	// Events to external client (ICDPConnection)
+	// Events to external clients
 	private readonly _onEvent = this._register(new Emitter<CDPEvent>());
 	readonly onEvent: Event<CDPEvent> = this._onEvent.event;
 	private readonly _onClose = this._register(new Emitter<void>());
 	readonly onClose: Event<void> = this._onClose.event;
+	private readonly _onMessage = this._register(new Emitter<CDPResponse | CDPEvent>());
+	readonly onMessage: Event<CDPResponse | CDPEvent> = this._onMessage.event;
 
 	/**
-	 * Send a CDP message and await the result.
+	 * Send a CDP command and await the result.
 	 * Browser-level handlers (Browser.*, Target.*) are checked first.
 	 * Other commands are routed to the page session identified by sessionId.
 	 */
-	async sendMessage(method: string, params: unknown = {}, sessionId?: string): Promise<unknown> {
+	async sendCommand(method: string, params: unknown = {}, sessionId?: string): Promise<unknown> {
 		try {
 			// Browser-level command handling
 			if (
@@ -131,7 +138,7 @@ export class CDPBrowserProxy extends Disposable implements ICDPConnection {
 				throw new CDPServerError(`Session not found: ${sessionId}`);
 			}
 
-			const result = await connection.sendMessage(method, params);
+			const result = await connection.sendCommand(method, params);
 			return result ?? {};
 		} catch (error) {
 			if (error instanceof CDPError) {
@@ -141,6 +148,27 @@ export class CDPBrowserProxy extends Disposable implements ICDPConnection {
 		}
 	}
 
+	/**
+	 * Accept a CDP request from a message-based transport (WebSocket, IPC, etc.), route it,
+	 * and deliver the response or error via {@link onMessage}.
+	 */
+	async sendMessage({ id, method, params, sessionId }: CDPRequest): Promise<void> {
+		return this.sendCommand(method, params, sessionId)
+			.then(result => {
+				this._onMessage.fire({ id, result, sessionId });
+			})
+			.catch((error: Error) => {
+				this._onMessage.fire({
+					id,
+					error: {
+						code: error instanceof CDPError ? error.code : CDPErrorCode.ServerError,
+						message: error.message || 'Unknown error'
+					},
+					sessionId
+				});
+			});
+	}
+
 	// #endregion
 
 	// #region CDP Commands
@@ -206,7 +234,7 @@ export class CDPBrowserProxy extends Disposable implements ICDPConnection {
 	}
 
 	private async handleTargetGetTargets() {
-		return { targetInfos: this._targets.getAllInfos() };
+		return { targetInfos: Array.from(this._targets.getAllInfos()) };
 	}
 
 	private async handleTargetGetTargetInfo({ targetId }: { targetId?: string } = {}) {
diff --git a/src/vs/platform/browserView/common/cdp/types.ts b/src/vs/platform/browserView/common/cdp/types.ts
index 603467e3ed2df..6fbfd30e26f9b 100644
--- a/src/vs/platform/browserView/common/cdp/types.ts
+++ b/src/vs/platform/browserView/common/cdp/types.ts
@@ -151,7 +151,7 @@ export interface ICDPBrowserTarget extends ICDPTarget {
 	/** Get all available targets */
 	getTargets(): IterableIterator<ICDPTarget>;
 	/** Create a new target in the specified browser context */
-	createTarget(url: string, browserContextId?: string): Promise<ICDPTarget>;
+	createTarget(url: string, browserContextId?: string, windowId?: number): Promise<ICDPTarget>;
 	/** Activate a target (bring to foreground) */
 	activateTarget(target: ICDPTarget): Promise<void>;
 	/** Close a target */
@@ -187,5 +187,5 @@ export interface ICDPConnection extends IDisposable {
 	 * @param sessionId Optional session ID for targeting a specific session
 	 * @returns Promise resolving to the result or rejecting with a CDPError
 	 */
-	sendMessage(method: string, params?: unknown, sessionId?: string): Promise<unknown>;
+	sendCommand(method: string, params?: unknown, sessionId?: string): Promise<unknown>;
 }
diff --git a/src/vs/platform/browserView/common/playwrightService.ts b/src/vs/platform/browserView/common/playwrightService.ts
index b49c50b5fb388..1615924a5cfe6 100644
--- a/src/vs/platform/browserView/common/playwrightService.ts
+++ b/src/vs/platform/browserView/common/playwrightService.ts
@@ -4,7 +4,6 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Event } from '../../../base/common/event.js';
-import { VSBuffer } from '../../../base/common/buffer.js';
 import { createDecorator } from '../../instantiation/common/instantiation.js';
 
 export const IPlaywrightService = createDecorator<IPlaywrightService>('playwrightService');
@@ -63,23 +62,24 @@ export interface IPlaywrightService {
 	getSummary(pageId: string): Promise<string>;
 
 	/**
-	 * Run a function with access to a Playwright page.
+	 * Run a function with access to a Playwright page and return its raw result, or throw an error.
 	 * The first function argument is always the Playwright `page` object, and additional arguments can be passed after.
 	 * @param pageId The browser view ID identifying the page to operate on.
 	 * @param fnDef The function code to execute. Should contain the function definition but not its invocation, e.g. `async (page, arg1, arg2) => { ... }`.
 	 * @param args Additional arguments to pass to the function after the `page` object.
-	 * @returns The result of the function execution, including a page summary.
+	 * @returns The result of the function execution.
 	 */
-	invokeFunction(pageId: string, fnDef: string, ...args: unknown[]): Promise<{ result: unknown; summary: string }>;
+	invokeFunctionRaw<T>(pageId: string, fnDef: string, ...args: unknown[]): Promise<T>;
 
 	/**
-	 * Takes a screenshot of the current page viewport and returns it as a VSBuffer.
-	 * @param pageId The browser view ID identifying the page to capture.
-	 * @param selector Optional Playwright selector to capture a specific element instead of the viewport.
-	 * @param fullPage Whether to capture the full scrollable page instead of just the viewport.
-	 * @returns The screenshot image data.
+	 * Run a function with access to a Playwright page and return a result for tool output, including error handling.
+	 * The first function argument is always the Playwright `page` object, and additional arguments can be passed after.
+	 * @param pageId The browser view ID identifying the page to operate on.
+	 * @param fnDef The function code to execute. Should contain the function definition but not its invocation, e.g. `async (page, arg1, arg2) => { ... }`.
+	 * @param args Additional arguments to pass to the function after the `page` object.
+	 * @returns The result of the function execution, including a page summary.
 	 */
-	captureScreenshot(pageId: string, selector?: string, fullPage?: boolean): Promise<VSBuffer>;
+	invokeFunction(pageId: string, fnDef: string, ...args: unknown[]): Promise<{ result: unknown; summary: string }>;
 
 	/**
 	 * Responds to a file chooser dialog on the given page.
diff --git a/src/vs/platform/browserView/electron-main/browserView.ts b/src/vs/platform/browserView/electron-main/browserView.ts
index 45e5d838d277c..d8a2d96987c61 100644
--- a/src/vs/platform/browserView/electron-main/browserView.ts
+++ b/src/vs/platform/browserView/electron-main/browserView.ts
@@ -8,18 +8,19 @@ import { FileAccess } from '../../../base/common/network.js';
 import { Disposable } from '../../../base/common/lifecycle.js';
 import { Emitter, Event } from '../../../base/common/event.js';
 import { VSBuffer } from '../../../base/common/buffer.js';
-import { IBrowserViewBounds, IBrowserViewDevToolsStateEvent, IBrowserViewFocusEvent, IBrowserViewKeyDownEvent, IBrowserViewState, IBrowserViewNavigationEvent, IBrowserViewLoadingEvent, IBrowserViewLoadError, IBrowserViewTitleChangeEvent, IBrowserViewFaviconChangeEvent, IBrowserViewNewPageRequest, IBrowserViewCaptureScreenshotOptions, IBrowserViewFindInPageOptions, IBrowserViewFindInPageResult, IBrowserViewVisibilityEvent, BrowserNewPageLocation, browserViewIsolatedWorldId } from '../common/browserView.js';
+import { IBrowserViewBounds, IBrowserViewDevToolsStateEvent, IBrowserViewFocusEvent, IBrowserViewKeyDownEvent, IBrowserViewState, IBrowserViewNavigationEvent, IBrowserViewLoadingEvent, IBrowserViewLoadError, IBrowserViewTitleChangeEvent, IBrowserViewFaviconChangeEvent, IBrowserViewNewPageRequest, IBrowserViewCaptureScreenshotOptions, IBrowserViewFindInPageOptions, IBrowserViewFindInPageResult, IBrowserViewVisibilityEvent, BrowserNewPageLocation, browserViewIsolatedWorldId, browserZoomFactors, browserZoomDefaultIndex } from '../common/browserView.js';
 import { EVENT_KEY_CODE_MAP, KeyCode, KeyMod, SCAN_CODE_STR_TO_EVENT_KEY_CODE } from '../../../base/common/keyCodes.js';
 import { IWindowsMainService } from '../../windows/electron-main/windows.js';
-import { IBaseWindow, ICodeWindow } from '../../window/electron-main/window.js';
+import { ICodeWindow } from '../../window/electron-main/window.js';
 import { IAuxiliaryWindowsMainService } from '../../auxiliaryWindow/electron-main/auxiliaryWindows.js';
-import { IAuxiliaryWindow } from '../../auxiliaryWindow/electron-main/auxiliaryWindow.js';
 import { isMacintosh } from '../../../base/common/platform.js';
 import { BrowserViewUri } from '../common/browserViewUri.js';
 import { BrowserViewDebugger } from './browserViewDebugger.js';
 import { ILogService } from '../../log/common/log.js';
 import { ICDPTarget, ICDPConnection, CDPTargetInfo } from '../common/cdp/types.js';
 import { BrowserSession } from './browserSession.js';
+import { IAuxiliaryWindow } from '../../auxiliaryWindow/electron-main/auxiliaryWindow.js';
+import { hasKey } from '../../../base/common/types.js';
 
 /** Key combinations that are used in system-level shortcuts. */
 const nativeShortcuts = new Set([
@@ -45,9 +46,10 @@ export class BrowserView extends Disposable implements ICDPTarget {
 	private _lastFavicon: string | undefined = undefined;
 	private _lastError: IBrowserViewLoadError | undefined = undefined;
 	private _lastUserGestureTimestamp: number = -Infinity;
+	private _browserZoomIndex: number = browserZoomDefaultIndex;
 
 	private _debugger: BrowserViewDebugger;
-	private _window: IBaseWindow | undefined;
+	private _window: ICodeWindow | IAuxiliaryWindow | undefined;
 	private _isSendingKeyEvent = false;
 	private _isDisposed = false;
 
@@ -88,6 +90,7 @@ export class BrowserView extends Disposable implements ICDPTarget {
 		public readonly id: string,
 		public readonly session: BrowserSession,
 		createChildView: (options?: Electron.WebContentsViewConstructorOptions) => BrowserView,
+		openContextMenu: (view: BrowserView, params: Electron.ContextMenuParams) => void,
 		options: Electron.WebContentsViewConstructorOptions | undefined,
 		@IWindowsMainService private readonly windowsMainService: IWindowsMainService,
 		@IAuxiliaryWindowsMainService private readonly auxiliaryWindowsMainService: IAuxiliaryWindowsMainService,
@@ -150,6 +153,10 @@ export class BrowserView extends Disposable implements ICDPTarget {
 			};
 		});
 
+		this._view.webContents.on('context-menu', (_event, params) => {
+			openContextMenu(this, params);
+		});
+
 		this._view.webContents.on('destroyed', () => {
 			this.dispose();
 		});
@@ -272,6 +279,12 @@ export class BrowserView extends Disposable implements ICDPTarget {
 		webContents.on('did-navigate', fireNavigationEvent);
 		webContents.on('did-navigate-in-page', fireNavigationEvent);
 
+		// Chromium resets the zoom factor to its per-origin default (100%) when
+		// navigating to a new document. Re-apply our stored zoom to override it.
+		webContents.on('did-navigate', () => {
+			this._view.webContents.setZoomFactor(browserZoomFactors[this._browserZoomIndex]);
+		});
+
 		// Focus events
 		webContents.on('focus', () => {
 			this._onDidChangeFocus.fire({ focused: true });
@@ -359,7 +372,8 @@ export class BrowserView extends Disposable implements ICDPTarget {
 			lastScreenshot: this._lastScreenshot,
 			lastFavicon: this._lastFavicon,
 			lastError: this._lastError,
-			storageScope: this.session.storageScope
+			storageScope: this.session.storageScope,
+			browserZoomIndex: this._browserZoomIndex
 		};
 	}
 
@@ -375,7 +389,7 @@ export class BrowserView extends Disposable implements ICDPTarget {
 	 */
 	layout(bounds: IBrowserViewBounds): void {
 		if (this._window?.win?.id !== bounds.windowId) {
-			const newWindow = this.windowById(bounds.windowId);
+			const newWindow = this._windowById(bounds.windowId);
 			if (newWindow) {
 				this._window?.win?.contentView.removeChildView(this._view);
 				this._window = newWindow;
@@ -383,7 +397,7 @@ export class BrowserView extends Disposable implements ICDPTarget {
 			}
 		}
 
-		this._view.webContents.setZoomFactor(bounds.zoomFactor);
+		this._view.setBorderRadius(Math.round(bounds.cornerRadius * bounds.zoomFactor));
 		this._view.setBounds({
 			x: Math.round(bounds.x * bounds.zoomFactor),
 			y: Math.round(bounds.y * bounds.zoomFactor),
@@ -392,6 +406,12 @@ export class BrowserView extends Disposable implements ICDPTarget {
 		});
 	}
 
+	setBrowserZoomIndex(zoomIndex: number): void {
+		this._browserZoomIndex = Math.max(0, Math.min(zoomIndex, browserZoomFactors.length - 1));
+		const browserZoomFactor = browserZoomFactors[this._browserZoomIndex];
+		this._view.webContents.setZoomFactor(browserZoomFactor);
+	}
+
 	/**
 	 * Set the visibility of this view
 	 */
@@ -444,8 +464,12 @@ export class BrowserView extends Disposable implements ICDPTarget {
 	/**
 	 * Reload the current page
 	 */
-	reload(): void {
-		this._view.webContents.reload();
+	reload(hard?: boolean): void {
+		if (hard) {
+			this._view.webContents.reloadIgnoringCache();
+		} else {
+			this._view.webContents.reload();
+		}
 	}
 
 	/**
@@ -468,8 +492,7 @@ export class BrowserView extends Disposable implements ICDPTarget {
 	async captureScreenshot(options?: IBrowserViewCaptureScreenshotOptions): Promise<VSBuffer> {
 		const quality = options?.quality ?? 80;
 		const image = await this._view.webContents.capturePage(options?.rect, {
-			stayHidden: true,
-			stayAwake: true
+			stayHidden: true
 		});
 		const buffer = image.toJPEG(quality);
 		const screenshot = VSBuffer.wrap(buffer);
@@ -509,13 +532,6 @@ export class BrowserView extends Disposable implements ICDPTarget {
 		}
 	}
 
-	/**
-	 * Set the zoom factor of this view
-	 */
-	async setZoomFactor(zoomFactor: number): Promise<void> {
-		await this._view.webContents.setZoomFactor(zoomFactor);
-	}
-
 	/**
 	 * Focus this view
 	 */
@@ -576,6 +592,22 @@ export class BrowserView extends Disposable implements ICDPTarget {
 		return this._view;
 	}
 
+	/**
+	 * Get the hosting Electron window for this view, if any.
+	 * This can be an auxiliary window, depending on where the view is currently hosted.
+	 */
+	getElectronWindow(): Electron.BrowserWindow | undefined {
+		return this._window?.win ?? undefined;
+	}
+
+	/**
+	 * Get the main code window hosting this browser view, if any. This is used for routing commands from the browser view to the correct window.
+	 * If the browser view is hosted in an auxiliary window, this will return the parent code window of that auxiliary window.
+	 */
+	getTopCodeWindow(): ICodeWindow | undefined {
+		return this._window && hasKey(this._window, { parentId: true }) ? this._codeWindowById(this._window.parentId) : undefined;
+	}
+
 	// ============ ICDPTarget implementation ============
 
 	/**
@@ -609,7 +641,9 @@ export class BrowserView extends Disposable implements ICDPTarget {
 		this._onDidClose.fire();
 
 		// Clean up the view and all its event listeners
-		this._view.webContents.close({ waitForBeforeUnload: false });
+		if (!this._view.webContents.isDestroyed()) {
+			this._view.webContents.close({ waitForBeforeUnload: false });
+		}
 
 		super.dispose();
 	}
@@ -624,6 +658,7 @@ export class BrowserView extends Disposable implements ICDPTarget {
 
 		const isArrowKey = keyCode >= KeyCode.LeftArrow && keyCode <= KeyCode.DownArrow;
 		const isNonEditingKey =
+			keyCode === KeyCode.Enter ||
 			keyCode === KeyCode.Escape ||
 			keyCode >= KeyCode.F1 && keyCode <= KeyCode.F24 ||
 			keyCode >= KeyCode.AudioVolumeMute;
@@ -663,11 +698,11 @@ export class BrowserView extends Disposable implements ICDPTarget {
 		return true;
 	}
 
-	private windowById(windowId: number | undefined): ICodeWindow | IAuxiliaryWindow | undefined {
-		return this.codeWindowById(windowId) ?? this.auxiliaryWindowById(windowId);
+	private _windowById(windowId: number | undefined): ICodeWindow | IAuxiliaryWindow | undefined {
+		return this._codeWindowById(windowId) ?? this._auxiliaryWindowById(windowId);
 	}
 
-	private codeWindowById(windowId: number | undefined): ICodeWindow | undefined {
+	private _codeWindowById(windowId: number | undefined): ICodeWindow | undefined {
 		if (typeof windowId !== 'number') {
 			return undefined;
 		}
@@ -675,7 +710,7 @@ export class BrowserView extends Disposable implements ICDPTarget {
 		return this.windowsMainService.getWindowById(windowId);
 	}
 
-	private auxiliaryWindowById(windowId: number | undefined): IAuxiliaryWindow | undefined {
+	private _auxiliaryWindowById(windowId: number | undefined): IAuxiliaryWindow | undefined {
 		if (typeof windowId !== 'number') {
 			return undefined;
 		}
diff --git a/src/vs/platform/browserView/electron-main/browserViewCDPProxyServer.ts b/src/vs/platform/browserView/electron-main/browserViewCDPProxyServer.ts
deleted file mode 100644
index 30ad512c042d0..0000000000000
--- a/src/vs/platform/browserView/electron-main/browserViewCDPProxyServer.ts
+++ /dev/null
@@ -1,269 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-import { Disposable, DisposableStore } from '../../../base/common/lifecycle.js';
-import { ILogService } from '../../log/common/log.js';
-import type * as http from 'http';
-import { AddressInfo, Socket } from 'net';
-import { upgradeToISocket } from '../../../base/parts/ipc/node/ipc.net.js';
-import { generateUuid } from '../../../base/common/uuid.js';
-import { VSBuffer } from '../../../base/common/buffer.js';
-import { CDPBrowserProxy } from '../common/cdp/proxy.js';
-import { CDPEvent, CDPRequest, CDPError, CDPErrorCode, ICDPBrowserTarget, ICDPConnection } from '../common/cdp/types.js';
-import { disposableTimeout } from '../../../base/common/async.js';
-import { ISocket } from '../../../base/parts/ipc/common/ipc.net.js';
-import { createDecorator } from '../../instantiation/common/instantiation.js';
-
-export const IBrowserViewCDPProxyServer = createDecorator<IBrowserViewCDPProxyServer>('browserViewCDPProxyServer');
-
-export interface IBrowserViewCDPProxyServer {
-	readonly _serviceBrand: undefined;
-
-	/**
-	 * Returns a debug endpoint with a short-lived, single-use token for a specific browser target.
-	 */
-	getWebSocketEndpointForTarget(target: ICDPBrowserTarget): Promise<string>;
-
-	/**
-	 * Unregister a previously registered browser target.
-	 */
-	removeTarget(target: ICDPBrowserTarget): Promise<void>;
-}
-
-/**
- * WebSocket server that provides CDP debugging for browser views.
- *
- * Manages a registry of {@link ICDPBrowserTarget} instances, each reachable
- * at its own `/devtools/browser/{id}` WebSocket endpoint.
- */
-export class BrowserViewCDPProxyServer extends Disposable implements IBrowserViewCDPProxyServer {
-	declare readonly _serviceBrand: undefined;
-
-	private server: http.Server | undefined;
-	private port: number | undefined;
-
-	private readonly tokens = this._register(new TokenManager<string>());
-	private readonly targets = new Map<string, ICDPBrowserTarget>();
-
-	constructor(
-		@ILogService private readonly logService: ILogService
-	) {
-		super();
-	}
-
-	/**
-	 * Register a browser target and return a WebSocket endpoint URL for it.
-	 * The target is reachable at `/devtools/browser/{targetId}`.
-	 */
-	async getWebSocketEndpointForTarget(target: ICDPBrowserTarget): Promise<string> {
-		await this.ensureServerStarted();
-
-		const targetInfo = await target.getTargetInfo();
-		const targetId = targetInfo.targetId;
-
-		// Register (or re-register) the target
-		this.targets.set(targetId, target);
-
-		const token = await this.tokens.issueToken(targetId);
-		return `ws://localhost:${this.port}/devtools/browser/${targetId}?token=${token}`;
-	}
-
-	/**
-	 * Unregister a previously registered browser target.
-	 */
-	async removeTarget(target: ICDPBrowserTarget): Promise<void> {
-		const targetInfo = await target.getTargetInfo();
-		this.targets.delete(targetInfo.targetId);
-	}
-
-	private async ensureServerStarted(): Promise<void> {
-		if (this.server) {
-			return;
-		}
-
-		const http = await import('http');
-		this.server = http.createServer();
-
-		await new Promise<void>((resolve, reject) => {
-			// Only listen on localhost to prevent external access
-			this.server!.listen(0, '127.0.0.1', () => resolve());
-			this.server!.once('error', reject);
-		});
-
-		const address = this.server.address() as AddressInfo;
-		this.port = address.port;
-
-		this.server.on('request', (req, res) => this.handleHttpRequest(req, res));
-		this.server.on('upgrade', (req: http.IncomingMessage, socket: Socket) => this.handleWebSocketUpgrade(req, socket));
-	}
-
-	private async handleHttpRequest(_req: http.IncomingMessage, res: http.ServerResponse): Promise<void> {
-		this.logService.debug(`[BrowserViewDebugProxy] HTTP request at ${_req.url}`);
-		// No support for HTTP endpoints for now.
-		res.writeHead(404);
-		res.end();
-	}
-
-	private handleWebSocketUpgrade(req: http.IncomingMessage, socket: Socket): void {
-		const [pathname, params] = (req.url || '').split('?');
-
-		const browserMatch = pathname.match(/^\/devtools\/browser\/([^/?]+)$/);
-
-		this.logService.debug(`[BrowserViewDebugProxy] WebSocket upgrade requested: ${pathname}`);
-
-		if (!browserMatch) {
-			this.logService.warn(`[BrowserViewDebugProxy] Rejecting WebSocket on unknown path: ${pathname}`);
-			socket.write('HTTP/1.1 404 Not Found\r\n\r\n');
-			socket.end();
-			return;
-		}
-
-		const targetId = browserMatch[1];
-
-		const token = new URLSearchParams(params).get('token');
-		const tokenTargetId = token && this.tokens.consumeToken(token);
-		if (!tokenTargetId || tokenTargetId !== targetId) {
-			socket.write('HTTP/1.1 401 Unauthorized\r\n\r\n');
-			socket.end();
-			return;
-		}
-
-		const target = this.targets.get(targetId);
-		if (!target) {
-			this.logService.warn(`[BrowserViewDebugProxy] Browser target not found: ${targetId}`);
-			socket.write('HTTP/1.1 404 Not Found\r\n\r\n');
-			socket.end();
-			return;
-		}
-
-		this.logService.debug(`[BrowserViewDebugProxy] WebSocket connected: ${pathname}`);
-
-		const upgraded = upgradeToISocket(req, socket, {
-			debugLabel: 'browser-view-cdp-' + generateUuid(),
-			enableMessageSplitting: false,
-		});
-
-		if (!upgraded) {
-			return;
-		}
-
-		const proxy = new CDPBrowserProxy(target);
-		const disposables = this.wireWebSocket(upgraded, proxy);
-		this._register(disposables);
-		this._register(upgraded);
-	}
-
-	/**
-	 * Wire a WebSocket (ISocket) to an ICDPConnection bidirectionally.
-	 * Returns a DisposableStore that cleans up all subscriptions.
-	 */
-	private wireWebSocket(upgraded: ISocket, connection: ICDPConnection): DisposableStore {
-		const disposables = new DisposableStore();
-
-		// Socket -> Connection: parse JSON, call sendMessage, write response/error
-		disposables.add(upgraded.onData((rawData: VSBuffer) => {
-			try {
-				const message = rawData.toString();
-				const { id, method, params, sessionId } = JSON.parse(message) as CDPRequest;
-				this.logService.debug(`[BrowserViewDebugProxy] <- ${message}`);
-				connection.sendMessage(method, params, sessionId)
-					.then((result: unknown) => {
-						const response = { id, result, sessionId };
-						const responseStr = JSON.stringify(response);
-						this.logService.debug(`[BrowserViewDebugProxy] -> ${responseStr}`);
-						upgraded.write(VSBuffer.fromString(responseStr));
-					})
-					.catch((error: Error) => {
-						const response = {
-							id,
-							error: {
-								code: error instanceof CDPError ? error.code : CDPErrorCode.ServerError,
-								message: error.message || 'Unknown error'
-							},
-							sessionId
-						};
-						const responseStr = JSON.stringify(response);
-						this.logService.debug(`[BrowserViewDebugProxy] -> ${responseStr}`);
-						upgraded.write(VSBuffer.fromString(responseStr));
-					});
-			} catch (error) {
-				this.logService.error('[BrowserViewDebugProxy] Error parsing message:', error);
-				upgraded.end();
-			}
-		}));
-
-		// Connection -> Socket: serialize events and write
-		disposables.add(connection.onEvent((event: CDPEvent) => {
-			const eventStr = JSON.stringify(event);
-			this.logService.debug(`[BrowserViewDebugProxy] -> ${eventStr}`);
-			upgraded.write(VSBuffer.fromString(eventStr));
-		}));
-
-		// Connection close -> close socket
-		disposables.add(connection.onClose(() => {
-			this.logService.debug(`[BrowserViewDebugProxy] WebSocket closing`);
-			upgraded.end();
-		}));
-
-		// Socket closed -> cleanup
-		disposables.add(upgraded.onClose(() => {
-			this.logService.debug(`[BrowserViewDebugProxy] WebSocket closed`);
-			connection.dispose();
-			disposables.dispose();
-		}));
-
-		return disposables;
-	}
-
-	override dispose(): void {
-		if (this.server) {
-			this.server.close();
-			this.server = undefined;
-		}
-
-		super.dispose();
-	}
-}
-
-class TokenManager<TDetails> extends Disposable {
-	/** Map of currently valid single-use tokens to their associated details. */
-	private readonly tokens = new Map<string, { details: TDetails; expiresAt: number }>();
-
-	/**
-	 * Creates a short-lived, single-use token bound to a specific target.
-	 * The token is revoked once consumed or after 30 seconds.
-	 */
-	async issueToken(details: TDetails): Promise<string> {
-		const token = this.makeToken();
-		this.tokens.set(token, { details: Object.freeze(details), expiresAt: Date.now() + 30_000 });
-		this._register(disposableTimeout(() => this.tokens.delete(token), 30_000));
-		return token;
-	}
-
-	/**
-	 * Consume a token. Returns the details it was issued with, or
-	 * `undefined` if the token is invalid or expired.
-	 */
-	consumeToken(token: string): TDetails | undefined {
-		if (!token) {
-			return undefined;
-		}
-		const info = this.tokens.get(token);
-		if (!info) {
-			return undefined;
-		}
-		this.tokens.delete(token);
-		return Date.now() <= info.expiresAt ? info.details : undefined;
-	}
-
-	private makeToken(): string {
-		const bytes = crypto.getRandomValues(new Uint8Array(32));
-		const binary = Array.from(bytes).map(b => String.fromCharCode(b)).join('');
-		const base64 = btoa(binary);
-		const urlSafeToken = base64.replace(/\+/g, '-').replace(/\//g, '_').replace(/=+$/g, '');
-
-		return urlSafeToken;
-	}
-}
diff --git a/src/vs/platform/browserView/electron-main/browserViewDebugger.ts b/src/vs/platform/browserView/electron-main/browserViewDebugger.ts
index e9956c91b185e..c0bdb734ef708 100644
--- a/src/vs/platform/browserView/electron-main/browserViewDebugger.ts
+++ b/src/vs/platform/browserView/electron-main/browserViewDebugger.ts
@@ -60,7 +60,7 @@ export class BrowserViewDebugger extends Disposable implements ICDPTarget {
 		}) as { sessionId: string };
 
 		const sessionId = result.sessionId;
-		const session = new DebugSession(sessionId, this._electronDebugger);
+		const session = new DebugSession(sessionId, this.view, this._electronDebugger);
 		this._sessions.set(sessionId, session);
 		session.onClose(() => this._sessions.deleteAndDispose(sessionId));
 
@@ -182,18 +182,27 @@ class DebugSession extends Disposable implements ICDPConnection {
 
 	constructor(
 		public readonly sessionId: string,
+		private readonly _view: BrowserView,
 		private readonly _electronDebugger: Electron.Debugger
 	) {
 		super();
 	}
 
-	async sendMessage(method: string, params?: unknown, _sessionId?: string): Promise<unknown> {
+	async sendCommand(method: string, params?: unknown, _sessionId?: string): Promise<unknown> {
 		// This crashes Electron. Don't pass it through.
 		if (method === 'Emulation.setDeviceMetricsOverride') {
 			return Promise.resolve({});
 		}
 
-		return this._electronDebugger.sendCommand(method, params, this.sessionId);
+		const result = await this._electronDebugger.sendCommand(method, params, this.sessionId);
+
+		// Electron overrides dialog behavior in a way that this command does not auto-dismiss the dialog.
+		// So we manually emit the (internal) event to dismiss open dialogs when this command is sent.
+		if (method === 'Page.handleJavaScriptDialog') {
+			this._view.webContents.emit('-cancel-dialogs');
+		}
+
+		return result;
 	}
 
 	override dispose(): void {
diff --git a/src/vs/platform/browserView/electron-main/browserViewGroup.ts b/src/vs/platform/browserView/electron-main/browserViewGroup.ts
index d7d59c2701889..beed4f6042e9f 100644
--- a/src/vs/platform/browserView/electron-main/browserViewGroup.ts
+++ b/src/vs/platform/browserView/electron-main/browserViewGroup.ts
@@ -6,10 +6,9 @@
 import { Disposable, DisposableStore } from '../../../base/common/lifecycle.js';
 import { Emitter, Event } from '../../../base/common/event.js';
 import { BrowserView } from './browserView.js';
-import { ICDPTarget, CDPBrowserVersion, CDPWindowBounds, CDPTargetInfo, ICDPConnection, ICDPBrowserTarget } from '../common/cdp/types.js';
+import { ICDPTarget, CDPBrowserVersion, CDPWindowBounds, CDPTargetInfo, ICDPConnection, ICDPBrowserTarget, CDPRequest, CDPResponse, CDPEvent } from '../common/cdp/types.js';
 import { CDPBrowserProxy } from '../common/cdp/proxy.js';
 import { IBrowserViewGroup, IBrowserViewGroupViewEvent } from '../common/browserViewGroup.js';
-import { IBrowserViewCDPProxyServer } from './browserViewCDPProxyServer.js';
 import { IBrowserViewMainService } from './browserViewMainService.js';
 
 /**
@@ -49,8 +48,8 @@ export class BrowserViewGroup extends Disposable implements ICDPBrowserTarget, I
 
 	constructor(
 		readonly id: string,
-		@IBrowserViewMainService private readonly browserViewMainService: IBrowserViewMainService,
-		@IBrowserViewCDPProxyServer private readonly cdpProxyServer: IBrowserViewCDPProxyServer,
+		private readonly windowId: number,
+		@IBrowserViewMainService private readonly browserViewMainService: IBrowserViewMainService
 	) {
 		super();
 	}
@@ -127,12 +126,12 @@ export class BrowserViewGroup extends Disposable implements ICDPBrowserTarget, I
 		return this.views.values();
 	}
 
-	async createTarget(url: string, browserContextId?: string): Promise<ICDPTarget> {
+	async createTarget(url: string, browserContextId?: string, windowId = this.windowId): Promise<ICDPTarget> {
 		if (browserContextId && !this.knownContextIds.has(browserContextId)) {
 			throw new Error(`Unknown browser context ${browserContextId}`);
 		}
 
-		const target = await this.browserViewMainService.createTarget(url, browserContextId);
+		const target = await this.browserViewMainService.createTarget(url, browserContextId, windowId);
 		if (target instanceof BrowserView) {
 			await this.addView(target.id);
 		}
@@ -188,19 +187,26 @@ export class BrowserViewGroup extends Disposable implements ICDPBrowserTarget, I
 
 	// #region CDP endpoint
 
-	/**
-	 * Get a WebSocket endpoint URL for connecting to this group's CDP
-	 * session. The URL contains a short-lived, single-use token.
-	 */
-	async getDebugWebSocketEndpoint(): Promise<string> {
-		return this.cdpProxyServer.getWebSocketEndpointForTarget(this);
+	private _debugger: CDPBrowserProxy | undefined;
+	get debugger(): CDPBrowserProxy {
+		if (!this._debugger) {
+			this._debugger = this._register(new CDPBrowserProxy(this));
+		}
+		return this._debugger;
+	}
+
+	async sendCDPMessage(msg: CDPRequest): Promise<void> {
+		return this.debugger.sendMessage(msg);
+	}
+
+	get onCDPMessage(): Event<CDPResponse | CDPEvent> {
+		return this.debugger.onMessage;
 	}
 
 	// #endregion
 
 	override dispose(): void {
 		this._onDidDestroy.fire();
-		this.cdpProxyServer.removeTarget(this);
 		super.dispose();
 	}
 }
diff --git a/src/vs/platform/browserView/electron-main/browserViewGroupMainService.ts b/src/vs/platform/browserView/electron-main/browserViewGroupMainService.ts
index 20dd6331c0ea5..c34bfa16b9d92 100644
--- a/src/vs/platform/browserView/electron-main/browserViewGroupMainService.ts
+++ b/src/vs/platform/browserView/electron-main/browserViewGroupMainService.ts
@@ -9,6 +9,7 @@ import { createDecorator, IInstantiationService } from '../../instantiation/comm
 import { generateUuid } from '../../../base/common/uuid.js';
 import { IBrowserViewGroupService, IBrowserViewGroupViewEvent } from '../common/browserViewGroup.js';
 import { BrowserViewGroup } from './browserViewGroup.js';
+import { CDPEvent, CDPRequest, CDPResponse } from '../common/cdp/types.js';
 
 export const IBrowserViewGroupMainService = createDecorator<IBrowserViewGroupMainService>('browserViewGroupMainService');
 
@@ -33,9 +34,9 @@ export class BrowserViewGroupMainService extends Disposable implements IBrowserV
 		super();
 	}
 
-	async createGroup(): Promise<string> {
+	async createGroup(windowId: number): Promise<string> {
 		const id = generateUuid();
-		const group = this.instantiationService.createInstance(BrowserViewGroup, id);
+		const group = this.instantiationService.createInstance(BrowserViewGroup, id, windowId);
 		this.groups.set(id, group);
 
 		// Auto-cleanup when the group disposes itself
@@ -58,8 +59,8 @@ export class BrowserViewGroupMainService extends Disposable implements IBrowserV
 		return this._getGroup(groupId).removeView(viewId);
 	}
 
-	async getDebugWebSocketEndpoint(groupId: string): Promise<string> {
-		return this._getGroup(groupId).getDebugWebSocketEndpoint();
+	async sendCDPMessage(groupId: string, message: CDPRequest): Promise<void> {
+		return this._getGroup(groupId).debugger.sendMessage(message);
 	}
 
 	onDynamicDidAddView(groupId: string): Event<IBrowserViewGroupViewEvent> {
@@ -74,6 +75,10 @@ export class BrowserViewGroupMainService extends Disposable implements IBrowserV
 		return this._getGroup(groupId).onDidDestroy;
 	}
 
+	onDynamicCDPMessage(groupId: string): Event<CDPResponse | CDPEvent> {
+		return this._getGroup(groupId).debugger.onMessage;
+	}
+
 	/**
 	 * Get a group or throw if not found.
 	 */
diff --git a/src/vs/platform/browserView/electron-main/browserViewMainService.ts b/src/vs/platform/browserView/electron-main/browserViewMainService.ts
index 7db0af2ac3451..83901046a8e04 100644
--- a/src/vs/platform/browserView/electron-main/browserViewMainService.ts
+++ b/src/vs/platform/browserView/electron-main/browserViewMainService.ts
@@ -6,7 +6,8 @@
 import { Emitter, Event } from '../../../base/common/event.js';
 import { Disposable, DisposableMap } from '../../../base/common/lifecycle.js';
 import { VSBuffer } from '../../../base/common/buffer.js';
-import { IBrowserViewBounds, IBrowserViewKeyDownEvent, IBrowserViewState, IBrowserViewService, BrowserViewStorageScope, IBrowserViewCaptureScreenshotOptions, IBrowserViewFindInPageOptions } from '../common/browserView.js';
+import { IBrowserViewBounds, IBrowserViewKeyDownEvent, IBrowserViewState, IBrowserViewService, BrowserViewStorageScope, IBrowserViewCaptureScreenshotOptions, IBrowserViewFindInPageOptions, BrowserViewCommandId } from '../common/browserView.js';
+import { clipboard, Menu, MenuItem } from 'electron';
 import { ICDPTarget, CDPBrowserVersion, CDPWindowBounds, CDPTargetInfo, ICDPConnection, ICDPBrowserTarget } from '../common/cdp/types.js';
 import { IEnvironmentMainService } from '../../environment/electron-main/environmentMainService.js';
 import { createDecorator, IInstantiationService } from '../../instantiation/common/instantiation.js';
@@ -17,8 +18,13 @@ import { IWindowsMainService } from '../../windows/electron-main/windows.js';
 import { BrowserSession } from './browserSession.js';
 import { IProductService } from '../../product/common/productService.js';
 import { CDPBrowserProxy } from '../common/cdp/proxy.js';
-import { logBrowserOpen } from '../common/browserViewTelemetry.js';
+import { IntegratedBrowserOpenSource, logBrowserOpen } from '../common/browserViewTelemetry.js';
 import { ITelemetryService } from '../../telemetry/common/telemetry.js';
+import { CancellationToken } from '../../../base/common/cancellation.js';
+import { localize } from '../../../nls.js';
+import { INativeHostMainService } from '../../native/electron-main/nativeHostMainService.js';
+import { ITextEditorOptions } from '../../editor/common/editor.js';
+import { htmlAttributeEncodeValue } from '../../../base/common/strings.js';
 
 export const IBrowserViewMainService = createDecorator<IBrowserViewMainService>('browserViewMainService');
 
@@ -40,6 +46,7 @@ export class BrowserViewMainService extends Disposable implements IBrowserViewMa
 	}
 
 	private readonly browserViews = this._register(new DisposableMap<string, BrowserView>());
+	private _keybindings: { [commandId: string]: string } = Object.create(null);
 
 	// ICDPBrowserTarget events
 	private readonly _onTargetCreated = this._register(new Emitter<BrowserView>());
@@ -53,38 +60,12 @@ export class BrowserViewMainService extends Disposable implements IBrowserViewMa
 		@IInstantiationService private readonly instantiationService: IInstantiationService,
 		@IWindowsMainService private readonly windowsMainService: IWindowsMainService,
 		@IProductService private readonly productService: IProductService,
-		@ITelemetryService private readonly telemetryService: ITelemetryService
+		@ITelemetryService private readonly telemetryService: ITelemetryService,
+		@INativeHostMainService private readonly nativeHostMainService: INativeHostMainService
 	) {
 		super();
 	}
 
-	/**
-	 * Create a browser view backed by the given {@link BrowserSession}.
-	 */
-	private createBrowserView(id: string, browserSession: BrowserSession, options?: Electron.WebContentsViewConstructorOptions): BrowserView {
-		if (this.browserViews.has(id)) {
-			throw new Error(`Browser view with id ${id} already exists`);
-		}
-
-		const view = this.instantiationService.createInstance(
-			BrowserView,
-			id,
-			browserSession,
-			// Recursive factory for nested windows (child views share the same session)
-			(childOptions) => this.createBrowserView(generateUuid(), browserSession, childOptions),
-			options
-		);
-		this.browserViews.set(id, view);
-
-		this._onTargetCreated.fire(view);
-		Event.once(view.onDidClose)(() => {
-			this._onTargetDestroyed.fire(view);
-			this.browserViews.deleteAndDispose(id);
-		});
-
-		return view;
-	}
-
 	async getOrCreateBrowserView(id: string, scope: BrowserViewStorageScope, workspaceId?: string): Promise<IBrowserViewState> {
 		if (this.browserViews.has(id)) {
 			// Note: scope will be ignored if the view already exists.
@@ -158,22 +139,15 @@ export class BrowserViewMainService extends Disposable implements IBrowserViewMa
 		return this.browserViews.values();
 	}
 
-	async createTarget(url: string, browserContextId?: string): Promise<ICDPTarget> {
-		const targetId = generateUuid();
-		const browserSession = browserContextId && BrowserSession.get(browserContextId) || BrowserSession.getOrCreateEphemeral(targetId);
-
-		// Create the browser view (fires onTargetCreated)
-		const view = this.createBrowserView(targetId, browserSession);
-
-		logBrowserOpen(this.telemetryService, 'cdpCreated');
+	async createTarget(url: string, browserContextId?: string, windowId?: number): Promise<ICDPTarget> {
+		const browserSession = browserContextId ? BrowserSession.get(browserContextId) : undefined;
 
-		// Request the workbench to open the editor
-		this.windowsMainService.sendToFocused('vscode:runAction', {
-			id: 'vscode.open',
-			args: [BrowserViewUri.forUrl(url, targetId)]
+		return this.openNew(url, {
+			session: browserSession,
+			windowId,
+			editorOptions: { preserveFocus: true },
+			source: 'cdpCreated'
 		});
-
-		return view;
 	}
 
 	async activateTarget(target: ICDPTarget): Promise<void> {
@@ -278,6 +252,10 @@ export class BrowserViewMainService extends Disposable implements IBrowserViewMa
 		return this._getBrowserView(id).onDidClose;
 	}
 
+	async getState(id: string): Promise<IBrowserViewState> {
+		return this._getBrowserView(id).getState();
+	}
+
 	async destroyBrowserView(id: string): Promise<void> {
 		return this.browserViews.deleteAndDispose(id);
 	}
@@ -306,8 +284,8 @@ export class BrowserViewMainService extends Disposable implements IBrowserViewMa
 		return this._getBrowserView(id).goForward();
 	}
 
-	async reload(id: string): Promise<void> {
-		return this._getBrowserView(id).reload();
+	async reload(id: string, hard?: boolean): Promise<void> {
+		return this._getBrowserView(id).reload(hard);
 	}
 
 	async toggleDevTools(id: string): Promise<void> {
@@ -330,10 +308,6 @@ export class BrowserViewMainService extends Disposable implements IBrowserViewMa
 		return this._getBrowserView(id).dispatchKeyEvent(keyEvent);
 	}
 
-	async setZoomFactor(id: string, zoomFactor: number): Promise<void> {
-		return this._getBrowserView(id).setZoomFactor(zoomFactor);
-	}
-
 	async focus(id: string): Promise<void> {
 		return this._getBrowserView(id).focus();
 	}
@@ -354,6 +328,10 @@ export class BrowserViewMainService extends Disposable implements IBrowserViewMa
 		return this._getBrowserView(id).clearStorage();
 	}
 
+	async setBrowserZoomIndex(id: string, zoomIndex: number): Promise<void> {
+		return this._getBrowserView(id).setBrowserZoomIndex(zoomIndex);
+	}
+
 	async clearGlobalStorage(): Promise<void> {
 		const browserSession = BrowserSession.getOrCreateGlobal();
 		await browserSession.electronSession.clearData();
@@ -366,4 +344,182 @@ export class BrowserViewMainService extends Disposable implements IBrowserViewMa
 		);
 		await browserSession.electronSession.clearData();
 	}
+
+	async updateKeybindings(keybindings: { [commandId: string]: string }): Promise<void> {
+		this._keybindings = keybindings;
+	}
+
+	/**
+	 * Create a browser view backed by the given {@link BrowserSession}.
+	 */
+	private createBrowserView(id: string, browserSession: BrowserSession, options?: Electron.WebContentsViewConstructorOptions): BrowserView {
+		if (this.browserViews.has(id)) {
+			throw new Error(`Browser view with id ${id} already exists`);
+		}
+
+		const view = this.instantiationService.createInstance(
+			BrowserView,
+			id,
+			browserSession,
+			// Recursive factory for nested windows (child views share the same session)
+			(childOptions) => this.createBrowserView(generateUuid(), browserSession, childOptions),
+			(v, params) => this.showContextMenu(v, params),
+			options
+		);
+		this.browserViews.set(id, view);
+
+		this._onTargetCreated.fire(view);
+		Event.once(view.onDidClose)(() => {
+			this._onTargetDestroyed.fire(view);
+			this.browserViews.deleteAndDispose(id);
+		});
+
+		return view;
+	}
+
+	private async openNew(
+		url: string,
+		{
+			session,
+			windowId,
+			editorOptions,
+			source
+		}: {
+			session: BrowserSession | undefined;
+			windowId: number | undefined;
+			editorOptions: ITextEditorOptions;
+			source: IntegratedBrowserOpenSource;
+		}
+	): Promise<ICDPTarget> {
+		const targetId = generateUuid();
+		const view = this.createBrowserView(targetId, session || BrowserSession.getOrCreateEphemeral(targetId));
+
+		const window = windowId !== undefined ? this.windowsMainService.getWindowById(windowId) : this.windowsMainService.getFocusedWindow();
+		if (!window) {
+			throw new Error(`Window ${windowId} not found`);
+		}
+
+
+		logBrowserOpen(this.telemetryService, source);
+
+		// Request the workbench to open the editor
+		window.sendWhenReady('vscode:runAction', CancellationToken.None, {
+			id: '_workbench.open',
+			args: [BrowserViewUri.forUrl(url, targetId), [undefined, editorOptions], undefined]
+		});
+
+		return view;
+	}
+
+	private showContextMenu(view: BrowserView, params: Electron.ContextMenuParams): void {
+		const win = view.getElectronWindow();
+		if (!win) {
+			return;
+		}
+		const webContents = view.webContents;
+		if (webContents.isDestroyed()) {
+			return;
+		}
+		const menu = new Menu();
+
+		if (params.linkURL) {
+			menu.append(new MenuItem({
+				label: localize('browser.contextMenu.openLinkInNewTab', 'Open Link in New Tab'),
+				click: () => {
+					void this.openNew(params.linkURL, {
+						session: view.session,
+						windowId: view.getTopCodeWindow()?.id,
+						editorOptions: { preserveFocus: true, inactive: true },
+						source: 'browserLinkBackground'
+					});
+				}
+			}));
+			menu.append(new MenuItem({
+				label: localize('browser.contextMenu.openLinkInExternalBrowser', 'Open Link in External Browser'),
+				click: () => { void this.nativeHostMainService.openExternal(undefined, params.linkURL); }
+			}));
+			menu.append(new MenuItem({ type: 'separator' }));
+			menu.append(new MenuItem({
+				label: localize('browser.contextMenu.copyLink', 'Copy Link'),
+				click: () => {
+					clipboard.write({
+						text: params.linkURL,
+						html: `<a href="${encodeURI(params.linkURL)}">${htmlAttributeEncodeValue(params.linkText || params.linkURL)}</a>`
+					});
+				}
+			}));
+		}
+
+		if (params.hasImageContents && params.srcURL) {
+			if (menu.items.length > 0) {
+				menu.append(new MenuItem({ type: 'separator' }));
+			}
+			menu.append(new MenuItem({
+				label: localize('browser.contextMenu.openImageInNewTab', 'Open Image in New Tab'),
+				click: () => {
+					void this.openNew(params.srcURL!, {
+						session: view.session,
+						windowId: view.getTopCodeWindow()?.id,
+						editorOptions: { preserveFocus: true, inactive: true },
+						source: 'browserLinkBackground'
+					});
+				}
+			}));
+			menu.append(new MenuItem({
+				label: localize('browser.contextMenu.copyImage', 'Copy Image'),
+				click: () => { view.webContents.copyImageAt(params.x, params.y); }
+			}));
+			menu.append(new MenuItem({
+				label: localize('browser.contextMenu.copyImageUrl', 'Copy Image URL'),
+				click: () => { clipboard.writeText(params.srcURL!); }
+			}));
+		}
+
+		if (params.isEditable) {
+			menu.append(new MenuItem({ role: 'cut', enabled: params.editFlags.canCut }));
+			menu.append(new MenuItem({ role: 'copy', enabled: params.editFlags.canCopy }));
+			menu.append(new MenuItem({ role: 'paste', enabled: params.editFlags.canPaste }));
+			menu.append(new MenuItem({ role: 'pasteAndMatchStyle', enabled: params.editFlags.canPaste }));
+			menu.append(new MenuItem({ role: 'selectAll', enabled: params.editFlags.canSelectAll }));
+		} else if (params.selectionText) {
+			menu.append(new MenuItem({ role: 'copy' }));
+		}
+
+		// Add navigation items as defaults
+		if (menu.items.length === 0) {
+			if (webContents.navigationHistory.canGoBack()) {
+				menu.append(new MenuItem({
+					label: localize('browser.contextMenu.back', 'Back'),
+					accelerator: this._keybindings[BrowserViewCommandId.GoBack],
+					click: () => webContents.navigationHistory.goBack()
+				}));
+			}
+			if (webContents.navigationHistory.canGoForward()) {
+				menu.append(new MenuItem({
+					label: localize('browser.contextMenu.forward', 'Forward'),
+					accelerator: this._keybindings[BrowserViewCommandId.GoForward],
+					click: () => webContents.navigationHistory.goForward()
+				}));
+			}
+			menu.append(new MenuItem({
+				label: localize('browser.contextMenu.reload', 'Reload'),
+				accelerator: this._keybindings[BrowserViewCommandId.Reload],
+				click: () => webContents.reload()
+			}));
+		}
+
+		menu.append(new MenuItem({ type: 'separator' }));
+		menu.append(new MenuItem({
+			label: localize('browser.contextMenu.inspect', 'Inspect'),
+			click: () => webContents.inspectElement(params.x, params.y)
+		}));
+
+		const viewBounds = view.getWebContentsView().getBounds();
+		menu.popup({
+			window: win,
+			x: viewBounds.x + params.x,
+			y: viewBounds.y + params.y,
+			sourceType: params.menuSourceType
+		});
+	}
 }
diff --git a/src/vs/platform/browserView/node/browserViewGroupRemoteService.ts b/src/vs/platform/browserView/node/browserViewGroupRemoteService.ts
index b4aaffb612d17..063a5b158b543 100644
--- a/src/vs/platform/browserView/node/browserViewGroupRemoteService.ts
+++ b/src/vs/platform/browserView/node/browserViewGroupRemoteService.ts
@@ -6,11 +6,9 @@
 import { Event } from '../../../base/common/event.js';
 import { Disposable } from '../../../base/common/lifecycle.js';
 import { ProxyChannel } from '../../../base/parts/ipc/common/ipc.js';
-import { createDecorator } from '../../instantiation/common/instantiation.js';
 import { IMainProcessService } from '../../ipc/common/mainProcessService.js';
 import { IBrowserViewGroup, IBrowserViewGroupService, IBrowserViewGroupViewEvent, ipcBrowserViewGroupChannelName } from '../common/browserViewGroup.js';
-
-export const IBrowserViewGroupRemoteService = createDecorator<IBrowserViewGroupRemoteService>('browserViewGroupRemoteService');
+import { CDPEvent, CDPRequest, CDPResponse } from '../common/cdp/types.js';
 
 /**
  * Remote-process service for managing browser view groups.
@@ -22,12 +20,11 @@ export const IBrowserViewGroupRemoteService = createDecorator<IBrowserViewGroupR
  * Usable from the shared process.
  */
 export interface IBrowserViewGroupRemoteService {
-	readonly _serviceBrand: undefined;
-
 	/**
 	 * Create a new browser view group.
+	 * @param windowId The ID of the primary window the group should be associated with.
 	 */
-	createGroup(): Promise<IBrowserViewGroup>;
+	createGroup(windowId: number): Promise<IBrowserViewGroup>;
 }
 
 /**
@@ -66,8 +63,12 @@ class RemoteBrowserViewGroup extends Disposable implements IBrowserViewGroup {
 		return this.groupService.removeViewFromGroup(this.id, viewId);
 	}
 
-	async getDebugWebSocketEndpoint(): Promise<string> {
-		return this.groupService.getDebugWebSocketEndpoint(this.id);
+	async sendCDPMessage(msg: CDPRequest): Promise<void> {
+		return this.groupService.sendCDPMessage(this.id, msg);
+	}
+
+	get onCDPMessage(): Event<CDPResponse | CDPEvent> {
+		return this.groupService.onDynamicCDPMessage(this.id);
 	}
 
 	override dispose(fromService = false): void {
@@ -79,20 +80,18 @@ class RemoteBrowserViewGroup extends Disposable implements IBrowserViewGroup {
 }
 
 export class BrowserViewGroupRemoteService implements IBrowserViewGroupRemoteService {
-	declare readonly _serviceBrand: undefined;
-
 	private readonly _groupService: IBrowserViewGroupService;
 	private readonly _groups = new Map<string, IBrowserViewGroup>();
 
 	constructor(
-		@IMainProcessService mainProcessService: IMainProcessService,
+		mainProcessService: IMainProcessService,
 	) {
 		const channel = mainProcessService.getChannel(ipcBrowserViewGroupChannelName);
 		this._groupService = ProxyChannel.toService<IBrowserViewGroupService>(channel);
 	}
 
-	async createGroup(): Promise<IBrowserViewGroup> {
-		const id = await this._groupService.createGroup();
+	async createGroup(windowId: number): Promise<IBrowserViewGroup> {
+		const id = await this._groupService.createGroup(windowId);
 		return this._wrap(id);
 	}
 
diff --git a/src/vs/platform/browserView/node/playwrightChannel.ts b/src/vs/platform/browserView/node/playwrightChannel.ts
new file mode 100644
index 0000000000000..ca3e83c00a2e5
--- /dev/null
+++ b/src/vs/platform/browserView/node/playwrightChannel.ts
@@ -0,0 +1,82 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Event } from '../../../base/common/event.js';
+import { Disposable, DisposableMap } from '../../../base/common/lifecycle.js';
+import { IPCServer, IServerChannel } from '../../../base/parts/ipc/common/ipc.js';
+import { IMainProcessService } from '../../ipc/common/mainProcessService.js';
+import { ILogService } from '../../log/common/log.js';
+import { BrowserViewGroupRemoteService } from './browserViewGroupRemoteService.js';
+import { PlaywrightService } from './playwrightService.js';
+
+/**
+ * IPC channel for the Playwright service.
+ *
+ * Each connected window gets its own {@link PlaywrightService},
+ * keyed by the opaque IPC connection context. The client sends an
+ * `__initialize` call with its numeric window ID before any other
+ * method calls, which eagerly creates the instance. When a window
+ * disconnects the instance is automatically disposed.
+ */
+export class PlaywrightChannel extends Disposable implements IServerChannel<string> {
+
+	private readonly _instances = this._register(new DisposableMap<string, PlaywrightService>());
+	private readonly browserViewGroupRemoteService: BrowserViewGroupRemoteService;
+
+	constructor(
+		ipcServer: IPCServer<string>,
+		mainProcessService: IMainProcessService,
+		private readonly logService: ILogService,
+	) {
+		super();
+		this.browserViewGroupRemoteService = new BrowserViewGroupRemoteService(mainProcessService);
+		this._register(ipcServer.onDidRemoveConnection(c => {
+			this._instances.deleteAndDispose(c.ctx);
+		}));
+	}
+
+	listen<T>(ctx: string, event: string): Event<T> {
+		const instance = this._instances.get(ctx);
+		if (!instance) {
+			throw new Error(`Window not initialized for context: ${ctx}`);
+		}
+		const source = (instance as unknown as Record<string, Event<unknown>>)[event];
+		if (typeof source !== 'function') {
+			throw new Error(`Event not found: ${event}`);
+		}
+		return source as Event<T>;
+	}
+
+	call<T>(ctx: string, command: string, arg?: unknown): Promise<T> {
+		// Handle the one-time initialization call that creates the instance
+		if (command === '__initialize') {
+			if (typeof arg !== 'number') {
+				throw new Error(`Invalid argument for __initialize: expected window ID as number, got ${typeof arg}`);
+			}
+			if (!this._instances.has(ctx)) {
+				const windowId = arg as number;
+				this._instances.set(ctx, new PlaywrightService(windowId, this.browserViewGroupRemoteService, this.logService));
+			}
+			return Promise.resolve(undefined as T);
+		}
+
+		const instance = this._instances.get(ctx);
+		if (!instance) {
+			throw new Error(`Window not initialized for context: ${ctx}`);
+		}
+
+		const target = (instance as unknown as Record<string, unknown>)[command];
+		if (typeof target !== 'function') {
+			throw new Error(`Method not found: ${command}`);
+		}
+
+		const methodArgs = Array.isArray(arg) ? arg : [];
+		let res = target.apply(instance, methodArgs);
+		if (!(res instanceof Promise)) {
+			res = Promise.resolve(res);
+		}
+		return res;
+	}
+}
diff --git a/src/vs/platform/browserView/node/playwrightService.ts b/src/vs/platform/browserView/node/playwrightService.ts
index 3016e0a3659e2..8abf560a5c315 100644
--- a/src/vs/platform/browserView/node/playwrightService.ts
+++ b/src/vs/platform/browserView/node/playwrightService.ts
@@ -10,12 +10,25 @@ import { ILogService } from '../../log/common/log.js';
 import { IPlaywrightService } from '../common/playwrightService.js';
 import { IBrowserViewGroupRemoteService } from '../node/browserViewGroupRemoteService.js';
 import { IBrowserViewGroup } from '../common/browserViewGroup.js';
-import { VSBuffer } from '../../../base/common/buffer.js';
 import { PlaywrightTab } from './playwrightTab.js';
+import { CDPEvent, CDPRequest, CDPResponse } from '../common/cdp/types.js';
 
 // eslint-disable-next-line local/code-import-patterns
 import type { Browser, BrowserContext, Page } from 'playwright-core';
 
+interface PlaywrightTransport {
+	send(s: CDPRequest): void;
+	close(): void;  // Note: calling close is expected to issue onclose at some point.
+	onmessage?: (message: CDPResponse | CDPEvent) => void;
+	onclose?: (reason?: string) => void;
+}
+
+declare module 'playwright-core' {
+	interface BrowserType {
+		_connectOverCDPTransport(transport: PlaywrightTransport): Promise<Browser>;
+	}
+}
+
 /**
  * Shared-process implementation of {@link IPlaywrightService}.
  *
@@ -33,8 +46,9 @@ export class PlaywrightService extends Disposable implements IPlaywrightService
 	private _initPromise: Promise<void> | undefined;
 
 	constructor(
-		@IBrowserViewGroupRemoteService private readonly browserViewGroupRemoteService: IBrowserViewGroupRemoteService,
-		@ILogService private readonly logService: ILogService,
+		private readonly windowId: number,
+		private readonly browserViewGroupRemoteService: IBrowserViewGroupRemoteService,
+		private readonly logService: ILogService,
 	) {
 		super();
 		this._pages = this._register(new PlaywrightPageManager(logService));
@@ -77,12 +91,21 @@ export class PlaywrightService extends Disposable implements IPlaywrightService
 		this._initPromise = (async () => {
 			try {
 				this.logService.debug('[PlaywrightService] Creating browser view group');
-				const group = await this.browserViewGroupRemoteService.createGroup();
+				const group = await this.browserViewGroupRemoteService.createGroup(this.windowId);
 
 				this.logService.debug('[PlaywrightService] Connecting to browser via CDP');
 				const playwright = await import('playwright-core');
-				const endpoint = await group.getDebugWebSocketEndpoint();
-				const browser = await playwright.chromium.connectOverCDP(endpoint);
+				const sub = group.onCDPMessage(msg => transport.onmessage?.(msg));
+				const transport: PlaywrightTransport = {
+					close() {
+						sub.dispose();
+						this.onclose?.();
+					},
+					send(message) {
+						void group.sendCDPMessage(message);
+					}
+				};
+				const browser = await playwright.chromium._connectOverCDPTransport(transport);
 
 				this.logService.debug('[PlaywrightService] Connected to browser');
 
@@ -125,18 +148,22 @@ export class PlaywrightService extends Disposable implements IPlaywrightService
 		return this._pages.getSummary(pageId, true);
 	}
 
+	async invokeFunctionRaw<T>(pageId: string, fnDef: string, ...args: unknown[]): Promise<T> {
+		await this.initialize();
+
+		const vm = await import('vm');
+		const fn = vm.compileFunction(`return (${fnDef})(page, ...args)`, ['page', 'args'], { parsingContext: vm.createContext() });
+
+		return this._pages.runAgainstPage(pageId, (page) => fn(page, args));
+	}
+
 	async invokeFunction(pageId: string, fnDef: string, ...args: unknown[]): Promise<{ result: unknown; summary: string }> {
 		this.logService.info(`[PlaywrightService] Invoking function on view ${pageId}`);
 
 		try {
-			await this.initialize();
-
-			const vm = await import('vm');
-			const fn = vm.compileFunction(`return (${fnDef})(page, ...args)`, ['page', 'args'], { parsingContext: vm.createContext() });
-
 			let result;
 			try {
-				result = await this._pages.runAgainstPage(pageId, (page) => fn(page, args));
+				result = await this.invokeFunctionRaw(pageId, fnDef, ...args);
 			} catch (err: unknown) {
 				result = err instanceof Error ? err.message : String(err);
 			}
@@ -155,16 +182,6 @@ export class PlaywrightService extends Disposable implements IPlaywrightService
 		}
 	}
 
-	async captureScreenshot(pageId: string, selector?: string, fullPage?: boolean): Promise<VSBuffer> {
-		await this.initialize();
-		return this._pages.runAgainstPage(pageId, async page => {
-			const screenshotBuffer = selector
-				? await page.locator(selector).screenshot({ type: 'jpeg', quality: 80 })
-				: await page.screenshot({ type: 'jpeg', quality: 80, fullPage: fullPage ?? false });
-			return VSBuffer.wrap(screenshotBuffer);
-		});
-	}
-
 	async replyToFileChooser(pageId: string, files: string[]): Promise<{ summary: string }> {
 		await this.initialize();
 		const summary = await this._pages.replyToFileChooser(pageId, files);
diff --git a/src/vs/platform/browserView/node/playwrightTab.ts b/src/vs/platform/browserView/node/playwrightTab.ts
index 231daf0fba047..0a73676455fe1 100644
--- a/src/vs/platform/browserView/node/playwrightTab.ts
+++ b/src/vs/platform/browserView/node/playwrightTab.ts
@@ -42,7 +42,6 @@ export class PlaywrightTab {
 		page.on('console', event => this._handleConsoleMessage(event))
 			.on('pageerror', error => this._handlePageError(error))
 			.on('requestfailed', request => this._handleRequestFailed(request))
-			.on('filechooser', chooser => this._handleFileChooser(chooser))
 			.on('dialog', dialog => this._handleDialog(dialog))
 			.on('download', download => this._handleDownload(download));
 
@@ -70,7 +69,7 @@ export class PlaywrightTab {
 
 	async replyToDialog(accept?: boolean, promptText?: string) {
 		if (!this._dialog) {
-			throw new Error('No active dialog to respond to');
+			throw new Error('No active modal dialog to respond to');
 		}
 		const dialog = this._dialog;
 		this._dialog = undefined;
@@ -90,7 +89,7 @@ export class PlaywrightTab {
 
 	async replyToFileChooser(files: string[]) {
 		if (!this._fileChooser) {
-			throw new Error('No active file chooser to respond to');
+			throw new Error('No active file chooser dialog to respond to');
 		}
 		const chooser = this._fileChooser;
 		this._fileChooser = undefined;
@@ -118,8 +117,12 @@ export class PlaywrightTab {
 
 	/**
 	 * Run a callback against the page and wait for it to complete.
+	 *
 	 * Because dialogs pause the page, execution races against any dialog that opens -- if a dialog
 	 * appears before the callback finishes, the method throws so the caller can surface it to the agent.
+	 *
+	 * Also allows for interactions to be handled differently when triggered by agents.
+	 * E.g. file dialogs should appear when the user triggers one, but not when the agent does.
 	 */
 	async safeRunAgainstPage<T>(action: (page: playwright.Page, token: CancellationToken) => Promise<T>): Promise<T> {
 		if (this._dialog) {
@@ -130,8 +133,20 @@ export class PlaywrightTab {
 		let result: T | void;
 		const dialogOpened = Event.toPromise(this._onDialogStateChanged.event);
 		const actionCompleted = createCancelablePromise(async (token) => {
-			result = await this.runAndWaitForCompletion((token) => action(this.page, token), token);
-			actionDidComplete = true;
+
+			// Whenever the page has a `filechooser` handler, the default file chooser is disabled.
+			// We don't want this during normal user interactions, but we do for agentic interactions.
+			// So we add a handler just during the action, and remove it afterwards.
+			// This isn't perfect (e.g. the user could trigger it while an action is running), but it's a best effort.
+			const handleFileChooser = (chooser: playwright.FileChooser) => this._handleFileChooser(chooser);
+			this.page.on('filechooser', handleFileChooser);
+
+			try {
+				result = await this.runAndWaitForCompletion((token) => action(this.page, token), token);
+				actionDidComplete = true;
+			} finally {
+				this.page.off('filechooser', handleFileChooser);
+			}
 		});
 
 		return raceCancellablePromises([dialogOpened, actionCompleted]).then(() => {
diff --git a/src/vs/platform/contextkey/common/contextkey.ts b/src/vs/platform/contextkey/common/contextkey.ts
index 22d31d714c99a..595a8d4bbd145 100644
--- a/src/vs/platform/contextkey/common/contextkey.ts
+++ b/src/vs/platform/contextkey/common/contextkey.ts
@@ -937,11 +937,29 @@ export class ContextKeyInExpr implements IContextKeyExpression {
 
 		if (Array.isArray(source)) {
 			// eslint-disable-next-line local/code-no-any-casts
-			return source.includes(item as any);
+			if (source.includes(item as any)) {
+				return true;
+			}
+			// On Windows, file paths are case-insensitive so file URI
+			// comparisons must be done in a case-insensitive manner.
+			if (isWindows && typeof item === 'string' && item.startsWith('file:///')) {
+				const itemLower = item.toLowerCase();
+				return source.some(s => typeof s === 'string' && s.toLowerCase() === itemLower);
+			}
+			return false;
 		}
 
 		if (typeof item === 'string' && typeof source === 'object' && source !== null) {
-			return hasOwnProperty.call(source, item);
+			if (hasOwnProperty.call(source, item)) {
+				return true;
+			}
+			// On Windows, file paths are case-insensitive so file URI
+			// property lookups must be done in a case-insensitive manner.
+			if (isWindows && item.startsWith('file:///')) {
+				const itemLower = item.toLowerCase();
+				return Object.keys(source).some(key => key.toLowerCase() === itemLower);
+			}
+			return false;
 		}
 		return false;
 	}
diff --git a/src/vs/platform/contextkey/test/common/contextkey.test.ts b/src/vs/platform/contextkey/test/common/contextkey.test.ts
index cf7ebe78a9669..8307e894e2fca 100644
--- a/src/vs/platform/contextkey/test/common/contextkey.test.ts
+++ b/src/vs/platform/contextkey/test/common/contextkey.test.ts
@@ -183,6 +183,19 @@ suite('ContextKeyExpr', () => {
 		assert.strictEqual(ainb.evaluate(createContext({ 'a': 'x', 'b': { 'x': false } })), true);
 		assert.strictEqual(ainb.evaluate(createContext({ 'a': 'x', 'b': { 'x': true } })), true);
 		assert.strictEqual(ainb.evaluate(createContext({ 'a': 'prototype', 'b': {} })), false);
+
+		// file URI case-insensitive comparison on Windows
+		if (isWindows) {
+			// Array source: file URIs with different casing should match on Windows
+			assert.strictEqual(ainb.evaluate(createContext({ 'a': 'file:///c%3A/Users/path/file.ts', 'b': ['file:///c%3A/users/path/file.ts'] })), true);
+			assert.strictEqual(ainb.evaluate(createContext({ 'a': 'file:///c%3A/users/path/file.ts', 'b': ['file:///c%3A/Users/path/file.ts'] })), true);
+			// Object source: file URIs with different casing should match on Windows
+			assert.strictEqual(ainb.evaluate(createContext({ 'a': 'file:///c%3A/Users/path/file.ts', 'b': { 'file:///c%3A/users/path/file.ts': true } })), true);
+			// Non-file URIs should still be case-sensitive
+			assert.strictEqual(ainb.evaluate(createContext({ 'a': 'git:/path/File.ts', 'b': ['git:/path/file.ts'] })), false);
+			// Exact match still works
+			assert.strictEqual(ainb.evaluate(createContext({ 'a': 'file:///c%3A/Users/path/file.ts', 'b': ['file:///c%3A/Users/path/file.ts'] })), true);
+		}
 	});
 
 	test('ContextKeyNotInExpr', () => {
@@ -198,6 +211,13 @@ suite('ContextKeyExpr', () => {
 		assert.strictEqual(aNotInB.evaluate(createContext({ 'a': 'x', 'b': { 'x': false } })), false);
 		assert.strictEqual(aNotInB.evaluate(createContext({ 'a': 'x', 'b': { 'x': true } })), false);
 		assert.strictEqual(aNotInB.evaluate(createContext({ 'a': 'prototype', 'b': {} })), true);
+
+		// file URI case-insensitive comparison on Windows
+		if (isWindows) {
+			assert.strictEqual(aNotInB.evaluate(createContext({ 'a': 'file:///c%3A/Users/path/file.ts', 'b': ['file:///c%3A/users/path/file.ts'] })), false);
+			assert.strictEqual(aNotInB.evaluate(createContext({ 'a': 'file:///c%3A/users/path/file.ts', 'b': ['file:///c%3A/Users/path/file.ts'] })), false);
+			assert.strictEqual(aNotInB.evaluate(createContext({ 'a': 'git:/path/File.ts', 'b': ['git:/path/file.ts'] })), true);
+		}
 	});
 
 	test('issue #106524: distributing AND should normalize', () => {
diff --git a/src/vs/platform/defaultAccount/common/defaultAccount.ts b/src/vs/platform/defaultAccount/common/defaultAccount.ts
index cd67c68841230..5e543ddd942a7 100644
--- a/src/vs/platform/defaultAccount/common/defaultAccount.ts
+++ b/src/vs/platform/defaultAccount/common/defaultAccount.ts
@@ -3,15 +3,17 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { createDecorator } from '../../instantiation/common/instantiation.js';
+import { ICopilotTokenInfo, IDefaultAccount, IDefaultAccountAuthenticationProvider, IPolicyData } from '../../../base/common/defaultAccount.js';
 import { Event } from '../../../base/common/event.js';
-import { IDefaultAccount, IDefaultAccountAuthenticationProvider, IPolicyData } from '../../../base/common/defaultAccount.js';
+import { createDecorator } from '../../instantiation/common/instantiation.js';
 
 export interface IDefaultAccountProvider {
 	readonly defaultAccount: IDefaultAccount | null;
 	readonly onDidChangeDefaultAccount: Event<IDefaultAccount | null>;
 	readonly policyData: IPolicyData | null;
 	readonly onDidChangePolicyData: Event<IPolicyData | null>;
+	readonly copilotTokenInfo: ICopilotTokenInfo | null;
+	readonly onDidChangeCopilotTokenInfo: Event<ICopilotTokenInfo | null>;
 	getDefaultAccountAuthenticationProvider(): IDefaultAccountAuthenticationProvider;
 	refresh(): Promise<IDefaultAccount | null>;
 	signIn(options?: { additionalScopes?: readonly string[];[key: string]: unknown }): Promise<IDefaultAccount | null>;
@@ -25,6 +27,8 @@ export interface IDefaultAccountService {
 	readonly onDidChangeDefaultAccount: Event<IDefaultAccount | null>;
 	readonly onDidChangePolicyData: Event<IPolicyData | null>;
 	readonly policyData: IPolicyData | null;
+	readonly copilotTokenInfo: ICopilotTokenInfo | null;
+	readonly onDidChangeCopilotTokenInfo: Event<ICopilotTokenInfo | null>;
 	getDefaultAccount(): Promise<IDefaultAccount | null>;
 	getDefaultAccountAuthenticationProvider(): IDefaultAccountAuthenticationProvider;
 	setDefaultAccountProvider(provider: IDefaultAccountProvider): void;
diff --git a/src/vs/platform/dialogs/common/dialogs.ts b/src/vs/platform/dialogs/common/dialogs.ts
index f80914ca0b58f..fc73e57f82433 100644
--- a/src/vs/platform/dialogs/common/dialogs.ts
+++ b/src/vs/platform/dialogs/common/dialogs.ts
@@ -3,6 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { CancellationToken } from '../../../base/common/cancellation.js';
 import { Event } from '../../../base/common/event.js';
 import { ThemeIcon } from '../../../base/common/themables.js';
 import { IMarkdownString } from '../../../base/common/htmlContent.js';
@@ -37,6 +38,17 @@ export interface IBaseDialogOptions {
 	 * Allows to enforce use of custom dialog even in native environments.
 	 */
 	readonly custom?: boolean | ICustomDialogOptions;
+
+	/**
+	 * An optional cancellation token that can be used to dismiss the dialog
+	 * programmatically for custom dialog implementations.
+	 *
+	 * When cancelled, the custom dialog resolves as if the cancel button was
+	 * pressed. Native dialog handlers cannot currently be dismissed
+	 * programmatically and ignore this option unless a custom dialog is
+	 * explicitly enforced via the {@link custom} option.
+	 */
+	readonly token?: CancellationToken;
 }
 
 export interface IConfirmDialogArgs {
diff --git a/src/vs/platform/download/common/download.ts b/src/vs/platform/download/common/download.ts
index d608e078ecbdc..8d26b20e5a35c 100644
--- a/src/vs/platform/download/common/download.ts
+++ b/src/vs/platform/download/common/download.ts
@@ -13,6 +13,6 @@ export interface IDownloadService {
 
 	readonly _serviceBrand: undefined;
 
-	download(uri: URI, to: URI, cancellationToken?: CancellationToken): Promise<void>;
+	download(uri: URI, to: URI, callSite: string, cancellationToken?: CancellationToken): Promise<void>;
 
 }
diff --git a/src/vs/platform/download/common/downloadIpc.ts b/src/vs/platform/download/common/downloadIpc.ts
index c3ba6d6c249de..efd3a3e2113c0 100644
--- a/src/vs/platform/download/common/downloadIpc.ts
+++ b/src/vs/platform/download/common/downloadIpc.ts
@@ -19,7 +19,7 @@ export class DownloadServiceChannel implements IServerChannel {
 
 	call(context: any, command: string, args?: any): Promise<any> {
 		switch (command) {
-			case 'download': return this.service.download(URI.revive(args[0]), URI.revive(args[1]));
+			case 'download': return this.service.download(URI.revive(args[0]), URI.revive(args[1]), args[2] ?? 'downloadIpc');
 		}
 		throw new Error('Invalid call');
 	}
@@ -31,7 +31,7 @@ export class DownloadServiceChannelClient implements IDownloadService {
 
 	constructor(private channel: IChannel, private getUriTransformer: () => IURITransformer | null) { }
 
-	async download(from: URI, to: URI): Promise<void> {
+	async download(from: URI, to: URI, _callSite?: string): Promise<void> {
 		const uriTransformer = this.getUriTransformer();
 		if (uriTransformer) {
 			from = uriTransformer.transformOutgoingURI(from);
diff --git a/src/vs/platform/download/common/downloadService.ts b/src/vs/platform/download/common/downloadService.ts
index 79cedcb1668ed..4782f50658835 100644
--- a/src/vs/platform/download/common/downloadService.ts
+++ b/src/vs/platform/download/common/downloadService.ts
@@ -19,13 +19,13 @@ export class DownloadService implements IDownloadService {
 		@IFileService private readonly fileService: IFileService
 	) { }
 
-	async download(resource: URI, target: URI, cancellationToken: CancellationToken = CancellationToken.None): Promise<void> {
+	async download(resource: URI, target: URI, callSite: string, cancellationToken: CancellationToken = CancellationToken.None): Promise<void> {
 		if (resource.scheme === Schemas.file || resource.scheme === Schemas.vscodeRemote) {
 			// Intentionally only support this for file|remote<->file|remote scenarios
 			await this.fileService.copy(resource, target);
 			return;
 		}
-		const options = { type: 'GET', url: resource.toString(true) };
+		const options = { type: 'GET' as const, url: resource.toString(true), callSite };
 		const context = await this.requestService.request(options, cancellationToken);
 		if (context.res.statusCode === 200) {
 			await this.fileService.writeFile(target, context.stream);
diff --git a/src/vs/platform/editor/common/editor.ts b/src/vs/platform/editor/common/editor.ts
index 281ee03246a20..d0751cb4bc983 100644
--- a/src/vs/platform/editor/common/editor.ts
+++ b/src/vs/platform/editor/common/editor.ts
@@ -329,6 +329,21 @@ export interface IEditorOptions {
 
 export interface IModalEditorPartOptions {
 
+	/**
+	 * Whether the modal editor should be maximized.
+	 */
+	readonly maximized?: boolean;
+
+	/**
+	 * Size of the modal editor part unless it is maximized.
+	 */
+	readonly size?: { readonly width: number; readonly height: number };
+
+	/**
+	 * Position of the modal editor part unless it is maximized.
+	 */
+	readonly position?: { readonly left: number; readonly top: number };
+
 	/**
 	 * The navigation context for navigating between items
 	 * within this modal editor. Pass `undefined` to clear.
diff --git a/src/vs/platform/environment/common/argv.ts b/src/vs/platform/environment/common/argv.ts
index 45cb23ba6f3f7..7293857263511 100644
--- a/src/vs/platform/environment/common/argv.ts
+++ b/src/vs/platform/environment/common/argv.ts
@@ -121,6 +121,7 @@ export interface NativeParsedArgs {
 	'file-write'?: boolean;
 	'file-chmod'?: boolean;
 	'enable-smoke-test-driver'?: boolean;
+	'skip-sessions-welcome'?: boolean;
 	'remote'?: string;
 	'force'?: boolean;
 	'do-not-sync'?: boolean;
diff --git a/src/vs/platform/environment/node/argv.ts b/src/vs/platform/environment/node/argv.ts
index 6d00ad0ae0908..9068c9ad77acf 100644
--- a/src/vs/platform/environment/node/argv.ts
+++ b/src/vs/platform/environment/node/argv.ts
@@ -166,6 +166,7 @@ export const OPTIONS: OptionDescriptions<Required<NativeParsedArgs>> = {
 	'export-policy-data': { type: 'string', allowEmptyValue: true },
 	'install-source': { type: 'string' },
 	'enable-smoke-test-driver': { type: 'boolean' },
+	'skip-sessions-welcome': { type: 'boolean' },
 	'logExtensionHostCommunication': { type: 'boolean' },
 	'skip-release-notes': { type: 'boolean' },
 	'skip-welcome': { type: 'boolean' },
diff --git a/src/vs/platform/extensionManagement/common/extensionGalleryService.ts b/src/vs/platform/extensionManagement/common/extensionGalleryService.ts
index 40349546ec845..6414a467547a0 100644
--- a/src/vs/platform/extensionManagement/common/extensionGalleryService.ts
+++ b/src/vs/platform/extensionManagement/common/extensionGalleryService.ts
@@ -825,7 +825,7 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 						extension: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Extension id' };
 						preRelease: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Get pre-release version' };
 						compatible: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Get compatible version' };
-						errorCode: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Error code' };
+						errorCode: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Error code or reason' };
 					}>('galleryService:fallbacktoquery', {
 						extension: extensionInfo.id,
 						preRelease: !!extensionInfo.preRelease,
@@ -1082,7 +1082,7 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 			this.telemetryService.publicLog2<GalleryServiceEngineFallbackEvent, GalleryServiceEngineFallbackClassification>('galleryService:engineFallback', { extension: extensionId, extensionVersion: version });
 
 			const headers = { 'Accept-Encoding': 'gzip' };
-			const context = await this.getAsset(extensionId, manifestAsset, AssetType.Manifest, version, { headers });
+			const context = await this.getAsset(extensionId, manifestAsset, AssetType.Manifest, version, 'extensionGalleryService.engineVersion', { headers });
 			const manifest = await asJson<IExtensionManifest>(context);
 			if (!manifest) {
 				this.logService.error(`Manifest was not found for the extension ${extensionId} with version ${version}`);
@@ -1439,7 +1439,8 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 				type: 'POST',
 				url: extensionsQueryApi,
 				data,
-				headers
+				headers,
+				callSite: 'extensionGalleryService.queryRawGalleryExtensions'
 			}, token);
 
 			if (context.res.statusCode && context.res.statusCode >= 400 && context.res.statusCode < 500) {
@@ -1588,7 +1589,8 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 				type: 'GET',
 				url: uri.toString(true),
 				headers,
-				timeout: this.getRequestTimeout()
+				timeout: this.getRequestTimeout(),
+				callSite: 'extensionGalleryService.getLatestRawGalleryExtension'
 			}, token);
 
 			if (context.res.statusCode === 404) {
@@ -1686,7 +1688,8 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 			await this.requestService.request({
 				type: 'POST',
 				url,
-				headers
+				headers,
+				callSite: 'extensionGalleryService.reportStatistic'
 			}, CancellationToken.None);
 		} catch (error) { /* Ignore */ }
 	}
@@ -1704,7 +1707,7 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 
 		const activityId = extension.queryContext?.[SEARCH_ACTIVITY_HEADER_NAME];
 		const headers: IHeaders | undefined = activityId && typeof activityId === 'string' ? { [SEARCH_ACTIVITY_HEADER_NAME]: activityId } : undefined;
-		const context = await this.getAsset(extension.identifier.id, downloadAsset, AssetType.VSIX, extension.version, headers ? { headers } : undefined);
+		const context = await this.getAsset(extension.identifier.id, downloadAsset, AssetType.VSIX, extension.version, 'extensionGalleryService.download', headers ? { headers } : undefined);
 
 		try {
 			await this.fileService.writeFile(location, context.stream);
@@ -1737,7 +1740,7 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 
 		this.logService.trace('ExtensionGalleryService#downloadSignatureArchive', extension.identifier.id);
 
-		const context = await this.getAsset(extension.identifier.id, extension.assets.signature, AssetType.Signature, extension.version);
+		const context = await this.getAsset(extension.identifier.id, extension.assets.signature, AssetType.Signature, extension.version, 'extensionGalleryService.signature');
 		try {
 			await this.fileService.writeFile(location, context.stream);
 		} catch (error) {
@@ -1754,7 +1757,7 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 
 	async getReadme(extension: IGalleryExtension, token: CancellationToken): Promise<string> {
 		if (extension.assets.readme) {
-			const context = await this.getAsset(extension.identifier.id, extension.assets.readme, AssetType.Details, extension.version, {}, token);
+			const context = await this.getAsset(extension.identifier.id, extension.assets.readme, AssetType.Details, extension.version, 'extensionGalleryService.readme', {}, token);
 			const content = await asTextOrError(context);
 			return content || '';
 		}
@@ -1763,7 +1766,7 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 
 	async getManifest(extension: IGalleryExtension, token: CancellationToken): Promise<IExtensionManifest | null> {
 		if (extension.assets.manifest) {
-			const context = await this.getAsset(extension.identifier.id, extension.assets.manifest, AssetType.Manifest, extension.version, {}, token);
+			const context = await this.getAsset(extension.identifier.id, extension.assets.manifest, AssetType.Manifest, extension.version, 'extensionGalleryService.manifest', {}, token);
 			const text = await asTextOrError(context);
 			return text ? JSON.parse(text) : null;
 		}
@@ -1773,7 +1776,7 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 	async getCoreTranslation(extension: IGalleryExtension, languageId: string): Promise<ITranslation | null> {
 		const asset = extension.assets.coreTranslations.filter(t => t[0] === languageId.toUpperCase())[0];
 		if (asset) {
-			const context = await this.getAsset(extension.identifier.id, asset[1], asset[0], extension.version);
+			const context = await this.getAsset(extension.identifier.id, asset[1], asset[0], extension.version, 'extensionGalleryService.coreTranslation');
 			const text = await asTextOrError(context);
 			return text ? JSON.parse(text) : null;
 		}
@@ -1782,7 +1785,7 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 
 	async getChangelog(extension: IGalleryExtension, token: CancellationToken): Promise<string> {
 		if (extension.assets.changelog) {
-			const context = await this.getAsset(extension.identifier.id, extension.assets.changelog, AssetType.Changelog, extension.version, {}, token);
+			const context = await this.getAsset(extension.identifier.id, extension.assets.changelog, AssetType.Changelog, extension.version, 'extensionGalleryService.changelog', {}, token);
 			const content = await asTextOrError(context);
 			return content || '';
 		}
@@ -1869,7 +1872,7 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 		return result;
 	}
 
-	private async getAsset(extension: string, asset: IGalleryExtensionAsset, assetType: string, extensionVersion: string, options: IRequestOptions = {}, token: CancellationToken = CancellationToken.None): Promise<IRequestContext> {
+	private async getAsset(extension: string, asset: IGalleryExtensionAsset, assetType: string, extensionVersion: string, callSite: string, options: Omit<IRequestOptions, 'callSite'> = {}, token: CancellationToken = CancellationToken.None): Promise<IRequestContext> {
 		const commonHeaders = await this.commonHeadersPromise;
 		const baseOptions = { type: 'GET' };
 		const headers = { ...commonHeaders, ...(options.headers || {}) };
@@ -1877,7 +1880,7 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 
 		const url = asset.uri;
 		const fallbackUrl = asset.fallbackUri;
-		const firstOptions = { ...options, url, timeout: this.getRequestTimeout() };
+		const firstOptions = { ...options, url, timeout: this.getRequestTimeout(), callSite };
 
 		let context;
 		try {
@@ -1923,7 +1926,7 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 				endToEndId: this.getHeaderValue(context?.res.headers, END_END_ID_HEADER_NAME),
 			});
 
-			const fallbackOptions = { ...options, url: fallbackUrl, timeout: this.getRequestTimeout() };
+			const fallbackOptions = { ...options, url: fallbackUrl, timeout: this.getRequestTimeout(), callSite: `${callSite}.fallback` };
 			return this.requestService.request(fallbackOptions, token);
 		}
 	}
@@ -1942,7 +1945,8 @@ export abstract class AbstractExtensionGalleryService implements IExtensionGalle
 		const context = await this.requestService.request({
 			type: 'GET',
 			url: this.extensionsControlUrl,
-			timeout: this.getRequestTimeout()
+			timeout: this.getRequestTimeout(),
+			callSite: 'extensionGalleryService.getExtensionsControlManifest'
 		}, CancellationToken.None);
 
 		if (context.res.statusCode !== 200) {
diff --git a/src/vs/platform/extensionManagement/common/extensionManagementIpc.ts b/src/vs/platform/extensionManagement/common/extensionManagementIpc.ts
index 47f9736ff5af5..63a60f3a3d9ca 100644
--- a/src/vs/platform/extensionManagement/common/extensionManagementIpc.ts
+++ b/src/vs/platform/extensionManagement/common/extensionManagementIpc.ts
@@ -54,11 +54,11 @@ export class ExtensionManagementChannel<TContext = RemoteAgentConnectionContext
 	readonly onDidUpdateExtensionMetadata: Event<DidUpdateExtensionMetadata>;
 
 	constructor(private service: IExtensionManagementService, private getUriTransformer: (requestContext: TContext) => IURITransformer | null) {
-		this.onInstallExtension = Event.buffer(service.onInstallExtension, true);
-		this.onDidInstallExtensions = Event.buffer(service.onDidInstallExtensions, true);
-		this.onUninstallExtension = Event.buffer(service.onUninstallExtension, true);
-		this.onDidUninstallExtension = Event.buffer(service.onDidUninstallExtension, true);
-		this.onDidUpdateExtensionMetadata = Event.buffer(service.onDidUpdateExtensionMetadata, true);
+		this.onInstallExtension = Event.buffer(service.onInstallExtension, 'onInstallExtension', true);
+		this.onDidInstallExtensions = Event.buffer(service.onDidInstallExtensions, 'onDidInstallExtensions', true);
+		this.onUninstallExtension = Event.buffer(service.onUninstallExtension, 'onUninstallExtension', true);
+		this.onDidUninstallExtension = Event.buffer(service.onDidUninstallExtension, 'onDidUninstallExtension', true);
+		this.onDidUpdateExtensionMetadata = Event.buffer(service.onDidUpdateExtensionMetadata, 'onDidUpdateExtensionMetadata', true);
 	}
 
 	// eslint-disable-next-line @typescript-eslint/no-explicit-any
diff --git a/src/vs/platform/extensionManagement/node/extensionManagementService.ts b/src/vs/platform/extensionManagement/node/extensionManagementService.ts
index cdf0c67facd71..cef0d3c59c1e0 100644
--- a/src/vs/platform/extensionManagement/node/extensionManagementService.ts
+++ b/src/vs/platform/extensionManagement/node/extensionManagementService.ts
@@ -261,7 +261,7 @@ export class ExtensionManagementService extends AbstractExtensionManagementServi
 		}
 		this.logService.trace('Downloading extension from', vsix.toString());
 		const location = joinPath(this.extensionsDownloader.extensionsDownloadDir, generateUuid());
-		await this.downloadService.download(vsix, location);
+		await this.downloadService.download(vsix, location, 'extensionManagement.downloadVsix');
 		this.logService.info('Downloaded extension to', location.toString());
 		const cleanup = async () => {
 			try {
diff --git a/src/vs/platform/extensionResourceLoader/common/extensionResourceLoaderService.ts b/src/vs/platform/extensionResourceLoader/common/extensionResourceLoaderService.ts
index e360b8431935b..638db3465469c 100644
--- a/src/vs/platform/extensionResourceLoader/common/extensionResourceLoaderService.ts
+++ b/src/vs/platform/extensionResourceLoader/common/extensionResourceLoaderService.ts
@@ -34,7 +34,7 @@ export class ExtensionResourceLoaderService extends AbstractExtensionResourceLoa
 	async readExtensionResource(uri: URI): Promise<string> {
 		if (await this.isExtensionGalleryResource(uri)) {
 			const headers = await this.getExtensionGalleryRequestHeaders();
-			const requestContext = await this._requestService.request({ url: uri.toString(), headers }, CancellationToken.None);
+			const requestContext = await this._requestService.request({ url: uri.toString(), headers, callSite: 'extensionResourceLoader.readExtensionResource' }, CancellationToken.None);
 			return (await asTextOrError(requestContext)) || '';
 		}
 		const result = await this._fileService.readFile(uri);
diff --git a/src/vs/platform/extensions/common/extensionsApiProposals.ts b/src/vs/platform/extensions/common/extensionsApiProposals.ts
index db714398cdaad..37e1901f0a7e1 100644
--- a/src/vs/platform/extensions/common/extensionsApiProposals.ts
+++ b/src/vs/platform/extensions/common/extensionsApiProposals.ts
@@ -37,6 +37,9 @@ const _allApiProposals = {
 	authenticationChallenges: {
 		proposal: 'https://raw.githubusercontent.com/microsoft/vscode/main/src/vscode-dts/vscode.proposed.authenticationChallenges.d.ts',
 	},
+	browser: {
+		proposal: 'https://raw.githubusercontent.com/microsoft/vscode/main/src/vscode-dts/vscode.proposed.browser.d.ts',
+	},
 	canonicalUriProvider: {
 		proposal: 'https://raw.githubusercontent.com/microsoft/vscode/main/src/vscode-dts/vscode.proposed.canonicalUriProvider.d.ts',
 	},
@@ -45,7 +48,7 @@ const _allApiProposals = {
 	},
 	chatDebug: {
 		proposal: 'https://raw.githubusercontent.com/microsoft/vscode/main/src/vscode-dts/vscode.proposed.chatDebug.d.ts',
-		version: 1
+		version: 3
 	},
 	chatHooks: {
 		proposal: 'https://raw.githubusercontent.com/microsoft/vscode/main/src/vscode-dts/vscode.proposed.chatHooks.d.ts',
@@ -60,7 +63,7 @@ const _allApiProposals = {
 	},
 	chatParticipantPrivate: {
 		proposal: 'https://raw.githubusercontent.com/microsoft/vscode/main/src/vscode-dts/vscode.proposed.chatParticipantPrivate.d.ts',
-		version: 14
+		version: 15
 	},
 	chatPromptFiles: {
 		proposal: 'https://raw.githubusercontent.com/microsoft/vscode/main/src/vscode-dts/vscode.proposed.chatPromptFiles.d.ts',
@@ -426,6 +429,9 @@ const _allApiProposals = {
 	taskProblemMatcherStatus: {
 		proposal: 'https://raw.githubusercontent.com/microsoft/vscode/main/src/vscode-dts/vscode.proposed.taskProblemMatcherStatus.d.ts',
 	},
+	taskRunOptions: {
+		proposal: 'https://raw.githubusercontent.com/microsoft/vscode/main/src/vscode-dts/vscode.proposed.taskRunOptions.d.ts',
+	},
 	telemetry: {
 		proposal: 'https://raw.githubusercontent.com/microsoft/vscode/main/src/vscode-dts/vscode.proposed.telemetry.d.ts',
 	},
diff --git a/src/vs/platform/hover/browser/hover.css b/src/vs/platform/hover/browser/hover.css
index 597738d306964..9a6b49d73fe90 100644
--- a/src/vs/platform/hover/browser/hover.css
+++ b/src/vs/platform/hover/browser/hover.css
@@ -17,7 +17,11 @@
 	border: 1px solid var(--vscode-editorHoverWidget-border);
 	border-radius: 5px;
 	color: var(--vscode-editorHoverWidget-foreground);
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-hover);
+}
+
+.monaco-hover.workbench-hover.with-pointer {
+	border-radius: 3px;
 }
 
 .monaco-hover.workbench-hover .monaco-action-bar .action-item .codicon {
diff --git a/src/vs/platform/hover/browser/hoverService.ts b/src/vs/platform/hover/browser/hoverService.ts
index 116bfe0824cc4..cfb53e2e686ae 100644
--- a/src/vs/platform/hover/browser/hoverService.ts
+++ b/src/vs/platform/hover/browser/hoverService.ts
@@ -248,6 +248,7 @@ export class HoverService extends Disposable implements IHoverService {
 	}
 
 	private _createHover(options: IHoverOptions, skipLastFocusedUpdate?: boolean): ICreateHoverResult | undefined {
+		this._currentDelayedHover?.dispose();
 		this._currentDelayedHover = undefined;
 
 		if (options.content === '') {
@@ -556,7 +557,7 @@ export class HoverService extends Disposable implements IHoverService {
 
 		if (targetElement.title !== '') {
 			console.warn('HTML element already has a title attribute, which will conflict with the custom hover. Please remove the title attribute.');
-			console.trace('Stack trace:', targetElement.title);
+			// console.trace('Stack trace:', targetElement.title);
 			targetElement.title = '';
 		}
 
diff --git a/src/vs/platform/hover/browser/hoverWidget.ts b/src/vs/platform/hover/browser/hoverWidget.ts
index 41c8723608abd..28af860840d15 100644
--- a/src/vs/platform/hover/browser/hoverWidget.ts
+++ b/src/vs/platform/hover/browser/hoverWidget.ts
@@ -138,6 +138,9 @@ export class HoverWidget extends Widget implements IHoverWidget {
 		if (options.appearance?.compact) {
 			this._hover.containerDomNode.classList.add('workbench-hover', 'compact');
 		}
+		if (this._hoverPointer) {
+			this._hover.containerDomNode.classList.add('with-pointer');
+		}
 		if (options.additionalClasses) {
 			this._hover.containerDomNode.classList.add(...options.additionalClasses);
 		}
diff --git a/src/vs/platform/instantiation/common/extensions.ts b/src/vs/platform/instantiation/common/extensions.ts
index 517a8cc2a3a08..e59cc837cc633 100644
--- a/src/vs/platform/instantiation/common/extensions.ts
+++ b/src/vs/platform/instantiation/common/extensions.ts
@@ -26,7 +26,7 @@ export function registerSingleton<T, Services extends BrandedService[]>(id: Serv
 export function registerSingleton<T, Services extends BrandedService[]>(id: ServiceIdentifier<T>, descriptor: SyncDescriptor<any>): void;
 export function registerSingleton<T, Services extends BrandedService[]>(id: ServiceIdentifier<T>, ctorOrDescriptor: { new(...services: Services): T } | SyncDescriptor<any>, supportsDelayedInstantiation?: boolean | InstantiationType): void {
 	if (!(ctorOrDescriptor instanceof SyncDescriptor)) {
-		ctorOrDescriptor = new SyncDescriptor<T>(ctorOrDescriptor as new (...args: any[]) => T, [], Boolean(supportsDelayedInstantiation));
+		ctorOrDescriptor = new SyncDescriptor<T>(ctorOrDescriptor as new (...args: unknown[]) => T, [], Boolean(supportsDelayedInstantiation));
 	}
 
 	_registry.push([id, ctorOrDescriptor]);
diff --git a/src/vs/platform/launch/electron-main/launchMainService.ts b/src/vs/platform/launch/electron-main/launchMainService.ts
index db2fd75d13495..274600742e45a 100644
--- a/src/vs/platform/launch/electron-main/launchMainService.ts
+++ b/src/vs/platform/launch/electron-main/launchMainService.ts
@@ -18,6 +18,7 @@ import { ICodeWindow } from '../../window/electron-main/window.js';
 import { IWindowSettings } from '../../window/common/window.js';
 import { IOpenConfiguration, IWindowsMainService, OpenContext } from '../../windows/electron-main/windows.js';
 import { IProtocolUrl } from '../../url/electron-main/url.js';
+import { IProductService } from '../../product/common/productService.js';
 
 export const ID = 'launchMainService';
 export const ILaunchMainService = createDecorator<ILaunchMainService>(ID);
@@ -45,6 +46,7 @@ export class LaunchMainService implements ILaunchMainService {
 		@IWindowsMainService private readonly windowsMainService: IWindowsMainService,
 		@IURLService private readonly urlService: IURLService,
 		@IConfigurationService private readonly configurationService: IConfigurationService,
+		@IProductService private readonly productService: IProductService,
 	) { }
 
 	async start(args: NativeParsedArgs, userEnv: IProcessEnvironment): Promise<void> {
@@ -111,6 +113,7 @@ export class LaunchMainService implements ILaunchMainService {
 
 	private async startOpenWindow(args: NativeParsedArgs, userEnv: IProcessEnvironment): Promise<void> {
 		const context = isLaunchedFromCli(userEnv) ? OpenContext.CLI : OpenContext.DESKTOP;
+
 		let usedWindows: ICodeWindow[] = [];
 
 		const waitMarkerFileURI = args.wait && args.waitMarkerFilePath ? URI.file(args.waitMarkerFilePath) : undefined;
@@ -142,6 +145,11 @@ export class LaunchMainService implements ILaunchMainService {
 			await this.windowsMainService.openExtensionDevelopmentHostWindow(args.extensionDevelopmentPath, baseConfig);
 		}
 
+		// Sessions window
+		else if (args['sessions'] && this.productService.quality !== 'stable') {
+			usedWindows = await this.windowsMainService.openSessionsWindow({ context, contextWindowId: undefined });
+		}
+
 		// Start without file/folder arguments
 		else if (!args._.length && !args['folder-uri'] && !args['file-uri']) {
 			let openNewWindow = false;
diff --git a/src/vs/platform/mcp/common/mcpGalleryManifestService.ts b/src/vs/platform/mcp/common/mcpGalleryManifestService.ts
index 377d30712606d..a86f67c36d46b 100644
--- a/src/vs/platform/mcp/common/mcpGalleryManifestService.ts
+++ b/src/vs/platform/mcp/common/mcpGalleryManifestService.ts
@@ -134,6 +134,7 @@ export class McpGalleryManifestService extends Disposable implements IMcpGallery
 			const context = await this.requestService.request({
 				type: 'GET',
 				url: `${url}/${version}/servers?limit=1`,
+				callSite: 'mcpGalleryManifestService.checkVersion'
 			}, CancellationToken.None);
 			if (isSuccess(context)) {
 				return true;
diff --git a/src/vs/platform/mcp/common/mcpGalleryService.ts b/src/vs/platform/mcp/common/mcpGalleryService.ts
index 5de645fe43699..6dbb16e296094 100644
--- a/src/vs/platform/mcp/common/mcpGalleryService.ts
+++ b/src/vs/platform/mcp/common/mcpGalleryService.ts
@@ -816,6 +816,7 @@ export class McpGalleryService extends Disposable implements IMcpGalleryService
 		const context = await this.requestService.request({
 			type: 'GET',
 			url: readmeUrl,
+			callSite: 'mcpGalleryService.getReadme'
 		}, token);
 
 		const result = await asText(context);
@@ -951,6 +952,7 @@ export class McpGalleryService extends Disposable implements IMcpGalleryService
 		const context = await this.requestService.request({
 			type: 'GET',
 			url,
+			callSite: 'mcpGalleryService.queryMcpServers'
 		}, token);
 
 		const data = await asJson(context);
@@ -972,6 +974,7 @@ export class McpGalleryService extends Disposable implements IMcpGalleryService
 		const context = await this.requestService.request({
 			type: 'GET',
 			url: mcpServerUrl,
+			callSite: 'mcpGalleryService.getMcpServer'
 		}, CancellationToken.None);
 
 		if (context.res.statusCode && context.res.statusCode >= 400 && context.res.statusCode < 500) {
diff --git a/src/vs/platform/mcp/common/mcpManagement.ts b/src/vs/platform/mcp/common/mcpManagement.ts
index 9c2b7e73d9023..834068a98b6c7 100644
--- a/src/vs/platform/mcp/common/mcpManagement.ts
+++ b/src/vs/platform/mcp/common/mcpManagement.ts
@@ -10,13 +10,14 @@ import { IIterativePager } from '../../../base/common/paging.js';
 import { URI } from '../../../base/common/uri.js';
 import { SortBy, SortOrder } from '../../extensionManagement/common/extensionManagement.js';
 import { createDecorator } from '../../instantiation/common/instantiation.js';
-import { IMcpServerConfiguration, IMcpServerVariable } from './mcpPlatformTypes.js';
+import { IMcpSandboxConfiguration, IMcpServerConfiguration, IMcpServerVariable } from './mcpPlatformTypes.js';
 
 export type InstallSource = 'gallery' | 'local';
 
 export interface ILocalMcpServer {
 	readonly name: string;
 	readonly config: IMcpServerConfiguration;
+	readonly rootSandbox?: IMcpSandboxConfiguration;
 	readonly version?: string;
 	readonly mcpResource: URI;
 	readonly location?: URI;
diff --git a/src/vs/platform/mcp/common/mcpManagementIpc.ts b/src/vs/platform/mcp/common/mcpManagementIpc.ts
index 733319fd2161a..570ede9d027df 100644
--- a/src/vs/platform/mcp/common/mcpManagementIpc.ts
+++ b/src/vs/platform/mcp/common/mcpManagementIpc.ts
@@ -46,11 +46,11 @@ export class McpManagementChannel<TContext = RemoteAgentConnectionContext | stri
 	readonly onDidUninstallMcpServer: Event<DidUninstallMcpServerEvent>;
 
 	constructor(private service: IMcpManagementService, private getUriTransformer: (requestContext: TContext) => IURITransformer | null) {
-		this.onInstallMcpServer = Event.buffer(service.onInstallMcpServer, true);
-		this.onDidInstallMcpServers = Event.buffer(service.onDidInstallMcpServers, true);
-		this.onDidUpdateMcpServers = Event.buffer(service.onDidUpdateMcpServers, true);
-		this.onUninstallMcpServer = Event.buffer(service.onUninstallMcpServer, true);
-		this.onDidUninstallMcpServer = Event.buffer(service.onDidUninstallMcpServer, true);
+		this.onInstallMcpServer = Event.buffer(service.onInstallMcpServer, 'onInstallMcpServer', true);
+		this.onDidInstallMcpServers = Event.buffer(service.onDidInstallMcpServers, 'onDidInstallMcpServers', true);
+		this.onDidUpdateMcpServers = Event.buffer(service.onDidUpdateMcpServers, 'onDidUpdateMcpServers', true);
+		this.onUninstallMcpServer = Event.buffer(service.onUninstallMcpServer, 'onUninstallMcpServer', true);
+		this.onDidUninstallMcpServer = Event.buffer(service.onDidUninstallMcpServer, 'onDidUninstallMcpServer', true);
 	}
 
 	listen<T>(context: TContext, event: string): Event<T> {
diff --git a/src/vs/platform/mcp/common/mcpManagementService.ts b/src/vs/platform/mcp/common/mcpManagementService.ts
index 5f72d29a8fe03..ec10b0f0ea947 100644
--- a/src/vs/platform/mcp/common/mcpManagementService.ts
+++ b/src/vs/platform/mcp/common/mcpManagementService.ts
@@ -22,7 +22,7 @@ import { ILogService } from '../../log/common/log.js';
 import { IUriIdentityService } from '../../uriIdentity/common/uriIdentity.js';
 import { IUserDataProfilesService } from '../../userDataProfile/common/userDataProfile.js';
 import { DidUninstallMcpServerEvent, IGalleryMcpServer, ILocalMcpServer, IMcpGalleryService, IMcpManagementService, IMcpServerInput, IGalleryMcpServerConfiguration, InstallMcpServerEvent, InstallMcpServerResult, RegistryType, UninstallMcpServerEvent, InstallOptions, UninstallOptions, IInstallableMcpServer, IAllowedMcpServersService, IMcpServerArgument, IMcpServerKeyValueInput, McpServerConfigurationParseResult } from './mcpManagement.js';
-import { IMcpServerVariable, McpServerVariableType, IMcpServerConfiguration, McpServerType } from './mcpPlatformTypes.js';
+import { IMcpSandboxConfiguration, IMcpServerVariable, McpServerVariableType, IMcpServerConfiguration, McpServerType } from './mcpPlatformTypes.js';
 import { IMcpResourceScannerService, McpResourceTarget } from './mcpResourceScannerService.js';
 
 export interface ILocalMcpServerInfo {
@@ -358,7 +358,7 @@ export abstract class AbstractMcpResourceManagementService extends AbstractCommo
 			const scannedMcpServers = await this.mcpResourceScannerService.scanMcpServers(this.mcpResource, this.target);
 			if (scannedMcpServers.servers) {
 				await Promise.allSettled(Object.entries(scannedMcpServers.servers).map(async ([name, scannedServer]) => {
-					const server = await this.scanLocalServer(name, scannedServer);
+					const server = await this.scanLocalServer(name, scannedServer, scannedMcpServers.sandbox);
 					local.set(name, server);
 				}));
 			}
@@ -426,7 +426,7 @@ export abstract class AbstractMcpResourceManagementService extends AbstractCommo
 		return Array.from(this.local.values());
 	}
 
-	protected async scanLocalServer(name: string, config: IMcpServerConfiguration): Promise<ILocalMcpServer> {
+	protected async scanLocalServer(name: string, config: IMcpServerConfiguration, rootSandbox?: IMcpSandboxConfiguration): Promise<ILocalMcpServer> {
 		let mcpServerInfo = await this.getLocalServerInfo(name, config);
 		if (!mcpServerInfo) {
 			mcpServerInfo = { name, version: config.version, galleryUrl: isString(config.gallery) ? config.gallery : undefined };
@@ -435,6 +435,7 @@ export abstract class AbstractMcpResourceManagementService extends AbstractCommo
 		return {
 			name,
 			config,
+			rootSandbox,
 			mcpResource: this.mcpResource,
 			version: mcpServerInfo.version,
 			location: mcpServerInfo.location,
diff --git a/src/vs/platform/mcp/common/mcpPlatformTypes.ts b/src/vs/platform/mcp/common/mcpPlatformTypes.ts
index 985d17f1dc7ac..dc4fb38172e7c 100644
--- a/src/vs/platform/mcp/common/mcpPlatformTypes.ts
+++ b/src/vs/platform/mcp/common/mcpPlatformTypes.ts
@@ -58,7 +58,6 @@ export interface IMcpStdioServerConfiguration extends ICommonMcpServerConfigurat
 	readonly envFile?: string;
 	readonly cwd?: string;
 	readonly sandboxEnabled?: boolean;
-	readonly sandbox?: IMcpSandboxConfiguration;
 	readonly dev?: IMcpDevModeConfig;
 }
 
diff --git a/src/vs/platform/mcp/common/mcpResourceScannerService.ts b/src/vs/platform/mcp/common/mcpResourceScannerService.ts
index cd8e0a9f0eb88..151238228b5e3 100644
--- a/src/vs/platform/mcp/common/mcpResourceScannerService.ts
+++ b/src/vs/platform/mcp/common/mcpResourceScannerService.ts
@@ -47,6 +47,7 @@ export interface IMcpResourceScannerService {
 	readonly _serviceBrand: undefined;
 	scanMcpServers(mcpResource: URI, target?: McpResourceTarget): Promise<IScannedMcpServers>;
 	addMcpServers(servers: IInstallableMcpServer[], mcpResource: URI, target?: McpResourceTarget): Promise<void>;
+	updateSandboxConfig(updateFn: (data: IScannedMcpServers) => IScannedMcpServers, mcpResource: URI, target?: McpResourceTarget): Promise<void>;
 	removeMcpServers(serverNames: string[], mcpResource: URI, target?: McpResourceTarget): Promise<void>;
 }
 
@@ -82,6 +83,10 @@ export class McpResourceScannerService extends Disposable implements IMcpResourc
 		});
 	}
 
+	async updateSandboxConfig(updateFn: (data: IScannedMcpServers) => IScannedMcpServers, mcpResource: URI, target?: McpResourceTarget): Promise<void> {
+		await this.withProfileMcpServers(mcpResource, target, updateFn);
+	}
+
 	async removeMcpServers(serverNames: string[], mcpResource: URI, target?: McpResourceTarget): Promise<void> {
 		await this.withProfileMcpServers(mcpResource, target, scannedMcpServers => {
 			for (const serverName of serverNames) {
@@ -139,7 +144,9 @@ export class McpResourceScannerService extends Disposable implements IMcpResourc
 	}
 
 	private async writeScannedMcpServers(mcpResource: URI, scannedMcpServers: IScannedMcpServers): Promise<void> {
-		if ((scannedMcpServers.servers && Object.keys(scannedMcpServers.servers).length > 0) || (scannedMcpServers.inputs && scannedMcpServers.inputs.length > 0)) {
+		if ((scannedMcpServers.servers && Object.keys(scannedMcpServers.servers).length > 0)
+			|| (scannedMcpServers.inputs && scannedMcpServers.inputs.length > 0)
+			|| scannedMcpServers.sandbox !== undefined) {
 			await this.fileService.writeFile(mcpResource, VSBuffer.fromString(JSON.stringify(scannedMcpServers, null, '\t')));
 		} else {
 			await this.fileService.del(mcpResource);
@@ -181,7 +188,7 @@ export class McpResourceScannerService extends Disposable implements IMcpResourc
 		if (servers.length > 0) {
 			userMcpServers.servers = {};
 			for (const [serverName, server] of servers) {
-				userMcpServers.servers[serverName] = this.sanitizeServer(server, scannedMcpServers.sandbox);
+				userMcpServers.servers[serverName] = this.sanitizeServer(server);
 			}
 		}
 		return userMcpServers;
@@ -196,13 +203,14 @@ export class McpResourceScannerService extends Disposable implements IMcpResourc
 		if (servers.length > 0) {
 			scannedMcpServers.servers = {};
 			for (const [serverName, config] of servers) {
-				scannedMcpServers.servers[serverName] = this.sanitizeServer(config, scannedWorkspaceFolderMcpServers.sandbox);
+				const serverConfig = this.sanitizeServer(config);
+				scannedMcpServers.servers[serverName] = serverConfig;
 			}
 		}
 		return scannedMcpServers;
 	}
 
-	private sanitizeServer(serverOrConfig: IOldScannedMcpServer | Mutable<IMcpServerConfiguration>, sandbox?: IMcpSandboxConfiguration): IMcpServerConfiguration {
+	private sanitizeServer(serverOrConfig: IOldScannedMcpServer | Mutable<IMcpServerConfiguration>): IMcpServerConfiguration {
 		let server: IMcpServerConfiguration;
 		if ((<IOldScannedMcpServer>serverOrConfig).config) {
 			const oldScannedMcpServer = <IOldScannedMcpServer>serverOrConfig;
@@ -218,11 +226,6 @@ export class McpResourceScannerService extends Disposable implements IMcpResourc
 		if (server.type === undefined || (server.type !== McpServerType.REMOTE && server.type !== McpServerType.LOCAL)) {
 			(<Mutable<ICommonMcpServerConfiguration>>server).type = (<IMcpStdioServerConfiguration>server).command ? McpServerType.LOCAL : McpServerType.REMOTE;
 		}
-
-		if (sandbox && server.type === McpServerType.LOCAL && !(server as IMcpStdioServerConfiguration).sandbox && server.sandboxEnabled) {
-			(<Mutable<IMcpStdioServerConfiguration>>server).sandbox = sandbox;
-		}
-
 		return server;
 	}
 
diff --git a/src/vs/platform/mcp/common/modelContextProtocolApps.ts b/src/vs/platform/mcp/common/modelContextProtocolApps.ts
index 4569e8f25ac8d..86b891514e213 100644
--- a/src/vs/platform/mcp/common/modelContextProtocolApps.ts
+++ b/src/vs/platform/mcp/common/modelContextProtocolApps.ts
@@ -17,6 +17,7 @@ export namespace McpApps {
 		| MCP.ReadResourceRequest
 		| MCP.PingRequest
 		| (McpUiOpenLinkRequest & MCP.JSONRPCRequest)
+		| (McpUiDownloadFileRequest & MCP.JSONRPCRequest)
 		| (McpUiUpdateModelContextRequest & MCP.JSONRPCRequest)
 		| (McpUiMessageRequest & MCP.JSONRPCRequest)
 		| (McpUiRequestDisplayModeRequest & MCP.JSONRPCRequest)
@@ -37,6 +38,7 @@ export namespace McpApps {
 		| McpApps.McpUiInitializeResult
 		| McpUiMessageResult
 		| McpUiOpenLinkResult
+		| McpUiDownloadFileResult
 		| McpUiRequestDisplayModeResult;
 
 	export type HostNotification =
@@ -223,6 +225,33 @@ export namespace McpApps {
 		[key: string]: unknown;
 	}
 
+	/**
+	 * @description Request to download one or more files through the host.
+	 * Uses standard MCP resource types: EmbeddedResource for inline content
+	 * and ResourceLink for references the host resolves via resources/read.
+	 */
+	export interface McpUiDownloadFileRequest {
+		method: "ui/download-file";
+		params: {
+			/** @description Resources to download, either inline or as links for the host to resolve. */
+			contents: (MCP.EmbeddedResource | MCP.ResourceLink)[];
+		};
+	}
+
+	/**
+	 * @description Result from a download file request.
+	 * @see {@link McpUiDownloadFileRequest}
+	 */
+	export interface McpUiDownloadFileResult {
+		/** @description True if the host rejected or failed to process the download. */
+		isError?: boolean;
+		/**
+		 * Index signature required for MCP SDK `Protocol` class compatibility.
+		 * Note: The schema intentionally omits this to enforce strict validation.
+		 */
+		[key: string]: unknown;
+	}
+
 	/**
 	 * @description Request to send a message to the host's chat interface.
 	 * @see {@link app.App.sendMessage} for the method that sends this request
@@ -528,6 +557,8 @@ export namespace McpApps {
 		updateModelContext?: McpUiSupportedContentBlockModalities;
 		/** @description Host supports receiving content messages (ui/message) from the View. */
 		message?: McpUiSupportedContentBlockModalities;
+		/** @description Host supports file downloads (ui/download-file) from the View. */
+		downloadFile?: {};
 	}
 
 	/**
@@ -734,4 +765,6 @@ export namespace McpApps {
 		"ui/request-display-mode";
 	export const UPDATE_MODEL_CONTEXT_METHOD: McpUiUpdateModelContextRequest["method"] =
 		"ui/update-model-context";
+	export const DOWNLOAD_FILE_METHOD: McpUiDownloadFileRequest["method"] =
+		"ui/download-file";
 }
diff --git a/src/vs/platform/mcp/node/mcpGatewayChannel.ts b/src/vs/platform/mcp/node/mcpGatewayChannel.ts
index 0b0ce1edb0ac8..78d0e93a3f0d2 100644
--- a/src/vs/platform/mcp/node/mcpGatewayChannel.ts
+++ b/src/vs/platform/mcp/node/mcpGatewayChannel.ts
@@ -6,6 +6,7 @@
 import { Event } from '../../../base/common/event.js';
 import { Disposable } from '../../../base/common/lifecycle.js';
 import { IPCServer, IServerChannel } from '../../../base/parts/ipc/common/ipc.js';
+import { ILoggerService } from '../../log/common/log.js';
 import { IGatewayCallToolResult, IGatewayServerResources, IGatewayServerResourceTemplates, IMcpGatewayService, McpGatewayToolBrokerChannelName } from '../common/mcpGateway.js';
 import { MCP } from '../common/modelContextProtocol.js';
 
@@ -19,10 +20,14 @@ export class McpGatewayChannel<TContext> extends Disposable implements IServerCh
 
 	constructor(
 		private readonly _ipcServer: IPCServer<TContext>,
-		@IMcpGatewayService private readonly mcpGatewayService: IMcpGatewayService
+		@IMcpGatewayService private readonly mcpGatewayService: IMcpGatewayService,
+		@ILoggerService private readonly _loggerService: ILoggerService,
 	) {
 		super();
-		this._register(_ipcServer.onDidRemoveConnection(c => mcpGatewayService.disposeGatewaysForClient(c.ctx)));
+		this._register(_ipcServer.onDidRemoveConnection(c => {
+			this._loggerService.getLogger('mcpGateway')?.info(`[McpGateway][Channel] Client disconnected: ${c.ctx}, cleaning up gateways`);
+			mcpGatewayService.disposeGatewaysForClient(c.ctx);
+		}));
 	}
 
 	listen<T>(_ctx: TContext, _event: string): Event<T> {
@@ -30,6 +35,9 @@ export class McpGatewayChannel<TContext> extends Disposable implements IServerCh
 	}
 
 	async call<T>(ctx: TContext, command: string, args?: unknown): Promise<T> {
+		const logger = this._loggerService.getLogger('mcpGateway');
+		logger?.debug(`[McpGateway][Channel] IPC call: ${command} from client ${ctx}`);
+
 		switch (command) {
 			case 'createGateway': {
 				const brokerChannel = ipcChannelForContext(this._ipcServer, ctx);
@@ -42,9 +50,11 @@ export class McpGatewayChannel<TContext> extends Disposable implements IServerCh
 					readResource: (serverIndex, uri) => brokerChannel.call<MCP.ReadResourceResult>('readResource', { serverIndex, uri }),
 					listResourceTemplates: () => brokerChannel.call<readonly IGatewayServerResourceTemplates[]>('listResourceTemplates'),
 				});
+				logger?.info(`[McpGateway][Channel] Gateway created: ${result.gatewayId} for client ${ctx}`);
 				return result as T;
 			}
 			case 'disposeGateway': {
+				logger?.info(`[McpGateway][Channel] Disposing gateway: ${args as string} for client ${ctx}`);
 				await this.mcpGatewayService.disposeGateway(args as string);
 				return undefined as T;
 			}
diff --git a/src/vs/platform/mcp/node/mcpGatewayService.ts b/src/vs/platform/mcp/node/mcpGatewayService.ts
index 8225b3fffe8c3..6131c7677dab6 100644
--- a/src/vs/platform/mcp/node/mcpGatewayService.ts
+++ b/src/vs/platform/mcp/node/mcpGatewayService.ts
@@ -9,7 +9,7 @@ import { JsonRpcMessage, JsonRpcProtocol } from '../../../base/common/jsonRpcPro
 import { Disposable } from '../../../base/common/lifecycle.js';
 import { URI } from '../../../base/common/uri.js';
 import { generateUuid } from '../../../base/common/uuid.js';
-import { ILogService } from '../../log/common/log.js';
+import { ILogger, ILoggerService } from '../../log/common/log.js';
 import { IMcpGatewayInfo, IMcpGatewayService, IMcpGatewayToolInvoker } from '../common/mcpGateway.js';
 import { isInitializeMessage, McpGatewaySession } from './mcpGatewaySession.js';
 
@@ -28,11 +28,14 @@ export class McpGatewayService extends Disposable implements IMcpGatewayService
 	/** Maps gatewayId to clientId for tracking ownership */
 	private readonly _gatewayToClient = new Map<string, unknown>();
 	private _serverStartPromise: Promise<void> | undefined;
+	private readonly _logger: ILogger;
 
 	constructor(
-		@ILogService private readonly _logService: ILogService,
+		@ILoggerService loggerService: ILoggerService,
 	) {
 		super();
+		this._logger = this._register(loggerService.createLogger('mcpGateway', { name: 'MCP Gateway', logLevel: 'always' }));
+		this._logger.info('[McpGatewayService] Initialized');
 	}
 
 	async createGateway(clientId: unknown, toolInvoker?: IMcpGatewayToolInvoker): Promise<IMcpGatewayInfo> {
@@ -51,15 +54,16 @@ export class McpGatewayService extends Disposable implements IMcpGatewayService
 			throw new Error('[McpGatewayService] Tool invoker is required to create gateway');
 		}
 
-		const gateway = new McpGatewayRoute(gatewayId, this._logService, toolInvoker);
+		const gateway = new McpGatewayRoute(gatewayId, this._logger, toolInvoker);
 		this._gateways.set(gatewayId, gateway);
+		this._logger.info(`[McpGatewayService] Active gateways: ${this._gateways.size}`);
 
 		// Track client ownership if clientId provided (for cleanup on disconnect)
 		if (clientId) {
 			this._gatewayToClient.set(gatewayId, clientId);
-			this._logService.info(`[McpGatewayService] Created gateway at http://127.0.0.1:${this._port}/gateway/${gatewayId} for client ${clientId}`);
+			this._logger.info(`[McpGatewayService] Created gateway at http://127.0.0.1:${this._port}/gateway/${gatewayId} for client ${clientId}`);
 		} else {
-			this._logService.warn(`[McpGatewayService] Created gateway without client tracking at http://127.0.0.1:${this._port}/gateway/${gatewayId}`);
+			this._logger.warn(`[McpGatewayService] Created gateway without client tracking at http://127.0.0.1:${this._port}/gateway/${gatewayId}`);
 		}
 
 		const address = URI.parse(`http://127.0.0.1:${this._port}/gateway/${gatewayId}`);
@@ -73,14 +77,14 @@ export class McpGatewayService extends Disposable implements IMcpGatewayService
 	async disposeGateway(gatewayId: string): Promise<void> {
 		const gateway = this._gateways.get(gatewayId);
 		if (!gateway) {
-			this._logService.warn(`[McpGatewayService] Attempted to dispose unknown gateway: ${gatewayId}`);
+			this._logger.warn(`[McpGatewayService] Attempted to dispose unknown gateway: ${gatewayId}`);
 			return;
 		}
 
 		gateway.dispose();
 		this._gateways.delete(gatewayId);
 		this._gatewayToClient.delete(gatewayId);
-		this._logService.info(`[McpGatewayService] Disposed gateway: ${gatewayId}`);
+		this._logger.info(`[McpGatewayService] Disposed gateway: ${gatewayId} (remaining: ${this._gateways.size})`);
 
 		// If no more gateways, shut down the server
 		if (this._gateways.size === 0) {
@@ -98,7 +102,7 @@ export class McpGatewayService extends Disposable implements IMcpGatewayService
 		}
 
 		if (gatewaysToDispose.length > 0) {
-			this._logService.info(`[McpGatewayService] Disposing ${gatewaysToDispose.length} gateway(s) for disconnected client ${clientId}`);
+			this._logger.info(`[McpGatewayService] Disposing ${gatewaysToDispose.length} gateway(s) for disconnected client ${clientId}: [${gatewaysToDispose.join(', ')}]`);
 
 			for (const gatewayId of gatewaysToDispose) {
 				this._gateways.get(gatewayId)?.dispose();
@@ -156,19 +160,19 @@ export class McpGatewayService extends Disposable implements IMcpGatewayService
 			}
 
 			clearTimeout(portTimeout);
-			this._logService.info(`[McpGatewayService] Server started on port ${this._port}`);
+			this._logger.info(`[McpGatewayService] Server started on port ${this._port}`);
 			deferredPromise.complete();
 		});
 
 		this._server.on('error', (err: NodeJS.ErrnoException) => {
 			if (err.code === 'EADDRINUSE') {
-				this._logService.warn('[McpGatewayService] Port in use, retrying with random port...');
+				this._logger.warn('[McpGatewayService] Port in use, retrying with random port...');
 				// Try with a random port
 				this._server!.listen(0, '127.0.0.1');
 				return;
 			}
 			clearTimeout(portTimeout);
-			this._logService.error(`[McpGatewayService] Server error: ${err}`);
+			this._logger.error(`[McpGatewayService] Server error: ${err}`);
 			deferredPromise.error(err);
 		});
 
@@ -183,13 +187,13 @@ export class McpGatewayService extends Disposable implements IMcpGatewayService
 			return;
 		}
 
-		this._logService.info('[McpGatewayService] Stopping server (no more gateways)');
+		this._logger.info('[McpGatewayService] Stopping server (no more gateways)');
 
 		this._server.close(err => {
 			if (err) {
-				this._logService.error(`[McpGatewayService] Error closing server: ${err}`);
+				this._logger.error(`[McpGatewayService] Error closing server: ${err}`);
 			} else {
-				this._logService.info('[McpGatewayService] Server stopped');
+				this._logger.info('[McpGatewayService] Server stopped');
 			}
 		});
 
@@ -201,6 +205,8 @@ export class McpGatewayService extends Disposable implements IMcpGatewayService
 		const url = new URL(req.url!, `http://${req.headers.host}`);
 		const pathParts = url.pathname.split('/').filter(Boolean);
 
+		this._logger.debug(`[McpGatewayService] ${req.method} ${url.pathname} (active gateways: ${this._gateways.size})`);
+
 		// Expected path: /gateway/{gatewayId}
 		if (pathParts.length >= 2 && pathParts[0] === 'gateway') {
 			const gatewayId = pathParts[1];
@@ -213,11 +219,13 @@ export class McpGatewayService extends Disposable implements IMcpGatewayService
 		}
 
 		// Not found
+		this._logger.warn(`[McpGatewayService] ${req.method} ${url.pathname}: gateway not found`);
 		res.writeHead(404, { 'Content-Type': 'application/json' });
 		res.end(JSON.stringify({ error: 'Gateway not found' }));
 	}
 
 	override dispose(): void {
+		this._logger.info(`[McpGatewayService] Disposing service (gateways: ${this._gateways.size})`);
 		this._stopServer();
 		for (const gateway of this._gateways.values()) {
 			gateway.dispose();
@@ -237,13 +245,15 @@ class McpGatewayRoute extends Disposable {
 
 	constructor(
 		public readonly gatewayId: string,
-		private readonly _logService: ILogService,
+		private readonly _logger: ILogger,
 		private readonly _toolInvoker: IMcpGatewayToolInvoker,
 	) {
 		super();
 	}
 
 	handleRequest(req: http.IncomingMessage, res: http.ServerResponse): void {
+		this._logger.debug(`[McpGateway][route ${this.gatewayId}] ${req.method} request (sessions: ${this._sessions.size})`);
+
 		if (req.method === 'POST') {
 			void this._handlePost(req, res);
 			return;
@@ -263,6 +273,7 @@ class McpGatewayRoute extends Disposable {
 	}
 
 	public override dispose(): void {
+		this._logger.info(`[McpGateway][route ${this.gatewayId}] Disposing route (sessions: ${this._sessions.size})`);
 		for (const session of this._sessions.values()) {
 			session.dispose();
 		}
@@ -283,6 +294,7 @@ class McpGatewayRoute extends Disposable {
 			return;
 		}
 
+		this._logger.info(`[McpGateway][route ${this.gatewayId}] Deleting session ${sessionId}`);
 		session.dispose();
 		this._sessions.delete(sessionId);
 		res.writeHead(204);
@@ -302,6 +314,7 @@ class McpGatewayRoute extends Disposable {
 			return;
 		}
 
+		this._logger.info(`[McpGateway][route ${this.gatewayId}] SSE connection requested for session ${sessionId}`);
 		session.attachSseClient(req, res);
 	}
 
@@ -312,10 +325,13 @@ class McpGatewayRoute extends Disposable {
 			return;
 		}
 
+		this._logger.debug(`[McpGateway][route ${this.gatewayId}] Handling POST`);
+
 		let message: JsonRpcMessage | JsonRpcMessage[];
 		try {
 			message = JSON.parse(body) as JsonRpcMessage | JsonRpcMessage[];
 		} catch (error) {
+			this._logger.warn(`[McpGateway][route ${this.gatewayId}] JSON parse error: ${error instanceof Error ? error.message : String(error)}`);
 			res.writeHead(400, { 'Content-Type': 'application/json' });
 			res.end(JSON.stringify(JsonRpcProtocol.createParseError('Parse error', error instanceof Error ? error.message : String(error))));
 			return;
@@ -336,15 +352,18 @@ class McpGatewayRoute extends Disposable {
 			};
 
 			if (responses.length === 0) {
+				this._logger.debug(`[McpGateway][route ${this.gatewayId}] POST response: 202 (no content)`);
 				res.writeHead(202, headers);
 				res.end();
 				return;
 			}
 
+			const responseBody = JSON.stringify(Array.isArray(message) ? responses : responses[0]);
+			this._logger.debug(`[McpGateway][route ${this.gatewayId}] POST response: 200, body: ${responseBody}`);
 			res.writeHead(200, headers);
-			res.end(JSON.stringify(Array.isArray(message) ? responses : responses[0]));
+			res.end(responseBody);
 		} catch (error) {
-			this._logService.error('[McpGatewayService] Failed handling gateway request', error);
+			this._logger.error('[McpGatewayService] Failed handling gateway request', error);
 			this._respondHttpError(res, 500, 'Internal server error');
 		}
 	}
@@ -353,6 +372,7 @@ class McpGatewayRoute extends Disposable {
 		if (headerSessionId) {
 			const existing = this._sessions.get(headerSessionId);
 			if (!existing) {
+				this._logger.warn(`[McpGateway][route ${this.gatewayId}] Session not found: ${headerSessionId}`);
 				this._respondHttpError(res, 404, 'Session not found');
 				return undefined;
 			}
@@ -366,7 +386,8 @@ class McpGatewayRoute extends Disposable {
 		}
 
 		const sessionId = generateUuid();
-		const session = new McpGatewaySession(sessionId, this._logService, () => {
+		this._logger.info(`[McpGateway][route ${this.gatewayId}] Creating new session ${sessionId}`);
+		const session = new McpGatewaySession(sessionId, this._logger, () => {
 			this._sessions.delete(sessionId);
 		}, this._toolInvoker);
 		this._sessions.set(sessionId, session);
@@ -374,6 +395,7 @@ class McpGatewayRoute extends Disposable {
 	}
 
 	private _respondHttpError(res: http.ServerResponse, statusCode: number, error: string): void {
+		this._logger.debug(`[McpGateway][route ${this.gatewayId}] HTTP error response: ${statusCode} ${error}`);
 		res.writeHead(statusCode, { 'Content-Type': 'application/json' });
 		res.end(JSON.stringify({ jsonrpc: '2.0', error: { code: statusCode, message: error } } satisfies JsonRpcMessage));
 	}
diff --git a/src/vs/platform/mcp/node/mcpGatewaySession.ts b/src/vs/platform/mcp/node/mcpGatewaySession.ts
index 836d6571e3b5b..20f6d23dc7162 100644
--- a/src/vs/platform/mcp/node/mcpGatewaySession.ts
+++ b/src/vs/platform/mcp/node/mcpGatewaySession.ts
@@ -6,15 +6,22 @@
 import type * as http from 'http';
 import {
 	IJsonRpcNotification, IJsonRpcRequest,
-	isJsonRpcNotification, isJsonRpcResponse, JsonRpcError, JsonRpcMessage, JsonRpcProtocol
+	isJsonRpcNotification, isJsonRpcResponse, JsonRpcError, JsonRpcMessage, JsonRpcProtocol, JsonRpcResponse
 } from '../../../base/common/jsonRpcProtocol.js';
 import { Disposable } from '../../../base/common/lifecycle.js';
 import { hasKey } from '../../../base/common/types.js';
-import { ILogService } from '../../log/common/log.js';
+import { ILogger } from '../../log/common/log.js';
 import { IMcpGatewayToolInvoker } from '../common/mcpGateway.js';
 import { MCP } from '../common/modelContextProtocol.js';
 
 const MCP_LATEST_PROTOCOL_VERSION = '2025-11-25';
+const MCP_SUPPORTED_PROTOCOL_VERSIONS = [
+	'2025-11-25',
+	'2025-06-18',
+	'2025-03-26',
+	'2024-11-05',
+	'2024-10-07',
+];
 const MCP_INVALID_REQUEST = -32600;
 const MCP_METHOD_NOT_FOUND = -32601;
 const MCP_INVALID_PARAMS = -32602;
@@ -72,14 +79,12 @@ function encodeResourceUrisInContent(content: MCP.ContentBlock[], serverIndex: n
 export class McpGatewaySession extends Disposable {
 	private readonly _rpc: JsonRpcProtocol;
 	private readonly _sseClients = new Set<http.ServerResponse>();
-	private readonly _pendingResponses: JsonRpcMessage[] = [];
-	private _isCollectingPostResponses = false;
 	private _lastEventId = 0;
 	private _isInitialized = false;
 
 	constructor(
 		public readonly id: string,
-		private readonly _logService: ILogService,
+		private readonly _logService: ILogger,
 		private readonly _onDidDispose: () => void,
 		private readonly _toolInvoker: IMcpGatewayToolInvoker,
 	) {
@@ -98,6 +103,7 @@ export class McpGatewaySession extends Disposable {
 				return;
 			}
 
+			this._logService.info(`[McpGateway][session ${this.id}] Tools changed, notifying client`);
 			this._rpc.sendNotification({ method: 'notifications/tools/list_changed' });
 		}));
 
@@ -106,6 +112,7 @@ export class McpGatewaySession extends Disposable {
 				return;
 			}
 
+			this._logService.info(`[McpGateway][session ${this.id}] Resources changed, notifying client`);
 			this._rpc.sendNotification({ method: 'notifications/resources/list_changed' });
 		}));
 	}
@@ -119,25 +126,20 @@ export class McpGatewaySession extends Disposable {
 
 		res.write(': connected\n\n');
 		this._sseClients.add(res);
+		this._logService.info(`[McpGateway][session ${this.id}] SSE client attached (total: ${this._sseClients.size})`);
 
 		res.on('close', () => {
 			this._sseClients.delete(res);
+			this._logService.info(`[McpGateway][session ${this.id}] SSE client detached (total: ${this._sseClients.size})`);
 		});
 	}
 
-	public async handleIncoming(message: JsonRpcMessage | JsonRpcMessage[]): Promise<JsonRpcMessage[]> {
-		this._pendingResponses.length = 0;
-		this._isCollectingPostResponses = true;
-		try {
-			await this._rpc.handleMessage(message);
-			return [...this._pendingResponses];
-		} finally {
-			this._isCollectingPostResponses = false;
-			this._pendingResponses.length = 0;
-		}
+	public async handleIncoming(message: JsonRpcMessage | JsonRpcMessage[]): Promise<JsonRpcResponse[]> {
+		return this._rpc.handleMessage(message);
 	}
 
 	public override dispose(): void {
+		this._logService.info(`[McpGateway][session ${this.id}] Disposing session (SSE clients: ${this._sseClients.size})`);
 		for (const client of this._sseClients) {
 			if (!client.destroyed) {
 				client.end();
@@ -150,13 +152,12 @@ export class McpGatewaySession extends Disposable {
 
 	private _handleOutgoingMessage(message: JsonRpcMessage): void {
 		if (isJsonRpcResponse(message)) {
-			if (this._isCollectingPostResponses) {
-				this._pendingResponses.push(message);
-			}
+			this._logService.debug(`[McpGateway][session ${this.id}] --> response: ${JSON.stringify(message)}`);
 			return;
 		}
 
 		if (isJsonRpcNotification(message)) {
+			this._logService.debug(`[McpGateway][session ${this.id}] --> notification: ${(message as IJsonRpcNotification).method}`);
 			this._broadcastSse(message);
 			return;
 		}
@@ -166,11 +167,13 @@ export class McpGatewaySession extends Disposable {
 
 	private _broadcastSse(message: JsonRpcMessage): void {
 		if (this._sseClients.size === 0) {
+			this._logService.debug(`[McpGateway][session ${this.id}] No SSE clients to broadcast to, dropping message`);
 			return;
 		}
 
 		const payload = JSON.stringify(message);
 		const eventId = String(++this._lastEventId);
+		this._logService.debug(`[McpGateway][session ${this.id}] Broadcasting SSE event id=${eventId} to ${this._sseClients.size}`);
 		const lines = payload.split(/\r?\n/g);
 		const data = [
 			`id: ${eventId}`,
@@ -191,11 +194,14 @@ export class McpGatewaySession extends Disposable {
 	}
 
 	private async _handleRequest(request: IJsonRpcRequest): Promise<unknown> {
+		this._logService.debug(`[McpGateway][session ${this.id}] <-- request: ${request.method} (id=${String(request.id)})`);
+
 		if (request.method === 'initialize') {
-			return this._handleInitialize();
+			return this._handleInitialize(request);
 		}
 
 		if (!this._isInitialized) {
+			this._logService.warn(`[McpGateway][session ${this.id}] Rejected request '${request.method}': session not initialized`);
 			throw new JsonRpcError(MCP_INVALID_REQUEST, 'Session is not initialized');
 		}
 
@@ -213,21 +219,37 @@ export class McpGatewaySession extends Disposable {
 			case 'resources/templates/list':
 				return this._handleListResourceTemplates();
 			default:
+				this._logService.warn(`[McpGateway][session ${this.id}] Unknown method: ${request.method}`);
 				throw new JsonRpcError(MCP_METHOD_NOT_FOUND, `Method not found: ${request.method}`);
 		}
 	}
 
 	private _handleNotification(notification: IJsonRpcNotification): void {
+		this._logService.debug(`[McpGateway][session ${this.id}] <-- notification: ${notification.method}`);
+
 		if (notification.method === 'notifications/initialized') {
 			this._isInitialized = true;
+			this._logService.info(`[McpGateway][session ${this.id}] Session initialized`);
 			this._rpc.sendNotification({ method: 'notifications/tools/list_changed' });
 			this._rpc.sendNotification({ method: 'notifications/resources/list_changed' });
 		}
 	}
 
-	private _handleInitialize(): MCP.InitializeResult {
+	private _handleInitialize(request: IJsonRpcRequest): MCP.InitializeResult {
+		const params = typeof request.params === 'object' && request.params ? request.params as Record<string, unknown> : undefined;
+		const clientVersion = typeof params?.protocolVersion === 'string' ? params.protocolVersion : undefined;
+		const clientInfo = params?.clientInfo as { name?: string; version?: string } | undefined;
+		const negotiatedVersion = clientVersion && MCP_SUPPORTED_PROTOCOL_VERSIONS.includes(clientVersion)
+			? clientVersion
+			: MCP_LATEST_PROTOCOL_VERSION;
+
+		this._logService.info(`[McpGateway] Initialize: client=${clientInfo?.name ?? 'unknown'}/${clientInfo?.version ?? '?'}, clientProtocol=${clientVersion ?? '(none)'}, negotiated=${negotiatedVersion}`);
+		if (clientVersion && clientVersion !== negotiatedVersion) {
+			this._logService.warn(`[McpGateway] Client requested unsupported protocol version '${clientVersion}', falling back to '${negotiatedVersion}'`);
+		}
+
 		return {
-			protocolVersion: MCP_LATEST_PROTOCOL_VERSION,
+			protocolVersion: negotiatedVersion,
 			capabilities: {
 				tools: {
 					listChanged: true,
@@ -257,21 +279,27 @@ export class McpGatewaySession extends Disposable {
 			? params.arguments as Record<string, unknown>
 			: {};
 
+		this._logService.debug(`[McpGateway][session ${this.id}] Calling tool '${params.name}' with args: ${JSON.stringify(argumentsValue)}`);
+
 		try {
 			const { result, serverIndex } = await this._toolInvoker.callTool(params.name, argumentsValue);
+			this._logService.debug(`[McpGateway][session ${this.id}] Tool '${params.name}' completed (isError=${result.isError ?? false}, content blocks=${result.content.length})`);
 			return {
 				...result,
 				content: encodeResourceUrisInContent(result.content, serverIndex),
 			};
 		} catch (error) {
-			this._logService.error('[McpGatewayService] Tool call invocation failed', error);
+			this._logService.error(`[McpGateway][session ${this.id}] Tool '${params.name}' invocation failed`, error);
 			throw new JsonRpcError(MCP_INVALID_PARAMS, String(error));
 		}
 	}
 
 	private _handleListTools(): unknown {
 		return this._toolInvoker.listTools()
-			.then(tools => ({ tools }));
+			.then(tools => {
+				this._logService.debug(`[McpGateway][session ${this.id}] Listed ${tools.length} tool(s): [${tools.map(t => t.name).join(', ')}]`);
+				return { tools };
+			});
 	}
 
 	private async _handleListResources(): Promise<MCP.ListResourcesResult> {
@@ -285,6 +313,7 @@ export class McpGatewaySession extends Disposable {
 				});
 			}
 		}
+		this._logService.debug(`[McpGateway][session ${this.id}] Listed ${allResources.length} resource(s) from ${serverResults.length} server(s)`);
 		return { resources: allResources };
 	}
 
@@ -295,8 +324,10 @@ export class McpGatewaySession extends Disposable {
 		}
 
 		const { serverIndex, originalUri } = decodeGatewayResourceUri(params.uri);
+		this._logService.debug(`[McpGateway][session ${this.id}] Reading resource '${originalUri}' from server ${serverIndex}`);
 		try {
 			const result = await this._toolInvoker.readResource(serverIndex, originalUri);
+			this._logService.debug(`[McpGateway][session ${this.id}] Resource read returned ${result.contents.length} content(s)`);
 			return {
 				contents: result.contents.map(content => ({
 					...content,
@@ -304,7 +335,7 @@ export class McpGatewaySession extends Disposable {
 				})),
 			};
 		} catch (error) {
-			this._logService.error('[McpGatewayService] Resource read failed', error);
+			this._logService.error(`[McpGateway][session ${this.id}] Resource read failed for '${originalUri}'`, error);
 			throw new JsonRpcError(MCP_INVALID_PARAMS, String(error));
 		}
 	}
@@ -320,6 +351,7 @@ export class McpGatewaySession extends Disposable {
 				});
 			}
 		}
+		this._logService.debug(`[McpGateway][session ${this.id}] Listed ${allTemplates.length} resource template(s) from ${serverResults.length} server(s)`);
 		return { resourceTemplates: allTemplates };
 	}
 }
diff --git a/src/vs/platform/mcp/test/common/mcpManagementService.test.ts b/src/vs/platform/mcp/test/common/mcpManagementService.test.ts
index 78ee329965290..7245ffd376bdd 100644
--- a/src/vs/platform/mcp/test/common/mcpManagementService.test.ts
+++ b/src/vs/platform/mcp/test/common/mcpManagementService.test.ts
@@ -4,14 +4,22 @@
  *--------------------------------------------------------------------------------------------*/
 
 import assert from 'assert';
+import { VSBuffer } from '../../../../base/common/buffer.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../base/test/common/utils.js';
-import { AbstractCommonMcpManagementService } from '../../common/mcpManagementService.js';
-import { IGalleryMcpServer, IGalleryMcpServerConfiguration, IInstallableMcpServer, ILocalMcpServer, InstallOptions, RegistryType, TransportType, UninstallOptions } from '../../common/mcpManagement.js';
-import { McpServerType, McpServerVariableType, IMcpServerVariable } from '../../common/mcpPlatformTypes.js';
+import { DisposableStore } from '../../../../base/common/lifecycle.js';
+import { Schemas } from '../../../../base/common/network.js';
+import { AbstractCommonMcpManagementService, AbstractMcpResourceManagementService } from '../../common/mcpManagementService.js';
+import { IGalleryMcpServer, IGalleryMcpServerConfiguration, IInstallableMcpServer, ILocalMcpServer, IMcpGalleryService, InstallOptions, RegistryType, TransportType, UninstallOptions } from '../../common/mcpManagement.js';
+import { IMcpSandboxConfiguration, McpServerType, McpServerVariableType, IMcpServerConfiguration, IMcpServerVariable } from '../../common/mcpPlatformTypes.js';
 import { IMarkdownString } from '../../../../base/common/htmlContent.js';
 import { Event } from '../../../../base/common/event.js';
 import { URI } from '../../../../base/common/uri.js';
+import { ConfigurationTarget } from '../../../configuration/common/configuration.js';
+import { FileService } from '../../../files/common/fileService.js';
+import { InMemoryFileSystemProvider } from '../../../files/common/inMemoryFilesystemProvider.js';
 import { NullLogService } from '../../../log/common/log.js';
+import { McpResourceScannerService } from '../../common/mcpResourceScannerService.js';
+import { UriIdentityService } from '../../../uriIdentity/common/uriIdentityService.js';
 
 class TestMcpManagementService extends AbstractCommonMcpManagementService {
 
@@ -42,6 +50,44 @@ class TestMcpManagementService extends AbstractCommonMcpManagementService {
 	}
 }
 
+class TestMcpResourceManagementService extends AbstractMcpResourceManagementService {
+	constructor(mcpResource: URI, fileService: FileService, uriIdentityService: UriIdentityService, mcpResourceScannerService: McpResourceScannerService) {
+		super(
+			mcpResource,
+			ConfigurationTarget.USER,
+			{} as IMcpGalleryService,
+			fileService,
+			uriIdentityService,
+			new NullLogService(),
+			mcpResourceScannerService,
+		);
+	}
+
+	public reload(): Promise<void> {
+		return this.updateLocal();
+	}
+
+	override canInstall(_server: IGalleryMcpServer | IInstallableMcpServer): true | IMarkdownString {
+		throw new Error('Not supported');
+	}
+
+	protected override getLocalServerInfo(_name: string, _mcpServerConfig: IMcpServerConfiguration) {
+		return Promise.resolve(undefined);
+	}
+
+	protected override installFromUri(_uri: URI): Promise<ILocalMcpServer> {
+		throw new Error('Not supported');
+	}
+
+	override installFromGallery(_server: IGalleryMcpServer, _options?: InstallOptions): Promise<ILocalMcpServer> {
+		throw new Error('Not supported');
+	}
+
+	override updateMetadata(_local: ILocalMcpServer, _server: IGalleryMcpServer): Promise<ILocalMcpServer> {
+		throw new Error('Not supported');
+	}
+}
+
 suite('McpManagementService - getMcpServerConfigurationFromManifest', () => {
 	let service: TestMcpManagementService;
 
@@ -1073,3 +1119,74 @@ suite('McpManagementService - getMcpServerConfigurationFromManifest', () => {
 		});
 	});
 });
+
+suite('McpResourceManagementService', () => {
+	const mcpResource = URI.from({ scheme: Schemas.inMemory, path: '/mcp.json' });
+	let disposables: DisposableStore;
+	let fileService: FileService;
+	let service: TestMcpResourceManagementService;
+
+	setup(async () => {
+		disposables = new DisposableStore();
+		fileService = disposables.add(new FileService(new NullLogService()));
+		disposables.add(fileService.registerProvider(Schemas.inMemory, disposables.add(new InMemoryFileSystemProvider())));
+		const uriIdentityService = disposables.add(new UriIdentityService(fileService));
+		const scannerService = disposables.add(new McpResourceScannerService(fileService, uriIdentityService));
+		service = disposables.add(new TestMcpResourceManagementService(mcpResource, fileService, uriIdentityService, scannerService));
+
+		await fileService.writeFile(mcpResource, VSBuffer.fromString(JSON.stringify({
+			sandbox: {
+				network: { allowedDomains: ['example.com'] }
+			},
+			servers: {
+				test: {
+					type: 'stdio',
+					command: 'node',
+					sandboxEnabled: true
+				}
+			}
+		}, null, '\t')));
+	});
+
+	teardown(() => {
+		disposables.dispose();
+	});
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('fires update when root sandbox changes', async () => {
+		const initial = await service.getInstalled();
+		assert.strictEqual(initial.length, 1);
+		assert.deepStrictEqual(initial[0].rootSandbox, {
+			network: { allowedDomains: ['example.com'] }
+		});
+
+		let updateCount = 0;
+		const updatePromise = new Promise<void>(resolve => disposables.add(service.onDidUpdateMcpServers(e => {
+			assert.strictEqual(e.length, 1);
+			updateCount++;
+			resolve();
+		})));
+
+		const updatedSandbox: IMcpSandboxConfiguration = {
+			network: { allowedDomains: ['changed.example.com'] }
+		};
+
+		await fileService.writeFile(mcpResource, VSBuffer.fromString(JSON.stringify({
+			sandbox: updatedSandbox,
+			servers: {
+				test: {
+					type: 'stdio',
+					command: 'node',
+					sandboxEnabled: true
+				}
+			}
+		}, null, '\t')));
+		await service.reload();
+		await updatePromise;
+		const updated = await service.getInstalled();
+
+		assert.strictEqual(updateCount, 1);
+		assert.deepStrictEqual(updated[0].rootSandbox, updatedSandbox);
+	});
+});
diff --git a/src/vs/platform/mcp/test/node/mcpGatewaySession.test.ts b/src/vs/platform/mcp/test/node/mcpGatewaySession.test.ts
index 98712bb96810a..d30d166d09fbf 100644
--- a/src/vs/platform/mcp/test/node/mcpGatewaySession.test.ts
+++ b/src/vs/platform/mcp/test/node/mcpGatewaySession.test.ts
@@ -112,6 +112,145 @@ suite('McpGatewaySession', () => {
 		onDidChangeResources.dispose();
 	});
 
+	test('negotiates to older protocol version when client requests it', async () => {
+		const { invoker, onDidChangeTools, onDidChangeResources } = createInvoker();
+		const session = new McpGatewaySession('session-negotiate-1', new NullLogService(), () => { }, invoker);
+
+		const responses = await session.handleIncoming({
+			jsonrpc: '2.0',
+			id: 1,
+			method: 'initialize',
+			params: {
+				protocolVersion: '2025-03-26',
+				capabilities: {},
+				clientInfo: { name: 'test-client', version: '1.0.0' },
+			},
+		});
+
+		assert.strictEqual(responses.length, 1);
+		const response = responses[0] as IJsonRpcSuccessResponse;
+		assert.strictEqual((response.result as { protocolVersion: string }).protocolVersion, '2025-03-26');
+		session.dispose();
+		onDidChangeTools.dispose();
+		onDidChangeResources.dispose();
+	});
+
+	test('negotiates to each supported protocol version', async () => {
+		const supportedVersions = ['2025-11-25', '2025-06-18', '2025-03-26', '2024-11-05', '2024-10-07'];
+		for (const version of supportedVersions) {
+			const { invoker, onDidChangeTools, onDidChangeResources } = createInvoker();
+			const session = new McpGatewaySession(`session-ver-${version}`, new NullLogService(), () => { }, invoker);
+
+			const responses = await session.handleIncoming({
+				jsonrpc: '2.0',
+				id: 1,
+				method: 'initialize',
+				params: { protocolVersion: version, capabilities: {} },
+			});
+
+			const response = responses[0] as IJsonRpcSuccessResponse;
+			assert.strictEqual(
+				(response.result as { protocolVersion: string }).protocolVersion,
+				version,
+				`Expected server to negotiate to ${version}`
+			);
+			session.dispose();
+			onDidChangeTools.dispose();
+			onDidChangeResources.dispose();
+		}
+	});
+
+	test('falls back to latest version for unsupported client version', async () => {
+		const { invoker, onDidChangeTools, onDidChangeResources } = createInvoker();
+		const session = new McpGatewaySession('session-negotiate-2', new NullLogService(), () => { }, invoker);
+
+		const responses = await session.handleIncoming({
+			jsonrpc: '2.0',
+			id: 1,
+			method: 'initialize',
+			params: {
+				protocolVersion: '2099-01-01',
+				capabilities: {},
+				clientInfo: { name: 'test-client', version: '1.0.0' },
+			},
+		});
+
+		assert.strictEqual(responses.length, 1);
+		const response = responses[0] as IJsonRpcSuccessResponse;
+		assert.strictEqual((response.result as { protocolVersion: string }).protocolVersion, '2025-11-25');
+		session.dispose();
+		onDidChangeTools.dispose();
+		onDidChangeResources.dispose();
+	});
+
+	test('falls back to latest version when no params provided', async () => {
+		const { invoker, onDidChangeTools, onDidChangeResources } = createInvoker();
+		const session = new McpGatewaySession('session-negotiate-3', new NullLogService(), () => { }, invoker);
+
+		const responses = await session.handleIncoming({
+			jsonrpc: '2.0',
+			id: 1,
+			method: 'initialize',
+		});
+
+		assert.strictEqual(responses.length, 1);
+		const response = responses[0] as IJsonRpcSuccessResponse;
+		assert.strictEqual((response.result as { protocolVersion: string }).protocolVersion, '2025-11-25');
+		session.dispose();
+		onDidChangeTools.dispose();
+		onDidChangeResources.dispose();
+	});
+
+	test('falls back to latest version when protocolVersion is not a string', async () => {
+		const { invoker, onDidChangeTools, onDidChangeResources } = createInvoker();
+		const session = new McpGatewaySession('session-negotiate-4', new NullLogService(), () => { }, invoker);
+
+		const responses = await session.handleIncoming({
+			jsonrpc: '2.0',
+			id: 1,
+			method: 'initialize',
+			params: {
+				protocolVersion: 42,
+				capabilities: {},
+			},
+		});
+
+		assert.strictEqual(responses.length, 1);
+		const response = responses[0] as IJsonRpcSuccessResponse;
+		assert.strictEqual((response.result as { protocolVersion: string }).protocolVersion, '2025-11-25');
+		session.dispose();
+		onDidChangeTools.dispose();
+		onDidChangeResources.dispose();
+	});
+
+	test('initialize response includes server info and capabilities', async () => {
+		const { invoker, onDidChangeTools, onDidChangeResources } = createInvoker();
+		const session = new McpGatewaySession('session-init-caps', new NullLogService(), () => { }, invoker);
+
+		const responses = await session.handleIncoming({
+			jsonrpc: '2.0',
+			id: 1,
+			method: 'initialize',
+			params: { protocolVersion: '2025-03-26', capabilities: {} },
+		});
+
+		const result = (responses[0] as IJsonRpcSuccessResponse).result as MCP.InitializeResult;
+		assert.deepStrictEqual(result, {
+			protocolVersion: '2025-03-26',
+			capabilities: {
+				tools: { listChanged: true },
+				resources: { listChanged: true },
+			},
+			serverInfo: {
+				name: 'VS Code MCP Gateway',
+				version: '1.0.0',
+			},
+		});
+		session.dispose();
+		onDidChangeTools.dispose();
+		onDidChangeResources.dispose();
+	});
+
 	test('rejects non-initialize requests before initialized notification', async () => {
 		const { invoker, onDidChangeTools, onDidChangeResources } = createInvoker();
 		const session = new McpGatewaySession('session-2', new NullLogService(), () => { }, invoker);
diff --git a/src/vs/platform/quickinput/browser/media/quickInput.css b/src/vs/platform/quickinput/browser/media/quickInput.css
index bd509719a3cce..aa48f0b90f236 100644
--- a/src/vs/platform/quickinput/browser/media/quickInput.css
+++ b/src/vs/platform/quickinput/browser/media/quickInput.css
@@ -9,7 +9,8 @@
 	z-index: 2550;
 	left: 50%;
 	-webkit-app-region: no-drag;
-	border-radius: 8px;
+	border-radius: var(--vscode-cornerRadius-xLarge);
+	box-shadow: var(--vscode-shadow-xl);
 }
 
 .quick-input-titlebar {
@@ -97,6 +98,10 @@
 	padding: 6px 6px 4px 6px;
 }
 
+.quick-input-widget .quick-input-filter .monaco-inputbox {
+	border-radius: var(--vscode-cornerRadius-medium);
+}
+
 .quick-input-widget.hidden-input .quick-input-header {
 	/* reduce margins and paddings when input box hidden */
 	padding: 0;
@@ -303,6 +308,8 @@
 
 .quick-input-list .quick-input-list-entry .quick-input-list-separator {
 	margin-right: 4px;
+	font-size: var(--vscode-bodyFontSize-xSmall);
+	color: var(--vscode-descriptionForeground);
 	/* separate from keybindings or actions */
 }
 
diff --git a/src/vs/platform/quickinput/browser/quickInputController.ts b/src/vs/platform/quickinput/browser/quickInputController.ts
index 8e5283ef9ad92..162d90de81b21 100644
--- a/src/vs/platform/quickinput/browser/quickInputController.ts
+++ b/src/vs/platform/quickinput/browser/quickInputController.ts
@@ -922,13 +922,12 @@ export class QuickInputController extends Disposable {
 	private updateStyles() {
 		if (this.ui) {
 			const {
-				quickInputTitleBackground, quickInputBackground, quickInputForeground, widgetBorder, widgetShadow,
+				quickInputTitleBackground, quickInputBackground, quickInputForeground, widgetBorder,
 			} = this.styles.widget;
 			this.ui.titleBar.style.backgroundColor = quickInputTitleBackground ?? '';
 			this.ui.container.style.backgroundColor = quickInputBackground ?? '';
 			this.ui.container.style.color = quickInputForeground ?? '';
 			this.ui.container.style.border = widgetBorder ? `1px solid ${widgetBorder}` : '';
-			this.ui.container.style.boxShadow = widgetShadow ? `0 0 8px 2px ${widgetShadow}` : '';
 			this.ui.list.style(this.styles.list);
 			this.ui.tree.tree.style(this.styles.list);
 
diff --git a/src/vs/platform/quickinput/browser/tree/quickTree.ts b/src/vs/platform/quickinput/browser/tree/quickTree.ts
index e506021a05892..3c9a614694866 100644
--- a/src/vs/platform/quickinput/browser/tree/quickTree.ts
+++ b/src/vs/platform/quickinput/browser/tree/quickTree.ts
@@ -104,6 +104,11 @@ export class QuickTree<T extends IQuickTreeItem> extends QuickInput implements I
 		this.ui.inputBox.setFocus();
 	}
 
+	reveal(element: T): void {
+		this.ui.tree.tree.reveal(element);
+		this.ui.tree.tree.setFocus([element]);
+	}
+
 	override show() {
 		if (!this.visible) {
 			const visibilities: Visibilities = {
diff --git a/src/vs/platform/quickinput/common/quickInput.ts b/src/vs/platform/quickinput/common/quickInput.ts
index 9426be48e2f4a..04d91e66aa488 100644
--- a/src/vs/platform/quickinput/common/quickInput.ts
+++ b/src/vs/platform/quickinput/common/quickInput.ts
@@ -1172,6 +1172,12 @@ export interface IQuickTree<T extends IQuickTreeItem> extends IQuickInput {
 	 */
 	focusOnInput(): void;
 
+	/**
+	 * Reveals and focuses a specific item in the tree.
+	 * @param element The item to reveal and focus.
+	 */
+	reveal(element: T): void;
+
 	/**
 	 * Focus a particular item in the list. Used internally for keyboard navigation.
 	 * @param focus The focus behavior.
diff --git a/src/vs/platform/quickinput/test/browser/quickinput.test.ts b/src/vs/platform/quickinput/test/browser/quickinput.test.ts
index 217fef3990695..db57dedbffa01 100644
--- a/src/vs/platform/quickinput/test/browser/quickinput.test.ts
+++ b/src/vs/platform/quickinput/test/browser/quickinput.test.ts
@@ -66,8 +66,7 @@ suite('QuickInput', () => { // https://github.com/microsoft/vscode/issues/147543
 		instantiationService.stub(IConfigurationService, new TestConfigurationService());
 		instantiationService.stub(IAccessibilityService, new TestAccessibilityService());
 		instantiationService.stub(IListService, store.add(new ListService()));
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(ILayoutService, { activeContainer: fixture, onDidLayoutContainer: Event.None } as any);
+		instantiationService.stub(ILayoutService, { _serviceBrand: undefined, activeContainer: fixture, onDidLayoutContainer: Event.None });
 		instantiationService.stub(IContextViewService, store.add(instantiationService.createInstance(ContextViewService)));
 		instantiationService.stub(IContextKeyService, store.add(instantiationService.createInstance(ContextKeyService)));
 		instantiationService.stub(IKeybindingService, {
diff --git a/src/vs/platform/remote/browser/browserSocketFactory.ts b/src/vs/platform/remote/browser/browserSocketFactory.ts
index eafeef861a19b..d558e4eef58c1 100644
--- a/src/vs/platform/remote/browser/browserSocketFactory.ts
+++ b/src/vs/platform/remote/browser/browserSocketFactory.ts
@@ -43,7 +43,7 @@ export interface IWebSocket {
 	readonly onError: Event<unknown>;
 
 	traceSocketEvent?(type: SocketDiagnosticsEventType, data?: VSBuffer | Uint8Array | ArrayBuffer | ArrayBufferView | unknown): void;
-	send(data: ArrayBuffer | ArrayBufferView): void;
+	send(data: ArrayBuffer | ArrayBufferView<ArrayBuffer>): void;
 	close(): void;
 }
 
@@ -182,7 +182,7 @@ class BrowserWebSocket extends Disposable implements IWebSocket {
 		}));
 	}
 
-	send(data: ArrayBuffer | ArrayBufferView): void {
+	send(data: ArrayBuffer | ArrayBufferView<ArrayBuffer>): void {
 		if (this._isClosed) {
 			// Refuse to write data to closed WebSocket...
 			return;
@@ -254,7 +254,7 @@ class BrowserSocket implements ISocket {
 	}
 
 	public write(buffer: VSBuffer): void {
-		this.socket.send(buffer.buffer);
+		this.socket.send(buffer.buffer as Uint8Array<ArrayBuffer>);
 	}
 
 	public end(): void {
diff --git a/src/vs/platform/request/common/request.ts b/src/vs/platform/request/common/request.ts
index df18c523dd720..8db0214ed89d8 100644
--- a/src/vs/platform/request/common/request.ts
+++ b/src/vs/platform/request/common/request.ts
@@ -6,6 +6,7 @@
 import { streamToBuffer } from '../../../base/common/buffer.js';
 import { CancellationToken } from '../../../base/common/cancellation.js';
 import { getErrorMessage } from '../../../base/common/errors.js';
+import { Emitter, Event } from '../../../base/common/event.js';
 import { Disposable } from '../../../base/common/lifecycle.js';
 import { IHeaders, IRequestContext, IRequestOptions } from '../../../base/parts/request/common/request.js';
 import { localize } from '../../../nls.js';
@@ -16,6 +17,19 @@ import { Registry } from '../../registry/common/platform.js';
 
 export const IRequestService = createDecorator<IRequestService>('requestService');
 
+/**
+ * Use as the {@link IRequestOptions.callSite} value to prevent
+ * request telemetry from being emitted. This is needed for
+ * callers such as the telemetry sender to avoid cyclical calls.
+ */
+export const NO_FETCH_TELEMETRY = 'NO_FETCH_TELEMETRY';
+
+export interface IRequestCompleteEvent {
+	readonly callSite: string;
+	readonly latency: number;
+	readonly statusCode: number | undefined;
+}
+
 export interface AuthInfo {
 	isProxy: boolean;
 	scheme: string;
@@ -33,6 +47,11 @@ export interface Credentials {
 export interface IRequestService {
 	readonly _serviceBrand: undefined;
 
+	/**
+	 * Fires when a request completes (successfully or with an error response).
+	 */
+	readonly onDidCompleteRequest: Event<IRequestCompleteEvent>;
+
 	request(options: IRequestOptions, token: CancellationToken): Promise<IRequestContext>;
 
 	resolveProxy(url: string): Promise<string | undefined>;
@@ -70,6 +89,9 @@ export abstract class AbstractRequestService extends Disposable implements IRequ
 
 	private counter = 0;
 
+	private readonly _onDidCompleteRequest = this._register(new Emitter<IRequestCompleteEvent>());
+	readonly onDidCompleteRequest = this._onDidCompleteRequest.event;
+
 	constructor(protected readonly logService: ILogService) {
 		super();
 	}
@@ -77,9 +99,15 @@ export abstract class AbstractRequestService extends Disposable implements IRequ
 	protected async logAndRequest(options: IRequestOptions, request: () => Promise<IRequestContext>): Promise<IRequestContext> {
 		const prefix = `#${++this.counter}: ${options.url}`;
 		this.logService.trace(`${prefix} - begin`, options.type, new LoggableHeaders(options.headers ?? {}));
+		const startTime = Date.now();
 		try {
 			const result = await request();
 			this.logService.trace(`${prefix} - end`, options.type, result.res.statusCode, result.res.headers);
+			this._onDidCompleteRequest.fire({
+				callSite: options.callSite,
+				latency: Date.now() - startTime,
+				statusCode: result.res.statusCode,
+			});
 			return result;
 		} catch (error) {
 			this.logService.error(`${prefix} - error`, options.type, getErrorMessage(error));
@@ -284,6 +312,12 @@ function registerProxyConfigurations(useHostProxy = true, useHostProxyDefault =
 					markdownDescription: localize('fetchAdditionalSupport', "Controls whether Node.js' fetch implementation should be extended with additional support. Currently proxy support ({1}) and system certificates ({2}) are added when the corresponding settings are enabled. When during [remote development](https://aka.ms/vscode-remote) the {0} setting is disabled this setting can be configured in the local and the remote settings separately.", '`#http.useLocalProxyConfiguration#`', '`#http.proxySupport#`', '`#http.systemCertificates#`'),
 					restricted: true
 				},
+				'http.webSocketAdditionalSupport': {
+					type: 'boolean',
+					default: true,
+					markdownDescription: localize('webSocketAdditionalSupport', "Controls whether the built-in WebSocket implementation should be extended with additional support. Currently proxy support ({1}) and system certificates ({2}) are added when the corresponding settings are enabled. When during [remote development](https://aka.ms/vscode-remote) the {0} setting is disabled this setting can be configured in the local and the remote settings separately.", '`#http.useLocalProxyConfiguration#`', '`#http.proxySupport#`', '`#http.systemCertificates#`'),
+					restricted: true
+				},
 				'http.experimental.networkInterfaceCheckInterval': {
 					type: 'number',
 					default: 300,
diff --git a/src/vs/platform/request/common/requestIpc.ts b/src/vs/platform/request/common/requestIpc.ts
index 0b3aff1a886d2..341556406fca5 100644
--- a/src/vs/platform/request/common/requestIpc.ts
+++ b/src/vs/platform/request/common/requestIpc.ts
@@ -8,7 +8,7 @@ import { CancellationToken } from '../../../base/common/cancellation.js';
 import { Event } from '../../../base/common/event.js';
 import { IChannel, IServerChannel } from '../../../base/parts/ipc/common/ipc.js';
 import { IHeaders, IRequestContext, IRequestOptions } from '../../../base/parts/request/common/request.js';
-import { AuthInfo, Credentials, IRequestService } from './request.js';
+import { AuthInfo, Credentials, IRequestCompleteEvent, IRequestService } from './request.js';
 
 type RequestResponse = [
 	{
@@ -46,6 +46,8 @@ export class RequestChannelClient implements IRequestService {
 
 	declare readonly _serviceBrand: undefined;
 
+	readonly onDidCompleteRequest = Event.None as Event<IRequestCompleteEvent>;
+
 	constructor(private readonly channel: IChannel) { }
 
 	async request(options: IRequestOptions, token: CancellationToken): Promise<IRequestContext> {
diff --git a/src/vs/platform/request/test/common/requestService.test.ts b/src/vs/platform/request/test/common/requestService.test.ts
new file mode 100644
index 0000000000000..3760902fb1f9c
--- /dev/null
+++ b/src/vs/platform/request/test/common/requestService.test.ts
@@ -0,0 +1,101 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { bufferToStream, VSBuffer } from '../../../../base/common/buffer.js';
+import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { IRequestContext, IRequestOptions } from '../../../../base/parts/request/common/request.js';
+import { NullLogService } from '../../../log/common/log.js';
+import { AbstractRequestService, AuthInfo, Credentials, IRequestCompleteEvent, NO_FETCH_TELEMETRY } from '../../common/request.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../base/test/common/utils.js';
+
+class TestRequestService extends AbstractRequestService {
+
+	constructor(private readonly handler: (options: IRequestOptions) => Promise<IRequestContext>) {
+		super(new NullLogService());
+	}
+
+	async request(options: IRequestOptions, token: CancellationToken): Promise<IRequestContext> {
+		return this.logAndRequest(options, () => this.handler(options));
+	}
+
+	async resolveProxy(_url: string): Promise<string | undefined> { return undefined; }
+	async lookupAuthorization(_authInfo: AuthInfo): Promise<Credentials | undefined> { return undefined; }
+	async lookupKerberosAuthorization(_url: string): Promise<string | undefined> { return undefined; }
+	async loadCertificates(): Promise<string[]> { return []; }
+}
+
+function makeResponse(statusCode: number): IRequestContext {
+	return {
+		res: { headers: {}, statusCode },
+		stream: bufferToStream(VSBuffer.fromString(''))
+	};
+}
+
+suite('AbstractRequestService', () => {
+
+	const store = ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('onDidCompleteRequest fires with correct data', async () => {
+		const service = store.add(new TestRequestService(() => Promise.resolve(makeResponse(200))));
+
+		const events: IRequestCompleteEvent[] = [];
+		store.add(service.onDidCompleteRequest(e => events.push(e)));
+
+		await service.request({ url: 'http://test', callSite: 'test.callSite' }, CancellationToken.None);
+
+		assert.strictEqual(events.length, 1);
+		assert.strictEqual(events[0].callSite, 'test.callSite');
+		assert.strictEqual(events[0].statusCode, 200);
+		assert.ok(events[0].latency >= 0);
+	});
+
+	test('onDidCompleteRequest reports status code from response', async () => {
+		const service = store.add(new TestRequestService(() => Promise.resolve(makeResponse(404))));
+
+		const events: IRequestCompleteEvent[] = [];
+		store.add(service.onDidCompleteRequest(e => events.push(e)));
+
+		await service.request({ url: 'http://test', callSite: 'test.notFound' }, CancellationToken.None);
+
+		assert.strictEqual(events.length, 1);
+		assert.strictEqual(events[0].statusCode, 404);
+	});
+
+	test('onDidCompleteRequest fires for NO_FETCH_TELEMETRY', async () => {
+		const service = store.add(new TestRequestService(() => Promise.resolve(makeResponse(200))));
+
+		const events: IRequestCompleteEvent[] = [];
+		store.add(service.onDidCompleteRequest(e => events.push(e)));
+
+		await service.request({ url: 'http://test', callSite: NO_FETCH_TELEMETRY }, CancellationToken.None);
+
+		assert.strictEqual(events.length, 1);
+		assert.strictEqual(events[0].callSite, NO_FETCH_TELEMETRY);
+	});
+
+	test('onDidCompleteRequest does not fire when request throws', async () => {
+		const service = store.add(new TestRequestService(() => Promise.reject(new Error('network error'))));
+
+		const events: IRequestCompleteEvent[] = [];
+		store.add(service.onDidCompleteRequest(e => events.push(e)));
+
+		await assert.rejects(() => service.request({ url: 'http://test', callSite: 'test.error' }, CancellationToken.None));
+
+		assert.strictEqual(events.length, 0);
+	});
+
+	test('onDidCompleteRequest fires for each request', async () => {
+		const service = store.add(new TestRequestService(() => Promise.resolve(makeResponse(200))));
+
+		const events: IRequestCompleteEvent[] = [];
+		store.add(service.onDidCompleteRequest(e => events.push(e)));
+
+		await service.request({ url: 'http://test/1', callSite: 'first' }, CancellationToken.None);
+		await service.request({ url: 'http://test/2', callSite: 'second' }, CancellationToken.None);
+
+		assert.deepStrictEqual(events.map(e => e.callSite), ['first', 'second']);
+	});
+});
diff --git a/src/vs/platform/request/test/node/requestService.test.ts b/src/vs/platform/request/test/node/requestService.test.ts
index 8e8c885014921..50f7d72068ab9 100644
--- a/src/vs/platform/request/test/node/requestService.test.ts
+++ b/src/vs/platform/request/test/node/requestService.test.ts
@@ -36,7 +36,7 @@ suite('Request Service', () => {
 		setTimeout(() => cts.cancel(), 50);
 
 		try {
-			await nodeRequest({ url: 'http://localhost:9999/nonexistent' }, cts.token);
+			await nodeRequest({ url: 'http://localhost:9999/nonexistent', callSite: 'requestService.test.cancellation' }, cts.token);
 			assert.fail('Request should have been cancelled');
 		} catch (err) {
 			const elapsed = Date.now() - startTime;
@@ -74,7 +74,8 @@ suite('Request Service', () => {
 			await nodeRequest({
 				url: 'http://example.com',
 				type: 'GET',
-				getRawRequest: () => mockRawRequest as IRawRequestFunction
+				getRawRequest: () => mockRawRequest as IRawRequestFunction,
+				callSite: 'requestService.test.retryGET'
 			}, CancellationToken.None);
 		} catch (err) {
 			// Expected to eventually succeed or fail after retries
@@ -106,7 +107,8 @@ suite('Request Service', () => {
 			await nodeRequest({
 				url: 'http://example.com',
 				type: 'POST',
-				getRawRequest: () => mockRawRequest
+				getRawRequest: () => mockRawRequest,
+				callSite: 'requestService.test.noRetryPOST'
 			}, CancellationToken.None);
 			assert.fail('Should have thrown an error');
 		} catch (err) {
@@ -144,7 +146,8 @@ suite('Request Service', () => {
 			await nodeRequest({
 				url: 'http://example.com',
 				type: 'HEAD',
-				getRawRequest: () => mockRawRequest as IRawRequestFunction
+				getRawRequest: () => mockRawRequest as IRawRequestFunction,
+				callSite: 'requestService.test.retryHEAD'
 			}, CancellationToken.None);
 		} catch (err) {
 			// Expected to eventually succeed or fail after retries
@@ -181,7 +184,8 @@ suite('Request Service', () => {
 			await nodeRequest({
 				url: 'http://example.com',
 				type: 'OPTIONS',
-				getRawRequest: () => mockRawRequest as IRawRequestFunction
+				getRawRequest: () => mockRawRequest as IRawRequestFunction,
+				callSite: 'requestService.test.retryOPTIONS'
 			}, CancellationToken.None);
 		} catch (err) {
 			// Expected to eventually succeed or fail after retries
@@ -213,7 +217,8 @@ suite('Request Service', () => {
 			await nodeRequest({
 				url: 'http://example.com',
 				type: 'DELETE',
-				getRawRequest: () => mockRawRequest
+				getRawRequest: () => mockRawRequest,
+				callSite: 'requestService.test.noRetryDELETE'
 			}, CancellationToken.None);
 			assert.fail('Should have thrown an error');
 		} catch (err) {
@@ -246,7 +251,8 @@ suite('Request Service', () => {
 			await nodeRequest({
 				url: 'http://example.com',
 				type: 'PUT',
-				getRawRequest: () => mockRawRequest
+				getRawRequest: () => mockRawRequest,
+				callSite: 'requestService.test.noRetryPUT'
 			}, CancellationToken.None);
 			assert.fail('Should have thrown an error');
 		} catch (err) {
@@ -279,7 +285,8 @@ suite('Request Service', () => {
 			await nodeRequest({
 				url: 'http://example.com',
 				type: 'PATCH',
-				getRawRequest: () => mockRawRequest
+				getRawRequest: () => mockRawRequest,
+				callSite: 'requestService.test.noRetryPATCH'
 			}, CancellationToken.None);
 			assert.fail('Should have thrown an error');
 		} catch (err) {
diff --git a/src/vs/platform/sandbox/common/sandboxHelperIpc.ts b/src/vs/platform/sandbox/common/sandboxHelperIpc.ts
new file mode 100644
index 0000000000000..bbcdf499df193
--- /dev/null
+++ b/src/vs/platform/sandbox/common/sandboxHelperIpc.ts
@@ -0,0 +1,45 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+export const SandboxHelperChannelName = 'SandboxHelper';
+
+export interface ISandboxNetworkHostPattern {
+	readonly host: string;
+	readonly port: number | undefined;
+}
+
+export interface ISandboxNetworkConfig {
+	readonly allowedDomains?: string[];
+	readonly deniedDomains?: string[];
+	readonly allowUnixSockets?: string[];
+	readonly allowAllUnixSockets?: boolean;
+	readonly allowLocalBinding?: boolean;
+	readonly httpProxyPort?: number;
+	readonly socksProxyPort?: number;
+}
+
+export interface ISandboxFilesystemConfig {
+	readonly denyRead?: string[];
+	readonly allowWrite?: string[];
+	readonly denyWrite?: string[];
+	readonly allowGitConfig?: boolean;
+}
+
+export interface ISandboxRuntimeConfig {
+	readonly network?: ISandboxNetworkConfig;
+	readonly filesystem?: ISandboxFilesystemConfig;
+	readonly ignoreViolations?: Record<string, string[]>;
+	readonly enableWeakerNestedSandbox?: boolean;
+	readonly ripgrep?: {
+		readonly command: string;
+		readonly args?: string[];
+	};
+	readonly mandatoryDenySearchDepth?: number;
+	readonly allowPty?: boolean;
+}
+
+export interface ISandboxPermissionRequest extends ISandboxNetworkHostPattern {
+	readonly requestId: string;
+}
diff --git a/src/vs/platform/sandbox/common/sandboxHelperService.ts b/src/vs/platform/sandbox/common/sandboxHelperService.ts
new file mode 100644
index 0000000000000..4556c74bc546e
--- /dev/null
+++ b/src/vs/platform/sandbox/common/sandboxHelperService.ts
@@ -0,0 +1,19 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Event } from '../../../base/common/event.js';
+import { createDecorator } from '../../instantiation/common/instantiation.js';
+import { type ISandboxPermissionRequest, type ISandboxRuntimeConfig } from './sandboxHelperIpc.js';
+
+export const ISandboxHelperService = createDecorator<ISandboxHelperService>('ISandboxHelperService');
+
+export interface ISandboxHelperService {
+	readonly _serviceBrand: undefined;
+	readonly onDidRequestSandboxPermission: Event<ISandboxPermissionRequest>;
+
+	resetSandbox(): Promise<void>;
+	resolveSandboxPermissionRequest(requestId: string, allowed: boolean): Promise<void>;
+	wrapWithSandbox(runtimeConfig: ISandboxRuntimeConfig, command: string): Promise<string>;
+}
diff --git a/extensions/github-authentication/extension.webpack.config.js b/src/vs/platform/sandbox/electron-browser/sandboxHelperService.ts
similarity index 52%
rename from extensions/github-authentication/extension.webpack.config.js
rename to src/vs/platform/sandbox/electron-browser/sandboxHelperService.ts
index 166c1d8b1e340..19778b5bf4bc6 100644
--- a/extensions/github-authentication/extension.webpack.config.js
+++ b/src/vs/platform/sandbox/electron-browser/sandboxHelperService.ts
@@ -2,12 +2,9 @@
  *  Copyright (c) Microsoft Corporation. All rights reserved.
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
-// @ts-check
-import withDefaults from '../shared.webpack.config.mjs';
 
-export default withDefaults({
-	context: import.meta.dirname,
-	entry: {
-		extension: './src/extension.ts',
-	},
-});
+import { registerMainProcessRemoteService } from '../../ipc/electron-browser/services.js';
+import { SandboxHelperChannelName } from '../common/sandboxHelperIpc.js';
+import { ISandboxHelperService } from '../common/sandboxHelperService.js';
+
+registerMainProcessRemoteService(ISandboxHelperService, SandboxHelperChannelName);
diff --git a/src/vs/platform/sandbox/node/sandboxHelperChannel.ts b/src/vs/platform/sandbox/node/sandboxHelperChannel.ts
new file mode 100644
index 0000000000000..9b861b011e954
--- /dev/null
+++ b/src/vs/platform/sandbox/node/sandboxHelperChannel.ts
@@ -0,0 +1,44 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Event } from '../../../base/common/event.js';
+import { IServerChannel } from '../../../base/parts/ipc/common/ipc.js';
+import { RemoteAgentConnectionContext } from '../../remote/common/remoteAgentEnvironment.js';
+import { type ISandboxRuntimeConfig } from '../common/sandboxHelperIpc.js';
+import { ISandboxHelperService } from '../common/sandboxHelperService.js';
+
+export class SandboxHelperChannel implements IServerChannel<RemoteAgentConnectionContext> {
+
+	constructor(
+		@ISandboxHelperService private readonly sandboxHelperService: ISandboxHelperService
+	) { }
+
+	listen<T>(context: RemoteAgentConnectionContext, event: string): Event<T> {
+		switch (event) {
+			case 'onDidRequestSandboxPermission': {
+				return this.sandboxHelperService.onDidRequestSandboxPermission as Event<T>;
+			}
+		}
+
+		throw new Error('Invalid listen');
+	}
+
+	async call<T>(context: RemoteAgentConnectionContext, command: string, args?: unknown): Promise<T> {
+		const argsArray = Array.isArray(args) ? args : [];
+		switch (command) {
+			case 'resetSandbox': {
+				return this.sandboxHelperService.resetSandbox() as T;
+			}
+			case 'resolveSandboxPermissionRequest': {
+				return this.sandboxHelperService.resolveSandboxPermissionRequest(argsArray[0] as string, argsArray[1] as boolean) as T;
+			}
+			case 'wrapWithSandbox': {
+				return this.sandboxHelperService.wrapWithSandbox(argsArray[0] as ISandboxRuntimeConfig, argsArray[1] as string) as T;
+			}
+		}
+
+		throw new Error('Invalid call');
+	}
+}
diff --git a/src/vs/platform/sandbox/node/sandboxHelperService.ts b/src/vs/platform/sandbox/node/sandboxHelperService.ts
new file mode 100644
index 0000000000000..90ba6e217d7ab
--- /dev/null
+++ b/src/vs/platform/sandbox/node/sandboxHelperService.ts
@@ -0,0 +1,128 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { SandboxManager, type NetworkHostPattern } from '@anthropic-ai/sandbox-runtime';
+import { Emitter } from '../../../base/common/event.js';
+import { Disposable } from '../../../base/common/lifecycle.js';
+import { dirname, posix, win32 } from '../../../base/common/path.js';
+import { generateUuid } from '../../../base/common/uuid.js';
+import { IEnvironmentService, INativeEnvironmentService } from '../../environment/common/environment.js';
+import { type ISandboxPermissionRequest, type ISandboxRuntimeConfig } from '../common/sandboxHelperIpc.js';
+import { ISandboxHelperService } from '../common/sandboxHelperService.js';
+
+export class SandboxHelperService extends Disposable implements ISandboxHelperService {
+	declare readonly _serviceBrand: undefined;
+	private readonly _onDidRequestSandboxPermission = this._register(new Emitter<ISandboxPermissionRequest>());
+	readonly onDidRequestSandboxPermission = this._onDidRequestSandboxPermission.event;
+	private readonly _pendingPermissionRequests = new Map<string, (allowed: boolean) => void>();
+	private readonly _rgPath: string | undefined;
+	private readonly _tempDir: string | undefined;
+
+	constructor(
+		@IEnvironmentService environmentService: IEnvironmentService,
+	) {
+		super();
+		const nativeEnvironmentService = environmentService as IEnvironmentService & Partial<INativeEnvironmentService>;
+		this._rgPath = nativeEnvironmentService.appRoot
+			? this._pathJoin(nativeEnvironmentService.appRoot, 'node_modules', '@vscode', 'ripgrep', 'bin', 'rg')
+			: undefined;
+		this._tempDir = nativeEnvironmentService.tmpDir?.path;
+	}
+
+	async resolveSandboxPermissionRequest(requestId: string, allowed: boolean): Promise<void> {
+		const resolver = this._pendingPermissionRequests.get(requestId);
+		if (!resolver) {
+			throw new Error(`No pending sandbox permission request with id ${requestId}`);
+		}
+		this._pendingPermissionRequests.delete(requestId);
+		resolver(allowed);
+	}
+
+	async resetSandbox(): Promise<void> {
+		await SandboxManager.reset();
+	}
+
+	async wrapWithSandbox(runtimeConfig: ISandboxRuntimeConfig, command: string): Promise<string> {
+		const normalizedRuntimeConfig = {
+			network: {
+				// adding at least one domain or else the sandbox doesnt do any proxy setup.
+				allowedDomains: runtimeConfig.network?.allowedDomains?.length ? [...runtimeConfig.network.allowedDomains] : ['microsoft.com'],
+				deniedDomains: [...(runtimeConfig.network?.deniedDomains ?? [])],
+				allowUnixSockets: runtimeConfig.network?.allowUnixSockets ? [...runtimeConfig.network.allowUnixSockets] : undefined,
+				allowAllUnixSockets: runtimeConfig.network?.allowAllUnixSockets,
+				allowLocalBinding: runtimeConfig.network?.allowLocalBinding,
+				httpProxyPort: runtimeConfig.network?.httpProxyPort,
+				socksProxyPort: runtimeConfig.network?.socksProxyPort,
+			},
+			filesystem: {
+				denyRead: [...(runtimeConfig.filesystem?.denyRead ?? [])],
+				allowWrite: [
+					...(runtimeConfig.filesystem?.allowWrite ?? []),
+					...(this._tempDir ? [this._tempDir] : []),
+				],
+				denyWrite: [...(runtimeConfig.filesystem?.denyWrite ?? [])],
+				allowGitConfig: runtimeConfig.filesystem?.allowGitConfig,
+			},
+			ignoreViolations: runtimeConfig.ignoreViolations,
+			enableWeakerNestedSandbox: runtimeConfig.enableWeakerNestedSandbox,
+			ripgrep: runtimeConfig.ripgrep ? {
+				command: runtimeConfig.ripgrep.command,
+				args: runtimeConfig.ripgrep.args ? [...runtimeConfig.ripgrep.args] : undefined,
+			} : undefined,
+			mandatoryDenySearchDepth: runtimeConfig.mandatoryDenySearchDepth,
+			allowPty: runtimeConfig.allowPty,
+		};
+		await SandboxManager.initialize(normalizedRuntimeConfig, request => this._requestSandboxPermission(request));
+		return SandboxManager.wrapWithSandbox(`${this._getSandboxEnvironmentPrefix()} ${command}`);
+	}
+
+	private _getSandboxEnvironmentPrefix(): string {
+		const env: string[] = ['NODE_USE_ENV_PROXY=1'];
+
+		if (this._tempDir) {
+			env.push(this._toEnvironmentAssignment('TMPDIR', this._tempDir));
+		}
+
+		const pathWithRipgrep = this._getPathWithRipgrepDir();
+		if (pathWithRipgrep) {
+			env.push(this._toEnvironmentAssignment('PATH', pathWithRipgrep));
+		}
+
+		return env.join(' ');
+	}
+
+	private _getPathWithRipgrepDir(): string | undefined {
+		if (!this._rgPath) {
+			return undefined;
+		}
+		const rgDir = dirname(this._rgPath);
+		const currentPath = process.env['PATH'];
+		const pathModule = process.platform === 'win32' ? win32 : posix;
+		const delimiter = pathModule.delimiter;
+		return currentPath ? `${currentPath}${delimiter}${rgDir}` : rgDir;
+	}
+
+	private _toEnvironmentAssignment(name: string, value: string): string {
+		return `${name}="${value}"`;
+	}
+
+	private _pathJoin(...segments: string[]): string {
+		const path = process.platform === 'win32' ? win32 : posix;
+		return path.join(...segments);
+	}
+
+	private _requestSandboxPermission(request: NetworkHostPattern): Promise<boolean> {
+		const requestId = generateUuid();
+
+		return new Promise<boolean>(resolve => {
+			this._pendingPermissionRequests.set(requestId, resolve);
+			this._onDidRequestSandboxPermission.fire({
+				requestId,
+				host: request.host,
+				port: request.port,
+			});
+		});
+	}
+}
diff --git a/src/vs/platform/telemetry/common/telemetryUtils.ts b/src/vs/platform/telemetry/common/telemetryUtils.ts
index 7c5c89eae0886..d1acea8ff5ddc 100644
--- a/src/vs/platform/telemetry/common/telemetryUtils.ts
+++ b/src/vs/platform/telemetry/common/telemetryUtils.ts
@@ -309,13 +309,14 @@ function anonymizeFilePaths(stack: string, cleanupPatterns: RegExp[]): string {
 		}
 	}
 
-	const nodeModulesRegex = /^[\\\/]?(node_modules|node_modules\.asar)[\\\/]/;
+	// Match node_modules or node_modules.asar at any position in the path, capturing the node_modules/... suffix
+	const nodeModulesRegex = /(?:^|[\\\/])((node_modules|node_modules\.asar)[\\\/].*)$/;
 	// Match VS Code extension paths:
 	// 1. User extensions: .vscode/extensions/, .vscode-insiders/extensions/, .vscode-server/extensions/, .vscode-server-insiders/extensions/, etc.
 	// 2. Built-in extensions: resources/app/extensions/
 	// Capture everything from the vscode folder or resources/app/extensions onwards
 	const vscodeExtensionsPathRegex = /^(.*?)((?:\.vscode(?:-[a-z]+)*|resources[\\\/]app)[\\\/]extensions[\\\/].*)$/i;
-	const fileRegex = /(file:\/\/)?([a-zA-Z]:(\\\\|\\|\/)|(\\\\|\\|\/))?([\w-\._]+(\\\\|\\|\/))+[\w-\._]*/g;
+	const fileRegex = /(file:\/\/)?([a-zA-Z]:(\\\\|\\|\/)|(\\\\|\\|\/))?([\w\-\._@]+(\\\\|\\|\/))+[\w\-\._@]*/g;
 	let lastIndex = 0;
 	updatedStack = '';
 
@@ -329,14 +330,20 @@ function anonymizeFilePaths(stack: string, cleanupPatterns: RegExp[]): string {
 		const overlappingRange = cleanUpIndexes.some(([start, end]) => result.index < end && start < fileRegex.lastIndex);
 
 		// anoynimize user file paths that do not need to be retained or cleaned up.
-		if (!nodeModulesRegex.test(result[0]) && !overlappingRange) {
+		if (!overlappingRange) {
 			// Check if this is a VS Code extension path - if so, preserve the .vscode*/extensions/... portion
 			const vscodeExtMatch = vscodeExtensionsPathRegex.exec(result[0]);
 			if (vscodeExtMatch) {
 				// Keep ".vscode[-variant]/extensions/extension-name/..." but redact the parent folder
 				updatedStack += stack.substring(lastIndex, result.index) + '<REDACTED: user-file-path>/' + vscodeExtMatch[2];
 			} else {
-				updatedStack += stack.substring(lastIndex, result.index) + '<REDACTED: user-file-path>';
+				// Check if node_modules appears in the path — preserve node_modules/... suffix
+				const nodeModulesMatch = nodeModulesRegex.exec(result[0]);
+				if (nodeModulesMatch) {
+					updatedStack += stack.substring(lastIndex, result.index) + '<REDACTED: user-file-path>/' + nodeModulesMatch[1];
+				} else {
+					updatedStack += stack.substring(lastIndex, result.index) + '<REDACTED: user-file-path>';
+				}
 			}
 			lastIndex = fileRegex.lastIndex;
 		}
diff --git a/src/vs/platform/telemetry/node/1dsAppender.ts b/src/vs/platform/telemetry/node/1dsAppender.ts
index 0d3f9369eb56c..0fdbbd1a73257 100644
--- a/src/vs/platform/telemetry/node/1dsAppender.ts
+++ b/src/vs/platform/telemetry/node/1dsAppender.ts
@@ -7,7 +7,7 @@ import type { IPayloadData, IXHROverride } from '@microsoft/1ds-post-js';
 import { streamToBuffer } from '../../../base/common/buffer.js';
 import { CancellationToken } from '../../../base/common/cancellation.js';
 import { IRequestOptions } from '../../../base/parts/request/common/request.js';
-import { IRequestService } from '../../request/common/request.js';
+import { IRequestService, NO_FETCH_TELEMETRY } from '../../request/common/request.js';
 import { AbstractOneDataSystemAppender, IAppInsightsCore } from '../common/1dsAppender.js';
 
 type OnCompleteFunc = (status: number, headers: { [headerName: string]: string }, response?: string) => void;
@@ -81,7 +81,8 @@ async function sendPostAsync(requestService: IRequestService | undefined, payloa
 			'Content-Length': Buffer.byteLength(payload.data).toString()
 		},
 		url: payload.urlString,
-		data: telemetryRequestData
+		data: telemetryRequestData,
+		callSite: NO_FETCH_TELEMETRY
 	};
 
 	try {
diff --git a/src/vs/platform/telemetry/test/browser/telemetryService.test.ts b/src/vs/platform/telemetry/test/browser/telemetryService.test.ts
index d6a1b2370d511..dff2debea1131 100644
--- a/src/vs/platform/telemetry/test/browser/telemetryService.test.ts
+++ b/src/vs/platform/telemetry/test/browser/telemetryService.test.ts
@@ -57,7 +57,13 @@ class ErrorTestingSettings {
 	public randomUserFile: string = 'a/path/that/doe_snt/con-tain/code/names.js';
 	public anonymizedRandomUserFile: string = '<REDACTED: user-file-path>';
 	public nodeModulePathToRetain: string = 'node_modules/path/that/shouldbe/retained/names.js:14:15854';
+	public anonymizedNodeModulePath: string = '<REDACTED: user-file-path>/node_modules/path/that/shouldbe/retained/names.js:14:15854';
 	public nodeModuleAsarPathToRetain: string = 'node_modules.asar/path/that/shouldbe/retained/names.js:14:12354';
+	public anonymizedNodeModuleAsarPath: string = '<REDACTED: user-file-path>/node_modules.asar/path/that/shouldbe/retained/names.js:14:12354';
+	public fullNodeModulePath: string = '/Users/username/projects/vscode/node_modules/@xterm/xterm/lib/xterm.js:1:243732';
+	public anonymizedFullNodeModulePath: string = '<REDACTED: user-file-path>/node_modules/@xterm/xterm/lib/xterm.js:1:243732';
+	public fullNodeModuleAsarPath: string = '/Users/username/projects/vscode/node_modules.asar/@xterm/xterm/lib/xterm.js:1:376066';
+	public anonymizedFullNodeModuleAsarPath: string = '<REDACTED: user-file-path>/node_modules.asar/@xterm/xterm/lib/xterm.js:1:376066';
 	public extensionPathToRetain: string = '.vscode/extensions/ms-python.python-2024.0.1/out/extension.js:144:145516';
 	public fullExtensionPath: string = '/Users/username/.vscode/extensions/ms-python.python-2024.0.1/out/extension.js:144:145516';
 	public anonymizedExtensionPath: string = '<REDACTED: user-file-path>/.vscode/extensions/ms-python.python-2024.0.1/out/extension.js:144:145516';
@@ -90,6 +96,8 @@ class ErrorTestingSettings {
 		`    at t._handleMessage (${this.nodeModuleAsarPathToRetain})`,
 		`    at t._onmessage (/${this.nodeModulePathToRetain})`,
 		`    at t.onmessage (${this.nodeModulePathToRetain})`,
+		`    at get dimensions (${this.fullNodeModulePath})`,
+		`    at _._refreshCanvasDimensions (${this.fullNodeModuleAsarPath})`,
 		`    at uv.provideCodeActions (${this.fullExtensionPath})`,
 		`    at remote.handleConnection (${this.fullServerInsidersExtensionPath})`,
 		`    at git.getRepositoryState (${this.fullBuiltinExtensionPath})`,
@@ -468,10 +476,8 @@ suite('TelemetryService', () => {
 
 		assert.strictEqual(errorStub.callCount, 1);
 		// Test that important information remains but personal info does not
-		assert.notStrictEqual(testAppender.events[0].data.callstack.indexOf('(' + settings.nodeModuleAsarPathToRetain), -1);
-		assert.notStrictEqual(testAppender.events[0].data.callstack.indexOf('(' + settings.nodeModulePathToRetain), -1);
-		assert.notStrictEqual(testAppender.events[0].data.callstack.indexOf('(/' + settings.nodeModuleAsarPathToRetain), -1);
-		assert.notStrictEqual(testAppender.events[0].data.callstack.indexOf('(/' + settings.nodeModulePathToRetain), -1);
+		assert.notStrictEqual(testAppender.events[0].data.callstack.indexOf(settings.anonymizedNodeModuleAsarPath), -1, 'bare node_modules.asar path');
+		assert.notStrictEqual(testAppender.events[0].data.callstack.indexOf(settings.anonymizedNodeModulePath), -1, 'bare node_modules path');
 		assert.notStrictEqual(testAppender.events[0].data.msg.indexOf(settings.importantInfo), -1);
 		assert.strictEqual(testAppender.events[0].data.msg.indexOf(settings.personalInfo), -1);
 		assert.strictEqual(testAppender.events[0].data.msg.indexOf(settings.filePrefix), -1);
@@ -504,10 +510,12 @@ suite('TelemetryService', () => {
 			Errors.onUnexpectedError(dangerousPathWithImportantInfoError);
 			this.clock.tick(ErrorTelemetry.ERROR_FLUSH_TIMEOUT);
 
-			assert.notStrictEqual(testAppender.events[0].data.callstack.indexOf('(' + settings.nodeModuleAsarPathToRetain), -1);
-			assert.notStrictEqual(testAppender.events[0].data.callstack.indexOf('(' + settings.nodeModulePathToRetain), -1);
-			assert.notStrictEqual(testAppender.events[0].data.callstack.indexOf('(/' + settings.nodeModuleAsarPathToRetain), -1);
-			assert.notStrictEqual(testAppender.events[0].data.callstack.indexOf('(/' + settings.nodeModulePathToRetain), -1);
+			// All node_modules paths (bare and full) should preserve the node_modules/... suffix after redaction
+			const cs = testAppender.events[0].data.callstack;
+			assert.notStrictEqual(cs.indexOf(settings.anonymizedNodeModuleAsarPath), -1, 'bare node_modules.asar path');
+			assert.notStrictEqual(cs.indexOf(settings.anonymizedNodeModulePath), -1, 'bare node_modules path');
+			assert.notStrictEqual(cs.indexOf(settings.anonymizedFullNodeModulePath), -1, 'full node_modules path');
+			assert.notStrictEqual(cs.indexOf(settings.anonymizedFullNodeModuleAsarPath), -1, 'full node_modules.asar path');
 
 			errorTelemetry.dispose();
 			service.dispose();
diff --git a/src/vs/platform/terminal/common/terminal.ts b/src/vs/platform/terminal/common/terminal.ts
index dc7c596c346ca..44e53e09a6449 100644
--- a/src/vs/platform/terminal/common/terminal.ts
+++ b/src/vs/platform/terminal/common/terminal.ts
@@ -122,6 +122,7 @@ export const enum TerminalSettingId {
 	FontLigaturesFallbackLigatures = 'terminal.integrated.fontLigatures.fallbackLigatures',
 	EnableKittyKeyboardProtocol = 'terminal.integrated.enableKittyKeyboardProtocol',
 	EnableWin32InputMode = 'terminal.integrated.enableWin32InputMode',
+	ExperimentalAiProfileGrouping = 'terminal.integrated.experimental.aiProfileGrouping',
 	AllowInUntrustedWorkspace = 'terminal.integrated.allowInUntrustedWorkspace',
 
 	// Developer/debug settings
diff --git a/src/vs/platform/terminal/node/terminalEnvironment.ts b/src/vs/platform/terminal/node/terminalEnvironment.ts
index 5aa0a0dd13a6e..178bed35e83c2 100644
--- a/src/vs/platform/terminal/node/terminalEnvironment.ts
+++ b/src/vs/platform/terminal/node/terminalEnvironment.ts
@@ -118,6 +118,7 @@ export async function getShellIntegrationInjection(
 			if (!newArgs) {
 				return { type: 'failure', reason: ShellIntegrationInjectionFailureReason.UnsupportedArgs };
 			}
+			newArgs = [...newArgs];
 			newArgs[newArgs.length - 1] = format(newArgs[newArgs.length - 1], appRoot, '');
 			envMixin['VSCODE_STABLE'] = productService.quality === 'stable' ? '1' : '0';
 			return { type, newArgs, envMixin };
diff --git a/src/vs/platform/theme/browser/defaultStyles.ts b/src/vs/platform/theme/browser/defaultStyles.ts
index 49e08fbf8dab6..bd8147af0d4ac 100644
--- a/src/vs/platform/theme/browser/defaultStyles.ts
+++ b/src/vs/platform/theme/browser/defaultStyles.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 import { IButtonStyles } from '../../../base/browser/ui/button/button.js';
 import { IKeybindingLabelStyles } from '../../../base/browser/ui/keybindingLabel/keybindingLabel.js';
-import { ColorIdentifier, keybindingLabelBackground, keybindingLabelBorder, keybindingLabelBottomBorder, keybindingLabelForeground, asCssVariable, widgetShadow, buttonForeground, buttonSeparator, buttonBackground, buttonHoverBackground, buttonSecondaryForeground, buttonSecondaryBackground, buttonSecondaryHoverBackground, buttonBorder, progressBarBackground, inputActiveOptionBorder, inputActiveOptionForeground, inputActiveOptionBackground, editorWidgetBackground, editorWidgetForeground, contrastBorder, checkboxBorder, checkboxBackground, checkboxForeground, problemsErrorIconForeground, problemsWarningIconForeground, problemsInfoIconForeground, inputBackground, inputForeground, inputBorder, textLinkForeground, inputValidationInfoBorder, inputValidationInfoBackground, inputValidationInfoForeground, inputValidationWarningBorder, inputValidationWarningBackground, inputValidationWarningForeground, inputValidationErrorBorder, inputValidationErrorBackground, inputValidationErrorForeground, listFilterWidgetBackground, listFilterWidgetNoMatchesOutline, listFilterWidgetOutline, listFilterWidgetShadow, badgeBackground, badgeForeground, breadcrumbsBackground, breadcrumbsForeground, breadcrumbsFocusForeground, breadcrumbsActiveSelectionForeground, activeContrastBorder, listActiveSelectionBackground, listActiveSelectionForeground, listActiveSelectionIconForeground, listDropOverBackground, listFocusAndSelectionOutline, listFocusBackground, listFocusForeground, listFocusOutline, listHoverBackground, listHoverForeground, listInactiveFocusBackground, listInactiveFocusOutline, listInactiveSelectionBackground, listInactiveSelectionForeground, listInactiveSelectionIconForeground, tableColumnsBorder, tableOddRowsBackgroundColor, treeIndentGuidesStroke, asCssVariableWithDefault, editorWidgetBorder, focusBorder, pickerGroupForeground, quickInputListFocusBackground, quickInputListFocusForeground, quickInputListFocusIconForeground, selectBackground, selectBorder, selectForeground, selectListBackground, treeInactiveIndentGuidesStroke, menuBorder, menuForeground, menuBackground, menuSelectionForeground, menuSelectionBackground, menuSelectionBorder, menuSeparatorBackground, scrollbarShadow, scrollbarSliderActiveBackground, scrollbarSliderBackground, scrollbarSliderHoverBackground, listDropBetweenBackground, radioActiveBackground, radioActiveForeground, radioInactiveBackground, radioInactiveForeground, radioInactiveBorder, radioInactiveHoverBackground, radioActiveBorder, checkboxDisabledBackground, checkboxDisabledForeground, widgetBorder } from '../common/colorRegistry.js';
+import { ColorIdentifier, keybindingLabelBackground, keybindingLabelBorder, keybindingLabelBottomBorder, keybindingLabelForeground, asCssVariable, widgetShadow, buttonForeground, buttonSeparator, buttonBackground, buttonHoverBackground, buttonSecondaryForeground, buttonSecondaryBackground, buttonSecondaryHoverBackground, buttonBorder, progressBarBackground, inputActiveOptionBorder, inputActiveOptionForeground, inputActiveOptionBackground, editorWidgetBackground, editorWidgetForeground, contrastBorder, checkboxBorder, checkboxBackground, checkboxForeground, problemsErrorIconForeground, problemsWarningIconForeground, problemsInfoIconForeground, inputBackground, inputForeground, inputBorder, textLinkForeground, inputValidationInfoBorder, inputValidationInfoBackground, inputValidationInfoForeground, inputValidationWarningBorder, inputValidationWarningBackground, inputValidationWarningForeground, inputValidationErrorBorder, inputValidationErrorBackground, inputValidationErrorForeground, listFilterWidgetBackground, listFilterWidgetNoMatchesOutline, listFilterWidgetOutline, listFilterWidgetShadow, badgeBackground, badgeForeground, breadcrumbsBackground, breadcrumbsForeground, breadcrumbsFocusForeground, breadcrumbsActiveSelectionForeground, activeContrastBorder, listActiveSelectionBackground, listActiveSelectionForeground, listActiveSelectionIconForeground, listDropOverBackground, listFocusAndSelectionOutline, listFocusBackground, listFocusForeground, listFocusOutline, listHoverBackground, listHoverForeground, listInactiveFocusBackground, listInactiveFocusOutline, listInactiveSelectionBackground, listInactiveSelectionForeground, listInactiveSelectionIconForeground, tableColumnsBorder, tableOddRowsBackgroundColor, treeIndentGuidesStroke, asCssVariableWithDefault, editorWidgetBorder, focusBorder, pickerGroupForeground, quickInputListFocusBackground, quickInputListFocusForeground, quickInputListFocusIconForeground, selectBackground, selectBorder, selectForeground, selectListBackground, treeInactiveIndentGuidesStroke, menuBorder, menuForeground, menuBackground, menuSelectionBorder, menuSeparatorBackground, scrollbarShadow, scrollbarSliderActiveBackground, scrollbarSliderBackground, scrollbarSliderHoverBackground, listDropBetweenBackground, radioActiveBackground, radioActiveForeground, radioInactiveBackground, radioInactiveForeground, radioInactiveBorder, radioInactiveHoverBackground, radioActiveBorder, checkboxDisabledBackground, checkboxDisabledForeground, widgetBorder } from '../common/colorRegistry.js';
 import { IProgressBarStyles } from '../../../base/browser/ui/progressbar/progressbar.js';
 import { ICheckboxStyles, IToggleStyles } from '../../../base/browser/ui/toggle/toggle.js';
 import { IDialogStyles } from '../../../base/browser/ui/dialog/dialog.js';
@@ -244,8 +244,8 @@ export const defaultMenuStyles: IMenuStyles = {
 	borderColor: asCssVariable(menuBorder),
 	foregroundColor: asCssVariable(menuForeground),
 	backgroundColor: asCssVariable(menuBackground),
-	selectionForegroundColor: asCssVariable(menuSelectionForeground),
-	selectionBackgroundColor: asCssVariable(menuSelectionBackground),
+	selectionForegroundColor: asCssVariable(listHoverForeground),
+	selectionBackgroundColor: asCssVariable(listHoverBackground),
 	selectionBorderColor: asCssVariable(menuSelectionBorder),
 	separatorColor: asCssVariable(menuSeparatorBackground),
 	scrollbarShadow: asCssVariable(scrollbarShadow),
diff --git a/src/vs/platform/update/common/update.config.contribution.ts b/src/vs/platform/update/common/update.config.contribution.ts
index 93dd62df97ec6..53e3a783872ff 100644
--- a/src/vs/platform/update/common/update.config.contribution.ts
+++ b/src/vs/platform/update/common/update.config.contribution.ts
@@ -7,6 +7,7 @@ import { isWeb, isWindows } from '../../../base/common/platform.js';
 import { PolicyCategory } from '../../../base/common/policy.js';
 import { localize } from '../../../nls.js';
 import { ConfigurationScope, Extensions as ConfigurationExtensions, IConfigurationRegistry } from '../../configuration/common/configurationRegistry.js';
+import product from '../../product/common/product.js';
 import { Registry } from '../../registry/common/platform.js';
 
 const configurationRegistry = Registry.as<IConfigurationRegistry>(ConfigurationExtensions.Configuration);
@@ -89,6 +90,21 @@ configurationRegistry.registerConfiguration({
 				localize('actionable', "The status bar entry is shown when an action is required (e.g., download, install, or restart)."),
 				localize('detailed', "The status bar entry is shown for all update states including progress.")
 			]
+		},
+		'update.titleBar': {
+			type: 'string',
+			enum: ['none', 'actionable', 'detailed', 'always'],
+			default: product.quality !== 'stable' ? 'actionable' : 'none',
+			scope: ConfigurationScope.APPLICATION,
+			tags: ['experimental'],
+			experiment: { mode: 'startup' },
+			description: localize('titleBar', "Controls the experimental update title bar entry."),
+			enumDescriptions: [
+				localize('titleBarNone', "The title bar entry is never shown."),
+				localize('titleBarActionable', "The title bar entry is shown when an action is required (e.g., download, install, or restart)."),
+				localize('titleBarDetailed', "The title bar entry is shown for progress and actionable update states, but not for idle or disabled states."),
+				localize('titleBarAlways', "The title bar entry is shown for all update states.")
+			]
 		}
 	}
 });
diff --git a/src/vs/platform/update/common/update.ts b/src/vs/platform/update/common/update.ts
index 7f30494da4a37..bc90a03ad8c78 100644
--- a/src/vs/platform/update/common/update.ts
+++ b/src/vs/platform/update/common/update.ts
@@ -59,17 +59,17 @@ export const enum DisablementReason {
 	NotBuilt,
 	DisabledByEnvironment,
 	ManuallyDisabled,
+	Policy,
 	MissingConfiguration,
 	InvalidConfiguration,
 	RunningAsAdmin,
-	EmbeddedApp,
 }
 
 export type Uninitialized = { type: StateType.Uninitialized };
 export type Disabled = { type: StateType.Disabled; reason: DisablementReason };
-export type Idle = { type: StateType.Idle; updateType: UpdateType; error?: string };
+export type Idle = { type: StateType.Idle; updateType: UpdateType; error?: string; notAvailable?: boolean };
 export type CheckingForUpdates = { type: StateType.CheckingForUpdates; explicit: boolean };
-export type AvailableForDownload = { type: StateType.AvailableForDownload; update: IUpdate };
+export type AvailableForDownload = { type: StateType.AvailableForDownload; update: IUpdate; canInstall?: boolean };
 export type Downloading = { type: StateType.Downloading; update?: IUpdate; explicit: boolean; overwrite: boolean; downloadedBytes?: number; totalBytes?: number; startTime?: number };
 export type Downloaded = { type: StateType.Downloaded; update: IUpdate; explicit: boolean; overwrite: boolean };
 export type Updating = { type: StateType.Updating; update: IUpdate; currentProgress?: number; maxProgress?: number };
@@ -81,9 +81,9 @@ export type State = Uninitialized | Disabled | Idle | CheckingForUpdates | Avail
 export const State = {
 	Uninitialized: upcast<Uninitialized>({ type: StateType.Uninitialized }),
 	Disabled: (reason: DisablementReason): Disabled => ({ type: StateType.Disabled, reason }),
-	Idle: (updateType: UpdateType, error?: string): Idle => ({ type: StateType.Idle, updateType, error }),
+	Idle: (updateType: UpdateType, error?: string, notAvailable?: boolean): Idle => ({ type: StateType.Idle, updateType, error, notAvailable }),
 	CheckingForUpdates: (explicit: boolean): CheckingForUpdates => ({ type: StateType.CheckingForUpdates, explicit }),
-	AvailableForDownload: (update: IUpdate): AvailableForDownload => ({ type: StateType.AvailableForDownload, update }),
+	AvailableForDownload: (update: IUpdate, canInstall?: boolean): AvailableForDownload => ({ type: StateType.AvailableForDownload, update, canInstall }),
 	Downloading: (update: IUpdate | undefined, explicit: boolean, overwrite: boolean, downloadedBytes?: number, totalBytes?: number, startTime?: number): Downloading => ({ type: StateType.Downloading, update, explicit, overwrite, downloadedBytes, totalBytes, startTime }),
 	Downloaded: (update: IUpdate, explicit: boolean, overwrite: boolean): Downloaded => ({ type: StateType.Downloaded, update, explicit, overwrite }),
 	Updating: (update: IUpdate, currentProgress?: number, maxProgress?: number): Updating => ({ type: StateType.Updating, update, currentProgress, maxProgress }),
@@ -111,7 +111,10 @@ export interface IUpdateService {
 	applyUpdate(): Promise<void>;
 	quitAndInstall(): Promise<void>;
 
+	/**
+	 * @deprecated This method should not be used any more. It will be removed in a future release.
+	*/
 	isLatestVersion(): Promise<boolean | undefined>;
 	_applySpecificUpdate(packagePath: string): Promise<void>;
-	disableProgressiveReleases(): Promise<void>;
+	setInternalOrg(internalOrg: string | undefined): Promise<void>;
 }
diff --git a/src/vs/platform/update/common/updateIpc.ts b/src/vs/platform/update/common/updateIpc.ts
index 9eaf8210757e2..6b165c49d2146 100644
--- a/src/vs/platform/update/common/updateIpc.ts
+++ b/src/vs/platform/update/common/updateIpc.ts
@@ -29,7 +29,7 @@ export class UpdateChannel implements IServerChannel {
 			case '_getInitialState': return Promise.resolve(this.service.state);
 			case 'isLatestVersion': return this.service.isLatestVersion();
 			case '_applySpecificUpdate': return this.service._applySpecificUpdate(arg);
-			case 'disableProgressiveReleases': return this.service.disableProgressiveReleases();
+			case 'setInternalOrg': return this.service.setInternalOrg(arg);
 		}
 
 		throw new Error(`Call not found: ${command}`);
@@ -80,8 +80,8 @@ export class UpdateChannelClient implements IUpdateService {
 		return this.channel.call('_applySpecificUpdate', packagePath);
 	}
 
-	disableProgressiveReleases(): Promise<void> {
-		return this.channel.call('disableProgressiveReleases');
+	setInternalOrg(internalOrg: string | undefined): Promise<void> {
+		return this.channel.call('setInternalOrg', internalOrg);
 	}
 
 	dispose(): void {
diff --git a/src/vs/platform/update/electron-main/abstractUpdateService.ts b/src/vs/platform/update/electron-main/abstractUpdateService.ts
index 698d277ca288b..c943bca4f5efb 100644
--- a/src/vs/platform/update/electron-main/abstractUpdateService.ts
+++ b/src/vs/platform/update/electron-main/abstractUpdateService.ts
@@ -20,6 +20,7 @@ import { AvailableForDownload, DisablementReason, IUpdateService, State, StateTy
 
 export interface IUpdateURLOptions {
 	readonly background?: boolean;
+	readonly internalOrg?: string;
 }
 
 export function createUpdateURL(baseUpdateUrl: string, platform: string, quality: string, commit: string, options?: IUpdateURLOptions): string {
@@ -29,6 +30,8 @@ export function createUpdateURL(baseUpdateUrl: string, platform: string, quality
 		url.searchParams.set('bg', 'true');
 	}
 
+	url.searchParams.set('u', options?.internalOrg ?? 'none');
+
 	return url.toString();
 }
 
@@ -77,7 +80,7 @@ export abstract class AbstractUpdateService implements IUpdateService {
 	protected _overwrite: boolean = false;
 	private _hasCheckedForOverwriteOnQuit: boolean = false;
 	private readonly overwriteUpdatesCheckInterval = new IntervalTimer();
-	private _disableProgressiveReleases: boolean = false;
+	private _internalOrg: string | undefined = undefined;
 
 	private readonly _onStateChange = new Emitter<State>();
 	readonly onStateChange: Event<State> = this._onStateChange.event;
@@ -139,11 +142,18 @@ export abstract class AbstractUpdateService implements IUpdateService {
 		}
 
 		const updateMode = this.configurationService.getValue<'none' | 'manual' | 'start' | 'default'>('update.mode');
+		const updateModeInspection = this.configurationService.inspect<'none' | 'manual' | 'start' | 'default'>('update.mode');
+		const policyDisablesUpdates = updateModeInspection.policyValue !== undefined && !this.getProductQuality(updateModeInspection.policyValue);
 		const quality = this.getProductQuality(updateMode);
 
 		if (!quality) {
-			this.setState(State.Disabled(DisablementReason.ManuallyDisabled));
-			this.logService.info('update#ctor - updates are disabled by user preference');
+			if (policyDisablesUpdates) {
+				this.setState(State.Disabled(DisablementReason.Policy));
+				this.logService.info('update#ctor - updates are disabled by policy');
+			} else {
+				this.setState(State.Disabled(DisablementReason.ManuallyDisabled));
+				this.logService.info('update#ctor - updates are disabled by user preference');
+			}
 			return;
 		}
 
@@ -314,7 +324,7 @@ export abstract class AbstractUpdateService implements IUpdateService {
 			return undefined;
 		}
 
-		const url = this.buildUpdateFeedUrl(this.quality, commit ?? this.productService.commit!);
+		const url = this.buildUpdateFeedUrl(this.quality, commit ?? this.productService.commit!, { internalOrg: this.getInternalOrg() });
 
 		if (!url) {
 			return undefined;
@@ -324,7 +334,7 @@ export abstract class AbstractUpdateService implements IUpdateService {
 		this.logService.trace('update#isLatestVersion() - checking update server', { url, headers });
 
 		try {
-			const context = await this.requestService.request({ url, headers }, token);
+			const context = await this.requestService.request({ url, headers, callSite: 'updateService.isLatestVersion' }, token);
 			const statusCode = context.res.statusCode;
 			this.logService.trace('update#isLatestVersion() - response', { statusCode });
 			// The update server replies with 204 (No Content) when no
@@ -342,13 +352,17 @@ export abstract class AbstractUpdateService implements IUpdateService {
 		// noop
 	}
 
-	async disableProgressiveReleases(): Promise<void> {
-		this.logService.info('update#disableProgressiveReleases');
-		this._disableProgressiveReleases = true;
+	async setInternalOrg(internalOrg: string | undefined): Promise<void> {
+		if (this._internalOrg === internalOrg) {
+			return;
+		}
+
+		this.logService.info('update#setInternalOrg', internalOrg);
+		this._internalOrg = internalOrg;
 	}
 
-	protected shouldDisableProgressiveReleases(): boolean {
-		return this._disableProgressiveReleases;
+	protected getInternalOrg(): string | undefined {
+		return this._internalOrg;
 	}
 
 	protected getUpdateType(): UpdateType {
diff --git a/src/vs/platform/update/electron-main/updateService.darwin.ts b/src/vs/platform/update/electron-main/updateService.darwin.ts
index a0c89233f3d4b..40b38a2ecb9c7 100644
--- a/src/vs/platform/update/electron-main/updateService.darwin.ts
+++ b/src/vs/platform/update/electron-main/updateService.darwin.ts
@@ -16,7 +16,7 @@ import { ILogService } from '../../log/common/log.js';
 import { IProductService } from '../../product/common/productService.js';
 import { asJson, IRequestService } from '../../request/common/request.js';
 import { ITelemetryService } from '../../telemetry/common/telemetry.js';
-import { AvailableForDownload, DisablementReason, IUpdate, State, StateType, UpdateType } from '../common/update.js';
+import { AvailableForDownload, IUpdate, State, StateType, UpdateType } from '../common/update.js';
 import { IMeteredConnectionService } from '../../meteredConnection/common/meteredConnection.js';
 import { AbstractUpdateService, createUpdateURL, getUpdateRequestHeaders, IUpdateURLOptions, UpdateErrorClassification } from './abstractUpdateService.js';
 import { INodeProcess } from '../../../base/common/platform.js';
@@ -68,13 +68,15 @@ export class DarwinUpdateService extends AbstractUpdateService implements IRelau
 	}
 
 	protected override async initialize(): Promise<void> {
+		await super.initialize();
+
+		// In the embedded app we still want to detect available updates via HTTP,
+		// but we must not wire up Electron's autoUpdater (which auto-downloads).
 		if ((process as INodeProcess).isEmbeddedApp) {
-			this.setState(State.Disabled(DisablementReason.EmbeddedApp));
-			this.logService.info('update#ctor - updates are disabled for embedded app');
+			this.logService.info('update#ctor - embedded app: checking for updates without auto-download');
 			return;
 		}
 
-		await super.initialize();
 		this.onRawError(this.onError, this, this.disposables);
 		this.onRawCheckingForUpdate(this.onCheckingForUpdate, this, this.disposables);
 		this.onRawUpdateAvailable(this.onUpdateAvailable, this, this.disposables);
@@ -127,13 +129,21 @@ export class DarwinUpdateService extends AbstractUpdateService implements IRelau
 
 		this.setState(State.CheckingForUpdates(explicit));
 
-		const background = !explicit && !this.shouldDisableProgressiveReleases();
-		const url = this.buildUpdateFeedUrl(this.quality, pendingCommit ?? this.productService.commit!, { background });
+		const internalOrg = this.getInternalOrg();
+		const background = !explicit && !internalOrg;
+		const url = this.buildUpdateFeedUrl(this.quality, pendingCommit ?? this.productService.commit!, { background, internalOrg });
 
 		if (!url) {
 			return;
 		}
 
+		// In the embedded app, always check without triggering Electron's auto-download.
+		if ((process as INodeProcess).isEmbeddedApp) {
+			this.logService.info('update#doCheckForUpdates - embedded app: checking for update without auto-download');
+			this.checkForUpdateNoDownload(url, /* canInstall */ false);
+			return;
+		}
+
 		// When connection is metered and this is not an explicit check, avoid electron call as to not to trigger auto-download.
 		if (!explicit && this.meteredConnectionService.isConnectionMetered) {
 			this.logService.info('update#doCheckForUpdates - checking for update without auto-download because connection is metered');
@@ -147,24 +157,26 @@ export class DarwinUpdateService extends AbstractUpdateService implements IRelau
 
 	/**
 	 * Manually check the update feed URL without triggering Electron's auto-download.
-	 * Used when connection is metered to show update availability without downloading.
+	 * Used when connection is metered or in the embedded app.
+	 * @param canInstall When false, signals that the update cannot be installed from this app.
 	 */
-	private async checkForUpdateNoDownload(url: string): Promise<void> {
+	private async checkForUpdateNoDownload(url: string, canInstall?: boolean): Promise<void> {
 		const headers = getUpdateRequestHeaders(this.productService.version);
 		this.logService.trace('update#checkForUpdateNoDownload - checking update server', { url, headers });
 
 		try {
-			const context = await this.requestService.request({ url, headers }, CancellationToken.None);
+			const context = await this.requestService.request({ url, headers, callSite: 'updateService.darwin.checkForUpdates' }, CancellationToken.None);
 			const statusCode = context.res.statusCode;
 			this.logService.trace('update#checkForUpdateNoDownload - response', { statusCode });
 
 			const update = await asJson<IUpdate>(context);
 			if (!update || !update.url || !update.version || !update.productVersion) {
 				this.logService.trace('update#checkForUpdateNoDownload - no update available');
-				this.setState(State.Idle(UpdateType.Archive));
+				const notAvailable = this.state.type === StateType.CheckingForUpdates && this.state.explicit;
+				this.setState(State.Idle(UpdateType.Archive, undefined, notAvailable || undefined));
 			} else {
 				this.logService.trace('update#checkForUpdateNoDownload - update available', { version: update.version, productVersion: update.productVersion });
-				this.setState(State.AvailableForDownload(update));
+				this.setState(State.AvailableForDownload(update, canInstall));
 			}
 		} catch (err) {
 			this.logService.error('update#checkForUpdateNoDownload - failed to check for update', err);
@@ -200,12 +212,13 @@ export class DarwinUpdateService extends AbstractUpdateService implements IRelau
 			return;
 		}
 
-		this.setState(State.Idle(UpdateType.Archive));
+		const notAvailable = this.state.explicit;
+		this.setState(State.Idle(UpdateType.Archive, undefined, notAvailable || undefined));
 	}
 
 	protected override async doDownloadUpdate(state: AvailableForDownload): Promise<void> {
 		// Rebuild feed URL and trigger download via Electron's auto-updater
-		this.buildUpdateFeedUrl(this.quality!, state.update.version);
+		this.buildUpdateFeedUrl(this.quality!, state.update.version, { internalOrg: this.getInternalOrg() });
 		this.setState(State.CheckingForUpdates(true));
 		electron.autoUpdater.checkForUpdates();
 	}
diff --git a/src/vs/platform/update/electron-main/updateService.linux.ts b/src/vs/platform/update/electron-main/updateService.linux.ts
index ee4b291a87ad3..0eb5d74364fca 100644
--- a/src/vs/platform/update/electron-main/updateService.linux.ts
+++ b/src/vs/platform/update/electron-main/updateService.linux.ts
@@ -39,15 +39,16 @@ export class LinuxUpdateService extends AbstractUpdateService {
 			return;
 		}
 
-		const background = !explicit && !this.shouldDisableProgressiveReleases();
-		const url = this.buildUpdateFeedUrl(this.quality, this.productService.commit!, { background });
+		const internalOrg = this.getInternalOrg();
+		const background = !explicit && !internalOrg;
+		const url = this.buildUpdateFeedUrl(this.quality, this.productService.commit!, { background, internalOrg });
 		this.setState(State.CheckingForUpdates(explicit));
 
-		this.requestService.request({ url }, CancellationToken.None)
+		this.requestService.request({ url, callSite: 'updateService.linux.checkForUpdates' }, CancellationToken.None)
 			.then<IUpdate | null>(asJson)
 			.then(update => {
 				if (!update || !update.url || !update.version || !update.productVersion) {
-					this.setState(State.Idle(UpdateType.Archive));
+					this.setState(State.Idle(UpdateType.Archive, undefined, explicit || undefined));
 				} else {
 					this.setState(State.AvailableForDownload(update));
 				}
diff --git a/src/vs/platform/update/electron-main/updateService.snap.ts b/src/vs/platform/update/electron-main/updateService.snap.ts
index b09111d023506..ae2df6ac89dc5 100644
--- a/src/vs/platform/update/electron-main/updateService.snap.ts
+++ b/src/vs/platform/update/electron-main/updateService.snap.ts
@@ -133,7 +133,7 @@ abstract class AbstractUpdateService implements IUpdateService {
 		// noop
 	}
 
-	async disableProgressiveReleases(): Promise<void> {
+	async setInternalOrg(_internalOrg: string | undefined): Promise<void> {
 		// noop - not applicable for snap
 	}
 
@@ -176,7 +176,7 @@ export class SnapUpdateService extends AbstractUpdateService {
 			if (result) {
 				this.setState(State.Ready({ version: 'something' }, false, false));
 			} else {
-				this.setState(State.Idle(UpdateType.Snap));
+				this.setState(State.Idle(UpdateType.Snap, undefined, undefined));
 			}
 		}, err => {
 			this.logService.error(err);
diff --git a/src/vs/platform/update/electron-main/updateService.win32.ts b/src/vs/platform/update/electron-main/updateService.win32.ts
index c4b6083f99a69..d02d7c3b8d80d 100644
--- a/src/vs/platform/update/electron-main/updateService.win32.ts
+++ b/src/vs/platform/update/electron-main/updateService.win32.ts
@@ -33,6 +33,7 @@ import { asJson, IRequestService } from '../../request/common/request.js';
 import { ITelemetryService } from '../../telemetry/common/telemetry.js';
 import { AvailableForDownload, DisablementReason, IUpdate, State, StateType, UpdateType } from '../common/update.js';
 import { AbstractUpdateService, createUpdateURL, getUpdateRequestHeaders, IUpdateURLOptions, UpdateErrorClassification } from './abstractUpdateService.js';
+import { INodeProcess } from '../../../base/common/platform.js';
 
 interface IAvailableUpdate {
 	packagePath: string;
@@ -98,6 +99,14 @@ export class Win32UpdateService extends AbstractUpdateService implements IRelaun
 	}
 
 	protected override async initialize(): Promise<void> {
+		// In the embedded app, skip win32-specific setup (cache paths, telemetry)
+		// but still run the base initialization to detect available updates.
+		if ((process as INodeProcess).isEmbeddedApp) {
+			this.logService.info('update#ctor - embedded app: checking for updates without auto-download');
+			await super.initialize();
+			return;
+		}
+
 		if (this.productService.win32VersionedUpdate) {
 			const cachePath = await this.cachePath;
 			app.setPath('appUpdate', cachePath);
@@ -188,8 +197,9 @@ export class Win32UpdateService extends AbstractUpdateService implements IRelaun
 			return;
 		}
 
-		const background = !explicit && !this.shouldDisableProgressiveReleases();
-		const url = this.buildUpdateFeedUrl(this.quality, pendingCommit ?? this.productService.commit!, { background });
+		const internalOrg = this.getInternalOrg();
+		const background = !explicit && !internalOrg;
+		const url = this.buildUpdateFeedUrl(this.quality, pendingCommit ?? this.productService.commit!, { background, internalOrg });
 
 		// Only set CheckingForUpdates if we're not already in Overwriting state
 		if (this.state.type !== StateType.Overwriting) {
@@ -197,7 +207,7 @@ export class Win32UpdateService extends AbstractUpdateService implements IRelaun
 		}
 
 		const headers = getUpdateRequestHeaders(this.productService.version);
-		this.requestService.request({ url, headers }, CancellationToken.None)
+		this.requestService.request({ url, headers, callSite: 'updateService.win32.checkForUpdates' }, CancellationToken.None)
 			.then<IUpdate | null>(asJson)
 			.then(update => {
 				const updateType = getUpdateType();
@@ -209,7 +219,7 @@ export class Win32UpdateService extends AbstractUpdateService implements IRelaun
 						this._overwrite = false;
 						this.setState(State.Ready(this.state.update, this.state.explicit, false));
 					} else {
-						this.setState(State.Idle(updateType));
+						this.setState(State.Idle(updateType, undefined, explicit || undefined));
 					}
 					return Promise.resolve(null);
 				}
@@ -219,6 +229,13 @@ export class Win32UpdateService extends AbstractUpdateService implements IRelaun
 					return Promise.resolve(null);
 				}
 
+				// In the embedded app, signal that an update exists but can't be installed here.
+				if ((process as INodeProcess).isEmbeddedApp) {
+					this.logService.info('update#doCheckForUpdates - embedded app: update available, skipping download');
+					this.setState(State.AvailableForDownload(update, /* canInstall */ false));
+					return Promise.resolve(null);
+				}
+
 				// When connection is metered and this is not an explicit check,
 				// show update is available but don't start downloading
 				if (!explicit && this.meteredConnectionService.isConnectionMetered) {
@@ -239,7 +256,7 @@ export class Win32UpdateService extends AbstractUpdateService implements IRelaun
 
 							const downloadPath = `${updatePackagePath}.tmp`;
 
-							return this.requestService.request({ url: update.url }, CancellationToken.None)
+							return this.requestService.request({ url: update.url, callSite: 'updateService.win32.downloadUpdate' }, CancellationToken.None)
 								.then(context => {
 									// Get total size from Content-Length header
 									const contentLengthHeader = context.res.headers['content-length'];
diff --git a/src/vs/platform/userDataSync/common/userDataSyncStoreService.ts b/src/vs/platform/userDataSync/common/userDataSyncStoreService.ts
index e5642bc2b8c40..cda7b80d8bc4c 100644
--- a/src/vs/platform/userDataSync/common/userDataSyncStoreService.ts
+++ b/src/vs/platform/userDataSync/common/userDataSyncStoreService.ts
@@ -258,7 +258,7 @@ export class UserDataSyncStoreClient extends Disposable {
 		headers = { ...headers };
 		headers['Content-Type'] = 'application/json';
 
-		const context = await this.request(url, { type: 'GET', headers }, [], CancellationToken.None);
+		const context = await this.request(url, { type: 'GET', headers, callSite: 'userDataSync.getAllCollections' }, [], CancellationToken.None);
 
 		return (await asJson<{ id: string }[]>(context))?.map(({ id }) => id) || [];
 	}
@@ -272,7 +272,7 @@ export class UserDataSyncStoreClient extends Disposable {
 		headers = { ...headers };
 		headers['Content-Type'] = Mimes.text;
 
-		const context = await this.request(url, { type: 'POST', headers }, [], CancellationToken.None);
+		const context = await this.request(url, { type: 'POST', headers, callSite: 'userDataSync.createCollection' }, [], CancellationToken.None);
 		const collectionId = await asTextOrError(context);
 		if (!collectionId) {
 			throw new UserDataSyncStoreError('Server did not return the collection id', url, UserDataSyncErrorCode.NoCollection, context.res.statusCode, context.res.headers[HEADER_OPERATION_ID]);
@@ -288,7 +288,7 @@ export class UserDataSyncStoreClient extends Disposable {
 		const url = collection ? joinPath(this.userDataSyncStoreUrl, 'collection', collection).toString() : joinPath(this.userDataSyncStoreUrl, 'collection').toString();
 		headers = { ...headers };
 
-		await this.request(url, { type: 'DELETE', headers }, [], CancellationToken.None);
+		await this.request(url, { type: 'DELETE', headers, callSite: 'userDataSync.deleteCollection' }, [], CancellationToken.None);
 	}
 
 	// #endregion
@@ -303,7 +303,7 @@ export class UserDataSyncStoreClient extends Disposable {
 		const uri = this.getResourceUrl(this.userDataSyncStoreUrl, collection, resource);
 		const headers: IHeaders = {};
 
-		const context = await this.request(uri.toString(), { type: 'GET', headers }, [], CancellationToken.None);
+		const context = await this.request(uri.toString(), { type: 'GET', headers, callSite: 'userDataSync.getAllResourceRefs' }, [], CancellationToken.None);
 
 		const result = await asJson<{ url: string; created: number }[]>(context) || [];
 		return result.map(({ url, created }) => ({ ref: relativePath(uri, uri.with({ path: url }))!, created: created * 1000 /* Server returns in seconds */ }));
@@ -318,7 +318,7 @@ export class UserDataSyncStoreClient extends Disposable {
 		headers = { ...headers };
 		headers['Cache-Control'] = 'no-cache';
 
-		const context = await this.request(url, { type: 'GET', headers }, [], CancellationToken.None);
+		const context = await this.request(url, { type: 'GET', headers, callSite: 'userDataSync.resolveResourceContent' }, [], CancellationToken.None);
 		const content = await asTextOrError(context);
 		return content;
 	}
@@ -331,7 +331,7 @@ export class UserDataSyncStoreClient extends Disposable {
 		const url = ref !== null ? joinPath(this.getResourceUrl(this.userDataSyncStoreUrl, collection, resource), ref).toString() : this.getResourceUrl(this.userDataSyncStoreUrl, collection, resource).toString();
 		const headers: IHeaders = {};
 
-		await this.request(url, { type: 'DELETE', headers }, [], CancellationToken.None);
+		await this.request(url, { type: 'DELETE', headers, callSite: 'userDataSync.deleteResource' }, [], CancellationToken.None);
 	}
 
 	async deleteResources(): Promise<void> {
@@ -342,7 +342,7 @@ export class UserDataSyncStoreClient extends Disposable {
 		const url = joinPath(this.userDataSyncStoreUrl, 'resource').toString();
 		const headers: IHeaders = { 'Content-Type': Mimes.text };
 
-		await this.request(url, { type: 'DELETE', headers }, [], CancellationToken.None);
+		await this.request(url, { type: 'DELETE', headers, callSite: 'userDataSync.deleteResources' }, [], CancellationToken.None);
 	}
 
 	async readResource(resource: ServerResource, oldValue: IUserData | null, collection?: string, headers: IHeaders = {}): Promise<IUserData> {
@@ -358,7 +358,7 @@ export class UserDataSyncStoreClient extends Disposable {
 			headers['If-None-Match'] = oldValue.ref;
 		}
 
-		const context = await this.request(url, { type: 'GET', headers }, [304], CancellationToken.None);
+		const context = await this.request(url, { type: 'GET', headers, callSite: 'userDataSync.readResource' }, [304], CancellationToken.None);
 
 		let userData: IUserData | null = null;
 		if (context.res.statusCode === 304) {
@@ -394,7 +394,7 @@ export class UserDataSyncStoreClient extends Disposable {
 			headers['If-Match'] = ref;
 		}
 
-		const context = await this.request(url, { type: 'POST', data, headers }, [], CancellationToken.None);
+		const context = await this.request(url, { type: 'POST', data, headers, callSite: 'userDataSync.writeResource' }, [], CancellationToken.None);
 
 		const newRef = context.res.headers['etag'];
 		if (!newRef) {
@@ -417,7 +417,7 @@ export class UserDataSyncStoreClient extends Disposable {
 			headers['If-None-Match'] = oldValue.ref;
 		}
 
-		const context = await this.request(url, { type: 'GET', headers }, [304], CancellationToken.None);
+		const context = await this.request(url, { type: 'GET', headers, callSite: 'userDataSync.manifest' }, [304], CancellationToken.None);
 
 		let manifest: IUserDataManifest | null = null;
 		if (context.res.statusCode === 304) {
@@ -481,7 +481,7 @@ export class UserDataSyncStoreClient extends Disposable {
 
 		headers = { ...headers };
 		headers['Content-Type'] = 'application/json';
-		const context = await this.request(url, { type: 'GET', headers }, [], CancellationToken.None);
+		const context = await this.request(url, { type: 'GET', headers, callSite: 'userDataSync.getLatestData' }, [], CancellationToken.None);
 
 		if (!isSuccess(context)) {
 			throw new UserDataSyncStoreError('Server returned ' + context.res.statusCode, url, UserDataSyncErrorCode.EmptyResponse, context.res.statusCode, context.res.headers[HEADER_OPERATION_ID]);
@@ -530,7 +530,7 @@ export class UserDataSyncStoreClient extends Disposable {
 		const url = joinPath(this.userDataSyncStoreUrl, 'download').toString();
 		const headers: IHeaders = {};
 
-		const context = await this.request(url, { type: 'GET', headers }, [], CancellationToken.None);
+		const context = await this.request(url, { type: 'GET', headers, callSite: 'userDataSync.getActivityData' }, [], CancellationToken.None);
 
 		if (!isSuccess(context)) {
 			throw new UserDataSyncStoreError('Server returned ' + context.res.statusCode, url, UserDataSyncErrorCode.EmptyResponse, context.res.statusCode, context.res.headers[HEADER_OPERATION_ID]);
diff --git a/src/vs/platform/userDataSync/test/common/userDataSyncClient.ts b/src/vs/platform/userDataSync/test/common/userDataSyncClient.ts
index e53e777741648..058eab04cfb52 100644
--- a/src/vs/platform/userDataSync/test/common/userDataSyncClient.ts
+++ b/src/vs/platform/userDataSync/test/common/userDataSyncClient.ts
@@ -6,7 +6,7 @@
 import { bufferToStream, VSBuffer } from '../../../../base/common/buffer.js';
 import { CancellationToken } from '../../../../base/common/cancellation.js';
 import { IStringDictionary } from '../../../../base/common/collections.js';
-import { Emitter } from '../../../../base/common/event.js';
+import { Emitter, Event } from '../../../../base/common/event.js';
 import { FormattingOptions } from '../../../../base/common/jsonFormatter.js';
 import { Disposable } from '../../../../base/common/lifecycle.js';
 import { Schemas } from '../../../../base/common/network.js';
@@ -26,7 +26,7 @@ import { TestInstantiationService } from '../../../instantiation/test/common/ins
 import { ILogService, NullLogService } from '../../../log/common/log.js';
 import product from '../../../product/common/product.js';
 import { IProductService } from '../../../product/common/productService.js';
-import { AuthInfo, Credentials, IRequestService } from '../../../request/common/request.js';
+import { AuthInfo, Credentials, IRequestCompleteEvent, IRequestService } from '../../../request/common/request.js';
 import { InMemoryStorageService, IStorageService } from '../../../storage/common/storage.js';
 import { ITelemetryService } from '../../../telemetry/common/telemetry.js';
 import { NullTelemetryService } from '../../../telemetry/common/telemetryUtils.js';
@@ -181,6 +181,8 @@ export class UserDataSyncTestServer implements IRequestService {
 
 	_serviceBrand: undefined;
 
+	readonly onDidCompleteRequest = Event.None as Event<IRequestCompleteEvent>;
+
 	readonly url: string = 'http://host:3000';
 	private session: string | null = null;
 	private readonly collections = new Map<string, Map<ServerResource, IUserData>>();
diff --git a/src/vs/platform/userDataSync/test/common/userDataSyncStoreService.test.ts b/src/vs/platform/userDataSync/test/common/userDataSyncStoreService.test.ts
index 4f720f7d23198..847a38470899f 100644
--- a/src/vs/platform/userDataSync/test/common/userDataSyncStoreService.test.ts
+++ b/src/vs/platform/userDataSync/test/common/userDataSyncStoreService.test.ts
@@ -13,7 +13,7 @@ import { runWithFakedTimers } from '../../../../base/test/common/timeTravelSched
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../base/test/common/utils.js';
 import { NullLogService } from '../../../log/common/log.js';
 import { IProductService } from '../../../product/common/productService.js';
-import { IRequestService } from '../../../request/common/request.js';
+import { IRequestCompleteEvent, IRequestService } from '../../../request/common/request.js';
 import { IUserDataSyncStoreService, SyncResource, UserDataSyncErrorCode, UserDataSyncStoreError } from '../../common/userDataSync.js';
 import { RequestsSession, UserDataSyncStoreService } from '../../common/userDataSyncStoreService.js';
 import { UserDataSyncClient, UserDataSyncTestServer } from './userDataSyncClient.js';
@@ -412,6 +412,7 @@ suite('UserDataSyncRequestsSession', () => {
 
 	const requestService: IRequestService = {
 		_serviceBrand: undefined,
+		onDidCompleteRequest: Event.None as Event<IRequestCompleteEvent>,
 		async request() { return { res: { headers: {} }, stream: newWriteableBufferStream() }; },
 		async resolveProxy() { return undefined; },
 		async lookupAuthorization() { return undefined; },
@@ -424,10 +425,10 @@ suite('UserDataSyncRequestsSession', () => {
 
 	test('too many requests are thrown when limit exceeded', async () => {
 		const testObject = new RequestsSession(1, 500, requestService, new NullLogService());
-		await testObject.request('url', {}, CancellationToken.None);
+		await testObject.request('url', { callSite: 'test' }, CancellationToken.None);
 
 		try {
-			await testObject.request('url', {}, CancellationToken.None);
+			await testObject.request('url', { callSite: 'test' }, CancellationToken.None);
 		} catch (error) {
 			assert.ok(error instanceof UserDataSyncStoreError);
 			assert.strictEqual((<UserDataSyncStoreError>error).code, UserDataSyncErrorCode.LocalTooManyRequests);
@@ -438,19 +439,19 @@ suite('UserDataSyncRequestsSession', () => {
 
 	test('requests are handled after session is expired', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
 		const testObject = new RequestsSession(1, 100, requestService, new NullLogService());
-		await testObject.request('url', {}, CancellationToken.None);
+		await testObject.request('url', { callSite: 'test' }, CancellationToken.None);
 		await timeout(125);
-		await testObject.request('url', {}, CancellationToken.None);
+		await testObject.request('url', { callSite: 'test' }, CancellationToken.None);
 	}));
 
 	test('too many requests are thrown after session is expired', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
 		const testObject = new RequestsSession(1, 100, requestService, new NullLogService());
-		await testObject.request('url', {}, CancellationToken.None);
+		await testObject.request('url', { callSite: 'test' }, CancellationToken.None);
 		await timeout(125);
-		await testObject.request('url', {}, CancellationToken.None);
+		await testObject.request('url', { callSite: 'test' }, CancellationToken.None);
 
 		try {
-			await testObject.request('url', {}, CancellationToken.None);
+			await testObject.request('url', { callSite: 'test' }, CancellationToken.None);
 		} catch (error) {
 			assert.ok(error instanceof UserDataSyncStoreError);
 			assert.strictEqual((<UserDataSyncStoreError>error).code, UserDataSyncErrorCode.LocalTooManyRequests);
diff --git a/src/vs/platform/utilityProcess/electron-main/utilityProcess.ts b/src/vs/platform/utilityProcess/electron-main/utilityProcess.ts
index fccddba015651..c1dd46b4c1771 100644
--- a/src/vs/platform/utilityProcess/electron-main/utilityProcess.ts
+++ b/src/vs/platform/utilityProcess/electron-main/utilityProcess.ts
@@ -245,8 +245,12 @@ export class UtilityProcess extends Disposable {
 		const serviceName = `${this.configuration.type}-${this.id}`;
 		const modulePath = FileAccess.asFileUri('bootstrap-fork.js').fsPath;
 		const args = this.configuration.args ?? [];
-		const execArgv = this.configuration.execArgv ?? [];
+		const execArgv = [...(this.configuration.execArgv ?? [])];
 		const allowLoadingUnsignedLibraries = this.configuration.allowLoadingUnsignedLibraries;
+		const jsFlags = app.commandLine.getSwitchValue('js-flags');
+		if (jsFlags) {
+			execArgv.push(`--js-flags=${jsFlags}`);
+		}
 		const respondToAuthRequestsFromMainProcess = this.configuration.respondToAuthRequestsFromMainProcess;
 		const stdio = 'pipe';
 		const env = this.createEnv(configuration);
diff --git a/src/vs/platform/webContentExtractor/test/electron-main/cdpAccessibilityDomain.test.ts b/src/vs/platform/webContentExtractor/test/electron-main/cdpAccessibilityDomain.test.ts
index 5085922319585..f4ec49d643be5 100644
--- a/src/vs/platform/webContentExtractor/test/electron-main/cdpAccessibilityDomain.test.ts
+++ b/src/vs/platform/webContentExtractor/test/electron-main/cdpAccessibilityDomain.test.ts
@@ -5,7 +5,7 @@
 
 import * as assert from 'assert';
 import { URI } from '../../../../base/common/uri.js';
-import { AXNode, AXProperty, AXValueType, convertAXTreeToMarkdown } from '../../electron-main/cdpAccessibilityDomain.js';
+import { AXNode, AXProperty, AXPropertyName, AXValueType, convertAXTreeToMarkdown } from '../../electron-main/cdpAccessibilityDomain.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../base/test/common/utils.js';
 
 suite('CDP Accessibility Domain', () => {
@@ -17,10 +17,9 @@ suite('CDP Accessibility Domain', () => {
 		return { type, value };
 	}
 
-	function createAXProperty(name: string, value: any, type: AXValueType = 'string'): AXProperty {
+	function createAXProperty(name: AXPropertyName, value: any, type: AXValueType = 'string'): AXProperty {
 		return {
-			// eslint-disable-next-line local/code-no-any-casts
-			name: name as any,
+			name,
 			value: createAXValue(type, value)
 		};
 	}
diff --git a/src/vs/platform/windows/electron-main/windowImpl.ts b/src/vs/platform/windows/electron-main/windowImpl.ts
index 7455376e3f45c..07551319546ce 100644
--- a/src/vs/platform/windows/electron-main/windowImpl.ts
+++ b/src/vs/platform/windows/electron-main/windowImpl.ts
@@ -11,7 +11,7 @@ import { Emitter, Event } from '../../../base/common/event.js';
 import { Disposable, DisposableStore, IDisposable, MutableDisposable, toDisposable } from '../../../base/common/lifecycle.js';
 import { FileAccess, Schemas } from '../../../base/common/network.js';
 import { getMarks, mark } from '../../../base/common/performance.js';
-import { isTahoeOrNewer, isLinux, isMacintosh, isWindows } from '../../../base/common/platform.js';
+import { isTahoeOrNewer, isLinux, isMacintosh, isWindows, INodeProcess } from '../../../base/common/platform.js';
 import { URI } from '../../../base/common/uri.js';
 import { localize } from '../../../nls.js';
 import { release } from 'os';
@@ -702,11 +702,16 @@ export class CodeWindow extends BaseWindow implements ICodeWindow {
 			this.windowState = state;
 			this.logService.trace('window#ctor: using window state', state);
 
-			const options = instantiationService.invokeFunction(defaultBrowserWindowOptions, this.windowState, undefined, {
+			const webPreferences: electron.WebPreferences = {
 				preload: FileAccess.asFileUri('vs/base/parts/sandbox/electron-browser/preload.js').fsPath,
 				additionalArguments: [`--vscode-window-config=${this.configObjectUrl.resource.toString()}`],
-				v8CacheOptions: this.environmentMainService.useCodeCache ? 'bypassHeatCheck' : 'none',
-			});
+				v8CacheOptions: this.environmentMainService.useCodeCache ? 'bypassHeatCheck' : 'none'
+			};
+			if ((process as INodeProcess).isEmbeddedApp) {
+				webPreferences.backgroundThrottling = false; // disable for sub-app
+			}
+
+			const options = instantiationService.invokeFunction(defaultBrowserWindowOptions, this.windowState, undefined, webPreferences);
 
 			// Create the browser window
 			mark('code/willCreateCodeBrowserWindow');
diff --git a/src/vs/platform/windows/electron-main/windows.ts b/src/vs/platform/windows/electron-main/windows.ts
index 50b1321e83e30..75bcee0c678ad 100644
--- a/src/vs/platform/windows/electron-main/windows.ts
+++ b/src/vs/platform/windows/electron-main/windows.ts
@@ -7,7 +7,7 @@ import electron, { Display, Rectangle } from 'electron';
 import { Color } from '../../../base/common/color.js';
 import { Event } from '../../../base/common/event.js';
 import { join } from '../../../base/common/path.js';
-import { IProcessEnvironment, isLinux, isMacintosh, isWindows } from '../../../base/common/platform.js';
+import { INodeProcess, IProcessEnvironment, isLinux, isMacintosh, isWindows } from '../../../base/common/platform.js';
 import { URI } from '../../../base/common/uri.js';
 import { IAuxiliaryWindow } from '../../auxiliaryWindow/electron-main/auxiliaryWindow.js';
 import { IConfigurationService } from '../../configuration/common/configuration.js';
@@ -177,8 +177,15 @@ export function defaultBrowserWindowOptions(accessor: ServicesAccessor, windowSt
 
 	if (isLinux) {
 		options.icon = join(environmentMainService.appRoot, 'resources/linux/code.png'); // always on Linux
-	} else if (isWindows && !environmentMainService.isBuilt) {
-		options.icon = join(environmentMainService.appRoot, 'resources/win32/code_150x150.png'); // only when running out of sources on Windows
+	} else if (isWindows) {
+		if (!environmentMainService.isBuilt) {
+			options.icon = join(environmentMainService.appRoot, 'resources/win32/code_150x150.png'); // only when running out of sources on Windows
+		} else if ((process as INodeProcess).isEmbeddedApp) {
+			// For sub app the proxy executable acts as a launcher to the main executable whose
+			// icon will be used when creating windows if the following override is not set.
+			// This avoids sharing icon with the main application.
+			options.icon = join(environmentMainService.appRoot, 'resources/win32/sessions.ico');
+		}
 	}
 
 	if (isMacintosh) {
diff --git a/src/vs/platform/workspace/common/workspace.ts b/src/vs/platform/workspace/common/workspace.ts
index a0459d077e6ea..691e1a3bf2e89 100644
--- a/src/vs/platform/workspace/common/workspace.ts
+++ b/src/vs/platform/workspace/common/workspace.ts
@@ -74,6 +74,11 @@ export interface IWorkspaceContextService {
 	 * Returns if the provided resource is inside the workspace or not.
 	 */
 	isInsideWorkspace(resource: URI): boolean;
+
+	/**
+	 * Return `true` if the current workspace has data (e.g. folders or a workspace configuration) that can be sent to the extension host, otherwise `false`.
+	 */
+	hasWorkspaceData(): boolean;
 }
 
 export interface IResolvedWorkspace extends IWorkspaceIdentifier, IBaseWorkspace {
diff --git a/src/vs/server/node/remoteExtensionManagement.ts b/src/vs/server/node/remoteExtensionManagement.ts
index df587cf746828..4a38e83ea25a0 100644
--- a/src/vs/server/node/remoteExtensionManagement.ts
+++ b/src/vs/server/node/remoteExtensionManagement.ts
@@ -8,6 +8,7 @@ import { ILogService } from '../../platform/log/common/log.js';
 import { Emitter, Event } from '../../base/common/event.js';
 import { VSBuffer } from '../../base/common/buffer.js';
 import { ProcessTimeRunOnceScheduler } from '../../base/common/async.js';
+import { IDisposable } from '../../base/common/lifecycle.js';
 
 function printTime(ms: number): string {
 	let h = 0;
@@ -45,6 +46,7 @@ export class ManagementConnection {
 	private _disposed: boolean;
 	private _disconnectRunner1: ProcessTimeRunOnceScheduler;
 	private _disconnectRunner2: ProcessTimeRunOnceScheduler;
+	private readonly _socketCloseListener: IDisposable;
 
 	constructor(
 		private readonly _logService: ILogService,
@@ -69,11 +71,11 @@ export class ManagementConnection {
 			this._cleanResources();
 		}, this._reconnectionShortGraceTime);
 
-		this.protocol.onDidDispose(() => {
+		Event.once(this.protocol.onDidDispose)(() => {
 			this._log(`The client has disconnected gracefully, so the connection will be disposed.`);
 			this._cleanResources();
 		});
-		this.protocol.onSocketClose(() => {
+		this._socketCloseListener = this.protocol.onSocketClose(() => {
 			this._log(`The client has disconnected, will wait for reconnection ${printTime(this._reconnectionGraceTime)} before disposing...`);
 			// The socket has closed, let's give the renderer a certain amount of time to reconnect
 			this._disconnectRunner1.schedule();
@@ -106,6 +108,7 @@ export class ManagementConnection {
 		this._disposed = true;
 		this._disconnectRunner1.dispose();
 		this._disconnectRunner2.dispose();
+		this._socketCloseListener.dispose();
 		const socket = this.protocol.getSocket();
 		this.protocol.sendDisconnect();
 		this.protocol.dispose();
diff --git a/src/vs/server/node/remoteTerminalChannel.ts b/src/vs/server/node/remoteTerminalChannel.ts
index a455eba42679c..ab6f98f02561c 100644
--- a/src/vs/server/node/remoteTerminalChannel.ts
+++ b/src/vs/server/node/remoteTerminalChannel.ts
@@ -226,7 +226,7 @@ export class RemoteTerminalChannel extends Disposable implements IServerChannel<
 		const activeWorkspaceFolder = args.activeWorkspaceFolder ? reviveWorkspaceFolder(args.activeWorkspaceFolder) : undefined;
 		const activeFileResource = args.activeFileResource ? URI.revive(uriTransformer.transformIncoming(args.activeFileResource)) : undefined;
 		const customVariableResolver = new CustomVariableResolver(baseEnv, workspaceFolders, activeFileResource, args.resolvedVariables, this._extensionManagementService);
-		const variableResolver = terminalEnvironment.createVariableResolver(activeWorkspaceFolder, process.env, customVariableResolver);
+		const variableResolver = terminalEnvironment.createVariableResolver(activeWorkspaceFolder, baseEnv, customVariableResolver);
 
 		// Get the initial cwd
 		const initialCwd = await terminalEnvironment.getCwd(shellLaunchConfig, os.homedir(), variableResolver, activeWorkspaceFolder?.uri, args.configuration['terminal.integrated.cwd'], this._logService);
diff --git a/src/vs/server/node/serverServices.ts b/src/vs/server/node/serverServices.ts
index d37663dfefb4c..1ef575e8637d4 100644
--- a/src/vs/server/node/serverServices.ts
+++ b/src/vs/server/node/serverServices.ts
@@ -86,6 +86,10 @@ import { NativeMcpDiscoveryHelperService } from '../../platform/mcp/node/nativeM
 import { IMcpGatewayService, McpGatewayChannelName } from '../../platform/mcp/common/mcpGateway.js';
 import { McpGatewayService } from '../../platform/mcp/node/mcpGatewayService.js';
 import { McpGatewayChannel } from '../../platform/mcp/node/mcpGatewayChannel.js';
+import { SandboxHelperChannelName } from '../../platform/sandbox/common/sandboxHelperIpc.js';
+import { ISandboxHelperService } from '../../platform/sandbox/common/sandboxHelperService.js';
+import { SandboxHelperChannel } from '../../platform/sandbox/node/sandboxHelperChannel.js';
+import { SandboxHelperService } from '../../platform/sandbox/node/sandboxHelperService.js';
 import { IExtensionGalleryManifestService } from '../../platform/extensionManagement/common/extensionGalleryManifest.js';
 import { ExtensionGalleryManifestIPCService } from '../../platform/extensionManagement/common/extensionGalleryManifestServiceIpc.js';
 import { IAllowedMcpServersService, IMcpGalleryService, IMcpManagementService } from '../../platform/mcp/common/mcpManagement.js';
@@ -211,6 +215,7 @@ export async function setupServerServices(connectionToken: ServerConnectionToken
 	services.set(IExtensionSignatureVerificationService, new SyncDescriptor(ExtensionSignatureVerificationService));
 	services.set(IAllowedExtensionsService, new SyncDescriptor(AllowedExtensionsService));
 	services.set(INativeServerExtensionManagementService, new SyncDescriptor(ExtensionManagementService));
+	services.set(ISandboxHelperService, new SyncDescriptor(SandboxHelperService));
 	services.set(INativeMcpDiscoveryHelperService, new SyncDescriptor(NativeMcpDiscoveryHelperService));
 	services.set(IMcpGatewayService, new SyncDescriptor(McpGatewayService));
 
@@ -250,6 +255,7 @@ export async function setupServerServices(connectionToken: ServerConnectionToken
 		const remoteExtensionsScanner = new RemoteExtensionsScannerService(instantiationService.createInstance(ExtensionManagementCLI, productService.extensionsForceVersionByQuality ?? [], logService), environmentService, userDataProfilesService, extensionsScannerService, logService, extensionGalleryService, languagePackService, extensionManagementService);
 		socketServer.registerChannel(RemoteExtensionsScannerChannelName, new RemoteExtensionsScannerChannel(remoteExtensionsScanner, (ctx: RemoteAgentConnectionContext) => getUriTransformer(ctx.remoteAuthority)));
 
+		socketServer.registerChannel(SandboxHelperChannelName, instantiationService.createInstance(SandboxHelperChannel));
 		socketServer.registerChannel(NativeMcpDiscoveryHelperChannelName, instantiationService.createInstance(NativeMcpDiscoveryHelperChannel, (ctx: RemoteAgentConnectionContext) => getUriTransformer(ctx.remoteAuthority)));
 		socketServer.registerChannel(McpGatewayChannelName, instantiationService.createInstance(McpGatewayChannel<RemoteAgentConnectionContext>, socketServer));
 
diff --git a/src/vs/server/node/webClientServer.ts b/src/vs/server/node/webClientServer.ts
index 7881ad0393d70..028a056717b1e 100644
--- a/src/vs/server/node/webClientServer.ts
+++ b/src/vs/server/node/webClientServer.ts
@@ -206,7 +206,8 @@ export class WebClientServer {
 		const context = await this._requestService.request({
 			type: 'GET',
 			url: uri.toString(true),
-			headers
+			headers,
+			callSite: 'webClientServer.fetchAndWriteFile'
 		}, CancellationToken.None);
 
 		const status = context.res.statusCode || 500;
diff --git a/src/vs/sessions/AI_CUSTOMIZATIONS.md b/src/vs/sessions/AI_CUSTOMIZATIONS.md
index 9dceeac3a2b24..e3c8ec0b8d1ce 100644
--- a/src/vs/sessions/AI_CUSTOMIZATIONS.md
+++ b/src/vs/sessions/AI_CUSTOMIZATIONS.md
@@ -1,94 +1,148 @@
 # AI Customizations – Design Document
 
-This document describes the current AI customization experience in this branch: a management editor and tree view that surface items across worktree, user, and extension storage.
+This document describes the AI customization experience: a management editor and tree view that surface customization items (agents, skills, instructions, prompts, hooks, MCP servers) across workspace, user, and extension storage.
 
-## Current Architecture
+## Architecture
 
-### File Structure (Agentic)
+### File Structure
+
+The management editor lives in `vs/workbench` (shared between core VS Code and sessions):
 
 ```
-src/vs/sessions/contrib/aiCustomizationManagement/browser/
+src/vs/workbench/contrib/chat/browser/aiCustomization/
 ├── aiCustomizationManagement.contribution.ts   # Commands + context menus
 ├── aiCustomizationManagement.ts                # IDs + context keys
 ├── aiCustomizationManagementEditor.ts          # SplitView list/editor
 ├── aiCustomizationManagementEditorInput.ts     # Singleton input
 ├── aiCustomizationListWidget.ts                # Search + grouped list
-├── aiCustomizationOverviewView.ts              # Overview view (counts + deep links)
+├── aiCustomizationDebugPanel.ts                # Debug diagnostics panel
+├── aiCustomizationWorkspaceService.ts          # Core VS Code workspace service impl
 ├── customizationCreatorService.ts              # AI-guided creation flow
 ├── mcpListWidget.ts                            # MCP servers section
-├── SPEC.md                                     # Feature specification
+├── aiCustomizationIcons.ts                     # Icons
 └── media/
     └── aiCustomizationManagement.css
 
+src/vs/workbench/contrib/chat/common/
+└── aiCustomizationWorkspaceService.ts          # IAICustomizationWorkspaceService + IStorageSourceFilter
+```
+
+The tree view and overview live in `vs/sessions` (sessions window only):
+
+```
 src/vs/sessions/contrib/aiCustomizationTreeView/browser/
 ├── aiCustomizationTreeView.contribution.ts     # View + actions
 ├── aiCustomizationTreeView.ts                  # IDs + menu IDs
 ├── aiCustomizationTreeViewViews.ts             # Tree data source + view
-├── aiCustomizationTreeViewIcons.ts             # Icons
-├── SPEC.md                                     # Feature specification
+├── aiCustomizationOverviewView.ts              # Overview view (counts + deep links)
 └── media/
     └── aiCustomizationTreeView.css
 ```
 
----
+Sessions-specific overrides:
 
-## Service Alignment (Required)
+```
+src/vs/sessions/contrib/chat/browser/
+├── aiCustomizationWorkspaceService.ts          # Sessions workspace service override
+└── promptsService.ts                           # AgenticPromptsService (CLI user roots)
+src/vs/sessions/contrib/sessions/browser/
+├── customizationCounts.ts                      # Source count utilities (type-aware)
+└── customizationsToolbar.contribution.ts       # Sidebar customization links
+```
 
-AI customizations must lean on existing VS Code services with well-defined interfaces. This avoids duplicated parsing logic, keeps discovery consistent across the workbench, and ensures prompt/hook behavior stays authoritative.
+### IAICustomizationWorkspaceService
 
-Browser compatibility is required. Do not use Node.js APIs; rely on VS Code services that work in browser contexts.
+The `IAICustomizationWorkspaceService` interface controls per-window behavior:
 
-Key services to rely on:
-- Prompt discovery, parsing, and lifecycle: [src/vs/workbench/contrib/chat/common/promptSyntax/service/promptsService.ts](../workbench/contrib/chat/common/promptSyntax/service/promptsService.ts)
-- Active session scoping for worktree filtering: [src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsService.ts](../workbench/contrib/chat/browser/agentSessions/agentSessionsService.ts)
-- MCP servers and tool access: [src/vs/workbench/contrib/mcp/common/mcpService.ts](../workbench/contrib/mcp/common/mcpService.ts)
-- MCP management and gallery: [src/vs/platform/mcp/common/mcpManagement.ts](../platform/mcp/common/mcpManagement.ts)
-- Chat models and session state: [src/vs/workbench/contrib/chat/common/chatService/chatService.ts](../workbench/contrib/chat/common/chatService/chatService.ts)
-- File and model plumbing: [src/vs/platform/files/common/files.ts](../platform/files/common/files.ts), [src/vs/editor/common/services/resolverService.ts](../editor/common/services/resolverService.ts)
+| Property / Method | Core VS Code | Sessions Window |
+|----------|-------------|----------|
+| `managementSections` | All sections except Models | Same minus MCP |
+| `getStorageSourceFilter(type)` | All sources, no user root filter | Per-type (see below) |
+| `isSessionsWindow` | `false` | `true` |
+| `activeProjectRoot` | First workspace folder | Active session worktree |
 
-The active worktree comes from `IActiveSessionService` and is the source of truth for any workspace/worktree scoping.
+### IStorageSourceFilter
 
-In the agentic workbench, prompt discovery is scoped by an agentic prompt service override that uses the active session root for workspace folders. See [src/vs/sessions/contrib/chat/browser/promptsService.ts](contrib/chat/browser/promptsService.ts).
+A unified per-type filter controlling which storage sources and user file roots are visible.
+Replaces the old `visibleStorageSources`, `getVisibleStorageSources(type)`, and `excludedUserFileRoots`.
 
-## Implemented Experience
+```typescript
+interface IStorageSourceFilter {
+  sources: readonly PromptsStorage[];         // Which storage groups to display
+  includedUserFileRoots?: readonly URI[];     // Allowlist for user roots (undefined = all)
+}
+```
 
-### Management Editor (Current)
+The shared `applyStorageSourceFilter()` helper applies this filter to any `{uri, storage}` array.
 
-- A singleton editor surfaces Agents, Skills, Instructions, Prompts, Hooks, MCP Servers, and Models.
-- Prompts-based sections use a grouped list (Worktree/User/Extensions) with search, context menus, and an embedded editor.
-- Embedded editor uses a full `CodeEditorWidget` and auto-commits worktree files on exit (agent session workflow).
-- Creation supports manual or AI-guided flows; AI-guided creation opens a new chat with hidden system instructions.
+**Sessions filter behavior by type:**
 
-### Tree View (Current)
+| Type | sources | includedUserFileRoots |
+|------|---------|----------------------|
+| Hooks | `[local]` | N/A |
+| Prompts | `[local, user]` | `undefined` (all roots) |
+| Agents, Skills, Instructions | `[local, user]` | `[~/.copilot, ~/.claude, ~/.agents]` |
 
-- Unified sidebar tree with Type -> Storage -> File hierarchy.
-- Auto-expands categories to reveal storage groups.
-- Context menus provide Open and Run Prompt.
-- Creation actions are centralized in the management editor.
+**Core VS Code:** All types use `[local, user, extension, plugin]` with no user root filter.
 
-### Additional Surfaces (Current)
+### AgenticPromptsService (Sessions)
 
-- Overview view provides counts and deep-links into the management editor.
-- Management list groups by storage with empty states, git status, and path copy actions.
+Sessions overrides `PromptsService` via `AgenticPromptsService` (in `promptsService.ts`):
 
----
+- **Discovery**: `AgenticPromptFilesLocator` scopes workspace folders to the active session's worktree
+- **Built-in prompts**: Discovers bundled `.prompt.md` files from `vs/sessions/prompts/` and surfaces them with `PromptsStorage.builtin` storage type
+- **User override**: Built-in prompts are omitted when a user or workspace prompt with the same name exists
+- **Creation targets**: `getSourceFolders()` override replaces VS Code profile user roots with `~/.copilot/{subfolder}` for CLI compatibility
+- **Hook folders**: Falls back to `.github/hooks` in the active worktree
 
-## AI Feature Gating
+### Built-in Prompts
 
-All commands and UI must respect `ChatContextKeys.enabled`:
+Prompt files bundled with the Sessions app live in `src/vs/sessions/prompts/`. They are:
 
-```typescript
-All entry points (view contributions, commands) respect `ChatContextKeys.enabled`.
-```
+- Discovered at runtime via `FileAccess.asFileUri('vs/sessions/prompts')`
+- Tagged with `PromptsStorage.builtin` storage type
+- Shown in a "Built-in" group in the AI Customization tree view and management editor
+- Filtered out when a user/workspace prompt shares the same clean name (override behavior)
+- Included in storage filters for prompts and CLI-user types
+
+### Count Consistency
+
+`customizationCounts.ts` uses the **same data sources** as the list widget's `loadItems()`:
+
+| Type | Data Source | Notes |
+|------|-------------|-------|
+| Agents | `getCustomAgents()` | Parsed agents, not raw files |
+| Skills | `findAgentSkills()` | Parsed skills with frontmatter |
+| Prompts | `getPromptSlashCommands()` | Filters out skill-type commands |
+| Instructions | `listPromptFiles()` + `listAgentInstructions()` | Includes AGENTS.md, CLAUDE.md etc. |
+| Hooks | `listPromptFiles()` | Raw hook files |
+
+### Debug Panel
+
+Toggle via Command Palette: "Toggle Customizations Debug Panel". Shows a 4-stage pipeline view:
+
+1. **Raw PromptsService data** — per-storage file lists + type-specific extras
+2. **After applyStorageSourceFilter** — what was removed and why
+3. **Widget state** — allItems vs displayEntries with group counts
+4. **Source/resolved folders** — creation targets and discovery order
+
+## Key Services
+
+- **Prompt discovery**: `IPromptsService` — parsing, lifecycle, storage enumeration
+- **MCP servers**: `IMcpService` — server list, tool access
+- **Active worktree**: `IActiveSessionService` — source of truth for workspace scoping (sessions only)
+- **File operations**: `IFileService`, `ITextModelService` — file and model plumbing
+
+Browser compatibility is required — no Node.js APIs.
+
+## Feature Gating
+
+All commands and UI respect `ChatContextKeys.enabled` and the `chat.customizationsMenu.enabled` setting.
 
----
+## Settings
 
-## References
+Settings use the `chat.customizationsMenu.` namespace:
 
-- [Settings Editor](../src/vs/workbench/contrib/preferences/browser/settingsEditor2.ts)
-- [Keybindings Editor](../src/vs/workbench/contrib/preferences/browser/keybindingsEditor.ts)
-- [Webview Editor](../src/vs/workbench/contrib/webviewPanel/browser/webviewEditorInput.ts)
-- [AI Customization Management (agentic)](../src/vs/sessions/contrib/aiCustomizationManagement/browser/)
-- [AI Customization Overview View](../src/vs/sessions/contrib/aiCustomizationManagement/browser/aiCustomizationOverviewView.ts)
-- [AI Customization Tree View (agentic)](../src/vs/sessions/contrib/aiCustomizationTreeView/browser/)
-- [IPromptsService](../src/vs/workbench/contrib/chat/common/promptSyntax/service/promptsService.ts)
+| Setting | Default | Description |
+|---------|---------|-------------|
+| `chat.customizationsMenu.enabled` | `true` | Show the Chat Customizations editor in the Command Palette |
diff --git a/src/vs/sessions/LAYOUT.md b/src/vs/sessions/LAYOUT.md
index fea9a1c370b86..ad54a086c7fb1 100644
--- a/src/vs/sessions/LAYOUT.md
+++ b/src/vs/sessions/LAYOUT.md
@@ -440,7 +440,7 @@ The `AuxiliaryBarPart` provides a custom `DropdownWithPrimaryActionViewItem` for
 
 The `SidebarPart` includes a footer section (35px height) positioned below the pane composite content. The sidebar uses a custom `layout()` override that reduces the content height by `FOOTER_HEIGHT` and renders a `MenuWorkbenchToolBar` driven by `Menus.SidebarFooter`. The footer hosts the account widget (see Section 3.6).
 
-On macOS native, the sidebar title area includes a traffic light spacer (70px) to push content past the system window controls, which is hidden in fullscreen mode.
+On macOS native with custom titlebar, the sidebar title area includes a traffic light spacer (70px) to push content past the system window controls. The spacer is hidden in fullscreen mode and is not created when using native titlebar (since the OS renders traffic lights in its own title bar).
 
 ---
 
@@ -640,6 +640,7 @@ interface IPartVisibilityState {
 
 | Date | Change |
 |------|--------|
+| 2026-03-02 | Fixed macOS sidebar traffic light spacer to only render with custom titlebar; added `!hasNativeTitlebar()` guard to `SidebarPart.createTitleArea()` so the 70px spacer is not created when using native titlebar (traffic lights are in the OS title bar, not overlapping the sidebar) |
 | 2026-02-20 | Replaced custom `EditorModal` with standard `ModalEditorPart` via `MODAL_GROUP`; main editor part created but hidden; changed `workbench.editor.useModal` from boolean to enum (`off`/`some`/`all`); sessions config uses `all`; removed `editorModal.ts` and editor modal CSS |
 | 2026-02-17 | Added `-webkit-app-region: drag` to sidebar title area so it can be used to drag the window; interactive children (actions, composite bar, labels) marked `no-drag`; CSS rules scoped to `.agent-sessions-workbench` in `parts/media/sidebarPart.css` |
 | 2026-02-13 | Documentation sync: Updated all file names, class names, and references to match current implementation. `AgenticWorkbench` → `Workbench`, `AgenticSidebarPart` → `SidebarPart`, `AgenticAuxiliaryBarPart` → `AuxiliaryBarPart`, `AgenticPanelPart` → `PanelPart`, `agenticWorkbench.ts` → `workbench.ts`, `agenticWorkbenchMenus.ts` → `menus.ts`, `agenticLayoutActions.ts` → `layoutActions.ts`, `AgenticTitleBarWidget` → `SessionsTitleBarWidget`, `AgenticTitleBarContribution` → `SessionsTitleBarContribution`. Removed references to deleted files (`sidebarRevealButton.ts`, `floatingToolbar.ts`, `agentic.contributions.ts`, `agenticTitleBarWidget.ts`). Updated pane composite architecture from `SyncDescriptor`-based to `AgenticPaneCompositePartService`. Moved account widget docs from titlebar to sidebar footer. Added documentation for sidebar footer, project bar, traffic light spacer, card appearance styling, widget directory, and new contrib structure (`accountMenu/`, `chat/`, `configuration/`, `sessions/`). Updated titlebar actions to reflect Run Script split button and Open submenu. Removed Toggle Maximize panel action (no longer registered). Updated contributions section with all current contributions and their locations. |
diff --git a/src/vs/sessions/browser/layoutActions.ts b/src/vs/sessions/browser/layoutActions.ts
index 39f7697ed7280..c9bf983b7c963 100644
--- a/src/vs/sessions/browser/layoutActions.ts
+++ b/src/vs/sessions/browser/layoutActions.ts
@@ -9,12 +9,14 @@ import { KeyCode, KeyMod } from '../../base/common/keyCodes.js';
 import { localize, localize2 } from '../../nls.js';
 import { Categories } from '../../platform/action/common/actionCommonCategories.js';
 import { Action2, MenuRegistry, registerAction2 } from '../../platform/actions/common/actions.js';
+import { ContextKeyExpr } from '../../platform/contextkey/common/contextkey.js';
 import { Menus } from './menus.js';
 import { ServicesAccessor } from '../../platform/instantiation/common/instantiation.js';
 import { KeybindingWeight } from '../../platform/keybinding/common/keybindingsRegistry.js';
 import { registerIcon } from '../../platform/theme/common/iconRegistry.js';
 import { AuxiliaryBarVisibleContext, IsAuxiliaryWindowContext, IsWindowAlwaysOnTopContext, SideBarVisibleContext } from '../../workbench/common/contextkeys.js';
 import { IWorkbenchLayoutService, Parts } from '../../workbench/services/layout/browser/layoutService.js';
+import { SessionsWelcomeVisibleContext } from '../common/contextkeys.js';
 
 // Register Icons
 const panelLeftIcon = registerIcon('agent-panel-left', Codicon.layoutSidebarLeft, localize('panelLeft', "Represents a side bar in the left position"));
@@ -50,10 +52,10 @@ class ToggleSidebarVisibilityAction extends Action2 {
 			},
 			menu: [
 				{
-					id: Menus.TitleBarLeft,
+					id: Menus.TitleBarLeftLayout,
 					group: 'navigation',
 					order: 0,
-					when: IsAuxiliaryWindowContext.toNegated()
+					when: ContextKeyExpr.and(IsAuxiliaryWindowContext.toNegated(), SessionsWelcomeVisibleContext.toNegated())
 				},
 				{
 					id: Menus.TitleBarContext,
@@ -102,10 +104,10 @@ class ToggleSecondarySidebarVisibilityAction extends Action2 {
 			f1: true,
 			menu: [
 				{
-					id: Menus.TitleBarRight,
+					id: Menus.TitleBarRightLayout,
 					group: 'navigation',
 					order: 10,
-					when: IsAuxiliaryWindowContext.toNegated()
+					when: ContextKeyExpr.and(IsAuxiliaryWindowContext.toNegated(), SessionsWelcomeVisibleContext.toNegated())
 				},
 				{
 					id: Menus.TitleBarContext,
@@ -163,7 +165,7 @@ registerAction2(ToggleSecondarySidebarVisibilityAction);
 registerAction2(TogglePanelVisibilityAction);
 
 // Floating window controls: always-on-top
-MenuRegistry.appendMenuItem(Menus.TitleBarRight, {
+MenuRegistry.appendMenuItem(Menus.TitleBarRightLayout, {
 	command: {
 		id: 'workbench.action.toggleWindowAlwaysOnTop',
 		title: localize('toggleWindowAlwaysOnTop', "Toggle Always on Top"),
diff --git a/src/vs/sessions/browser/media/style.css b/src/vs/sessions/browser/media/style.css
index 1ba1c29e04b1b..0a57fa73f7d0c 100644
--- a/src/vs/sessions/browser/media/style.css
+++ b/src/vs/sessions/browser/media/style.css
@@ -43,14 +43,42 @@
 	background-color: var(--vscode-sideBar-background);
 }
 
+/* ---- Chat Layout ---- */
+
+/* Remove max-width from the session container so the scrollbar extends full width */
+.agent-sessions-workbench .interactive-session {
+	max-width: none;
+}
+
+/* Constrain content items to the same max-width, centered */
+.agent-sessions-workbench .interactive-session .interactive-item-container {
+	max-width: 950px;
+	margin: 0 auto;
+	padding-left: 8px;
+	padding-right: 8px;
+	box-sizing: border-box;
+}
+
+.agent-sessions-workbench .interactive-session > .chat-suggest-next-widget {
+	max-width: 950px;
+	margin: 0 auto;
+	padding-left: 8px;
+	padding-right: 8px;
+	box-sizing: border-box;
+}
+
 /* ---- Chat Input ---- */
 
 .agent-sessions-workbench .interactive-session .chat-input-container {
-	border-radius: 8px !important;
+	border-radius: var(--vscode-cornerRadius-large) !important;
 }
 
 .agent-sessions-workbench .interactive-session .interactive-input-part {
-	margin: 0 8px !important;
+	width: 100%;
+	max-width: 950px;
+	margin: 0 auto !important;
 	display: inherit !important;
-	padding: 4px 0 8px 0px !important;
+	/* Align with panel (terminal) card margin */
+	padding: 4px 8px 6px 8px !important;
+	box-sizing: border-box;
 }
diff --git a/src/vs/sessions/browser/menus.ts b/src/vs/sessions/browser/menus.ts
index ed06a0221d951..c322fba968b6b 100644
--- a/src/vs/sessions/browser/menus.ts
+++ b/src/vs/sessions/browser/menus.ts
@@ -13,11 +13,10 @@ export const Menus = {
 	CommandCenter: new MenuId('SessionsCommandCenter'),
 	CommandCenterCenter: new MenuId('SessionsCommandCenterCenter'),
 	TitleBarContext: new MenuId('SessionsTitleBarContext'),
-	TitleBarControlMenu: new MenuId('SessionsTitleBarControlMenu'),
-	TitleBarLeft: new MenuId('SessionsTitleBarLeft'),
-	TitleBarCenter: new MenuId('SessionsTitleBarCenter'),
-	TitleBarRight: new MenuId('SessionsTitleBarRight'),
-	OpenSubMenu: new MenuId('SessionsOpenSubMenu'),
+	TitleBarLeftLayout: new MenuId('SessionsTitleBarLeftLayout'),
+	TitleBarSessionTitle: new MenuId('SessionsTitleBarSessionTitle'),
+	TitleBarSessionMenu: new MenuId('SessionsTitleBarSessionMenu'),
+	TitleBarRightLayout: new MenuId('SessionsTitleBarRightLayout'),
 	PanelTitle: new MenuId('SessionsPanelTitle'),
 	SidebarTitle: new MenuId('SessionsSidebarTitle'),
 	AuxiliaryBarTitle: new MenuId('SessionsAuxiliaryBarTitle'),
diff --git a/src/vs/sessions/browser/parts/auxiliaryBarPart.ts b/src/vs/sessions/browser/parts/auxiliaryBarPart.ts
index c7dbddc3e33c3..cef38cedc82ec 100644
--- a/src/vs/sessions/browser/parts/auxiliaryBarPart.ts
+++ b/src/vs/sessions/browser/parts/auxiliaryBarPart.ts
@@ -12,8 +12,9 @@ import { INotificationService } from '../../../platform/notification/common/noti
 import { IStorageService } from '../../../platform/storage/common/storage.js';
 import { IThemeService } from '../../../platform/theme/common/themeService.js';
 import { ActiveAuxiliaryContext, AuxiliaryBarFocusContext } from '../../../workbench/common/contextkeys.js';
-import { ACTIVITY_BAR_BADGE_BACKGROUND, ACTIVITY_BAR_BADGE_FOREGROUND, ACTIVITY_BAR_TOP_ACTIVE_BORDER, ACTIVITY_BAR_TOP_DRAG_AND_DROP_BORDER, ACTIVITY_BAR_TOP_FOREGROUND, ACTIVITY_BAR_TOP_INACTIVE_FOREGROUND, PANEL_ACTIVE_TITLE_BORDER, PANEL_ACTIVE_TITLE_FOREGROUND, PANEL_DRAG_AND_DROP_BORDER, PANEL_INACTIVE_TITLE_FOREGROUND, SIDE_BAR_BACKGROUND, SIDE_BAR_BORDER, SIDE_BAR_TITLE_BORDER, SIDE_BAR_FOREGROUND } from '../../../workbench/common/theme.js';
+import { ACTIVITY_BAR_BADGE_BACKGROUND, ACTIVITY_BAR_BADGE_FOREGROUND, ACTIVITY_BAR_TOP_ACTIVE_BORDER, ACTIVITY_BAR_TOP_DRAG_AND_DROP_BORDER, ACTIVITY_BAR_TOP_FOREGROUND, ACTIVITY_BAR_TOP_INACTIVE_FOREGROUND, PANEL_ACTIVE_TITLE_BORDER, PANEL_ACTIVE_TITLE_FOREGROUND, PANEL_DRAG_AND_DROP_BORDER, PANEL_INACTIVE_TITLE_FOREGROUND, SIDE_BAR_BACKGROUND, SIDE_BAR_TITLE_BORDER, SIDE_BAR_FOREGROUND } from '../../../workbench/common/theme.js';
 import { contrastBorder } from '../../../platform/theme/common/colorRegistry.js';
+import { sessionsSidebarBorder } from '../../common/theme.js';
 import { IViewDescriptorService, ViewContainerLocation } from '../../../workbench/common/views.js';
 import { IExtensionService } from '../../../workbench/services/extensions/common/extensions.js';
 import { IWorkbenchLayoutService, Parts } from '../../../workbench/services/layout/browser/layoutService.js';
@@ -81,7 +82,7 @@ export class AuxiliaryBarPart extends AbstractPaneCompositePart {
 			return undefined;
 		}
 
-		return Math.max(width, 300);
+		return Math.max(width, 340);
 	}
 
 	readonly priority = LayoutPriority.Low;
@@ -105,7 +106,7 @@ export class AuxiliaryBarPart extends AbstractPaneCompositePart {
 			{
 				hasTitle: true,
 				trailingSeparator: false,
-				borderWidth: () => (this.getColor(SIDE_BAR_BORDER) || this.getColor(contrastBorder)) ? 1 : 0,
+				borderWidth: () => (this.getColor(sessionsSidebarBorder) || this.getColor(contrastBorder)) ? 1 : 0,
 			},
 			AuxiliaryBarPart.activeViewSettingsKey,
 			ActiveAuxiliaryContext.bindTo(contextKeyService),
@@ -141,7 +142,7 @@ export class AuxiliaryBarPart extends AbstractPaneCompositePart {
 
 		// Store background and border as CSS variables for the card styling on .part
 		container.style.setProperty('--part-background', this.getColor(SIDE_BAR_BACKGROUND) || '');
-		container.style.setProperty('--part-border-color', this.getColor(SIDE_BAR_BORDER) || this.getColor(contrastBorder) || 'transparent');
+		container.style.setProperty('--part-border-color', this.getColor(sessionsSidebarBorder) || this.getColor(contrastBorder) || 'transparent');
 		container.style.backgroundColor = 'transparent';
 		container.style.color = this.getColor(SIDE_BAR_FOREGROUND) || '';
 
diff --git a/src/vs/sessions/browser/parts/chatBarPart.ts b/src/vs/sessions/browser/parts/chatBarPart.ts
index 9a74bb7021bd0..ebafc12e5c3b5 100644
--- a/src/vs/sessions/browser/parts/chatBarPart.ts
+++ b/src/vs/sessions/browser/parts/chatBarPart.ts
@@ -34,8 +34,7 @@ export class ChatBarPart extends AbstractPaneCompositePart {
 	static readonly placeholderViewContainersKey = 'workbench.chatbar.placeholderPanels';
 	static readonly viewContainersWorkspaceStateKey = 'workbench.chatbar.viewContainersWorkspaceState';
 
-	// Use the side bar dimensions
-	override readonly minimumWidth: number = 170;
+	override readonly minimumWidth: number = 300;
 	override readonly maximumWidth: number = Number.POSITIVE_INFINITY;
 	override readonly minimumHeight: number = 0;
 	override readonly maximumHeight: number = Number.POSITIVE_INFINITY;
@@ -44,21 +43,6 @@ export class ChatBarPart extends AbstractPaneCompositePart {
 		return this.layoutService.mainContainerDimension.height * 0.4;
 	}
 
-	get preferredWidth(): number | undefined {
-		const activeComposite = this.getActivePaneComposite();
-
-		if (!activeComposite) {
-			return undefined;
-		}
-
-		const width = activeComposite.getOptimalWidth();
-		if (typeof width !== 'number') {
-			return undefined;
-		}
-
-		return Math.max(width, 300);
-	}
-
 	readonly priority = LayoutPriority.High;
 
 	constructor(
diff --git a/src/vs/sessions/browser/parts/media/titlebarpart.css b/src/vs/sessions/browser/parts/media/titlebarpart.css
index 22273655103c7..146ed67fa619d 100644
--- a/src/vs/sessions/browser/parts/media/titlebarpart.css
+++ b/src/vs/sessions/browser/parts/media/titlebarpart.css
@@ -3,8 +3,81 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-left {
+	display: flex;
+	height: 100%;
+	align-items: center;
+	order: 0;
+	flex-grow: 0;
+	flex-shrink: 0;
+	width: auto;
+	justify-content: flex-start;
+}
+
+.monaco-workbench .part.titlebar > .sessions-titlebar-container.has-center > .titlebar-center {
+	order: 1;
+	width: auto;
+	flex-grow: 0;
+	flex-shrink: 1;
+	min-width: 0px;
+	margin: 0;
+	justify-content: flex-start;
+}
+
+.agent-sessions-workbench.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-left {
+	width: fit-content;
+	flex-grow: 0;
+}
+
+.agent-sessions-workbench.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-center {
+	flex: 1;
+	max-width: none;
+}
+
+.agent-sessions-workbench.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-center .window-title {
+	margin: unset;
+}
+
+.agent-sessions-workbench.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-right {
+	order: 2;
+	width: fit-content;
+	flex-grow: 0;
+	justify-content: flex-end;
+	margin-right: 10px;
+}
+
+/* Session Title Actions Container (before right toolbar) */
+.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-right > .titlebar-actions-container {
+	display: none;
+	flex-shrink: 0;
+	-webkit-app-region: no-drag;
+	height: 100%;
+}
+
+.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-right > .titlebar-actions-container:not(.has-no-actions) {
+	display: flex;
+	align-items: center;
+}
+
+/* Separator between session actions and layout actions toolbar */
+.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-right > .titlebar-session-actions-container:not(.has-no-actions) + .titlebar-layout-actions-container:not(.has-no-actions)::before {
+	content: '';
+	width: 1px;
+	height: 16px;
+	margin: 0 4px;
+	background-color: var(--vscode-disabledForeground);
+}
+
+.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-right > .titlebar-actions-container .codicon {
+	color: inherit;
+}
+
+.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-right > .titlebar-actions-container .monaco-action-bar .action-item {
+	display: flex;
+}
+
 /* Left Tool Bar Container */
-.monaco-workbench .part.titlebar > .titlebar-container > .titlebar-left > .left-toolbar-container {
+.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-left > .left-toolbar-container {
 	display: none;
 	padding-left: 8px;
 	flex-grow: 0;
@@ -17,25 +90,22 @@
 	order: 2;
 }
 
-.monaco-workbench .part.titlebar > .titlebar-container > .titlebar-left > .left-toolbar-container:not(.has-no-actions) {
+.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-left > .left-toolbar-container:not(.has-no-actions) {
 	display: flex;
 	justify-content: center;
 	align-items: center;
 }
 
-.monaco-workbench .part.titlebar > .titlebar-container > .titlebar-left > .left-toolbar-container .codicon {
+.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-left > .left-toolbar-container .codicon {
 	color: inherit;
 }
 
-.monaco-workbench .part.titlebar > .titlebar-container > .titlebar-left > .left-toolbar-container .monaco-action-bar .action-item {
+.monaco-workbench .part.titlebar > .sessions-titlebar-container > .titlebar-left > .left-toolbar-container .monaco-action-bar .action-item {
 	display: flex;
 }
 
-/* TODO: Hack to avoid flicker when sidebar becomes visible.
- * The contribution swaps the menu item synchronously, but the toolbar
- * re-render is async, causing a brief flash. Hide the container via
- * CSS when sidebar is visible (nosidebar class is removed synchronously). */
-.agent-sessions-workbench:not(.nosidebar) .part.titlebar > .titlebar-container > .titlebar-left > .left-toolbar-container {
+/* Hide the entire titlebar left when the sidebar is visible */
+.agent-sessions-workbench:not(.nosidebar) .part.titlebar > .sessions-titlebar-container > .titlebar-left {
 	display: none !important;
 }
 
diff --git a/src/vs/sessions/browser/parts/panelPart.ts b/src/vs/sessions/browser/parts/panelPart.ts
index 867760bd11228..2fccc865f15e1 100644
--- a/src/vs/sessions/browser/parts/panelPart.ts
+++ b/src/vs/sessions/browser/parts/panelPart.ts
@@ -14,8 +14,9 @@ import { IContextMenuService } from '../../../platform/contextview/browser/conte
 import { IKeybindingService } from '../../../platform/keybinding/common/keybinding.js';
 import { IInstantiationService } from '../../../platform/instantiation/common/instantiation.js';
 import { IThemeService } from '../../../platform/theme/common/themeService.js';
-import { PANEL_BACKGROUND, PANEL_BORDER, PANEL_TITLE_BORDER, PANEL_ACTIVE_TITLE_FOREGROUND, PANEL_INACTIVE_TITLE_FOREGROUND, PANEL_ACTIVE_TITLE_BORDER, PANEL_DRAG_AND_DROP_BORDER, PANEL_TITLE_BADGE_BACKGROUND, PANEL_TITLE_BADGE_FOREGROUND } from '../../../workbench/common/theme.js';
+import { PANEL_BACKGROUND, PANEL_TITLE_BORDER, PANEL_ACTIVE_TITLE_FOREGROUND, PANEL_INACTIVE_TITLE_FOREGROUND, PANEL_ACTIVE_TITLE_BORDER, PANEL_DRAG_AND_DROP_BORDER, PANEL_TITLE_BADGE_BACKGROUND, PANEL_TITLE_BADGE_FOREGROUND } from '../../../workbench/common/theme.js';
 import { contrastBorder } from '../../../platform/theme/common/colorRegistry.js';
+import { sessionsSidebarBorder } from '../../common/theme.js';
 import { INotificationService } from '../../../platform/notification/common/notification.js';
 import { IContextKeyService } from '../../../platform/contextkey/common/contextkey.js';
 import { assertReturnsDefined } from '../../../base/common/types.js';
@@ -129,7 +130,7 @@ export class PanelPart extends AbstractPaneCompositePart {
 
 		// Store background and border as CSS variables for the card styling on .part
 		container.style.setProperty('--part-background', this.getColor(PANEL_BACKGROUND) || '');
-		container.style.setProperty('--part-border-color', this.getColor(PANEL_BORDER) || this.getColor(contrastBorder) || 'transparent');
+		container.style.setProperty('--part-border-color', this.getColor(sessionsSidebarBorder) || this.getColor(contrastBorder) || 'transparent');
 		container.style.backgroundColor = 'transparent';
 
 		// Clear inline borders - the card appearance uses CSS border-radius instead
diff --git a/src/vs/sessions/browser/parts/sidebarPart.ts b/src/vs/sessions/browser/parts/sidebarPart.ts
index 5f8cce31cf807..75eb74869ddc4 100644
--- a/src/vs/sessions/browser/parts/sidebarPart.ts
+++ b/src/vs/sessions/browser/parts/sidebarPart.ts
@@ -38,6 +38,8 @@ import { HiddenItemStrategy, MenuWorkbenchToolBar } from '../../../platform/acti
 import { isMacintosh, isNative } from '../../../base/common/platform.js';
 import { isFullscreen, onDidChangeFullscreen } from '../../../base/browser/browser.js';
 import { mainWindow } from '../../../base/browser/window.js';
+import { IConfigurationService } from '../../../platform/configuration/common/configuration.js';
+import { hasNativeTitlebar, getTitleBarStyle } from '../../../platform/window/common/window.js';
 
 /**
  * Sidebar part specifically for agent sessions workbench.
@@ -103,6 +105,7 @@ export class SidebarPart extends AbstractPaneCompositePart {
 		@IContextKeyService contextKeyService: IContextKeyService,
 		@IExtensionService extensionService: IExtensionService,
 		@IMenuService menuService: IMenuService,
+		@IConfigurationService private readonly configurationService: IConfigurationService,
 	) {
 		super(
 			Parts.SIDEBAR_PART,
@@ -117,7 +120,7 @@ export class SidebarPart extends AbstractPaneCompositePart {
 			ViewContainerLocation.Sidebar,
 			Extensions.Viewlets,
 			Menus.SidebarTitle,
-			Menus.TitleBarLeft,
+			Menus.TitleBarLeftLayout,
 			notificationService,
 			storageService,
 			contextMenuService,
@@ -151,7 +154,7 @@ export class SidebarPart extends AbstractPaneCompositePart {
 		// macOS native: the sidebar spans full height and the traffic lights
 		// overlay the top-left corner. Add a fixed-width spacer inside the
 		// title area to push content horizontally past the traffic lights.
-		if (titleArea && isMacintosh && isNative) {
+		if (titleArea && isMacintosh && isNative && !hasNativeTitlebar(this.configurationService, getTitleBarStyle(this.configurationService))) {
 			const spacer = $('div.window-controls-container');
 			spacer.style.width = '70px';
 			spacer.style.height = '100%';
diff --git a/src/vs/sessions/browser/parts/titlebarPart.ts b/src/vs/sessions/browser/parts/titlebarPart.ts
index 8eab246ab644e..18c2d2867f08d 100644
--- a/src/vs/sessions/browser/parts/titlebarPart.ts
+++ b/src/vs/sessions/browser/parts/titlebarPart.ts
@@ -18,7 +18,7 @@ import { WORKBENCH_BACKGROUND } from '../../../workbench/common/theme.js';
 import { chatBarTitleBackground, chatBarTitleForeground } from '../../common/theme.js';
 import { isMacintosh, isWeb, isNative, platformLocale } from '../../../base/common/platform.js';
 import { Color } from '../../../base/common/color.js';
-import { EventType, EventHelper, Dimension, append, $, addDisposableListener, prepend, getWindow, getWindowId } from '../../../base/browser/dom.js';
+import { EventType, EventHelper, append, $, addDisposableListener, prepend, getWindow, getWindowId } from '../../../base/browser/dom.js';
 import { IInstantiationService } from '../../../platform/instantiation/common/instantiation.js';
 import { Emitter, Event } from '../../../base/common/event.js';
 import { IStorageService } from '../../../platform/storage/common/storage.js';
@@ -132,7 +132,7 @@ export class TitlebarPart extends Part implements ITitlebarPart {
 
 	protected override createContentArea(parent: HTMLElement): HTMLElement {
 		this.element = parent;
-		this.rootContainer = append(parent, $('.titlebar-container.has-center'));
+		this.rootContainer = append(parent, $('.titlebar-container.sessions-titlebar-container.has-center'));
 
 		// Draggable region
 		prepend(this.rootContainer, $('div.titlebar-drag-region'));
@@ -185,7 +185,7 @@ export class TitlebarPart extends Part implements ITitlebarPart {
 
 		// Left toolbar (driven by Menus.TitleBarLeft, rendered after window controls via CSS order)
 		const leftToolbarContainer = append(this.leftContent, $('div.left-toolbar-container'));
-		this._register(this.instantiationService.createInstance(MenuWorkbenchToolBar, leftToolbarContainer, Menus.TitleBarLeft, {
+		this._register(this.instantiationService.createInstance(MenuWorkbenchToolBar, leftToolbarContainer, Menus.TitleBarLeftLayout, {
 			contextMenu: Menus.TitleBarContext,
 			telemetrySource: 'titlePart.left',
 			hiddenItemStrategy: HiddenItemStrategy.NoHide,
@@ -204,13 +204,22 @@ export class TitlebarPart extends Part implements ITitlebarPart {
 		}));
 
 		// Right toolbar (driven by Menus.TitleBarRight - includes account submenu)
-		const rightToolbarContainer = prepend(this.rightContent, $('div.action-toolbar-container'));
-		this._register(this.instantiationService.createInstance(MenuWorkbenchToolBar, rightToolbarContainer, Menus.TitleBarRight, {
+		const rightToolbarContainer = prepend(this.rightContent, $('div.titlebar-actions-container.titlebar-layout-actions-container'));
+		this._register(this.instantiationService.createInstance(MenuWorkbenchToolBar, rightToolbarContainer, Menus.TitleBarRightLayout, {
 			contextMenu: Menus.TitleBarContext,
 			telemetrySource: 'titlePart.right',
 			toolbarOptions: { primaryGroup: () => true },
 		}));
 
+		// Session title actions toolbar (before right toolbar)
+		const sessionActionsContainer = prepend(this.rightContent, $('div.titlebar-actions-container.titlebar-session-actions-container'));
+		this._register(this.instantiationService.createInstance(MenuWorkbenchToolBar, sessionActionsContainer, Menus.TitleBarSessionMenu, {
+			contextMenu: Menus.TitleBarContext,
+			hiddenItemStrategy: HiddenItemStrategy.NoHide,
+			telemetrySource: 'titlePart.sessionActions',
+			toolbarOptions: { primaryGroup: () => true },
+		}));
+
 		// Context menu on the titlebar
 		this._register(addDisposableListener(this.rootContainer, EventType.CONTEXT_MENU, e => {
 			EventHelper.stop(e);
@@ -254,8 +263,6 @@ export class TitlebarPart extends Part implements ITitlebarPart {
 		});
 	}
 
-	private lastLayoutDimension: Dimension | undefined;
-
 	get hasZoomableElements(): boolean {
 		return true; // sessions titlebar always has command center and toolbar actions
 	}
@@ -268,7 +275,6 @@ export class TitlebarPart extends Part implements ITitlebarPart {
 	}
 
 	override layout(width: number, height: number): void {
-		this.lastLayoutDimension = new Dimension(width, height);
 		this.updateLayout();
 		super.layoutContents(width, height);
 	}
@@ -281,24 +287,6 @@ export class TitlebarPart extends Part implements ITitlebarPart {
 		const zoomFactor = getZoomFactor(getWindow(this.element));
 		this.element.style.setProperty('--zoom-factor', zoomFactor.toString());
 		this.rootContainer.classList.toggle('counter-zoom', this.preventZoom);
-
-		this.updateCenterOffset();
-	}
-
-	private updateCenterOffset(): void {
-		if (!this.centerContent || !this.lastLayoutDimension) {
-			return;
-		}
-
-		// Center the command center relative to the viewport.
-		// The titlebar only covers the right section (sidebar is to the left),
-		// so we shift the center content left by half the sidebar width
-		// using a negative margin.
-		const windowWidth = this.layoutService.mainContainerDimension.width;
-		const titlebarWidth = this.lastLayoutDimension.width;
-		const leftOffset = windowWidth - titlebarWidth;
-		this.centerContent.style.marginLeft = leftOffset > 0 ? `${-leftOffset / 2}px` : '';
-		this.centerContent.style.marginRight = leftOffset > 0 ? `${leftOffset / 2}px` : '';
 	}
 
 	focus(): void {
diff --git a/src/vs/sessions/browser/web.factory.ts b/src/vs/sessions/browser/web.factory.ts
new file mode 100644
index 0000000000000..e33129acea8a8
--- /dev/null
+++ b/src/vs/sessions/browser/web.factory.ts
@@ -0,0 +1,34 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { IWorkbench, IWorkbenchConstructionOptions } from '../../workbench/browser/web.api.js';
+import { SessionsBrowserMain } from './web.main.js';
+import { IDisposable, toDisposable } from '../../base/common/lifecycle.js';
+import { mark } from '../../base/common/performance.js';
+import { DeferredPromise } from '../../base/common/async.js';
+
+const workbenchPromise = new DeferredPromise<IWorkbench>();
+
+/**
+ * Creates the Sessions workbench with the provided options in the provided container.
+ */
+export function create(domElement: HTMLElement, options: IWorkbenchConstructionOptions): IDisposable {
+
+	mark('code/didLoadWorkbenchMain');
+
+	let instantiatedWorkbench: IWorkbench | undefined = undefined;
+	new SessionsBrowserMain(domElement, options).open().then(workbench => {
+		instantiatedWorkbench = workbench;
+		workbenchPromise.complete(workbench);
+	});
+
+	return toDisposable(() => {
+		if (instantiatedWorkbench) {
+			instantiatedWorkbench.shutdown();
+		} else {
+			workbenchPromise.p.then(w => w.shutdown());
+		}
+	});
+}
diff --git a/src/vs/sessions/browser/web.main.ts b/src/vs/sessions/browser/web.main.ts
new file mode 100644
index 0000000000000..0c57fb902f6c8
--- /dev/null
+++ b/src/vs/sessions/browser/web.main.ts
@@ -0,0 +1,17 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { ServiceCollection } from '../../platform/instantiation/common/serviceCollection.js';
+import { ILogService } from '../../platform/log/common/log.js';
+import { BrowserMain, IBrowserMainWorkbench } from '../../workbench/browser/web.main.js';
+import { Workbench as SessionsWorkbench } from './workbench.js';
+
+export class SessionsBrowserMain extends BrowserMain {
+
+	protected override createWorkbench(domElement: HTMLElement, serviceCollection: ServiceCollection, logService: ILogService): IBrowserMainWorkbench {
+		console.log('[Sessions Web] Creating Sessions workbench (not standard workbench)');
+		return new SessionsWorkbench(domElement, undefined, serviceCollection, logService);
+	}
+}
diff --git a/src/vs/sessions/browser/workbench.ts b/src/vs/sessions/browser/workbench.ts
index 66e41f3a74276..b94d04f64be03 100644
--- a/src/vs/sessions/browser/workbench.ts
+++ b/src/vs/sessions/browser/workbench.ts
@@ -81,6 +81,7 @@ enum LayoutClasses {
 	PANEL_HIDDEN = 'nopanel',
 	AUXILIARYBAR_HIDDEN = 'noauxiliarybar',
 	CHATBAR_HIDDEN = 'nochatbar',
+	STATUSBAR_HIDDEN = 'nostatusbar',
 	FULLSCREEN = 'fullscreen',
 	MAXIMIZED = 'maximized'
 }
@@ -398,15 +399,6 @@ export class Workbench extends Disposable implements IWorkbenchLayoutService {
 		// Wrap up
 		instantiationService.invokeFunction(accessor => {
 			const lifecycleService = accessor.get(ILifecycleService);
-
-			// TODO@Sandeep debt around cyclic dependencies
-			const configurationService = accessor.get(IConfigurationService);
-			// eslint-disable-next-line local/code-no-in-operator
-			if (configurationService && 'acquireInstantiationService' in configurationService) {
-				(configurationService as { acquireInstantiationService: (instantiationService: unknown) => void }).acquireInstantiationService(instantiationService);
-			}
-
-			// Signal to lifecycle that services are set
 			lifecycleService.phase = LifecyclePhase.Ready;
 		});
 
@@ -599,6 +591,8 @@ export class Workbench extends Disposable implements IWorkbenchLayoutService {
 		this.getPart(Parts.EDITOR_PART).create(editorPartContainer, { restorePreviousState: false });
 		mark('code/didCreatePart/workbench.parts.editor');
 
+		this.getPart(Parts.EDITOR_PART).layout(0, 0, 0, 0); // needed to make some view methods work
+
 		this.mainContainer.appendChild(editorPartContainer);
 	}
 
@@ -789,7 +783,7 @@ export class Workbench extends Disposable implements IWorkbenchLayoutService {
 
 		// Default sizes
 		const sideBarSize = 300;
-		const auxiliaryBarSize = 300;
+		const auxiliaryBarSize = 340;
 		const panelSize = 300;
 		const titleBarHeight = this.titleBarPartView?.minimumHeight ?? 30;
 
@@ -902,6 +896,7 @@ export class Workbench extends Disposable implements IWorkbenchLayoutService {
 			!this.partVisibility.panel ? LayoutClasses.PANEL_HIDDEN : undefined,
 			!this.partVisibility.auxiliaryBar ? LayoutClasses.AUXILIARYBAR_HIDDEN : undefined,
 			!this.partVisibility.chatBar ? LayoutClasses.CHATBAR_HIDDEN : undefined,
+			LayoutClasses.STATUSBAR_HIDDEN, // sessions window never has a status bar
 			this.mainWindowFullscreen ? LayoutClasses.FULLSCREEN : undefined
 		]);
 	}
diff --git a/src/vs/sessions/common/contextkeys.ts b/src/vs/sessions/common/contextkeys.ts
index d95d7411ac4cf..76d7136d14c5a 100644
--- a/src/vs/sessions/common/contextkeys.ts
+++ b/src/vs/sessions/common/contextkeys.ts
@@ -6,12 +6,6 @@
 import { localize } from '../../nls.js';
 import { RawContextKey } from '../../platform/contextkey/common/contextkey.js';
 
-//#region < --- Welcome --- >
-
-export const SessionsWelcomeCompleteContext = new RawContextKey<boolean>('sessionsWelcomeComplete', false, localize('sessionsWelcomeComplete', "Whether the sessions welcome setup is complete"));
-
-//#endregion
-
 //#region < --- Chat Bar --- >
 
 export const ActiveChatBarContext = new RawContextKey<string>('activeChatBar', '', localize('activeChatBar', "The identifier of the active chat bar panel"));
@@ -19,3 +13,9 @@ export const ChatBarFocusContext = new RawContextKey<boolean>('chatBarFocus', fa
 export const ChatBarVisibleContext = new RawContextKey<boolean>('chatBarVisible', false, localize('chatBarVisible', "Whether the chat bar is visible"));
 
 //#endregion
+
+//#region < --- Welcome --- >
+
+export const SessionsWelcomeVisibleContext = new RawContextKey<boolean>('sessionsWelcomeVisible', false, localize('sessionsWelcomeVisible', "Whether the sessions welcome overlay is visible"));
+
+//#endregion
diff --git a/src/vs/sessions/common/theme.ts b/src/vs/sessions/common/theme.ts
index 4d17842818037..2f928d12aecbb 100644
--- a/src/vs/sessions/common/theme.ts
+++ b/src/vs/sessions/common/theme.ts
@@ -4,9 +4,10 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { localize } from '../../nls.js';
-import { registerColor } from '../../platform/theme/common/colorUtils.js';
-import { contrastBorder } from '../../platform/theme/common/colorRegistry.js';
+import { registerColor, transparent } from '../../platform/theme/common/colorUtils.js';
+import { contrastBorder, iconForeground } from '../../platform/theme/common/colorRegistry.js';
 import { Color } from '../../base/common/color.js';
+import { buttonBackground } from '../../platform/theme/common/colors/inputColors.js';
 import { SIDE_BAR_BACKGROUND, SIDE_BAR_FOREGROUND } from '../../workbench/common/theme.js';
 
 // Sessions sidebar background color
@@ -48,3 +49,23 @@ export const chatBarTitleForeground = registerColor(
 	SIDE_BAR_FOREGROUND,
 	localize('chatBarTitle.foreground', 'Foreground color of the chat bar title area in the agent sessions window.')
 );
+
+// Agent feedback input widget border color
+export const agentFeedbackInputWidgetBorder = registerColor(
+	'agentFeedbackInputWidget.border',
+	{ dark: transparent(iconForeground, 0.8), light: transparent(iconForeground, 0.8), hcDark: contrastBorder, hcLight: contrastBorder },
+	localize('agentFeedbackInputWidget.border', 'Border color of the agent feedback input widget shown in the editor.')
+);
+
+// Sessions update button colors
+export const sessionsUpdateButtonDownloadingBackground = registerColor(
+	'sessionsUpdateButton.downloadingBackground',
+	transparent(buttonBackground, 0.4),
+	localize('sessionsUpdateButton.downloadingBackground', 'Background color of the update button to show download progress in the agent sessions window.')
+);
+
+export const sessionsUpdateButtonDownloadedBackground = registerColor(
+	'sessionsUpdateButton.downloadedBackground',
+	transparent(buttonBackground, 0.7),
+	localize('sessionsUpdateButton.downloadedBackground', 'Background color of the update button when download is complete in the agent sessions window.')
+);
diff --git a/src/vs/sessions/contrib/accountMenu/browser/account.contribution.ts b/src/vs/sessions/contrib/accountMenu/browser/account.contribution.ts
index cbff23edc4c94..c4d28d533855d 100644
--- a/src/vs/sessions/contrib/accountMenu/browser/account.contribution.ts
+++ b/src/vs/sessions/contrib/accountMenu/browser/account.contribution.ts
@@ -12,7 +12,7 @@ import { ContextKeyExpr, IContextKeyService } from '../../../../platform/context
 import { IDefaultAccountService } from '../../../../platform/defaultAccount/common/defaultAccount.js';
 import { IInstantiationService, ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
 import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../../workbench/common/contributions.js';
-import { appendUpdateMenuItems as registerUpdateMenuItems, CONTEXT_UPDATE_STATE } from '../../../../workbench/contrib/update/browser/update.js';
+import { appendUpdateMenuItems as registerUpdateMenuItems } from '../../../../workbench/contrib/update/browser/update.js';
 import { Menus } from '../../../browser/menus.js';
 import { IActionViewItemService } from '../../../../platform/actions/browser/actionViewItemService.js';
 import { IContextMenuService } from '../../../../platform/contextview/browser/contextView.js';
@@ -24,6 +24,13 @@ import { Button } from '../../../../base/browser/ui/button/button.js';
 import { defaultButtonStyles } from '../../../../platform/theme/browser/defaultStyles.js';
 import { Codicon } from '../../../../base/common/codicons.js';
 import { IUpdateService, StateType } from '../../../../platform/update/common/update.js';
+import { IHoverService } from '../../../../platform/hover/browser/hover.js';
+import { IProductService } from '../../../../platform/product/common/productService.js';
+import { IOpenerService } from '../../../../platform/opener/common/opener.js';
+import { IDialogService } from '../../../../platform/dialogs/common/dialogs.js';
+import { IHostService } from '../../../../workbench/services/host/browser/host.js';
+import { URI } from '../../../../base/common/uri.js';
+import { UpdateHoverWidget } from './updateHoverWidget.js';
 
 // --- Account Menu Items --- //
 const AccountMenu = new MenuId('SessionsAccountMenu');
@@ -81,20 +88,29 @@ MenuRegistry.appendMenuItem(AccountMenu, {
 // Update actions
 registerUpdateMenuItems(AccountMenu, '3_updates');
 
-class AccountWidget extends ActionViewItem {
+export class AccountWidget extends ActionViewItem {
 
 	private accountButton: Button | undefined;
+	private updateButton: Button | undefined;
+	private readonly updateHoverWidget: UpdateHoverWidget;
 	private readonly viewItemDisposables = this._register(new DisposableStore());
 
 	constructor(
 		action: IAction,
 		options: IBaseActionViewItemOptions,
 		@IDefaultAccountService private readonly defaultAccountService: IDefaultAccountService,
+		@IUpdateService private readonly updateService: IUpdateService,
 		@IContextMenuService private readonly contextMenuService: IContextMenuService,
 		@IMenuService private readonly menuService: IMenuService,
 		@IContextKeyService private readonly contextKeyService: IContextKeyService,
+		@IHoverService private readonly hoverService: IHoverService,
+		@IProductService private readonly productService: IProductService,
+		@IOpenerService private readonly openerService: IOpenerService,
+		@IDialogService private readonly dialogService: IDialogService,
+		@IHostService private readonly hostService: IHostService,
 	) {
 		super(undefined, action, { ...options, icon: false, label: false });
+		this.updateHoverWidget = new UpdateHoverWidget(this.updateService, this.productService, this.hoverService);
 	}
 
 	protected override getTooltip(): string | undefined {
@@ -119,14 +135,33 @@ class AccountWidget extends ActionViewItem {
 		}));
 		this.accountButton.element.classList.add('account-widget-account-button', 'sidebar-action-button');
 
+		// Update button (right)
+		const updateContainer = append(container, $('.account-widget-update'));
+		this.updateButton = this.viewItemDisposables.add(new Button(updateContainer, {
+			...defaultButtonStyles,
+			secondary: true,
+			title: false,
+			supportIcons: true,
+			buttonSecondaryBackground: 'transparent',
+			buttonSecondaryHoverBackground: undefined,
+			buttonSecondaryForeground: undefined,
+			buttonSecondaryBorder: undefined,
+		}));
+		this.updateButton.element.classList.add('account-widget-update-button', 'sidebar-action-button');
+		this.viewItemDisposables.add(this.updateHoverWidget.attachTo(this.updateButton.element));
+
 		this.updateAccountButton();
 		this.viewItemDisposables.add(this.defaultAccountService.onDidChangeDefaultAccount(() => this.updateAccountButton()));
+		this.updateUpdateButton();
+		this.viewItemDisposables.add(this.updateService.onStateChange(() => this.updateUpdateButton()));
 
 		this.viewItemDisposables.add(this.accountButton.onDidClick(e => {
 			e?.preventDefault();
 			e?.stopPropagation();
 			this.showAccountMenu(this.accountButton!.element);
 		}));
+
+		this.viewItemDisposables.add(this.updateButton.onDidClick(() => this.update()));
 	}
 
 	private showAccountMenu(anchor: HTMLElement): void {
@@ -154,101 +189,100 @@ class AccountWidget extends ActionViewItem {
 			: `$(${Codicon.account.id}) ${localize('signInLabel', "Sign In")}`;
 	}
 
+	private updateUpdateButton(): void {
+		if (!this.updateButton) {
+			return;
+		}
 
-	override onClick(): void {
-		// Handled by custom click handlers
-	}
-}
-
-class UpdateWidget extends ActionViewItem {
-
-	private updateButton: Button | undefined;
-	private readonly viewItemDisposables = this._register(new DisposableStore());
+		const state = this.updateService.state;
 
-	constructor(
-		action: IAction,
-		options: IBaseActionViewItemOptions,
-		@IUpdateService private readonly updateService: IUpdateService,
-	) {
-		super(undefined, action, { ...options, icon: false, label: false });
-	}
+		// In the embedded app, updates are detected but cannot be installed directly.
+		// Show a hint button to update via VS Code only when an update is actually available.
+		if (state.type === StateType.AvailableForDownload && state.canInstall === false) {
+			this.updateButton.element.classList.remove('hidden');
+			this.updateButton.element.classList.remove('account-widget-update-button-ready');
+			this.updateButton.element.classList.add('account-widget-update-button-hint');
+			this.updateButton.enabled = true;
+			this.updateButton.label = localize('updateAvailable', "Update Available");
+			this.updateButton.element.title = localize('updateInVSCodeHover', "Updates are managed by VS Code. Click to open VS Code.");
+			return;
+		}
 
-	protected override getTooltip(): string | undefined {
-		return undefined;
-	}
+		if (this.shouldHideUpdateButton(state.type)) {
+			this.clearUpdateButtonStyling();
+			this.updateButton.element.classList.add('hidden');
+			return;
+		}
 
-	override render(container: HTMLElement): void {
-		super.render(container);
-		container.classList.add('update-widget', 'sidebar-action');
+		this.updateButton.element.classList.remove('hidden');
+		this.updateButton.element.style.backgroundImage = '';
+		this.updateButton.enabled = state.type === StateType.Ready;
+		this.updateButton.label = this.getUpdateProgressMessage(state.type);
 
-		const updateContainer = append(container, $('.update-widget-action'));
-		this.updateButton = this.viewItemDisposables.add(new Button(updateContainer, {
-			...defaultButtonStyles,
-			secondary: true,
-			title: false,
-			supportIcons: true,
-			buttonSecondaryBackground: 'transparent',
-			buttonSecondaryHoverBackground: undefined,
-			buttonSecondaryForeground: undefined,
-			buttonSecondaryBorder: undefined,
-		}));
-		this.updateButton.element.classList.add('update-widget-button', 'sidebar-action-button');
-		this.viewItemDisposables.add(this.updateButton.onDidClick(() => this.update()));
-
-		this.updateUpdateButton();
-		this.viewItemDisposables.add(this.updateService.onStateChange(() => this.updateUpdateButton()));
-	}
+		if (state.type === StateType.Ready) {
+			this.updateButton.element.classList.add('account-widget-update-button-ready');
+			return;
+		}
 
-	private isUpdateReady(): boolean {
-		return this.updateService.state.type === StateType.Ready;
+		this.updateButton.element.classList.remove('account-widget-update-button-ready');
 	}
 
-	private isUpdatePending(): boolean {
-		const type = this.updateService.state.type;
-		return type === StateType.AvailableForDownload
-			|| type === StateType.CheckingForUpdates
-			|| type === StateType.Downloading
-			|| type === StateType.Downloaded
-			|| type === StateType.Updating
-			|| type === StateType.Overwriting;
+	private shouldHideUpdateButton(type: StateType): boolean {
+		return type === StateType.Uninitialized
+			|| type === StateType.Idle
+			|| type === StateType.Disabled
+			|| type === StateType.CheckingForUpdates;
 	}
 
-	private updateUpdateButton(): void {
-		if (!this.updateButton) {
-			return;
-		}
-
-		const state = this.updateService.state;
-		if (this.isUpdatePending() && !this.isUpdateReady()) {
-			this.updateButton.enabled = false;
-			this.updateButton.label = `$(${Codicon.loading.id}~spin) ${this.getUpdateProgressMessage(state.type)}`;
-		} else {
-			this.updateButton.enabled = true;
-			this.updateButton.label = `$(${Codicon.debugRestart.id}) ${localize('update', "Update")}`;
+	private clearUpdateButtonStyling(): void {
+		if (this.updateButton) {
+			this.updateButton.element.style.backgroundImage = '';
+			this.updateButton.element.classList.remove('account-widget-update-button-ready');
 		}
 	}
 
 	private getUpdateProgressMessage(type: StateType): string {
 		switch (type) {
-			case StateType.CheckingForUpdates:
-				return localize('checkingForUpdates', "Checking for Updates...");
+			case StateType.Ready:
+				return localize('update', "Update");
+			case StateType.AvailableForDownload:
 			case StateType.Downloading:
-				return localize('downloadingUpdate', "Downloading Update...");
+			case StateType.Overwriting:
+				return localize('downloadingUpdate', "Downloading...");
 			case StateType.Downloaded:
-				return localize('installingUpdate', "Installing Update...");
+				return localize('installingUpdate', "Installing...");
 			case StateType.Updating:
 				return localize('updatingApp', "Updating...");
-			case StateType.Overwriting:
-				return localize('overwritingUpdate', "Downloading Update...");
 			default:
 				return localize('updating', "Updating...");
 		}
 	}
 
 	private async update(): Promise<void> {
+		const state = this.updateService.state;
+		if (state.type === StateType.AvailableForDownload && state.canInstall === false) {
+			const { confirmed } = await this.dialogService.confirm({
+				message: localize('updateFromVSCode.title', "Update from VS Code"),
+				detail: localize('updateFromVSCode.detail', "This will close the Sessions app and open VS Code so you can install the update.\n\nLaunch Sessions again after the update is complete."),
+				primaryButton: localize('updateFromVSCode.open', "Close and Open VS Code"),
+			});
+			if (confirmed) {
+				await this.openVSCode();
+				await this.hostService.close();
+			}
+			return;
+		}
 		await this.updateService.quitAndInstall();
 	}
 
+	private async openVSCode(): Promise<void> {
+		await this.openerService.open(URI.from({
+			scheme: this.productService.urlProtocol,
+			query: 'windowId=_blank',
+		}), { openExternal: true });
+	}
+
+
 	override onClick(): void {
 		// Handled by custom click handlers
 	}
@@ -271,11 +305,6 @@ class AccountWidgetContribution extends Disposable implements IWorkbenchContribu
 			return instantiationService.createInstance(AccountWidget, action, options);
 		}, undefined));
 
-		const sessionsUpdateWidgetAction = 'sessions.action.updateWidget';
-		this._register(actionViewItemService.register(Menus.SidebarFooter, sessionsUpdateWidgetAction, (action, options) => {
-			return instantiationService.createInstance(UpdateWidget, action, options);
-		}, undefined));
-
 		// Register the action with menu item after the view item provider
 		// so the toolbar picks up the custom widget
 		this._register(registerAction2(class extends Action2 {
@@ -295,30 +324,6 @@ class AccountWidgetContribution extends Disposable implements IWorkbenchContribu
 			}
 		}));
 
-		this._register(registerAction2(class extends Action2 {
-			constructor() {
-				super({
-					id: sessionsUpdateWidgetAction,
-					title: localize2('sessionsUpdateWidget', 'Sessions Update'),
-					menu: {
-						id: Menus.SidebarFooter,
-						group: 'navigation',
-						order: 0,
-						when: ContextKeyExpr.or(
-							CONTEXT_UPDATE_STATE.isEqualTo(StateType.Ready),
-							CONTEXT_UPDATE_STATE.isEqualTo(StateType.AvailableForDownload),
-							CONTEXT_UPDATE_STATE.isEqualTo(StateType.Downloading),
-							CONTEXT_UPDATE_STATE.isEqualTo(StateType.Downloaded),
-							CONTEXT_UPDATE_STATE.isEqualTo(StateType.Updating),
-							CONTEXT_UPDATE_STATE.isEqualTo(StateType.Overwriting),
-						)
-					}
-				});
-			}
-			async run(): Promise<void> {
-				// Handled by the custom view item
-			}
-		}));
 	}
 }
 
diff --git a/src/vs/sessions/contrib/accountMenu/browser/media/accountWidget.css b/src/vs/sessions/contrib/accountMenu/browser/media/accountWidget.css
index 01bdd2c100b03..3e852ea53ba47 100644
--- a/src/vs/sessions/contrib/accountMenu/browser/media/accountWidget.css
+++ b/src/vs/sessions/contrib/accountMenu/browser/media/accountWidget.css
@@ -3,6 +3,22 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+.monaco-workbench .part.sidebar > .sidebar-footer .account-widget {
+	display: flex;
+	align-items: center;
+	gap: 4px;
+	width: 100%;
+	min-width: 0;
+}
+
+.account-widget {
+	display: flex;
+	align-items: center;
+	gap: 4px;
+	width: 100%;
+	min-width: 0;
+}
+
 /* Account Button */
 .monaco-workbench .part.sidebar > .sidebar-footer .account-widget-account {
 	overflow: hidden;
@@ -10,9 +26,132 @@
 	flex: 1;
 }
 
+.account-widget-account {
+	overflow: hidden;
+	min-width: 0;
+	flex: 1;
+}
+
 /* Update Button */
-.monaco-workbench .part.sidebar > .sidebar-footer .update-widget-action {
+.monaco-workbench .part.sidebar > .sidebar-footer .account-widget-update {
+	flex: 0 0 auto;
+	width: fit-content;
+	min-width: 0;
+	overflow: hidden;
+}
+
+.account-widget-update {
+	flex: 0 0 auto;
+	width: fit-content;
+	min-width: 0;
+	overflow: hidden;
+}
+
+.monaco-workbench .part.sidebar > .sidebar-footer .account-widget-update .account-widget-update-button {
+	width: auto;
+	max-width: none;
+}
+
+.account-widget-update .account-widget-update-button {
+	width: auto;
+	max-width: none;
+}
+
+.monaco-workbench .part.sidebar > .sidebar-footer .account-widget-update .account-widget-update-button.account-widget-update-button-ready {
+	background-color: var(--vscode-button-background) !important;
+	color: var(--vscode-button-foreground) !important;
+}
+
+.account-widget-update .account-widget-update-button.account-widget-update-button-ready {
+	background-color: var(--vscode-button-background) !important;
+	color: var(--vscode-button-foreground) !important;
+}
+
+/* Boxed hint style for embedded app update indicator — outlined, no fill */
+.account-widget-update .account-widget-update-button.account-widget-update-button-hint {
+	background-color: transparent !important;
+	color: var(--vscode-button-foreground) !important;
+	border: 1px solid var(--vscode-button-background) !important;
+}
+
+.account-widget-update .account-widget-update-button.account-widget-update-button-hint:hover {
+	background-color: color-mix(in srgb, var(--vscode-button-background) 20%, transparent) !important;
+}
+
+.monaco-workbench .part.sidebar > .sidebar-footer .account-widget-update .account-widget-update-button.account-widget-update-button-ready:hover {
+	background-color: var(--vscode-button-background) !important;
+}
+
+.account-widget-update .account-widget-update-button.account-widget-update-button-ready:hover {
+	background-color: var(--vscode-button-background) !important;
+}
+
+.monaco-workbench .part.sidebar > .sidebar-footer .account-widget-update .account-widget-update-button.account-widget-update-button-ready:focus {
+	background-color: var(--vscode-button-background) !important;
+}
+
+.account-widget-update .account-widget-update-button.account-widget-update-button-ready:focus {
+	background-color: var(--vscode-button-background) !important;
+}
+
+.monaco-workbench .part.sidebar > .sidebar-footer .account-widget-update .account-widget-update-button.hidden {
+	display: none;
+}
+
+.account-widget-update .account-widget-update-button.hidden {
+	display: none;
+}
+
+.monaco-workbench .part.sidebar > .sidebar-footer .account-widget-account .account-widget-account-button {
 	overflow: hidden;
+	text-overflow: ellipsis;
+	min-width: 0;
+}
+
+.account-widget-account .account-widget-account-button {
+	overflow: hidden;
+	text-overflow: ellipsis;
+	min-width: 0;
+}
+
+.monaco-workbench .part.sidebar > .sidebar-footer .account-widget-account .account-widget-account-button > .codicon {
+	flex: 0 0 auto;
+}
+
+.account-widget-account .account-widget-account-button > .codicon {
+	flex: 0 0 auto;
+}
+
+.monaco-workbench .part.sidebar > .sidebar-footer .account-widget-account .account-widget-account-button > span:last-child {
+	flex: 1;
 	min-width: 0;
+	overflow: hidden;
+	text-overflow: ellipsis;
+	white-space: nowrap;
+}
+
+.account-widget-account .account-widget-account-button > span:last-child {
 	flex: 1;
+	min-width: 0;
+	overflow: hidden;
+	text-overflow: ellipsis;
+	white-space: nowrap;
+}
+
+.monaco-workbench .part.sidebar > .sidebar-footer .account-widget-account .account-widget-account-button > .monaco-button-label {
+	display: block;
+	width: 100%;
+	overflow: hidden;
+	text-overflow: ellipsis;
+	white-space: nowrap;
+	min-width: 0;
+}
+
+.account-widget-account .account-widget-account-button > .monaco-button-label {
+	display: block;
+	width: 100%;
+	overflow: hidden;
+	text-overflow: ellipsis;
+	white-space: nowrap;
+	min-width: 0;
 }
diff --git a/src/vs/sessions/contrib/accountMenu/browser/media/updateHoverWidget.css b/src/vs/sessions/contrib/accountMenu/browser/media/updateHoverWidget.css
new file mode 100644
index 0000000000000..6291d8e292250
--- /dev/null
+++ b/src/vs/sessions/contrib/accountMenu/browser/media/updateHoverWidget.css
@@ -0,0 +1,65 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+.sessions-update-hover {
+	display: flex;
+	flex-direction: column;
+	gap: 8px;
+	min-width: 200px;
+	padding: 12px 16px;
+}
+
+.sessions-update-hover-header {
+	font-weight: 600;
+	font-size: 13px;
+}
+
+/* Progress bar track */
+.sessions-update-hover-progress-track {
+	height: 4px;
+	border-radius: 2px;
+	background-color: var(--vscode-editorWidget-border, rgba(128, 128, 128, 0.3));
+	overflow: hidden;
+}
+
+/* Progress bar fill */
+.sessions-update-hover-progress-fill {
+	height: 100%;
+	border-radius: 2px;
+	background-color: var(--vscode-progressBar-background, #0078d4);
+	transition: width 0.2s ease;
+}
+
+/* Details grid */
+.sessions-update-hover-grid {
+	display: grid;
+	grid-template-columns: auto auto auto auto;
+	column-gap: 8px;
+	row-gap: 2px;
+	font-size: 12px;
+	align-items: baseline;
+}
+
+.sessions-update-hover-label {
+	color: var(--vscode-descriptionForeground);
+}
+
+/* Version number emphasis */
+.sessions-update-hover-version {
+	color: var(--vscode-textLink-foreground);
+}
+
+/* Compact age label */
+.sessions-update-hover-age {
+	color: var(--vscode-descriptionForeground);
+	font-size: 11px;
+}
+
+/* Commit hashes - subtle */
+.sessions-update-hover-commit {
+	color: var(--vscode-descriptionForeground);
+	font-family: var(--monaco-monospace-font);
+	font-size: 11px;
+}
diff --git a/src/vs/sessions/contrib/accountMenu/browser/updateHoverWidget.ts b/src/vs/sessions/contrib/accountMenu/browser/updateHoverWidget.ts
new file mode 100644
index 0000000000000..fc80636b0a8f7
--- /dev/null
+++ b/src/vs/sessions/contrib/accountMenu/browser/updateHoverWidget.ts
@@ -0,0 +1,187 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { HoverPosition } from '../../../../base/browser/ui/hover/hoverWidget.js';
+import { localize } from '../../../../nls.js';
+import { IHoverService } from '../../../../platform/hover/browser/hover.js';
+import { IProductService } from '../../../../platform/product/common/productService.js';
+import { Downloading, IUpdate, IUpdateService, State, StateType, Updating } from '../../../../platform/update/common/update.js';
+import './media/updateHoverWidget.css';
+
+export class UpdateHoverWidget {
+
+	constructor(
+		private readonly updateService: IUpdateService,
+		private readonly productService: IProductService,
+		private readonly hoverService: IHoverService,
+	) { }
+
+	attachTo(target: HTMLElement) {
+		return this.hoverService.setupDelayedHover(
+			target,
+			() => ({
+				content: this.createHoverContent(),
+				position: { hoverPosition: HoverPosition.RIGHT },
+				appearance: { showPointer: true }
+			}),
+			{ groupId: 'sessions-account-update' }
+		);
+	}
+
+	createHoverContent(state: State = this.updateService.state): HTMLElement {
+		const update = this.getUpdateFromState(state);
+		const currentVersion = this.productService.version ?? localize('unknownVersion', "Unknown");
+		const targetVersion = update?.productVersion ?? update?.version ?? localize('unknownVersion', "Unknown");
+		const currentCommit = this.productService.commit;
+		const targetCommit = update?.version;
+		const progressPercent = this.getUpdateProgressPercent(state);
+
+		const container = document.createElement('div');
+		container.classList.add('sessions-update-hover');
+
+		// Header: e.g. "Downloading VS Code Insiders"
+		const header = document.createElement('div');
+		header.classList.add('sessions-update-hover-header');
+		header.textContent = this.getUpdateHeaderLabel(state.type);
+		container.appendChild(header);
+
+		// Progress bar
+		if (progressPercent !== undefined) {
+			const progressTrack = document.createElement('div');
+			progressTrack.classList.add('sessions-update-hover-progress-track');
+			const progressFill = document.createElement('div');
+			progressFill.classList.add('sessions-update-hover-progress-fill');
+			progressFill.style.width = `${progressPercent}%`;
+			progressTrack.appendChild(progressFill);
+			container.appendChild(progressTrack);
+		}
+
+		// Version info grid
+		const detailsGrid = document.createElement('div');
+		detailsGrid.classList.add('sessions-update-hover-grid');
+
+		const currentDate = this.productService.date ? new Date(this.productService.date) : undefined;
+		const currentAge = currentDate ? this.formatCompactAge(currentDate.getTime()) : undefined;
+		const newAge = update?.timestamp ? this.formatCompactAge(update.timestamp) : undefined;
+
+		this.appendGridRow(detailsGrid, localize('updateHoverCurrentVersionLabel', "Current"), currentVersion, currentAge, currentCommit);
+		this.appendGridRow(detailsGrid, localize('updateHoverNewVersionLabel', "New"), targetVersion, newAge, targetCommit);
+
+		container.appendChild(detailsGrid);
+
+		return container;
+	}
+
+	private appendGridRow(grid: HTMLElement, label: string, version: string, age?: string, commit?: string): void {
+		const labelEl = document.createElement('span');
+		labelEl.classList.add('sessions-update-hover-label');
+		labelEl.textContent = label;
+		grid.appendChild(labelEl);
+
+		const versionEl = document.createElement('span');
+		versionEl.classList.add('sessions-update-hover-version');
+		versionEl.textContent = version;
+		grid.appendChild(versionEl);
+
+		const ageEl = document.createElement('span');
+		ageEl.classList.add('sessions-update-hover-age');
+		ageEl.textContent = age ?? '';
+		grid.appendChild(ageEl);
+
+		const commitEl = document.createElement('span');
+		commitEl.classList.add('sessions-update-hover-commit');
+		commitEl.textContent = commit ? commit.substring(0, 7) : '';
+		grid.appendChild(commitEl);
+	}
+
+	private formatCompactAge(timestamp: number): string {
+		const seconds = Math.round((Date.now() - timestamp) / 1000);
+		if (seconds < 60) {
+			return localize('compactAgeNow', "now");
+		}
+		const minutes = Math.round(seconds / 60);
+		if (minutes < 60) {
+			return localize('compactAgeMinutes', "{0}m ago", minutes);
+		}
+		const hours = Math.round(seconds / 3600);
+		if (hours < 24) {
+			return localize('compactAgeHours', "{0}h ago", hours);
+		}
+		const days = Math.round(seconds / 86400);
+		if (days < 7) {
+			return localize('compactAgeDays', "{0}d ago", days);
+		}
+		const weeks = Math.round(days / 7);
+		if (weeks < 5) {
+			return localize('compactAgeWeeks', "{0}w ago", weeks);
+		}
+		const months = Math.round(days / 30);
+		return localize('compactAgeMonths', "{0}mo ago", months);
+	}
+
+	private getUpdateFromState(state: State): IUpdate | undefined {
+		switch (state.type) {
+			case StateType.AvailableForDownload:
+			case StateType.Downloaded:
+			case StateType.Ready:
+			case StateType.Overwriting:
+			case StateType.Updating:
+				return state.update;
+			case StateType.Downloading:
+				return state.update;
+			default:
+				return undefined;
+		}
+	}
+
+	/**
+	 * Returns progress as a percentage (0-100), or undefined if progress is not applicable.
+	 */
+	private getUpdateProgressPercent(state: State): number | undefined {
+		switch (state.type) {
+			case StateType.Downloading: {
+				const downloadingState = state as Downloading;
+				if (downloadingState.downloadedBytes !== undefined && downloadingState.totalBytes && downloadingState.totalBytes > 0) {
+					return Math.min(100, Math.round((downloadingState.downloadedBytes / downloadingState.totalBytes) * 100));
+				}
+				return 0;
+			}
+			case StateType.Updating: {
+				const updatingState = state as Updating;
+				if (updatingState.currentProgress !== undefined && updatingState.maxProgress && updatingState.maxProgress > 0) {
+					return Math.min(100, Math.round((updatingState.currentProgress / updatingState.maxProgress) * 100));
+				}
+				return 0;
+			}
+			case StateType.Downloaded:
+			case StateType.Ready:
+				return 100;
+			case StateType.AvailableForDownload:
+			case StateType.Overwriting:
+				return 0;
+			default:
+				return undefined;
+		}
+	}
+
+	private getUpdateHeaderLabel(type: StateType): string {
+		const productName = this.productService.nameShort;
+		switch (type) {
+			case StateType.Ready:
+				return localize('updateReady', "{0} Update Ready", productName);
+			case StateType.AvailableForDownload:
+				return localize('downloadAvailable', "{0} Update Available", productName);
+			case StateType.Downloading:
+			case StateType.Overwriting:
+				return localize('downloadingUpdate', "Downloading {0}", productName);
+			case StateType.Downloaded:
+				return localize('installingUpdate', "Installing {0}", productName);
+			case StateType.Updating:
+				return localize('updatingApp', "Updating {0}", productName);
+			default:
+				return localize('updating', "Updating {0}", productName);
+		}
+	}
+}
diff --git a/src/vs/sessions/contrib/accountMenu/test/browser/accountWidget.fixture.ts b/src/vs/sessions/contrib/accountMenu/test/browser/accountWidget.fixture.ts
new file mode 100644
index 0000000000000..143b89aad169b
--- /dev/null
+++ b/src/vs/sessions/contrib/accountMenu/test/browser/accountWidget.fixture.ts
@@ -0,0 +1,158 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { ICopilotTokenInfo, IDefaultAccount, IPolicyData } from '../../../../../base/common/defaultAccount.js';
+import { Action } from '../../../../../base/common/actions.js';
+import { Emitter } from '../../../../../base/common/event.js';
+import { IMenuService } from '../../../../../platform/actions/common/actions.js';
+import { IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
+import { IDefaultAccountService } from '../../../../../platform/defaultAccount/common/defaultAccount.js';
+import { IContextMenuService } from '../../../../../platform/contextview/browser/contextView.js';
+import { IHoverService } from '../../../../../platform/hover/browser/hover.js';
+import { IProductService } from '../../../../../platform/product/common/productService.js';
+import { IUpdateService, State, UpdateType } from '../../../../../platform/update/common/update.js';
+import { IOpenerService } from '../../../../../platform/opener/common/opener.js';
+import { IDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
+import { IHostService } from '../../../../../workbench/services/host/browser/host.js';
+import { ComponentFixtureContext, createEditorServices, defineComponentFixture, defineThemedFixtureGroup, registerWorkbenchServices } from '../../../../../workbench/test/browser/componentFixtures/fixtureUtils.js';
+import { AccountWidget } from '../../browser/account.contribution.js';
+
+// Ensure color registrations are loaded
+import '../../../../common/theme.js';
+import '../../../../../platform/theme/common/colors/inputColors.js';
+
+// Import the CSS
+import '../../../../browser/media/sidebarActionButton.css';
+import '../../browser/media/accountWidget.css';
+
+const mockUpdate = { version: '1.0.0' };
+
+function createMockUpdateService(state: State): IUpdateService {
+	const onStateChange = new Emitter<State>();
+	const service: IUpdateService = {
+		_serviceBrand: undefined,
+		state,
+		onStateChange: onStateChange.event,
+		checkForUpdates: async () => { },
+		downloadUpdate: async () => { },
+		applyUpdate: async () => { },
+		quitAndInstall: async () => { },
+		isLatestVersion: async () => true,
+		_applySpecificUpdate: async () => { },
+		setInternalOrg: async () => { },
+	};
+	return service;
+}
+
+function createMockDefaultAccountService(accountPromise: Promise<IDefaultAccount | null>): IDefaultAccountService {
+	const onDidChangeDefaultAccount = new Emitter<IDefaultAccount | null>();
+	const onDidChangePolicyData = new Emitter<IPolicyData | null>();
+	const onDidChangeCopilotTokenInfo = new Emitter<ICopilotTokenInfo | null>();
+	const service: IDefaultAccountService = {
+		_serviceBrand: undefined,
+		onDidChangeDefaultAccount: onDidChangeDefaultAccount.event,
+		onDidChangePolicyData: onDidChangePolicyData.event,
+		onDidChangeCopilotTokenInfo: onDidChangeCopilotTokenInfo.event,
+		policyData: null,
+		copilotTokenInfo: null,
+		getDefaultAccount: () => accountPromise,
+		getDefaultAccountAuthenticationProvider: () => ({ id: 'github', name: 'GitHub', enterprise: false }),
+		setDefaultAccountProvider: () => { },
+		refresh: () => accountPromise,
+		signIn: async () => null,
+		signOut: async () => { },
+	};
+	return service;
+}
+
+function renderAccountWidget(ctx: ComponentFixtureContext, state: State, accountPromise: Promise<IDefaultAccount | null>): void {
+	ctx.container.style.padding = '16px';
+	ctx.container.style.width = '340px';
+	ctx.container.style.backgroundColor = 'var(--vscode-sideBar-background)';
+
+	const mockUpdateService = createMockUpdateService(state);
+	const mockAccountService = createMockDefaultAccountService(accountPromise);
+
+	const instantiationService = createEditorServices(ctx.disposableStore, {
+		colorTheme: ctx.theme,
+		additionalServices: registerWorkbenchServices,
+	});
+
+	const action = ctx.disposableStore.add(new Action('sessions.action.accountWidget', 'Sessions Account'));
+	const contextMenuService = instantiationService.get(IContextMenuService);
+	const menuService = instantiationService.get(IMenuService);
+	const contextKeyService = instantiationService.get(IContextKeyService);
+	const hoverService = instantiationService.get(IHoverService);
+	const productService = instantiationService.get(IProductService);
+	const openerService = instantiationService.get(IOpenerService);
+	const dialogService = instantiationService.get(IDialogService);
+	const hostService = instantiationService.get(IHostService);
+	const widget = new AccountWidget(action, {}, mockAccountService, mockUpdateService, contextMenuService, menuService, contextKeyService, hoverService, productService, openerService, dialogService, hostService);
+	ctx.disposableStore.add(widget);
+	widget.render(ctx.container);
+}
+
+const signedInAccount: IDefaultAccount = {
+	authenticationProvider: {
+		id: 'github',
+		name: 'GitHub',
+		enterprise: false,
+	},
+	accountName: 'avery.long.account.name@example.com',
+	sessionId: 'session-id',
+	enterprise: false,
+};
+
+export default defineThemedFixtureGroup({ path: 'sessions/' }, {
+	LoadingSignedOutNoUpdate: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderAccountWidget(ctx, State.Idle(UpdateType.Setup), new Promise<IDefaultAccount | null>(() => { })),
+	}),
+
+	SignedOutNoUpdate: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderAccountWidget(ctx, State.Idle(UpdateType.Setup), Promise.resolve(null)),
+	}),
+
+	SignedInNoUpdate: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderAccountWidget(ctx, State.Idle(UpdateType.Setup), Promise.resolve(signedInAccount)),
+	}),
+
+	CheckingForUpdatesHidden: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderAccountWidget(ctx, State.CheckingForUpdates(true), Promise.resolve(signedInAccount)),
+	}),
+
+	Ready: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderAccountWidget(ctx, State.Ready(mockUpdate, true, false), Promise.resolve(signedInAccount)),
+	}),
+
+	AvailableForDownload: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderAccountWidget(ctx, State.AvailableForDownload(mockUpdate), Promise.resolve(signedInAccount)),
+	}),
+
+	Downloading30Percent: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderAccountWidget(ctx, State.Downloading(mockUpdate, true, false, 30_000_000, 100_000_000), Promise.resolve(signedInAccount)),
+	}),
+
+	DownloadedInstalling: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderAccountWidget(ctx, State.Downloaded(mockUpdate, true, false), Promise.resolve(signedInAccount)),
+	}),
+
+	Updating: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderAccountWidget(ctx, State.Updating(mockUpdate), Promise.resolve(signedInAccount)),
+	}),
+
+	Overwriting: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderAccountWidget(ctx, State.Overwriting(mockUpdate, true), Promise.resolve(signedInAccount)),
+	}),
+});
diff --git a/src/vs/sessions/contrib/accountMenu/test/browser/updateHoverWidget.fixture.ts b/src/vs/sessions/contrib/accountMenu/test/browser/updateHoverWidget.fixture.ts
new file mode 100644
index 0000000000000..6ca47e2ee1b88
--- /dev/null
+++ b/src/vs/sessions/contrib/accountMenu/test/browser/updateHoverWidget.fixture.ts
@@ -0,0 +1,83 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Emitter } from '../../../../../base/common/event.js';
+import { mock } from '../../../../../base/test/common/mock.js';
+import { IHoverService } from '../../../../../platform/hover/browser/hover.js';
+import { IProductService } from '../../../../../platform/product/common/productService.js';
+import { IUpdateService, State } from '../../../../../platform/update/common/update.js';
+import { ComponentFixtureContext, createEditorServices, defineComponentFixture, defineThemedFixtureGroup } from '../../../../../workbench/test/browser/componentFixtures/fixtureUtils.js';
+import { UpdateHoverWidget } from '../../browser/updateHoverWidget.js';
+
+const mockUpdate = { version: 'a1b2c3d4e5f6', productVersion: '1.100.0', timestamp: Date.now() - 2 * 60 * 60 * 1000 };
+const mockUpdateSameVersion = { version: 'a1b2c3d4e5f6', productVersion: '1.99.0', timestamp: Date.now() - 3 * 24 * 60 * 60 * 1000 };
+
+function createMockUpdateService(state: State): IUpdateService {
+	const onStateChange = new Emitter<State>();
+	const service: IUpdateService = {
+		_serviceBrand: undefined,
+		state,
+		onStateChange: onStateChange.event,
+		checkForUpdates: async () => { },
+		downloadUpdate: async () => { },
+		applyUpdate: async () => { },
+		quitAndInstall: async () => { },
+		isLatestVersion: async () => true,
+		_applySpecificUpdate: async () => { },
+		setInternalOrg: async () => { },
+	};
+	return service;
+}
+
+function renderHoverWidget(ctx: ComponentFixtureContext, state: State): void {
+	ctx.container.style.backgroundColor = 'var(--vscode-editorHoverWidget-background)';
+
+	const instantiationService = createEditorServices(ctx.disposableStore, {
+		colorTheme: ctx.theme,
+	});
+
+	const updateService = createMockUpdateService(state);
+	const productService = new class extends mock<IProductService>() {
+		override readonly version = '1.99.0';
+		override readonly nameShort = 'VS Code Insiders';
+		override readonly commit = 'f0e1d2c3b4a5';
+		override readonly date = new Date(Date.now() - 7 * 24 * 60 * 60 * 1000).toISOString();
+	};
+	const hoverService = instantiationService.get(IHoverService);
+	const widget = new UpdateHoverWidget(updateService, productService, hoverService);
+	ctx.container.appendChild(widget.createHoverContent(state));
+}
+
+export default defineThemedFixtureGroup({ path: 'sessions/' }, {
+	UpdateHoverReady: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderHoverWidget(ctx, State.Ready(mockUpdate, true, false)),
+	}),
+
+	UpdateHoverAvailableForDownload: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderHoverWidget(ctx, State.AvailableForDownload(mockUpdate)),
+	}),
+
+	UpdateHoverDownloading30Percent: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderHoverWidget(ctx, State.Downloading(mockUpdate, true, false, 30_000_000, 100_000_000)),
+	}),
+
+	UpdateHoverInstalling: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderHoverWidget(ctx, State.Downloaded(mockUpdate, true, false)),
+	}),
+
+	UpdateHoverUpdating: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderHoverWidget(ctx, State.Updating(mockUpdate, 40, 100)),
+	}),
+
+	UpdateHoverSameVersion: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderHoverWidget(ctx, State.Ready(mockUpdateSameVersion, true, false)),
+	}),
+});
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedback.contribution.ts b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedback.contribution.ts
index 7f5708a85d8d0..7ff02612cc13f 100644
--- a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedback.contribution.ts
+++ b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedback.contribution.ts
@@ -5,7 +5,6 @@
 
 import './agentFeedbackEditorInputContribution.js';
 import './agentFeedbackEditorWidgetContribution.js';
-import './agentFeedbackLineDecorationContribution.js';
 import './agentFeedbackOverviewRulerContribution.js';
 import { InstantiationType, registerSingleton } from '../../../../platform/instantiation/common/extensions.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackAttachment.ts b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackAttachment.ts
index e45f96e488d06..04e66cf8dd099 100644
--- a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackAttachment.ts
+++ b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackAttachment.ts
@@ -74,6 +74,7 @@ export class AgentFeedbackAttachmentContribution extends Disposable {
 				text: f.text,
 				resourceUri: f.resourceUri,
 				range: f.range,
+				codeSelection: this._snippetCache.get(f.id),
 			})),
 			value,
 		};
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackAttachmentWidget.ts b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackAttachmentWidget.ts
index fb2b68188e315..33a887638e83f 100644
--- a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackAttachmentWidget.ts
+++ b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackAttachmentWidget.ts
@@ -73,6 +73,6 @@ export class AgentFeedbackAttachmentWidget extends Disposable {
 		this.element.ariaLabel = localize('chat.agentFeedback', "Attached agent feedback, {0}", this._attachment.name);
 
 		// Custom interactive hover
-		this._store.add(this._instantiationService.createInstance(AgentFeedbackHover, this.element, this._attachment));
+		this._store.add(this._instantiationService.createInstance(AgentFeedbackHover, this.element, this._attachment, options.supportsDeletion));
 	}
 }
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorActions.ts b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorActions.ts
index 620cf99ae3db9..c16e39d3bde5c 100644
--- a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorActions.ts
+++ b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorActions.ts
@@ -6,24 +6,32 @@
 import { Codicon } from '../../../../base/common/codicons.js';
 import { localize, localize2 } from '../../../../nls.js';
 import { Action2, MenuRegistry, registerAction2 } from '../../../../platform/actions/common/actions.js';
-import { ContextKeyExpr } from '../../../../platform/contextkey/common/contextkey.js';
+import { ContextKeyExpr, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
 import { ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
 import { URI } from '../../../../base/common/uri.js';
 import { isEqual } from '../../../../base/common/resources.js';
 import { EditorsOrder, IEditorIdentifier } from '../../../../workbench/common/editor.js';
 import { IEditorService } from '../../../../workbench/services/editor/common/editorService.js';
+import { GroupsOrder, IEditorGroupsService } from '../../../../workbench/services/editor/common/editorGroupsService.js';
 import { IChatWidgetService } from '../../../../workbench/contrib/chat/browser/chat.js';
 import { ChatContextKeys } from '../../../../workbench/contrib/chat/common/actions/chatContextKeys.js';
 import { CHAT_CATEGORY } from '../../../../workbench/contrib/chat/browser/actions/chatActions.js';
 import { IAgentFeedbackService } from './agentFeedbackService.js';
-import { getActiveResourceCandidates } from './agentFeedbackEditorUtils.js';
+import { getActiveResourceCandidates, getSessionForResource } from './agentFeedbackEditorUtils.js';
 import { Menus } from '../../../browser/menus.js';
+import { IChatEditingService } from '../../../../workbench/contrib/chat/common/editing/chatEditingService.js';
+import { IAgentSessionsService } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
+import { ICodeReviewService } from '../../codeReview/browser/codeReviewService.js';
+import { getSessionEditorComments } from './sessionEditorComments.js';
 
 export const submitFeedbackActionId = 'agentFeedbackEditor.action.submit';
 export const navigatePreviousFeedbackActionId = 'agentFeedbackEditor.action.navigatePrevious';
 export const navigateNextFeedbackActionId = 'agentFeedbackEditor.action.navigateNext';
 export const clearAllFeedbackActionId = 'agentFeedbackEditor.action.clearAll';
 export const navigationBearingFakeActionId = 'agentFeedbackEditor.navigation.bearings';
+export const hasSessionEditorComments = new RawContextKey<boolean>('agentFeedbackEditor.hasSessionComments', false);
+export const hasSessionAgentFeedback = new RawContextKey<boolean>('agentFeedbackEditor.hasAgentFeedback', false);
 
 abstract class AgentFeedbackEditorAction extends Action2 {
 
@@ -37,16 +45,33 @@ abstract class AgentFeedbackEditorAction extends Action2 {
 	override async run(accessor: ServicesAccessor): Promise<void> {
 		const editorService = accessor.get(IEditorService);
 		const agentFeedbackService = accessor.get(IAgentFeedbackService);
+		const chatEditingService = accessor.get(IChatEditingService);
+		const agentSessionsService = accessor.get(IAgentSessionsService);
+		const codeReviewService = accessor.get(ICodeReviewService);
+
+		const editorGroupsService = accessor.get(IEditorGroupsService);
+
+		const activePane = editorService.activeEditorPane
+			?? editorGroupsService.getGroups(GroupsOrder.MOST_RECENTLY_ACTIVE).find(g => g.activeEditorPane)?.activeEditorPane
+			?? editorService.visibleEditorPanes[0];
+		const candidates = getActiveResourceCandidates(activePane?.input);
+		for (const candidate of candidates) {
+			const sessionResource = getSessionForResource(candidate, chatEditingService, agentSessionsService)
+				?? agentFeedbackService.getMostRecentSessionForResource(candidate);
+			if (!sessionResource) {
+				continue;
+			}
 
-		const candidates = getActiveResourceCandidates(editorService.activeEditorPane?.input);
-		const sessionResource = candidates
-			.map(candidate => agentFeedbackService.getMostRecentSessionForResource(candidate))
-			.find((value): value is URI => !!value);
-		if (!sessionResource) {
-			return;
+			const comments = getSessionEditorComments(
+				sessionResource,
+				agentFeedbackService.getFeedback(sessionResource),
+				codeReviewService.getReviewState(sessionResource).get(),
+				codeReviewService.getPRReviewState(sessionResource).get(),
+			);
+			if (comments.length > 0) {
+				return this.runWithSession(accessor, sessionResource);
+			}
 		}
-
-		return this.runWithSession(accessor, sessionResource);
 	}
 
 	abstract runWithSession(accessor: ServicesAccessor, sessionResource: URI): Promise<void> | void;
@@ -65,7 +90,7 @@ class SubmitFeedbackAction extends AgentFeedbackEditorAction {
 				id: Menus.AgentFeedbackEditorContent,
 				group: 'a_submit',
 				order: 0,
-				when: ChatContextKeys.enabled,
+				when: ContextKeyExpr.and(ChatContextKeys.enabled, hasSessionAgentFeedback),
 			},
 		});
 	}
@@ -74,9 +99,11 @@ class SubmitFeedbackAction extends AgentFeedbackEditorAction {
 		const chatWidgetService = accessor.get(IChatWidgetService);
 		const agentFeedbackService = accessor.get(IAgentFeedbackService);
 		const editorService = accessor.get(IEditorService);
+		const logService = accessor.get(ILogService);
 
 		const widget = chatWidgetService.getWidgetBySessionResource(sessionResource);
 		if (!widget) {
+			logService.error('[AgentFeedback] Cannot submit feedback: no chat widget found for session', sessionResource.toString());
 			return;
 		}
 
@@ -114,27 +141,27 @@ class NavigateFeedbackAction extends AgentFeedbackEditorAction {
 				id: Menus.AgentFeedbackEditorContent,
 				group: 'navigate',
 				order: _next ? 2 : 1,
-				when: ChatContextKeys.enabled,
+				when: ContextKeyExpr.and(ChatContextKeys.enabled, hasSessionEditorComments),
 			},
 		});
 	}
 
-	override runWithSession(accessor: ServicesAccessor, sessionResource: URI): void {
+	override async runWithSession(accessor: ServicesAccessor, sessionResource: URI): Promise<void> {
 		const agentFeedbackService = accessor.get(IAgentFeedbackService);
-		const editorService = accessor.get(IEditorService);
-
-		const feedback = agentFeedbackService.getNextFeedback(sessionResource, this._next);
-		if (!feedback) {
+		const codeReviewService = accessor.get(ICodeReviewService);
+		const comments = getSessionEditorComments(
+			sessionResource,
+			agentFeedbackService.getFeedback(sessionResource),
+			codeReviewService.getReviewState(sessionResource).get(),
+			codeReviewService.getPRReviewState(sessionResource).get(),
+		);
+
+		const comment = agentFeedbackService.getNextNavigableItem(sessionResource, comments, this._next);
+		if (!comment) {
 			return;
 		}
 
-		editorService.openEditor({
-			resource: feedback.resourceUri,
-			options: {
-				preserveFocus: false,
-				revealIfVisible: true,
-			}
-		});
+		await agentFeedbackService.revealSessionComment(sessionResource, comment.id, comment.resourceUri, comment.range);
 	}
 }
 
@@ -152,7 +179,7 @@ class ClearAllFeedbackAction extends AgentFeedbackEditorAction {
 				id: Menus.AgentFeedbackEditorContent,
 				group: 'a_submit',
 				order: 1,
-				when: ChatContextKeys.enabled,
+				when: ContextKeyExpr.and(ChatContextKeys.enabled, hasSessionAgentFeedback),
 			},
 		});
 	}
@@ -177,6 +204,6 @@ export function registerAgentFeedbackEditorActions(): void {
 		},
 		group: 'navigate',
 		order: -1,
-		when: ChatContextKeys.enabled,
+		when: ContextKeyExpr.and(ChatContextKeys.enabled, hasSessionEditorComments),
 	});
 }
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorInputContribution.ts b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorInputContribution.ts
index 6e733fd5a1015..1f881cc12231a 100644
--- a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorInputContribution.ts
+++ b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorInputContribution.ts
@@ -11,13 +11,18 @@ import { EditorContributionInstantiation, registerEditorContribution } from '../
 import { EditorOption } from '../../../../editor/common/config/editorOptions.js';
 import { SelectionDirection } from '../../../../editor/common/core/selection.js';
 import { URI } from '../../../../base/common/uri.js';
-import { addStandardDisposableListener, getWindow } from '../../../../base/browser/dom.js';
+import { addStandardDisposableListener, getWindow, ModifierKeyEmitter } from '../../../../base/browser/dom.js';
 import { KeyCode } from '../../../../base/common/keyCodes.js';
 import { IAgentFeedbackService } from './agentFeedbackService.js';
 import { IChatEditingService } from '../../../../workbench/contrib/chat/common/editing/chatEditingService.js';
 import { IAgentSessionsService } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
 import { getSessionForResource } from './agentFeedbackEditorUtils.js';
 import { localize } from '../../../../nls.js';
+import { ActionBar } from '../../../../base/browser/ui/actionbar/actionbar.js';
+import { Action } from '../../../../base/common/actions.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { ThemeIcon } from '../../../../base/common/themables.js';
+import { Emitter, Event } from '../../../../base/common/event.js';
 
 class AgentFeedbackInputWidget implements IOverlayWidget {
 
@@ -30,9 +35,18 @@ class AgentFeedbackInputWidget implements IOverlayWidget {
 	private readonly _domNode: HTMLElement;
 	private readonly _inputElement: HTMLTextAreaElement;
 	private readonly _measureElement: HTMLElement;
+	private readonly _actionBar: ActionBar;
+	private readonly _addAction: Action;
+	private readonly _addAndSubmitAction: Action;
 	private _position: IOverlayWidgetPosition | null = null;
 	private _lineHeight = 0;
 
+	private readonly _onDidTriggerAdd = new Emitter<void>();
+	readonly onDidTriggerAdd: Event<void> = this._onDidTriggerAdd.event;
+
+	private readonly _onDidTriggerAddAndSubmit = new Emitter<void>();
+	readonly onDidTriggerAddAndSubmit: Event<void> = this._onDidTriggerAddAndSubmit.event;
+
 	constructor(
 		private readonly _editor: ICodeEditor,
 	) {
@@ -50,9 +64,54 @@ class AgentFeedbackInputWidget implements IOverlayWidget {
 		this._measureElement.classList.add('agent-feedback-input-measure');
 		this._domNode.appendChild(this._measureElement);
 
+		// Action bar with add/submit actions
+		const actionsContainer = document.createElement('div');
+		actionsContainer.classList.add('agent-feedback-input-actions');
+		this._domNode.appendChild(actionsContainer);
+
+		this._addAction = new Action(
+			'agentFeedback.add',
+			localize('agentFeedback.add', "Add Feedback (Enter)"),
+			ThemeIcon.asClassName(Codicon.plus),
+			false,
+			() => { this._onDidTriggerAdd.fire(); return Promise.resolve(); }
+		);
+
+		this._addAndSubmitAction = new Action(
+			'agentFeedback.addAndSubmit',
+			localize('agentFeedback.addAndSubmit', "Add Feedback and Submit (Alt+Enter)"),
+			ThemeIcon.asClassName(Codicon.send),
+			false,
+			() => { this._onDidTriggerAddAndSubmit.fire(); return Promise.resolve(); }
+		);
+
+		this._actionBar = new ActionBar(actionsContainer);
+		this._actionBar.push(this._addAction, { icon: true, label: false, keybinding: localize('enter', "Enter") });
+
+		// Toggle to alt action when Alt key is held
+		const modifierKeyEmitter = ModifierKeyEmitter.getInstance();
+		modifierKeyEmitter.event(status => {
+			this._updateActionForAlt(status.altKey);
+		});
+
 		this._editor.applyFontInfo(this._inputElement);
 		this._editor.applyFontInfo(this._measureElement);
-		this._lineHeight = this._editor.getOption(EditorOption.lineHeight);
+		this._lineHeight = 22;
+		this._inputElement.style.lineHeight = `${this._lineHeight}px`;
+	}
+
+	private _isShowingAlt = false;
+
+	private _updateActionForAlt(altKey: boolean): void {
+		if (altKey && !this._isShowingAlt) {
+			this._isShowingAlt = true;
+			this._actionBar.clear();
+			this._actionBar.push(this._addAndSubmitAction, { icon: true, label: false, keybinding: localize('altEnter', "Alt+Enter") });
+		} else if (!altKey && this._isShowingAlt) {
+			this._isShowingAlt = false;
+			this._actionBar.clear();
+			this._actionBar.push(this._addAction, { icon: true, label: false, keybinding: localize('enter', "Enter") });
+		}
 	}
 
 	getId(): string {
@@ -86,6 +145,7 @@ class AgentFeedbackInputWidget implements IOverlayWidget {
 
 	clearInput(): void {
 		this._inputElement.value = '';
+		this._updateActionEnabled();
 		this._autoSize();
 	}
 
@@ -93,6 +153,16 @@ class AgentFeedbackInputWidget implements IOverlayWidget {
 		this._autoSize();
 	}
 
+	updateActionEnabled(): void {
+		this._updateActionEnabled();
+	}
+
+	private _updateActionEnabled(): void {
+		const hasText = this._inputElement.value.trim().length > 0;
+		this._addAction.enabled = hasText;
+		this._addAndSubmitAction.enabled = hasText;
+	}
+
 	private _autoSize(): void {
 		const text = this._inputElement.value || this._inputElement.placeholder;
 
@@ -109,6 +179,14 @@ class AgentFeedbackInputWidget implements IOverlayWidget {
 		const newHeight = Math.max(this._inputElement.scrollHeight, this._lineHeight);
 		this._inputElement.style.height = `${newHeight}px`;
 	}
+
+	dispose(): void {
+		this._actionBar.dispose();
+		this._addAction.dispose();
+		this._addAndSubmitAction.dispose();
+		this._onDidTriggerAdd.dispose();
+		this._onDidTriggerAddAndSubmit.dispose();
+	}
 }
 
 export class AgentFeedbackEditorInputContribution extends Disposable implements IEditorContribution {
@@ -118,6 +196,7 @@ export class AgentFeedbackEditorInputContribution extends Disposable implements
 	private _widget: AgentFeedbackInputWidget | undefined;
 	private _visible = false;
 	private _mouseDown = false;
+	private _suppressSelectionChangeOnce = false;
 	private _sessionResource: URI | undefined;
 	private readonly _widgetListeners = this._store.add(new DisposableStore());
 
@@ -165,7 +244,7 @@ export class AgentFeedbackEditorInputContribution extends Disposable implements
 				this._hide();
 			}, 0);
 		}));
-		this._store.add(this._editor.onDidFocusEditorWidget(() => this._onSelectionChanged()));
+		this._store.add(this._editor.onDidFocusEditorText(() => this._onSelectionChanged()));
 	}
 
 	private _isWidgetTarget(target: EventTarget | Element | null): boolean {
@@ -175,6 +254,8 @@ export class AgentFeedbackEditorInputContribution extends Disposable implements
 	private _ensureWidget(): AgentFeedbackInputWidget {
 		if (!this._widget) {
 			this._widget = new AgentFeedbackInputWidget(this._editor);
+			this._store.add(this._widget.onDidTriggerAdd(() => this._addFeedback()));
+			this._store.add(this._widget.onDidTriggerAddAndSubmit(() => this._addFeedbackAndSubmit()));
 			this._editor.addOverlayWidget(this._widget);
 		}
 		return this._widget;
@@ -182,11 +263,17 @@ export class AgentFeedbackEditorInputContribution extends Disposable implements
 
 	private _onModelChanged(): void {
 		this._hide();
+		this._suppressSelectionChangeOnce = false;
 		this._sessionResource = undefined;
 	}
 
 	private _onSelectionChanged(): void {
-		if (this._mouseDown || !this._editor.hasWidgetFocus()) {
+		if (this._suppressSelectionChangeOnce) {
+			this._suppressSelectionChangeOnce = false;
+			return;
+		}
+
+		if (this._mouseDown || !this._editor.hasTextFocus()) {
 			return;
 		}
 
@@ -251,13 +338,14 @@ export class AgentFeedbackEditorInputContribution extends Disposable implements
 					return;
 				}
 
-				// Don't focus if a modifier key is pressed alone
-				if (e.keyCode === KeyCode.Ctrl || e.keyCode === KeyCode.Shift || e.keyCode === KeyCode.Alt || e.keyCode === KeyCode.Meta) {
+				// Only steal focus when the editor text area itself is focused,
+				// not when an overlay widget (e.g. find widget) has focus
+				if (!this._editor.hasTextFocus()) {
 					return;
 				}
 
-				// Don't focus if any modifier is held (keyboard shortcuts)
-				if (e.ctrlKey || e.altKey || e.metaKey) {
+				// Don't focus if a modifier key is pressed alone
+				if (e.keyCode === KeyCode.Ctrl || e.keyCode === KeyCode.Shift || e.keyCode === KeyCode.Alt || e.keyCode === KeyCode.Meta) {
 					return;
 				}
 
@@ -268,6 +356,25 @@ export class AgentFeedbackEditorInputContribution extends Disposable implements
 					return;
 				}
 
+				// Ctrl+I / Cmd+I explicitly focuses the feedback input
+				if ((e.ctrlKey || e.metaKey) && e.keyCode === KeyCode.KeyI) {
+					e.preventDefault();
+					e.stopPropagation();
+					widget.inputElement.focus();
+					return;
+				}
+
+				// Don't focus if any modifier is held (keyboard shortcuts)
+				if (e.ctrlKey || e.altKey || e.metaKey) {
+					return;
+				}
+
+				// Only auto-focus the input on typing when the document is readonly;
+				// when editable the user must click or use Ctrl+I to focus.
+				if (!this._editor.getOption(EditorOption.readOnly)) {
+					return;
+				}
+
 				// If the input is not focused, focus it and let the keystroke go through
 				if (getWindow(widget.inputElement).document.activeElement !== widget.inputElement) {
 					widget.inputElement.focus();
@@ -285,10 +392,17 @@ export class AgentFeedbackEditorInputContribution extends Disposable implements
 				return;
 			}
 
+			if (e.keyCode === KeyCode.Enter && e.altKey) {
+				e.preventDefault();
+				e.stopPropagation();
+				this._addFeedbackAndSubmit();
+				return;
+			}
+
 			if (e.keyCode === KeyCode.Enter) {
 				e.preventDefault();
 				e.stopPropagation();
-				this._submit(widget);
+				this._addFeedback();
 				return;
 			}
 		}));
@@ -301,6 +415,7 @@ export class AgentFeedbackEditorInputContribution extends Disposable implements
 		// Auto-size the textarea as the user types
 		this._widgetListeners.add(addStandardDisposableListener(widget.inputElement, 'input', () => {
 			widget.autoSize();
+			widget.updateActionEnabled();
 			this._updatePosition();
 		}));
 
@@ -319,8 +434,45 @@ export class AgentFeedbackEditorInputContribution extends Disposable implements
 		}));
 	}
 
-	private _submit(widget: AgentFeedbackInputWidget): void {
-		const text = widget.inputElement.value.trim();
+	focusInput(): void {
+		if (this._visible && this._widget) {
+			this._widget.inputElement.focus();
+		}
+	}
+
+	private _hideAndRefocusEditor(): void {
+		this._suppressSelectionChangeOnce = true;
+		this._hide();
+		this._editor.focus();
+	}
+
+	private _addFeedback(): boolean {
+		if (!this._widget) {
+			return false;
+		}
+
+		const text = this._widget.inputElement.value.trim();
+		if (!text) {
+			return false;
+		}
+
+		const selection = this._editor.getSelection();
+		const model = this._editor.getModel();
+		if (!selection || !model || !this._sessionResource) {
+			return false;
+		}
+
+		this._agentFeedbackService.addFeedback(this._sessionResource, model.uri, selection, text);
+		this._hideAndRefocusEditor();
+		return true;
+	}
+
+	private _addFeedbackAndSubmit(): void {
+		if (!this._widget) {
+			return;
+		}
+
+		const text = this._widget.inputElement.value.trim();
 		if (!text) {
 			return;
 		}
@@ -331,9 +483,9 @@ export class AgentFeedbackEditorInputContribution extends Disposable implements
 			return;
 		}
 
-		this._agentFeedbackService.addFeedback(this._sessionResource, model.uri, selection, text);
-		this._hide();
-		this._editor.focus();
+		const sessionResource = this._sessionResource;
+		this._hideAndRefocusEditor();
+		this._agentFeedbackService.addFeedbackAndSubmit(sessionResource, model.uri, selection, text);
 	}
 
 	private _updatePosition(): void {
@@ -393,6 +545,7 @@ export class AgentFeedbackEditorInputContribution extends Disposable implements
 	override dispose(): void {
 		if (this._widget) {
 			this._editor.removeOverlayWidget(this._widget);
+			this._widget.dispose();
 			this._widget = undefined;
 		}
 		super.dispose();
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorOverlay.ts b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorOverlay.ts
index 56cb43ad9347d..7780c40acab20 100644
--- a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorOverlay.ts
+++ b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorOverlay.ts
@@ -18,13 +18,15 @@ import { IWorkbenchContribution } from '../../../../workbench/common/contributio
 import { EditorGroupView } from '../../../../workbench/browser/parts/editor/editorGroupView.js';
 import { IEditorGroup, IEditorGroupsService } from '../../../../workbench/services/editor/common/editorGroupsService.js';
 import { IAgentFeedbackService } from './agentFeedbackService.js';
-import { navigateNextFeedbackActionId, navigatePreviousFeedbackActionId, navigationBearingFakeActionId, submitFeedbackActionId } from './agentFeedbackEditorActions.js';
+import { hasSessionAgentFeedback, hasSessionEditorComments, navigateNextFeedbackActionId, navigatePreviousFeedbackActionId, navigationBearingFakeActionId, submitFeedbackActionId } from './agentFeedbackEditorActions.js';
 import { assertType } from '../../../../base/common/types.js';
 import { localize } from '../../../../nls.js';
 import { getActiveResourceCandidates, getSessionForResource } from './agentFeedbackEditorUtils.js';
 import { Menus } from '../../../browser/menus.js';
 import { IChatEditingService } from '../../../../workbench/contrib/chat/common/editing/chatEditingService.js';
 import { IAgentSessionsService } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
+import { ICodeReviewService } from '../../codeReview/browser/codeReviewService.js';
+import { getSessionEditorComments, hasAgentFeedbackComments } from './sessionEditorComments.js';
 
 class AgentFeedbackActionViewItem extends ActionViewItem {
 
@@ -54,7 +56,7 @@ class AgentFeedbackActionViewItem extends ActionViewItem {
 	}
 }
 
-class AgentFeedbackOverlayWidget extends Disposable {
+export class AgentFeedbackOverlayWidget extends Disposable {
 
 	private readonly _domNode: HTMLElement;
 	private readonly _toolbarNode: HTMLElement;
@@ -145,6 +147,8 @@ class AgentFeedbackOverlayController {
 		@IAgentSessionsService agentSessionsService: IAgentSessionsService,
 		@IInstantiationService instaService: IInstantiationService,
 		@IChatEditingService chatEditingService: IChatEditingService,
+		@IContextKeyService contextKeyService: IContextKeyService,
+		@ICodeReviewService codeReviewService: ICodeReviewService,
 	) {
 		this._domNode.classList.add('agent-feedback-editor-overlay');
 		this._domNode.style.position = 'absolute';
@@ -155,6 +159,8 @@ class AgentFeedbackOverlayController {
 		const widget = this._store.add(instaService.createInstance(AgentFeedbackOverlayWidget));
 		this._domNode.appendChild(widget.getDomNode());
 		this._store.add(toDisposable(() => this._domNode.remove()));
+		const hasCommentsContext = hasSessionEditorComments.bindTo(contextKeyService);
+		const hasAgentFeedbackContext = hasSessionAgentFeedback.bindTo(contextKeyService);
 
 		const show = () => {
 			if (!container.contains(this._domNode)) {
@@ -181,19 +187,35 @@ class AgentFeedbackOverlayController {
 
 			const candidates = getActiveResourceCandidates(group.activeEditorPane?.input);
 			let navigationBearings = undefined;
+			let hasAgentFeedback = false;
 			for (const candidate of candidates) {
 				const sessionResource = getSessionForResource(candidate, chatEditingService, agentSessionsService);
-				if (sessionResource && agentFeedbackService.getFeedback(sessionResource).length > 0) {
-					navigationBearings = agentFeedbackService.getNavigationBearing(sessionResource);
+				if (!sessionResource) {
+					continue;
+				}
+
+				const comments = getSessionEditorComments(
+					sessionResource,
+					agentFeedbackService.getFeedback(sessionResource),
+					codeReviewService.getReviewState(sessionResource).read(r),
+					codeReviewService.getPRReviewState(sessionResource).read(r),
+				);
+				if (comments.length > 0) {
+					navigationBearings = agentFeedbackService.getNavigationBearing(sessionResource, comments);
+					hasAgentFeedback = hasAgentFeedbackComments(comments);
 					break;
 				}
 			}
 
 			if (!navigationBearings) {
+				hasCommentsContext.set(false);
+				hasAgentFeedbackContext.set(false);
 				hide();
 				return;
 			}
 
+			hasCommentsContext.set(true);
+			hasAgentFeedbackContext.set(hasAgentFeedback);
 			widget.show(navigationBearings);
 			show();
 		}));
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorWidgetContribution.ts b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorWidgetContribution.ts
index 5232f8633eef4..09ccece771785 100644
--- a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorWidgetContribution.ts
+++ b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackEditorWidgetContribution.ts
@@ -5,9 +5,11 @@
 
 import './media/agentFeedbackEditorWidget.css';
 
+import { Action } from '../../../../base/common/actions.js';
 import { Codicon } from '../../../../base/common/codicons.js';
 import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
 import { Event } from '../../../../base/common/event.js';
+import { autorun, observableSignalFromEvent } from '../../../../base/common/observable.js';
 import { ICodeEditor, IOverlayWidget, IOverlayWidgetPosition } from '../../../../editor/browser/editorBrowser.js';
 import { IEditorContribution, IEditorDecorationsCollection, ScrollType } from '../../../../editor/common/editorCommon.js';
 import { EditorContributionInstantiation, registerEditorContribution } from '../../../../editor/browser/editorExtensions.js';
@@ -19,46 +21,20 @@ import { Range } from '../../../../editor/common/core/range.js';
 import { overviewRulerRangeHighlight } from '../../../../editor/common/core/editorColorRegistry.js';
 import { OverviewRulerLane } from '../../../../editor/common/model.js';
 import { themeColorFromId } from '../../../../platform/theme/common/themeService.js';
+import { ThemeIcon } from '../../../../base/common/themables.js';
 import * as nls from '../../../../nls.js';
-import { IAgentFeedback, IAgentFeedbackService } from './agentFeedbackService.js';
+import { IAgentFeedbackService } from './agentFeedbackService.js';
 import { IChatEditingService } from '../../../../workbench/contrib/chat/common/editing/chatEditingService.js';
+import { IChatSessionFileChange, IChatSessionFileChange2, isIChatSessionFileChange2 } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
 import { IAgentSessionsService } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
 import { getSessionForResource } from './agentFeedbackEditorUtils.js';
-
-/**
- * Groups nearby feedback items within a threshold number of lines.
- */
-function groupNearbyFeedback(items: readonly IAgentFeedback[], lineThreshold: number = 5): IAgentFeedback[][] {
-	if (items.length === 0) {
-		return [];
-	}
-
-	// Sort by start line number
-	const sorted = [...items].sort((a, b) => a.range.startLineNumber - b.range.startLineNumber);
-
-	const groups: IAgentFeedback[][] = [];
-	let currentGroup: IAgentFeedback[] = [sorted[0]];
-
-	for (let i = 1; i < sorted.length; i++) {
-		const firstItem = currentGroup[0];
-		const currentItem = sorted[i];
-
-		const verticalSpan = currentItem.range.startLineNumber - firstItem.range.startLineNumber;
-
-		if (verticalSpan <= lineThreshold) {
-			currentGroup.push(currentItem);
-		} else {
-			groups.push(currentGroup);
-			currentGroup = [currentItem];
-		}
-	}
-
-	if (currentGroup.length > 0) {
-		groups.push(currentGroup);
-	}
-
-	return groups;
-}
+import { ICodeReviewService, IPRReviewState } from '../../codeReview/browser/codeReviewService.js';
+import { getSessionEditorComments, groupNearbySessionEditorComments, ISessionEditorComment, SessionEditorCommentSource, toSessionEditorCommentId } from './sessionEditorComments.js';
+import { ActionBar } from '../../../../base/browser/ui/actionbar/actionbar.js';
+import { isEqual } from '../../../../base/common/resources.js';
+import { IMarkdownRendererService } from '../../../../platform/markdown/browser/markdownRenderer.js';
+import { MarkdownString } from '../../../../base/common/htmlContent.js';
+import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 
 /**
  * Widget that displays agent feedback comments for a group of nearby feedback items.
@@ -72,7 +48,6 @@ export class AgentFeedbackEditorWidget extends Disposable implements IOverlayWid
 	private readonly _domNode: HTMLElement;
 	private readonly _headerNode: HTMLElement;
 	private readonly _titleNode: HTMLElement;
-	private readonly _dismissButton: HTMLElement;
 	private readonly _toggleButton: HTMLElement;
 	private readonly _bodyNode: HTMLElement;
 	private readonly _itemElements = new Map<string, HTMLElement>();
@@ -87,9 +62,11 @@ export class AgentFeedbackEditorWidget extends Disposable implements IOverlayWid
 
 	constructor(
 		private readonly _editor: ICodeEditor,
-		private readonly _feedbackItems: readonly IAgentFeedback[],
-		private readonly _agentFeedbackService: IAgentFeedbackService,
+		private readonly _commentItems: readonly ISessionEditorComment[],
 		private readonly _sessionResource: URI,
+		@IAgentFeedbackService private readonly _agentFeedbackService: IAgentFeedbackService,
+		@ICodeReviewService private readonly _codeReviewService: ICodeReviewService,
+		@IMarkdownRendererService private readonly _markdownRendererService: IMarkdownRendererService,
 	) {
 		super();
 
@@ -115,12 +92,6 @@ export class AgentFeedbackEditorWidget extends Disposable implements IOverlayWid
 		this._updateToggleButton();
 		this._headerNode.appendChild(this._toggleButton);
 
-		// Dismiss button
-		this._dismissButton = $('div.agent-feedback-widget-dismiss');
-		this._dismissButton.appendChild(renderIcon(Codicon.close));
-		this._dismissButton.title = nls.localize('dismiss', "Dismiss");
-		this._headerNode.appendChild(this._dismissButton);
-
 		this._domNode.appendChild(this._headerNode);
 
 		// Body (collapsible) — starts collapsed
@@ -155,11 +126,6 @@ export class AgentFeedbackEditorWidget extends Disposable implements IOverlayWid
 			this._toggleExpanded();
 		}));
 
-		// Dismiss button click
-		this._eventStore.add(addDisposableListener(this._dismissButton, 'click', (e) => {
-			e.stopPropagation();
-			this._dismiss();
-		}));
 	}
 
 	private _toggleExpanded(): void {
@@ -170,27 +136,8 @@ export class AgentFeedbackEditorWidget extends Disposable implements IOverlayWid
 		}
 	}
 
-	private _dismiss(): void {
-		// Remove all feedback items in this widget from the service
-		for (const feedback of this._feedbackItems) {
-			this._agentFeedbackService.removeFeedback(this._sessionResource, feedback.id);
-		}
-
-		this._domNode.classList.add('fadeOut');
-
-		const dispose = () => {
-			this.dispose();
-		};
-
-		const handle = setTimeout(dispose, 150);
-		this._domNode.addEventListener('animationend', () => {
-			clearTimeout(handle);
-			dispose();
-		}, { once: true });
-	}
-
 	private _updateTitle(): void {
-		const count = this._feedbackItems.length;
+		const count = this._commentItems.length;
 		if (count === 1) {
 			this._titleNode.textContent = nls.localize('oneComment', "1 comment");
 		} else {
@@ -213,37 +160,151 @@ export class AgentFeedbackEditorWidget extends Disposable implements IOverlayWid
 		clearNode(this._bodyNode);
 		this._itemElements.clear();
 
-		for (const feedback of this._feedbackItems) {
+		for (const comment of this._commentItems) {
 			const item = $('div.agent-feedback-widget-item');
-			this._itemElements.set(feedback.id, item);
+			item.classList.add(`agent-feedback-widget-item-${comment.source}`);
+			if (comment.suggestion) {
+				item.classList.add('agent-feedback-widget-item-suggestion');
+			}
+			this._itemElements.set(comment.id, item);
+
+			const itemHeader = $('div.agent-feedback-widget-item-header');
+			const itemMeta = $('div.agent-feedback-widget-item-meta');
 
-			// Line indicator
 			const lineInfo = $('span.agent-feedback-widget-line-info');
-			if (feedback.range.startLineNumber === feedback.range.endLineNumber) {
-				lineInfo.textContent = nls.localize('lineNumber', "Line {0}", feedback.range.startLineNumber);
+			if (comment.range.startLineNumber === comment.range.endLineNumber) {
+				lineInfo.textContent = nls.localize('lineNumber', "Line {0}", comment.range.startLineNumber);
 			} else {
-				lineInfo.textContent = nls.localize('lineRange', "Lines {0}-{1}", feedback.range.startLineNumber, feedback.range.endLineNumber);
+				lineInfo.textContent = nls.localize('lineRange', "Lines {0}-{1}", comment.range.startLineNumber, comment.range.endLineNumber);
 			}
-			item.appendChild(lineInfo);
+			itemMeta.appendChild(lineInfo);
 
-			// Feedback text
-			const text = $('span.agent-feedback-widget-text');
-			text.textContent = feedback.text;
+			if (comment.source !== SessionEditorCommentSource.AgentFeedback) {
+				const typeBadge = $('span.agent-feedback-widget-item-type');
+				typeBadge.textContent = this._getTypeLabel(comment);
+				itemMeta.appendChild(typeBadge);
+			}
+
+			itemHeader.appendChild(itemMeta);
+
+			const actionBarContainer = $('div.agent-feedback-widget-item-actions');
+			const actionBar = this._eventStore.add(new ActionBar(actionBarContainer));
+			if (comment.canConvertToAgentFeedback) {
+				actionBar.push(new Action(
+					'agentFeedback.widget.convert',
+					nls.localize('convertComment', "Convert to Agent Feedback"),
+					ThemeIcon.asClassName(Codicon.check),
+					true,
+					() => this._convertToAgentFeedback(comment),
+				), { icon: true, label: false });
+			}
+			actionBar.push(new Action(
+				'agentFeedback.widget.remove',
+				nls.localize('removeComment', "Remove"),
+				ThemeIcon.asClassName(Codicon.close),
+				true,
+				() => this._removeComment(comment),
+			), { icon: true, label: false });
+			itemHeader.appendChild(actionBarContainer);
+			item.appendChild(itemHeader);
+
+			const text = $('div.agent-feedback-widget-text');
+			const rendered = this._markdownRendererService.render(new MarkdownString(comment.text));
+			this._eventStore.add(rendered);
+			text.appendChild(rendered.element);
 			item.appendChild(text);
 
-			// Hover handlers for range highlighting
+			if (comment.suggestion?.edits.length) {
+				item.appendChild(this._renderSuggestion(comment));
+			}
+
 			this._eventStore.add(addDisposableListener(item, 'mouseenter', () => {
-				this._highlightRange(feedback);
+				this._highlightRange(comment);
 			}));
 
 			this._eventStore.add(addDisposableListener(item, 'mouseleave', () => {
 				this._rangeHighlightDecoration.clear();
 			}));
 
+			this._eventStore.add(addDisposableListener(item, 'click', e => {
+				if ((e.target as HTMLElement | null)?.closest('.action-bar')) {
+					return;
+				}
+				this.focusFeedback(comment.id);
+				this._agentFeedbackService.setNavigationAnchor(this._sessionResource, comment.id);
+				this._revealComment(comment);
+			}));
+
 			this._bodyNode.appendChild(item);
 		}
 	}
 
+	private _getTypeLabel(comment: ISessionEditorComment): string {
+		if (comment.source === SessionEditorCommentSource.PRReview) {
+			return nls.localize('prReviewComment', "PR Review");
+		}
+
+		if (comment.source === SessionEditorCommentSource.CodeReview) {
+			return comment.suggestion
+				? nls.localize('reviewSuggestion', "Review Suggestion")
+				: nls.localize('reviewComment', "Review");
+		}
+
+		return comment.suggestion
+			? nls.localize('feedbackSuggestion', "Feedback Suggestion")
+			: nls.localize('feedbackComment', "Feedback");
+	}
+
+	private _renderSuggestion(comment: ISessionEditorComment): HTMLElement {
+		const suggestionNode = $('div.agent-feedback-widget-suggestion');
+		const title = $('div.agent-feedback-widget-suggestion-title');
+		title.textContent = nls.localize('suggestedChange', "Suggested Change");
+		suggestionNode.appendChild(title);
+
+		for (const edit of comment.suggestion?.edits ?? []) {
+			const editNode = $('div.agent-feedback-widget-suggestion-edit');
+			const rangeLabel = $('div.agent-feedback-widget-suggestion-range');
+			if (edit.range.startLineNumber === edit.range.endLineNumber) {
+				rangeLabel.textContent = nls.localize('suggestionLineNumber', "Line {0}", edit.range.startLineNumber);
+			} else {
+				rangeLabel.textContent = nls.localize('suggestionLineRange', "Lines {0}-{1}", edit.range.startLineNumber, edit.range.endLineNumber);
+			}
+			editNode.appendChild(rangeLabel);
+
+			const newText = $('pre.agent-feedback-widget-suggestion-text');
+			newText.textContent = edit.newText;
+			editNode.appendChild(newText);
+			suggestionNode.appendChild(editNode);
+		}
+
+		return suggestionNode;
+	}
+
+	private _removeComment(comment: ISessionEditorComment): void {
+		if (comment.source === SessionEditorCommentSource.PRReview) {
+			this._codeReviewService.resolvePRReviewThread(this._sessionResource!, comment.sourceId);
+			return;
+		}
+		if (comment.source === SessionEditorCommentSource.CodeReview) {
+			this._codeReviewService.removeComment(this._sessionResource, comment.sourceId);
+			return;
+		}
+
+		this._agentFeedbackService.removeFeedback(this._sessionResource, comment.sourceId);
+	}
+
+	private _convertToAgentFeedback(comment: ISessionEditorComment): void {
+		if (!comment.canConvertToAgentFeedback) {
+			return;
+		}
+
+		const feedback = this._agentFeedbackService.addFeedback(this._sessionResource, comment.resourceUri, comment.range, comment.text, comment.suggestion);
+		this._agentFeedbackService.setNavigationAnchor(this._sessionResource, toSessionEditorCommentId(SessionEditorCommentSource.AgentFeedback, feedback.id));
+		if (comment.source === SessionEditorCommentSource.CodeReview) {
+			this._codeReviewService.removeComment(this._sessionResource, comment.sourceId);
+		}
+	}
+
 	/**
 	 * Expand the widget body.
 	 */
@@ -277,7 +338,7 @@ export class AgentFeedbackEditorWidget extends Disposable implements IOverlayWid
 			el.classList.remove('focused');
 		}
 
-		const feedback = this._feedbackItems.find(f => f.id === feedbackId);
+		const feedback = this._commentItems.find(f => f.id === feedbackId);
 		if (!feedback) {
 			return;
 		}
@@ -300,7 +361,7 @@ export class AgentFeedbackEditorWidget extends Disposable implements IOverlayWid
 		this._rangeHighlightDecoration.clear();
 	}
 
-	private _highlightRange(feedback: IAgentFeedback): void {
+	private _highlightRange(feedback: ISessionEditorComment): void {
 		const endLineNumber = feedback.range.endLineNumber;
 		const range = new Range(
 			feedback.range.startLineNumber, 1,
@@ -333,7 +394,7 @@ export class AgentFeedbackEditorWidget extends Disposable implements IOverlayWid
 	 * Returns true if this widget contains the given feedback item (by id).
 	 */
 	containsFeedback(feedbackId: string): boolean {
-		return this._feedbackItems.some(f => f.id === feedbackId);
+		return this._commentItems.some(f => f.id === feedbackId);
 	}
 
 	/**
@@ -351,11 +412,17 @@ export class AgentFeedbackEditorWidget extends Disposable implements IOverlayWid
 		const scrollTop = this._editor.getScrollTop();
 
 		const widgetWidth = getTotalWidth(this._domNode) || 280;
+		const widgetHeight = this._domNode.offsetHeight || 0;
+
+		// Compute content-relative top and clamp to keep the widget within the editor content area
+		const contentRelativeTop = this._editor.getTopForLineNumber(startLineNumber) - lineHeight;
+		const scrollHeight = this._editor.getScrollHeight();
+		const clampedContentTop = Math.min(Math.max(0, contentRelativeTop), Math.max(0, scrollHeight - widgetHeight));
 
 		this._position = {
 			stackOrdinal: 2,
 			preference: {
-				top: this._editor.getTopForLineNumber(startLineNumber) - scrollTop - lineHeight,
+				top: clampedContentTop - scrollTop,
 				left: contentLeft + contentWidth - (2 * verticalScrollbarWidth + widgetWidth)
 			}
 		};
@@ -368,8 +435,8 @@ export class AgentFeedbackEditorWidget extends Disposable implements IOverlayWid
 	 */
 	toggle(show: boolean): void {
 		this._domNode.classList.toggle('visible', show);
-		if (show && this._feedbackItems.length > 0) {
-			this.layout(this._feedbackItems[0].range.startLineNumber);
+		if (show && this._commentItems.length > 0) {
+			this.layout(this._commentItems[0].range.startLineNumber);
 		}
 	}
 
@@ -405,6 +472,16 @@ export class AgentFeedbackEditorWidget extends Disposable implements IOverlayWid
 		this._editor.removeOverlayWidget(this);
 		super.dispose();
 	}
+
+	private _revealComment(comment: ISessionEditorComment): void {
+		const range = new Range(
+			comment.range.startLineNumber,
+			1,
+			comment.range.endLineNumber,
+			this._editor.getModel()?.getLineMaxColumn(comment.range.endLineNumber) ?? 1,
+		);
+		this._editor.revealRangeInCenterIfOutsideViewport(range, ScrollType.Smooth);
+	}
 }
 
 /**
@@ -424,25 +501,21 @@ class AgentFeedbackEditorWidgetContribution extends Disposable implements IEdito
 		@IAgentFeedbackService private readonly _agentFeedbackService: IAgentFeedbackService,
 		@IChatEditingService private readonly _chatEditingService: IChatEditingService,
 		@IAgentSessionsService private readonly _agentSessionsService: IAgentSessionsService,
+		@ICodeReviewService private readonly _codeReviewService: ICodeReviewService,
+		@IInstantiationService private readonly _instantiationService: IInstantiationService,
 	) {
 		super();
 
-		this._store.add(this._agentFeedbackService.onDidChangeFeedback(e => {
-			if (this._sessionResource && e.sessionResource.toString() === this._sessionResource.toString()) {
-				this._rebuildWidgets();
-			}
-		}));
-
 		this._store.add(this._agentFeedbackService.onDidChangeNavigation(sessionResource => {
 			if (this._sessionResource && sessionResource.toString() === this._sessionResource.toString()) {
 				this._handleNavigation();
 			}
 		}));
 
-		this._store.add(this._editor.onDidChangeModel(() => {
-			this._resolveSession();
-			this._rebuildWidgets();
-		}));
+		const rebuildSignal = observableSignalFromEvent(this, Event.any(
+			this._agentFeedbackService.onDidChangeFeedback,
+			this._editor.onDidChangeModel,
+		));
 
 		this._store.add(Event.any(this._editor.onDidScrollChange, this._editor.onDidLayoutChange)(() => {
 			for (const widget of this._widgets) {
@@ -450,8 +523,20 @@ class AgentFeedbackEditorWidgetContribution extends Disposable implements IEdito
 			}
 		}));
 
-		this._resolveSession();
-		this._rebuildWidgets();
+		this._store.add(autorun(reader => {
+			rebuildSignal.read(reader);
+			this._resolveSession();
+			if (!this._sessionResource) {
+				this._clearWidgets();
+				return;
+			}
+
+			this._rebuildWidgets(
+				this._codeReviewService.getReviewState(this._sessionResource).read(reader),
+				this._codeReviewService.getPRReviewState(this._sessionResource).read(reader),
+			);
+			this._handleNavigation();
+		}));
 	}
 
 	private _resolveSession(): void {
@@ -463,10 +548,13 @@ class AgentFeedbackEditorWidgetContribution extends Disposable implements IEdito
 		this._sessionResource = getSessionForResource(model.uri, this._chatEditingService, this._agentSessionsService);
 	}
 
-	private _rebuildWidgets(): void {
+	private _rebuildWidgets(
+		reviewState = this._sessionResource ? this._codeReviewService.getReviewState(this._sessionResource).get() : undefined,
+		prReviewState: IPRReviewState | undefined = this._sessionResource ? this._codeReviewService.getPRReviewState(this._sessionResource).get() : undefined,
+	): void {
 		this._clearWidgets();
 
-		if (!this._sessionResource) {
+		if (!this._sessionResource || !reviewState) {
 			return;
 		}
 
@@ -475,39 +563,105 @@ class AgentFeedbackEditorWidgetContribution extends Disposable implements IEdito
 			return;
 		}
 
-		const allFeedback = this._agentFeedbackService.getFeedback(this._sessionResource);
-		// Filter to feedback items belonging to this editor's file
-		const fileFeedback = allFeedback.filter(f => f.resourceUri.toString() === model.uri.toString());
-		if (fileFeedback.length === 0) {
+		const comments = getSessionEditorComments(
+			this._sessionResource,
+			this._agentFeedbackService.getFeedback(this._sessionResource),
+			reviewState,
+			prReviewState,
+		);
+		const fileComments = this._getCommentsForModel(model.uri, comments);
+		if (fileComments.length === 0) {
 			return;
 		}
 
-		const groups = groupNearbyFeedback(fileFeedback, 5);
+		const groups = groupNearbySessionEditorComments(fileComments, 5);
 
 		for (const group of groups) {
-			const widget = new AgentFeedbackEditorWidget(this._editor, group, this._agentFeedbackService, this._sessionResource);
+			const widget = this._instantiationService.createInstance(AgentFeedbackEditorWidget, this._editor, group, this._sessionResource);
 			this._widgets.push(widget);
 
 			widget.layout(group[0].range.startLineNumber);
 		}
 	}
 
+	private _getCommentsForModel(resourceUri: URI, comments: readonly ISessionEditorComment[]): readonly ISessionEditorComment[] {
+		const change = this._getSessionChangeForResource(resourceUri);
+		if (!change) {
+			return comments.filter(comment => isEqual(comment.resourceUri, resourceUri));
+		}
+
+		if (!this._isCurrentOrModifiedResource(change, resourceUri)) {
+			return [];
+		}
+
+		return comments.filter(comment => comment.resourceUri.fsPath === resourceUri.fsPath);
+	}
+
+	private _getSessionChangeForResource(resourceUri: URI): IChatSessionFileChange | IChatSessionFileChange2 | undefined {
+		if (!this._sessionResource) {
+			return undefined;
+		}
+
+		const changes = this._agentSessionsService.getSession(this._sessionResource)?.changes;
+		if (!(changes instanceof Array)) {
+			return undefined;
+		}
+
+		return changes.find(change => this._changeMatchesFsPath(change, resourceUri));
+	}
+
+	private _changeMatchesFsPath(change: IChatSessionFileChange | IChatSessionFileChange2, resourceUri: URI): boolean {
+		if (isIChatSessionFileChange2(change)) {
+			return change.uri.fsPath === resourceUri.fsPath
+				|| change.modifiedUri?.fsPath === resourceUri.fsPath
+				|| change.originalUri?.fsPath === resourceUri.fsPath;
+		}
+
+		return change.modifiedUri.fsPath === resourceUri.fsPath
+			|| change.originalUri?.fsPath === resourceUri.fsPath;
+	}
+
+	private _isCurrentOrModifiedResource(change: IChatSessionFileChange | IChatSessionFileChange2, resourceUri: URI): boolean {
+		if (isIChatSessionFileChange2(change)) {
+			return isEqual(change.uri, resourceUri) || (change.modifiedUri ? isEqual(change.modifiedUri, resourceUri) : false);
+		}
+
+		return isEqual(change.modifiedUri, resourceUri);
+	}
+
 	private _handleNavigation(): void {
 		if (!this._sessionResource) {
 			return;
 		}
 
-		const bearing = this._agentFeedbackService.getNavigationBearing(this._sessionResource);
+		const model = this._editor.getModel();
+		if (!model) {
+			return;
+		}
+
+		const comments = getSessionEditorComments(
+			this._sessionResource,
+			this._agentFeedbackService.getFeedback(this._sessionResource),
+			this._codeReviewService.getReviewState(this._sessionResource).get(),
+			this._codeReviewService.getPRReviewState(this._sessionResource).get(),
+		);
+		const bearing = this._agentFeedbackService.getNavigationBearing(this._sessionResource, comments);
 		if (bearing.activeIdx < 0) {
 			return;
 		}
 
-		const allFeedback = this._agentFeedbackService.getFeedback(this._sessionResource);
-		const activeFeedback = allFeedback[bearing.activeIdx];
+		const activeFeedback = comments[bearing.activeIdx];
 		if (!activeFeedback) {
 			return;
 		}
 
+		if (this._getCommentsForModel(model.uri, [activeFeedback]).length === 0) {
+			for (const widget of this._widgets) {
+				widget.collapse();
+			}
+			return;
+		}
+
 		// Expand the widget containing the active feedback, collapse all others
 		for (const widget of this._widgets) {
 			if (widget.containsFeedback(activeFeedback.id)) {
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackHover.ts b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackHover.ts
index d02c9725cd1b8..ea4414455e5db 100644
--- a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackHover.ts
+++ b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackHover.ts
@@ -11,11 +11,12 @@ import { IListVirtualDelegate } from '../../../../base/browser/ui/list/list.js';
 import { IObjectTreeElement, ITreeNode, ITreeRenderer } from '../../../../base/browser/ui/tree/tree.js';
 import { Action } from '../../../../base/common/actions.js';
 import { Codicon } from '../../../../base/common/codicons.js';
-import { Disposable, DisposableStore, IDisposable } from '../../../../base/common/lifecycle.js';
+import { MarkdownString } from '../../../../base/common/htmlContent.js';
+import { Disposable, DisposableStore, IDisposable, MutableDisposable } from '../../../../base/common/lifecycle.js';
 import { basename } from '../../../../base/common/path.js';
 import { ThemeIcon } from '../../../../base/common/themables.js';
-import { IRange } from '../../../../editor/common/core/range.js';
 import { URI } from '../../../../base/common/uri.js';
+import { ILanguageService } from '../../../../editor/common/languages/language.js';
 import { localize } from '../../../../nls.js';
 import { FileKind } from '../../../../platform/files/common/files.js';
 import { IHoverService } from '../../../../platform/hover/browser/hover.js';
@@ -41,7 +42,7 @@ interface IFeedbackCommentElement {
 	readonly id: string;
 	readonly text: string;
 	readonly resourceUri: URI;
-	readonly range: IRange;
+	readonly codeSelection?: string;
 }
 
 type FeedbackTreeElement = IFeedbackFileElement | IFeedbackCommentElement;
@@ -78,7 +79,7 @@ class FeedbackFileRenderer implements ITreeRenderer<IFeedbackFileElement, void,
 
 	constructor(
 		private readonly _labels: ResourceLabels,
-		private readonly _agentFeedbackService: IAgentFeedbackService,
+		private readonly _agentFeedbackService: IAgentFeedbackService | undefined,
 		private readonly _sessionResource: URI,
 	) { }
 
@@ -107,17 +108,21 @@ class FeedbackFileRenderer implements ITreeRenderer<IFeedbackFileElement, void,
 		);
 
 		templateData.actionBar.clear();
-		templateData.actionBar.push(new Action(
-			'agentFeedback.removeFileComments',
-			localize('agentFeedbackHover.removeAll', "Remove All"),
-			ThemeIcon.asClassName(Codicon.close),
-			true,
-			() => {
-				for (const item of element.items) {
-					this._agentFeedbackService.removeFeedback(this._sessionResource, item.id);
+		if (this._agentFeedbackService) {
+			const service = this._agentFeedbackService;
+			const sessionResource = this._sessionResource;
+			templateData.actionBar.push(new Action(
+				'agentFeedback.removeFileComments',
+				localize('agentFeedbackHover.removeAll', "Remove All"),
+				ThemeIcon.asClassName(Codicon.close),
+				true,
+				() => {
+					for (const item of element.items) {
+						service.removeFeedback(sessionResource, item.id);
+					}
 				}
-			}
-		), { icon: true, label: false });
+			), { icon: true, label: false });
+		}
 	}
 
 	disposeTemplate(templateData: IFeedbackFileTemplate): void {
@@ -129,8 +134,10 @@ class FeedbackFileRenderer implements ITreeRenderer<IFeedbackFileElement, void,
 
 interface IFeedbackCommentTemplate {
 	readonly textElement: HTMLElement;
+	readonly row: HTMLElement;
 	readonly actionBar: ActionBar;
 	readonly templateDisposables: DisposableStore;
+	readonly hoverDisposable: MutableDisposable<IDisposable>;
 	element: IFeedbackCommentElement | undefined;
 }
 
@@ -139,8 +146,10 @@ class FeedbackCommentRenderer implements ITreeRenderer<IFeedbackCommentElement,
 	readonly templateId = FeedbackCommentRenderer.TEMPLATE_ID;
 
 	constructor(
-		private readonly _agentFeedbackService: IAgentFeedbackService,
+		private readonly _agentFeedbackService: IAgentFeedbackService | undefined,
 		private readonly _sessionResource: URI,
+		private readonly _hoverService: IHoverService,
+		private readonly _languageService: ILanguageService,
 	) { }
 
 	renderTemplate(container: HTMLElement): IFeedbackCommentTemplate {
@@ -153,16 +162,22 @@ class FeedbackCommentRenderer implements ITreeRenderer<IFeedbackCommentElement,
 		const actionBarContainer = dom.append(row, $('div.agent-feedback-hover-action-bar'));
 		const actionBar = templateDisposables.add(new ActionBar(actionBarContainer));
 
-		const templateData: IFeedbackCommentTemplate = { textElement, actionBar, templateDisposables, element: undefined };
+		const hoverDisposable = templateDisposables.add(new MutableDisposable());
 
-		templateDisposables.add(dom.addDisposableListener(row, dom.EventType.CLICK, (e) => {
-			const data = templateData.element;
-			if (data) {
-				e.preventDefault();
-				e.stopPropagation();
-				this._agentFeedbackService.revealFeedback(this._sessionResource, data.id);
-			}
-		}));
+		const templateData: IFeedbackCommentTemplate = { textElement, row, actionBar, templateDisposables, hoverDisposable, element: undefined };
+
+		if (this._agentFeedbackService) {
+			const service = this._agentFeedbackService;
+			const sessionResource = this._sessionResource;
+			templateDisposables.add(dom.addDisposableListener(row, dom.EventType.CLICK, (e) => {
+				const data = templateData.element;
+				if (data) {
+					e.preventDefault();
+					e.stopPropagation();
+					service.revealFeedback(sessionResource, data.id);
+				}
+			}));
+		}
 
 		return templateData;
 	}
@@ -173,21 +188,53 @@ class FeedbackCommentRenderer implements ITreeRenderer<IFeedbackCommentElement,
 		templateData.textElement.textContent = element.text;
 		templateData.element = element;
 
+		// In read-only mode, set up a rich markdown hover with comment + code snippet
+		if (!this._agentFeedbackService) {
+			templateData.hoverDisposable.value = this._hoverService.setupDelayedHover(
+				templateData.row,
+				() => this._buildCommentHover(element),
+				{ groupId: 'agent-feedback-comment' }
+			);
+		}
+
 		templateData.actionBar.clear();
-		templateData.actionBar.push(new Action(
-			'agentFeedback.removeComment',
-			localize('agentFeedbackHover.remove', "Remove"),
-			ThemeIcon.asClassName(Codicon.close),
-			true,
-			() => {
-				this._agentFeedbackService.removeFeedback(this._sessionResource, element.id);
-			}
-		), { icon: true, label: false });
+		if (this._agentFeedbackService) {
+			const service = this._agentFeedbackService;
+			const sessionResource = this._sessionResource;
+			templateData.actionBar.push(new Action(
+				'agentFeedback.removeComment',
+				localize('agentFeedbackHover.remove', "Remove"),
+				ThemeIcon.asClassName(Codicon.close),
+				true,
+				() => {
+					service.removeFeedback(sessionResource, element.id);
+				}
+			), { icon: true, label: false });
+		}
 	}
 
 	disposeTemplate(templateData: IFeedbackCommentTemplate): void {
 		templateData.templateDisposables.dispose();
 	}
+
+	private _buildCommentHover(element: IFeedbackCommentElement): IDelayedHoverOptions {
+		const markdown = new MarkdownString('', { isTrusted: true, supportThemeIcons: true });
+		markdown.appendText(element.text);
+
+		if (element.codeSelection) {
+			const languageId = this._languageService.guessLanguageIdByFilepathOrFirstLine(element.resourceUri);
+			markdown.appendMarkdown('\n\n');
+			markdown.appendCodeblock(languageId ?? '', element.codeSelection);
+		}
+
+		return {
+			content: markdown,
+			style: HoverStyle.Pointer,
+			position: {
+				hoverPosition: HoverPosition.RIGHT,
+			},
+		};
+	}
 }
 
 // --- Hover ---
@@ -202,16 +249,18 @@ export class AgentFeedbackHover extends Disposable {
 	constructor(
 		private readonly _element: HTMLElement,
 		private readonly _attachment: IAgentFeedbackVariableEntry,
+		private readonly _canDelete: boolean,
 		@IHoverService private readonly _hoverService: IHoverService,
 		@IInstantiationService private readonly _instantiationService: IInstantiationService,
 		@IAgentFeedbackService private readonly _agentFeedbackService: IAgentFeedbackService,
+		@ILanguageService private readonly _languageService: ILanguageService,
 	) {
 		super();
 
 		// Show on hover (delayed)
 		this._store.add(this._hoverService.setupDelayedHover(
 			this._element,
-			() => this._store.add(this._buildHoverContent()), // needs a better disposable story
+			() => this._store.add(this._buildHoverContent()),
 			{ groupId: 'chat-attachments' }
 		));
 
@@ -252,8 +301,8 @@ export class AgentFeedbackHover extends Disposable {
 			treeContainer,
 			new FeedbackTreeDelegate(),
 			[
-				new FeedbackFileRenderer(resourceLabels, this._agentFeedbackService, this._attachment.sessionResource),
-				new FeedbackCommentRenderer(this._agentFeedbackService, this._attachment.sessionResource),
+				new FeedbackFileRenderer(resourceLabels, this._canDelete ? this._agentFeedbackService : undefined, this._attachment.sessionResource),
+				new FeedbackCommentRenderer(this._canDelete ? this._agentFeedbackService : undefined, this._attachment.sessionResource, this._hoverService, this._languageService),
 			],
 			{
 				defaultIndent: 0,
@@ -313,6 +362,7 @@ export class AgentFeedbackHover extends Disposable {
 	private _buildTreeData(): { children: IObjectTreeElement<FeedbackTreeElement>[]; commentElements: IFeedbackCommentElement[] } {
 		// Group feedback items by file
 		const byFile = new Map<string, { uri: URI; comments: IFeedbackCommentElement[] }>();
+
 		for (const item of this._attachment.feedbackItems) {
 			const key = item.resourceUri.toString();
 			let group = byFile.get(key);
@@ -325,7 +375,7 @@ export class AgentFeedbackHover extends Disposable {
 				id: item.id,
 				text: item.text,
 				resourceUri: item.resourceUri,
-				range: item.range,
+				codeSelection: item.codeSelection,
 			});
 		}
 
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackLineDecorationContribution.ts b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackLineDecorationContribution.ts
deleted file mode 100644
index 119bbad2fc0ae..0000000000000
--- a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackLineDecorationContribution.ts
+++ /dev/null
@@ -1,169 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-import './media/agentFeedbackLineDecoration.css';
-import { Disposable } from '../../../../base/common/lifecycle.js';
-import { ICodeEditor, IEditorMouseEvent, MouseTargetType } from '../../../../editor/browser/editorBrowser.js';
-import { IEditorContribution } from '../../../../editor/common/editorCommon.js';
-import { EditorContributionInstantiation, registerEditorContribution } from '../../../../editor/browser/editorExtensions.js';
-import { TrackedRangeStickiness } from '../../../../editor/common/model.js';
-import { ModelDecorationOptions } from '../../../../editor/common/model/textModel.js';
-import { Range } from '../../../../editor/common/core/range.js';
-import { ThemeIcon } from '../../../../base/common/themables.js';
-import { Codicon } from '../../../../base/common/codicons.js';
-import { URI } from '../../../../base/common/uri.js';
-import { IAgentFeedbackService } from './agentFeedbackService.js';
-import { IChatEditingService } from '../../../../workbench/contrib/chat/common/editing/chatEditingService.js';
-import { IAgentSessionsService } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
-import { getSessionForResource } from './agentFeedbackEditorUtils.js';
-import { Selection } from '../../../../editor/common/core/selection.js';
-
-const addFeedbackHintDecoration = ModelDecorationOptions.register({
-	description: 'agent-feedback-add-hint',
-	linesDecorationsClassName: `${ThemeIcon.asClassName(Codicon.add)} agent-feedback-add-hint`,
-	stickiness: TrackedRangeStickiness.NeverGrowsWhenTypingAtEdges,
-});
-
-export class AgentFeedbackLineDecorationContribution extends Disposable implements IEditorContribution {
-
-	static readonly ID = 'agentFeedback.lineDecorationContribution';
-
-	private _hintDecorationId: string | null = null;
-	private _hintLine = -1;
-	private _sessionResource: URI | undefined;
-	private _feedbackLines = new Set<number>();
-
-	constructor(
-		private readonly _editor: ICodeEditor,
-		@IAgentFeedbackService private readonly _agentFeedbackService: IAgentFeedbackService,
-		@IChatEditingService private readonly _chatEditingService: IChatEditingService,
-		@IAgentSessionsService private readonly _agentSessionsService: IAgentSessionsService,
-	) {
-		super();
-
-		this._store.add(this._agentFeedbackService.onDidChangeFeedback(() => this._updateFeedbackLines()));
-		this._store.add(this._editor.onDidChangeModel(() => this._onModelChanged()));
-		this._store.add(this._editor.onMouseMove((e: IEditorMouseEvent) => this._onMouseMove(e)));
-		this._store.add(this._editor.onMouseLeave(() => this._updateHintDecoration(-1)));
-		this._store.add(this._editor.onMouseDown((e: IEditorMouseEvent) => this._onMouseDown(e)));
-
-		this._resolveSession();
-		this._updateFeedbackLines();
-	}
-
-	private _onModelChanged(): void {
-		this._updateHintDecoration(-1);
-		this._resolveSession();
-		this._updateFeedbackLines();
-	}
-
-	private _resolveSession(): void {
-		const model = this._editor.getModel();
-		if (!model) {
-			this._sessionResource = undefined;
-			return;
-		}
-		this._sessionResource = getSessionForResource(model.uri, this._chatEditingService, this._agentSessionsService);
-	}
-
-	private _updateFeedbackLines(): void {
-		if (!this._sessionResource) {
-			this._feedbackLines.clear();
-			return;
-		}
-
-		const feedbackItems = this._agentFeedbackService.getFeedback(this._sessionResource);
-		const lines = new Set<number>();
-
-		for (const item of feedbackItems) {
-			const model = this._editor.getModel();
-			if (!model || item.resourceUri.toString() !== model.uri.toString()) {
-				continue;
-			}
-
-			lines.add(item.range.startLineNumber);
-		}
-
-		this._feedbackLines = lines;
-	}
-
-	private _onMouseMove(e: IEditorMouseEvent): void {
-		if (!this._sessionResource) {
-			this._updateHintDecoration(-1);
-			return;
-		}
-
-		const isLineDecoration = e.target.type === MouseTargetType.GUTTER_LINE_DECORATIONS && !e.target.detail.isAfterLines;
-		const isContentArea = e.target.type === MouseTargetType.CONTENT_TEXT || e.target.type === MouseTargetType.CONTENT_EMPTY;
-		if (e.target.position
-			&& (isLineDecoration || isContentArea)
-			&& !this._feedbackLines.has(e.target.position.lineNumber)
-		) {
-			this._updateHintDecoration(e.target.position.lineNumber);
-		} else {
-			this._updateHintDecoration(-1);
-		}
-	}
-
-	private _updateHintDecoration(line: number): void {
-		if (line === this._hintLine) {
-			return;
-		}
-
-		this._hintLine = line;
-		this._editor.changeDecorations(accessor => {
-			if (this._hintDecorationId) {
-				accessor.removeDecoration(this._hintDecorationId);
-				this._hintDecorationId = null;
-			}
-			if (line !== -1) {
-				this._hintDecorationId = accessor.addDecoration(
-					new Range(line, 1, line, 1),
-					addFeedbackHintDecoration,
-				);
-			}
-		});
-	}
-
-	private _onMouseDown(e: IEditorMouseEvent): void {
-		if (!e.target.position
-			|| e.target.type !== MouseTargetType.GUTTER_LINE_DECORATIONS
-			|| e.target.detail.isAfterLines
-			|| !this._sessionResource
-		) {
-			return;
-		}
-
-		const lineNumber = e.target.position.lineNumber;
-
-		// Lines with existing feedback - do nothing
-		if (this._feedbackLines.has(lineNumber)) {
-			return;
-		}
-
-		// Select the line content and focus the editor
-		const model = this._editor.getModel();
-		if (!model) {
-			return;
-		}
-
-		const startColumn = model.getLineFirstNonWhitespaceColumn(lineNumber);
-		const endColumn = model.getLineLastNonWhitespaceColumn(lineNumber);
-		if (startColumn === 0 || endColumn === 0) {
-			// Empty line - select the whole line range
-			this._editor.setSelection(new Selection(lineNumber, model.getLineMaxColumn(lineNumber), lineNumber, 1));
-		} else {
-			this._editor.setSelection(new Selection(lineNumber, endColumn, lineNumber, startColumn));
-		}
-		this._editor.focus();
-	}
-
-	override dispose(): void {
-		this._updateHintDecoration(-1);
-		super.dispose();
-	}
-}
-
-registerEditorContribution(AgentFeedbackLineDecorationContribution.ID, AgentFeedbackLineDecorationContribution, EditorContributionInstantiation.Eventually);
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackService.ts b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackService.ts
index 03c6e09a1757c..c92a4ab67c448 100644
--- a/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackService.ts
+++ b/src/vs/sessions/contrib/agentFeedback/browser/agentFeedbackService.ts
@@ -11,9 +11,14 @@ import { createDecorator } from '../../../../platform/instantiation/common/insta
 import { generateUuid } from '../../../../base/common/uuid.js';
 import { isEqual } from '../../../../base/common/resources.js';
 import { IChatEditingService } from '../../../../workbench/contrib/chat/common/editing/chatEditingService.js';
+import { IChatSessionFileChange, IChatSessionFileChange2, isIChatSessionFileChange2 } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
 import { IAgentSessionsService } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
 import { agentSessionContainsResource, editingEntriesContainResource } from '../../../../workbench/contrib/chat/browser/sessionResourceMatching.js';
-import { IEditorService } from '../../../../workbench/services/editor/common/editorService.js';
+import { IEditorService, MODAL_GROUP } from '../../../../workbench/services/editor/common/editorService.js';
+import { IChatWidgetService } from '../../../../workbench/contrib/chat/browser/chat.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
+import { ICodeReviewSuggestion } from '../../codeReview/browser/codeReviewService.js';
 
 // --- Types --------------------------------------------------------------------
 
@@ -23,6 +28,11 @@ export interface IAgentFeedback {
 	readonly resourceUri: URI;
 	readonly range: IRange;
 	readonly sessionResource: URI;
+	readonly suggestion?: ICodeReviewSuggestion;
+}
+
+export interface INavigableSessionComment {
+	readonly id: string;
 }
 
 export interface IAgentFeedbackChangeEvent {
@@ -48,7 +58,7 @@ export interface IAgentFeedbackService {
 	/**
 	 * Add a feedback item for the given session.
 	 */
-	addFeedback(sessionResource: URI, resourceUri: URI, range: IRange, text: string): IAgentFeedback;
+	addFeedback(sessionResource: URI, resourceUri: URI, range: IRange, text: string, suggestion?: ICodeReviewSuggestion): IAgentFeedback;
 
 	/**
 	 * Remove a single feedback item.
@@ -70,20 +80,34 @@ export interface IAgentFeedbackService {
 	 */
 	revealFeedback(sessionResource: URI, feedbackId: string): Promise<void>;
 
+	/**
+	 * Open an editor for the given session comment (feedback or code-review) at its range
+	 * and set it as the navigation anchor.
+	 */
+	revealSessionComment(sessionResource: URI, commentId: string, resourceUri: URI, range: IRange): Promise<void>;
+
 	/**
 	 * Navigate to next/previous feedback item in a session.
 	 */
 	getNextFeedback(sessionResource: URI, next: boolean): IAgentFeedback | undefined;
+	getNextNavigableItem<T extends INavigableSessionComment>(sessionResource: URI, items: readonly T[], next: boolean): T | undefined;
+	setNavigationAnchor(sessionResource: URI, itemId: string | undefined): void;
 
 	/**
 	 * Get the current navigation bearings for a session.
 	 */
-	getNavigationBearing(sessionResource: URI): IAgentFeedbackNavigationBearing;
+	getNavigationBearing(sessionResource: URI, items?: readonly INavigableSessionComment[]): IAgentFeedbackNavigationBearing;
 
 	/**
 	 * Clear all feedback items for a session (e.g., after sending).
 	 */
 	clearFeedback(sessionResource: URI): void;
+
+	/**
+	 * Add a feedback item and then submit the feedback. Waits for the
+	 * attachment to be updated in the chat widget before submitting.
+	 */
+	addFeedbackAndSubmit(sessionResource: URI, resourceUri: URI, range: IRange, text: string, suggestion?: ICodeReviewSuggestion): Promise<void>;
 }
 
 // --- Implementation -----------------------------------------------------------
@@ -107,11 +131,14 @@ export class AgentFeedbackService extends Disposable implements IAgentFeedbackSe
 		@IChatEditingService private readonly _chatEditingService: IChatEditingService,
 		@IAgentSessionsService private readonly _agentSessionsService: IAgentSessionsService,
 		@IEditorService private readonly _editorService: IEditorService,
+		@IChatWidgetService private readonly _chatWidgetService: IChatWidgetService,
+		@ICommandService private readonly _commandService: ICommandService,
+		@ILogService private readonly _logService: ILogService,
 	) {
 		super();
 	}
 
-	addFeedback(sessionResource: URI, resourceUri: URI, range: IRange, text: string): IAgentFeedback {
+	addFeedback(sessionResource: URI, resourceUri: URI, range: IRange, text: string, suggestion?: ICodeReviewSuggestion): IAgentFeedback {
 		const key = sessionResource.toString();
 		let feedbackItems = this._feedbackBySession.get(key);
 		if (!feedbackItems) {
@@ -125,6 +152,7 @@ export class AgentFeedbackService extends Disposable implements IAgentFeedbackSe
 			resourceUri,
 			range,
 			sessionResource,
+			suggestion,
 		};
 
 		// Insert at the correct sorted position.
@@ -250,50 +278,131 @@ export class AgentFeedbackService extends Disposable implements IAgentFeedbackSe
 		if (!feedback) {
 			return;
 		}
-		await this._editorService.openEditor({
-			resource: feedback.resourceUri,
-			options: {
-				preserveFocus: false,
-				revealIfVisible: true,
-			}
-		});
-		setTimeout(() => {
-			this._navigationAnchorBySession.set(key, feedbackId);
-			this._onDidChangeNavigation.fire(sessionResource);
-		}, 50); // delay to ensure editor has revealed the correct position before firing navigation event
+		await this.revealSessionComment(sessionResource, feedbackId, feedback.resourceUri, feedback.range);
+	}
+
+	async revealSessionComment(sessionResource: URI, commentId: string, resourceUri: URI, range: IRange): Promise<void> {
+		const selection = { startLineNumber: range.startLineNumber, startColumn: range.startColumn };
+		const sessionChange = this._getSessionChange(resourceUri, this._agentSessionsService.getSession(sessionResource)?.changes);
+
+		if (sessionChange?.isDeletion && sessionChange.originalUri) {
+			await this._editorService.openEditor({
+				resource: sessionChange.originalUri,
+				options: {
+					modal: {},
+					preserveFocus: false,
+					revealIfVisible: true,
+					selection,
+				}
+			}, MODAL_GROUP);
+		} else if (sessionChange?.originalUri) {
+			await this._editorService.openEditor({
+				original: { resource: sessionChange.originalUri },
+				modified: { resource: sessionChange.modifiedUri },
+				options: {
+					modal: {},
+					preserveFocus: false,
+					revealIfVisible: true,
+					selection,
+				}
+			}, MODAL_GROUP);
+		} else {
+			await this._editorService.openEditor({
+				resource: sessionChange?.modifiedUri ?? resourceUri,
+				options: {
+					modal: {},
+					preserveFocus: false,
+					revealIfVisible: true,
+					selection,
+				}
+			}, MODAL_GROUP);
+		}
+
+		this.setNavigationAnchor(sessionResource, commentId);
+	}
+
+	private _getSessionChange(resourceUri: URI, changes: readonly IChatSessionFileChange[] | readonly IChatSessionFileChange2[] | {
+		readonly files: number;
+		readonly insertions: number;
+		readonly deletions: number;
+	} | undefined): { originalUri?: URI; modifiedUri: URI; isDeletion: boolean } | undefined {
+		if (!(changes instanceof Array)) {
+			return undefined;
+		}
+
+		const matchingChange = changes.find(change => this._changeContainsResource(change, resourceUri));
+		if (!matchingChange) {
+			return undefined;
+		}
+
+		if (isIChatSessionFileChange2(matchingChange)) {
+			return {
+				originalUri: matchingChange.originalUri,
+				modifiedUri: matchingChange.modifiedUri ?? matchingChange.uri,
+				isDeletion: matchingChange.modifiedUri === undefined,
+			};
+		}
+
+		return {
+			originalUri: matchingChange.originalUri,
+			modifiedUri: matchingChange.modifiedUri,
+			isDeletion: false,
+		};
+	}
+
+	private _changeContainsResource(change: IChatSessionFileChange | IChatSessionFileChange2, resourceUri: URI): boolean {
+		if (isIChatSessionFileChange2(change)) {
+			return change.uri.fsPath === resourceUri.fsPath
+				|| change.originalUri?.fsPath === resourceUri.fsPath
+				|| change.modifiedUri?.fsPath === resourceUri.fsPath;
+		}
+
+		return change.modifiedUri.fsPath === resourceUri.fsPath
+			|| change.originalUri?.fsPath === resourceUri.fsPath;
 	}
 
 	getNextFeedback(sessionResource: URI, next: boolean): IAgentFeedback | undefined {
+		return this.getNextNavigableItem(sessionResource, this.getFeedback(sessionResource), next);
+	}
+
+	getNextNavigableItem<T extends INavigableSessionComment>(sessionResource: URI, items: readonly T[], next: boolean): T | undefined {
 		const key = sessionResource.toString();
-		const feedbackItems = this._feedbackBySession.get(key);
-		if (!feedbackItems?.length) {
+		if (!items.length) {
 			this._navigationAnchorBySession.delete(key);
 			return undefined;
 		}
 
 		const anchorId = this._navigationAnchorBySession.get(key);
-		let anchorIndex = anchorId ? feedbackItems.findIndex(item => item.id === anchorId) : -1;
+		let anchorIndex = anchorId ? items.findIndex(item => item.id === anchorId) : -1;
 
 		if (anchorIndex < 0 && !next) {
 			anchorIndex = 0;
 		}
 
 		const nextIndex = next
-			? (anchorIndex + 1) % feedbackItems.length
-			: (anchorIndex - 1 + feedbackItems.length) % feedbackItems.length;
+			? (anchorIndex + 1) % items.length
+			: (anchorIndex - 1 + items.length) % items.length;
 
-		const feedback = feedbackItems[nextIndex];
-		this._navigationAnchorBySession.set(key, feedback.id);
+		const item = items[nextIndex];
+		this.setNavigationAnchor(sessionResource, item.id);
+		return item;
+	}
+
+	setNavigationAnchor(sessionResource: URI, itemId: string | undefined): void {
+		const key = sessionResource.toString();
+		if (itemId) {
+			this._navigationAnchorBySession.set(key, itemId);
+		} else {
+			this._navigationAnchorBySession.delete(key);
+		}
 		this._onDidChangeNavigation.fire(sessionResource);
-		return feedback;
 	}
 
-	getNavigationBearing(sessionResource: URI): IAgentFeedbackNavigationBearing {
+	getNavigationBearing(sessionResource: URI, items: readonly INavigableSessionComment[] = this._feedbackBySession.get(sessionResource.toString()) ?? []): IAgentFeedbackNavigationBearing {
 		const key = sessionResource.toString();
-		const feedbackItems = this._feedbackBySession.get(key) ?? [];
 		const anchorId = this._navigationAnchorBySession.get(key);
-		const activeIdx = anchorId ? feedbackItems.findIndex(item => item.id === anchorId) : -1;
-		return { activeIdx, totalCount: feedbackItems.length };
+		const activeIdx = anchorId ? items.findIndex(item => item.id === anchorId) : -1;
+		return { activeIdx, totalCount: items.length };
 	}
 
 	clearFeedback(sessionResource: URI): void {
@@ -304,4 +413,30 @@ export class AgentFeedbackService extends Disposable implements IAgentFeedbackSe
 		this._onDidChangeNavigation.fire(sessionResource);
 		this._onDidChangeFeedback.fire({ sessionResource, feedbackItems: [] });
 	}
+
+	async addFeedbackAndSubmit(sessionResource: URI, resourceUri: URI, range: IRange, text: string, suggestion?: ICodeReviewSuggestion): Promise<void> {
+		this.addFeedback(sessionResource, resourceUri, range, text, suggestion);
+
+		// Wait for the attachment contribution to update the chat widget's attachment model
+		const widget = this._chatWidgetService.getWidgetBySessionResource(sessionResource);
+		if (widget) {
+			const attachmentId = 'agentFeedback:' + sessionResource.toString();
+			const hasAttachment = () => widget.attachmentModel.attachments.some(a => a.id === attachmentId);
+
+			if (!hasAttachment()) {
+				await Event.toPromise(
+					Event.filter(widget.attachmentModel.onDidChange, () => hasAttachment())
+				);
+			}
+		} else {
+			this._logService.error('[AgentFeedback] addFeedbackAndSubmit: no chat widget found for session, feedback may not be submitted correctly', sessionResource.toString());
+			await new Promise(resolve => setTimeout(resolve, 100));
+		}
+
+		try {
+			await this._commandService.executeCommand('agentFeedbackEditor.action.submit');
+		} catch (err) {
+			this._logService.error('[AgentFeedback] Failed to execute submit feedback command', err);
+		}
+	}
 }
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackEditorInput.css b/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackEditorInput.css
index f8d62a4fe28e7..b467ff7f7aa8d 100644
--- a/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackEditorInput.css
+++ b/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackEditorInput.css
@@ -7,10 +7,13 @@
 	position: absolute;
 	z-index: 10000;
 	background-color: var(--vscode-panel-background);
-	border: 1px solid var(--vscode-menu-border, var(--vscode-widget-border));
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	border: 1px solid var(--vscode-agentFeedbackInputWidget-border, var(--vscode-input-border, var(--vscode-widget-border)));
+	box-shadow: var(--vscode-shadow-lg);
 	border-radius: 8px;
 	padding: 4px;
+	display: flex;
+	flex-direction: row;
+	align-items: flex-end;
 }
 
 .agent-feedback-input-widget textarea {
@@ -18,7 +21,7 @@
 	border: none;
 	color: var(--vscode-input-foreground);
 	border-radius: 4px;
-	padding: 0;
+	padding: 0 0 0 6px;
 	outline: none;
 	min-width: 150px;
 	max-width: 400px;
@@ -28,6 +31,7 @@
 	word-wrap: break-word;
 	box-sizing: border-box;
 	display: block;
+	flex: 1;
 }
 
 .agent-feedback-input-widget textarea:focus {
@@ -46,3 +50,15 @@
 	overflow: hidden;
 	white-space: pre;
 }
+
+.agent-feedback-input-widget .agent-feedback-input-actions {
+	display: flex;
+	align-items: center;
+	margin-left: 2px;
+	flex-shrink: 0;
+}
+
+.agent-feedback-input-widget .agent-feedback-input-actions .action-bar .action-item .action-label {
+	width: 16px;
+	height: 16px;
+}
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackEditorOverlay.css b/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackEditorOverlay.css
index 1acdbe228ce56..766e481b9eb51 100644
--- a/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackEditorOverlay.css
+++ b/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackEditorOverlay.css
@@ -8,13 +8,13 @@
 	color: var(--vscode-foreground);
 	background-color: var(--vscode-editorWidget-background);
 	border-radius: 6px;
-	border: 1px solid var(--vscode-contrastBorder);
+	border: 1px solid var(--vscode-editorHoverWidget-border);
 	display: flex;
 	align-items: center;
 	justify-content: center;
 	gap: 4px;
 	z-index: 10;
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	overflow: hidden;
 }
 
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackEditorWidget.css b/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackEditorWidget.css
index 3ca674d2cf444..938da413b02e9 100644
--- a/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackEditorWidget.css
+++ b/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackEditorWidget.css
@@ -11,7 +11,7 @@
 	background-color: var(--vscode-editorWidget-background);
 	border: 1px solid var(--vscode-editorWidget-border, var(--vscode-contrastBorder));
 	border-radius: 8px;
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	font-size: 12px;
 	line-height: 1.4;
 	opacity: 0;
@@ -113,24 +113,6 @@
 }
 
 /* Dismiss button */
-.agent-feedback-widget-dismiss {
-	display: flex;
-	align-items: center;
-	justify-content: center;
-	width: 18px;
-	height: 18px;
-	border-radius: 4px;
-	cursor: pointer;
-	color: var(--vscode-foreground);
-	opacity: 0.7;
-	transition: opacity 0.1s;
-}
-
-.agent-feedback-widget-dismiss:hover {
-	opacity: 1;
-	background-color: var(--vscode-toolbar-hoverBackground);
-}
-
 /* Body - collapsible */
 .agent-feedback-widget-body {
 	transition: max-height 0.2s ease-in-out, padding 0.2s ease-in-out;
@@ -152,6 +134,7 @@
 	border-bottom: 1px solid var(--vscode-editorWidget-border, var(--vscode-widget-border));
 	cursor: pointer;
 	position: relative;
+	gap: 6px;
 }
 
 .agent-feedback-widget-item:last-child {
@@ -167,12 +150,70 @@
 	color: var(--vscode-list-activeSelectionForeground);
 }
 
+.agent-feedback-widget-item-codeReview {
+	box-shadow: inset 2px 0 0 var(--vscode-editorWarning-foreground);
+}
+
+.agent-feedback-widget-item-prReview {
+	box-shadow: inset 2px 0 0 var(--vscode-editorInfo-foreground);
+}
+
+.agent-feedback-widget-item-header {
+	display: flex;
+	align-items: flex-start;
+	justify-content: space-between;
+	gap: 8px;
+}
+
+.agent-feedback-widget-item-meta {
+	display: flex;
+	align-items: center;
+	gap: 6px;
+	min-width: 0;
+	flex-wrap: wrap;
+}
+
+.agent-feedback-widget-item-actions {
+	margin-left: auto;
+	flex: 0 0 auto;
+	opacity: 0;
+	visibility: hidden;
+	pointer-events: none;
+}
+
+.agent-feedback-widget-item:hover .agent-feedback-widget-item-actions {
+	opacity: 1;
+	visibility: visible;
+	pointer-events: auto;
+}
+
+.agent-feedback-widget-item-type {
+	display: inline-flex;
+	align-items: center;
+	padding: 1px 6px;
+	border-radius: 999px;
+	font-size: 10px;
+	font-weight: 600;
+	letter-spacing: 0.2px;
+	background: color-mix(in srgb, var(--vscode-editorWidget-border, var(--vscode-widget-border)) 25%, transparent);
+	color: var(--vscode-descriptionForeground);
+}
+
+.agent-feedback-widget-item-codeReview .agent-feedback-widget-item-type {
+	background: color-mix(in srgb, var(--vscode-editorWarning-foreground) 22%, transparent);
+	color: var(--vscode-editorWarning-foreground);
+}
+
+.agent-feedback-widget-item-prReview .agent-feedback-widget-item-type {
+	background: color-mix(in srgb, var(--vscode-editorInfo-foreground) 22%, transparent);
+	color: var(--vscode-editorInfo-foreground);
+}
+
 /* Line info */
 .agent-feedback-widget-line-info {
 	font-size: 10px;
 	font-weight: 600;
 	color: var(--vscode-descriptionForeground);
-	margin-bottom: 4px;
 	text-transform: uppercase;
 	letter-spacing: 0.5px;
 }
@@ -183,6 +224,62 @@
 	word-wrap: break-word;
 }
 
+.agent-feedback-widget-text .rendered-markdown p {
+	margin: 0;
+}
+
+.agent-feedback-widget-text .rendered-markdown code {
+	font-family: var(--monaco-monospace-font);
+	font-size: 11px;
+	padding: 1px 4px;
+	border-radius: 3px;
+	background: color-mix(in srgb, var(--vscode-editorWidget-border, var(--vscode-widget-border)) 25%, transparent);
+}
+
+.agent-feedback-widget-suggestion {
+	display: flex;
+	flex-direction: column;
+	gap: 6px;
+	padding: 8px;
+	border-radius: 6px;
+	background: color-mix(in srgb, var(--vscode-editorWidget-border, var(--vscode-widget-border)) 12%, transparent);
+}
+
+.agent-feedback-widget-item-codeReview .agent-feedback-widget-suggestion {
+	background: color-mix(in srgb, var(--vscode-editorWarning-foreground) 10%, transparent);
+}
+
+.agent-feedback-widget-item-prReview .agent-feedback-widget-suggestion {
+	background: color-mix(in srgb, var(--vscode-editorInfo-foreground) 10%, transparent);
+}
+
+.agent-feedback-widget-suggestion-title,
+.agent-feedback-widget-suggestion-range {
+	font-size: 10px;
+	font-weight: 600;
+	text-transform: uppercase;
+	letter-spacing: 0.4px;
+	color: var(--vscode-descriptionForeground);
+}
+
+.agent-feedback-widget-suggestion-edit {
+	display: flex;
+	flex-direction: column;
+	gap: 4px;
+}
+
+.agent-feedback-widget-suggestion-text {
+	margin: 0;
+	padding: 6px 8px;
+	border-radius: 4px;
+	overflow-x: auto;
+	white-space: pre-wrap;
+	font-family: monospace;
+	font-size: 11px;
+	line-height: 1.45;
+	background: color-mix(in srgb, var(--vscode-editor-background) 65%, transparent);
+}
+
 /* Gutter decoration for range indicator on hover */
 .agent-feedback-widget-range-glyph {
 	margin-left: 8px;
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackLineDecoration.css b/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackLineDecoration.css
deleted file mode 100644
index 6f503b0143fbb..0000000000000
--- a/src/vs/sessions/contrib/agentFeedback/browser/media/agentFeedbackLineDecoration.css
+++ /dev/null
@@ -1,29 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-.monaco-editor .agent-feedback-line-decoration,
-.monaco-editor .agent-feedback-add-hint {
-	border-radius: 3px;
-	display: flex !important;
-	align-items: center;
-	justify-content: center;
-	background-color: var(--vscode-editorHoverWidget-background);
-	cursor: pointer;
-	border: 1px solid var(--vscode-editorHoverWidget-border);
-	box-sizing: border-box;
-}
-
-.monaco-editor .agent-feedback-line-decoration:hover,
-.monaco-editor .agent-feedback-add-hint:hover {
-	background-color: var(--vscode-editorHoverWidget-border);
-}
-
-.monaco-editor .agent-feedback-add-hint {
-	opacity: 0.7;
-}
-
-.monaco-editor .agent-feedback-add-hint:hover {
-	opacity: 1;
-}
diff --git a/src/vs/sessions/contrib/agentFeedback/browser/sessionEditorComments.ts b/src/vs/sessions/contrib/agentFeedback/browser/sessionEditorComments.ts
new file mode 100644
index 0000000000000..ef756423d42d2
--- /dev/null
+++ b/src/vs/sessions/contrib/agentFeedback/browser/sessionEditorComments.ts
@@ -0,0 +1,138 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { IRange, Range } from '../../../../editor/common/core/range.js';
+import { URI } from '../../../../base/common/uri.js';
+import { IAgentFeedback } from './agentFeedbackService.js';
+import { CodeReviewStateKind, ICodeReviewComment, ICodeReviewState, ICodeReviewSuggestion, IPRReviewComment, IPRReviewState, PRReviewStateKind } from '../../codeReview/browser/codeReviewService.js';
+
+export const enum SessionEditorCommentSource {
+	AgentFeedback = 'agentFeedback',
+	CodeReview = 'codeReview',
+	PRReview = 'prReview',
+}
+
+export interface ISessionEditorComment {
+	readonly id: string;
+	readonly sourceId: string;
+	readonly source: SessionEditorCommentSource;
+	readonly sessionResource: URI;
+	readonly resourceUri: URI;
+	readonly range: IRange;
+	readonly text: string;
+	readonly suggestion?: ICodeReviewSuggestion;
+	readonly severity?: string;
+	readonly canConvertToAgentFeedback: boolean;
+}
+
+export function getCodeReviewComments(reviewState: ICodeReviewState): readonly ICodeReviewComment[] {
+	return reviewState.kind === CodeReviewStateKind.Result ? reviewState.comments : [];
+}
+
+export function getPRReviewComments(prReviewState: IPRReviewState | undefined): readonly IPRReviewComment[] {
+	return prReviewState?.kind === PRReviewStateKind.Loaded ? prReviewState.comments : [];
+}
+
+export function getSessionEditorComments(
+	sessionResource: URI,
+	agentFeedbackItems: readonly IAgentFeedback[],
+	reviewState: ICodeReviewState,
+	prReviewState?: IPRReviewState,
+): readonly ISessionEditorComment[] {
+	const comments: ISessionEditorComment[] = [];
+
+	for (const item of agentFeedbackItems) {
+		comments.push({
+			id: toSessionEditorCommentId(SessionEditorCommentSource.AgentFeedback, item.id),
+			sourceId: item.id,
+			source: SessionEditorCommentSource.AgentFeedback,
+			sessionResource,
+			resourceUri: item.resourceUri,
+			range: item.range,
+			text: item.text,
+			suggestion: item.suggestion,
+			canConvertToAgentFeedback: false,
+		});
+	}
+
+	for (const item of getCodeReviewComments(reviewState)) {
+		comments.push({
+			id: toSessionEditorCommentId(SessionEditorCommentSource.CodeReview, item.id),
+			sourceId: item.id,
+			source: SessionEditorCommentSource.CodeReview,
+			sessionResource,
+			resourceUri: item.uri,
+			range: item.range,
+			text: item.body,
+			suggestion: item.suggestion,
+			severity: item.severity,
+			canConvertToAgentFeedback: true,
+		});
+	}
+
+	for (const item of getPRReviewComments(prReviewState)) {
+		comments.push({
+			id: toSessionEditorCommentId(SessionEditorCommentSource.PRReview, item.id),
+			sourceId: item.id,
+			source: SessionEditorCommentSource.PRReview,
+			sessionResource,
+			resourceUri: item.uri,
+			range: item.range,
+			text: item.body,
+			canConvertToAgentFeedback: true,
+		});
+	}
+
+	comments.sort(compareSessionEditorComments);
+	return comments;
+}
+
+export function compareSessionEditorComments(a: ISessionEditorComment, b: ISessionEditorComment): number {
+	return a.resourceUri.toString().localeCompare(b.resourceUri.toString())
+		|| Range.compareRangesUsingStarts(Range.lift(a.range), Range.lift(b.range))
+		|| a.source.localeCompare(b.source)
+		|| a.sourceId.localeCompare(b.sourceId);
+}
+
+export function groupNearbySessionEditorComments(items: readonly ISessionEditorComment[], lineThreshold: number = 5): ISessionEditorComment[][] {
+	if (items.length === 0) {
+		return [];
+	}
+
+	const sorted = [...items].sort(compareSessionEditorComments);
+	const groups: ISessionEditorComment[][] = [];
+	let currentGroup: ISessionEditorComment[] = [sorted[0]];
+
+	for (let i = 1; i < sorted.length; i++) {
+		const firstItem = currentGroup[0];
+		const currentItem = sorted[i];
+
+		const sameResource = currentItem.resourceUri.toString() === firstItem.resourceUri.toString();
+		const verticalSpan = currentItem.range.startLineNumber - firstItem.range.startLineNumber;
+
+		if (sameResource && verticalSpan <= lineThreshold) {
+			currentGroup.push(currentItem);
+		} else {
+			groups.push(currentGroup);
+			currentGroup = [currentItem];
+		}
+	}
+
+	groups.push(currentGroup);
+	return groups;
+}
+
+export function getResourceEditorComments(resourceUri: URI, comments: readonly ISessionEditorComment[]): readonly ISessionEditorComment[] {
+	const resource = resourceUri.toString();
+	return comments.filter(comment => comment.resourceUri.toString() === resource);
+}
+
+export function toSessionEditorCommentId(source: SessionEditorCommentSource, sourceId: string): string {
+	return `${source}:${sourceId}`;
+}
+
+export function hasAgentFeedbackComments(comments: readonly ISessionEditorComment[]): boolean {
+	return comments.some(comment => comment.source === SessionEditorCommentSource.AgentFeedback);
+}
diff --git a/src/vs/sessions/contrib/agentFeedback/test/browser/agentFeedbackEditorOverlayWidget.fixture.ts b/src/vs/sessions/contrib/agentFeedback/test/browser/agentFeedbackEditorOverlayWidget.fixture.ts
new file mode 100644
index 0000000000000..2314f52bc38b5
--- /dev/null
+++ b/src/vs/sessions/contrib/agentFeedback/test/browser/agentFeedbackEditorOverlayWidget.fixture.ts
@@ -0,0 +1,136 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { toAction } from '../../../../../base/common/actions.js';
+import { Event } from '../../../../../base/common/event.js';
+import { IMenu, IMenuActionOptions, IMenuService, MenuId, MenuItemAction, SubmenuItemAction } from '../../../../../platform/actions/common/actions.js';
+import { ComponentFixtureContext, createEditorServices, defineComponentFixture, defineThemedFixtureGroup, registerWorkbenchServices } from '../../../../../workbench/test/browser/componentFixtures/fixtureUtils.js';
+import { AgentFeedbackOverlayWidget } from '../../browser/agentFeedbackEditorOverlay.js';
+import { clearAllFeedbackActionId, navigateNextFeedbackActionId, navigatePreviousFeedbackActionId, navigationBearingFakeActionId, submitFeedbackActionId } from '../../browser/agentFeedbackEditorActions.js';
+
+interface INavigationBearings {
+	readonly activeIdx: number;
+	readonly totalCount: number;
+}
+
+interface IFixtureOptions {
+	readonly navigationBearings: INavigationBearings;
+	readonly hasAgentFeedbackActions?: boolean;
+}
+
+class FixtureMenuService implements IMenuService {
+	constructor(private readonly _hasAgentFeedbackActions: boolean) {
+	}
+
+	declare readonly _serviceBrand: undefined;
+
+	createMenu(_id: MenuId): IMenu {
+		const navigateActions = [
+			toAction({ id: navigationBearingFakeActionId, label: 'Navigation Status', run: () => { } }),
+			toAction({ id: navigatePreviousFeedbackActionId, label: 'Previous', class: 'codicon codicon-arrow-up', run: () => { } }),
+			toAction({ id: navigateNextFeedbackActionId, label: 'Next', class: 'codicon codicon-arrow-down', run: () => { } }),
+		] as unknown as (MenuItemAction | SubmenuItemAction)[];
+
+		const submitActions = this._hasAgentFeedbackActions
+			? [
+				toAction({ id: submitFeedbackActionId, label: 'Submit', class: 'codicon codicon-send', run: () => { } }),
+				toAction({ id: clearAllFeedbackActionId, label: 'Clear', class: 'codicon codicon-clear-all', run: () => { } }),
+			] as unknown as (MenuItemAction | SubmenuItemAction)[]
+			: [];
+
+		return {
+			onDidChange: Event.None,
+			dispose: () => { },
+			getActions: () => submitActions.length > 0
+				? [
+					['navigate', navigateActions],
+					['a_submit', submitActions],
+				]
+				: [
+					['navigate', navigateActions],
+				],
+		};
+	}
+
+	getMenuActions(_id: MenuId, _contextKeyService: unknown, _options?: IMenuActionOptions) { return []; }
+	getMenuContexts() { return new Set<string>(); }
+	resetHiddenStates() { }
+}
+
+function renderWidget(context: ComponentFixtureContext, options: IFixtureOptions): void {
+	const scopedDisposables = context.disposableStore.add(new DisposableStore());
+	context.container.classList.add('monaco-workbench');
+	context.container.style.width = '420px';
+	context.container.style.height = '64px';
+	context.container.style.padding = '12px';
+	context.container.style.background = 'var(--vscode-editor-background)';
+
+	const instantiationService = createEditorServices(scopedDisposables, {
+		colorTheme: context.theme,
+		additionalServices: reg => {
+			reg.defineInstance(IMenuService, new FixtureMenuService(options.hasAgentFeedbackActions ?? true));
+			registerWorkbenchServices(reg);
+		},
+	});
+
+	const widget = scopedDisposables.add(instantiationService.createInstance(AgentFeedbackOverlayWidget));
+	widget.show(options.navigationBearings);
+	context.container.appendChild(widget.getDomNode());
+}
+
+export default defineThemedFixtureGroup({ path: 'sessions/agentFeedback/' }, {
+	ZeroOfZero: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			navigationBearings: { activeIdx: -1, totalCount: 0 },
+			hasAgentFeedbackActions: false,
+		}),
+	}),
+
+	SingleFeedback: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			navigationBearings: { activeIdx: 0, totalCount: 1 },
+		}),
+	}),
+
+	FirstOfThree: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			navigationBearings: { activeIdx: -1, totalCount: 3 },
+		}),
+	}),
+
+	ReviewOnlyTwoComments: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			navigationBearings: { activeIdx: 0, totalCount: 2 },
+			hasAgentFeedbackActions: false,
+		}),
+	}),
+
+	MiddleOfThree: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			navigationBearings: { activeIdx: 1, totalCount: 3 },
+		}),
+	}),
+
+	MixedFourComments: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			navigationBearings: { activeIdx: 2, totalCount: 4 },
+			hasAgentFeedbackActions: true,
+		}),
+	}),
+
+	LastOfThree: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			navigationBearings: { activeIdx: 2, totalCount: 3 },
+		}),
+	}),
+});
diff --git a/src/vs/sessions/contrib/agentFeedback/test/browser/agentFeedbackEditorWidget.fixture.ts b/src/vs/sessions/contrib/agentFeedback/test/browser/agentFeedbackEditorWidget.fixture.ts
new file mode 100644
index 0000000000000..3beeee9243db4
--- /dev/null
+++ b/src/vs/sessions/contrib/agentFeedback/test/browser/agentFeedbackEditorWidget.fixture.ts
@@ -0,0 +1,413 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Event } from '../../../../../base/common/event.js';
+import { Color } from '../../../../../base/common/color.js';
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { IMarkdownRendererService, MarkdownRendererService } from '../../../../../platform/markdown/browser/markdownRenderer.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { mock } from '../../../../../base/test/common/mock.js';
+import { observableValue } from '../../../../../base/common/observable.js';
+import { CodeEditorWidget, ICodeEditorWidgetOptions } from '../../../../../editor/browser/widget/codeEditor/codeEditorWidget.js';
+import { IRange } from '../../../../../editor/common/core/range.js';
+import { TokenizationRegistry } from '../../../../../editor/common/languages.js';
+import { IAgentFeedback, IAgentFeedbackService } from '../../browser/agentFeedbackService.js';
+import { AgentFeedbackEditorWidget } from '../../browser/agentFeedbackEditorWidgetContribution.js';
+import { ComponentFixtureContext, createEditorServices, createTextModel, defineComponentFixture, defineThemedFixtureGroup } from '../../../../../workbench/test/browser/componentFixtures/fixtureUtils.js';
+import { CodeReviewStateKind, ICodeReviewService, ICodeReviewState, ICodeReviewSuggestion, IPRReviewState, PRReviewStateKind } from '../../../codeReview/browser/codeReviewService.js';
+import { ISessionEditorComment, SessionEditorCommentSource } from '../../browser/sessionEditorComments.js';
+
+const sessionResource = URI.parse('vscode-agent-session://fixture/session-1');
+const fileResource = URI.parse('inmemory://model/agent-feedback-widget.ts');
+
+const sampleCode = [
+	'function alpha() {',
+	'\tconst first = 1;',
+	'\treturn first;',
+	'}',
+	'',
+	'function beta() {',
+	'\tconst second = 2;',
+	'\tconst third = second + 1;',
+	'\treturn third;',
+	'}',
+	'',
+	'function gamma() {',
+	'\tconst done = true;',
+	'\treturn done;',
+	'}',
+].join('\n');
+
+interface IFixtureOptions {
+	readonly expanded?: boolean;
+	readonly focusedCommentId?: string;
+	readonly hidden?: boolean;
+	readonly commentItems: readonly ISessionEditorComment[];
+}
+
+function createRange(startLineNumber: number, endLineNumber: number = startLineNumber): IRange {
+	return {
+		startLineNumber,
+		startColumn: 1,
+		endLineNumber,
+		endColumn: 1,
+	};
+}
+
+function createFeedbackComment(id: string, text: string, startLineNumber: number, endLineNumber: number = startLineNumber, suggestion?: ICodeReviewSuggestion): ISessionEditorComment {
+	return {
+		id: `agentFeedback:${id}`,
+		sourceId: id,
+		source: SessionEditorCommentSource.AgentFeedback,
+		sessionResource,
+		resourceUri: fileResource,
+		range: createRange(startLineNumber, endLineNumber),
+		text,
+		suggestion,
+		canConvertToAgentFeedback: false,
+	};
+}
+
+function createReviewComment(id: string, text: string, startLineNumber: number, endLineNumber: number = startLineNumber, suggestion?: ICodeReviewSuggestion): ISessionEditorComment {
+	const range: IRange = {
+		startLineNumber,
+		startColumn: 1,
+		endLineNumber,
+		endColumn: 1,
+	};
+
+	return {
+		id: `codeReview:${id}`,
+		sourceId: id,
+		source: SessionEditorCommentSource.CodeReview,
+		text,
+		resourceUri: fileResource,
+		range,
+		sessionResource,
+		suggestion,
+		severity: 'warning',
+		canConvertToAgentFeedback: true,
+	};
+}
+
+function createPRReviewComment(id: string, text: string, startLineNumber: number, endLineNumber: number = startLineNumber): ISessionEditorComment {
+	return {
+		id: `prReview:${id}`,
+		sourceId: id,
+		source: SessionEditorCommentSource.PRReview,
+		text,
+		resourceUri: fileResource,
+		range: createRange(startLineNumber, endLineNumber),
+		sessionResource,
+		canConvertToAgentFeedback: true,
+	};
+}
+
+function createMockAgentFeedbackService(): IAgentFeedbackService {
+	return new class extends mock<IAgentFeedbackService>() {
+		override readonly onDidChangeFeedback = Event.None;
+		override readonly onDidChangeNavigation = Event.None;
+
+		override addFeedback(): IAgentFeedback {
+			throw new Error('Not implemented for fixture');
+		}
+
+		override removeFeedback(): void { }
+
+		override getFeedback(): readonly IAgentFeedback[] {
+			return [];
+		}
+
+		override getMostRecentSessionForResource(): URI | undefined {
+			return undefined;
+		}
+
+		override async revealFeedback(): Promise<void> { }
+
+		override getNextFeedback(): IAgentFeedback | undefined {
+			return undefined;
+		}
+
+		override getNavigationBearing() {
+			return { activeIdx: -1, totalCount: 0 };
+		}
+
+		override getNextNavigableItem() {
+			return undefined;
+		}
+
+		override setNavigationAnchor(): void { }
+
+		override clearFeedback(): void { }
+
+		override async addFeedbackAndSubmit(): Promise<void> { }
+	}();
+}
+
+function createMockCodeReviewService(): ICodeReviewService {
+	return new class extends mock<ICodeReviewService>() {
+		private readonly _state = observableValue<ICodeReviewState>('fixture.reviewState', { kind: CodeReviewStateKind.Idle });
+
+		override getReviewState() {
+			return this._state;
+		}
+
+		override hasReview(): boolean {
+			return false;
+		}
+
+		override requestReview(): void { }
+
+		override removeComment(): void { }
+
+		override dismissReview(): void { }
+
+		private readonly _prState = observableValue<IPRReviewState>('fixture.prReviewState', { kind: PRReviewStateKind.None });
+
+		override getPRReviewState() {
+			return this._prState;
+		}
+
+		override async resolvePRReviewThread(): Promise<void> { }
+	}();
+}
+
+function ensureTokenColorMap(): void {
+	if (TokenizationRegistry.getColorMap()?.length) {
+		return;
+	}
+
+	const colorMap = [
+		Color.fromHex('#000000'),
+		Color.fromHex('#d4d4d4'),
+		Color.fromHex('#9cdcfe'),
+		Color.fromHex('#ce9178'),
+		Color.fromHex('#b5cea8'),
+		Color.fromHex('#4fc1ff'),
+		Color.fromHex('#c586c0'),
+		Color.fromHex('#569cd6'),
+		Color.fromHex('#dcdcaa'),
+		Color.fromHex('#f44747'),
+	];
+
+	TokenizationRegistry.setColorMap(colorMap);
+}
+
+function renderWidget(context: ComponentFixtureContext, options: IFixtureOptions): void {
+	const scopedDisposables = context.disposableStore.add(new DisposableStore());
+	context.container.style.width = '760px';
+	context.container.style.height = '420px';
+	context.container.style.border = '1px solid var(--vscode-editorWidget-border)';
+	context.container.style.background = 'var(--vscode-editor-background)';
+
+	ensureTokenColorMap();
+
+	const agentFeedbackService = createMockAgentFeedbackService();
+	const codeReviewService = createMockCodeReviewService();
+	const instantiationService = createEditorServices(scopedDisposables, {
+		colorTheme: context.theme,
+		additionalServices: reg => {
+			reg.defineInstance(IAgentFeedbackService, agentFeedbackService);
+			reg.defineInstance(ICodeReviewService, codeReviewService);
+			reg.define(IMarkdownRendererService, MarkdownRendererService);
+		},
+	});
+	const model = scopedDisposables.add(createTextModel(instantiationService, sampleCode, fileResource, 'typescript'));
+
+	const editorOptions: ICodeEditorWidgetOptions = {
+		contributions: [],
+	};
+
+	const editor = scopedDisposables.add(instantiationService.createInstance(
+		CodeEditorWidget,
+		context.container,
+		{
+			automaticLayout: true,
+			lineNumbers: 'on',
+			minimap: { enabled: false },
+			scrollBeyondLastLine: false,
+			fontSize: 13,
+			lineHeight: 20,
+		},
+		editorOptions
+	));
+
+	editor.setModel(model);
+
+	const widget = scopedDisposables.add(instantiationService.createInstance(
+		AgentFeedbackEditorWidget,
+		editor,
+		options.commentItems,
+		sessionResource,
+	));
+
+	widget.layout(options.commentItems[0].range.startLineNumber);
+
+	if (options.expanded) {
+		widget.expand();
+	}
+
+	if (options.focusedCommentId) {
+		widget.focusFeedback(options.focusedCommentId);
+	}
+
+	if (options.hidden) {
+		const domNode = widget.getDomNode();
+		domNode.style.transition = 'none';
+		domNode.style.animation = 'none';
+		widget.toggle(false);
+	}
+}
+
+const singleFeedback = [
+	createFeedbackComment('f-1', 'Prefer a clearer variable name on this line.', 2),
+];
+
+const groupedFeedback = [
+	createFeedbackComment('f-1', 'Prefer a clearer variable name on this line.', 2),
+	createFeedbackComment('f-2', 'This return statement can be simplified.', 3),
+	createFeedbackComment('f-3', 'Consider documenting why this branch is needed.', 6, 8),
+];
+
+const reviewOnly = [
+	createReviewComment('r-1', 'Handle the null case before returning here.', 7),
+	createReviewComment('r-2', 'This branch needs a stronger explanation.', 8),
+];
+
+const mixedComments = [
+	createFeedbackComment('f-1', 'Prefer a clearer variable name on this line.', 2),
+	createReviewComment('r-1', 'This should be extracted into a helper.', 3),
+	createFeedbackComment('f-2', 'Consider renaming this for readability.', 4),
+];
+
+const reviewSuggestion: ICodeReviewSuggestion = {
+	edits: [
+		{ range: createRange(8), oldText: '\tconst third = second + 1;', newText: '\tconst third = second + computeOffset();' },
+	],
+};
+
+const suggestionMix = [
+	createReviewComment('r-3', 'Prefer using the helper so the intent is explicit.', 8, 8, reviewSuggestion),
+	createFeedbackComment('f-3', 'Keep the helper name aligned with the domain concept.', 9),
+];
+
+const prReviewOnly = [
+	createPRReviewComment('pr-1', 'This variable should be renamed to match our naming conventions.', 2),
+	createPRReviewComment('pr-2', 'Please add error handling for the edge case when second is zero.', 7, 8),
+];
+
+const allSourcesMixed = [
+	createFeedbackComment('f-1', 'Prefer a clearer variable name on this line.', 2),
+	createPRReviewComment('pr-1', 'Our style guide says to use descriptive names here.', 3),
+	createReviewComment('r-1', 'This should be extracted into a helper.', 6),
+	createPRReviewComment('pr-2', 'This logic duplicates what we have in utils.ts — consider reusing.', 8, 9),
+];
+
+export default defineThemedFixtureGroup({ path: 'sessions/agentFeedback/' }, {
+	CollapsedSingleComment: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: singleFeedback,
+		}),
+	}),
+
+	ExpandedSingleComment: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: singleFeedback,
+			expanded: true,
+		}),
+	}),
+
+	CollapsedMultiComment: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: groupedFeedback,
+		}),
+	}),
+
+	ExpandedMultiComment: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: groupedFeedback,
+			expanded: true,
+		}),
+	}),
+
+	ExpandedFocusedFeedback: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: groupedFeedback,
+			expanded: true,
+			focusedCommentId: 'agentFeedback:f-2',
+		}),
+	}),
+
+	ExpandedReviewOnly: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: reviewOnly,
+			expanded: true,
+		}),
+	}),
+
+	ExpandedMixedComments: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: mixedComments,
+			expanded: true,
+		}),
+	}),
+
+	ExpandedFocusedReviewComment: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: mixedComments,
+			expanded: true,
+			focusedCommentId: 'codeReview:r-1',
+		}),
+	}),
+
+	ExpandedReviewSuggestion: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: suggestionMix,
+			expanded: true,
+		}),
+	}),
+
+	ExpandedPRReviewOnly: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: prReviewOnly,
+			expanded: true,
+		}),
+	}),
+
+	ExpandedAllSourcesMixed: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: allSourcesMixed,
+			expanded: true,
+		}),
+	}),
+
+	ExpandedFocusedPRReview: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: allSourcesMixed,
+			expanded: true,
+			focusedCommentId: 'prReview:pr-2',
+		}),
+	}),
+
+	HiddenWidget: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: context => renderWidget(context, {
+			commentItems: mixedComments,
+			hidden: true,
+		}),
+	}),
+});
diff --git a/src/vs/sessions/contrib/agentFeedback/test/browser/sessionEditorComments.test.ts b/src/vs/sessions/contrib/agentFeedback/test/browser/sessionEditorComments.test.ts
new file mode 100644
index 0000000000000..f7bb4f0aa5b30
--- /dev/null
+++ b/src/vs/sessions/contrib/agentFeedback/test/browser/sessionEditorComments.test.ts
@@ -0,0 +1,144 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { URI } from '../../../../../base/common/uri.js';
+import { Range } from '../../../../../editor/common/core/range.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { CodeReviewStateKind, ICodeReviewState, IPRReviewState, PRReviewStateKind } from '../../../codeReview/browser/codeReviewService.js';
+import { getResourceEditorComments, getSessionEditorComments, groupNearbySessionEditorComments, hasAgentFeedbackComments, SessionEditorCommentSource } from '../../browser/sessionEditorComments.js';
+
+type ICodeReviewResultState = Extract<ICodeReviewState, { kind: CodeReviewStateKind.Result }>;
+
+suite('SessionEditorComments', () => {
+	const session = URI.parse('test://session/1');
+	const fileA = URI.parse('file:///a.ts');
+	const fileB = URI.parse('file:///b.ts');
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	function reviewState(comments: ICodeReviewResultState['comments']): ICodeReviewState {
+		return {
+			kind: CodeReviewStateKind.Result,
+			version: 'v1',
+			comments,
+		};
+	}
+
+	test('merges and sorts feedback and review comments by resource and range', () => {
+		const comments = getSessionEditorComments(session, [
+			{ id: 'feedback-b', text: 'feedback b', resourceUri: fileB, range: new Range(8, 1, 8, 1), sessionResource: session },
+			{ id: 'feedback-a', text: 'feedback a', resourceUri: fileA, range: new Range(12, 1, 12, 1), sessionResource: session },
+		], reviewState([
+			{ id: 'review-a', uri: fileA, range: new Range(3, 1, 3, 1), body: 'review a', kind: 'issue', severity: 'warning' },
+			{ id: 'review-b', uri: fileB, range: new Range(2, 1, 2, 1), body: 'review b', kind: 'issue', severity: 'warning' },
+		]));
+
+		assert.deepStrictEqual(comments.map(comment => `${comment.resourceUri.path}:${comment.range.startLineNumber}:${comment.source}`), [
+			'/a.ts:3:codeReview',
+			'/a.ts:12:agentFeedback',
+			'/b.ts:2:codeReview',
+			'/b.ts:8:agentFeedback',
+		]);
+	});
+
+	test('groups nearby comments only within the same resource', () => {
+		const comments = getSessionEditorComments(session, [
+			{ id: 'feedback-a', text: 'feedback a', resourceUri: fileA, range: new Range(10, 1, 10, 1), sessionResource: session },
+		], reviewState([
+			{ id: 'review-a', uri: fileA, range: new Range(13, 1, 13, 1), body: 'review a', kind: 'issue', severity: 'warning' },
+			{ id: 'review-b', uri: fileB, range: new Range(11, 1, 11, 1), body: 'review b', kind: 'issue', severity: 'warning' },
+		]));
+
+		const groups = groupNearbySessionEditorComments(comments, 5);
+		assert.strictEqual(groups.length, 2);
+		assert.deepStrictEqual(groups[0].map(comment => `${comment.resourceUri.path}:${comment.range.startLineNumber}:${comment.source}`), [
+			'/a.ts:10:agentFeedback',
+			'/a.ts:13:codeReview',
+		]);
+		assert.deepStrictEqual(groups[1].map(comment => `${comment.resourceUri.path}:${comment.range.startLineNumber}:${comment.source}`), [
+			'/b.ts:11:codeReview',
+		]);
+	});
+
+	test('preserves review suggestion metadata and capability flags', () => {
+		const comments = getSessionEditorComments(session, [], reviewState([
+			{
+				id: 'review-suggestion',
+				uri: fileA,
+				range: new Range(7, 1, 7, 1),
+				body: 'prefer a constant',
+				kind: 'suggestion',
+				severity: 'info',
+				suggestion: {
+					edits: [{ range: new Range(7, 1, 7, 10), oldText: 'let value', newText: 'const value' }],
+				},
+			},
+		]));
+
+		assert.strictEqual(comments.length, 1);
+		assert.strictEqual(comments[0].source, SessionEditorCommentSource.CodeReview);
+		assert.strictEqual(comments[0].canConvertToAgentFeedback, true);
+		assert.strictEqual(comments[0].suggestion?.edits[0].newText, 'const value');
+	});
+
+	test('filters resource comments and detects authored feedback presence', () => {
+		const comments = getSessionEditorComments(session, [
+			{ id: 'feedback-a', text: 'feedback a', resourceUri: fileA, range: new Range(1, 1, 1, 1), sessionResource: session },
+		], reviewState([
+			{ id: 'review-b', uri: fileB, range: new Range(2, 1, 2, 1), body: 'review b', kind: 'issue', severity: 'warning' },
+		]));
+
+		assert.strictEqual(hasAgentFeedbackComments(comments), true);
+		assert.deepStrictEqual(getResourceEditorComments(fileA, comments).map(comment => comment.source), [SessionEditorCommentSource.AgentFeedback]);
+		assert.deepStrictEqual(getResourceEditorComments(fileB, comments).map(comment => comment.source), [SessionEditorCommentSource.CodeReview]);
+	});
+
+	test('includes PR review comments when prReviewState is loaded', () => {
+		const prState: IPRReviewState = {
+			kind: PRReviewStateKind.Loaded,
+			comments: [
+				{ id: 'pr-thread-1', uri: fileA, range: new Range(5, 1, 5, 1), body: 'Please fix this', author: 'reviewer' },
+				{ id: 'pr-thread-2', uri: fileB, range: new Range(1, 1, 1, 1), body: 'Looks wrong', author: 'reviewer' },
+			],
+		};
+
+		const comments = getSessionEditorComments(session, [], reviewState([]), prState);
+		assert.strictEqual(comments.length, 2);
+		assert.deepStrictEqual(comments.map(c => `${c.resourceUri.path}:${c.range.startLineNumber}:${c.source}`), [
+			'/a.ts:5:prReview',
+			'/b.ts:1:prReview',
+		]);
+		assert.strictEqual(comments[0].canConvertToAgentFeedback, true);
+	});
+
+	test('merges PR review comments with other sources sorted correctly', () => {
+		const prState: IPRReviewState = {
+			kind: PRReviewStateKind.Loaded,
+			comments: [
+				{ id: 'pr-thread-1', uri: fileA, range: new Range(7, 1, 7, 1), body: 'PR comment', author: 'reviewer' },
+			],
+		};
+
+		const comments = getSessionEditorComments(session, [
+			{ id: 'feedback-a', text: 'feedback a', resourceUri: fileA, range: new Range(3, 1, 3, 1), sessionResource: session },
+		], reviewState([
+			{ id: 'review-a', uri: fileA, range: new Range(10, 1, 10, 1), body: 'review', kind: 'issue', severity: 'warning' },
+		]), prState);
+
+		assert.strictEqual(comments.length, 3);
+		assert.deepStrictEqual(comments.map(c => `${c.range.startLineNumber}:${c.source}`), [
+			'3:agentFeedback',
+			'7:prReview',
+			'10:codeReview',
+		]);
+	});
+
+	test('omits PR review comments when prReviewState is not loaded', () => {
+		const prState: IPRReviewState = { kind: PRReviewStateKind.None };
+		const comments = getSessionEditorComments(session, [], reviewState([]), prState);
+		assert.strictEqual(comments.length, 0);
+	});
+});
diff --git a/src/vs/sessions/contrib/aiCustomizationTreeView/browser/aiCustomizationOverviewView.ts b/src/vs/sessions/contrib/aiCustomizationTreeView/browser/aiCustomizationOverviewView.ts
index 7e335ef732616..2bcd3717a81b6 100644
--- a/src/vs/sessions/contrib/aiCustomizationTreeView/browser/aiCustomizationOverviewView.ts
+++ b/src/vs/sessions/contrib/aiCustomizationTreeView/browser/aiCustomizationOverviewView.ts
@@ -24,10 +24,12 @@ import { PromptsType } from '../../../../workbench/contrib/chat/common/promptSyn
 import { AICustomizationManagementSection } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.js';
 import { AICustomizationManagementEditorInput } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagementEditorInput.js';
 import { AICustomizationManagementEditor } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagementEditor.js';
-import { agentIcon, instructionsIcon, promptIcon, skillIcon } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationIcons.js';
+import { agentIcon, instructionsIcon, mcpServerIcon, pluginIcon, promptIcon, skillIcon } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationIcons.js';
 import { IWorkspaceContextService } from '../../../../platform/workspace/common/workspace.js';
 import { IAICustomizationWorkspaceService } from '../../../../workbench/contrib/chat/common/aiCustomizationWorkspaceService.js';
-import { IEditorService } from '../../../../workbench/services/editor/common/editorService.js';
+import { IEditorService, MODAL_GROUP } from '../../../../workbench/services/editor/common/editorService.js';
+import { IMcpService } from '../../../../workbench/contrib/mcp/common/mcpTypes.js';
+import { IAgentPluginService } from '../../../../workbench/contrib/chat/common/plugins/agentPluginService.js';
 
 const $ = DOM.$;
 
@@ -67,6 +69,8 @@ export class AICustomizationOverviewView extends ViewPane {
 		@IPromptsService private readonly promptsService: IPromptsService,
 		@IWorkspaceContextService private readonly workspaceContextService: IWorkspaceContextService,
 		@IAICustomizationWorkspaceService private readonly workspaceService: IAICustomizationWorkspaceService,
+		@IMcpService private readonly mcpService: IMcpService,
+		@IAgentPluginService private readonly agentPluginService: IAgentPluginService,
 	) {
 		super(options, keybindingService, contextMenuService, configurationService, contextKeyService, viewDescriptorService, instantiationService, openerService, themeService, hoverService);
 
@@ -76,6 +80,8 @@ export class AICustomizationOverviewView extends ViewPane {
 			{ id: AICustomizationManagementSection.Skills, label: localize('skills', "Skills"), icon: skillIcon, count: 0 },
 			{ id: AICustomizationManagementSection.Instructions, label: localize('instructions', "Instructions"), icon: instructionsIcon, count: 0 },
 			{ id: AICustomizationManagementSection.Prompts, label: localize('prompts', "Prompts"), icon: promptIcon, count: 0 },
+			{ id: AICustomizationManagementSection.McpServers, label: localize('mcpServers', "MCP Servers"), icon: mcpServerIcon, count: 0 },
+			{ id: AICustomizationManagementSection.Plugins, label: localize('plugins', "Plugins"), icon: pluginIcon, count: 0 },
 		);
 
 		// Listen to changes
@@ -173,6 +179,26 @@ export class AICustomizationOverviewView extends ViewPane {
 			}
 		}));
 
+		// Update MCP server count reactively
+		const mcpSection = this.sections.find(s => s.id === AICustomizationManagementSection.McpServers);
+		if (mcpSection) {
+			this._register(autorun(reader => {
+				const servers = this.mcpService.servers.read(reader);
+				mcpSection.count = servers.length;
+				this.updateCountElements();
+			}));
+		}
+
+		// Update plugin count reactively
+		const pluginSection = this.sections.find(s => s.id === AICustomizationManagementSection.Plugins);
+		if (pluginSection) {
+			this._register(autorun(reader => {
+				const plugins = this.agentPluginService.plugins.read(reader);
+				pluginSection.count = plugins.length;
+				this.updateCountElements();
+			}));
+		}
+
 		this.updateCountElements();
 	}
 
@@ -187,7 +213,7 @@ export class AICustomizationOverviewView extends ViewPane {
 
 	private async openSection(sectionId: AICustomizationManagementSection): Promise<void> {
 		const input = AICustomizationManagementEditorInput.getOrCreate();
-		const editor = await this.editorService.openEditor(input, { pinned: true });
+		const editor = await this.editorService.openEditor(input, { pinned: true }, MODAL_GROUP);
 
 		// Deep-link to the section
 		if (editor instanceof AICustomizationManagementEditor) {
diff --git a/src/vs/sessions/contrib/aiCustomizationTreeView/browser/aiCustomizationTreeView.contribution.ts b/src/vs/sessions/contrib/aiCustomizationTreeView/browser/aiCustomizationTreeView.contribution.ts
index a7edc620be229..d090de545769e 100644
--- a/src/vs/sessions/contrib/aiCustomizationTreeView/browser/aiCustomizationTreeView.contribution.ts
+++ b/src/vs/sessions/contrib/aiCustomizationTreeView/browser/aiCustomizationTreeView.contribution.ts
@@ -14,6 +14,9 @@ import { Codicon } from '../../../../base/common/codicons.js';
 import { ICommandService } from '../../../../platform/commands/common/commands.js';
 import { URI } from '../../../../base/common/uri.js';
 import { IEditorService } from '../../../../workbench/services/editor/common/editorService.js';
+import { IFileService, FileSystemProviderCapabilities } from '../../../../platform/files/common/files.js';
+import { IClipboardService } from '../../../../platform/clipboard/common/clipboardService.js';
+import { IDialogService } from '../../../../platform/dialogs/common/dialogs.js';
 
 //#region Utilities
 
@@ -79,7 +82,66 @@ registerAction2(class extends Action2 {
 	}
 });
 
+// Delete file action
+const DELETE_AI_CUSTOMIZATION_FILE_ID = 'aiCustomization.deleteFile';
+registerAction2(class extends Action2 {
+	constructor() {
+		super({
+			id: DELETE_AI_CUSTOMIZATION_FILE_ID,
+			title: localize2('delete', "Delete"),
+			icon: Codicon.trash,
+		});
+	}
+	async run(accessor: ServicesAccessor, context: URIContext): Promise<void> {
+		const fileService = accessor.get(IFileService);
+		const dialogService = accessor.get(IDialogService);
+		const uri = extractURI(context);
+		const name = typeof context === 'object' && !URI.isUri(context) ? (context as { name?: string }).name ?? '' : '';
+
+		if (uri.scheme !== 'file') {
+			return;
+		}
+
+		const confirmation = await dialogService.confirm({
+			message: localize('confirmDelete', "Are you sure you want to delete '{0}'?", name || uri.path),
+			primaryButton: localize('delete', "Delete"),
+		});
+
+		if (confirmation.confirmed) {
+			const useTrash = fileService.hasCapability(uri, FileSystemProviderCapabilities.Trash);
+			await fileService.del(uri, { useTrash, recursive: true });
+		}
+	}
+});
+
+// Copy path action
+const COPY_AI_CUSTOMIZATION_PATH_ID = 'aiCustomization.copyPath';
+registerAction2(class extends Action2 {
+	constructor() {
+		super({
+			id: COPY_AI_CUSTOMIZATION_PATH_ID,
+			title: localize2('copyPath', "Copy Path"),
+			icon: Codicon.clippy,
+		});
+	}
+	async run(accessor: ServicesAccessor, context: URIContext): Promise<void> {
+		const clipboardService = accessor.get(IClipboardService);
+		const uri = extractURI(context);
+		const textToCopy = uri.scheme === 'file' ? uri.fsPath : uri.toString(true);
+		await clipboardService.writeText(textToCopy);
+	}
+});
+
 // Register context menu items
+
+// Inline hover actions (shown as icon buttons on hover)
+MenuRegistry.appendMenuItem(AICustomizationItemMenuId, {
+	command: { id: DELETE_AI_CUSTOMIZATION_FILE_ID, title: localize('delete', "Delete"), icon: Codicon.trash },
+	group: 'inline',
+	order: 10,
+});
+
+// Context menu items (shown on right-click)
 MenuRegistry.appendMenuItem(AICustomizationItemMenuId, {
 	command: { id: OPEN_AI_CUSTOMIZATION_FILE_ID, title: localize('open', "Open") },
 	group: '1_open',
@@ -93,4 +155,16 @@ MenuRegistry.appendMenuItem(AICustomizationItemMenuId, {
 	when: ContextKeyExpr.equals(AICustomizationItemTypeContextKey.key, PromptsType.prompt),
 });
 
+MenuRegistry.appendMenuItem(AICustomizationItemMenuId, {
+	command: { id: COPY_AI_CUSTOMIZATION_PATH_ID, title: localize('copyPath', "Copy Path") },
+	group: '3_modify',
+	order: 1,
+});
+
+MenuRegistry.appendMenuItem(AICustomizationItemMenuId, {
+	command: { id: DELETE_AI_CUSTOMIZATION_FILE_ID, title: localize('delete', "Delete") },
+	group: '3_modify',
+	order: 10,
+});
+
 //#endregion
diff --git a/src/vs/sessions/contrib/aiCustomizationTreeView/browser/aiCustomizationTreeViewViews.ts b/src/vs/sessions/contrib/aiCustomizationTreeView/browser/aiCustomizationTreeViewViews.ts
index d2e6fcf1933d6..4b92d3f59a820 100644
--- a/src/vs/sessions/contrib/aiCustomizationTreeView/browser/aiCustomizationTreeViewViews.ts
+++ b/src/vs/sessions/contrib/aiCustomizationTreeView/browser/aiCustomizationTreeViewViews.ts
@@ -5,6 +5,7 @@
 
 import './media/aiCustomizationTreeView.css';
 import * as dom from '../../../../base/browser/dom.js';
+import { ActionBar } from '../../../../base/browser/ui/actionbar/actionbar.js';
 import { CancellationToken } from '../../../../base/common/cancellation.js';
 import { DisposableStore } from '../../../../base/common/lifecycle.js';
 import { autorun } from '../../../../base/common/observable.js';
@@ -12,7 +13,7 @@ import { basename, dirname } from '../../../../base/common/resources.js';
 import { ThemeIcon } from '../../../../base/common/themables.js';
 import { URI } from '../../../../base/common/uri.js';
 import { localize } from '../../../../nls.js';
-import { getContextMenuActions } from '../../../../platform/actions/browser/menuEntryActionViewItem.js';
+import { createActionViewItem, getContextMenuActions } from '../../../../platform/actions/browser/menuEntryActionViewItem.js';
 import { IMenuService } from '../../../../platform/actions/common/actions.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { IContextKey, IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
@@ -27,12 +28,16 @@ import { IViewPaneOptions, ViewPane } from '../../../../workbench/browser/parts/
 import { IViewDescriptorService } from '../../../../workbench/common/views.js';
 import { IPromptsService, PromptsStorage, IAgentSkill, IPromptPath } from '../../../../workbench/contrib/chat/common/promptSyntax/service/promptsService.js';
 import { PromptsType } from '../../../../workbench/contrib/chat/common/promptSyntax/promptTypes.js';
-import { agentIcon, extensionIcon, instructionsIcon, promptIcon, skillIcon, userIcon, workspaceIcon } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationIcons.js';
+import { agentIcon, extensionIcon, instructionsIcon, mcpServerIcon, pluginIcon, promptIcon, skillIcon, userIcon, workspaceIcon, builtinIcon } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationIcons.js';
 import { AICustomizationItemMenuId } from './aiCustomizationTreeView.js';
+import { AICustomizationManagementSection } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.js';
+import { AICustomizationPromptsStorage, BUILTIN_STORAGE } from '../../chat/common/builtinPromptsStorage.js';
+import { AICustomizationManagementEditorInput } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagementEditorInput.js';
+import { AICustomizationManagementEditor } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagementEditor.js';
 import { IAsyncDataSource, ITreeNode, ITreeRenderer, ITreeContextMenuEvent } from '../../../../base/browser/ui/tree/tree.js';
 import { FuzzyScore } from '../../../../base/common/filters.js';
 import { IListVirtualDelegate } from '../../../../base/browser/ui/list/list.js';
-import { IEditorService } from '../../../../workbench/services/editor/common/editorService.js';
+import { IEditorService, MODAL_GROUP } from '../../../../workbench/services/editor/common/editorService.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
 import { IWorkspaceContextService } from '../../../../platform/workspace/common/workspace.js';
 import { IAICustomizationWorkspaceService } from '../../../../workbench/contrib/chat/common/aiCustomizationWorkspaceService.js';
@@ -77,7 +82,7 @@ interface IAICustomizationGroupItem {
 	readonly type: 'group';
 	readonly id: string;
 	readonly label: string;
-	readonly storage: PromptsStorage;
+	readonly storage: AICustomizationPromptsStorage;
 	readonly promptType: PromptsType;
 	readonly icon: ThemeIcon;
 }
@@ -91,11 +96,22 @@ interface IAICustomizationFileItem {
 	readonly uri: URI;
 	readonly name: string;
 	readonly description?: string;
-	readonly storage: PromptsStorage;
+	readonly storage: AICustomizationPromptsStorage;
 	readonly promptType: PromptsType;
 }
 
-type AICustomizationTreeItem = IAICustomizationTypeItem | IAICustomizationGroupItem | IAICustomizationFileItem;
+/**
+ * Represents a link item that navigates to the management editor.
+ */
+interface IAICustomizationLinkItem {
+	readonly type: 'link';
+	readonly id: string;
+	readonly label: string;
+	readonly icon: ThemeIcon;
+	readonly section: AICustomizationManagementSection;
+}
+
+type AICustomizationTreeItem = IAICustomizationTypeItem | IAICustomizationGroupItem | IAICustomizationFileItem | IAICustomizationLinkItem;
 
 //#endregion
 
@@ -109,6 +125,7 @@ class AICustomizationTreeDelegate implements IListVirtualDelegate<AICustomizatio
 	getTemplateId(element: AICustomizationTreeItem): string {
 		switch (element.type) {
 			case 'category':
+			case 'link':
 				return 'category';
 			case 'group':
 				return 'group';
@@ -133,9 +150,12 @@ interface IFileTemplateData {
 	readonly container: HTMLElement;
 	readonly icon: HTMLElement;
 	readonly name: HTMLElement;
+	readonly actionBar: ActionBar;
+	readonly elementDisposables: DisposableStore;
+	readonly templateDisposables: DisposableStore;
 }
 
-class AICustomizationCategoryRenderer implements ITreeRenderer<IAICustomizationTypeItem, FuzzyScore, ICategoryTemplateData> {
+class AICustomizationCategoryRenderer implements ITreeRenderer<IAICustomizationTypeItem | IAICustomizationLinkItem, FuzzyScore, ICategoryTemplateData> {
 	readonly templateId = 'category';
 
 	renderTemplate(container: HTMLElement): ICategoryTemplateData {
@@ -145,7 +165,7 @@ class AICustomizationCategoryRenderer implements ITreeRenderer<IAICustomizationT
 		return { container: element, icon, label };
 	}
 
-	renderElement(node: ITreeNode<IAICustomizationTypeItem, FuzzyScore>, _index: number, templateData: ICategoryTemplateData): void {
+	renderElement(node: ITreeNode<IAICustomizationTypeItem | IAICustomizationLinkItem, FuzzyScore>, _index: number, templateData: ICategoryTemplateData): void {
 		templateData.icon.className = 'icon';
 		templateData.icon.classList.add(...ThemeIcon.asClassNameArray(node.element.icon));
 		templateData.label.textContent = node.element.label;
@@ -173,15 +193,29 @@ class AICustomizationGroupRenderer implements ITreeRenderer<IAICustomizationGrou
 class AICustomizationFileRenderer implements ITreeRenderer<IAICustomizationFileItem, FuzzyScore, IFileTemplateData> {
 	readonly templateId = 'file';
 
+	constructor(
+		private readonly menuService: IMenuService,
+		private readonly contextKeyService: IContextKeyService,
+		private readonly instantiationService: IInstantiationService,
+	) { }
+
 	renderTemplate(container: HTMLElement): IFileTemplateData {
 		const element = dom.append(container, dom.$('.ai-customization-tree-item'));
 		const icon = dom.append(element, dom.$('.icon'));
 		const name = dom.append(element, dom.$('.name'));
-		return { container: element, icon, name };
+		const actionsContainer = dom.append(element, dom.$('.actions'));
+
+		const templateDisposables = new DisposableStore();
+		const actionBar = templateDisposables.add(new ActionBar(actionsContainer, {
+			actionViewItemProvider: createActionViewItem.bind(undefined, this.instantiationService),
+		}));
+
+		return { container: element, icon, name, actionBar, elementDisposables: new DisposableStore(), templateDisposables };
 	}
 
 	renderElement(node: ITreeNode<IAICustomizationFileItem, FuzzyScore>, _index: number, templateData: IFileTemplateData): void {
 		const item = node.element;
+		templateData.elementDisposables.clear();
 
 		// Set icon based on prompt type
 		let icon: ThemeIcon;
@@ -209,9 +243,45 @@ class AICustomizationFileRenderer implements ITreeRenderer<IAICustomizationFileI
 		// Set tooltip with name and description
 		const tooltip = item.description ? `${item.name} - ${item.description}` : item.name;
 		templateData.container.title = tooltip;
+
+		// Build context for menu actions
+		const context = {
+			uri: item.uri.toString(),
+			name: item.name,
+			promptType: item.promptType,
+			storage: item.storage,
+		};
+
+		// Create scoped context key service with item type for when-clause filtering
+		const overlay = this.contextKeyService.createOverlay([
+			[AICustomizationItemTypeContextKey.key, item.promptType],
+		]);
+
+		// Create menu and extract inline actions
+		const menu = templateData.elementDisposables.add(
+			this.menuService.createMenu(AICustomizationItemMenuId, overlay)
+		);
+
+		const updateActions = () => {
+			const actions = menu.getActions({ arg: context, shouldForwardArgs: true });
+			const { primary } = getContextMenuActions(actions, 'inline');
+			templateData.actionBar.clear();
+			templateData.actionBar.push(primary, { icon: true, label: false });
+		};
+		updateActions();
+		templateData.elementDisposables.add(menu.onDidChange(updateActions));
+
+		templateData.actionBar.context = context;
 	}
 
-	disposeTemplate(_templateData: IFileTemplateData): void { }
+	disposeElement(_node: ITreeNode<IAICustomizationFileItem, FuzzyScore>, _index: number, templateData: IFileTemplateData): void {
+		templateData.elementDisposables.clear();
+	}
+
+	disposeTemplate(templateData: IFileTemplateData): void {
+		templateData.templateDisposables.dispose();
+		templateData.elementDisposables.dispose();
+	}
 }
 
 /**
@@ -219,7 +289,7 @@ class AICustomizationFileRenderer implements ITreeRenderer<IAICustomizationFileI
  */
 interface ICachedTypeData {
 	skills?: IAgentSkill[];
-	files?: Map<PromptsStorage, readonly IPromptPath[]>;
+	files?: Map<string, readonly IPromptPath[]>;
 }
 
 /**
@@ -248,6 +318,9 @@ class UnifiedAICustomizationDataSource implements IAsyncDataSource<RootElement,
 		if (element === ROOT_ELEMENT) {
 			return true;
 		}
+		if (element.type === 'link') {
+			return false;
+		}
 		return element.type === 'category' || element.type === 'group';
 	}
 
@@ -272,7 +345,7 @@ class UnifiedAICustomizationDataSource implements IAsyncDataSource<RootElement,
 		}
 	}
 
-	private getTypeCategories(): IAICustomizationTypeItem[] {
+	private getTypeCategories(): (IAICustomizationTypeItem | IAICustomizationLinkItem)[] {
 		return [
 			{
 				type: 'category',
@@ -302,6 +375,13 @@ class UnifiedAICustomizationDataSource implements IAsyncDataSource<RootElement,
 				promptType: PromptsType.prompt,
 				icon: promptIcon,
 			},
+			{
+				type: 'link',
+				id: 'link-mcp-servers',
+				label: localize('mcpServers', "MCP Servers"),
+				icon: mcpServerIcon,
+				section: AICustomizationManagementSection.McpServers,
+			},
 		];
 	}
 
@@ -330,6 +410,7 @@ class UnifiedAICustomizationDataSource implements IAsyncDataSource<RootElement,
 			const workspaceSkills = cached.skills.filter(s => s.storage === PromptsStorage.local);
 			const userSkills = cached.skills.filter(s => s.storage === PromptsStorage.user);
 			const extensionSkills = cached.skills.filter(s => s.storage === PromptsStorage.extension);
+			const builtinSkills = cached.skills.filter(s => s.storage === BUILTIN_STORAGE);
 
 			if (workspaceSkills.length > 0) {
 				groups.push(this.createGroupItem(promptType, PromptsStorage.local, workspaceSkills.length));
@@ -340,6 +421,9 @@ class UnifiedAICustomizationDataSource implements IAsyncDataSource<RootElement,
 			if (extensionSkills.length > 0) {
 				groups.push(this.createGroupItem(promptType, PromptsStorage.extension, extensionSkills.length));
 			}
+			if (builtinSkills.length > 0) {
+				groups.push(this.createGroupItem(promptType, BUILTIN_STORAGE, builtinSkills.length));
+			}
 
 			return groups;
 		}
@@ -350,11 +434,13 @@ class UnifiedAICustomizationDataSource implements IAsyncDataSource<RootElement,
 			const workspaceItems = allItems.filter(item => item.storage === PromptsStorage.local);
 			const userItems = allItems.filter(item => item.storage === PromptsStorage.user);
 			const extensionItems = allItems.filter(item => item.storage === PromptsStorage.extension);
+			const builtinItems = allItems.filter(item => item.storage === BUILTIN_STORAGE);
 
-			cached.files = new Map<PromptsStorage, readonly IPromptPath[]>([
+			cached.files = new Map<string, readonly IPromptPath[]>([
 				[PromptsStorage.local, workspaceItems],
 				[PromptsStorage.user, userItems],
 				[PromptsStorage.extension, extensionItems],
+				[BUILTIN_STORAGE, builtinItems],
 			]);
 
 			const itemCount = allItems.length;
@@ -365,6 +451,7 @@ class UnifiedAICustomizationDataSource implements IAsyncDataSource<RootElement,
 		const workspaceItems = cached.files!.get(PromptsStorage.local) || [];
 		const userItems = cached.files!.get(PromptsStorage.user) || [];
 		const extensionItems = cached.files!.get(PromptsStorage.extension) || [];
+		const builtinItems = cached.files!.get(BUILTIN_STORAGE) || [];
 
 		if (workspaceItems.length > 0) {
 			groups.push(this.createGroupItem(promptType, PromptsStorage.local, workspaceItems.length));
@@ -375,6 +462,9 @@ class UnifiedAICustomizationDataSource implements IAsyncDataSource<RootElement,
 		if (extensionItems.length > 0) {
 			groups.push(this.createGroupItem(promptType, PromptsStorage.extension, extensionItems.length));
 		}
+		if (builtinItems.length > 0) {
+			groups.push(this.createGroupItem(promptType, BUILTIN_STORAGE, builtinItems.length));
+		}
 
 		return groups;
 	}
@@ -382,23 +472,29 @@ class UnifiedAICustomizationDataSource implements IAsyncDataSource<RootElement,
 	/**
 	 * Creates a group item with consistent structure.
 	 */
-	private createGroupItem(promptType: PromptsType, storage: PromptsStorage, count: number): IAICustomizationGroupItem {
-		const storageLabels: Record<PromptsStorage, string> = {
+	private createGroupItem(promptType: PromptsType, storage: AICustomizationPromptsStorage, count: number): IAICustomizationGroupItem {
+		const storageLabels: Record<string, string> = {
 			[PromptsStorage.local]: localize('workspaceWithCount', "Workspace ({0})", count),
 			[PromptsStorage.user]: localize('userWithCount', "User ({0})", count),
 			[PromptsStorage.extension]: localize('extensionsWithCount', "Extensions ({0})", count),
+			[PromptsStorage.plugin]: localize('pluginsWithCount', "Plugins ({0})", count),
+			[BUILTIN_STORAGE]: localize('builtinWithCount', "Built-in ({0})", count),
 		};
 
-		const storageIcons: Record<PromptsStorage, ThemeIcon> = {
+		const storageIcons: Record<string, ThemeIcon> = {
 			[PromptsStorage.local]: workspaceIcon,
 			[PromptsStorage.user]: userIcon,
 			[PromptsStorage.extension]: extensionIcon,
+			[PromptsStorage.plugin]: pluginIcon,
+			[BUILTIN_STORAGE]: builtinIcon,
 		};
 
-		const storageSuffixes: Record<PromptsStorage, string> = {
+		const storageSuffixes: Record<string, string> = {
 			[PromptsStorage.local]: 'workspace',
 			[PromptsStorage.user]: 'user',
 			[PromptsStorage.extension]: 'extensions',
+			[PromptsStorage.plugin]: 'plugins',
+			[BUILTIN_STORAGE]: 'builtin',
 		};
 
 		return {
@@ -415,7 +511,7 @@ class UnifiedAICustomizationDataSource implements IAsyncDataSource<RootElement,
 	 * Returns files for a specific storage/type combination from cache.
 	 * getStorageGroups must be called first to populate the cache.
 	 */
-	private async getFilesForStorageAndType(storage: PromptsStorage, promptType: PromptsType): Promise<IAICustomizationFileItem[]> {
+	private async getFilesForStorageAndType(storage: AICustomizationPromptsStorage, promptType: PromptsType): Promise<IAICustomizationFileItem[]> {
 		const cached = this.cache.get(promptType);
 
 		// For skills, use the cached skills data
@@ -537,7 +633,7 @@ export class AICustomizationViewPane extends ViewPane {
 			[
 				new AICustomizationCategoryRenderer(),
 				new AICustomizationGroupRenderer(),
-				new AICustomizationFileRenderer(),
+				new AICustomizationFileRenderer(this.menuService, this.contextKeyService, this.instantiationService),
 			],
 			this.dataSource,
 			{
@@ -546,7 +642,7 @@ export class AICustomizationViewPane extends ViewPane {
 				},
 				accessibilityProvider: {
 					getAriaLabel: (element: AICustomizationTreeItem) => {
-						if (element.type === 'category') {
+						if (element.type === 'category' || element.type === 'link') {
 							return element.label;
 						}
 						if (element.type === 'group') {
@@ -570,12 +666,18 @@ export class AICustomizationViewPane extends ViewPane {
 			}
 		));
 
-		// Handle double-click to open file
-		this.treeDisposables.add(this.tree.onDidOpen(e => {
+		// Handle double-click to open file or navigate to section
+		this.treeDisposables.add(this.tree.onDidOpen(async e => {
 			if (e.element && e.element.type === 'file') {
 				this.editorService.openEditor({
-					resource: e.element.uri
+					resource: e.element.uri,
 				});
+			} else if (e.element && e.element.type === 'link') {
+				const input = AICustomizationManagementEditorInput.getOrCreate();
+				const editor = await this.editorService.openEditor(input, { pinned: true }, MODAL_GROUP);
+				if (editor instanceof AICustomizationManagementEditor) {
+					editor.selectSectionById(e.element.section);
+				}
 			}
 		}));
 
diff --git a/src/vs/sessions/contrib/aiCustomizationTreeView/browser/media/aiCustomizationTreeView.css b/src/vs/sessions/contrib/aiCustomizationTreeView/browser/media/aiCustomizationTreeView.css
index 0756725fc2b39..3e3d9be3b356a 100644
--- a/src/vs/sessions/contrib/aiCustomizationTreeView/browser/media/aiCustomizationTreeView.css
+++ b/src/vs/sessions/contrib/aiCustomizationTreeView/browser/media/aiCustomizationTreeView.css
@@ -31,11 +31,24 @@
 }
 
 .ai-customization-view .ai-customization-tree-item .name {
+	flex: 1;
 	overflow: hidden;
 	text-overflow: ellipsis;
 	white-space: nowrap;
 }
 
+.ai-customization-view .ai-customization-tree-item .actions {
+	display: none;
+	flex-shrink: 0;
+	max-width: fit-content;
+}
+
+.ai-customization-view .monaco-list .monaco-list-row:hover .ai-customization-tree-item > .actions,
+.ai-customization-view .monaco-list .monaco-list-row.focused .ai-customization-tree-item > .actions,
+.ai-customization-view .monaco-list .monaco-list-row.selected .ai-customization-tree-item > .actions {
+	display: flex;
+}
+
 .ai-customization-view .ai-customization-tree-item .description {
 	flex-shrink: 1;
 	color: var(--vscode-descriptionForeground);
diff --git a/src/vs/sessions/contrib/applyCommitsToParentRepo/browser/applyChangesToParentRepo.ts b/src/vs/sessions/contrib/applyCommitsToParentRepo/browser/applyChangesToParentRepo.ts
new file mode 100644
index 0000000000000..1c02efa68e675
--- /dev/null
+++ b/src/vs/sessions/contrib/applyCommitsToParentRepo/browser/applyChangesToParentRepo.ts
@@ -0,0 +1,172 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { toAction } from '../../../../base/common/actions.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { Schemas } from '../../../../base/common/network.js';
+import { autorun } from '../../../../base/common/observable.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { localize, localize2 } from '../../../../nls.js';
+import { Action2, MenuId, MenuRegistry, registerAction2 } from '../../../../platform/actions/common/actions.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { ContextKeyExpr, IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
+import { ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
+import { INotificationService, Severity } from '../../../../platform/notification/common/notification.js';
+import { IOpenerService } from '../../../../platform/opener/common/opener.js';
+import { IProductService } from '../../../../platform/product/common/productService.js';
+import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../../workbench/common/contributions.js';
+import { IsSessionsWindowContext } from '../../../../workbench/common/contextkeys.js';
+import { CHAT_CATEGORY } from '../../../../workbench/contrib/chat/browser/actions/chatActions.js';
+import { ChatContextKeys } from '../../../../workbench/contrib/chat/common/actions/chatContextKeys.js';
+import { ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
+import { URI } from '../../../../base/common/uri.js';
+
+const hasWorktreeAndRepositoryContextKey = new RawContextKey<boolean>('agentSessionHasWorktreeAndRepository', false, {
+	type: 'boolean',
+	description: localize('agentSessionHasWorktreeAndRepository', "True when the active agent session has both a worktree and a parent repository.")
+});
+
+class ApplyChangesToParentRepoContribution extends Disposable implements IWorkbenchContribution {
+
+	static readonly ID = 'sessions.contrib.applyChangesToParentRepo';
+
+	constructor(
+		@IContextKeyService contextKeyService: IContextKeyService,
+		@ISessionsManagementService sessionManagementService: ISessionsManagementService,
+	) {
+		super();
+
+		const worktreeAndRepoKey = hasWorktreeAndRepositoryContextKey.bindTo(contextKeyService);
+
+		this._register(autorun(reader => {
+			const activeSession = sessionManagementService.activeSession.read(reader);
+			const hasWorktreeAndRepo = !!activeSession?.worktree && !!activeSession?.repository;
+			worktreeAndRepoKey.set(hasWorktreeAndRepo);
+		}));
+	}
+}
+
+class ApplyChangesToParentRepoAction extends Action2 {
+	static readonly ID = 'chatEditing.applyChangesToParentRepo';
+
+	constructor() {
+		super({
+			id: ApplyChangesToParentRepoAction.ID,
+			title: localize2('applyChangesToParentRepo', 'Apply Changes to Parent Repository'),
+			icon: Codicon.desktopDownload,
+			category: CHAT_CATEGORY,
+			precondition: ContextKeyExpr.and(
+				IsSessionsWindowContext,
+				hasWorktreeAndRepositoryContextKey,
+			),
+			menu: [
+				{
+					id: MenuId.ChatEditingSessionApplySubmenu,
+					group: 'navigation',
+					order: 2,
+					when: ContextKeyExpr.and(
+						ContextKeyExpr.false(),
+						IsSessionsWindowContext,
+						hasWorktreeAndRepositoryContextKey
+					),
+				},
+			],
+		});
+	}
+
+	override async run(accessor: ServicesAccessor): Promise<void> {
+		const sessionManagementService = accessor.get(ISessionsManagementService);
+		const commandService = accessor.get(ICommandService);
+		const notificationService = accessor.get(INotificationService);
+		const logService = accessor.get(ILogService);
+		const openerService = accessor.get(IOpenerService);
+		const productService = accessor.get(IProductService);
+
+		const activeSession = sessionManagementService.getActiveSession();
+		if (!activeSession?.worktree || !activeSession?.repository) {
+			return;
+		}
+
+		const worktreeRoot = activeSession.worktree;
+		const repoRoot = activeSession.repository;
+
+		const openFolderAction = toAction({
+			id: 'applyChangesToParentRepo.openFolder',
+			label: localize('openInVSCode', "Open in VS Code"),
+			run: () => {
+				const scheme = productService.quality === 'stable'
+					? 'vscode'
+					: productService.quality === 'exploration'
+						? 'vscode-exploration'
+						: 'vscode-insiders';
+
+				const params = new URLSearchParams();
+				params.set('windowId', '_blank');
+				params.set('session', activeSession.resource.toString());
+
+				openerService.open(URI.from({
+					scheme,
+					authority: Schemas.file,
+					path: repoRoot.path,
+					query: params.toString(),
+				}), { openExternal: true });
+			}
+		});
+
+		try {
+			// Get the worktree branch name. Since the worktree and parent repo
+			// share the same git object store, the parent can directly reference
+			// this branch for a merge.
+			const worktreeBranch = await commandService.executeCommand<string>(
+				'_git.revParseAbbrevRef',
+				worktreeRoot.fsPath
+			);
+
+			if (!worktreeBranch) {
+				notificationService.notify({
+					severity: Severity.Warning,
+					message: localize('applyChangesNoBranch', "Could not determine worktree branch name."),
+				});
+				return;
+			}
+
+			// Merge the worktree branch into the parent repo.
+			// This is idempotent: if already merged, git says "Already up to date."
+			// If new commits exist, they're brought in. Handles partial applies naturally.
+			const result = await commandService.executeCommand('_git.mergeBranch', repoRoot.fsPath, worktreeBranch);
+			if (!result) {
+				logService.warn('[ApplyChangesToParentRepo] No result from merge command');
+			} else {
+				notificationService.notify({
+					severity: Severity.Info,
+					message: typeof result === 'string' && result.startsWith('Already up to date')
+						? localize('alreadyUpToDate', 'Parent repository is up to date with worktree.')
+						: localize('applyChangesSuccess', 'Applied changes to parent repository.'),
+					actions: { primary: [openFolderAction] }
+				});
+			}
+		} catch (err) {
+			logService.error('[ApplyChangesToParentRepo] Failed to apply changes', err);
+			notificationService.notify({
+				severity: Severity.Warning,
+				message: localize('applyChangesConflict', "Failed to apply changes to parent repo. The parent repo may have diverged — resolve conflicts manually."),
+				actions: { primary: [openFolderAction] }
+			});
+		}
+	}
+}
+
+registerAction2(ApplyChangesToParentRepoAction);
+registerWorkbenchContribution2(ApplyChangesToParentRepoContribution.ID, ApplyChangesToParentRepoContribution, WorkbenchPhase.AfterRestored);
+
+// Register the apply submenu in the session changes toolbar
+MenuRegistry.appendMenuItem(MenuId.ChatEditingSessionChangesToolbar, {
+	submenu: MenuId.ChatEditingSessionApplySubmenu,
+	title: localize2('applyActions', 'Apply Actions'),
+	group: 'navigation',
+	order: 1,
+	when: ContextKeyExpr.and(IsSessionsWindowContext, ChatContextKeys.hasAgentSessionChanges),
+});
diff --git a/src/vs/sessions/contrib/changesView/browser/changesView.contribution.ts b/src/vs/sessions/contrib/changes/browser/changesView.contribution.ts
similarity index 85%
rename from src/vs/sessions/contrib/changesView/browser/changesView.contribution.ts
rename to src/vs/sessions/contrib/changes/browser/changesView.contribution.ts
index 3e69bba8dfa4f..9da044d818d4b 100644
--- a/src/vs/sessions/contrib/changesView/browser/changesView.contribution.ts
+++ b/src/vs/sessions/contrib/changes/browser/changesView.contribution.ts
@@ -8,8 +8,11 @@ import { localize2 } from '../../../../nls.js';
 import { SyncDescriptor } from '../../../../platform/instantiation/common/descriptors.js';
 import { Registry } from '../../../../platform/registry/common/platform.js';
 import { registerIcon } from '../../../../platform/theme/common/iconRegistry.js';
+import { registerWorkbenchContribution2, WorkbenchPhase } from '../../../../workbench/common/contributions.js';
 import { IViewContainersRegistry, ViewContainerLocation, IViewsRegistry, Extensions as ViewContainerExtensions, WindowVisibility } from '../../../../workbench/common/views.js';
 import { CHANGES_VIEW_CONTAINER_ID, CHANGES_VIEW_ID, ChangesViewPane, ChangesViewPaneContainer } from './changesView.js';
+import './changesViewActions.js';
+import { ToggleChangesViewContribution } from './toggleChangesView.js';
 
 const changesViewIcon = registerIcon('changes-view-icon', Codicon.gitCompare, localize2('changesViewIcon', 'View icon for the Changes view.').value);
 
@@ -38,3 +41,5 @@ viewsRegistry.registerViews([{
 	order: 1,
 	windowVisibility: WindowVisibility.Sessions
 }], changesViewContainer);
+
+registerWorkbenchContribution2(ToggleChangesViewContribution.ID, ToggleChangesViewContribution, WorkbenchPhase.BlockRestore);
diff --git a/src/vs/sessions/contrib/changesView/browser/changesView.ts b/src/vs/sessions/contrib/changes/browser/changesView.ts
similarity index 64%
rename from src/vs/sessions/contrib/changesView/browser/changesView.ts
rename to src/vs/sessions/contrib/changes/browser/changesView.ts
index 973e8e2ba1b4b..d7997d39bbd03 100644
--- a/src/vs/sessions/contrib/changesView/browser/changesView.ts
+++ b/src/vs/sessions/contrib/changes/browser/changesView.ts
@@ -13,15 +13,15 @@ import { Codicon } from '../../../../base/common/codicons.js';
 import { MarkdownString } from '../../../../base/common/htmlContent.js';
 import { Iterable } from '../../../../base/common/iterator.js';
 import { DisposableStore, MutableDisposable } from '../../../../base/common/lifecycle.js';
-import { autorun, derived, derivedOpts, IObservable, IObservableWithChange, observableFromEvent, observableValue } from '../../../../base/common/observable.js';
+import { autorun, constObservable, derived, derivedOpts, IObservable, IObservableWithChange, observableFromEvent, ObservablePromise, observableValue } from '../../../../base/common/observable.js';
 import { basename, dirname } from '../../../../base/common/path.js';
-import { isEqual } from '../../../../base/common/resources.js';
+import { extUriBiasedIgnorePathCase, isEqual } from '../../../../base/common/resources.js';
 import { ThemeIcon } from '../../../../base/common/themables.js';
 import { URI } from '../../../../base/common/uri.js';
-import { localize } from '../../../../nls.js';
+import { localize, localize2 } from '../../../../nls.js';
 import { MenuWorkbenchButtonBar } from '../../../../platform/actions/browser/buttonbar.js';
 import { MenuWorkbenchToolBar } from '../../../../platform/actions/browser/toolbar.js';
-import { MenuId, registerAction2 } from '../../../../platform/actions/common/actions.js';
+import { MenuId, Action2, MenuRegistry, registerAction2 } from '../../../../platform/actions/common/actions.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { ContextKeyExpr, IContextKey, IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
 import { IContextMenuService } from '../../../../platform/contextview/browser/contextView.js';
@@ -44,18 +44,25 @@ import { IResourceLabel, ResourceLabels } from '../../../../workbench/browser/la
 import { ViewPane, IViewPaneOptions, ViewAction } from '../../../../workbench/browser/parts/views/viewPane.js';
 import { ViewPaneContainer } from '../../../../workbench/browser/parts/views/viewPaneContainer.js';
 import { IViewDescriptorService } from '../../../../workbench/common/views.js';
+import { IViewsService } from '../../../../workbench/services/views/common/viewsService.js';
+import { IsSessionsWindowContext } from '../../../../workbench/common/contextkeys.js';
+import { CHAT_CATEGORY } from '../../../../workbench/contrib/chat/browser/actions/chatActions.js';
 import { IAgentSessionsService } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
 import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
 import { ChatContextKeys } from '../../../../workbench/contrib/chat/common/actions/chatContextKeys.js';
-import { isIChatSessionFileChange2 } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
+import { IChatSessionFileChange, IChatSessionFileChange2, isIChatSessionFileChange2 } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
 import { chatEditingWidgetFileStateContextKey, hasAppliedChatEditsContextKey, hasUndecidedChatEditingResourceContextKey, IChatEditingService, ModifiedFileEntryState } from '../../../../workbench/contrib/chat/common/editing/chatEditingService.js';
-import { getChatSessionType } from '../../../../workbench/contrib/chat/common/model/chatUri.js';
 import { createFileIconThemableTreeContainerScope } from '../../../../workbench/contrib/files/browser/views/explorerView.js';
 import { IActivityService, NumberBadge } from '../../../../workbench/services/activity/common/activity.js';
 import { IEditorService, MODAL_GROUP, SIDE_GROUP } from '../../../../workbench/services/editor/common/editorService.js';
 import { IExtensionService } from '../../../../workbench/services/extensions/common/extensions.js';
 import { IWorkbenchLayoutService } from '../../../../workbench/services/layout/browser/layoutService.js';
-import { ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
+import { IActiveSessionItem, ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
+import { GITHUB_REMOTE_FILE_SCHEME } from '../../fileTreeView/browser/githubFileSystemProvider.js';
+import { CodeReviewStateKind, getCodeReviewFilesFromSessionChanges, getCodeReviewVersion, ICodeReviewService, PRReviewStateKind } from '../../codeReview/browser/codeReviewService.js';
+import { IGitRepository, IGitService } from '../../../../workbench/contrib/git/common/gitService.js';
+import { IGitHubService } from '../../github/browser/githubService.js';
+import { CIStatusWidget } from './ciStatusWidget.js';
 
 const $ = dom.$;
 
@@ -63,6 +70,7 @@ const $ = dom.$;
 
 export const CHANGES_VIEW_CONTAINER_ID = 'workbench.view.agentSessions.changesContainer';
 export const CHANGES_VIEW_ID = 'workbench.view.agentSessions.changes';
+const RUN_SESSION_CODE_REVIEW_ACTION_ID = 'sessions.codeReview.run';
 
 // --- View Mode
 
@@ -73,6 +81,19 @@ export const enum ChangesViewMode {
 
 const changesViewModeContextKey = new RawContextKey<ChangesViewMode>('changesViewMode', ChangesViewMode.List);
 
+// --- Versions Mode
+
+const enum ChangesVersionMode {
+	AllChanges = 'allChanges',
+	LastTurn = 'lastTurn',
+	Uncommitted = 'uncommitted'
+}
+
+const changesVersionModeContextKey = new RawContextKey<ChangesVersionMode>('sessions.changesVersionMode', ChangesVersionMode.AllChanges);
+const isMergeBaseBranchProtectedContextKey = new RawContextKey<boolean>('sessions.isMergeBaseBranchProtected', false);
+const hasOpenPullRequestContextKey = new RawContextKey<boolean>('sessions.hasOpenPullRequest', false);
+const hasUncommittedChangesContextKey = new RawContextKey<boolean>('sessions.hasUncommittedChanges', false);
+
 // --- List Item
 
 type ChangeType = 'added' | 'modified' | 'deleted';
@@ -86,6 +107,7 @@ interface IChangesFileItem {
 	readonly changeType: ChangeType;
 	readonly linesAdded: number;
 	readonly linesRemoved: number;
+	readonly reviewCommentCount: number;
 }
 
 interface IChangesFolderItem {
@@ -94,11 +116,6 @@ interface IChangesFolderItem {
 	readonly name: string;
 }
 
-interface IActiveSession {
-	readonly resource: URI;
-	readonly sessionType: string;
-}
-
 type ChangesTreeElement = IChangesFileItem | IChangesFolderItem;
 
 function isChangesFileItem(element: ChangesTreeElement): element is IChangesFileItem {
@@ -124,17 +141,33 @@ function buildTreeChildren(items: IChangesFileItem[]): IObjectTreeElement<Change
 	const root: FolderNode = { name: '', uri: URI.file('/'), children: new Map(), files: [] };
 
 	for (const item of items) {
-		const dirPath = dirname(item.uri.path);
-		const segments = dirPath.split('/').filter(Boolean);
+		const fullDirPath = dirname(item.uri.path);
+
+		// For github-remote-file URIs, strip the /{owner}/{repo}/{ref} prefix
+		// so the tree shows repo-relative paths instead of internal URI segments.
+		let displayDirPath = fullDirPath;
+		let uriBasePrefix = '';
+		if (item.uri.scheme === GITHUB_REMOTE_FILE_SCHEME) {
+			const parts = fullDirPath.split('/').filter(Boolean);
+			if (parts.length >= 3) {
+				uriBasePrefix = '/' + parts.slice(0, 3).join('/');
+				displayDirPath = '/' + parts.slice(3).join('/');
+			} else {
+				uriBasePrefix = '/' + parts.join('/');
+				displayDirPath = '/';
+			}
+		}
+
+		const segments = displayDirPath.split('/').filter(Boolean);
 
 		let current = root;
-		let currentPath = '';
+		let currentFullPath = uriBasePrefix;
 		for (const segment of segments) {
-			currentPath += '/' + segment;
+			currentFullPath += '/' + segment;
 			if (!current.children.has(segment)) {
 				current.children.set(segment, {
 					name: segment,
-					uri: item.uri.with({ path: currentPath }),
+					uri: item.uri.with({ path: currentFullPath }),
 					children: new Map(),
 					files: []
 				});
@@ -185,6 +218,7 @@ export class ChangesViewPane extends ViewPane {
 	private actionsContainer: HTMLElement | undefined;
 
 	private tree: WorkbenchCompressibleObjectTree<ChangesTreeElement> | undefined;
+	private ciStatusWidget: CIStatusWidget | undefined;
 
 	private readonly renderDisposables = this._register(new DisposableStore());
 
@@ -206,10 +240,24 @@ export class ChangesViewPane extends ViewPane {
 		this.storageService.store('changesView.viewMode', mode, StorageScope.WORKSPACE, StorageTarget.USER);
 	}
 
+	// Version mode (all changes, last turn, uncommitted)
+	private readonly versionModeObs = observableValue<ChangesVersionMode>(this, ChangesVersionMode.AllChanges);
+	private readonly versionModeContextKey: IContextKey<ChangesVersionMode>;
+
+	setVersionMode(mode: ChangesVersionMode): void {
+		if (this.versionModeObs.get() === mode) {
+			return;
+		}
+		this.versionModeObs.set(mode, undefined);
+		this.versionModeContextKey.set(mode);
+	}
+
 	// Track the active session used by this view
-	private readonly activeSession: IObservableWithChange<IActiveSession | undefined>;
+	private readonly activeSession: IObservableWithChange<IActiveSessionItem | undefined>;
 	private readonly activeSessionFileCountObs: IObservableWithChange<number>;
 	private readonly activeSessionHasChangesObs: IObservableWithChange<boolean>;
+	private readonly activeSessionRepositoryChangesObs: IObservableWithChange<IChangesFileItem[] | undefined>;
+	private readonly activeSessionRepositoryObs: IObservableWithChange<IGitRepository | undefined>;
 
 	get activeSessionHasChanges(): IObservable<boolean> {
 		return this.activeSessionHasChangesObs;
@@ -236,6 +284,9 @@ export class ChangesViewPane extends ViewPane {
 		@ISessionsManagementService private readonly sessionManagementService: ISessionsManagementService,
 		@ILabelService private readonly labelService: ILabelService,
 		@IStorageService private readonly storageService: IStorageService,
+		@ICodeReviewService private readonly codeReviewService: ICodeReviewService,
+		@IGitService private readonly gitService: IGitService,
+		@IGitHubService private readonly gitHubService: IGitHubService,
 	) {
 		super(options, keybindingService, contextMenuService, configurationService, contextKeyService, viewDescriptorService, instantiationService, openerService, themeService, hoverService);
 
@@ -246,8 +297,12 @@ export class ChangesViewPane extends ViewPane {
 		this.viewModeContextKey = changesViewModeContextKey.bindTo(contextKeyService);
 		this.viewModeContextKey.set(initialMode);
 
+		// Version mode
+		this.versionModeContextKey = changesVersionModeContextKey.bindTo(contextKeyService);
+		this.versionModeContextKey.set(ChangesVersionMode.AllChanges);
+
 		// Track active session from sessions management service
-		this.activeSession = derivedOpts<IActiveSession | undefined>({
+		this.activeSession = derivedOpts<IActiveSessionItem | undefined>({
 			equalsFn: (a, b) => isEqual(a?.resource, b?.resource),
 		}, reader => {
 			const activeSession = this.sessionManagementService.activeSession.read(reader);
@@ -255,33 +310,65 @@ export class ChangesViewPane extends ViewPane {
 				return undefined;
 			}
 
-			return {
-				resource: activeSession.resource,
-				sessionType: getChatSessionType(activeSession.resource),
-			};
+			return activeSession;
 		}).recomputeInitiallyAndOnChange(this._store);
 
+		// Track active session repository changes
+		const activeSessionRepositoryPromiseObs = derived(reader => {
+			const activeSessionWorktree = this.activeSession.read(reader)?.worktree;
+			if (!activeSessionWorktree) {
+				return constObservable(undefined);
+			}
+
+			return new ObservablePromise(this.gitService.openRepository(activeSessionWorktree)).resolvedValue;
+		});
+
+		this.activeSessionRepositoryObs = derived<IGitRepository | undefined>(reader => {
+			const activeSessionRepositoryPromise = activeSessionRepositoryPromiseObs.read(reader);
+			if (activeSessionRepositoryPromise === undefined) {
+				return undefined;
+			}
+
+			return activeSessionRepositoryPromise.read(reader);
+		});
+
+		this.activeSessionRepositoryChangesObs = derived(reader => {
+			const repository = this.activeSessionRepositoryObs.read(reader);
+			if (!repository) {
+				return undefined;
+			}
+
+			const state = repository.state.read(reader);
+			const headCommit = state?.HEAD?.commit;
+			return (state?.workingTreeChanges ?? []).map(change => {
+				const isDeletion = change.modifiedUri === undefined;
+				const isAddition = change.originalUri === undefined;
+				const fileUri = change.modifiedUri ?? change.uri;
+				return {
+					type: 'file',
+					uri: fileUri,
+					originalUri: isDeletion || !headCommit ? change.originalUri
+						: fileUri.with({ scheme: 'git', query: JSON.stringify({ path: fileUri.fsPath, ref: headCommit }) }),
+					state: ModifiedFileEntryState.Accepted,
+					isDeletion,
+					changeType: isDeletion ? 'deleted' : isAddition ? 'added' : 'modified',
+					reviewCommentCount: 0,
+					linesAdded: 0,
+					linesRemoved: 0,
+				} satisfies IChangesFileItem;
+			});
+		});
+
 		this.activeSessionFileCountObs = this.createActiveSessionFileCountObservable();
 		this.activeSessionHasChangesObs = this.activeSessionFileCountObs.map(fileCount => fileCount > 0).recomputeInitiallyAndOnChange(this._store);
 
-		// Setup badge tracking
-		this.registerBadgeTracking();
-
 		// Set chatSessionType on the view's context key service so ViewTitle
 		// menu items can use it in their `when` clauses. Update reactively
 		// when the active session changes.
 		const viewSessionTypeKey = this.scopedContextKeyService.createKey<string>(ChatContextKeys.agentSessionType.key, '');
 		this._register(autorun(reader => {
 			const activeSession = this.activeSession.read(reader);
-			viewSessionTypeKey.set(activeSession?.sessionType ?? '');
-		}));
-	}
-
-	private registerBadgeTracking(): void {
-		// Update badge when file count changes
-		this._register(autorun(reader => {
-			const fileCount = this.activeSessionFileCountObs.read(reader);
-			this.updateBadge(fileCount);
+			viewSessionTypeKey.set(activeSession?.providerType ?? '');
 		}));
 	}
 
@@ -311,10 +398,8 @@ export class ChangesViewPane extends ViewPane {
 				return 0;
 			}
 
-			const isBackgroundSession = activeSession.sessionType === AgentSessionProviders.Background;
-
 			let editingSessionCount = 0;
-			if (!isBackgroundSession) {
+			if (activeSession.providerType !== AgentSessionProviders.Background) {
 				const sessions = this.chatEditingService.editingSessionsObs.read(reader);
 				const session = sessions.find(candidate => isEqual(candidate.chatSessionResource, activeSession.resource));
 				editingSessionCount = session ? session.entries.read(reader).length : 0;
@@ -371,6 +456,9 @@ export class ChangesViewPane extends ViewPane {
 		// List container
 		this.listContainer = dom.append(this.contentContainer, $('.chat-editing-session-list'));
 
+		// CI Status widget beneath the card
+		this.ciStatusWidget = this._register(this.instantiationService.createInstance(CIStatusWidget, this.bodyContainer));
+
 		this._register(this.onDidChangeBodyVisibility(visible => {
 			if (visible) {
 				this.onVisible();
@@ -406,7 +494,7 @@ export class ChangesViewPane extends ViewPane {
 			const activeSession = this.activeSession.read(reader);
 
 			// Background chat sessions render the working set based on the session files, not the editing session
-			if (activeSession?.sessionType === AgentSessionProviders.Background) {
+			if (activeSession?.providerType === AgentSessionProviders.Background) {
 				return [];
 			}
 
@@ -432,6 +520,7 @@ export class ChangesViewPane extends ViewPane {
 					changeType: isDeletion ? 'deleted' : 'modified',
 					linesAdded,
 					linesRemoved,
+					reviewCommentCount: 0,
 				});
 			}
 
@@ -457,37 +546,139 @@ export class ChangesViewPane extends ViewPane {
 			return model?.changes instanceof Array ? model.changes : Iterable.empty();
 		});
 
+		const reviewCommentCountByFileObs = derived(reader => {
+			const sessionResource = activeSessionResource.read(reader);
+			const sessionChanges = [...sessionFileChangesObs.read(reader)];
+
+			if (!sessionResource) {
+				return new Map<string, number>();
+			}
+
+			const result = new Map<string, number>();
+			const prReviewState = this.codeReviewService.getPRReviewState(sessionResource).read(reader);
+			if (prReviewState.kind === PRReviewStateKind.Loaded) {
+				for (const comment of prReviewState.comments) {
+					const uriKey = comment.uri.fsPath;
+					result.set(uriKey, (result.get(uriKey) ?? 0) + 1);
+				}
+			}
+
+			if (sessionChanges.length === 0) {
+				return result;
+			}
+
+			const reviewFiles = getCodeReviewFilesFromSessionChanges(sessionChanges as readonly IChatSessionFileChange[] | readonly IChatSessionFileChange2[]);
+			const reviewVersion = getCodeReviewVersion(reviewFiles);
+			const reviewState = this.codeReviewService.getReviewState(sessionResource).read(reader);
+
+			if (reviewState.kind !== CodeReviewStateKind.Result || reviewState.version !== reviewVersion) {
+				return result;
+			}
+
+			for (const comment of reviewState.comments) {
+				const uriKey = comment.uri.fsPath;
+				result.set(uriKey, (result.get(uriKey) ?? 0) + 1);
+			}
+
+			return result;
+		});
+
 		// Convert session file changes to list items (cloud/background sessions)
-		const sessionFilesObs = derived(reader =>
-			[...sessionFileChangesObs.read(reader)].map((entry): IChangesFileItem => {
+		const sessionFilesObs = derived(reader => {
+			const reviewCommentCountByFile = reviewCommentCountByFileObs.read(reader);
+
+			return [...sessionFileChangesObs.read(reader)].map((entry): IChangesFileItem => {
 				const isDeletion = entry.modifiedUri === undefined;
 				const isAddition = entry.originalUri === undefined;
+				const uri = isIChatSessionFileChange2(entry)
+					? entry.modifiedUri ?? entry.uri
+					: entry.modifiedUri;
 				return {
 					type: 'file',
-					uri: isIChatSessionFileChange2(entry)
-						? entry.modifiedUri ?? entry.uri
-						: entry.modifiedUri,
+					uri,
 					originalUri: entry.originalUri,
 					state: ModifiedFileEntryState.Accepted,
 					isDeletion,
 					changeType: isDeletion ? 'deleted' : isAddition ? 'added' : 'modified',
 					linesAdded: entry.insertions,
 					linesRemoved: entry.deletions,
+					reviewCommentCount: reviewCommentCountByFile.get(uri.fsPath) ?? 0,
 				};
-			})
-		);
+			});
+		});
+
+		// Create observable for last turn changes using diffBetweenWithStats
+		// Reactively computes the diff between HEAD^ and HEAD. Memoize the diff observable so
+		// that we only recompute it when the HEAD commit id actually changes.
+		const headCommitObs = derived(reader => {
+			const repository = this.activeSessionRepositoryObs.read(reader);
+			return repository?.state.read(reader)?.HEAD?.commit;
+		});
+
+		const lastTurnChangesObs = derived(reader => {
+			const repository = this.activeSessionRepositoryObs.read(reader);
+			const headCommit = headCommitObs.read(reader);
+			if (!repository || !headCommit) {
+				return constObservable(undefined);
+			}
+
+			return new ObservablePromise(repository.diffBetweenWithStats(`${headCommit}^`, headCommit)).resolvedValue;
+		});
 
 		// Combine both entry sources for display
 		const combinedEntriesObs = derived(reader => {
+			const headCommit = headCommitObs.read(reader);
+			const versionMode = this.versionModeObs.read(reader);
 			const editEntries = editSessionEntriesObs.read(reader);
 			const sessionFiles = sessionFilesObs.read(reader);
-			return [...editEntries, ...sessionFiles];
+			const repositoryFiles = this.activeSessionRepositoryChangesObs.read(reader) ?? [];
+			const lastTurnDiffChanges = lastTurnChangesObs.read(reader).read(reader);
+
+			let sourceEntries: IChangesFileItem[];
+			if (versionMode === ChangesVersionMode.Uncommitted) {
+				sourceEntries = repositoryFiles;
+			} else if (versionMode === ChangesVersionMode.LastTurn) {
+				const diffChanges = lastTurnDiffChanges ?? [];
+				const parentRef = headCommit ? `${headCommit}^` : '';
+				sourceEntries = diffChanges.map(change => {
+					const isDeletion = change.modifiedUri === undefined;
+					const isAddition = change.originalUri === undefined;
+					const fileUri = change.modifiedUri ?? change.uri;
+					const originalUri = isAddition ? change.originalUri
+						: headCommit ? fileUri.with({ scheme: 'git', query: JSON.stringify({ path: fileUri.fsPath, ref: parentRef }) })
+							: change.originalUri;
+					return {
+						type: 'file',
+						uri: fileUri,
+						originalUri,
+						state: ModifiedFileEntryState.Accepted,
+						isDeletion,
+						changeType: isDeletion ? 'deleted' : isAddition ? 'added' : 'modified',
+						linesAdded: change.insertions,
+						linesRemoved: change.deletions,
+						reviewCommentCount: 0,
+					} satisfies IChangesFileItem;
+				});
+			} else {
+				sourceEntries = [...editEntries, ...sessionFiles, ...repositoryFiles];
+			}
+
+			const resources = new Set();
+			const entries: IChangesFileItem[] = [];
+			for (const item of sourceEntries) {
+				if (!resources.has(item.uri.fsPath)) {
+					resources.add(item.uri.fsPath);
+					entries.push(item);
+				}
+			}
+			return entries.sort((a, b) => extUriBiasedIgnorePathCase.compare(a.uri, b.uri));
 		});
 
 		// Calculate stats from combined entries
 		const topLevelStats = derived(reader => {
 			const editEntries = editSessionEntriesObs.read(reader);
 			const sessionFiles = sessionFilesObs.read(reader);
+			const repositoryFiles = this.activeSessionRepositoryChangesObs.read(reader) ?? [];
 			const entries = combinedEntriesObs.read(reader);
 
 			let added = 0, removed = 0;
@@ -498,7 +689,7 @@ export class ChangesViewPane extends ViewPane {
 			}
 
 			const files = entries.length;
-			const isSessionMenu = editEntries.length === 0 && sessionFiles.length > 0;
+			const isSessionMenu = editEntries.length === 0 && (sessionFiles.length > 0 || repositoryFiles.length > 0);
 
 			return { files, added, removed, isSessionMenu };
 		});
@@ -507,19 +698,18 @@ export class ChangesViewPane extends ViewPane {
 		if (this.actionsContainer) {
 			dom.clearNode(this.actionsContainer);
 
-			const scopedContextKeyService = this.renderDisposables.add(this.contextKeyService.createScoped(this.actionsContainer));
-			const scopedInstantiationService = this.renderDisposables.add(this.instantiationService.createChild(new ServiceCollection([IContextKeyService, scopedContextKeyService])));
+			const scopedInstantiationService = this.renderDisposables.add(this.instantiationService.createChild(new ServiceCollection([IContextKeyService, this.scopedContextKeyService])));
 
 			// Set the chat session type context key reactively so that menu items with
 			// `chatSessionType == copilotcli` (e.g. Create Pull Request) are shown
-			const chatSessionTypeKey = scopedContextKeyService.createKey<string>(ChatContextKeys.agentSessionType.key, '');
+			const chatSessionTypeKey = this.scopedContextKeyService.createKey<string>(ChatContextKeys.agentSessionType.key, '');
 			this.renderDisposables.add(autorun(reader => {
 				const activeSession = this.activeSession.read(reader);
-				chatSessionTypeKey.set(activeSession?.sessionType ?? '');
+				chatSessionTypeKey.set(activeSession?.providerType ?? '');
 			}));
 
 			// Bind required context keys for the menu buttons
-			this.renderDisposables.add(bindContextKey(hasUndecidedChatEditingResourceContextKey, scopedContextKeyService, r => {
+			this.renderDisposables.add(bindContextKey(hasUndecidedChatEditingResourceContextKey, this.scopedContextKeyService, r => {
 				const session = activeEditingSessionObs.read(r);
 				if (!session) {
 					return false;
@@ -528,7 +718,7 @@ export class ChangesViewPane extends ViewPane {
 				return entries.some(entry => entry.state.read(r) === ModifiedFileEntryState.Modified);
 			}));
 
-			this.renderDisposables.add(bindContextKey(hasAppliedChatEditsContextKey, scopedContextKeyService, r => {
+			this.renderDisposables.add(bindContextKey(hasAppliedChatEditsContextKey, this.scopedContextKeyService, r => {
 				const session = activeEditingSessionObs.read(r);
 				if (!session) {
 					return false;
@@ -537,20 +727,79 @@ export class ChangesViewPane extends ViewPane {
 				return entries.length > 0;
 			}));
 
-			this.renderDisposables.add(bindContextKey(ChatContextKeys.hasAgentSessionChanges, scopedContextKeyService, r => {
-				const { files } = topLevelStats.read(r);
+			const hasAgentSessionChangesObs = derived(reader => {
+				const { files } = topLevelStats.read(reader);
 				return files > 0;
-			}));
+			});
+
+			this.renderDisposables.add(bindContextKey(ChatContextKeys.hasAgentSessionChanges, this.scopedContextKeyService, r => hasAgentSessionChangesObs.read(r)));
+
+			const hasUncommittedChangesObs = derived(reader => {
+				const repositoryFiles = this.activeSessionRepositoryChangesObs.read(reader);
+				return (repositoryFiles?.length ?? 0) > 0;
+			});
+
+			this.renderDisposables.add(bindContextKey(hasUncommittedChangesContextKey, this.scopedContextKeyService, r => hasUncommittedChangesObs.read(r)));
+
+			const isMergeBaseBranchProtectedObs = derived(reader => {
+				const activeSession = this.activeSession.read(reader);
+				return activeSession?.worktreeBaseBranchProtected === true;
+			});
+
+			this.renderDisposables.add(bindContextKey(isMergeBaseBranchProtectedContextKey, this.scopedContextKeyService, r => isMergeBaseBranchProtectedObs.read(r)));
+
+			const hasOpenPullRequestObs = derived(reader => {
+				const sessionResource = activeSessionResource.read(reader);
+				if (!sessionResource) {
+					return false;
+				}
+
+				sessionsChangedSignal.read(reader);
+
+				const metadata = this.agentSessionsService.getSession(sessionResource)?.metadata;
+				return !!metadata?.pullRequestUrl;
+			});
+
+			this.renderDisposables.add(bindContextKey(hasOpenPullRequestContextKey, this.scopedContextKeyService, r => hasOpenPullRequestObs.read(r)));
 
 			this.renderDisposables.add(autorun(reader => {
 				const { isSessionMenu, added, removed } = topLevelStats.read(reader);
 				const sessionResource = activeSessionResource.read(reader);
+				sessionsChangedSignal.read(reader); // Re-evaluate when session metadata changes (e.g. pullRequestUrl)
+				const menuId = isSessionMenu ? MenuId.ChatEditingSessionChangesToolbar : MenuId.ChatEditingWidgetToolbar;
+
+				// Read code review state to update the button label dynamically
+				let reviewCommentCount: number | undefined;
+				let codeReviewLoading = false;
+				if (sessionResource) {
+					const prReviewState = this.codeReviewService.getPRReviewState(sessionResource).read(reader);
+					const prReviewCommentCount = prReviewState.kind === PRReviewStateKind.Loaded ? prReviewState.comments.length : 0;
+					const sessionChanges = this.agentSessionsService.getSession(sessionResource)?.changes;
+					if (sessionChanges instanceof Array && sessionChanges.length > 0) {
+						const reviewFiles = getCodeReviewFilesFromSessionChanges(sessionChanges as readonly IChatSessionFileChange[] | readonly IChatSessionFileChange2[]);
+						const reviewVersion = getCodeReviewVersion(reviewFiles);
+						const reviewState = this.codeReviewService.getReviewState(sessionResource).read(reader);
+						if (reviewState.kind === CodeReviewStateKind.Loading && reviewState.version === reviewVersion) {
+							codeReviewLoading = true;
+						} else {
+							const codeReviewCommentCount = reviewState.kind === CodeReviewStateKind.Result && reviewState.version === reviewVersion ? reviewState.comments.length : 0;
+							const totalReviewCommentCount = codeReviewCommentCount + prReviewCommentCount;
+							if (totalReviewCommentCount > 0) {
+								reviewCommentCount = totalReviewCommentCount;
+							}
+						}
+					} else if (prReviewCommentCount > 0) {
+						reviewCommentCount = prReviewCommentCount;
+					}
+				}
+
 				reader.store.add(scopedInstantiationService.createInstance(
 					MenuWorkbenchButtonBar,
 					this.actionsContainer!,
-					isSessionMenu ? MenuId.ChatEditingSessionChangesToolbar : MenuId.ChatEditingWidgetToolbar,
+					menuId,
 					{
 						telemetrySource: 'changesView',
+						disableWhileRunning: isSessionMenu,
 						menuOptions: isSessionMenu && sessionResource
 							? { args: [sessionResource, this.agentSessionsService.getSession(sessionResource)?.metadata] }
 							: { shouldForwardArgs: true },
@@ -562,8 +811,26 @@ export class ChangesViewPane extends ViewPane {
 								);
 								return { showIcon: true, showLabel: true, isSecondary: true, customClass: 'working-set-diff-stats', customLabel: diffStatsLabel };
 							}
-							if (action.id === 'github.createPullRequest') {
-								return { showIcon: true, showLabel: true, isSecondary: true, customClass: 'flex-grow' };
+							if (action.id === RUN_SESSION_CODE_REVIEW_ACTION_ID) {
+								if (codeReviewLoading) {
+									return { showIcon: true, showLabel: true, isSecondary: true, customLabel: '$(loading~spin)', customClass: 'code-review-loading' };
+								}
+								if (reviewCommentCount !== undefined) {
+									return { showIcon: true, showLabel: true, isSecondary: true, customLabel: String(reviewCommentCount), customClass: 'code-review-comments' };
+								}
+								return { showIcon: true, showLabel: false, isSecondary: true };
+							}
+							if (action.id === 'chatEditing.synchronizeChanges') {
+								return { showIcon: true, showLabel: true, isSecondary: false };
+							}
+							if (action.id === 'github.copilot.chat.createPullRequestCopilotCLIAgentSession.createPR') {
+								return { showIcon: true, showLabel: true, isSecondary: false };
+							}
+							if (action.id === 'github.copilot.chat.openPullRequestCopilotCLIAgentSession.openPR') {
+								return { showIcon: true, showLabel: false, isSecondary: true };
+							}
+							if (action.id === 'github.copilot.chat.mergeCopilotCLIAgentSessionChanges.merge') {
+								return { showIcon: true, showLabel: true, isSecondary: false };
 							}
 							return undefined;
 						}
@@ -582,6 +849,11 @@ export class ChangesViewPane extends ViewPane {
 			dom.setVisibility(!hasEntries, this.welcomeContainer!);
 		}));
 
+		// Update badge when file count changes
+		this.renderDisposables.add(autorun(reader => {
+			this.updateBadge(topLevelStats.read(reader).files);
+		}));
+
 		// Update summary text (line counts only, file count is shown in badge)
 		if (this.summaryContainer) {
 			dom.clearNode(this.summaryContainer);
@@ -642,11 +914,9 @@ export class ChangesViewPane extends ViewPane {
 					},
 					compressionEnabled: true,
 					twistieAdditionalCssClass: (e: unknown) => {
-						if (this.viewMode === ChangesViewMode.List) {
-							return 'force-no-twistie';
-						}
-						// In tree mode, hide twistie for file items (they are never collapsible)
-						return isChangesFileItem(e as ChangesTreeElement) ? 'force-no-twistie' : undefined;
+						return this.viewMode === ChangesViewMode.List
+							? 'force-no-twistie'
+							: undefined;
 					},
 				}
 			);
@@ -656,6 +926,9 @@ export class ChangesViewPane extends ViewPane {
 		if (this.tree) {
 			const tree = this.tree;
 
+			// Re-layout when collapse state changes so the card height adjusts
+			this.renderDisposables.add(tree.onDidChangeContentHeight(() => this.layoutTree()));
+
 			const openFileItem = (item: IChangesFileItem, items: IChangesFileItem[], sideBySide: boolean) => {
 				const { uri: modifiedFileUri, originalUri, isDeletion } = item;
 				const currentIndex = items.indexOf(item);
@@ -706,6 +979,33 @@ export class ChangesViewPane extends ViewPane {
 			}));
 		}
 
+		// Bind CI status widget to active session's PR CI model
+		if (this.ciStatusWidget) {
+			const activeSessionResourceObs = derived(this, reader => this.sessionManagementService.activeSession.read(reader)?.resource);
+			const ciModelObs = derived(this, reader => {
+				const session = this.sessionManagementService.activeSession.read(reader);
+				if (!session) {
+					return undefined;
+				}
+				const context = this.sessionManagementService.getGitHubContextForSession(session.resource);
+				if (!context || context.prNumber === undefined) {
+					return undefined;
+				}
+				// Use the PR's headRef from the PR model to get CI checks
+				const prModel = this.gitHubService.getPullRequest(context.owner, context.repo, context.prNumber);
+				const pr = prModel.pullRequest.read(reader);
+				if (!pr) {
+					// Trigger a refresh if PR data isn't loaded yet
+					prModel.refresh();
+					return undefined;
+				}
+				const ciModel = this.gitHubService.getPullRequestCI(context.owner, context.repo, pr.headRef);
+				ciModel.refresh();
+				return ciModel;
+			});
+			this.renderDisposables.add(this.ciStatusWidget.bind(ciModelObs, activeSessionResourceObs));
+		}
+
 		// Update tree data with combined entries
 		this.renderDisposables.add(autorun(reader => {
 			const entries = combinedEntriesObs.read(reader);
@@ -753,8 +1053,10 @@ export class ChangesViewPane extends ViewPane {
 		const overviewHeight = this.overviewContainer?.offsetHeight ?? 0;
 		const containerPadding = 8; // 4px top + 4px bottom from .chat-editing-session-container
 		const containerBorder = 2; // 1px top + 1px bottom border
+		const ciWidgetHeight = this.ciStatusWidget?.element.offsetHeight ?? 0;
+		const ciWidgetMargin = ciWidgetHeight > 0 ? 8 : 0; // margin-top on CI widget
 
-		const usedHeight = bodyPadding + actionsHeight + actionsMargin + overviewHeight + containerPadding + containerBorder;
+		const usedHeight = bodyPadding + actionsHeight + actionsMargin + overviewHeight + containerPadding + containerBorder + ciWidgetHeight + ciWidgetMargin;
 		const availableHeight = Math.max(0, bodyHeight - usedHeight);
 
 		// Limit height to the content so the tree doesn't exceed its items
@@ -824,6 +1126,7 @@ interface IChangesTreeTemplate {
 	readonly templateDisposables: DisposableStore;
 	readonly toolbar: MenuWorkbenchToolBar | undefined;
 	readonly contextKeyService: IContextKeyService | undefined;
+	readonly reviewCommentsBadge: HTMLElement;
 	readonly decorationBadge: HTMLElement;
 	readonly addedSpan: HTMLElement;
 	readonly removedSpan: HTMLElement;
@@ -846,6 +1149,9 @@ class ChangesTreeRenderer implements ICompressibleTreeRenderer<ChangesTreeElemen
 		const templateDisposables = new DisposableStore();
 		const label = templateDisposables.add(this.labels.create(container, { supportHighlights: true, supportIcons: true }));
 
+		const reviewCommentsBadge = dom.$('.changes-review-comments-badge');
+		label.element.appendChild(reviewCommentsBadge);
+
 		const lineCountsContainer = $('.working-set-line-counts');
 		const addedSpan = dom.$('.working-set-lines-added');
 		const removedSpan = dom.$('.working-set-lines-removed');
@@ -866,7 +1172,7 @@ class ChangesTreeRenderer implements ICompressibleTreeRenderer<ChangesTreeElemen
 			label.element.appendChild(actionBarContainer);
 		}
 
-		return { templateDisposables, label, toolbar, contextKeyService, decorationBadge, addedSpan, removedSpan, lineCountsContainer };
+		return { templateDisposables, label, toolbar, contextKeyService, reviewCommentsBadge, decorationBadge, addedSpan, removedSpan, lineCountsContainer };
 	}
 
 	renderElement(node: ITreeNode<ChangesTreeElement, void>, _index: number, templateData: IChangesTreeTemplate): void {
@@ -898,6 +1204,7 @@ class ChangesTreeRenderer implements ICompressibleTreeRenderer<ChangesTreeElemen
 			});
 
 			// Hide file-specific decorations for folders
+			templateData.reviewCommentsBadge.style.display = 'none';
 			templateData.decorationBadge.style.display = 'none';
 			templateData.lineCountsContainer.style.display = 'none';
 
@@ -922,6 +1229,18 @@ class ChangesTreeRenderer implements ICompressibleTreeRenderer<ChangesTreeElemen
 		templateData.lineCountsContainer.style.display = '';
 		templateData.decorationBadge.style.display = '';
 
+		if (data.reviewCommentCount > 0) {
+			templateData.reviewCommentsBadge.style.display = '';
+			templateData.reviewCommentsBadge.className = 'changes-review-comments-badge';
+			templateData.reviewCommentsBadge.replaceChildren(
+				dom.$('.codicon.codicon-comment-unresolved'),
+				dom.$('span', undefined, `${data.reviewCommentCount}`)
+			);
+		} else {
+			templateData.reviewCommentsBadge.style.display = 'none';
+			templateData.reviewCommentsBadge.replaceChildren();
+		}
+
 		// Update decoration badge (A/M/D)
 		const badge = templateData.decorationBadge;
 		badge.className = 'changes-decoration-badge';
@@ -961,6 +1280,7 @@ class ChangesTreeRenderer implements ICompressibleTreeRenderer<ChangesTreeElemen
 		});
 
 		// Hide file-specific decorations for folders
+		templateData.reviewCommentsBadge.style.display = 'none';
 		templateData.decorationBadge.style.display = 'none';
 		templateData.lineCountsContainer.style.display = 'none';
 
@@ -1027,3 +1347,84 @@ class SetChangesTreeViewModeAction extends ViewAction<ChangesViewPane> {
 
 registerAction2(SetChangesListViewModeAction);
 registerAction2(SetChangesTreeViewModeAction);
+
+// --- Versions Submenu
+
+MenuRegistry.appendMenuItem(MenuId.ViewTitle, {
+	submenu: MenuId.ChatEditingSessionChangesVersionsSubmenu,
+	title: localize2('versionsActions', 'Versions'),
+	icon: Codicon.versions,
+	group: 'navigation',
+	order: 9,
+	when: ContextKeyExpr.and(ContextKeyExpr.equals('view', CHANGES_VIEW_ID), IsSessionsWindowContext, ChatContextKeys.hasAgentSessionChanges),
+});
+
+class AllChangesAction extends Action2 {
+	constructor() {
+		super({
+			id: 'chatEditing.versionsAllChanges',
+			title: localize2('chatEditing.versionsAllChanges', 'All Changes'),
+			category: CHAT_CATEGORY,
+			toggled: changesVersionModeContextKey.isEqualTo(ChangesVersionMode.AllChanges),
+			menu: [{
+				id: MenuId.ChatEditingSessionChangesVersionsSubmenu,
+				group: '1_changes',
+				order: 1,
+			}],
+		});
+	}
+
+	override async run(accessor: ServicesAccessor): Promise<void> {
+		const viewsService = accessor.get(IViewsService);
+		const view = viewsService.getActiveViewWithId<ChangesViewPane>(CHANGES_VIEW_ID);
+		view?.setVersionMode(ChangesVersionMode.AllChanges);
+	}
+}
+registerAction2(AllChangesAction);
+
+class LastTurnChangesAction extends Action2 {
+	constructor() {
+		super({
+			id: 'chatEditing.versionsLastTurnChanges',
+			title: localize2('chatEditing.versionsLastTurnChanges', "Last Turn's Changes"),
+			category: CHAT_CATEGORY,
+			toggled: changesVersionModeContextKey.isEqualTo(ChangesVersionMode.LastTurn),
+			menu: [{
+				id: MenuId.ChatEditingSessionChangesVersionsSubmenu,
+				group: '1_changes',
+				order: 2,
+			}],
+		});
+	}
+
+	override async run(accessor: ServicesAccessor): Promise<void> {
+		const viewsService = accessor.get(IViewsService);
+		const view = viewsService.getActiveViewWithId<ChangesViewPane>(CHANGES_VIEW_ID);
+		view?.setVersionMode(ChangesVersionMode.LastTurn);
+	}
+}
+registerAction2(LastTurnChangesAction);
+
+class UncommittedChangesAction extends Action2 {
+	constructor() {
+		super({
+			id: 'chatEditing.versionsUncommittedChanges',
+			title: localize2('chatEditing.versionsUncommittedChanges', 'Uncommitted Changes'),
+			category: CHAT_CATEGORY,
+			toggled: changesVersionModeContextKey.isEqualTo(ChangesVersionMode.Uncommitted),
+			precondition: hasUncommittedChangesContextKey,
+			menu: [{
+				id: MenuId.ChatEditingSessionChangesVersionsSubmenu,
+				group: '2_uncommitted',
+				order: 1,
+			}],
+		});
+	}
+
+	override async run(accessor: ServicesAccessor): Promise<void> {
+		const viewsService = accessor.get(IViewsService);
+		const view = viewsService.getActiveViewWithId<ChangesViewPane>(CHANGES_VIEW_ID);
+		view?.setVersionMode(ChangesVersionMode.Uncommitted);
+	}
+}
+registerAction2(UncommittedChangesAction);
diff --git a/src/vs/sessions/contrib/changes/browser/changesViewActions.ts b/src/vs/sessions/contrib/changes/browser/changesViewActions.ts
new file mode 100644
index 0000000000000..9ca4eeb503dcf
--- /dev/null
+++ b/src/vs/sessions/contrib/changes/browser/changesViewActions.ts
@@ -0,0 +1,72 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Codicon } from '../../../../base/common/codicons.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { observableFromEvent } from '../../../../base/common/observable.js';
+import { localize2 } from '../../../../nls.js';
+import { Action2, IAction2Options, registerAction2 } from '../../../../platform/actions/common/actions.js';
+import { ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
+import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../../workbench/common/contributions.js';
+import { hasValidDiff } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsModel.js';
+import { IAgentSessionsService } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
+import { IViewsService } from '../../../../workbench/services/views/common/viewsService.js';
+import { ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
+import { CHANGES_VIEW_ID } from './changesView.js';
+import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
+import { bindContextKey } from '../../../../platform/observable/common/platformObservableUtils.js';
+
+import { activeSessionHasChangesContextKey } from '../common/changes.js';
+
+const openChangesViewActionOptions: IAction2Options = {
+	id: 'workbench.action.agentSessions.openChangesView',
+	title: localize2('openChangesView', "Changes"),
+	icon: Codicon.diffMultiple,
+	f1: false,
+};
+
+class OpenChangesViewAction extends Action2 {
+
+	static readonly ID = openChangesViewActionOptions.id;
+
+	constructor() {
+		super(openChangesViewActionOptions);
+	}
+
+	async run(accessor: ServicesAccessor): Promise<void> {
+		const viewsService = accessor.get(IViewsService);
+		await viewsService.openView(CHANGES_VIEW_ID, true);
+	}
+}
+
+registerAction2(OpenChangesViewAction);
+
+class ChangesViewActionsContribution extends Disposable implements IWorkbenchContribution {
+
+	static readonly ID = 'workbench.contrib.changesViewActions';
+
+	constructor(
+		@IContextKeyService contextKeyService: IContextKeyService,
+		@ISessionsManagementService sessionManagementService: ISessionsManagementService,
+		@IAgentSessionsService agentSessionsService: IAgentSessionsService,
+	) {
+		super();
+
+		// Bind context key: true when the active session has changes
+		const sessionsChanged = observableFromEvent(this, agentSessionsService.model.onDidChangeSessions, () => { });
+		this._register(bindContextKey(activeSessionHasChangesContextKey, contextKeyService, reader => {
+			sessionManagementService.activeSession.read(reader);
+			sessionsChanged.read(reader);
+			const activeSession = sessionManagementService.getActiveSession();
+			if (!activeSession) {
+				return false;
+			}
+			const agentSession = agentSessionsService.getSession(activeSession.resource);
+			return !!agentSession?.changes && hasValidDiff(agentSession.changes);
+		}));
+	}
+}
+
+registerWorkbenchContribution2(ChangesViewActionsContribution.ID, ChangesViewActionsContribution, WorkbenchPhase.AfterRestored);
diff --git a/src/vs/sessions/contrib/changes/browser/ciStatusWidget.ts b/src/vs/sessions/contrib/changes/browser/ciStatusWidget.ts
new file mode 100644
index 0000000000000..78023d8bff411
--- /dev/null
+++ b/src/vs/sessions/contrib/changes/browser/ciStatusWidget.ts
@@ -0,0 +1,519 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import './media/ciStatusWidget.css';
+import * as dom from '../../../../base/browser/dom.js';
+import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
+import { IListRenderer, IListVirtualDelegate } from '../../../../base/browser/ui/list/list.js';
+import { Action } from '../../../../base/common/actions.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { Disposable, DisposableStore, IDisposable } from '../../../../base/common/lifecycle.js';
+import { autorun, IObservable } from '../../../../base/common/observable.js';
+import { ThemeIcon } from '../../../../base/common/themables.js';
+import { URI } from '../../../../base/common/uri.js';
+import { localize } from '../../../../nls.js';
+import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
+import { WorkbenchList } from '../../../../platform/list/browser/listService.js';
+import { IOpenerService } from '../../../../platform/opener/common/opener.js';
+import { spinningLoading } from '../../../../platform/theme/common/iconRegistry.js';
+import { ChatViewPaneTarget, IChatWidgetService } from '../../../../workbench/contrib/chat/browser/chat.js';
+import { DEFAULT_LABELS_CONTAINER, IResourceLabel, ResourceLabels } from '../../../../workbench/browser/labels.js';
+import { ActionBar } from '../../../../base/browser/ui/actionbar/actionbar.js';
+import { GitHubCheckConclusion, GitHubCheckStatus, GitHubCIOverallStatus, IGitHubCICheck } from '../../github/common/types.js';
+import { GitHubPullRequestCIModel } from '../../github/browser/models/githubPullRequestCIModel.js';
+
+const $ = dom.$;
+
+const enum CICheckGroup {
+	Running,
+	Pending,
+	Failed,
+	Successful,
+}
+
+interface ICICheckListItem {
+	readonly check: IGitHubCICheck;
+	readonly group: CICheckGroup;
+}
+
+interface ICICheckCounts {
+	readonly running: number;
+	readonly pending: number;
+	readonly failed: number;
+	readonly successful: number;
+}
+
+class CICheckListDelegate implements IListVirtualDelegate<ICICheckListItem> {
+	static readonly ITEM_HEIGHT = 24;
+
+	getHeight(_element: ICICheckListItem): number {
+		return CICheckListDelegate.ITEM_HEIGHT;
+	}
+
+	getTemplateId(_element: ICICheckListItem): string {
+		return CICheckListRenderer.TEMPLATE_ID;
+	}
+}
+
+interface ICICheckTemplateData {
+	readonly row: HTMLElement;
+	readonly label: IResourceLabel;
+	readonly actionBar: ActionBar;
+	readonly templateDisposables: DisposableStore;
+	readonly elementDisposables: DisposableStore;
+}
+
+class CICheckListRenderer implements IListRenderer<ICICheckListItem, ICICheckTemplateData> {
+	static readonly TEMPLATE_ID = 'ciCheck';
+	readonly templateId = CICheckListRenderer.TEMPLATE_ID;
+
+	constructor(
+		private readonly _labels: ResourceLabels,
+		private readonly _openerService: IOpenerService,
+	) { }
+
+	renderTemplate(container: HTMLElement): ICICheckTemplateData {
+		const templateDisposables = new DisposableStore();
+		const row = dom.append(container, $('.ci-status-widget-check'));
+
+		const labelContainer = dom.append(row, $('.ci-status-widget-check-label'));
+		const label = templateDisposables.add(this._labels.create(labelContainer, { supportIcons: true }));
+
+		const actionBarContainer = dom.append(row, $('.ci-status-widget-check-actions'));
+		const actionBar = templateDisposables.add(new ActionBar(actionBarContainer));
+
+		return {
+			row,
+			label,
+			actionBar,
+			templateDisposables,
+			elementDisposables: templateDisposables.add(new DisposableStore()),
+		};
+	}
+
+	renderElement(element: ICICheckListItem, _index: number, templateData: ICICheckTemplateData): void {
+		templateData.elementDisposables.clear();
+		templateData.actionBar.clear();
+
+		templateData.row.className = `ci-status-widget-check ${getCheckStatusClass(element.check)}`;
+
+		const title = localize('ci.checkTitle', "{0}: {1}", element.check.name, getCheckStateLabel(element.check));
+		templateData.label.setResource({
+			name: element.check.name,
+			resource: URI.from({ scheme: 'github-check', path: `/${element.check.id}/${element.check.name}` }),
+		}, {
+			icon: getCheckIcon(element.check),
+			title,
+		});
+
+		const actions: Action[] = [];
+
+		if (element.check.detailsUrl) {
+			actions.push(templateData.elementDisposables.add(new Action(
+				'ci.openOnGitHub',
+				localize('ci.openOnGitHub', "Open on GitHub"),
+				ThemeIcon.asClassName(Codicon.linkExternal),
+				true,
+				async () => {
+					await this._openerService.open(URI.parse(element.check.detailsUrl!));
+				},
+			)));
+		}
+
+		templateData.actionBar.push(actions, { icon: true, label: false });
+	}
+
+	disposeElement(_element: ICICheckListItem, _index: number, templateData: ICICheckTemplateData): void {
+		templateData.elementDisposables.clear();
+		templateData.actionBar.clear();
+	}
+
+	disposeTemplate(templateData: ICICheckTemplateData): void {
+		templateData.templateDisposables.dispose();
+	}
+}
+
+/**
+ * A collapsible widget that shows the CI status of a PR.
+ * Rendered beneath the changes tree in the changes view.
+ */
+export class CIStatusWidget extends Disposable {
+
+	private readonly _domNode: HTMLElement;
+	private readonly _headerNode: HTMLElement;
+	private readonly _titleNode: HTMLElement;
+	private readonly _titleLabel: IResourceLabel;
+	private readonly _headerActionBarContainer: HTMLElement;
+	private readonly _headerActionBar: ActionBar;
+	private readonly _twistieNode: HTMLElement;
+	private readonly _bodyNode: HTMLElement;
+	private readonly _list: WorkbenchList<ICICheckListItem>;
+	private readonly _labels: ResourceLabels;
+	private readonly _headerActionDisposables = this._register(new DisposableStore());
+
+	private _collapsed = true;
+	private _model: GitHubPullRequestCIModel | undefined;
+	private _sessionResource: URI | undefined;
+
+	get element(): HTMLElement {
+		return this._domNode;
+	}
+
+	constructor(
+		container: HTMLElement,
+		@IOpenerService private readonly _openerService: IOpenerService,
+		@IChatWidgetService private readonly _chatWidgetService: IChatWidgetService,
+		@IInstantiationService private readonly _instantiationService: IInstantiationService,
+	) {
+		super();
+		this._labels = this._register(this._instantiationService.createInstance(ResourceLabels, DEFAULT_LABELS_CONTAINER));
+
+		this._domNode = dom.append(container, $('.ci-status-widget'));
+		this._domNode.style.display = 'none';
+
+		// Header (always visible)
+		this._headerNode = dom.append(this._domNode, $('.ci-status-widget-header'));
+		this._titleNode = dom.append(this._headerNode, $('.ci-status-widget-title'));
+		this._titleLabel = this._register(this._labels.create(this._titleNode, { supportIcons: true }));
+		this._headerActionBarContainer = dom.append(this._headerNode, $('.ci-status-widget-header-actions'));
+		this._headerActionBar = this._register(new ActionBar(this._headerActionBarContainer));
+		this._headerActionBarContainer.style.display = 'none';
+		this._register(dom.addDisposableListener(this._headerActionBarContainer, dom.EventType.CLICK, e => {
+			e.preventDefault();
+			e.stopPropagation();
+		}));
+		this._twistieNode = dom.append(this._headerNode, $('.ci-status-widget-twistie'));
+		this._updateTwistie();
+
+		this._register(dom.addDisposableListener(this._headerNode, 'click', () => this._toggle()));
+
+		// Body (collapsible list of checks)
+		this._bodyNode = dom.append(this._domNode, $('.ci-status-widget-body'));
+		this._bodyNode.style.display = 'none';
+
+		const listContainer = $('.ci-status-widget-list');
+		this._list = this._register(this._instantiationService.createInstance(
+			WorkbenchList<ICICheckListItem>,
+			'CIStatusWidget',
+			listContainer,
+			new CICheckListDelegate(),
+			[new CICheckListRenderer(this._labels, this._openerService)],
+			{
+				multipleSelectionSupport: false,
+				openOnSingleClick: false,
+				accessibilityProvider: {
+					getWidgetAriaLabel: () => localize('ci.checksListAriaLabel', "Checks"),
+					getAriaLabel: item => localize('ci.checkAriaLabel', "{0}, {1}", item.check.name, getCheckStateLabel(item.check)),
+				},
+				keyboardNavigationLabelProvider: {
+					getKeyboardNavigationLabel: item => item.check.name,
+				},
+			},
+		));
+		this._bodyNode.appendChild(this._list.getHTMLElement());
+	}
+
+	/**
+	 * Bind to a CI model. When `ciModel` is undefined, the widget hides.
+	 * Returns a disposable that stops observation.
+	 */
+	bind(ciModel: IObservable<GitHubPullRequestCIModel | undefined>, sessionResource: IObservable<URI | undefined>): IDisposable {
+		return autorun(reader => {
+			const model = ciModel.read(reader);
+			this._sessionResource = sessionResource.read(reader);
+			this._model = model;
+			if (!model) {
+				this._renderBody([]);
+				this._renderHeaderActions([]);
+				this._domNode.style.display = 'none';
+				return;
+			}
+
+			const checks = model.checks.read(reader);
+			const overallStatus = model.overallStatus.read(reader);
+
+			if (checks.length === 0) {
+				this._renderBody([]);
+				this._renderHeaderActions([]);
+				this._domNode.style.display = 'none';
+				return;
+			}
+
+			this._domNode.style.display = '';
+			this._renderHeader(checks, overallStatus);
+			this._renderHeaderActions(getFailedChecks(checks));
+			this._renderBody(sortChecks(checks));
+		});
+	}
+
+	private _toggle(): void {
+		this._collapsed = !this._collapsed;
+		this._bodyNode.style.display = this._collapsed ? 'none' : '';
+		this._updateTwistie();
+	}
+
+	private _updateTwistie(): void {
+		dom.clearNode(this._twistieNode);
+		this._twistieNode.appendChild(renderIcon(this._collapsed ? Codicon.chevronRight : Codicon.chevronDown));
+	}
+
+	private _renderHeader(checks: readonly IGitHubCICheck[], overallStatus: GitHubCIOverallStatus): void {
+		const { icon, className } = getHeaderIconAndClass(checks, overallStatus);
+		this._titleNode.className = `ci-status-widget-title ${className}`;
+
+		const summary = getChecksSummary(checks);
+		const title = localize('ci.headerTitle', "Checks: {0}", summary);
+		this._titleLabel.setResource({
+			name: title,
+			resource: URI.from({ scheme: 'github-checks', path: '/summary' }),
+		}, {
+			icon: icon,
+			title,
+		});
+	}
+
+	private _renderHeaderActions(failedChecks: readonly IGitHubCICheck[]): void {
+		this._headerActionDisposables.clear();
+		this._headerActionBar.clear();
+
+		if (failedChecks.length === 0) {
+			this._headerActionBarContainer.style.display = 'none';
+			return;
+		}
+
+		const fixChecksAction = this._headerActionDisposables.add(new Action(
+			'ci.fixChecks',
+			localize('ci.fixChecks', "Fix Checks"),
+			ThemeIcon.asClassName(Codicon.sparkle),
+			true,
+			async () => {
+				await this._sendFixChecksPrompt(failedChecks);
+			},
+		));
+
+		this._headerActionBar.push([fixChecksAction], { icon: true, label: false });
+		this._headerActionBarContainer.style.display = 'flex';
+	}
+
+	private _renderBody(checks: readonly ICICheckListItem[]): void {
+		const height = checks.length * CICheckListDelegate.ITEM_HEIGHT;
+		this._list.getHTMLElement().style.height = `${height}px`;
+		this._list.layout(height);
+		this._list.splice(0, this._list.length, checks);
+	}
+
+	private async _sendFixChecksPrompt(failedChecks: readonly IGitHubCICheck[]): Promise<void> {
+		const model = this._model;
+		const sessionResource = this._sessionResource;
+		if (!model || !sessionResource || failedChecks.length === 0) {
+			return;
+		}
+
+		const failedCheckDetails = await Promise.all(failedChecks.map(async check => {
+			const annotations = await model.getCheckRunAnnotations(check.id);
+			return {
+				check,
+				annotations,
+			};
+		}));
+
+		const prompt = buildFixChecksPrompt(failedCheckDetails);
+		const chatWidget = this._chatWidgetService.getWidgetBySessionResource(sessionResource)
+			?? await this._chatWidgetService.openSession(sessionResource, ChatViewPaneTarget);
+		if (!chatWidget) {
+			return;
+		}
+
+		await chatWidget.acceptInput(prompt, { noCommandDetection: true });
+	}
+}
+
+function sortChecks(checks: readonly IGitHubCICheck[]): ICICheckListItem[] {
+	return [...checks]
+		.sort(compareChecks)
+		.map(check => ({ check, group: getCheckGroup(check) }));
+}
+
+function compareChecks(a: IGitHubCICheck, b: IGitHubCICheck): number {
+	const groupDiff = getCheckGroup(a) - getCheckGroup(b);
+	if (groupDiff !== 0) {
+		return groupDiff;
+	}
+
+	return a.name.localeCompare(b.name, undefined, { sensitivity: 'base' });
+}
+
+function getCheckGroup(check: IGitHubCICheck): CICheckGroup {
+	switch (check.status) {
+		case GitHubCheckStatus.InProgress:
+			return CICheckGroup.Running;
+		case GitHubCheckStatus.Queued:
+			return CICheckGroup.Pending;
+		case GitHubCheckStatus.Completed:
+			return isFailedConclusion(check.conclusion) ? CICheckGroup.Failed : CICheckGroup.Successful;
+	}
+}
+
+function getCheckCounts(checks: readonly IGitHubCICheck[]): ICICheckCounts {
+	let running = 0;
+	let pending = 0;
+	let failed = 0;
+	let successful = 0;
+
+	for (const check of checks) {
+		switch (getCheckGroup(check)) {
+			case CICheckGroup.Running:
+				running++;
+				break;
+			case CICheckGroup.Pending:
+				pending++;
+				break;
+			case CICheckGroup.Failed:
+				failed++;
+				break;
+			case CICheckGroup.Successful:
+				successful++;
+				break;
+		}
+	}
+
+	return { running, pending, failed, successful };
+}
+
+function getFailedChecks(checks: readonly IGitHubCICheck[]): readonly IGitHubCICheck[] {
+	return checks.filter(check => getCheckGroup(check) === CICheckGroup.Failed);
+}
+
+function getChecksSummary(checks: readonly IGitHubCICheck[]): string {
+	const counts = getCheckCounts(checks);
+	const parts: string[] = [];
+
+	if (counts.running > 0) {
+		parts.push(counts.running === 1
+			? localize('ci.oneRunning', "1 running")
+			: localize('ci.manyRunning', "{0} running", counts.running));
+	}
+
+	if (counts.pending > 0) {
+		parts.push(counts.pending === 1
+			? localize('ci.onePending', "1 pending")
+			: localize('ci.manyPending', "{0} pending", counts.pending));
+	}
+
+	if (counts.failed > 0) {
+		parts.push(counts.failed === 1
+			? localize('ci.oneFailed', "1 failed")
+			: localize('ci.manyFailed', "{0} failed", counts.failed));
+	}
+
+	if (counts.successful > 0) {
+		parts.push(counts.successful === 1
+			? localize('ci.oneSuccessful', "1 successful")
+			: localize('ci.manySuccessful', "{0} successful", counts.successful));
+	}
+
+	return parts.join(', ');
+}
+
+function buildFixChecksPrompt(failedChecks: ReadonlyArray<{ check: IGitHubCICheck; annotations: string }>): string {
+	const sections = failedChecks.map(({ check, annotations }) => {
+		const parts = [
+			`Check: ${check.name}`,
+			`Status: ${getCheckStateLabel(check)}`,
+			`Conclusion: ${check.conclusion ?? 'unknown'}`,
+		];
+
+		if (check.detailsUrl) {
+			parts.push(`Details: ${check.detailsUrl}`);
+		}
+
+		parts.push('', 'Annotations and output:', annotations || 'No output available for this check run.');
+		return parts.join('\n');
+	});
+
+	return [
+		'Please fix the failed CI checks for this session immediately.',
+		'Use the failed check information below, including annotations and check output, to identify the root causes and make the necessary code changes.',
+		'Focus on resolving these CI failures. Avoid unrelated changes unless they are required to fix the checks.',
+		'',
+		'Failed CI checks:',
+		'',
+		sections.join('\n\n---\n\n'),
+	].join('\n');
+}
+
+function getHeaderIconAndClass(checks: readonly IGitHubCICheck[], overallStatus: GitHubCIOverallStatus): { icon: ThemeIcon; className: string } {
+	const counts = getCheckCounts(checks);
+	if (counts.running > 0) {
+		return { icon: spinningLoading, className: 'ci-status-running' };
+	}
+
+	switch (overallStatus) {
+		case GitHubCIOverallStatus.Success:
+			return { icon: Codicon.passFilled, className: 'ci-status-success' };
+		case GitHubCIOverallStatus.Failure:
+			return { icon: Codicon.error, className: 'ci-status-failure' };
+		case GitHubCIOverallStatus.Pending:
+			return { icon: Codicon.circle, className: 'ci-status-pending' };
+		default:
+			return { icon: Codicon.circleFilled, className: 'ci-status-neutral' };
+	}
+}
+
+function getCheckIcon(check: IGitHubCICheck): ThemeIcon {
+	switch (check.status) {
+		case GitHubCheckStatus.InProgress:
+			return spinningLoading;
+		case GitHubCheckStatus.Queued:
+			return Codicon.circle;
+		case GitHubCheckStatus.Completed:
+			switch (check.conclusion) {
+				case GitHubCheckConclusion.Success:
+					return Codicon.passFilled;
+				case GitHubCheckConclusion.Failure:
+				case GitHubCheckConclusion.TimedOut:
+				case GitHubCheckConclusion.ActionRequired:
+					return Codicon.error;
+				case GitHubCheckConclusion.Cancelled:
+					return Codicon.circleSlash;
+				case GitHubCheckConclusion.Skipped:
+					return Codicon.debugStepOver;
+				default:
+					return Codicon.circleFilled;
+			}
+	}
+}
+
+function getCheckStatusClass(check: IGitHubCICheck): string {
+	switch (getCheckGroup(check)) {
+		case CICheckGroup.Running:
+			return 'ci-status-running';
+		case CICheckGroup.Pending:
+			return 'ci-status-pending';
+		case CICheckGroup.Failed:
+			return 'ci-status-failure';
+		case CICheckGroup.Successful:
+			return 'ci-status-success';
+	}
+}
+
+function getCheckStateLabel(check: IGitHubCICheck): string {
+	switch (getCheckGroup(check)) {
+		case CICheckGroup.Running:
+			return localize('ci.runningState', "running");
+		case CICheckGroup.Pending:
+			return localize('ci.pendingState', "pending");
+		case CICheckGroup.Failed:
+			return localize('ci.failedState', "failed");
+		case CICheckGroup.Successful:
+			return localize('ci.successfulState', "successful");
+	}
+}
+
+function isFailedConclusion(conclusion: GitHubCheckConclusion | undefined): boolean {
+	return conclusion === GitHubCheckConclusion.Failure
+		|| conclusion === GitHubCheckConclusion.TimedOut
+		|| conclusion === GitHubCheckConclusion.ActionRequired;
+}
diff --git a/src/vs/sessions/contrib/changesView/browser/media/changesView.css b/src/vs/sessions/contrib/changes/browser/media/changesView.css
similarity index 82%
rename from src/vs/sessions/contrib/changesView/browser/media/changesView.css
rename to src/vs/sessions/contrib/changes/browser/media/changesView.css
index 1300b886cbcd8..1b18723383299 100644
--- a/src/vs/sessions/contrib/changesView/browser/media/changesView.css
+++ b/src/vs/sessions/contrib/changes/browser/media/changesView.css
@@ -104,7 +104,6 @@
 .changes-view-body .chat-editing-session-actions.outside-card .monaco-button {
 	height: 26px;
 	padding: 4px 14px;
-	border-radius: 4px;
 	font-size: 12px;
 	line-height: 18px;
 }
@@ -114,6 +113,29 @@
 	flex: 1;
 }
 
+/* ButtonWithDropdown container grows to fill available space */
+.changes-view-body .chat-editing-session-actions.outside-card .monaco-button-dropdown {
+	flex: 1;
+	display: flex;
+}
+
+.changes-view-body .chat-editing-session-actions.outside-card .monaco-button-dropdown > .monaco-button {
+	flex: 1;
+	box-sizing: border-box;
+}
+
+.changes-view-body .chat-editing-session-actions.outside-card .monaco-button-dropdown > .monaco-button-dropdown-separator {
+	flex: 0;
+}
+
+.changes-view-body .chat-editing-session-actions.outside-card .monaco-button-dropdown > .monaco-button.monaco-dropdown-button {
+	flex: 0 0 auto;
+	padding: 4px;
+	width: auto;
+	min-width: 0;
+	border-radius: 0px 4px 4px 0px;
+}
+
 .changes-view-body .chat-editing-session-actions.outside-card .monaco-button.secondary.monaco-text-button.codicon {
 	padding: 4px 8px;
 	font-size: 16px !important;
@@ -136,6 +158,10 @@
 	color: var(--vscode-button-secondaryForeground);
 }
 
+.changes-view-body .chat-editing-session-actions.outside-card .monaco-button-dropdown > .monaco-button.secondary.monaco-text-button {
+	border-radius: 4px 0px 0px 4px;
+}
+
 .changes-view-body .chat-editing-session-actions .monaco-button.secondary:hover {
 	background-color: var(--vscode-button-secondaryHoverBackground);
 	color: var(--vscode-button-secondaryForeground);
@@ -213,6 +239,19 @@
 	font-size: 11px;
 }
 
+.changes-view-body .chat-editing-session-list .changes-review-comments-badge {
+	display: inline-flex;
+	align-items: center;
+	gap: 4px;
+	font-size: 11px;
+	margin-right: 6px;
+	color: var(--vscode-descriptionForeground);
+}
+
+.changes-view-body .chat-editing-session-list .changes-review-comments-badge .codicon {
+	font-size: 12px;
+}
+
 .changes-view-body .chat-editing-session-list .working-set-lines-added {
 	color: var(--vscode-chat-linesAddedForeground);
 }
@@ -235,3 +274,9 @@
 .changes-view-body .chat-editing-session-actions .monaco-button .working-set-lines-removed {
 	color: var(--vscode-chat-linesRemovedForeground);
 }
+
+.changes-view-body .chat-editing-session-actions .monaco-button.code-review-comments,
+.changes-view-body .chat-editing-session-actions .monaco-button.code-review-loading {
+	padding-left: 4px;
+	padding-right: 4px;
+}
diff --git a/src/vs/sessions/contrib/changes/browser/media/changesViewActions.css b/src/vs/sessions/contrib/changes/browser/media/changesViewActions.css
new file mode 100644
index 0000000000000..b848ca2f2d161
--- /dev/null
+++ b/src/vs/sessions/contrib/changes/browser/media/changesViewActions.css
@@ -0,0 +1,32 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+.changes-action-view-item {
+	display: flex;
+	align-items: center;
+	gap: 3px;
+	cursor: pointer;
+	padding: 0 4px;
+	border-radius: 3px;
+}
+
+.changes-action-view-item:hover {
+	background-color: var(--vscode-toolbar-hoverBackground);
+}
+
+.changes-action-view-item .changes-action-icon {
+	display: flex;
+	align-items: center;
+	flex-shrink: 0;
+	font-size: 14px;
+}
+
+.changes-action-view-item .changes-action-added {
+	color: var(--vscode-gitDecoration-addedResourceForeground);
+}
+
+.changes-action-view-item .changes-action-removed {
+	color: var(--vscode-gitDecoration-deletedResourceForeground);
+}
diff --git a/src/vs/sessions/contrib/changes/browser/media/ciStatusWidget.css b/src/vs/sessions/contrib/changes/browser/media/ciStatusWidget.css
new file mode 100644
index 0000000000000..2acaa1fa18d76
--- /dev/null
+++ b/src/vs/sessions/contrib/changes/browser/media/ciStatusWidget.css
@@ -0,0 +1,188 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+/* CI Status Widget - beneath the changes tree */
+.ci-status-widget {
+	margin-top: 8px;
+	border: 1px solid var(--vscode-input-border, transparent);
+	border-radius: 4px;
+	background-color: var(--vscode-editor-background);
+	overflow: hidden;
+	font-size: 12px;
+}
+
+/* Header - always visible, clickable */
+.ci-status-widget-header {
+	display: flex;
+	align-items: center;
+	gap: 6px;
+	padding: 4px 8px 4px 4px;
+	cursor: pointer;
+	-webkit-user-select: none;
+	user-select: none;
+	min-height: 22px;
+}
+
+.ci-status-widget-header:hover {
+	background-color: var(--vscode-list-hoverBackground);
+}
+
+/* Title - single line, overflow ellipsis */
+.ci-status-widget-title {
+	flex: 1;
+	overflow: hidden;
+	color: var(--vscode-foreground);
+}
+
+.ci-status-widget-title .monaco-icon-label {
+	width: 100%;
+}
+
+.ci-status-widget-title .monaco-icon-label-container,
+.ci-status-widget-title .monaco-icon-name-container {
+	display: block;
+	overflow: hidden;
+}
+
+.ci-status-widget-title .label-name {
+	overflow: hidden;
+	text-overflow: ellipsis;
+	white-space: nowrap;
+}
+
+.ci-status-widget-header-actions {
+	flex: 0 0 auto;
+	display: none;
+	align-items: center;
+	margin-left: auto;
+}
+
+.ci-status-widget-header-actions .monaco-action-bar {
+	display: flex;
+	align-items: center;
+}
+
+.ci-status-widget-header-actions .action-item .action-label {
+	width: 16px;
+	height: 16px;
+}
+
+/* Twistie icon on the right */
+.ci-status-widget-twistie {
+	flex: 0 0 auto;
+	display: flex;
+	align-items: center;
+	color: var(--vscode-foreground);
+	opacity: 0.7;
+}
+
+/* Body - collapsible list */
+.ci-status-widget-body {
+	border-top: 1px solid var(--vscode-input-border, transparent);
+}
+
+.ci-status-widget-list {
+	background-color: transparent;
+}
+
+.ci-status-widget-list > .monaco-list,
+.ci-status-widget-list > .monaco-list > .monaco-scrollable-element {
+	background-color: transparent;
+}
+
+/* Individual check row */
+.ci-status-widget-check {
+	display: flex;
+	align-items: center;
+	gap: 6px;
+	padding: 4px 8px 4px 4px;
+	height: 100%;
+	width: 100%;
+	box-sizing: border-box;
+	min-width: 0;
+}
+
+.ci-status-widget-list .monaco-list-row:hover .ci-status-widget-check,
+.ci-status-widget-list .monaco-list-row.focused .ci-status-widget-check,
+.ci-status-widget-list .monaco-list-row.selected .ci-status-widget-check {
+	background-color: var(--vscode-list-hoverBackground);
+}
+
+.ci-status-widget-check-label {
+	display: flex;
+	flex: 1;
+	min-width: 0;
+	overflow: hidden;
+}
+
+
+.ci-status-widget-check-label .monaco-icon-label {
+	display: flex;
+	flex: 1;
+	min-width: 0;
+	width: 100%;
+}
+
+.ci-status-widget-check-label .monaco-icon-label-container,
+.ci-status-widget-check-label .monaco-icon-name-container {
+	display: block;
+	min-width: 0;
+	overflow: hidden;
+}
+
+.ci-status-widget-check-label .label-name {
+	display: block;
+	overflow: hidden;
+	text-overflow: ellipsis;
+	white-space: nowrap;
+	color: var(--vscode-foreground);
+}
+
+.ci-status-widget-title.ci-status-success .monaco-icon-label::before,
+.ci-status-widget-check.ci-status-success .monaco-icon-label::before {
+	color: var(--vscode-testing-iconPassed, #73c991);
+}
+
+.ci-status-widget-title.ci-status-failure .monaco-icon-label::before,
+.ci-status-widget-check.ci-status-failure .monaco-icon-label::before {
+	color: var(--vscode-testing-iconFailed, #f14c4c);
+}
+
+.ci-status-widget-title.ci-status-running .monaco-icon-label::before,
+.ci-status-widget-check.ci-status-running .monaco-icon-label::before,
+.ci-status-widget-title.ci-status-pending .monaco-icon-label::before,
+.ci-status-widget-check.ci-status-pending .monaco-icon-label::before {
+	color: var(--vscode-testing-iconQueued, var(--vscode-editorWarning-foreground));
+}
+
+.ci-status-widget-title.ci-status-neutral .monaco-icon-label::before,
+.ci-status-widget-check.ci-status-neutral .monaco-icon-label::before {
+	color: var(--vscode-descriptionForeground);
+}
+
+/* Actions - float to the right, visible on hover */
+.ci-status-widget-check-actions {
+	display: none;
+	flex: 0 0 auto;
+	flex-shrink: 0;
+	margin-left: auto;
+}
+
+.ci-status-widget-list .monaco-list-row:hover .ci-status-widget-check-actions,
+.ci-status-widget-list .monaco-list-row.focused .ci-status-widget-check-actions,
+.ci-status-widget-list .monaco-list-row.selected .ci-status-widget-check-actions,
+.ci-status-widget-check:hover .ci-status-widget-check-actions {
+	display: flex;
+}
+
+.ci-status-widget-check-actions .monaco-action-bar {
+	display: flex;
+	align-items: center;
+}
+
+.ci-status-widget-check-actions .action-bar .action-item .action-label {
+	width: 16px;
+	height: 16px;
+}
diff --git a/src/vs/sessions/contrib/sessions/browser/sessionsAuxiliaryBarContribution.ts b/src/vs/sessions/contrib/changes/browser/toggleChangesView.ts
similarity index 89%
rename from src/vs/sessions/contrib/sessions/browser/sessionsAuxiliaryBarContribution.ts
rename to src/vs/sessions/contrib/changes/browser/toggleChangesView.ts
index eb36b915ad62d..abc40780aa638 100644
--- a/src/vs/sessions/contrib/sessions/browser/sessionsAuxiliaryBarContribution.ts
+++ b/src/vs/sessions/contrib/changes/browser/toggleChangesView.ts
@@ -14,16 +14,18 @@ import { IChatService } from '../../../../workbench/contrib/chat/common/chatServ
 import { IChatEditingService } from '../../../../workbench/contrib/chat/common/editing/chatEditingService.js';
 import { getChatSessionType } from '../../../../workbench/contrib/chat/common/model/chatUri.js';
 import { IWorkbenchLayoutService, Parts } from '../../../../workbench/services/layout/browser/layoutService.js';
-import { ISessionsManagementService } from './sessionsManagementService.js';
+import { ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
+import { IViewsService } from '../../../../workbench/services/views/common/viewsService.js';
+import { CHANGES_VIEW_ID } from './changesView.js';
 
 interface IPendingTurnState {
 	readonly hadChangesBeforeSend: boolean;
 	readonly submittedAt: number;
 }
 
-export class SessionsAuxiliaryBarContribution extends Disposable {
+export class ToggleChangesViewContribution extends Disposable {
 
-	static readonly ID = 'workbench.contrib.sessionsAuxiliaryBarContribution';
+	static readonly ID = 'workbench.contrib.toggleChangesView';
 
 	private readonly pendingTurnStateByResource = new ResourceMap<IPendingTurnState>();
 
@@ -33,6 +35,7 @@ export class SessionsAuxiliaryBarContribution extends Disposable {
 		@IChatEditingService private readonly chatEditingService: IChatEditingService,
 		@IAgentSessionsService private readonly agentSessionsService: IAgentSessionsService,
 		@IChatService private readonly chatService: IChatService,
+		@IViewsService private readonly viewsService: IViewsService,
 	) {
 		super();
 
@@ -106,12 +109,10 @@ export class SessionsAuxiliaryBarContribution extends Disposable {
 	}
 
 	private syncAuxiliaryBarVisibility(hasChanges: boolean): void {
-		const shouldHideAuxiliaryBar = !hasChanges;
-		const isAuxiliaryBarVisible = this.layoutService.isVisible(Parts.AUXILIARYBAR_PART);
-		if (shouldHideAuxiliaryBar === !isAuxiliaryBarVisible) {
-			return;
+		if (hasChanges) {
+			this.viewsService.openView(CHANGES_VIEW_ID, false);
+		} else {
+			this.layoutService.setPartHidden(true, Parts.AUXILIARYBAR_PART);
 		}
-
-		this.layoutService.setPartHidden(shouldHideAuxiliaryBar, Parts.AUXILIARYBAR_PART);
 	}
 }
diff --git a/extensions/git/extension.webpack.config.js b/src/vs/sessions/contrib/changes/common/changes.ts
similarity index 59%
rename from extensions/git/extension.webpack.config.js
rename to src/vs/sessions/contrib/changes/common/changes.ts
index 34f801e2eca4e..23c69cd418217 100644
--- a/extensions/git/extension.webpack.config.js
+++ b/src/vs/sessions/contrib/changes/common/changes.ts
@@ -2,16 +2,8 @@
  *  Copyright (c) Microsoft Corporation. All rights reserved.
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
-// @ts-check
-import withDefaults from '../shared.webpack.config.mjs';
 
-export default withDefaults({
-	context: import.meta.dirname,
-	entry: {
-		main: './src/main.ts',
-		['askpass-main']: './src/askpass-main.ts',
-		['git-editor-main']: './src/git-editor-main.ts'
-	}
-});
+import { localize } from '../../../../nls.js';
+import { RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
 
-export const StripOutSourceMaps = ['dist/askpass-main.js'];
+export const activeSessionHasChangesContextKey = new RawContextKey<boolean>('activeSessionHasChanges', false, localize('activeSessionHasChanges', "Whether the active session has changes."));
diff --git a/src/vs/sessions/contrib/chat/browser/aiCustomizationWorkspaceService.ts b/src/vs/sessions/contrib/chat/browser/aiCustomizationWorkspaceService.ts
index 32d2236832b09..1f0fd2142adaf 100644
--- a/src/vs/sessions/contrib/chat/browser/aiCustomizationWorkspaceService.ts
+++ b/src/vs/sessions/contrib/chat/browser/aiCustomizationWorkspaceService.ts
@@ -3,39 +3,110 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { derived, IObservable } from '../../../../base/common/observable.js';
+import { derived, IObservable, observableValue, ISettableObservable } from '../../../../base/common/observable.js';
+import { joinPath, relativePath } from '../../../../base/common/resources.js';
 import { URI } from '../../../../base/common/uri.js';
-import { IAICustomizationWorkspaceService, AICustomizationManagementSection } from '../../../../workbench/contrib/chat/common/aiCustomizationWorkspaceService.js';
+import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { IAICustomizationWorkspaceService, AICustomizationManagementSection, IStorageSourceFilter, applyStorageSourceFilter } from '../../../../workbench/contrib/chat/common/aiCustomizationWorkspaceService.js';
+import { IChatPromptSlashCommand, IPromptsService, PromptsStorage } from '../../../../workbench/contrib/chat/common/promptSyntax/service/promptsService.js';
+import { BUILTIN_STORAGE } from '../../chat/common/builtinPromptsStorage.js';
 import { ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { CustomizationCreatorService } from '../../../../workbench/contrib/chat/browser/aiCustomization/customizationCreatorService.js';
 import { PromptsType } from '../../../../workbench/contrib/chat/common/promptSyntax/promptTypes.js';
+import { IPathService } from '../../../../workbench/services/path/common/pathService.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
+import { IFileService } from '../../../../platform/files/common/files.js';
+import { INotificationService, Severity } from '../../../../platform/notification/common/notification.js';
+import { localize } from '../../../../nls.js';
 
 /**
  * Agent Sessions override of IAICustomizationWorkspaceService.
  * Delegates to ISessionsManagementService to provide the active session's
  * worktree/repository as the project root, and supports worktree commit.
+ *
+ * Customization files are always committed to the main repository so they
+ * persist across worktrees. When a worktree is active the file is also
+ * copied into the worktree and committed there so the running session
+ * picks it up immediately.
  */
 export class SessionsAICustomizationWorkspaceService implements IAICustomizationWorkspaceService {
 	declare readonly _serviceBrand: undefined;
 
 	readonly activeProjectRoot: IObservable<URI | undefined>;
+	readonly hasOverrideProjectRoot: IObservable<boolean>;
+
+	/**
+	 * Transient override for the project root. When set, `activeProjectRoot`
+	 * returns this value instead of the session-derived root.
+	 */
+	private readonly _overrideRoot: ISettableObservable<URI | undefined>;
+
+	/**
+	 * CLI-accessible user directories for customization file filtering and creation.
+	 */
+	private readonly _cliUserRoots: readonly URI[];
+
+	/**
+	 * Pre-built filter for types that should only show CLI-accessible user roots.
+	 */
+	private readonly _cliUserFilter: IStorageSourceFilter;
 
 	constructor(
 		@ISessionsManagementService private readonly sessionsService: ISessionsManagementService,
 		@IInstantiationService private readonly instantiationService: IInstantiationService,
+		@IPromptsService private readonly promptsService: IPromptsService,
+		@IPathService pathService: IPathService,
+		@ICommandService private readonly commandService: ICommandService,
+		@ILogService private readonly logService: ILogService,
+		@IFileService private readonly fileService: IFileService,
+		@INotificationService private readonly notificationService: INotificationService,
 	) {
+		const userHome = pathService.userHome({ preferLocal: true });
+		this._cliUserRoots = [
+			joinPath(userHome, '.copilot'),
+			joinPath(userHome, '.claude'),
+			joinPath(userHome, '.agents'),
+		];
+		this._cliUserFilter = {
+			sources: [PromptsStorage.local, PromptsStorage.user, PromptsStorage.plugin, BUILTIN_STORAGE],
+			includedUserFileRoots: this._cliUserRoots,
+		};
+
+		this._overrideRoot = observableValue(this, undefined);
+
 		this.activeProjectRoot = derived(reader => {
+			const override = this._overrideRoot.read(reader);
+			if (override) {
+				return override;
+			}
 			const session = this.sessionsService.activeSession.read(reader);
 			return session?.worktree ?? session?.repository;
 		});
+
+		this.hasOverrideProjectRoot = derived(reader => {
+			return this._overrideRoot.read(reader) !== undefined;
+		});
 	}
 
 	getActiveProjectRoot(): URI | undefined {
+		const override = this._overrideRoot.get();
+		if (override) {
+			return override;
+		}
 		const session = this.sessionsService.getActiveSession();
 		return session?.worktree ?? session?.repository;
 	}
 
+	setOverrideProjectRoot(root: URI): void {
+		this._overrideRoot.set(root, undefined);
+	}
+
+	clearOverrideProjectRoot(): void {
+		this._overrideRoot.set(undefined, undefined);
+	}
+
 	readonly managementSections: readonly AICustomizationManagementSection[] = [
 		AICustomizationManagementSection.Agents,
 		AICustomizationManagementSection.Skills,
@@ -43,15 +114,172 @@ export class SessionsAICustomizationWorkspaceService implements IAICustomization
 		AICustomizationManagementSection.Prompts,
 		AICustomizationManagementSection.Hooks,
 		AICustomizationManagementSection.McpServers,
-		AICustomizationManagementSection.Models,
+		AICustomizationManagementSection.Plugins,
 	];
 
-	readonly preferManualCreation = true;
+	private static readonly _hooksFilter: IStorageSourceFilter = {
+		sources: [PromptsStorage.local, PromptsStorage.plugin],
+	};
+
+	private static readonly _allUserRootsFilter: IStorageSourceFilter = {
+		sources: [PromptsStorage.local, PromptsStorage.user, PromptsStorage.plugin, BUILTIN_STORAGE],
+	};
+
+	getStorageSourceFilter(type: PromptsType): IStorageSourceFilter {
+		if (type === PromptsType.hook) {
+			return SessionsAICustomizationWorkspaceService._hooksFilter;
+		}
+		if (type === PromptsType.prompt) {
+			// Prompts are shown from all user roots (including VS Code profile)
+			return SessionsAICustomizationWorkspaceService._allUserRootsFilter;
+		}
+		// Other types only show user files from CLI-accessible roots (~/.copilot, ~/.claude, ~/.agents)
+		return this._cliUserFilter;
+	}
+
+	readonly isSessionsWindow = true;
+
+	/**
+	 * Commits customization files. Always commits to the main repository
+	 * so the change persists across worktrees. When a worktree is active
+	 * the file is also committed there so the session sees it immediately.
+	 */
+	async commitFiles(_projectRoot: URI, fileUris: URI[]): Promise<void> {
+		const session = this.sessionsService.getActiveSession();
+		if (!session?.repository) {
+			return;
+		}
+
+		for (const fileUri of fileUris) {
+			await this.commitFileToRepos(fileUri, session.repository, session.worktree);
+		}
+	}
 
-	async commitFiles(projectRoot: URI, fileUris: URI[]): Promise<void> {
+	/**
+	 * Commits the deletion of files that have already been removed from disk.
+	 * Always stages + commits the removal in the main repository, and also
+	 * in the worktree if one is active.
+	 */
+	async deleteFiles(_projectRoot: URI, fileUris: URI[]): Promise<void> {
 		const session = this.sessionsService.getActiveSession();
-		if (session) {
-			await this.sessionsService.commitWorktreeFiles(session, fileUris);
+		if (!session?.repository) {
+			return;
+		}
+
+		for (const fileUri of fileUris) {
+			await this.commitDeletionToRepos(fileUri, session.repository, session.worktree);
+		}
+	}
+
+	/**
+	 * Computes the repository-relative path for a file. The file may be
+	 * located under the worktree or the repository root.
+	 */
+	private getRelativePath(fileUri: URI, repositoryUri: URI, worktreeUri: URI | undefined): string | undefined {
+		// Try worktree first (when active, files are written under it)
+		if (worktreeUri) {
+			const rel = relativePath(worktreeUri, fileUri);
+			if (rel) {
+				return rel;
+			}
+		}
+		return relativePath(repositoryUri, fileUri);
+	}
+
+	/**
+	 * Commits a single file to the main repository and optionally the worktree.
+	 * Copies the file content between trees when needed.
+	 */
+	private async commitFileToRepos(fileUri: URI, repositoryUri: URI, worktreeUri: URI | undefined): Promise<void> {
+		const relPath = this.getRelativePath(fileUri, repositoryUri, worktreeUri);
+		if (!relPath) {
+			return;
+		}
+
+		const repoFileUri = URI.joinPath(repositoryUri, relPath);
+
+		// 1. Always commit to main repository
+		try {
+			if (repoFileUri.toString() !== fileUri.toString()) {
+				const content = await this.fileService.readFile(fileUri);
+				await this.fileService.writeFile(repoFileUri, content.value);
+			}
+			await this.commandService.executeCommand(
+				'github.copilot.cli.sessions.commitToRepository',
+				{ repositoryUri, fileUri: repoFileUri }
+			);
+		} catch (error) {
+			this.logService.error('[SessionsAICustomizationWorkspaceService] Failed to commit to repository:', error);
+			if (worktreeUri) {
+				this.notificationService.notify({
+					severity: Severity.Warning,
+					message: localize('commitToRepoFailed', "Your customization was saved to this session's worktree, but we couldn't apply it to the default branch. You may need to apply it manually."),
+				});
+			}
+		}
+
+		// 2. Also commit to the worktree if active
+		if (worktreeUri) {
+			const worktreeFileUri = URI.joinPath(worktreeUri, relPath);
+			try {
+				if (worktreeFileUri.toString() !== fileUri.toString()) {
+					const content = await this.fileService.readFile(fileUri);
+					await this.fileService.writeFile(worktreeFileUri, content.value);
+				}
+				await this.commandService.executeCommand(
+					'github.copilot.cli.sessions.commitToWorktree',
+					{ worktreeUri, fileUri: worktreeFileUri }
+				);
+			} catch (error) {
+				this.logService.error('[SessionsAICustomizationWorkspaceService] Failed to commit to worktree:', error);
+			}
+		}
+	}
+
+	/**
+	 * Commits the deletion of a file to the main repository and optionally
+	 * the worktree. The file is already deleted from disk before this is called;
+	 * `git add` on a deleted path stages the removal.
+	 */
+	private async commitDeletionToRepos(fileUri: URI, repositoryUri: URI, worktreeUri: URI | undefined): Promise<void> {
+		const relPath = this.getRelativePath(fileUri, repositoryUri, worktreeUri);
+		if (!relPath) {
+			return;
+		}
+
+		const repoFileUri = URI.joinPath(repositoryUri, relPath);
+
+		// 1. Delete from main repository if it exists there, then commit
+		try {
+			if (await this.fileService.exists(repoFileUri)) {
+				await this.fileService.del(repoFileUri, { useTrash: true, recursive: true });
+			}
+			await this.commandService.executeCommand(
+				'github.copilot.cli.sessions.commitToRepository',
+				{ repositoryUri, fileUri: repoFileUri }
+			);
+		} catch (error) {
+			this.logService.error('[SessionsAICustomizationWorkspaceService] Failed to commit deletion to repository:', error);
+			if (worktreeUri) {
+				this.notificationService.notify({
+					severity: Severity.Warning,
+					message: localize('deleteFromRepoFailed', "Your customization was removed from this session's worktree, but we couldn't apply the change to the default branch. You may need to remove it manually."),
+				});
+			}
+		}
+
+		// 2. Also commit the deletion in the worktree if active
+		if (worktreeUri) {
+			const worktreeFileUri = URI.joinPath(worktreeUri, relPath);
+			try {
+				// The file may already be deleted from the worktree by the caller
+				await this.commandService.executeCommand(
+					'github.copilot.cli.sessions.commitToWorktree',
+					{ worktreeUri, fileUri: worktreeFileUri }
+				);
+			} catch (error) {
+				this.logService.error('[SessionsAICustomizationWorkspaceService] Failed to commit deletion to worktree:', error);
+			}
 		}
 	}
 
@@ -59,4 +287,12 @@ export class SessionsAICustomizationWorkspaceService implements IAICustomization
 		const creator = this.instantiationService.createInstance(CustomizationCreatorService);
 		await creator.createWithAI(type);
 	}
+
+	async getFilteredPromptSlashCommands(token: CancellationToken): Promise<readonly IChatPromptSlashCommand[]> {
+		const allCommands = await this.promptsService.getPromptSlashCommands(token);
+		return allCommands.filter(cmd => {
+			const filter = this.getStorageSourceFilter(cmd.promptPath.type);
+			return applyStorageSourceFilter([cmd.promptPath], filter).length > 0;
+		});
+	}
 }
diff --git a/src/vs/sessions/contrib/chat/browser/branchPicker.ts b/src/vs/sessions/contrib/chat/browser/branchPicker.ts
index 7744e54a3dacf..0e4ff4ce967ce 100644
--- a/src/vs/sessions/contrib/chat/browser/branchPicker.ts
+++ b/src/vs/sessions/contrib/chat/browser/branchPicker.ts
@@ -12,8 +12,6 @@ import { IActionWidgetService } from '../../../../platform/actionWidget/browser/
 import { ActionListItemKind, IActionListDelegate, IActionListItem } from '../../../../platform/actionWidget/browser/actionList.js';
 import { IGitRepository } from '../../../../workbench/contrib/git/common/gitService.js';
 import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
-import { INewSession } from './newSession.js';
-
 const COPILOT_WORKTREE_PATTERN = 'copilot-worktree-';
 const FILTER_THRESHOLD = 10;
 
@@ -31,7 +29,7 @@ interface IBranchItem {
 export class BranchPicker extends Disposable {
 
 	private _selectedBranch: string | undefined;
-	private _newSession: INewSession | undefined;
+	private _preferredBranch: string | undefined;
 	private _branches: string[] = [];
 
 	private readonly _onDidChange = this._register(new Emitter<string | undefined>());
@@ -48,19 +46,19 @@ export class BranchPicker extends Disposable {
 		return this._selectedBranch;
 	}
 
+	/**
+	 * Sets a preferred branch to select when branches are loaded.
+	 */
+	setPreferredBranch(branch: string | undefined): void {
+		this._preferredBranch = branch;
+	}
+
 	constructor(
 		@IActionWidgetService private readonly actionWidgetService: IActionWidgetService,
 	) {
 		super();
 	}
 
-	/**
-	 * Sets the new session that this picker writes to.
-	 */
-	setNewSession(session: INewSession | undefined): void {
-		this._newSession = session;
-	}
-
 	/**
 	 * Sets the git repository and loads its branches.
 	 * When undefined, the picker is shown disabled.
@@ -70,7 +68,7 @@ export class BranchPicker extends Disposable {
 		this._selectedBranch = undefined;
 
 		if (!repository) {
-			this._newSession?.setBranch(undefined);
+			this._onDidChange.fire(undefined);
 			this._setLoading(false);
 			this._updateTriggerLabel();
 			return;
@@ -85,8 +83,11 @@ export class BranchPicker extends Disposable {
 				.filter((name): name is string => !!name)
 				.filter(name => !name.includes(COPILOT_WORKTREE_PATTERN));
 
-			// Select active branch, main, master, or the first branch by default
-			const defaultBranch = this._branches.find(b => b === repository.state.get().HEAD?.name)
+			// Select preferred branch (from draft), active branch, main, master, or the first branch
+			const preferred = this._preferredBranch;
+			this._preferredBranch = undefined;
+			const defaultBranch = (preferred ? this._branches.find(b => b === preferred) : undefined)
+				?? this._branches.find(b => b === repository.state.get().HEAD?.name)
 				?? this._branches.find(b => b === 'main')
 				?? this._branches.find(b => b === 'master')
 				?? this._branches[0];
@@ -177,7 +178,7 @@ export class BranchPicker extends Disposable {
 		return this._branches.map(branch => ({
 			kind: ActionListItemKind.Action,
 			label: branch,
-			group: { title: '', icon: this._selectedBranch === branch ? Codicon.check : Codicon.blank },
+			group: { title: '', icon: Codicon.gitBranch },
 			item: { name: branch },
 		}));
 	}
@@ -185,7 +186,6 @@ export class BranchPicker extends Disposable {
 	private _selectBranch(branch: string): void {
 		if (this._selectedBranch !== branch) {
 			this._selectedBranch = branch;
-			this._newSession?.setBranch(branch);
 			this._onDidChange.fire(branch);
 			this._updateTriggerLabel();
 		}
diff --git a/src/vs/sessions/contrib/chat/browser/chat.contribution.ts b/src/vs/sessions/contrib/chat/browser/chat.contribution.ts
index b7879423464a0..5e49081cc2bf9 100644
--- a/src/vs/sessions/contrib/chat/browser/chat.contribution.ts
+++ b/src/vs/sessions/contrib/chat/browser/chat.contribution.ts
@@ -17,8 +17,7 @@ import { IViewContainersRegistry, IViewsRegistry, ViewContainerLocation, Extensi
 import { Registry } from '../../../../platform/registry/common/platform.js';
 import { SyncDescriptor } from '../../../../platform/instantiation/common/descriptors.js';
 import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
-import { isAgentSession } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsModel.js';
-import { ISessionsManagementService, IsNewChatSessionContext } from '../../sessions/browser/sessionsManagementService.js';
+import { IsActiveSessionBackgroundProviderContext, ISessionsManagementService, IsNewChatSessionContext } from '../../sessions/browser/sessionsManagementService.js';
 import { Menus } from '../../../browser/menus.js';
 import { BranchChatSessionAction } from './branchChatSessionAction.js';
 import { RunScriptContribution } from './runScriptAction.js';
@@ -37,6 +36,8 @@ import { ViewPaneContainer } from '../../../../workbench/browser/parts/views/vie
 import { registerIcon } from '../../../../platform/theme/common/iconRegistry.js';
 import { ChatViewPane } from '../../../../workbench/contrib/chat/browser/widgetHosts/viewPane/chatViewPane.js';
 import { IsAuxiliaryWindowContext } from '../../../../workbench/common/contextkeys.js';
+import { ContextKeyExpr } from '../../../../platform/contextkey/common/contextkey.js';
+import { SessionsWelcomeVisibleContext } from '../../../common/contextkeys.js';
 
 export class OpenSessionWorktreeInVSCodeAction extends Action2 {
 	static readonly ID = 'chat.openSessionWorktreeInVSCode';
@@ -46,11 +47,12 @@ export class OpenSessionWorktreeInVSCodeAction extends Action2 {
 			id: OpenSessionWorktreeInVSCodeAction.ID,
 			title: localize2('openInVSCode', 'Open in VS Code'),
 			icon: Codicon.vscodeInsiders,
+			precondition: IsActiveSessionBackgroundProviderContext,
 			menu: [{
-				id: Menus.TitleBarRight,
+				id: Menus.TitleBarSessionMenu,
 				group: 'navigation',
 				order: 10,
-				when: IsAuxiliaryWindowContext.toNegated()
+				when: ContextKeyExpr.and(IsAuxiliaryWindowContext.toNegated(), SessionsWelcomeVisibleContext.toNegated(), IsActiveSessionBackgroundProviderContext),
 			}]
 		});
 	}
@@ -65,7 +67,7 @@ export class OpenSessionWorktreeInVSCodeAction extends Action2 {
 			return;
 		}
 
-		const folderUri = isAgentSession(activeSession) && activeSession.providerType !== AgentSessionProviders.Cloud ? activeSession.worktree : undefined;
+		const folderUri = activeSession.providerType === AgentSessionProviders.Background ? activeSession?.worktree ?? activeSession?.repository : undefined;
 
 		if (!folderUri) {
 			return;
@@ -137,11 +139,11 @@ class RegisterChatViewContainerContribution implements IWorkbenchContribution {
 		const viewsRegistry = Registry.as<IViewsRegistry>(ViewExtensions.ViewsRegistry);
 		let chatViewContainer = viewContainerRegistry.get(ChatViewContainerId);
 		if (chatViewContainer) {
-			viewContainerRegistry.deregisterViewContainer(chatViewContainer);
 			const view = viewsRegistry.getView(ChatViewId);
 			if (view) {
 				viewsRegistry.deregisterViews([view], chatViewContainer);
 			}
+			viewContainerRegistry.deregisterViewContainer(chatViewContainer);
 		}
 
 		chatViewContainer = viewContainerRegistry.registerViewContainer({
diff --git a/src/vs/sessions/contrib/chat/browser/customizationsDebugLog.contribution.ts b/src/vs/sessions/contrib/chat/browser/customizationsDebugLog.contribution.ts
new file mode 100644
index 0000000000000..fcda250ebc96c
--- /dev/null
+++ b/src/vs/sessions/contrib/chat/browser/customizationsDebugLog.contribution.ts
@@ -0,0 +1,179 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { autorun } from '../../../../base/common/observable.js';
+import { ILogger, ILoggerService } from '../../../../platform/log/common/log.js';
+import { IWorkspaceContextService } from '../../../../platform/workspace/common/workspace.js';
+import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../../workbench/common/contributions.js';
+import { IAICustomizationWorkspaceService, applyStorageSourceFilter, IStorageSourceFilter } from '../../../../workbench/contrib/chat/common/aiCustomizationWorkspaceService.js';
+import { IPromptsService, PromptsStorage, IPromptPath } from '../../../../workbench/contrib/chat/common/promptSyntax/service/promptsService.js';
+import { PromptsType } from '../../../../workbench/contrib/chat/common/promptSyntax/promptTypes.js';
+import { AICustomizationManagementSection } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.js';
+import { IMcpService } from '../../../../workbench/contrib/mcp/common/mcpTypes.js';
+
+const PROMPT_SECTIONS: { section: AICustomizationManagementSection; type: PromptsType }[] = [
+	{ section: AICustomizationManagementSection.Agents, type: PromptsType.agent },
+	{ section: AICustomizationManagementSection.Skills, type: PromptsType.skill },
+	{ section: AICustomizationManagementSection.Instructions, type: PromptsType.instructions },
+	{ section: AICustomizationManagementSection.Prompts, type: PromptsType.prompt },
+	{ section: AICustomizationManagementSection.Hooks, type: PromptsType.hook },
+];
+
+class CustomizationsDebugLogContribution extends Disposable implements IWorkbenchContribution {
+
+	static readonly ID = 'sessions.customizationsDebugLog';
+
+	private readonly _logger: ILogger;
+
+	constructor(
+		@ILoggerService loggerService: ILoggerService,
+		@IPromptsService private readonly _promptsService: IPromptsService,
+		@IAICustomizationWorkspaceService private readonly _workspaceService: IAICustomizationWorkspaceService,
+		@IWorkspaceContextService private readonly _workspaceContextService: IWorkspaceContextService,
+		@IMcpService private readonly _mcpService: IMcpService,
+	) {
+		super();
+		this._logger = this._register(loggerService.createLogger('customizationsDebug', { name: 'Customizations Debug' }));
+
+		this._register(this._promptsService.onDidChangeCustomAgents(() => this._logSnapshot()));
+		this._register(this._promptsService.onDidChangeSlashCommands(() => this._logSnapshot()));
+		this._register(this._workspaceContextService.onDidChangeWorkspaceFolders(() => this._logSnapshot()));
+		this._register(autorun(reader => {
+			this._workspaceService.activeProjectRoot.read(reader);
+			this._logSnapshot();
+		}));
+		this._register(autorun(reader => {
+			this._mcpService.servers.read(reader);
+			this._logSnapshot();
+		}));
+	}
+
+	private _pendingSnapshot: Promise<void> | undefined;
+	private _snapshotDirty = false;
+
+	private _logSnapshot(): void {
+		if (this._pendingSnapshot) {
+			this._snapshotDirty = true;
+			return;
+		}
+		this._pendingSnapshot = this._doLogSnapshot().finally(() => {
+			this._pendingSnapshot = undefined;
+			if (this._snapshotDirty) {
+				this._snapshotDirty = false;
+				this._logSnapshot();
+			}
+		});
+	}
+
+	private async _doLogSnapshot(): Promise<void> {
+		const root = this._workspaceService.getActiveProjectRoot()?.fsPath ?? '(none)';
+
+		this._logger.info('');
+		this._logger.info('=== Customizations Snapshot ===');
+		this._logger.info(`  Root: ${root}`);
+		this._logger.info(`  Sections: ${this._workspaceService.managementSections.join(', ')}`);
+		this._logger.info('');
+
+		// Header
+		this._logger.info(`  ${'Section'.padEnd(16)} ${'Local'.padStart(6)} ${'User'.padStart(6)} ${'Ext'.padStart(6)} ${'Total'.padStart(7)}`);
+		this._logger.info(`  ${'--------'.padEnd(16)} ${'-----'.padStart(6)} ${'----'.padStart(6)} ${'---'.padStart(6)} ${'-----'.padStart(7)}`);
+
+		for (const { section, type } of PROMPT_SECTIONS) {
+			const filter = this._workspaceService.getStorageSourceFilter(type);
+			await this._logSectionRow(section, type, filter);
+		}
+
+		this._logger.info('');
+
+		// Details per section
+		for (const { section, type } of PROMPT_SECTIONS) {
+			const filter = this._workspaceService.getStorageSourceFilter(type);
+			await this._logSectionDetails(section, type, filter);
+		}
+
+		// MCP Servers
+		this._logMcpServers();
+	}
+
+	private _logMcpServers(): void {
+		const servers = this._mcpService.servers.get();
+		this._logger.info(`  -- MCP Servers (${servers.length}) --`);
+		if (servers.length === 0) {
+			this._logger.info('     (none registered)');
+		}
+		for (const server of servers) {
+			const state = server.connectionState.get();
+			const stateStr = state?.state ?? 'unknown';
+			this._logger.info(`     ${server.definition.label} [${stateStr}] id=${server.definition.id}`);
+		}
+		this._logger.info('');
+	}
+
+	private async _logSectionRow(section: AICustomizationManagementSection, type: PromptsType, filter: IStorageSourceFilter): Promise<void> {
+		try {
+			const [localFiles, userFiles, extensionFiles] = await Promise.all([
+				this._promptsService.listPromptFilesForStorage(type, PromptsStorage.local, CancellationToken.None),
+				this._promptsService.listPromptFilesForStorage(type, PromptsStorage.user, CancellationToken.None),
+				this._promptsService.listPromptFilesForStorage(type, PromptsStorage.extension, CancellationToken.None),
+			]);
+			const all: IPromptPath[] = [...localFiles, ...userFiles, ...extensionFiles];
+			const filtered = applyStorageSourceFilter(all, filter);
+			const local = filtered.filter(f => f.storage === PromptsStorage.local).length;
+			const user = filtered.filter(f => f.storage === PromptsStorage.user).length;
+			const ext = filtered.filter(f => f.storage === PromptsStorage.extension).length;
+
+			this._logger.info(`  ${section.padEnd(16)} ${String(local).padStart(6)} ${String(user).padStart(6)} ${String(ext).padStart(6)} ${String(filtered.length).padStart(7)}`);
+		} catch {
+			this._logger.info(`  ${section.padEnd(16)}  (error)`);
+		}
+	}
+
+	private async _logSectionDetails(section: AICustomizationManagementSection, type: PromptsType, filter: IStorageSourceFilter): Promise<void> {
+		try {
+			// Source folders - where we look for files
+			const sourceFolders = await this._promptsService.getSourceFolders(type);
+			if (sourceFolders.length > 0) {
+				this._logger.info(`  -- ${section} --`);
+				this._logger.info(`     Search paths:`);
+				for (const sf of sourceFolders) {
+					this._logger.info(`       [${sf.storage}] ${sf.uri.fsPath}`);
+				}
+			}
+
+			const [localFiles, userFiles, extensionFiles] = await Promise.all([
+				this._promptsService.listPromptFilesForStorage(type, PromptsStorage.local, CancellationToken.None),
+				this._promptsService.listPromptFilesForStorage(type, PromptsStorage.user, CancellationToken.None),
+				this._promptsService.listPromptFilesForStorage(type, PromptsStorage.extension, CancellationToken.None),
+			]);
+			const all: IPromptPath[] = [...localFiles, ...userFiles, ...extensionFiles];
+			const filtered = applyStorageSourceFilter(all, filter);
+
+			if (filtered.length > 0) {
+				if (sourceFolders.length === 0) {
+					this._logger.info(`  -- ${section} --`);
+				}
+				this._logger.info(`     Filter: sources=[${filter.sources.join(', ')}]${filter.includedUserFileRoots ? `, roots=[${filter.includedUserFileRoots.map(r => r.fsPath).join(', ')}]` : ''}`);
+				this._logger.info(`     Found ${filtered.length} item(s):`);
+				for (const f of filtered) {
+					this._logger.info(`       [${f.storage}] ${f.uri.fsPath}`);
+				}
+			}
+
+			if (sourceFolders.length > 0 || filtered.length > 0) {
+				this._logger.info('');
+			}
+		} catch {
+			// already logged in row
+		}
+	}
+}
+
+registerWorkbenchContribution2(
+	CustomizationsDebugLogContribution.ID,
+	CustomizationsDebugLogContribution,
+	WorkbenchPhase.AfterRestored,
+);
diff --git a/src/vs/sessions/contrib/chat/browser/folderPicker.ts b/src/vs/sessions/contrib/chat/browser/folderPicker.ts
index 1080d93df7dce..26d7626d54698 100644
--- a/src/vs/sessions/contrib/chat/browser/folderPicker.ts
+++ b/src/vs/sessions/contrib/chat/browser/folderPicker.ts
@@ -7,19 +7,15 @@ import * as dom from '../../../../base/browser/dom.js';
 import { Codicon } from '../../../../base/common/codicons.js';
 import { Emitter, Event } from '../../../../base/common/event.js';
 import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
-import { basename, isEqual } from '../../../../base/common/resources.js';
+import { basename, extUriBiasedIgnorePathCase, isEqual } from '../../../../base/common/resources.js';
 import { URI } from '../../../../base/common/uri.js';
 import { localize } from '../../../../nls.js';
 import { IActionWidgetService } from '../../../../platform/actionWidget/browser/actionWidget.js';
 import { ActionListItemKind, IActionListDelegate, IActionListItem } from '../../../../platform/actionWidget/browser/actionList.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
 import { IFileDialogService } from '../../../../platform/dialogs/common/dialogs.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
-import { IWorkspaceContextService } from '../../../../platform/workspace/common/workspace.js';
-import { IWorkspacesService, isRecentFolder } from '../../../../platform/workspaces/common/workspaces.js';
 import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
-import { INewSession } from './newSession.js';
-import { toAction } from '../../../../base/common/actions.js';
-import { ThemeIcon } from '../../../../base/common/themables.js';
 
 const STORAGE_KEY_LAST_FOLDER = 'agentSessions.lastPickedFolder';
 const STORAGE_KEY_RECENT_FOLDERS = 'agentSessions.recentlyPickedFolders';
@@ -29,6 +25,7 @@ const FILTER_THRESHOLD = 10;
 interface IFolderItem {
 	readonly uri: URI;
 	readonly label: string;
+	readonly checked?: boolean;
 }
 
 /**
@@ -44,8 +41,6 @@ export class FolderPicker extends Disposable {
 
 	private _selectedFolderUri: URI | undefined;
 	private _recentlyPickedFolders: URI[] = [];
-	private _cachedRecentFolders: { uri: URI; label?: string }[] = [];
-	private _newSession: INewSession | undefined;
 
 	private _triggerElement: HTMLElement | undefined;
 	private readonly _renderDisposables = this._register(new DisposableStore());
@@ -54,20 +49,11 @@ export class FolderPicker extends Disposable {
 		return this._selectedFolderUri;
 	}
 
-	/**
-	 * Sets the pending session that this picker writes to.
-	 * When the user selects a folder, it calls `setRepoUri` on the session.
-	 */
-	setNewSession(session: INewSession | undefined): void {
-		this._newSession = session;
-	}
-
 	constructor(
 		@IActionWidgetService private readonly actionWidgetService: IActionWidgetService,
 		@IStorageService private readonly storageService: IStorageService,
-		@IWorkspaceContextService private readonly workspaceContextService: IWorkspaceContextService,
-		@IWorkspacesService private readonly workspacesService: IWorkspacesService,
 		@IFileDialogService private readonly fileDialogService: IFileDialogService,
+		@ICommandService private readonly commandService: ICommandService,
 	) {
 		super();
 
@@ -84,15 +70,6 @@ export class FolderPicker extends Disposable {
 				this._recentlyPickedFolders = JSON.parse(stored).map((s: string) => URI.parse(s));
 			}
 		} catch { /* ignore */ }
-
-		// Pre-fetch recently opened folders, filtering out copilot worktrees
-		this.workspacesService.getRecentlyOpened().then(recent => {
-			this._cachedRecentFolders = recent.workspaces
-				.filter(isRecentFolder)
-				.filter(r => !this._isCopilotWorktree(r.folderUri))
-				.slice(0, MAX_RECENT_FOLDERS)
-				.map(r => ({ uri: r.folderUri, label: r.label }));
-		}).catch(() => { /* ignore */ });
 	}
 
 	/**
@@ -135,7 +112,7 @@ export class FolderPicker extends Disposable {
 			return;
 		}
 
-		const currentFolderUri = this._selectedFolderUri ?? this.workspaceContextService.getWorkspace().folders[0]?.uri;
+		const currentFolderUri = this._selectedFolderUri;
 		const items = this._buildItems(currentFolderUri);
 		const showFilter = items.filter(i => i.kind === ActionListItemKind.Action).length > FILTER_THRESHOLD;
 
@@ -145,6 +122,8 @@ export class FolderPicker extends Disposable {
 				this.actionWidgetService.hide();
 				if (item.uri.scheme === 'command' && item.uri.path === 'browse') {
 					this._browseForFolder();
+				} else if (item.uri.scheme === 'command' && item.uri.path === 'clone') {
+					this._cloneRepository();
 				} else {
 					this._selectFolder(item.uri);
 				}
@@ -152,6 +131,8 @@ export class FolderPicker extends Disposable {
 			onHide: () => { triggerElement.focus(); },
 		};
 
+		const listOptions = showFilter ? { showFilter: true, filterPlaceholder: localize('folderPicker.filter', "Filter folders...") } : undefined;
+
 		this.actionWidgetService.show<IFolderItem>(
 			'folderPicker',
 			false,
@@ -164,12 +145,12 @@ export class FolderPicker extends Disposable {
 				getAriaLabel: (item) => item.label ?? '',
 				getWidgetAriaLabel: () => localize('folderPicker.ariaLabel', "Folder Picker"),
 			},
-			showFilter ? { showFilter: true, filterPlaceholder: localize('folderPicker.filter', "Filter folders...") } : undefined,
+			listOptions,
 		);
 	}
 
 	/**
-	 * Programmatically set the selected folder.
+	 * Programmatically set the selected folder (e.g. restoring draft state).
 	 */
 	setSelectedFolder(folderUri: URI): void {
 		this._selectFolder(folderUri);
@@ -188,7 +169,6 @@ export class FolderPicker extends Disposable {
 		this._addToRecentlyPickedFolders(folderUri);
 		this.storageService.store(STORAGE_KEY_LAST_FOLDER, folderUri.toString(), StorageScope.PROFILE, StorageTarget.MACHINE);
 		this._updateTriggerLabel(this._triggerElement);
-		this._newSession?.setRepoUri(folderUri);
 		this._onDidSelectFolder.fire(folderUri);
 	}
 
@@ -208,6 +188,17 @@ export class FolderPicker extends Disposable {
 		}
 	}
 
+	private async _cloneRepository(): Promise<void> {
+		try {
+			const clonedPath: string | undefined = await this.commandService.executeCommand('git.clone', undefined, undefined, { postCloneAction: 'none' });
+			if (clonedPath) {
+				this._selectFolder(URI.file(clonedPath));
+			}
+		} catch {
+			// clone was cancelled or failed — nothing to do
+		}
+	}
+
 	private _addToRecentlyPickedFolders(folderUri: URI): void {
 		this._recentlyPickedFolders = [folderUri, ...this._recentlyPickedFolders.filter(f => !isEqual(f, folderUri))].slice(0, MAX_RECENT_FOLDERS);
 		this.storageService.store(STORAGE_KEY_RECENT_FOLDERS, JSON.stringify(this._recentlyPickedFolders.map(f => f.toString())), StorageScope.PROFILE, StorageTarget.MACHINE);
@@ -215,45 +206,32 @@ export class FolderPicker extends Disposable {
 
 	private _buildItems(currentFolderUri: URI | undefined): IActionListItem<IFolderItem>[] {
 		const seenUris = new Set<string>();
-		if (currentFolderUri) {
-			seenUris.add(currentFolderUri.toString());
-		}
 
 		const items: IActionListItem<IFolderItem>[] = [];
 
-		// Currently selected folder (shown first, checked)
+		// Collect all folders (current + recently picked), deduplicated and sorted by name
+		const allFolders: { uri: URI; label: string }[] = [];
 		if (currentFolderUri) {
-			items.push({
-				kind: ActionListItemKind.Action,
-				label: basename(currentFolderUri),
-				group: { title: '', icon: Codicon.check },
-				item: { uri: currentFolderUri, label: basename(currentFolderUri) },
-			});
+			seenUris.add(currentFolderUri.toString());
+			allFolders.push({ uri: currentFolderUri, label: basename(currentFolderUri) });
 		}
-
-		// Combine recently picked folders and recently opened folders
-		const allFolders: { uri: URI; label?: string }[] = [
-			...this._recentlyPickedFolders.map(uri => ({ uri })),
-			...this._cachedRecentFolders,
-		];
-		for (const folder of allFolders) {
-			const key = folder.uri.toString();
+		for (const folderUri of this._recentlyPickedFolders) {
+			const key = folderUri.toString();
 			if (seenUris.has(key)) {
 				continue;
 			}
 			seenUris.add(key);
-			const label = folder.label || basename(folder.uri);
+			allFolders.push({ uri: folderUri, label: basename(folderUri) });
+		}
+		allFolders.sort((a, b) => extUriBiasedIgnorePathCase.compare(a.uri, b.uri));
+		for (const folder of allFolders) {
+			const isCurrent = currentFolderUri && isEqual(folder.uri, currentFolderUri);
 			items.push({
 				kind: ActionListItemKind.Action,
-				label,
-				group: { title: '', icon: Codicon.blank },
-				item: { uri: folder.uri, label },
-				toolbarActions: [toAction({
-					id: 'folderPicker.remove',
-					label: localize('folderPicker.remove', "Remove"),
-					class: ThemeIcon.asClassName(Codicon.close),
-					run: () => this._removeFolder(folder.uri),
-				})],
+				label: folder.label,
+				group: { title: '', icon: Codicon.folder },
+				item: { uri: folder.uri, label: folder.label, checked: isCurrent || false },
+				...(!isCurrent ? { onRemove: () => this._removeFolder(folder.uri) } : {}),
 			});
 		}
 
@@ -267,32 +245,36 @@ export class FolderPicker extends Disposable {
 		items.push({
 			kind: ActionListItemKind.Action,
 			label: localize('browseFolder', "Browse..."),
-			group: { title: '', icon: Codicon.folderOpened },
+			group: { title: '', icon: Codicon.search },
 			item: { uri: URI.from({ scheme: 'command', path: 'browse' }), label: localize('browseFolder', "Browse...") },
 		});
+		items.push({
+			kind: ActionListItemKind.Action,
+			label: localize('cloneRepository', "Clone..."),
+			group: { title: '', icon: Codicon.repoClone },
+			item: { uri: URI.from({ scheme: 'command', path: 'clone' }), label: localize('cloneRepository', "Clone...") },
+		});
 
 		return items;
 	}
 
-	private _removeFolder(folderUri: URI): void {
-		// Remove from recently picked folders
+	/**
+	 * Removes a folder from the recently picked list and storage.
+	 */
+	removeFromRecents(folderUri: URI): void {
 		this._recentlyPickedFolders = this._recentlyPickedFolders.filter(f => !isEqual(f, folderUri));
 		this.storageService.store(STORAGE_KEY_RECENT_FOLDERS, JSON.stringify(this._recentlyPickedFolders.map(f => f.toString())), StorageScope.PROFILE, StorageTarget.MACHINE);
-
-		// Remove from cached recent folders
-		this._cachedRecentFolders = this._cachedRecentFolders.filter(f => !isEqual(f.uri, folderUri));
-
-		// Remove from globally recently opened
-		this.workspacesService.removeRecentlyOpened([folderUri]);
-
-		// Re-show the picker with updated items
-		this.actionWidgetService.hide();
-		this.showPicker();
+		// If this was the last picked folder, clear it
+		if (this._selectedFolderUri && isEqual(this._selectedFolderUri, folderUri)) {
+			this._selectedFolderUri = undefined;
+			this.storageService.remove(STORAGE_KEY_LAST_FOLDER, StorageScope.PROFILE);
+			this._updateTriggerLabel(this._triggerElement);
+		}
 	}
 
-	private _isCopilotWorktree(uri: URI): boolean {
-		const name = basename(uri);
-		return name.startsWith('copilot-worktree-');
+	private _removeFolder(folderUri: URI): void {
+		this._recentlyPickedFolders = this._recentlyPickedFolders.filter(f => !isEqual(f, folderUri));
+		this.storageService.store(STORAGE_KEY_RECENT_FOLDERS, JSON.stringify(this._recentlyPickedFolders.map(f => f.toString())), StorageScope.PROFILE, StorageTarget.MACHINE);
 	}
 
 	private _updateTriggerLabel(trigger: HTMLElement | undefined): void {
@@ -301,7 +283,7 @@ export class FolderPicker extends Disposable {
 		}
 
 		dom.clearNode(trigger);
-		const folderUri = this._selectedFolderUri ?? this.workspaceContextService.getWorkspace().folders[0]?.uri;
+		const folderUri = this._selectedFolderUri;
 		const label = folderUri ? basename(folderUri) : localize('pickFolder', "Pick Folder");
 
 		dom.append(trigger, renderIcon(Codicon.folder));
diff --git a/src/vs/sessions/contrib/chat/browser/media/chatWelcomePart.css b/src/vs/sessions/contrib/chat/browser/media/chatWelcomePart.css
index 89375629adb1a..16e1ab73d4742 100644
--- a/src/vs/sessions/contrib/chat/browser/media/chatWelcomePart.css
+++ b/src/vs/sessions/contrib/chat/browser/media/chatWelcomePart.css
@@ -12,7 +12,7 @@
 	height: 100%;
 	box-sizing: border-box;
 	overflow: hidden;
-	padding-bottom: 10%;
+	padding: 0 12px 48px 12px;
 	container-type: size;
 }
 
@@ -35,7 +35,7 @@
 	width: 100%;
 	max-width: 200px;
 	aspect-ratio: 1/1;
-	background-image: url('../../../../../workbench/browser/parts/editor/media/letterpress-dark.svg');
+	background-image: url('./letterpress-sessions-dark.svg');
 	background-size: contain;
 	background-position: center;
 	background-repeat: no-repeat;
@@ -43,16 +43,9 @@
 	margin-bottom: 20px;
 }
 
-.vs .chat-full-welcome-letterpress {
-	background-image: url('../../../../../workbench/browser/parts/editor/media/letterpress-light.svg');
-}
-
+.vs .chat-full-welcome-letterpress,
 .hc-light .chat-full-welcome-letterpress {
-	background-image: url('../../../../../workbench/browser/parts/editor/media/letterpress-hcLight.svg');
-}
-
-.hc-black .chat-full-welcome-letterpress {
-	background-image: url('../../../../../workbench/browser/parts/editor/media/letterpress-hcDark.svg');
+	background-image: url('./letterpress-sessions-light.svg');
 }
 
 @container (max-height: 350px) {
@@ -116,6 +109,7 @@
 	display: none;
 	flex-direction: row;
 	align-items: center;
+	gap: 4px;
 	min-height: 28px;
 }
 
@@ -361,3 +355,12 @@
 .sessions-chat-picker-slot .action-label span + .chat-session-option-label {
 	margin-left: 2px;
 }
+
+/* Sync indicator: a slim non-interactive-looking separator before the button */
+.sessions-chat-sync-indicator {
+	margin-left: 4px;
+}
+
+.sessions-chat-sync-indicator .action-label .sessions-chat-dropdown-label {
+	margin-left: 3px;
+}
diff --git a/src/vs/sessions/contrib/chat/browser/media/chatWidget.css b/src/vs/sessions/contrib/chat/browser/media/chatWidget.css
index 4fca1a7a5018a..b9e7bbe6a02d4 100644
--- a/src/vs/sessions/contrib/chat/browser/media/chatWidget.css
+++ b/src/vs/sessions/contrib/chat/browser/media/chatWidget.css
@@ -8,6 +8,7 @@
 	flex-direction: column;
 	height: 100%;
 	width: 100%;
+	position: relative;
 }
 
 /* Welcome container fills available space and centers content */
@@ -38,11 +39,9 @@
 }
 
 /* Editor */
+/* Height constraints are driven by MIN_EDITOR_HEIGHT / MAX_EDITOR_HEIGHT in newChatViewPane.ts */
 .sessions-chat-editor {
 	padding: 0 6px 6px 6px;
-	height: 50px;
-	min-height: 36px;
-	max-height: 200px;
 	flex-shrink: 1;
 }
 
@@ -66,6 +65,12 @@
 	flex: 1;
 }
 
+.sessions-chat-toolbar-pickers {
+	display: flex;
+	align-items: center;
+	gap: 4px;
+}
+
 /* Model picker - uses workbench ModelPickerActionItem */
 .sessions-chat-model-picker {
 	display: flex;
@@ -110,6 +115,11 @@
 	color: var(--vscode-icon-foreground);
 	background: transparent !important;
 	border: none !important;
+	cursor: pointer;
+}
+
+.sessions-chat-send-button .monaco-button.disabled {
+	cursor: default;
 }
 
 .sessions-chat-send-button .monaco-button:not(.disabled):hover {
@@ -222,6 +232,29 @@
 	padding: 0 3px;
 }
 
+.sessions-chat-attachment-pill .monaco-icon-label {
+	gap: 4px;
+}
+
+.sessions-chat-attachment-pill .monaco-icon-label::before {
+	height: auto;
+	padding: 0 0 0 2px;
+	line-height: 100% !important;
+	align-self: center;
+}
+
+.sessions-chat-attachment-pill .monaco-icon-label .monaco-icon-label-container {
+	display: flex;
+}
+
+.sessions-chat-attachment-pill .monaco-icon-label .monaco-icon-label-container .monaco-highlighted-label {
+	display: inline-flex;
+	align-items: center;
+	overflow: hidden;
+	white-space: nowrap;
+	text-overflow: ellipsis;
+}
+
 .sessions-chat-attachment-remove {
 	display: flex;
 	align-items: center;
@@ -246,17 +279,37 @@
 }
 
 /* Drag and drop */
-.sessions-chat-drop-overlay {
-	display: none;
+.sessions-chat-dnd-overlay {
 	position: absolute;
 	top: 0;
 	left: 0;
-	right: 0;
-	bottom: 0;
+	width: 100%;
+	height: 100%;
+	box-sizing: border-box;
+	display: none;
 	z-index: 10;
+	background-color: var(--vscode-sideBar-dropBackground, var(--vscode-list-dropBackground));
+}
+
+.sessions-chat-dnd-overlay.visible {
+	display: flex;
+	align-items: center;
+	justify-content: center;
+}
+
+.sessions-chat-dnd-overlay .attach-context-overlay-text {
+	padding: 0.6em;
+	margin: 0.2em;
+	line-height: 12px;
+	height: 12px;
+	display: flex;
+	align-items: center;
+	text-align: center;
+	background-color: var(--vscode-sideBar-background, var(--vscode-editor-background));
 }
 
-.sessions-chat-input-area.sessions-chat-drop-active {
-	border-color: var(--vscode-focusBorder);
-	background-color: var(--vscode-list-dropBackground);
+.sessions-chat-dnd-overlay .attach-context-overlay-text .codicon {
+	height: 12px;
+	font-size: 12px;
+	margin-right: 3px;
 }
diff --git a/src/vs/sessions/contrib/chat/browser/media/code-icon-agent-sessions-exploration.svg b/src/vs/sessions/contrib/chat/browser/media/code-icon-agent-sessions-exploration.svg
deleted file mode 100644
index 81991ee80fa80..0000000000000
--- a/src/vs/sessions/contrib/chat/browser/media/code-icon-agent-sessions-exploration.svg
+++ /dev/null
@@ -1,49 +0,0 @@
-<svg width="256" height="256" viewBox="0 0 256 256" fill="none" xmlns="http://www.w3.org/2000/svg">
-<mask id="mask0" mask-type="alpha" maskUnits="userSpaceOnUse" x="0" y="0" width="256" height="256">
-<path d="M176.049 250.669C180.838 255.459 188.13 256.7 194.234 253.764L246.94 228.419C252.478 225.755 256 220.154 256 214.008V42.1479C256 36.0025 252.478 30.4008 246.94 27.7374L194.234 2.39089C188.13 -0.544416 180.838 0.696607 176.049 5.48572C181.95 -0.41506 192.039 3.76413 192.039 12.1091V244.046C192.039 252.391 181.95 256.57 176.049 250.669Z" fill="white"/>
-<path d="M181.379 180.646L114.33 128.633L181.379 75.5114V17.794C181.379 10.8477 173.128 7.20673 167.996 11.8862L74.6514 97.8518L31.1994 64.1438C27.1081 61.039 21.3851 61.294 17.5853 64.7476L3.48974 77.5627C-1.15847 81.7893 -1.16367 89.0948 3.47672 93.3292L167.98 244.185C173.107 248.887 181.379 245.249 181.379 238.292V180.646Z" fill="white"/>
-<path d="M36.6937 134.195L3.47672 162.828C-1.16367 167.062 -1.15847 174.37 3.48974 178.594L17.5853 191.409C21.3851 194.863 27.1081 195.118 31.1994 192.013L69.4472 164.057L36.6937 134.195Z" fill="white"/>
-</mask>
-<g mask="url(#mask0)">
-<path d="M167.996 11.8857C173.128 7.20627 181.379 10.8473 181.379 17.7936V75.5109L104.938 136.073L65.5742 106.211L167.996 11.8857Z" fill="#E56E00"/>
-<path d="M36.6937 134.194L3.47672 162.827C-1.16367 167.062 -1.15847 174.37 3.48974 178.594L17.5853 191.409C21.3851 194.863 27.1081 195.118 31.1994 192.013L69.4472 164.056L36.6937 134.194Z" fill="#E56E00"/>
-<g filter="url(#filter0_d)">
-<path d="M181.379 180.645L31.1994 64.1428C27.1081 61.038 21.3851 61.293 17.5853 64.7466L3.48974 77.5617C-1.15847 81.7883 -1.16367 89.0938 3.47672 93.3282L167.972 244.176C173.102 248.881 181.379 245.242 181.379 238.28V180.645Z" fill="#FF8C00"/>
-</g>
-<g filter="url(#filter1_d)">
-<path d="M194.233 253.766C188.13 256.701 180.837 255.46 176.048 250.671C181.949 256.571 192.039 252.392 192.039 244.047V12.1104C192.039 3.76543 181.949 -0.413762 176.048 5.48702C180.837 0.6979 188.129 -0.543115 194.233 2.39218L246.939 27.7387C252.478 30.4021 256 36.0038 256 42.1492V214.009C256 220.155 252.478 225.757 246.939 228.42L194.233 253.766Z" fill="#FFA639"/>
-</g>
-</g>
-<!-- Eye -->
-<g class="mascot-eye">
-<ellipse cx="170" cy="118" rx="14" ry="15" fill="white"/>
-<!-- Pupil -->
-<ellipse cx="173" cy="120" rx="7.5" ry="8" fill="#1B1B1F"/>
-<!-- Eye shine -->
-<circle cx="176" cy="115" r="3.5" fill="white" opacity="0.95"/>
-<!-- Eyelid (blink overlay) -->
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+</svg>
diff --git a/src/vs/sessions/contrib/chat/browser/media/letterpress-sessions-light.svg b/src/vs/sessions/contrib/chat/browser/media/letterpress-sessions-light.svg
new file mode 100644
index 0000000000000..29dfd5459d13c
--- /dev/null
+++ b/src/vs/sessions/contrib/chat/browser/media/letterpress-sessions-light.svg
@@ -0,0 +1,6 @@
+<svg width="128" height="128" viewBox="0 0 128 128" fill="none" xmlns="http://www.w3.org/2000/svg">
+<path d="M6 93.2529V37.8398H10C10 40.8834 11.5856 43.6395 14.084 45.1855L14.3291 45.332L14.333 45.334L60.667 72.0713V116.347C60.6669 118.957 59.2702 121.374 57.0039 122.689C54.7312 124.009 51.9403 124.01 49.667 122.692L9.66699 99.5986L9.45215 99.4697C7.30992 98.1291 6 95.7813 6 93.2529ZM10 93.2529C10 94.4295 10.6306 95.5326 11.6709 96.1367L51.667 119.228L51.6709 119.23C52.7033 119.83 53.9637 119.83 54.9961 119.23C56.0363 118.626 56.6669 117.523 56.667 116.347V74.3818L12.334 48.7988C11.4848 48.3111 10.703 47.7295 10 47.0713V93.2529Z" fill="#D9D9D9"/>
+<path d="M56.667 11.6533C56.6669 10.4769 56.0363 9.37358 54.9961 8.76956C53.9638 8.17014 52.7032 8.17019 51.6709 8.76956L51.666 8.77248L14.333 30.3194C11.6446 31.8825 10.0002 34.7424 10 37.8399C10 40.8835 11.5854 43.6405 14.084 45.1865L14.3291 45.3321L14.333 45.335L56.667 69.7637V11.6533ZM60.667 76.6905L12.3379 48.8008C8.47075 46.5817 6 42.4312 6 37.8399C6.00017 33.3128 8.40716 29.1347 12.3291 26.8574L12.334 26.8545L49.6621 5.31155C51.9363 3.99105 54.7297 3.99021 57.0039 5.31057C59.2701 6.62645 60.6669 9.04345 60.667 11.6533V76.6905Z" fill="#D9D9D9"/>
+<path d="M67.3334 11.6533C67.3335 9.0435 68.7293 6.62647 70.9955 5.31057C73.2697 3.99008 76.063 3.99021 78.3373 5.31057L78.3363 5.31155L118.333 28.4014L118.337 28.4043C120.604 29.7203 122 32.1371 122 34.7471V90.1602H118C118 87.0185 116.31 84.1823 113.671 82.668L113.666 82.6651L67.3334 55.9014V11.6533ZM71.3334 53.5928L115.662 79.1992L116.021 79.4121C116.734 79.8534 117.396 80.3622 118 80.9278V34.7471C118 33.5706 117.37 32.4674 116.329 31.8633L76.3334 8.77248L76.3295 8.76956C75.2971 8.17014 74.0366 8.17019 73.0043 8.76956C71.964 9.37357 71.3335 10.4768 71.3334 11.6533V53.5928Z" fill="#D9D9D9"/>
+<path d="M118 90.1599C118 87.0182 116.31 84.1829 113.671 82.6686L113.666 82.6657L71.3334 58.2106V116.346C71.3334 117.523 71.964 118.626 73.0043 119.23C74.0366 119.83 75.2971 119.83 76.3295 119.23L76.3334 119.228L113.667 97.6813C116.361 96.1153 118 93.3052 118 90.1599ZM122 90.1599C122 94.7459 119.588 98.8687 115.671 101.143L115.666 101.145L78.3363 122.689L78.3373 122.69C76.0631 124.01 73.2696 124.011 70.9955 122.69C68.7292 121.374 67.3334 118.956 67.3334 116.346V51.2819L115.662 79.1989L116.021 79.4128C119.682 81.678 122 85.7121 122 90.1599Z" fill="#D9D9D9"/>
+</svg>
diff --git a/src/vs/sessions/contrib/chat/browser/media/runScriptAction.css b/src/vs/sessions/contrib/chat/browser/media/runScriptAction.css
new file mode 100644
index 0000000000000..0837bc7b8c0e8
--- /dev/null
+++ b/src/vs/sessions/contrib/chat/browser/media/runScriptAction.css
@@ -0,0 +1,57 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+.run-script-action-widget {
+	display: flex;
+	flex-direction: column;
+	gap: 12px;
+	background-color: var(--vscode-quickInput-background);
+	padding: 8px 8px 12px;
+}
+
+.run-script-action-section {
+	display: flex;
+	flex-direction: column;
+	gap: 6px;
+}
+
+.run-script-action-label {
+	font-size: 12px;
+	font-weight: 600;
+}
+
+.run-script-action-input .monaco-inputbox {
+	width: 100%;
+}
+
+.run-script-action-option-row {
+	display: flex;
+	align-items: center;
+	min-height: 22px;
+	gap: 8px;
+}
+
+.run-script-action-option-text {
+	cursor: pointer;
+	-webkit-user-select: none;
+	user-select: none;
+}
+
+.run-script-action-section .monaco-custom-radio {
+	width: fit-content;
+	max-width: 100%;
+}
+
+.run-script-action-hint {
+	font-size: 12px;
+	opacity: 0.8;
+}
+
+.run-script-action-buttons {
+	display: flex;
+	justify-content: flex-end;
+	gap: 8px;
+	padding-top: 4px;
+}
diff --git a/src/vs/sessions/contrib/chat/browser/modePicker.ts b/src/vs/sessions/contrib/chat/browser/modePicker.ts
new file mode 100644
index 0000000000000..d7cc8df61b379
--- /dev/null
+++ b/src/vs/sessions/contrib/chat/browser/modePicker.ts
@@ -0,0 +1,243 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../base/browser/dom.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { Emitter, Event } from '../../../../base/common/event.js';
+import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
+import { localize } from '../../../../nls.js';
+import { IActionWidgetService } from '../../../../platform/actionWidget/browser/actionWidget.js';
+import { ActionListItemKind, IActionListDelegate, IActionListItem } from '../../../../platform/actionWidget/browser/actionList.js';
+import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
+import { ChatMode, IChatMode, IChatModeService } from '../../../../workbench/contrib/chat/common/chatModes.js';
+import { IGitRepository } from '../../../../workbench/contrib/git/common/gitService.js';
+import { IChatSessionsService } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
+import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { Target } from '../../../../workbench/contrib/chat/common/promptSyntax/promptTypes.js';
+import { AICustomizationManagementCommands } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.js';
+
+interface IModePickerItem {
+	readonly kind: 'mode';
+	readonly mode: IChatMode;
+}
+
+interface IConfigurePickerItem {
+	readonly kind: 'configure';
+}
+
+type ModePickerItem = IModePickerItem | IConfigurePickerItem;
+
+/**
+ * A self-contained widget for selecting a chat mode (Agent, custom agents)
+ * for local/Background sessions. Shows only modes whose target matches
+ * the Background session type's customAgentTarget.
+ */
+export class ModePicker extends Disposable {
+
+	private readonly _onDidChange = this._register(new Emitter<IChatMode>());
+	readonly onDidChange: Event<IChatMode> = this._onDidChange.event;
+
+	private _triggerElement: HTMLElement | undefined;
+	private _slotElement: HTMLElement | undefined;
+	private readonly _renderDisposables = this._register(new DisposableStore());
+
+	private _selectedMode: IChatMode = ChatMode.Agent;
+
+	get selectedMode(): IChatMode {
+		return this._selectedMode;
+	}
+
+	constructor(
+		@IActionWidgetService private readonly actionWidgetService: IActionWidgetService,
+		@IChatModeService private readonly chatModeService: IChatModeService,
+		@IChatSessionsService private readonly chatSessionsService: IChatSessionsService,
+		@ICommandService private readonly commandService: ICommandService,
+	) {
+		super();
+
+		this._register(this.chatModeService.onDidChangeChatModes(() => {
+			// Refresh the trigger label when available chat modes change
+			if (this._triggerElement) {
+				this._updateTriggerLabel();
+			}
+		}));
+	}
+
+	/**
+	 * Sets the git repository. When the repository changes, resets the selected mode
+	 * back to the default Agent mode.
+	 */
+	setRepository(repository: IGitRepository | undefined): void {
+		this._selectedMode = ChatMode.Agent;
+		this._updateTriggerLabel();
+	}
+
+	/**
+	 * Renders the mode picker trigger button into the given container.
+	 */
+	render(container: HTMLElement): HTMLElement {
+		this._renderDisposables.clear();
+
+		const slot = dom.append(container, dom.$('.sessions-chat-picker-slot'));
+		this._slotElement = slot;
+		this._renderDisposables.add({ dispose: () => slot.remove() });
+
+		const trigger = dom.append(slot, dom.$('a.action-label'));
+		trigger.tabIndex = 0;
+		trigger.role = 'button';
+		trigger.setAttribute('aria-label', localize('sessions.modePicker.ariaLabel', "Select chat mode"));
+		this._triggerElement = trigger;
+
+		this._updateTriggerLabel();
+
+		this._renderDisposables.add(dom.addDisposableListener(trigger, dom.EventType.CLICK, (e) => {
+			dom.EventHelper.stop(e, true);
+			this._showPicker();
+		}));
+
+		this._renderDisposables.add(dom.addDisposableListener(trigger, dom.EventType.KEY_DOWN, (e) => {
+			if (e.key === 'Enter' || e.key === ' ') {
+				dom.EventHelper.stop(e, true);
+				this._showPicker();
+			}
+		}));
+
+		return slot;
+	}
+
+	/**
+	 * Shows or hides the picker.
+	 */
+	setVisible(visible: boolean): void {
+		if (this._slotElement) {
+			this._slotElement.style.display = visible ? '' : 'none';
+		}
+	}
+
+	private _getAvailableModes(): IChatMode[] {
+		const customAgentTarget = this.chatSessionsService.getCustomAgentTargetForSessionType(AgentSessionProviders.Background);
+		const effectiveTarget = customAgentTarget && customAgentTarget !== Target.Undefined ? customAgentTarget : Target.GitHubCopilot;
+		const modes = this.chatModeService.getModes();
+
+		// Always include the default Agent mode
+		const result: IChatMode[] = [ChatMode.Agent];
+
+		// Add custom modes matching the target and visible to users
+		for (const mode of modes.custom) {
+			const target = mode.target.get();
+			if (target === effectiveTarget || target === Target.Undefined) {
+				const visibility = mode.visibility?.get();
+				if (visibility && !visibility.userInvocable) {
+					continue;
+				}
+				result.push(mode);
+			}
+		}
+
+		return result;
+	}
+
+	private _showPicker(): void {
+		if (!this._triggerElement || this.actionWidgetService.isVisible) {
+			return;
+		}
+
+		const modes = this._getAvailableModes();
+
+		const items = this._buildItems(modes);
+
+		const triggerElement = this._triggerElement;
+		const delegate: IActionListDelegate<ModePickerItem> = {
+			onSelect: (item) => {
+				this.actionWidgetService.hide();
+				if (item.kind === 'mode') {
+					this._selectMode(item.mode);
+				} else {
+					this.commandService.executeCommand(AICustomizationManagementCommands.OpenEditor);
+				}
+			},
+			onHide: () => { triggerElement.focus(); },
+		};
+
+		this.actionWidgetService.show<ModePickerItem>(
+			'localModePicker',
+			false,
+			items,
+			delegate,
+			this._triggerElement,
+			undefined,
+			[],
+			{
+				getAriaLabel: (item) => item.label ?? '',
+				getWidgetAriaLabel: () => localize('modePicker.ariaLabel', "Mode Picker"),
+			},
+		);
+	}
+
+	private _buildItems(modes: IChatMode[]): IActionListItem<ModePickerItem>[] {
+		const items: IActionListItem<ModePickerItem>[] = [];
+
+		// Default Agent mode
+		const agentMode = modes[0];
+		items.push({
+			kind: ActionListItemKind.Action,
+			label: agentMode.label.get(),
+			group: { title: '', icon: this._selectedMode.id === agentMode.id ? Codicon.check : Codicon.blank },
+			item: { kind: 'mode', mode: agentMode },
+		});
+
+		// Custom modes (with separator if any exist)
+		const customModes = modes.slice(1);
+		if (customModes.length > 0) {
+			items.push({ kind: ActionListItemKind.Separator, label: '' });
+			for (const mode of customModes) {
+				items.push({
+					kind: ActionListItemKind.Action,
+					label: mode.label.get(),
+					group: { title: '', icon: this._selectedMode.id === mode.id ? Codicon.check : Codicon.blank },
+					item: { kind: 'mode', mode },
+				});
+			}
+		}
+
+		// Configure Custom Agents action
+		items.push({ kind: ActionListItemKind.Separator, label: '' });
+		items.push({
+			kind: ActionListItemKind.Action,
+			label: localize('configureCustomAgents', "Configure Custom Agents..."),
+			group: { title: '', icon: Codicon.blank },
+			item: { kind: 'configure' },
+		});
+
+		return items;
+	}
+
+	private _selectMode(mode: IChatMode): void {
+		this._selectedMode = mode;
+		this._updateTriggerLabel();
+		this._onDidChange.fire(mode);
+	}
+
+	private _updateTriggerLabel(): void {
+		if (!this._triggerElement) {
+			return;
+		}
+
+		dom.clearNode(this._triggerElement);
+
+		const icon = this._selectedMode.icon.get();
+		if (icon) {
+			dom.append(this._triggerElement, renderIcon(icon));
+		}
+
+		const labelSpan = dom.append(this._triggerElement, dom.$('span.sessions-chat-dropdown-label'));
+		labelSpan.textContent = this._selectedMode.label.get();
+		dom.append(this._triggerElement, renderIcon(Codicon.chevronDown));
+
+		const modes = this._getAvailableModes();
+		this._slotElement?.classList.toggle('disabled', modes.length <= 1);
+	}
+}
diff --git a/src/vs/sessions/contrib/chat/browser/modelPicker.ts b/src/vs/sessions/contrib/chat/browser/modelPicker.ts
new file mode 100644
index 0000000000000..1cdae827ae9b1
--- /dev/null
+++ b/src/vs/sessions/contrib/chat/browser/modelPicker.ts
@@ -0,0 +1,204 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../base/browser/dom.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { Emitter, Event } from '../../../../base/common/event.js';
+import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
+import { localize } from '../../../../nls.js';
+import { IActionWidgetService } from '../../../../platform/actionWidget/browser/actionWidget.js';
+import { ActionListItemKind, IActionListDelegate, IActionListItem } from '../../../../platform/actionWidget/browser/actionList.js';
+import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
+import { IChatSessionProviderOptionItem } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
+import { RemoteNewSession } from './newSession.js';
+
+const FILTER_THRESHOLD = 10;
+
+interface IModelItem {
+	readonly id: string;
+	readonly name: string;
+	readonly description?: string;
+}
+
+/**
+ * A self-contained widget for selecting a model in cloud sessions.
+ * Reads the model option group from the {@link RemoteNewSession} and
+ * renders an action list dropdown with the available models.
+ */
+export class CloudModelPicker extends Disposable {
+
+	private readonly _onDidChange = this._register(new Emitter<IChatSessionProviderOptionItem>());
+	readonly onDidChange: Event<IChatSessionProviderOptionItem> = this._onDidChange.event;
+
+	private _triggerElement: HTMLElement | undefined;
+	private _slotElement: HTMLElement | undefined;
+	private readonly _renderDisposables = this._register(new DisposableStore());
+	private readonly _sessionDisposables = this._register(new DisposableStore());
+
+	private _session: RemoteNewSession | undefined;
+	private _selectedModel: IModelItem | undefined;
+	private _models: IModelItem[] = [];
+
+	get selectedModel(): IModelItem | undefined {
+		return this._selectedModel;
+	}
+
+	constructor(
+		@IActionWidgetService private readonly actionWidgetService: IActionWidgetService,
+	) {
+		super();
+	}
+
+	/**
+	 * Sets the remote session and loads the available models from it.
+	 */
+	setSession(session: RemoteNewSession): void {
+		this._session = session;
+		this._sessionDisposables.clear();
+		this._loadModels(session);
+
+		// Sync selected model to the new session
+		if (this._selectedModel) {
+			session.setModelId(this._selectedModel.id);
+			session.setOptionValue('models', { id: this._selectedModel.id, name: this._selectedModel.name });
+		}
+
+		// Re-load models when option groups change
+		this._sessionDisposables.add(session.onDidChangeOptionGroups(() => {
+			this._loadModels(session);
+		}));
+	}
+
+	/**
+	 * Renders the model picker trigger button into the given container.
+	 */
+	render(container: HTMLElement): HTMLElement {
+		this._renderDisposables.clear();
+
+		const slot = dom.append(container, dom.$('.sessions-chat-picker-slot'));
+		this._slotElement = slot;
+		this._renderDisposables.add({ dispose: () => slot.remove() });
+
+		const trigger = dom.append(slot, dom.$('a.action-label'));
+		trigger.tabIndex = 0;
+		trigger.role = 'button';
+		this._triggerElement = trigger;
+
+		this._updateTriggerLabel();
+
+		this._renderDisposables.add(dom.addDisposableListener(trigger, dom.EventType.CLICK, (e) => {
+			dom.EventHelper.stop(e, true);
+			this._showPicker();
+		}));
+
+		this._renderDisposables.add(dom.addDisposableListener(trigger, dom.EventType.KEY_DOWN, (e) => {
+			if (e.key === 'Enter' || e.key === ' ') {
+				dom.EventHelper.stop(e, true);
+				this._showPicker();
+			}
+		}));
+
+		return slot;
+	}
+
+	/**
+	 * Shows or hides the picker.
+	 */
+	setVisible(visible: boolean): void {
+		if (this._slotElement) {
+			this._slotElement.style.display = visible ? '' : 'none';
+		}
+	}
+
+	private _loadModels(session: RemoteNewSession): void {
+		const modelOption = session.getModelOptionGroup();
+		if (modelOption?.group.items.length) {
+			this._models = modelOption.group.items.map(item => ({
+				id: item.id,
+				name: item.name,
+				description: item.description,
+			}));
+
+			// Select the session's current value, or the default, or the first
+			if (!this._selectedModel || !this._models.some(m => m.id === this._selectedModel!.id)) {
+				const value = modelOption.value;
+				this._selectedModel = value
+					? { id: value.id, name: value.name, description: value.description }
+					: this._models[0];
+			}
+		} else {
+			this._models = [];
+		}
+		this._updateTriggerLabel();
+	}
+
+	private _showPicker(): void {
+		if (!this._triggerElement || this.actionWidgetService.isVisible || this._models.length === 0) {
+			return;
+		}
+
+		const items = this._buildItems();
+		const showFilter = items.filter(i => i.kind === ActionListItemKind.Action).length > FILTER_THRESHOLD;
+
+		const triggerElement = this._triggerElement;
+		const delegate: IActionListDelegate<IModelItem> = {
+			onSelect: (item) => {
+				this.actionWidgetService.hide();
+				this._selectModel(item);
+			},
+			onHide: () => { triggerElement.focus(); },
+		};
+
+		this.actionWidgetService.show<IModelItem>(
+			'remoteModelPicker',
+			false,
+			items,
+			delegate,
+			this._triggerElement,
+			undefined,
+			[],
+			{
+				getAriaLabel: (item) => item.label ?? '',
+				getWidgetAriaLabel: () => localize('modelPicker.ariaLabel', "Model Picker"),
+			},
+			showFilter ? { showFilter: true, filterPlaceholder: localize('modelPicker.filter', "Filter models...") } : undefined,
+		);
+	}
+
+	private _buildItems(): IActionListItem<IModelItem>[] {
+		return this._models.map(model => ({
+			kind: ActionListItemKind.Action,
+			label: model.name,
+			group: { title: '', icon: this._selectedModel?.id === model.id ? Codicon.check : Codicon.blank },
+			item: model,
+		}));
+	}
+
+	private _selectModel(item: IModelItem): void {
+		this._selectedModel = item;
+		this._updateTriggerLabel();
+
+		if (this._session) {
+			this._session.setModelId(item.id);
+			this._session.setOptionValue('models', { id: item.id, name: item.name });
+		}
+		this._onDidChange.fire({ id: item.id, name: item.name, description: item.description });
+	}
+
+	private _updateTriggerLabel(): void {
+		if (!this._triggerElement) {
+			return;
+		}
+
+		dom.clearNode(this._triggerElement);
+		const label = this._selectedModel?.name ?? localize('modelPicker.auto', "Auto");
+
+		const labelSpan = dom.append(this._triggerElement, dom.$('span.sessions-chat-dropdown-label'));
+		labelSpan.textContent = label;
+		dom.append(this._triggerElement, renderIcon(Codicon.chevronDown));
+
+		this._slotElement?.classList.toggle('disabled', this._models.length === 0);
+	}
+}
diff --git a/src/vs/sessions/contrib/chat/browser/newChatContextAttachments.ts b/src/vs/sessions/contrib/chat/browser/newChatContextAttachments.ts
index 7219eaeafd80f..9acac072639ed 100644
--- a/src/vs/sessions/contrib/chat/browser/newChatContextAttachments.ts
+++ b/src/vs/sessions/contrib/chat/browser/newChatContextAttachments.ts
@@ -4,12 +4,13 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as dom from '../../../../base/browser/dom.js';
+import { DragAndDropObserver } from '../../../../base/browser/dom.js';
 import { Codicon } from '../../../../base/common/codicons.js';
 import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
 import { URI } from '../../../../base/common/uri.js';
 import { CancellationToken, CancellationTokenSource } from '../../../../base/common/cancellation.js';
 import { Emitter } from '../../../../base/common/event.js';
-import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
+import { renderIcon, renderLabelWithIcons } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
 import { localize } from '../../../../nls.js';
 import { ThemeIcon } from '../../../../base/common/themables.js';
 import { registerOpenEditorListeners } from '../../../../platform/editor/browser/editor.js';
@@ -17,19 +18,25 @@ import { IOpenerService } from '../../../../platform/opener/common/opener.js';
 
 import { IQuickInputService, IQuickPickItem, IQuickPickSeparator } from '../../../../platform/quickinput/common/quickInput.js';
 import { ITextModelService } from '../../../../editor/common/services/resolverService.js';
-import { IFileService } from '../../../../platform/files/common/files.js';
+import { FileKind, IFileService } from '../../../../platform/files/common/files.js';
 import { IClipboardService } from '../../../../platform/clipboard/common/clipboardService.js';
 import { IFileDialogService } from '../../../../platform/dialogs/common/dialogs.js';
 import { ILabelService } from '../../../../platform/label/common/label.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
+import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
+import { IModelService } from '../../../../editor/common/services/model.js';
+import { ILanguageService } from '../../../../editor/common/languages/language.js';
+import { getIconClasses } from '../../../../editor/common/services/getIconClasses.js';
 import { basename } from '../../../../base/common/resources.js';
 import { Schemas } from '../../../../base/common/network.js';
+import { DEFAULT_LABELS_CONTAINER, ResourceLabels } from '../../../../workbench/browser/labels.js';
 
 import { IChatRequestVariableEntry, OmittedState } from '../../../../workbench/contrib/chat/common/attachments/chatVariableEntries.js';
 import { isLocation } from '../../../../editor/common/languages.js';
 import { resizeImage } from '../../../../workbench/contrib/chat/browser/chatImageUtils.js';
 import { imageToHash, isImage } from '../../../../workbench/contrib/chat/browser/widget/input/editor/chatPasteProviders.js';
-import { getPathForFile } from '../../../../platform/dnd/browser/dnd.js';
+import { CodeDataTransfers, containsDragType, extractEditorsDropData, getPathForFile } from '../../../../platform/dnd/browser/dnd.js';
+import { DataTransfers } from '../../../../base/browser/dnd.js';
 import { getExcludes, ISearchConfiguration, ISearchService, QueryType } from '../../../../workbench/services/search/common/search.js';
 
 /**
@@ -54,6 +61,15 @@ export class NewChatContextAttachments extends Disposable {
 		return this._attachedContext;
 	}
 
+	setAttachments(entries: readonly IChatRequestVariableEntry[]): void {
+		this._attachedContext.length = 0;
+		this._attachedContext.push(...entries);
+		this._updateRendering();
+		this._onDidChangeContext.fire();
+	}
+
+	private readonly _resourceLabels: ResourceLabels;
+
 	constructor(
 		@IQuickInputService private readonly quickInputService: IQuickInputService,
 		@ITextModelService private readonly textModelService: ITextModelService,
@@ -64,8 +80,12 @@ export class NewChatContextAttachments extends Disposable {
 		@ISearchService private readonly searchService: ISearchService,
 		@IConfigurationService private readonly configurationService: IConfigurationService,
 		@IOpenerService private readonly openerService: IOpenerService,
+		@IInstantiationService private readonly instantiationService: IInstantiationService,
+		@IModelService private readonly modelService: IModelService,
+		@ILanguageService private readonly languageService: ILanguageService,
 	) {
 		super();
+		this._resourceLabels = this._register(this.instantiationService.createInstance(ResourceLabels, DEFAULT_LABELS_CONTAINER));
 	}
 
 	// --- Rendering ---
@@ -81,6 +101,7 @@ export class NewChatContextAttachments extends Disposable {
 		}
 
 		this._renderDisposables.clear();
+		this._resourceLabels.clear();
 		dom.clearNode(this._container);
 
 		if (this._attachedContext.length === 0) {
@@ -89,17 +110,30 @@ export class NewChatContextAttachments extends Disposable {
 		}
 
 		this._container.style.display = '';
+		this._container.classList.add('show-file-icons');
 
 		for (const entry of this._attachedContext) {
 			const pill = dom.append(this._container, dom.$('.sessions-chat-attachment-pill'));
 			pill.tabIndex = 0;
 			pill.role = 'button';
-			const icon = entry.kind === 'image' ? Codicon.fileMedia : Codicon.file;
-			dom.append(pill, renderIcon(icon));
-			dom.append(pill, dom.$('span.sessions-chat-attachment-name', undefined, entry.name));
+			const resource = URI.isUri(entry.value) ? entry.value : isLocation(entry.value) ? entry.value.uri : undefined;
+			if (entry.kind === 'image') {
+				dom.append(pill, renderIcon(Codicon.fileMedia));
+				dom.append(pill, dom.$('span.sessions-chat-attachment-name', undefined, entry.name));
+			} else {
+				const label = this._resourceLabels.create(pill, { supportIcons: true });
+				this._renderDisposables.add(label);
+				if (resource) {
+					label.setFile(resource, {
+						fileKind: entry.kind === 'directory' ? FileKind.FOLDER : FileKind.FILE,
+						hidePath: true,
+					});
+				} else {
+					label.setLabel(entry.name);
+				}
+			}
 
 			// Click to open the resource
-			const resource = URI.isUri(entry.value) ? entry.value : isLocation(entry.value) ? entry.value.uri : undefined;
 			if (resource) {
 				pill.style.cursor = 'pointer';
 				this._renderDisposables.add(registerOpenEditorListeners(pill, async () => {
@@ -120,68 +154,85 @@ export class NewChatContextAttachments extends Disposable {
 
 	// --- Drag and drop ---
 
-	registerDropTarget(element: HTMLElement): void {
-		// Use a transparent overlay during drag to capture events over the Monaco editor
-		const overlay = dom.append(element, dom.$('.sessions-chat-drop-overlay'));
+	registerDropTarget(dndContainer: HTMLElement): void {
+		const overlay = dom.append(dndContainer, dom.$('.sessions-chat-dnd-overlay'));
+		let overlayText: HTMLElement | undefined;
 
-		// Use capture phase to intercept drag events before Monaco editor handles them
-		this._register(dom.addDisposableListener(element, dom.EventType.DRAG_ENTER, (e: DragEvent) => {
-			if (e.dataTransfer && Array.from(e.dataTransfer.types).includes('Files')) {
-				e.preventDefault();
-				e.dataTransfer.dropEffect = 'copy';
-				overlay.style.display = 'block';
-				element.classList.add('sessions-chat-drop-active');
-			}
-		}, true));
+		const isDropSupported = (e: DragEvent): boolean => {
+			return containsDragType(e, DataTransfers.FILES, CodeDataTransfers.EDITORS, CodeDataTransfers.FILES, DataTransfers.RESOURCES, DataTransfers.INTERNAL_URI_LIST);
+		};
 
-		this._register(dom.addDisposableListener(element, dom.EventType.DRAG_OVER, (e: DragEvent) => {
-			if (e.dataTransfer && Array.from(e.dataTransfer.types).includes('Files')) {
-				e.preventDefault();
-				e.dataTransfer.dropEffect = 'copy';
-				if (overlay.style.display !== 'block') {
-					overlay.style.display = 'block';
-					element.classList.add('sessions-chat-drop-active');
-				}
+		const showOverlay = () => {
+			overlay.classList.add('visible');
+			if (!overlayText) {
+				const label = localize('attachAsContext', "Attach as Context");
+				const iconAndTextElements = renderLabelWithIcons(`$(${Codicon.attach.id}) ${label}`);
+				const htmlElements = iconAndTextElements.map(element => {
+					if (typeof element === 'string') {
+						return dom.$('span.overlay-text', undefined, element);
+					}
+					return element;
+				});
+				overlayText = dom.$('span.attach-context-overlay-text', undefined, ...htmlElements);
+				overlay.appendChild(overlayText);
 			}
-		}, true));
-
-		this._register(dom.addDisposableListener(overlay, dom.EventType.DRAG_OVER, (e) => {
-			e.preventDefault();
-			e.dataTransfer!.dropEffect = 'copy';
-		}));
+		};
 
-		this._register(dom.addDisposableListener(overlay, dom.EventType.DRAG_LEAVE, (e) => {
-			if (e.relatedTarget && element.contains(e.relatedTarget as Node)) {
-				return;
-			}
-			overlay.style.display = 'none';
-			element.classList.remove('sessions-chat-drop-active');
-		}));
+		const hideOverlay = () => {
+			overlay.classList.remove('visible');
+			overlayText?.remove();
+			overlayText = undefined;
+		};
 
-		this._register(dom.addDisposableListener(overlay, dom.EventType.DROP, async (e) => {
-			e.preventDefault();
-			e.stopPropagation();
-			overlay.style.display = 'none';
-			element.classList.remove('sessions-chat-drop-active');
-
-			// Try items first (for URI-based drops from VS Code tree views)
-			const items = e.dataTransfer?.items;
-			if (items) {
-				for (const item of Array.from(items)) {
-					if (item.kind === 'file') {
-						const file = item.getAsFile();
-						if (!file) {
-							continue;
+		this._register(new DragAndDropObserver(dndContainer, {
+			onDragOver: (e) => {
+				if (isDropSupported(e)) {
+					e.preventDefault();
+					e.stopPropagation();
+					if (e.dataTransfer) {
+						e.dataTransfer.dropEffect = 'copy';
+					}
+					showOverlay();
+				}
+			},
+			onDragLeave: () => {
+				hideOverlay();
+			},
+			onDrop: async (e) => {
+				e.preventDefault();
+				e.stopPropagation();
+				hideOverlay();
+
+				// Extract editor data from VS Code internal drags (e.g., explorer view)
+				const editorDropData = extractEditorsDropData(e);
+				if (editorDropData.length > 0) {
+					for (const editor of editorDropData) {
+						if (editor.resource) {
+							await this._attachFileUri(editor.resource, basename(editor.resource));
 						}
-						const filePath = getPathForFile(file);
-						if (!filePath) {
-							continue;
+					}
+					return;
+				}
+
+				// Fallback: try native file items
+				const items = e.dataTransfer?.items;
+				if (items) {
+					for (const item of Array.from(items)) {
+						if (item.kind === 'file') {
+							const file = item.getAsFile();
+							if (!file) {
+								continue;
+							}
+							const filePath = getPathForFile(file);
+							if (!filePath) {
+								continue;
+							}
+							const uri = URI.file(filePath);
+							await this._attachFileUri(uri, file.name);
 						}
-						const uri = URI.file(filePath);
-						await this._attachFileUri(uri, file.name);
 					}
 				}
-			}
+			},
 		}));
 	}
 
@@ -364,7 +415,7 @@ export class NewChatContextAttachments extends Disposable {
 			return searchResult.results.map(result => ({
 				label: basename(result.resource),
 				description: this.labelService.getUriLabel(result.resource, { relative: true }),
-				iconClass: ThemeIcon.asClassName(Codicon.file),
+				iconClasses: getIconClasses(this.modelService, this.languageService, result.resource, FileKind.FILE),
 				id: result.resource.toString(),
 			} satisfies IQuickPickItem));
 		} catch {
@@ -408,7 +459,7 @@ export class NewChatContextAttachments extends Disposable {
 						picks.push({
 							label: child.name,
 							description: this.labelService.getUriLabel(child.resource, { relative: true }),
-							iconClass: ThemeIcon.asClassName(Codicon.file),
+							iconClasses: getIconClasses(this.modelService, this.languageService, child.resource, FileKind.FILE),
 							id: child.resource.toString(),
 						});
 					}
@@ -439,6 +490,23 @@ export class NewChatContextAttachments extends Disposable {
 	}
 
 	private async _attachFileUri(uri: URI, name: string): Promise<void> {
+		let stat;
+		try {
+			stat = await this.fileService.stat(uri);
+		} catch {
+			return;
+		}
+
+		if (stat.isDirectory) {
+			this._addAttachments({
+				kind: 'directory',
+				id: uri.toString(),
+				value: uri,
+				name,
+			});
+			return;
+		}
+
 		if (/\.(png|jpg|jpeg|bmp|gif|tiff)$/i.test(uri.path)) {
 			const readFile = await this.fileService.readFile(uri);
 			const resizedImage = await resizeImage(readFile.value.buffer);
diff --git a/src/vs/sessions/contrib/chat/browser/newChatPermissionPicker.ts b/src/vs/sessions/contrib/chat/browser/newChatPermissionPicker.ts
new file mode 100644
index 0000000000000..83c775b304b23
--- /dev/null
+++ b/src/vs/sessions/contrib/chat/browser/newChatPermissionPicker.ts
@@ -0,0 +1,257 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../base/browser/dom.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { Emitter, Event } from '../../../../base/common/event.js';
+import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
+import { localize } from '../../../../nls.js';
+import { IActionWidgetService } from '../../../../platform/actionWidget/browser/actionWidget.js';
+import { ActionListItemKind, IActionListDelegate, IActionListItem } from '../../../../platform/actionWidget/browser/actionList.js';
+import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
+import { IDialogService } from '../../../../platform/dialogs/common/dialogs.js';
+import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
+import { ThemeIcon } from '../../../../base/common/themables.js';
+import { ChatConfiguration, ChatPermissionLevel } from '../../../../workbench/contrib/chat/common/constants.js';
+import Severity from '../../../../base/common/severity.js';
+import { MarkdownString } from '../../../../base/common/htmlContent.js';
+
+// Track whether warnings have been shown this VS Code session
+const shownWarnings = new Set<ChatPermissionLevel>();
+
+interface IPermissionItem {
+	readonly level: ChatPermissionLevel;
+	readonly label: string;
+	readonly icon: ThemeIcon;
+	readonly checked: boolean;
+}
+
+/**
+ * A permission picker for the new-session welcome view.
+ * Shows Default Approvals, Bypass Approvals, and Autopilot options.
+ */
+export class NewChatPermissionPicker extends Disposable {
+
+	private readonly _onDidChangeLevel = this._register(new Emitter<ChatPermissionLevel>());
+	readonly onDidChangeLevel: Event<ChatPermissionLevel> = this._onDidChangeLevel.event;
+
+	private _currentLevel: ChatPermissionLevel = ChatPermissionLevel.Default;
+	private _triggerElement: HTMLElement | undefined;
+	private _container: HTMLElement | undefined;
+	private readonly _renderDisposables = this._register(new DisposableStore());
+
+	get permissionLevel(): ChatPermissionLevel {
+		return this._currentLevel;
+	}
+
+	constructor(
+		@IActionWidgetService private readonly actionWidgetService: IActionWidgetService,
+		@IConfigurationService private readonly configurationService: IConfigurationService,
+		@IDialogService private readonly dialogService: IDialogService,
+	) {
+		super();
+	}
+
+	render(container: HTMLElement): HTMLElement {
+		this._renderDisposables.clear();
+
+		const slot = dom.append(container, dom.$('.sessions-chat-picker-slot'));
+		this._container = slot;
+		this._renderDisposables.add({ dispose: () => slot.remove() });
+
+		const trigger = dom.append(slot, dom.$('a.action-label'));
+		trigger.tabIndex = 0;
+		trigger.role = 'button';
+		this._triggerElement = trigger;
+
+		this._updateTriggerLabel(trigger);
+
+		this._renderDisposables.add(dom.addDisposableListener(trigger, dom.EventType.CLICK, (e) => {
+			dom.EventHelper.stop(e, true);
+			this.showPicker();
+		}));
+
+		this._renderDisposables.add(dom.addDisposableListener(trigger, dom.EventType.KEY_DOWN, (e) => {
+			if (e.key === 'Enter' || e.key === ' ') {
+				dom.EventHelper.stop(e, true);
+				this.showPicker();
+			}
+		}));
+
+		return slot;
+	}
+
+	setVisible(visible: boolean): void {
+		if (this._container) {
+			this._container.style.display = visible ? '' : 'none';
+		}
+	}
+
+	showPicker(): void {
+		if (!this._triggerElement || this.actionWidgetService.isVisible) {
+			return;
+		}
+
+		const policyRestricted = this.configurationService.inspect<boolean>(ChatConfiguration.GlobalAutoApprove).policyValue === false;
+		const isAutopilotEnabled = this.configurationService.getValue<boolean>(ChatConfiguration.AutopilotEnabled) !== false;
+
+		const items: IActionListItem<IPermissionItem>[] = [
+			{
+				kind: ActionListItemKind.Action,
+				group: { kind: ActionListItemKind.Header, title: '', icon: Codicon.shield },
+				item: {
+					level: ChatPermissionLevel.Default,
+					label: localize('permissions.default', "Default Approvals"),
+					icon: Codicon.shield,
+					checked: this._currentLevel === ChatPermissionLevel.Default,
+				},
+				label: localize('permissions.default', "Default Approvals"),
+				description: localize('permissions.default.subtext', "Copilot uses your configured settings"),
+				disabled: false,
+			},
+			{
+				kind: ActionListItemKind.Action,
+				group: { kind: ActionListItemKind.Header, title: '', icon: Codicon.warning },
+				item: {
+					level: ChatPermissionLevel.AutoApprove,
+					label: localize('permissions.autoApprove', "Bypass Approvals"),
+					icon: Codicon.warning,
+					checked: this._currentLevel === ChatPermissionLevel.AutoApprove,
+				},
+				label: localize('permissions.autoApprove', "Bypass Approvals"),
+				description: localize('permissions.autoApprove.subtext', "All tool calls are auto-approved"),
+				disabled: policyRestricted,
+			},
+		];
+
+		if (isAutopilotEnabled) {
+			items.push({
+				kind: ActionListItemKind.Action,
+				group: { kind: ActionListItemKind.Header, title: '', icon: Codicon.rocket },
+				item: {
+					level: ChatPermissionLevel.Autopilot,
+					label: localize('permissions.autopilot', "Autopilot (Preview)"),
+					icon: Codicon.rocket,
+					checked: this._currentLevel === ChatPermissionLevel.Autopilot,
+				},
+				label: localize('permissions.autopilot', "Autopilot (Preview)"),
+				description: localize('permissions.autopilot.subtext', "Autonomously iterates from start to finish"),
+				disabled: policyRestricted,
+			});
+		}
+
+		const triggerElement = this._triggerElement;
+		const delegate: IActionListDelegate<IPermissionItem> = {
+			onSelect: async (item) => {
+				this.actionWidgetService.hide();
+				await this._selectLevel(item.level);
+			},
+			onHide: () => { triggerElement.focus(); },
+		};
+
+		this.actionWidgetService.show<IPermissionItem>(
+			'permissionPicker',
+			false,
+			items,
+			delegate,
+			this._triggerElement,
+			undefined,
+			[],
+			{
+				getAriaLabel: (item) => item.label ?? '',
+				getWidgetAriaLabel: () => localize('permissionPicker.ariaLabel', "Permission Picker"),
+			},
+		);
+	}
+
+	private async _selectLevel(level: ChatPermissionLevel): Promise<void> {
+		if (level === ChatPermissionLevel.AutoApprove && !shownWarnings.has(ChatPermissionLevel.AutoApprove)) {
+			const result = await this.dialogService.prompt({
+				type: Severity.Warning,
+				message: localize('permissions.autoApprove.warning.title', "Enable Bypass Approvals?"),
+				buttons: [
+					{
+						label: localize('permissions.autoApprove.warning.confirm', "Enable"),
+						run: () => true
+					},
+					{
+						label: localize('permissions.autoApprove.warning.cancel', "Cancel"),
+						run: () => false
+					},
+				],
+				custom: {
+					icon: Codicon.warning,
+					markdownDetails: [{
+						markdown: new MarkdownString(localize('permissions.autoApprove.warning.detail', "Bypass Approvals will auto-approve all tool calls without asking for confirmation. This includes file edits, terminal commands, and external tool calls.")),
+					}],
+				},
+			});
+			if (result.result !== true) {
+				return;
+			}
+			shownWarnings.add(ChatPermissionLevel.AutoApprove);
+		}
+
+		if (level === ChatPermissionLevel.Autopilot && !shownWarnings.has(ChatPermissionLevel.Autopilot)) {
+			const result = await this.dialogService.prompt({
+				type: Severity.Warning,
+				message: localize('permissions.autopilot.warning.title', "Enable Autopilot?"),
+				buttons: [
+					{
+						label: localize('permissions.autopilot.warning.confirm', "Enable"),
+						run: () => true
+					},
+					{
+						label: localize('permissions.autopilot.warning.cancel', "Cancel"),
+						run: () => false
+					},
+				],
+				custom: {
+					icon: Codicon.rocket,
+					markdownDetails: [{
+						markdown: new MarkdownString(localize('permissions.autopilot.warning.detail', "Autopilot will auto-approve all tool calls and continue working autonomously until the task is complete. The agent will make decisions on your behalf without asking for confirmation.\n\nYou can stop the agent at any time by clicking the stop button. This applies to the current session only.")),
+					}],
+				},
+			});
+			if (result.result !== true) {
+				return;
+			}
+			shownWarnings.add(ChatPermissionLevel.Autopilot);
+		}
+
+		this._currentLevel = level;
+		this._updateTriggerLabel(this._triggerElement);
+		this._onDidChangeLevel.fire(level);
+	}
+
+	private _updateTriggerLabel(trigger: HTMLElement | undefined): void {
+		if (!trigger) {
+			return;
+		}
+
+		dom.clearNode(trigger);
+		let icon: ThemeIcon;
+		let label: string;
+		switch (this._currentLevel) {
+			case ChatPermissionLevel.Autopilot:
+				icon = Codicon.rocket;
+				label = localize('permissions.autopilot.label', "Autopilot (Preview)");
+				break;
+			case ChatPermissionLevel.AutoApprove:
+				icon = Codicon.warning;
+				label = localize('permissions.autoApprove.label', "Bypass Approvals");
+				break;
+			default:
+				icon = Codicon.shield;
+				label = localize('permissions.default.label', "Default Approvals");
+				break;
+		}
+
+		dom.append(trigger, renderIcon(icon));
+		const labelSpan = dom.append(trigger, dom.$('span.sessions-chat-dropdown-label'));
+		labelSpan.textContent = label;
+		dom.append(trigger, renderIcon(Codicon.chevronDown));
+	}
+}
diff --git a/src/vs/sessions/contrib/chat/browser/newChatViewPane.ts b/src/vs/sessions/contrib/chat/browser/newChatViewPane.ts
index 7fbfe0a318729..fc7078fa224c3 100644
--- a/src/vs/sessions/contrib/chat/browser/newChatViewPane.ts
+++ b/src/vs/sessions/contrib/chat/browser/newChatViewPane.ts
@@ -11,17 +11,19 @@ import { toAction } from '../../../../base/common/actions.js';
 import { Emitter } from '../../../../base/common/event.js';
 import { KeyCode } from '../../../../base/common/keyCodes.js';
 import { Disposable, DisposableStore, MutableDisposable, toDisposable } from '../../../../base/common/lifecycle.js';
-import { observableValue } from '../../../../base/common/observable.js';
+import { autorun, observableValue } from '../../../../base/common/observable.js';
 import { URI } from '../../../../base/common/uri.js';
 import { CancellationTokenSource } from '../../../../base/common/cancellation.js';
 import { Button } from '../../../../base/browser/ui/button/button.js';
-
 import { CodeEditorWidget, ICodeEditorWidgetOptions } from '../../../../editor/browser/widget/codeEditor/codeEditorWidget.js';
 import { EditorExtensionsRegistry } from '../../../../editor/browser/editorExtensions.js';
 import { IEditorConstructionOptions } from '../../../../editor/browser/config/editorConfiguration.js';
 import { IModelService } from '../../../../editor/common/services/model.js';
+import { SuggestController } from '../../../../editor/contrib/suggest/browser/suggestController.js';
+import { SnippetController2 } from '../../../../editor/contrib/snippet/browser/snippetController2.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
-import { IContextKeyService, IContextKey, RawContextKey, ContextKeyExpr } from '../../../../platform/contextkey/common/contextkey.js';
+import { IContextKeyService, IContextKey, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
+import { ServiceCollection } from '../../../../platform/instantiation/common/serviceCollection.js';
 import { IContextMenuService } from '../../../../platform/contextview/browser/contextView.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
@@ -34,32 +36,55 @@ import { getDefaultHoverDelegate } from '../../../../base/browser/ui/hover/hover
 import { HoverPosition } from '../../../../base/browser/ui/hover/hoverWidget.js';
 import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
 import { localize } from '../../../../nls.js';
+import * as aria from '../../../../base/browser/ui/aria/aria.js';
 import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
 import { ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
 import { ChatSessionPosition, getResourceForNewChatSession } from '../../../../workbench/contrib/chat/browser/chatSessions/chatSessions.contribution.js';
 import { ChatSessionPickerActionItem, IChatSessionPickerDelegate } from '../../../../workbench/contrib/chat/browser/chatSessions/chatSessionPickerActionItem.js';
 import { SearchableOptionPickerActionItem } from '../../../../workbench/contrib/chat/browser/chatSessions/searchableOptionPickerActionItem.js';
-import { IChatSessionProviderOptionGroup, IChatSessionProviderOptionItem, IChatSessionsService } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
+import { IChatSessionProviderOptionItem } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
 import { ILanguageModelChatMetadataAndIdentifier, ILanguageModelsService } from '../../../../workbench/contrib/chat/common/languageModels.js';
 import { IModelPickerDelegate } from '../../../../workbench/contrib/chat/browser/widget/input/modelPickerActionItem.js';
 import { EnhancedModelPickerActionItem } from '../../../../workbench/contrib/chat/browser/widget/input/modelPickerActionItem2.js';
 import { IChatInputPickerOptions } from '../../../../workbench/contrib/chat/browser/widget/input/chatInputPickerActionItem.js';
 import { IViewDescriptorService } from '../../../../workbench/common/views.js';
 import { IWorkspaceContextService } from '../../../../platform/workspace/common/workspace.js';
+import { IWorkspaceTrustRequestService } from '../../../../platform/workspace/common/workspaceTrust.js';
 import { IViewPaneOptions, ViewPane } from '../../../../workbench/browser/parts/views/viewPane.js';
 import { ContextMenuController } from '../../../../editor/contrib/contextmenu/browser/contextmenu.js';
 import { getSimpleEditorOptions } from '../../../../workbench/contrib/codeEditor/browser/simpleEditorOptions.js';
-import { isString } from '../../../../base/common/types.js';
 import { NewChatContextAttachments } from './newChatContextAttachments.js';
 import { GITHUB_REMOTE_FILE_SCHEME } from '../../fileTreeView/browser/githubFileSystemProvider.js';
 import { FolderPicker } from './folderPicker.js';
 import { IGitService } from '../../../../workbench/contrib/git/common/gitService.js';
-import { IsolationModePicker, SessionTargetPicker } from './sessionTargetPicker.js';
+import { IsolationMode, IsolationModePicker, SessionTargetPicker } from './sessionTargetPicker.js';
 import { BranchPicker } from './branchPicker.js';
-import { INewSession } from './newSession.js';
+import { SyncIndicator } from './syncIndicator.js';
+import { INewSession, ISessionOptionGroup, RemoteNewSession } from './newSession.js';
+import { RepoPicker } from './repoPicker.js';
+import { CloudModelPicker } from './modelPicker.js';
+import { ModePicker } from './modePicker.js';
 import { getErrorMessage } from '../../../../base/common/errors.js';
-
-const STORAGE_KEY_LAST_MODEL = 'sessions.selectedModel';
+import { SlashCommandHandler } from './slashCommands.js';
+import { IChatModelInputState } from '../../../../workbench/contrib/chat/common/model/chatModel.js';
+import { IChatRequestVariableEntry } from '../../../../workbench/contrib/chat/common/attachments/chatVariableEntries.js';
+import { ChatAgentLocation, ChatModeKind } from '../../../../workbench/contrib/chat/common/constants.js';
+import { ChatHistoryNavigator } from '../../../../workbench/contrib/chat/common/widget/chatWidgetHistoryService.js';
+import { IHistoryNavigationWidget } from '../../../../base/browser/history.js';
+import { NewChatPermissionPicker } from './newChatPermissionPicker.js';
+import { registerAndCreateHistoryNavigationContext, IHistoryNavigationContext } from '../../../../platform/history/browser/contextScopedHistoryWidget.js';
+
+const STORAGE_KEY_DRAFT_STATE = 'sessions.draftState';
+const MIN_EDITOR_HEIGHT = 50;
+const MAX_EDITOR_HEIGHT = 200;
+
+interface IDraftState extends IChatModelInputState {
+	target?: AgentSessionProviders;
+	isolationMode?: IsolationMode;
+	branch?: string;
+	folderUri?: string;
+	repo?: string;
+}
 
 // #region --- Chat Welcome Widget ---
 
@@ -79,15 +104,24 @@ interface INewChatWidgetOptions {
  * This widget is shown only in the empty/welcome state. Once the user sends
  * a message, a session is created and the workbench ChatViewPane takes over.
  */
-class NewChatWidget extends Disposable {
+class NewChatWidget extends Disposable implements IHistoryNavigationWidget {
 
 	private readonly _targetPicker: SessionTargetPicker;
 	private readonly _isolationModePicker: IsolationModePicker;
 	private readonly _branchPicker: BranchPicker;
+	private readonly _syncIndicator: SyncIndicator;
 	private readonly _options: INewChatWidgetOptions;
 
+	// IHistoryNavigationWidget
+	private readonly _onDidFocus = this._register(new Emitter<void>());
+	readonly onDidFocus = this._onDidFocus.event;
+	private readonly _onDidBlur = this._register(new Emitter<void>());
+	readonly onDidBlur = this._onDidBlur.event;
+	get element(): HTMLElement { return this._editorContainer; }
+
 	// Input
 	private _editor!: CodeEditorWidget;
+	private _editorContainer!: HTMLElement;
 	private readonly _currentLanguageModel = observableValue<ILanguageModelChatMetadataAndIdentifier | undefined>('currentLanguageModel', undefined);
 	private readonly _modelPickerDisposable = this._register(new MutableDisposable());
 
@@ -109,81 +143,171 @@ class NewChatWidget extends Disposable {
 	// Welcome part
 	private _pickersContainer: HTMLElement | undefined;
 	private _extensionPickersLeftContainer: HTMLElement | undefined;
-	private _extensionPickersRightContainer: HTMLElement | undefined;
+	private _toolbarPickersContainer: HTMLElement | undefined;
+	private _localModelPickerContainer: HTMLElement | undefined;
 	private _inputSlot: HTMLElement | undefined;
 	private readonly _folderPicker: FolderPicker;
 	private _folderPickerContainer: HTMLElement | undefined;
-	private readonly _pickerWidgets = new Map<string, ChatSessionPickerActionItem | SearchableOptionPickerActionItem>();
-	private readonly _pickerWidgetDisposables = this._register(new DisposableStore());
+	private readonly _permissionPicker: NewChatPermissionPicker;
+	private readonly _repoPicker: RepoPicker;
+	private _repoPickerContainer: HTMLElement | undefined;
+	private readonly _cloudModelPicker: CloudModelPicker;
+	private readonly _modePicker: ModePicker;
+	private readonly _toolbarPickerWidgets = new Map<string, ChatSessionPickerActionItem | SearchableOptionPickerActionItem>();
+	private readonly _toolbarPickerDisposables = this._register(new DisposableStore());
 	private readonly _optionEmitters = new Map<string, Emitter<IChatSessionProviderOptionItem>>();
-	private readonly _selectedOptions = new Map<string, IChatSessionProviderOptionItem>();
 	private readonly _optionContextKeys = new Map<string, IContextKey<string>>();
-	private readonly _whenClauseKeys = new Set<string>();
 
 	// Attached context
 	private readonly _contextAttachments: NewChatContextAttachments;
 
+	// Slash commands
+	private _slashCommandHandler: SlashCommandHandler | undefined;
+
+	// Input state
+	private _draftState: IDraftState | undefined = {
+		inputText: '',
+		attachments: [],
+		mode: { id: ChatModeKind.Agent, kind: ChatModeKind.Agent },
+		selectedModel: undefined,
+		selections: [],
+		contrib: {}
+	};
+
+	// Input history
+	private readonly _history: ChatHistoryNavigator;
+	private _historyNavigationBackwardsEnablement!: IHistoryNavigationContext['historyNavigationBackwardsEnablement'];
+	private _historyNavigationForwardsEnablement!: IHistoryNavigationContext['historyNavigationForwardsEnablement'];
+
 	constructor(
 		options: INewChatWidgetOptions,
 		@IInstantiationService private readonly instantiationService: IInstantiationService,
-		@IChatSessionsService private readonly chatSessionsService: IChatSessionsService,
 		@IModelService private readonly modelService: IModelService,
 		@IConfigurationService private readonly configurationService: IConfigurationService,
 		@ILanguageModelsService private readonly languageModelsService: ILanguageModelsService,
 		@IContextKeyService private readonly contextKeyService: IContextKeyService,
-		@IContextMenuService contextMenuService: IContextMenuService,
 		@ILogService private readonly logService: ILogService,
 		@IHoverService private readonly hoverService: IHoverService,
-		@IWorkspaceContextService private readonly workspaceContextService: IWorkspaceContextService,
 		@ISessionsManagementService private readonly sessionsManagementService: ISessionsManagementService,
 		@IGitService private readonly gitService: IGitService,
 		@IStorageService private readonly storageService: IStorageService,
+		@IWorkspaceTrustRequestService private readonly workspaceTrustRequestService: IWorkspaceTrustRequestService,
 	) {
 		super();
+		this._history = this._register(this.instantiationService.createInstance(ChatHistoryNavigator, ChatAgentLocation.Chat));
 		this._contextAttachments = this._register(this.instantiationService.createInstance(NewChatContextAttachments));
 		this._folderPicker = this._register(this.instantiationService.createInstance(FolderPicker));
-		this._targetPicker = this._register(new SessionTargetPicker(options.allowedTargets, options.defaultTarget));
+		this._permissionPicker = this._register(this.instantiationService.createInstance(NewChatPermissionPicker));
+		this._repoPicker = this._register(this.instantiationService.createInstance(RepoPicker));
+		this._cloudModelPicker = this._register(this.instantiationService.createInstance(CloudModelPicker));
+		this._modePicker = this._register(this.instantiationService.createInstance(ModePicker));
+		this._targetPicker = this._register(new SessionTargetPicker(options.allowedTargets, this._resolveDefaultTarget(options)));
 		this._isolationModePicker = this._register(this.instantiationService.createInstance(IsolationModePicker));
 		this._branchPicker = this._register(this.instantiationService.createInstance(BranchPicker));
+		this._syncIndicator = this._register(this.instantiationService.createInstance(SyncIndicator));
 		this._options = options;
 
 		// When target changes, create new session
 		this._register(this._targetPicker.onDidChangeTarget((target) => {
 			this._createNewSession();
 			const isLocal = target === AgentSessionProviders.Background;
-			this._isolationModePicker.setVisible(isLocal);
+			this._updateIsolationPickerVisibility();
+			this._permissionPicker.setVisible(isLocal);
 			this._branchPicker.setVisible(isLocal);
+			this._syncIndicator.setVisible(isLocal);
+			this._updateDraftState();
 			this._focusEditor();
 		}));
 
-		this._register(this.contextKeyService.onDidChangeContext(e => {
-			if (this._whenClauseKeys.size > 0 && e.affectsSome(this._whenClauseKeys)) {
-				this._renderExtensionPickers(true);
-			}
-		}));
-
 		this._register(this._branchPicker.onDidChangeLoading(loading => {
 			this._branchLoading = loading;
 			this._updateInputLoadingState();
 		}));
 
-		this._register(this._branchPicker.onDidChange(() => {
+		this._register(this._branchPicker.onDidChange((branch) => {
+			this._newSession.value?.setBranch(branch);
+			this._syncIndicator.setBranch(branch);
+			this._updateDraftState();
+			this._focusEditor();
+		}));
+
+		this._register(this._folderPicker.onDidSelectFolder(async (folderUri) => {
+			const trusted = await this._requestFolderTrust(folderUri);
+			if (trusted) {
+				this._newSession.value?.setRepoUri(folderUri);
+			}
+			this._updateDraftState();
+			this._focusEditor();
+		}));
+
+		this._register(this._isolationModePicker.onDidChange((mode) => {
+			this._newSession.value?.setIsolationMode(mode);
+			this._branchPicker.setVisible(mode === 'worktree');
+			this._syncIndicator.setVisible(mode === 'worktree');
+			this._updateDraftState();
 			this._focusEditor();
 		}));
 
-		this._register(this._folderPicker.onDidSelectFolder(() => {
+		// When mode changes, update the session
+		this._register(this._modePicker.onDidChange((mode) => {
+			this._newSession.value?.setMode(mode);
 			this._focusEditor();
 		}));
 
-		this._register(this._isolationModePicker.onDidChange(() => {
+		this._register(this._repoPicker.onDidSelectRepo((repoId) => {
+			if (this._targetPicker.selectedTarget !== AgentSessionProviders.Background) {
+				this._newSession.value?.setRepoUri(this._getRepoUri(repoId));
+			}
+			this._updateDraftState();
+		}));
+
+		// When language models change (e.g., extension activates), reinitialize if no model selected
+		this._register(this.languageModelsService.onDidChangeLanguageModels(() => {
+			this._initDefaultModel();
+		}));
+
+		// Update input state when attachments or model change
+		this._register(this._contextAttachments.onDidChangeContext(() => {
+			this._updateDraftState();
 			this._focusEditor();
 		}));
+		this._register(autorun(reader => {
+			this._currentLanguageModel.read(reader);
+			this._updateDraftState();
+		}));
+
+		// When isolation option config changes, update picker visibility
+		this._register(this.configurationService.onDidChangeConfiguration(e => {
+			if (e.affectsConfiguration('github.copilot.chat.cli.isolationOption.enabled')) {
+				this._updateIsolationPickerVisibility();
+			}
+		}));
+	}
+
+	private get _isIsolationOptionEnabled(): boolean {
+		return this.configurationService.getValue<boolean>('github.copilot.chat.cli.isolationOption.enabled') !== false;
+	}
+
+	private _updateIsolationPickerVisibility(): void {
+		const isLocal = this._targetPicker.selectedTarget === AgentSessionProviders.Background;
+		const enabled = this._isIsolationOptionEnabled;
+		if (!enabled) {
+			this._isolationModePicker.setPreferredIsolationMode('worktree');
+		}
+		this._isolationModePicker.setVisible(isLocal);
+		this._isolationModePicker.setEnabled(enabled);
 	}
 
 	// --- Rendering ---
 
 	render(container: HTMLElement): void {
 		const wrapper = dom.append(container, dom.$('.sessions-chat-widget'));
+
+		// Overflow widget DOM node at the top level so the suggest widget
+		// is not clipped by any overflow:hidden ancestor.
+		const editorOverflowWidgetsDomNode = dom.append(container, dom.$('.sessions-chat-editor-overflow.monaco-editor'));
+		this._register({ dispose: () => editorOverflowWidgetsDomNode.remove() });
+
 		const welcomeElement = dom.append(wrapper, dom.$('.chat-full-welcome'));
 
 		// Watermark letterpress
@@ -198,7 +322,7 @@ class NewChatWidget extends Disposable {
 
 		// Input area inside the input slot
 		const inputArea = dom.$('.sessions-chat-input-area');
-		this._contextAttachments.registerDropTarget(inputArea);
+		this._contextAttachments.registerDropTarget(wrapper);
 		this._contextAttachments.registerPasteHandler(inputArea);
 
 		// Attachments row (pills only) inside input area, above editor
@@ -206,21 +330,26 @@ class NewChatWidget extends Disposable {
 		const attachedContextContainer = dom.append(attachRow, dom.$('.sessions-chat-attached-context'));
 		this._contextAttachments.renderAttachedContext(attachedContextContainer);
 
-		this._createEditor(inputArea);
+		this._createEditor(inputArea, editorOverflowWidgetsDomNode);
 		this._createBottomToolbar(inputArea);
 		this._inputSlot.appendChild(inputArea);
 
 		// Isolation mode and branch pickers (below the input, shown when Local target is selected)
 		const isolationContainer = dom.append(welcomeElement, dom.$('.chat-full-welcome-local-mode'));
 		this._isolationModePicker.render(isolationContainer);
+		this._permissionPicker.render(isolationContainer);
 		dom.append(isolationContainer, dom.$('.sessions-chat-local-mode-spacer'));
 		const branchContainer = dom.append(isolationContainer, dom.$('.sessions-chat-local-mode-right'));
 		this._branchPicker.render(branchContainer);
+		this._syncIndicator.render(branchContainer);
 
-		// Set initial visibility based on default target
+		// Set initial visibility based on default target and isolation mode
 		const isLocal = this._targetPicker.selectedTarget === AgentSessionProviders.Background;
-		this._isolationModePicker.setVisible(isLocal);
-		this._branchPicker.setVisible(isLocal);
+		this._updateIsolationPickerVisibility();
+		this._permissionPicker.setVisible(isLocal);
+		const isWorktree = this._isolationModePicker.isolationMode === 'worktree';
+		this._branchPicker.setVisible(isLocal && isWorktree);
+		this._syncIndicator.setVisible(isLocal && isWorktree);
 
 		// Render target buttons & extension pickers
 		this._renderOptionGroupPickers();
@@ -228,6 +357,9 @@ class NewChatWidget extends Disposable {
 		// Initialize model picker
 		this._initDefaultModel();
 
+		// Restore draft input state from storage
+		this._restoreState();
+
 		// Create initial session
 		this._createNewSession();
 
@@ -242,7 +374,16 @@ class NewChatWidget extends Disposable {
 
 	private async _createNewSession(): Promise<void> {
 		const target = this._targetPicker.selectedTarget;
-		const defaultRepoUri = this._folderPicker.selectedFolderUri ?? this.workspaceContextService.getWorkspace().folders[0]?.uri;
+		let defaultRepoUri = this._folderPicker.selectedFolderUri;
+
+		// For local targets, request workspace trust before creating the session
+		if (target === AgentSessionProviders.Background && defaultRepoUri) {
+			const trusted = await this._requestFolderTrust(defaultRepoUri);
+			if (!trusted) {
+				defaultRepoUri = undefined;
+			}
+		}
+
 		const resource = getResourceForNewChatSession({
 			type: target,
 			position: this._options.sessionPosition ?? ChatSessionPosition.Sidebar,
@@ -260,42 +401,58 @@ class NewChatWidget extends Disposable {
 	private _setNewSession(session: INewSession): void {
 		this._newSession.value = session;
 
-		// Wire pickers to the new session
-		this._folderPicker.setNewSession(session);
-		this._isolationModePicker.setNewSession(session);
-		this._branchPicker.setNewSession(session);
+		// Wire pickers to the new session and disconnect inactive ones
+		const target = this._targetPicker.selectedTarget;
+		if (target === AgentSessionProviders.Background) {
+			session.setIsolationMode(this._isolationModePicker.isolationMode);
+			if (this._branchPicker.selectedBranch) {
+				session.setBranch(this._branchPicker.selectedBranch);
+			}
+		} else {
+			const selectedRepo = this._repoPicker.selectedRepo;
+			if (selectedRepo) {
+				session.setRepoUri(this._getRepoUri(selectedRepo));
+			}
+		}
 
-		// Set the current model on the session
+		// Set the current model on the session (for local sessions)
 		const currentModel = this._currentLanguageModel.get();
 		if (currentModel) {
 			session.setModelId(currentModel.identifier);
 		}
 
+		// Set the current mode on the session (for local sessions)
+		session.setMode(this._modePicker.selectedMode);
+
 		// Open repository for the session's repoUri
 		if (session.repoUri) {
 			this._openRepository(session.repoUri);
 		}
 
-		// Render extension pickers for the new session
-		this._renderExtensionPickers(true);
-
 		// Listen for session changes
-		this._newSessionListener.value = session.onDidChange((changeType) => {
+		const listeners = new DisposableStore();
+		listeners.add(session.onDidChange((changeType) => {
 			if (changeType === 'repoUri' && session.repoUri) {
 				this._openRepository(session.repoUri);
 			}
 			if (changeType === 'isolationMode') {
 				this._branchPicker.setVisible(session.isolationMode === 'worktree');
 			}
-			if (changeType === 'options') {
-				this._syncOptionsFromSession(session.resource);
-				this._renderExtensionPickers();
-			}
 			if (changeType === 'disabled') {
 				this._updateSendButtonState();
 			}
-		});
+		}));
 
+		if (session instanceof RemoteNewSession) {
+			this._renderRemoteSessionPickers(session, true);
+			listeners.add(session.onDidChangeOptionGroups(() => {
+				this._renderRemoteSessionPickers(session);
+			}));
+		} else {
+			this._renderLocalSessionPickers();
+		}
+
+		this._newSessionListener.value = listeners;
 		this._updateSendButtonState();
 	}
 
@@ -307,6 +464,9 @@ class NewChatWidget extends Disposable {
 		this._updateInputLoadingState();
 		this._branchPicker.setRepository(undefined);
 		this._isolationModePicker.setRepository(undefined);
+		this._updateIsolationPickerVisibility();
+		this._syncIndicator.setRepository(undefined);
+		this._modePicker.setRepository(undefined);
 
 		this.gitService.openRepository(folderUri).then(repository => {
 			if (cts.token.isCancellationRequested) {
@@ -315,7 +475,10 @@ class NewChatWidget extends Disposable {
 			this._repositoryLoading = false;
 			this._updateInputLoadingState();
 			this._isolationModePicker.setRepository(repository);
+			this._updateIsolationPickerVisibility();
 			this._branchPicker.setRepository(repository);
+			this._syncIndicator.setRepository(repository);
+			this._modePicker.setRepository(repository);
 		}).catch(e => {
 			if (cts.token.isCancellationRequested) {
 				return;
@@ -324,7 +487,10 @@ class NewChatWidget extends Disposable {
 			this._repositoryLoading = false;
 			this._updateInputLoadingState();
 			this._isolationModePicker.setRepository(undefined);
+			this._updateIsolationPickerVisibility();
 			this._branchPicker.setRepository(undefined);
+			this._syncIndicator.setRepository(undefined);
+			this._modePicker.setRepository(undefined);
 		});
 	}
 
@@ -348,8 +514,18 @@ class NewChatWidget extends Disposable {
 
 	// --- Editor ---
 
-	private _createEditor(container: HTMLElement): void {
-		const editorContainer = dom.append(container, dom.$('.sessions-chat-editor'));
+	private _createEditor(container: HTMLElement, overflowWidgetsDomNode: HTMLElement): void {
+		const editorContainer = this._editorContainer = dom.append(container, dom.$('.sessions-chat-editor'));
+		editorContainer.style.height = `${MIN_EDITOR_HEIGHT}px`;
+
+		// Create scoped context key service and register history navigation
+		// BEFORE creating the editor, so the editor's context key scope is a child
+		const inputScopedContextKeyService = this._register(this.contextKeyService.createScoped(container));
+		const { historyNavigationBackwardsEnablement, historyNavigationForwardsEnablement } = this._register(registerAndCreateHistoryNavigationContext(inputScopedContextKeyService, this));
+		this._historyNavigationBackwardsEnablement = historyNavigationBackwardsEnablement;
+		this._historyNavigationForwardsEnablement = historyNavigationForwardsEnablement;
+
+		const scopedInstantiationService = this._register(this.instantiationService.createChild(new ServiceCollection([IContextKeyService, inputScopedContextKeyService])));
 
 		const uri = URI.from({ scheme: 'sessions-chat', path: `input-${Date.now()}` });
 		const textModel = this._register(this.modelService.createModel('', null, uri, true));
@@ -362,37 +538,91 @@ class NewChatWidget extends Disposable {
 			fontFamily: 'system-ui, -apple-system, sans-serif',
 			fontSize: 13,
 			lineHeight: 20,
+			cursorWidth: 1,
 			padding: { top: 8, bottom: 2 },
 			wrappingStrategy: 'advanced',
 			stickyScroll: { enabled: false },
 			renderWhitespace: 'none',
+			overflowWidgetsDomNode,
+			suggest: {
+				showIcons: false,
+				showSnippets: false,
+				showWords: true,
+				showStatusBar: false,
+				insertMode: 'insert',
+			},
 		};
 
 		const widgetOptions: ICodeEditorWidgetOptions = {
 			isSimpleWidget: true,
 			contributions: EditorExtensionsRegistry.getSomeEditorContributions([
 				ContextMenuController.ID,
+				SuggestController.ID,
+				SnippetController2.ID,
 			]),
 		};
 
-		this._editor = this._register(this.instantiationService.createInstance(
+		this._editor = this._register(scopedInstantiationService.createInstance(
 			CodeEditorWidget, editorContainer, editorOptions, widgetOptions,
 		));
 		this._editor.setModel(textModel);
 
+		// Ensure suggest widget renders above the input (not clipped by container)
+		SuggestController.get(this._editor)?.forceRenderingAbove();
+
+		this._register(this._editor.onDidFocusEditorWidget(() => this._onDidFocus.fire()));
+		this._register(this._editor.onDidBlurEditorWidget(() => this._onDidBlur.fire()));
+
 		this._register(this._editor.onKeyDown(e => {
 			if (e.keyCode === KeyCode.Enter && !e.shiftKey && !e.ctrlKey && !e.altKey) {
+				// Don't send if the suggest widget is visible (let it accept the completion)
+				if (this._editor.contextKeyService.getContextKeyValue<boolean>('suggestWidgetVisible')) {
+					return;
+				}
+				e.preventDefault();
+				e.stopPropagation();
+				this._send();
+			}
+			if (e.keyCode === KeyCode.Enter && !e.shiftKey && !e.ctrlKey && e.altKey) {
 				e.preventDefault();
 				e.stopPropagation();
 				this._send();
 			}
 		}));
 
-		this._register(this._editor.onDidContentSizeChange(() => {
+		// Update history navigation enablement based on cursor position
+		const updateHistoryNavigationEnablement = () => {
+			const model = this._editor.getModel();
+			const position = this._editor.getPosition();
+			if (!model || !position) {
+				return;
+			}
+			this._historyNavigationBackwardsEnablement.set(position.lineNumber === 1 && position.column === 1);
+			this._historyNavigationForwardsEnablement.set(position.lineNumber === model.getLineCount() && position.column === model.getLineMaxColumn(position.lineNumber));
+		};
+		this._register(this._editor.onDidChangeCursorPosition(() => updateHistoryNavigationEnablement()));
+		updateHistoryNavigationEnablement();
+
+		let previousHeight = -1;
+		this._register(this._editor.onDidContentSizeChange(e => {
+			if (!e.contentHeightChanged) {
+				return;
+			}
+			const contentHeight = this._editor.getContentHeight();
+			const clampedHeight = Math.min(MAX_EDITOR_HEIGHT, Math.max(MIN_EDITOR_HEIGHT, contentHeight));
+			if (clampedHeight === previousHeight) {
+				return;
+			}
+			previousHeight = clampedHeight;
+			this._editorContainer.style.height = `${clampedHeight}px`;
 			this._editor.layout();
 		}));
 
+		// Slash commands
+		this._slashCommandHandler = this._register(this.instantiationService.createInstance(SlashCommandHandler, this._editor));
+
 		this._register(this._editor.onDidChangeModelContent(() => {
+			this._updateDraftState();
 			this._updateSendButtonState();
 		}));
 	}
@@ -403,10 +633,15 @@ class NewChatWidget extends Disposable {
 
 	private _createAttachButton(container: HTMLElement): void {
 		const attachButton = dom.append(container, dom.$('.sessions-chat-attach-button'));
+		const attachButtonLabel = localize('addContext', "Add Context...");
 		attachButton.tabIndex = 0;
 		attachButton.role = 'button';
-		attachButton.title = localize('addContext', "Add Context...");
-		attachButton.ariaLabel = localize('addContext', "Add Context...");
+		attachButton.ariaLabel = attachButtonLabel;
+		this._register(this.hoverService.setupDelayedHover(attachButton, {
+			content: attachButtonLabel,
+			position: { hoverPosition: HoverPosition.BELOW },
+			appearance: { showPointer: true }
+		}));
 		dom.append(attachButton, renderIcon(Codicon.add));
 		this._register(dom.addDisposableListener(attachButton, dom.EventType.CLICK, () => {
 			this._contextAttachments.showPicker(this._getContextFolderUri());
@@ -421,33 +656,44 @@ class NewChatWidget extends Disposable {
 		const target = this._targetPicker.selectedTarget;
 
 		if (target === AgentSessionProviders.Background) {
-			return this._folderPicker.selectedFolderUri ?? this.workspaceContextService.getWorkspace().folders[0]?.uri;
-		}
-
-		// For cloud targets, look for a repository option in the selected options
-		for (const [groupId, option] of this._selectedOptions) {
-			if (isRepoOrFolderGroup({ id: groupId, name: groupId, items: [] })) {
-				const nwo = option.id; // e.g. "owner/repo"
-				if (nwo && nwo.includes('/')) {
-					return URI.from({
-						scheme: GITHUB_REMOTE_FILE_SCHEME,
-						authority: 'github',
-						path: `/${nwo}/HEAD`,
-					});
-				}
-			}
+			return this._folderPicker.selectedFolderUri;
+		}
+
+		// For cloud targets, use the repo picker's selection
+		const selectedRepo = this._repoPicker.selectedRepo;
+		if (selectedRepo && selectedRepo.includes('/')) {
+			return this._getRepoUri(selectedRepo);
 		}
 
 		return undefined;
 	}
 
+	private _getRepoUri(repoId: string): URI {
+		return URI.from({
+			scheme: GITHUB_REMOTE_FILE_SCHEME,
+			authority: 'github',
+			path: `/${repoId}/HEAD`,
+		});
+	}
+
 	private _createBottomToolbar(container: HTMLElement): void {
 		const toolbar = dom.append(container, dom.$('.sessions-chat-toolbar'));
 
 		this._createAttachButton(toolbar);
 
-		const modelPickerContainer = dom.append(toolbar, dom.$('.sessions-chat-model-picker'));
-		this._createModelPicker(modelPickerContainer);
+		// Mode picker (before model pickers)
+		this._modePicker.render(toolbar);
+		this._modePicker.setVisible(false);
+
+		// Local model picker (EnhancedModelPickerActionItem)
+		this._localModelPickerContainer = dom.append(toolbar, dom.$('.sessions-chat-model-picker'));
+		this._createLocalModelPicker(this._localModelPickerContainer);
+
+		// Remote model picker (action list dropdown)
+		this._cloudModelPicker.render(toolbar);
+		this._cloudModelPicker.setVisible(false);
+
+		this._toolbarPickersContainer = dom.append(toolbar, dom.$('.sessions-chat-toolbar-pickers'));
 
 		dom.append(toolbar, dom.$('.sessions-chat-toolbar-spacer'));
 
@@ -467,21 +713,23 @@ class NewChatWidget extends Disposable {
 
 	// --- Model picker ---
 
-	private _createModelPicker(container: HTMLElement): void {
+	private _createLocalModelPicker(container: HTMLElement): void {
 		const delegate: IModelPickerDelegate = {
 			currentModel: this._currentLanguageModel,
 			setModel: (model: ILanguageModelChatMetadataAndIdentifier) => {
 				this._currentLanguageModel.set(model, undefined);
-				this.storageService.store(STORAGE_KEY_LAST_MODEL, model.identifier, StorageScope.PROFILE, StorageTarget.MACHINE);
 				this._newSession.value?.setModelId(model.identifier);
 				this._focusEditor();
 			},
 			getModels: () => this._getAvailableModels(),
-			canManageModels: () => false,
+			useGroupedModelPicker: () => true,
+			showManageModelsAction: () => false,
+			showUnavailableFeatured: () => false,
+			showFeatured: () => true,
 		};
 
 		const pickerOptions: IChatInputPickerOptions = {
-			onlyShowIconsForDefaultActions: observableValue('onlyShowIcons', false),
+			hideChevrons: observableValue('hideChevrons', false),
 			hoverPosition: { hoverPosition: HoverPosition.ABOVE },
 		};
 
@@ -495,27 +743,11 @@ class NewChatWidget extends Disposable {
 	}
 
 	private _initDefaultModel(): void {
-		const lastModelId = this.storageService.get(STORAGE_KEY_LAST_MODEL, StorageScope.PROFILE);
 		const models = this._getAvailableModels();
-		const lastModel = lastModelId ? models.find(m => m.identifier === lastModelId) : undefined;
-		if (lastModel) {
-			this._currentLanguageModel.set(lastModel, undefined);
-		} else if (models.length > 0) {
-			this._currentLanguageModel.set(models[0], undefined);
-		}
-
-		this._register(this.languageModelsService.onDidChangeLanguageModels(() => {
-			if (!this._currentLanguageModel.get()) {
-				const storedId = this.storageService.get(STORAGE_KEY_LAST_MODEL, StorageScope.PROFILE);
-				const updated = this._getAvailableModels();
-				const stored = storedId ? updated.find(m => m.identifier === storedId) : undefined;
-				if (stored) {
-					this._currentLanguageModel.set(stored, undefined);
-				} else if (updated.length > 0) {
-					this._currentLanguageModel.set(updated[0], undefined);
-				}
-			}
-		}));
+		const draft = this._getDraftState();
+		const lastModelId = draft?.selectedModel?.identifier ?? this._history.values.at(-1)?.selectedModel?.identifier;
+		const defaultModel = (lastModelId ? models.find(m => m.identifier === lastModelId) : undefined) ?? models[0];
+		this._currentLanguageModel.set(defaultModel, undefined);
 	}
 
 	private _getAvailableModels(): ILanguageModelChatMetadataAndIdentifier[] {
@@ -534,7 +766,7 @@ class NewChatWidget extends Disposable {
 			return;
 		}
 
-		this._clearExtensionPickers();
+		this._clearAllPickers();
 		dom.clearNode(this._pickersContainer);
 
 		const pickersRow = dom.append(this._pickersContainer, dom.$('.chat-full-welcome-pickers'));
@@ -547,178 +779,137 @@ class NewChatWidget extends Disposable {
 		// Right half: separator + pickers (left-justified within its half)
 		const rightHalf = dom.append(pickersRow, dom.$('.sessions-chat-pickers-right-half'));
 		this._extensionPickersLeftContainer = dom.append(rightHalf, dom.$('.sessions-chat-pickers-left-separator'));
-		this._extensionPickersRightContainer = dom.append(rightHalf, dom.$('.sessions-chat-extension-pickers-right'));
+		this._extensionPickersLeftContainer.style.display = 'none';
 
-		// Folder picker (rendered once, shown/hidden based on target)
+		// Repo picker for cloud (rendered once, shown/hidden based on target)
+		this._repoPickerContainer = dom.append(rightHalf, dom.$('.sessions-chat-extension-pickers-right'));
+		this._repoPickerContainer.style.display = 'none';
+		this._repoPicker.render(this._repoPickerContainer);
+
+		// Folder picker for local (rendered once, shown/hidden based on target)
 		this._folderPickerContainer = this._folderPicker.render(rightHalf);
 		this._folderPickerContainer.style.display = 'none';
-
-		this._renderExtensionPickers();
 	}
 
-	// --- Welcome: Extension option pickers (Cloud target only) ---
+	// --- Local session pickers ---
 
-	private _renderExtensionPickers(force?: boolean): void {
-		if (!this._extensionPickersRightContainer) {
-			return;
+	private _renderLocalSessionPickers(): void {
+		this._clearAllPickers();
+		if (this._folderPickerContainer) {
+			this._folderPickerContainer.style.display = '';
 		}
-
-		const activeSessionType = this._targetPicker.selectedTarget;
-
-		// Extension pickers are only shown for Cloud target
-		if (activeSessionType === AgentSessionProviders.Background) {
-			this._clearExtensionPickers();
-			if (this._folderPickerContainer) {
-				this._folderPickerContainer.style.display = '';
-			}
-			if (this._extensionPickersLeftContainer) {
-				this._extensionPickersLeftContainer.style.display = 'block';
-			}
-			return;
+		if (this._extensionPickersLeftContainer) {
+			this._extensionPickersLeftContainer.style.display = 'block';
 		}
-
-		const optionGroups = this.chatSessionsService.getOptionGroupsForSessionType(activeSessionType);
-		if (!optionGroups || optionGroups.length === 0) {
-			this._clearExtensionPickers();
-			return;
+		// Show local model and mode pickers, hide remote
+		if (this._localModelPickerContainer) {
+			this._localModelPickerContainer.style.display = '';
 		}
+		this._modePicker.setVisible(true);
+		this._cloudModelPicker.setVisible(false);
+	}
 
-		const visibleGroups: IChatSessionProviderOptionGroup[] = [];
-		this._whenClauseKeys.clear();
-		for (const group of optionGroups) {
-			if (isModelOptionGroup(group)) {
-				continue;
-			}
-			if (group.when) {
-				const expr = ContextKeyExpr.deserialize(group.when);
-				if (expr) {
-					for (const key of expr.keys()) {
-						this._whenClauseKeys.add(key);
-					}
-				}
-			}
-			const hasItems = group.items.length > 0 || (group.commands || []).length > 0 || !!group.searchable;
-			const passesWhenClause = this._evaluateOptionGroupVisibility(group);
-			if (hasItems && passesWhenClause) {
-				visibleGroups.push(group);
-			}
-		}
+	// --- Remote session pickers ---
 
-		if (visibleGroups.length === 0) {
-			this._clearExtensionPickers();
+	private _renderRemoteSessionPickers(session: RemoteNewSession, force?: boolean): void {
+		if (!this._repoPickerContainer) {
 			return;
 		}
 
-		if (!force && this._pickerWidgets.size === visibleGroups.length) {
-			const allMatch = visibleGroups.every(g => this._pickerWidgets.has(g.id));
-			if (allMatch) {
-				return;
-			}
+		// Hide local-only pickers
+		if (this._folderPickerContainer) {
+			this._folderPickerContainer.style.display = 'none';
 		}
 
-		this._clearExtensionPickers();
+		// Show remote model picker, hide local pickers
+		if (this._localModelPickerContainer) {
+			this._localModelPickerContainer.style.display = 'none';
+		}
+		this._modePicker.setVisible(false);
+		this._cloudModelPicker.setSession(session);
+		this._cloudModelPicker.setVisible(true);
 
+		// Show repo picker and separator
 		if (this._extensionPickersLeftContainer) {
 			this._extensionPickersLeftContainer.style.display = 'block';
 		}
+		this._repoPickerContainer.style.display = '';
 
-		for (const optionGroup of visibleGroups) {
-			const initialItem = this._getDefaultOptionForGroup(optionGroup);
-			const initialState = { group: optionGroup, item: initialItem };
-
-			if (initialItem) {
-				this._updateOptionContextKey(optionGroup.id, initialItem.id);
-			}
+		// Render toolbar pickers (other groups)
+		this._renderToolbarPickers(session, force);
+	}
 
-			const emitter = this._getOrCreateOptionEmitter(optionGroup.id);
-			const itemDelegate: IChatSessionPickerDelegate = {
-				getCurrentOption: () => this._selectedOptions.get(optionGroup.id) ?? this._getDefaultOptionForGroup(optionGroup),
-				onDidChangeOption: emitter.event,
-				setOption: (option: IChatSessionProviderOptionItem) => {
-					this._selectedOptions.set(optionGroup.id, option);
-					this._updateOptionContextKey(optionGroup.id, option.id);
-					emitter.fire(option);
-
-					this._newSession.value?.setOption(optionGroup.id, option);
-
-					this._renderExtensionPickers(true);
-					this._focusEditor();
-				},
-				getOptionGroup: () => {
-					const groups = this.chatSessionsService.getOptionGroupsForSessionType(activeSessionType);
-					return groups?.find((g: { id: string }) => g.id === optionGroup.id);
-				},
-				getSessionResource: () => this._newSession.value?.resource,
-			};
+	private _renderToolbarPickers(session: RemoteNewSession, force?: boolean): void {
+		if (!this._toolbarPickersContainer) {
+			return;
+		}
 
-			const action = toAction({ id: optionGroup.id, label: optionGroup.name, run: () => { } });
-			const widget = this.instantiationService.createInstance(
-				optionGroup.searchable ? SearchableOptionPickerActionItem : ChatSessionPickerActionItem,
-				action, initialState, itemDelegate
-			);
+		const toolbarOptions = session.getOtherOptionGroups();
 
-			this._pickerWidgetDisposables.add(widget);
-			this._pickerWidgets.set(optionGroup.id, widget);
+		// Filter by item availability (when-clause filtering is done by the session)
+		const visibleGroups = toolbarOptions.filter(option => {
+			const group = option.group;
+			return group.items.length > 0 || (group.commands || []).length > 0 || !!group.searchable;
+		});
 
-			const slot = dom.append(this._extensionPickersRightContainer!, dom.$('.sessions-chat-picker-slot'));
-			widget.render(slot);
+		if (visibleGroups.length === 0) {
+			this._clearToolbarPickers();
+			return;
 		}
-	}
 
-	private _evaluateOptionGroupVisibility(optionGroup: { id: string; when?: string }): boolean {
-		if (!optionGroup.when) {
-			return true;
+		if (!force) {
+			const allMatch = visibleGroups.length === this._toolbarPickerWidgets.size && visibleGroups.every(o => this._toolbarPickerWidgets.has(o.group.id));
+			if (allMatch) {
+				return;
+			}
 		}
-		const expr = ContextKeyExpr.deserialize(optionGroup.when);
-		return !expr || this.contextKeyService.contextMatchesRules(expr);
-	}
 
-	private _getDefaultOptionForGroup(optionGroup: IChatSessionProviderOptionGroup): IChatSessionProviderOptionItem | undefined {
-		const selectedOption = this._selectedOptions.get(optionGroup.id);
-		if (selectedOption) {
-			return selectedOption;
-		}
+		this._clearToolbarPickers();
 
-		if (this._newSession.value) {
-			const sessionOption = this.chatSessionsService.getSessionOption(this._newSession.value.resource, optionGroup.id);
-			if (!isString(sessionOption)) {
-				return sessionOption;
-			}
+		for (const option of visibleGroups) {
+			this._renderToolbarPickerWidget(option, session);
 		}
-
-		return optionGroup.items.find((item) => item.default === true);
 	}
 
-	private _syncOptionsFromSession(sessionResource: URI): void {
-		const activeSessionType = this._targetPicker.selectedTarget;
-		if (!activeSessionType) {
-			return;
-		}
-		const optionGroups = this.chatSessionsService.getOptionGroupsForSessionType(activeSessionType);
-		if (!optionGroups) {
-			return;
+	private _renderToolbarPickerWidget(option: ISessionOptionGroup, session: RemoteNewSession): void {
+		const { group: optionGroup, value: initialItem } = option;
+
+		if (initialItem) {
+			this._updateOptionContextKey(optionGroup.id, initialItem.id);
 		}
-		for (const optionGroup of optionGroups) {
-			if (isModelOptionGroup(optionGroup)) {
-				continue;
-			}
-			const currentOption = this.chatSessionsService.getSessionOption(sessionResource, optionGroup.id);
-			if (!currentOption) {
-				continue;
-			}
-			let item: IChatSessionProviderOptionItem | undefined;
-			if (typeof currentOption === 'string') {
-				item = optionGroup.items.find((m: { id: string }) => m.id === currentOption.trim());
-			} else {
-				item = currentOption;
-			}
-			if (item) {
-				const { locked: _locked, ...unlocked } = item;
-				this._selectedOptions.set(optionGroup.id, unlocked as IChatSessionProviderOptionItem);
+
+		const initialState = { group: optionGroup, item: initialItem };
+		const emitter = this._getOrCreateOptionEmitter(optionGroup.id);
+		const itemDelegate: IChatSessionPickerDelegate = {
+			getCurrentOption: () => session.getOptionValue(optionGroup.id) ?? initialItem,
+			onDidChangeOption: emitter.event,
+			setOption: (item: IChatSessionProviderOptionItem) => {
 				this._updateOptionContextKey(optionGroup.id, item.id);
-				this._optionEmitters.get(optionGroup.id)?.fire(item);
-			}
-		}
+				emitter.fire(item);
+				session.setOptionValue(optionGroup.id, item);
+				this._focusEditor();
+			},
+			getOptionGroup: () => {
+				const modelOpt = session.getModelOptionGroup();
+				if (modelOpt?.group.id === optionGroup.id) {
+					return modelOpt.group;
+				}
+				return session.getOtherOptionGroups().find(o => o.group.id === optionGroup.id)?.group;
+			},
+			getSessionResource: () => session.resource,
+		};
+
+		const action = toAction({ id: optionGroup.id, label: optionGroup.name, run: () => { } });
+		const widget = this.instantiationService.createInstance(
+			optionGroup.searchable ? SearchableOptionPickerActionItem : ChatSessionPickerActionItem,
+			action, initialState, itemDelegate, undefined
+		);
+
+		this._toolbarPickerDisposables.add(widget);
+		this._toolbarPickerWidgets.set(optionGroup.id, widget);
+
+		const slot = dom.append(this._toolbarPickersContainer!, dom.$('.sessions-chat-picker-slot'));
+		widget.render(slot);
 	}
 
 	private _updateOptionContextKey(optionGroupId: string, optionItemId: string): void {
@@ -736,23 +927,88 @@ class NewChatWidget extends Disposable {
 		if (!emitter) {
 			emitter = new Emitter<IChatSessionProviderOptionItem>();
 			this._optionEmitters.set(optionGroupId, emitter);
-			this._pickerWidgetDisposables.add(emitter);
+			this._toolbarPickerDisposables.add(emitter);
 		}
 		return emitter;
 	}
 
-	private _clearExtensionPickers(): void {
-		this._pickerWidgetDisposables.clear();
-		this._pickerWidgets.clear();
+	private _clearToolbarPickers(): void {
+		this._toolbarPickerDisposables.clear();
+		this._toolbarPickerWidgets.clear();
 		this._optionEmitters.clear();
+		if (this._toolbarPickersContainer) {
+			dom.clearNode(this._toolbarPickersContainer);
+		}
+	}
+
+	private _clearAllPickers(): void {
+		this._clearToolbarPickers();
 		if (this._folderPickerContainer) {
 			this._folderPickerContainer.style.display = 'none';
 		}
+		if (this._repoPickerContainer) {
+			this._repoPickerContainer.style.display = 'none';
+		}
 		if (this._extensionPickersLeftContainer) {
 			this._extensionPickersLeftContainer.style.display = 'none';
 		}
-		if (this._extensionPickersRightContainer) {
-			dom.clearNode(this._extensionPickersRightContainer);
+	}
+
+	// --- Input History (IHistoryNavigationWidget) ---
+
+	showPreviousValue(): void {
+		if (this._history.isAtStart()) {
+			return;
+		}
+		if (this._draftState?.inputText || this._draftState?.attachments.length) {
+			this._history.overlay(this._draftState);
+		}
+		this._navigateHistory(true);
+	}
+
+	showNextValue(): void {
+		if (this._history.isAtEnd()) {
+			return;
+		}
+		if (this._draftState?.inputText || this._draftState?.attachments.length) {
+			this._history.overlay(this._draftState);
+		}
+		this._navigateHistory(false);
+	}
+
+	private _updateDraftState(): void {
+		const attachments = [...this._contextAttachments.attachments];
+		this._draftState = {
+			inputText: this._editor?.getModel()?.getValue() ?? '',
+			attachments,
+			mode: { id: ChatModeKind.Agent, kind: ChatModeKind.Agent },
+			selectedModel: this._currentLanguageModel.get(),
+			selections: this._editor?.getSelections() ?? [],
+			contrib: {},
+			target: this._targetPicker.selectedTarget,
+			isolationMode: this._isolationModePicker.isolationMode,
+			branch: this._branchPicker.selectedBranch,
+			folderUri: this._folderPicker.selectedFolderUri?.toString(),
+			repo: this._repoPicker.selectedRepo,
+		};
+	}
+
+	private _navigateHistory(previous: boolean): void {
+		const entry = previous ? this._history.previous() : this._history.next();
+		const inputText = entry?.inputText ?? '';
+		if (entry) {
+			this._editor?.getModel()?.setValue(inputText);
+			this._contextAttachments.setAttachments(entry.attachments);
+		}
+		aria.status(inputText);
+		if (previous) {
+			this._editor.setPosition({ lineNumber: 1, column: 1 });
+		} else {
+			const model = this._editor.getModel();
+			if (model) {
+				const lastLine = model.getLineCount();
+				this._editor.setPosition({ lineNumber: lastLine, column: model.getLineMaxColumn(lastLine) });
+			}
 		}
 	}
 
@@ -766,41 +1022,193 @@ class NewChatWidget extends Disposable {
 		this._sendButton.enabled = !this._sending && hasText && !(this._newSession.value?.disabled ?? true);
 	}
 
-	private _send(): void {
-		const query = this._editor.getModel()?.getValue().trim();
+	private async _send(): Promise<void> {
+		let query = this._editor.getModel()?.getValue().trim();
 		const session = this._newSession.value;
-		if (!query || !session || session.disabled || this._sending) {
+		if (!query || !session || this._sending) {
 			return;
 		}
 
+		// If the session is disabled due to missing folder/repo, open the picker
+		if (session.disabled) {
+			if (!this._hasRequiredRepoOrFolderSelection(session.target)) {
+				this._openRepoOrFolderPicker(session.target);
+			}
+			return;
+		}
+
+		// Check for slash commands first
+		if (this._slashCommandHandler?.tryExecuteSlashCommand(query)) {
+			this._editor.getModel()?.setValue('');
+			return;
+		}
+
+		// Expand prompt/skill slash commands into a CLI-friendly reference
+		const expanded = this._slashCommandHandler?.tryExpandPromptSlashCommand(query);
+		if (expanded) {
+			query = expanded;
+		}
+
 		session.setQuery(query);
 		session.setAttachedContext(
 			this._contextAttachments.attachments.length > 0 ? [...this._contextAttachments.attachments] : undefined
 		);
 
+		if (this._draftState) {
+			this._history.append(this._draftState);
+		}
+		this._clearDraftState();
+
 		this._sending = true;
 		this._editor.updateOptions({ readOnly: true });
 		this._updateSendButtonState();
 		this._updateInputLoadingState();
 
-		this.sessionsManagementService.sendRequestForNewSession(
-			session.resource
-		).then(() => {
-			// Release ref without disposing - the service owns disposal
-			this._newSession.clearAndLeak();
+
+		try {
+			await this.sessionsManagementService.sendRequestForNewSession(
+				session.resource,
+				{
+					permissionLevel: this._permissionPicker.permissionLevel,
+				}
+			);
 			this._newSessionListener.clear();
 			this._contextAttachments.clear();
-		}, e => {
+			this._editor.getModel()?.setValue('');
+		} catch (e) {
 			this.logService.error('Failed to send request:', e);
-		}).finally(() => {
-			this._sending = false;
-			this._editor.updateOptions({ readOnly: false });
-			this._updateSendButtonState();
-			this._updateInputLoadingState();
+		}
+
+
+		this._sending = false;
+		this._editor.updateOptions({ readOnly: false });
+		this._updateSendButtonState();
+		this._updateInputLoadingState();
+	}
+
+	/**
+	 * Checks whether the required folder/repo selection exists for the given session type.
+	 * For Local/Background targets, checks the folder picker.
+	 * For other targets, checks extension-contributed repo/folder option groups.
+	 */
+	private _hasRequiredRepoOrFolderSelection(sessionType: AgentSessionProviders): boolean {
+		if (sessionType === AgentSessionProviders.Local || sessionType === AgentSessionProviders.Background) {
+			return !!this._folderPicker.selectedFolderUri;
+		}
+		return !!this._repoPicker.selectedRepo;
+	}
+
+	private _openRepoOrFolderPicker(sessionType: AgentSessionProviders): void {
+		if (sessionType === AgentSessionProviders.Local || sessionType === AgentSessionProviders.Background) {
+			this._folderPicker.showPicker();
+		} else {
+			this._repoPicker.showPicker();
+		}
+	}
+
+	private async _requestFolderTrust(folderUri: URI): Promise<boolean> {
+		const trusted = await this.workspaceTrustRequestService.requestResourcesTrust({
+			uri: folderUri,
+			message: localize('trustFolderMessage', "An agent session will be able to read files, run commands, and make changes in this folder."),
 		});
+		if (!trusted) {
+			this._folderPicker.removeFromRecents(folderUri);
+			const previousFolderUri = this._newSession.value?.repoUri;
+			if (previousFolderUri) {
+				this._folderPicker.setSelectedFolder(previousFolderUri);
+			} else {
+				this._folderPicker.clearSelection();
+			}
+		}
+		return !!trusted;
+	}
+
+
+	private _resolveDefaultTarget(options: INewChatWidgetOptions): AgentSessionProviders {
+		const draft = this._getDraftState();
+		if (draft?.target && options.allowedTargets.includes(draft.target)) {
+			return draft.target;
+		}
+		return options.defaultTarget;
+	}
+
+	private _restoreState(): void {
+		const draft = this._getDraftState();
+		if (draft) {
+			this._editor?.getModel()?.setValue(draft.inputText);
+			if (draft.attachments?.length) {
+				this._contextAttachments.setAttachments(draft.attachments.map(IChatRequestVariableEntry.fromExport));
+			}
+			if (draft.selectedModel) {
+				const models = this._getAvailableModels();
+				const model = models.find(m => m.identifier === draft.selectedModel?.identifier);
+				if (model) {
+					this._currentLanguageModel.set(model, undefined);
+				}
+			}
+			if (draft.isolationMode) {
+				if (this._isIsolationOptionEnabled) {
+					this._isolationModePicker.setPreferredIsolationMode(draft.isolationMode);
+					this._isolationModePicker.setIsolationMode(draft.isolationMode);
+				} else {
+					this._isolationModePicker.setPreferredIsolationMode('worktree');
+					this._isolationModePicker.setIsolationMode('worktree');
+				}
+			}
+			if (draft.branch) {
+				this._branchPicker.setPreferredBranch(draft.branch);
+			}
+			if (draft.folderUri) {
+				try { this._folderPicker.setSelectedFolder(URI.parse(draft.folderUri)); } catch { /* ignore */ }
+			}
+			if (draft.repo) {
+				this._repoPicker.setSelectedRepo(draft.repo);
+			}
+		}
 	}
 
-	// --- Layout ---
+	private _getDraftState(): IDraftState | undefined {
+		const raw = this.storageService.get(STORAGE_KEY_DRAFT_STATE, StorageScope.WORKSPACE);
+		if (!raw) {
+			return undefined;
+		}
+		try {
+			return JSON.parse(raw);
+		} catch {
+			return undefined;
+		}
+	}
+
+	private _clearDraftState(): void {
+		// Preserve picker preferences so they survive widget recreation
+		const target = this._targetPicker.selectedTarget;
+		const isLocal = target === AgentSessionProviders.Background;
+		const preserved: IDraftState = {
+			inputText: '',
+			attachments: [],
+			mode: { id: ChatModeKind.Agent, kind: ChatModeKind.Agent },
+			selectedModel: this._draftState?.selectedModel,
+			selections: [],
+			contrib: {},
+			target,
+			isolationMode: isLocal ? this._isolationModePicker.isolationMode : undefined,
+			branch: isLocal ? this._branchPicker.selectedBranch : undefined,
+			folderUri: isLocal ? this._folderPicker.selectedFolderUri?.toString() : undefined,
+			repo: isLocal ? undefined : this._repoPicker.selectedRepo,
+		};
+		this._draftState = preserved;
+		this.storageService.store(STORAGE_KEY_DRAFT_STATE, JSON.stringify(preserved), StorageScope.WORKSPACE, StorageTarget.MACHINE);
+	}
+
+	saveState(): void {
+		if (this._draftState) {
+			const state = {
+				...this._draftState,
+				attachments: this._draftState.attachments.map(IChatRequestVariableEntry.toExport),
+			};
+			this.storageService.store(STORAGE_KEY_DRAFT_STATE, JSON.stringify(state), StorageScope.WORKSPACE, StorageTarget.MACHINE);
+		}
+	}
 
 	layout(_height: number, _width: number): void {
 		this._editor?.layout();
@@ -810,6 +1218,26 @@ class NewChatWidget extends Disposable {
 		this._editor?.focus();
 	}
 
+	prefillInput(text: string): void {
+		const editor = this._editor;
+		const model = editor?.getModel();
+		if (editor && model) {
+			model.setValue(text);
+			const lastLine = model.getLineCount();
+			const maxColumn = model.getLineMaxColumn(lastLine);
+			editor.setPosition({ lineNumber: lastLine, column: maxColumn });
+			editor.focus();
+		}
+	}
+
+	sendQuery(text: string): void {
+		const model = this._editor?.getModel();
+		if (model) {
+			model.setValue(text);
+			this._send();
+		}
+	}
+
 	updateAllowedTargets(targets: AgentSessionProviders[]): void {
 		this._targetPicker.updateAllowedTargets(targets);
 	}
@@ -878,37 +1306,29 @@ export class NewChatViewPane extends ViewPane {
 		this._widget?.focusInput();
 	}
 
+	prefillInput(text: string): void {
+		this._widget?.prefillInput(text);
+	}
+
+	sendQuery(text: string): void {
+		this._widget?.sendQuery(text);
+	}
+
 	override setVisible(visible: boolean): void {
 		super.setVisible(visible);
 		if (visible) {
 			this._widget?.focusInput();
 		}
 	}
-}
 
-// #endregion
+	override saveState(): void {
+		this._widget?.saveState();
+	}
 
-/**
- * Check whether an option group represents the model picker.
- * The convention is `id: 'models'` but extensions may use different IDs
- * per session type, so we also fall back to name matching.
- */
-function isModelOptionGroup(group: IChatSessionProviderOptionGroup): boolean {
-	if (group.id === 'models') {
-		return true;
+	override dispose(): void {
+		this._widget?.saveState();
+		super.dispose();
 	}
-	const nameLower = group.name.toLowerCase();
-	return nameLower === 'model' || nameLower === 'models';
 }
 
-/**
- * Check whether an option group represents a repository or folder picker.
- * These are placed on the right side of the pickers row.
- */
-function isRepoOrFolderGroup(group: IChatSessionProviderOptionGroup): boolean {
-	const idLower = group.id.toLowerCase();
-	const nameLower = group.name.toLowerCase();
-	return idLower === 'repositories' || idLower === 'folders' ||
-		nameLower === 'repository' || nameLower === 'repositories' ||
-		nameLower === 'folder' || nameLower === 'folders';
-}
+// #endregion
diff --git a/src/vs/sessions/contrib/chat/browser/newSession.ts b/src/vs/sessions/contrib/chat/browser/newSession.ts
index 2e601215b535a..232f56251cc88 100644
--- a/src/vs/sessions/contrib/chat/browser/newSession.ts
+++ b/src/vs/sessions/contrib/chat/browser/newSession.ts
@@ -6,15 +6,24 @@
 import { Emitter, Event } from '../../../../base/common/event.js';
 import { Disposable, IDisposable } from '../../../../base/common/lifecycle.js';
 import { URI } from '../../../../base/common/uri.js';
-import { isEqual } from '../../../../base/common/resources.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
-import { IChatSessionProviderOptionItem, IChatSessionsService } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
+import { IChatSessionProviderOptionGroup, IChatSessionProviderOptionItem, IChatSessionsService } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
 import { IsolationMode } from './sessionTargetPicker.js';
 import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
+import { ContextKeyExpr, IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
 
 import { IChatRequestVariableEntry } from '../../../../workbench/contrib/chat/common/attachments/chatVariableEntries.js';
+import { IChatMode } from '../../../../workbench/contrib/chat/common/chatModes.js';
 
-export type NewSessionChangeType = 'repoUri' | 'isolationMode' | 'branch' | 'options' | 'disabled';
+export type NewSessionChangeType = 'repoUri' | 'isolationMode' | 'branch' | 'options' | 'disabled' | 'agent';
+
+/**
+ * Represents a resolved option group with its current selected value.
+ */
+export interface ISessionOptionGroup {
+	readonly group: IChatSessionProviderOptionGroup;
+	readonly value: IChatSessionProviderOptionItem | undefined;
+}
 
 /**
  * A new session represents a session being configured before the first
@@ -28,6 +37,7 @@ export interface INewSession extends IDisposable {
 	readonly isolationMode: IsolationMode;
 	readonly branch: string | undefined;
 	readonly modelId: string | undefined;
+	readonly mode: IChatMode | undefined;
 	readonly query: string | undefined;
 	readonly attachedContext: IChatRequestVariableEntry[] | undefined;
 	readonly selectedOptions: ReadonlyMap<string, IChatSessionProviderOptionItem>;
@@ -37,6 +47,7 @@ export interface INewSession extends IDisposable {
 	setIsolationMode(mode: IsolationMode): void;
 	setBranch(branch: string | undefined): void;
 	setModelId(modelId: string | undefined): void;
+	setMode(mode: IChatMode | undefined): void;
 	setQuery(query: string): void;
 	setAttachedContext(context: IChatRequestVariableEntry[] | undefined): void;
 	setOption(optionId: string, value: IChatSessionProviderOptionItem | string): void;
@@ -45,6 +56,7 @@ export interface INewSession extends IDisposable {
 const REPOSITORY_OPTION_ID = 'repository';
 const BRANCH_OPTION_ID = 'branch';
 const ISOLATION_OPTION_ID = 'isolation';
+const AGENT_OPTION_ID = 'agent';
 
 /**
  * Local new session for Background agent sessions.
@@ -57,6 +69,7 @@ export class LocalNewSession extends Disposable implements INewSession {
 	private _isolationMode: IsolationMode = 'worktree';
 	private _branch: string | undefined;
 	private _modelId: string | undefined;
+	private _mode: IChatMode | undefined;
 	private _query: string | undefined;
 	private _attachedContext: IChatRequestVariableEntry[] | undefined;
 
@@ -70,6 +83,7 @@ export class LocalNewSession extends Disposable implements INewSession {
 	get isolationMode(): IsolationMode { return this._isolationMode; }
 	get branch(): string | undefined { return this._branch; }
 	get modelId(): string | undefined { return this._modelId; }
+	get mode(): IChatMode | undefined { return this._mode; }
 	get query(): string | undefined { return this._query; }
 	get attachedContext(): IChatRequestVariableEntry[] | undefined { return this._attachedContext; }
 	get disabled(): boolean {
@@ -85,8 +99,8 @@ export class LocalNewSession extends Disposable implements INewSession {
 	constructor(
 		readonly resource: URI,
 		defaultRepoUri: URI | undefined,
-		private readonly chatSessionsService: IChatSessionsService,
-		private readonly logService: ILogService,
+		@IChatSessionsService private readonly chatSessionsService: IChatSessionsService,
+		@ILogService private readonly logService: ILogService,
 	) {
 		super();
 		if (defaultRepoUri) {
@@ -126,6 +140,15 @@ export class LocalNewSession extends Disposable implements INewSession {
 		this._modelId = modelId;
 	}
 
+	setMode(mode: IChatMode | undefined): void {
+		if (this._mode?.id !== mode?.id) {
+			this._mode = mode;
+			this._onDidChange.fire('agent');
+			const modeName = mode?.isBuiltin ? undefined : mode?.name.get();
+			this.setOption(AGENT_OPTION_ID, modeName ?? '');
+		}
+	}
+
 	setQuery(query: string): void {
 		this._query = query;
 	}
@@ -149,13 +172,12 @@ export class LocalNewSession extends Disposable implements INewSession {
 
 /**
  * Remote new session for Cloud agent sessions.
- * Fires `onDidChange` and notifies the extension service when `repoUri` changes.
- * Ignores `isolationMode` (not relevant for cloud).
+ * Manages extension-driven option groups (models, etc.) and their values.
+ * Fires events for option group changes.
  */
 export class RemoteNewSession extends Disposable implements INewSession {
 
 	private _repoUri: URI | undefined;
-	private _isolationMode: IsolationMode = 'worktree';
 	private _modelId: string | undefined;
 	private _query: string | undefined;
 	private _attachedContext: IChatRequestVariableEntry[] | undefined;
@@ -163,33 +185,43 @@ export class RemoteNewSession extends Disposable implements INewSession {
 	private readonly _onDidChange = this._register(new Emitter<NewSessionChangeType>());
 	readonly onDidChange: Event<NewSessionChangeType> = this._onDidChange.event;
 
+	private readonly _onDidChangeOptionGroups = this._register(new Emitter<void>());
+	readonly onDidChangeOptionGroups: Event<void> = this._onDidChangeOptionGroups.event;
+
 	readonly selectedOptions = new Map<string, IChatSessionProviderOptionItem>();
 
 	get repoUri(): URI | undefined { return this._repoUri; }
-	get isolationMode(): IsolationMode { return this._isolationMode; }
+	get isolationMode(): IsolationMode { return 'worktree'; }
 	get branch(): string | undefined { return undefined; }
 	get modelId(): string | undefined { return this._modelId; }
+	get mode(): IChatMode | undefined { return undefined; }
 	get query(): string | undefined { return this._query; }
 	get attachedContext(): IChatRequestVariableEntry[] | undefined { return this._attachedContext; }
 	get disabled(): boolean {
-		return !this._repoUri && !this._hasRepositoryOption();
+		return !this._repoUri && !this.selectedOptions.has('repositories');
 	}
 
+	private readonly _whenClauseKeys = new Set<string>();
+
 	constructor(
 		readonly resource: URI,
 		readonly target: AgentSessionProviders,
-		private readonly chatSessionsService: IChatSessionsService,
-		private readonly logService: ILogService,
+		@IChatSessionsService private readonly chatSessionsService: IChatSessionsService,
+		@IContextKeyService private readonly contextKeyService: IContextKeyService,
+		@ILogService private readonly logService: ILogService,
 	) {
 		super();
 
-		// Listen for extension-driven option group and session option changes
+		this._updateWhenClauseKeys();
+
 		this._register(this.chatSessionsService.onDidChangeOptionGroups(() => {
+			this._updateWhenClauseKeys();
+			this._onDidChangeOptionGroups.fire();
 			this._onDidChange.fire('options');
 		}));
-		this._register(this.chatSessionsService.onDidChangeSessionOptions((e: URI | undefined) => {
-			if (isEqual(this.resource, e)) {
-				this._onDidChange.fire('options');
+		this._register(this.contextKeyService.onDidChangeContext(e => {
+			if (this._whenClauseKeys.size > 0 && e.affectsSome(this._whenClauseKeys)) {
+				this._onDidChangeOptionGroups.fire();
 			}
 		}));
 	}
@@ -198,21 +230,27 @@ export class RemoteNewSession extends Disposable implements INewSession {
 		this._repoUri = uri;
 		this._onDidChange.fire('repoUri');
 		this._onDidChange.fire('disabled');
-		this.setOption('repository', uri.fsPath);
+		const id = uri.path.substring(1);
+		this.setOption('repositories', { id, name: id });
 	}
 
 	setIsolationMode(_mode: IsolationMode): void {
-		// No-op for remote sessions — isolation mode is not relevant
+		// No-op for remote sessions
 	}
 
 	setBranch(_branch: string | undefined): void {
-		// No-op for remote sessions — branch is not relevant
+		// No-op for remote sessions
 	}
 
 	setModelId(modelId: string | undefined): void {
 		this._modelId = modelId;
 	}
 
+	setMode(_mode: IChatMode | undefined): void {
+		// Intentionally a no-op: remote sessions do not support client-side mode selection.
+		// Any mode or behavior differences are determined by the remote session provider/server.
+	}
+
 	setQuery(query: string): void {
 		this._query = query;
 	}
@@ -233,7 +271,99 @@ export class RemoteNewSession extends Disposable implements INewSession {
 		).catch((err) => this.logService.error(`Failed to notify extension of ${optionId} change:`, err));
 	}
 
-	private _hasRepositoryOption(): boolean {
-		return this.selectedOptions.has('repositories');
+	// --- Option group accessors ---
+
+	getModelOptionGroup(): ISessionOptionGroup | undefined {
+		const groups = this._getOptionGroups();
+		if (!groups) {
+			return undefined;
+		}
+		const group = groups.find(g => isModelOptionGroup(g));
+		if (!group) {
+			return undefined;
+		}
+		return { group, value: this._getValueForGroup(group) };
+	}
+
+	getOtherOptionGroups(): ISessionOptionGroup[] {
+		const groups = this._getOptionGroups();
+		if (!groups) {
+			return [];
+		}
+		return groups
+			.filter(g => !isModelOptionGroup(g) && !isRepositoriesOptionGroup(g) && this._isOptionGroupVisible(g))
+			.map(g => ({ group: g, value: this._getValueForGroup(g) }));
+	}
+
+	getOptionValue(groupId: string): IChatSessionProviderOptionItem | undefined {
+		return this.selectedOptions.get(groupId);
+	}
+
+	setOptionValue(groupId: string, value: IChatSessionProviderOptionItem): void {
+		this.setOption(groupId, value);
 	}
+
+	// --- Internals ---
+
+	private _getOptionGroups(): IChatSessionProviderOptionGroup[] | undefined {
+		return this.chatSessionsService.getOptionGroupsForSessionType(this.target);
+	}
+
+	private _isOptionGroupVisible(group: IChatSessionProviderOptionGroup): boolean {
+		if (!group.when) {
+			return true;
+		}
+		const expr = ContextKeyExpr.deserialize(group.when);
+		return !expr || this.contextKeyService.contextMatchesRules(expr);
+	}
+
+	private _updateWhenClauseKeys(): void {
+		this._whenClauseKeys.clear();
+		const groups = this._getOptionGroups();
+		if (!groups) {
+			return;
+		}
+		for (const group of groups) {
+			if (group.when) {
+				const expr = ContextKeyExpr.deserialize(group.when);
+				if (expr) {
+					for (const key of expr.keys()) {
+						this._whenClauseKeys.add(key);
+					}
+				}
+			}
+		}
+	}
+
+	private _getValueForGroup(group: IChatSessionProviderOptionGroup): IChatSessionProviderOptionItem | undefined {
+		const selected = this.selectedOptions.get(group.id);
+		if (selected) {
+			return selected;
+		}
+		// Check for extension-set session option
+		const sessionOption = this.chatSessionsService.getSessionOption(this.resource, group.id);
+		if (sessionOption && typeof sessionOption !== 'string') {
+			return sessionOption;
+		}
+		if (typeof sessionOption === 'string') {
+			const item = group.items.find(i => i.id === sessionOption.trim());
+			if (item) {
+				return item;
+			}
+		}
+		// Default to first item marked as default, or first item
+		return group.items.find(i => i.default === true) ?? group.items[0];
+	}
+}
+
+function isModelOptionGroup(group: IChatSessionProviderOptionGroup): boolean {
+	if (group.id === 'models') {
+		return true;
+	}
+	const nameLower = group.name.toLowerCase();
+	return nameLower === 'model' || nameLower === 'models';
+}
+
+function isRepositoriesOptionGroup(group: IChatSessionProviderOptionGroup): boolean {
+	return group.id === 'repositories';
 }
diff --git a/src/vs/sessions/contrib/chat/browser/promptsService.ts b/src/vs/sessions/contrib/chat/browser/promptsService.ts
index 69c0e8e2497dd..8cc51fa370ea1 100644
--- a/src/vs/sessions/contrib/chat/browser/promptsService.ts
+++ b/src/vs/sessions/contrib/chat/browser/promptsService.ts
@@ -6,23 +6,246 @@
 import { PromptsService } from '../../../../workbench/contrib/chat/common/promptSyntax/service/promptsServiceImpl.js';
 import { PromptFilesLocator } from '../../../../workbench/contrib/chat/common/promptSyntax/utils/promptFilesLocator.js';
 import { Event } from '../../../../base/common/event.js';
-import { basename, isEqualOrParent, joinPath } from '../../../../base/common/resources.js';
+import { basename, dirname, isEqualOrParent, joinPath } from '../../../../base/common/resources.js';
 import { URI } from '../../../../base/common/uri.js';
+import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { FileAccess } from '../../../../base/common/network.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { IFileService } from '../../../../platform/files/common/files.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
 import { IWorkspaceContextService, IWorkspaceFolder } from '../../../../platform/workspace/common/workspace.js';
-import { HOOKS_SOURCE_FOLDER } from '../../../../workbench/contrib/chat/common/promptSyntax/config/promptFileLocations.js';
+import { HOOKS_SOURCE_FOLDER, SKILL_FILENAME, getCleanPromptName } from '../../../../workbench/contrib/chat/common/promptSyntax/config/promptFileLocations.js';
+import { PromptsType } from '../../../../workbench/contrib/chat/common/promptSyntax/promptTypes.js';
+import { IAgentSkill, IPromptPath, PromptsStorage } from '../../../../workbench/contrib/chat/common/promptSyntax/service/promptsService.js';
+import { BUILTIN_STORAGE, IBuiltinPromptPath } from '../../chat/common/builtinPromptsStorage.js';
 import { IWorkbenchEnvironmentService } from '../../../../workbench/services/environment/common/environmentService.js';
 import { IPathService } from '../../../../workbench/services/path/common/pathService.js';
 import { ISearchService } from '../../../../workbench/services/search/common/search.js';
 import { IUserDataProfileService } from '../../../../workbench/services/userDataProfile/common/userDataProfile.js';
-import { ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
+import { IAICustomizationWorkspaceService } from '../../../../workbench/contrib/chat/common/aiCustomizationWorkspaceService.js';
+import { IWorkspaceTrustManagementService } from '../../../../platform/workspace/common/workspaceTrust.js';
+
+/** URI root for built-in prompts bundled with the Sessions app. */
+export const BUILTIN_PROMPTS_URI = FileAccess.asFileUri('vs/sessions/prompts');
+
+/** URI root for built-in skills bundled with the Sessions app. */
+export const BUILTIN_SKILLS_URI = FileAccess.asFileUri('vs/sessions/skills');
 
 export class AgenticPromptsService extends PromptsService {
+	private _copilotRoot: URI | undefined;
+	private _builtinPromptsCache: Map<PromptsType, Promise<readonly IBuiltinPromptPath[]>> | undefined;
+	private _builtinSkillsCache: Promise<readonly IAgentSkill[]> | undefined;
+
 	protected override createPromptFilesLocator(): PromptFilesLocator {
 		return this.instantiationService.createInstance(AgenticPromptFilesLocator);
 	}
+
+	private getCopilotRoot(): URI {
+		if (!this._copilotRoot) {
+			const pathService = this.instantiationService.invokeFunction(accessor => accessor.get(IPathService));
+			this._copilotRoot = joinPath(pathService.userHome({ preferLocal: true }), '.copilot');
+		}
+		return this._copilotRoot;
+	}
+
+	/**
+	 * Returns built-in prompt files bundled with the Sessions app.
+	 */
+	private async getBuiltinPromptFiles(type: PromptsType): Promise<readonly IBuiltinPromptPath[]> {
+		if (type !== PromptsType.prompt) {
+			return [];
+		}
+
+		if (!this._builtinPromptsCache) {
+			this._builtinPromptsCache = new Map();
+		}
+
+		let cached = this._builtinPromptsCache.get(type);
+		if (!cached) {
+			cached = this.discoverBuiltinPrompts(type);
+			this._builtinPromptsCache.set(type, cached);
+		}
+		return cached;
+	}
+
+	private async discoverBuiltinPrompts(type: PromptsType): Promise<readonly IBuiltinPromptPath[]> {
+		const fileService = this.instantiationService.invokeFunction(accessor => accessor.get(IFileService));
+		const promptsDir = FileAccess.asFileUri('vs/sessions/prompts');
+		try {
+			const stat = await fileService.resolve(promptsDir);
+			if (!stat.children) {
+				return [];
+			}
+			return stat.children
+				.filter(child => !child.isDirectory && child.name.endsWith('.prompt.md'))
+				.map(child => ({ uri: child.resource, storage: BUILTIN_STORAGE, type }));
+		} catch {
+			return [];
+		}
+	}
+
+	//#region Built-in Skills
+
+	/**
+	 * Returns built-in skill metadata, discovering and parsing SKILL.md files
+	 * bundled in the `vs/sessions/skills/` directory.
+	 */
+	private async getBuiltinSkills(): Promise<readonly IAgentSkill[]> {
+		if (!this._builtinSkillsCache) {
+			this._builtinSkillsCache = this.discoverBuiltinSkills();
+		}
+		return this._builtinSkillsCache;
+	}
+
+	/**
+	 * Discovers built-in skills from `vs/sessions/skills/{name}/SKILL.md`.
+	 * Each subdirectory containing a SKILL.md is treated as a skill.
+	 */
+	private async discoverBuiltinSkills(): Promise<readonly IAgentSkill[]> {
+		const fileService = this.instantiationService.invokeFunction(accessor => accessor.get(IFileService));
+		try {
+			const stat = await fileService.resolve(BUILTIN_SKILLS_URI);
+			if (!stat.children) {
+				return [];
+			}
+
+			const skills: IAgentSkill[] = [];
+			for (const child of stat.children) {
+				if (!child.isDirectory) {
+					continue;
+				}
+				const skillFileUri = joinPath(child.resource, SKILL_FILENAME);
+				try {
+					const parsed = await this.parseNew(skillFileUri, CancellationToken.None);
+					const rawName = parsed.header?.name;
+					const rawDescription = parsed.header?.description;
+					if (!rawName || !rawDescription) {
+						continue;
+					}
+					const name = sanitizeSkillText(rawName, 64);
+					const description = sanitizeSkillText(rawDescription, 1024);
+					const folderName = basename(child.resource);
+					if (name !== folderName) {
+						continue;
+					}
+					skills.push({
+						uri: skillFileUri,
+						storage: BUILTIN_STORAGE as PromptsStorage,
+						name,
+						description,
+						disableModelInvocation: parsed.header?.disableModelInvocation === true,
+						userInvocable: parsed.header?.userInvocable !== false,
+					});
+				} catch (e) {
+					this.logger.warn(`[discoverBuiltinSkills] Failed to parse built-in skill: ${skillFileUri}`, e instanceof Error ? e.message : String(e));
+				}
+			}
+			return skills;
+		} catch {
+			return [];
+		}
+	}
+
+	/**
+	 * Returns built-in skill file paths for listing in the UI.
+	 */
+	private async getBuiltinSkillPaths(): Promise<readonly IBuiltinPromptPath[]> {
+		const skills = await this.getBuiltinSkills();
+		return skills.map(s => ({
+			uri: s.uri,
+			storage: BUILTIN_STORAGE,
+			type: PromptsType.skill,
+		}));
+	}
+
+	/**
+	 * Override to include built-in skills, appending them with lowest priority.
+	 * Skills from any other source (workspace, user, extension, internal) take precedence.
+	 */
+	public override async findAgentSkills(token: CancellationToken, sessionResource?: URI): Promise<IAgentSkill[] | undefined> {
+		const baseResult = await super.findAgentSkills(token, sessionResource);
+		if (baseResult === undefined) {
+			return undefined;
+		}
+
+		const builtinSkills = await this.getBuiltinSkills();
+		if (builtinSkills.length === 0) {
+			return baseResult;
+		}
+
+		// Collect names already present from other sources
+		const existingNames = new Set(baseResult.map(s => s.name));
+		const nonOverridden = builtinSkills.filter(s => !existingNames.has(s.name));
+		if (nonOverridden.length === 0) {
+			return baseResult;
+		}
+
+		return [...baseResult, ...nonOverridden];
+	}
+
+	//#endregion
+
+	/**
+	 * Override to include built-in prompts and built-in skills, filtering out
+	 * those overridden by user or workspace items with the same name.
+	 */
+	public override async listPromptFiles(type: PromptsType, token: CancellationToken): Promise<readonly IPromptPath[]> {
+		const baseResults = await super.listPromptFiles(type, token);
+
+		let builtinItems: readonly IBuiltinPromptPath[];
+		if (type === PromptsType.skill) {
+			builtinItems = await this.getBuiltinSkillPaths();
+		} else {
+			builtinItems = await this.getBuiltinPromptFiles(type);
+		}
+		if (builtinItems.length === 0) {
+			return baseResults;
+		}
+
+		// Collect names of user/workspace items to detect overrides
+		const overriddenNames = new Set<string>();
+		for (const p of baseResults) {
+			if (p.storage === PromptsStorage.local || p.storage === PromptsStorage.user) {
+				overriddenNames.add(type === PromptsType.skill ? basename(dirname(p.uri)) : getCleanPromptName(p.uri));
+			}
+		}
+
+		const nonOverridden = builtinItems.filter(
+			p => !overriddenNames.has(type === PromptsType.skill ? basename(dirname(p.uri)) : getCleanPromptName(p.uri))
+		);
+		// Built-in items use BUILTIN_STORAGE ('builtin') which is not in the
+		// core IPromptPath union but is handled by the sessions UI layer.
+		return [...baseResults, ...nonOverridden] as readonly IPromptPath[];
+	}
+
+	public override async listPromptFilesForStorage(type: PromptsType, storage: PromptsStorage, token: CancellationToken): Promise<readonly IPromptPath[]> {
+		if (storage === BUILTIN_STORAGE) {
+			if (type === PromptsType.skill) {
+				return this.getBuiltinSkillPaths() as Promise<readonly IPromptPath[]>;
+			}
+			return this.getBuiltinPromptFiles(type) as Promise<readonly IPromptPath[]>;
+		}
+		return super.listPromptFilesForStorage(type, storage, token);
+	}
+
+	/**
+	 * Override to use ~/.copilot as the user-level source folder for creation,
+	 * instead of the VS Code profile's promptsHome.
+	 */
+	public override async getSourceFolders(type: PromptsType): Promise<readonly IPromptPath[]> {
+		const folders = await super.getSourceFolders(type);
+		const copilotRoot = this.getCopilotRoot();
+		// Replace any user-storage folders with the CLI-accessible ~/.copilot root
+		return folders.map(folder => {
+			if (folder.storage === PromptsStorage.user) {
+				const subfolder = getCliUserSubfolder(type);
+				return subfolder
+					? { ...folder, uri: joinPath(copilotRoot, subfolder) }
+					: folder;
+			}
+			return folder;
+		});
+	}
 }
 
 class AgenticPromptFilesLocator extends PromptFilesLocator {
@@ -36,7 +259,8 @@ class AgenticPromptFilesLocator extends PromptFilesLocator {
 		@IUserDataProfileService userDataService: IUserDataProfileService,
 		@ILogService logService: ILogService,
 		@IPathService pathService: IPathService,
-		@ISessionsManagementService private readonly activeSessionService: ISessionsManagementService,
+		@IWorkspaceTrustManagementService workspaceTrustManagementService: IWorkspaceTrustManagementService,
+		@IAICustomizationWorkspaceService private readonly customizationWorkspaceService: IAICustomizationWorkspaceService,
 	) {
 		super(
 			fileService,
@@ -46,7 +270,8 @@ class AgenticPromptFilesLocator extends PromptFilesLocator {
 			searchService,
 			userDataService,
 			logService,
-			pathService
+			pathService,
+			workspaceTrustManagementService
 		);
 	}
 
@@ -64,7 +289,7 @@ class AgenticPromptFilesLocator extends PromptFilesLocator {
 	}
 
 	protected override onDidChangeWorkspaceFolders(): Event<void> {
-		return Event.fromObservableLight(this.activeSessionService.activeSession);
+		return Event.fromObservableLight(this.customizationWorkspaceService.activeProjectRoot);
 	}
 
 	public override async getHookSourceFolders(): Promise<readonly URI[]> {
@@ -77,8 +302,7 @@ class AgenticPromptFilesLocator extends PromptFilesLocator {
 	}
 
 	private getActiveWorkspaceFolder(): IWorkspaceFolder | undefined {
-		const session = this.activeSessionService.getActiveSession();
-		const root = session?.worktree ?? session?.repository;
+		const root = this.customizationWorkspaceService.getActiveProjectRoot();
 		if (!root) {
 			return undefined;
 		}
@@ -91,3 +315,28 @@ class AgenticPromptFilesLocator extends PromptFilesLocator {
 	}
 }
 
+/**
+ * Returns the subfolder name under ~/.copilot/ for a given customization type.
+ * Used to determine the CLI-accessible user creation target.
+ *
+ * Prompts are a VS Code concept and use the standard profile promptsHome,
+ * so they are intentionally excluded here.
+ */
+function getCliUserSubfolder(type: PromptsType): string | undefined {
+	switch (type) {
+		case PromptsType.instructions: return 'instructions';
+		case PromptsType.skill: return 'skills';
+		case PromptsType.agent: return 'agents';
+		default: return undefined;
+	}
+}
+
+/**
+ * Strips XML tags and truncates to the given max length.
+ * Matches the sanitization applied by PromptsService for other skill sources.
+ */
+function sanitizeSkillText(text: string, maxLength: number): string {
+	const sanitized = text.replace(/<[^>]+>/g, '');
+	return sanitized.length > maxLength ? sanitized.substring(0, maxLength) : sanitized;
+}
+
diff --git a/src/vs/sessions/contrib/chat/browser/repoPicker.ts b/src/vs/sessions/contrib/chat/browser/repoPicker.ts
new file mode 100644
index 0000000000000..0ac9de839be2a
--- /dev/null
+++ b/src/vs/sessions/contrib/chat/browser/repoPicker.ts
@@ -0,0 +1,254 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../base/browser/dom.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { Emitter, Event } from '../../../../base/common/event.js';
+import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
+import { localize } from '../../../../nls.js';
+import { IActionWidgetService } from '../../../../platform/actionWidget/browser/actionWidget.js';
+import { ActionListItemKind, IActionListDelegate, IActionListItem } from '../../../../platform/actionWidget/browser/actionList.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
+import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+
+const OPEN_REPO_COMMAND = 'github.copilot.chat.cloudSessions.openRepository';
+const STORAGE_KEY_LAST_REPO = 'agentSessions.lastPickedRepo';
+const STORAGE_KEY_RECENT_REPOS = 'agentSessions.recentlyPickedRepos';
+const MAX_RECENT_REPOS = 10;
+const FILTER_THRESHOLD = 10;
+
+interface IRepoItem {
+	readonly id: string;
+	readonly name: string;
+}
+
+/**
+ * A self-contained widget for selecting the repository in cloud sessions.
+ * Uses the `github.copilot.chat.cloudSessions.openRepository` command for
+ * browsing repositories. Manages recently used repos in storage.
+ * Behaves like FolderPicker: trigger button with dropdown, storage persistence,
+ * recently used list with remove buttons.
+ */
+export class RepoPicker extends Disposable {
+
+	private readonly _onDidSelectRepo = this._register(new Emitter<string>());
+	readonly onDidSelectRepo: Event<string> = this._onDidSelectRepo.event;
+
+	private _triggerElement: HTMLElement | undefined;
+	private readonly _renderDisposables = this._register(new DisposableStore());
+
+	private _selectedRepo: IRepoItem | undefined;
+	private _recentlyPickedRepos: IRepoItem[] = [];
+
+	get selectedRepo(): string | undefined {
+		return this._selectedRepo?.id;
+	}
+
+	constructor(
+		@IActionWidgetService private readonly actionWidgetService: IActionWidgetService,
+		@IStorageService private readonly storageService: IStorageService,
+		@ICommandService private readonly commandService: ICommandService,
+	) {
+		super();
+
+		// Restore last picked repo
+		try {
+			const last = this.storageService.get(STORAGE_KEY_LAST_REPO, StorageScope.PROFILE);
+			if (last) {
+				this._selectedRepo = JSON.parse(last);
+			}
+		} catch { /* ignore */ }
+
+		// Restore recently picked repos
+		try {
+			const stored = this.storageService.get(STORAGE_KEY_RECENT_REPOS, StorageScope.PROFILE);
+			if (stored) {
+				this._recentlyPickedRepos = JSON.parse(stored);
+			}
+		} catch { /* ignore */ }
+	}
+
+	/**
+	 * Renders the repo picker trigger button into the given container.
+	 * Returns the container element.
+	 */
+	render(container: HTMLElement): HTMLElement {
+		this._renderDisposables.clear();
+
+		const slot = dom.append(container, dom.$('.sessions-chat-picker-slot'));
+		this._renderDisposables.add({ dispose: () => slot.remove() });
+
+		const trigger = dom.append(slot, dom.$('a.action-label'));
+		trigger.tabIndex = 0;
+		trigger.role = 'button';
+		this._triggerElement = trigger;
+
+		this._updateTriggerLabel();
+
+		this._renderDisposables.add(dom.addDisposableListener(trigger, dom.EventType.CLICK, (e) => {
+			dom.EventHelper.stop(e, true);
+			this.showPicker();
+		}));
+
+		this._renderDisposables.add(dom.addDisposableListener(trigger, dom.EventType.KEY_DOWN, (e) => {
+			if (e.key === 'Enter' || e.key === ' ') {
+				dom.EventHelper.stop(e, true);
+				this.showPicker();
+			}
+		}));
+
+		return slot;
+	}
+
+	/**
+	 * Shows the repo picker dropdown anchored to the trigger element.
+	 */
+	showPicker(): void {
+		if (!this._triggerElement || this.actionWidgetService.isVisible) {
+			return;
+		}
+
+		const items = this._buildItems();
+		const showFilter = items.filter(i => i.kind === ActionListItemKind.Action).length > FILTER_THRESHOLD;
+
+		const triggerElement = this._triggerElement;
+		const delegate: IActionListDelegate<IRepoItem> = {
+			onSelect: (item) => {
+				this.actionWidgetService.hide();
+				if (item.id === 'browse') {
+					this._browseForRepo();
+				} else {
+					this._selectRepo(item);
+				}
+			},
+			onHide: () => { triggerElement.focus(); },
+		};
+
+		this.actionWidgetService.show<IRepoItem>(
+			'repoPicker',
+			false,
+			items,
+			delegate,
+			this._triggerElement,
+			undefined,
+			[],
+			{
+				getAriaLabel: (item) => item.label ?? '',
+				getWidgetAriaLabel: () => localize('repoPicker.ariaLabel', "Repository Picker"),
+			},
+			showFilter ? { showFilter: true, filterPlaceholder: localize('repoPicker.filter', "Filter repositories...") } : undefined,
+		);
+	}
+
+	/**
+	 * Programmatically set the selected repository.
+	 */
+	setSelectedRepo(repoPath: string): void {
+		this._selectRepo({ id: repoPath, name: repoPath });
+	}
+
+	/**
+	 * Clears the selected repository.
+	 */
+	clearSelection(): void {
+		this._selectedRepo = undefined;
+		this._updateTriggerLabel();
+	}
+
+	private _selectRepo(item: IRepoItem): void {
+		this._selectedRepo = item;
+		this._addToRecentlyPicked(item);
+		this.storageService.store(STORAGE_KEY_LAST_REPO, JSON.stringify(item), StorageScope.PROFILE, StorageTarget.MACHINE);
+		this._updateTriggerLabel();
+		this._onDidSelectRepo.fire(item.id);
+	}
+
+	private async _browseForRepo(): Promise<void> {
+		try {
+			const result: string | undefined = await this.commandService.executeCommand(OPEN_REPO_COMMAND);
+			if (result) {
+				this._selectRepo({ id: result, name: result });
+			}
+		} catch {
+			// command was cancelled or failed — nothing to do
+		}
+	}
+
+	private _addToRecentlyPicked(item: IRepoItem): void {
+		this._recentlyPickedRepos = [
+			{ id: item.id, name: item.name },
+			...this._recentlyPickedRepos.filter(r => r.id !== item.id),
+		].slice(0, MAX_RECENT_REPOS);
+		this.storageService.store(STORAGE_KEY_RECENT_REPOS, JSON.stringify(this._recentlyPickedRepos), StorageScope.PROFILE, StorageTarget.MACHINE);
+	}
+
+	private _buildItems(): IActionListItem<IRepoItem>[] {
+		const seenIds = new Set<string>();
+		const items: IActionListItem<IRepoItem>[] = [];
+
+		// Currently selected (shown first, checked)
+		if (this._selectedRepo) {
+			seenIds.add(this._selectedRepo.id);
+			items.push({
+				kind: ActionListItemKind.Action,
+				label: this._selectedRepo.name,
+				group: { title: '', icon: Codicon.repo },
+				item: this._selectedRepo,
+			});
+		}
+
+		// Recently picked repos (sorted by name)
+		const dedupedRepos = this._recentlyPickedRepos.filter(r => !seenIds.has(r.id));
+		dedupedRepos.sort((a, b) => a.name.localeCompare(b.name));
+		for (const repo of dedupedRepos) {
+			seenIds.add(repo.id);
+			items.push({
+				kind: ActionListItemKind.Action,
+				label: repo.name,
+				group: { title: '', icon: Codicon.repo },
+				item: repo,
+				onRemove: () => this._removeRepo(repo.id),
+			});
+		}
+
+		// Separator + Browse...
+		if (items.length > 0) {
+			items.push({ kind: ActionListItemKind.Separator, label: '' });
+		}
+		items.push({
+			kind: ActionListItemKind.Action,
+			label: localize('browseRepo', "Browse..."),
+			group: { title: '', icon: Codicon.search },
+			item: { id: 'browse', name: localize('browseRepo', "Browse...") },
+		});
+
+		return items;
+	}
+
+	private _removeRepo(repoId: string): void {
+		this._recentlyPickedRepos = this._recentlyPickedRepos.filter(r => r.id !== repoId);
+		this.storageService.store(STORAGE_KEY_RECENT_REPOS, JSON.stringify(this._recentlyPickedRepos), StorageScope.PROFILE, StorageTarget.MACHINE);
+
+		// Re-show picker with updated items
+		this.actionWidgetService.hide();
+		this.showPicker();
+	}
+
+	private _updateTriggerLabel(): void {
+		if (!this._triggerElement) {
+			return;
+		}
+
+		dom.clearNode(this._triggerElement);
+		const label = this._selectedRepo?.name ?? localize('pickRepo', "Pick Repository");
+
+		dom.append(this._triggerElement, renderIcon(Codicon.repo));
+		const labelSpan = dom.append(this._triggerElement, dom.$('span.sessions-chat-dropdown-label'));
+		labelSpan.textContent = label;
+		dom.append(this._triggerElement, renderIcon(Codicon.chevronDown));
+	}
+
+}
diff --git a/src/vs/sessions/contrib/chat/browser/runScriptAction.ts b/src/vs/sessions/contrib/chat/browser/runScriptAction.ts
index 765f8466e2f92..096104d345432 100644
--- a/src/vs/sessions/contrib/chat/browser/runScriptAction.ts
+++ b/src/vs/sessions/contrib/chat/browser/runScriptAction.ts
@@ -5,18 +5,26 @@
 
 import { equals } from '../../../../base/common/arrays.js';
 import { Codicon } from '../../../../base/common/codicons.js';
-import { Disposable } from '../../../../base/common/lifecycle.js';
+import { KeyCode } from '../../../../base/common/keyCodes.js';
+import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
 import { autorun, derivedOpts, IObservable } from '../../../../base/common/observable.js';
 import { localize, localize2 } from '../../../../nls.js';
 import { MenuId, registerAction2, Action2, MenuRegistry } from '../../../../platform/actions/common/actions.js';
+import { ContextKeyExpr } from '../../../../platform/contextkey/common/contextkey.js';
+import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
+import { KeybindingsRegistry, KeybindingWeight } from '../../../../platform/keybinding/common/keybindingsRegistry.js';
 import { IQuickInputService, IQuickPickItem, IQuickPickSeparator } from '../../../../platform/quickinput/common/quickInput.js';
 import { IWorkbenchContribution } from '../../../../workbench/common/contributions.js';
+import { IChatWidgetService } from '../../../../workbench/contrib/chat/browser/chat.js';
+import { IViewsService } from '../../../../workbench/services/views/common/viewsService.js';
 import { SessionsCategories } from '../../../common/categories.js';
-import { IActiveSessionItem, ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
+import { IActiveSessionItem, IsActiveSessionBackgroundProviderContext, ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
 import { Menus } from '../../../browser/menus.js';
-import { ISessionsConfigurationService, ITaskEntry, TaskStorageTarget } from './sessionsConfigurationService.js';
-import { ContextKeyExpr } from '../../../../platform/contextkey/common/contextkey.js';
+import { INonSessionTaskEntry, ISessionsConfigurationService, ITaskEntry, TaskStorageTarget } from './sessionsConfigurationService.js';
 import { IsAuxiliaryWindowContext } from '../../../../workbench/common/contextkeys.js';
+import { SessionsWelcomeVisibleContext } from '../../../common/contextkeys.js';
+import { IRunScriptCustomTaskWidgetResult, RunScriptCustomTaskWidget } from './runScriptCustomTaskWidget.js';
+import { NewChatViewPane, SessionsViewId } from './newChatViewPane.js';
 
 
 
@@ -25,8 +33,9 @@ export const RunScriptDropdownMenuId = MenuId.for('AgentSessionsRunScriptDropdow
 
 // Action IDs
 const RUN_SCRIPT_ACTION_ID = 'workbench.action.agentSessions.runScript';
+const RUN_SCRIPT_ACTION_PRIMARY_ID = 'workbench.action.agentSessions.runScriptPrimary';
 const CONFIGURE_DEFAULT_RUN_ACTION_ID = 'workbench.action.agentSessions.configureDefaultRunAction';
-
+const GENERATE_RUN_ACTION_ID = 'workbench.action.agentSessions.generateRunAction';
 function getTaskDisplayLabel(task: ITaskEntry): string {
 	if (task.label && task.label.length > 0) {
 		return task.label;
@@ -43,6 +52,19 @@ function getTaskDisplayLabel(task: ITaskEntry): string {
 	return '';
 }
 
+function getTaskCommandPreview(task: ITaskEntry): string {
+	if (task.command && task.command.length > 0) {
+		return task.command;
+	}
+	if (task.script && task.script.length > 0) {
+		return localize('npmTaskCommandPreview', "npm run {0}", task.script);
+	}
+	if (task.task && task.task.toString().length > 0) {
+		return task.task.toString();
+	}
+	return getTaskDisplayLabel(task);
+}
+
 interface IRunScriptActionContext {
 	readonly session: IActiveSessionItem;
 	readonly tasks: readonly ITaskEntry[];
@@ -61,8 +83,11 @@ export class RunScriptContribution extends Disposable implements IWorkbenchContr
 
 	constructor(
 		@ISessionsManagementService private readonly _activeSessionService: ISessionsManagementService,
+		@IKeybindingService private readonly _keybindingService: IKeybindingService,
 		@IQuickInputService private readonly _quickInputService: IQuickInputService,
 		@ISessionsConfigurationService private readonly _sessionsConfigService: ISessionsConfigurationService,
+		@IChatWidgetService private readonly _chatWidgetService: IChatWidgetService,
+		@IViewsService private readonly _viewsService: IViewsService,
 	) {
 		super();
 
@@ -93,6 +118,40 @@ export class RunScriptContribution extends Disposable implements IWorkbenchContr
 	private _registerActions(): void {
 		const that = this;
 
+		this._register(registerAction2(class extends Action2 {
+			constructor() {
+				super({
+					id: RUN_SCRIPT_ACTION_PRIMARY_ID,
+					title: { value: localize('runPrimaryTask', 'Run Primary Task'), original: 'Run Primary Task' },
+					icon: Codicon.play,
+					category: SessionsCategories.Sessions,
+					f1: true,
+				});
+			}
+
+			async run(): Promise<void> {
+				const activeState = that._activeRunState.get();
+				if (!activeState) {
+					return;
+				}
+
+				const { tasks, session, lastRunTaskLabel } = activeState;
+				if (tasks.length === 0) {
+					const task = await that._showConfigureQuickPick(session);
+					if (task) {
+						await that._sessionsConfigService.runTask(task, session);
+					}
+					return;
+				}
+
+				const mruIndex = lastRunTaskLabel !== undefined
+					? tasks.findIndex(t => t.label === lastRunTaskLabel)
+					: -1;
+				const primaryTask = tasks[mruIndex >= 0 ? mruIndex : 0];
+				await that._sessionsConfigService.runTask(primaryTask, session);
+			}
+		}));
+
 		this._register(autorun(reader => {
 			const activeState = this._activeRunState.read(reader);
 			if (!activeState) {
@@ -111,13 +170,15 @@ export class RunScriptContribution extends Disposable implements IWorkbenchContr
 				for (let i = 0; i < tasks.length; i++) {
 					const task = tasks[i];
 					const actionId = `${RUN_SCRIPT_ACTION_ID}.${i}`;
+					const isPrimary = i === (mruIndex >= 0 ? mruIndex : 0);
 
 					reader.store.add(registerAction2(class extends Action2 {
 						constructor() {
 							super({
 								id: actionId,
 								title: getTaskDisplayLabel(task),
-								tooltip: localize('runActionTooltip', "Run '{0}' in terminal", getTaskDisplayLabel(task)),
+								tooltip: !isPrimary ? localize('runActionTooltip', "Run '{0}' in terminal", getTaskDisplayLabel(task))
+									: localize('runActionTooltipKeybinding', "Run '{0}' in terminal ({1})", getTaskDisplayLabel(task), that._keybindingService.lookupKeybinding(RUN_SCRIPT_ACTION_PRIMARY_ID)?.getLabel() ?? ''),
 								icon: Codicon.play,
 								category: SessionsCategories.Sessions,
 								menu: [{
@@ -140,7 +201,7 @@ export class RunScriptContribution extends Disposable implements IWorkbenchContr
 				constructor() {
 					super({
 						id: CONFIGURE_DEFAULT_RUN_ACTION_ID,
-						title: localize2('configureDefaultRunAction', "Add Run Action..."),
+						title: localize2('configureDefaultRunAction', "Add Action..."),
 						category: SessionsCategories.Sessions,
 						icon: Codicon.play,
 						precondition: configureScriptPrecondition,
@@ -153,18 +214,47 @@ export class RunScriptContribution extends Disposable implements IWorkbenchContr
 				}
 
 				async run(): Promise<void> {
-					await that._showConfigureQuickPick(session);
+					const task = await that._showConfigureQuickPick(session);
+					if (task) {
+						await that._sessionsConfigService.runTask(task, session);
+					}
+				}
+			}));
+
+			// Generate new action via Copilot (only shown when there is an active session)
+			reader.store.add(registerAction2(class extends Action2 {
+				constructor() {
+					super({
+						id: GENERATE_RUN_ACTION_ID,
+						title: localize2('generateRunAction', "Generate New Action..."),
+						category: SessionsCategories.Sessions,
+						precondition: IsActiveSessionBackgroundProviderContext,
+						menu: [{
+							id: RunScriptDropdownMenuId,
+							group: tasks.length === 0 ? 'navigation' : '1_configure',
+							order: 1
+						}]
+					});
+				}
+
+				async run(): Promise<void> {
+					if (session.isUntitled) {
+						const viewPane = that._viewsService.getViewWithId<NewChatViewPane>(SessionsViewId);
+						viewPane?.sendQuery('/generate-run-commands');
+					} else {
+						const widget = that._chatWidgetService.getWidgetBySessionResource(session.resource);
+						await widget?.acceptInput('/generate-run-commands');
+					}
 				}
 			}));
 		}));
 	}
 
-	private async _showConfigureQuickPick(session: IActiveSessionItem): Promise<void> {
+	private async _showConfigureQuickPick(session: IActiveSessionItem): Promise<ITaskEntry | undefined> {
 		const nonSessionTasks = await this._sessionsConfigService.getNonSessionTasks(session);
 		if (nonSessionTasks.length === 0) {
 			// No existing tasks, go straight to custom command input
-			await this._showCustomCommandInput(session);
-			return;
+			return this._showCustomCommandInput(session);
 		}
 
 		interface ITaskPickItem extends IQuickPickItem {
@@ -182,12 +272,12 @@ export class RunScriptContribution extends Disposable implements IWorkbenchContr
 
 		if (nonSessionTasks.length > 0) {
 			items.push({ type: 'separator', label: localize('existingTasks', "Existing Tasks") });
-			for (const task of nonSessionTasks) {
+			for (const { task, target } of nonSessionTasks) {
 				items.push({
 					label: getTaskDisplayLabel(task),
 					description: task.command,
 					task,
-					source: 'workspace',
+					source: target,
 				});
 			}
 		}
@@ -197,96 +287,135 @@ export class RunScriptContribution extends Disposable implements IWorkbenchContr
 		});
 
 		if (!picked) {
-			return;
+			return undefined;
 		}
 
 		const pickedItem = picked as ITaskPickItem;
 		if (pickedItem.task) {
-			// Existing task — set inSessions: true
-			await this._sessionsConfigService.addTaskToSessions(pickedItem.task, session, pickedItem.source ?? 'workspace');
+			return this._showCustomCommandInput(session, { task: pickedItem.task, target: pickedItem.source ?? 'workspace' });
 		} else {
 			// Custom command path
-			await this._showCustomCommandInput(session);
+			return this._showCustomCommandInput(session);
 		}
 	}
 
-	private async _showCustomCommandInput(session: IActiveSessionItem): Promise<void> {
-		const command = await this._quickInputService.input({
-			placeHolder: localize('enterCommandPlaceholder', "Enter command (e.g., npm run dev)"),
-			prompt: localize('enterCommandPrompt', "This command will be run as a task in the integrated terminal")
-		});
-
-		if (!command) {
-			return;
+	private async _showCustomCommandInput(session: IActiveSessionItem, existingTask?: INonSessionTaskEntry): Promise<ITaskEntry | undefined> {
+		const taskConfiguration = await this._showCustomCommandWidget(session, existingTask);
+		if (!taskConfiguration) {
+			return undefined;
 		}
 
-		const target = await this._pickStorageTarget(session);
-		if (!target) {
-			return;
+		if (existingTask) {
+			await this._sessionsConfigService.addTaskToSessions(existingTask.task, session, existingTask.target, { runOn: taskConfiguration.runOn ?? 'default' });
+			return {
+				...existingTask.task,
+				inSessions: true,
+				...(taskConfiguration.runOn ? { runOptions: { runOn: taskConfiguration.runOn } } : {}),
+			};
 		}
 
-		await this._sessionsConfigService.createAndAddTask(command, session, target);
+		return this._sessionsConfigService.createAndAddTask(
+			taskConfiguration.label,
+			taskConfiguration.command,
+			session,
+			taskConfiguration.target,
+			taskConfiguration.runOn ? { runOn: taskConfiguration.runOn } : undefined
+		);
 	}
 
-	private async _pickStorageTarget(session: IActiveSessionItem): Promise<TaskStorageTarget | undefined> {
-		const hasWorktree = !!session.worktree;
-		const hasRepository = !!session.repository;
-
-		interface IStorageTargetItem extends IQuickPickItem {
-			target: TaskStorageTarget;
-		}
+	private _showCustomCommandWidget(session: IActiveSessionItem, existingTask?: INonSessionTaskEntry): Promise<IRunScriptCustomTaskWidgetResult | undefined> {
+		const workspaceTargetDisabledReason = !(session.worktree ?? session.repository)
+			? localize('workspaceStorageUnavailableTooltip', "Workspace storage is unavailable for this session")
+			: undefined;
+
+		return new Promise<IRunScriptCustomTaskWidgetResult | undefined>(resolve => {
+			const disposables = new DisposableStore();
+			let settled = false;
+
+			const quickWidget = disposables.add(this._quickInputService.createQuickWidget());
+			quickWidget.title = existingTask
+				? localize('addExistingActionWidgetTitle', "Add Existing Action...")
+				: localize('addActionWidgetTitle', "Add Action...");
+			quickWidget.description = existingTask
+				? localize('addExistingActionWidgetDescription', "Enable an existing task for sessions and configure when it should run")
+				: localize('addActionWidgetDescription', "Create a shell task and configure how it should be saved and run");
+			quickWidget.ignoreFocusOut = true;
+			const widget = disposables.add(new RunScriptCustomTaskWidget({
+				label: existingTask?.task.label,
+				labelDisabledReason: existingTask ? localize('existingTaskLabelLocked', "This name comes from an existing task and cannot be changed here.") : undefined,
+				command: existingTask ? getTaskCommandPreview(existingTask.task) : undefined,
+				commandDisabledReason: existingTask ? localize('existingTaskCommandLocked', "This command comes from an existing task and cannot be changed here.") : undefined,
+				target: existingTask?.target,
+				targetDisabledReason: existingTask ? localize('existingTaskTargetLocked', "This existing task cannot be moved between workspace and user storage.") : workspaceTargetDisabledReason,
+				runOn: existingTask?.task.runOptions?.runOn === 'worktreeCreated' ? 'worktreeCreated' : undefined,
+			}));
+			quickWidget.widget = widget.domNode;
 
-		const items: IStorageTargetItem[] = [
-			{
-				target: 'user',
-				label: localize('storeInUserSettings', "User Settings"),
-				description: localize('storeInUserSettingsDesc', "Available in all sessions"),
-			},
-			hasWorktree ? {
-				target: 'workspace',
-				label: localize('storeInWorkspaceWorktreeSettings', "Workspace (Worktree)"),
-				description: localize('storeInWorkspaceWorktreeSettingsDesc', "Stored in session worktree"),
-			} : hasRepository ? {
-				target: 'workspace',
-				label: localize('storeInWorkspaceSettings', "Workspace"),
-				description: localize('storeInWorkspace', "Stored in the workspace"),
-			} : {
-				target: 'workspace',
-				label: localize('storeInWorkspaceSettingsDisable', "Workspace Unavailable"),
-				description: localize('storeInWorkspaceDisabled', "Stored in the workspace Unavailable"),
-				disabled: true,
-				italic: true,
-			}
-		];
-
-		return new Promise<TaskStorageTarget | undefined>(resolve => {
-			const picker = this._quickInputService.createQuickPick<IStorageTargetItem>({ useSeparators: true });
-			picker.placeholder = localize('pickStorageTarget', "Where should this action be saved?");
-			picker.items = items;
-
-			picker.onDidAccept(() => {
-				const selected = picker.activeItems[0];
-				if (selected && (selected.target !== 'workspace' || hasWorktree)) {
-					picker.dispose();
-					resolve(selected.target);
+			const complete = (result: IRunScriptCustomTaskWidgetResult | undefined) => {
+				if (settled) {
+					return;
 				}
-			});
-			picker.onDidHide(() => {
-				picker.dispose();
-				resolve(undefined);
-			});
-			picker.show();
+				settled = true;
+				resolve(result);
+				quickWidget.hide();
+			};
+
+			disposables.add(widget.onDidSubmit(result => complete(result)));
+			disposables.add(widget.onDidCancel(() => complete(undefined)));
+			disposables.add(quickWidget.onDidHide(() => {
+				if (!settled) {
+					settled = true;
+					resolve(undefined);
+				}
+				disposables.dispose();
+			}));
+
+			quickWidget.show();
+			widget.focus();
 		});
 	}
 }
 
-// Register the Run split button submenu on the workbench title bar
-MenuRegistry.appendMenuItem(Menus.TitleBarRight, {
+// Register the Run split button submenu on the workbench title bar (background sessions only)
+MenuRegistry.appendMenuItem(Menus.TitleBarSessionMenu, {
 	submenu: RunScriptDropdownMenuId,
 	isSplitButton: true,
 	title: localize2('run', "Run"),
 	icon: Codicon.play,
 	group: 'navigation',
 	order: 8,
+	when: ContextKeyExpr.and(IsAuxiliaryWindowContext.toNegated(), SessionsWelcomeVisibleContext.toNegated(), IsActiveSessionBackgroundProviderContext)
+});
+
+// Disabled placeholder shown in the titlebar when the active session does not support running scripts
+class RunScriptNotAvailableAction extends Action2 {
+	constructor() {
+		super({
+			id: 'workbench.action.agentSessions.runScript.notAvailable',
+			title: localize2('run', "Run"),
+			tooltip: localize('runScriptNotAvailableTooltip', "Run Script is not available for this session type"),
+			icon: Codicon.play,
+			precondition: ContextKeyExpr.false(),
+			menu: [{
+				id: Menus.TitleBarSessionMenu,
+				group: 'navigation',
+				order: 8,
+				when: ContextKeyExpr.and(IsAuxiliaryWindowContext.toNegated(), SessionsWelcomeVisibleContext.toNegated(), IsActiveSessionBackgroundProviderContext.toNegated())
+			}]
+		});
+	}
+
+	override run(): void { }
+}
+
+registerAction2(RunScriptNotAvailableAction);
+
+// Register F5 keybinding at module level to ensure it's in the registry
+// before the keybinding resolver is cached. The command handler is
+// registered later by RunScriptContribution.
+KeybindingsRegistry.registerKeybindingRule({
+	id: RUN_SCRIPT_ACTION_PRIMARY_ID,
+	primary: KeyCode.F5,
+	weight: KeybindingWeight.WorkbenchContrib + 100,
 	when: IsAuxiliaryWindowContext.toNegated()
 });
diff --git a/src/vs/sessions/contrib/chat/browser/runScriptCustomTaskWidget.ts b/src/vs/sessions/contrib/chat/browser/runScriptCustomTaskWidget.ts
new file mode 100644
index 0000000000000..32259cd6446d6
--- /dev/null
+++ b/src/vs/sessions/contrib/chat/browser/runScriptCustomTaskWidget.ts
@@ -0,0 +1,204 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import './media/runScriptAction.css';
+
+import * as dom from '../../../../base/browser/dom.js';
+import { StandardKeyboardEvent } from '../../../../base/browser/keyboardEvent.js';
+import { Button } from '../../../../base/browser/ui/button/button.js';
+import { InputBox } from '../../../../base/browser/ui/inputbox/inputBox.js';
+import { Radio } from '../../../../base/browser/ui/radio/radio.js';
+import { Checkbox } from '../../../../base/browser/ui/toggle/toggle.js';
+import { Emitter, Event } from '../../../../base/common/event.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { KeyCode } from '../../../../base/common/keyCodes.js';
+import { localize } from '../../../../nls.js';
+import { defaultButtonStyles, defaultCheckboxStyles, defaultInputBoxStyles } from '../../../../platform/theme/browser/defaultStyles.js';
+import { TaskStorageTarget } from './sessionsConfigurationService.js';
+
+export const WORKTREE_CREATED_RUN_ON = 'worktreeCreated' as const;
+
+export interface IRunScriptCustomTaskWidgetState {
+	readonly label?: string;
+	readonly labelDisabledReason?: string;
+	readonly command?: string;
+	readonly commandDisabledReason?: string;
+	readonly target?: TaskStorageTarget;
+	readonly targetDisabledReason?: string;
+	readonly runOn?: typeof WORKTREE_CREATED_RUN_ON;
+}
+
+export interface IRunScriptCustomTaskWidgetResult {
+	readonly label?: string;
+	readonly command: string;
+	readonly target: TaskStorageTarget;
+	readonly runOn?: typeof WORKTREE_CREATED_RUN_ON;
+}
+
+export class RunScriptCustomTaskWidget extends Disposable {
+
+	readonly domNode: HTMLElement;
+
+	private readonly _labelInput: InputBox;
+	private readonly _commandInput: InputBox;
+	private readonly _runOnCheckbox: Checkbox;
+	private readonly _storageOptions: Radio;
+	private readonly _submitButton: Button;
+	private readonly _cancelButton: Button;
+	private readonly _labelLocked: boolean;
+	private readonly _commandLocked: boolean;
+	private readonly _targetLocked: boolean;
+	private _selectedTarget: TaskStorageTarget;
+
+	private readonly _onDidSubmit = this._register(new Emitter<IRunScriptCustomTaskWidgetResult>());
+	readonly onDidSubmit: Event<IRunScriptCustomTaskWidgetResult> = this._onDidSubmit.event;
+
+	private readonly _onDidCancel = this._register(new Emitter<void>());
+	readonly onDidCancel: Event<void> = this._onDidCancel.event;
+
+	constructor(state: IRunScriptCustomTaskWidgetState) {
+		super();
+
+		this._labelLocked = !!state.labelDisabledReason;
+		this._commandLocked = !!state.commandDisabledReason;
+		this._targetLocked = !!state.targetDisabledReason && state.target !== undefined;
+		this._selectedTarget = state.target ?? (state.targetDisabledReason ? 'user' : 'workspace');
+
+		this.domNode = dom.$('.run-script-action-widget');
+
+		const labelSection = dom.append(this.domNode, dom.$('.run-script-action-section'));
+		dom.append(labelSection, dom.$('label.run-script-action-label', undefined, localize('labelFieldLabel', "Name")));
+		const labelInputContainer = dom.append(labelSection, dom.$('.run-script-action-input'));
+		this._labelInput = this._register(new InputBox(labelInputContainer, undefined, {
+			placeholder: localize('enterLabelPlaceholder', "Enter a name for this action (optional)"),
+			tooltip: state.labelDisabledReason,
+			ariaLabel: localize('enterLabelAriaLabel', "Task name"),
+			inputBoxStyles: defaultInputBoxStyles,
+		}));
+		this._labelInput.value = state.label ?? '';
+		if (state.labelDisabledReason) {
+			this._labelInput.disable();
+		}
+
+		const commandSection = dom.append(this.domNode, dom.$('.run-script-action-section'));
+		dom.append(commandSection, dom.$('label.run-script-action-label', undefined, localize('commandFieldLabel', "Command")));
+		const commandInputContainer = dom.append(commandSection, dom.$('.run-script-action-input'));
+		this._commandInput = this._register(new InputBox(commandInputContainer, undefined, {
+			placeholder: localize('enterCommandPlaceholder', "Enter command (for example, npm run dev)"),
+			tooltip: state.commandDisabledReason,
+			ariaLabel: localize('enterCommandAriaLabel', "Task command"),
+			inputBoxStyles: defaultInputBoxStyles,
+		}));
+		this._commandInput.value = state.command ?? '';
+		if (state.commandDisabledReason) {
+			this._commandInput.disable();
+		}
+
+		const runOnSection = dom.append(this.domNode, dom.$('.run-script-action-section'));
+		dom.append(runOnSection, dom.$('div.run-script-action-label', undefined, localize('runOptionsLabel', "Run Options")));
+		const runOnRow = dom.append(runOnSection, dom.$('.run-script-action-option-row'));
+		this._runOnCheckbox = this._register(new Checkbox(localize('runOnWorktreeCreated', "Run When Worktree Is Created"), state.runOn === WORKTREE_CREATED_RUN_ON, defaultCheckboxStyles));
+		runOnRow.appendChild(this._runOnCheckbox.domNode);
+		const runOnText = dom.append(runOnRow, dom.$('span.run-script-action-option-text', undefined, localize('runOnWorktreeCreatedDescription', "Automatically run this action when the session worktree is created")));
+		this._register(dom.addDisposableListener(runOnText, dom.EventType.CLICK, () => this._runOnCheckbox.checked = !this._runOnCheckbox.checked));
+
+		const storageSection = dom.append(this.domNode, dom.$('.run-script-action-section'));
+		dom.append(storageSection, dom.$('div.run-script-action-label', undefined, localize('storageLabel', "Save In")));
+		const storageDisabledReason = state.targetDisabledReason;
+		const workspaceTargetDisabled = !!storageDisabledReason;
+		this._storageOptions = this._register(new Radio({
+			items: [
+				{
+					text: localize('workspaceStorageLabel', "Workspace"),
+					tooltip: storageDisabledReason ?? localize('workspaceStorageTooltip', "Save this action in the current workspace"),
+					isActive: this._selectedTarget === 'workspace',
+					disabled: workspaceTargetDisabled,
+				},
+				{
+					text: localize('userStorageLabel', "User"),
+					tooltip: this._targetLocked ? storageDisabledReason : localize('userStorageTooltip', "Save this action in your user tasks and make it available in all sessions"),
+					isActive: this._selectedTarget === 'user',
+					disabled: this._targetLocked,
+				}
+			]
+		}));
+		this._storageOptions.domNode.setAttribute('aria-label', localize('storageAriaLabel', "Task storage target"));
+		storageSection.appendChild(this._storageOptions.domNode);
+		if (storageDisabledReason && !this._targetLocked) {
+			dom.append(storageSection, dom.$('div.run-script-action-hint', undefined, storageDisabledReason));
+		}
+
+		const buttonRow = dom.append(this.domNode, dom.$('.run-script-action-buttons'));
+		this._cancelButton = this._register(new Button(buttonRow, { ...defaultButtonStyles, secondary: true }));
+		this._cancelButton.label = localize('cancelAddAction', "Cancel");
+		this._submitButton = this._register(new Button(buttonRow, defaultButtonStyles));
+		this._submitButton.label = localize('confirmAddAction', "Add Action");
+
+		this._register(this._labelInput.onDidChange(() => this._updateButtonEnablement()));
+		this._register(this._commandInput.onDidChange(() => this._updateButtonEnablement()));
+		this._register(this._storageOptions.onDidSelect(index => {
+			this._selectedTarget = index === 0 ? 'workspace' : 'user';
+		}));
+		this._register(this._submitButton.onDidClick(() => this._submit()));
+		this._register(this._cancelButton.onDidClick(() => this._onDidCancel.fire()));
+		this._register(dom.addDisposableListener(this._labelInput.inputElement, dom.EventType.KEY_DOWN, event => {
+			const keyboardEvent = new StandardKeyboardEvent(event);
+			if (keyboardEvent.equals(KeyCode.Enter)) {
+				keyboardEvent.preventDefault();
+				keyboardEvent.stopPropagation();
+				this._submit();
+			}
+		}));
+		this._register(dom.addDisposableListener(this._commandInput.inputElement, dom.EventType.KEY_DOWN, event => {
+			const keyboardEvent = new StandardKeyboardEvent(event);
+			if (keyboardEvent.equals(KeyCode.Enter)) {
+				keyboardEvent.preventDefault();
+				keyboardEvent.stopPropagation();
+				this._submit();
+			}
+		}));
+		this._register(dom.addDisposableListener(this.domNode, dom.EventType.KEY_DOWN, event => {
+			const keyboardEvent = new StandardKeyboardEvent(event);
+			if (keyboardEvent.equals(KeyCode.Escape)) {
+				keyboardEvent.preventDefault();
+				keyboardEvent.stopPropagation();
+				this._onDidCancel.fire();
+			}
+		}));
+
+		this._updateButtonEnablement();
+	}
+
+	focus(): void {
+		if (!this._labelLocked) {
+			this._labelInput.focus();
+			return;
+		}
+		if (this._commandLocked) {
+			this._runOnCheckbox.focus();
+			return;
+		}
+		this._commandInput.focus();
+	}
+
+	private _submit(): void {
+		const label = this._labelInput.value.trim();
+		const command = this._commandInput.value.trim();
+		if (!command) {
+			return;
+		}
+
+		this._onDidSubmit.fire({
+			label: label.length > 0 ? label : undefined,
+			command,
+			target: this._selectedTarget,
+			runOn: this._runOnCheckbox.checked ? WORKTREE_CREATED_RUN_ON : undefined,
+		});
+	}
+
+	private _updateButtonEnablement(): void {
+		this._submitButton.enabled = this._commandInput.value.trim().length > 0;
+	}
+}
diff --git a/src/vs/sessions/contrib/chat/browser/sessionTargetPicker.ts b/src/vs/sessions/contrib/chat/browser/sessionTargetPicker.ts
index 1d762632f9f71..ecf9e9b782f9d 100644
--- a/src/vs/sessions/contrib/chat/browser/sessionTargetPicker.ts
+++ b/src/vs/sessions/contrib/chat/browser/sessionTargetPicker.ts
@@ -5,40 +5,15 @@
 
 import * as dom from '../../../../base/browser/dom.js';
 import { Codicon } from '../../../../base/common/codicons.js';
-import { ThemeIcon } from '../../../../base/common/themables.js';
-import { toAction } from '../../../../base/common/actions.js';
 import { Radio } from '../../../../base/browser/ui/radio/radio.js';
-import { DropdownMenuActionViewItem } from '../../../../base/browser/ui/dropdown/dropdownActionViewItem.js';
 import { Emitter, Event } from '../../../../base/common/event.js';
 import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
 import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
 import { localize } from '../../../../nls.js';
-import { IContextMenuService } from '../../../../platform/contextview/browser/contextView.js';
+import { IActionWidgetService } from '../../../../platform/actionWidget/browser/actionWidget.js';
+import { ActionListItemKind, IActionListDelegate, IActionListItem } from '../../../../platform/actionWidget/browser/actionList.js';
 import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
 import { IGitRepository } from '../../../../workbench/contrib/git/common/gitService.js';
-import { INewSession } from './newSession.js';
-
-/**
- * A dropdown menu action item that shows an icon, a text label, and a chevron.
- */
-class LabeledDropdownMenuActionViewItem extends DropdownMenuActionViewItem {
-	protected override renderLabel(element: HTMLElement): null {
-		const classNames = typeof this.options.classNames === 'string'
-			? this.options.classNames.split(/\s+/g).filter(s => !!s)
-			: (this.options.classNames ?? []);
-		if (classNames.length > 0) {
-			const icon = dom.append(element, dom.$('span'));
-			icon.classList.add('codicon', ...classNames);
-		}
-
-		const label = dom.append(element, dom.$('span.sessions-chat-dropdown-label'));
-		label.textContent = this._action.label;
-
-		dom.append(element, renderIcon(Codicon.chevronDown));
-
-		return null;
-	}
-}
 
 // #region --- Session Target Picker ---
 
@@ -161,33 +136,27 @@ export type IsolationMode = 'worktree' | 'workspace';
 export class IsolationModePicker extends Disposable {
 
 	private _isolationMode: IsolationMode = 'worktree';
-	private _newSession: INewSession | undefined;
+	private _preferredIsolationMode: IsolationMode | undefined;
 	private _repository: IGitRepository | undefined;
+	private _enabled: boolean = true;
 
 	private readonly _onDidChange = this._register(new Emitter<IsolationMode>());
 	readonly onDidChange: Event<IsolationMode> = this._onDidChange.event;
 
 	private readonly _renderDisposables = this._register(new DisposableStore());
-	private _container: HTMLElement | undefined;
-	private _dropdownContainer: HTMLElement | undefined;
+	private _slotElement: HTMLElement | undefined;
+	private _triggerElement: HTMLElement | undefined;
 
 	get isolationMode(): IsolationMode {
 		return this._isolationMode;
 	}
 
 	constructor(
-		@IContextMenuService private readonly contextMenuService: IContextMenuService,
+		@IActionWidgetService private readonly actionWidgetService: IActionWidgetService,
 	) {
 		super();
 	}
 
-	/**
-	 * Sets the pending session that this picker writes to.
-	 */
-	setNewSession(session: INewSession | undefined): void {
-		this._newSession = session;
-	}
-
 	/**
 	 * Sets the git repository. When undefined, worktree option is hidden
 	 * and isolation mode falls back to 'workspace'.
@@ -195,78 +164,150 @@ export class IsolationModePicker extends Disposable {
 	setRepository(repository: IGitRepository | undefined): void {
 		this._repository = repository;
 		if (repository) {
-			this._setMode('worktree');
+			const preferred = this._preferredIsolationMode;
+			this._preferredIsolationMode = undefined;
+			this._setMode(preferred ?? this._isolationMode);
 		} else if (this._isolationMode === 'worktree') {
+			this._preferredIsolationMode ??= this._isolationMode;
 			this._setMode('workspace');
 		}
-		this._renderDropdown();
+		this._updateTriggerLabel();
 	}
 
 	/**
-	 * Renders the isolation mode dropdown into the given container.
+	 * Renders the isolation mode picker into the given container.
 	 */
 	render(container: HTMLElement): void {
-		this._container = container;
-		this._dropdownContainer = dom.append(container, dom.$('.sessions-chat-local-mode-left'));
-		this._renderDropdown();
+		this._renderDisposables.clear();
+
+		const slot = dom.append(container, dom.$('.sessions-chat-picker-slot'));
+		this._slotElement = slot;
+		this._renderDisposables.add({ dispose: () => slot.remove() });
+
+		const trigger = dom.append(slot, dom.$('a.action-label'));
+		trigger.tabIndex = 0;
+		trigger.role = 'button';
+		this._triggerElement = trigger;
+		this._updateTriggerLabel();
+
+		this._renderDisposables.add(dom.addDisposableListener(trigger, dom.EventType.CLICK, (e) => {
+			dom.EventHelper.stop(e, true);
+			this._showPicker();
+		}));
+
+		this._renderDisposables.add(dom.addDisposableListener(trigger, dom.EventType.KEY_DOWN, (e) => {
+			if (e.key === 'Enter' || e.key === ' ') {
+				dom.EventHelper.stop(e, true);
+				this._showPicker();
+			}
+		}));
+	}
+
+	/**
+	 * Sets a preferred isolation mode to apply when a repository is set.
+	 */
+	setPreferredIsolationMode(mode: IsolationMode): void {
+		this._preferredIsolationMode = mode;
+	}
+
+	/**
+	 * Programmatically set the isolation mode.
+	 */
+	setIsolationMode(mode: IsolationMode): void {
+		this._setMode(mode);
 	}
 
 	/**
 	 * Shows or hides the picker.
 	 */
 	setVisible(visible: boolean): void {
-		if (this._container) {
-			this._container.style.visibility = visible ? '' : 'hidden';
+		if (this._slotElement) {
+			this._slotElement.style.display = visible ? '' : 'none';
 		}
 	}
 
-	private _renderDropdown(): void {
-		if (!this._dropdownContainer) {
+	/**
+	 * Enables or disables the picker. When disabled, the picker is shown
+	 * but cannot be interacted with.
+	 */
+	setEnabled(enabled: boolean): void {
+		this._enabled = enabled;
+		this._updateTriggerLabel();
+	}
+
+	private _showPicker(): void {
+		if (!this._triggerElement || this.actionWidgetService.isVisible || !this._repository || !this._enabled) {
 			return;
 		}
 
-		this._renderDisposables.clear();
-		dom.clearNode(this._dropdownContainer);
-
-		const modeLabel = this._isolationMode === 'worktree'
-			? localize('isolationMode.worktree', "Worktree")
-			: localize('isolationMode.folder', "Folder");
-		const modeIcon = this._isolationMode === 'worktree' ? Codicon.worktree : Codicon.folder;
-		const isDisabled = !this._repository;
+		const items: IActionListItem<IsolationMode>[] = [
+			{
+				kind: ActionListItemKind.Action,
+				label: localize('isolationMode.worktree', "Worktree"),
+				group: { title: '', icon: Codicon.worktree },
+				item: 'worktree',
+			},
+			{
+				kind: ActionListItemKind.Action,
+				label: localize('isolationMode.folder', "Folder"),
+				group: { title: '', icon: Codicon.folder },
+				item: 'workspace',
+			},
+		];
 
-		const modeAction = toAction({ id: 'isolationMode', label: modeLabel, run: () => { } });
-		const modeDropdown = this._renderDisposables.add(new LabeledDropdownMenuActionViewItem(
-			modeAction,
+		const triggerElement = this._triggerElement;
+		const delegate: IActionListDelegate<IsolationMode> = {
+			onSelect: (mode) => {
+				this.actionWidgetService.hide();
+				this._setMode(mode);
+			},
+			onHide: () => { triggerElement.focus(); },
+		};
+
+		this.actionWidgetService.show<IsolationMode>(
+			'isolationModePicker',
+			false,
+			items,
+			delegate,
+			this._triggerElement,
+			undefined,
+			[],
 			{
-				getActions: () => isDisabled ? [] : [
-					toAction({
-						id: 'isolationMode.worktree',
-						label: localize('isolationMode.worktree', "Worktree"),
-						checked: this._isolationMode === 'worktree',
-						run: () => this._setMode('worktree'),
-					}),
-					toAction({
-						id: 'isolationMode.folder',
-						label: localize('isolationMode.folder', "Folder"),
-						checked: this._isolationMode === 'workspace',
-						run: () => this._setMode('workspace'),
-					}),
-				],
+				getAriaLabel: (item) => item.label ?? '',
+				getWidgetAriaLabel: () => localize('isolationModePicker.ariaLabel', "Isolation Mode"),
 			},
-			this.contextMenuService,
-			{ classNames: [...ThemeIcon.asClassNameArray(modeIcon)] }
-		));
-		const modeSlot = dom.append(this._dropdownContainer, dom.$('.sessions-chat-picker-slot'));
-		modeDropdown.render(modeSlot);
-		modeSlot.classList.toggle('disabled', isDisabled);
+		);
 	}
 
 	private _setMode(mode: IsolationMode): void {
 		if (this._isolationMode !== mode) {
 			this._isolationMode = mode;
-			this._newSession?.setIsolationMode(mode);
 			this._onDidChange.fire(mode);
-			this._renderDropdown();
+			this._updateTriggerLabel();
+		}
+	}
+
+	private _updateTriggerLabel(): void {
+		if (!this._triggerElement) {
+			return;
+		}
+
+		dom.clearNode(this._triggerElement);
+		const isDisabled = !this._repository;
+		const modeIcon = this._isolationMode === 'worktree' ? Codicon.worktree : Codicon.folder;
+		const modeLabel = this._isolationMode === 'worktree'
+			? localize('isolationMode.worktree', "Worktree")
+			: localize('isolationMode.folder', "Folder");
+
+		dom.append(this._triggerElement, renderIcon(modeIcon));
+		const labelSpan = dom.append(this._triggerElement, dom.$('span.sessions-chat-dropdown-label'));
+		labelSpan.textContent = modeLabel;
+		dom.append(this._triggerElement, renderIcon(Codicon.chevronDown));
+
+		this._slotElement?.classList.toggle('disabled', isDisabled || !this._enabled);
+		if (this._triggerElement) {
+			this._triggerElement.tabIndex = (!isDisabled && this._enabled) ? 0 : -1;
+			this._triggerElement.setAttribute('aria-disabled', String(isDisabled || !this._enabled));
 		}
 	}
 }
diff --git a/src/vs/sessions/contrib/chat/browser/sessionsConfigurationService.ts b/src/vs/sessions/contrib/chat/browser/sessionsConfigurationService.ts
index 4183a311f60a2..5ba62f2c0a0c5 100644
--- a/src/vs/sessions/contrib/chat/browser/sessionsConfigurationService.ts
+++ b/src/vs/sessions/contrib/chat/browser/sessionsConfigurationService.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Disposable, DisposableStore, MutableDisposable } from '../../../../base/common/lifecycle.js';
-import { IObservable, observableValue, transaction } from '../../../../base/common/observable.js';
+import { autorun, IObservable, observableValue, transaction } from '../../../../base/common/observable.js';
 import { joinPath, dirname, isEqual } from '../../../../base/common/resources.js';
 import { parse } from '../../../../base/common/jsonc.js';
 import { isMacintosh, isWindows } from '../../../../base/common/platform.js';
@@ -20,6 +20,11 @@ import { ITerminalInstance, ITerminalService } from '../../../../workbench/contr
 import { CommandString } from '../../../../workbench/contrib/tasks/common/taskConfiguration.js';
 
 export type TaskStorageTarget = 'user' | 'workspace';
+type TaskRunOnOption = 'default' | 'folderOpen' | 'worktreeCreated';
+
+interface ITaskRunOptions {
+	readonly runOn?: TaskRunOnOption;
+}
 
 /**
  * Shape of a single task entry inside tasks.json.
@@ -30,13 +35,20 @@ export interface ITaskEntry {
 	readonly script?: string;
 	readonly type?: string;
 	readonly command?: string;
+	readonly args?: CommandString[];
 	readonly inSessions?: boolean;
-	readonly windows?: { command?: string };
-	readonly osx?: { command?: string };
-	readonly linux?: { command?: string };
+	readonly runOptions?: ITaskRunOptions;
+	readonly windows?: { command?: string; args?: CommandString[] };
+	readonly osx?: { command?: string; args?: CommandString[] };
+	readonly linux?: { command?: string; args?: CommandString[] };
 	readonly [key: string]: unknown;
 }
 
+export interface INonSessionTaskEntry {
+	readonly task: ITaskEntry;
+	readonly target: TaskStorageTarget;
+}
+
 interface ITasksJson {
 	version?: string;
 	tasks?: ITaskEntry[];
@@ -55,19 +67,19 @@ export interface ISessionsConfigurationService {
 	 * Returns tasks that do NOT have `inSessions: true` — used as
 	 * suggestions in the "Add Run Action" picker.
 	 */
-	getNonSessionTasks(session: IActiveSessionItem): Promise<readonly ITaskEntry[]>;
+	getNonSessionTasks(session: IActiveSessionItem): Promise<readonly INonSessionTaskEntry[]>;
 
 	/**
 	 * Sets `inSessions: true` on an existing task (identified by label),
 	 * updating it in place in its tasks.json.
 	 */
-	addTaskToSessions(task: ITaskEntry, session: IActiveSessionItem, target: TaskStorageTarget): Promise<void>;
+	addTaskToSessions(task: ITaskEntry, session: IActiveSessionItem, target: TaskStorageTarget, options?: ITaskRunOptions): Promise<void>;
 
 	/**
 	 * Creates a new shell task with `inSessions: true` and writes it to
 	 * the appropriate tasks.json (user or workspace).
 	 */
-	createAndAddTask(command: string, session: IActiveSessionItem, target: TaskStorageTarget): Promise<void>;
+	createAndAddTask(label: string | undefined, command: string, session: IActiveSessionItem, target: TaskStorageTarget, options?: ITaskRunOptions): Promise<ITaskEntry | undefined>;
 
 	/**
 	 * Runs a task entry in a terminal, resolving the correct platform
@@ -88,11 +100,13 @@ export class SessionsConfigurationService extends Disposable implements ISession
 	declare readonly _serviceBrand: undefined;
 
 	private static readonly _LAST_RUN_TASK_LABELS_KEY = 'agentSessions.lastRunTaskLabels';
+	private static readonly _SUPPORTED_TASK_TYPES = new Set(['shell', 'npm']);
 
 	private readonly _sessionTasks = observableValue<readonly ITaskEntry[]>(this, []);
 	private readonly _fileWatcher = this._register(new MutableDisposable());
 	/** Maps `cwd.toString() + command` to the terminal `instanceId`. */
 	private readonly _taskTerminals = new Map<string, number>();
+	private readonly _knownSessionWorktrees = new Map<string, string | undefined>();
 	private readonly _lastRunTaskLabels: Map<string, string>;
 	private readonly _lastRunTaskObservables = new Map<string, ReturnType<typeof observableValue<string | undefined>>>();
 
@@ -109,6 +123,11 @@ export class SessionsConfigurationService extends Disposable implements ISession
 	) {
 		super();
 		this._lastRunTaskLabels = this._loadLastRunTaskLabels();
+
+		this._register(autorun(reader => {
+			const activeSession = this._sessionsManagementService.activeSession.read(reader);
+			this._handleActiveSessionChange(activeSession);
+		}));
 	}
 
 	getSessionTasks(session: IActiveSessionItem): IObservable<readonly ITaskEntry[]> {
@@ -124,12 +143,33 @@ export class SessionsConfigurationService extends Disposable implements ISession
 		return this._sessionTasks;
 	}
 
-	async getNonSessionTasks(session: IActiveSessionItem): Promise<readonly ITaskEntry[]> {
-		const allTasks = await this._readAllTasks(session);
-		return allTasks.filter(t => !t.inSessions);
+	async getNonSessionTasks(session: IActiveSessionItem): Promise<readonly INonSessionTaskEntry[]> {
+		const result: INonSessionTaskEntry[] = [];
+
+		const workspaceUri = this._getTasksJsonUri(session, 'workspace');
+		if (workspaceUri) {
+			const workspaceJson = await this._readTasksJson(workspaceUri);
+			for (const task of workspaceJson.tasks ?? []) {
+				if (!task.inSessions && this._isSupportedTask(task)) {
+					result.push({ task, target: 'workspace' });
+				}
+			}
+		}
+
+		const userUri = this._getTasksJsonUri(session, 'user');
+		if (userUri) {
+			const userJson = await this._readTasksJson(userUri);
+			for (const task of userJson.tasks ?? []) {
+				if (!task.inSessions && this._isSupportedTask(task)) {
+					result.push({ task, target: 'user' });
+				}
+			}
+		}
+
+		return result;
 	}
 
-	async addTaskToSessions(task: ITaskEntry, session: IActiveSessionItem, target: TaskStorageTarget): Promise<void> {
+	async addTaskToSessions(task: ITaskEntry, session: IActiveSessionItem, target: TaskStorageTarget, options?: ITaskRunOptions): Promise<void> {
 		const tasksJsonUri = this._getTasksJsonUri(session, target);
 		if (!tasksJsonUri) {
 			return;
@@ -142,28 +182,39 @@ export class SessionsConfigurationService extends Disposable implements ISession
 			return;
 		}
 
-		await this._jsonEditingService.write(tasksJsonUri, [
-			{ path: ['tasks', index, 'inSessions'], value: true }
-		], true);
+		const edits: { path: (string | number)[]; value: unknown }[] = [
+			{ path: ['tasks', index, 'inSessions'], value: true },
+		];
+
+		if (options) {
+			edits.push({
+				path: ['tasks', index, 'runOptions'],
+				value: options.runOn && options.runOn !== 'default' ? { runOn: options.runOn } : undefined,
+			});
+		}
+
+		await this._jsonEditingService.write(tasksJsonUri, edits, true);
 
 		if (target === 'workspace') {
 			await this._commitTasksFile(session);
 		}
 	}
 
-	async createAndAddTask(command: string, session: IActiveSessionItem, target: TaskStorageTarget): Promise<void> {
+	async createAndAddTask(label: string | undefined, command: string, session: IActiveSessionItem, target: TaskStorageTarget, options?: ITaskRunOptions): Promise<ITaskEntry | undefined> {
 		const tasksJsonUri = this._getTasksJsonUri(session, target);
 		if (!tasksJsonUri) {
-			return;
+			return undefined;
 		}
 
 		const tasksJson = await this._readTasksJson(tasksJsonUri);
 		const tasks = tasksJson.tasks ?? [];
+		const resolvedLabel = label?.trim() || command;
 		const newTask: ITaskEntry = {
-			label: command,
+			label: resolvedLabel,
 			type: 'shell',
 			command,
 			inSessions: true,
+			...(options?.runOn && options.runOn !== 'default' ? { runOptions: { runOn: options.runOn } } : {}),
 		};
 
 		await this._jsonEditingService.write(tasksJsonUri, [
@@ -174,6 +225,8 @@ export class SessionsConfigurationService extends Disposable implements ISession
 		if (target === 'workspace') {
 			await this._commitTasksFile(session);
 		}
+
+		return newTask;
 	}
 
 	async runTask(task: ITaskEntry, session: IActiveSessionItem): Promise<void> {
@@ -265,7 +318,7 @@ export class SessionsConfigurationService extends Disposable implements ISession
 		if (workspaceUri) {
 			const workspaceJson = await this._readTasksJson(workspaceUri);
 			if (workspaceJson.tasks) {
-				result.push(...workspaceJson.tasks);
+				result.push(...workspaceJson.tasks.filter(t => this._isSupportedTask(t)));
 			}
 		}
 
@@ -274,24 +327,89 @@ export class SessionsConfigurationService extends Disposable implements ISession
 		if (userUri) {
 			const userJson = await this._readTasksJson(userUri);
 			if (userJson.tasks) {
-				result.push(...userJson.tasks);
+				result.push(...userJson.tasks.filter(t => this._isSupportedTask(t)));
 			}
 		}
 
 		return result;
 	}
 
+	private _isSupportedTask(task: ITaskEntry): boolean {
+		return !!task.type && SessionsConfigurationService._SUPPORTED_TASK_TYPES.has(task.type);
+	}
+
 	private _resolveCommand(task: ITaskEntry): string | undefined {
+		if (task.type === 'npm') {
+			if (!task.script) {
+				return undefined;
+			}
+			const base = task.path
+				? `npm --prefix ${task.path} run ${task.script}`
+				: `npm run ${task.script}`;
+			return this._appendArgs(base, task.args);
+		}
+
+		let command: string | undefined;
+		let platformArgs: CommandString[] | undefined;
+
 		if (isWindows && task.windows?.command) {
-			return task.windows.command;
+			command = task.windows.command;
+			platformArgs = task.windows.args;
+		} else if (isMacintosh && task.osx?.command) {
+			command = task.osx.command;
+			platformArgs = task.osx.args;
+		} else if (!isWindows && !isMacintosh && task.linux?.command) {
+			command = task.linux.command;
+			platformArgs = task.linux.args;
+		} else {
+			command = task.command;
 		}
-		if (isMacintosh && task.osx?.command) {
-			return task.osx.command;
+
+		// Platform-specific args override task-level args
+		const args = platformArgs ?? task.args;
+		return this._appendArgs(command, args);
+	}
+
+	private _appendArgs(command: string | undefined, args: CommandString[] | undefined): string | undefined {
+		if (!command) {
+			return undefined;
+		}
+		if (!args || args.length === 0) {
+			return command;
 		}
-		if (!isWindows && !isMacintosh && task.linux?.command) {
-			return task.linux.command;
+		const resolvedArgs = args.map(a => CommandString.value(a)).join(' ');
+		return `${command} ${resolvedArgs}`;
+	}
+
+	private _handleActiveSessionChange(session: IActiveSessionItem | undefined): void {
+		if (!session) {
+			return;
+		}
+
+		const sessionKey = session.resource.toString();
+		const currentWorktree = session.worktree?.toString();
+		if (!this._knownSessionWorktrees.has(sessionKey)) {
+			this._knownSessionWorktrees.set(sessionKey, currentWorktree);
+			return;
+		}
+
+		const previousWorktree = this._knownSessionWorktrees.get(sessionKey);
+		this._knownSessionWorktrees.set(sessionKey, currentWorktree);
+		if (!currentWorktree || previousWorktree === currentWorktree) {
+			return;
+		}
+
+		void this._runWorktreeCreatedTasks(session);
+	}
+
+	private async _runWorktreeCreatedTasks(session: IActiveSessionItem): Promise<void> {
+		const tasks = await this._readAllTasks(session);
+		for (const task of tasks) {
+			if (!task.inSessions || task.runOptions?.runOn !== 'worktreeCreated') {
+				continue;
+			}
+			await this.runTask(task, session);
 		}
-		return task.command;
 	}
 
 	private _ensureFileWatch(folder: URI): void {
@@ -321,12 +439,12 @@ export class SessionsConfigurationService extends Disposable implements ISession
 
 		const tasksUri = joinPath(folder, '.vscode', 'tasks.json');
 		const tasksJson = await this._readTasksJson(tasksUri);
-		const sessionTasks = (tasksJson.tasks ?? []).filter(t => t.inSessions);
+		const sessionTasks = (tasksJson.tasks ?? []).filter(t => t.inSessions && this._isSupportedTask(t));
 
 		// Also include user-level session tasks
 		const userUri = joinPath(dirname(this._preferencesService.userSettingsResource), 'tasks.json');
 		const userJson = await this._readTasksJson(userUri);
-		const userSessionTasks = (userJson.tasks ?? []).filter(t => t.inSessions);
+		const userSessionTasks = (userJson.tasks ?? []).filter(t => t.inSessions && this._isSupportedTask(t));
 
 		transaction(tx => this._sessionTasks.set([...sessionTasks, ...userSessionTasks], tx));
 	}
diff --git a/src/vs/sessions/contrib/chat/browser/slashCommands.ts b/src/vs/sessions/contrib/chat/browser/slashCommands.ts
new file mode 100644
index 0000000000000..4cf481f915e2f
--- /dev/null
+++ b/src/vs/sessions/contrib/chat/browser/slashCommands.ts
@@ -0,0 +1,346 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { themeColorFromId } from '../../../../base/common/themables.js';
+import { CodeEditorWidget } from '../../../../editor/browser/widget/codeEditor/codeEditorWidget.js';
+import { ICodeEditorService } from '../../../../editor/browser/services/codeEditorService.js';
+import { CompletionContext, CompletionItem, CompletionItemKind } from '../../../../editor/common/languages.js';
+import { ITextModel } from '../../../../editor/common/model.js';
+import { IDecorationOptions } from '../../../../editor/common/editorCommon.js';
+import { Position } from '../../../../editor/common/core/position.js';
+import { Range } from '../../../../editor/common/core/range.js';
+import { getWordAtText } from '../../../../editor/common/core/wordHelper.js';
+import { ILanguageFeaturesService } from '../../../../editor/common/services/languageFeatures.js';
+import { CommandsRegistry, ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IThemeService } from '../../../../platform/theme/common/themeService.js';
+import { inputPlaceholderForeground } from '../../../../platform/theme/common/colorRegistry.js';
+import { localize } from '../../../../nls.js';
+import { chatSlashCommandBackground, chatSlashCommandForeground } from '../../../../workbench/contrib/chat/common/widget/chatColors.js';
+import { AICustomizationManagementCommands, AICustomizationManagementSection } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.js';
+import { IAICustomizationWorkspaceService } from '../../../../workbench/contrib/chat/common/aiCustomizationWorkspaceService.js';
+import { IChatPromptSlashCommand, IPromptsService } from '../../../../workbench/contrib/chat/common/promptSyntax/service/promptsService.js';
+import { PromptsType } from '../../../../workbench/contrib/chat/common/promptSyntax/promptTypes.js';
+
+/**
+ * Static command ID used by completion items to trigger immediate slash command execution,
+ * mirroring the pattern of core's `ChatSubmitAction` for `executeImmediately` commands.
+ */
+export const SESSIONS_EXECUTE_SLASH_COMMAND_ID = 'sessions.chat.executeSlashCommand';
+
+CommandsRegistry.registerCommand(SESSIONS_EXECUTE_SLASH_COMMAND_ID, (_, handler: SlashCommandHandler, slashCommandStr: string) => {
+	handler.tryExecuteSlashCommand(slashCommandStr);
+	handler.clearInput();
+});
+
+/**
+ * Minimal slash command descriptor for the sessions new-chat widget.
+ * Self-contained copy of the essential fields from core's `IChatSlashData`
+ * to avoid a direct dependency on the workbench chat slash command service.
+ */
+interface ISessionsSlashCommandData {
+	readonly command: string;
+	readonly detail: string;
+	readonly sortText?: string;
+	readonly executeImmediately?: boolean;
+	readonly execute: (args: string) => void;
+}
+
+/**
+ * Manages slash commands for the sessions new-chat input widget — registration,
+ * autocompletion, decorations (syntax highlighting + placeholder text), and execution.
+ */
+export class SlashCommandHandler extends Disposable {
+
+	private static readonly _slashDecoType = 'sessions-slash-command';
+	private static readonly _slashPlaceholderDecoType = 'sessions-slash-placeholder';
+	private static _slashDecosRegistered = false;
+
+	private readonly _slashCommands: ISessionsSlashCommandData[] = [];
+	private _cachedPromptCommands: readonly IChatPromptSlashCommand[] = [];
+
+	constructor(
+		private readonly _editor: CodeEditorWidget,
+		@ICommandService private readonly commandService: ICommandService,
+		@ICodeEditorService private readonly codeEditorService: ICodeEditorService,
+		@ILanguageFeaturesService private readonly languageFeaturesService: ILanguageFeaturesService,
+		@IThemeService private readonly themeService: IThemeService,
+		@IAICustomizationWorkspaceService private readonly aiCustomizationWorkspaceService: IAICustomizationWorkspaceService,
+		@IPromptsService private readonly promptsService: IPromptsService,
+	) {
+		super();
+		this._registerSlashCommands();
+		this._registerCompletions();
+		this._registerDecorations();
+		this._refreshPromptCommands();
+		this._register(this.promptsService.onDidChangeSlashCommands(() => this._refreshPromptCommands()));
+	}
+
+	clearInput(): void {
+		this._editor.getModel()?.setValue('');
+	}
+
+	private _refreshPromptCommands(): void {
+		this.aiCustomizationWorkspaceService.getFilteredPromptSlashCommands(CancellationToken.None).then(commands => {
+			this._cachedPromptCommands = commands;
+			this._updateDecorations();
+		}, () => { /* swallow errors from stale refresh */ });
+	}
+
+	/**
+	 * Attempts to parse and execute a slash command from the input.
+	 * Returns `true` if a command was handled.
+	 */
+	tryExecuteSlashCommand(query: string): boolean {
+		const match = query.match(/^\/([\w\p{L}\d_\-\.:]+)\s*(.*)/su);
+		if (!match) {
+			return false;
+		}
+
+		const commandName = match[1];
+		const slashCommand = this._slashCommands.find(c => c.command === commandName);
+		if (!slashCommand) {
+			return false;
+		}
+
+		slashCommand.execute(match[2]?.trim() ?? '');
+		return true;
+	}
+
+	/**
+	 * If the query starts with a prompt/skill slash command (e.g. `/my-prompt args`),
+	 * expands it into a CLI-friendly markdown reference so the agent can locate the
+	 * file. Returns `undefined` when the query is not a prompt slash command.
+	 */
+	tryExpandPromptSlashCommand(query: string): string | undefined {
+		const match = query.match(/^\/([\w\p{L}\d_\-\.:]+)\s*(.*)/su);
+		if (!match) {
+			return undefined;
+		}
+
+		const commandName = match[1];
+		const promptCommand = this._cachedPromptCommands.find(c => c.name === commandName);
+		if (!promptCommand) {
+			return undefined;
+		}
+
+		const args = match[2]?.trim() ?? '';
+		const uri = promptCommand.promptPath.uri;
+		const typeLabel = promptCommand.promptPath.type === PromptsType.skill ? 'skill' : 'prompt file';
+		const expanded = `Use the ${typeLabel} located at [${promptCommand.name}](${uri.toString()}).`;
+		return args ? `${expanded} ${args}` : expanded;
+	}
+
+	private _registerSlashCommands(): void {
+		const openSection = (section: AICustomizationManagementSection) =>
+			() => this.commandService.executeCommand(AICustomizationManagementCommands.OpenEditor, section);
+
+		this._slashCommands.push({
+			command: 'agents',
+			detail: localize('slashCommand.agents', "View and manage custom agents"),
+			sortText: 'z3_agents',
+			executeImmediately: true,
+			execute: openSection(AICustomizationManagementSection.Agents),
+		});
+		this._slashCommands.push({
+			command: 'skills',
+			detail: localize('slashCommand.skills', "View and manage skills"),
+			sortText: 'z3_skills',
+			executeImmediately: true,
+			execute: openSection(AICustomizationManagementSection.Skills),
+		});
+		this._slashCommands.push({
+			command: 'instructions',
+			detail: localize('slashCommand.instructions', "View and manage instructions"),
+			sortText: 'z3_instructions',
+			executeImmediately: true,
+			execute: openSection(AICustomizationManagementSection.Instructions),
+		});
+		this._slashCommands.push({
+			command: 'prompts',
+			detail: localize('slashCommand.prompts', "View and manage prompt files"),
+			sortText: 'z3_prompts',
+			executeImmediately: true,
+			execute: openSection(AICustomizationManagementSection.Prompts),
+		});
+		this._slashCommands.push({
+			command: 'hooks',
+			detail: localize('slashCommand.hooks', "View and manage hooks"),
+			sortText: 'z3_hooks',
+			executeImmediately: true,
+			execute: openSection(AICustomizationManagementSection.Hooks),
+		});
+	}
+
+	private _registerDecorations(): void {
+		if (!SlashCommandHandler._slashDecosRegistered) {
+			SlashCommandHandler._slashDecosRegistered = true;
+			this.codeEditorService.registerDecorationType('sessions-chat', SlashCommandHandler._slashDecoType, {
+				color: themeColorFromId(chatSlashCommandForeground),
+				backgroundColor: themeColorFromId(chatSlashCommandBackground),
+				borderRadius: '3px',
+			});
+			this.codeEditorService.registerDecorationType('sessions-chat', SlashCommandHandler._slashPlaceholderDecoType, {});
+		}
+
+		this._register(this._editor.onDidChangeModelContent(() => this._updateDecorations()));
+		this._updateDecorations();
+	}
+
+	private _updateDecorations(): void {
+		const model = this._editor.getModel();
+		const value = model?.getValue() ?? '';
+		const match = value.match(/^\/([\w\p{L}\d_\-\.:]+)\s?/u);
+
+		if (!match) {
+			this._editor.setDecorationsByType('sessions-chat', SlashCommandHandler._slashDecoType, []);
+			this._editor.setDecorationsByType('sessions-chat', SlashCommandHandler._slashPlaceholderDecoType, []);
+			return;
+		}
+
+		const commandName = match[1];
+		const slashCommand = this._slashCommands.find(c => c.command === commandName);
+		const promptCommand = this._cachedPromptCommands.find(c => c.name === commandName);
+		if (!slashCommand && !promptCommand) {
+			this._editor.setDecorationsByType('sessions-chat', SlashCommandHandler._slashDecoType, []);
+			this._editor.setDecorationsByType('sessions-chat', SlashCommandHandler._slashPlaceholderDecoType, []);
+			return;
+		}
+
+		// Highlight the slash command text
+		const commandEnd = match[0].trimEnd().length;
+		const commandDeco: IDecorationOptions[] = [{
+			range: { startLineNumber: 1, startColumn: 1, endLineNumber: 1, endColumn: commandEnd + 1 },
+		}];
+		this._editor.setDecorationsByType('sessions-chat', SlashCommandHandler._slashDecoType, commandDeco);
+
+		// Show the command description as a placeholder after the command
+		const restOfInput = value.slice(match[0].length).trim();
+		const detail = slashCommand?.detail ?? promptCommand?.description;
+		if (!restOfInput && detail) {
+			const placeholderCol = match[0].length + 1;
+			const placeholderDeco: IDecorationOptions[] = [{
+				range: { startLineNumber: 1, startColumn: placeholderCol, endLineNumber: 1, endColumn: model!.getLineMaxColumn(1) },
+				renderOptions: {
+					after: {
+						contentText: detail,
+						color: this._getPlaceholderColor(),
+					}
+				}
+			}];
+			this._editor.setDecorationsByType('sessions-chat', SlashCommandHandler._slashPlaceholderDecoType, placeholderDeco);
+		} else {
+			this._editor.setDecorationsByType('sessions-chat', SlashCommandHandler._slashPlaceholderDecoType, []);
+		}
+	}
+
+	private _getPlaceholderColor(): string | undefined {
+		const theme = this.themeService.getColorTheme();
+		return theme.getColor(inputPlaceholderForeground)?.toString();
+	}
+
+	private _registerCompletions(): void {
+		const uri = this._editor.getModel()?.uri;
+		if (!uri) {
+			return;
+		}
+
+		this._register(this.languageFeaturesService.completionProvider.register({ scheme: uri.scheme, hasAccessToAllModels: true }, {
+			_debugDisplayName: 'sessionsSlashCommands',
+			triggerCharacters: ['/'],
+			provideCompletionItems: (model: ITextModel, position: Position, _context: CompletionContext, _token: CancellationToken) => {
+				const range = this._computeCompletionRanges(model, position, /\/\w*/g);
+				if (!range) {
+					return null;
+				}
+
+				// Only allow slash commands at the start of input
+				const textBefore = model.getValueInRange(new Range(1, 1, range.replace.startLineNumber, range.replace.startColumn));
+				if (textBefore.trim() !== '') {
+					return null;
+				}
+
+				return {
+					suggestions: this._slashCommands.map((c, i): CompletionItem => {
+						const withSlash = `/${c.command}`;
+						return {
+							label: withSlash,
+							insertText: c.executeImmediately ? '' : `${withSlash} `,
+							detail: c.detail,
+							range,
+							sortText: c.sortText ?? 'a'.repeat(i + 1),
+							kind: CompletionItemKind.Text,
+							command: c.executeImmediately ? { id: SESSIONS_EXECUTE_SLASH_COMMAND_ID, title: withSlash, arguments: [this, withSlash] } : undefined,
+						};
+					})
+				};
+			}
+		}));
+
+		// Dynamic completions for individual prompt/skill files (filtered to match
+		// what the sessions customizations view shows).
+		this._register(this.languageFeaturesService.completionProvider.register({ scheme: uri.scheme, hasAccessToAllModels: true }, {
+			_debugDisplayName: 'sessionsPromptSlashCommands',
+			triggerCharacters: ['/'],
+			provideCompletionItems: async (model: ITextModel, position: Position, _context: CompletionContext, token: CancellationToken) => {
+				const range = this._computeCompletionRanges(model, position, /\/[\p{L}0-9_.:-]*/gu);
+				if (!range) {
+					return null;
+				}
+
+				const textBefore = model.getValueInRange(new Range(1, 1, range.replace.startLineNumber, range.replace.startColumn));
+				if (textBefore.trim() !== '') {
+					return null;
+				}
+
+				const promptCommands = await this.aiCustomizationWorkspaceService.getFilteredPromptSlashCommands(token);
+				const userInvocable = promptCommands.filter(c => c.parsedPromptFile?.header?.userInvocable !== false);
+				if (userInvocable.length === 0) {
+					return null;
+				}
+
+				return {
+					suggestions: userInvocable.map((c, i): CompletionItem => {
+						const label = `/${c.name}`;
+						return {
+							label: { label, description: c.description },
+							insertText: `${label} `,
+							documentation: c.description,
+							range,
+							sortText: 'b'.repeat(i + 1),
+							kind: CompletionItemKind.Text,
+						};
+					})
+				};
+			}
+		}));
+	}
+
+	private _computeCompletionRanges(model: ITextModel, position: Position, reg: RegExp): { insert: Range; replace: Range } | undefined {
+		const varWord = getWordAtText(position.column, reg, model.getLineContent(position.lineNumber), 0);
+		if (!varWord && model.getWordUntilPosition(position).word) {
+			return;
+		}
+
+		if (!varWord && position.column > 1) {
+			const textBefore = model.getValueInRange(new Range(position.lineNumber, position.column - 1, position.lineNumber, position.column));
+			if (textBefore !== ' ') {
+				return;
+			}
+		}
+
+		let insert: Range;
+		let replace: Range;
+		if (!varWord) {
+			insert = replace = Range.fromPositions(position);
+		} else {
+			insert = new Range(position.lineNumber, varWord.startColumn, position.lineNumber, position.column);
+			replace = new Range(position.lineNumber, varWord.startColumn, position.lineNumber, varWord.endColumn);
+		}
+
+		return { insert, replace };
+	}
+}
diff --git a/src/vs/sessions/contrib/chat/browser/syncIndicator.ts b/src/vs/sessions/contrib/chat/browser/syncIndicator.ts
new file mode 100644
index 0000000000000..b63411982720a
--- /dev/null
+++ b/src/vs/sessions/contrib/chat/browser/syncIndicator.ts
@@ -0,0 +1,181 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../base/browser/dom.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
+import { autorun } from '../../../../base/common/observable.js';
+import { ThemeIcon } from '../../../../base/common/themables.js';
+import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
+import { localize } from '../../../../nls.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IGitRepository } from '../../../../workbench/contrib/git/common/gitService.js';
+
+const GIT_SYNC_COMMAND = 'git.sync';
+
+/**
+ * Renders a compact "Synchronize Changes" button next to the branch picker.
+ * Shows ahead/behind counts (e.g. "3↓ 2↑") and is only visible when
+ * the selected branch matches the repository HEAD and has changes to sync.
+ */
+export class SyncIndicator extends Disposable {
+
+	private _repository: IGitRepository | undefined;
+	private _selectedBranch: string | undefined;
+	private _visible = true;
+	private _syncing = false;
+
+	private readonly _renderDisposables = this._register(new DisposableStore());
+	private readonly _stateDisposables = this._register(new DisposableStore());
+
+	private _slotElement: HTMLElement | undefined;
+	private _buttonElement: HTMLElement | undefined;
+
+	constructor(
+		@ICommandService private readonly commandService: ICommandService,
+	) {
+		super();
+	}
+
+	/**
+	 * Sets the git repository. Subscribes to its state observable to react to
+	 * ahead/behind changes.
+	 */
+	setRepository(repository: IGitRepository | undefined): void {
+		this._stateDisposables.clear();
+		this._repository = repository;
+
+		if (repository) {
+			this._stateDisposables.add(autorun(reader => {
+				repository.state.read(reader);
+				this._update();
+			}));
+		} else {
+			this._update();
+		}
+	}
+
+	/**
+	 * Sets the currently selected branch name (from the branch picker).
+	 * The sync indicator is only shown when the selected branch is the HEAD branch.
+	 */
+	setBranch(branch: string | undefined): void {
+		this._selectedBranch = branch;
+		this._update();
+	}
+
+	/**
+	 * Renders the sync indicator button into the given container.
+	 */
+	render(container: HTMLElement): void {
+		this._renderDisposables.clear();
+
+		const slot = dom.append(container, dom.$('.sessions-chat-picker-slot.sessions-chat-sync-indicator'));
+		this._slotElement = slot;
+		this._renderDisposables.add({ dispose: () => slot.remove() });
+
+		const button = dom.append(slot, dom.$('a.action-label'));
+		button.tabIndex = 0;
+		button.role = 'button';
+		this._buttonElement = button;
+
+		this._renderDisposables.add(dom.addDisposableListener(button, dom.EventType.CLICK, (e) => {
+			dom.EventHelper.stop(e, true);
+			this._executeSyncCommand();
+		}));
+
+		this._renderDisposables.add(dom.addDisposableListener(button, dom.EventType.KEY_DOWN, (e) => {
+			if (e.key === 'Enter' || e.key === ' ') {
+				dom.EventHelper.stop(e, true);
+				this._executeSyncCommand();
+			}
+		}));
+
+		this._update();
+	}
+
+	/**
+	 * Shows or hides the sync indicator slot.
+	 */
+	setVisible(visible: boolean): void {
+		this._visible = visible;
+		this._update();
+	}
+
+	private async _executeSyncCommand(): Promise<void> {
+		if (this._syncing) {
+			return;
+		}
+		this._syncing = true;
+		this._update();
+		try {
+			await this.commandService.executeCommand(GIT_SYNC_COMMAND, this._repository?.rootUri);
+		} finally {
+			this._syncing = false;
+			this._update();
+		}
+	}
+
+	private _getAheadBehind(): { ahead: number; behind: number } | undefined {
+		if (!this._repository) {
+			return undefined;
+		}
+
+		const head = this._repository.state.get().HEAD;
+		if (!head?.upstream) {
+			return undefined;
+		}
+
+		// Only show sync for the HEAD branch (i.e. the selected branch must match the actual HEAD)
+		if (head.name !== this._selectedBranch) {
+			return undefined;
+		}
+
+		const ahead = head.ahead ?? 0;
+		const behind = head.behind ?? 0;
+		if (ahead === 0 && behind === 0) {
+			return undefined;
+		}
+
+		return { ahead, behind };
+	}
+
+	private _update(): void {
+		if (!this._slotElement || !this._buttonElement) {
+			return;
+		}
+
+		const counts = this._getAheadBehind();
+		if ((!counts && !this._syncing) || !this._visible) {
+			this._slotElement.style.display = 'none';
+			return;
+		}
+
+		this._slotElement.style.display = '';
+
+		dom.clearNode(this._buttonElement);
+		dom.append(this._buttonElement, renderIcon(this._syncing ? ThemeIcon.modify(Codicon.sync, 'spin') : Codicon.sync));
+
+		if (counts) {
+			const parts: string[] = [];
+			if (counts.behind > 0) {
+				parts.push(`${counts.behind}↓`);
+			}
+			if (counts.ahead > 0) {
+				parts.push(`${counts.ahead}↑`);
+			}
+
+			const label = dom.append(this._buttonElement, dom.$('span.sessions-chat-dropdown-label'));
+			label.textContent = parts.join('\u00a0');
+		}
+
+		this._buttonElement.title = localize(
+			'syncIndicator.tooltip',
+			"Synchronize Changes ({0} to pull, {1} to push)",
+			counts?.behind ?? 0,
+			counts?.ahead ?? 0,
+		);
+	}
+}
diff --git a/src/vs/sessions/contrib/chat/common/builtinPromptsStorage.ts b/src/vs/sessions/contrib/chat/common/builtinPromptsStorage.ts
new file mode 100644
index 0000000000000..fb3efadd52f41
--- /dev/null
+++ b/src/vs/sessions/contrib/chat/common/builtinPromptsStorage.ts
@@ -0,0 +1,28 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { URI } from '../../../../base/common/uri.js';
+import { PromptsStorage } from '../../../../workbench/contrib/chat/common/promptSyntax/service/promptsService.js';
+import { PromptsType } from '../../../../workbench/contrib/chat/common/promptSyntax/promptTypes.js';
+
+/**
+ * Extended storage type for AI Customization that includes built-in prompts
+ * shipped with the application, alongside the core `PromptsStorage` values.
+ */
+export type AICustomizationPromptsStorage = PromptsStorage | 'builtin';
+
+/**
+ * Storage type discriminator for built-in prompts shipped with the application.
+ */
+export const BUILTIN_STORAGE: AICustomizationPromptsStorage = 'builtin';
+
+/**
+ * Prompt path for built-in prompts bundled with the Sessions app.
+ */
+export interface IBuiltinPromptPath {
+	readonly uri: URI;
+	readonly storage: AICustomizationPromptsStorage;
+	readonly type: PromptsType;
+}
diff --git a/src/vs/sessions/contrib/chat/test/browser/runScriptCustomTaskWidget.fixture.ts b/src/vs/sessions/contrib/chat/test/browser/runScriptCustomTaskWidget.fixture.ts
new file mode 100644
index 0000000000000..e20913a9a98c8
--- /dev/null
+++ b/src/vs/sessions/contrib/chat/test/browser/runScriptCustomTaskWidget.fixture.ts
@@ -0,0 +1,124 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { ComponentFixtureContext, defineComponentFixture, defineThemedFixtureGroup } from '../../../../../workbench/test/browser/componentFixtures/fixtureUtils.js';
+import { IRunScriptCustomTaskWidgetState, RunScriptCustomTaskWidget, WORKTREE_CREATED_RUN_ON } from '../../browser/runScriptCustomTaskWidget.js';
+
+// Ensure color registrations are loaded
+import '../../../../common/theme.js';
+import '../../../../../platform/theme/common/colors/inputColors.js';
+
+const filledLabel = 'Start Dev Server';
+const filledCommand = 'npm run dev';
+const workspaceUnavailableReason = 'Workspace storage is unavailable for this session';
+
+function renderWidget(ctx: ComponentFixtureContext, state: IRunScriptCustomTaskWidgetState): void {
+	ctx.container.style.width = '600px';
+	ctx.container.style.padding = '0';
+	ctx.container.style.borderRadius = 'var(--vscode-cornerRadius-xLarge)';
+	ctx.container.style.backgroundColor = 'var(--vscode-quickInput-background)';
+	ctx.container.style.overflow = 'hidden';
+
+	const widget = ctx.disposableStore.add(new RunScriptCustomTaskWidget(state));
+	ctx.container.appendChild(widget.domNode);
+}
+
+function defineFixture(state: IRunScriptCustomTaskWidgetState) {
+	return defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: ctx => renderWidget(ctx, state),
+	});
+}
+
+export default defineThemedFixtureGroup({ path: 'sessions/' }, {
+	WorkspaceSelectedEmpty: defineFixture({
+		target: 'workspace',
+	}),
+
+	WorkspaceSelectedCheckedEmpty: defineFixture({
+		target: 'workspace',
+		runOn: WORKTREE_CREATED_RUN_ON,
+	}),
+
+	WorkspaceSelectedFilled: defineFixture({
+		label: filledLabel,
+		target: 'workspace',
+		command: filledCommand,
+	}),
+
+	WorkspaceSelectedCheckedFilled: defineFixture({
+		label: filledLabel,
+		target: 'workspace',
+		command: filledCommand,
+		runOn: WORKTREE_CREATED_RUN_ON,
+	}),
+
+	UserSelectedEmpty: defineFixture({
+		target: 'user',
+	}),
+
+	UserSelectedCheckedEmpty: defineFixture({
+		target: 'user',
+		runOn: WORKTREE_CREATED_RUN_ON,
+	}),
+
+	UserSelectedFilled: defineFixture({
+		label: filledLabel,
+		target: 'user',
+		command: filledCommand,
+	}),
+
+	UserSelectedCheckedFilled: defineFixture({
+		label: filledLabel,
+		target: 'user',
+		command: filledCommand,
+		runOn: WORKTREE_CREATED_RUN_ON,
+	}),
+
+	WorkspaceUnavailableEmpty: defineFixture({
+		target: 'user',
+		targetDisabledReason: workspaceUnavailableReason,
+	}),
+
+	WorkspaceUnavailableCheckedEmpty: defineFixture({
+		target: 'user',
+		targetDisabledReason: workspaceUnavailableReason,
+		runOn: WORKTREE_CREATED_RUN_ON,
+	}),
+
+	WorkspaceUnavailableFilled: defineFixture({
+		label: filledLabel,
+		target: 'user',
+		command: filledCommand,
+		targetDisabledReason: workspaceUnavailableReason,
+	}),
+
+	WorkspaceUnavailableCheckedFilled: defineFixture({
+		label: filledLabel,
+		target: 'user',
+		command: filledCommand,
+		targetDisabledReason: workspaceUnavailableReason,
+		runOn: WORKTREE_CREATED_RUN_ON,
+	}),
+
+	ExistingWorkspaceTaskLocked: defineFixture({
+		label: filledLabel,
+		labelDisabledReason: 'This name comes from an existing task and cannot be changed here.',
+		command: filledCommand,
+		commandDisabledReason: 'This command comes from an existing task and cannot be changed here.',
+		target: 'workspace',
+		targetDisabledReason: 'This existing task cannot be moved between workspace and user storage.',
+	}),
+
+	ExistingUserTaskLockedChecked: defineFixture({
+		label: filledLabel,
+		labelDisabledReason: 'This name comes from an existing task and cannot be changed here.',
+		command: filledCommand,
+		commandDisabledReason: 'This command comes from an existing task and cannot be changed here.',
+		target: 'user',
+		targetDisabledReason: 'This existing task cannot be moved between workspace and user storage.',
+		runOn: WORKTREE_CREATED_RUN_ON,
+	}),
+});
diff --git a/src/vs/sessions/contrib/chat/test/browser/sessionsConfigurationService.test.ts b/src/vs/sessions/contrib/chat/test/browser/sessionsConfigurationService.test.ts
index 46e663337003c..073e6c42d02b3 100644
--- a/src/vs/sessions/contrib/chat/test/browser/sessionsConfigurationService.test.ts
+++ b/src/vs/sessions/contrib/chat/test/browser/sessionsConfigurationService.test.ts
@@ -15,14 +15,19 @@ import { IJSONEditingService, IJSONValue } from '../../../../../workbench/servic
 import { IPreferencesService } from '../../../../../workbench/services/preferences/common/preferences.js';
 import { ITerminalInstance, ITerminalService } from '../../../../../workbench/contrib/terminal/browser/terminal.js';
 import { IActiveSessionItem, ISessionsManagementService } from '../../../sessions/browser/sessionsManagementService.js';
-import { ISessionsConfigurationService, SessionsConfigurationService, ITaskEntry } from '../../browser/sessionsConfigurationService.js';
+import { INonSessionTaskEntry, ISessionsConfigurationService, SessionsConfigurationService, ITaskEntry } from '../../browser/sessionsConfigurationService.js';
 import { VSBuffer } from '../../../../../base/common/buffer.js';
 import { observableValue } from '../../../../../base/common/observable.js';
 
 function makeSession(opts: { repository?: URI; worktree?: URI } = {}): IActiveSessionItem {
 	return {
+		resource: URI.parse('file:///session'),
+		isUntitled: false,
+		label: 'session',
 		repository: opts.repository,
 		worktree: opts.worktree,
+		worktreeBranchName: undefined,
+		providerType: 'background',
 	} as IActiveSessionItem;
 }
 
@@ -30,6 +35,14 @@ function makeTask(label: string, command?: string, inSessions?: boolean): ITaskE
 	return { label, type: 'shell', command: command ?? label, inSessions };
 }
 
+function makeNpmTask(label: string, script: string, inSessions?: boolean): ITaskEntry {
+	return { label, type: 'npm', script, inSessions };
+}
+
+function makeUnsupportedTask(label: string, inSessions?: boolean): ITaskEntry {
+	return { label, type: 'gulp', command: label, inSessions };
+}
+
 function tasksJsonContent(tasks: ITaskEntry[]): string {
 	return JSON.stringify({ version: '2.0.0', tasks });
 }
@@ -44,6 +57,8 @@ suite('SessionsConfigurationService', () => {
 	let sentCommands: { command: string }[];
 	let committedFiles: { session: IActiveSessionItem; fileUris: URI[] }[];
 	let storageService: InMemoryStorageService;
+	let readFileCalls: URI[];
+	let activeSessionObs: ReturnType<typeof observableValue<IActiveSessionItem | undefined>>;
 
 	const userSettingsUri = URI.parse('file:///user/settings.json');
 	const repoUri = URI.parse('file:///repo');
@@ -55,11 +70,14 @@ suite('SessionsConfigurationService', () => {
 		createdTerminals = [];
 		sentCommands = [];
 		committedFiles = [];
+		readFileCalls = [];
 
 		const instantiationService = store.add(new TestInstantiationService());
+		activeSessionObs = observableValue('activeSession', undefined);
 
 		instantiationService.stub(IFileService, new class extends mock<IFileService>() {
 			override async readFile(resource: URI) {
+				readFileCalls.push(resource);
 				const content = fileContents.get(resource.toString());
 				if (content === undefined) {
 					throw new Error('file not found');
@@ -104,7 +122,7 @@ suite('SessionsConfigurationService', () => {
 		instantiationService.stub(ITerminalService, terminalServiceMock);
 
 		instantiationService.stub(ISessionsManagementService, new class extends mock<ISessionsManagementService>() {
-			override activeSession = observableValue('activeSession', undefined);
+			override activeSession = activeSessionObs;
 			override async commitWorktreeFiles(session: IActiveSessionItem, fileUris: URI[]) { committedFiles.push({ session, fileUris }); }
 		});
 
@@ -128,6 +146,8 @@ suite('SessionsConfigurationService', () => {
 			makeTask('build', 'npm run build', true),
 			makeTask('lint', 'npm run lint', false),
 			makeTask('test', 'npm test', true),
+			makeNpmTask('watch', 'watch', true),
+			makeUnsupportedTask('gulp-task', true),
 		]));
 		// user tasks.json — empty
 		const userTasksUri = URI.from({ scheme: userSettingsUri.scheme, path: '/user/tasks.json' });
@@ -140,7 +160,7 @@ suite('SessionsConfigurationService', () => {
 		await new Promise(r => setTimeout(r, 10));
 		const tasks = obs.get();
 
-		assert.deepStrictEqual(tasks.map(t => t.label), ['build', 'test']);
+		assert.deepStrictEqual(tasks.map(t => t.label), ['build', 'test', 'watch']);
 	});
 
 	test('getSessionTasks returns empty array when no worktree', async () => {
@@ -167,14 +187,38 @@ suite('SessionsConfigurationService', () => {
 		assert.deepStrictEqual(obs.get().map(t => t.label), ['serve']);
 	});
 
+	test('getSessionTasks does not re-read files on repeated calls for the same folder', async () => {
+		const worktreeTasksUri = URI.parse('file:///worktree/.vscode/tasks.json');
+		const userTasksUri = URI.from({ scheme: userSettingsUri.scheme, path: '/user/tasks.json' });
+		fileContents.set(worktreeTasksUri.toString(), tasksJsonContent([
+			makeTask('build', 'npm run build', true),
+		]));
+		fileContents.set(userTasksUri.toString(), tasksJsonContent([]));
+
+		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
+
+		// Call getSessionTasks multiple times for the same session/folder
+		service.getSessionTasks(session);
+		service.getSessionTasks(session);
+		service.getSessionTasks(session);
+
+		await new Promise(r => setTimeout(r, 10));
+
+		// _refreshSessionTasks reads two files (workspace + user tasks.json).
+		// If refresh triggered more than once, we'd see > 2 reads.
+		assert.strictEqual(readFileCalls.length, 2, 'should read files only once (no duplicate refresh)');
+	});
+
 	// --- getNonSessionTasks ---
 
-	test('getNonSessionTasks returns only tasks without inSessions', async () => {
+	test('getNonSessionTasks returns only tasks without inSessions and with supported types', async () => {
 		const worktreeTasksUri = URI.parse('file:///worktree/.vscode/tasks.json');
 		fileContents.set(worktreeTasksUri.toString(), tasksJsonContent([
 			makeTask('build', 'npm run build', true),
 			makeTask('lint', 'npm run lint', false),
 			makeTask('test', 'npm test'),
+			makeNpmTask('watch', 'watch', false),
+			makeUnsupportedTask('gulp-task', false),
 		]));
 		const userTasksUri = URI.from({ scheme: userSettingsUri.scheme, path: '/user/tasks.json' });
 		fileContents.set(userTasksUri.toString(), tasksJsonContent([]));
@@ -182,7 +226,7 @@ suite('SessionsConfigurationService', () => {
 		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
 		const nonSessionTasks = await service.getNonSessionTasks(session);
 
-		assert.deepStrictEqual(nonSessionTasks.map(t => t.label), ['lint', 'test']);
+		assert.deepStrictEqual(nonSessionTasks.map(t => t.task.label), ['lint', 'test', 'watch']);
 	});
 
 	test('getNonSessionTasks reads from repository when no worktree', async () => {
@@ -197,7 +241,26 @@ suite('SessionsConfigurationService', () => {
 		const session = makeSession({ repository: repoUri });
 		const nonSessionTasks = await service.getNonSessionTasks(session);
 
-		assert.deepStrictEqual(nonSessionTasks.map(t => t.label), ['lint']);
+		assert.deepStrictEqual(nonSessionTasks.map(t => t.task.label), ['lint']);
+	});
+
+	test('getNonSessionTasks preserves the source target for workspace and user tasks', async () => {
+		const worktreeTasksUri = URI.parse('file:///worktree/.vscode/tasks.json');
+		const userTasksUri = URI.from({ scheme: userSettingsUri.scheme, path: '/user/tasks.json' });
+		fileContents.set(worktreeTasksUri.toString(), tasksJsonContent([
+			makeTask('workspaceTask', 'npm run workspace'),
+		]));
+		fileContents.set(userTasksUri.toString(), tasksJsonContent([
+			makeTask('userTask', 'npm run user'),
+		]));
+
+		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
+		const nonSessionTasks = await service.getNonSessionTasks(session);
+
+		assert.deepStrictEqual(nonSessionTasks, [
+			{ task: { label: 'workspaceTask', type: 'shell', command: 'npm run workspace' }, target: 'workspace' },
+			{ task: { label: 'userTask', type: 'shell', command: 'npm run user' }, target: 'user' },
+		] satisfies INonSessionTaskEntry[]);
 	});
 
 	// --- addTaskToSessions ---
@@ -247,6 +310,36 @@ suite('SessionsConfigurationService', () => {
 		assert.strictEqual(committedFiles.length, 0, 'should not commit when there is no worktree');
 	});
 
+	test('addTaskToSessions updates runOptions when provided', async () => {
+		const worktreeTasksUri = URI.parse('file:///worktree/.vscode/tasks.json');
+		fileContents.set(worktreeTasksUri.toString(), tasksJsonContent([
+			makeTask('build', 'npm run build'),
+		]));
+
+		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
+		await service.addTaskToSessions(makeTask('build', 'npm run build'), session, 'workspace', { runOn: 'worktreeCreated' });
+
+		assert.deepStrictEqual(jsonEdits[0].values, [
+			{ path: ['tasks', 0, 'inSessions'], value: true },
+			{ path: ['tasks', 0, 'runOptions'], value: { runOn: 'worktreeCreated' } },
+		]);
+	});
+
+	test('addTaskToSessions clears runOptions when default is requested', async () => {
+		const worktreeTasksUri = URI.parse('file:///worktree/.vscode/tasks.json');
+		fileContents.set(worktreeTasksUri.toString(), tasksJsonContent([
+			{ ...makeTask('build', 'npm run build'), runOptions: { runOn: 'worktreeCreated' } },
+		]));
+
+		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
+		await service.addTaskToSessions(makeTask('build', 'npm run build'), session, 'workspace', { runOn: 'default' });
+
+		assert.deepStrictEqual(jsonEdits[0].values, [
+			{ path: ['tasks', 0, 'inSessions'], value: true },
+			{ path: ['tasks', 0, 'runOptions'], value: undefined },
+		]);
+	});
+
 	// --- createAndAddTask ---
 
 	test('createAndAddTask writes new task with inSessions: true', async () => {
@@ -256,7 +349,7 @@ suite('SessionsConfigurationService', () => {
 		]));
 
 		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
-		await service.createAndAddTask('npm run dev', session, 'workspace');
+		await service.createAndAddTask(undefined, 'npm run dev', session, 'workspace');
 
 		assert.strictEqual(jsonEdits.length, 1);
 		const edit = jsonEdits[0];
@@ -278,7 +371,7 @@ suite('SessionsConfigurationService', () => {
 		]));
 
 		const session = makeSession({ repository: repoUri });
-		await service.createAndAddTask('npm run dev', session, 'workspace');
+		await service.createAndAddTask(undefined, 'npm run dev', session, 'workspace');
 
 		assert.strictEqual(jsonEdits.length, 1);
 		assert.strictEqual(jsonEdits[0].uri.toString(), repoTasksUri.toString());
@@ -291,6 +384,35 @@ suite('SessionsConfigurationService', () => {
 		assert.strictEqual(committedFiles.length, 0, 'should not commit when there is no worktree');
 	});
 
+	test('createAndAddTask writes worktreeCreated run option when requested', async () => {
+		const worktreeTasksUri = URI.parse('file:///worktree/.vscode/tasks.json');
+		fileContents.set(worktreeTasksUri.toString(), tasksJsonContent([]));
+
+		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
+		await service.createAndAddTask(undefined, 'npm run dev', session, 'workspace', { runOn: 'worktreeCreated' });
+
+		assert.strictEqual(jsonEdits.length, 1);
+		const tasksValue = jsonEdits[0].values.find(v => v.path[0] === 'tasks');
+		assert.ok(tasksValue);
+		const tasks = tasksValue!.value as ITaskEntry[];
+		assert.deepStrictEqual(tasks[0].runOptions, { runOn: 'worktreeCreated' });
+	});
+
+	test('createAndAddTask writes a custom label when provided', async () => {
+		const worktreeTasksUri = URI.parse('file:///worktree/.vscode/tasks.json');
+		fileContents.set(worktreeTasksUri.toString(), tasksJsonContent([]));
+
+		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
+		await service.createAndAddTask('Start Dev Server', 'npm run dev', session, 'workspace');
+
+		assert.strictEqual(jsonEdits.length, 1);
+		const tasksValue = jsonEdits[0].values.find(v => v.path[0] === 'tasks');
+		assert.ok(tasksValue);
+		const tasks = tasksValue!.value as ITaskEntry[];
+		assert.strictEqual(tasks[0].label, 'Start Dev Server');
+		assert.strictEqual(tasks[0].command, 'npm run dev');
+	});
+
 	// --- runTask ---
 
 	test('runTask creates terminal and sends command', async () => {
@@ -305,6 +427,28 @@ suite('SessionsConfigurationService', () => {
 		assert.strictEqual(sentCommands[0].command, 'npm run build');
 	});
 
+	test('runTask resolves npm task to npm run <script>', async () => {
+		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
+		const task = makeNpmTask('watch', 'watch');
+
+		await service.runTask(task, session);
+
+		assert.strictEqual(createdTerminals.length, 1);
+		assert.strictEqual(createdTerminals[0].name, 'watch');
+		assert.strictEqual(sentCommands.length, 1);
+		assert.strictEqual(sentCommands[0].command, 'npm run watch');
+	});
+
+	test('runTask does nothing for npm task without script', async () => {
+		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
+		const task: ITaskEntry = { label: 'broken', type: 'npm', inSessions: true };
+
+		await service.runTask(task, session);
+
+		assert.strictEqual(createdTerminals.length, 0);
+		assert.strictEqual(sentCommands.length, 0);
+	});
+
 	test('runTask does nothing when no cwd available', async () => {
 		const session = makeSession({ repository: undefined, worktree: undefined });
 		await service.runTask(makeTask('build', 'npm run build'), session);
@@ -337,6 +481,54 @@ suite('SessionsConfigurationService', () => {
 		assert.strictEqual(createdTerminals[1].name, 'test');
 	});
 
+	test('runTask appends args to shell command', async () => {
+		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
+		const task: ITaskEntry = { label: 'build', type: 'shell', command: 'dotnet', args: ['build', '--configuration', 'Release'], inSessions: true };
+
+		await service.runTask(task, session);
+
+		assert.strictEqual(sentCommands.length, 1);
+		assert.strictEqual(sentCommands[0].command, 'dotnet build --configuration Release');
+	});
+
+	test('runTask appends args to npm task', async () => {
+		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
+		const task: ITaskEntry = { label: 'test', type: 'npm', script: 'test', args: ['--', '--coverage'], inSessions: true };
+
+		await service.runTask(task, session);
+
+		assert.strictEqual(sentCommands.length, 1);
+		assert.strictEqual(sentCommands[0].command, 'npm run test -- --coverage');
+	});
+
+	test('runTask resolves CommandString objects in args', async () => {
+		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
+		const task: ITaskEntry = {
+			label: 'build', type: 'shell', command: 'gcc',
+			args: [
+				{ value: '-o', quoting: 'escape' as const },
+				'output.exe',
+				'main.c',
+			],
+			inSessions: true
+		};
+
+		await service.runTask(task, session);
+
+		assert.strictEqual(sentCommands.length, 1);
+		assert.strictEqual(sentCommands[0].command, 'gcc -o output.exe main.c');
+	});
+
+	test('runTask sends only command when args is empty', async () => {
+		const session = makeSession({ worktree: worktreeUri, repository: repoUri });
+		const task: ITaskEntry = { label: 'build', type: 'shell', command: 'make', args: [], inSessions: true };
+
+		await service.runTask(task, session);
+
+		assert.strictEqual(sentCommands.length, 1);
+		assert.strictEqual(sentCommands[0].command, 'make');
+	});
+
 	test('runTask creates different terminals for same command in different worktrees', async () => {
 		const wt1 = URI.parse('file:///worktree1');
 		const wt2 = URI.parse('file:///worktree2');
@@ -349,6 +541,26 @@ suite('SessionsConfigurationService', () => {
 		assert.strictEqual(createdTerminals.length, 2, 'should create two terminals for different worktrees');
 	});
 
+	test('runs worktreeCreated session tasks when a session gains a worktree', async () => {
+		const sessionResource = URI.parse('file:///session-worktree-created');
+		const worktreeTasksUri = URI.parse('file:///worktree/.vscode/tasks.json');
+		const userTasksUri = URI.from({ scheme: userSettingsUri.scheme, path: '/user/tasks.json' });
+		fileContents.set(worktreeTasksUri.toString(), tasksJsonContent([
+			{ label: 'build', type: 'shell', command: 'npm run build', inSessions: true, runOptions: { runOn: 'worktreeCreated' } },
+			makeTask('manual', 'npm test', true),
+		]));
+		fileContents.set(userTasksUri.toString(), tasksJsonContent([]));
+
+		activeSessionObs.set({ ...makeSession({ repository: repoUri }), resource: sessionResource }, undefined);
+		await new Promise(r => setTimeout(r, 10));
+
+		activeSessionObs.set({ ...makeSession({ repository: repoUri, worktree: worktreeUri }), resource: sessionResource }, undefined);
+		await new Promise(r => setTimeout(r, 10));
+
+		assert.strictEqual(sentCommands.length, 1);
+		assert.strictEqual(sentCommands[0].command, 'npm run build');
+	});
+
 	// --- getLastRunTaskLabel (MRU) ---
 
 	test('getLastRunTaskLabel returns undefined when no task has been run', () => {
diff --git a/src/vs/sessions/contrib/codeReview/browser/codeReview.contributions.ts b/src/vs/sessions/contrib/codeReview/browser/codeReview.contributions.ts
new file mode 100644
index 0000000000000..1efe64e6aa203
--- /dev/null
+++ b/src/vs/sessions/contrib/codeReview/browser/codeReview.contributions.ts
@@ -0,0 +1,181 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Codicon } from '../../../../base/common/codicons.js';
+import { Disposable, MutableDisposable } from '../../../../base/common/lifecycle.js';
+import { autorun, observableFromEvent } from '../../../../base/common/observable.js';
+import { URI } from '../../../../base/common/uri.js';
+import { localize } from '../../../../nls.js';
+import { Action2, MenuId, registerAction2 } from '../../../../platform/actions/common/actions.js';
+import { ContextKeyExpr, IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
+import { InstantiationType, registerSingleton } from '../../../../platform/instantiation/common/extensions.js';
+import { ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
+import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../../workbench/common/contributions.js';
+import { IsSessionsWindowContext } from '../../../../workbench/common/contextkeys.js';
+import { ChatContextKeys } from '../../../../workbench/contrib/chat/common/actions/chatContextKeys.js';
+import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
+import { IAgentSessionsService } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
+import { CHAT_CATEGORY } from '../../../../workbench/contrib/chat/browser/actions/chatActions.js';
+import { ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
+import { CodeReviewService, CodeReviewStateKind, getCodeReviewFilesFromSessionChanges, getCodeReviewVersion, ICodeReviewService, PRReviewStateKind } from './codeReviewService.js';
+import { ThemeIcon } from '../../../../base/common/themables.js';
+import { IAgentFeedbackService } from '../../agentFeedback/browser/agentFeedbackService.js';
+import { getSessionEditorComments } from '../../agentFeedback/browser/sessionEditorComments.js';
+
+registerSingleton(ICodeReviewService, CodeReviewService, InstantiationType.Delayed);
+
+const canRunSessionCodeReviewContextKey = new RawContextKey<boolean>('sessions.canRunCodeReview', true, {
+	type: 'boolean',
+	description: localize('sessions.canRunCodeReview', "True when a new code review can be started for the active session version."),
+});
+
+function registerSessionCodeReviewAction(tooltip: string, icon: ThemeIcon): Disposable {
+	class RunSessionCodeReviewAction extends Action2 {
+		static readonly ID = 'sessions.codeReview.run';
+
+		constructor() {
+			super({
+				id: RunSessionCodeReviewAction.ID,
+				title: localize('sessions.runCodeReview', "Run Code Review"),
+				tooltip,
+				category: CHAT_CATEGORY,
+				icon,
+				precondition: canRunSessionCodeReviewContextKey,
+				menu: [
+					{
+						id: MenuId.ChatEditingSessionChangesToolbar,
+						group: 'navigation',
+						order: 7,
+						when: ContextKeyExpr.and(
+							IsSessionsWindowContext,
+							ChatContextKeys.hasAgentSessionChanges,
+							ChatContextKeys.agentSessionType.notEqualsTo(AgentSessionProviders.Cloud),
+						),
+					},
+				],
+			});
+		}
+
+		override async run(accessor: ServicesAccessor, sessionResource?: URI): Promise<void> {
+			const sessionManagementService = accessor.get(ISessionsManagementService);
+			const agentSessionsService = accessor.get(IAgentSessionsService);
+			const codeReviewService = accessor.get(ICodeReviewService);
+			const agentFeedbackService = accessor.get(IAgentFeedbackService);
+
+			const resource = URI.isUri(sessionResource)
+				? sessionResource
+				: sessionManagementService.getActiveSession()?.resource;
+			if (!resource) {
+				return;
+			}
+
+			const session = agentSessionsService.getSession(resource);
+			if (!(session?.changes instanceof Array) || session.changes.length === 0) {
+				return;
+			}
+
+			const files = getCodeReviewFilesFromSessionChanges(session.changes);
+			const version = getCodeReviewVersion(files);
+
+			// If there are existing comments (code review or PR review), navigate to the first one
+			const reviewState = codeReviewService.getReviewState(resource).get();
+			const prReviewState = codeReviewService.getPRReviewState(resource).get();
+			const codeReviewCount = reviewState.kind === CodeReviewStateKind.Result && reviewState.version === version ? reviewState.comments.length : 0;
+			const prReviewCount = prReviewState.kind === PRReviewStateKind.Loaded ? prReviewState.comments.length : 0;
+
+			if (codeReviewCount > 0 || prReviewCount > 0) {
+				const comments = getSessionEditorComments(
+					resource,
+					agentFeedbackService.getFeedback(resource),
+					reviewState,
+					prReviewState,
+				);
+				const first = agentFeedbackService.getNextNavigableItem(resource, comments, true);
+				if (first) {
+					await agentFeedbackService.revealSessionComment(resource, first.id, first.resourceUri, first.range);
+				}
+				return;
+			}
+
+
+			codeReviewService.requestReview(resource, version, files);
+		}
+	}
+
+	return registerAction2(RunSessionCodeReviewAction) as Disposable;
+}
+
+class CodeReviewToolbarContribution extends Disposable implements IWorkbenchContribution {
+
+	static readonly ID = 'sessions.contrib.codeReviewToolbar';
+
+	private readonly _actionRegistration = this._register(new MutableDisposable<Disposable>());
+
+	constructor(
+		@IContextKeyService contextKeyService: IContextKeyService,
+		@IAgentSessionsService private readonly _agentSessionsService: IAgentSessionsService,
+		@ISessionsManagementService private readonly _sessionManagementService: ISessionsManagementService,
+		@ICodeReviewService private readonly _codeReviewService: ICodeReviewService,
+	) {
+		super();
+
+		const canRunCodeReviewContext = canRunSessionCodeReviewContextKey.bindTo(contextKeyService);
+		const sessionsChangedSignal = observableFromEvent(this, this._agentSessionsService.model.onDidChangeSessions, () => undefined);
+
+		this._register(autorun(reader => {
+			const activeSession = this._sessionManagementService.activeSession.read(reader);
+			sessionsChangedSignal.read(reader);
+			this._actionRegistration.clear();
+
+			const sessionResource = activeSession?.resource;
+			if (!sessionResource) {
+				canRunCodeReviewContext.set(false);
+				this._actionRegistration.value = registerSessionCodeReviewAction(localize('sessions.runCodeReview.noSession', "No active session available for code review."), Codicon.codeReview);
+				return;
+			}
+
+			const session = this._agentSessionsService.getSession(sessionResource);
+			if (!(session?.changes instanceof Array) || session.changes.length === 0) {
+				canRunCodeReviewContext.set(false);
+				this._actionRegistration.value = registerSessionCodeReviewAction(localize('sessions.runCodeReview.noChanges', "No changes available for code review."), Codicon.codeReview);
+				return;
+			}
+
+			const files = getCodeReviewFilesFromSessionChanges(session.changes);
+			const version = getCodeReviewVersion(files);
+			const reviewState = this._codeReviewService.getReviewState(sessionResource).read(reader);
+			const prReviewState = this._codeReviewService.getPRReviewState(sessionResource).read(reader);
+
+			const codeReviewCount = reviewState.kind === CodeReviewStateKind.Result && reviewState.version === version ? reviewState.comments.length : 0;
+			const prReviewCount = prReviewState.kind === PRReviewStateKind.Loaded ? prReviewState.comments.length : 0;
+			const totalCommentCount = codeReviewCount + prReviewCount;
+
+			let canRunCodeReview = true;
+			let tooltip = localize('sessions.runCodeReview.tooltip.default', "Run Code Review");
+			let icon = Codicon.codeReview;
+
+			if (reviewState.kind === CodeReviewStateKind.Loading && reviewState.version === version) {
+				canRunCodeReview = false;
+				tooltip = localize('sessions.runCodeReview.tooltip.loading', "Creating code review...");
+				icon = Codicon.commentDraft;
+			} else if (totalCommentCount > 0) {
+				canRunCodeReview = true;
+				icon = Codicon.commentUnresolved;
+				tooltip = totalCommentCount === 1
+					? localize('sessions.runCodeReview.tooltip.oneUnresolved', "1 review comment unresolved.")
+					: localize('sessions.runCodeReview.tooltip.manyUnresolved', "{0} review comments unresolved.", totalCommentCount);
+			} else if (reviewState.kind === CodeReviewStateKind.Result && reviewState.version === version) {
+				canRunCodeReview = false;
+				tooltip = localize('sessions.runCodeReview.tooltip.allResolved', "All review comments have been addressed.");
+				icon = Codicon.comment;
+			}
+
+			canRunCodeReviewContext.set(canRunCodeReview);
+			this._actionRegistration.value = registerSessionCodeReviewAction(tooltip, icon);
+		}));
+	}
+}
+
+registerWorkbenchContribution2(CodeReviewToolbarContribution.ID, CodeReviewToolbarContribution, WorkbenchPhase.AfterRestored);
diff --git a/src/vs/sessions/contrib/codeReview/browser/codeReviewService.ts b/src/vs/sessions/contrib/codeReview/browser/codeReviewService.ts
new file mode 100644
index 0000000000000..689c409ffe4d7
--- /dev/null
+++ b/src/vs/sessions/contrib/codeReview/browser/codeReviewService.ts
@@ -0,0 +1,662 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
+import { autorun, IObservable, observableValue, transaction } from '../../../../base/common/observable.js';
+import { URI, UriComponents } from '../../../../base/common/uri.js';
+import { IRange, Range } from '../../../../editor/common/core/range.js';
+import { createDecorator } from '../../../../platform/instantiation/common/instantiation.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
+import { generateUuid } from '../../../../base/common/uuid.js';
+import { hash } from '../../../../base/common/hash.js';
+import { hasKey } from '../../../../base/common/types.js';
+import { IChatSessionFileChange, IChatSessionFileChange2, isIChatSessionFileChange2 } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
+import { IAgentSessionsService } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
+import { IGitHubService } from '../../github/browser/githubService.js';
+import { ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
+
+// --- Types -------------------------------------------------------------------
+
+export interface ICodeReviewComment {
+	readonly id: string;
+	readonly uri: URI;
+	readonly range: IRange;
+	readonly body: string;
+	readonly kind: string;
+	readonly severity: string;
+	readonly suggestion?: ICodeReviewSuggestion;
+}
+
+export interface ICodeReviewSuggestion {
+	readonly edits: readonly ICodeReviewSuggestionChange[];
+}
+
+export interface ICodeReviewSuggestionChange {
+	readonly range: IRange;
+	readonly newText: string;
+	readonly oldText: string;
+}
+
+export interface ICodeReviewFile {
+	readonly currentUri: URI;
+	readonly baseUri?: URI;
+}
+
+export function getCodeReviewFilesFromSessionChanges(changes: readonly (IChatSessionFileChange | IChatSessionFileChange2)[]): readonly ICodeReviewFile[] {
+	return changes.map(change => {
+		if (isIChatSessionFileChange2(change)) {
+			return {
+				currentUri: change.modifiedUri ?? change.uri,
+				baseUri: change.originalUri,
+			};
+		}
+
+		return {
+			currentUri: change.modifiedUri,
+			baseUri: change.originalUri,
+		};
+	});
+}
+
+export function getCodeReviewVersion(files: readonly ICodeReviewFile[]): string {
+	const stableFileList = files
+		.map(file => `${file.currentUri.toString()}|${file.baseUri?.toString() ?? ''}`)
+		.sort();
+
+	return `v1:${stableFileList.length}:${hash(stableFileList)}`;
+}
+
+export const enum CodeReviewStateKind {
+	Idle = 'idle',
+	Loading = 'loading',
+	Result = 'result',
+	Error = 'error',
+}
+
+export type ICodeReviewState =
+	| { readonly kind: CodeReviewStateKind.Idle }
+	| { readonly kind: CodeReviewStateKind.Loading; readonly version: string }
+	| { readonly kind: CodeReviewStateKind.Result; readonly version: string; readonly comments: readonly ICodeReviewComment[] }
+	| { readonly kind: CodeReviewStateKind.Error; readonly version: string; readonly reason: string };
+
+// --- PR Review Types ---------------------------------------------------------
+
+export const enum PRReviewStateKind {
+	None = 'none',
+	Loading = 'loading',
+	Loaded = 'loaded',
+	Error = 'error',
+}
+
+export type IPRReviewState =
+	| { readonly kind: PRReviewStateKind.None }
+	| { readonly kind: PRReviewStateKind.Loading }
+	| { readonly kind: PRReviewStateKind.Loaded; readonly comments: readonly IPRReviewComment[] }
+	| { readonly kind: PRReviewStateKind.Error; readonly reason: string };
+
+export interface IPRReviewComment {
+	readonly id: string;
+	readonly uri: URI;
+	readonly range: IRange;
+	readonly body: string;
+	readonly author: string;
+}
+
+/** Shape of a single comment as returned by the code review command. */
+interface IRawCodeReviewComment {
+	readonly uri: IRawCodeReviewUri;
+	readonly range: IRawCodeReviewRange;
+	readonly body?: string;
+	readonly kind?: string;
+	readonly severity?: string;
+	readonly suggestion?: IRawCodeReviewSuggestion;
+}
+
+type IRawCodeReviewUri = URI | UriComponents | string;
+
+interface IRawCodeReviewPosition {
+	readonly line?: number;
+	readonly character?: number;
+}
+
+interface IRawCodeReviewRangeWithPositions {
+	readonly start?: IRawCodeReviewPosition;
+	readonly end?: IRawCodeReviewPosition;
+}
+
+interface IRawCodeReviewRangeWithLines {
+	readonly startLine?: number;
+	readonly startColumn?: number;
+	readonly endLine?: number;
+	readonly endColumn?: number;
+}
+
+type IRawCodeReviewRangeTuple = readonly [IRawCodeReviewPosition, IRawCodeReviewPosition];
+
+type IRawCodeReviewRange = IRange | IRawCodeReviewRangeWithPositions | IRawCodeReviewRangeWithLines | IRawCodeReviewRangeTuple;
+
+interface IRawCodeReviewSuggestion {
+	readonly edits: readonly IRawCodeReviewSuggestionChange[];
+}
+
+interface IRawCodeReviewSuggestionChange {
+	readonly range: IRawCodeReviewRange;
+	readonly newText: string;
+	readonly oldText: string;
+}
+
+// --- Service Interface -------------------------------------------------------
+
+export const ICodeReviewService = createDecorator<ICodeReviewService>('codeReviewService');
+
+export interface ICodeReviewService {
+	readonly _serviceBrand: undefined;
+
+	/**
+	 * Get the observable review state for a session.
+	 */
+	getReviewState(sessionResource: URI): IObservable<ICodeReviewState>;
+
+	/**
+	 * Synchronously check if a completed review exists for the given session+version.
+	 */
+	hasReview(sessionResource: URI, version: string): boolean;
+
+	/**
+	 * Request a code review for the given session. The review is associated with
+	 * a version string (fingerprint of changed files). If a review is already in
+	 * progress or completed for this version, this is a no-op.
+	 */
+	requestReview(sessionResource: URI, version: string, files: readonly { readonly currentUri: URI; readonly baseUri?: URI }[]): void;
+
+	/**
+	 * Remove a single comment from the review results.
+	 */
+	removeComment(sessionResource: URI, commentId: string): void;
+
+	/**
+	 * Dismiss/clear the review for a session entirely.
+	 */
+	dismissReview(sessionResource: URI): void;
+
+	/**
+	 * Get the observable PR review state for a session.
+	 * Returns unresolved review comments from the PR associated with the session.
+	 */
+	getPRReviewState(sessionResource: URI): IObservable<IPRReviewState>;
+
+	/**
+	 * Resolve a PR review thread on GitHub and remove it from local state.
+	 */
+	resolvePRReviewThread(sessionResource: URI, threadId: string): Promise<void>;
+}
+
+// --- Storage Types -----------------------------------------------------------
+
+interface IStoredCodeReview {
+	readonly version: string;
+	readonly comments: readonly IStoredCodeReviewComment[];
+}
+
+interface IStoredCodeReviewComment {
+	readonly id: string;
+	readonly uri: UriComponents;
+	readonly range: IRange;
+	readonly body: string;
+	readonly kind: string;
+	readonly severity: string;
+	readonly suggestion?: ICodeReviewSuggestion;
+}
+
+// --- Implementation ----------------------------------------------------------
+
+interface ISessionReviewData {
+	readonly state: ReturnType<typeof observableValue<ICodeReviewState>>;
+}
+
+interface IPRSessionReviewData {
+	readonly state: ReturnType<typeof observableValue<IPRReviewState>>;
+	readonly disposables: DisposableStore;
+	initialized: boolean;
+}
+
+function isRawCodeReviewRangeWithPositions(range: IRawCodeReviewRange): range is IRawCodeReviewRangeWithPositions {
+	return typeof range === 'object' && range !== null && hasKey(range, { start: true, end: true });
+}
+
+function isRawCodeReviewRangeTuple(range: IRawCodeReviewRange): range is IRawCodeReviewRangeTuple {
+	return Array.isArray(range) && range.length >= 2;
+}
+
+function normalizeCodeReviewUri(uri: IRawCodeReviewUri): URI {
+	return typeof uri === 'string' ? URI.parse(uri) : URI.revive(uri);
+}
+
+function normalizeCodeReviewRange(range: IRawCodeReviewRange): IRange {
+	if (Range.isIRange(range)) {
+		return Range.lift(range);
+	}
+
+	if (isRawCodeReviewRangeTuple(range)) {
+		const [start, end] = range;
+		return new Range(
+			(start.line ?? 0) + 1,
+			(start.character ?? 0) + 1,
+			(end.line ?? start.line ?? 0) + 1,
+			(end.character ?? start.character ?? 0) + 1,
+		);
+	}
+
+	if (isRawCodeReviewRangeWithPositions(range) && range.start && range.end) {
+		return new Range(
+			(range.start.line ?? 0) + 1,
+			(range.start.character ?? 0) + 1,
+			(range.end.line ?? range.start.line ?? 0) + 1,
+			(range.end.character ?? range.start.character ?? 0) + 1,
+		);
+	}
+
+	const lineRange = range as IRawCodeReviewRangeWithLines;
+	return new Range(
+		(lineRange.startLine ?? 0) + 1,
+		(lineRange.startColumn ?? 0) + 1,
+		(lineRange.endLine ?? lineRange.startLine ?? 0) + 1,
+		(lineRange.endColumn ?? lineRange.startColumn ?? 0) + 1,
+	);
+}
+
+function normalizeCodeReviewSuggestion(suggestion: IRawCodeReviewSuggestion | undefined): ICodeReviewSuggestion | undefined {
+	if (!suggestion) {
+		return undefined;
+	}
+
+	return {
+		edits: suggestion.edits.map(edit => ({
+			range: normalizeCodeReviewRange(edit.range),
+			newText: edit.newText,
+			oldText: edit.oldText,
+		})),
+	};
+}
+
+export class CodeReviewService extends Disposable implements ICodeReviewService {
+
+	declare readonly _serviceBrand: undefined;
+
+	private static readonly _STORAGE_KEY = 'codeReview.reviews';
+
+	private readonly _reviewsBySession = new Map<string, ISessionReviewData>();
+	private readonly _prReviewBySession = new Map<string, IPRSessionReviewData>();
+
+	constructor(
+		@ICommandService private readonly _commandService: ICommandService,
+		@ILogService private readonly _logService: ILogService,
+		@IStorageService private readonly _storageService: IStorageService,
+		@IGitHubService private readonly _gitHubService: IGitHubService,
+		@ISessionsManagementService private readonly _sessionsManagementService: ISessionsManagementService,
+		@IAgentSessionsService private readonly _agentSessionsService: IAgentSessionsService,
+	) {
+		super();
+		this._loadFromStorage();
+		this._registerSessionListeners();
+
+		this._register(autorun(reader => {
+			const activeSession = this._sessionsManagementService.activeSession.read(reader);
+			if (activeSession) {
+				this._ensurePRReviewInitialized(activeSession.resource);
+			}
+		}));
+
+		this._register(this._agentSessionsService.model.onDidChangeSessions(() => {
+			for (const session of this._agentSessionsService.model.sessions) {
+				if (!session.isArchived()) {
+					this._ensurePRReviewInitialized(session.resource);
+				}
+			}
+		}));
+
+		this._register(this._agentSessionsService.model.onDidChangeSessionArchivedState(e => {
+			if (e.isArchived()) {
+				this._disposePRReview(e.resource);
+			}
+		}));
+	}
+
+	getReviewState(sessionResource: URI): IObservable<ICodeReviewState> {
+		return this._getOrCreateData(sessionResource).state;
+	}
+
+	hasReview(sessionResource: URI, version: string): boolean {
+		const data = this._reviewsBySession.get(sessionResource.toString());
+		if (!data) {
+			return false;
+		}
+		const state = data.state.get();
+		return state.kind === CodeReviewStateKind.Result && state.version === version;
+	}
+
+	requestReview(sessionResource: URI, version: string, files: readonly { readonly currentUri: URI; readonly baseUri?: URI }[]): void {
+		const data = this._getOrCreateData(sessionResource);
+		const currentState = data.state.get();
+
+		// Don't re-request if already loading or completed for this version
+		if (currentState.kind === CodeReviewStateKind.Loading && currentState.version === version) {
+			return;
+		}
+		if (currentState.kind === CodeReviewStateKind.Result && currentState.version === version) {
+			return;
+		}
+
+		data.state.set({ kind: CodeReviewStateKind.Loading, version }, undefined);
+
+		this._executeReview(sessionResource, version, files, data);
+	}
+
+	removeComment(sessionResource: URI, commentId: string): void {
+		const data = this._reviewsBySession.get(sessionResource.toString());
+		if (!data) {
+			return;
+		}
+
+		const state = data.state.get();
+		if (state.kind !== CodeReviewStateKind.Result) {
+			return;
+		}
+
+		const filtered = state.comments.filter(c => c.id !== commentId);
+		data.state.set({ kind: CodeReviewStateKind.Result, version: state.version, comments: filtered }, undefined);
+		this._saveToStorage();
+	}
+
+	dismissReview(sessionResource: URI): void {
+		const data = this._reviewsBySession.get(sessionResource.toString());
+		if (data) {
+			data.state.set({ kind: CodeReviewStateKind.Idle }, undefined);
+			this._saveToStorage();
+		}
+	}
+
+	private _getOrCreateData(sessionResource: URI): ISessionReviewData {
+		const key = sessionResource.toString();
+		let data = this._reviewsBySession.get(key);
+		if (!data) {
+			data = {
+				state: observableValue<ICodeReviewState>(`codeReview.state.${key}`, { kind: CodeReviewStateKind.Idle }),
+			};
+			this._reviewsBySession.set(key, data);
+		}
+		return data;
+	}
+
+	private async _executeReview(
+		sessionResource: URI,
+		version: string,
+		files: readonly { readonly currentUri: URI; readonly baseUri?: URI }[],
+		data: ISessionReviewData,
+	): Promise<void> {
+		try {
+			const result: { type: string; comments?: IRawCodeReviewComment[]; reason?: string } | undefined =
+				await this._commandService.executeCommand('chat.internal.codeReview.run', {
+					files: files.map(f => ({
+						currentUri: f.currentUri,
+						baseUri: f.baseUri,
+					})),
+				});
+
+			// Check if version is still current (hasn't been dismissed or replaced)
+			const currentState = data.state.get();
+			if (currentState.kind !== CodeReviewStateKind.Loading || currentState.version !== version) {
+				return;
+			}
+
+			if (!result || result.type === 'cancelled') {
+				data.state.set({ kind: CodeReviewStateKind.Idle }, undefined);
+				return;
+			}
+
+			if (result.type === 'error') {
+				data.state.set({ kind: CodeReviewStateKind.Error, version, reason: result.reason ?? 'Unknown error' }, undefined);
+				return;
+			}
+
+			if (result.type === 'success') {
+				const comments: ICodeReviewComment[] = (result.comments ?? []).map((raw) => ({
+					id: generateUuid(),
+					uri: normalizeCodeReviewUri(raw.uri),
+					range: normalizeCodeReviewRange(raw.range),
+					body: raw.body ?? '',
+					kind: raw.kind ?? '',
+					severity: raw.severity ?? '',
+					suggestion: normalizeCodeReviewSuggestion(raw.suggestion),
+				}));
+
+				transaction(tx => {
+					data.state.set({ kind: CodeReviewStateKind.Result, version, comments }, tx);
+				});
+				this._saveToStorage();
+			}
+		} catch (err) {
+			const currentState = data.state.get();
+			if (currentState.kind === CodeReviewStateKind.Loading && currentState.version === version) {
+				data.state.set({ kind: CodeReviewStateKind.Error, version, reason: String(err) }, undefined);
+			}
+		}
+	}
+
+	private _loadFromStorage(): void {
+		const raw = this._storageService.get(CodeReviewService._STORAGE_KEY, StorageScope.WORKSPACE);
+		if (!raw) {
+			return;
+		}
+
+		try {
+			const stored: Record<string, IStoredCodeReview> = JSON.parse(raw);
+			for (const [key, review] of Object.entries(stored)) {
+				const comments: ICodeReviewComment[] = review.comments.map(c => ({
+					id: c.id,
+					uri: URI.revive(c.uri),
+					range: c.range,
+					body: c.body,
+					kind: c.kind,
+					severity: c.severity,
+					suggestion: c.suggestion,
+				}));
+				const data = this._getOrCreateData(URI.parse(key));
+				data.state.set({ kind: CodeReviewStateKind.Result, version: review.version, comments }, undefined);
+			}
+		} catch {
+			// Corrupted storage data — ignore
+		}
+	}
+
+	private _saveToStorage(): void {
+		const stored: Record<string, IStoredCodeReview> = {};
+		for (const [key, data] of this._reviewsBySession) {
+			const state = data.state.get();
+			if (state.kind === CodeReviewStateKind.Result) {
+				stored[key] = {
+					version: state.version,
+					comments: state.comments.map(c => ({
+						id: c.id,
+						uri: c.uri.toJSON(),
+						range: c.range,
+						body: c.body,
+						kind: c.kind,
+						severity: c.severity,
+						suggestion: c.suggestion,
+					})),
+				};
+			}
+		}
+
+		if (Object.keys(stored).length === 0) {
+			this._storageService.remove(CodeReviewService._STORAGE_KEY, StorageScope.WORKSPACE);
+		} else {
+			this._storageService.store(CodeReviewService._STORAGE_KEY, JSON.stringify(stored), StorageScope.WORKSPACE, StorageTarget.MACHINE);
+		}
+	}
+
+	private _registerSessionListeners(): void {
+		// Clean up when a session is archived
+		this._register(this._agentSessionsService.onDidChangeSessionArchivedState(session => {
+			if (session.isArchived()) {
+				const key = session.resource.toString();
+				const data = this._reviewsBySession.get(key);
+				if (data) {
+					data.state.set({ kind: CodeReviewStateKind.Idle }, undefined);
+					this._saveToStorage();
+				}
+			}
+		}));
+
+		// Clean up when session changes make a review version outdated
+		this._register(this._agentSessionsService.model.onDidChangeSessions(() => {
+			let changed = false;
+			for (const [key, data] of this._reviewsBySession) {
+				const state = data.state.get();
+				if (state.kind !== CodeReviewStateKind.Result) {
+					continue;
+				}
+
+				const session = this._agentSessionsService.getSession(URI.parse(key));
+				if (!session) {
+					// Session no longer exists — clean up
+					data.state.set({ kind: CodeReviewStateKind.Idle }, undefined);
+					changed = true;
+					continue;
+				}
+
+				if (!(session.changes instanceof Array) || session.changes.length === 0) {
+					// Session has no file-level changes — clean up
+					data.state.set({ kind: CodeReviewStateKind.Idle }, undefined);
+					changed = true;
+					continue;
+				}
+
+				const files = getCodeReviewFilesFromSessionChanges(session.changes);
+				const currentVersion = getCodeReviewVersion(files);
+				if (state.version !== currentVersion) {
+					// Version mismatch — review is stale
+					data.state.set({ kind: CodeReviewStateKind.Idle }, undefined);
+					changed = true;
+				}
+			}
+
+			if (changed) {
+				this._saveToStorage();
+			}
+		}));
+	}
+
+	getPRReviewState(sessionResource: URI): IObservable<IPRReviewState> {
+		return this._getOrCreatePRReviewData(sessionResource).state;
+	}
+
+	async resolvePRReviewThread(sessionResource: URI, threadId: string): Promise<void> {
+		const context = this._sessionsManagementService.getGitHubContextForSession(sessionResource);
+		if (context?.prNumber !== undefined) {
+			const prModel = this._gitHubService.getPullRequest(context.owner, context.repo, context.prNumber);
+			try {
+				await prModel.resolveThread(threadId);
+			} catch (err) {
+				this._logService.warn('[CodeReviewService] Failed to resolve PR thread on GitHub:', err);
+			}
+		}
+
+		// Remove from local state regardless of GitHub success
+		const data = this._prReviewBySession.get(sessionResource.toString());
+		if (data) {
+			const currentState = data.state.get();
+			if (currentState.kind === PRReviewStateKind.Loaded) {
+				const filtered = currentState.comments.filter(c => c.id !== threadId);
+				data.state.set({ kind: PRReviewStateKind.Loaded, comments: filtered }, undefined);
+			}
+		}
+	}
+
+	private _getOrCreatePRReviewData(sessionResource: URI): IPRSessionReviewData {
+		const key = sessionResource.toString();
+		let data = this._prReviewBySession.get(key);
+		if (!data) {
+			data = {
+				state: observableValue<IPRReviewState>(`prReview.state.${key}`, { kind: PRReviewStateKind.None }),
+				disposables: new DisposableStore(),
+				initialized: false,
+			};
+			this._prReviewBySession.set(key, data);
+		}
+		return data;
+	}
+
+	private _ensurePRReviewInitialized(sessionResource: URI): void {
+		const data = this._getOrCreatePRReviewData(sessionResource);
+		if (data.initialized) {
+			return;
+		}
+
+		const context = this._sessionsManagementService.getGitHubContextForSession(sessionResource);
+		if (!context || context.prNumber === undefined) {
+			return;
+		}
+
+		data.initialized = true;
+		data.state.set({ kind: PRReviewStateKind.Loading }, undefined);
+
+		const prModel = this._gitHubService.getPullRequest(context.owner, context.repo, context.prNumber);
+
+		// Watch the PR model's review threads and map to local state
+		data.disposables.add(autorun(reader => {
+			const threads = prModel.reviewThreads.read(reader);
+			const comments: IPRReviewComment[] = [];
+
+			for (const thread of threads) {
+				if (thread.isResolved) {
+					continue;
+				}
+				const fileUri = this._sessionsManagementService.resolveSessionFileUri(sessionResource, thread.path);
+				if (!fileUri) {
+					continue;
+				}
+				const line = thread.line ?? 1;
+				const firstComment = thread.comments[0];
+				comments.push({
+					id: String(thread.id),
+					uri: fileUri,
+					range: new Range(line, 1, line, 1),
+					body: firstComment?.body ?? '',
+					author: firstComment?.author.login ?? '',
+				});
+			}
+
+			data.state.set({ kind: PRReviewStateKind.Loaded, comments }, undefined);
+		}));
+
+		// Start polling and initial fetch
+		prModel.refreshThreads().catch(err => {
+			this._logService.error('[CodeReviewService] Failed to fetch PR review threads:', err);
+			data.state.set({ kind: PRReviewStateKind.Error, reason: String(err) }, undefined);
+		});
+		prModel.startPolling();
+	}
+
+	private _disposePRReview(sessionResource: URI): void {
+		const key = sessionResource.toString();
+		const data = this._prReviewBySession.get(key);
+		if (data) {
+			data.disposables.dispose();
+			this._prReviewBySession.delete(key);
+		}
+	}
+
+	override dispose(): void {
+		for (const data of this._prReviewBySession.values()) {
+			data.disposables.dispose();
+		}
+		this._prReviewBySession.clear();
+		super.dispose();
+	}
+}
diff --git a/src/vs/sessions/contrib/codeReview/test/browser/codeReviewService.test.ts b/src/vs/sessions/contrib/codeReview/test/browser/codeReviewService.test.ts
new file mode 100644
index 0000000000000..193a55925b264
--- /dev/null
+++ b/src/vs/sessions/contrib/codeReview/test/browser/codeReviewService.test.ts
@@ -0,0 +1,961 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { URI } from '../../../../../base/common/uri.js';
+import { Range } from '../../../../../editor/common/core/range.js';
+import { observableValue } from '../../../../../base/common/observable.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { TestInstantiationService } from '../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { ICommandService } from '../../../../../platform/commands/common/commands.js';
+import { Emitter, Event } from '../../../../../base/common/event.js';
+import { mock } from '../../../../../base/test/common/mock.js';
+import { ILogService, NullLogService } from '../../../../../platform/log/common/log.js';
+import { InMemoryStorageService, IStorageService, StorageScope, StorageTarget } from '../../../../../platform/storage/common/storage.js';
+import { IAgentSession, IAgentSessionsModel } from '../../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsModel.js';
+import { IChatSessionFileChange2 } from '../../../../../workbench/contrib/chat/common/chatSessionsService.js';
+import { IAgentSessionsService } from '../../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
+import { CodeReviewService, CodeReviewStateKind, getCodeReviewFilesFromSessionChanges, getCodeReviewVersion, ICodeReviewService } from '../../browser/codeReviewService.js';
+import { IGitHubService } from '../../../github/browser/githubService.js';
+import { IActiveSessionItem, ISessionsManagementService } from '../../../sessions/browser/sessionsManagementService.js';
+
+suite('CodeReviewService', () => {
+
+	const store = new DisposableStore();
+	let instantiationService: TestInstantiationService;
+	let service: ICodeReviewService;
+	let commandService: MockCommandService;
+	let storageService: InMemoryStorageService;
+	let agentSessionsService: MockAgentSessionsService;
+
+	let session: URI;
+	let fileA: URI;
+	let fileB: URI;
+
+	class MockCommandService implements ICommandService {
+		declare readonly _serviceBrand: undefined;
+		readonly onWillExecuteCommand = Event.None;
+		readonly onDidExecuteCommand = Event.None;
+
+		result: unknown = undefined;
+		lastCommandId: string | undefined;
+		lastArgs: unknown[] | undefined;
+		executeDeferred: { resolve: (v: unknown) => void; reject: (e: unknown) => void } | undefined;
+
+		async executeCommand<T>(commandId: string, ...args: unknown[]): Promise<T> {
+			this.lastCommandId = commandId;
+			this.lastArgs = args;
+
+			if (this.executeDeferred) {
+				return await new Promise<T>((resolve, reject) => {
+					this.executeDeferred = { resolve: resolve as (v: unknown) => void, reject };
+				});
+			}
+
+			return this.result as T;
+		}
+
+		/**
+		 * Configure the mock to defer execution until manually resolved/rejected.
+		 */
+		deferNextExecution(): void {
+			this.executeDeferred = undefined;
+			const self = this;
+			const originalResult = this.result;
+
+			// Override executeCommand for next call to capture the deferred promise
+			const origExecute = this.executeCommand.bind(this);
+			this.executeCommand = async function <T>(commandId: string, ...args: unknown[]): Promise<T> {
+				self.lastCommandId = commandId;
+				self.lastArgs = args;
+
+				return new Promise<T>((resolve, reject) => {
+					self.executeDeferred = { resolve: resolve as (v: unknown) => void, reject };
+				});
+			} as typeof origExecute;
+
+			// Restore after use
+			this._restoreExecute = () => {
+				this.executeCommand = origExecute;
+				this.result = originalResult;
+			};
+		}
+
+		private _restoreExecute: (() => void) | undefined;
+
+		resolveExecution(value: unknown): void {
+			this.executeDeferred?.resolve(value);
+			this.executeDeferred = undefined;
+			this._restoreExecute?.();
+		}
+
+		rejectExecution(error: unknown): void {
+			this.executeDeferred?.reject(error);
+			this.executeDeferred = undefined;
+			this._restoreExecute?.();
+		}
+	}
+
+	class MockAgentSessionsService {
+		declare readonly _serviceBrand: undefined;
+
+		private readonly _onDidChangeSessionArchivedState: Emitter<IAgentSession>;
+		readonly onDidChangeSessionArchivedState: Event<IAgentSession>;
+		private readonly _onDidChangeSessions: Emitter<void>;
+		readonly model: IAgentSessionsModel;
+		private readonly _sessions = new Map<string, IAgentSession>();
+
+		constructor(disposables: DisposableStore) {
+			this._onDidChangeSessionArchivedState = disposables.add(new Emitter<IAgentSession>());
+			this.onDidChangeSessionArchivedState = this._onDidChangeSessionArchivedState.event;
+			this._onDidChangeSessions = disposables.add(new Emitter<void>());
+			this.model = {
+				onWillResolve: Event.None,
+				onDidResolve: Event.None,
+				onDidChangeSessions: this._onDidChangeSessions.event,
+				onDidChangeSessionArchivedState: this._onDidChangeSessionArchivedState.event,
+				resolved: true,
+				sessions: [],
+				getSession: (resource: URI) => this._sessions.get(resource.toString()),
+				resolve: async () => { },
+			};
+		}
+
+		getSession(resource: URI): IAgentSession | undefined {
+			return this._sessions.get(resource.toString());
+		}
+
+		setSession(resource: URI, changes?: readonly IChatSessionFileChange2[], archived = false): IAgentSession {
+			let _archived = archived;
+			const session = {
+				resource,
+				changes,
+				isArchived: () => _archived,
+				setArchived: (v: boolean) => { _archived = v; },
+				isRead: () => true,
+				setRead: () => { },
+			} as unknown as IAgentSession;
+			this._sessions.set(resource.toString(), session);
+			return session;
+		}
+
+		updateSessionChanges(resource: URI, changes: readonly IChatSessionFileChange2[] | undefined): void {
+			const session = this._sessions.get(resource.toString()) as Record<string, unknown> | undefined;
+			if (session) {
+				session.changes = changes;
+			}
+		}
+
+		removeSession(resource: URI): void {
+			this._sessions.delete(resource.toString());
+		}
+
+		fireSessionArchivedState(session: IAgentSession): void {
+			this._onDidChangeSessionArchivedState.fire(session);
+		}
+
+		fireSessionsChanged(): void {
+			this._onDidChangeSessions.fire();
+		}
+	}
+
+	setup(() => {
+		instantiationService = store.add(new TestInstantiationService());
+
+		commandService = new MockCommandService();
+		instantiationService.stub(ICommandService, commandService);
+		instantiationService.stub(ILogService, new NullLogService());
+		instantiationService.stub(IGitHubService, new class extends mock<IGitHubService>() { }());
+		instantiationService.stub(ISessionsManagementService, new class extends mock<ISessionsManagementService>() {
+			override readonly activeSession = observableValue<IActiveSessionItem | undefined>('test.activeSession', undefined);
+		}());
+
+		storageService = store.add(new InMemoryStorageService());
+		instantiationService.stub(IStorageService, storageService);
+
+		agentSessionsService = new MockAgentSessionsService(store);
+		instantiationService.stub(IAgentSessionsService, agentSessionsService);
+
+		service = store.add(instantiationService.createInstance(CodeReviewService));
+		session = URI.parse('test://session/1');
+		fileA = URI.parse('file:///a.ts');
+		fileB = URI.parse('file:///b.ts');
+	});
+
+	teardown(() => {
+		store.clear();
+	});
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	// --- getReviewState ---
+
+	test('initial state is idle', () => {
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Idle);
+	});
+
+	test('getReviewState returns the same observable for the same session', () => {
+		const obs1 = service.getReviewState(session);
+		const obs2 = service.getReviewState(session);
+		assert.strictEqual(obs1, obs2);
+	});
+
+	test('getReviewState returns different observables for different sessions', () => {
+		const session2 = URI.parse('test://session/2');
+		const obs1 = service.getReviewState(session);
+		const obs2 = service.getReviewState(session2);
+		assert.notStrictEqual(obs1, obs2);
+	});
+
+	// --- hasReview ---
+
+	test('hasReview returns false when no review exists', () => {
+		assert.strictEqual(service.hasReview(session, 'v1'), false);
+	});
+
+	test('hasReview returns false when review is for a different version', async () => {
+		commandService.result = { type: 'success', comments: [] };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+
+		// Wait for async command to complete
+		await tick();
+
+		assert.strictEqual(service.hasReview(session, 'v1'), true);
+		assert.strictEqual(service.hasReview(session, 'v2'), false);
+	});
+
+	test('hasReview returns true after successful review', async () => {
+		commandService.result = { type: 'success', comments: [] };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+
+		await tick();
+
+		assert.strictEqual(service.hasReview(session, 'v1'), true);
+	});
+
+	// --- requestReview ---
+
+	test('requestReview transitions to loading state', () => {
+		commandService.deferNextExecution();
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Loading);
+		if (state.kind === CodeReviewStateKind.Loading) {
+			assert.strictEqual(state.version, 'v1');
+		}
+
+		// Resolve to avoid leaking
+		commandService.resolveExecution({ type: 'success', comments: [] });
+	});
+
+	test('requestReview calls command with correct arguments', async () => {
+		commandService.result = { type: 'success', comments: [] };
+		service.requestReview(session, 'v1', [
+			{ currentUri: fileA, baseUri: fileB },
+			{ currentUri: fileB },
+		]);
+
+		await tick();
+
+		assert.strictEqual(commandService.lastCommandId, 'chat.internal.codeReview.run');
+		const args = commandService.lastArgs?.[0] as { files: { currentUri: URI; baseUri?: URI }[] };
+		assert.strictEqual(args.files.length, 2);
+		assert.strictEqual(args.files[0].currentUri.toString(), fileA.toString());
+		assert.strictEqual(args.files[0].baseUri?.toString(), fileB.toString());
+		assert.strictEqual(args.files[1].currentUri.toString(), fileB.toString());
+		assert.strictEqual(args.files[1].baseUri, undefined);
+	});
+
+	test('requestReview with success populates comments', async () => {
+		commandService.result = {
+			type: 'success',
+			comments: [
+				{
+					uri: fileA,
+					range: new Range(1, 1, 5, 1),
+					body: 'Bug found',
+					kind: 'bug',
+					severity: 'high',
+				},
+				{
+					uri: fileB,
+					range: new Range(10, 1, 15, 1),
+					body: 'Style issue',
+					kind: 'style',
+					severity: 'low',
+				},
+			],
+		};
+
+		service.requestReview(session, 'v1', [{ currentUri: fileA }, { currentUri: fileB }]);
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Result);
+		if (state.kind === CodeReviewStateKind.Result) {
+			assert.strictEqual(state.version, 'v1');
+			assert.strictEqual(state.comments.length, 2);
+			assert.strictEqual(state.comments[0].body, 'Bug found');
+			assert.strictEqual(state.comments[0].kind, 'bug');
+			assert.strictEqual(state.comments[0].severity, 'high');
+			assert.strictEqual(state.comments[0].uri.toString(), fileA.toString());
+			assert.strictEqual(state.comments[1].body, 'Style issue');
+		}
+	});
+
+	test('requestReview with error transitions to error state', async () => {
+		commandService.result = { type: 'error', reason: 'Auth failed' };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Error);
+		if (state.kind === CodeReviewStateKind.Error) {
+			assert.strictEqual(state.version, 'v1');
+			assert.strictEqual(state.reason, 'Auth failed');
+		}
+	});
+
+	test('requestReview with cancelled result transitions to idle', async () => {
+		commandService.result = { type: 'cancelled' };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Idle);
+	});
+
+	test('requestReview with undefined result transitions to idle', async () => {
+		commandService.result = undefined;
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Idle);
+	});
+
+	test('requestReview with thrown error transitions to error state', async () => {
+		commandService.deferNextExecution();
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		commandService.rejectExecution(new Error('Network error'));
+
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Error);
+		if (state.kind === CodeReviewStateKind.Error) {
+			assert.ok(state.reason.includes('Network error'));
+		}
+	});
+
+	test('requestReview is a no-op when loading for the same version', () => {
+		commandService.deferNextExecution();
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+
+		// Attempt to request again for the same version
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+
+		// Should still be loading (not re-triggered)
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Loading);
+
+		commandService.resolveExecution({ type: 'success', comments: [] });
+	});
+
+	test('requestReview is a no-op when result exists for the same version', async () => {
+		commandService.result = { type: 'success', comments: [] };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		// Attempt to request again
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+
+		// Should still have the result
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Result);
+	});
+
+	test('requestReview for a new version replaces loading state', async () => {
+		// Start v1 review — it will complete immediately with empty result
+		commandService.result = { type: 'success', comments: [] };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		assert.strictEqual(service.hasReview(session, 'v1'), true);
+
+		// Request v2 — since v1 is a different version, it should proceed
+		commandService.result = { type: 'success', comments: [{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'v2 comment' }] };
+		service.requestReview(session, 'v2', [{ currentUri: fileA }]);
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Result);
+		if (state.kind === CodeReviewStateKind.Result) {
+			assert.strictEqual(state.version, 'v2');
+			assert.strictEqual(state.comments.length, 1);
+			assert.strictEqual(state.comments[0].body, 'v2 comment');
+		}
+
+		// v1 is no longer valid
+		assert.strictEqual(service.hasReview(session, 'v1'), false);
+	});
+
+	// --- removeComment ---
+
+	test('removeComment removes a specific comment', async () => {
+		commandService.result = {
+			type: 'success',
+			comments: [
+				{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'comment1' },
+				{ uri: fileA, range: new Range(5, 1, 5, 1), body: 'comment2' },
+				{ uri: fileB, range: new Range(10, 1, 10, 1), body: 'comment3' },
+			],
+		};
+
+		service.requestReview(session, 'v1', [{ currentUri: fileA }, { currentUri: fileB }]);
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Result);
+		if (state.kind !== CodeReviewStateKind.Result) { return; }
+
+		const commentToRemove = state.comments[1];
+		service.removeComment(session, commentToRemove.id);
+
+		const newState = service.getReviewState(session).get();
+		assert.strictEqual(newState.kind, CodeReviewStateKind.Result);
+		if (newState.kind === CodeReviewStateKind.Result) {
+			assert.strictEqual(newState.comments.length, 2);
+			assert.strictEqual(newState.comments[0].body, 'comment1');
+			assert.strictEqual(newState.comments[1].body, 'comment3');
+		}
+	});
+
+	test('removeComment is a no-op for unknown comment id', async () => {
+		commandService.result = {
+			type: 'success',
+			comments: [{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'comment1' }],
+		};
+
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		service.removeComment(session, 'nonexistent-id');
+
+		const state = service.getReviewState(session).get();
+		if (state.kind === CodeReviewStateKind.Result) {
+			assert.strictEqual(state.comments.length, 1);
+		}
+	});
+
+	test('removeComment is a no-op when no review exists', () => {
+		// Should not throw
+		service.removeComment(session, 'some-id');
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Idle);
+	});
+
+	test('removeComment is a no-op when state is not result', () => {
+		commandService.deferNextExecution();
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+
+		// State is loading — removeComment should be ignored
+		service.removeComment(session, 'some-id');
+
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Loading);
+
+		commandService.resolveExecution({ type: 'success', comments: [] });
+	});
+
+	test('removeComment preserves version in result', async () => {
+		commandService.result = {
+			type: 'success',
+			comments: [
+				{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'comment1' },
+				{ uri: fileA, range: new Range(5, 1, 5, 1), body: 'comment2' },
+			],
+		};
+
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		if (state.kind !== CodeReviewStateKind.Result) { return; }
+
+		service.removeComment(session, state.comments[0].id);
+
+		const newState = service.getReviewState(session).get();
+		if (newState.kind === CodeReviewStateKind.Result) {
+			assert.strictEqual(newState.version, 'v1');
+		}
+	});
+
+	// --- dismissReview ---
+
+	test('dismissReview resets to idle', async () => {
+		commandService.result = { type: 'success', comments: [] };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Result);
+
+		service.dismissReview(session);
+
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Idle);
+	});
+
+	test('dismissReview while loading resets to idle', () => {
+		commandService.deferNextExecution();
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Loading);
+
+		service.dismissReview(session);
+
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Idle);
+
+		// Resolve the pending command — should be ignored since dismissed
+		commandService.resolveExecution({ type: 'success', comments: [{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'late' }] });
+	});
+
+	test('dismissReview is a no-op when no data exists', () => {
+		// Should not throw
+		service.dismissReview(session);
+	});
+
+	test('hasReview returns false after dismissReview', async () => {
+		commandService.result = { type: 'success', comments: [] };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		assert.strictEqual(service.hasReview(session, 'v1'), true);
+
+		service.dismissReview(session);
+
+		assert.strictEqual(service.hasReview(session, 'v1'), false);
+	});
+
+	// --- Isolation between sessions ---
+
+	test('different sessions are independent', async () => {
+		const session2 = URI.parse('test://session/2');
+
+		commandService.result = {
+			type: 'success',
+			comments: [{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'session1 comment' }],
+		};
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		commandService.result = {
+			type: 'success',
+			comments: [{ uri: fileB, range: new Range(2, 1, 2, 1), body: 'session2 comment' }],
+		};
+		service.requestReview(session2, 'v2', [{ currentUri: fileB }]);
+		await tick();
+
+		const state1 = service.getReviewState(session).get();
+		const state2 = service.getReviewState(session2).get();
+
+		assert.strictEqual(state1.kind, CodeReviewStateKind.Result);
+		assert.strictEqual(state2.kind, CodeReviewStateKind.Result);
+
+		if (state1.kind === CodeReviewStateKind.Result && state2.kind === CodeReviewStateKind.Result) {
+			assert.strictEqual(state1.comments[0].body, 'session1 comment');
+			assert.strictEqual(state2.comments[0].body, 'session2 comment');
+		}
+
+		// Dismissing session1 doesn't affect session2
+		service.dismissReview(session);
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Idle);
+		assert.strictEqual(service.getReviewState(session2).get().kind, CodeReviewStateKind.Result);
+	});
+
+	// --- Comment parsing ---
+
+	test('comments with string URIs are parsed correctly', async () => {
+		commandService.result = {
+			type: 'success',
+			comments: [
+				{
+					uri: 'file:///parsed.ts',
+					range: new Range(1, 1, 1, 1),
+					body: 'parsed comment',
+				},
+			],
+		};
+
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		if (state.kind === CodeReviewStateKind.Result) {
+			assert.strictEqual(state.comments[0].uri.toString(), 'file:///parsed.ts');
+		}
+	});
+
+	test('comments with missing optional fields get defaults', async () => {
+		commandService.result = {
+			type: 'success',
+			comments: [
+				{
+					uri: fileA,
+					range: new Range(1, 1, 1, 1),
+					// body, kind, severity omitted
+				},
+			],
+		};
+
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		if (state.kind === CodeReviewStateKind.Result) {
+			assert.strictEqual(state.comments[0].body, '');
+			assert.strictEqual(state.comments[0].kind, '');
+			assert.strictEqual(state.comments[0].severity, '');
+			assert.strictEqual(state.comments[0].suggestion, undefined);
+		}
+	});
+
+	test('comments normalize VS Code API style ranges', async () => {
+		commandService.result = {
+			type: 'success',
+			comments: [
+				{
+					uri: fileA,
+					range: {
+						start: { line: 4, character: 2 },
+						end: { line: 6, character: 5 },
+					},
+					body: 'normalized comment',
+					suggestion: {
+						edits: [
+							{
+								range: {
+									start: { line: 8, character: 1 },
+									end: { line: 8, character: 9 },
+								},
+								oldText: 'let value',
+								newText: 'const value',
+							},
+						],
+					},
+				},
+			],
+		};
+
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Result);
+		if (state.kind === CodeReviewStateKind.Result) {
+			assert.deepStrictEqual(state.comments[0].range, new Range(5, 3, 7, 6));
+			assert.deepStrictEqual(state.comments[0].suggestion?.edits[0].range, new Range(9, 2, 9, 10));
+		}
+	});
+
+	test('comments normalize serialized URIs and tuple ranges from API payloads', async () => {
+		const serializedUri = JSON.parse(JSON.stringify(URI.parse('git:/c%3A/Code/vscode.worktrees/copilot-worktree-2026-03-04T14-44-38/src/vs/sessions/contrib/changesView/test/browser/codeReviewService.test.ts?%7B%22path%22%3A%22c%3A%5C%5CCode%5C%5Cvscode.worktrees%5C%5Ccopilot-worktree-2026-03-04T14-44-38%5C%5Csrc%5C%5Cvs%5C%5Csessions%5C%5Ccontrib%5C%5CchangesView%5C%5Ctest%5C%5Cbrowser%5C%5CcodeReviewService.test.ts%22%2C%22ref%22%3A%22copilot-worktree-2026-03-04T14-44-38%22%7D')));
+
+		commandService.result = {
+			type: 'success',
+			comments: [
+				{
+					uri: serializedUri,
+					range: [
+						{ line: 72, character: 2 },
+						{ line: 72, character: 3 },
+					],
+					body: 'tuple range comment',
+					kind: 'bug',
+					severity: 'medium',
+				},
+			],
+		};
+
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Result);
+		if (state.kind === CodeReviewStateKind.Result) {
+			assert.strictEqual(state.comments[0].uri.toString(), URI.revive(serializedUri).toString());
+			assert.deepStrictEqual(state.comments[0].range, new Range(73, 3, 73, 4));
+		}
+	});
+
+	test('each comment gets a unique id', async () => {
+		commandService.result = {
+			type: 'success',
+			comments: [
+				{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'a' },
+				{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'b' },
+			],
+		};
+
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		if (state.kind === CodeReviewStateKind.Result) {
+			assert.notStrictEqual(state.comments[0].id, state.comments[1].id);
+		}
+	});
+
+	// --- Observable reactivity ---
+
+	test('observable fires on state transitions', async () => {
+		const states: string[] = [];
+		const obs = service.getReviewState(session);
+
+		// Collect initial state
+		states.push(obs.get().kind);
+
+		commandService.deferNextExecution();
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		states.push(obs.get().kind);
+
+		commandService.resolveExecution({ type: 'success', comments: [] });
+		await tick();
+		states.push(obs.get().kind);
+
+		service.dismissReview(session);
+		states.push(obs.get().kind);
+
+		assert.deepStrictEqual(states, [
+			CodeReviewStateKind.Idle,
+			CodeReviewStateKind.Loading,
+			CodeReviewStateKind.Result,
+			CodeReviewStateKind.Idle,
+		]);
+	});
+
+	// --- Storage persistence ---
+
+	test('review results are persisted to storage', async () => {
+		commandService.result = {
+			type: 'success',
+			comments: [{ uri: fileA, range: new Range(1, 1, 5, 1), body: 'Persisted comment', kind: 'bug', severity: 'high' }],
+		};
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		const raw = storageService.get('codeReview.reviews', StorageScope.WORKSPACE);
+		assert.ok(raw, 'Storage should contain review data');
+		const stored = JSON.parse(raw!);
+		const reviewData = stored[session.toString()];
+		assert.ok(reviewData);
+		assert.strictEqual(reviewData.version, 'v1');
+		assert.strictEqual(reviewData.comments.length, 1);
+		assert.strictEqual(reviewData.comments[0].body, 'Persisted comment');
+	});
+
+	test('reviews are restored from storage on service creation', async () => {
+		commandService.result = {
+			type: 'success',
+			comments: [{ uri: fileA, range: new Range(1, 1, 5, 1), body: 'Restored comment', kind: 'bug', severity: 'high' }],
+		};
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		// Create a second service with the same storage
+		const service2 = store.add(instantiationService.createInstance(CodeReviewService));
+		const state = service2.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Result);
+		if (state.kind === CodeReviewStateKind.Result) {
+			assert.strictEqual(state.version, 'v1');
+			assert.strictEqual(state.comments.length, 1);
+			assert.strictEqual(state.comments[0].body, 'Restored comment');
+			assert.strictEqual(state.comments[0].uri.toString(), fileA.toString());
+			assert.deepStrictEqual(state.comments[0].range, { startLineNumber: 1, startColumn: 1, endLineNumber: 5, endColumn: 1 });
+		}
+	});
+
+	test('suggestions are persisted and restored correctly', async () => {
+		commandService.result = {
+			type: 'success',
+			comments: [{
+				uri: fileA,
+				range: new Range(1, 1, 5, 1),
+				body: 'suggestion comment',
+				suggestion: {
+					edits: [{
+						range: new Range(2, 1, 3, 10),
+						oldText: 'let x = 1;',
+						newText: 'const x = 1;',
+					}],
+				},
+			}],
+		};
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		const service2 = store.add(instantiationService.createInstance(CodeReviewService));
+		const state = service2.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Result);
+		if (state.kind === CodeReviewStateKind.Result) {
+			assert.strictEqual(state.comments[0].suggestion?.edits.length, 1);
+			assert.strictEqual(state.comments[0].suggestion?.edits[0].oldText, 'let x = 1;');
+			assert.strictEqual(state.comments[0].suggestion?.edits[0].newText, 'const x = 1;');
+		}
+	});
+
+	test('removeComment updates storage', async () => {
+		commandService.result = {
+			type: 'success',
+			comments: [
+				{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'comment1' },
+				{ uri: fileA, range: new Range(5, 1, 5, 1), body: 'comment2' },
+			],
+		};
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		const state = service.getReviewState(session).get();
+		if (state.kind !== CodeReviewStateKind.Result) { return; }
+
+		service.removeComment(session, state.comments[0].id);
+
+		const raw = storageService.get('codeReview.reviews', StorageScope.WORKSPACE);
+		const stored = JSON.parse(raw!);
+		assert.strictEqual(stored[session.toString()].comments.length, 1);
+		assert.strictEqual(stored[session.toString()].comments[0].body, 'comment2');
+	});
+
+	test('dismissReview removes session from storage', async () => {
+		commandService.result = { type: 'success', comments: [{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'c' }] };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		assert.ok(storageService.get('codeReview.reviews', StorageScope.WORKSPACE));
+
+		service.dismissReview(session);
+
+		assert.strictEqual(storageService.get('codeReview.reviews', StorageScope.WORKSPACE), undefined);
+	});
+
+	test('corrupted storage is handled gracefully', () => {
+		storageService.store('codeReview.reviews', 'not-valid-json{{{', StorageScope.WORKSPACE, StorageTarget.MACHINE);
+
+		const service2 = store.add(instantiationService.createInstance(CodeReviewService));
+		const state = service2.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Idle);
+	});
+
+	// --- Session lifecycle cleanup ---
+
+	test('archived session reviews are cleaned up', async () => {
+		commandService.result = { type: 'success', comments: [{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'comment' }] };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Result);
+
+		const mockSession = agentSessionsService.setSession(session, undefined, true);
+		agentSessionsService.fireSessionArchivedState(mockSession);
+
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Idle);
+		assert.strictEqual(storageService.get('codeReview.reviews', StorageScope.WORKSPACE), undefined);
+	});
+
+	test('non-archived session change does not clean up review', async () => {
+		commandService.result = { type: 'success', comments: [{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'comment' }] };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		const mockSession = agentSessionsService.setSession(session, undefined, false);
+		agentSessionsService.fireSessionArchivedState(mockSession);
+
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Result);
+	});
+
+	test('session with changed version has review cleaned up', async () => {
+		const changes: IChatSessionFileChange2[] = [
+			{ uri: fileA, modifiedUri: fileA, insertions: 1, deletions: 0 },
+		];
+		agentSessionsService.setSession(session, changes);
+
+		const files = getCodeReviewFilesFromSessionChanges(changes);
+		const version = getCodeReviewVersion(files);
+
+		commandService.result = { type: 'success', comments: [{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'stale comment' }] };
+		service.requestReview(session, version, files);
+		await tick();
+
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Result);
+
+		const newChanges: IChatSessionFileChange2[] = [
+			{ uri: fileA, modifiedUri: fileA, insertions: 1, deletions: 0 },
+			{ uri: fileB, modifiedUri: fileB, insertions: 2, deletions: 0 },
+		];
+		agentSessionsService.updateSessionChanges(session, newChanges);
+		agentSessionsService.fireSessionsChanged();
+
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Idle);
+		assert.strictEqual(storageService.get('codeReview.reviews', StorageScope.WORKSPACE), undefined);
+	});
+
+	test('session that no longer exists has review cleaned up', async () => {
+		commandService.result = { type: 'success', comments: [{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'orphaned comment' }] };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Result);
+
+		agentSessionsService.fireSessionsChanged();
+
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Idle);
+	});
+
+	test('session with no changes has review cleaned up', async () => {
+		agentSessionsService.setSession(session, [
+			{ uri: fileA, modifiedUri: fileA, insertions: 1, deletions: 0 },
+		]);
+
+		commandService.result = { type: 'success', comments: [{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'comment' }] };
+		service.requestReview(session, 'v1', [{ currentUri: fileA }]);
+		await tick();
+
+		agentSessionsService.updateSessionChanges(session, undefined);
+		agentSessionsService.fireSessionsChanged();
+
+		assert.strictEqual(service.getReviewState(session).get().kind, CodeReviewStateKind.Idle);
+	});
+
+	test('session with matching version keeps review intact', async () => {
+		const changes: IChatSessionFileChange2[] = [
+			{ uri: fileA, modifiedUri: fileA, insertions: 1, deletions: 0 },
+		];
+		agentSessionsService.setSession(session, changes);
+
+		const files = getCodeReviewFilesFromSessionChanges(changes);
+		const version = getCodeReviewVersion(files);
+
+		commandService.result = { type: 'success', comments: [{ uri: fileA, range: new Range(1, 1, 1, 1), body: 'valid comment' }] };
+		service.requestReview(session, version, files);
+		await tick();
+
+		agentSessionsService.fireSessionsChanged();
+
+		const state = service.getReviewState(session).get();
+		assert.strictEqual(state.kind, CodeReviewStateKind.Result);
+		if (state.kind === CodeReviewStateKind.Result) {
+			assert.strictEqual(state.comments[0].body, 'valid comment');
+		}
+	});
+});
+
+function tick(): Promise<void> {
+	return new Promise(resolve => setTimeout(resolve, 0));
+}
diff --git a/src/vs/sessions/contrib/configuration/browser/configuration.contribution.ts b/src/vs/sessions/contrib/configuration/browser/configuration.contribution.ts
index 4ed1b598aa25e..22e2a3bd28dec 100644
--- a/src/vs/sessions/contrib/configuration/browser/configuration.contribution.ts
+++ b/src/vs/sessions/contrib/configuration/browser/configuration.contribution.ts
@@ -8,23 +8,38 @@ import { Registry } from '../../../../platform/registry/common/platform.js';
 
 Registry.as<IConfigurationRegistry>(Extensions.Configuration).registerDefaultConfigurations([{
 	overrides: {
-		'chat.agentsControl.enabled': true,
+		'chat.experimentalSessionsWindowOverride': true,
+		'chat.hookFilesLocations': {
+			'.claude/settings.local.json': false,
+			'.claude/settings.json': false,
+			'~/.claude/settings.json': false,
+		},
 		'chat.agent.maxRequests': 1000,
-		'chat.restoreLastPanelSession': true,
-		'chat.unifiedAgentsBar.enabled': true,
+		'chat.customizationsMenu.userStoragePath': '~/.copilot',
 		'chat.viewSessions.enabled': false,
+		'chat.implicitContext.suggestedContext': false,
+		'chat.implicitContext.enabled': { 'panel': 'never' },
+		'chat.tools.terminal.enableAutoApprove': true,
+		'github.copilot.chat.githubMcpServer.enabled': true,
 
 		'breadcrumbs.enabled': false,
 
-		'diffEditor.renderSideBySide': false,
 		'diffEditor.hideUnchangedRegions.enabled': true,
 
+		'extensions.ignoreRecommendations': true,
+
 		'files.autoSave': 'afterDelay',
 
 		'git.autofetch': true,
+		'git.branchRandomName.enable': true,
 		'git.detectWorktrees': false,
 		'git.showProgress': false,
 
+		'github.copilot.enable': {
+			'markdown': true,
+			'plaintext': true,
+		},
+
 		'github.copilot.chat.claudeCode.enabled': true,
 		'github.copilot.chat.cli.branchSupport.enabled': true,
 		'github.copilot.chat.languageContext.typescript.enabled': true,
@@ -33,18 +48,20 @@ Registry.as<IConfigurationRegistry>(Extensions.Configuration).registerDefaultCon
 		'inlineChat.affordance': 'editor',
 		'inlineChat.renderMode': 'hover',
 
+		'terminal.integrated.initialHint': false,
+
+		'workbench.editor.doubleClickTabToToggleEditorGroupSizes': 'maximize',
 		'workbench.editor.restoreEditors': false,
-		'workbench.editor.showTabs': 'single',
 		'workbench.startupEditor': 'none',
 		'workbench.tips.enabled': false,
 		'workbench.layoutControl.type': 'toggles',
 		'workbench.editor.useModal': 'all',
-		'workbench.editor.labelFormat': 'short',
 		'workbench.panel.showLabels': false,
+		'workbench.colorTheme': 'Experimental Dark',
+		'search.quickOpen.includeHistory': false,
+
 		'window.menuStyle': 'custom',
 		'window.dialogStyle': 'custom',
-
-		'terminal.integrated.initialHint': false
 	},
 	donotCache: true,
 	preventExperimentOverride: true,
diff --git a/src/vs/sessions/contrib/fileTreeView/browser/fileTreeView.ts b/src/vs/sessions/contrib/fileTreeView/browser/fileTreeView.ts
index 0ef758704325e..4861f7d9df16d 100644
--- a/src/vs/sessions/contrib/fileTreeView/browser/fileTreeView.ts
+++ b/src/vs/sessions/contrib/fileTreeView/browser/fileTreeView.ts
@@ -43,7 +43,7 @@ import { IStorageService } from '../../../../platform/storage/common/storage.js'
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
 import { ISessionsManagementService, IActiveSessionItem } from '../../sessions/browser/sessionsManagementService.js';
-import { GITHUB_REMOTE_FILE_SCHEME } from './githubFileSystemProvider.js';
+import { GITHUB_REMOTE_FILE_SCHEME, getGitHubRemoteFileDisplayName } from './githubFileSystemProvider.js';
 import { basename } from '../../../../base/common/path.js';
 import { isEqual } from '../../../../base/common/resources.js';
 
@@ -315,6 +315,9 @@ export class FileTreeViewPane extends ViewPane {
 	 * Extracts a github-remote-file:// URI from session metadata, trying various known fields.
 	 */
 	private extractRepoUriFromMetadata(metadata: { readonly [key: string]: unknown }): URI | undefined {
+		const branch = typeof metadata.branch === 'string' ? metadata.branch : 'HEAD';
+		const encodedRef = encodeURIComponent(branch);
+
 		// repositoryNwo: "owner/repo"
 		const repositoryNwo = metadata.repositoryNwo as string | undefined;
 		if (repositoryNwo && repositoryNwo.includes('/')) {
@@ -322,7 +325,7 @@ export class FileTreeViewPane extends ViewPane {
 			return URI.from({
 				scheme: GITHUB_REMOTE_FILE_SCHEME,
 				authority: 'github',
-				path: `/${repositoryNwo}/HEAD`,
+				path: `/${repositoryNwo}/${encodedRef}`,
 			});
 		}
 
@@ -335,7 +338,7 @@ export class FileTreeViewPane extends ViewPane {
 				return URI.from({
 					scheme: GITHUB_REMOTE_FILE_SCHEME,
 					authority: 'github',
-					path: `/${parsed.owner}/${parsed.repo}/HEAD`,
+					path: `/${parsed.owner}/${parsed.repo}/${encodedRef}`,
 				});
 			}
 		}
@@ -349,7 +352,7 @@ export class FileTreeViewPane extends ViewPane {
 				return URI.from({
 					scheme: GITHUB_REMOTE_FILE_SCHEME,
 					authority: 'github',
-					path: `/${repository}/HEAD`,
+					path: `/${repository}/${encodedRef}`,
 				});
 			}
 			const parsed = this.parseGitHubUrl(repository);
@@ -358,7 +361,7 @@ export class FileTreeViewPane extends ViewPane {
 				return URI.from({
 					scheme: GITHUB_REMOTE_FILE_SCHEME,
 					authority: 'github',
-					path: `/${parsed.owner}/${parsed.repo}/HEAD`,
+					path: `/${parsed.owner}/${parsed.repo}/${encodedRef}`,
 				});
 			}
 		}
@@ -514,7 +517,7 @@ export class FileTreeViewPane extends ViewPane {
 
 			if (this.tree && rootUri && !isEqual(rootUri, lastRootUri)) {
 				lastRootUri = rootUri;
-				this.updateTitle(basename(rootUri.path) || rootUri.toString());
+				this.updateTitle(this.getTreeTitle(rootUri));
 				this.treeInputDisposable.clear();
 				this.tree.setInput(rootUri).then(() => {
 					this.layoutTree();
@@ -525,6 +528,10 @@ export class FileTreeViewPane extends ViewPane {
 		}));
 	}
 
+	private getTreeTitle(rootUri: URI): string {
+		return getGitHubRemoteFileDisplayName(rootUri) ?? (basename(rootUri.path) || rootUri.toString());
+	}
+
 	private layoutTree(): void {
 		if (!this.tree) {
 			return;
diff --git a/src/vs/sessions/contrib/fileTreeView/browser/githubFileSystemProvider.ts b/src/vs/sessions/contrib/fileTreeView/browser/githubFileSystemProvider.ts
index 289911e399578..9fc89e146514c 100644
--- a/src/vs/sessions/contrib/fileTreeView/browser/githubFileSystemProvider.ts
+++ b/src/vs/sessions/contrib/fileTreeView/browser/githubFileSystemProvider.ts
@@ -14,6 +14,28 @@ import { ILogService } from '../../../../platform/log/common/log.js';
 
 export const GITHUB_REMOTE_FILE_SCHEME = 'github-remote-file';
 
+/**
+ * Derives a display name from a github-remote-file URI.
+ * Returns "repo (branch)" or just "repo" when on HEAD.
+ */
+export function getGitHubRemoteFileDisplayName(uri: URI): string | undefined {
+	if (uri.scheme !== GITHUB_REMOTE_FILE_SCHEME) {
+		return undefined;
+	}
+	const parts = uri.path.split('/').filter(Boolean);
+	// path = /{owner}/{repo}/{ref}/...
+	if (parts.length >= 3) {
+		const [, repo, ref] = parts;
+		const decodedRepo = decodeURIComponent(repo);
+		const decodedRef = decodeURIComponent(ref);
+		if (decodedRef === 'HEAD') {
+			return decodedRepo;
+		}
+		return `${decodedRepo} (${decodedRef})`;
+	}
+	return undefined;
+}
+
 /**
  * GitHub REST API response for the Trees endpoint.
  * GET /repos/{owner}/{repo}/git/trees/{tree_sha}?recursive=1
@@ -67,9 +89,18 @@ export class GitHubFileSystemProvider extends Disposable implements IFileSystemP
 	/** Cache keyed by "owner/repo/ref" */
 	private readonly treeCache = new Map<string, ITreeCacheEntry>();
 
+	/** Negative cache for refs that returned 404, keyed by "owner/repo/ref" */
+	private readonly notFoundCache = new Map<string, number>();
+
+	/** In-flight fetch promises keyed by "owner/repo/ref" to deduplicate concurrent requests */
+	private readonly pendingFetches = new Map<string, Promise<ITreeCacheEntry>>();
+
 	/** Cache TTL - 5 minutes */
 	private static readonly CACHE_TTL_MS = 5 * 60 * 1000;
 
+	/** Negative cache TTL - 1 minute */
+	private static readonly NOT_FOUND_CACHE_TTL_MS = 60 * 1000;
+
 	constructor(
 		@IRequestService private readonly requestService: IRequestService,
 		@IAuthenticationService private readonly authenticationService: IAuthenticationService,
@@ -92,10 +123,10 @@ export class GitHubFileSystemProvider extends Disposable implements IFileSystemP
 			throw createFileSystemProviderError('Invalid github-remote-file URI: expected /{owner}/{repo}/{ref}/...', FileSystemProviderErrorCode.FileNotFound);
 		}
 
-		const owner = parts[0];
-		const repo = parts[1];
-		const ref = parts[2];
-		const path = parts.slice(3).join('/');
+		const owner = decodeURIComponent(parts[0]);
+		const repo = decodeURIComponent(parts[1]);
+		const ref = decodeURIComponent(parts[2]);
+		const path = parts.slice(3).map(decodeURIComponent).join('/');
 
 		return { owner, repo, ref, path };
 	}
@@ -107,23 +138,45 @@ export class GitHubFileSystemProvider extends Disposable implements IFileSystemP
 	// --- GitHub API
 
 	private async getAuthToken(): Promise<string> {
-		const sessions = await this.authenticationService.getSessions('github', ['repo']);
-		if (sessions.length > 0) {
-			return sessions[0].accessToken;
+		let sessions = await this.authenticationService.getSessions('github', [], { silent: true });
+		if (!sessions || sessions.length === 0) {
+			sessions = await this.authenticationService.getSessions('github', [], { createIfNone: true });
 		}
-
-		// Try to create a session if none exists
-		const session = await this.authenticationService.createSession('github', ['repo']);
-		return session.accessToken;
+		if (!sessions || sessions.length === 0) {
+			throw createFileSystemProviderError('No GitHub authentication sessions available', FileSystemProviderErrorCode.Unavailable);
+		}
+		return sessions[0].accessToken ?? '';
 	}
 
-	private async fetchTree(owner: string, repo: string, ref: string): Promise<ITreeCacheEntry> {
+	private fetchTree(owner: string, repo: string, ref: string): Promise<ITreeCacheEntry> {
 		const cacheKey = this.getCacheKey(owner, repo, ref);
+
+		// Check positive cache
 		const cached = this.treeCache.get(cacheKey);
 		if (cached && (Date.now() - cached.fetchedAt) < GitHubFileSystemProvider.CACHE_TTL_MS) {
-			return cached;
+			return Promise.resolve(cached);
+		}
+
+		// Check negative cache (recently returned 404)
+		const notFoundAt = this.notFoundCache.get(cacheKey);
+		if (notFoundAt !== undefined && (Date.now() - notFoundAt) < GitHubFileSystemProvider.NOT_FOUND_CACHE_TTL_MS) {
+			return Promise.reject(createFileSystemProviderError(`Tree not found for ${owner}/${repo}@${ref}`, FileSystemProviderErrorCode.FileNotFound));
 		}
 
+		// Deduplicate concurrent requests for the same tree
+		const pending = this.pendingFetches.get(cacheKey);
+		if (pending) {
+			return pending;
+		}
+
+		const promise = this.doFetchTree(owner, repo, ref, cacheKey).finally(() => {
+			this.pendingFetches.delete(cacheKey);
+		});
+		this.pendingFetches.set(cacheKey, promise);
+		return promise;
+	}
+
+	private async doFetchTree(owner: string, repo: string, ref: string, cacheKey: string): Promise<ITreeCacheEntry> {
 		this.logService.info(`[SessionRepoFS] Fetching tree for ${owner}/${repo}@${ref}`);
 		const token = await this.getAuthToken();
 
@@ -136,9 +189,17 @@ export class GitHubFileSystemProvider extends Disposable implements IFileSystemP
 				'Accept': 'application/vnd.github.v3+json',
 				'User-Agent': 'VSCode-SessionRepoFS',
 			},
+			callSite: 'githubFileSystemProvider.fetchTree'
 		}, CancellationToken.None);
 
+		// Cache 404s so we don't keep re-fetching missing trees
+		if (response.res.statusCode === 404) {
+			this.notFoundCache.set(cacheKey, Date.now());
+			throw createFileSystemProviderError(`Tree not found for ${owner}/${repo}@${ref}`, FileSystemProviderErrorCode.FileNotFound);
+		}
+
 		const data = await asJson<IGitHubTreeResponse>(response);
+
 		if (!data) {
 			throw createFileSystemProviderError(`Failed to fetch tree for ${owner}/${repo}@${ref}`, FileSystemProviderErrorCode.Unavailable);
 		}
@@ -239,6 +300,7 @@ export class GitHubFileSystemProvider extends Disposable implements IFileSystemP
 				'Accept': 'application/vnd.github.v3+json',
 				'User-Agent': 'VSCode-SessionRepoFS',
 			},
+			callSite: 'githubFileSystemProvider.readFile'
 		}, CancellationToken.None);
 
 		const data = await asJson<{ content: string; encoding: string }>(response);
@@ -283,11 +345,15 @@ export class GitHubFileSystemProvider extends Disposable implements IFileSystemP
 	// --- Cache management
 
 	invalidateCache(owner: string, repo: string, ref: string): void {
-		this.treeCache.delete(this.getCacheKey(owner, repo, ref));
+		const cacheKey = this.getCacheKey(owner, repo, ref);
+		this.treeCache.delete(cacheKey);
+		this.notFoundCache.delete(cacheKey);
 	}
 
 	override dispose(): void {
 		this.treeCache.clear();
+		this.notFoundCache.clear();
+		this.pendingFetches.clear();
 		super.dispose();
 	}
 }
diff --git a/src/vs/sessions/contrib/files/browser/files.contribution.ts b/src/vs/sessions/contrib/files/browser/files.contribution.ts
new file mode 100644
index 0000000000000..6d9f6fa696a4e
--- /dev/null
+++ b/src/vs/sessions/contrib/files/browser/files.contribution.ts
@@ -0,0 +1,83 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Codicon } from '../../../../base/common/codicons.js';
+import { localize2 } from '../../../../nls.js';
+import { Action2, MenuId, registerAction2 } from '../../../../platform/actions/common/actions.js';
+import { ContextKeyExpr } from '../../../../platform/contextkey/common/contextkey.js';
+import { SyncDescriptor } from '../../../../platform/instantiation/common/descriptors.js';
+import { ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
+import { Registry } from '../../../../platform/registry/common/platform.js';
+import { registerIcon } from '../../../../platform/theme/common/iconRegistry.js';
+import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../../workbench/common/contributions.js';
+import { IViewContainersRegistry, IViewsRegistry, ViewContainerLocation, Extensions as ViewContainerExtensions, WindowVisibility } from '../../../../workbench/common/views.js';
+import { WorkspaceFolderCountContext } from '../../../../workbench/common/contextkeys.js';
+import { ExplorerView } from '../../../../workbench/contrib/files/browser/views/explorerView.js';
+import { ViewPaneContainer } from '../../../../workbench/browser/parts/views/viewPaneContainer.js';
+import { IViewsService } from '../../../../workbench/services/views/common/viewsService.js';
+
+const SESSIONS_FILES_CONTAINER_ID = 'workbench.sessions.auxiliaryBar.filesContainer';
+const SESSIONS_FILES_VIEW_ID = 'sessions.files.explorer';
+
+const filesViewIcon = registerIcon('sessions-files-view-icon', Codicon.files, localize2('sessionsFilesViewIcon', 'View icon of the files view in the sessions window.').value);
+
+class RegisterFilesViewContribution implements IWorkbenchContribution {
+
+	static readonly ID = 'sessions.registerFilesView';
+
+	constructor() {
+		const viewContainerRegistry = Registry.as<IViewContainersRegistry>(ViewContainerExtensions.ViewContainersRegistry);
+		const viewsRegistry = Registry.as<IViewsRegistry>(ViewContainerExtensions.ViewsRegistry);
+
+		// Register a new Files view container in the auxiliary bar for the sessions window
+		const filesViewContainer = viewContainerRegistry.registerViewContainer({
+			id: SESSIONS_FILES_CONTAINER_ID,
+			title: localize2('files', "Files"),
+			icon: filesViewIcon,
+			order: 11,
+			ctorDescriptor: new SyncDescriptor(ViewPaneContainer, [SESSIONS_FILES_CONTAINER_ID, { mergeViewWithContainerWhenSingleView: true }]),
+			storageId: SESSIONS_FILES_CONTAINER_ID,
+			hideIfEmpty: true,
+			windowVisibility: WindowVisibility.Sessions,
+		}, ViewContainerLocation.AuxiliaryBar, { doNotRegisterOpenCommand: true });
+
+		// Re-register the explorer view inside the new Files container
+		viewsRegistry.registerViews([{
+			id: SESSIONS_FILES_VIEW_ID,
+			name: localize2('files', "Files"),
+			containerIcon: filesViewIcon,
+			ctorDescriptor: new SyncDescriptor(ExplorerView),
+			canToggleVisibility: true,
+			canMoveView: false,
+			when: WorkspaceFolderCountContext.notEqualsTo('0'),
+			windowVisibility: WindowVisibility.Sessions,
+		}], filesViewContainer);
+	}
+}
+
+registerWorkbenchContribution2(RegisterFilesViewContribution.ID, RegisterFilesViewContribution, WorkbenchPhase.AfterRestored);
+
+registerAction2(class extends Action2 {
+	constructor() {
+		super({
+			id: 'sessions.files.action.collapseExplorerFolders',
+			title: localize2('collapseExplorerFolders', "Collapse Folders in Explorer"),
+			icon: Codicon.collapseAll,
+			menu: {
+				id: MenuId.ViewTitle,
+				group: 'navigation',
+				when: ContextKeyExpr.equals('view', SESSIONS_FILES_VIEW_ID),
+			},
+		});
+	}
+
+	run(accessor: ServicesAccessor) {
+		const viewsService = accessor.get(IViewsService);
+		const view = viewsService.getViewWithId(SESSIONS_FILES_VIEW_ID);
+		if (view !== null) {
+			(view as ExplorerView).collapseAll();
+		}
+	}
+});
diff --git a/src/vs/sessions/contrib/git/browser/git.contribution.ts b/src/vs/sessions/contrib/git/browser/git.contribution.ts
new file mode 100644
index 0000000000000..ad28526fdb629
--- /dev/null
+++ b/src/vs/sessions/contrib/git/browser/git.contribution.ts
@@ -0,0 +1,137 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Disposable, IDisposable } from '../../../../base/common/lifecycle.js';
+import { autorun, constObservable, derived, ObservablePromise, observableValue } from '../../../../base/common/observable.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { ThemeIcon } from '../../../../base/common/themables.js';
+import { localize } from '../../../../nls.js';
+import { Action2, MenuId, registerAction2 } from '../../../../platform/actions/common/actions.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
+import { ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
+import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../../workbench/common/contributions.js';
+import { CHAT_CATEGORY } from '../../../../workbench/contrib/chat/browser/actions/chatActions.js';
+import { GitBranch, GitRepositoryState, IGitService } from '../../../../workbench/contrib/git/common/gitService.js';
+import { ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
+
+const hasUpstreamBranchContextKey = new RawContextKey<boolean>('agentSessionGitHasUpstreamBranch', false, {
+	type: 'boolean',
+	description: localize('agentSessionGitHasUpstreamBranch', "True when the active agent session worktree has an upstream branch."),
+});
+
+class GitSyncContribution extends Disposable implements IWorkbenchContribution {
+
+	static readonly ID = 'sessions.contrib.gitSync';
+
+	private readonly _isSyncingObs = observableValue<boolean>(this, false);
+
+	constructor(
+		@IContextKeyService private readonly contextKeyService: IContextKeyService,
+		@ISessionsManagementService private readonly sessionManagementService: ISessionsManagementService,
+		@IGitService private readonly gitService: IGitService,
+	) {
+		super();
+
+		const hasUpstreamBranch = hasUpstreamBranchContextKey.bindTo(this.contextKeyService);
+
+		const activeSessionWorktreeObs = derived(reader => {
+			const activeSession = this.sessionManagementService.activeSession.read(reader);
+			return activeSession?.worktree;
+		});
+
+		const activeSessionRepositoryPromiseObs = derived(reader => {
+			const worktreeUri = activeSessionWorktreeObs.read(reader);
+			if (!worktreeUri) {
+				return constObservable(undefined);
+			}
+
+			return new ObservablePromise(this.gitService.openRepository(worktreeUri)).resolvedValue;
+		});
+
+		const activeSessionRepositoryStateObs = derived<GitRepositoryState | undefined>(reader => {
+			const activeSessionRepository = activeSessionRepositoryPromiseObs.read(reader).read(reader);
+			if (activeSessionRepository === undefined) {
+				return undefined;
+			}
+
+			return activeSessionRepository.state.read(reader);
+		});
+
+		this._register(autorun(reader => {
+			const isSyncing = this._isSyncingObs.read(reader);
+			const activeSessionRepositoryState = activeSessionRepositoryStateObs.read(reader);
+			if (!activeSessionRepositoryState) {
+				hasUpstreamBranch.set(false);
+				return;
+			}
+
+			const head = activeSessionRepositoryState.HEAD;
+			hasUpstreamBranch.set(head?.upstream !== undefined);
+
+			if (!head?.upstream) {
+				return;
+			}
+
+			reader.store.add(registerSyncAction(head, isSyncing, (syncing) => {
+				this._isSyncingObs.set(syncing, undefined);
+			}));
+		}));
+	}
+}
+
+function registerSyncAction(branch: GitBranch, isSyncing: boolean, setSyncing: (syncing: boolean) => void): IDisposable {
+	const ahead = branch.ahead ?? 0;
+	const behind = branch.behind ?? 0;
+
+	const titleSegments = [localize('synchronizeChangesTitle', "Sync Changes")];
+	if (behind > 0) {
+		titleSegments.push(`${behind}↓`);
+	}
+	if (ahead > 0) {
+		titleSegments.push(`${ahead}↑`);
+	}
+
+	const icon = isSyncing
+		? ThemeIcon.modify(Codicon.sync, 'spin')
+		: Codicon.sync;
+
+	class SynchronizeChangesAction extends Action2 {
+		static readonly ID = 'chatEditing.synchronizeChanges';
+
+		constructor() {
+			super({
+				id: SynchronizeChangesAction.ID,
+				title: titleSegments.join(' '),
+				tooltip: localize('synchronizeChanges', "Synchronize Changes with Git (Behind {0}, Ahead {1})", behind, ahead),
+				icon,
+				category: CHAT_CATEGORY,
+				menu: [
+					{
+						id: MenuId.ChatEditingSessionApplySubmenu,
+						group: 'navigation',
+						order: 0,
+						when: hasUpstreamBranchContextKey,
+					},
+				],
+			});
+		}
+
+		override async run(accessor: ServicesAccessor): Promise<void> {
+			const commandService = accessor.get(ICommandService);
+			const sessionManagementService = accessor.get(ISessionsManagementService);
+			const worktreeUri = sessionManagementService.getActiveSession()?.worktree;
+			setSyncing(true);
+			try {
+				await commandService.executeCommand('git.sync', worktreeUri);
+			} finally {
+				setSyncing(false);
+			}
+		}
+	}
+	return registerAction2(SynchronizeChangesAction);
+}
+
+registerWorkbenchContribution2(GitSyncContribution.ID, GitSyncContribution, WorkbenchPhase.AfterRestored);
diff --git a/src/vs/sessions/contrib/github/browser/fetchers/githubPRCIFetcher.ts b/src/vs/sessions/contrib/github/browser/fetchers/githubPRCIFetcher.ts
new file mode 100644
index 0000000000000..c212fa79443d4
--- /dev/null
+++ b/src/vs/sessions/contrib/github/browser/fetchers/githubPRCIFetcher.ts
@@ -0,0 +1,204 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { GitHubCheckConclusion, GitHubCheckStatus, GitHubCIOverallStatus, IGitHubCICheck } from '../../common/types.js';
+import { GitHubApiClient } from '../githubApiClient.js';
+
+//#region GitHub API response types
+
+interface IGitHubCheckRunResponse {
+	readonly id: number;
+	readonly name: string;
+	readonly status: string;
+	readonly conclusion: string | null;
+	readonly started_at: string | null;
+	readonly completed_at: string | null;
+	readonly details_url: string | null;
+}
+
+interface IGitHubCheckRunsListResponse {
+	readonly total_count: number;
+	readonly check_runs: readonly IGitHubCheckRunResponse[];
+}
+
+interface IGitHubCheckRunAnnotationResponse {
+	readonly path: string;
+	readonly start_line: number;
+	readonly end_line: number;
+	readonly annotation_level: string;
+	readonly message: string;
+	readonly title: string | null;
+}
+
+interface IGitHubCheckRunDetailResponse {
+	readonly id: number;
+	readonly name: string;
+	readonly details_url: string | null;
+	readonly app: {
+		readonly slug: string;
+	} | null;
+	readonly output: {
+		readonly title: string | null;
+		readonly summary: string | null;
+		readonly text: string | null;
+		readonly annotations_count: number;
+	};
+}
+
+//#endregion
+
+/**
+ * Stateless fetcher for GitHub CI check data (check runs, check suites).
+ * All methods return raw typed data with no caching or state.
+ */
+export class GitHubPRCIFetcher {
+
+	constructor(
+		private readonly _apiClient: GitHubApiClient,
+	) { }
+
+	async getCheckRuns(owner: string, repo: string, ref: string): Promise<IGitHubCICheck[]> {
+		const data = await this._apiClient.request<IGitHubCheckRunsListResponse>(
+			'GET',
+			`/repos/${e(owner)}/${e(repo)}/commits/${e(ref)}/check-runs`,
+			'githubApi.getCheckRuns'
+		);
+		return data.check_runs.map(mapCheckRun);
+	}
+
+	/**
+	 * Get logs/output for a specific check run.
+	 *
+	 * Tries multiple sources in order:
+	 * 1. The check run's own output fields (title, summary, text) — set by the
+	 *    check run creator via the Checks API.
+	 * 2. Annotations attached to the check run.
+	 * 3. GitHub Actions job logs (only works for GitHub Actions workflows).
+	 */
+	async getCheckRunAnnotations(owner: string, repo: string, checkRunId: number): Promise<string> {
+		const sections: string[] = [];
+		let detail: IGitHubCheckRunDetailResponse | undefined;
+
+		// 1. Fetch check run detail for output fields
+		try {
+			detail = await this._apiClient.request<IGitHubCheckRunDetailResponse>(
+				'GET',
+				`/repos/${e(owner)}/${e(repo)}/check-runs/${checkRunId}`,
+				'githubApi.getCheckRunAnnotations'
+			);
+			const output = detail.output;
+			if (output.title) {
+				sections.push(`# ${output.title}`);
+			}
+			if (output.summary) {
+				sections.push(output.summary);
+			}
+			if (output.text) {
+				sections.push(output.text);
+			}
+		} catch {
+			// Ignore — output may not be available
+		}
+
+		// 2. Fetch annotations
+		try {
+			const annotations = await this._apiClient.request<readonly IGitHubCheckRunAnnotationResponse[]>(
+				'GET',
+				`/repos/${e(owner)}/${e(repo)}/check-runs/${checkRunId}/annotations`,
+				'githubApi.getCheckRunAnnotations.annotations'
+			);
+			if (annotations.length > 0) {
+				sections.push(
+					annotations.map(a =>
+						`[${a.annotation_level}] ${a.path}:${a.start_line}${a.end_line !== a.start_line ? `-${a.end_line}` : ''} ${a.title ? `(${a.title}) ` : ''}${a.message}`
+					).join('\n')
+				);
+			}
+		} catch {
+			// Ignore — annotations may not be available
+		}
+
+		if (sections.length > 0) {
+			return sections.join('\n\n');
+		}
+
+		return 'No output available for this check run.';
+	}
+}
+
+//#region Helpers
+
+function e(value: string): string {
+	return encodeURIComponent(value);
+}
+
+function mapCheckRun(data: IGitHubCheckRunResponse): IGitHubCICheck {
+	return {
+		id: data.id,
+		name: data.name,
+		status: mapCheckStatus(data.status),
+		conclusion: data.conclusion ? mapCheckConclusion(data.conclusion) : undefined,
+		startedAt: data.started_at ?? undefined,
+		completedAt: data.completed_at ?? undefined,
+		detailsUrl: data.details_url ?? undefined,
+	};
+}
+
+function mapCheckStatus(status: string): GitHubCheckStatus {
+	switch (status) {
+		case 'queued': return GitHubCheckStatus.Queued;
+		case 'in_progress': return GitHubCheckStatus.InProgress;
+		case 'completed': return GitHubCheckStatus.Completed;
+		default: return GitHubCheckStatus.Queued;
+	}
+}
+
+function mapCheckConclusion(conclusion: string): GitHubCheckConclusion {
+	switch (conclusion) {
+		case 'success': return GitHubCheckConclusion.Success;
+		case 'failure': return GitHubCheckConclusion.Failure;
+		case 'neutral': return GitHubCheckConclusion.Neutral;
+		case 'cancelled': return GitHubCheckConclusion.Cancelled;
+		case 'skipped': return GitHubCheckConclusion.Skipped;
+		case 'timed_out': return GitHubCheckConclusion.TimedOut;
+		case 'action_required': return GitHubCheckConclusion.ActionRequired;
+		case 'stale': return GitHubCheckConclusion.Stale;
+		default: return GitHubCheckConclusion.Neutral;
+	}
+}
+
+/**
+ * Compute an overall CI status from a list of check runs.
+ */
+export function computeOverallCIStatus(checks: readonly IGitHubCICheck[]): GitHubCIOverallStatus {
+	if (checks.length === 0) {
+		return GitHubCIOverallStatus.Neutral;
+	}
+
+	let hasFailure = false;
+	let hasPending = false;
+
+	for (const check of checks) {
+		if (check.status !== GitHubCheckStatus.Completed) {
+			hasPending = true;
+			continue;
+		}
+		if (check.conclusion === GitHubCheckConclusion.Failure ||
+			check.conclusion === GitHubCheckConclusion.TimedOut ||
+			check.conclusion === GitHubCheckConclusion.ActionRequired) {
+			hasFailure = true;
+		}
+	}
+
+	if (hasFailure) {
+		return GitHubCIOverallStatus.Failure;
+	}
+	if (hasPending) {
+		return GitHubCIOverallStatus.Pending;
+	}
+	return GitHubCIOverallStatus.Success;
+}
+
+//#endregion
diff --git a/src/vs/sessions/contrib/github/browser/fetchers/githubPRFetcher.ts b/src/vs/sessions/contrib/github/browser/fetchers/githubPRFetcher.ts
new file mode 100644
index 0000000000000..e900a5995879a
--- /dev/null
+++ b/src/vs/sessions/contrib/github/browser/fetchers/githubPRFetcher.ts
@@ -0,0 +1,367 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import {
+	GitHubPullRequestState,
+	IGitHubPRComment,
+	IGitHubPRReviewThread,
+	IGitHubPullRequest,
+	IGitHubPullRequestMergeability,
+	IGitHubUser,
+	IMergeBlocker,
+	MergeBlockerKind,
+} from '../../common/types.js';
+import { GitHubApiClient } from '../githubApiClient.js';
+
+//#region GitHub API response types
+
+interface IGitHubPRResponse {
+	readonly number: number;
+	readonly title: string;
+	readonly body: string | null;
+	readonly state: 'open' | 'closed';
+	readonly draft: boolean;
+	readonly user: { readonly login: string; readonly avatar_url: string };
+	readonly head: { readonly ref: string };
+	readonly base: { readonly ref: string };
+	readonly created_at: string;
+	readonly updated_at: string;
+	readonly merged_at: string | null;
+	readonly mergeable: boolean | null;
+	readonly mergeable_state: string;
+	readonly merged: boolean;
+}
+
+interface IGitHubReviewResponse {
+	readonly id: number;
+	readonly user: { readonly login: string; readonly avatar_url: string };
+	readonly state: string;
+	readonly submitted_at: string;
+}
+
+interface IGitHubReviewCommentResponse {
+	readonly id: number;
+	readonly body: string;
+	readonly user: { readonly login: string; readonly avatar_url: string };
+	readonly created_at: string;
+	readonly updated_at: string;
+	readonly path: string;
+	readonly line: number | null;
+	readonly original_line: number | null;
+	readonly in_reply_to_id?: number;
+}
+
+interface IGitHubIssueCommentResponse {
+	readonly id: number;
+	readonly body: string | null;
+	readonly user: { readonly login: string; readonly avatar_url: string };
+	readonly created_at: string;
+	readonly updated_at: string;
+}
+
+interface IGitHubGraphQLPullRequestReviewThreadsResponse {
+	readonly repository: {
+		readonly pullRequest: {
+			readonly reviewThreads: {
+				readonly nodes: readonly IGitHubGraphQLReviewThreadNode[];
+			};
+		} | null;
+	} | null;
+}
+
+interface IGitHubGraphQLReviewThreadNode {
+	readonly id: string;
+	readonly isResolved: boolean;
+	readonly path: string;
+	readonly line: number | null;
+	readonly comments: {
+		readonly nodes: readonly IGitHubGraphQLReviewCommentNode[];
+	};
+}
+
+interface IGitHubGraphQLReviewCommentNode {
+	readonly databaseId: number | null;
+	readonly body: string;
+	readonly createdAt: string;
+	readonly updatedAt: string;
+	readonly path: string | null;
+	readonly line: number | null;
+	readonly originalLine: number | null;
+	readonly replyTo: { readonly databaseId: number | null } | null;
+	readonly author: { readonly login: string; readonly avatarUrl: string } | null;
+}
+
+interface IGitHubGraphQLResolveReviewThreadResponse {
+	readonly resolveReviewThread: {
+		readonly thread: {
+			readonly isResolved: boolean;
+		} | null;
+	} | null;
+}
+
+//#endregion
+
+const GET_REVIEW_THREADS_QUERY = [
+	'query GetReviewThreads($owner: String!, $repo: String!, $prNumber: Int!) {',
+	'  repository(owner: $owner, name: $repo) {',
+	'    pullRequest(number: $prNumber) {',
+	'      reviewThreads(first: 100) {',
+	'        nodes {',
+	'          id',
+	'          isResolved',
+	'          path',
+	'          line',
+	'          comments(first: 100) {',
+	'            nodes {',
+	'              databaseId',
+	'              body',
+	'              createdAt',
+	'              updatedAt',
+	'              path',
+	'              line',
+	'              originalLine',
+	'              replyTo {',
+	'                databaseId',
+	'              }',
+	'              author {',
+	'                login',
+	'                avatarUrl',
+	'              }',
+	'            }',
+	'          }',
+	'        }',
+	'      }',
+	'    }',
+	'  }',
+	'}',
+].join('\n');
+
+const RESOLVE_REVIEW_THREAD_MUTATION = [
+	'mutation ResolveReviewThread($threadId: ID!) {',
+	'  resolveReviewThread(input: { threadId: $threadId }) {',
+	'    thread {',
+	'      isResolved',
+	'    }',
+	'  }',
+	'}',
+].join('\n');
+
+/**
+ * Stateless fetcher for GitHub pull request data.
+ * Handles all PR-related REST API calls including reviews, comments, and mergeability.
+ */
+export class GitHubPRFetcher {
+
+	constructor(
+		private readonly _apiClient: GitHubApiClient,
+	) { }
+
+	async getPullRequest(owner: string, repo: string, prNumber: number): Promise<IGitHubPullRequest> {
+		const data = await this._apiClient.request<IGitHubPRResponse>(
+			'GET',
+			`/repos/${e(owner)}/${e(repo)}/pulls/${prNumber}`,
+			'githubApi.getPullRequest'
+		);
+		return mapPullRequest(data);
+	}
+
+	async getMergeability(owner: string, repo: string, prNumber: number): Promise<IGitHubPullRequestMergeability> {
+		const [pr, reviews] = await Promise.all([
+			this._apiClient.request<IGitHubPRResponse>('GET', `/repos/${e(owner)}/${e(repo)}/pulls/${prNumber}`, 'githubApi.getMergeability.pr'),
+			this._apiClient.request<readonly IGitHubReviewResponse[]>('GET', `/repos/${e(owner)}/${e(repo)}/pulls/${prNumber}/reviews`, 'githubApi.getMergeability.reviews'),
+		]);
+
+		const blockers: IMergeBlocker[] = [];
+
+		// Draft
+		if (pr.draft) {
+			blockers.push({ kind: MergeBlockerKind.Draft, description: 'Pull request is a draft' });
+		}
+
+		// Merge conflicts
+		if (pr.mergeable === false) {
+			blockers.push({ kind: MergeBlockerKind.Conflicts, description: 'Pull request has merge conflicts' });
+		}
+
+		// Changes requested — check most recent review per reviewer
+		const latestReviewByUser = new Map<string, string>();
+		for (const review of reviews) {
+			if (review.state === 'APPROVED' || review.state === 'CHANGES_REQUESTED' || review.state === 'DISMISSED') {
+				latestReviewByUser.set(review.user.login, review.state);
+			}
+		}
+		const hasChangesRequested = [...latestReviewByUser.values()].some(s => s === 'CHANGES_REQUESTED');
+		if (hasChangesRequested) {
+			blockers.push({ kind: MergeBlockerKind.ChangesRequested, description: 'Changes have been requested' });
+		}
+
+		// Approval needed — check mergeable_state
+		if (pr.mergeable_state === 'blocked') {
+			const hasApproval = [...latestReviewByUser.values()].some(s => s === 'APPROVED');
+			if (!hasApproval) {
+				blockers.push({ kind: MergeBlockerKind.ApprovalNeeded, description: 'Approval is required' });
+			}
+		}
+
+		// CI failures — mergeable_state 'unstable' indicates check failures
+		if (pr.mergeable_state === 'unstable') {
+			blockers.push({ kind: MergeBlockerKind.CIFailed, description: 'CI checks have failed' });
+		}
+
+		return {
+			canMerge: blockers.length === 0 && pr.mergeable !== false && pr.state === 'open',
+			blockers,
+		};
+	}
+
+	async getReviewThreads(owner: string, repo: string, prNumber: number): Promise<IGitHubPRReviewThread[]> {
+		const data = await this._apiClient.graphql<IGitHubGraphQLPullRequestReviewThreadsResponse>(
+			GET_REVIEW_THREADS_QUERY,
+			'githubApi.getReviewThreads',
+			{ owner, repo, prNumber },
+		);
+
+		const reviewThreads = data.repository?.pullRequest?.reviewThreads.nodes;
+		if (!reviewThreads) {
+			throw new Error(`Pull request not found: ${owner}/${repo}#${prNumber}`);
+		}
+
+		return reviewThreads.map(mapReviewThread);
+	}
+
+	async postReviewComment(
+		owner: string,
+		repo: string,
+		prNumber: number,
+		body: string,
+		inReplyTo: number,
+	): Promise<IGitHubPRComment> {
+		const data = await this._apiClient.request<IGitHubReviewCommentResponse>(
+			'POST',
+			`/repos/${e(owner)}/${e(repo)}/pulls/${prNumber}/comments`,
+			'githubApi.postReviewComment',
+			{ body, in_reply_to: inReplyTo },
+		);
+		return mapReviewComment(data);
+	}
+
+	async postIssueComment(
+		owner: string,
+		repo: string,
+		prNumber: number,
+		body: string,
+	): Promise<IGitHubPRComment> {
+		const data = await this._apiClient.request<IGitHubIssueCommentResponse>(
+			'POST',
+			`/repos/${e(owner)}/${e(repo)}/issues/${prNumber}/comments`,
+			'githubApi.postIssueComment',
+			{ body },
+		);
+		return {
+			id: data.id,
+			body: data.body ?? '',
+			author: mapUser(data.user),
+			createdAt: data.created_at,
+			updatedAt: data.updated_at,
+			path: undefined,
+			line: undefined,
+			threadId: String(data.id),
+			inReplyToId: undefined,
+		};
+	}
+
+	async resolveThread(_owner: string, _repo: string, threadId: string): Promise<void> {
+		const data = await this._apiClient.graphql<IGitHubGraphQLResolveReviewThreadResponse>(
+			RESOLVE_REVIEW_THREAD_MUTATION,
+			'githubApi.resolveThread',
+			{ threadId },
+		);
+
+		if (!data.resolveReviewThread?.thread?.isResolved) {
+			throw new Error(`Failed to resolve review thread ${threadId}`);
+		}
+	}
+}
+
+//#region Helpers
+
+function e(value: string): string {
+	return encodeURIComponent(value);
+}
+
+function mapUser(user: { readonly login: string; readonly avatar_url: string }): IGitHubUser {
+	return { login: user.login, avatarUrl: user.avatar_url };
+}
+
+function mapPullRequest(data: IGitHubPRResponse): IGitHubPullRequest {
+	let state: GitHubPullRequestState;
+	if (data.merged) {
+		state = GitHubPullRequestState.Merged;
+	} else if (data.state === 'closed') {
+		state = GitHubPullRequestState.Closed;
+	} else {
+		state = GitHubPullRequestState.Open;
+	}
+
+	return {
+		number: data.number,
+		title: data.title,
+		body: data.body ?? '',
+		state,
+		author: mapUser(data.user),
+		headRef: data.head.ref,
+		baseRef: data.base.ref,
+		isDraft: data.draft,
+		createdAt: data.created_at,
+		updatedAt: data.updated_at,
+		mergedAt: data.merged_at ?? undefined,
+		mergeable: data.mergeable ?? undefined,
+		mergeableState: data.mergeable_state,
+	};
+}
+
+function mapReviewComment(data: IGitHubReviewCommentResponse): IGitHubPRComment {
+	return {
+		id: data.id,
+		body: data.body,
+		author: mapUser(data.user),
+		createdAt: data.created_at,
+		updatedAt: data.updated_at,
+		path: data.path,
+		line: data.line ?? data.original_line ?? undefined,
+		threadId: String(data.in_reply_to_id ?? data.id),
+		inReplyToId: data.in_reply_to_id,
+	};
+}
+
+function mapReviewThread(thread: IGitHubGraphQLReviewThreadNode): IGitHubPRReviewThread {
+	return {
+		id: thread.id,
+		isResolved: thread.isResolved,
+		path: thread.path,
+		line: thread.line ?? undefined,
+		comments: thread.comments.nodes.flatMap(comment => mapGraphQLReviewComment(comment, thread)),
+	};
+}
+
+function mapGraphQLReviewComment(comment: IGitHubGraphQLReviewCommentNode, thread: IGitHubGraphQLReviewThreadNode): readonly IGitHubPRComment[] {
+	if (comment.databaseId === null || comment.author === null) {
+		return [];
+	}
+
+	return [{
+		id: comment.databaseId,
+		body: comment.body,
+		author: { login: comment.author.login, avatarUrl: comment.author.avatarUrl },
+		createdAt: comment.createdAt,
+		updatedAt: comment.updatedAt,
+		path: comment.path ?? thread.path,
+		line: comment.line ?? comment.originalLine ?? thread.line ?? undefined,
+		threadId: thread.id,
+		inReplyToId: comment.replyTo?.databaseId ?? undefined,
+	}];
+}
+
+//#endregion
diff --git a/src/vs/sessions/contrib/github/browser/fetchers/githubRepositoryFetcher.ts b/src/vs/sessions/contrib/github/browser/fetchers/githubRepositoryFetcher.ts
new file mode 100644
index 0000000000000..5e4a90dfa90d1
--- /dev/null
+++ b/src/vs/sessions/contrib/github/browser/fetchers/githubRepositoryFetcher.ts
@@ -0,0 +1,43 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { IGitHubRepository } from '../../common/types.js';
+import { GitHubApiClient } from '../githubApiClient.js';
+
+interface IGitHubRepoResponse {
+	readonly name: string;
+	readonly full_name: string;
+	readonly owner: { readonly login: string };
+	readonly default_branch: string;
+	readonly private: boolean;
+	readonly description: string | null;
+}
+
+/**
+ * Stateless fetcher for GitHub repository data.
+ * All methods return raw typed data with no caching or state.
+ */
+export class GitHubRepositoryFetcher {
+
+	constructor(
+		private readonly _apiClient: GitHubApiClient,
+	) { }
+
+	async getRepository(owner: string, repo: string): Promise<IGitHubRepository> {
+		const data = await this._apiClient.request<IGitHubRepoResponse>(
+			'GET',
+			`/repos/${encodeURIComponent(owner)}/${encodeURIComponent(repo)}`,
+			'githubApi.getRepository'
+		);
+		return {
+			owner: data.owner.login,
+			name: data.name,
+			fullName: data.full_name,
+			defaultBranch: data.default_branch,
+			isPrivate: data.private,
+			description: data.description ?? '',
+		};
+	}
+}
diff --git a/src/vs/workbench/contrib/inlineChat/electron-browser/inlineChat.contribution.ts b/src/vs/sessions/contrib/github/browser/github.contribution.ts
similarity index 57%
rename from src/vs/workbench/contrib/inlineChat/electron-browser/inlineChat.contribution.ts
rename to src/vs/sessions/contrib/github/browser/github.contribution.ts
index 99549752c8ab5..af80df37852db 100644
--- a/src/vs/workbench/contrib/inlineChat/electron-browser/inlineChat.contribution.ts
+++ b/src/vs/sessions/contrib/github/browser/github.contribution.ts
@@ -3,9 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { registerAction2 } from '../../../../platform/actions/common/actions.js';
-import { HoldToSpeak } from './inlineChatActions.js';
+import { InstantiationType, registerSingleton } from '../../../../platform/instantiation/common/extensions.js';
+import { GitHubService, IGitHubService } from './githubService.js';
 
-// start and hold for voice
-
-registerAction2(HoldToSpeak);
+registerSingleton(IGitHubService, GitHubService, InstantiationType.Delayed);
diff --git a/src/vs/sessions/contrib/github/browser/githubApiClient.ts b/src/vs/sessions/contrib/github/browser/githubApiClient.ts
new file mode 100644
index 0000000000000..ba6e1f3fc5168
--- /dev/null
+++ b/src/vs/sessions/contrib/github/browser/githubApiClient.ts
@@ -0,0 +1,150 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
+import { IRequestService, asJson } from '../../../../platform/request/common/request.js';
+import { IAuthenticationService } from '../../../../workbench/services/authentication/common/authentication.js';
+
+const LOG_PREFIX = '[GitHubApiClient]';
+const GITHUB_API_BASE = 'https://api.github.com';
+const GITHUB_GRAPHQL_ENDPOINT = `${GITHUB_API_BASE}/graphql`;
+
+interface IGitHubGraphQLError {
+	readonly message: string;
+}
+
+interface IGitHubGraphQLResponse<T> {
+	readonly data?: T;
+	readonly errors?: readonly IGitHubGraphQLError[];
+}
+
+export class GitHubApiError extends Error {
+	constructor(
+		message: string,
+		readonly statusCode: number,
+		readonly rateLimitRemaining: number | undefined,
+	) {
+		super(message);
+		this.name = 'GitHubApiError';
+	}
+}
+
+/**
+ * Low-level GitHub REST API client. Handles authentication,
+ * request construction, and error classification.
+ *
+ * This class is stateless with respect to domain data — it only
+ * manages auth tokens and raw HTTP communication.
+ */
+export class GitHubApiClient extends Disposable {
+
+	constructor(
+		@IRequestService private readonly _requestService: IRequestService,
+		@IAuthenticationService private readonly _authenticationService: IAuthenticationService,
+		@ILogService private readonly _logService: ILogService,
+	) {
+		super();
+	}
+
+	async request<T>(method: string, path: string, callSite: string, body?: unknown): Promise<T> {
+		return this._request<T>(method, `${GITHUB_API_BASE}${path}`, path, 'application/vnd.github.v3+json', callSite, body);
+	}
+
+	async graphql<T>(query: string, callSite: string, variables?: Record<string, unknown>): Promise<T> {
+		const response = await this._request<IGitHubGraphQLResponse<T>>(
+			'POST',
+			GITHUB_GRAPHQL_ENDPOINT,
+			'/graphql',
+			'application/vnd.github+json',
+			callSite,
+			{ query, variables },
+		);
+
+		if (response.errors?.length) {
+			throw new GitHubApiError(
+				response.errors.map(error => error.message).join('; '),
+				200,
+				undefined,
+			);
+		}
+
+		if (!response.data) {
+			throw new GitHubApiError('GitHub GraphQL response did not include data', 200, undefined);
+		}
+
+		return response.data;
+	}
+
+	private async _request<T>(method: string, url: string, pathForLogging: string, accept: string, callSite: string, body?: unknown): Promise<T> {
+		const token = await this._getAuthToken();
+
+		this._logService.trace(`${LOG_PREFIX} ${method} ${pathForLogging}`);
+
+		const response = await this._requestService.request({
+			type: method,
+			url,
+			headers: {
+				'Authorization': `token ${token}`,
+				'Accept': accept,
+				'User-Agent': 'VSCode-Sessions-GitHub',
+				...(body !== undefined ? { 'Content-Type': 'application/json' } : {}),
+			},
+			data: body !== undefined ? JSON.stringify(body) : undefined,
+			callSite
+		}, CancellationToken.None);
+
+		const rateLimitRemaining = parseRateLimitHeader(response.res.headers?.['x-ratelimit-remaining']);
+		if (rateLimitRemaining !== undefined && rateLimitRemaining < 100) {
+			this._logService.warn(`${LOG_PREFIX} GitHub API rate limit low: ${rateLimitRemaining} remaining`);
+		}
+
+		const statusCode = response.res.statusCode ?? 0;
+		if (statusCode < 200 || statusCode >= 300) {
+			const errorBody = await asJson<{ message?: string }>(response).catch(() => undefined);
+			throw new GitHubApiError(
+				errorBody?.message ?? `GitHub API request failed: ${method} ${pathForLogging} (${statusCode})`,
+				statusCode,
+				rateLimitRemaining,
+			);
+		}
+
+		if (statusCode === 204) {
+			return undefined as unknown as T;
+		}
+
+		const data = await asJson<T>(response);
+		if (!data) {
+			throw new GitHubApiError(
+				`Failed to parse response for ${method} ${pathForLogging}`,
+				statusCode,
+				rateLimitRemaining,
+			);
+		}
+
+		return data;
+	}
+
+	private async _getAuthToken(): Promise<string> {
+		let sessions = await this._authenticationService.getSessions('github', [], { silent: true });
+		if (!sessions || sessions.length === 0) {
+			sessions = await this._authenticationService.getSessions('github', [], { createIfNone: true });
+		}
+		if (!sessions || sessions.length === 0) {
+			throw new Error('No GitHub authentication sessions available');
+		}
+		return sessions[0].accessToken ?? '';
+	}
+}
+
+function parseRateLimitHeader(value: string | string[] | undefined): number | undefined {
+	if (value === undefined) {
+		return undefined;
+	}
+	const str = Array.isArray(value) ? value[0] : value;
+	const parsed = parseInt(str, 10);
+	return isNaN(parsed) ? undefined : parsed;
+}
diff --git a/src/vs/sessions/contrib/github/browser/githubService.ts b/src/vs/sessions/contrib/github/browser/githubService.ts
new file mode 100644
index 0000000000000..ac6a5ab7de836
--- /dev/null
+++ b/src/vs/sessions/contrib/github/browser/githubService.ts
@@ -0,0 +1,100 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Disposable, DisposableMap } from '../../../../base/common/lifecycle.js';
+import { createDecorator, IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
+import { GitHubApiClient } from './githubApiClient.js';
+import { GitHubRepositoryFetcher } from './fetchers/githubRepositoryFetcher.js';
+import { GitHubPRFetcher } from './fetchers/githubPRFetcher.js';
+import { GitHubPRCIFetcher } from './fetchers/githubPRCIFetcher.js';
+import { GitHubRepositoryModel } from './models/githubRepositoryModel.js';
+import { GitHubPullRequestModel } from './models/githubPullRequestModel.js';
+import { GitHubPullRequestCIModel } from './models/githubPullRequestCIModel.js';
+
+export interface IGitHubService {
+	readonly _serviceBrand: undefined;
+
+	/**
+	 * Get or create a reactive model for a GitHub repository.
+	 * The model is cached by owner/repo key and disposed when the service is disposed.
+	 */
+	getRepository(owner: string, repo: string): GitHubRepositoryModel;
+
+	/**
+	 * Get or create a reactive model for a GitHub pull request.
+	 * The model is cached by owner/repo/prNumber key and disposed when the service is disposed.
+	 */
+	getPullRequest(owner: string, repo: string, prNumber: number): GitHubPullRequestModel;
+
+	/**
+	 * Get or create a reactive model for CI checks on a pull request head ref.
+	 * The model is cached by owner/repo/headRef key and disposed when the service is disposed.
+	 */
+	getPullRequestCI(owner: string, repo: string, headRef: string): GitHubPullRequestCIModel;
+}
+
+export const IGitHubService = createDecorator<IGitHubService>('sessionsGitHubService');
+
+const LOG_PREFIX = '[GitHubService]';
+
+export class GitHubService extends Disposable implements IGitHubService {
+
+	declare readonly _serviceBrand: undefined;
+
+	private readonly _apiClient: GitHubApiClient;
+	private readonly _repoFetcher: GitHubRepositoryFetcher;
+	private readonly _prFetcher: GitHubPRFetcher;
+	private readonly _ciFetcher: GitHubPRCIFetcher;
+
+	private readonly _repositories = this._register(new DisposableMap<string, GitHubRepositoryModel>());
+	private readonly _pullRequests = this._register(new DisposableMap<string, GitHubPullRequestModel>());
+	private readonly _ciModels = this._register(new DisposableMap<string, GitHubPullRequestCIModel>());
+
+	constructor(
+		@IInstantiationService instantiationService: IInstantiationService,
+		@ILogService private readonly _logService: ILogService,
+	) {
+		super();
+
+		this._apiClient = this._register(instantiationService.createInstance(GitHubApiClient));
+		this._repoFetcher = new GitHubRepositoryFetcher(this._apiClient);
+		this._prFetcher = new GitHubPRFetcher(this._apiClient);
+		this._ciFetcher = new GitHubPRCIFetcher(this._apiClient);
+	}
+
+	getRepository(owner: string, repo: string): GitHubRepositoryModel {
+		const key = `${owner}/${repo}`;
+		let model = this._repositories.get(key);
+		if (!model) {
+			this._logService.trace(`${LOG_PREFIX} Creating repository model for ${key}`);
+			model = new GitHubRepositoryModel(owner, repo, this._repoFetcher, this._logService);
+			this._repositories.set(key, model);
+		}
+		return model;
+	}
+
+	getPullRequest(owner: string, repo: string, prNumber: number): GitHubPullRequestModel {
+		const key = `${owner}/${repo}/${prNumber}`;
+		let model = this._pullRequests.get(key);
+		if (!model) {
+			this._logService.trace(`${LOG_PREFIX} Creating PR model for ${key}`);
+			model = new GitHubPullRequestModel(owner, repo, prNumber, this._prFetcher, this._logService);
+			this._pullRequests.set(key, model);
+		}
+		return model;
+	}
+
+	getPullRequestCI(owner: string, repo: string, headRef: string): GitHubPullRequestCIModel {
+		const key = `${owner}/${repo}/${headRef}`;
+		let model = this._ciModels.get(key);
+		if (!model) {
+			this._logService.trace(`${LOG_PREFIX} Creating CI model for ${key}`);
+			model = new GitHubPullRequestCIModel(owner, repo, headRef, this._ciFetcher, this._logService);
+			this._ciModels.set(key, model);
+		}
+		return model;
+	}
+}
diff --git a/src/vs/sessions/contrib/github/browser/models/githubPullRequestCIModel.ts b/src/vs/sessions/contrib/github/browser/models/githubPullRequestCIModel.ts
new file mode 100644
index 0000000000000..6a1dd490aaf88
--- /dev/null
+++ b/src/vs/sessions/contrib/github/browser/models/githubPullRequestCIModel.ts
@@ -0,0 +1,90 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { RunOnceScheduler } from '../../../../../base/common/async.js';
+import { Disposable } from '../../../../../base/common/lifecycle.js';
+import { IObservable, observableValue } from '../../../../../base/common/observable.js';
+import { ILogService } from '../../../../../platform/log/common/log.js';
+import { GitHubCIOverallStatus, IGitHubCICheck } from '../../common/types.js';
+import { computeOverallCIStatus, GitHubPRCIFetcher } from '../fetchers/githubPRCIFetcher.js';
+
+const LOG_PREFIX = '[GitHubPullRequestCIModel]';
+const DEFAULT_POLL_INTERVAL_MS = 60_000;
+
+/**
+ * Reactive model for CI check status on a pull request head ref.
+ * Wraps fetcher data in observables and supports periodic polling.
+ */
+export class GitHubPullRequestCIModel extends Disposable {
+
+	private readonly _checks = observableValue<readonly IGitHubCICheck[]>(this, []);
+	readonly checks: IObservable<readonly IGitHubCICheck[]> = this._checks;
+
+	private readonly _overallStatus = observableValue<GitHubCIOverallStatus>(this, GitHubCIOverallStatus.Neutral);
+	readonly overallStatus: IObservable<GitHubCIOverallStatus> = this._overallStatus;
+
+	private readonly _pollScheduler: RunOnceScheduler;
+	private _disposed = false;
+
+	constructor(
+		readonly owner: string,
+		readonly repo: string,
+		readonly headRef: string,
+		private readonly _fetcher: GitHubPRCIFetcher,
+		private readonly _logService: ILogService,
+	) {
+		super();
+
+		this._pollScheduler = this._register(new RunOnceScheduler(() => this._poll(), DEFAULT_POLL_INTERVAL_MS));
+	}
+
+	/**
+	 * Refresh all CI check data.
+	 */
+	async refresh(): Promise<void> {
+		try {
+			const checks = await this._fetcher.getCheckRuns(this.owner, this.repo, this.headRef);
+			this._checks.set(checks, undefined);
+			this._overallStatus.set(computeOverallCIStatus(checks), undefined);
+		} catch (err) {
+			this._logService.error(`${LOG_PREFIX} Failed to refresh CI checks for ${this.owner}/${this.repo}@${this.headRef}:`, err);
+		}
+	}
+
+	/**
+	 * Get annotations (structured logs) for a specific check run.
+	 */
+	async getCheckRunAnnotations(checkRunId: number): Promise<string> {
+		return this._fetcher.getCheckRunAnnotations(this.owner, this.repo, checkRunId);
+	}
+
+	/**
+	 * Start periodic polling. Each cycle refreshes CI check data.
+	 */
+	startPolling(intervalMs: number = DEFAULT_POLL_INTERVAL_MS): void {
+		this._pollScheduler.cancel();
+		this._pollScheduler.schedule(intervalMs);
+	}
+
+	/**
+	 * Stop periodic polling.
+	 */
+	stopPolling(): void {
+		this._pollScheduler.cancel();
+	}
+
+	private async _poll(): Promise<void> {
+		await this.refresh();
+		// Re-schedule if not disposed (RunOnceScheduler is one-shot)
+		if (!this._disposed) {
+			this._pollScheduler.schedule();
+		}
+	}
+
+	override dispose(): void {
+		this._disposed = true;
+		super.dispose();
+	}
+}
diff --git a/src/vs/sessions/contrib/github/browser/models/githubPullRequestModel.ts b/src/vs/sessions/contrib/github/browser/models/githubPullRequestModel.ts
new file mode 100644
index 0000000000000..8c5a667460c71
--- /dev/null
+++ b/src/vs/sessions/contrib/github/browser/models/githubPullRequestModel.ts
@@ -0,0 +1,142 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { RunOnceScheduler } from '../../../../../base/common/async.js';
+import { Disposable } from '../../../../../base/common/lifecycle.js';
+import { IObservable, observableValue } from '../../../../../base/common/observable.js';
+import { ILogService } from '../../../../../platform/log/common/log.js';
+import { IGitHubPRComment, IGitHubPRReviewThread, IGitHubPullRequest, IGitHubPullRequestMergeability } from '../../common/types.js';
+import { GitHubPRFetcher } from '../fetchers/githubPRFetcher.js';
+
+const LOG_PREFIX = '[GitHubPullRequestModel]';
+const DEFAULT_POLL_INTERVAL_MS = 30_000;
+
+/**
+ * Reactive model for a GitHub pull request. Wraps fetcher data in
+ * observables, supports on-demand refresh, and can poll periodically.
+ */
+export class GitHubPullRequestModel extends Disposable {
+
+	private readonly _pullRequest = observableValue<IGitHubPullRequest | undefined>(this, undefined);
+	readonly pullRequest: IObservable<IGitHubPullRequest | undefined> = this._pullRequest;
+
+	private readonly _mergeability = observableValue<IGitHubPullRequestMergeability | undefined>(this, undefined);
+	readonly mergeability: IObservable<IGitHubPullRequestMergeability | undefined> = this._mergeability;
+
+	private readonly _reviewThreads = observableValue<readonly IGitHubPRReviewThread[]>(this, []);
+	readonly reviewThreads: IObservable<readonly IGitHubPRReviewThread[]> = this._reviewThreads;
+
+	private readonly _pollScheduler: RunOnceScheduler;
+	private _disposed = false;
+
+	constructor(
+		readonly owner: string,
+		readonly repo: string,
+		readonly prNumber: number,
+		private readonly _fetcher: GitHubPRFetcher,
+		private readonly _logService: ILogService,
+	) {
+		super();
+
+		this._pollScheduler = this._register(new RunOnceScheduler(() => this._poll(), DEFAULT_POLL_INTERVAL_MS));
+	}
+
+	/**
+	 * Refresh all PR data: pull request info, mergeability, and review threads.
+	 */
+	async refresh(): Promise<void> {
+		await Promise.all([
+			this._refreshPullRequest(),
+			this._refreshMergeability(),
+			this._refreshThreads(),
+		]);
+	}
+
+	/**
+	 * Refresh only the review threads.
+	 */
+	async refreshThreads(): Promise<void> {
+		await this._refreshThreads();
+	}
+
+	/**
+	 * Post a reply to an existing review thread and refresh threads.
+	 */
+	async postReviewComment(body: string, inReplyTo: number): Promise<IGitHubPRComment> {
+		const comment = await this._fetcher.postReviewComment(this.owner, this.repo, this.prNumber, body, inReplyTo);
+		await this._refreshThreads();
+		return comment;
+	}
+
+	/**
+	 * Post a top-level issue comment on the PR.
+	 */
+	async postIssueComment(body: string): Promise<IGitHubPRComment> {
+		return this._fetcher.postIssueComment(this.owner, this.repo, this.prNumber, body);
+	}
+
+	/**
+	 * Resolve a review thread and refresh the thread list.
+	 */
+	async resolveThread(threadId: string): Promise<void> {
+		await this._fetcher.resolveThread(this.owner, this.repo, threadId);
+		await this._refreshThreads();
+	}
+
+	/**
+	 * Start periodic polling. Each cycle refreshes all PR data.
+	 */
+	startPolling(intervalMs: number = DEFAULT_POLL_INTERVAL_MS): void {
+		this._pollScheduler.cancel();
+		this._pollScheduler.schedule(intervalMs);
+	}
+
+	/**
+	 * Stop periodic polling.
+	 */
+	stopPolling(): void {
+		this._pollScheduler.cancel();
+	}
+
+	private async _poll(): Promise<void> {
+		await this.refresh();
+		// Re-schedule for next poll cycle (RunOnceScheduler is one-shot)
+		if (!this._disposed) {
+			this._pollScheduler.schedule();
+		}
+	}
+
+	override dispose(): void {
+		this._disposed = true;
+		super.dispose();
+	}
+
+	private async _refreshPullRequest(): Promise<void> {
+		try {
+			const data = await this._fetcher.getPullRequest(this.owner, this.repo, this.prNumber);
+			this._pullRequest.set(data, undefined);
+		} catch (err) {
+			this._logService.error(`${LOG_PREFIX} Failed to refresh PR #${this.prNumber}:`, err);
+		}
+	}
+
+	private async _refreshMergeability(): Promise<void> {
+		try {
+			const data = await this._fetcher.getMergeability(this.owner, this.repo, this.prNumber);
+			this._mergeability.set(data, undefined);
+		} catch (err) {
+			this._logService.error(`${LOG_PREFIX} Failed to refresh mergeability for PR #${this.prNumber}:`, err);
+		}
+	}
+
+	private async _refreshThreads(): Promise<void> {
+		try {
+			const data = await this._fetcher.getReviewThreads(this.owner, this.repo, this.prNumber);
+			this._reviewThreads.set(data, undefined);
+		} catch (err) {
+			this._logService.error(`${LOG_PREFIX} Failed to refresh threads for PR #${this.prNumber}:`, err);
+		}
+	}
+}
diff --git a/src/vs/sessions/contrib/github/browser/models/githubRepositoryModel.ts b/src/vs/sessions/contrib/github/browser/models/githubRepositoryModel.ts
new file mode 100644
index 0000000000000..9e2c368a329ab
--- /dev/null
+++ b/src/vs/sessions/contrib/github/browser/models/githubRepositoryModel.ts
@@ -0,0 +1,40 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Disposable } from '../../../../../base/common/lifecycle.js';
+import { IObservable, observableValue } from '../../../../../base/common/observable.js';
+import { ILogService } from '../../../../../platform/log/common/log.js';
+import { IGitHubRepository } from '../../common/types.js';
+import { GitHubRepositoryFetcher } from '../fetchers/githubRepositoryFetcher.js';
+
+const LOG_PREFIX = '[GitHubRepositoryModel]';
+
+/**
+ * Reactive model for a GitHub repository. Wraps fetcher data
+ * in observables and supports on-demand refresh.
+ */
+export class GitHubRepositoryModel extends Disposable {
+
+	private readonly _repository = observableValue<IGitHubRepository | undefined>(this, undefined);
+	readonly repository: IObservable<IGitHubRepository | undefined> = this._repository;
+
+	constructor(
+		readonly owner: string,
+		readonly repo: string,
+		private readonly _fetcher: GitHubRepositoryFetcher,
+		private readonly _logService: ILogService,
+	) {
+		super();
+	}
+
+	async refresh(): Promise<void> {
+		try {
+			const data = await this._fetcher.getRepository(this.owner, this.repo);
+			this._repository.set(data, undefined);
+		} catch (err) {
+			this._logService.error(`${LOG_PREFIX} Failed to refresh repository ${this.owner}/${this.repo}:`, err);
+		}
+	}
+}
diff --git a/src/vs/sessions/contrib/github/common/types.ts b/src/vs/sessions/contrib/github/common/types.ts
new file mode 100644
index 0000000000000..bc447c21c909b
--- /dev/null
+++ b/src/vs/sessions/contrib/github/common/types.ts
@@ -0,0 +1,147 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+//#region Session Context
+
+/**
+ * GitHub context derived from an active session, providing
+ * the owner/repo and optionally the PR number.
+ */
+export interface IGitHubSessionContext {
+	readonly owner: string;
+	readonly repo: string;
+	readonly prNumber: number | undefined;
+}
+
+//#endregion
+
+//#region Repository
+
+export interface IGitHubRepository {
+	readonly owner: string;
+	readonly name: string;
+	readonly fullName: string;
+	readonly defaultBranch: string;
+	readonly isPrivate: boolean;
+	readonly description: string;
+}
+
+//#endregion
+
+//#region Pull Request
+
+export const enum GitHubPullRequestState {
+	Open = 'open',
+	Closed = 'closed',
+	Merged = 'merged',
+}
+
+export interface IGitHubUser {
+	readonly login: string;
+	readonly avatarUrl: string;
+}
+
+export interface IGitHubPullRequest {
+	readonly number: number;
+	readonly title: string;
+	readonly body: string;
+	readonly state: GitHubPullRequestState;
+	readonly author: IGitHubUser;
+	readonly headRef: string;
+	readonly baseRef: string;
+	readonly isDraft: boolean;
+	readonly createdAt: string;
+	readonly updatedAt: string;
+	readonly mergedAt: string | undefined;
+	readonly mergeable: boolean | undefined;
+	readonly mergeableState: string;
+}
+
+export const enum MergeBlockerKind {
+	ChangesRequested = 'changesRequested',
+	CIFailed = 'ciFailed',
+	ApprovalNeeded = 'approvalNeeded',
+	Conflicts = 'conflicts',
+	Draft = 'draft',
+	Unknown = 'unknown',
+}
+
+export interface IMergeBlocker {
+	readonly kind: MergeBlockerKind;
+	readonly description: string;
+}
+
+export interface IGitHubPullRequestMergeability {
+	readonly canMerge: boolean;
+	readonly blockers: readonly IMergeBlocker[];
+}
+
+//#endregion
+
+//#region Review Comments & Threads
+
+export interface IGitHubPRComment {
+	readonly id: number;
+	readonly body: string;
+	readonly author: IGitHubUser;
+	readonly createdAt: string;
+	readonly updatedAt: string;
+	/** File path the comment is attached to (undefined for issue-level comments). */
+	readonly path: string | undefined;
+	/** Line number in the diff the comment is attached to. */
+	readonly line: number | undefined;
+	/** The id of the thread this comment belongs to. */
+	readonly threadId: string;
+	/** Whether this is a reply to another comment in the thread. */
+	readonly inReplyToId: number | undefined;
+}
+
+export interface IGitHubPRReviewThread {
+	readonly id: string;
+	readonly isResolved: boolean;
+	readonly path: string;
+	readonly line: number | undefined;
+	readonly comments: readonly IGitHubPRComment[];
+}
+
+//#endregion
+
+//#region CI Checks
+
+export const enum GitHubCheckStatus {
+	Queued = 'queued',
+	InProgress = 'in_progress',
+	Completed = 'completed',
+}
+
+export const enum GitHubCheckConclusion {
+	Success = 'success',
+	Failure = 'failure',
+	Neutral = 'neutral',
+	Cancelled = 'cancelled',
+	Skipped = 'skipped',
+	TimedOut = 'timed_out',
+	ActionRequired = 'action_required',
+	Stale = 'stale',
+}
+
+export interface IGitHubCICheck {
+	readonly id: number;
+	readonly name: string;
+	readonly status: GitHubCheckStatus;
+	readonly conclusion: GitHubCheckConclusion | undefined;
+	readonly startedAt: string | undefined;
+	readonly completedAt: string | undefined;
+	readonly detailsUrl: string | undefined;
+}
+
+export const enum GitHubCIOverallStatus {
+	Pending = 'pending',
+	Success = 'success',
+	Failure = 'failure',
+	Neutral = 'neutral',
+}
+
+//#endregion
diff --git a/src/vs/sessions/contrib/github/test/browser/githubFetchers.test.ts b/src/vs/sessions/contrib/github/test/browser/githubFetchers.test.ts
new file mode 100644
index 0000000000000..db4a8b5d88323
--- /dev/null
+++ b/src/vs/sessions/contrib/github/test/browser/githubFetchers.test.ts
@@ -0,0 +1,446 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { GitHubPRFetcher } from '../../browser/fetchers/githubPRFetcher.js';
+import { GitHubPRCIFetcher, computeOverallCIStatus } from '../../browser/fetchers/githubPRCIFetcher.js';
+import { GitHubRepositoryFetcher } from '../../browser/fetchers/githubRepositoryFetcher.js';
+import { GitHubApiClient, GitHubApiError } from '../../browser/githubApiClient.js';
+import { GitHubCheckConclusion, GitHubCheckStatus, GitHubCIOverallStatus, GitHubPullRequestState, MergeBlockerKind } from '../../common/types.js';
+
+class MockApiClient {
+
+	private _nextResponse: unknown;
+	private _nextError: Error | undefined;
+	readonly requestCalls: { method: string; path: string; body?: unknown }[] = [];
+	readonly graphqlCalls: { query: string; variables?: Record<string, unknown> }[] = [];
+
+	setNextResponse(data: unknown): void {
+		this._nextResponse = data;
+		this._nextError = undefined;
+	}
+
+	setNextError(error: Error): void {
+		this._nextError = error;
+		this._nextResponse = undefined;
+	}
+
+	async request<T>(_method: string, _path: string, _callSite: string, _body?: unknown): Promise<T> {
+		this.requestCalls.push({ method: _method, path: _path, body: _body });
+		if (this._nextError) {
+			throw this._nextError;
+		}
+		return this._nextResponse as T;
+	}
+
+	async graphql<T>(query: string, _callSite: string, variables?: Record<string, unknown>): Promise<T> {
+		this.graphqlCalls.push({ query, variables });
+		if (this._nextError) {
+			throw this._nextError;
+		}
+		return this._nextResponse as T;
+	}
+}
+
+suite('GitHubRepositoryFetcher', () => {
+
+	const store = new DisposableStore();
+	let mockApi: MockApiClient;
+	let fetcher: GitHubRepositoryFetcher;
+
+	setup(() => {
+		mockApi = new MockApiClient();
+		fetcher = new GitHubRepositoryFetcher(mockApi as unknown as GitHubApiClient);
+	});
+
+	teardown(() => store.clear());
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('getRepository returns mapped data', async () => {
+		mockApi.setNextResponse({
+			name: 'vscode',
+			full_name: 'microsoft/vscode',
+			owner: { login: 'microsoft' },
+			default_branch: 'main',
+			private: false,
+			description: 'Visual Studio Code',
+		});
+
+		const repo = await fetcher.getRepository('microsoft', 'vscode');
+		assert.deepStrictEqual(repo, {
+			owner: 'microsoft',
+			name: 'vscode',
+			fullName: 'microsoft/vscode',
+			defaultBranch: 'main',
+			isPrivate: false,
+			description: 'Visual Studio Code',
+		});
+		assert.strictEqual(mockApi.requestCalls[0].path, '/repos/microsoft/vscode');
+	});
+
+	test('getRepository handles null description', async () => {
+		mockApi.setNextResponse({
+			name: 'test',
+			full_name: 'owner/test',
+			owner: { login: 'owner' },
+			default_branch: 'main',
+			private: true,
+			description: null,
+		});
+
+		const repo = await fetcher.getRepository('owner', 'test');
+		assert.strictEqual(repo.description, '');
+	});
+
+	test('getRepository propagates API errors', async () => {
+		mockApi.setNextError(new GitHubApiError('Not found', 404, undefined));
+		await assert.rejects(
+			() => fetcher.getRepository('owner', 'nonexistent'),
+			(err: Error) => err instanceof GitHubApiError && (err as GitHubApiError).statusCode === 404,
+		);
+	});
+});
+
+suite('GitHubPRFetcher', () => {
+
+	const store = new DisposableStore();
+	let mockApi: MockApiClient;
+	let fetcher: GitHubPRFetcher;
+
+	setup(() => {
+		mockApi = new MockApiClient();
+		fetcher = new GitHubPRFetcher(mockApi as unknown as GitHubApiClient);
+	});
+
+	teardown(() => store.clear());
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('getPullRequest maps open PR', async () => {
+		mockApi.setNextResponse(makePRResponse({ state: 'open', merged: false, draft: false }));
+
+		const pr = await fetcher.getPullRequest('owner', 'repo', 1);
+		assert.strictEqual(pr.state, GitHubPullRequestState.Open);
+		assert.strictEqual(pr.isDraft, false);
+		assert.strictEqual(pr.number, 1);
+		assert.strictEqual(pr.title, 'Test PR');
+	});
+
+	test('getPullRequest maps merged PR', async () => {
+		mockApi.setNextResponse(makePRResponse({ state: 'closed', merged: true, draft: false }));
+
+		const pr = await fetcher.getPullRequest('owner', 'repo', 1);
+		assert.strictEqual(pr.state, GitHubPullRequestState.Merged);
+		assert.ok(pr.mergedAt);
+	});
+
+	test('getPullRequest maps closed PR', async () => {
+		mockApi.setNextResponse(makePRResponse({ state: 'closed', merged: false, draft: false }));
+
+		const pr = await fetcher.getPullRequest('owner', 'repo', 1);
+		assert.strictEqual(pr.state, GitHubPullRequestState.Closed);
+	});
+
+	test('getReviewThreads returns GraphQL thread metadata', async () => {
+		mockApi.setNextResponse(makeGraphQLReviewThreadsResponse([
+			makeGraphQLReviewThread({
+				id: 'thread-a',
+				path: 'src/a.ts',
+				line: 10,
+				isResolved: false,
+				comments: [
+					makeGraphQLReviewComment({ databaseId: 100, path: 'src/a.ts', line: 10 }),
+					makeGraphQLReviewComment({ databaseId: 101, path: 'src/a.ts', line: 10, replyToDatabaseId: 100 }),
+				],
+			}),
+			makeGraphQLReviewThread({
+				id: 'thread-b',
+				path: 'src/b.ts',
+				line: 20,
+				isResolved: true,
+				comments: [makeGraphQLReviewComment({ databaseId: 200, path: 'src/b.ts', line: 20 })],
+			}),
+		]));
+
+		const threads = await fetcher.getReviewThreads('owner', 'repo', 1);
+		assert.strictEqual(threads.length, 2);
+
+		const thread1 = threads.find(t => t.id === 'thread-a')!;
+		assert.ok(thread1);
+		assert.strictEqual(thread1.comments.length, 2);
+		assert.strictEqual(thread1.path, 'src/a.ts');
+		assert.strictEqual(thread1.line, 10);
+		assert.strictEqual(thread1.comments[0].threadId, 'thread-a');
+
+		const thread2 = threads.find(t => t.id === 'thread-b')!;
+		assert.ok(thread2);
+		assert.strictEqual(thread2.comments.length, 1);
+		assert.strictEqual(thread2.path, 'src/b.ts');
+		assert.strictEqual(thread2.isResolved, true);
+	});
+
+	test('resolveThread uses GraphQL mutation', async () => {
+		mockApi.setNextResponse({
+			resolveReviewThread: {
+				thread: {
+					isResolved: true,
+				},
+			},
+		});
+
+		await fetcher.resolveThread('owner', 'repo', 'thread-a');
+		assert.strictEqual(mockApi.graphqlCalls.length, 1);
+		assert.deepStrictEqual(mockApi.graphqlCalls[0].variables, { threadId: 'thread-a' });
+	});
+
+	test('getMergeability detects draft blocker', async () => {
+		// getMergeability makes two requests (PR then reviews)
+		// Use a counter to return different responses
+		let callCount = 0;
+		const originalRequest = mockApi.request.bind(mockApi);
+		mockApi.request = async function <T>(_method: string, _path: string, _body?: unknown): Promise<T> {
+			if (callCount++ === 0) {
+				return makePRResponse({ state: 'open', merged: false, draft: true, mergeable: true, mergeable_state: 'clean' }) as T;
+			}
+			return [] as unknown as T;
+		};
+
+		const result = await fetcher.getMergeability('owner', 'repo', 1);
+		assert.strictEqual(result.canMerge, false);
+		assert.ok(result.blockers.some(b => b.kind === MergeBlockerKind.Draft));
+
+		// Restore
+		mockApi.request = originalRequest;
+	});
+
+	test('getMergeability detects conflicts blocker', async () => {
+		let callCount = 0;
+		const originalRequest = mockApi.request.bind(mockApi);
+		mockApi.request = async function <T>(): Promise<T> {
+			if (callCount++ === 0) {
+				return makePRResponse({ state: 'open', merged: false, draft: false, mergeable: false, mergeable_state: 'dirty' }) as T;
+			}
+			return [] as unknown as T;
+		};
+
+		const result = await fetcher.getMergeability('owner', 'repo', 1);
+		assert.strictEqual(result.canMerge, false);
+		assert.ok(result.blockers.some(b => b.kind === MergeBlockerKind.Conflicts));
+
+		mockApi.request = originalRequest;
+	});
+
+	test('getMergeability detects changes requested blocker', async () => {
+		let callCount = 0;
+		const originalRequest = mockApi.request.bind(mockApi);
+		mockApi.request = async function <T>(): Promise<T> {
+			if (callCount++ === 0) {
+				return makePRResponse({ state: 'open', merged: false, draft: false, mergeable: true, mergeable_state: 'clean' }) as T;
+			}
+			return [
+				{ id: 1, user: { login: 'reviewer', avatar_url: '' }, state: 'CHANGES_REQUESTED', submitted_at: '2024-01-01T00:00:00Z' },
+			] as unknown as T;
+		};
+
+		const result = await fetcher.getMergeability('owner', 'repo', 1);
+		assert.strictEqual(result.canMerge, false);
+		assert.ok(result.blockers.some(b => b.kind === MergeBlockerKind.ChangesRequested));
+
+		mockApi.request = originalRequest;
+	});
+});
+
+suite('GitHubPRCIFetcher', () => {
+
+	const store = new DisposableStore();
+	let mockApi: MockApiClient;
+	let fetcher: GitHubPRCIFetcher;
+
+	setup(() => {
+		mockApi = new MockApiClient();
+		fetcher = new GitHubPRCIFetcher(mockApi as unknown as GitHubApiClient);
+	});
+
+	teardown(() => store.clear());
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('getCheckRuns maps check runs', async () => {
+		mockApi.setNextResponse({
+			total_count: 2,
+			check_runs: [
+				{ id: 1, name: 'build', status: 'completed', conclusion: 'success', started_at: '2024-01-01T00:00:00Z', completed_at: '2024-01-01T00:10:00Z', details_url: 'https://example.com/1' },
+				{ id: 2, name: 'test', status: 'in_progress', conclusion: null, started_at: '2024-01-01T00:00:00Z', completed_at: null, details_url: null },
+			],
+		});
+
+		const checks = await fetcher.getCheckRuns('owner', 'repo', 'abc123');
+		assert.strictEqual(checks.length, 2);
+		assert.deepStrictEqual(checks[0], {
+			id: 1,
+			name: 'build',
+			status: GitHubCheckStatus.Completed,
+			conclusion: GitHubCheckConclusion.Success,
+			startedAt: '2024-01-01T00:00:00Z',
+			completedAt: '2024-01-01T00:10:00Z',
+			detailsUrl: 'https://example.com/1',
+		});
+		assert.strictEqual(checks[1].conclusion, undefined);
+	});
+
+	test('getCheckRunAnnotations returns formatted annotations', async () => {
+		mockApi.setNextResponse([
+			{ path: 'src/a.ts', start_line: 10, end_line: 10, annotation_level: 'failure', message: 'type error', title: 'TS2345' },
+			{ path: 'src/b.ts', start_line: 5, end_line: 8, annotation_level: 'warning', message: 'unused var', title: null },
+		]);
+
+		const result = await fetcher.getCheckRunAnnotations('owner', 'repo', 1);
+		assert.ok(result.includes('[failure] src/a.ts:10'));
+		assert.ok(result.includes('(TS2345)'));
+		assert.ok(result.includes('[warning] src/b.ts:5-8'));
+	});
+});
+
+suite('computeOverallCIStatus', () => {
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('returns neutral for empty checks', () => {
+		assert.strictEqual(computeOverallCIStatus([]), GitHubCIOverallStatus.Neutral);
+	});
+
+	test('returns success when all completed successfully', () => {
+		const checks = [
+			makeCheck({ status: GitHubCheckStatus.Completed, conclusion: GitHubCheckConclusion.Success }),
+			makeCheck({ status: GitHubCheckStatus.Completed, conclusion: GitHubCheckConclusion.Neutral }),
+		];
+		assert.strictEqual(computeOverallCIStatus(checks), GitHubCIOverallStatus.Success);
+	});
+
+	test('returns failure when any check failed', () => {
+		const checks = [
+			makeCheck({ status: GitHubCheckStatus.Completed, conclusion: GitHubCheckConclusion.Success }),
+			makeCheck({ status: GitHubCheckStatus.Completed, conclusion: GitHubCheckConclusion.Failure }),
+		];
+		assert.strictEqual(computeOverallCIStatus(checks), GitHubCIOverallStatus.Failure);
+	});
+
+	test('returns pending when any check is in progress', () => {
+		const checks = [
+			makeCheck({ status: GitHubCheckStatus.Completed, conclusion: GitHubCheckConclusion.Success }),
+			makeCheck({ status: GitHubCheckStatus.InProgress, conclusion: undefined }),
+		];
+		assert.strictEqual(computeOverallCIStatus(checks), GitHubCIOverallStatus.Pending);
+	});
+
+	test('failure takes precedence over pending', () => {
+		const checks = [
+			makeCheck({ status: GitHubCheckStatus.Completed, conclusion: GitHubCheckConclusion.Failure }),
+			makeCheck({ status: GitHubCheckStatus.InProgress, conclusion: undefined }),
+		];
+		assert.strictEqual(computeOverallCIStatus(checks), GitHubCIOverallStatus.Failure);
+	});
+});
+
+
+//#region Test Helpers
+
+function makePRResponse(overrides: {
+	state: 'open' | 'closed';
+	merged: boolean;
+	draft: boolean;
+	mergeable?: boolean | null;
+	mergeable_state?: string;
+}): unknown {
+	return {
+		number: 1,
+		title: 'Test PR',
+		body: 'Test body',
+		state: overrides.state,
+		draft: overrides.draft,
+		user: { login: 'author', avatar_url: 'https://example.com/avatar' },
+		head: { ref: 'feature-branch' },
+		base: { ref: 'main' },
+		created_at: '2024-01-01T00:00:00Z',
+		updated_at: '2024-01-02T00:00:00Z',
+		merged_at: overrides.merged ? '2024-01-02T00:00:00Z' : null,
+		mergeable: overrides.mergeable ?? true,
+		mergeable_state: overrides.mergeable_state ?? 'clean',
+		merged: overrides.merged,
+	};
+}
+
+function makeGraphQLReviewThreadsResponse(threads: readonly ReturnType<typeof makeGraphQLReviewThread>[]): unknown {
+	return {
+		repository: {
+			pullRequest: {
+				reviewThreads: {
+					nodes: threads,
+				},
+			},
+		},
+	};
+}
+
+function makeGraphQLReviewThread(overrides: Partial<{
+	id: string;
+	isResolved: boolean;
+	path: string;
+	line: number;
+	comments: readonly ReturnType<typeof makeGraphQLReviewComment>[];
+}> = {}): unknown {
+	return {
+		id: overrides.id ?? 'thread-1',
+		isResolved: overrides.isResolved ?? false,
+		path: overrides.path ?? 'src/a.ts',
+		line: overrides.line ?? 10,
+		comments: {
+			nodes: overrides.comments ?? [makeGraphQLReviewComment()],
+		},
+	};
+}
+
+function makeGraphQLReviewComment(overrides: Partial<{
+	databaseId: number;
+	body: string;
+	path: string;
+	line: number;
+	replyToDatabaseId: number;
+}> = {}): unknown {
+	return {
+		databaseId: overrides.databaseId ?? 100,
+		body: overrides.body ?? 'Test comment',
+		createdAt: '2024-01-01T00:00:00Z',
+		updatedAt: '2024-01-01T00:00:00Z',
+		path: overrides.path ?? 'src/a.ts',
+		line: overrides.line ?? 10,
+		originalLine: overrides.line ?? 10,
+		replyTo: overrides.replyToDatabaseId !== undefined ? { databaseId: overrides.replyToDatabaseId } : null,
+		author: {
+			login: 'reviewer',
+			avatarUrl: 'https://example.com/avatar',
+		},
+	};
+}
+
+function makeCheck(overrides: {
+	status: GitHubCheckStatus;
+	conclusion: GitHubCheckConclusion | undefined;
+}): { id: number; name: string; status: GitHubCheckStatus; conclusion: GitHubCheckConclusion | undefined; startedAt: string | undefined; completedAt: string | undefined; detailsUrl: string | undefined } {
+	return {
+		id: 1,
+		name: 'test-check',
+		status: overrides.status,
+		conclusion: overrides.conclusion,
+		startedAt: undefined,
+		completedAt: undefined,
+		detailsUrl: undefined,
+	};
+}
+
+//#endregion
diff --git a/src/vs/sessions/contrib/github/test/browser/githubModels.test.ts b/src/vs/sessions/contrib/github/test/browser/githubModels.test.ts
new file mode 100644
index 0000000000000..24ce18ead0b13
--- /dev/null
+++ b/src/vs/sessions/contrib/github/test/browser/githubModels.test.ts
@@ -0,0 +1,279 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { NullLogService } from '../../../../../platform/log/common/log.js';
+import { GitHubPullRequestModel } from '../../browser/models/githubPullRequestModel.js';
+import { GitHubPullRequestCIModel } from '../../browser/models/githubPullRequestCIModel.js';
+import { GitHubRepositoryModel } from '../../browser/models/githubRepositoryModel.js';
+import { GitHubPRFetcher } from '../../browser/fetchers/githubPRFetcher.js';
+import { GitHubPRCIFetcher } from '../../browser/fetchers/githubPRCIFetcher.js';
+import { GitHubRepositoryFetcher } from '../../browser/fetchers/githubRepositoryFetcher.js';
+import { GitHubCIOverallStatus, GitHubCheckConclusion, GitHubCheckStatus, GitHubPullRequestState, IGitHubCICheck, IGitHubPRComment, IGitHubPRReviewThread, IGitHubPullRequest, IGitHubPullRequestMergeability, IGitHubRepository } from '../../common/types.js';
+
+//#region Mock Fetchers
+
+class MockRepositoryFetcher {
+	nextResult: IGitHubRepository | undefined;
+
+	async getRepository(_owner: string, _repo: string): Promise<IGitHubRepository> {
+		if (!this.nextResult) {
+			throw new Error('No mock result');
+		}
+		return this.nextResult;
+	}
+}
+
+class MockPRFetcher {
+	nextPR: IGitHubPullRequest | undefined;
+	nextMergeability: IGitHubPullRequestMergeability | undefined;
+	nextThreads: IGitHubPRReviewThread[] = [];
+	postReviewCommentCalls: { body: string; inReplyTo: number }[] = [];
+	postIssueCommentCalls: { body: string }[] = [];
+
+	async getPullRequest(_owner: string, _repo: string, _prNumber: number): Promise<IGitHubPullRequest> {
+		if (!this.nextPR) {
+			throw new Error('No mock PR');
+		}
+		return this.nextPR;
+	}
+
+	async getMergeability(_owner: string, _repo: string, _prNumber: number): Promise<IGitHubPullRequestMergeability> {
+		if (!this.nextMergeability) {
+			throw new Error('No mock mergeability');
+		}
+		return this.nextMergeability;
+	}
+
+	async getReviewThreads(_owner: string, _repo: string, _prNumber: number): Promise<IGitHubPRReviewThread[]> {
+		return this.nextThreads;
+	}
+
+	async postReviewComment(_owner: string, _repo: string, _prNumber: number, body: string, inReplyTo: number): Promise<IGitHubPRComment> {
+		this.postReviewCommentCalls.push({ body, inReplyTo });
+		return makeComment(999, body);
+	}
+
+	async postIssueComment(_owner: string, _repo: string, _prNumber: number, body: string): Promise<IGitHubPRComment> {
+		this.postIssueCommentCalls.push({ body });
+		return makeComment(998, body);
+	}
+
+	async resolveThread(): Promise<void> {
+		throw new Error('Not implemented');
+	}
+}
+
+class MockCIFetcher {
+	nextChecks: IGitHubCICheck[] = [];
+
+	async getCheckRuns(_owner: string, _repo: string, _ref: string): Promise<IGitHubCICheck[]> {
+		return this.nextChecks;
+	}
+
+	async getCheckRunAnnotations(_owner: string, _repo: string, _checkRunId: number): Promise<string> {
+		return 'mock annotations';
+	}
+}
+
+//#endregion
+
+suite('GitHubRepositoryModel', () => {
+
+	const store = new DisposableStore();
+	let mockFetcher: MockRepositoryFetcher;
+	const logService = new NullLogService();
+
+	setup(() => {
+		mockFetcher = new MockRepositoryFetcher();
+	});
+
+	teardown(() => store.clear());
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('initial state is undefined', () => {
+		const model = store.add(new GitHubRepositoryModel('owner', 'repo', mockFetcher as unknown as GitHubRepositoryFetcher, logService));
+		assert.strictEqual(model.repository.get(), undefined);
+	});
+
+	test('refresh populates repository observable', async () => {
+		const model = store.add(new GitHubRepositoryModel('owner', 'repo', mockFetcher as unknown as GitHubRepositoryFetcher, logService));
+		mockFetcher.nextResult = {
+			owner: 'owner',
+			name: 'repo',
+			fullName: 'owner/repo',
+			defaultBranch: 'main',
+			isPrivate: false,
+			description: 'test',
+		};
+
+		await model.refresh();
+		assert.deepStrictEqual(model.repository.get(), mockFetcher.nextResult);
+	});
+
+	test('refresh handles errors gracefully', async () => {
+		const model = store.add(new GitHubRepositoryModel('owner', 'repo', mockFetcher as unknown as GitHubRepositoryFetcher, logService));
+		// No nextResult set, will throw
+		await model.refresh();
+		assert.strictEqual(model.repository.get(), undefined);
+	});
+});
+
+suite('GitHubPullRequestModel', () => {
+
+	const store = new DisposableStore();
+	let mockFetcher: MockPRFetcher;
+	const logService = new NullLogService();
+
+	setup(() => {
+		mockFetcher = new MockPRFetcher();
+	});
+
+	teardown(() => store.clear());
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('initial state has empty observables', () => {
+		const model = store.add(new GitHubPullRequestModel('owner', 'repo', 1, mockFetcher as unknown as GitHubPRFetcher, logService));
+		assert.strictEqual(model.pullRequest.get(), undefined);
+		assert.strictEqual(model.mergeability.get(), undefined);
+		assert.deepStrictEqual(model.reviewThreads.get(), []);
+	});
+
+	test('refresh populates all observables', async () => {
+		const model = store.add(new GitHubPullRequestModel('owner', 'repo', 1, mockFetcher as unknown as GitHubPRFetcher, logService));
+		mockFetcher.nextPR = makePR();
+		mockFetcher.nextMergeability = { canMerge: true, blockers: [] };
+		mockFetcher.nextThreads = [makeThread('thread-100', 'src/a.ts')];
+
+		await model.refresh();
+		assert.strictEqual(model.pullRequest.get()?.number, 1);
+		assert.strictEqual(model.mergeability.get()?.canMerge, true);
+		assert.strictEqual(model.reviewThreads.get().length, 1);
+	});
+
+	test('refreshThreads only updates threads', async () => {
+		const model = store.add(new GitHubPullRequestModel('owner', 'repo', 1, mockFetcher as unknown as GitHubPRFetcher, logService));
+		mockFetcher.nextThreads = [makeThread('thread-100', 'src/a.ts'), makeThread('thread-200', 'src/b.ts')];
+
+		await model.refreshThreads();
+		assert.strictEqual(model.pullRequest.get(), undefined); // not refreshed
+		assert.strictEqual(model.reviewThreads.get().length, 2);
+	});
+
+	test('postReviewComment calls fetcher and refreshes threads', async () => {
+		const model = store.add(new GitHubPullRequestModel('owner', 'repo', 1, mockFetcher as unknown as GitHubPRFetcher, logService));
+		mockFetcher.nextThreads = [];
+
+		const comment = await model.postReviewComment('LGTM', 100);
+		assert.strictEqual(comment.body, 'LGTM');
+		assert.strictEqual(mockFetcher.postReviewCommentCalls.length, 1);
+		assert.strictEqual(mockFetcher.postReviewCommentCalls[0].body, 'LGTM');
+	});
+
+	test('postIssueComment calls fetcher', async () => {
+		const model = store.add(new GitHubPullRequestModel('owner', 'repo', 1, mockFetcher as unknown as GitHubPRFetcher, logService));
+
+		const comment = await model.postIssueComment('Great work!');
+		assert.strictEqual(comment.body, 'Great work!');
+		assert.strictEqual(mockFetcher.postIssueCommentCalls.length, 1);
+	});
+
+	test('polling can be started and stopped', () => {
+		const model = store.add(new GitHubPullRequestModel('owner', 'repo', 1, mockFetcher as unknown as GitHubPRFetcher, logService));
+		// Just ensure no errors; actual polling behavior is timer-based
+		model.startPolling(60_000);
+		model.stopPolling();
+	});
+});
+
+suite('GitHubPullRequestCIModel', () => {
+
+	const store = new DisposableStore();
+	let mockFetcher: MockCIFetcher;
+	const logService = new NullLogService();
+
+	setup(() => {
+		mockFetcher = new MockCIFetcher();
+	});
+
+	teardown(() => store.clear());
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('initial state is empty', () => {
+		const model = store.add(new GitHubPullRequestCIModel('owner', 'repo', 'abc', mockFetcher as unknown as GitHubPRCIFetcher, logService));
+		assert.deepStrictEqual(model.checks.get(), []);
+		assert.strictEqual(model.overallStatus.get(), GitHubCIOverallStatus.Neutral);
+	});
+
+	test('refresh populates checks and computes overall status', async () => {
+		const model = store.add(new GitHubPullRequestCIModel('owner', 'repo', 'abc', mockFetcher as unknown as GitHubPRCIFetcher, logService));
+		mockFetcher.nextChecks = [
+			{ id: 1, name: 'build', status: GitHubCheckStatus.Completed, conclusion: GitHubCheckConclusion.Success, startedAt: undefined, completedAt: undefined, detailsUrl: undefined },
+			{ id: 2, name: 'test', status: GitHubCheckStatus.Completed, conclusion: GitHubCheckConclusion.Failure, startedAt: undefined, completedAt: undefined, detailsUrl: undefined },
+		];
+
+		await model.refresh();
+		assert.strictEqual(model.checks.get().length, 2);
+		assert.strictEqual(model.overallStatus.get(), GitHubCIOverallStatus.Failure);
+	});
+
+	test('getCheckRunAnnotations delegates to fetcher', async () => {
+		const model = store.add(new GitHubPullRequestCIModel('owner', 'repo', 'abc', mockFetcher as unknown as GitHubPRCIFetcher, logService));
+		const result = await model.getCheckRunAnnotations(1);
+		assert.strictEqual(result, 'mock annotations');
+	});
+});
+
+
+//#region Test Helpers
+
+function makePR(): IGitHubPullRequest {
+	return {
+		number: 1,
+		title: 'Test PR',
+		body: 'Test body',
+		state: GitHubPullRequestState.Open,
+		author: { login: 'author', avatarUrl: '' },
+		headRef: 'feature',
+		baseRef: 'main',
+		isDraft: false,
+		createdAt: '2024-01-01T00:00:00Z',
+		updatedAt: '2024-01-02T00:00:00Z',
+		mergedAt: undefined,
+		mergeable: true,
+		mergeableState: 'clean',
+	};
+}
+
+function makeThread(id: string, path: string): IGitHubPRReviewThread {
+	return {
+		id,
+		isResolved: false,
+		path,
+		line: 10,
+		comments: [makeComment(100, `Comment on ${path}`, id)],
+	};
+}
+
+function makeComment(id: number, body: string, threadId: string = String(id)): IGitHubPRComment {
+	return {
+		id,
+		body,
+		author: { login: 'reviewer', avatarUrl: '' },
+		createdAt: '2024-01-01T00:00:00Z',
+		updatedAt: '2024-01-01T00:00:00Z',
+		path: undefined,
+		line: undefined,
+		threadId,
+		inReplyToId: undefined,
+	};
+}
+
+//#endregion
diff --git a/src/vs/sessions/contrib/github/test/browser/githubService.test.ts b/src/vs/sessions/contrib/github/test/browser/githubService.test.ts
new file mode 100644
index 0000000000000..2a2085556e05d
--- /dev/null
+++ b/src/vs/sessions/contrib/github/test/browser/githubService.test.ts
@@ -0,0 +1,134 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { NullLogService, ILogService } from '../../../../../platform/log/common/log.js';
+import { TestInstantiationService } from '../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import { GitHubService } from '../../browser/githubService.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { GITHUB_REMOTE_FILE_SCHEME } from '../../../fileTreeView/browser/githubFileSystemProvider.js';
+import { IActiveSessionItem } from '../../../sessions/browser/sessionsManagementService.js';
+
+suite('GitHubService', () => {
+
+	const store = new DisposableStore();
+	let service: GitHubService;
+
+	setup(() => {
+		const instantiationService = store.add(new TestInstantiationService());
+		instantiationService.stub(ILogService, new NullLogService());
+
+		service = store.add(instantiationService.createInstance(GitHubService));
+	});
+
+	teardown(() => store.clear());
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('getRepository returns cached model for same key', () => {
+		const model1 = service.getRepository('owner', 'repo');
+		const model2 = service.getRepository('owner', 'repo');
+		assert.strictEqual(model1, model2);
+	});
+
+	test('getRepository returns different models for different repos', () => {
+		const model1 = service.getRepository('owner', 'repo1');
+		const model2 = service.getRepository('owner', 'repo2');
+		assert.notStrictEqual(model1, model2);
+	});
+
+	test('getPullRequest returns cached model for same key', () => {
+		const model1 = service.getPullRequest('owner', 'repo', 1);
+		const model2 = service.getPullRequest('owner', 'repo', 1);
+		assert.strictEqual(model1, model2);
+	});
+
+	test('getPullRequest returns different models for different PRs', () => {
+		const model1 = service.getPullRequest('owner', 'repo', 1);
+		const model2 = service.getPullRequest('owner', 'repo', 2);
+		assert.notStrictEqual(model1, model2);
+	});
+
+	test('getPullRequestCI returns cached model for same key', () => {
+		const model1 = service.getPullRequestCI('owner', 'repo', 'abc123');
+		const model2 = service.getPullRequestCI('owner', 'repo', 'abc123');
+		assert.strictEqual(model1, model2);
+	});
+
+	test('getPullRequestCI returns different models for different refs', () => {
+		const model1 = service.getPullRequestCI('owner', 'repo', 'abc');
+		const model2 = service.getPullRequestCI('owner', 'repo', 'def');
+		assert.notStrictEqual(model1, model2);
+	});
+
+	test('disposing service does not throw', () => {
+		service.getRepository('owner', 'repo');
+		service.getPullRequest('owner', 'repo', 1);
+		service.getPullRequestCI('owner', 'repo', 'abc');
+
+		// Disposing the service should not throw and should clean up models
+		assert.doesNotThrow(() => service.dispose());
+	});
+});
+
+suite('getGitHubContext', () => {
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	function makeSession(overrides: Partial<IActiveSessionItem>): IActiveSessionItem {
+		return {
+			resource: URI.parse('test://session/1'),
+			isUntitled: false,
+			label: 'Test Session',
+			repository: undefined,
+			worktree: undefined,
+			worktreeBranchName: undefined,
+			worktreeBaseBranchProtected: undefined,
+			providerType: 'copilot-cloud-agent',
+			...overrides,
+		};
+	}
+
+	test('parses owner/repo from github-remote-file URI', () => {
+		const session = makeSession({
+			repository: URI.from({
+				scheme: GITHUB_REMOTE_FILE_SCHEME,
+				authority: 'github',
+				path: '/microsoft/vscode/main'
+			}),
+		});
+
+		const parts = session.repository!.path.split('/').filter(Boolean);
+		assert.strictEqual(parts.length >= 2, true);
+		assert.strictEqual(decodeURIComponent(parts[0]), 'microsoft');
+		assert.strictEqual(decodeURIComponent(parts[1]), 'vscode');
+	});
+
+	test('parses PR number from pullRequestUrl', () => {
+		const url = 'https://github.com/microsoft/vscode/pull/12345';
+		const match = /\/pull\/(\d+)/.exec(url);
+		assert.ok(match);
+		assert.strictEqual(parseInt(match![1], 10), 12345);
+	});
+
+	test('parses owner/repo from repositoryNwo', () => {
+		const nwo = 'microsoft/vscode';
+		const parts = nwo.split('/');
+		assert.strictEqual(parts.length, 2);
+		assert.strictEqual(parts[0], 'microsoft');
+		assert.strictEqual(parts[1], 'vscode');
+	});
+
+	test('returns undefined for non-GitHub file URI', () => {
+		const session = makeSession({
+			repository: URI.file('/local/path/to/repo'),
+		});
+
+		// file:// scheme is not github-remote-file
+		assert.notStrictEqual(session.repository!.scheme, GITHUB_REMOTE_FILE_SCHEME);
+	});
+});
diff --git a/src/vs/sessions/contrib/logs/browser/logs.contribution.ts b/src/vs/sessions/contrib/logs/browser/logs.contribution.ts
index e6de07b259404..8a562ce4977c8 100644
--- a/src/vs/sessions/contrib/logs/browser/logs.contribution.ts
+++ b/src/vs/sessions/contrib/logs/browser/logs.contribution.ts
@@ -5,11 +5,8 @@
 
 import { Codicon } from '../../../../base/common/codicons.js';
 import { localize, localize2 } from '../../../../nls.js';
-import { Action2, registerAction2 } from '../../../../platform/actions/common/actions.js';
-import { SessionsCategories } from '../../../common/categories.js';
-import { IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
+import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
 import { SyncDescriptor } from '../../../../platform/instantiation/common/descriptors.js';
-import { ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
 import { Registry } from '../../../../platform/registry/common/platform.js';
 import { registerIcon } from '../../../../platform/theme/common/iconRegistry.js';
 import { ViewPaneContainer } from '../../../../workbench/browser/parts/views/viewPaneContainer.js';
@@ -17,19 +14,18 @@ import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase
 import { IViewContainersRegistry, IViewsRegistry, ViewContainerLocation, Extensions as ViewContainerExtensions, WindowVisibility } from '../../../../workbench/common/views.js';
 import { OutputViewPane } from '../../../../workbench/contrib/output/browser/outputView.js';
 import { OUTPUT_VIEW_ID } from '../../../../workbench/services/output/common/output.js';
-import { IViewsService } from '../../../../workbench/services/views/common/viewsService.js';
 
 const SESSIONS_LOGS_CONTAINER_ID = 'workbench.sessions.panel.logsContainer';
 
-const CONTEXT_SESSIONS_SHOW_LOGS = new RawContextKey<boolean>('sessionsShowLogs', false);
-
 const logsViewIcon = registerIcon('sessions-logs-view-icon', Codicon.output, localize('sessionsLogsViewIcon', 'View icon of the logs view in the sessions window.'));
 
 class RegisterLogsViewContainerContribution implements IWorkbenchContribution {
 
 	static readonly ID = 'sessions.registerLogsViewContainer';
 
-	constructor() {
+	constructor(
+		@IContextKeyService contextKeyService: IContextKeyService,
+	) {
 		const viewContainerRegistry = Registry.as<IViewContainersRegistry>(ViewContainerExtensions.ViewContainersRegistry);
 		const viewsRegistry = Registry.as<IViewsRegistry>(ViewContainerExtensions.ViewsRegistry);
 
@@ -63,28 +59,9 @@ class RegisterLogsViewContainerContribution implements IWorkbenchContribution {
 			ctorDescriptor: new SyncDescriptor(OutputViewPane),
 			canToggleVisibility: true,
 			canMoveView: false,
-			when: CONTEXT_SESSIONS_SHOW_LOGS,
 			windowVisibility: WindowVisibility.Sessions,
 		}], logsViewContainer);
 	}
 }
 
 registerWorkbenchContribution2(RegisterLogsViewContainerContribution.ID, RegisterLogsViewContainerContribution, WorkbenchPhase.BlockStartup);
-
-// Command: Sessions: Show Logs
-registerAction2(class extends Action2 {
-	constructor() {
-		super({
-			id: 'workbench.sessions.action.showLogs',
-			title: localize2('sessionsShowLogs', "Show Logs"),
-			category: SessionsCategories.Sessions,
-			f1: true,
-		});
-	}
-	async run(accessor: ServicesAccessor): Promise<void> {
-		const contextKeyService = accessor.get(IContextKeyService);
-		const viewsService = accessor.get(IViewsService);
-		CONTEXT_SESSIONS_SHOW_LOGS.bindTo(contextKeyService).set(true);
-		await viewsService.openView(OUTPUT_VIEW_ID, true);
-	}
-});
diff --git a/src/vs/sessions/contrib/sessions/browser/aiCustomizationShortcutsWidget.ts b/src/vs/sessions/contrib/sessions/browser/aiCustomizationShortcutsWidget.ts
new file mode 100644
index 0000000000000..58c814528b3d5
--- /dev/null
+++ b/src/vs/sessions/contrib/sessions/browser/aiCustomizationShortcutsWidget.ts
@@ -0,0 +1,139 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import '../../../browser/media/sidebarActionButton.css';
+import './media/customizationsToolbar.css';
+import * as DOM from '../../../../base/browser/dom.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { Disposable, MutableDisposable } from '../../../../base/common/lifecycle.js';
+import { autorun } from '../../../../base/common/observable.js';
+import { ThemeIcon } from '../../../../base/common/themables.js';
+import { localize } from '../../../../nls.js';
+import { HiddenItemStrategy, MenuWorkbenchToolBar } from '../../../../platform/actions/browser/toolbar.js';
+import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
+import { IWorkspaceContextService } from '../../../../platform/workspace/common/workspace.js';
+import { Button } from '../../../../base/browser/ui/button/button.js';
+import { defaultButtonStyles } from '../../../../platform/theme/browser/defaultStyles.js';
+import { IPromptsService } from '../../../../workbench/contrib/chat/common/promptSyntax/service/promptsService.js';
+import { IMcpService } from '../../../../workbench/contrib/mcp/common/mcpTypes.js';
+import { IAICustomizationWorkspaceService } from '../../../../workbench/contrib/chat/common/aiCustomizationWorkspaceService.js';
+import { Menus } from '../../../browser/menus.js';
+import { getCustomizationTotalCount } from './customizationCounts.js';
+import { IAgentPluginService } from '../../../../workbench/contrib/chat/common/plugins/agentPluginService.js';
+
+const $ = DOM.$;
+
+const CUSTOMIZATIONS_COLLAPSED_KEY = 'agentSessions.customizationsCollapsed';
+
+export interface IAICustomizationShortcutsWidgetOptions {
+	readonly onDidToggleCollapse?: () => void;
+}
+
+export class AICustomizationShortcutsWidget extends Disposable {
+
+	constructor(
+		container: HTMLElement,
+		options: IAICustomizationShortcutsWidgetOptions | undefined,
+		@IInstantiationService private readonly instantiationService: IInstantiationService,
+		@IStorageService private readonly storageService: IStorageService,
+		@IPromptsService private readonly promptsService: IPromptsService,
+		@IMcpService private readonly mcpService: IMcpService,
+		@IWorkspaceContextService private readonly workspaceContextService: IWorkspaceContextService,
+		@IAICustomizationWorkspaceService private readonly workspaceService: IAICustomizationWorkspaceService,
+		@IAgentPluginService private readonly agentPluginService: IAgentPluginService,
+	) {
+		super();
+
+		this._render(container, options);
+	}
+
+	private _render(parent: HTMLElement, options: IAICustomizationShortcutsWidgetOptions | undefined): void {
+		// Get initial collapsed state
+		const isCollapsed = this.storageService.getBoolean(CUSTOMIZATIONS_COLLAPSED_KEY, StorageScope.PROFILE, false);
+
+		const container = DOM.append(parent, $('.ai-customization-toolbar'));
+		if (isCollapsed) {
+			container.classList.add('collapsed');
+		}
+
+		// Header (clickable to toggle)
+		const header = DOM.append(container, $('.ai-customization-header'));
+		header.classList.toggle('collapsed', isCollapsed);
+
+		const headerButtonContainer = DOM.append(header, $('.customization-link-button-container'));
+		const headerButton = this._register(new Button(headerButtonContainer, {
+			...defaultButtonStyles,
+			secondary: true,
+			title: false,
+			supportIcons: true,
+			buttonSecondaryBackground: 'transparent',
+			buttonSecondaryHoverBackground: undefined,
+			buttonSecondaryForeground: undefined,
+			buttonSecondaryBorder: undefined,
+		}));
+		headerButton.element.classList.add('customization-link-button', 'sidebar-action-button');
+		headerButton.element.setAttribute('aria-expanded', String(!isCollapsed));
+		headerButton.label = localize('customizations', "CUSTOMIZATIONS");
+
+		const chevronContainer = DOM.append(headerButton.element, $('span.customization-link-counts'));
+		const chevron = DOM.append(chevronContainer, $('.ai-customization-chevron'));
+		const headerTotalCount = DOM.append(chevronContainer, $('span.ai-customization-header-total.hidden'));
+		chevron.classList.add(...ThemeIcon.asClassNameArray(isCollapsed ? Codicon.chevronRight : Codicon.chevronDown));
+
+		// Toolbar container
+		const toolbarContainer = DOM.append(container, $('.ai-customization-toolbar-content.sidebar-action-list'));
+
+		this._register(this.instantiationService.createInstance(MenuWorkbenchToolBar, toolbarContainer, Menus.SidebarCustomizations, {
+			hiddenItemStrategy: HiddenItemStrategy.NoHide,
+			toolbarOptions: { primaryGroup: () => true },
+			telemetrySource: 'sidebarCustomizations',
+		}));
+
+		let updateCountRequestId = 0;
+		const updateHeaderTotalCount = async () => {
+			const requestId = ++updateCountRequestId;
+			const totalCount = await getCustomizationTotalCount(this.promptsService, this.mcpService, this.workspaceService, this.workspaceContextService, this.agentPluginService);
+			if (requestId !== updateCountRequestId) {
+				return;
+			}
+
+			headerTotalCount.classList.toggle('hidden', totalCount === 0);
+			headerTotalCount.textContent = `${totalCount}`;
+		};
+
+		this._register(this.promptsService.onDidChangeCustomAgents(() => updateHeaderTotalCount()));
+		this._register(this.promptsService.onDidChangeSlashCommands(() => updateHeaderTotalCount()));
+		this._register(this.workspaceContextService.onDidChangeWorkspaceFolders(() => updateHeaderTotalCount()));
+		this._register(autorun(reader => {
+			this.mcpService.servers.read(reader);
+			updateHeaderTotalCount();
+		}));
+		this._register(autorun(reader => {
+			this.workspaceService.activeProjectRoot.read(reader);
+			updateHeaderTotalCount();
+		}));
+		updateHeaderTotalCount();
+
+		// Toggle collapse on header click
+		const transitionListener = this._register(new MutableDisposable());
+		const toggleCollapse = () => {
+			const collapsed = container.classList.toggle('collapsed');
+			header.classList.toggle('collapsed', collapsed);
+			this.storageService.store(CUSTOMIZATIONS_COLLAPSED_KEY, collapsed, StorageScope.PROFILE, StorageTarget.USER);
+			headerButton.element.setAttribute('aria-expanded', String(!collapsed));
+			chevron.classList.remove(...ThemeIcon.asClassNameArray(Codicon.chevronRight), ...ThemeIcon.asClassNameArray(Codicon.chevronDown));
+			chevron.classList.add(...ThemeIcon.asClassNameArray(collapsed ? Codicon.chevronRight : Codicon.chevronDown));
+
+			// Re-layout after the transition
+			transitionListener.value = DOM.addDisposableListener(toolbarContainer, 'transitionend', () => {
+				transitionListener.clear();
+				options?.onDidToggleCollapse?.();
+			});
+		};
+
+		this._register(headerButton.onDidClick(() => toggleCollapse()));
+	}
+}
diff --git a/src/vs/sessions/contrib/sessions/browser/customizationCounts.ts b/src/vs/sessions/contrib/sessions/browser/customizationCounts.ts
index dd874c3e86c71..88d932c7ee5d9 100644
--- a/src/vs/sessions/contrib/sessions/browser/customizationCounts.ts
+++ b/src/vs/sessions/contrib/sessions/browser/customizationCounts.ts
@@ -4,58 +4,151 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { isEqualOrParent } from '../../../../base/common/resources.js';
+import { URI } from '../../../../base/common/uri.js';
+import { IWorkspaceContextService } from '../../../../platform/workspace/common/workspace.js';
+import { IFileService } from '../../../../platform/files/common/files.js';
 import { PromptsType } from '../../../../workbench/contrib/chat/common/promptSyntax/promptTypes.js';
 import { IPromptsService, PromptsStorage } from '../../../../workbench/contrib/chat/common/promptSyntax/service/promptsService.js';
+import { BUILTIN_STORAGE } from '../../chat/common/builtinPromptsStorage.js';
 import { IMcpService } from '../../../../workbench/contrib/mcp/common/mcpTypes.js';
+import { IAICustomizationWorkspaceService, applyStorageSourceFilter, IStorageSourceFilter } from '../../../../workbench/contrib/chat/common/aiCustomizationWorkspaceService.js';
+import { parseHooksFromFile } from '../../../../workbench/contrib/chat/common/promptSyntax/hookCompatibility.js';
+import { IAgentPluginService } from '../../../../workbench/contrib/chat/common/plugins/agentPluginService.js';
+import { parse as parseJSONC } from '../../../../base/common/jsonc.js';
 
 export interface ISourceCounts {
 	readonly workspace: number;
 	readonly user: number;
 	readonly extension: number;
+	readonly builtin: number;
 }
 
-export function getSourceCountsTotal(counts: ISourceCounts): number {
-	return counts.workspace + counts.user + counts.extension;
-}
+const storageToCountKey: Partial<Record<string, keyof ISourceCounts>> = {
+	[PromptsStorage.local]: 'workspace',
+	[PromptsStorage.user]: 'user',
+	[PromptsStorage.extension]: 'extension',
+	[BUILTIN_STORAGE]: 'builtin',
+};
 
-export async function getPromptSourceCounts(promptsService: IPromptsService, promptType: PromptsType): Promise<ISourceCounts> {
-	const [workspaceItems, userItems, extensionItems] = await Promise.all([
-		promptsService.listPromptFilesForStorage(promptType, PromptsStorage.local, CancellationToken.None),
-		promptsService.listPromptFilesForStorage(promptType, PromptsStorage.user, CancellationToken.None),
-		promptsService.listPromptFilesForStorage(promptType, PromptsStorage.extension, CancellationToken.None),
-	]);
-	return {
-		workspace: workspaceItems.length,
-		user: userItems.length,
-		extension: extensionItems.length,
-	};
+export function getSourceCountsTotal(counts: ISourceCounts, filter: IStorageSourceFilter): number {
+	let total = 0;
+	for (const storage of filter.sources) {
+		const key = storageToCountKey[storage];
+		if (key) {
+			total += counts[key];
+		}
+	}
+	return total;
 }
 
-export async function getSkillSourceCounts(promptsService: IPromptsService): Promise<ISourceCounts> {
-	const skills = await promptsService.findAgentSkills(CancellationToken.None);
-	if (!skills || skills.length === 0) {
-		return { workspace: 0, user: 0, extension: 0 };
+/**
+ * Gets source counts for a prompt type, using the SAME data sources as
+ * loadItems() in the list widget to avoid count mismatches.
+ */
+export async function getSourceCounts(
+	promptsService: IPromptsService,
+	promptType: PromptsType,
+	filter: IStorageSourceFilter,
+	workspaceContextService: IWorkspaceContextService,
+	workspaceService: IAICustomizationWorkspaceService,
+	fileService?: IFileService,
+): Promise<ISourceCounts> {
+	const items: { storage: PromptsStorage; uri: URI }[] = [];
+
+	if (promptType === PromptsType.agent) {
+		// Must match loadItems: uses getCustomAgents()
+		const agents = await promptsService.getCustomAgents(CancellationToken.None);
+		for (const a of agents) {
+			items.push({ storage: a.source.storage, uri: a.uri });
+		}
+	} else if (promptType === PromptsType.skill) {
+		// Must match loadItems: uses findAgentSkills()
+		const skills = await promptsService.findAgentSkills(CancellationToken.None);
+		for (const s of skills ?? []) {
+			items.push({ storage: s.storage, uri: s.uri });
+		}
+	} else if (promptType === PromptsType.prompt) {
+		// Must match loadItems: uses getPromptSlashCommands() filtering out skills
+		const commands = await promptsService.getPromptSlashCommands(CancellationToken.None);
+		for (const c of commands) {
+			if (c.promptPath.type === PromptsType.skill) {
+				continue;
+			}
+			items.push({ storage: c.promptPath.storage, uri: c.promptPath.uri });
+		}
+	} else if (promptType === PromptsType.instructions) {
+		// Must match loadItems: uses listPromptFiles + listAgentInstructions
+		const promptFiles = await promptsService.listPromptFiles(promptType, CancellationToken.None);
+		for (const f of promptFiles) {
+			items.push({ storage: f.storage, uri: f.uri });
+		}
+		const agentInstructions = await promptsService.listAgentInstructions(CancellationToken.None, undefined);
+		const workspaceFolderUris = workspaceContextService.getWorkspace().folders.map(f => f.uri);
+		const activeRoot = workspaceService.getActiveProjectRoot();
+		if (activeRoot) {
+			workspaceFolderUris.push(activeRoot);
+		}
+		for (const file of agentInstructions) {
+			const isWorkspaceFile = workspaceFolderUris.some(root => isEqualOrParent(file.uri, root));
+			items.push({
+				storage: isWorkspaceFile ? PromptsStorage.local : PromptsStorage.user,
+				uri: file.uri,
+			});
+		}
+	} else if (promptType === PromptsType.hook && fileService) {
+		// Must match loadItems: parse individual hooks from each file
+		const hookFiles = await promptsService.listPromptFiles(PromptsType.hook, CancellationToken.None);
+		const activeRoot = workspaceService.getActiveProjectRoot();
+		for (const hookFile of hookFiles) {
+			try {
+				const content = await fileService.readFile(hookFile.uri);
+				const json = parseJSONC(content.value.toString());
+				const { hooks } = parseHooksFromFile(hookFile.uri, json, activeRoot, '');
+				if (hooks.size > 0) {
+					for (const [, entry] of hooks) {
+						for (let i = 0; i < entry.hooks.length; i++) {
+							items.push({ storage: hookFile.storage, uri: hookFile.uri });
+						}
+					}
+				} else {
+					items.push({ storage: hookFile.storage, uri: hookFile.uri });
+				}
+			} catch {
+				items.push({ storage: hookFile.storage, uri: hookFile.uri });
+			}
+		}
+	} else {
+		// hooks and anything else: uses listPromptFiles
+		const files = await promptsService.listPromptFiles(promptType, CancellationToken.None);
+		for (const f of files) {
+			items.push({ storage: f.storage, uri: f.uri });
+		}
 	}
+
+	// Apply the same storage source filter as the list widget
+	const filtered = applyStorageSourceFilter(items, filter);
 	return {
-		workspace: skills.filter(s => s.storage === PromptsStorage.local).length,
-		user: skills.filter(s => s.storage === PromptsStorage.user).length,
-		extension: skills.filter(s => s.storage === PromptsStorage.extension).length,
+		workspace: filtered.filter(i => i.storage === PromptsStorage.local).length,
+		user: filtered.filter(i => i.storage === PromptsStorage.user).length,
+		extension: filtered.filter(i => i.storage === PromptsStorage.extension).length,
+		builtin: filtered.filter(i => i.storage === BUILTIN_STORAGE).length,
 	};
 }
 
-export async function getCustomizationTotalCount(promptsService: IPromptsService, mcpService: IMcpService): Promise<number> {
-	const [agentCounts, skillCounts, instructionCounts, promptCounts, hookCounts] = await Promise.all([
-		getPromptSourceCounts(promptsService, PromptsType.agent),
-		getSkillSourceCounts(promptsService),
-		getPromptSourceCounts(promptsService, PromptsType.instructions),
-		getPromptSourceCounts(promptsService, PromptsType.prompt),
-		getPromptSourceCounts(promptsService, PromptsType.hook),
-	]);
-
-	return getSourceCountsTotal(agentCounts)
-		+ getSourceCountsTotal(skillCounts)
-		+ getSourceCountsTotal(instructionCounts)
-		+ getSourceCountsTotal(promptCounts)
-		+ getSourceCountsTotal(hookCounts)
-		+ mcpService.servers.get().length;
+export async function getCustomizationTotalCount(
+	promptsService: IPromptsService,
+	mcpService: IMcpService,
+	workspaceService: IAICustomizationWorkspaceService,
+	workspaceContextService: IWorkspaceContextService,
+	agentPluginService?: IAgentPluginService,
+): Promise<number> {
+	const types: PromptsType[] = [PromptsType.agent, PromptsType.skill, PromptsType.instructions, PromptsType.prompt, PromptsType.hook];
+	const results = await Promise.all(types.map(type => {
+		const filter = workspaceService.getStorageSourceFilter(type);
+		return getSourceCounts(promptsService, type, filter, workspaceContextService, workspaceService)
+			.then(counts => getSourceCountsTotal(counts, filter));
+	}));
+	const pluginCount = agentPluginService?.plugins.get().length ?? 0;
+	return results.reduce((sum, n) => sum + n, 0) + mcpService.servers.get().length + pluginCount;
 }
diff --git a/src/vs/sessions/contrib/sessions/browser/customizationsToolbar.contribution.ts b/src/vs/sessions/contrib/sessions/browser/customizationsToolbar.contribution.ts
index f2e6d9e45e71b..07c6cf93903fe 100644
--- a/src/vs/sessions/contrib/sessions/browser/customizationsToolbar.contribution.ts
+++ b/src/vs/sessions/contrib/sessions/browser/customizationsToolbar.contribution.ts
@@ -5,7 +5,6 @@
 
 import '../../../browser/media/sidebarActionButton.css';
 import './media/customizationsToolbar.css';
-import { Codicon } from '../../../../base/common/codicons.js';
 import { Disposable, DisposableStore } from '../../../../base/common/lifecycle.js';
 import { ThemeIcon } from '../../../../base/common/themables.js';
 import { localize, localize2 } from '../../../../nls.js';
@@ -21,76 +20,80 @@ import { PromptsType } from '../../../../workbench/contrib/chat/common/promptSyn
 import { ILanguageModelsService } from '../../../../workbench/contrib/chat/common/languageModels.js';
 import { IMcpService } from '../../../../workbench/contrib/mcp/common/mcpTypes.js';
 import { Menus } from '../../../browser/menus.js';
-import { agentIcon, instructionsIcon, promptIcon, skillIcon, hookIcon, workspaceIcon, userIcon, extensionIcon } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationIcons.js';
+import { agentIcon, instructionsIcon, mcpServerIcon, pluginIcon, promptIcon, skillIcon, hookIcon } from '../../../../workbench/contrib/chat/browser/aiCustomization/aiCustomizationIcons.js';
 import { ActionViewItem, IBaseActionViewItemOptions } from '../../../../base/browser/ui/actionbar/actionViewItems.js';
 import { IAction } from '../../../../base/common/actions.js';
 import { $, append } from '../../../../base/browser/dom.js';
 import { autorun } from '../../../../base/common/observable.js';
 import { IWorkspaceContextService } from '../../../../platform/workspace/common/workspace.js';
+import { IFileService } from '../../../../platform/files/common/files.js';
 import { ISessionsManagementService } from './sessionsManagementService.js';
 import { Button } from '../../../../base/browser/ui/button/button.js';
 import { defaultButtonStyles } from '../../../../platform/theme/browser/defaultStyles.js';
-import { getPromptSourceCounts, getSkillSourceCounts, getSourceCountsTotal, ISourceCounts } from './customizationCounts.js';
-import { IEditorService } from '../../../../workbench/services/editor/common/editorService.js';
+import { getSourceCounts, getSourceCountsTotal } from './customizationCounts.js';
+import { IEditorService, MODAL_GROUP } from '../../../../workbench/services/editor/common/editorService.js';
+import { IAICustomizationWorkspaceService } from '../../../../workbench/contrib/chat/common/aiCustomizationWorkspaceService.js';
+import { IAgentPluginService } from '../../../../workbench/contrib/chat/common/plugins/agentPluginService.js';
 
-interface ICustomizationItemConfig {
+export interface ICustomizationItemConfig {
 	readonly id: string;
 	readonly label: string;
 	readonly icon: ThemeIcon;
 	readonly section: AICustomizationManagementSection;
-	readonly getSourceCounts?: (promptsService: IPromptsService) => Promise<ISourceCounts>;
-	readonly getCount?: (languageModelsService: ILanguageModelsService, mcpService: IMcpService) => Promise<number>;
+	readonly promptType?: PromptsType;
+	readonly isMcp?: boolean;
+	readonly isPlugins?: boolean;
 }
 
-const CUSTOMIZATION_ITEMS: ICustomizationItemConfig[] = [
+export const CUSTOMIZATION_ITEMS: ICustomizationItemConfig[] = [
 	{
 		id: 'sessions.customization.agents',
 		label: localize('agents', "Agents"),
 		icon: agentIcon,
 		section: AICustomizationManagementSection.Agents,
-		getSourceCounts: (ps) => getPromptSourceCounts(ps, PromptsType.agent),
+		promptType: PromptsType.agent,
 	},
 	{
 		id: 'sessions.customization.skills',
 		label: localize('skills', "Skills"),
 		icon: skillIcon,
 		section: AICustomizationManagementSection.Skills,
-		getSourceCounts: (ps) => getSkillSourceCounts(ps),
+		promptType: PromptsType.skill,
 	},
 	{
 		id: 'sessions.customization.instructions',
 		label: localize('instructions', "Instructions"),
 		icon: instructionsIcon,
 		section: AICustomizationManagementSection.Instructions,
-		getSourceCounts: (ps) => getPromptSourceCounts(ps, PromptsType.instructions),
+		promptType: PromptsType.instructions,
 	},
 	{
 		id: 'sessions.customization.prompts',
 		label: localize('prompts', "Prompts"),
 		icon: promptIcon,
 		section: AICustomizationManagementSection.Prompts,
-		getSourceCounts: (ps) => getPromptSourceCounts(ps, PromptsType.prompt),
+		promptType: PromptsType.prompt,
 	},
 	{
 		id: 'sessions.customization.hooks',
 		label: localize('hooks', "Hooks"),
 		icon: hookIcon,
 		section: AICustomizationManagementSection.Hooks,
-		getSourceCounts: (ps) => getPromptSourceCounts(ps, PromptsType.hook),
+		promptType: PromptsType.hook,
 	},
 	{
 		id: 'sessions.customization.mcpServers',
 		label: localize('mcpServers', "MCP Servers"),
-		icon: Codicon.server,
+		icon: mcpServerIcon,
 		section: AICustomizationManagementSection.McpServers,
-		getCount: (_lm, mcp) => Promise.resolve(mcp.servers.get().length),
+		isMcp: true,
 	},
 	{
-		id: 'sessions.customization.models',
-		label: localize('models', "Models"),
-		icon: Codicon.vm,
-		section: AICustomizationManagementSection.Models,
-		getCount: (lm) => Promise.resolve(lm.getLanguageModelIds().length),
+		id: 'sessions.customization.plugins',
+		label: localize('plugins', "Plugins"),
+		icon: pluginIcon,
+		section: AICustomizationManagementSection.Plugins,
+		isPlugins: true,
 	},
 ];
 
@@ -98,7 +101,7 @@ const CUSTOMIZATION_ITEMS: ICustomizationItemConfig[] = [
  * Custom ActionViewItem for each customization link in the toolbar.
  * Renders icon + label + source count badges, matching the sidebar footer style.
  */
-class CustomizationLinkViewItem extends ActionViewItem {
+export class CustomizationLinkViewItem extends ActionViewItem {
 
 	private readonly _viewItemDisposables: DisposableStore;
 	private _button: Button | undefined;
@@ -113,6 +116,9 @@ class CustomizationLinkViewItem extends ActionViewItem {
 		@IMcpService private readonly _mcpService: IMcpService,
 		@IWorkspaceContextService private readonly _workspaceContextService: IWorkspaceContextService,
 		@ISessionsManagementService private readonly _activeSessionService: ISessionsManagementService,
+		@IAICustomizationWorkspaceService private readonly _workspaceService: IAICustomizationWorkspaceService,
+		@IFileService private readonly _fileService: IFileService,
+		@IAgentPluginService private readonly _agentPluginService: IAgentPluginService,
 	) {
 		super(undefined, action, { ...options, icon: false, label: false });
 		this._viewItemDisposables = this._register(new DisposableStore());
@@ -156,6 +162,10 @@ class CustomizationLinkViewItem extends ActionViewItem {
 			this._mcpService.servers.read(reader);
 			this._updateCounts();
 		}));
+		this._viewItemDisposables.add(autorun(reader => {
+			this._agentPluginService.plugins.read(reader);
+			this._updateCounts();
+		}));
 		this._viewItemDisposables.add(this._workspaceContextService.onDidChangeWorkspaceFolders(() => this._updateCounts()));
 		this._viewItemDisposables.add(autorun(reader => {
 			this._activeSessionService.activeSession.read(reader);
@@ -166,48 +176,34 @@ class CustomizationLinkViewItem extends ActionViewItem {
 		this._updateCounts();
 	}
 
+	private _updateCountsRequestId = 0;
+
 	private async _updateCounts(): Promise<void> {
 		if (!this._countContainer) {
 			return;
 		}
 
-		if (this._config.getSourceCounts) {
-			const counts = await this._config.getSourceCounts(this._promptsService);
-			this._renderSourceCounts(this._countContainer, counts);
-		} else if (this._config.getCount) {
-			const count = await this._config.getCount(this._languageModelsService, this._mcpService);
-			this._renderSimpleCount(this._countContainer, count);
-		}
-	}
+		const requestId = ++this._updateCountsRequestId;
 
-	private _renderSourceCounts(container: HTMLElement, counts: ISourceCounts): void {
-		container.textContent = '';
-		const total = getSourceCountsTotal(counts);
-		container.classList.toggle('hidden', total === 0);
-		if (total === 0) {
-			return;
-		}
-
-		const sources: { count: number; icon: ThemeIcon; title: string }[] = [
-			{ count: counts.workspace, icon: workspaceIcon, title: localize('workspaceCount', "{0} from workspace", counts.workspace) },
-			{ count: counts.user, icon: userIcon, title: localize('userCount', "{0} from user", counts.user) },
-			{ count: counts.extension, icon: extensionIcon, title: localize('extensionCount', "{0} from extensions", counts.extension) },
-		];
-
-		for (const source of sources) {
-			if (source.count === 0) {
-				continue;
+		if (this._config.promptType) {
+			const type = this._config.promptType;
+			const filter = this._workspaceService.getStorageSourceFilter(type);
+			const counts = await getSourceCounts(this._promptsService, type, filter, this._workspaceContextService, this._workspaceService, this._fileService);
+			if (requestId !== this._updateCountsRequestId) {
+				return;
 			}
-			const badge = append(container, $('span.source-count-badge'));
-			badge.title = source.title;
-			const icon = append(badge, $('span.source-count-icon'));
-			icon.classList.add(...ThemeIcon.asClassNameArray(source.icon));
-			const num = append(badge, $('span.source-count-num'));
-			num.textContent = `${source.count}`;
+			const total = getSourceCountsTotal(counts, filter);
+			this._renderTotalCount(this._countContainer, total);
+		} else if (this._config.isMcp) {
+			const total = this._mcpService.servers.get().length;
+			this._renderTotalCount(this._countContainer, total);
+		} else if (this._config.isPlugins) {
+			const total = this._agentPluginService.plugins.get().length;
+			this._renderTotalCount(this._countContainer, total);
 		}
 	}
 
-	private _renderSimpleCount(container: HTMLElement, count: number): void {
+	private _renderTotalCount(container: HTMLElement, count: number): void {
 		container.textContent = '';
 		container.classList.toggle('hidden', count === 0);
 		if (count > 0) {
@@ -220,7 +216,7 @@ class CustomizationLinkViewItem extends ActionViewItem {
 
 // --- Register actions and view items --- //
 
-class CustomizationsToolbarContribution extends Disposable implements IWorkbenchContribution {
+export class CustomizationsToolbarContribution extends Disposable implements IWorkbenchContribution {
 
 	static readonly ID = 'workbench.contrib.sessionsCustomizationsToolbar';
 
@@ -252,7 +248,7 @@ class CustomizationsToolbarContribution extends Disposable implements IWorkbench
 				async run(accessor: ServicesAccessor): Promise<void> {
 					const editorService = accessor.get(IEditorService);
 					const input = AICustomizationManagementEditorInput.getOrCreate();
-					const editor = await editorService.openEditor(input, { pinned: true });
+					const editor = await editorService.openEditor(input, { pinned: true }, MODAL_GROUP);
 					if (editor instanceof AICustomizationManagementEditor) {
 						editor.selectSectionById(config.section);
 					}
diff --git a/src/vs/sessions/contrib/sessions/browser/media/customizationsToolbar.css b/src/vs/sessions/contrib/sessions/browser/media/customizationsToolbar.css
index d671775dbd57c..bc08fc25eb54f 100644
--- a/src/vs/sessions/contrib/sessions/browser/media/customizationsToolbar.css
+++ b/src/vs/sessions/contrib/sessions/browser/media/customizationsToolbar.css
@@ -2,132 +2,129 @@
  *  Copyright (c) Microsoft Corporation. All rights reserved.
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
+/* AI Customization section - pinned to bottom */
+.ai-customization-toolbar {
+	display: flex;
+	flex-direction: column;
+	flex-shrink: 0;
+	border-top: 1px solid var(--vscode-widget-border);
+	padding: 6px;
+}
+
+/* Make the toolbar, action bar, and items fill full width and stack vertically */
+.ai-customization-toolbar .ai-customization-toolbar-content .monaco-toolbar,
+.ai-customization-toolbar .ai-customization-toolbar-content .monaco-action-bar {
+	width: 100%;
+}
+
+.ai-customization-toolbar .ai-customization-toolbar-content .monaco-action-bar .actions-container {
+	display: flex;
+	flex-direction: column;
+	width: 100%;
+}
+
+.ai-customization-toolbar .ai-customization-toolbar-content .monaco-action-bar .action-item {
+	width: 100%;
+	max-width: 100%;
+}
+
+.ai-customization-toolbar .customization-link-widget {
+	width: 100%;
+}
+
+/* Customization header - clickable for collapse */
+.ai-customization-toolbar .ai-customization-header {
+	display: flex;
+	align-items: center;
+	-webkit-user-select: none;
+	user-select: none;
+}
+
+.ai-customization-toolbar .ai-customization-header:not(.collapsed) {
+	margin-bottom: 4px;
+}
+
+.ai-customization-toolbar .ai-customization-chevron {
+	flex-shrink: 0;
+	opacity: 0;
+}
+
+.ai-customization-toolbar .ai-customization-header:not(.collapsed) .customization-link-button:hover .ai-customization-chevron,
+.ai-customization-toolbar .ai-customization-header:not(.collapsed) .customization-link-button:focus-within .ai-customization-chevron,
+.ai-customization-toolbar .ai-customization-header.collapsed .customization-link-button:hover .ai-customization-chevron,
+.ai-customization-toolbar .ai-customization-header.collapsed .customization-link-button:focus-within .ai-customization-chevron {
+	opacity: 0.7;
+}
+
+.ai-customization-toolbar .ai-customization-header-total {
+	display: none;
+	opacity: 0.7;
+	font-size: 11px;
+	line-height: 1;
+}
+
+.ai-customization-toolbar .ai-customization-header.collapsed .customization-link-button:not(:hover):not(:focus-within) .ai-customization-header-total:not(.hidden) {
+	display: inline;
+}
+
+.ai-customization-toolbar .ai-customization-header.collapsed .customization-link-button:hover .ai-customization-header-total,
+.ai-customization-toolbar .ai-customization-header.collapsed .customization-link-button:focus-within .ai-customization-header-total,
+.ai-customization-toolbar .ai-customization-header:not(.collapsed) .customization-link-button .ai-customization-header-total {
+	display: none;
+}
+
+/* Button container - fills available space */
+.ai-customization-toolbar .customization-link-button-container {
+	overflow: hidden;
+	min-width: 0;
+	flex: 1;
+}
+
+/* Button needs relative positioning for counts overlay */
+.ai-customization-toolbar .customization-link-button {
+	position: relative;
+}
+
+/* Counts - floating right inside the button */
+.ai-customization-toolbar .customization-link-counts {
+	position: absolute;
+	right: 8px;
+	top: 50%;
+	transform: translateY(-50%);
+	display: flex;
+	align-items: center;
+	gap: 6px;
+}
+
+.ai-customization-toolbar .customization-link-counts.hidden {
+	display: none;
+}
+
+.ai-customization-toolbar .source-count-badge {
+	display: flex;
+	align-items: center;
+	gap: 2px;
+}
+
+.ai-customization-toolbar .source-count-icon {
+	font-size: 12px;
+	opacity: 0.6;
+}
+
+.ai-customization-toolbar .source-count-num {
+	font-size: 11px;
+	color: var(--vscode-descriptionForeground);
+	opacity: 0.8;
+}
+
+/* Collapsed state */
+.ai-customization-toolbar .ai-customization-toolbar-content {
+	max-height: 500px;
+	overflow: hidden;
+	transition: max-height 0.2s ease-out;
+	padding-bottom: 2px;
+}
 
-.agent-sessions-viewpane {
-
-	/* AI Customization section - pinned to bottom */
-	.ai-customization-toolbar {
-		display: flex;
-		flex-direction: column;
-		flex-shrink: 0;
-		border-top: 1px solid var(--vscode-widget-border);
-		padding: 6px;
-	}
-
-	/* Make the toolbar, action bar, and items fill full width and stack vertically */
-	.ai-customization-toolbar .ai-customization-toolbar-content .monaco-toolbar,
-	.ai-customization-toolbar .ai-customization-toolbar-content .monaco-action-bar {
-		width: 100%;
-	}
-
-	.ai-customization-toolbar .ai-customization-toolbar-content .monaco-action-bar .actions-container {
-		display: flex;
-		flex-direction: column;
-		width: 100%;
-	}
-
-	.ai-customization-toolbar .ai-customization-toolbar-content .monaco-action-bar .action-item {
-		width: 100%;
-		max-width: 100%;
-	}
-
-	.ai-customization-toolbar .customization-link-widget {
-		width: 100%;
-	}
-
-	/* Customization header - clickable for collapse */
-	.ai-customization-toolbar .ai-customization-header {
-		display: flex;
-		align-items: center;
-		-webkit-user-select: none;
-		user-select: none;
-	}
-
-	.ai-customization-toolbar .ai-customization-header:not(.collapsed) {
-		margin-bottom: 4px;
-	}
-
-	.ai-customization-toolbar .ai-customization-chevron {
-		flex-shrink: 0;
-		opacity: 0;
-	}
-
-	.ai-customization-toolbar .ai-customization-header:not(.collapsed) .customization-link-button:hover .ai-customization-chevron,
-	.ai-customization-toolbar .ai-customization-header:not(.collapsed) .customization-link-button:focus-within .ai-customization-chevron,
-	.ai-customization-toolbar .ai-customization-header.collapsed .customization-link-button:hover .ai-customization-chevron,
-	.ai-customization-toolbar .ai-customization-header.collapsed .customization-link-button:focus-within .ai-customization-chevron {
-		opacity: 0.7;
-	}
-
-	.ai-customization-toolbar .ai-customization-header-total {
-		display: none;
-		opacity: 0.7;
-		font-size: 11px;
-		line-height: 1;
-	}
-
-	.ai-customization-toolbar .ai-customization-header.collapsed .customization-link-button:not(:hover):not(:focus-within) .ai-customization-header-total:not(.hidden) {
-		display: inline;
-	}
-
-	.ai-customization-toolbar .ai-customization-header.collapsed .customization-link-button:hover .ai-customization-header-total,
-	.ai-customization-toolbar .ai-customization-header.collapsed .customization-link-button:focus-within .ai-customization-header-total,
-	.ai-customization-toolbar .ai-customization-header:not(.collapsed) .customization-link-button .ai-customization-header-total {
-		display: none;
-	}
-
-	/* Button container - fills available space */
-	.ai-customization-toolbar .customization-link-button-container {
-		overflow: hidden;
-		min-width: 0;
-		flex: 1;
-	}
-
-	/* Button needs relative positioning for counts overlay */
-	.ai-customization-toolbar .customization-link-button {
-		position: relative;
-	}
-
-	/* Counts - floating right inside the button */
-	.ai-customization-toolbar .customization-link-counts {
-		position: absolute;
-		right: 8px;
-		top: 50%;
-		transform: translateY(-50%);
-		display: flex;
-		align-items: center;
-		gap: 6px;
-	}
-
-	.ai-customization-toolbar .customization-link-counts.hidden {
-		display: none;
-	}
-
-	.ai-customization-toolbar .source-count-badge {
-		display: flex;
-		align-items: center;
-		gap: 2px;
-	}
-
-	.ai-customization-toolbar .source-count-icon {
-		font-size: 12px;
-		opacity: 0.6;
-	}
-
-	.ai-customization-toolbar .source-count-num {
-		font-size: 11px;
-		color: var(--vscode-descriptionForeground);
-		opacity: 0.8;
-	}
-
-	/* Collapsed state */
-	.ai-customization-toolbar .ai-customization-toolbar-content {
-		max-height: 500px;
-		overflow: hidden;
-		transition: max-height 0.2s ease-out;
-	}
-
-	.ai-customization-toolbar.collapsed .ai-customization-toolbar-content {
-		max-height: 0;
-	}
+.ai-customization-toolbar.collapsed .ai-customization-toolbar-content {
+	max-height: 0;
 }
diff --git a/src/vs/sessions/contrib/sessions/browser/media/sessionsTitleBarWidget.css b/src/vs/sessions/contrib/sessions/browser/media/sessionsTitleBarWidget.css
index f8b2715466dbc..b9f14273091fa 100644
--- a/src/vs/sessions/contrib/sessions/browser/media/sessionsTitleBarWidget.css
+++ b/src/vs/sessions/contrib/sessions/browser/media/sessionsTitleBarWidget.css
@@ -6,24 +6,32 @@
 /* Container - button style hover */
 .command-center .agent-sessions-titlebar-container {
 	display: flex;
-	width: 38vw;
-	max-width: 600px;
-	display: flex;
+	width: 100%;
 	flex-direction: row;
 	flex-wrap: nowrap;
 	align-items: center;
-	justify-content: center;
+	justify-content: flex-start;
 	padding: 0 10px;
 	height: 22px;
 	border-radius: 4px;
-	cursor: pointer;
 	-webkit-app-region: no-drag;
 	overflow: hidden;
 	color: var(--vscode-commandCenter-foreground);
 	gap: 6px;
+	cursor: default;
 }
 
-.command-center .agent-sessions-titlebar-container:hover {
+/* Session pill - clickable area for session picker */
+.command-center .agent-sessions-titlebar-container .agent-sessions-titlebar-pill {
+	display: flex;
+	align-items: center;
+	padding: 0 4px;
+	border-radius: 4px;
+	min-width: 0;
+	max-width: 600px;
+}
+
+.command-center .agent-sessions-titlebar-container .agent-sessions-titlebar-pill:hover {
 	background-color: var(--vscode-toolbar-hoverBackground);
 }
 
@@ -32,16 +40,15 @@
 	outline-offset: -1px;
 }
 
-/* Center group: icon + label + folder + changes */
+/* Center group: icon + label + folder */
 .command-center .agent-sessions-titlebar-container .agent-sessions-titlebar-center {
 	display: flex;
 	align-items: center;
 	gap: 6px;
-	overflow: hidden;
-	justify-content: center;
+	min-width: 0;
+	justify-content: flex-start;
+	cursor: pointer;
 }
-
-/* Kind icon */
 .command-center .agent-sessions-titlebar-container .agent-sessions-titlebar-icon {
 	display: flex;
 	align-items: center;
@@ -70,34 +77,18 @@
 	flex-shrink: 0;
 }
 
-/* Changes container */
+/* Changes summary */
 .command-center .agent-sessions-titlebar-container .agent-sessions-titlebar-changes {
-	display: flex;
-	align-items: center;
-	gap: 3px;
-	cursor: pointer;
-	padding: 0 4px;
-	border-radius: 3px;
-}
-
-.command-center .agent-sessions-titlebar-container .agent-sessions-titlebar-changes:hover {
-	background-color: var(--vscode-toolbar-hoverBackground);
-}
-
-/* Changes icon */
-.command-center .agent-sessions-titlebar-container .agent-sessions-titlebar-changes-icon {
 	display: flex;
 	align-items: center;
 	flex-shrink: 0;
-	font-size: 14px;
+	gap: 3px;
 }
 
-/* Insertions */
-.command-center .agent-sessions-titlebar-container .agent-sessions-titlebar-added {
+.command-center .agent-sessions-titlebar-container .agent-sessions-titlebar-changes-added {
 	color: var(--vscode-gitDecoration-addedResourceForeground);
 }
 
-/* Deletions */
-.command-center .agent-sessions-titlebar-container .agent-sessions-titlebar-removed {
+.command-center .agent-sessions-titlebar-container .agent-sessions-titlebar-changes-removed {
 	color: var(--vscode-gitDecoration-deletedResourceForeground);
 }
diff --git a/src/vs/sessions/contrib/sessions/browser/sessions.contribution.ts b/src/vs/sessions/contrib/sessions/browser/sessions.contribution.ts
index b81e8fa62848f..52bd441711531 100644
--- a/src/vs/sessions/contrib/sessions/browser/sessions.contribution.ts
+++ b/src/vs/sessions/contrib/sessions/browser/sessions.contribution.ts
@@ -13,7 +13,6 @@ import { ViewPaneContainer } from '../../../../workbench/browser/parts/views/vie
 import { registerWorkbenchContribution2, WorkbenchPhase } from '../../../../workbench/common/contributions.js';
 import { InstantiationType, registerSingleton } from '../../../../platform/instantiation/common/extensions.js';
 import { SessionsTitleBarContribution } from './sessionsTitleBarWidget.js';
-import { SessionsAuxiliaryBarContribution } from './sessionsAuxiliaryBarContribution.js';
 import { AgenticSessionsViewPane, SessionsViewId } from './sessionsViewPane.js';
 import { SessionsManagementService, ISessionsManagementService } from './sessionsManagementService.js';
 
@@ -47,6 +46,5 @@ const agentSessionsViewDescriptor: IViewDescriptor = {
 Registry.as<IViewsRegistry>(ViewContainerExtensions.ViewsRegistry).registerViews([agentSessionsViewDescriptor], agentSessionsViewContainer);
 
 registerWorkbenchContribution2(SessionsTitleBarContribution.ID, SessionsTitleBarContribution, WorkbenchPhase.AfterRestored);
-registerWorkbenchContribution2(SessionsAuxiliaryBarContribution.ID, SessionsAuxiliaryBarContribution, WorkbenchPhase.AfterRestored);
 
 registerSingleton(ISessionsManagementService, SessionsManagementService, InstantiationType.Delayed);
diff --git a/src/vs/sessions/contrib/sessions/browser/sessionsManagementService.ts b/src/vs/sessions/contrib/sessions/browser/sessionsManagementService.ts
index 059c8e51cdd7f..463e338d24330 100644
--- a/src/vs/sessions/contrib/sessions/browser/sessionsManagementService.ts
+++ b/src/vs/sessions/contrib/sessions/browser/sessionsManagementService.ts
@@ -7,46 +7,56 @@ import { Disposable, DisposableStore, IDisposable, MutableDisposable } from '../
 import { CancellationToken } from '../../../../base/common/cancellation.js';
 import { IObservable, observableValue } from '../../../../base/common/observable.js';
 import { URI } from '../../../../base/common/uri.js';
+import { localize } from '../../../../nls.js';
 import { createDecorator, IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { IContextKey, IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
 import { ISessionOpenOptions, openSession as openSessionDefault } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsOpener.js';
-import { ChatViewPaneTarget, IChatWidgetService } from '../../../../workbench/contrib/chat/browser/chat.js';
+import { ChatViewPaneTarget, IChatWidget, IChatWidgetService } from '../../../../workbench/contrib/chat/browser/chat.js';
 import { IChatSessionProviderOptionItem, IChatSessionsService } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
 import { IChatService, IChatSendRequestOptions } from '../../../../workbench/contrib/chat/common/chatService/chatService.js';
-import { ChatAgentLocation, ChatModeKind } from '../../../../workbench/contrib/chat/common/constants.js';
+import { ChatAgentLocation, ChatModeKind, ChatPermissionLevel } from '../../../../workbench/contrib/chat/common/constants.js';
 import { IAgentSession, isAgentSession } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsModel.js';
 import { IAgentSessionsService } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
 import { ICommandService } from '../../../../platform/commands/common/commands.js';
 import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
 import { INewSession, LocalNewSession, RemoteNewSession } from '../../chat/browser/newSession.js';
 import { IUriIdentityService } from '../../../../platform/uriIdentity/common/uriIdentity.js';
+import { isBuiltinChatMode } from '../../../../workbench/contrib/chat/common/chatModes.js';
+import { ILanguageModelsService } from '../../../../workbench/contrib/chat/common/languageModels.js';
+import { ILanguageModelToolsService } from '../../../../workbench/contrib/chat/common/tools/languageModelToolsService.js';
+import { GITHUB_REMOTE_FILE_SCHEME } from '../../fileTreeView/browser/githubFileSystemProvider.js';
+import { IGitHubSessionContext } from '../../github/common/types.js';
+import { ResourceSet } from '../../../../base/common/map.js';
 
 export const IsNewChatSessionContext = new RawContextKey<boolean>('isNewChatSession', true);
 
+/**
+ * True when the active session uses the Background provider type (copilotcli).
+ * Used to gate actions that require a local worktree (run script, open in VS Code, terminal).
+ */
+export const IsActiveSessionBackgroundProviderContext = new RawContextKey<boolean>('isActiveSessionBackgroundProvider', false, localize('isActiveSessionBackgroundProvider', "Whether the active session uses the background agent provider"));
+
 //#region Active Session Service
 
 const LAST_SELECTED_SESSION_KEY = 'agentSessions.lastSelectedSession';
-const repositoryOptionId = 'repository';
 
 /**
  * An active session item extends IChatSessionItem with repository information.
  * - For agent session items: repository is the workingDirectory from metadata
  * - For new sessions: repository comes from the session option with id 'repository'
  */
-export type IActiveSessionItem = (INewSession | IAgentSession) & {
-	readonly label?: string;
-	/**
-	 * The repository URI for this session.
-	 */
+export interface IActiveSessionItem {
+	readonly resource: URI;
+	readonly isUntitled: boolean;
+	readonly label: string | undefined;
 	readonly repository: URI | undefined;
-
-	/**
-	 * The worktree URI for this session.
-	 */
 	readonly worktree: URI | undefined;
-};
+	readonly worktreeBranchName: string | undefined;
+	readonly worktreeBaseBranchProtected: boolean | undefined;
+	readonly providerType: string;
+}
 
 export interface ISessionsManagementService {
 	readonly _serviceBrand: undefined;
@@ -83,13 +93,30 @@ export interface ISessionsManagementService {
 	 * Open a new session, apply options, and send the initial request.
 	 * Looks up the session by resource URI and builds send options from it.
 	 */
-	sendRequestForNewSession(sessionResource: URI): Promise<void>;
+	sendRequestForNewSession(sessionResource: URI, options?: { permissionLevel?: ChatPermissionLevel }): Promise<void>;
 
 	/**
 	 * Commit files in a worktree and refresh the agent sessions model
 	 * so the Changes view reflects the update.
 	 */
 	commitWorktreeFiles(session: IActiveSessionItem, fileUris: URI[]): Promise<void>;
+
+	/**
+	 * Derive a GitHub context (owner, repo, prNumber) from an active session.
+	 * Returns `undefined` if the session is not associated with a GitHub repository.
+	 */
+	getGitHubContext(session: IActiveSessionItem): IGitHubSessionContext | undefined;
+
+	/**
+	 * Derive a GitHub context from a session resource URI.
+	 * Looks up the agent session internally and resolves repository info.
+	 */
+	getGitHubContextForSession(sessionResource: URI): IGitHubSessionContext | undefined;
+
+	/**
+	 * Resolve a relative file path to a full URI based on the session's repository/worktree.
+	 */
+	resolveSessionFileUri(sessionResource: URI, relativePath: string): URI | undefined;
 }
 
 export const ISessionsManagementService = createDecorator<ISessionsManagementService>('sessionsManagementService');
@@ -100,11 +127,12 @@ export class SessionsManagementService extends Disposable implements ISessionsMa
 
 	private readonly _activeSession = observableValue<IActiveSessionItem | undefined>(this, undefined);
 	readonly activeSession: IObservable<IActiveSessionItem | undefined> = this._activeSession;
-	private readonly _activeSessionDisposables = this._register(new DisposableStore());
+	private readonly _newActiveSessionDisposables = this._register(new DisposableStore());
 
 	private readonly _newSession = this._register(new MutableDisposable<INewSession>());
 	private lastSelectedSession: URI | undefined;
 	private readonly isNewChatSessionContext: IContextKey<boolean>;
+	private readonly _isBackgroundProvider: IContextKey<boolean>;
 
 	constructor(
 		@IStorageService private readonly storageService: IStorageService,
@@ -117,12 +145,15 @@ export class SessionsManagementService extends Disposable implements ISessionsMa
 		@ILogService private readonly logService: ILogService,
 		@IContextKeyService contextKeyService: IContextKeyService,
 		@ICommandService private readonly commandService: ICommandService,
+		@ILanguageModelsService private readonly languageModelsService: ILanguageModelsService,
+		@ILanguageModelToolsService private readonly toolsService: ILanguageModelToolsService,
 	) {
 		super();
 
 		// Bind context key to active session state.
 		// isNewSession is false when there are any established sessions in the model.
 		this.isNewChatSessionContext = IsNewChatSessionContext.bindTo(contextKeyService);
+		this._isBackgroundProvider = IsActiveSessionBackgroundProviderContext.bindTo(contextKeyService);
 
 		// Load last selected session
 		this.lastSelectedSession = this.loadLastSelectedSession();
@@ -150,18 +181,16 @@ export class SessionsManagementService extends Disposable implements ISessionsMa
 			return;
 		}
 
-		const agentSession = this.agentSessionsService.model.getSession(currentActive.resource);
-		if (!agentSession) {
-			// Only switch sessions if the active session was a known agent session
-			// that got deleted. New session resources that aren't yet in the model
-			// should not trigger a switch.
-			if (isAgentSession(currentActive)) {
-				this.showNextSession();
-			}
+		if (currentActive.isUntitled) {
 			return;
 		}
 
-		this.setActiveSession(agentSession);
+		const agentSession = this.agentSessionsService.model.getSession(currentActive.resource);
+		if (agentSession) {
+			this.setActiveSession(agentSession);
+		} else {
+			this.showNextSession();
+		}
 	}
 
 	private showNextSession(): void {
@@ -177,9 +206,26 @@ export class SessionsManagementService extends Disposable implements ISessionsMa
 		}
 	}
 
-	private getRepositoryFromMetadata(metadata: { readonly [key: string]: unknown } | undefined): [URI | undefined, URI | undefined] {
+	private getRepositoryFromMetadata(session: IAgentSession): [URI | undefined, URI | undefined, string | undefined, boolean | undefined] {
+		const metadata = session.metadata;
 		if (!metadata) {
-			return [undefined, undefined];
+			return [undefined, undefined, undefined, undefined];
+		}
+
+		if (session.providerType === AgentSessionProviders.Cloud) {
+			//TODO: @osortega pass branch in metadata from extension
+			const branch = typeof metadata.branch === 'string' ? metadata.branch : 'HEAD';
+			const repositoryUri = URI.from({
+				scheme: GITHUB_REMOTE_FILE_SCHEME,
+				authority: 'github',
+				path: `/${metadata.owner}/${metadata.name}/${encodeURIComponent(branch)}`
+			});
+			return [repositoryUri, undefined, undefined, undefined];
+		}
+
+		const workingDirectoryPath = metadata?.workingDirectoryPath as string | undefined;
+		if (workingDirectoryPath) {
+			return [URI.file(workingDirectoryPath), undefined, undefined, undefined];
 		}
 
 		const repositoryPath = metadata?.repositoryPath as string | undefined;
@@ -188,28 +234,14 @@ export class SessionsManagementService extends Disposable implements ISessionsMa
 		const worktreePath = metadata?.worktreePath as string | undefined;
 		const worktreePathUri = typeof worktreePath === 'string' ? URI.file(worktreePath) : undefined;
 
+		const worktreeBranchName = metadata?.branchName as string | undefined;
+		const worktreeBaseBranchProtected = metadata?.baseBranchProtected as boolean | undefined;
+
 		return [
 			URI.isUri(repositoryPathUri) ? repositoryPathUri : undefined,
-			URI.isUri(worktreePathUri) ? worktreePathUri : undefined];
-	}
-
-	private getRepositoryFromSessionOption(sessionResource: URI): URI | undefined {
-		const optionValue = this.chatSessionsService.getSessionOption(sessionResource, repositoryOptionId);
-		if (!optionValue) {
-			return undefined;
-		}
-
-		// Option value can be a string or IChatSessionProviderOptionItem
-		const optionId = typeof optionValue === 'string' ? optionValue : (optionValue as IChatSessionProviderOptionItem).id;
-		if (!optionId) {
-			return undefined;
-		}
-
-		try {
-			return URI.parse(optionId);
-		} catch {
-			return undefined;
-		}
+			URI.isUri(worktreePathUri) ? worktreePathUri : undefined,
+			worktreeBranchName,
+			worktreeBaseBranchProtected];
 	}
 
 	getActiveSession(): IActiveSessionItem | undefined {
@@ -217,13 +249,13 @@ export class SessionsManagementService extends Disposable implements ISessionsMa
 	}
 
 	async openSession(sessionResource: URI, openOptions?: ISessionOpenOptions): Promise<void> {
-		this.isNewChatSessionContext.set(false);
 		const existingSession = this.agentSessionsService.model.getSession(sessionResource);
-		if (existingSession) {
-			await this.openExistingSession(existingSession, openOptions);
-		} else if (this._newSession.value && this.uriIdentityService.extUri.isEqual(sessionResource, this._newSession.value.resource)) {
-			await this.openNewSession(this._newSession.value);
+		if (!existingSession) {
+			throw new Error(`Session with resource ${sessionResource.toString()} not found`);
 		}
+		this.isNewChatSessionContext.set(false);
+		this.setActiveSession(existingSession);
+		await this.instantiationService.invokeFunction(openSessionDefault, existingSession, openOptions);
 	}
 
 	async createNewSessionForTarget(target: AgentSessionProviders, sessionResource: URI, defaultRepoUri?: URI): Promise<INewSession> {
@@ -232,40 +264,17 @@ export class SessionsManagementService extends Disposable implements ISessionsMa
 		}
 
 		let newSession: INewSession;
-		if (target === AgentSessionProviders.Background || target === AgentSessionProviders.Local) {
-			newSession = new LocalNewSession(sessionResource, defaultRepoUri, this.chatSessionsService, this.logService);
+		if (target === AgentSessionProviders.Background) {
+			newSession = this.instantiationService.createInstance(LocalNewSession, sessionResource, defaultRepoUri);
 		} else {
-			newSession = new RemoteNewSession(sessionResource, target, this.chatSessionsService, this.logService);
+			newSession = this.instantiationService.createInstance(RemoteNewSession, sessionResource, target);
 		}
 		this._newSession.value = newSession;
 		this.setActiveSession(newSession);
 		return newSession;
 	}
 
-	/**
-	 * Open an existing agent session - set it as active and reveal it.
-	 */
-	private async openExistingSession(session: IAgentSession, openOptions?: ISessionOpenOptions): Promise<void> {
-		this.setActiveSession(session);
-		await this.instantiationService.invokeFunction(openSessionDefault, session, openOptions);
-	}
-
-	/**
-	 * Open a new remote session - load the model first, then show it in the ChatViewPane.
-	 */
-	private async openNewSession(newSession: INewSession): Promise<void> {
-		this.setActiveSession(newSession);
-		const sessionResource = newSession.resource;
-		const chatWidget = await this.chatWidgetService.openSession(sessionResource, ChatViewPaneTarget);
-		if (!chatWidget?.viewModel) {
-			this.logService.warn(`[ActiveSessionService] Failed to open session: ${sessionResource.toString()}`);
-			return;
-		}
-		const repository = this.getRepositoryFromSessionOption(sessionResource);
-		this.logService.info(`[ActiveSessionService] Active session changed (new): ${sessionResource.toString()}, repository: ${repository?.toString() ?? 'none'}`);
-	}
-
-	async sendRequestForNewSession(sessionResource: URI): Promise<void> {
+	async sendRequestForNewSession(sessionResource: URI, options?: { permissionLevel?: ChatPermissionLevel }): Promise<void> {
 		const session = this._newSession.value;
 		if (!session) {
 			this.logService.error(`[SessionsManagementService] No new session found for resource: ${sessionResource.toString()}`);
@@ -284,15 +293,30 @@ export class SessionsManagementService extends Disposable implements ISessionsMa
 		}
 
 		const contribution = this.chatSessionsService.getChatSessionContribution(session.target);
+
+		// Resolve mode from session's modeId (falls back to Agent)
+		const modeKind = session.mode?.kind ?? ChatModeKind.Agent;
+		const modeIsBuiltin = session.mode ? isBuiltinChatMode(session.mode) : true;
+		const modeId: 'ask' | 'agent' | 'edit' | 'custom' | undefined = modeIsBuiltin ? modeKind : 'custom';
+
+		const rawModeInstructions = session.mode?.modeInstructions?.get();
+		const modeInstructions = rawModeInstructions ? {
+			name: session.mode!.name.get(),
+			content: rawModeInstructions.content,
+			toolReferences: this.toolsService.toToolReferences(rawModeInstructions.toolReferences),
+			metadata: rawModeInstructions.metadata,
+		} : undefined;
+
 		const sendOptions: IChatSendRequestOptions = {
 			location: ChatAgentLocation.Chat,
 			userSelectedModelId: session.modelId,
 			modeInfo: {
-				kind: ChatModeKind.Agent,
-				isBuiltin: true,
-				modeInstructions: undefined,
-				modeId: 'agent',
+				kind: modeKind,
+				isBuiltin: modeIsBuiltin,
+				modeInstructions,
+				modeId,
 				applyCodeBlockSuggestionId: undefined,
+				permissionLevel: options?.permissionLevel ?? ChatPermissionLevel.Default,
 			},
 			agentIdSilent: contribution?.type,
 			attachedContext: session.attachedContext,
@@ -307,13 +331,67 @@ export class SessionsManagementService extends Disposable implements ISessionsMa
 
 	private async doSendRequestForNewSession(session: INewSession, query: string, sendOptions: IChatSendRequestOptions, selectedOptions?: ReadonlyMap<string, IChatSessionProviderOptionItem>): Promise<void> {
 		// 1. Open the session - loads the model and shows the ChatViewPane
-		await this.openSession(session.resource);
+		const chatWidget = await this.openNewSession(session);
+		const permissionLevel = sendOptions.modeInfo?.permissionLevel;
+		if (permissionLevel) {
+			chatWidget.input.setPermissionLevel(permissionLevel);
+		}
+
+		// 2. Load the session to apply selected options and have it ready when the view opens
+		await this.loadNewSession(session, selectedOptions);
+
+		//3. Send the initial request to kick off the session creation on the extension side
+		const existingResources = new ResourceSet(this.agentSessionsService.model.sessions.map(s => s.resource));
+		const result = await this.chatService.sendRequest(session.resource, query, sendOptions);
+		if (result.kind === 'rejected') {
+			this.logService.error(`[ActiveSessionService] sendRequest rejected: ${result.reason}`);
+			return;
+		}
+
+		// 4. This is just a heuristic to wait for the extension to create the session before trying to find the session associated with the chat widget, which is what we want to set as active.
+		// This allows to set the active session to the new session immediately instead of waiting for the chat widget to open, which results in a smoother user experience
+		const probableNewSession = await this.loadProbableNewAgentSession(session, existingResources);
+		this.setActiveSession(probableNewSession);
+
+		// 5. Wait for the real new session to appear in the chat widget
+		const newSession = await this.loadNewAgentSession(chatWidget, session);
+		this.setActiveSession(newSession);
+	}
+
+	private async openNewSession(session: INewSession): Promise<IChatWidget> {
+		this.isNewChatSessionContext.set(false);
+		const sessionResource = session.resource;
+		const chatWidget = await this.chatWidgetService.openSession(sessionResource, ChatViewPaneTarget);
+		if (!chatWidget) {
+			throw new Error(`Failed to open chat session for resource ${sessionResource.toString()}`);
+		}
+		return chatWidget;
+	}
 
-		// 2. Apply selected options (repository, branch, etc.) to the contributed session
-		if (selectedOptions && selectedOptions.size > 0) {
-			const modelRef = this.chatService.acquireExistingSession(session.resource);
-			if (modelRef) {
-				const model = modelRef.object;
+	private async loadNewSession(session: INewSession, selectedOptions?: ReadonlyMap<string, IChatSessionProviderOptionItem>): Promise<void> {
+		const modelRef = await this.chatService.acquireOrLoadSession(session.resource, ChatAgentLocation.Chat, CancellationToken.None);
+		if (modelRef) {
+			const model = modelRef.object;
+
+			// Set the selected model on the input model so the model picker reflects it
+			if (session.modelId) {
+				const languageModel = this.languageModelsService.lookupLanguageModel(session.modelId);
+				if (languageModel) {
+					model.inputModel.setState({
+						selectedModel: { identifier: session.modelId, metadata: languageModel }
+					});
+				}
+			}
+
+			// Set the selected mode on the input model so the mode picker reflects it
+			if (session.mode) {
+				model.inputModel.setState({
+					mode: { id: session.mode.id, kind: session.mode.kind }
+				});
+			}
+
+			// Apply selected options (repository, branch, etc.) to the contributed session
+			if (selectedOptions && selectedOptions.size > 0) {
 				const contributedSession = model.contributedChatSession;
 				if (contributedSession) {
 					const initialSessionOptions = [...selectedOptions.entries()].map(
@@ -324,45 +402,50 @@ export class SessionsManagementService extends Disposable implements ISessionsMa
 						initialSessionOptions,
 					});
 				}
-				modelRef.dispose();
 			}
+			modelRef.dispose();
 		}
+	}
 
-		// 3. Send the request
-		const existingResources = new Set(
-			this.agentSessionsService.model.sessions.map(s => s.resource.toString())
-		);
-		const result = await this.chatService.sendRequest(session.resource, query, sendOptions);
-		if (result.kind === 'rejected') {
-			this.logService.error(`[ActiveSessionService] sendRequest rejected: ${result.reason}`);
-			return;
+	private async loadProbableNewAgentSession(session: INewSession, existingSessions: ResourceSet): Promise<IAgentSession> {
+		const probableNewSession = this.agentSessionsService.model.sessions.find(s => s.providerType === session.target && !existingSessions.has(s.resource));
+		if (probableNewSession) {
+			return probableNewSession;
 		}
-
-		// 4. Wait for the extension to create an agent session, then set it as active
-		let newSession = this.agentSessionsService.model.sessions.find(
-			s => !existingResources.has(s.resource.toString())
-		);
-
-		if (!newSession) {
-			let listener: IDisposable | undefined;
-			newSession = await Promise.race([
-				new Promise<IAgentSession>(resolve => {
-					listener = this.agentSessionsService.model.onDidChangeSessions(() => {
-						const session = this.agentSessionsService.model.sessions.find(
-							s => !existingResources.has(s.resource.toString())
-						);
-						if (session) {
-							resolve(session);
-						}
-					});
-				}),
-				new Promise<undefined>(resolve => setTimeout(() => resolve(undefined), 30_000)),
-			]);
+		let listener: IDisposable | undefined;
+		try {
+			return await new Promise<IAgentSession>(resolve => {
+				listener = this.agentSessionsService.model.onDidChangeSessions(() => {
+					const s = this.agentSessionsService.model.sessions.find(s => s.providerType === session.target && !existingSessions.has(s.resource));
+					if (s) {
+						listener?.dispose();
+						resolve(s);
+					}
+				});
+			});
+		} finally {
 			listener?.dispose();
 		}
+	}
 
+	private async loadNewAgentSession(chatWidget: IChatWidget, session: INewSession): Promise<IAgentSession> {
+		const newSession = this.agentSessionsService.model.sessions.find(s => s.providerType === session.target && this.uriIdentityService.extUri.isEqual(s.resource, chatWidget.viewModel?.sessionResource));
 		if (newSession) {
-			this.setActiveSession(newSession);
+			return newSession;
+		}
+		let listener: IDisposable | undefined;
+		try {
+			return await new Promise<IAgentSession>(resolve => {
+				listener = chatWidget.onDidChangeViewModel(() => {
+					const s = this.agentSessionsService.model.sessions.find(s => s.providerType === session.target && this.uriIdentityService.extUri.isEqual(s.resource, chatWidget.viewModel?.sessionResource));
+					if (s) {
+						listener?.dispose();
+						resolve(s);
+					}
+				});
+			});
+		} finally {
+			listener?.dispose();
 		}
 	}
 
@@ -371,45 +454,92 @@ export class SessionsManagementService extends Disposable implements ISessionsMa
 		if (this.isNewChatSessionContext.get()) {
 			return;
 		}
+		this.setActiveSession(undefined);
 		this.isNewChatSessionContext.set(true);
-		this._activeSession.set(undefined, undefined);
 	}
 
 	private setActiveSession(session: IAgentSession | INewSession | undefined): void {
-		this._activeSessionDisposables.clear();
 		let activeSessionItem: IActiveSessionItem | undefined;
 		if (session) {
 			if (isAgentSession(session)) {
 				this.lastSelectedSession = session.resource;
-				const [repository, worktree] = this.getRepositoryFromMetadata(session.metadata);
+				const [repository, worktree, worktreeBranchName, worktreeBaseBranchProtected] = this.getRepositoryFromMetadata(session);
 				activeSessionItem = {
-					...session,
-					repository,
+					isUntitled: false,
+					label: session.label,
+					resource: session.resource,
+					repository: repository,
 					worktree,
+					worktreeBranchName: worktreeBranchName,
+					worktreeBaseBranchProtected: worktreeBaseBranchProtected === true,
+					providerType: session.providerType,
 				};
 			} else {
 				activeSessionItem = {
-					...session,
+					isUntitled: true,
+					label: undefined,
+					resource: session.resource,
 					repository: session.repoUri,
 					worktree: undefined,
+					worktreeBranchName: undefined,
+					worktreeBaseBranchProtected: undefined,
+					providerType: session.target,
 				};
-				this._activeSessionDisposables.add(session.onDidChange(e => {
+				this._newActiveSessionDisposables.clear();
+				this._newActiveSessionDisposables.add(session.onDidChange(e => {
 					if (e === 'repoUri') {
-						this._activeSession.set({
-							...session,
+						this.doSetActiveSession({
+							isUntitled: true,
+							label: undefined,
+							resource: session.resource,
 							repository: session.repoUri,
 							worktree: undefined,
-						}, undefined);
+							worktreeBranchName: undefined,
+							worktreeBaseBranchProtected: undefined,
+							providerType: session.target,
+						});
 					}
 				}));
 			}
-			this.logService.info(`[ActiveSessionService] Active session changed: ${session.resource.toString()}, repository: ${activeSessionItem.repository?.toString() ?? 'none'}`);
+		}
+
+		this.doSetActiveSession(activeSessionItem);
+	}
+
+	private doSetActiveSession(activeSessionItem: IActiveSessionItem | undefined): void {
+		if (this.equalsSessionItem(this._activeSession.get(), activeSessionItem)) {
+			return;
+		}
+
+		if (activeSessionItem) {
+			this.logService.info(`[ActiveSessionService] Active session changed: ${activeSessionItem.resource.toString()}`);
+			this.logService.trace(`[ActiveSessionService] Active session details: ${JSON.stringify(activeSessionItem)}`);
 		} else {
-			this.logService.info('[ActiveSessionService] Active session cleared');
+			this.logService.trace('[ActiveSessionService] Active session cleared');
 		}
+
+		this._isBackgroundProvider.set(activeSessionItem?.providerType === AgentSessionProviders.Background);
 		this._activeSession.set(activeSessionItem, undefined);
 	}
 
+	private equalsSessionItem(a: IActiveSessionItem | undefined, b: IActiveSessionItem | undefined): boolean {
+		if (a === b) {
+			return true;
+		}
+		if (!a || !b) {
+			return false;
+		}
+		return (
+			a.label === b.label &&
+			a.resource.toString() === b.resource.toString() &&
+			a.repository?.toString() === b.repository?.toString() &&
+			a.worktree?.toString() === b.worktree?.toString() &&
+			a.worktreeBranchName === b.worktreeBranchName &&
+			a.providerType === b.providerType &&
+			a.worktreeBaseBranchProtected === b.worktreeBaseBranchProtected
+		);
+	}
+
 	async commitWorktreeFiles(session: IActiveSessionItem, fileUris: URI[]): Promise<void> {
 		const worktreeUri = session.worktree;
 		if (!worktreeUri) {
@@ -424,6 +554,105 @@ export class SessionsManagementService extends Disposable implements ISessionsMa
 		await this.agentSessionsService.model.resolve(AgentSessionProviders.Background);
 	}
 
+	getGitHubContext(session: IActiveSessionItem): IGitHubSessionContext | undefined {
+		// 1. Try parsing a github-remote-file URI (Cloud sessions)
+		const repoUri = session.repository;
+		if (repoUri && repoUri.scheme === GITHUB_REMOTE_FILE_SCHEME) {
+			const parts = repoUri.path.split('/').filter(Boolean);
+			if (parts.length >= 2) {
+				const owner = decodeURIComponent(parts[0]);
+				const repo = decodeURIComponent(parts[1]);
+				const prNumber = this._parsePRNumberFromSession(session);
+				return { owner, repo, prNumber };
+			}
+		}
+
+		// 2. Try from agent session metadata (Background sessions)
+		const agentSession = this.agentSessionsService.model.getSession(session.resource);
+		if (agentSession?.metadata) {
+			const metadata = agentSession.metadata;
+
+			// owner + name fields
+			if (typeof metadata.owner === 'string' && typeof metadata.name === 'string') {
+				const prNumber = this._parsePRNumberFromSession(session);
+				return { owner: metadata.owner, repo: metadata.name, prNumber };
+			}
+
+			// repositoryNwo: "owner/repo"
+			if (typeof metadata.repositoryNwo === 'string') {
+				const parts = (metadata.repositoryNwo as string).split('/');
+				if (parts.length === 2) {
+					const prNumber = this._parsePRNumberFromSession(session);
+					return { owner: parts[0], repo: parts[1], prNumber };
+				}
+			}
+
+			// pullRequestUrl: "https://github.com/{owner}/{repo}/pull/{number}"
+			if (typeof metadata.pullRequestUrl === 'string') {
+				const match = /github\.com\/([^/]+)\/([^/]+)\/pull\/(\d+)/.exec(metadata.pullRequestUrl as string);
+				if (match) {
+					return { owner: match[1], repo: match[2], prNumber: parseInt(match[3], 10) };
+				}
+			}
+		}
+
+		return undefined;
+	}
+
+	getGitHubContextForSession(sessionResource: URI): IGitHubSessionContext | undefined {
+		const agentSession = this.agentSessionsService.model.getSession(sessionResource);
+		if (!agentSession) {
+			return undefined;
+		}
+		const [repository, worktree] = this.getRepositoryFromMetadata(agentSession);
+		return this.getGitHubContext({
+			resource: sessionResource,
+			isUntitled: false,
+			label: agentSession.label,
+			repository,
+			worktree,
+			worktreeBranchName: undefined,
+			worktreeBaseBranchProtected: undefined,
+			providerType: agentSession.providerType,
+		} satisfies IActiveSessionItem);
+	}
+
+	resolveSessionFileUri(sessionResource: URI, relativePath: string): URI | undefined {
+		const agentSession = this.agentSessionsService.model.getSession(sessionResource);
+		if (!agentSession) {
+			return undefined;
+		}
+		const [repository, worktree] = this.getRepositoryFromMetadata(agentSession);
+		const baseUri = worktree ?? repository;
+		if (!baseUri) {
+			return undefined;
+		}
+		return URI.joinPath(baseUri, relativePath);
+	}
+
+	private _parsePRNumberFromSession(session: IActiveSessionItem): number | undefined {
+		const agentSession = this.agentSessionsService.model.getSession(session.resource);
+		const metadata = agentSession?.metadata;
+		if (!metadata) {
+			return undefined;
+		}
+
+		// Direct prNumber field
+		if (typeof metadata.pullRequestNumber === 'number') {
+			return metadata.pullRequestNumber as number;
+		}
+
+		// Parse from pullRequestUrl: https://github.com/{owner}/{repo}/pull/{number}
+		if (typeof metadata.pullRequestUrl === 'string') {
+			const match = /\/pull\/(\d+)/.exec(metadata.pullRequestUrl as string);
+			if (match) {
+				return parseInt(match[1], 10);
+			}
+		}
+
+		return undefined;
+	}
+
 	private loadLastSelectedSession(): URI | undefined {
 		const cached = this.storageService.get(LAST_SELECTED_SESSION_KEY, StorageScope.WORKSPACE);
 		if (!cached) {
diff --git a/src/vs/sessions/contrib/sessions/browser/sessionsTitleBarWidget.ts b/src/vs/sessions/contrib/sessions/browser/sessionsTitleBarWidget.ts
index e21c25d56e9e7..08ae2d0a1e0e5 100644
--- a/src/vs/sessions/contrib/sessions/browser/sessionsTitleBarWidget.ts
+++ b/src/vs/sessions/contrib/sessions/browser/sessionsTitleBarWidget.ts
@@ -4,15 +4,23 @@
  *--------------------------------------------------------------------------------------------*/
 
 import './media/sessionsTitleBarWidget.css';
-import { $, addDisposableListener, EventType, reset } from '../../../../base/browser/dom.js';
+import { $, addDisposableListener, EventType, getActiveWindow, reset } from '../../../../base/browser/dom.js';
 
+import { Separator } from '../../../../base/common/actions.js';
 import { Disposable, DisposableStore, MutableDisposable } from '../../../../base/common/lifecycle.js';
+import { MarshalledId } from '../../../../base/common/marshallingIds.js';
+import { StandardMouseEvent } from '../../../../base/browser/mouseEvent.js';
 import { localize } from '../../../../nls.js';
 import { IHoverService } from '../../../../platform/hover/browser/hover.js';
 import { getDefaultHoverDelegate } from '../../../../base/browser/ui/hover/hoverDelegateFactory.js';
 import { BaseActionViewItem, IBaseActionViewItemOptions } from '../../../../base/browser/ui/actionbar/actionViewItems.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
-import { MenuRegistry, SubmenuItemAction } from '../../../../platform/actions/common/actions.js';
+import { IMenuService, MenuId, MenuRegistry, SubmenuItemAction } from '../../../../platform/actions/common/actions.js';
+import { IContextKeyService, ContextKeyExpr } from '../../../../platform/contextkey/common/contextkey.js';
+import { IContextMenuService } from '../../../../platform/contextview/browser/contextView.js';
+import { ChatContextKeys } from '../../../../workbench/contrib/chat/common/actions/chatContextKeys.js';
+import { IMarshalledAgentSessionContext, getAgentChangesSummary, hasValidDiff } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsModel.js';
+import { IChatSessionsService } from '../../../../workbench/contrib/chat/common/chatSessionsService.js';
 import { Menus } from '../../../browser/menus.js';
 import { IWorkbenchContribution } from '../../../../workbench/common/contributions.js';
 import { IActionViewItemService } from '../../../../platform/actions/browser/actionViewItemService.js';
@@ -24,13 +32,11 @@ import { AgentSessionsPicker } from '../../../../workbench/contrib/chat/browser/
 import { autorun } from '../../../../base/common/observable.js';
 import { IChatService } from '../../../../workbench/contrib/chat/common/chatService/chatService.js';
 import { ThemeIcon } from '../../../../base/common/themables.js';
+import { AgentSessionProviders, getAgentSessionProvider, getAgentSessionProviderIcon } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
 import { Codicon } from '../../../../base/common/codicons.js';
-import { getAgentChangesSummary, hasValidDiff, IAgentSession, isAgentSession } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsModel.js';
-import { getAgentSessionProvider, getAgentSessionProviderIcon } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
 import { basename } from '../../../../base/common/resources.js';
-import { ICommandService } from '../../../../platform/commands/common/commands.js';
-import { ViewAllSessionChangesAction } from '../../../../workbench/contrib/chat/browser/chatEditing/chatEditingActions.js';
 import { IsAuxiliaryWindowContext } from '../../../../workbench/common/contextkeys.js';
+import { SessionsWelcomeVisibleContext } from '../../../common/contextkeys.js';
 
 /**
  * Sessions Title Bar Widget - renders the active chat session title
@@ -40,7 +46,9 @@ import { IsAuxiliaryWindowContext } from '../../../../workbench/common/contextke
  * - Kind icon at the beginning (provider type icon)
  * - Session title
  * - Repository folder name
- * - Changes summary (+insertions -deletions)
+ *
+ * Session actions (changes, terminal, etc.) are rendered via the
+ * SessionTitleActions menu toolbar next to the session title.
  *
  * On click, opens the sessions picker.
  */
@@ -64,7 +72,10 @@ export class SessionsTitleBarWidget extends BaseActionViewItem {
 		@ISessionsManagementService private readonly activeSessionService: ISessionsManagementService,
 		@IChatService private readonly chatService: IChatService,
 		@IAgentSessionsService private readonly agentSessionsService: IAgentSessionsService,
-		@ICommandService private readonly commandService: ICommandService,
+		@IContextMenuService private readonly contextMenuService: IContextMenuService,
+		@IMenuService private readonly menuService: IMenuService,
+		@IContextKeyService private readonly contextKeyService: IContextKeyService,
+		@IChatSessionsService private readonly chatSessionsService: IChatSessionsService,
 	) {
 		super(undefined, action, options);
 
@@ -117,10 +128,10 @@ export class SessionsTitleBarWidget extends BaseActionViewItem {
 			const label = this._getActiveSessionLabel();
 			const icon = this._getActiveSessionIcon();
 			const repoLabel = this._getRepositoryLabel();
-			const changes = this._getChanges();
+			const changesSummary = this._getChangesSummary();
 
 			// Build a render-state key from all displayed data
-			const renderState = `${icon?.id ?? ''}|${label}|${repoLabel ?? ''}|${changes?.insertions ?? ''}|${changes?.deletions ?? ''}`;
+			const renderState = `${icon?.id ?? ''}|${label}|${repoLabel ?? ''}|${changesSummary?.insertions ?? ''}|${changesSummary?.deletions ?? ''}`;
 
 			// Skip re-render if state hasn't changed
 			if (this._lastRenderState === renderState) {
@@ -137,7 +148,10 @@ export class SessionsTitleBarWidget extends BaseActionViewItem {
 			this._container.setAttribute('aria-label', localize('agentSessionsShowSessions', "Show Sessions"));
 			this._container.tabIndex = 0;
 
-			// Center group: icon + label + folder + changes together
+			// Session pill: icon + label + folder together
+			const sessionPill = $('span.agent-sessions-titlebar-pill');
+
+			// Center group: icon + label + folder
 			const centerGroup = $('span.agent-sessions-titlebar-center');
 
 			// Kind icon at the beginning
@@ -151,74 +165,62 @@ export class SessionsTitleBarWidget extends BaseActionViewItem {
 			labelEl.textContent = label;
 			centerGroup.appendChild(labelEl);
 
-			// Folder and changes shown next to the title
-			if (repoLabel || changes) {
-				if (repoLabel) {
-					const separator1 = $('span.agent-sessions-titlebar-separator');
-					separator1.textContent = '\u00B7';
-					centerGroup.appendChild(separator1);
-
-					const repoEl = $('span.agent-sessions-titlebar-repo');
-					repoEl.textContent = repoLabel;
-					centerGroup.appendChild(repoEl);
-				}
-
-				if (changes) {
-					const separator2 = $('span.agent-sessions-titlebar-separator');
-					separator2.textContent = '\u00B7';
-					centerGroup.appendChild(separator2);
-
-					const changesEl = $('span.agent-sessions-titlebar-changes');
+			// Folder shown next to the title
+			if (repoLabel) {
+				const separator1 = $('span.agent-sessions-titlebar-separator');
+				separator1.textContent = '\u00B7';
+				centerGroup.appendChild(separator1);
 
-					// Diff icon
-					const changesIconEl = $('span.agent-sessions-titlebar-changes-icon' + ThemeIcon.asCSSSelector(Codicon.diffMultiple));
-					changesEl.appendChild(changesIconEl);
+				const repoEl = $('span.agent-sessions-titlebar-repo');
+				repoEl.textContent = repoLabel;
+				centerGroup.appendChild(repoEl);
+			}
 
-					const addedEl = $('span.agent-sessions-titlebar-added');
-					addedEl.textContent = `+${changes.insertions}`;
-					changesEl.appendChild(addedEl);
+			// Changes summary shown next to the repo
+			if (changesSummary) {
+				const separator2 = $('span.agent-sessions-titlebar-separator');
+				separator2.textContent = '\u00B7';
+				centerGroup.appendChild(separator2);
 
-					const removedEl = $('span.agent-sessions-titlebar-removed');
-					removedEl.textContent = `-${changes.deletions}`;
-					changesEl.appendChild(removedEl);
+				const changesEl = $('span.agent-sessions-titlebar-changes');
 
-					centerGroup.appendChild(changesEl);
+				const addedEl = $('span.agent-sessions-titlebar-changes-added');
+				addedEl.textContent = `+${changesSummary.insertions}`;
+				changesEl.appendChild(addedEl);
 
-					// Separate hover for changes
-					this._dynamicDisposables.add(this.hoverService.setupManagedHover(
-						getDefaultHoverDelegate('mouse'),
-						changesEl,
-						localize('agentSessions.viewChanges', "View All Changes")
-					));
+				const removedEl = $('span.agent-sessions-titlebar-changes-removed');
+				removedEl.textContent = `-${changesSummary.deletions}`;
+				changesEl.appendChild(removedEl);
 
-					// Click on changes opens multi-diff editor
-					this._dynamicDisposables.add(addDisposableListener(changesEl, EventType.CLICK, (e) => {
-						e.preventDefault();
-						e.stopPropagation();
-						this._openChanges();
-					}));
-				}
+				centerGroup.appendChild(changesEl);
 			}
 
-			this._container.appendChild(centerGroup);
+			sessionPill.appendChild(centerGroup);
 
-			// Hover
-			this._dynamicDisposables.add(this.hoverService.setupManagedHover(
-				getDefaultHoverDelegate('mouse'),
-				this._container,
-				label
-			));
-
-			// Click handler - show sessions picker
-			this._dynamicDisposables.add(addDisposableListener(this._container, EventType.MOUSE_DOWN, (e) => {
+			// Click handler on pill - show sessions picker
+			this._dynamicDisposables.add(addDisposableListener(sessionPill, EventType.MOUSE_DOWN, (e) => {
 				e.preventDefault();
 				e.stopPropagation();
 			}));
-			this._dynamicDisposables.add(addDisposableListener(this._container, EventType.CLICK, (e) => {
+			this._dynamicDisposables.add(addDisposableListener(sessionPill, EventType.CLICK, (e) => {
 				e.preventDefault();
 				e.stopPropagation();
 				this._showSessionsPicker();
 			}));
+			this._dynamicDisposables.add(addDisposableListener(sessionPill, EventType.CONTEXT_MENU, (e) => {
+				e.preventDefault();
+				e.stopPropagation();
+				this._showContextMenu(e);
+			}));
+
+			this._container.appendChild(sessionPill);
+
+			// Hover
+			this._dynamicDisposables.add(this.hoverService.setupManagedHover(
+				getDefaultHoverDelegate('mouse'),
+				sessionPill,
+				label
+			));
 
 			// Keyboard handler
 			this._dynamicDisposables.add(addDisposableListener(this._container, EventType.KEY_DOWN, (e: KeyboardEvent) => {
@@ -259,20 +261,19 @@ export class SessionsTitleBarWidget extends BaseActionViewItem {
 
 	/**
 	 * Get the label of the active chat session.
-	 * Prefers the live model title over the snapshot label from the active session service.
-	 * Falls back to a generic label if no active session is found.
 	 */
 	private _getActiveSessionLabel(): string {
 		const activeSession = this.activeSessionService.getActiveSession();
-		if (activeSession?.resource) {
-			const model = this.chatService.getSession(activeSession.resource);
-			if (model?.title) {
-				return model.title;
-			}
+		const label = activeSession?.label;
+		if (label) {
+			return label; // prefer session label to support renamed sessions
 		}
 
-		if (activeSession?.label) {
-			return activeSession.label;
+		if (activeSession) {
+			const activeModel = this.chatService.getSession(activeSession.resource);
+			if (activeModel?.title) {
+				return activeModel.title; // fall back to chat model title if available
+			}
 		}
 
 		return localize('agentSessions.newSession', "New Session");
@@ -290,6 +291,12 @@ export class SessionsTitleBarWidget extends BaseActionViewItem {
 		// Try to get icon from the agent session model (has provider-resolved icon)
 		const agentSession = this.agentSessionsService.getSession(activeSession.resource);
 		if (agentSession) {
+			// For background sessions, distinguish worktree vs folder based on metadata
+			if (agentSession.providerType === AgentSessionProviders.Background) {
+				const hasWorktree = typeof agentSession.metadata?.worktreePath === 'string';
+				return hasWorktree ? Codicon.worktree : Codicon.folder;
+			}
+
 			return agentSession.icon;
 		}
 
@@ -319,29 +326,58 @@ export class SessionsTitleBarWidget extends BaseActionViewItem {
 		return basename(uri);
 	}
 
-	/**
-	 * Get the changes summary (insertions/deletions) for the active session.
-	 */
-	private _getChanges(): { insertions: number; deletions: number } | undefined {
+	private _showContextMenu(e: MouseEvent): void {
 		const activeSession = this.activeSessionService.getActiveSession();
 		if (!activeSession) {
-			return undefined;
+			return;
+		}
+
+		const agentSession = this.agentSessionsService.getSession(activeSession.resource);
+		if (!agentSession) {
+			return;
 		}
 
-		let changes: IAgentSession['changes'] | undefined;
+		this.chatSessionsService.activateChatSessionItemProvider(agentSession.providerType);
+
+		const contextOverlay: Array<[string, boolean | string]> = [
+			[ChatContextKeys.isArchivedAgentSession.key, agentSession.isArchived()],
+			[ChatContextKeys.isReadAgentSession.key, agentSession.isRead()],
+			[ChatContextKeys.agentSessionType.key, agentSession.providerType],
+		];
+
+		const menu = this.menuService.createMenu(MenuId.AgentSessionsContext, this.contextKeyService.createOverlay(contextOverlay));
+
+		const marshalledContext: IMarshalledAgentSessionContext = {
+			session: agentSession,
+			sessions: [agentSession],
+			$mid: MarshalledId.AgentSessionContext,
+		};
+
+		this.contextMenuService.showContextMenu({
+			getActions: () => Separator.join(...menu.getActions({ arg: marshalledContext, shouldForwardArgs: true }).map(([, actions]) => actions)),
+			getAnchor: () => new StandardMouseEvent(getActiveWindow(), e),
+			getActionsContext: () => marshalledContext
+		});
+
+		menu.dispose();
+	}
 
-		if (isAgentSession(activeSession)) {
-			changes = activeSession.changes;
-		} else {
-			const agentSession = this.agentSessionsService.getSession(activeSession.resource);
-			changes = agentSession?.changes;
+	/**
+	 * Get the changes summary for the active session.
+	 */
+	private _getChangesSummary(): { insertions: number; deletions: number } | undefined {
+		const activeSession = this.activeSessionService.getActiveSession();
+		if (!activeSession) {
+			return undefined;
 		}
 
+		const agentSession = this.agentSessionsService.getSession(activeSession.resource);
+		const changes = agentSession?.changes;
 		if (!changes || !hasValidDiff(changes)) {
 			return undefined;
 		}
 
-		return getAgentChangesSummary(changes) ?? undefined;
+		return getAgentChangesSummary(changes);
 	}
 
 	private _showSessionsPicker(): void {
@@ -350,15 +386,6 @@ export class SessionsTitleBarWidget extends BaseActionViewItem {
 		});
 		picker.pickAgentSession();
 	}
-
-	private _openChanges(): void {
-		const activeSession = this.activeSessionService.getActiveSession();
-		if (!activeSession) {
-			return;
-		}
-
-		this.commandService.executeCommand(ViewAllSessionChangesAction.ID, activeSession.resource);
-	}
 }
 
 /**
@@ -378,14 +405,14 @@ export class SessionsTitleBarContribution extends Disposable implements IWorkben
 
 		// Register the submenu item in the Agent Sessions command center
 		this._register(MenuRegistry.appendMenuItem(Menus.CommandCenter, {
-			submenu: Menus.TitleBarControlMenu,
+			submenu: Menus.TitleBarSessionTitle,
 			title: localize('agentSessionsControl', "Agent Sessions"),
 			order: 101,
-			when: IsAuxiliaryWindowContext.negate()
+			when: ContextKeyExpr.and(IsAuxiliaryWindowContext.negate(), SessionsWelcomeVisibleContext.negate())
 		}));
 
 		// Register a placeholder action so the submenu appears
-		this._register(MenuRegistry.appendMenuItem(Menus.TitleBarControlMenu, {
+		this._register(MenuRegistry.appendMenuItem(Menus.TitleBarSessionTitle, {
 			command: {
 				id: FocusAgentSessionsAction.id,
 				title: localize('showSessions', "Show Sessions"),
@@ -395,7 +422,7 @@ export class SessionsTitleBarContribution extends Disposable implements IWorkben
 			when: IsAuxiliaryWindowContext.negate()
 		}));
 
-		this._register(actionViewItemService.register(Menus.CommandCenter, Menus.TitleBarControlMenu, (action, options) => {
+		this._register(actionViewItemService.register(Menus.CommandCenter, Menus.TitleBarSessionTitle, (action, options) => {
 			if (!(action instanceof SubmenuItemAction)) {
 				return undefined;
 			}
diff --git a/src/vs/sessions/contrib/sessions/browser/sessionsViewPane.ts b/src/vs/sessions/contrib/sessions/browser/sessionsViewPane.ts
index 9bef481d40592..cb9a87940253e 100644
--- a/src/vs/sessions/contrib/sessions/browser/sessionsViewPane.ts
+++ b/src/vs/sessions/contrib/sessions/browser/sessionsViewPane.ts
@@ -3,16 +3,13 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import '../../../browser/media/sidebarActionButton.css';
-import './media/customizationsToolbar.css';
 import './media/sessionsViewPane.css';
 import * as DOM from '../../../../base/browser/dom.js';
 import { Codicon } from '../../../../base/common/codicons.js';
 import { KeyCode, KeyMod } from '../../../../base/common/keyCodes.js';
-import { MutableDisposable } from '../../../../base/common/lifecycle.js';
 import { autorun } from '../../../../base/common/observable.js';
-import { ThemeIcon } from '../../../../base/common/themables.js';
-import { ContextKeyExpr, IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
+import { ContextKeyExpr, IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
+import { EditorsVisibleContext } from '../../../../workbench/common/contextkeys.js';
 import { IContextMenuService } from '../../../../platform/contextview/browser/contextView.js';
 import { IInstantiationService, ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
 import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
@@ -28,9 +25,7 @@ import { localize, localize2 } from '../../../../nls.js';
 import { AgentSessionsControl } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsControl.js';
 import { AgentSessionsFilter, AgentSessionsGrouping } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsFilter.js';
 import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
-import { IPromptsService } from '../../../../workbench/contrib/chat/common/promptSyntax/service/promptsService.js';
-import { IMcpService } from '../../../../workbench/contrib/mcp/common/mcpTypes.js';
-import { ISessionsManagementService } from './sessionsManagementService.js';
+import { ISessionsManagementService, IsNewChatSessionContext } from './sessionsManagementService.js';
 import { Action2, ISubmenuItem, MenuId, MenuRegistry, registerAction2 } from '../../../../platform/actions/common/actions.js';
 import { HoverPosition } from '../../../../base/browser/ui/hover/hoverWidget.js';
 import { IWorkbenchLayoutService } from '../../../../workbench/services/layout/browser/layoutService.js';
@@ -38,25 +33,24 @@ import { Button } from '../../../../base/browser/ui/button/button.js';
 import { defaultButtonStyles } from '../../../../platform/theme/browser/defaultStyles.js';
 import { KeybindingsRegistry, KeybindingWeight } from '../../../../platform/keybinding/common/keybindingsRegistry.js';
 import { ACTION_ID_NEW_CHAT } from '../../../../workbench/contrib/chat/browser/actions/chatActions.js';
-import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
-import { IWorkspaceContextService } from '../../../../platform/workspace/common/workspace.js';
 import { IViewsService } from '../../../../workbench/services/views/common/viewsService.js';
-import { HiddenItemStrategy, MenuWorkbenchToolBar } from '../../../../platform/actions/browser/toolbar.js';
-import { Menus } from '../../../browser/menus.js';
-import { getCustomizationTotalCount } from './customizationCounts.js';
+import { AICustomizationShortcutsWidget } from './aiCustomizationShortcutsWidget.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
+import { IHostService } from '../../../../workbench/services/host/browser/host.js';
 
 const $ = DOM.$;
 export const SessionsViewId = 'agentic.workbench.view.sessionsView';
 const SessionsViewFilterSubMenu = new MenuId('AgentSessionsViewFilterSubMenu');
-
-const CUSTOMIZATIONS_COLLAPSED_KEY = 'agentSessions.customizationsCollapsed';
+const IsGroupedByRepositoryContext = new RawContextKey<boolean>('sessionsView.isGroupedByRepository', false);
+const GROUPING_STORAGE_KEY = 'agentSessions.grouping';
 
 export class AgenticSessionsViewPane extends ViewPane {
 
 	private viewPaneContainer: HTMLElement | undefined;
 	private sessionsControlContainer: HTMLElement | undefined;
 	sessionsControl: AgentSessionsControl | undefined;
-	private aiCustomizationContainer: HTMLElement | undefined;
+	private currentGrouping: AgentSessionsGrouping = AgentSessionsGrouping.Date;
+	private isGroupedByRepoKey: ReturnType<typeof IsGroupedByRepositoryContext.bindTo> | undefined;
 
 	constructor(
 		options: IViewPaneOptions,
@@ -70,13 +64,17 @@ export class AgenticSessionsViewPane extends ViewPane {
 		@IThemeService themeService: IThemeService,
 		@IHoverService hoverService: IHoverService,
 		@IWorkbenchLayoutService private readonly layoutService: IWorkbenchLayoutService,
-		@IStorageService private readonly storageService: IStorageService,
-		@IPromptsService private readonly promptsService: IPromptsService,
-		@IMcpService private readonly mcpService: IMcpService,
-		@IWorkspaceContextService private readonly workspaceContextService: IWorkspaceContextService,
 		@ISessionsManagementService private readonly activeSessionService: ISessionsManagementService,
+		@IHostService private readonly hostService: IHostService,
+		@IStorageService private readonly storageService: IStorageService,
 	) {
 		super(options, keybindingService, contextMenuService, configurationService, contextKeyService, viewDescriptorService, instantiationService, openerService, themeService, hoverService);
+
+		// Restore persisted grouping
+		const stored = this.storageService.get(GROUPING_STORAGE_KEY, StorageScope.PROFILE);
+		if (stored && Object.values(AgentSessionsGrouping).includes(stored as AgentSessionsGrouping)) {
+			this.currentGrouping = stored as AgentSessionsGrouping;
+		}
 	}
 
 	protected override renderBody(parent: HTMLElement): void {
@@ -103,10 +101,14 @@ export class AgenticSessionsViewPane extends ViewPane {
 	private createControls(parent: HTMLElement): void {
 		const sessionsContainer = DOM.append(parent, $('.agent-sessions-container'));
 
+		// Track grouping state via context key for the toggle button
+		const isGroupedByRepoKey = this.isGroupedByRepoKey = IsGroupedByRepositoryContext.bindTo(this.contextKeyService);
+		isGroupedByRepoKey.set(this.currentGrouping === AgentSessionsGrouping.Repository);
+
 		// Sessions Filter (actions go to view title bar via menu registration)
 		const sessionsFilter = this._register(this.instantiationService.createInstance(AgentSessionsFilter, {
 			filterMenuId: SessionsViewFilterSubMenu,
-			groupResults: () => AgentSessionsGrouping.Date,
+			groupResults: () => this.currentGrouping,
 			allowedProviders: [AgentSessionProviders.Background, AgentSessionProviders.Cloud],
 			providerLabelOverrides: new Map([
 				[AgentSessionProviders.Background, localize('chat.session.providerLabel.local', "Local")],
@@ -139,6 +141,8 @@ export class AgenticSessionsViewPane extends ViewPane {
 			filter: sessionsFilter,
 			overrideStyles: this.getLocationBasedColors().listOverrideStyles,
 			disableHover: true,
+			showIsolationIcon: true,
+			enableApprovalRow: true,
 			getHoverPosition: () => this.getSessionHoverPosition(),
 			trackActiveEditorSession: () => true,
 			collapseOlderSections: () => true,
@@ -146,6 +150,13 @@ export class AgenticSessionsViewPane extends ViewPane {
 		}));
 		this._register(this.onDidChangeBodyVisibility(visible => sessionsControl.setVisible(visible)));
 
+		// Refresh sessions when window gets focus to compensate for missing events
+		this._register(this.hostService.onDidChangeFocus(hasFocus => {
+			if (hasFocus) {
+				sessionsControl.refresh();
+			}
+		}));
+
 		// Listen to tree updates and restore selection if nothing is selected
 		this._register(sessionsControl.onDidUpdate(() => {
 			if (!sessionsControl.hasFocusOrSelection()) {
@@ -166,8 +177,14 @@ export class AgenticSessionsViewPane extends ViewPane {
 		}));
 
 		// AI Customization toolbar (bottom, fixed height)
-		this.aiCustomizationContainer = DOM.append(sessionsContainer, $('div'));
-		this.createAICustomizationShortcuts(this.aiCustomizationContainer);
+		this._register(this.instantiationService.createInstance(AICustomizationShortcutsWidget, sessionsContainer, {
+			onDidToggleCollapse: () => {
+				if (this.viewPaneContainer) {
+					const { offsetHeight, offsetWidth } = this.viewPaneContainer;
+					this.layoutBody(offsetHeight, offsetWidth);
+				}
+			},
+		}));
 	}
 
 	private restoreLastSelectedSession(): void {
@@ -177,92 +194,6 @@ export class AgenticSessionsViewPane extends ViewPane {
 		}
 	}
 
-	private createAICustomizationShortcuts(container: HTMLElement): void {
-		// Get initial collapsed state
-		const isCollapsed = this.storageService.getBoolean(CUSTOMIZATIONS_COLLAPSED_KEY, StorageScope.PROFILE, false);
-
-		container.classList.add('ai-customization-toolbar');
-		if (isCollapsed) {
-			container.classList.add('collapsed');
-		}
-
-		// Header (clickable to toggle)
-		const header = DOM.append(container, $('.ai-customization-header'));
-		header.classList.toggle('collapsed', isCollapsed);
-
-		const headerButtonContainer = DOM.append(header, $('.customization-link-button-container'));
-		const headerButton = this._register(new Button(headerButtonContainer, {
-			...defaultButtonStyles,
-			secondary: true,
-			title: false,
-			supportIcons: true,
-			buttonSecondaryBackground: 'transparent',
-			buttonSecondaryHoverBackground: undefined,
-			buttonSecondaryForeground: undefined,
-			buttonSecondaryBorder: undefined,
-		}));
-		headerButton.element.classList.add('customization-link-button', 'sidebar-action-button');
-		headerButton.element.setAttribute('aria-expanded', String(!isCollapsed));
-		headerButton.label = localize('customizations', "CUSTOMIZATIONS");
-
-		const chevronContainer = DOM.append(headerButton.element, $('span.customization-link-counts'));
-		const chevron = DOM.append(chevronContainer, $('.ai-customization-chevron'));
-		const headerTotalCount = DOM.append(chevronContainer, $('span.ai-customization-header-total.hidden'));
-		chevron.classList.add(...ThemeIcon.asClassNameArray(isCollapsed ? Codicon.chevronRight : Codicon.chevronDown));
-
-		// Toolbar container
-		const toolbarContainer = DOM.append(container, $('.ai-customization-toolbar-content.sidebar-action-list'));
-
-		this._register(this.instantiationService.createInstance(MenuWorkbenchToolBar, toolbarContainer, Menus.SidebarCustomizations, {
-			hiddenItemStrategy: HiddenItemStrategy.NoHide,
-			toolbarOptions: { primaryGroup: () => true },
-			telemetrySource: 'sidebarCustomizations',
-		}));
-
-		let updateCountRequestId = 0;
-		const updateHeaderTotalCount = async () => {
-			const requestId = ++updateCountRequestId;
-			const totalCount = await getCustomizationTotalCount(this.promptsService, this.mcpService);
-			if (requestId !== updateCountRequestId) {
-				return;
-			}
-
-			headerTotalCount.classList.toggle('hidden', totalCount === 0);
-			headerTotalCount.textContent = `${totalCount}`;
-		};
-
-		this._register(this.promptsService.onDidChangeCustomAgents(() => updateHeaderTotalCount()));
-		this._register(this.promptsService.onDidChangeSlashCommands(() => updateHeaderTotalCount()));
-		this._register(this.workspaceContextService.onDidChangeWorkspaceFolders(() => updateHeaderTotalCount()));
-		this._register(autorun(reader => {
-			this.mcpService.servers.read(reader);
-			updateHeaderTotalCount();
-		}));
-		updateHeaderTotalCount();
-
-		// Toggle collapse on header click
-		const transitionListener = this._register(new MutableDisposable());
-		const toggleCollapse = () => {
-			const collapsed = container.classList.toggle('collapsed');
-			header.classList.toggle('collapsed', collapsed);
-			this.storageService.store(CUSTOMIZATIONS_COLLAPSED_KEY, collapsed, StorageScope.PROFILE, StorageTarget.USER);
-			headerButton.element.setAttribute('aria-expanded', String(!collapsed));
-			chevron.classList.remove(...ThemeIcon.asClassNameArray(Codicon.chevronRight), ...ThemeIcon.asClassNameArray(Codicon.chevronDown));
-			chevron.classList.add(...ThemeIcon.asClassNameArray(collapsed ? Codicon.chevronRight : Codicon.chevronDown));
-
-			// Re-layout after the transition so sessions control gets the right height
-			transitionListener.value = DOM.addDisposableListener(toolbarContainer, 'transitionend', () => {
-				transitionListener.clear();
-				if (this.viewPaneContainer) {
-					const { offsetHeight, offsetWidth } = this.viewPaneContainer;
-					this.layoutBody(offsetHeight, offsetWidth);
-				}
-			});
-		};
-
-		this._register(headerButton.onDidClick(() => toggleCollapse()));
-	}
-
 	private getSessionHoverPosition(): HoverPosition {
 		const viewLocation = this.viewDescriptorService.getViewLocationById(this.id);
 		const sideBarPosition = this.layoutService.getSideBarPosition();
@@ -298,6 +229,18 @@ export class AgenticSessionsViewPane extends ViewPane {
 	openFind(): void {
 		this.sessionsControl?.openFind();
 	}
+
+	toggleGroupByRepository(): void {
+		if (this.currentGrouping === AgentSessionsGrouping.Repository) {
+			this.currentGrouping = AgentSessionsGrouping.Date;
+		} else {
+			this.currentGrouping = AgentSessionsGrouping.Repository;
+		}
+
+		this.storageService.store(GROUPING_STORAGE_KEY, this.currentGrouping, StorageScope.PROFILE, StorageTarget.USER);
+		this.isGroupedByRepoKey?.set(this.currentGrouping === AgentSessionsGrouping.Repository);
+		this.sessionsControl?.update();
+	}
 }
 
 // Register Cmd+N / Ctrl+N keybinding for new session in the agent sessions window
@@ -307,6 +250,33 @@ KeybindingsRegistry.registerKeybindingRule({
 	primary: KeyMod.CtrlCmd | KeyCode.KeyN,
 });
 
+const CLOSE_SESSION_COMMAND_ID = 'agentSession.close';
+registerAction2(class CloseSessionAction extends Action2 {
+	constructor() {
+		super({
+			id: CLOSE_SESSION_COMMAND_ID,
+			title: localize2('closeSession', "Close Session"),
+			f1: true,
+			precondition: ContextKeyExpr.and(IsNewChatSessionContext.negate(), EditorsVisibleContext.negate()),
+			category: SessionsCategories.Sessions,
+		});
+	}
+	override async run(accessor: ServicesAccessor) {
+		const sessionsService = accessor.get(ISessionsManagementService);
+		await sessionsService.openNewSessionView();
+	}
+});
+
+// Register Cmd+W / Ctrl+W to close the current session and navigate to the new-session view,
+// mirroring how Cmd+W closes the active editor in the normal workbench.
+KeybindingsRegistry.registerKeybindingRule({
+	id: CLOSE_SESSION_COMMAND_ID,
+	weight: KeybindingWeight.WorkbenchContrib + 1,
+	when: ContextKeyExpr.and(IsNewChatSessionContext.negate(), EditorsVisibleContext.negate()),
+	primary: KeyMod.CtrlCmd | KeyCode.KeyW,
+	win: { primary: KeyMod.CtrlCmd | KeyCode.F4, secondary: [KeyMod.CtrlCmd | KeyCode.KeyW] },
+});
+
 MenuRegistry.appendMenuItem(MenuId.ViewTitle, {
 	submenu: SessionsViewFilterSubMenu,
 	title: localize2('filterAgentSessions', "Filter Sessions"),
@@ -316,6 +286,52 @@ MenuRegistry.appendMenuItem(MenuId.ViewTitle, {
 	when: ContextKeyExpr.equals('view', SessionsViewId)
 } satisfies ISubmenuItem);
 
+registerAction2(class GroupByRepositoryAction extends Action2 {
+	constructor() {
+		super({
+			id: 'sessionsView.groupByRepository',
+			title: localize2('groupByRepository', "Group by Repository"),
+			icon: Codicon.repo,
+			category: SessionsCategories.Sessions,
+			menu: [{
+				id: MenuId.ViewTitle,
+				group: 'navigation',
+				order: 1,
+				when: ContextKeyExpr.and(ContextKeyExpr.equals('view', SessionsViewId), IsGroupedByRepositoryContext.negate()),
+			}]
+		});
+	}
+
+	override run(accessor: ServicesAccessor) {
+		const viewsService = accessor.get(IViewsService);
+		const view = viewsService.getViewWithId<AgenticSessionsViewPane>(SessionsViewId);
+		view?.toggleGroupByRepository();
+	}
+});
+
+registerAction2(class GroupByDateAction extends Action2 {
+	constructor() {
+		super({
+			id: 'sessionsView.groupByDate',
+			title: localize2('groupByDate', "Group by Date"),
+			icon: Codicon.history,
+			category: SessionsCategories.Sessions,
+			menu: [{
+				id: MenuId.ViewTitle,
+				group: 'navigation',
+				order: 1,
+				when: ContextKeyExpr.and(ContextKeyExpr.equals('view', SessionsViewId), IsGroupedByRepositoryContext),
+			}]
+		});
+	}
+
+	override run(accessor: ServicesAccessor) {
+		const viewsService = accessor.get(IViewsService);
+		const view = viewsService.getViewWithId<AgenticSessionsViewPane>(SessionsViewId);
+		view?.toggleGroupByRepository();
+	}
+});
+
 registerAction2(class RefreshAgentSessionsViewerAction extends Action2 {
 	constructor() {
 		super({
diff --git a/src/vs/sessions/contrib/sessions/test/browser/aiCustomizationShortcutsWidget.fixture.ts b/src/vs/sessions/contrib/sessions/test/browser/aiCustomizationShortcutsWidget.fixture.ts
new file mode 100644
index 0000000000000..0f4a7bf7a28b3
--- /dev/null
+++ b/src/vs/sessions/contrib/sessions/test/browser/aiCustomizationShortcutsWidget.fixture.ts
@@ -0,0 +1,271 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { toAction } from '../../../../../base/common/actions.js';
+import { Emitter, Event } from '../../../../../base/common/event.js';
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { observableValue } from '../../../../../base/common/observable.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { mock } from '../../../../../base/test/common/mock.js';
+import { IActionViewItemFactory, IActionViewItemService } from '../../../../../platform/actions/browser/actionViewItemService.js';
+import { IMenu, IMenuActionOptions, IMenuService, isIMenuItem, MenuId, MenuItemAction, MenuRegistry, SubmenuItemAction } from '../../../../../platform/actions/common/actions.js';
+import { IStorageService, StorageScope } from '../../../../../platform/storage/common/storage.js';
+import { IFileService } from '../../../../../platform/files/common/files.js';
+import { IWorkspace, IWorkspaceContextService } from '../../../../../platform/workspace/common/workspace.js';
+import { IPromptsService, PromptsStorage } from '../../../../../workbench/contrib/chat/common/promptSyntax/service/promptsService.js';
+import { PromptsType } from '../../../../../workbench/contrib/chat/common/promptSyntax/promptTypes.js';
+import { ILanguageModelsService } from '../../../../../workbench/contrib/chat/common/languageModels.js';
+import { IMcpServer, IMcpService } from '../../../../../workbench/contrib/mcp/common/mcpTypes.js';
+import { IAICustomizationWorkspaceService, IStorageSourceFilter } from '../../../../../workbench/contrib/chat/common/aiCustomizationWorkspaceService.js';
+import { IAgentPluginService } from '../../../../../workbench/contrib/chat/common/plugins/agentPluginService.js';
+import { ComponentFixtureContext, createEditorServices, defineComponentFixture, defineThemedFixtureGroup, registerWorkbenchServices } from '../../../../../workbench/test/browser/componentFixtures/fixtureUtils.js';
+import { AICustomizationShortcutsWidget } from '../../browser/aiCustomizationShortcutsWidget.js';
+import { CUSTOMIZATION_ITEMS, CustomizationLinkViewItem } from '../../browser/customizationsToolbar.contribution.js';
+import { IActiveSessionItem, ISessionsManagementService } from '../../browser/sessionsManagementService.js';
+import { Menus } from '../../../../browser/menus.js';
+
+// Ensure color registrations are loaded
+import '../../../../common/theme.js';
+import '../../../../../platform/theme/common/colors/inputColors.js';
+
+// ============================================================================
+// One-time menu item registration (module-level).
+// MenuRegistry.appendMenuItem does not throw on duplicates, unlike registerAction2
+// which registers global commands and throws on the second call.
+// ============================================================================
+
+const menuRegistrations = new DisposableStore();
+for (const [index, config] of CUSTOMIZATION_ITEMS.entries()) {
+	menuRegistrations.add(MenuRegistry.appendMenuItem(Menus.SidebarCustomizations, {
+		command: { id: config.id, title: config.label },
+		group: 'navigation',
+		order: index + 1,
+	}));
+}
+
+// ============================================================================
+// FixtureMenuService — reads from MenuRegistry without context-key filtering
+// (MockContextKeyService.contextMatchesRules always returns false, which hides
+// every item when using the real MenuService.)
+// ============================================================================
+
+class FixtureMenuService implements IMenuService {
+	declare readonly _serviceBrand: undefined;
+
+	createMenu(id: MenuId): IMenu {
+		return {
+			onDidChange: Event.None,
+			dispose: () => { },
+			getActions: () => {
+				const items = MenuRegistry.getMenuItems(id).filter(isIMenuItem);
+				items.sort((a, b) => (a.order ?? 0) - (b.order ?? 0));
+				const actions = items.map(item => {
+					const title = typeof item.command.title === 'string' ? item.command.title : item.command.title.value;
+					return toAction({ id: item.command.id, label: title, run: () => { } });
+				});
+				return actions.length ? [['navigation', actions as unknown as (MenuItemAction | SubmenuItemAction)[]]] : [];
+			},
+		};
+	}
+
+	getMenuActions(_id: MenuId, _contextKeyService: unknown, _options?: IMenuActionOptions) { return []; }
+	getMenuContexts() { return new Set<string>(); }
+	resetHiddenStates() { }
+}
+
+// ============================================================================
+// Minimal IActionViewItemService that supports register/lookUp
+// ============================================================================
+
+class FixtureActionViewItemService implements IActionViewItemService {
+	declare _serviceBrand: undefined;
+
+	private readonly _providers = new Map<string, IActionViewItemFactory>();
+	private readonly _onDidChange = new Emitter<MenuId>();
+	readonly onDidChange = this._onDidChange.event;
+
+	register(menu: MenuId, commandId: string | MenuId, provider: IActionViewItemFactory): { dispose(): void } {
+		const key = `${menu.id}/${commandId instanceof MenuId ? commandId.id : commandId}`;
+		this._providers.set(key, provider);
+		return { dispose: () => { this._providers.delete(key); } };
+	}
+
+	lookUp(menu: MenuId, commandId: string | MenuId): IActionViewItemFactory | undefined {
+		const key = `${menu.id}/${commandId instanceof MenuId ? commandId.id : commandId}`;
+		return this._providers.get(key);
+	}
+}
+
+// ============================================================================
+// Mock helpers
+// ============================================================================
+
+const defaultFilter: IStorageSourceFilter = {
+	sources: [PromptsStorage.local, PromptsStorage.user, PromptsStorage.extension],
+};
+
+function createMockPromptsService(): IPromptsService {
+	return createMockPromptsServiceWithCounts();
+}
+
+interface ICustomizationCounts {
+	readonly agents?: number;
+	readonly skills?: number;
+	readonly instructions?: number;
+	readonly prompts?: number;
+	readonly hooks?: number;
+}
+
+function createMockPromptsServiceWithCounts(counts?: ICustomizationCounts): IPromptsService {
+	const fakeUri = (prefix: string, i: number) => URI.parse(`file:///mock/${prefix}-${i}.md`);
+	const fakeItem = (prefix: string, i: number) => ({ uri: fakeUri(prefix, i), storage: PromptsStorage.local });
+
+	const agents = Array.from({ length: counts?.agents ?? 0 }, (_, i) => ({
+		uri: fakeUri('agent', i),
+		source: { storage: PromptsStorage.local },
+	}));
+	const skills = Array.from({ length: counts?.skills ?? 0 }, (_, i) => fakeItem('skill', i));
+	const prompts = Array.from({ length: counts?.prompts ?? 0 }, (_, i) => ({
+		promptPath: { uri: fakeUri('prompt', i), storage: PromptsStorage.local, type: PromptsType.prompt },
+	}));
+	const instructions = Array.from({ length: counts?.instructions ?? 0 }, (_, i) => fakeItem('instructions', i));
+	const hooks = Array.from({ length: counts?.hooks ?? 0 }, (_, i) => fakeItem('hook', i));
+
+	return new class extends mock<IPromptsService>() {
+		override readonly onDidChangeCustomAgents = Event.None;
+		override readonly onDidChangeSlashCommands = Event.None;
+		override async getCustomAgents() { return agents as never[]; }
+		override async findAgentSkills() { return skills as never[]; }
+		override async getPromptSlashCommands() { return prompts as never[]; }
+		override async listPromptFiles(type: PromptsType) {
+			return (type === PromptsType.hook ? hooks : instructions) as never[];
+		}
+		override async listAgentInstructions() { return [] as never[]; }
+	}();
+}
+
+function createMockMcpService(serverCount: number = 0): IMcpService {
+	const MockServer = mock<IMcpServer>();
+	const servers = observableValue<readonly IMcpServer[]>('mockMcpServers', Array.from({ length: serverCount }, () => new MockServer()));
+	return new class extends mock<IMcpService>() {
+		override readonly servers = servers;
+	}();
+}
+
+function createMockWorkspaceService(): IAICustomizationWorkspaceService {
+	const activeProjectRoot = observableValue<URI | undefined>('mockActiveProjectRoot', undefined);
+	return new class extends mock<IAICustomizationWorkspaceService>() {
+		override readonly activeProjectRoot = activeProjectRoot;
+		override getActiveProjectRoot() { return undefined; }
+		override getStorageSourceFilter() { return defaultFilter; }
+	}();
+}
+
+function createMockWorkspaceContextService(): IWorkspaceContextService {
+	return new class extends mock<IWorkspaceContextService>() {
+		override readonly onDidChangeWorkspaceFolders = Event.None;
+		override getWorkspace(): IWorkspace { return { id: 'test', folders: [] }; }
+	}();
+}
+
+// ============================================================================
+// Render helper
+// ============================================================================
+
+function renderWidget(ctx: ComponentFixtureContext, options?: { mcpServerCount?: number; collapsed?: boolean; counts?: ICustomizationCounts }): void {
+	ctx.container.style.width = '300px';
+	ctx.container.style.backgroundColor = 'var(--vscode-sideBar-background)';
+
+	const actionViewItemService = new FixtureActionViewItemService();
+
+	const instantiationService = createEditorServices(ctx.disposableStore, {
+		colorTheme: ctx.theme,
+		additionalServices: (reg) => {
+			// Register overrides BEFORE registerWorkbenchServices so they take priority
+			reg.defineInstance(IMenuService, new FixtureMenuService());
+			reg.defineInstance(IActionViewItemService, actionViewItemService);
+			registerWorkbenchServices(reg);
+			// Services needed by AICustomizationShortcutsWidget
+			reg.defineInstance(IPromptsService, options?.counts ? createMockPromptsServiceWithCounts(options.counts) : createMockPromptsService());
+			reg.defineInstance(IMcpService, createMockMcpService(options?.mcpServerCount ?? 0));
+			reg.defineInstance(IAICustomizationWorkspaceService, createMockWorkspaceService());
+			reg.defineInstance(IWorkspaceContextService, createMockWorkspaceContextService());
+			reg.defineInstance(IAgentPluginService, new class extends mock<IAgentPluginService>() {
+				override readonly plugins = observableValue<readonly never[]>('mockPlugins', []);
+			}());
+			// Additional services needed by CustomizationLinkViewItem
+			reg.defineInstance(ILanguageModelsService, new class extends mock<ILanguageModelsService>() {
+				override readonly onDidChangeLanguageModels = Event.None;
+			}());
+			reg.defineInstance(ISessionsManagementService, new class extends mock<ISessionsManagementService>() {
+				override readonly activeSession = observableValue<IActiveSessionItem | undefined>('activeSession', undefined);
+			}());
+			reg.defineInstance(IFileService, new class extends mock<IFileService>() {
+				override readonly onDidFilesChange = Event.None;
+			}());
+		},
+	});
+
+	// Register view item factories from the real CustomizationLinkViewItem (per-render, instance-scoped)
+	for (const config of CUSTOMIZATION_ITEMS) {
+		ctx.disposableStore.add(actionViewItemService.register(Menus.SidebarCustomizations, config.id, (action, options) => {
+			return instantiationService.createInstance(CustomizationLinkViewItem, action, options, config);
+		}));
+	}
+
+	// Override storage to set initial collapsed state
+	if (options?.collapsed) {
+		const storageService = instantiationService.get(IStorageService);
+		instantiationService.set(IStorageService, new class extends mock<IStorageService>() {
+			override getBoolean(key: string, scope: StorageScope, fallbackValue?: boolean) {
+				if (key === 'agentSessions.customizationsCollapsed') {
+					return true;
+				}
+				return storageService.getBoolean(key, scope, fallbackValue!);
+			}
+			override store() { }
+		}());
+	}
+
+	// Create the widget (uses FixtureMenuService → reads MenuRegistry items registered above)
+	ctx.disposableStore.add(
+		instantiationService.createInstance(AICustomizationShortcutsWidget, ctx.container, undefined)
+	);
+}
+
+// ============================================================================
+// Fixtures
+// ============================================================================
+
+export default defineThemedFixtureGroup({ path: 'sessions/' }, {
+
+	Expanded: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (ctx) => renderWidget(ctx),
+	}),
+
+	Collapsed: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (ctx) => renderWidget(ctx, { collapsed: true }),
+	}),
+
+	WithMcpServers: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (ctx) => renderWidget(ctx, { mcpServerCount: 3 }),
+	}),
+
+	CollapsedWithMcpServers: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (ctx) => renderWidget(ctx, { mcpServerCount: 3, collapsed: true }),
+	}),
+
+	WithCounts: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (ctx) => renderWidget(ctx, {
+			mcpServerCount: 2,
+			counts: { agents: 2, skills: 30, instructions: 16, prompts: 17, hooks: 4 },
+		}),
+	}),
+});
diff --git a/src/vs/sessions/contrib/sessions/test/browser/customizationCounts.test.ts b/src/vs/sessions/contrib/sessions/test/browser/customizationCounts.test.ts
new file mode 100644
index 0000000000000..02d70905b805c
--- /dev/null
+++ b/src/vs/sessions/contrib/sessions/test/browser/customizationCounts.test.ts
@@ -0,0 +1,796 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { URI } from '../../../../../base/common/uri.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { PromptsType } from '../../../../../workbench/contrib/chat/common/promptSyntax/promptTypes.js';
+import { IPromptsService, PromptsStorage, IPromptPath, ILocalPromptPath, IUserPromptPath, IExtensionPromptPath, IResolvedAgentFile, AgentFileType } from '../../../../../workbench/contrib/chat/common/promptSyntax/service/promptsService.js';
+import { IAICustomizationWorkspaceService, IStorageSourceFilter } from '../../../../../workbench/contrib/chat/common/aiCustomizationWorkspaceService.js';
+import { IWorkspaceContextService, IWorkspace, IWorkspaceFolder, WorkbenchState } from '../../../../../platform/workspace/common/workspace.js';
+import { getSourceCounts, getSourceCountsTotal, getCustomizationTotalCount } from '../../browser/customizationCounts.js';
+import { IMcpService } from '../../../../../workbench/contrib/mcp/common/mcpTypes.js';
+import { Event } from '../../../../../base/common/event.js';
+import { observableValue } from '../../../../../base/common/observable.js';
+
+function localFile(path: string): ILocalPromptPath {
+	return { uri: URI.file(path), storage: PromptsStorage.local, type: PromptsType.instructions };
+}
+
+function userFile(path: string): IUserPromptPath {
+	return { uri: URI.file(path), storage: PromptsStorage.user, type: PromptsType.instructions };
+}
+
+function extensionFile(path: string): IExtensionPromptPath {
+	return {
+		uri: URI.file(path),
+		storage: PromptsStorage.extension,
+		type: PromptsType.instructions,
+		extension: undefined!,
+		source: undefined!,
+	};
+}
+
+function agentInstructionFile(path: string): IResolvedAgentFile {
+	return { uri: URI.file(path), realPath: undefined, type: AgentFileType.agentsMd };
+}
+
+function makeWorkspaceFolder(path: string, name?: string): IWorkspaceFolder {
+	const uri = URI.file(path);
+	return {
+		uri,
+		name: name ?? path.split('/').pop()!,
+		index: 0,
+		toResource: (rel: string) => URI.joinPath(uri, rel),
+	};
+}
+
+function createMockPromptsService(opts: {
+	localFiles?: IPromptPath[];
+	userFiles?: IPromptPath[];
+	extensionFiles?: IPromptPath[];
+	allFiles?: IPromptPath[];
+	agentInstructions?: IResolvedAgentFile[];
+	agents?: { name: string; uri: URI; storage: PromptsStorage }[];
+	skills?: { name: string; uri: URI; storage: PromptsStorage }[];
+	commands?: { name: string; uri: URI; storage: PromptsStorage; type: PromptsType }[];
+} = {}): IPromptsService {
+	return {
+		listPromptFilesForStorage: async (type: PromptsType, storage: PromptsStorage) => {
+			if (storage === PromptsStorage.local) { return opts.localFiles ?? []; }
+			if (storage === PromptsStorage.user) { return opts.userFiles ?? []; }
+			if (storage === PromptsStorage.extension) { return opts.extensionFiles ?? []; }
+			return [];
+		},
+		listPromptFiles: async () => opts.allFiles ?? [...(opts.localFiles ?? []), ...(opts.userFiles ?? []), ...(opts.extensionFiles ?? [])],
+		listAgentInstructions: async () => opts.agentInstructions ?? [],
+		getCustomAgents: async () => (opts.agents ?? []).map(a => ({
+			name: a.name,
+			uri: a.uri,
+			source: { storage: a.storage },
+		})),
+		findAgentSkills: async () => (opts.skills ?? []).map(s => ({
+			name: s.name,
+			uri: s.uri,
+			storage: s.storage,
+		})),
+		getPromptSlashCommands: async () => (opts.commands ?? []).map(c => ({
+			name: c.name,
+			promptPath: { uri: c.uri, storage: c.storage, type: c.type },
+		})),
+		getSourceFolders: async () => [],
+		getResolvedSourceFolders: async () => [],
+		onDidChangeCustomAgents: Event.None,
+		onDidChangeSlashCommands: Event.None,
+	} as unknown as IPromptsService;
+}
+
+function createMockWorkspaceService(opts: {
+	activeRoot?: URI;
+	filter?: IStorageSourceFilter;
+} = {}): IAICustomizationWorkspaceService {
+	const defaultFilter: IStorageSourceFilter = opts.filter ?? {
+		sources: [PromptsStorage.local, PromptsStorage.user, PromptsStorage.extension],
+	};
+	return {
+		_serviceBrand: undefined,
+		activeProjectRoot: observableValue('test', opts.activeRoot),
+		getActiveProjectRoot: () => opts.activeRoot,
+		managementSections: [],
+		getStorageSourceFilter: () => defaultFilter,
+		preferManualCreation: false,
+		commitFiles: async () => { },
+		generateCustomization: async () => { },
+	} as unknown as IAICustomizationWorkspaceService;
+}
+
+function createMockWorkspaceContextService(folders: IWorkspaceFolder[]): IWorkspaceContextService {
+	return {
+		getWorkspace: () => ({ folders } as IWorkspace),
+		getWorkbenchState: () => WorkbenchState.FOLDER,
+		getWorkspaceFolder: () => folders[0],
+		onDidChangeWorkspaceFolders: Event.None,
+		onDidChangeWorkbenchState: Event.None,
+		onDidChangeWorkspaceName: Event.None,
+		isInsideWorkspace: () => true,
+	} as unknown as IWorkspaceContextService;
+}
+
+suite('customizationCounts', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	const workspaceRoot = URI.file('/workspace');
+	const workspaceFolder = makeWorkspaceFolder('/workspace');
+
+	suite('getSourceCountsTotal', () => {
+		test('sums only visible sources', () => {
+			const counts = { workspace: 5, user: 3, extension: 2, builtin: 0 };
+			const filter: IStorageSourceFilter = { sources: [PromptsStorage.local, PromptsStorage.user] };
+			assert.strictEqual(getSourceCountsTotal(counts, filter), 8);
+		});
+
+		test('returns 0 for empty sources', () => {
+			const counts = { workspace: 5, user: 3, extension: 2, builtin: 0 };
+			const filter: IStorageSourceFilter = { sources: [] };
+			assert.strictEqual(getSourceCountsTotal(counts, filter), 0);
+		});
+
+		test('sums all sources', () => {
+			const counts = { workspace: 5, user: 3, extension: 2, builtin: 0 };
+			const filter: IStorageSourceFilter = { sources: [PromptsStorage.local, PromptsStorage.user, PromptsStorage.extension] };
+			assert.strictEqual(getSourceCountsTotal(counts, filter), 10);
+		});
+
+		test('handles single source', () => {
+			const counts = { workspace: 7, user: 0, extension: 0, builtin: 0 };
+			const filter: IStorageSourceFilter = { sources: [PromptsStorage.local] };
+			assert.strictEqual(getSourceCountsTotal(counts, filter), 7);
+		});
+
+		test('ignores plugin storage in totals (not in ISourceCounts)', () => {
+			const counts = { workspace: 1, user: 1, extension: 1, builtin: 0 };
+			const filter: IStorageSourceFilter = { sources: [PromptsStorage.plugin] };
+			assert.strictEqual(getSourceCountsTotal(counts, filter), 0);
+		});
+	});
+
+	suite('getSourceCounts - instructions', () => {
+		test('includes agent instruction files in workspace count', async () => {
+			const promptsService = createMockPromptsService({
+				localFiles: [
+					localFile('/workspace/.github/instructions/a.instructions.md'),
+				],
+				userFiles: [],
+				extensionFiles: [],
+				allFiles: [
+					localFile('/workspace/.github/instructions/a.instructions.md'),
+				],
+				agentInstructions: [
+					agentInstructionFile('/workspace/AGENTS.md'),
+					agentInstructionFile('/workspace/.github/copilot-instructions.md'),
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService,
+				PromptsType.instructions,
+				{ sources: [PromptsStorage.local, PromptsStorage.user] },
+				contextService,
+				workspaceService,
+			);
+
+			// 1 .instructions.md + 2 agent instruction files = 3 workspace
+			assert.strictEqual(counts.workspace, 3);
+			assert.strictEqual(counts.user, 0);
+		});
+
+		test('classifies agent instructions outside workspace as user', async () => {
+			const promptsService = createMockPromptsService({
+				localFiles: [],
+				userFiles: [],
+				extensionFiles: [],
+				allFiles: [],
+				agentInstructions: [
+					agentInstructionFile('/home/user/.claude/CLAUDE.md'),
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService,
+				PromptsType.instructions,
+				{ sources: [PromptsStorage.local, PromptsStorage.user] },
+				contextService,
+				workspaceService,
+			);
+
+			assert.strictEqual(counts.workspace, 0);
+			assert.strictEqual(counts.user, 1);
+		});
+
+		test('agent instructions under active root classified as workspace', async () => {
+			// Active root might not be in getWorkspace().folders (e.g. sessions worktree),
+			// but should still count as workspace
+			const activeRoot = URI.file('/session/worktree');
+			const promptsService = createMockPromptsService({
+				allFiles: [],
+				agentInstructions: [
+					agentInstructionFile('/session/worktree/AGENTS.md'),
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot });
+			// No workspace folders match — but active root does
+			const contextService = createMockWorkspaceContextService([]);
+
+			const counts = await getSourceCounts(
+				promptsService,
+				PromptsType.instructions,
+				{ sources: [PromptsStorage.local, PromptsStorage.user] },
+				contextService,
+				workspaceService,
+			);
+
+			assert.strictEqual(counts.workspace, 1);
+			assert.strictEqual(counts.user, 0);
+		});
+
+		test('no agent instructions returns only prompt file counts', async () => {
+			const promptsService = createMockPromptsService({
+				allFiles: [
+					localFile('/workspace/.github/instructions/a.instructions.md'),
+					localFile('/workspace/.github/instructions/b.instructions.md'),
+				],
+				agentInstructions: [],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService,
+				PromptsType.instructions,
+				{ sources: [PromptsStorage.local] },
+				contextService,
+				workspaceService,
+			);
+
+			assert.strictEqual(counts.workspace, 2);
+		});
+
+		test('mixed agent instructions across workspace and user', async () => {
+			const promptsService = createMockPromptsService({
+				allFiles: [
+					localFile('/workspace/.github/instructions/rules.instructions.md'),
+				],
+				agentInstructions: [
+					agentInstructionFile('/workspace/AGENTS.md'),
+					agentInstructionFile('/workspace/CLAUDE.md'),
+					agentInstructionFile('/home/user/.claude/CLAUDE.md'),
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService,
+				PromptsType.instructions,
+				{ sources: [PromptsStorage.local, PromptsStorage.user] },
+				contextService,
+				workspaceService,
+			);
+
+			// 1 .instructions.md + 2 workspace agent files = 3
+			assert.strictEqual(counts.workspace, 3);
+			// 1 user-level CLAUDE.md
+			assert.strictEqual(counts.user, 1);
+		});
+	});
+
+	suite('getSourceCounts - agents', () => {
+		test('uses getCustomAgents instead of listPromptFilesForStorage', async () => {
+			const promptsService = createMockPromptsService({
+				// listPromptFilesForStorage would return these — but agents should use getCustomAgents
+				localFiles: [localFile('/workspace/.github/agents/a.agent.md')],
+				agents: [
+					{ name: 'agent-a', uri: URI.file('/workspace/.github/agents/a.agent.md'), storage: PromptsStorage.local },
+					{ name: 'agent-b', uri: URI.file('/workspace/.github/agents/b.agent.md'), storage: PromptsStorage.local },
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService,
+				PromptsType.agent,
+				{ sources: [PromptsStorage.local] },
+				contextService,
+				workspaceService,
+			);
+
+			// Should use getCustomAgents (2), not listPromptFilesForStorage (1)
+			assert.strictEqual(counts.workspace, 2);
+		});
+
+		test('counts agents across storage types', async () => {
+			const promptsService = createMockPromptsService({
+				agents: [
+					{ name: 'local-agent', uri: URI.file('/workspace/.github/agents/a.agent.md'), storage: PromptsStorage.local },
+					{ name: 'user-agent', uri: URI.file('/home/.claude/agents/b.agent.md'), storage: PromptsStorage.user },
+					{ name: 'ext-agent', uri: URI.file('/ext/agents/c.agent.md'), storage: PromptsStorage.extension },
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService,
+				PromptsType.agent,
+				{ sources: [PromptsStorage.local, PromptsStorage.user, PromptsStorage.extension] },
+				contextService,
+				workspaceService,
+			);
+
+			assert.deepStrictEqual(counts, { workspace: 1, user: 1, extension: 1, builtin: 0 });
+		});
+
+		test('empty agents returns all zeros', async () => {
+			const promptsService = createMockPromptsService({ agents: [] });
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.agent,
+				{ sources: [PromptsStorage.local, PromptsStorage.user] },
+				contextService, workspaceService,
+			);
+
+			assert.deepStrictEqual(counts, { workspace: 0, user: 0, extension: 0, builtin: 0 });
+		});
+	});
+
+	suite('getSourceCounts - skills', () => {
+		test('uses findAgentSkills', async () => {
+			const promptsService = createMockPromptsService({
+				skills: [
+					{ name: 'skill-a', uri: URI.file('/workspace/.github/skills/a/SKILL.md'), storage: PromptsStorage.local },
+					{ name: 'skill-b', uri: URI.file('/home/user/.copilot/skills/b/SKILL.md'), storage: PromptsStorage.user },
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService,
+				PromptsType.skill,
+				{ sources: [PromptsStorage.local, PromptsStorage.user] },
+				contextService,
+				workspaceService,
+			);
+
+			assert.strictEqual(counts.workspace, 1);
+			assert.strictEqual(counts.user, 1);
+		});
+
+		test('empty skills returns zeros', async () => {
+			const promptsService = createMockPromptsService({ skills: [] });
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.skill,
+				{ sources: [PromptsStorage.local, PromptsStorage.user] },
+				contextService, workspaceService,
+			);
+
+			assert.deepStrictEqual(counts, { workspace: 0, user: 0, extension: 0, builtin: 0 });
+		});
+
+		test('skills filtered by storage source filter', async () => {
+			const promptsService = createMockPromptsService({
+				skills: [
+					{ name: 'skill-a', uri: URI.file('/workspace/.github/skills/a/SKILL.md'), storage: PromptsStorage.local },
+					{ name: 'skill-b', uri: URI.file('/home/user/.copilot/skills/b/SKILL.md'), storage: PromptsStorage.user },
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			// Only local sources visible
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.skill,
+				{ sources: [PromptsStorage.local] },
+				contextService, workspaceService,
+			);
+
+			assert.strictEqual(counts.workspace, 1);
+			assert.strictEqual(counts.user, 0);
+		});
+	});
+
+	suite('getSourceCounts - prompts', () => {
+		test('uses getPromptSlashCommands and filters out skills', async () => {
+			const promptsService = createMockPromptsService({
+				commands: [
+					{ name: 'my-prompt', uri: URI.file('/workspace/.github/prompts/a.prompt.md'), storage: PromptsStorage.local, type: PromptsType.prompt },
+					{ name: 'my-skill', uri: URI.file('/workspace/.github/skills/b/SKILL.md'), storage: PromptsStorage.local, type: PromptsType.skill },
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService,
+				PromptsType.prompt,
+				{ sources: [PromptsStorage.local] },
+				contextService,
+				workspaceService,
+			);
+
+			// Should exclude the skill command
+			assert.strictEqual(counts.workspace, 1);
+		});
+
+		test('counts prompts across storage types', async () => {
+			const promptsService = createMockPromptsService({
+				commands: [
+					{ name: 'wp', uri: URI.file('/workspace/.github/prompts/a.prompt.md'), storage: PromptsStorage.local, type: PromptsType.prompt },
+					{ name: 'up', uri: URI.file('/home/user/prompts/b.prompt.md'), storage: PromptsStorage.user, type: PromptsType.prompt },
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.prompt,
+				{ sources: [PromptsStorage.local, PromptsStorage.user] },
+				contextService, workspaceService,
+			);
+
+			assert.deepStrictEqual(counts, { workspace: 1, user: 1, extension: 0, builtin: 0 });
+		});
+
+		test('all skills are excluded from prompt counts', async () => {
+			const promptsService = createMockPromptsService({
+				commands: [
+					{ name: 's1', uri: URI.file('/w/s1/SKILL.md'), storage: PromptsStorage.local, type: PromptsType.skill },
+					{ name: 's2', uri: URI.file('/w/s2/SKILL.md'), storage: PromptsStorage.user, type: PromptsType.skill },
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.prompt,
+				{ sources: [PromptsStorage.local, PromptsStorage.user] },
+				contextService, workspaceService,
+			);
+
+			assert.deepStrictEqual(counts, { workspace: 0, user: 0, extension: 0, builtin: 0 });
+		});
+	});
+
+	suite('getSourceCounts - hooks', () => {
+		test('uses listPromptFiles for hooks', async () => {
+			const promptsService = createMockPromptsService({
+				allFiles: [
+					localFile('/workspace/.github/hooks/pre-commit.json'),
+					localFile('/workspace/.claude/settings.json'),
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.hook,
+				{ sources: [PromptsStorage.local] },
+				contextService, workspaceService,
+			);
+
+			assert.strictEqual(counts.workspace, 2);
+		});
+
+		test('hooks with only local source excludes user hooks', async () => {
+			const promptsService = createMockPromptsService({
+				allFiles: [
+					localFile('/workspace/.github/hooks/pre-commit.json'),
+					userFile('/home/user/.claude/settings.json'),
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.hook,
+				{ sources: [PromptsStorage.local] },
+				contextService, workspaceService,
+			);
+
+			assert.strictEqual(counts.workspace, 1);
+			assert.strictEqual(counts.user, 0);
+		});
+	});
+
+	suite('getSourceCounts - filter', () => {
+		test('applies includedUserFileRoots filter', async () => {
+			const copilotRoot = URI.file('/home/user/.copilot');
+			const promptsService = createMockPromptsService({
+				allFiles: [
+					localFile('/workspace/.github/instructions/a.instructions.md'),
+					userFile('/home/user/.copilot/instructions/b.instructions.md'),
+					userFile('/home/user/.vscode/instructions/c.instructions.md'),
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService,
+				PromptsType.instructions,
+				{
+					sources: [PromptsStorage.local, PromptsStorage.user],
+					includedUserFileRoots: [copilotRoot],
+				},
+				contextService,
+				workspaceService,
+			);
+
+			assert.strictEqual(counts.workspace, 1);
+			// Only the copilot file passes, not the vscode profile file
+			assert.strictEqual(counts.user, 1);
+		});
+
+		test('excludes storage types not in sources', async () => {
+			const promptsService = createMockPromptsService({
+				allFiles: [
+					localFile('/workspace/.github/instructions/a.instructions.md'),
+					extensionFile('/ext/instructions/b.instructions.md'),
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService,
+				PromptsType.instructions,
+				{ sources: [PromptsStorage.local] },
+				contextService,
+				workspaceService,
+			);
+
+			assert.strictEqual(counts.workspace, 1);
+			assert.strictEqual(counts.extension, 0);
+		});
+
+		test('includedUserFileRoots with multiple roots', async () => {
+			const copilotRoot = URI.file('/home/user/.copilot');
+			const claudeRoot = URI.file('/home/user/.claude');
+			const promptsService = createMockPromptsService({
+				allFiles: [
+					userFile('/home/user/.copilot/instructions/a.instructions.md'),
+					userFile('/home/user/.claude/rules/b.md'),
+					userFile('/home/user/.vscode/instructions/c.instructions.md'),
+					userFile('/home/user/.agents/instructions/d.instructions.md'),
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.instructions,
+				{
+					sources: [PromptsStorage.local, PromptsStorage.user],
+					includedUserFileRoots: [copilotRoot, claudeRoot],
+				},
+				contextService, workspaceService,
+			);
+
+			// copilot + claude pass, vscode + agents don't
+			assert.strictEqual(counts.user, 2);
+		});
+
+		test('undefined includedUserFileRoots shows all user files', async () => {
+			const promptsService = createMockPromptsService({
+				allFiles: [
+					userFile('/home/user/.copilot/instructions/a.instructions.md'),
+					userFile('/home/user/.vscode/instructions/b.instructions.md'),
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.instructions,
+				{ sources: [PromptsStorage.user] },
+				contextService, workspaceService,
+			);
+
+			assert.strictEqual(counts.user, 2);
+		});
+	});
+
+	suite('getCustomizationTotalCount', () => {
+		test('sums all sections', async () => {
+			const promptsService = createMockPromptsService({
+				agents: [
+					{ name: 'a', uri: URI.file('/w/a.agent.md'), storage: PromptsStorage.local },
+				],
+				skills: [
+					{ name: 's', uri: URI.file('/w/s/SKILL.md'), storage: PromptsStorage.local },
+				],
+				commands: [
+					{ name: 'p', uri: URI.file('/w/p.prompt.md'), storage: PromptsStorage.local, type: PromptsType.prompt },
+				],
+			});
+			const mcpService = {
+				servers: observableValue('test', [{ id: 'srv1' }]),
+			} as unknown as IMcpService;
+			const workspaceService = createMockWorkspaceService({
+				activeRoot: URI.file('/w'),
+				filter: { sources: [PromptsStorage.local] },
+			});
+			const contextService = createMockWorkspaceContextService([makeWorkspaceFolder('/w')]);
+
+			const total = await getCustomizationTotalCount(promptsService, mcpService, workspaceService, contextService);
+
+			// 1 agent + 1 skill + 0 instructions + 1 prompt + 0 hooks + 1 mcp = 4
+			assert.strictEqual(total, 4);
+		});
+
+		test('empty workspace returns only mcp count', async () => {
+			const promptsService = createMockPromptsService({});
+			const mcpService = {
+				servers: observableValue('test', [{ id: 's1' }, { id: 's2' }]),
+			} as unknown as IMcpService;
+			const workspaceService = createMockWorkspaceService({
+				filter: { sources: [PromptsStorage.local] },
+			});
+			const contextService = createMockWorkspaceContextService([]);
+
+			const total = await getCustomizationTotalCount(promptsService, mcpService, workspaceService, contextService);
+
+			assert.strictEqual(total, 2); // just 2 mcp servers
+		});
+
+		test('includes instructions with agent files in count', async () => {
+			const instructionFiles = [
+				localFile('/w/.github/instructions/a.instructions.md'),
+			];
+			const promptsService = createMockPromptsService({
+				allFiles: instructionFiles,
+				agentInstructions: [
+					agentInstructionFile('/w/AGENTS.md'),
+				],
+			});
+			// Override listPromptFiles to only return files for instructions type
+			promptsService.listPromptFiles = async (type: PromptsType) => {
+				return type === PromptsType.instructions ? instructionFiles : [];
+			};
+			const mcpService = {
+				servers: observableValue('test', []),
+			} as unknown as IMcpService;
+			const workspaceService = createMockWorkspaceService({
+				activeRoot: URI.file('/w'),
+				filter: { sources: [PromptsStorage.local] },
+			});
+			const contextService = createMockWorkspaceContextService([makeWorkspaceFolder('/w')]);
+
+			const total = await getCustomizationTotalCount(promptsService, mcpService, workspaceService, contextService);
+
+			// 0 agents + 0 skills + 2 instructions (1 file + 1 AGENTS.md) + 0 prompts + 0 hooks + 0 mcp = 2
+			assert.strictEqual(total, 2);
+		});
+	});
+
+	suite('data source consistency', () => {
+		// These tests verify that getSourceCounts uses the same data sources
+		// as the list widget's loadItems() — the root cause of the count mismatch bug.
+
+		test('instructions count matches widget: listPromptFiles + listAgentInstructions', async () => {
+			// Scenario: 13 .instructions.md files + 2 agent instruction files = 15 total
+			// The old bug: sidebar showed 13 (only listPromptFilesForStorage),
+			// editor showed 15 (listPromptFiles + listAgentInstructions)
+			const instructionFiles = Array.from({ length: 13 }, (_, i) =>
+				localFile(`/workspace/.github/instructions/rule-${i}.instructions.md`)
+			);
+			const promptsService = createMockPromptsService({
+				localFiles: instructionFiles,
+				allFiles: instructionFiles,
+				agentInstructions: [
+					agentInstructionFile('/workspace/AGENTS.md'),
+					agentInstructionFile('/workspace/.github/copilot-instructions.md'),
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.instructions,
+				{ sources: [PromptsStorage.local, PromptsStorage.user] },
+				contextService, workspaceService,
+			);
+
+			// Must be 15, not 13
+			assert.strictEqual(counts.workspace, 15);
+		});
+
+		test('agents count uses getCustomAgents not listPromptFilesForStorage', async () => {
+			// getCustomAgents parses frontmatter and may exclude invalid files
+			const promptsService = createMockPromptsService({
+				// Raw file count would be 3
+				localFiles: [
+					localFile('/workspace/.github/agents/a.agent.md'),
+					localFile('/workspace/.github/agents/b.agent.md'),
+					localFile('/workspace/.github/agents/README.md'), // would be excluded by getCustomAgents
+				],
+				// But parsed custom agents is only 2
+				agents: [
+					{ name: 'agent-a', uri: URI.file('/workspace/.github/agents/a.agent.md'), storage: PromptsStorage.local },
+					{ name: 'agent-b', uri: URI.file('/workspace/.github/agents/b.agent.md'), storage: PromptsStorage.local },
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.agent,
+				{ sources: [PromptsStorage.local] },
+				contextService, workspaceService,
+			);
+
+			// Must use getCustomAgents count (2), not raw file count (3)
+			assert.strictEqual(counts.workspace, 2);
+		});
+
+		test('prompts count excludes skills to match widget', async () => {
+			// The widget's loadItems filters out skill-type commands.
+			// Count must do the same.
+			const promptsService = createMockPromptsService({
+				localFiles: [
+					localFile('/workspace/.github/prompts/a.prompt.md'),
+					localFile('/workspace/.github/prompts/b.prompt.md'),
+				],
+				commands: [
+					{ name: 'prompt-a', uri: URI.file('/workspace/.github/prompts/a.prompt.md'), storage: PromptsStorage.local, type: PromptsType.prompt },
+					{ name: 'prompt-b', uri: URI.file('/workspace/.github/prompts/b.prompt.md'), storage: PromptsStorage.local, type: PromptsType.prompt },
+					{ name: 'skill-x', uri: URI.file('/workspace/.github/skills/x/SKILL.md'), storage: PromptsStorage.local, type: PromptsType.skill },
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: workspaceRoot });
+			const contextService = createMockWorkspaceContextService([workspaceFolder]);
+
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.prompt,
+				{ sources: [PromptsStorage.local] },
+				contextService, workspaceService,
+			);
+
+			// Must be 2 (prompts only), not 3 (including skill)
+			assert.strictEqual(counts.workspace, 2);
+		});
+
+		test('no active root: agent instructions classified as user', async () => {
+			const promptsService = createMockPromptsService({
+				allFiles: [],
+				agentInstructions: [
+					agentInstructionFile('/somewhere/AGENTS.md'),
+				],
+			});
+			const workspaceService = createMockWorkspaceService({ activeRoot: undefined });
+			const contextService = createMockWorkspaceContextService([]);
+
+			const counts = await getSourceCounts(
+				promptsService, PromptsType.instructions,
+				{ sources: [PromptsStorage.local, PromptsStorage.user] },
+				contextService, workspaceService,
+			);
+
+			// No workspace context → classified as user
+			assert.strictEqual(counts.workspace, 0);
+			assert.strictEqual(counts.user, 1);
+		});
+	});
+});
diff --git a/src/vs/sessions/contrib/terminal/browser/sessionsTerminalContribution.ts b/src/vs/sessions/contrib/terminal/browser/sessionsTerminalContribution.ts
index ff97b6ae70c44..c45ce72df32f1 100644
--- a/src/vs/sessions/contrib/terminal/browser/sessionsTerminalContribution.ts
+++ b/src/vs/sessions/contrib/terminal/browser/sessionsTerminalContribution.ts
@@ -12,53 +12,70 @@ import { localize2 } from '../../../../nls.js';
 import { Action2, registerAction2 } from '../../../../platform/actions/common/actions.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
 import { IWorkbenchContribution, getWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../../workbench/common/contributions.js';
-import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
-import { isAgentSession } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsModel.js';
 import { IAgentSessionsService } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
-import { ITerminalService } from '../../../../workbench/contrib/terminal/browser/terminal.js';
+import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
+import { ITerminalInstance, ITerminalService } from '../../../../workbench/contrib/terminal/browser/terminal.js';
+import { TerminalCapability } from '../../../../platform/terminal/common/capabilities/capabilities.js';
 import { IPathService } from '../../../../workbench/services/path/common/pathService.js';
 import { Menus } from '../../../browser/menus.js';
 import { IActiveSessionItem, ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
 import { IsAuxiliaryWindowContext } from '../../../../workbench/common/contextkeys.js';
+import { ContextKeyExpr } from '../../../../platform/contextkey/common/contextkey.js';
+import { SessionsWelcomeVisibleContext } from '../../../common/contextkeys.js';
+import { IViewsService } from '../../../../workbench/services/views/common/viewsService.js';
+import { TERMINAL_VIEW_ID } from '../../../../workbench/contrib/terminal/common/terminal.js';
 
 /**
- * Returns the cwd URI for the given session: worktree for non-cloud agent
- * sessions, repository otherwise, or `undefined` when neither is available.
+ * Returns the cwd URI for the given session: worktree or repository path for
+ * background sessions only. Returns `undefined` for non-background sessions
+ * (Cloud, Local, etc.) which have no local worktree, or when no path is available.
  */
 function getSessionCwd(session: IActiveSessionItem | undefined): URI | undefined {
-	if (isAgentSession(session) && session.providerType !== AgentSessionProviders.Cloud) {
-		return session.worktree ?? session.repository;
+	if (session?.providerType !== AgentSessionProviders.Background) {
+		return undefined;
 	}
-	return session?.repository;
+	return session.worktree ?? session.repository;
 }
 
 /**
  * Manages terminal instances in the sessions window, ensuring:
  * - A terminal exists for the active session's worktree (or repository if no worktree).
- * - A path→instanceId mapping tracks which terminal belongs to which worktree.
+ * - Terminals are shown/hidden based on their initial cwd matching the active path.
  * - All terminals for a worktree are closed when the session is archived.
  */
 export class SessionsTerminalContribution extends Disposable implements IWorkbenchContribution {
 
 	static readonly ID = 'workbench.contrib.sessionsTerminal';
 
-	/** Maps worktree/repository fsPath (lower-cased) to the terminal instance id. */
-	private readonly _pathToInstanceId = new Map<string, number>();
-	private _lastTargetFsPath: string | undefined;
+	private _activeKey: string | undefined;
 
 	constructor(
 		@ISessionsManagementService private readonly _sessionsManagementService: ISessionsManagementService,
 		@ITerminalService private readonly _terminalService: ITerminalService,
 		@IAgentSessionsService private readonly _agentSessionsService: IAgentSessionsService,
 		@ILogService private readonly _logService: ILogService,
+		@IPathService private readonly _pathService: IPathService,
 	) {
 		super();
 
-		// React to active session worktree/repository path changes
+		// React to active session changes — use worktree/repo for background sessions, home dir otherwise
 		this._register(autorun(reader => {
 			const session = this._sessionsManagementService.activeSession.read(reader);
-			const targetPath = getSessionCwd(session);
-			this._onActivePathChanged(targetPath);
+			this._onActiveSessionChanged(session);
+		}));
+
+		// Hide restored terminals from a previous window session that don't
+		// belong to the current active session. These arrive asynchronously
+		// during reconnection and would otherwise flash in the foreground.
+		this._register(this._terminalService.onDidCreateInstance(instance => {
+			if (instance.shellLaunchConfig.attachPersistentProcess && this._activeKey) {
+				instance.getInitialCwd().then(cwd => {
+					if (cwd.toLowerCase() !== this._activeKey) {
+						this._terminalService.moveToBackground(instance);
+						this._logService.trace(`[SessionsTerminal] Hid restored terminal ${instance.instanceId} (cwd: ${cwd})`);
+					}
+				});
+			}
 		}));
 
 		// When a session is archived, close all terminals for its worktree
@@ -70,66 +87,160 @@ export class SessionsTerminalContribution extends Disposable implements IWorkben
 				}
 			}
 		}));
-
-		// Clean up mapping when terminals are disposed
-		this._register(this._terminalService.onDidDisposeInstance(instance => {
-			for (const [path, id] of this._pathToInstanceId) {
-				if (id === instance.instanceId) {
-					this._pathToInstanceId.delete(path);
-					break;
-				}
-			}
-		}));
 	}
 
 	/**
-	 * Ensures a terminal exists for the given cwd, reusing an existing one
-	 * from the mapping or creating a new one. Sets it as active and optionally
-	 * focuses it.
+	 * Ensures a terminal exists for the given cwd by scanning all terminal
+	 * instances for a matching initial cwd. If none is found, creates a new
+	 * one. Sets it as active and optionally focuses it.
 	 */
-	async ensureTerminal(cwd: URI, focus: boolean): Promise<void> {
+	async ensureTerminal(cwd: URI, focus: boolean): Promise<ITerminalInstance[]> {
 		const key = cwd.fsPath.toLowerCase();
-		const existingId = this._pathToInstanceId.get(key);
-		const existing = existingId !== undefined ? this._terminalService.getInstanceFromId(existingId) : undefined;
-
-		if (existing) {
-			this._terminalService.setActiveInstance(existing);
-		} else {
-			const instance = await this._terminalService.createTerminal({ config: { cwd } });
-			this._pathToInstanceId.set(key, instance.instanceId);
-			this._terminalService.setActiveInstance(instance);
-			this._logService.trace(`[SessionsTerminal] Created terminal ${instance.instanceId} for ${cwd.fsPath}`);
+		let existing = await this._findTerminalsForKey(key);
+
+		if (existing.length === 0) {
+			try {
+				existing = [await this._terminalService.createTerminal({ config: { cwd } })];
+				this._terminalService.setActiveInstance(existing[0]);
+				this._logService.trace(`[SessionsTerminal] Created terminal ${existing[0].instanceId} for ${cwd.fsPath}`);
+			} catch (e) {
+				this._logService.trace(`[SessionsTerminal] Cannot create terminal for ${cwd.fsPath}: ${e}`);
+				return [];
+			}
 		}
 
 		if (focus) {
 			await this._terminalService.focusActiveInstance();
 		}
+
+		return existing;
 	}
 
-	private async _onActivePathChanged(targetPath: URI | undefined): Promise<void> {
-		if (!targetPath) {
+	private async _onActiveSessionChanged(session: IActiveSessionItem | undefined): Promise<void> {
+		if (!session) {
 			return;
 		}
 
-		const targetFsPath = targetPath.fsPath;
-		if (this._lastTargetFsPath?.toLowerCase() === targetFsPath.toLowerCase()) {
+		const sessionCwd = getSessionCwd(session);
+
+		const targetPath = sessionCwd ?? await this._pathService.userHome();
+		const targetKey = targetPath.fsPath.toLowerCase();
+		if (this._activeKey === targetKey) {
 			return;
 		}
-		this._lastTargetFsPath = targetFsPath;
+		this._activeKey = targetKey;
+
+		const instances = await this.ensureTerminal(targetPath, false);
 
-		await this.ensureTerminal(targetPath, false);
+		// If the active key changed while we were awaiting, a newer call has
+		// taken over — skip the visibility update to avoid flicker.
+		if (this._activeKey !== targetKey) {
+			return;
+		}
+		await this._updateTerminalVisibility(targetKey, instances.map(instance => instance.instanceId));
 	}
 
-	private _closeTerminalsForPath(fsPath: string): void {
+	/**
+	 * Finds the first terminal instance whose initial cwd (lower-cased) matches
+	 * the given key.
+	 */
+	private async _findTerminalsForKey(key: string): Promise<ITerminalInstance[]> {
+		const result: ITerminalInstance[] = [];
+		for (const instance of this._terminalService.instances) {
+			try {
+				const cwd = await instance.getInitialCwd();
+				if (cwd.toLowerCase() === key) {
+					result.push(instance);
+				}
+			} catch {
+				// ignore terminals whose cwd cannot be resolved
+			}
+		}
+		return result;
+	}
+
+	/**
+	 * Shows background terminals whose initial cwd matches the active key and
+	 * hides foreground terminals whose initial cwd does not match.
+	 */
+	private async _updateTerminalVisibility(activeKey: string, forceForegroundTerminalIds: number[]): Promise<void> {
+		const toShow: ITerminalInstance[] = [];
+		const toHide: ITerminalInstance[] = [];
+
+		for (const instance of [...this._terminalService.instances]) {
+			let cwd: string | undefined;
+			try {
+				cwd = (await instance.getInitialCwd()).toLowerCase();
+			} catch {
+				continue;
+			}
+
+			const isForeground = this._terminalService.foregroundInstances.includes(instance);
+			const isForceVisible = forceForegroundTerminalIds.includes(instance.instanceId);
+			const belongsToActiveSession = cwd === activeKey;
+			if ((belongsToActiveSession || isForceVisible) && !isForeground) {
+				toShow.push(instance);
+			} else if (!belongsToActiveSession && !isForceVisible && isForeground) {
+				toHide.push(instance);
+			}
+		}
+
+		for (const instance of toShow) {
+			await this._terminalService.showBackgroundTerminal(instance, true);
+		}
+		for (const instance of toHide) {
+			this._terminalService.moveToBackground(instance);
+		}
+
+		// Set the terminal with the most recent command as active
+		const foreground = this._terminalService.foregroundInstances;
+		let mostRecent: ITerminalInstance | undefined;
+		let mostRecentTimestamp = -1;
+		for (const instance of foreground) {
+			const cmdDetection = instance.capabilities.get(TerminalCapability.CommandDetection);
+			const lastCmd = cmdDetection?.commands.at(-1);
+			if (lastCmd && lastCmd.timestamp > mostRecentTimestamp) {
+				mostRecentTimestamp = lastCmd.timestamp;
+				mostRecent = instance;
+			}
+		}
+		if (mostRecent) {
+			this._terminalService.setActiveInstance(mostRecent);
+		}
+	}
+
+	private async _closeTerminalsForPath(fsPath: string): Promise<void> {
 		const key = fsPath.toLowerCase();
-		const instanceId = this._pathToInstanceId.get(key);
-		if (instanceId !== undefined) {
-			const instance = this._terminalService.getInstanceFromId(instanceId);
-			if (instance) {
-				this._terminalService.safeDisposeTerminal(instance);
-				this._logService.trace(`[SessionsTerminal] Closed archived terminal ${instanceId}`);
+		for (const instance of [...this._terminalService.instances]) {
+			try {
+				const cwd = (await instance.getInitialCwd()).toLowerCase();
+				if (cwd === key) {
+					this._terminalService.safeDisposeTerminal(instance);
+					this._logService.trace(`[SessionsTerminal] Closed archived terminal ${instance.instanceId}`);
+				}
+			} catch {
+				// ignore
+			}
+		}
+	}
+
+	async dumpTracking(): Promise<void> {
+		console.log(`[SessionsTerminal] Active key: ${this._activeKey ?? '<none>'}`);
+		console.log('[SessionsTerminal] === All Terminals ===');
+		for (const instance of this._terminalService.instances) {
+			let cwd = '<unknown>';
+			try { cwd = await instance.getInitialCwd(); } catch { /* ignored */ }
+			const isForeground = this._terminalService.foregroundInstances.includes(instance);
+			console.log(`  ${instance.instanceId} - ${cwd} - ${isForeground ? 'foreground' : 'background'}`);
+		}
+	}
+
+	async showAllTerminals(): Promise<void> {
+		for (const instance of this._terminalService.instances) {
+			if (!this._terminalService.foregroundInstances.includes(instance)) {
+				await this._terminalService.showBackgroundTerminal(instance, true);
+				this._logService.trace(`[SessionsTerminal] Moved terminal ${instance.instanceId} to foreground`);
 			}
-			this._pathToInstanceId.delete(key);
 		}
 	}
 }
@@ -144,10 +255,10 @@ class OpenSessionInTerminalAction extends Action2 {
 			title: localize2('openInTerminal', "Open Terminal"),
 			icon: Codicon.terminal,
 			menu: [{
-				id: Menus.TitleBarRight,
+				id: Menus.TitleBarSessionMenu,
 				group: 'navigation',
 				order: 9,
-				when: IsAuxiliaryWindowContext.toNegated()
+				when: ContextKeyExpr.and(IsAuxiliaryWindowContext.toNegated(), SessionsWelcomeVisibleContext.toNegated())
 			}]
 		});
 	}
@@ -156,11 +267,49 @@ class OpenSessionInTerminalAction extends Action2 {
 		const contribution = getWorkbenchContribution<SessionsTerminalContribution>(SessionsTerminalContribution.ID);
 		const sessionsManagementService = _accessor.get(ISessionsManagementService);
 		const pathService = _accessor.get(IPathService);
+		const viewsService = _accessor.get(IViewsService);
 
 		const activeSession = sessionsManagementService.activeSession.get();
 		const cwd = getSessionCwd(activeSession) ?? await pathService.userHome();
 		await contribution.ensureTerminal(cwd, true);
+		viewsService.openView(TERMINAL_VIEW_ID);
 	}
 }
 
 registerAction2(OpenSessionInTerminalAction);
+
+class DumpTerminalTrackingAction extends Action2 {
+
+	constructor() {
+		super({
+			id: 'agentSession.dumpTerminalTracking',
+			title: localize2('dumpTerminalTracking', "Dump Terminal Tracking"),
+			f1: true,
+		});
+	}
+
+	override async run(): Promise<void> {
+		const contribution = getWorkbenchContribution<SessionsTerminalContribution>(SessionsTerminalContribution.ID);
+		await contribution.dumpTracking();
+	}
+}
+
+registerAction2(DumpTerminalTrackingAction);
+
+class ShowAllTerminalsAction extends Action2 {
+
+	constructor() {
+		super({
+			id: 'agentSession.showAllTerminals',
+			title: localize2('showAllTerminals', "Show All Terminals"),
+			f1: true,
+		});
+	}
+
+	override async run(): Promise<void> {
+		const contribution = getWorkbenchContribution<SessionsTerminalContribution>(SessionsTerminalContribution.ID);
+		await contribution.showAllTerminals();
+	}
+}
+
+registerAction2(ShowAllTerminalsAction);
diff --git a/src/vs/sessions/contrib/terminal/test/browser/sessionsTerminalContribution.test.ts b/src/vs/sessions/contrib/terminal/test/browser/sessionsTerminalContribution.test.ts
new file mode 100644
index 0000000000000..0d84c3735df21
--- /dev/null
+++ b/src/vs/sessions/contrib/terminal/test/browser/sessionsTerminalContribution.test.ts
@@ -0,0 +1,544 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { Emitter, Event } from '../../../../../base/common/event.js';
+import { observableValue } from '../../../../../base/common/observable.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { mock } from '../../../../../base/test/common/mock.js';
+import { TestInstantiationService } from '../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import { NullLogService, ILogService } from '../../../../../platform/log/common/log.js';
+import { ITerminalInstance, ITerminalService } from '../../../../../workbench/contrib/terminal/browser/terminal.js';
+import { ITerminalCapabilityStore, ICommandDetectionCapability, TerminalCapability } from '../../../../../platform/terminal/common/capabilities/capabilities.js';
+import { IAgentSessionsService } from '../../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsService.js';
+import { IAgentSession, IAgentSessionsModel } from '../../../../../workbench/contrib/chat/browser/agentSessions/agentSessionsModel.js';
+import { AgentSessionProviders } from '../../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
+import { IActiveSessionItem, ISessionsManagementService } from '../../../sessions/browser/sessionsManagementService.js';
+import { SessionsTerminalContribution } from '../../browser/sessionsTerminalContribution.js';
+import { TestPathService } from '../../../../../workbench/test/browser/workbenchTestServices.js';
+import { IPathService } from '../../../../../workbench/services/path/common/pathService.js';
+
+const HOME_DIR = URI.file('/home/user');
+
+function makeAgentSession(opts: {
+	repository?: URI;
+	worktree?: URI;
+	providerType?: string;
+	isArchived?: boolean;
+	worktreePath?: string;
+}): IActiveSessionItem & IAgentSession {
+	return {
+		resource: URI.parse('file:///session'),
+		repository: opts.repository,
+		worktree: opts.worktree,
+		providerType: opts.providerType ?? AgentSessionProviders.Local,
+		setArchived: () => { },
+		setRead: () => { },
+		isArchived: () => opts.isArchived ?? false,
+		isRead: () => true,
+		metadata: opts.worktreePath ? { worktreePath: opts.worktreePath } : undefined,
+	} as unknown as IActiveSessionItem & IAgentSession;
+}
+
+function makeNonAgentSession(opts: { repository?: URI; worktree?: URI; providerType?: string }): IActiveSessionItem {
+	return {
+		repository: opts.repository,
+		worktree: opts.worktree,
+		providerType: opts.providerType ?? AgentSessionProviders.Local,
+	} as IActiveSessionItem;
+}
+
+function makeTerminalInstance(id: number, cwd: string): ITerminalInstance & { _testCommandHistory: { timestamp: number }[] } {
+	const commandHistory: { timestamp: number }[] = [];
+	const capabilities = {
+		get(cap: TerminalCapability) {
+			if (cap === TerminalCapability.CommandDetection && commandHistory.length > 0) {
+				return { commands: commandHistory } as unknown as ICommandDetectionCapability;
+			}
+			return undefined;
+		}
+	} as ITerminalCapabilityStore;
+
+	return {
+		instanceId: id,
+		isDisposed: false,
+		getInitialCwd: () => Promise.resolve(cwd),
+		capabilities,
+		_testCommandHistory: commandHistory,
+	} as unknown as ITerminalInstance & { _testCommandHistory: { timestamp: number }[] };
+}
+
+function addCommandToInstance(instance: ITerminalInstance, timestamp: number): void {
+	(instance as ITerminalInstance & { _testCommandHistory: { timestamp: number }[] })._testCommandHistory.push({ timestamp });
+}
+
+suite('SessionsTerminalContribution', () => {
+	const store = new DisposableStore();
+	let contribution: SessionsTerminalContribution;
+	let activeSessionObs: ReturnType<typeof observableValue<IActiveSessionItem | undefined>>;
+	let onDidChangeSessionArchivedState: Emitter<IAgentSession>;
+
+	let createdTerminals: { cwd: URI }[];
+	let activeInstanceSet: number[];
+	let focusCalls: number;
+	let disposedInstances: ITerminalInstance[];
+	let nextInstanceId: number;
+	let terminalInstances: Map<number, ITerminalInstance>;
+	let backgroundedInstances: Set<number>;
+	let moveToBackgroundCalls: number[];
+	let showBackgroundCalls: number[];
+
+	setup(() => {
+		createdTerminals = [];
+		activeInstanceSet = [];
+		focusCalls = 0;
+		disposedInstances = [];
+		nextInstanceId = 1;
+		terminalInstances = new Map();
+		backgroundedInstances = new Set();
+		moveToBackgroundCalls = [];
+		showBackgroundCalls = [];
+
+		const instantiationService = store.add(new TestInstantiationService());
+
+		activeSessionObs = observableValue('activeSession', undefined);
+		onDidChangeSessionArchivedState = store.add(new Emitter<IAgentSession>());
+
+		instantiationService.stub(ILogService, new NullLogService());
+
+		instantiationService.stub(ISessionsManagementService, new class extends mock<ISessionsManagementService>() {
+			override activeSession = activeSessionObs;
+		});
+
+		instantiationService.stub(ITerminalService, new class extends mock<ITerminalService>() {
+			override onDidCreateInstance = Event.None;
+			override get instances(): readonly ITerminalInstance[] {
+				return [...terminalInstances.values()];
+			}
+			override get foregroundInstances(): readonly ITerminalInstance[] {
+				return [...terminalInstances.values()].filter(i => !backgroundedInstances.has(i.instanceId));
+			}
+			override async createTerminal(opts?: any): Promise<ITerminalInstance> {
+				const id = nextInstanceId++;
+				const cwdUri: URI | undefined = opts?.config?.cwd;
+				const cwdStr = cwdUri?.fsPath ?? '';
+				const instance = makeTerminalInstance(id, cwdStr);
+				createdTerminals.push({ cwd: opts?.config?.cwd });
+				terminalInstances.set(id, instance);
+				return instance;
+			}
+			override getInstanceFromId(id: number): ITerminalInstance | undefined {
+				return terminalInstances.get(id);
+			}
+			override setActiveInstance(instance: ITerminalInstance): void {
+				activeInstanceSet.push(instance.instanceId);
+			}
+			override async focusActiveInstance(): Promise<void> {
+				focusCalls++;
+			}
+			override async safeDisposeTerminal(instance: ITerminalInstance): Promise<void> {
+				disposedInstances.push(instance);
+				terminalInstances.delete(instance.instanceId);
+				backgroundedInstances.delete(instance.instanceId);
+			}
+			override moveToBackground(instance: ITerminalInstance): void {
+				backgroundedInstances.add(instance.instanceId);
+				moveToBackgroundCalls.push(instance.instanceId);
+			}
+			override async showBackgroundTerminal(instance: ITerminalInstance): Promise<void> {
+				backgroundedInstances.delete(instance.instanceId);
+				showBackgroundCalls.push(instance.instanceId);
+			}
+		});
+
+		instantiationService.stub(IAgentSessionsService, new class extends mock<IAgentSessionsService>() {
+			override model = {
+				onDidChangeSessionArchivedState: onDidChangeSessionArchivedState.event,
+			} as unknown as IAgentSessionsModel;
+		});
+
+		instantiationService.stub(IPathService, new TestPathService(HOME_DIR));
+
+		contribution = store.add(instantiationService.createInstance(SessionsTerminalContribution));
+	});
+
+	teardown(() => {
+		store.clear();
+	});
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	// --- Background provider: uses worktree/repository path ---
+
+	test('creates a terminal at the worktree for a background session', async () => {
+		const worktreeUri = URI.file('/worktree');
+		const session = makeAgentSession({ worktree: worktreeUri, repository: URI.file('/repo'), providerType: AgentSessionProviders.Background });
+		activeSessionObs.set(session, undefined);
+		await tick();
+
+		assert.strictEqual(createdTerminals.length, 1);
+		assert.strictEqual(createdTerminals[0].cwd.fsPath, worktreeUri.fsPath);
+	});
+
+	test('falls back to repository when worktree is undefined for a background session', async () => {
+		const repoUri = URI.file('/repo');
+		const session = makeAgentSession({ repository: repoUri, providerType: AgentSessionProviders.Background });
+		activeSessionObs.set(session, undefined);
+		await tick();
+
+		assert.strictEqual(createdTerminals.length, 1);
+		assert.strictEqual(createdTerminals[0].cwd.fsPath, repoUri.fsPath);
+	});
+
+	// --- Non-background providers: use home directory ---
+
+	test('uses home directory for a cloud agent session', async () => {
+		const session = makeAgentSession({ worktree: URI.file('/worktree'), repository: URI.file('/repo'), providerType: AgentSessionProviders.Cloud });
+		activeSessionObs.set(session, undefined);
+		await tick();
+
+		assert.strictEqual(createdTerminals.length, 1);
+		assert.strictEqual(createdTerminals[0].cwd.fsPath, HOME_DIR.fsPath);
+	});
+
+	test('uses home directory for a local agent session', async () => {
+		const session = makeAgentSession({ worktree: URI.file('/worktree'), providerType: AgentSessionProviders.Local });
+		activeSessionObs.set(session, undefined);
+		await tick();
+
+		assert.strictEqual(createdTerminals.length, 1);
+		assert.strictEqual(createdTerminals[0].cwd.fsPath, HOME_DIR.fsPath);
+	});
+
+	test('uses home directory for a non-agent session', async () => {
+		const session = makeNonAgentSession({ repository: URI.file('/repo') });
+		activeSessionObs.set(session, undefined);
+		await tick();
+
+		assert.strictEqual(createdTerminals.length, 1);
+		assert.strictEqual(createdTerminals[0].cwd.fsPath, HOME_DIR.fsPath);
+	});
+
+	test('does not recreate terminal when multiple non-background sessions share the home directory', async () => {
+		const session1 = makeAgentSession({ providerType: AgentSessionProviders.Cloud });
+		activeSessionObs.set(session1, undefined);
+		await tick();
+		assert.strictEqual(createdTerminals.length, 1);
+
+		// Different non-background session — same home dir, no new terminal
+		const session2 = makeAgentSession({ providerType: AgentSessionProviders.Local });
+		activeSessionObs.set(session2, undefined);
+		await tick();
+		assert.strictEqual(createdTerminals.length, 1);
+	});
+
+	test('does not create a terminal when there is no active session', async () => {
+		activeSessionObs.set(undefined, undefined);
+		await tick();
+
+		assert.strictEqual(createdTerminals.length, 0);
+	});
+
+	test('does not recreate terminal for the same path', async () => {
+		const worktreeUri = URI.file('/worktree');
+		const session1 = makeAgentSession({ worktree: worktreeUri, providerType: AgentSessionProviders.Background });
+		activeSessionObs.set(session1, undefined);
+		await tick();
+
+		assert.strictEqual(createdTerminals.length, 1);
+
+		// Setting a different session with the same worktree should not create a new terminal
+		const session2 = makeAgentSession({ worktree: worktreeUri, providerType: AgentSessionProviders.Background });
+		activeSessionObs.set(session2, undefined);
+		await tick();
+
+		assert.strictEqual(createdTerminals.length, 1);
+	});
+
+	test('creates new terminal when switching to a different background path', async () => {
+		const worktree1 = URI.file('/worktree1');
+		const worktree2 = URI.file('/worktree2');
+
+		activeSessionObs.set(makeAgentSession({ worktree: worktree1, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		activeSessionObs.set(makeAgentSession({ worktree: worktree2, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		assert.strictEqual(createdTerminals.length, 2);
+		assert.strictEqual(createdTerminals[1].cwd.fsPath, worktree2.fsPath);
+	});
+
+	// --- ensureTerminal ---
+
+	test('ensureTerminal creates terminal and sets it active', async () => {
+		const cwd = URI.file('/test-cwd');
+		await contribution.ensureTerminal(cwd, false);
+
+		assert.strictEqual(createdTerminals.length, 1);
+		assert.strictEqual(createdTerminals[0].cwd.fsPath, cwd.fsPath);
+		assert.strictEqual(activeInstanceSet.length, 1);
+		assert.strictEqual(focusCalls, 0);
+	});
+
+	test('ensureTerminal focuses when requested', async () => {
+		const cwd = URI.file('/test-cwd');
+		await contribution.ensureTerminal(cwd, true);
+
+		assert.strictEqual(focusCalls, 1);
+	});
+
+	test('ensureTerminal reuses existing terminal for same path', async () => {
+		const cwd = URI.file('/test-cwd');
+		await contribution.ensureTerminal(cwd, false);
+		await contribution.ensureTerminal(cwd, false);
+
+		assert.strictEqual(createdTerminals.length, 1, 'should reuse the existing terminal');
+		assert.strictEqual(activeInstanceSet.length, 1, 'should only set active instance on creation');
+	});
+
+	test('ensureTerminal creates new terminal for different path', async () => {
+		await contribution.ensureTerminal(URI.file('/cwd1'), false);
+		await contribution.ensureTerminal(URI.file('/cwd2'), false);
+
+		assert.strictEqual(createdTerminals.length, 2);
+	});
+
+	test('ensureTerminal path comparison is case-insensitive', async () => {
+		await contribution.ensureTerminal(URI.file('/Test/CWD'), false);
+		await contribution.ensureTerminal(URI.file('/test/cwd'), false);
+
+		assert.strictEqual(createdTerminals.length, 1, 'should match case-insensitively');
+	});
+
+	// --- onDidChangeSessionArchivedState ---
+
+	test('closes terminals when session is archived', async () => {
+		const worktreeUri = URI.file('/worktree');
+		await contribution.ensureTerminal(worktreeUri, false);
+
+		assert.strictEqual(createdTerminals.length, 1);
+
+		const session = makeAgentSession({
+			isArchived: true,
+			worktreePath: worktreeUri.fsPath,
+		});
+		onDidChangeSessionArchivedState.fire(session);
+		await tick();
+
+		assert.strictEqual(disposedInstances.length, 1);
+	});
+
+	test('does not close terminals when session is not archived', async () => {
+		const worktreeUri = URI.file('/worktree');
+		await contribution.ensureTerminal(worktreeUri, false);
+
+		const session = makeAgentSession({
+			isArchived: false,
+			worktreePath: worktreeUri.fsPath,
+		});
+		onDidChangeSessionArchivedState.fire(session);
+		await tick();
+
+		assert.strictEqual(disposedInstances.length, 0);
+	});
+
+	test('does not close terminals when archived session has no worktreePath', async () => {
+		const worktreeUri = URI.file('/worktree');
+		await contribution.ensureTerminal(worktreeUri, false);
+
+		const session = makeAgentSession({ isArchived: true });
+		onDidChangeSessionArchivedState.fire(session);
+		await tick();
+
+		assert.strictEqual(disposedInstances.length, 0);
+	});
+
+	// --- switching back to previously used path reuses terminal ---
+
+	test('switching back to a previously used background path reuses the existing terminal', async () => {
+		const cwd1 = URI.file('/cwd1');
+		const cwd2 = URI.file('/cwd2');
+
+		activeSessionObs.set(makeAgentSession({ worktree: cwd1, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+		assert.strictEqual(createdTerminals.length, 1);
+
+		activeSessionObs.set(makeAgentSession({ worktree: cwd2, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+		assert.strictEqual(createdTerminals.length, 2);
+
+		// Switch back to cwd1 - should reuse terminal, not create a new one
+		activeSessionObs.set(makeAgentSession({ worktree: cwd1, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+		assert.strictEqual(createdTerminals.length, 2, 'should reuse the terminal for cwd1');
+	});
+
+	// --- Terminal visibility management (cwd-based) ---
+
+	test('hides terminals from previous session when switching to a new session', async () => {
+		const cwd1 = URI.file('/cwd1');
+		const cwd2 = URI.file('/cwd2');
+
+		activeSessionObs.set(makeAgentSession({ worktree: cwd1, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+		assert.strictEqual(createdTerminals.length, 1);
+
+		activeSessionObs.set(makeAgentSession({ worktree: cwd2, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		// The first terminal (id=1) should have been moved to background
+		assert.ok(moveToBackgroundCalls.includes(1), 'terminal for cwd1 should be backgrounded');
+		assert.ok(backgroundedInstances.has(1), 'terminal for cwd1 should remain backgrounded');
+	});
+
+	test('shows previously hidden terminals when switching back to their session', async () => {
+		const cwd1 = URI.file('/cwd1');
+		const cwd2 = URI.file('/cwd2');
+
+		activeSessionObs.set(makeAgentSession({ worktree: cwd1, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		activeSessionObs.set(makeAgentSession({ worktree: cwd2, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		// Switch back to cwd1
+		activeSessionObs.set(makeAgentSession({ worktree: cwd1, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		// Terminal for cwd1 (id=1) should be shown again
+		assert.ok(showBackgroundCalls.includes(1), 'terminal for cwd1 should be shown');
+		assert.ok(!backgroundedInstances.has(1), 'terminal for cwd1 should be foreground');
+		// Terminal for cwd2 (id=2) should now be backgrounded
+		assert.ok(backgroundedInstances.has(2), 'terminal for cwd2 should be backgrounded');
+	});
+
+	test('only terminals of the active session are visible after multiple switches', async () => {
+		const cwd1 = URI.file('/cwd1');
+		const cwd2 = URI.file('/cwd2');
+		const cwd3 = URI.file('/cwd3');
+
+		activeSessionObs.set(makeAgentSession({ worktree: cwd1, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		activeSessionObs.set(makeAgentSession({ worktree: cwd2, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		activeSessionObs.set(makeAgentSession({ worktree: cwd3, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		// Only terminal for cwd3 (id=3) should be foreground
+		assert.ok(backgroundedInstances.has(1), 'terminal for cwd1 should be backgrounded');
+		assert.ok(backgroundedInstances.has(2), 'terminal for cwd2 should be backgrounded');
+		assert.ok(!backgroundedInstances.has(3), 'terminal for cwd3 should be foreground');
+	});
+
+	test('shows pre-existing terminal with matching cwd instead of creating a new one', async () => {
+		// Manually add a terminal that already exists with a matching cwd
+		const cwd = URI.file('/worktree');
+		const existingInstance = makeTerminalInstance(nextInstanceId++, cwd.fsPath);
+		terminalInstances.set(existingInstance.instanceId, existingInstance);
+		backgroundedInstances.add(existingInstance.instanceId);
+
+		activeSessionObs.set(makeAgentSession({ worktree: cwd, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		assert.strictEqual(createdTerminals.length, 0, 'should reuse existing terminal, not create a new one');
+		assert.ok(showBackgroundCalls.includes(existingInstance.instanceId), 'should show the existing terminal');
+	});
+
+	test('hides pre-existing terminal with non-matching cwd when session changes', async () => {
+		// Manually add a terminal that already exists with a different cwd
+		const otherInstance = makeTerminalInstance(nextInstanceId++, '/other/path');
+		terminalInstances.set(otherInstance.instanceId, otherInstance);
+
+		const cwd = URI.file('/worktree');
+		activeSessionObs.set(makeAgentSession({ worktree: cwd, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		assert.ok(moveToBackgroundCalls.includes(otherInstance.instanceId), 'non-matching terminal should be backgrounded');
+	});
+
+	test('ensureTerminal finds a backgrounded terminal instead of creating a new one', async () => {
+		const cwd = URI.file('/test-cwd');
+		await contribution.ensureTerminal(cwd, false);
+		const instanceId = activeInstanceSet[0];
+
+		// Manually background it
+		backgroundedInstances.add(instanceId);
+
+		// ensureTerminal should find it by cwd, not create a new one
+		const result = await contribution.ensureTerminal(cwd, false);
+
+		assert.strictEqual(createdTerminals.length, 1, 'should not create a new terminal');
+		assert.strictEqual(result[0].instanceId, instanceId, 'should return the existing backgrounded terminal');
+	});
+
+	test('visibility is determined by initial cwd, not by stored IDs', async () => {
+		// Create a terminal externally (not via ensureTerminal) with a known cwd
+		const cwd1 = URI.file('/cwd1');
+		const cwd2 = URI.file('/cwd2');
+		const ext1 = makeTerminalInstance(nextInstanceId++, cwd1.fsPath);
+		const ext2 = makeTerminalInstance(nextInstanceId++, cwd2.fsPath);
+		terminalInstances.set(ext1.instanceId, ext1);
+		terminalInstances.set(ext2.instanceId, ext2);
+
+		// Switch to cwd1 — ext1 should stay visible, ext2 should be hidden
+		activeSessionObs.set(makeAgentSession({ worktree: cwd1, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		assert.ok(!backgroundedInstances.has(ext1.instanceId), 'ext1 should be foreground (matching cwd)');
+		assert.ok(backgroundedInstances.has(ext2.instanceId), 'ext2 should be backgrounded (non-matching cwd)');
+
+		// Switch to cwd2 — ext2 should be shown, ext1 should be hidden
+		activeSessionObs.set(makeAgentSession({ worktree: cwd2, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		assert.ok(backgroundedInstances.has(ext1.instanceId), 'ext1 should now be backgrounded');
+		assert.ok(!backgroundedInstances.has(ext2.instanceId), 'ext2 should now be foreground');
+	});
+
+	// --- Most-recent-command active terminal selection ---
+
+	test('sets the terminal with the most recent command as active after visibility update', async () => {
+		const cwd = URI.file('/worktree');
+		const t1 = makeTerminalInstance(nextInstanceId++, cwd.fsPath);
+		const t2 = makeTerminalInstance(nextInstanceId++, cwd.fsPath);
+		terminalInstances.set(t1.instanceId, t1);
+		terminalInstances.set(t2.instanceId, t2);
+
+		// t1 ran a command at timestamp 100, t2 at timestamp 200 (more recent)
+		addCommandToInstance(t1, 100);
+		addCommandToInstance(t2, 200);
+
+		activeSessionObs.set(makeAgentSession({ worktree: cwd, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		// The most recent setActiveInstance call should be for t2
+		assert.strictEqual(activeInstanceSet.at(-1), t2.instanceId, 'should set the terminal with the most recent command as active');
+	});
+
+	test('does not change active instance when no terminals have command history', async () => {
+		const cwd = URI.file('/worktree');
+		const t1 = makeTerminalInstance(nextInstanceId++, cwd.fsPath);
+		const t2 = makeTerminalInstance(nextInstanceId++, cwd.fsPath);
+		terminalInstances.set(t1.instanceId, t1);
+		terminalInstances.set(t2.instanceId, t2);
+
+		const activeCountBefore = activeInstanceSet.length;
+
+		activeSessionObs.set(makeAgentSession({ worktree: cwd, providerType: AgentSessionProviders.Background }), undefined);
+		await tick();
+
+		// No setActiveInstance calls from visibility update since no commands were run
+		assert.strictEqual(activeInstanceSet.length, activeCountBefore, 'should not call setActiveInstance when no command history exists');
+	});
+});
+
+function tick(): Promise<void> {
+	return new Promise(resolve => setTimeout(resolve, 0));
+}
diff --git a/src/vs/sessions/contrib/welcome/browser/media/welcomeOverlay.css b/src/vs/sessions/contrib/welcome/browser/media/welcomeOverlay.css
index e5203a11e7f67..9883b93456e88 100644
--- a/src/vs/sessions/contrib/welcome/browser/media/welcomeOverlay.css
+++ b/src/vs/sessions/contrib/welcome/browser/media/welcomeOverlay.css
@@ -22,93 +22,71 @@
 	pointer-events: none;
 }
 
-/* ---- Card ---- */
+/* ---- Card (borderless, centered content) ---- */
 
 .sessions-welcome-card {
-	width: 460px;
-	max-width: 90vw;
-	padding: 32px;
-	border-radius: 8px;
-	background: var(--vscode-sideBar-background);
-	border: 1px solid var(--vscode-widget-border, transparent);
-	box-shadow: 0 4px 24px rgba(0, 0, 0, 0.2);
 	display: flex;
 	flex-direction: column;
-	gap: 24px;
+	align-items: center;
+	gap: 20px;
+	text-align: center;
 }
 
 /* ---- Header ---- */
 
+.sessions-welcome-header {
+	display: flex;
+	flex-direction: column;
+	align-items: center;
+	gap: 12px;
+}
+
+.sessions-welcome-header .sessions-welcome-icon .codicon {
+	font-size: 96px;
+	color: var(--vscode-descriptionForeground);
+}
+
 .sessions-welcome-header h2 {
-	margin: 0 0 4px 0;
-	font-size: 18px;
+	margin: 0;
+	font-size: 22px;
 	font-weight: 600;
 	color: var(--vscode-foreground);
 }
 
-.sessions-welcome-subtitle {
+.sessions-welcome-header .sessions-welcome-subtitle {
 	margin: 0;
-	font-size: 13px;
+	font-size: 14px;
 	color: var(--vscode-descriptionForeground);
 }
 
-/* ---- Step List ---- */
+/* ---- Action Area ---- */
 
-.sessions-welcome-step-list {
+.sessions-welcome-action-area {
 	display: flex;
 	flex-direction: column;
-	gap: 8px;
-}
-
-.sessions-welcome-step-item {
-	display: flex;
 	align-items: center;
 	gap: 10px;
-	padding: 8px 12px;
-	border-radius: 4px;
-	font-size: 13px;
-	color: var(--vscode-descriptionForeground);
-	background: transparent;
-	transition: background 150ms, color 150ms;
+	width: 320px;
 }
 
-.sessions-welcome-step-item.current {
-	background: var(--vscode-list-hoverBackground);
-	color: var(--vscode-foreground);
-}
-
-.sessions-welcome-step-item.satisfied {
-	color: var(--vscode-testing-iconPassed, var(--vscode-descriptionForeground));
+.sessions-welcome-action-area .monaco-button {
+	width: 100%;
+	padding: 10px 16px;
+	font-size: 14px;
 }
 
-/* ---- Step Indicator (number or check icon) ---- */
+/* ---- Spinner ---- */
 
-.sessions-welcome-step-indicator {
+.sessions-welcome-spinner {
 	display: flex;
 	align-items: center;
 	justify-content: center;
-	width: 22px;
-	height: 22px;
-	border-radius: 50%;
-	font-size: 12px;
-	font-weight: 600;
-	flex-shrink: 0;
-	border: 1px solid var(--vscode-descriptionForeground);
+	gap: 8px;
+	font-size: 13px;
 	color: var(--vscode-descriptionForeground);
 }
 
-.sessions-welcome-step-item.current .sessions-welcome-step-indicator {
-	border-color: var(--vscode-focusBorder);
-	color: var(--vscode-focusBorder);
-}
-
-.sessions-welcome-step-item.satisfied .sessions-welcome-step-indicator {
-	border-color: var(--vscode-testing-iconPassed, var(--vscode-focusBorder));
-	color: var(--vscode-testing-iconPassed, var(--vscode-focusBorder));
-}
-
-.sessions-welcome-step-indicator.loading {
-	border: none;
+.sessions-welcome-spinner .codicon-loading {
 	animation: sessions-spin 1.5s linear infinite;
 }
 
@@ -116,28 +94,6 @@
 	to { transform: rotate(360deg); }
 }
 
-.sessions-welcome-step-title {
-	flex: 1;
-}
-
-/* ---- Action Area ---- */
-
-.sessions-welcome-action-area {
-	display: flex;
-	flex-direction: column;
-	gap: 10px;
-}
-
-.sessions-welcome-action-description {
-	margin: 0;
-	font-size: 13px;
-	color: var(--vscode-descriptionForeground);
-}
-
-.sessions-welcome-action-area .monaco-button {
-	width: 100%;
-}
-
 /* ---- Error ---- */
 
 .sessions-welcome-error {
diff --git a/src/vs/sessions/contrib/welcome/browser/sessionsWelcomeOverlay.ts b/src/vs/sessions/contrib/welcome/browser/sessionsWelcomeOverlay.ts
deleted file mode 100644
index 1eca99dd18359..0000000000000
--- a/src/vs/sessions/contrib/welcome/browser/sessionsWelcomeOverlay.ts
+++ /dev/null
@@ -1,145 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-import './media/welcomeOverlay.css';
-import { Disposable, toDisposable } from '../../../../base/common/lifecycle.js';
-import { $, append } from '../../../../base/browser/dom.js';
-import { autorun } from '../../../../base/common/observable.js';
-import { Emitter, Event } from '../../../../base/common/event.js';
-import { Button } from '../../../../base/browser/ui/button/button.js';
-import { defaultButtonStyles } from '../../../../platform/theme/browser/defaultStyles.js';
-import { Codicon } from '../../../../base/common/codicons.js';
-import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
-import { ISessionsWelcomeService, ISessionsWelcomeStep } from '../common/sessionsWelcomeService.js';
-import { localize } from '../../../../nls.js';
-
-export class SessionsWelcomeOverlay extends Disposable {
-
-	private readonly overlay: HTMLElement;
-	private actionRunning = false;
-	private runningStepId: string | undefined;
-
-	private readonly _onDidDismiss = this._register(new Emitter<void>());
-	readonly onDidDismiss: Event<void> = this._onDidDismiss.event;
-
-	constructor(
-		container: HTMLElement,
-		@ISessionsWelcomeService private readonly welcomeService: ISessionsWelcomeService,
-	) {
-		super();
-
-		// Root overlay element — blocks the entire window
-		this.overlay = append(container, $('.sessions-welcome-overlay'));
-		this._register({ dispose: () => this.overlay.remove() });
-
-		const card = append(this.overlay, $('.sessions-welcome-card'));
-
-		// Header
-		const header = append(card, $('.sessions-welcome-header'));
-		append(header, $('h2', undefined, localize('welcomeTitle', "VS Code - Sessions")));
-		append(header, $('p.sessions-welcome-subtitle', undefined, localize('welcomeSubtitle', "Complete the following steps to get started.")));
-
-		// Step list container
-		const stepList = append(card, $('.sessions-welcome-step-list'));
-
-		// Current step action area
-		const actionArea = append(card, $('.sessions-welcome-action-area'));
-		const actionDescription = append(actionArea, $('p.sessions-welcome-action-description'));
-		const actionButton = this._register(new Button(actionArea, { ...defaultButtonStyles }));
-
-		// Track state for error display
-		const errorContainer = append(actionArea, $('p.sessions-welcome-error'));
-		errorContainer.style.display = 'none';
-
-		// Reactively render the step list and current step
-		this._register(autorun(reader => {
-			const steps = this.welcomeService.steps.read(reader);
-			const current = this.welcomeService.currentStep.read(reader);
-			const isComplete = this.welcomeService.isComplete.read(reader);
-
-			if (isComplete) {
-				this.dismiss();
-				return;
-			}
-
-			// Render step indicators
-			this.renderStepList(stepList, steps, current);
-
-			// Render current step action area
-			if (current) {
-				actionDescription.textContent = current.description;
-				actionButton.label = current.actionLabel;
-				actionButton.enabled = !this.actionRunning;
-				actionArea.style.display = '';
-			} else {
-				actionArea.style.display = 'none';
-			}
-		}));
-
-		// Button click handler
-		this._register(actionButton.onDidClick(async () => {
-			const current = this.welcomeService.currentStep.get();
-			if (!current || this.actionRunning) {
-				return;
-			}
-
-			this.actionRunning = true;
-			this.runningStepId = current.id;
-			actionButton.enabled = false;
-			errorContainer.style.display = 'none';
-
-			// Re-render step list to show spinner
-			this.renderStepList(stepList, this.welcomeService.steps.get(), current);
-
-			try {
-				await current.action();
-			} catch (err) {
-				errorContainer.textContent = localize('stepError', "Something went wrong. Please try again.");
-				errorContainer.style.display = '';
-			} finally {
-				this.actionRunning = false;
-				this.runningStepId = undefined;
-				actionButton.enabled = true;
-			}
-		}));
-	}
-
-	private renderStepList(container: HTMLElement, steps: readonly ISessionsWelcomeStep[], current: ISessionsWelcomeStep | undefined): void {
-		container.textContent = '';
-		for (let i = 0; i < steps.length; i++) {
-			const step = steps[i];
-			const satisfied = step.isSatisfied.get();
-			const isCurrent = step === current;
-
-			const stepEl = append(container, $(
-				'.sessions-welcome-step-item' +
-				(satisfied ? '.satisfied' : '') +
-				(isCurrent ? '.current' : '')
-			));
-
-			// Step number / check icon / spinner
-			const indicator = append(stepEl, $('.sessions-welcome-step-indicator'));
-			if (satisfied) {
-				indicator.appendChild(renderIcon(Codicon.check));
-			} else if (this.runningStepId === step.id) {
-				indicator.appendChild(renderIcon(Codicon.loading));
-				indicator.classList.add('loading');
-			} else {
-				indicator.textContent = String(i + 1);
-			}
-
-			// Step title
-			append(stepEl, $('span.sessions-welcome-step-title', undefined, step.title));
-		}
-	}
-
-	private dismiss(): void {
-		this.overlay.classList.add('sessions-welcome-overlay-dismissed');
-		this._onDidDismiss.fire();
-		// Allow CSS transition to finish before disposing
-		const handle = setTimeout(() => this.dispose(), 200);
-		this._register(toDisposable(() => clearTimeout(handle)));
-	}
-}
diff --git a/src/vs/sessions/contrib/welcome/browser/sessionsWelcomeService.ts b/src/vs/sessions/contrib/welcome/browser/sessionsWelcomeService.ts
deleted file mode 100644
index e650e2a7b5c92..0000000000000
--- a/src/vs/sessions/contrib/welcome/browser/sessionsWelcomeService.ts
+++ /dev/null
@@ -1,59 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-import { Disposable, toDisposable } from '../../../../base/common/lifecycle.js';
-import { IObservable, derived, observableValue, transaction } from '../../../../base/common/observable.js';
-import { DeferredPromise } from '../../../../base/common/async.js';
-import { ISessionsWelcomeService, ISessionsWelcomeStep } from '../common/sessionsWelcomeService.js';
-
-export class SessionsWelcomeService extends Disposable implements ISessionsWelcomeService {
-
-	declare readonly _serviceBrand: undefined;
-
-	private readonly _steps = observableValue<readonly ISessionsWelcomeStep[]>(this, []);
-	private readonly _initializedDeferred = new DeferredPromise<void>();
-
-	readonly steps: IObservable<readonly ISessionsWelcomeStep[]> = this._steps;
-
-	readonly isComplete: IObservable<boolean> = derived(this, reader => {
-		const steps = this._steps.read(reader);
-		if (steps.length === 0) {
-			return true;
-		}
-		return steps.every(step => step.isSatisfied.read(reader));
-	});
-
-	readonly whenInitialized: Promise<void> = this._initializedDeferred.p;
-
-	readonly currentStep: IObservable<ISessionsWelcomeStep | undefined> = derived(this, reader => {
-		const steps = this._steps.read(reader);
-		return steps.find(step => !step.isSatisfied.read(reader));
-	});
-
-	registerStep(step: ISessionsWelcomeStep) {
-		transaction(tx => {
-			const current = this._steps.get();
-			const updated = [...current, step].sort((a, b) => a.order - b.order);
-			this._steps.set(updated, tx);
-		});
-
-		return toDisposable(() => {
-			transaction(tx => {
-				const current = this._steps.get();
-				this._steps.set(current.filter(s => s !== step), tx);
-			});
-		});
-	}
-
-	/**
-	 * Wait for all currently registered steps to finish their async initialization,
-	 * then mark the service as initialized.
-	 */
-	async initialize(): Promise<void> {
-		const steps = this._steps.get();
-		await Promise.all(steps.map(s => s.initialized));
-		this._initializedDeferred.complete();
-	}
-}
diff --git a/src/vs/sessions/contrib/welcome/browser/steps/copilotChatInstallStep.ts b/src/vs/sessions/contrib/welcome/browser/steps/copilotChatInstallStep.ts
deleted file mode 100644
index c9883d26f6225..0000000000000
--- a/src/vs/sessions/contrib/welcome/browser/steps/copilotChatInstallStep.ts
+++ /dev/null
@@ -1,58 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-import { IObservable, observableFromEvent } from '../../../../../base/common/observable.js';
-import { localize } from '../../../../../nls.js';
-import { IProductService } from '../../../../../platform/product/common/productService.js';
-import { IExtensionService } from '../../../../../workbench/services/extensions/common/extensions.js';
-import { IExtensionsWorkbenchService } from '../../../../../workbench/contrib/extensions/common/extensions.js';
-import { ISessionsWelcomeStep } from '../../common/sessionsWelcomeService.js';
-
-export class CopilotChatInstallStep implements ISessionsWelcomeStep {
-
-	readonly id = 'copilotChat.install';
-	readonly title = localize('copilotChatInstall.title', "Install Copilot Chat");
-	readonly description = localize('copilotChatInstall.description', "The Copilot Chat extension is required for Agent Sessions.");
-	readonly actionLabel = localize('copilotChatInstall.action', "Install Copilot Chat");
-	readonly order = 10;
-
-	readonly isSatisfied: IObservable<boolean>;
-	readonly initialized: Promise<void>;
-
-	private readonly chatExtensionId: string;
-
-	constructor(
-		@IExtensionService private readonly extensionService: IExtensionService,
-		@IExtensionsWorkbenchService private readonly extensionsWorkbenchService: IExtensionsWorkbenchService,
-		@IProductService private readonly productService: IProductService,
-	) {
-		this.chatExtensionId = this.productService.defaultChatAgent?.chatExtensionId ?? '';
-
-		this.isSatisfied = observableFromEvent<boolean>(
-			this,
-			this.extensionService.onDidChangeExtensionsStatus,
-			() => this.extensionService.extensions.some(
-				ext => ext.identifier.value.toLowerCase() === this.chatExtensionId.toLowerCase()
-			)
-		);
-
-		// Wait until the extension host has loaded installed extensions
-		this.initialized = this.extensionService.whenInstalledExtensionsRegistered().then(() => { });
-	}
-
-	async action(): Promise<void> {
-		if (!this.chatExtensionId) {
-			return;
-		}
-
-		await this.extensionsWorkbenchService.install(this.chatExtensionId, {
-			enable: true,
-			isApplicationScoped: true,
-			isMachineScoped: false,
-			installEverywhere: true,
-			installPreReleaseVersion: this.productService.quality !== 'stable',
-		});
-	}
-}
diff --git a/src/vs/sessions/contrib/welcome/browser/steps/gitHubSignInStep.ts b/src/vs/sessions/contrib/welcome/browser/steps/gitHubSignInStep.ts
deleted file mode 100644
index 26ea8f49f75e2..0000000000000
--- a/src/vs/sessions/contrib/welcome/browser/steps/gitHubSignInStep.ts
+++ /dev/null
@@ -1,56 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-import { IObservable, observableValue } from '../../../../../base/common/observable.js';
-import { localize } from '../../../../../nls.js';
-import { IDefaultAccountService } from '../../../../../platform/defaultAccount/common/defaultAccount.js';
-import { IDefaultAccount } from '../../../../../base/common/defaultAccount.js';
-import { Disposable } from '../../../../../base/common/lifecycle.js';
-import { ISessionsWelcomeStep } from '../../common/sessionsWelcomeService.js';
-
-export class GitHubSignInStep extends Disposable implements ISessionsWelcomeStep {
-
-	readonly id = 'github.signIn';
-	readonly title = localize('githubSignIn.title', "Sign In with GitHub");
-	readonly description = localize('githubSignIn.description', "Sign in to your GitHub account to use Agent Sessions.");
-	readonly actionLabel = localize('githubSignIn.action', "Sign In");
-	readonly order = 20;
-
-	readonly isSatisfied: IObservable<boolean>;
-	readonly initialized: Promise<void>;
-
-	private readonly _isSatisfied = observableValue<boolean>(this, false);
-
-	constructor(
-		@IDefaultAccountService private readonly defaultAccountService: IDefaultAccountService,
-	) {
-		super();
-
-		this.isSatisfied = this._isSatisfied;
-
-		// Listen for account changes
-		this._register(this.defaultAccountService.onDidChangeDefaultAccount(account => {
-			this._isSatisfied.set(this.isSignedInWithValidToken(account), undefined);
-		}));
-
-		// Check initial state and mark initialized when resolved
-		this.initialized = this.defaultAccountService.getDefaultAccount().then(account => {
-			this._isSatisfied.set(this.isSignedInWithValidToken(account), undefined);
-		});
-	}
-
-	/**
-	 * Returns `true` when the user is signed in and their token has not
-	 * expired. A `null` value for {@link IDefaultAccount.entitlementsData}
-	 * indicates the OAuth token is expired or revoked (HTTP 401).
-	 */
-	private isSignedInWithValidToken(account: IDefaultAccount | null | undefined): boolean {
-		return account !== null && account !== undefined && account.entitlementsData !== null;
-	}
-
-	async action(): Promise<void> {
-		await this.defaultAccountService.signIn();
-	}
-}
diff --git a/src/vs/sessions/contrib/welcome/browser/welcome.contribution.ts b/src/vs/sessions/contrib/welcome/browser/welcome.contribution.ts
index fbc9149ceeb86..f22ddd122c584 100644
--- a/src/vs/sessions/contrib/welcome/browser/welcome.contribution.ts
+++ b/src/vs/sessions/contrib/welcome/browser/welcome.contribution.ts
@@ -3,30 +3,127 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { Disposable, DisposableStore, MutableDisposable } from '../../../../base/common/lifecycle.js';
-import { InstantiationType, registerSingleton } from '../../../../platform/instantiation/common/extensions.js';
-import { IInstantiationService, ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
+import './media/welcomeOverlay.css';
+import { Disposable, DisposableStore, MutableDisposable, toDisposable } from '../../../../base/common/lifecycle.js';
+import { SessionsWelcomeVisibleContext } from '../../../common/contextkeys.js';
+import { $, append } from '../../../../base/browser/dom.js';
+import { autorun } from '../../../../base/common/observable.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { renderIcon } from '../../../../base/browser/ui/iconLabel/iconLabels.js';
+import { Button } from '../../../../base/browser/ui/button/button.js';
+import { defaultButtonStyles } from '../../../../platform/theme/browser/defaultStyles.js';
+import { localize, localize2 } from '../../../../nls.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
 import { IProductService } from '../../../../platform/product/common/productService.js';
-import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
-import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
-import { IWorkbenchLayoutService } from '../../../../workbench/services/layout/browser/layoutService.js';
 import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../../workbench/common/contributions.js';
-import { bindContextKey } from '../../../../platform/observable/common/platformObservableUtils.js';
-import { autorun } from '../../../../base/common/observable.js';
+import { IWorkbenchLayoutService } from '../../../../workbench/services/layout/browser/layoutService.js';
+import { IExtensionService } from '../../../../workbench/services/extensions/common/extensions.js';
+import { ChatEntitlement, ChatEntitlementService, IChatEntitlementService } from '../../../../workbench/services/chat/common/chatEntitlementService.js';
+import { CHAT_SETUP_SUPPORT_ANONYMOUS_ACTION_ID } from '../../../../workbench/contrib/chat/browser/actions/chatActions.js';
+import { IInstantiationService, ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
 import { Action2, registerAction2 } from '../../../../platform/actions/common/actions.js';
 import { Categories } from '../../../../platform/action/common/actionCommonCategories.js';
-import { localize2 } from '../../../../nls.js';
-import { ISessionsWelcomeService } from '../common/sessionsWelcomeService.js';
-import { SessionsWelcomeService } from './sessionsWelcomeService.js';
-import { SessionsWelcomeOverlay } from './sessionsWelcomeOverlay.js';
-import { CopilotChatInstallStep } from './steps/copilotChatInstallStep.js';
-import { GitHubSignInStep } from './steps/gitHubSignInStep.js';
-import { SessionsWelcomeCompleteContext } from '../../../common/contextkeys.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
+import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
+import { IWorkbenchEnvironmentService } from '../../../../workbench/services/environment/common/environmentService.js';
 
 const WELCOME_COMPLETE_KEY = 'workbench.agentsession.welcomeComplete';
 
-// Register the service
-registerSingleton(ISessionsWelcomeService, SessionsWelcomeService, InstantiationType.Eager);
+class SessionsWelcomeOverlay extends Disposable {
+
+	private readonly overlay: HTMLElement;
+
+	constructor(
+		container: HTMLElement,
+		@IChatEntitlementService private readonly chatEntitlementService: ChatEntitlementService,
+		@ICommandService private readonly commandService: ICommandService,
+		@IExtensionService private readonly extensionService: IExtensionService,
+		@ILogService private readonly logService: ILogService,
+	) {
+		super();
+
+		this.overlay = append(container, $('.sessions-welcome-overlay'));
+		this.overlay.setAttribute('role', 'dialog');
+		this.overlay.setAttribute('aria-modal', 'true');
+		this.overlay.setAttribute('aria-label', localize('welcomeOverlay.aria', "Sign in to use Sessions"));
+		this._register(toDisposable(() => this.overlay.remove()));
+
+		const card = append(this.overlay, $('.sessions-welcome-card'));
+
+		// Header — large icon + title, centered
+		const header = append(card, $('.sessions-welcome-header'));
+		const iconEl = append(header, $('span.sessions-welcome-icon'));
+		iconEl.appendChild(renderIcon(Codicon.agent));
+		append(header, $('h2', undefined, localize('welcomeTitle', "Sign in to use Sessions")));
+		append(header, $('p.sessions-welcome-subtitle', undefined, localize('welcomeSubtitle', "Agent-powered development")));
+
+		// Action area
+		const actionArea = append(card, $('.sessions-welcome-action-area'));
+		const actionButton = this._register(new Button(actionArea, { ...defaultButtonStyles }));
+		actionButton.label = localize('sessions.getStarted', "Get Started");
+
+		const spinnerContainer = append(actionArea, $('.sessions-welcome-spinner'));
+		spinnerContainer.style.display = 'none';
+
+		const errorContainer = append(actionArea, $('p.sessions-welcome-error'));
+		errorContainer.style.display = 'none';
+
+		this._register(actionButton.onDidClick(() => this._runSetup(actionButton, spinnerContainer, errorContainer)));
+
+		// Focus the button so the overlay traps keyboard input
+		actionButton.focus();
+	}
+
+	private async _runSetup(button: Button, spinner: HTMLElement, error: HTMLElement): Promise<void> {
+		button.enabled = false;
+		error.style.display = 'none';
+
+		spinner.textContent = '';
+		spinner.appendChild(renderIcon(Codicon.loading));
+		append(spinner, $('span', undefined, localize('sessions.settingUp', "Setting up…")));
+		spinner.style.display = '';
+
+		try {
+			const success = await this.commandService.executeCommand<boolean>(CHAT_SETUP_SUPPORT_ANONYMOUS_ACTION_ID, {
+				dialogIcon: Codicon.agent,
+				dialogTitle: this.chatEntitlementService.anonymous ?
+					localize('sessions.startUsingSessions', "Start using Sessions") :
+					localize('sessions.signinRequired', "Sign in to use Sessions"),
+				dialogHideSkip: true
+			});
+
+			if (success) {
+				spinner.textContent = '';
+				spinner.appendChild(renderIcon(Codicon.loading));
+				append(spinner, $('span', undefined, localize('sessions.restarting', "Completing setup…")));
+
+				this.logService.info('[sessions welcome] Restarting extension host after setup completion');
+				const stopped = await this.extensionService.stopExtensionHosts(
+					localize('sessionsWelcome.restart', "Completing sessions setup")
+				);
+				if (stopped) {
+					await this.extensionService.startExtensionHosts();
+				}
+			} else {
+				button.enabled = true;
+				spinner.style.display = 'none';
+			}
+		} catch (err) {
+			this.logService.error('[sessions welcome] Setup failed:', err);
+			error.textContent = localize('sessions.setupError', "Something went wrong. Please try again.");
+			error.style.display = '';
+			button.enabled = true;
+			spinner.style.display = 'none';
+		}
+	}
+
+	dismiss(): void {
+		this.overlay.classList.add('sessions-welcome-overlay-dismissed');
+		const handle = setTimeout(() => this.dispose(), 200);
+		this._register(toDisposable(() => clearTimeout(handle)));
+	}
+}
 
 class SessionsWelcomeContribution extends Disposable implements IWorkbenchContribution {
 
@@ -36,109 +133,113 @@ class SessionsWelcomeContribution extends Disposable implements IWorkbenchContri
 	private readonly watcherRef = this._register(new MutableDisposable());
 
 	constructor(
-		@ISessionsWelcomeService private readonly welcomeService: ISessionsWelcomeService,
+		@IChatEntitlementService private readonly chatEntitlementService: ChatEntitlementService,
 		@IWorkbenchLayoutService private readonly layoutService: IWorkbenchLayoutService,
 		@IInstantiationService private readonly instantiationService: IInstantiationService,
 		@IProductService private readonly productService: IProductService,
-		@IContextKeyService private readonly contextKeyService: IContextKeyService,
 		@IStorageService private readonly storageService: IStorageService,
+		@IContextKeyService private readonly contextKeyService: IContextKeyService,
+		@IWorkbenchEnvironmentService private readonly environmentService: IWorkbenchEnvironmentService,
 	) {
 		super();
 
-		// Bind context key to the observable
-		this._register(bindContextKey(
-			SessionsWelcomeCompleteContext,
-			this.contextKeyService,
-			reader => this.welcomeService.isComplete.read(reader),
-		));
-
-		// Only proceed if the product is configured with a default chat agent
 		if (!this.productService.defaultChatAgent?.chatExtensionId) {
 			return;
 		}
 
-		const isFirstLaunch = !this.storageService.getBoolean(WELCOME_COMPLETE_KEY, StorageScope.APPLICATION, false);
-
-		this.registerSteps();
-		this.welcomeService.initialize();
+		// Allow automated tests to skip the welcome overlay entirely.
+		// Desktop: --skip-sessions-welcome CLI flag
+		// Web: ?skip-sessions-welcome query parameter
+		const envArgs = (this.environmentService as IWorkbenchEnvironmentService & { args?: Record<string, unknown> }).args;
+		if (envArgs?.['skip-sessions-welcome']) {
+			return;
+		}
+		if (typeof globalThis.location !== 'undefined' && new URLSearchParams(globalThis.location.search).has('skip-sessions-welcome')) {
+			return;
+		}
 
+		const isFirstLaunch = !this.storageService.getBoolean(WELCOME_COMPLETE_KEY, StorageScope.APPLICATION, false);
 		if (isFirstLaunch) {
-			// First launch: show the welcome overlay immediately
 			this.showOverlay();
 		} else {
-			// Returning user: only show if Copilot Chat is not installed
-			this.showOverlayIfNeededAfterInit();
+			this.showOverlayIfNeeded();
 		}
 	}
 
-	private registerSteps(): void {
-		const stepStore = this._register(new DisposableStore());
-
-		// Step 1: Install Copilot Chat extension
-		const copilotStep = this.instantiationService.createInstance(CopilotChatInstallStep);
-		stepStore.add(this.welcomeService.registerStep(copilotStep));
-
-		// Step 2: Sign in with GitHub
-		const signInStep = this.instantiationService.createInstance(GitHubSignInStep);
-		stepStore.add(signInStep);
-		stepStore.add(this.welcomeService.registerStep(signInStep));
-	}
-
-	private async showOverlayIfNeededAfterInit(): Promise<void> {
-		// Wait for extension host to know what's installed
-		await this.welcomeService.whenInitialized;
-
-		// For returning users, only the Copilot Chat install state is a
-		// reliable trigger. Auth session restore races at startup, so we
-		// don't re-show the overlay just because sign-in hasn't resolved.
-		// If everything is already satisfied, skip.
-		if (this.welcomeService.isComplete.get()) {
-			this.watchForSignOutOrTokenExpiry();
-			return;
+	private showOverlayIfNeeded(): void {
+		if (this._needsChatSetup()) {
+			this.showOverlay();
+		} else {
+			this.watchForRegressions();
 		}
-
-		this.showOverlay();
 	}
 
-	/**
-	 * After the welcome flow has been completed once, watch for sign-out
-	 * or token expiry and re-show the overlay when that happens.
-	 */
-	private watchForSignOutOrTokenExpiry(): void {
-		let wasComplete = this.welcomeService.isComplete.get();
+	private watchForRegressions(): void {
+		let wasComplete = !this._needsChatSetup();
 		this.watcherRef.value = autorun(reader => {
-			const isComplete = this.welcomeService.isComplete.read(reader);
-			if (wasComplete && !isComplete) {
+			this.chatEntitlementService.sentimentObs.read(reader);
+			this.chatEntitlementService.entitlementObs.read(reader);
+
+			const needsSetup = this._needsChatSetup();
+			if (wasComplete && needsSetup) {
 				this.showOverlay();
 			}
-			wasComplete = isComplete;
+			wasComplete = !needsSetup;
 		});
 	}
 
+	private _needsChatSetup(): boolean {
+		const { sentiment, entitlement } = this.chatEntitlementService;
+		if (
+			!sentiment?.installed ||						// Extension not installed: run setup to install
+			sentiment?.disabled ||							// Extension disabled: run setup to enable
+			entitlement === ChatEntitlement.Available ||	// Entitlement available: run setup to sign up
+			(
+				entitlement === ChatEntitlement.Unknown &&	// Entitlement unknown: run setup to sign in / sign up
+				!this.chatEntitlementService.anonymous		// unless anonymous access is enabled
+			)
+		) {
+			return true;
+		}
+
+		return false;
+	}
+
 	private showOverlay(): void {
 		if (this.overlayRef.value) {
-			return; // overlay already shown
+			return;
 		}
 
+		this.watcherRef.clear();
 		this.overlayRef.value = new DisposableStore();
 
+		// Mark the welcome overlay as visible for titlebar disabling
+		const welcomeVisibleKey = SessionsWelcomeVisibleContext.bindTo(this.contextKeyService);
+		welcomeVisibleKey.set(true);
+		this.overlayRef.value.add(toDisposable(() => welcomeVisibleKey.reset()));
+
 		const overlay = this.overlayRef.value.add(this.instantiationService.createInstance(
 			SessionsWelcomeOverlay,
 			this.layoutService.mainContainer,
 		));
 
-		// Mark welcome as complete once the overlay is dismissed (all steps satisfied)
-		this.overlayRef.value.add(overlay.onDidDismiss(() => {
-			this.overlayRef.clear();
-			this.storageService.store(WELCOME_COMPLETE_KEY, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
-			this.watchForSignOutOrTokenExpiry();
+		// When setup completes (observables flip), dismiss and watch again
+		this.overlayRef.value.add(autorun(reader => {
+			this.chatEntitlementService.sentimentObs.read(reader);
+			this.chatEntitlementService.entitlementObs.read(reader);
+
+			if (!this._needsChatSetup()) {
+				this.storageService.store(WELCOME_COMPLETE_KEY, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
+				overlay.dismiss();
+				this.overlayRef.clear();
+				this.watchForRegressions();
+			}
 		}));
 	}
 }
 
 registerWorkbenchContribution2(SessionsWelcomeContribution.ID, SessionsWelcomeContribution, WorkbenchPhase.BlockRestore);
 
-// Debug command to reset welcome state so the overlay shows again on next launch
 registerAction2(class extends Action2 {
 	constructor() {
 		super({
diff --git a/src/vs/sessions/contrib/welcome/common/sessionsWelcomeService.ts b/src/vs/sessions/contrib/welcome/common/sessionsWelcomeService.ts
deleted file mode 100644
index 6438542619d47..0000000000000
--- a/src/vs/sessions/contrib/welcome/common/sessionsWelcomeService.ts
+++ /dev/null
@@ -1,76 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-import { IObservable } from '../../../../base/common/observable.js';
-import { IDisposable } from '../../../../base/common/lifecycle.js';
-import { createDecorator } from '../../../../platform/instantiation/common/instantiation.js';
-
-/**
- * A single setup step in the sessions welcome flow.
- *
- * Steps are rendered sequentially by {@link order}. The overlay
- * advances to the next step once {@link isSatisfied} becomes `true`.
- */
-export interface ISessionsWelcomeStep {
-	/** Unique identifier for this step. */
-	readonly id: string;
-
-	/** Display title (localized). */
-	readonly title: string;
-
-	/** Short description shown when this step is the current step (localized). */
-	readonly description: string;
-
-	/** Reactive flag — `true` when this step's requirement is met. */
-	readonly isSatisfied: IObservable<boolean>;
-
-	/**
-	 * Resolves once the step has determined its initial satisfied state.
-	 * Until this resolves, {@link isSatisfied} may not reflect reality.
-	 */
-	readonly initialized: Promise<void>;
-
-	/** Label for the primary action button (localized). */
-	readonly actionLabel: string;
-
-	/**
-	 * Execute the primary action for this step.
-	 * For example, install an extension or trigger a sign-in flow.
-	 */
-	action(): Promise<void>;
-
-	/** Sorting order — lower values run first. */
-	readonly order: number;
-}
-
-export const ISessionsWelcomeService = createDecorator<ISessionsWelcomeService>('sessionsWelcomeService');
-
-export interface ISessionsWelcomeService {
-	readonly _serviceBrand: undefined;
-
-	/** All registered steps sorted by {@link ISessionsWelcomeStep.order}. */
-	readonly steps: IObservable<readonly ISessionsWelcomeStep[]>;
-
-	/** `true` when every registered step is satisfied. */
-	readonly isComplete: IObservable<boolean>;
-
-	/** Resolves once all registered steps have determined their initial state. */
-	readonly whenInitialized: Promise<void>;
-
-	/**
-	 * Wait for all currently registered steps to finish their async initialization,
-	 * then mark the service as initialized.
-	 */
-	initialize(): Promise<void>;
-
-	/** The first unsatisfied step, or `undefined` when all are done. */
-	readonly currentStep: IObservable<ISessionsWelcomeStep | undefined>;
-
-	/**
-	 * Register a new welcome step.
-	 * The returned disposable removes the step on disposal.
-	 */
-	registerStep(step: ISessionsWelcomeStep): IDisposable;
-}
diff --git a/src/vs/sessions/contrib/welcome/test/browser/gitHubSignInStep.test.ts b/src/vs/sessions/contrib/welcome/test/browser/gitHubSignInStep.test.ts
deleted file mode 100644
index 525ce00241ddf..0000000000000
--- a/src/vs/sessions/contrib/welcome/test/browser/gitHubSignInStep.test.ts
+++ /dev/null
@@ -1,123 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-import assert from 'assert';
-import { Emitter, Event } from '../../../../../base/common/event.js';
-import { DisposableStore } from '../../../../../base/common/lifecycle.js';
-import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
-import { IDefaultAccount } from '../../../../../base/common/defaultAccount.js';
-import { IDefaultAccountService } from '../../../../../platform/defaultAccount/common/defaultAccount.js';
-import { GitHubSignInStep } from '../../browser/steps/gitHubSignInStep.js';
-
-const VALID_ENTITLEMENTS: IDefaultAccount['entitlementsData'] = {
-	access_type_sku: 'free',
-	assigned_date: '',
-	can_signup_for_limited: false,
-	copilot_plan: 'free',
-	organization_login_list: [],
-	analytics_tracking_id: '',
-};
-
-function createAccount(entitlementsData?: IDefaultAccount['entitlementsData']): IDefaultAccount {
-	return {
-		authenticationProvider: { id: 'github', name: 'GitHub', enterprise: false },
-		accountName: 'testuser',
-		sessionId: 'session-1',
-		enterprise: false,
-		entitlementsData,
-	};
-}
-
-suite('GitHubSignInStep', () => {
-
-	const store = new DisposableStore();
-	let onDidChange: Emitter<IDefaultAccount | null>;
-	let resolveGetAccount: (account: IDefaultAccount | null) => void;
-
-	function createStep(): GitHubSignInStep {
-		onDidChange = store.add(new Emitter<IDefaultAccount | null>());
-		let resolve: (account: IDefaultAccount | null) => void;
-		const getAccountPromise = new Promise<IDefaultAccount | null>(r => resolve = r);
-		resolveGetAccount = resolve!;
-
-		const mockService = {
-			_serviceBrand: undefined,
-			onDidChangeDefaultAccount: onDidChange.event,
-			onDidChangePolicyData: Event.None,
-			policyData: null,
-			getDefaultAccount: () => getAccountPromise,
-			getDefaultAccountAuthenticationProvider: () => ({ id: 'github', name: 'GitHub', enterprise: false }),
-			setDefaultAccountProvider: () => { },
-			refresh: async () => null,
-			signIn: async () => null,
-			signOut: async () => { },
-		} satisfies IDefaultAccountService;
-
-		const step = new GitHubSignInStep(mockService);
-		store.add(step);
-		return step;
-	}
-
-	teardown(() => store.clear());
-	ensureNoDisposablesAreLeakedInTestSuite();
-
-	test('isSatisfied is true when account has valid entitlements', async () => {
-		const step = createStep();
-		resolveGetAccount(createAccount(VALID_ENTITLEMENTS));
-		await step.initialized;
-		assert.strictEqual(step.isSatisfied.get(), true);
-	});
-
-	test('isSatisfied is true when account has undefined entitlements', async () => {
-		const step = createStep();
-		resolveGetAccount(createAccount(undefined));
-		await step.initialized;
-		assert.strictEqual(step.isSatisfied.get(), true); // undefined means not configured, user is signed in
-	});
-
-	test('isSatisfied is false when account is null (signed out)', async () => {
-		const step = createStep();
-		resolveGetAccount(null);
-		await step.initialized;
-		assert.strictEqual(step.isSatisfied.get(), false);
-	});
-
-	test('isSatisfied is false when account has null entitlements (token expired)', async () => {
-		const step = createStep();
-		resolveGetAccount(createAccount(null));
-		await step.initialized;
-		assert.strictEqual(step.isSatisfied.get(), false);
-	});
-
-	test('isSatisfied reacts to sign-out event', async () => {
-		const step = createStep();
-		resolveGetAccount(createAccount(VALID_ENTITLEMENTS));
-		await step.initialized;
-		assert.strictEqual(step.isSatisfied.get(), true);
-
-		onDidChange.fire(null);
-		assert.strictEqual(step.isSatisfied.get(), false);
-	});
-
-	test('isSatisfied reacts to token expiry event', async () => {
-		const step = createStep();
-		resolveGetAccount(createAccount(VALID_ENTITLEMENTS));
-		await step.initialized;
-		assert.strictEqual(step.isSatisfied.get(), true);
-
-		onDidChange.fire(createAccount(null)); // token expired: account exists but entitlements null
-		assert.strictEqual(step.isSatisfied.get(), false);
-	});
-
-	test('isSatisfied recovers when token is refreshed', async () => {
-		const step = createStep();
-		resolveGetAccount(createAccount(null)); // start with expired token
-		await step.initialized;
-		assert.strictEqual(step.isSatisfied.get(), false);
-
-		onDidChange.fire(createAccount(VALID_ENTITLEMENTS));
-		assert.strictEqual(step.isSatisfied.get(), true);
-	});
-});
diff --git a/src/vs/sessions/contrib/workspace/browser/workspace.contribution.ts b/src/vs/sessions/contrib/workspace/browser/workspace.contribution.ts
new file mode 100644
index 0000000000000..4351598efa6b2
--- /dev/null
+++ b/src/vs/sessions/contrib/workspace/browser/workspace.contribution.ts
@@ -0,0 +1,9 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { registerWorkbenchContribution2, WorkbenchPhase } from '../../../../workbench/common/contributions.js';
+import { WorkspaceFolderManagementContribution } from './workspaceFolderManagement.js';
+
+registerWorkbenchContribution2(WorkspaceFolderManagementContribution.ID, WorkspaceFolderManagementContribution, WorkbenchPhase.AfterRestored);
diff --git a/src/vs/sessions/contrib/workspace/browser/workspaceFolderManagement.ts b/src/vs/sessions/contrib/workspace/browser/workspaceFolderManagement.ts
new file mode 100644
index 0000000000000..15104c8280e66
--- /dev/null
+++ b/src/vs/sessions/contrib/workspace/browser/workspaceFolderManagement.ts
@@ -0,0 +1,107 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { IWorkbenchContribution } from '../../../../workbench/common/contributions.js';
+import { IActiveSessionItem, ISessionsManagementService } from '../../sessions/browser/sessionsManagementService.js';
+import { AgentSessionProviders } from '../../../../workbench/contrib/chat/browser/agentSessions/agentSessions.js';
+import { IWorkspaceContextService } from '../../../../platform/workspace/common/workspace.js';
+import { IWorkspaceEditingService } from '../../../../workbench/services/workspaces/common/workspaceEditing.js';
+import { IWorkspaceTrustManagementService } from '../../../../platform/workspace/common/workspaceTrust.js';
+import { IUriIdentityService } from '../../../../platform/uriIdentity/common/uriIdentity.js';
+import { URI } from '../../../../base/common/uri.js';
+import { autorun } from '../../../../base/common/observable.js';
+import { IWorkspaceFolderCreationData } from '../../../../platform/workspaces/common/workspaces.js';
+import { getGitHubRemoteFileDisplayName } from '../../fileTreeView/browser/githubFileSystemProvider.js';
+import { Queue } from '../../../../base/common/async.js';
+
+export class WorkspaceFolderManagementContribution extends Disposable implements IWorkbenchContribution {
+
+	static readonly ID = 'workbench.contrib.workspaceFolderManagement';
+	private queue = this._register(new Queue<void>());
+
+	constructor(
+		@ISessionsManagementService private readonly sessionManagementService: ISessionsManagementService,
+		@IUriIdentityService private readonly uriIdentityService: IUriIdentityService,
+		@IWorkspaceContextService private readonly workspaceContextService: IWorkspaceContextService,
+		@IWorkspaceEditingService private readonly workspaceEditingService: IWorkspaceEditingService,
+		@IWorkspaceTrustManagementService private readonly workspaceTrustManagementService: IWorkspaceTrustManagementService,
+	) {
+		super();
+		this._register(autorun(reader => {
+			const activeSession = this.sessionManagementService.activeSession.read(reader);
+			this.queue.queue(() => this.updateWorkspaceFoldersForSession(activeSession));
+		}));
+	}
+
+	private async updateWorkspaceFoldersForSession(session: IActiveSessionItem | undefined): Promise<void> {
+		await this.manageTrustWorkspaceForSession(session);
+		const activeSessionFolderData = this.getActiveSessionFolderData(session);
+		const currentRepo = this.workspaceContextService.getWorkspace().folders[0]?.uri;
+
+		if (!activeSessionFolderData) {
+			if (currentRepo) {
+				await this.workspaceEditingService.removeFolders([currentRepo], true);
+			}
+			return;
+		}
+
+		if (!currentRepo) {
+			await this.workspaceEditingService.addFolders([activeSessionFolderData], true);
+			return;
+		}
+
+		if (this.uriIdentityService.extUri.isEqual(currentRepo, activeSessionFolderData.uri)) {
+			return;
+		}
+
+		await this.workspaceEditingService.updateFolders(0, 1, [activeSessionFolderData], true);
+	}
+
+	private getActiveSessionFolderData(session: IActiveSessionItem | undefined): IWorkspaceFolderCreationData | undefined {
+		if (!session) {
+			return undefined;
+		}
+
+		if (session.worktree) {
+			return {
+				uri: session.worktree,
+				name: session.repository ? `${this.uriIdentityService.extUri.basename(session.repository)} (${session.worktreeBranchName ?? this.uriIdentityService.extUri.basename(session.worktree)})` : this.uriIdentityService.extUri.basename(session.worktree)
+			};
+		}
+
+		if (session.repository) {
+			if (session.providerType === AgentSessionProviders.Background) {
+				return { uri: session.repository };
+			}
+			if (session.providerType === AgentSessionProviders.Cloud) {
+				return {
+					uri: session.repository,
+					name: getGitHubRemoteFileDisplayName(session.repository),
+				};
+			}
+		}
+
+		return undefined;
+	}
+
+	private async manageTrustWorkspaceForSession(session: IActiveSessionItem | undefined): Promise<void> {
+		if (session?.providerType !== AgentSessionProviders.Background) {
+			return;
+		}
+
+		if (!session.repository || !session.worktree) {
+			return;
+		}
+
+		if (!this.isUriTrusted(session.worktree)) {
+			await this.workspaceTrustManagementService.setUrisTrust([session.worktree], true);
+		}
+	}
+
+	private isUriTrusted(uri: URI): boolean {
+		return this.workspaceTrustManagementService.getTrustedUris().some(trustedUri => this.uriIdentityService.extUri.isEqual(trustedUri, uri));
+	}
+}
diff --git a/src/vs/sessions/copilot-customizations-spec.md b/src/vs/sessions/copilot-customizations-spec.md
new file mode 100644
index 0000000000000..2b39296618014
--- /dev/null
+++ b/src/vs/sessions/copilot-customizations-spec.md
@@ -0,0 +1,356 @@
+# Copilot Agent Runtime — Customization Surface Spec
+
+> **Purpose:** Definitive reference for every customization mechanism that affects agent behavior when a user sends a message. Intended for building a UI that collects all customizations into a single view.
+>
+> **Source:** `github/copilot-agent-runtime` codebase as of 2026-02-25.
+
+> Some information has been removed by the human compiling this spec, scoping to what is deemed most relevant for the sessions window implementation. For the full details, see the source code (for maintainers likely checked out side-by-side).
+
+---
+
+## Overview
+
+When a user sends a message, the agent assembles its behavior from **10 customization categories**, each discovered from well-known file paths, environment variables, or runtime APIs. This document enumerates every source, file pattern, and merge rule.
+
+---
+
+## 1. Instructions
+
+System-prompt additions that shape how the agent responds. Multiple sources are discovered and merged in priority order.
+
+### 1.1 Repo-Level Instruction Files
+
+Each pattern is defined in `src/helpers/repo-helpers.ts` → `instructionPatterns`:
+
+| Convention | File Pattern | Notes |
+|------------|-------------|-------|
+| Copilot | `{repo}/.github/copilot-instructions.md` | Primary repo instructions |
+| Codex / OpenAI | `{repo}/AGENTS.md` | OpenAI model convention |
+| Claude / Anthropic | `{repo}/CLAUDE.md` | Claude model convention |
+| Claude (alt) | `{repo}/.claude/CLAUDE.md` | Secondary Claude location |
+| Gemini / Google | `{repo}/GEMINI.md` | Gemini model convention |
+
+### 1.2 VSCode-Style Instruction Files
+
+Glob-matched instruction files with metadata (applyTo patterns, description).
+
+| Scope | File Pattern | Code Reference |
+|-------|-------------|----------------|
+| Repo | `{repo}/.github/instructions/**/*.instructions.md` | `readVSCodeInstructions()` |
+| User | `~/.copilot/instructions/**/*.instructions.md` | `readUserCopilotInstructions()` |
+
+### 1.3 User-Level Instructions
+
+| Scope | File Pattern | Code Reference |
+|-------|-------------|----------------|
+| User global | `~/.copilot/copilot-instructions.md` | `hasHomeCopilotInstructions()` |
+
+### 1.4 CWD-Specific Instructions
+
+When the working directory differs from the repo root, the same instruction patterns are re-checked relative to `{cwd}`:
+
+- `{cwd}/.github/copilot-instructions.md`
+- `{cwd}/CLAUDE.md`, `{cwd}/.claude/CLAUDE.md`
+- `{cwd}/AGENTS.md`
+- `{cwd}/GEMINI.md`
+
+### 1.5 Nested / Child Instructions
+
+Breadth-first traversal from `{cwd}` up to **2 levels deep** (`CHILD_INSTRUCTIONS_MAX_DEPTH = 2`), scanning all instruction patterns in subdirectories.
+
+**Ignored directories:** `node_modules`, `.git`, `vendor`, `dist`, `build`, `.next`, `.nuxt`, `out`, `coverage` (plus `.gitignore` patterns when available).
+
+Feature-gated via `enableChildInstructions` option.
+
+### 1.6 Additional Sources
+
+| Source | Mechanism |
+|--------|-----------|
+| Env var | `COPILOT_CUSTOM_INSTRUCTIONS_DIRS` — comma-separated list of additional directories to scan |
+| Organization | `RuntimeContext.organizationCustomInstructions` — injected at runtime via API (not file-based) |
+
+### 1.7 Merge Order
+
+Instructions are concatenated in this order (all additive):
+
+1. User global (`~/.copilot/copilot-instructions.md`)
+2. Repo-level instruction files (all patterns above)
+3. VSCode-style instruction files (repo, then user)
+4. CWD-specific overrides (when cwd ≠ repo root)
+5. Child/nested instructions
+6. Organization instructions (API-injected)
+
+Duplicate content is deduplicated by file content hash.
+
+---
+
+## 2. Skills
+
+Reusable prompt-based capabilities exposed as `/skill-name` slash commands.
+
+### 2.1 Discovery Paths
+
+| Source | File Pattern | Code Reference |
+|--------|-------------|----------------|
+| Repo (Copilot) | `{repo}/.github/skills/*/SKILL.md` | `loader.ts` collectProjectDirs |
+| Repo (Agents) | `{repo}/.agents/skills/*/SKILL.md` | `loader.ts` collectProjectDirs |
+| Repo (Claude) | `{repo}/.claude/skills/*/SKILL.md` | `loader.ts` collectProjectDirs |
+| User (Copilot) | `~/.copilot/skills/*/SKILL.md` | `loader.ts` personalDirs |
+| User (Claude) | `~/.claude/skills/*/SKILL.md` | `loader.ts` personalDirs |
+| Env var | Dirs listed in `COPILOT_SKILLS_DIRS` (comma-separated) | `loader.ts` |
+| Plugins | `{pluginRoot}/skills/*/SKILL.md` | `skills.ts` |
+
+### 2.2 File Structure
+
+Each skill is a directory containing a `SKILL.md` file with YAML frontmatter:
+
+```
+.github/skills/
+  my-skill/
+    SKILL.md       ← markdown with frontmatter
+```
+
+Or a flat `SKILL.md` directly in the skills directory (single-skill mode).
+
+### 2.3 Frontmatter Schema
+
+```yaml
+---
+name: skill-name                      # Optional; derived from folder name if absent
+description: "What this skill does"   # Optional; derived from first 3 lines of body
+allowed-tools: grep,view              # Comma-separated tool whitelist (optional)
+user-invocable: true                  # Whether user can invoke via slash command (default: true)
+disable-model-invocation: false       # Whether model can invoke autonomously (default: false)
+---
+
+Skill prompt content here...
+```
+
+---
+
+## 3. Commands
+
+A variant of skills, loaded from `.claude/commands/` only.
+
+| Source | File Pattern | Code Reference |
+|--------|-------------|----------------|
+| Project | `{repo}/.claude/commands/*.md` | `loader.ts` getCommandDirectories |
+| User | `~/.claude/commands/*.md` | `loader.ts` getCommandDirectories |
+
+**Note:** Commands use only the `.claude/` convention — not `.github/` or `.agents/`.
+
+Any `.md` file in the directory is treated as a command. Same frontmatter schema as skills. Treated internally as skills with `isCommand: true`. Skills take priority over commands on name conflicts.
+
+---
+
+## 4. Custom Agents
+
+Sub-agent definitions available via the task tool or direct user selection.
+
+### 4.1 Discovery Paths
+
+| Source | File Pattern | Code Reference |
+|--------|-------------|----------------|
+| Repo (Copilot) | `{repo}/.github/agents/*.md`, `*.agent.md` | `useCustomAgents.ts` |
+| Repo (Claude) | `{repo}/.claude/agents/*.md`, `*.agent.md` | `useCustomAgents.ts` |
+| User (Copilot) | `~/.github/agents/*.md`, `*.agent.md` | `useCustomAgents.ts` |
+| User (Claude) | `~/.claude/agents/*.md`, `*.agent.md` | `useCustomAgents.ts` |
+| Plugins | `{pluginRoot}/agents/*.md`, `*.agent.md` | `agent-loader.ts` |
+| Builtin | `src/agents/definitions/*.agent.yaml` | YAML agent loader |
+
+### 4.2 Priority Rules
+
+- `*.agent.md` takes precedence over `*.md` when both exist for the same base name.
+- `.github/agents/` sources have higher priority than `.claude/agents/`.
+
+### 4.3 Frontmatter Schema
+
+```yaml
+---
+name: agent-name
+displayName: "Human-Readable Name"
+description: "What this agent does"
+tools: ["*"]                          # or ["tool1", "tool2"] — required
+model: claude-sonnet-4-20250514                  # Optional model override
+disableModelInvocation: false         # Cannot be auto-invoked as a tool
+userInvocable: true                   # User can select it
+mcp-servers:                          # Inline MCP server config (optional)
+  server-name:
+    command: "npx"
+    args: ["@some/mcp-server"]
+---
+
+Agent system prompt content here...
+Supports {{cwd}} placeholder.
+```
+
+---
+
+## 5. MCP Servers
+
+Model Context Protocol servers that expose additional tools and resources.
+
+### 5.1 Config Sources (merge order, last wins)
+
+| Priority | Source | File Pattern | Code Reference |
+|----------|--------|-------------|----------------|
+| 1 (lowest) | User | `~/.copilot/mcp-config.json` | `mcp-config.ts` |
+| 2 | Workspace | `{cwd}/.mcp.json` | `mcpConfigMerger.ts` |
+| 3 | VSCode | `{cwd}/.vscode/mcp.json` | `vsCodeWorkspaceMcpConfig.ts` |
+| 4 | Plugins | `{pluginRoot}/.mcp.json`, `{pluginRoot}/.github/mcp.json` | `mcp-loader.ts` |
+| 5 | Windows ODR | Registry `HKLM\SOFTWARE\Microsoft\Windows\CurrentVersion\Mcp` | `odrMcpRegistry.ts` |
+| 6 (highest) | CLI flag | `--additional-mcp-config <json\|@filepath>` | `mcpConfigMerger.ts` |
+
+### 5.2 Config Schema
+
+```json
+{
+  "mcpServers": {
+    "server-name": {
+      "type": "local | http | sse",
+      "command": "path/to/server",
+      "args": ["--flag"],
+      "cwd": "/optional/working/dir",
+      "env": {
+        "KEY": "$ENV_VAR",
+        "URL": "https://${HOST}:${PORT}",
+        "WITH_DEFAULT": "${VAR:-fallback}"
+      },
+      "url": "https://remote-server/endpoint",
+      "headers": { "Authorization": "Bearer ${TOKEN}" },
+      "tools": ["*"],
+      "timeout": 30000,
+      "filterMapping": "hidden_characters | markdown | none",
+      "displayName": "My Server",
+      "oauthClientId": "client-id",
+      "oauthPublicClient": false
+    }
+  }
+}
+```
+
+**Environment variable expansion:** `$VAR`, `${VAR}`, `${VAR:-default}` are all supported in `env`, `args`, `url`, and `headers` fields.
+
+---
+
+## 6. Hooks
+
+Scripts that execute at specific agent lifecycle events, with the ability to approve/deny/modify behavior.
+
+### 6.1 Config Sources
+
+| Source | File Pattern | Code Reference |
+|--------|-------------|----------------|
+| Config dirs | `{configDir}/**/*.json` | `hookConfigLoader.ts` |
+| Plugins | `{pluginRoot}/hooks.json` | `hooks.ts` |
+| Plugins (alt) | `{pluginRoot}/hooks/hooks.json` | `hooks.ts` |
+| Plugin manifest | Inline in `plugin.json` → `hooks` field (object) | `hooks.ts` |
+
+### 6.2 Hook Events
+
+| Event | Trigger | Can Modify? |
+|-------|---------|-------------|
+| `sessionStart` | Session begins | No (informational) |
+| `sessionEnd` | Session ends | No (informational) |
+| `userPromptSubmitted` | User sends a message | Yes (can modify prompt) |
+| `preToolUse` | Before tool execution | Yes (allow / deny / modify args) |
+| `postToolUse` | After tool execution | Yes (can modify result) |
+| `errorOccurred` | Error happens | Yes (retry / skip / abort) |
+| `agentStop` | Main agent finishes | Yes (can force continuation) |
+| `subagentStop` | Sub-agent completes | Yes (can force continuation) |
+
+### 6.3 Config Schema
+
+```json
+{
+  "version": 1,
+  "hooks": {
+    "preToolUse": [
+      {
+        "type": "command",
+        "command": "bash",
+        "args": ["-c", "echo checking"],
+        "cwd": "/optional/cwd",
+        "env": { "KEY": "value" },
+        "timeout": 30000
+      }
+    ]
+  }
+}
+```
+
+---
+
+## 7. Plugins
+
+Bundles that install combinations of skills, agents, hooks, and MCP servers.
+
+### 7.1 Plugin Manifest Locations
+
+Within a plugin repository, the manifest is searched at:
+
+| File Pattern | Code Reference |
+|-------------|----------------|
+| `plugin.json` | `marketplace-loader.ts` PLUGIN_JSON_PATHS |
+| `.github/plugin/plugin.json` | `marketplace-loader.ts` PLUGIN_JSON_PATHS |
+| `.claude-plugin/plugin.json` | `marketplace-loader.ts` PLUGIN_JSON_PATHS |
+
+
+Each field (`skills`, `agents`, `hooks`) can be a string path, array of paths, or (for hooks) an inline object.
+
+---
+
+## Appendix A: XDG Base Directory Compliance
+
+All `~/.copilot/` paths respect XDG overrides:
+
+| Type | Default | XDG Override |
+|------|---------|-------------|
+| Config files | `~/.copilot/` | `$XDG_CONFIG_HOME/.copilot/` |
+| State/cache | `~/.copilot/` | `$XDG_STATE_HOME/.copilot/` |
+
+The base directory name is always `.copilot` (`APP_DIRECTORY` in `path-helpers.ts`).
+
+---
+
+## Appendix B: Complete Discovery Summary
+
+```
+Message received
+ │
+ ├─ Feature flags resolved
+ │   ├─ Tier defaults
+ │   ├─ config.json → feature_flags.enabled
+ │   └─ Env vars (COPILOT_CLI_ENABLED_FEATURE_FLAGS, individual)
+ │
+ ├─ System prompt assembled
+ │   ├─ Base agent prompt
+ │   ├─ User instructions      ~/.copilot/copilot-instructions.md
+ │   ├─ Repo instructions       .github/copilot-instructions.md, AGENTS.md, CLAUDE.md, GEMINI.md
+ │   ├─ VSCode instructions     .github/instructions/**/*.instructions.md
+ │   ├─ CWD instructions        (when cwd ≠ repo root)
+ │   ├─ Child instructions      (depth=2 traversal)
+ │   └─ Org instructions        (API-injected)
+ │
+ ├─ Tools assembled
+ │   ├─ Built-in tools
+ │   ├─ MCP servers             ~/.copilot/mcp-config.json + .mcp.json + .vscode/mcp.json + plugins
+ │   └─ Content exclusion       (org API restrictions applied)
+ │
+ ├─ Skills listed               .github/skills/ + .agents/skills/ + .claude/skills/ + personal + plugins
+ ├─ Commands listed             .claude/commands/ + personal
+ ├─ Custom agents listed        .github/agents/ + .claude/agents/ + personal + plugins
+ │
+ ├─ userPromptSubmitted hooks fire
+ │
+ ├─ Model selected              config.json → model, agent override, or default
+ │
+ ├─ For each tool call:
+ │   ├─ preToolUse hooks        (allow / deny / modify)
+ │   ├─ Permission check
+ │   ├─ Firewall policy
+ │   ├─ Tool executes
+ │   └─ postToolUse hooks       (modify result)
+ │
+ └─ Session telemetry emitted
+```
diff --git a/src/vs/sessions/electron-browser/sessions-dev.html b/src/vs/sessions/electron-browser/sessions-dev.html
index 56f1b22575beb..f453fb51b7fe7 100644
--- a/src/vs/sessions/electron-browser/sessions-dev.html
+++ b/src/vs/sessions/electron-browser/sessions-dev.html
@@ -65,6 +65,7 @@
 					tokenizeToString
 					notebookChatEditController
 					richScreenReaderContent
+					chatDebugTokenizer
 				;
 		"/>
 	</head>
diff --git a/src/vs/sessions/electron-browser/sessions.html b/src/vs/sessions/electron-browser/sessions.html
index afb0a45e67ec7..de2f45b136e5c 100644
--- a/src/vs/sessions/electron-browser/sessions.html
+++ b/src/vs/sessions/electron-browser/sessions.html
@@ -63,6 +63,7 @@
 					tokenizeToString
 					notebookChatEditController
 					richScreenReaderContent
+					chatDebugTokenizer
 				;
 		"/>
 
diff --git a/src/vs/sessions/electron-browser/sessions.main.ts b/src/vs/sessions/electron-browser/sessions.main.ts
index 87669d73043a2..4cb60de615791 100644
--- a/src/vs/sessions/electron-browser/sessions.main.ts
+++ b/src/vs/sessions/electron-browser/sessions.main.ts
@@ -11,12 +11,11 @@ import { setFullscreen } from '../../base/browser/browser.js';
 import { domContentLoaded } from '../../base/browser/dom.js';
 import { onUnexpectedError } from '../../base/common/errors.js';
 import { URI } from '../../base/common/uri.js';
-import { WorkspaceService } from '../../workbench/services/configuration/browser/configurationService.js';
 import { INativeWorkbenchEnvironmentService, NativeWorkbenchEnvironmentService } from '../../workbench/services/environment/electron-browser/environmentService.js';
 import { ServiceCollection } from '../../platform/instantiation/common/serviceCollection.js';
 import { ILoggerService, ILogService, LogLevel } from '../../platform/log/common/log.js';
 import { NativeWorkbenchStorageService } from '../../workbench/services/storage/electron-browser/storageService.js';
-import { IWorkspaceContextService, isSingleFolderWorkspaceIdentifier, isWorkspaceIdentifier, IAnyWorkspaceIdentifier, reviveIdentifier, toWorkspaceIdentifier } from '../../platform/workspace/common/workspace.js';
+import { IWorkspaceContextService, isSingleFolderWorkspaceIdentifier, isWorkspaceIdentifier, IAnyWorkspaceIdentifier, reviveIdentifier } from '../../platform/workspace/common/workspace.js';
 import { IWorkbenchConfigurationService } from '../../workbench/services/configuration/common/configuration.js';
 import { IStorageService } from '../../platform/storage/common/storage.js';
 import { Disposable } from '../../base/common/lifecycle.js';
@@ -30,7 +29,6 @@ import { IRemoteAgentService } from '../../workbench/services/remote/common/remo
 import { FileService } from '../../platform/files/common/fileService.js';
 import { IFileService } from '../../platform/files/common/files.js';
 import { RemoteFileSystemProviderClient } from '../../workbench/services/remote/common/remoteFileSystemProviderClient.js';
-import { ConfigurationCache } from '../../workbench/services/configuration/common/configurationCache.js';
 import { ISignService } from '../../platform/sign/common/sign.js';
 import { IProductService } from '../../platform/product/common/productService.js';
 import { IUriIdentityService } from '../../platform/uriIdentity/common/uriIdentity.js';
@@ -66,8 +64,12 @@ import { AccountPolicyService } from '../../workbench/services/policies/common/a
 import { MultiplexPolicyService } from '../../workbench/services/policies/common/multiplexPolicyService.js';
 import { Workbench as AgenticWorkbench } from '../browser/workbench.js';
 import { NativeMenubarControl } from '../../workbench/electron-browser/parts/titlebar/menubarControl.js';
+import { IWorkspaceEditingService } from '../../workbench/services/workspaces/common/workspaceEditing.js';
+import { ConfigurationService } from '../services/configuration/browser/configurationService.js';
+import { SessionsWorkspaceContextService } from '../services/workspace/browser/workspaceContextService.js';
+import { getWorkspaceIdentifier } from '../../workbench/services/workspaces/browser/workspaces.js';
 
-export class AgenticMain extends Disposable {
+export class SessionsMain extends Disposable {
 
 	constructor(
 		private readonly configuration: INativeWindowConfiguration
@@ -167,7 +169,7 @@ export class AgenticMain extends Disposable {
 		this._register(workbench.onDidShutdown(() => this.dispose()));
 	}
 
-	private async initServices(): Promise<{ serviceCollection: ServiceCollection; logService: ILogService; storageService: NativeWorkbenchStorageService; configurationService: WorkspaceService }> {
+	private async initServices(): Promise<{ serviceCollection: ServiceCollection; logService: ILogService; storageService: NativeWorkbenchStorageService; configurationService: ConfigurationService }> {
 		const serviceCollection = new ServiceCollection();
 
 
@@ -290,21 +292,23 @@ export class AgenticMain extends Disposable {
 		//
 		// !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
 
-		// Create services that require resolving in parallel
-		const workspace = this.resolveWorkspaceIdentifier(environmentService);
-		const [configurationService, storageService] = await Promise.all([
-			this.createWorkspaceService(workspace, environmentService, userDataProfileService, userDataProfilesService, fileService, remoteAgentService, uriIdentityService, logService, policyService).then(service => {
+		const workspaceIdentifier = getWorkspaceIdentifier(environmentService.agentSessionsWorkspace);
+		const workspaceContextService = new SessionsWorkspaceContextService(workspaceIdentifier, uriIdentityService);
 
-				// Workspace
-				serviceCollection.set(IWorkspaceContextService, service);
+		// Workspace
+		serviceCollection.set(IWorkspaceContextService, workspaceContextService);
+		serviceCollection.set(IWorkspaceEditingService, workspaceContextService);
+
+		const [configurationService, storageService] = await Promise.all([
+			this.createConfigurationService(workspaceContextService, userDataProfileService, uriIdentityService, fileService, logService, policyService).then(configurationService => {
 
 				// Configuration
-				serviceCollection.set(IWorkbenchConfigurationService, service);
+				serviceCollection.set(IWorkbenchConfigurationService, configurationService);
 
-				return service;
+				return configurationService;
 			}),
 
-			this.createStorageService(workspace, environmentService, userDataProfileService, userDataProfilesService, mainProcessService).then(service => {
+			this.createStorageService(workspaceIdentifier, environmentService, userDataProfileService, userDataProfilesService, mainProcessService).then(service => {
 
 				// Storage
 				serviceCollection.set(IStorageService, service);
@@ -325,13 +329,9 @@ export class AgenticMain extends Disposable {
 		const workspaceTrustEnablementService = new WorkspaceTrustEnablementService(configurationService, environmentService);
 		serviceCollection.set(IWorkspaceTrustEnablementService, workspaceTrustEnablementService);
 
-		const workspaceTrustManagementService = new WorkspaceTrustManagementService(configurationService, remoteAuthorityResolverService, storageService, uriIdentityService, environmentService, configurationService, workspaceTrustEnablementService, fileService);
+		const workspaceTrustManagementService = new WorkspaceTrustManagementService(configurationService, remoteAuthorityResolverService, storageService, uriIdentityService, environmentService, workspaceContextService, workspaceTrustEnablementService, fileService);
 		serviceCollection.set(IWorkspaceTrustManagementService, workspaceTrustManagementService);
 
-		// Update workspace trust so that configuration is updated accordingly
-		configurationService.updateWorkspaceTrust(workspaceTrustManagementService.isWorkspaceTrusted());
-		this._register(workspaceTrustManagementService.onDidChangeTrust(() => configurationService.updateWorkspaceTrust(workspaceTrustManagementService.isWorkspaceTrusted())));
-
 
 		// !!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!!
 		//
@@ -346,40 +346,22 @@ export class AgenticMain extends Disposable {
 		return { serviceCollection, logService, storageService, configurationService };
 	}
 
-	private resolveWorkspaceIdentifier(environmentService: INativeWorkbenchEnvironmentService): IAnyWorkspaceIdentifier {
-
-		// Return early for when a folder or multi-root is opened
-		if (this.configuration.workspace) {
-			return this.configuration.workspace;
-		}
-
-		// Otherwise, workspace is empty, so we derive an identifier
-		return toWorkspaceIdentifier(this.configuration.backupPath, environmentService.isExtensionDevelopment);
-	}
-
-	private async createWorkspaceService(
-		workspace: IAnyWorkspaceIdentifier,
-		environmentService: INativeWorkbenchEnvironmentService,
+	private async createConfigurationService(
+		workspaceContextService: SessionsWorkspaceContextService,
 		userDataProfileService: IUserDataProfileService,
-		userDataProfilesService: IUserDataProfilesService,
-		fileService: FileService,
-		remoteAgentService: IRemoteAgentService,
 		uriIdentityService: IUriIdentityService,
+		fileService: FileService,
 		logService: ILogService,
 		policyService: IPolicyService
-	): Promise<WorkspaceService> {
-		const configurationCache = new ConfigurationCache([Schemas.file, Schemas.vscodeUserData] /* Cache all non native resources */, environmentService, fileService);
-		const workspaceService = new WorkspaceService({ remoteAuthority: environmentService.remoteAuthority, configurationCache }, environmentService, userDataProfileService, userDataProfilesService, fileService, remoteAgentService, uriIdentityService, logService, policyService);
-
+	): Promise<ConfigurationService> {
+		const configurationService = new ConfigurationService(userDataProfileService, workspaceContextService, uriIdentityService, fileService, policyService, logService);
 		try {
-			await workspaceService.initialize(workspace);
-
-			return workspaceService;
+			await configurationService.initialize();
 		} catch (error) {
 			onUnexpectedError(error);
-
-			return workspaceService;
 		}
+
+		return configurationService;
 	}
 
 	private async createStorageService(workspace: IAnyWorkspaceIdentifier, environmentService: INativeWorkbenchEnvironmentService, userDataProfileService: IUserDataProfileService, userDataProfilesService: IUserDataProfilesService, mainProcessService: IMainProcessService): Promise<NativeWorkbenchStorageService> {
@@ -416,7 +398,7 @@ export interface IDesktopMain {
 }
 
 export function main(configuration: INativeWindowConfiguration): Promise<void> {
-	const workbench = new AgenticMain(configuration);
+	const workbench = new SessionsMain(configuration);
 
 	return workbench.open();
 }
diff --git a/src/vs/sessions/prompts/create-draft-pr.prompt.md b/src/vs/sessions/prompts/create-draft-pr.prompt.md
new file mode 100644
index 0000000000000..4def295b9fcff
--- /dev/null
+++ b/src/vs/sessions/prompts/create-draft-pr.prompt.md
@@ -0,0 +1,11 @@
+---
+description: Create a draft pull request for the current session
+---
+<!-- Customize this prompt and select save to override its behavior. Delete that copy to restore the built-in behavior. -->
+
+Use the GitHub MCP server to create a draft pull request — do NOT use the `gh` CLI.
+
+1. Review all changes in the current session
+2. Write a clear, concise PR title with a short area prefix (e.g. "sessions: …", "editor: …")
+3. Write a description covering what changed, why, and anything reviewers should know
+4. Create the draft pull request
diff --git a/src/vs/sessions/prompts/create-pr.prompt.md b/src/vs/sessions/prompts/create-pr.prompt.md
new file mode 100644
index 0000000000000..02208021e3a28
--- /dev/null
+++ b/src/vs/sessions/prompts/create-pr.prompt.md
@@ -0,0 +1,12 @@
+---
+description: Create a pull request for the current session
+---
+<!-- Customize this prompt and select save to override its behavior. Delete that copy to restore the built-in behavior. -->
+
+Use the GitHub MCP server to create a pull request — do NOT use the `gh` CLI.
+
+1. Run the compile and hygiene tasks (fixing any errors)
+2. Review all changes in the current session
+3. Write a clear, concise PR title with a short area prefix (e.g. "sessions: …", "editor: …")
+4. Write a description covering what changed, why, and anything reviewers should know
+5. Create the pull request
diff --git a/src/vs/sessions/prompts/generate-run-commands.prompt.md b/src/vs/sessions/prompts/generate-run-commands.prompt.md
new file mode 100644
index 0000000000000..e1744cf92c38a
--- /dev/null
+++ b/src/vs/sessions/prompts/generate-run-commands.prompt.md
@@ -0,0 +1,50 @@
+---
+description: Generate or modify run commands for the current session
+---
+<!-- Customize this prompt and select save to override its behavior. Delete that copy to restore the built-in behavior. -->
+
+Help the user set up run commands for the current Agent Session workspace. Run commands appear in the session's Run button in the title bar.
+
+## Understanding the task schema
+
+A run command is a `tasks.json` task with:
+- `"inSessions": true` — required: makes the task appear in the Sessions run button
+- `"runOptions": { "runOn": "worktreeCreated" }` — optional: auto-runs the task whenever a new worktree is created (use for setup/install commands)
+
+```json
+{
+  "tasks": [
+    {
+      "label": "Install dependencies",
+      "type": "shell",
+      "command": "npm install",
+      "inSessions": true,
+      "runOptions": { "runOn": "worktreeCreated" }
+    },
+    {
+      "label": "Start dev server",
+      "type": "shell",
+      "command": "npm run dev",
+      "inSessions": true
+    }
+  ]
+}
+```
+
+## Decision logic
+
+**First, read the existing `.vscode/tasks.json`** to check for existing run commands (`inSessions: true` tasks).
+
+**If run commands already exist:** treat this as a modify request — ask the user what they'd like to change (add, remove, or update a command).
+
+**If no run commands exist:** try to infer the right commands from the workspace:
+- Check `package.json`, `Makefile`, `pyproject.toml`, `Cargo.toml`, `go.mod`, `.nvmrc`, or other project files to understand the stack and common commands.
+- If it's clear what the setup command is (e.g., `npm install`, `pip install -r requirements.txt`), add it with `"runOptions": { "runOn": "worktreeCreated" }` — no need to ask.
+- If it's clear what the primary run/dev command is (e.g., `npm run dev`, `cargo run`), add it with just `"inSessions": true`.
+- **Only ask the user** if the commands are ambiguous (e.g., multiple equally valid options, no recognizable project structure, or the project uses a non-standard setup).
+
+## Writing the file
+
+Always write to `.vscode/tasks.json` in the workspace root. If the file already exists, merge — do not overwrite unrelated tasks.
+
+After writing, briefly confirm what was added and how to trigger it from the Run button.
diff --git a/src/vs/sessions/services/configuration/browser/configurationService.ts b/src/vs/sessions/services/configuration/browser/configurationService.ts
new file mode 100644
index 0000000000000..01fb00152a6a1
--- /dev/null
+++ b/src/vs/sessions/services/configuration/browser/configurationService.ts
@@ -0,0 +1,377 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { onUnexpectedError } from '../../../../base/common/errors.js';
+import { Emitter, Event } from '../../../../base/common/event.js';
+import { Disposable, DisposableMap } from '../../../../base/common/lifecycle.js';
+import { ResourceMap } from '../../../../base/common/map.js';
+import { URI } from '../../../../base/common/uri.js';
+import { Queue } from '../../../../base/common/async.js';
+import { VSBuffer } from '../../../../base/common/buffer.js';
+import { JSONPath, ParseError, parse } from '../../../../base/common/json.js';
+import { applyEdits, setProperty } from '../../../../base/common/jsonEdit.js';
+import { Edit, FormattingOptions } from '../../../../base/common/jsonFormatter.js';
+import { equals } from '../../../../base/common/objects.js';
+import { distinct, equals as arrayEquals } from '../../../../base/common/arrays.js';
+import { OS, OperatingSystem } from '../../../../base/common/platform.js';
+import { IConfigurationChange, IConfigurationChangeEvent, IConfigurationData, IConfigurationOverrides, IConfigurationUpdateOptions, IConfigurationUpdateOverrides, IConfigurationValue, ConfigurationTarget, isConfigurationOverrides, isConfigurationUpdateOverrides } from '../../../../platform/configuration/common/configuration.js';
+import { ConfigurationChangeEvent, ConfigurationModel } from '../../../../platform/configuration/common/configurationModels.js';
+import { DefaultConfiguration, IPolicyConfiguration, NullPolicyConfiguration, PolicyConfiguration } from '../../../../platform/configuration/common/configurations.js';
+import { Extensions, IConfigurationRegistry, keyFromOverrideIdentifiers } from '../../../../platform/configuration/common/configurationRegistry.js';
+import { IFileService, FileOperationError, FileOperationResult } from '../../../../platform/files/common/files.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
+import { IPolicyService, NullPolicyService } from '../../../../platform/policy/common/policy.js';
+import { Registry } from '../../../../platform/registry/common/platform.js';
+import { IUriIdentityService } from '../../../../platform/uriIdentity/common/uriIdentity.js';
+import { IWorkspaceContextService, IWorkspaceFoldersChangeEvent, IWorkspaceFolder, WorkbenchState, Workspace } from '../../../../platform/workspace/common/workspace.js';
+import { FolderConfiguration, UserConfiguration } from '../../../../workbench/services/configuration/browser/configuration.js';
+import { APPLICATION_SCOPES, APPLY_ALL_PROFILES_SETTING, FOLDER_CONFIG_FOLDER_NAME, FOLDER_SETTINGS_PATH, IWorkbenchConfigurationService, RestrictedSettings } from '../../../../workbench/services/configuration/common/configuration.js';
+import { Configuration } from '../../../../workbench/services/configuration/common/configurationModels.js';
+import { IUserDataProfileService } from '../../../../workbench/services/userDataProfile/common/userDataProfile.js';
+
+// Import to register configuration contributions
+import '../../../../workbench/services/configuration/browser/configurationService.js';
+
+export class ConfigurationService extends Disposable implements IWorkbenchConfigurationService {
+
+	declare readonly _serviceBrand: undefined;
+
+	private _configuration: Configuration;
+	private readonly defaultConfiguration: DefaultConfiguration;
+	private readonly policyConfiguration: IPolicyConfiguration;
+	private readonly userConfiguration: UserConfiguration;
+	private readonly cachedFolderConfigs = this._register(new DisposableMap<URI, FolderConfiguration>(new ResourceMap()));
+
+	private readonly _onDidChangeConfiguration = this._register(new Emitter<IConfigurationChangeEvent>());
+	readonly onDidChangeConfiguration = this._onDidChangeConfiguration.event;
+
+	readonly onDidChangeRestrictedSettings = Event.None;
+	readonly restrictedSettings: RestrictedSettings = { default: [] };
+
+	private readonly configurationRegistry = Registry.as<IConfigurationRegistry>(Extensions.Configuration);
+
+	private readonly settingsResource: URI;
+	private readonly configurationEditing: ConfigurationEditing;
+
+	constructor(
+		userDataProfileService: IUserDataProfileService,
+		private readonly workspaceService: IWorkspaceContextService,
+		private readonly uriIdentityService: IUriIdentityService,
+		private readonly fileService: IFileService,
+		policyService: IPolicyService,
+		private readonly logService: ILogService,
+	) {
+		super();
+
+		this.settingsResource = userDataProfileService.currentProfile.settingsResource;
+		this.defaultConfiguration = this._register(new DefaultConfiguration(logService));
+		this.policyConfiguration = policyService instanceof NullPolicyService ? new NullPolicyConfiguration() : this._register(new PolicyConfiguration(this.defaultConfiguration, policyService, logService));
+		this.userConfiguration = this._register(new UserConfiguration(userDataProfileService.currentProfile.settingsResource, userDataProfileService.currentProfile.tasksResource, userDataProfileService.currentProfile.mcpResource, {}, fileService, uriIdentityService, logService));
+		this.configurationEditing = new ConfigurationEditing(fileService, this);
+
+		this._configuration = new Configuration(
+			ConfigurationModel.createEmptyModel(logService),
+			ConfigurationModel.createEmptyModel(logService),
+			ConfigurationModel.createEmptyModel(logService),
+			ConfigurationModel.createEmptyModel(logService),
+			ConfigurationModel.createEmptyModel(logService),
+			ConfigurationModel.createEmptyModel(logService),
+			new ResourceMap(),
+			ConfigurationModel.createEmptyModel(logService),
+			new ResourceMap<ConfigurationModel>(),
+			this.workspaceService.getWorkspace() as Workspace,
+			this.logService
+		);
+
+		this._register(this.defaultConfiguration.onDidChangeConfiguration(({ defaults, properties }) => this.onDefaultConfigurationChanged(defaults, properties)));
+		this._register(this.policyConfiguration.onDidChangeConfiguration(configurationModel => this.onPolicyConfigurationChanged(configurationModel)));
+		this._register(this.userConfiguration.onDidChangeConfiguration(userConfiguration => this.onUserConfigurationChanged(userConfiguration)));
+		this._register(this.workspaceService.onWillChangeWorkspaceFolders(e => e.join(this.loadFolderConfigurations(e.changes.added))));
+		this._register(this.workspaceService.onDidChangeWorkspaceFolders(e => this.onWorkspaceFoldersChanged(e)));
+	}
+
+	async initialize(): Promise<void> {
+		const [defaultModel, policyModel, userModel] = await Promise.all([
+			this.defaultConfiguration.initialize(),
+			this.policyConfiguration.initialize(),
+			this.userConfiguration.initialize()
+		]);
+		const workspace = this.workspaceService.getWorkspace() as Workspace;
+		this._configuration = new Configuration(
+			defaultModel,
+			policyModel,
+			ConfigurationModel.createEmptyModel(this.logService),
+			userModel,
+			ConfigurationModel.createEmptyModel(this.logService),
+			ConfigurationModel.createEmptyModel(this.logService),
+			new ResourceMap(),
+			ConfigurationModel.createEmptyModel(this.logService),
+			new ResourceMap<ConfigurationModel>(),
+			workspace,
+			this.logService
+		);
+		await this.loadFolderConfigurations(workspace.folders);
+	}
+
+	// #region IWorkbenchConfigurationService
+
+	getConfigurationData(): IConfigurationData {
+		return this._configuration.toData();
+	}
+
+	getValue<T>(): T;
+	getValue<T>(section: string): T;
+	getValue<T>(overrides: IConfigurationOverrides): T;
+	getValue<T>(section: string, overrides: IConfigurationOverrides): T;
+	getValue(arg1?: unknown, arg2?: unknown): unknown {
+		const section = typeof arg1 === 'string' ? arg1 : undefined;
+		const overrides = isConfigurationOverrides(arg1) ? arg1 : isConfigurationOverrides(arg2) ? arg2 : undefined;
+		return this._configuration.getValue(section, overrides);
+	}
+
+	updateValue(key: string, value: unknown): Promise<void>;
+	updateValue(key: string, value: unknown, overrides: IConfigurationOverrides | IConfigurationUpdateOverrides): Promise<void>;
+	updateValue(key: string, value: unknown, target: ConfigurationTarget): Promise<void>;
+	updateValue(key: string, value: unknown, overrides: IConfigurationOverrides | IConfigurationUpdateOverrides, target: ConfigurationTarget, options?: IConfigurationUpdateOptions): Promise<void>;
+	async updateValue(key: string, value: unknown, arg3?: unknown, arg4?: unknown, _options?: IConfigurationUpdateOptions): Promise<void> {
+		const overrides: IConfigurationUpdateOverrides | undefined = isConfigurationUpdateOverrides(arg3) ? arg3
+			: isConfigurationOverrides(arg3) ? { resource: arg3.resource, overrideIdentifiers: arg3.overrideIdentifier ? [arg3.overrideIdentifier] : undefined } : undefined;
+		const target: ConfigurationTarget | undefined = (overrides ? arg4 : arg3) as ConfigurationTarget | undefined;
+
+		if (overrides?.overrideIdentifiers) {
+			overrides.overrideIdentifiers = distinct(overrides.overrideIdentifiers);
+			overrides.overrideIdentifiers = overrides.overrideIdentifiers.length ? overrides.overrideIdentifiers : undefined;
+		}
+
+		const inspect = this.inspect(key, { resource: overrides?.resource, overrideIdentifier: overrides?.overrideIdentifiers ? overrides.overrideIdentifiers[0] : undefined });
+		if (inspect.policyValue !== undefined) {
+			throw new Error(`Unable to write ${key} because it is configured in system policy.`);
+		}
+
+		// Remove the setting, if the value is same as default value
+		if (equals(value, inspect.defaultValue)) {
+			value = undefined;
+		}
+
+		if (overrides?.overrideIdentifiers?.length && overrides.overrideIdentifiers.length > 1) {
+			const overrideIdentifiers = overrides.overrideIdentifiers.sort();
+			const existingOverrides = this._configuration.localUserConfiguration.overrides.find(override => arrayEquals([...override.identifiers].sort(), overrideIdentifiers));
+			if (existingOverrides) {
+				overrides.overrideIdentifiers = existingOverrides.identifiers;
+			}
+		}
+
+		const path = overrides?.overrideIdentifiers?.length ? [keyFromOverrideIdentifiers(overrides.overrideIdentifiers), key] : [key];
+
+		const settingsResource = this.getSettingsResource(target, overrides?.resource ?? undefined);
+		await this.configurationEditing.write(settingsResource, path, value);
+		await this.reloadConfiguration();
+	}
+
+	private getSettingsResource(target: ConfigurationTarget | undefined, resource: URI | undefined): URI {
+		if (target === ConfigurationTarget.WORKSPACE_FOLDER || target === ConfigurationTarget.WORKSPACE) {
+			if (resource) {
+				const folder = this.workspaceService.getWorkspaceFolder(resource);
+				if (folder) {
+					return this.uriIdentityService.extUri.joinPath(folder.uri, FOLDER_SETTINGS_PATH);
+				}
+			}
+		}
+		return this.settingsResource;
+	}
+
+	inspect<T>(key: string, overrides?: IConfigurationOverrides): IConfigurationValue<T> {
+		return this._configuration.inspect<T>(key, overrides);
+	}
+
+	keys(): { default: string[]; policy: string[]; user: string[]; workspace: string[]; workspaceFolder: string[] } {
+		return this._configuration.keys();
+	}
+
+	async reloadConfiguration(_target?: ConfigurationTarget | IWorkspaceFolder): Promise<void> {
+		const userModel = await this.userConfiguration.initialize();
+		const previousData = this._configuration.toData();
+		const change = this._configuration.compareAndUpdateLocalUserConfiguration(userModel);
+
+		// Reload folder configurations
+		for (const folder of this.workspaceService.getWorkspace().folders) {
+			const folderConfiguration = this.cachedFolderConfigs.get(folder.uri);
+			if (folderConfiguration) {
+				const folderModel = await folderConfiguration.loadConfiguration();
+				const folderChange = this._configuration.compareAndUpdateFolderConfiguration(folder.uri, folderModel);
+				change.keys.push(...folderChange.keys);
+				change.overrides.push(...folderChange.overrides);
+			}
+		}
+
+		this.triggerConfigurationChange(change, previousData, ConfigurationTarget.USER);
+	}
+
+	hasCachedConfigurationDefaultsOverrides(): boolean {
+		return false;
+	}
+
+	async whenRemoteConfigurationLoaded(): Promise<void> { }
+
+	isSettingAppliedForAllProfiles(key: string): boolean {
+		const scope = this.configurationRegistry.getConfigurationProperties()[key]?.scope;
+		if (scope && APPLICATION_SCOPES.includes(scope)) {
+			return true;
+		}
+		const allProfilesSettings = this.getValue<string[]>(APPLY_ALL_PROFILES_SETTING) ?? [];
+		return Array.isArray(allProfilesSettings) && allProfilesSettings.includes(key);
+	}
+
+	// #endregion
+
+	// #region Configuration change handlers
+
+	private onDefaultConfigurationChanged(defaults: ConfigurationModel, properties?: string[]): void {
+		const previousData = this._configuration.toData();
+		const change = this._configuration.compareAndUpdateDefaultConfiguration(defaults, properties);
+		this._configuration.updateLocalUserConfiguration(this.userConfiguration.reparse());
+		for (const folder of this.workspaceService.getWorkspace().folders) {
+			const folderConfiguration = this.cachedFolderConfigs.get(folder.uri);
+			if (folderConfiguration) {
+				this._configuration.updateFolderConfiguration(folder.uri, folderConfiguration.reparse());
+			}
+		}
+		this.triggerConfigurationChange(change, previousData, ConfigurationTarget.DEFAULT);
+	}
+
+	private onPolicyConfigurationChanged(policyConfiguration: ConfigurationModel): void {
+		const previousData = this._configuration.toData();
+		const change = this._configuration.compareAndUpdatePolicyConfiguration(policyConfiguration);
+		this.triggerConfigurationChange(change, previousData, ConfigurationTarget.DEFAULT);
+	}
+
+	private onUserConfigurationChanged(userConfiguration: ConfigurationModel): void {
+		const previousData = this._configuration.toData();
+		const change = this._configuration.compareAndUpdateLocalUserConfiguration(userConfiguration);
+		this.triggerConfigurationChange(change, previousData, ConfigurationTarget.USER);
+	}
+
+	private onWorkspaceFoldersChanged(e: IWorkspaceFoldersChangeEvent): void {
+		// Remove configurations for removed folders
+		const previousData = this._configuration.toData();
+		const keys: string[] = [];
+		const overrides: [string, string[]][] = [];
+		for (const folder of e.removed) {
+			const change = this._configuration.compareAndDeleteFolderConfiguration(folder.uri);
+			keys.push(...change.keys);
+			overrides.push(...change.overrides);
+			this.cachedFolderConfigs.deleteAndDispose(folder.uri);
+		}
+		if (keys.length || overrides.length) {
+			this.triggerConfigurationChange({ keys, overrides }, previousData, ConfigurationTarget.WORKSPACE_FOLDER);
+		}
+	}
+
+	private onWorkspaceFolderConfigurationChanged(folder: IWorkspaceFolder): void {
+		const folderConfiguration = this.cachedFolderConfigs.get(folder.uri);
+		if (folderConfiguration) {
+			folderConfiguration.loadConfiguration().then(configurationModel => {
+				const previousData = this._configuration.toData();
+				const change = this._configuration.compareAndUpdateFolderConfiguration(folder.uri, configurationModel);
+				this.triggerConfigurationChange(change, previousData, ConfigurationTarget.WORKSPACE_FOLDER);
+			}, onUnexpectedError);
+		}
+	}
+
+	private async loadFolderConfigurations(folders: readonly IWorkspaceFolder[]): Promise<void> {
+		for (const folder of folders) {
+			let folderConfiguration = this.cachedFolderConfigs.get(folder.uri);
+			if (!folderConfiguration) {
+				folderConfiguration = new FolderConfiguration(false, folder, FOLDER_CONFIG_FOLDER_NAME, WorkbenchState.WORKSPACE, true, this.fileService, this.uriIdentityService, this.logService, { needsCaching: () => false, read: async () => '', write: async () => { }, remove: async () => { } });
+				folderConfiguration.addRelated(folderConfiguration.onDidChange(() => this.onWorkspaceFolderConfigurationChanged(folder)));
+				this.cachedFolderConfigs.set(folder.uri, folderConfiguration);
+			}
+			const configurationModel = await folderConfiguration.loadConfiguration();
+			this._configuration.updateFolderConfiguration(folder.uri, configurationModel);
+		}
+	}
+
+	private triggerConfigurationChange(change: IConfigurationChange, previousData: IConfigurationData, target: ConfigurationTarget): void {
+		if (change.keys.length) {
+			const workspace = this.workspaceService.getWorkspace() as Workspace;
+			const event = new ConfigurationChangeEvent(change, { data: previousData, workspace }, this._configuration, workspace, this.logService);
+			event.source = target;
+			this._onDidChangeConfiguration.fire(event);
+		}
+	}
+
+	// #endregion
+}
+
+class ConfigurationEditing {
+
+	private readonly queue = new Queue<void>();
+
+	constructor(
+		private readonly fileService: IFileService,
+		private readonly configurationService: ConfigurationService,
+	) { }
+
+	write(settingsResource: URI, path: JSONPath, value: unknown): Promise<void> {
+		return this.queue.queue(() => this.doWriteConfiguration(settingsResource, path, value));
+	}
+
+	private async doWriteConfiguration(settingsResource: URI, path: JSONPath, value: unknown): Promise<void> {
+		let content: string;
+		try {
+			const fileContent = await this.fileService.readFile(settingsResource);
+			content = fileContent.value.toString();
+		} catch (error) {
+			if ((error as FileOperationError).fileOperationResult === FileOperationResult.FILE_NOT_FOUND) {
+				content = '{}';
+			} else {
+				throw error;
+			}
+		}
+
+		const parseErrors: ParseError[] = [];
+		parse(content, parseErrors, { allowTrailingComma: true, allowEmptyContent: true });
+		if (parseErrors.length > 0) {
+			throw new Error('Unable to write into the settings file. Please open the file to correct errors/warnings in the file and try again.');
+		}
+
+		const edits = this.getEdits(content, path, value);
+		content = applyEdits(content, edits);
+
+		await this.fileService.writeFile(settingsResource, VSBuffer.fromString(content));
+	}
+
+	private getEdits(content: string, path: JSONPath, value: unknown): Edit[] {
+		const { tabSize, insertSpaces, eol } = this.formattingOptions;
+
+		if (!path.length) {
+			const newContent = JSON.stringify(value, null, insertSpaces ? ' '.repeat(tabSize) : '\t');
+			return [{
+				content: newContent,
+				length: content.length,
+				offset: 0
+			}];
+		}
+
+		return setProperty(content, path, value, { tabSize, insertSpaces, eol });
+	}
+
+	private _formattingOptions: Required<FormattingOptions> | undefined;
+	private get formattingOptions(): Required<FormattingOptions> {
+		if (!this._formattingOptions) {
+			let eol = OS === OperatingSystem.Linux || OS === OperatingSystem.Macintosh ? '\n' : '\r\n';
+			const configuredEol = this.configurationService.getValue<string>('files.eol', { overrideIdentifier: 'jsonc' });
+			if (configuredEol && typeof configuredEol === 'string' && configuredEol !== 'auto') {
+				eol = configuredEol;
+			}
+			this._formattingOptions = {
+				eol,
+				insertSpaces: !!this.configurationService.getValue('editor.insertSpaces', { overrideIdentifier: 'jsonc' }),
+				tabSize: this.configurationService.getValue('editor.tabSize', { overrideIdentifier: 'jsonc' })
+			};
+		}
+		return this._formattingOptions;
+	}
+}
diff --git a/src/vs/sessions/services/configuration/test/browser/configurationService.test.ts b/src/vs/sessions/services/configuration/test/browser/configurationService.test.ts
new file mode 100644
index 0000000000000..fdfd8a4f1e9f4
--- /dev/null
+++ b/src/vs/sessions/services/configuration/test/browser/configurationService.test.ts
@@ -0,0 +1,339 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { URI } from '../../../../../base/common/uri.js';
+import { Registry } from '../../../../../platform/registry/common/platform.js';
+import { IConfigurationRegistry, Extensions as ConfigurationExtensions, ConfigurationScope } from '../../../../../platform/configuration/common/configurationRegistry.js';
+import { ConfigurationTarget } from '../../../../../platform/configuration/common/configuration.js';
+import { FileService } from '../../../../../platform/files/common/fileService.js';
+import { NullLogService } from '../../../../../platform/log/common/log.js';
+import { NullPolicyService } from '../../../../../platform/policy/common/policy.js';
+import { VSBuffer } from '../../../../../base/common/buffer.js';
+import { UriIdentityService } from '../../../../../platform/uriIdentity/common/uriIdentityService.js';
+import { InMemoryFileSystemProvider } from '../../../../../platform/files/common/inMemoryFilesystemProvider.js';
+import { joinPath } from '../../../../../base/common/resources.js';
+import { Schemas } from '../../../../../base/common/network.js';
+import { UserDataProfilesService } from '../../../../../platform/userDataProfile/common/userDataProfile.js';
+import { UserDataProfileService } from '../../../../../workbench/services/userDataProfile/common/userDataProfileService.js';
+import { FileUserDataProvider } from '../../../../../platform/userData/common/fileUserDataProvider.js';
+import { TestEnvironmentService } from '../../../../../workbench/test/browser/workbenchTestServices.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { runWithFakedTimers } from '../../../../../base/test/common/timeTravelScheduler.js';
+import { ConfigurationService } from '../../browser/configurationService.js';
+import { SessionsWorkspaceContextService } from '../../../workspace/browser/workspaceContextService.js';
+import { getWorkspaceIdentifier } from '../../../../../workbench/services/workspaces/browser/workspaces.js';
+import { Event } from '../../../../../base/common/event.js';
+import { IUserDataProfileService } from '../../../../../workbench/services/userDataProfile/common/userDataProfile.js';
+
+const ROOT = URI.file('tests').with({ scheme: 'vscode-tests' });
+
+suite('Sessions ConfigurationService', () => {
+
+	let testObject: ConfigurationService;
+	let workspaceService: SessionsWorkspaceContextService;
+	let fileService: FileService;
+	let userDataProfileService: IUserDataProfileService;
+	const configurationRegistry = Registry.as<IConfigurationRegistry>(ConfigurationExtensions.Configuration);
+	const disposables = ensureNoDisposablesAreLeakedInTestSuite();
+
+	suiteSetup(() => {
+		configurationRegistry.registerConfiguration({
+			'id': '_test_sessions',
+			'type': 'object',
+			'properties': {
+				'sessionsConfigurationService.testSetting': {
+					'type': 'string',
+					'default': 'defaultValue',
+					scope: ConfigurationScope.RESOURCE
+				},
+				'sessionsConfigurationService.machineSetting': {
+					'type': 'string',
+					'default': 'defaultValue',
+					scope: ConfigurationScope.MACHINE
+				},
+				'sessionsConfigurationService.applicationSetting': {
+					'type': 'string',
+					'default': 'defaultValue',
+					scope: ConfigurationScope.APPLICATION
+				},
+			}
+		});
+	});
+
+	setup(async () => {
+		const logService = new NullLogService();
+		fileService = disposables.add(new FileService(logService));
+		const fileSystemProvider = disposables.add(new InMemoryFileSystemProvider());
+		disposables.add(fileService.registerProvider(ROOT.scheme, fileSystemProvider));
+
+		const environmentService = TestEnvironmentService;
+		const uriIdentityService = disposables.add(new UriIdentityService(fileService));
+		const userDataProfilesService = disposables.add(new UserDataProfilesService(environmentService, fileService, uriIdentityService, logService));
+		disposables.add(fileService.registerProvider(Schemas.vscodeUserData, disposables.add(new FileUserDataProvider(ROOT.scheme, fileSystemProvider, Schemas.vscodeUserData, userDataProfilesService, uriIdentityService, logService))));
+		userDataProfileService = disposables.add(new UserDataProfileService(userDataProfilesService.defaultProfile));
+
+		const configResource = joinPath(ROOT, 'agent-sessions.code-workspace');
+		await fileService.writeFile(configResource, VSBuffer.fromString(JSON.stringify({ folders: [] })));
+
+		workspaceService = disposables.add(new SessionsWorkspaceContextService(getWorkspaceIdentifier(configResource), uriIdentityService));
+		testObject = disposables.add(new ConfigurationService(userDataProfileService, workspaceService, uriIdentityService, fileService, new NullPolicyService(), logService));
+		await testObject.initialize();
+	});
+
+	// #region Reading
+
+	test('defaults', () => {
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting'), 'defaultValue');
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.machineSetting'), 'defaultValue');
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.applicationSetting'), 'defaultValue');
+	});
+
+	test('user settings override defaults', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		await fileService.writeFile(userDataProfileService.currentProfile.settingsResource, VSBuffer.fromString('{ "sessionsConfigurationService.testSetting": "userValue" }'));
+		await testObject.reloadConfiguration();
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting'), 'userValue');
+	}));
+
+	test('workspace folder settings override user settings', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'myFolder');
+		await fileService.createFolder(folder);
+		await fileService.writeFile(userDataProfileService.currentProfile.settingsResource, VSBuffer.fromString('{ "sessionsConfigurationService.testSetting": "userValue" }'));
+		await testObject.reloadConfiguration();
+		await fileService.writeFile(joinPath(folder, '.vscode', 'settings.json'), VSBuffer.fromString('{ "sessionsConfigurationService.testSetting": "folderValue" }'));
+		await workspaceService.addFolders([{ uri: folder }]);
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'folderValue');
+	}));
+
+	test('folder settings are read when folders are added', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'addedFolder');
+		await fileService.createFolder(folder);
+		await fileService.writeFile(joinPath(folder, '.vscode', 'settings.json'), VSBuffer.fromString('{ "sessionsConfigurationService.testSetting": "folderValue" }'));
+		await workspaceService.addFolders([{ uri: folder }]);
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'folderValue');
+	}));
+
+	test('folder settings are removed when folders are removed', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'removedFolder');
+		await fileService.createFolder(folder);
+		await fileService.writeFile(joinPath(folder, '.vscode', 'settings.json'), VSBuffer.fromString('{ "sessionsConfigurationService.testSetting": "folderValue" }'));
+		await workspaceService.addFolders([{ uri: folder }]);
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'folderValue');
+		await workspaceService.removeFolders([folder]);
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'defaultValue');
+	}));
+
+	test('configuration change event is fired when folders with settings are removed', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'removedFolder2');
+		await fileService.createFolder(folder);
+		await fileService.writeFile(joinPath(folder, '.vscode', 'settings.json'), VSBuffer.fromString('{ "sessionsConfigurationService.testSetting": "folderValue" }'));
+		await workspaceService.addFolders([{ uri: folder }]);
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'folderValue');
+
+		const promise = Event.toPromise(testObject.onDidChangeConfiguration);
+		await workspaceService.removeFolders([folder]);
+		const event = await promise;
+		assert.ok(event.affectsConfiguration('sessionsConfigurationService.testSetting'));
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'defaultValue');
+	}));
+
+	test('configuration change event is fired on user settings change', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const promise = Event.toPromise(testObject.onDidChangeConfiguration);
+		await fileService.writeFile(userDataProfileService.currentProfile.settingsResource, VSBuffer.fromString('{ "sessionsConfigurationService.testSetting": "userValue" }'));
+		await testObject.reloadConfiguration();
+		const event = await promise;
+		assert.ok(event.affectsConfiguration('sessionsConfigurationService.testSetting'));
+	}));
+
+	test('inspect returns correct values per layer', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'inspectFolder');
+		await fileService.createFolder(folder);
+		await fileService.writeFile(userDataProfileService.currentProfile.settingsResource, VSBuffer.fromString('{ "sessionsConfigurationService.testSetting": "userValue" }'));
+		await testObject.reloadConfiguration();
+		await fileService.writeFile(joinPath(folder, '.vscode', 'settings.json'), VSBuffer.fromString('{ "sessionsConfigurationService.testSetting": "folderValue" }'));
+		await workspaceService.addFolders([{ uri: folder }]);
+
+		const inspection = testObject.inspect('sessionsConfigurationService.testSetting', { resource: folder });
+		assert.strictEqual(inspection.defaultValue, 'defaultValue');
+		assert.strictEqual(inspection.userValue, 'userValue');
+		assert.strictEqual(inspection.workspaceFolderValue, 'folderValue');
+	}));
+
+	test('application settings are not read from workspace folder', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'appFolder');
+		await fileService.createFolder(folder);
+		await fileService.writeFile(joinPath(folder, '.vscode', 'settings.json'), VSBuffer.fromString('{ "sessionsConfigurationService.applicationSetting": "folderValue" }'));
+		await workspaceService.addFolders([{ uri: folder }]);
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.applicationSetting', { resource: folder }), 'defaultValue');
+	}));
+
+	test('machine settings are not read from workspace folder', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'machineFolder');
+		await fileService.createFolder(folder);
+		await fileService.writeFile(joinPath(folder, '.vscode', 'settings.json'), VSBuffer.fromString('{ "sessionsConfigurationService.machineSetting": "folderValue" }'));
+		await workspaceService.addFolders([{ uri: folder }]);
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.machineSetting', { resource: folder }), 'defaultValue');
+	}));
+
+	test('folder settings change fires configuration change event', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'changeFolder');
+		await fileService.createFolder(folder);
+		await fileService.writeFile(joinPath(folder, '.vscode', 'settings.json'), VSBuffer.fromString('{ "sessionsConfigurationService.testSetting": "initialValue" }'));
+		await workspaceService.addFolders([{ uri: folder }]);
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'initialValue');
+
+		const promise = Event.toPromise(testObject.onDidChangeConfiguration);
+		await fileService.writeFile(joinPath(folder, '.vscode', 'settings.json'), VSBuffer.fromString('{ "sessionsConfigurationService.testSetting": "updatedValue" }'));
+		const event = await promise;
+		assert.ok(event.affectsConfiguration('sessionsConfigurationService.testSetting'));
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'updatedValue');
+	}));
+
+	// #endregion
+
+	// #region Writing
+
+	test('updateValue writes to user settings', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'writtenValue');
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting'), 'writtenValue');
+	}));
+
+	test('updateValue persists to settings file', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'persistedValue');
+
+		const content = (await fileService.readFile(userDataProfileService.currentProfile.settingsResource)).value.toString();
+		assert.ok(content.includes('"sessionsConfigurationService.testSetting"'));
+		assert.ok(content.includes('persistedValue'));
+	}));
+
+	test('updateValue fires change event', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const promise = Event.toPromise(testObject.onDidChangeConfiguration);
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'eventValue');
+		const event = await promise;
+		assert.ok(event.affectsConfiguration('sessionsConfigurationService.testSetting'));
+	}));
+
+	test('updateValue removes setting when value equals default', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'nonDefault');
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting'), 'nonDefault');
+
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'defaultValue');
+		const content = (await fileService.readFile(userDataProfileService.currentProfile.settingsResource)).value.toString();
+		assert.ok(!content.includes('sessionsConfigurationService.testSetting'));
+	}));
+
+	test('updateValue can update multiple settings', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'value1');
+		await testObject.updateValue('sessionsConfigurationService.machineSetting', 'value2');
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting'), 'value1');
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.machineSetting'), 'value2');
+	}));
+
+	test('updateValue with language override', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'langValue', { overrideIdentifier: 'jsonc' });
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { overrideIdentifier: 'jsonc' }), 'langValue');
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting'), 'defaultValue');
+	}));
+
+	test('updateValue is reflected in inspect', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'inspectedValue');
+		const inspection = testObject.inspect('sessionsConfigurationService.testSetting');
+		assert.strictEqual(inspection.defaultValue, 'defaultValue');
+		assert.strictEqual(inspection.userValue, 'inspectedValue');
+	}));
+
+	// #endregion
+
+	// #region Workspace Folder - Read and Write
+
+	test('read setting from workspace folder', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'readFolder');
+		await fileService.createFolder(folder);
+		await fileService.writeFile(joinPath(folder, '.vscode', 'settings.json'), VSBuffer.fromString('{ "sessionsConfigurationService.testSetting": "folderValue" }'));
+
+		await workspaceService.addFolders([{ uri: folder }]);
+
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'folderValue');
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting'), 'defaultValue');
+	}));
+
+	test('write setting to workspace folder', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'writeFolder');
+		await fileService.createFolder(folder);
+
+		await workspaceService.addFolders([{ uri: folder }]);
+
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'writtenFolderValue', { resource: folder }, ConfigurationTarget.WORKSPACE_FOLDER);
+
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'writtenFolderValue');
+	}));
+
+	test('write setting to workspace folder persists to folder settings file', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'persistFolder');
+		await fileService.createFolder(folder);
+
+		await workspaceService.addFolders([{ uri: folder }]);
+
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'persistedFolderValue', { resource: folder }, ConfigurationTarget.WORKSPACE_FOLDER);
+
+		const content = (await fileService.readFile(joinPath(folder, '.vscode', 'settings.json'))).value.toString();
+		assert.ok(content.includes('"sessionsConfigurationService.testSetting"'));
+		assert.ok(content.includes('persistedFolderValue'));
+	}));
+
+	test('write setting to workspace folder does not affect user settings', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'isolateFolder');
+		await fileService.createFolder(folder);
+
+		await workspaceService.addFolders([{ uri: folder }]);
+
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'folderOnly', { resource: folder }, ConfigurationTarget.WORKSPACE_FOLDER);
+
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'folderOnly');
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting'), 'defaultValue');
+	}));
+
+	test('workspace folder setting overrides user setting for resource', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'overrideFolder');
+		await fileService.createFolder(folder);
+
+		await workspaceService.addFolders([{ uri: folder }]);
+
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'userValue');
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'folderValue', { resource: folder }, ConfigurationTarget.WORKSPACE_FOLDER);
+
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'folderValue');
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting'), 'userValue');
+	}));
+
+	test('inspect shows workspace folder value after write', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'inspectWriteFolder');
+		await fileService.createFolder(folder);
+
+		await workspaceService.addFolders([{ uri: folder }]);
+
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'userVal');
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'folderVal', { resource: folder }, ConfigurationTarget.WORKSPACE_FOLDER);
+
+		const inspection = testObject.inspect('sessionsConfigurationService.testSetting', { resource: folder });
+		assert.strictEqual(inspection.defaultValue, 'defaultValue');
+		assert.strictEqual(inspection.userValue, 'userVal');
+		assert.strictEqual(inspection.workspaceFolderValue, 'folderVal');
+	}));
+
+	test('removing folder clears its written settings', () => runWithFakedTimers<void>({ useFakeTimers: true }, async () => {
+		const folder = joinPath(ROOT, 'clearFolder');
+		await fileService.createFolder(folder);
+
+		await workspaceService.addFolders([{ uri: folder }]);
+		await testObject.updateValue('sessionsConfigurationService.testSetting', 'folderValue', { resource: folder }, ConfigurationTarget.WORKSPACE_FOLDER);
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'folderValue');
+
+		await workspaceService.removeFolders([folder]);
+		assert.strictEqual(testObject.getValue('sessionsConfigurationService.testSetting', { resource: folder }), 'defaultValue');
+	}));
+
+	// #endregion
+});
diff --git a/src/vs/sessions/services/title/browser/titleService.ts b/src/vs/sessions/services/title/browser/titleService.ts
new file mode 100644
index 0000000000000..b04868f061e1f
--- /dev/null
+++ b/src/vs/sessions/services/title/browser/titleService.ts
@@ -0,0 +1,10 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { InstantiationType, registerSingleton } from '../../../../platform/instantiation/common/extensions.js';
+import { ITitleService } from '../../../../workbench/services/title/browser/titleService.js';
+import { TitleService } from '../../../browser/parts/titlebarPart.js';
+
+registerSingleton(ITitleService, TitleService, InstantiationType.Eager);
diff --git a/src/vs/sessions/electron-browser/titleService.ts b/src/vs/sessions/services/title/electron-browser/titleService.ts
similarity index 59%
rename from src/vs/sessions/electron-browser/titleService.ts
rename to src/vs/sessions/services/title/electron-browser/titleService.ts
index 9ffc7a93650af..070b1eb7bc4fc 100644
--- a/src/vs/sessions/electron-browser/titleService.ts
+++ b/src/vs/sessions/services/title/electron-browser/titleService.ts
@@ -3,8 +3,8 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { InstantiationType, registerSingleton } from '../../platform/instantiation/common/extensions.js';
-import { ITitleService } from '../../workbench/services/title/browser/titleService.js';
-import { NativeTitleService } from './parts/titlebarPart.js';
+import { InstantiationType, registerSingleton } from '../../../../platform/instantiation/common/extensions.js';
+import { ITitleService } from '../../../../workbench/services/title/browser/titleService.js';
+import { NativeTitleService } from '../../../electron-browser/parts/titlebarPart.js';
 
 registerSingleton(ITitleService, NativeTitleService, InstantiationType.Eager);
diff --git a/src/vs/sessions/services/workspace/browser/workspaceContextService.ts b/src/vs/sessions/services/workspace/browser/workspaceContextService.ts
new file mode 100644
index 0000000000000..0e2aab0e8fcb0
--- /dev/null
+++ b/src/vs/sessions/services/workspace/browser/workspaceContextService.ts
@@ -0,0 +1,165 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Emitter, Event } from '../../../../base/common/event.js';
+import { Queue } from '../../../../base/common/async.js';
+import { removeTrailingPathSeparator } from '../../../../base/common/resources.js';
+import { URI } from '../../../../base/common/uri.js';
+import { IUriIdentityService } from '../../../../platform/uriIdentity/common/uriIdentity.js';
+import { Workspace, WorkspaceFolder, IWorkspace, IWorkspaceContextService, IWorkspaceFoldersChangeEvent, IWorkspaceFoldersWillChangeEvent, IWorkspaceIdentifier, ISingleFolderWorkspaceIdentifier, IWorkspaceFolder, WorkbenchState } from '../../../../platform/workspace/common/workspace.js';
+import { IWorkspaceFolderCreationData } from '../../../../platform/workspaces/common/workspaces.js';
+import { getWorkspaceIdentifier } from '../../../../workbench/services/workspaces/browser/workspaces.js';
+import { IWorkspaceEditingService } from '../../../../workbench/services/workspaces/common/workspaceEditing.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
+export class SessionsWorkspaceContextService extends Disposable implements IWorkspaceContextService, IWorkspaceEditingService {
+
+	declare readonly _serviceBrand: undefined;
+
+	readonly onDidChangeWorkbenchState = Event.None;
+	readonly onDidChangeWorkspaceName = Event.None;
+	readonly onDidEnterWorkspace = Event.None;
+
+	private readonly _onWillChangeWorkspaceFolders = new Emitter<IWorkspaceFoldersWillChangeEvent>();
+	readonly onWillChangeWorkspaceFolders = this._onWillChangeWorkspaceFolders.event;
+
+	private readonly _onDidChangeWorkspaceFolders = this._register(new Emitter<IWorkspaceFoldersChangeEvent>());
+	readonly onDidChangeWorkspaceFolders = this._onDidChangeWorkspaceFolders.event;
+
+	private workspace: Workspace;
+	private readonly _updateFoldersQueue = this._register(new Queue<void>());
+
+	constructor(
+		workspaceIdentifier: IWorkspaceIdentifier,
+		private readonly uriIdentityService: IUriIdentityService,
+	) {
+		super();
+		this.workspace = new Workspace(workspaceIdentifier.id, [], false, workspaceIdentifier.configPath, uri => uriIdentityService.extUri.ignorePathCasing(uri));
+	}
+
+	getCompleteWorkspace(): Promise<IWorkspace> {
+		return Promise.resolve(this.workspace);
+	}
+
+	getWorkspace(): IWorkspace {
+		return this.workspace;
+	}
+
+	getWorkbenchState(): WorkbenchState {
+		return WorkbenchState.WORKSPACE;
+	}
+
+	hasWorkspaceData(): boolean {
+		return true;
+	}
+
+	getWorkspaceFolder(resource: URI): IWorkspaceFolder | null {
+		return this.workspace.getFolder(resource);
+	}
+
+	public isInsideWorkspace(resource: URI): boolean {
+		return !!this.getWorkspaceFolder(resource);
+	}
+
+	public isCurrentWorkspace(workspaceIdOrFolder: IWorkspaceIdentifier | ISingleFolderWorkspaceIdentifier | URI): boolean {
+		return false;
+	}
+
+	public addFolders(foldersToAdd: IWorkspaceFolderCreationData[]): Promise<void> {
+		return this.doUpdateFolders(foldersToAdd, []);
+	}
+
+	public removeFolders(foldersToRemove: URI[]): Promise<void> {
+		return this.doUpdateFolders([], foldersToRemove);
+	}
+
+	public async updateFolders(index: number, deleteCount?: number, foldersToAddCandidates?: IWorkspaceFolderCreationData[]): Promise<void> {
+		const folders = this.workspace.folders;
+
+		let foldersToDelete: URI[] = [];
+		if (typeof deleteCount === 'number') {
+			foldersToDelete = folders.slice(index, index + deleteCount).map(folder => folder.uri);
+		}
+
+		let foldersToAdd: IWorkspaceFolderCreationData[] = [];
+		if (Array.isArray(foldersToAddCandidates)) {
+			foldersToAdd = foldersToAddCandidates.map(folderToAdd => ({ uri: removeTrailingPathSeparator(folderToAdd.uri), name: folderToAdd.name }));
+		}
+
+		return this.doUpdateFolders(foldersToAdd, foldersToDelete, index);
+	}
+
+	async enterWorkspace(_path: URI): Promise<void> { }
+
+	async createAndEnterWorkspace(_folders: IWorkspaceFolderCreationData[], _path?: URI): Promise<void> { }
+
+	async saveAndEnterWorkspace(_path: URI): Promise<void> { }
+
+	async copyWorkspaceSettings(_toWorkspace: IWorkspaceIdentifier): Promise<void> { }
+
+	async pickNewWorkspacePath(): Promise<URI | undefined> { return undefined; }
+
+	private doUpdateFolders(foldersToAdd: IWorkspaceFolderCreationData[], foldersToRemove: URI[], index?: number): Promise<void> {
+		return this._updateFoldersQueue.queue(() => this._doUpdateFolders(foldersToAdd, foldersToRemove, index));
+	}
+
+	private async _doUpdateFolders(foldersToAdd: IWorkspaceFolderCreationData[], foldersToRemove: URI[], index?: number): Promise<void> {
+		if (foldersToAdd.length === 0 && foldersToRemove.length === 0) {
+			return;
+		}
+
+		const currentFolders = this.workspace.folders;
+
+		// Remove folders
+		let newFolders = currentFolders.filter(folder =>
+			!foldersToRemove.some(toRemove => this.uriIdentityService.extUri.isEqual(folder.uri, toRemove))
+		);
+
+		// Add folders
+		const foldersToAddWorkspaceFolders = foldersToAdd
+			.filter(folderToAdd => !newFolders.some(existing => this.uriIdentityService.extUri.isEqual(existing.uri, folderToAdd.uri)))
+			.map(folderToAdd => new WorkspaceFolder(
+				{ uri: folderToAdd.uri, name: folderToAdd.name || this.uriIdentityService.extUri.basenameOrAuthority(folderToAdd.uri), index: 0 },
+				{ uri: folderToAdd.uri.toString() }
+			));
+
+		if (foldersToAddWorkspaceFolders.length > 0) {
+			if (typeof index === 'number' && index >= 0 && index < newFolders.length) {
+				newFolders = [...newFolders.slice(0, index), ...foldersToAddWorkspaceFolders, ...newFolders.slice(index)];
+			} else {
+				newFolders = [...newFolders, ...foldersToAddWorkspaceFolders];
+			}
+		}
+
+		// Recompute indices
+		newFolders = newFolders.map((f, i) => new WorkspaceFolder({ uri: f.uri, name: f.name, index: i }, f.raw));
+
+		// Compute change event
+		const added = newFolders.filter(folder => !currentFolders.some(existing => this.uriIdentityService.extUri.isEqual(existing.uri, folder.uri)));
+		const removed = currentFolders.filter(folder => !newFolders.some(existing => this.uriIdentityService.extUri.isEqual(existing.uri, folder.uri)));
+		const changed: IWorkspaceFolder[] = [];
+		const changes: IWorkspaceFoldersChangeEvent = { added, removed, changed };
+
+		if (added.length === 0 && removed.length === 0) {
+			return;
+		}
+
+		// Fire will change event
+		const joinPromises: Promise<void>[] = [];
+		this._onWillChangeWorkspaceFolders.fire({
+			changes,
+			fromCache: false,
+			join(promise: Promise<void>) { joinPromises.push(promise); }
+		});
+		await Promise.allSettled(joinPromises);
+
+		// Update workspace
+		const workspaceIdentifier = getWorkspaceIdentifier(this.workspace.configuration!);
+		const workspace = new Workspace(workspaceIdentifier.id, newFolders, false, workspaceIdentifier.configPath, uri => this.uriIdentityService.extUri.ignorePathCasing(uri));
+		this.workspace.update(workspace);
+
+		// Fire did change event
+		this._onDidChangeWorkspaceFolders.fire(changes);
+	}
+}
diff --git a/src/vs/sessions/sessions.desktop.main.ts b/src/vs/sessions/sessions.desktop.main.ts
index fcf7a0bc195d5..587ce438dd0ac 100644
--- a/src/vs/sessions/sessions.desktop.main.ts
+++ b/src/vs/sessions/sessions.desktop.main.ts
@@ -42,12 +42,11 @@ import '../workbench/services/update/electron-browser/updateService.js';
 import '../workbench/services/url/electron-browser/urlService.js';
 import '../workbench/services/lifecycle/electron-browser/lifecycleService.js';
 import '../workbench/services/host/electron-browser/nativeHostService.js';
-import './electron-browser/titleService.js';
+import './services/title/electron-browser/titleService.js';
 import '../platform/meteredConnection/electron-browser/meteredConnectionService.js';
 import '../workbench/services/request/electron-browser/requestService.js';
 import '../workbench/services/clipboard/electron-browser/clipboardService.js';
 import '../workbench/services/contextmenu/electron-browser/contextmenuService.js';
-import '../workbench/services/workspaces/electron-browser/workspaceEditingService.js';
 import '../workbench/services/configurationResolver/electron-browser/configurationResolverService.js';
 import '../workbench/services/accessibility/electron-browser/accessibilityService.js';
 import '../workbench/services/keybinding/electron-browser/nativeKeyboardLayout.js';
@@ -178,7 +177,6 @@ import '../workbench/contrib/remoteTunnel/electron-browser/remoteTunnel.contribu
 
 // Chat
 import '../workbench/contrib/chat/electron-browser/chat.contribution.js';
-//import '../workbench/contrib/inlineChat/electron-browser/inlineChat.contribution.js';
 import './contrib/agentFeedback/browser/agentFeedback.contribution.js';
 
 // Encryption
@@ -204,14 +202,22 @@ import './browser/layoutActions.js';
 import './contrib/accountMenu/browser/account.contribution.js';
 import './contrib/aiCustomizationTreeView/browser/aiCustomizationTreeView.contribution.js';
 import './contrib/chat/browser/chat.contribution.js';
+import './contrib/chat/browser/customizationsDebugLog.contribution.js';
 import './contrib/sessions/browser/sessions.contribution.js';
 import './contrib/sessions/browser/customizationsToolbar.contribution.js';
-import './contrib/changesView/browser/changesView.contribution.js';
+import './contrib/changes/browser/changesView.contribution.js';
+import './contrib/codeReview/browser/codeReview.contributions.js';
+import './contrib/files/browser/files.contribution.js';
+import './contrib/git/browser/git.contribution.js';
+import './contrib/github/browser/github.contribution.js';
+import './contrib/applyCommitsToParentRepo/browser/applyChangesToParentRepo.js';
 import './contrib/fileTreeView/browser/fileTreeView.contribution.js'; // view registration disabled; filesystem provider still needed
 import './contrib/configuration/browser/configuration.contribution.js';
-import './contrib/welcome/browser/welcome.contribution.js';
+
 import './contrib/terminal/browser/sessionsTerminalContribution.js';
 import './contrib/logs/browser/logs.contribution.js';
+import './contrib/workspace/browser/workspace.contribution.js';
+import './contrib/welcome/browser/welcome.contribution.js';
 
 //#endregion
 
diff --git a/src/vs/sessions/sessions.web.main.internal.ts b/src/vs/sessions/sessions.web.main.internal.ts
new file mode 100644
index 0000000000000..4e7ae75ffc2bd
--- /dev/null
+++ b/src/vs/sessions/sessions.web.main.internal.ts
@@ -0,0 +1,24 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+// This file is the web embedder entry point for the Sessions workbench.
+// It mirrors workbench.web.main.internal.ts but loads the sessions entry
+// point and factory instead of the standard workbench ones.
+
+import './sessions.web.main.js';
+import { create } from './browser/web.factory.js';
+import { URI } from '../base/common/uri.js';
+import { Event, Emitter } from '../base/common/event.js';
+import { Disposable } from '../base/common/lifecycle.js';
+import { LogLevel } from '../platform/log/common/log.js';
+
+export {
+	create,
+	URI,
+	Event,
+	Emitter,
+	Disposable,
+	LogLevel,
+};
diff --git a/src/vs/sessions/sessions.web.main.ts b/src/vs/sessions/sessions.web.main.ts
new file mode 100644
index 0000000000000..b265cc7ea9fe4
--- /dev/null
+++ b/src/vs/sessions/sessions.web.main.ts
@@ -0,0 +1,167 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+
+// #######################################################################
+// ###                                                                 ###
+// ### !!! PLEASE ADD COMMON IMPORTS INTO SESSIONS.COMMON.MAIN.TS !!!  ###
+// ###                                                                 ###
+// #######################################################################
+
+//#region --- sessions common
+
+import './sessions.common.main.js';
+
+//#endregion
+
+
+//#region --- workbench parts
+
+import '../workbench/browser/parts/dialogs/dialog.web.contribution.js';
+
+//#endregion
+
+
+//#region --- sessions (web main) — sessions-specific web bootstrap
+
+import './browser/web.main.js';
+
+//#endregion
+
+
+//#region --- workbench services (browser equivalents of the electron services)
+
+import '../workbench/services/integrity/browser/integrityService.js';
+import '../workbench/services/search/browser/searchService.js';
+import '../workbench/services/textfile/browser/browserTextFileService.js';
+import '../workbench/services/keybinding/browser/keyboardLayoutService.js';
+import '../workbench/services/extensions/browser/extensionService.js';
+import '../workbench/services/extensionManagement/browser/extensionsProfileScannerService.js';
+import '../workbench/services/extensions/browser/extensionsScannerService.js';
+import '../workbench/services/extensionManagement/browser/webExtensionsScannerService.js';
+import '../workbench/services/extensionManagement/common/extensionManagementServerService.js';
+import '../workbench/services/mcp/browser/mcpWorkbenchManagementService.js';
+import '../workbench/services/extensionManagement/browser/extensionGalleryManifestService.js';
+import '../workbench/services/telemetry/browser/telemetryService.js';
+import '../workbench/services/url/browser/urlService.js';
+import '../workbench/services/update/browser/updateService.js';
+import '../workbench/services/workspaces/browser/workspacesService.js';
+import '../workbench/services/workspaces/browser/workspaceEditingService.js';
+import '../workbench/services/dialogs/browser/fileDialogService.js';
+import '../workbench/services/host/browser/browserHostService.js';
+import '../platform/meteredConnection/browser/meteredConnectionService.js';
+import '../workbench/services/lifecycle/browser/lifecycleService.js';
+import '../workbench/services/clipboard/browser/clipboardService.js';
+import '../workbench/services/localization/browser/localeService.js';
+import '../workbench/services/path/browser/pathService.js';
+import '../workbench/services/themes/browser/browserHostColorSchemeService.js';
+import '../workbench/services/encryption/browser/encryptionService.js';
+import '../workbench/services/imageResize/browser/imageResizeService.js';
+import '../workbench/services/secrets/browser/secretStorageService.js';
+import '../workbench/services/workingCopy/browser/workingCopyBackupService.js';
+import '../workbench/services/tunnel/browser/tunnelService.js';
+import '../workbench/services/files/browser/elevatedFileService.js';
+import '../workbench/services/workingCopy/browser/workingCopyHistoryService.js';
+import '../workbench/services/userDataSync/browser/webUserDataSyncEnablementService.js';
+import '../workbench/services/userDataProfile/browser/userDataProfileStorageService.js';
+import '../workbench/services/configurationResolver/browser/configurationResolverService.js';
+import '../platform/extensionResourceLoader/browser/extensionResourceLoaderService.js';
+import '../workbench/services/auxiliaryWindow/browser/auxiliaryWindowService.js';
+import '../workbench/services/browserElements/browser/webBrowserElementsService.js';
+import '../workbench/services/power/browser/powerService.js';
+
+import { InstantiationType, registerSingleton } from '../platform/instantiation/common/extensions.js';
+import { IAccessibilityService } from '../platform/accessibility/common/accessibility.js';
+import { IContextMenuService } from '../platform/contextview/browser/contextView.js';
+import { ContextMenuService } from '../platform/contextview/browser/contextMenuService.js';
+import { IExtensionTipsService } from '../platform/extensionManagement/common/extensionManagement.js';
+import { ExtensionTipsService } from '../platform/extensionManagement/common/extensionTipsService.js';
+import { IWorkbenchExtensionManagementService } from '../workbench/services/extensionManagement/common/extensionManagement.js';
+import { ExtensionManagementService } from '../workbench/services/extensionManagement/common/extensionManagementService.js';
+import { UserDataSyncMachinesService, IUserDataSyncMachinesService } from '../platform/userDataSync/common/userDataSyncMachines.js';
+import { IUserDataSyncStoreService, IUserDataSyncService, IUserDataAutoSyncService, IUserDataSyncLocalStoreService, IUserDataSyncResourceProviderService } from '../platform/userDataSync/common/userDataSync.js';
+import { UserDataSyncStoreService } from '../platform/userDataSync/common/userDataSyncStoreService.js';
+import { UserDataSyncLocalStoreService } from '../platform/userDataSync/common/userDataSyncLocalStoreService.js';
+import { UserDataSyncService } from '../platform/userDataSync/common/userDataSyncService.js';
+import { IUserDataSyncAccountService, UserDataSyncAccountService } from '../platform/userDataSync/common/userDataSyncAccount.js';
+import { UserDataAutoSyncService } from '../platform/userDataSync/common/userDataAutoSyncService.js';
+import { AccessibilityService } from '../platform/accessibility/browser/accessibilityService.js';
+import { ICustomEndpointTelemetryService } from '../platform/telemetry/common/telemetry.js';
+import { NullEndpointTelemetryService } from '../platform/telemetry/common/telemetryUtils.js';
+import './services/title/browser/titleService.js';
+import { ITimerService, TimerService } from '../workbench/services/timer/browser/timerService.js';
+import { IDiagnosticsService, NullDiagnosticsService } from '../platform/diagnostics/common/diagnostics.js';
+import { ILanguagePackService } from '../platform/languagePacks/common/languagePacks.js';
+import { WebLanguagePacksService } from '../platform/languagePacks/browser/languagePacks.js';
+import { IWebContentExtractorService, NullWebContentExtractorService, ISharedWebContentExtractorService, NullSharedWebContentExtractorService } from '../platform/webContentExtractor/common/webContentExtractor.js';
+import { IMcpGalleryManifestService } from '../platform/mcp/common/mcpGalleryManifest.js';
+import { WorkbenchMcpGalleryManifestService } from '../workbench/services/mcp/browser/mcpGalleryManifestService.js';
+import { UserDataSyncResourceProviderService } from '../platform/userDataSync/common/userDataSyncResourceProvider.js';
+
+registerSingleton(IWorkbenchExtensionManagementService, ExtensionManagementService, InstantiationType.Delayed);
+registerSingleton(IAccessibilityService, AccessibilityService, InstantiationType.Delayed);
+registerSingleton(IContextMenuService, ContextMenuService, InstantiationType.Delayed);
+registerSingleton(IUserDataSyncStoreService, UserDataSyncStoreService, InstantiationType.Delayed);
+registerSingleton(IUserDataSyncMachinesService, UserDataSyncMachinesService, InstantiationType.Delayed);
+registerSingleton(IUserDataSyncLocalStoreService, UserDataSyncLocalStoreService, InstantiationType.Delayed);
+registerSingleton(IUserDataSyncAccountService, UserDataSyncAccountService, InstantiationType.Delayed);
+registerSingleton(IUserDataSyncService, UserDataSyncService, InstantiationType.Delayed);
+registerSingleton(IUserDataSyncResourceProviderService, UserDataSyncResourceProviderService, InstantiationType.Delayed);
+registerSingleton(IUserDataAutoSyncService, UserDataAutoSyncService, InstantiationType.Eager);
+registerSingleton(IExtensionTipsService, ExtensionTipsService, InstantiationType.Delayed);
+registerSingleton(ITimerService, TimerService, InstantiationType.Delayed);
+registerSingleton(ICustomEndpointTelemetryService, NullEndpointTelemetryService, InstantiationType.Delayed);
+registerSingleton(IDiagnosticsService, NullDiagnosticsService, InstantiationType.Delayed);
+registerSingleton(ILanguagePackService, WebLanguagePacksService, InstantiationType.Delayed);
+registerSingleton(IWebContentExtractorService, NullWebContentExtractorService, InstantiationType.Delayed);
+registerSingleton(ISharedWebContentExtractorService, NullSharedWebContentExtractorService, InstantiationType.Delayed);
+registerSingleton(IMcpGalleryManifestService, WorkbenchMcpGalleryManifestService, InstantiationType.Delayed);
+
+//#endregion
+
+
+//#region --- workbench contributions (browser versions)
+
+import '../workbench/contrib/logs/browser/logs.contribution.js';
+import '../workbench/contrib/localization/browser/localization.contribution.js';
+import '../workbench/contrib/performance/browser/performance.web.contribution.js';
+import '../workbench/contrib/preferences/browser/keyboardLayoutPicker.js';
+import '../workbench/contrib/debug/browser/extensionHostDebugService.js';
+import '../workbench/contrib/welcomeBanner/browser/welcomeBanner.contribution.js';
+import '../workbench/contrib/webview/browser/webview.web.contribution.js';
+import '../workbench/contrib/extensions/browser/extensions.web.contribution.js';
+import '../workbench/contrib/terminal/browser/terminal.web.contribution.js';
+import '../workbench/contrib/externalTerminal/browser/externalTerminal.contribution.js';
+import '../workbench/contrib/terminal/browser/terminalInstanceService.js';
+import '../workbench/contrib/tasks/browser/taskService.js';
+import '../workbench/contrib/tags/browser/workspaceTagsService.js';
+import '../workbench/contrib/issue/browser/issue.contribution.js';
+import '../workbench/contrib/splash/browser/splash.contribution.js';
+import '../workbench/contrib/remote/browser/remoteStartEntry.contribution.js';
+import '../workbench/contrib/processExplorer/browser/processExplorer.web.contribution.js';
+
+//#endregion
+
+
+//#region --- sessions contributions (same as desktop — these are all browser-safe)
+
+import './browser/paneCompositePartService.js';
+import './browser/layoutActions.js';
+
+import './contrib/accountMenu/browser/account.contribution.js';
+import './contrib/aiCustomizationTreeView/browser/aiCustomizationTreeView.contribution.js';
+import './contrib/applyCommitsToParentRepo/browser/applyChangesToParentRepo.js';
+import './contrib/chat/browser/chat.contribution.js';
+import './contrib/terminal/browser/sessionsTerminalContribution.js';
+import './contrib/sessions/browser/sessions.contribution.js';
+import './contrib/sessions/browser/customizationsToolbar.contribution.js';
+import './contrib/changes/browser/changesView.contribution.js';
+import './contrib/codeReview/browser/codeReview.contributions.js';
+import './contrib/github/browser/github.contribution.js';
+import './contrib/fileTreeView/browser/fileTreeView.contribution.js';
+import './contrib/configuration/browser/configuration.contribution.js';
+import './contrib/welcome/browser/welcome.contribution.js';
+
+//#endregion
diff --git a/src/vs/sessions/skills/update-skills/SKILL.md b/src/vs/sessions/skills/update-skills/SKILL.md
new file mode 100644
index 0000000000000..56dad1140f239
--- /dev/null
+++ b/src/vs/sessions/skills/update-skills/SKILL.md
@@ -0,0 +1,114 @@
+---
+name: update-skills
+description: Create or update repository skills and instructions when major learnings are discovered during a session. Use when the user says "learn!", when a significant pattern or pitfall is identified, or when reusable domain knowledge should be captured for future sessions.
+---
+<!-- Customize this skill and select save to override its behavior. Delete that copy to restore the built-in behavior. -->
+
+# Update Skills & Instructions
+
+When a major repository learning is discovered — a recurring pattern, a non-obvious pitfall, a crucial architectural constraint, or domain knowledge that would save future sessions significant time — capture it as a skill or instruction so it persists across sessions.
+
+## When to Use
+
+- The user explicitly says **"learn!"** or asks to capture a learning
+- You discover a significant pattern or constraint that cost meaningful debugging time
+- You identify reusable domain knowledge that isn't documented anywhere in the repo
+- A correction from the user reveals a general principle worth preserving
+
+## Decision: Skill vs Instruction vs Learning
+
+**Add a learning to an existing instruction** when:
+- The insight is small (1-4 sentences) and fits naturally into an existing instruction file
+- It refines or extends an existing guideline
+- Follow the pattern in `.github/instructions/learnings.instructions.md`
+
+**Create or update a skill** (`.github/skills/{name}/SKILL.md` or `.agents/skills/{name}/SKILL.md`) when:
+- The knowledge is substantial (multi-step procedure, detailed guidelines, or rich examples)
+- It covers a distinct domain area (e.g., "how to debug X", "patterns for Y")
+- Future sessions should be able to invoke it by name
+
+**Create or update an instruction** (`.github/instructions/{name}.instructions.md`) when:
+- The rule should apply automatically based on file patterns (`applyTo`) or globally
+- It's a coding convention, architectural constraint, or process rule
+- It doesn't need to be invoked on demand
+
+## Procedure
+
+### 1. Identify the Learning
+
+Reflect on what went wrong or what was discovered:
+- What was the problem or unexpected behavior?
+- Why was it a problem? (root cause, not symptoms)
+- How was it fixed or what's the correct approach?
+- Can it be generalized beyond this specific instance?
+
+### 2. Check for Existing Files
+
+Before creating new files, search for existing skills and instructions that might be the right home:
+
+```
+# Check existing skills
+ls .github/skills/ .agents/skills/ 2>/dev/null
+
+# Check existing instructions
+ls .github/instructions/ 2>/dev/null
+
+# Search for related content
+grep -r "related-keyword" .github/skills/ .github/instructions/ .agents/skills/
+```
+
+### 3a. Add to Existing File
+
+If an appropriate file exists, add the learning to its `## Learnings` section (create the section if it doesn't exist). Each learning should be 1-4 sentences.
+
+### 3b. Create a New Skill
+
+If the knowledge warrants a standalone skill:
+
+1. Choose the location:
+   - `.github/skills/{name}/SKILL.md` for project-level skills (committed to repo)
+   - `.agents/skills/{name}/SKILL.md` for agent-specific skills
+2. Create the directory and SKILL.md with frontmatter:
+
+```markdown
+---
+name: {skill-name}
+description: {One-line description of when and why to use this skill.}
+---
+
+# {Skill Title}
+
+{Body with guidelines, procedures, examples, and learnings.}
+```
+
+3. The `name` field **must match** the parent folder name exactly.
+4. Include concrete examples — skills with examples are far more useful than abstract rules.
+
+### 3c. Create a New Instruction
+
+If the knowledge should apply automatically:
+
+```markdown
+---
+description: {When these instructions should be loaded}
+applyTo: '{glob pattern}' # optional — auto-load when matching files are attached
+---
+
+{Content of the instruction.}
+```
+
+### 4. Quality Checks
+
+Before saving:
+- Is the learning **general enough** to help future sessions, not just this one?
+- Is it **specific enough** to be actionable, not just a vague principle?
+- Does it include a **concrete example** of right vs wrong?
+- Does it avoid duplicating knowledge already captured elsewhere?
+- Is the description clear enough that the agent will know **when** to invoke/apply it?
+
+### 5. Inform the User
+
+After creating or updating the file:
+- Summarize what was captured and where
+- Explain why this location was chosen
+- Note if any existing content was updated vs new content created
diff --git a/src/vs/sessions/test/ai-customizations.test.md b/src/vs/sessions/test/ai-customizations.test.md
new file mode 100644
index 0000000000000..75fa33d55de82
--- /dev/null
+++ b/src/vs/sessions/test/ai-customizations.test.md
@@ -0,0 +1,207 @@
+# AI Customizations Test Plan
+
+The following test plan outlines the scenarios and specifications for the AI Customizations feature, which includes a management editor and tree view for managing customization items.
+
+## SPECS
+
+- [`../AI_CUSTOMIZATIONS.md`](../AI_CUSTOMIZATIONS.md)
+
+## SCENARIOS
+
+### Scenario 1: Empty state — no session, no customizations
+
+#### Description
+
+This tests the baseline empty state before any session or workspace is active. The 'new AI developer' state - who doesn't have any customizations on their machine yet.
+
+#### Preconditions
+
+- On 'New Session' screen
+- No folder selected
+- No user customizations created (from this tool or others i.e. Copilot CLI)
+
+#### Actions
+
+1. Open the sidebar customizations section
+2. Observe no sidebar counts are shown for any section (Agents, Skills, Instructions, Prompts, Hooks)
+3. Open the management editor by clicking on one of the sections (e.g., "Instructions")
+4. Observe the empty state messages
+5. Click through each section in the sidebar
+6. Run Developer: Customizations Debug and read the report
+
+#### Expected Results
+
+- All sidebar counts are hidden (no badges visible)
+- Management editor shows empty state for each section with "No X yet" message
+- Create button for **user** customizations is visible but disabled until a workspace folder or repository is selected (Hooks should also show a disabled button, since there is no 'user' scoped hooks)
+
+#### Notes
+
+- The `Window: Sessions` should be verified by running `Developer: Customizations Debug`
+- No workspace root should be active, verified via `Developer: Customizations Debug` (active root = none)
+
+---
+
+### Scenario 2: Active workspace selected from new session state
+
+#### Description
+
+This tests the transition from the empty state to having an active workspace selected, but before a worktree is checked out (i.e., before starting a task). This is the 'new session' state where the user has selected a repository but hasn't started working in a specific branch or worktree yet. Customizations should be loaded from the repository root, not a worktree, and counts should reflect that.
+
+#### Preconditions
+
+- On 'New Session' screen (Scenario 1 completed)
+- A git repository, cloned on the machine, is available to select
+  - For this test use `microsoft/vscode` cloned to a test folder
+
+#### Actions
+
+1. From the new session screen, select a workspace folder
+2. Observe the sidebar customization counts update
+3. Open the management editor by clicking on "Instructions"
+4. Observe items appear in the "Workspace" group
+5. Note the workspace item count in the group header
+6. Compare the sidebar badge count with the editor's workspace item count — they should match
+7. Click "Agents" in the sidebar
+8. Observe agent items listed with parsed friendly names (not raw filenames) and a description
+9. Click "Skills" in the sidebar
+10. Observe skills listed with names derived from folder names
+11. Click "Prompts" in the sidebar
+12. Observe only prompt-type items (no skills mixed in, although note there may be similarly named items)
+13. Click "Hooks" in the sidebar
+14. Observe only workspace-scoped hook files (no user-level `~/.claude/settings.json`)
+15. Run Developer: Customizations Debug and read the report
+
+#### Expected Results
+
+- Sidebar counts update from 0 to reflect the selected workspace's customizations
+- Sidebar badge count matches editor list count for every section
+- Instructions includes root-level files (AGENTS.md, CLAUDE.md, copilot-instructions.md) under "Workspace"
+- Instructions includes `.instructions.md` files from `.github/instructions/`
+- Agents shows friendly names (e.g., "Optimize" not "optimize.agent.md")
+- Prompts excludes skill-type slash commands
+- Hooks shows only workspace-local files (filter: `sources: [local]`)
+- No "Extensions" or "Plugins" groups visible
+- If user-level files exist in `~/.copilot/` or `~/.claude/`, a "User" group appears for applicable sections
+- Debug report shows `Window: Sessions`, `Active root: /path/to/repository`
+- Create button shows both "Workspace" and "User" options in dropdown
+
+#### Notes
+
+- The active root comes from the repository, not a worktree
+
+---
+
+### Scenario 3: Create new workspace instruction in an active worktree session
+
+#### Preconditions
+
+- Active session with a worktree checked out (task started and running)
+- Use the same repository as Scenario 2 (`microsoft/vscode`)
+
+#### Actions
+
+1. Observe sidebar customization counts reflect the worktree's customizations and are the same as Scenario 2 (since new worktree inherits from repo root, counts should be the same)
+2. Open the management editor by clicking on "Instructions"
+3. Observe items listed — should match files in the worktree (not the bare repo)
+4. Verify there is a primary button "New Instructions (Workspace)" and another option in the dropdown for "New Instructions (User)"
+5. Click the "+ New Instructions (Workspace)" button (primary action)
+6. Select a name `<name>` when the quickpick appears and confirm
+7. Verify the file opens in the embedded editor
+8. Verify the file path shown in the editor header is `<WORKTREE_PATH>/.github/instructions/<name>.instructions.md`
+9. Update the instruction file with some content, then press the back button
+10. Confirm the instruction file was auto-committed and shows up in the worktree changes list
+11. Reopen the customization management editor and click on "Instructions" again
+12. Observe the new instruction appears in the "Workspace" group
+13. Observe the sidebar badge count has incremented by 1
+
+#### Expected Results
+
+- Active root is the worktree path, not the repository path
+- File is created under the worktree's `.github/instructions/` folder (not the bare repo)
+- File auto-saves and auto-commits to the worktree
+- Item count updates in both the sidebar badge and editor list after creation
+- The new file appears in the list with a friendly name derived from the filename
+
+#### Notes
+
+- This is the primary creation flow — workspace instructions are the most common customization type
+- Key difference from Scenario 2: active root is the worktree, creation targets the worktree
+
+---
+
+### Scenario 4: Create new user instruction in an active worktree session
+
+#### Preconditions
+
+- Active session with a worktree checked out (continuing from Scenario 3)
+
+#### Actions
+
+1. Open the management editor by clicking on "Instructions"
+2. Click the "Add" dropdown arrow → click "New Instruction (User)"
+3. Select a name `<name>` when the quickpick appears and confirm
+4. Verify the file opens in the embedded editor
+5. Verify the file path shown in the editor header is `~/.copilot/instructions/<name>.instructions.md`
+6. Confirm the path is NOT the VS Code profile folder (e.g., NOT `~/.vscode-oss-sessions-dev/User/...`)
+7. Press the back button to return to the list
+8. Observe the new instruction appears in the "User" group
+9. Observe the sidebar badge count reflects the new user instruction
+10. Run Developer: Customizations Debug
+11. Check the "Source Folders (creation targets)" section — verify `[user]` points to `~/.copilot/instructions`
+
+#### Expected Results
+
+- User file is created under `~/.copilot/instructions/` (not the VS Code profile folder)
+- The file appears in the "User" group in the list
+- Sidebar badge count includes the new user file
+- Debug report confirms the user creation target is `~/.copilot/instructions`
+
+#### Notes
+
+- This validates that `AgenticPromptsService.getSourceFolders()` correctly redirects user creation to `~/.copilot/`
+- The VS Code profile folder should never be used for user creation in sessions
+
+---
+
+### Scenario 5: Create a new hook in an active worktree session
+
+#### Preconditions
+
+- Active session with a worktree checked out (continuing from Scenario 3)
+- No existing `hooks.json` in the worktree's `.github/hooks/` folder
+
+#### Actions
+
+1. Open the management editor by clicking on "Hooks"
+2. Observe the current hook items (if any)
+3. Click the "Add" button → observe a `hooks.json` is created
+4. Verify the hooks.json opens in the embedded editor
+5. Verify the file path is `<WORKTREE_PATH>/.github/hooks/hooks.json`
+6. Read the generated JSON and check:
+   - `"version": 1` is present at the top level
+   - Hook entries use `"bash"` as the shell field (not `"command"`)
+   - All hook event types are present: `sessionStart`, `userPromptSubmitted`, `preToolUse`, `postToolUse`
+   - Each event has a `[{ "type": "command", "bash": "" }]` skeleton
+7. Edit one of the hook entries (e.g., add a bash command to `sessionStart`)
+8. Press the back button to return to the list
+9. Observe the hooks.json appears in the "Workspace" group
+10. Observe the sidebar badge count for Hooks has updated
+11. Run Developer: Customizations Debug on the Hooks section
+12. Verify `Active root` points to the worktree path
+13. Compare Stage 1 counts with Stage 3 counts — they should be consistent
+
+#### Expected Results
+
+- Hooks.json is created in the worktree's `.github/hooks/` folder
+- JSON skeleton has correct Copilot CLI format: `"version": 1`, `"bash"` field
+- All hook events from `COPILOT_CLI_HOOK_TYPE_MAP` are present in the skeleton
+- Hooks section shows only workspace-local hook files (no user-level hooks visible)
+- Item count updates after creation
+- Debug report Stage 1 → Stage 3 pipeline shows no unexpected filtering
+
+#### Notes
+
+- Hook events are derived from `COPILOT_CLI_HOOK_TYPE_MAP` — adding new events to the schema auto-includes them in the skeleton
+- Only `"bash"` is used (not `"command"`) to match the Copilot CLI schema
+- The `"version": 1` field is required by the CLI for format detection
diff --git a/src/vs/sessions/test/browser/layoutActions.test.ts b/src/vs/sessions/test/browser/layoutActions.test.ts
index 786236ec9703a..f8362f7d6549b 100644
--- a/src/vs/sessions/test/browser/layoutActions.test.ts
+++ b/src/vs/sessions/test/browser/layoutActions.test.ts
@@ -16,7 +16,7 @@ suite('Sessions - Layout Actions', () => {
 	ensureNoDisposablesAreLeakedInTestSuite();
 
 	test('always-on-top toggle action is contributed to TitleBarRight', () => {
-		const items = MenuRegistry.getMenuItems(Menus.TitleBarRight);
+		const items = MenuRegistry.getMenuItems(Menus.TitleBarRightLayout);
 		const menuItems = items.filter(isIMenuItem);
 
 		const toggleAlwaysOnTop = menuItems.find(item => item.command.id === 'workbench.action.toggleWindowAlwaysOnTop');
diff --git a/src/vs/sessions/test/e2e/.gitignore b/src/vs/sessions/test/e2e/.gitignore
new file mode 100644
index 0000000000000..141d99daed58e
--- /dev/null
+++ b/src/vs/sessions/test/e2e/.gitignore
@@ -0,0 +1,3 @@
+out/
+*.png
+node_modules/
diff --git a/src/vs/sessions/test/e2e/README.md b/src/vs/sessions/test/e2e/README.md
new file mode 100644
index 0000000000000..347d0660da970
--- /dev/null
+++ b/src/vs/sessions/test/e2e/README.md
@@ -0,0 +1,392 @@
+# Agent Sessions — E2E Tests
+
+Automated dogfooding tests for the Agent Sessions window using a
+**compile-and-replay** architecture powered by
+[`playwright-cli`](https://github.com/microsoft/playwright-cli) and Copilot CLI.
+
+## Mocking Architecture
+
+These tests run the **real** Sessions workbench with only the minimal set of
+services mocked — specifically the services that require external backends
+(auth, LLM, git). Everything downstream from the mock agent's canned response
+runs through the real code paths.
+
+### What's Mocked (Minimal)
+
+| Service | Mock | Why |
+|---------|------|-----|
+| `IChatEntitlementService` | Returns `ChatEntitlement.Free` | No real Copilot account in CI |
+| `IDefaultAccountService` | Returns a fake signed-in account | Hides the "Sign In" button |
+| `IGitService` | Resolves immediately (no 10s barrier) | No real git extension in web tests |
+| Chat agents (`copilotcli`, etc.) | Canned keyword-matched responses with `textEdit` progress items | No real LLM backend |
+| `mock-fs://` FileSystemProvider | `InMemoryFileSystemProvider` registered directly in the workbench (not extension host) | Must be available before any service tries to resolve workspace files |
+| GitHub authentication | Always-signed-in mock provider (extension) | No real OAuth flow |
+| Code Review command | Returns canned review comments per file (extension) | No real Copilot AI review |
+| PR commands (Create/Open/Merge) | No-op handlers that log and show info messages (extension) | No real GitHub API |
+
+### What's Real (Everything Else)
+
+The following services run with their **real** implementations, ensuring tests
+exercise the actual code paths:
+
+- **`ChatEditingService`** — Processes `textEdit` progress items from the mock
+  agent, creates `IModifiedFileEntry` objects with real before/after diffs, and
+  computes actual `linesAdded`/`linesRemoved` from content changes
+- **`ChatModel`** — Routes agent progress through `acceptResponseProgress()`
+- **`ChangesViewPane`** — Reads file modification state from `IChatEditingService`
+  observables and renders the tree with real diff stats
+- **Diff editor** — Opens a real diff view when clicking files in the changes list
+- **Context keys** — `hasUndecidedChatEditingResourceContextKey`,
+  `hasAppliedChatEditsContextKey` are set by real `ModifiedFileEntryState`
+  observations
+- **Menu actions** — "Create PR", "Accept", "Reject" buttons appear based on
+  real context key state
+- **`CodeReviewService`** — Orchestrates review requests, processes results from
+  the mock `github.copilot.chat.codeReview.run` command, and stores comments
+- **`CodeReviewToolbarContribution`** — Shows the Code Review button in the
+  Changes view toolbar based on real context key state
+
+### Data Flow
+
+```
+User types message → Chat Widget → ChatService
+  → Mock Agent invoke() → progress([{ kind: 'textEdit', uri, edits }])
+    → ChatModel.acceptResponseProgress()
+      → ChatEditingService observes textEditGroup parts
+        → Creates IModifiedFileEntry per file
+        → Reads original content from mock-fs:// FileSystemProvider
+        → Computes real diff (linesAdded, linesRemoved)
+          → ChangesViewPane renders via observable chain
+            → Click file → Opens real diff editor
+```
+
+The mock agent is the **only** point where canned data enters the system.
+Everything downstream uses real service implementations.
+
+### Code Review & PR Button Flow
+
+```
+Code Review button clicked → sessions.codeReview.run (core action)
+  → CodeReviewService.requestReview()
+    → commandService.executeCommand('chat.internal.codeReview.run')
+      → Bridge forwards to 'github.copilot.chat.codeReview.run'
+        → Mock extension returns canned comments
+          → CodeReviewService stores results, updates observable state
+            → CodeReviewToolbarContribution updates button icon/badge
+
+Create PR button clicked → github.copilot.chat.createPullRequestCopilotCLIAgentSession.createPR
+  → Mock extension logs and shows info message
+```
+
+The PR buttons (Create PR, Open PR, Merge) are contributed via the mock
+extension's `package.json` menus, gated by `chatSessionType == copilotcli`.
+The `chatSessionType` context key is derived from the session URI scheme
+(`getChatSessionType()`), which returns `copilotcli` for mock sessions.
+
+### Why the FileSystem Provider Is Registered in the Workbench
+
+The `mock-fs://` `InMemoryFileSystemProvider` is registered directly on
+`IFileService` inside `TestSessionsBrowserMain.createWorkbench()` — **not** in
+the mock extension. This is critical because several workbench services
+(SnippetsService, AgenticPromptFilesLocator, MCP, etc.) try to resolve files
+in the workspace folder **before** the extension host activates. If the
+provider were only registered via `vscode.workspace.registerFileSystemProvider()`
+in the extension, these services would see `ENOPRO: No file system provider`
+errors and fail silently.
+
+The mock extension still registers a `mock-fs` provider via the extension API
+(needed for extension host operations), but the workbench-level registration
+is the source of truth.
+
+### File Edit Strategy
+
+Mock edits target files that exist in the `mock-fs://` file store so the
+`ChatEditingService` can compute real before/after diffs:
+
+- **Existing files** (e.g. `/mock-repo/src/index.ts`, `/mock-repo/package.json`) — edits use a
+  full-file replacement range (`line 1 → line 99999`) so the editing service
+  diffs the old content against the new content
+- **New files** (e.g. `/mock-repo/src/build.ts`) — edits use an insert-at-beginning
+  range, producing a "file created" entry in the changes view
+
+### Mock Workspace Folder
+
+The workspace folder URI is `mock-fs://mock-repo/mock-repo`. The path
+`/mock-repo` (not root `/`) is used so that `basename(folderUri)` returns
+`"mock-repo"` — this is what the folder picker displays. All mock files are
+stored under this path in the in-memory file store.
+
+## How It Works
+
+There are two phases:
+
+### Phase 1: Generate (uses LLM — slow, run once)
+
+```bash
+npm run generate
+```
+
+For each `.scenario.md` file, the generate script:
+1. Starts the Sessions web server and opens the page in `playwright-cli`
+2. Takes an accessibility tree snapshot of the current page
+3. Sends each natural-language step + snapshot to **Copilot CLI**, which returns
+   the exact `playwright-cli` commands (e.g. `click e43`, `type "hello"`)
+4. Executes the commands to advance the UI state for the next step
+5. Writes the compiled commands to a `.commands.json` file in the `scenarios/generated/` folder
+
+```
+scenarios/
+├── 01-repo-picker-on-submit.scenario.md       ← human-written
+├── 02-cloud-disables-add-run-action.scenario.md
+└── generated/
+    ├── 01-repo-picker-on-submit.commands.json  ← agent-generated
+    └── 02-cloud-disables-add-run-action.commands.json
+```
+
+The `.commands.json` files are **committed to git** — they're the deterministic
+test plan that everyone runs.
+
+### Phase 2: Test (no LLM — fast, deterministic)
+
+```bash
+npm test
+```
+
+The test runner reads each `.commands.json` and replays the `playwright-cli`
+commands mechanically. No LLM calls, no regex matching, no icon stripping.
+Just sequential commands and assertions.
+
+### When to Re-generate
+
+Run `npm run generate` when:
+- You add a new `.scenario.md` file
+- The UI changes and refs are stale (tests start failing)
+- You modify an existing scenario's steps
+
+## File Structure
+
+```
+e2e/
+├── common.cjs               # Shared helpers (server, playwright-cli, parser)
+├── generate.cjs              # Compiles scenarios → .commands.json via Copilot CLI
+├── test.cjs                  # Replays .commands.json deterministically
+├── package.json              # npm scripts: generate, test
+├── extensions/
+│   └── sessions-e2e-mock/    # Mock extension (auth + mock-fs:// file system)
+├── scenarios/
+│   ├── 01-chat-response.scenario.md
+│   ├── 02-chat-with-changes.scenario.md
+│   └── generated/
+│       ├── 01-chat-response.commands.json
+│       └── 02-chat-with-changes.commands.json
+├── .gitignore
+└── README.md
+```
+
+Supporting files outside `e2e/`:
+
+```
+src/vs/sessions/test/
+├── web.test.ts              # TestSessionsBrowserMain + MockChatAgentContribution
+├── web.test.factory.ts      # Factory for test workbench (replaces web.factory.ts)
+└── sessions.web.test.internal.ts  # Test entry point
+
+scripts/
+├── code-sessions-web.js      # HTTP server that serves Sessions as a web app
+└── code-sessions-web.sh      # Shell wrapper
+```
+
+## Prerequisites
+
+- VS Code compiled (`out/` at the repo root):
+  ```bash
+  npm install && npm run compile
+  ```
+- Dependencies installed:
+  ```bash
+  cd src/vs/sessions/test/e2e && npm install
+  ```
+- Copilot CLI available (for `npm run generate` only):
+  ```bash
+  copilot --version
+  ```
+
+## Running
+
+```bash
+cd src/vs/sessions/test/e2e
+
+# First time or after UI changes:
+npm run generate
+
+# Run tests (fast, deterministic):
+npm test
+```
+
+Example test output:
+
+```
+Found 2 compiled scenario(s)
+
+Starting sessions web server on port 9542…
+Server ready.
+
+▶ Scenario: Repository picker opens when submitting without a repo
+  ✅   step 1: Click button "Cloud"
+  ✅   step 2: Type "build the project" in the chat input
+  ✅   step 3: Press Enter to submit
+  ✅   step 4: Verify the repository picker dropdown is visible
+
+▶ Scenario: Switching to Cloud target disables the Add Run Action button
+  ✅   step 1: Click button "Cloud"
+  ✅   step 2: Click button "Local"
+
+Results: 6 passed, 0 failed
+```
+
+## Writing a New Scenario
+
+1. Create a new `NN-description.scenario.md` file in `scenarios/`.
+   Files are sorted by name and run in order.
+
+2. Use this format:
+
+```markdown
+# Scenario: Short description of what this tests
+
+## Steps
+1. Click button "Cloud"
+2. Type "build the project" in the chat input
+3. Press Enter to submit
+4. Verify the repository picker dropdown is visible
+```
+
+3. Run `npm run generate` to compile it into a `.commands.json` file.
+
+4. Run `npm test` to verify it works.
+
+5. Commit both the `.scenario.md` and `.commands.json` files.
+
+### Step Language
+
+Write steps in plain English. The Copilot agent interprets them against the
+page's accessibility tree. Common patterns:
+
+| Pattern | Example |
+|---------|---------|
+| Click a button | `Click button "Cloud"` |
+| Type in an input | `Type "hello" in the chat input` |
+| Press a key | `Press Enter` |
+| Verify visibility | `Verify the repository picker dropdown is visible` |
+| Verify button state | `Verify the "Send" button is disabled` |
+
+You're not limited to these patterns — the agent understands natural language.
+
+### The .commands.json Format
+
+Each compiled step looks like:
+
+```json
+{
+  "description": "Click button \"Cloud\"",
+  "commands": [
+    "click e143"
+  ]
+}
+```
+
+For assertions, the agent outputs a `snapshot` command followed by an assertion comment:
+
+```json
+{
+  "description": "Verify the repository picker dropdown is visible",
+  "commands": [
+    "snapshot",
+    "# ASSERT_VISIBLE: Repository Picker"
+  ]
+}
+```
+
+The test runner understands these comment-based assertions:
+- `# ASSERT_VISIBLE: <text>` — checks snapshot contains the text
+- `# ASSERT_DISABLED: <label>` — checks button has `[disabled]`
+- `# ASSERT_ENABLED: <label>` — checks button doesn't have `[disabled]`
+
+### How a Step Executes (Worked Example)
+
+Let's trace `Click button "Cloud"` through both phases.
+
+**Generate phase** — the agent sees the accessibility tree snapshot:
+
+```yaml
+- group "Session target"
+  - button "Local" [ref=e141]
+  - button "Cloud" [ref=e143]
+```
+
+Copilot CLI returns: `click e143`
+
+This is saved to `.commands.json` and the click is executed to advance state.
+
+**Test phase** — the runner reads:
+
+```json
+{ "commands": ["click e143"] }
+```
+
+It shells out to `playwright-cli click e143`. Done. No parsing, no matching.
+
+### Tips
+
+- **Use exact button labels** as they appear in the UI.
+- **One action per step** — keep steps atomic for clear failure messages.
+- **Order matters** — scenarios run sequentially; an Escape is pressed between them.
+- **Prefix filenames** with numbers (`01-`, `02-`, …) to control execution order.
+- **Re-generate selectively**: `npm run generate -- 01-repo` to recompile one scenario.
+
+### Testing File Diffs
+
+To test that chat responses produce real file diffs:
+
+1. Use a message keyword that triggers file edits in the mock agent
+   (e.g. "build", "fix" — see `getMockResponseWithEdits()` in `web.test.ts`)
+2. The mock agent emits `textEdit` progress items that flow through the
+   **real** `ChatEditingService`
+3. Open the secondary side bar to see the Changes view
+4. Assert file names are visible in the changes tree
+5. Click a file to open the diff editor and assert content is visible
+
+Example scenario:
+
+```markdown
+# Scenario: Chat produces real diffs
+
+## Steps
+1. Type "build the project" in the chat input
+2. Press Enter to submit
+3. Verify there is a response in the chat
+4. Toggle the secondary side bar
+5. Verify the changes view shows modified files
+6. Click on "index.ts" in the changes list
+7. Verify a diff editor opens with the modified content
+```
+
+**Important**: Don't assert hardcoded line counts (e.g. `+23`). Instead assert
+on file names and content snippets — the real diff engine computes the actual
+counts, which may change as mock file content evolves.
+
+### Adding Mock File Edits
+
+To add new keyword-matched responses with file edits, update
+`getMockResponseWithEdits()` in `src/vs/sessions/test/web.test.ts`:
+
+1. **For existing files** — target URIs whose paths match `EXISTING_MOCK_FILES`
+   (files pre-seeded in the mock extension's file store). The `emitFileEdits()`
+   helper uses a full-file replacement range so the `ChatEditingService`
+   computes a real diff.
+2. **For new files** — target any other path. The helper uses an insert range
+   for these, producing a "file created" entry.
+3. **Mock file store** — to add or change pre-seeded files, update `MOCK_FILES`
+   in `extensions/sessions-e2e-mock/extension.js` AND update
+   `EXISTING_MOCK_FILES` in `web.test.ts` to match. All paths must be under
+   `/mock-repo/` (e.g. `/mock-repo/src/newfile.ts`).
diff --git a/src/vs/sessions/test/e2e/common.cjs b/src/vs/sessions/test/e2e/common.cjs
new file mode 100644
index 0000000000000..dc61926e48621
--- /dev/null
+++ b/src/vs/sessions/test/e2e/common.cjs
@@ -0,0 +1,151 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+// @ts-check
+
+/**
+ * Shared helpers for the Sessions E2E test infrastructure.
+ */
+
+const fs = require('fs');
+const path = require('path');
+const cp = require('child_process');
+
+const APP_ROOT = path.resolve(__dirname, '..', '..', '..', '..', '..');
+const SCENARIOS_DIR = path.join(__dirname, 'scenarios');
+
+// ---------------------------------------------------------------------------
+// Scenario parser
+// ---------------------------------------------------------------------------
+
+function parseScenario(filePath) {
+	const raw = fs.readFileSync(filePath, 'utf-8');
+	const lines = raw.split('\n');
+	let name = path.basename(filePath, '.scenario.md');
+	const steps = [];
+	let inSteps = false;
+
+	for (const line of lines) {
+		const trimmed = line.trim();
+		if (trimmed.startsWith('# ')) { name = trimmed.slice(2).trim(); }
+		if (/^## steps?$/i.test(trimmed)) { inSteps = true; continue; }
+		if (trimmed.startsWith('## ')) { inSteps = false; continue; }
+		if (inSteps) {
+			const m = trimmed.match(/^(?:-|\d+\.)\s+(.*)/);
+			if (m) { steps.push(m[1].trim()); }
+		}
+	}
+	return { name, steps, filePath };
+}
+
+function discoverScenarios() {
+	return fs.readdirSync(SCENARIOS_DIR)
+		.filter(f => f.endsWith('.scenario.md'))
+		.sort()
+		.map(f => parseScenario(path.join(SCENARIOS_DIR, f)));
+}
+
+// ---------------------------------------------------------------------------
+// playwright-cli wrapper
+// ---------------------------------------------------------------------------
+
+function runPlaywrightCli(args) {
+	const argList = Array.isArray(args)
+		? args
+		: (args.match(/"[^"]*"|\S+/g) || []).map(s => s.replace(/^"|"$/g, ''));
+	const result = cp.spawnSync('playwright-cli', argList, {
+		cwd: APP_ROOT,
+		stdio: ['ignore', 'pipe', 'pipe'],
+		timeout: 30_000,
+		env: { ...process.env },
+	});
+	const stdout = (result.stdout || '').toString();
+	const stderr = (result.stderr || '').toString();
+	return { ok: result.status === 0, stdout, stderr };
+}
+
+function getSnapshot() {
+	const result = runPlaywrightCli(['snapshot']);
+	if (!result.ok) {
+		console.error(`  [snapshot] failed: ${result.stderr}`);
+		return {
+			stdout: '',
+			path: ''
+		};
+	}
+	const fileMatch = result.stdout.match(/\[Snapshot\]\((.+?\.yml)\)/);
+	let pathStr = '';
+	if (fileMatch) {
+		pathStr = path.join(APP_ROOT, fileMatch[1]);
+		try {
+			const content = fs.readFileSync(pathStr, 'utf-8');
+			if (!content.trim()) { console.error(`  [snapshot] file is empty`); }
+			return { stdout: content, path: pathStr };
+		} catch (e) {
+			console.error(`  [snapshot] failed to read: ${e.message}`);
+		}
+	}
+	return {
+		stdout: result.stdout,
+		path: pathStr
+	};
+}
+
+// ---------------------------------------------------------------------------
+// Server management
+// ---------------------------------------------------------------------------
+
+function startServer(port, { mock = false } = {}) {
+	const args = ['--no-open', '--port', String(port)];
+	if (mock) { args.push('--mock'); }
+	const server = cp.spawn(process.execPath, [
+		path.join(APP_ROOT, 'scripts', 'code-sessions-web.js'),
+		...args,
+	], {
+		cwd: APP_ROOT,
+		stdio: ['ignore', 'pipe', 'pipe'],
+		env: { ...process.env },
+	});
+	server.stdout.on('data', () => { });
+	server.stderr.on('data', () => { });
+	return server;
+}
+
+async function waitForServer(url, timeoutMs) {
+	const http = require('http');
+	const deadline = Date.now() + timeoutMs;
+	while (Date.now() < deadline) {
+		const ok = await new Promise(resolve => {
+			const req = http.get(url, res => { res.resume(); resolve(res.statusCode === 200); });
+			req.on('error', () => resolve(false));
+			req.setTimeout(1000, () => { req.destroy(); resolve(false); });
+		});
+		if (ok) { return; }
+		await new Promise(r => setTimeout(r, 500));
+	}
+	throw new Error(`Server at ${url} did not start within ${timeoutMs}ms`);
+}
+
+// ---------------------------------------------------------------------------
+// Commands file paths
+// ---------------------------------------------------------------------------
+
+function commandsPathForScenario(scenarioPath) {
+	const dir = path.join(path.dirname(scenarioPath), 'generated');
+	const name = path.basename(scenarioPath, '.scenario.md') + '.commands.json';
+	return path.join(dir, name);
+}
+
+module.exports = {
+	APP_ROOT,
+	SCENARIOS_DIR,
+	parseScenario,
+	discoverScenarios,
+	runPlaywrightCli,
+	getSnapshot,
+	startServer,
+	waitForServer,
+	commandsPathForScenario,
+};
diff --git a/src/vs/sessions/test/e2e/extensions/sessions-e2e-mock/extension.js b/src/vs/sessions/test/e2e/extensions/sessions-e2e-mock/extension.js
new file mode 100644
index 0000000000000..461ffb8207dd1
--- /dev/null
+++ b/src/vs/sessions/test/e2e/extensions/sessions-e2e-mock/extension.js
@@ -0,0 +1,176 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+// @ts-check
+
+/// <reference types="vscode" />
+
+/**
+ * Mock extension for Sessions E2E testing.
+ *
+ * Provides:
+ * - A fake GitHub authentication provider (skips sign-in)
+ * - Mock command handlers for Code Review, Create PR, Open PR, and Merge
+ *
+ * The mock-fs:// FileSystemProvider and chat agents are registered
+ * directly in the workbench (web.test.ts), not here.
+ */
+
+// ---------------------------------------------------------------------------
+// Activation
+// ---------------------------------------------------------------------------
+
+/**
+ * @param {import('vscode').ExtensionContext} context
+ */
+function activate(context) {
+	const vscode = require('vscode');
+
+	console.log('[sessions-e2e-mock] Activating mock extension');
+
+	// 1. Mock GitHub Authentication Provider
+	context.subscriptions.push(registerMockAuth(vscode));
+
+	// 2. Mock command handlers for Code Review and PR actions
+	context.subscriptions.push(...registerMockCommands(vscode));
+
+	// Note: The mock-fs:// FileSystemProvider is registered directly in the
+	// workbench (web.test.ts → registerMockFileSystemProvider) so it is
+	// available before any service tries to resolve workspace files.
+	// Do NOT register it here — it would cause a duplicate provider error.
+
+	console.log('[sessions-e2e-mock] All mocks registered');
+}
+
+// ---------------------------------------------------------------------------
+// Mock Authentication Provider
+// ---------------------------------------------------------------------------
+
+/**
+ * @param {typeof import('vscode')} vscode
+ * @returns {import('vscode').Disposable}
+ */
+function registerMockAuth(vscode) {
+	const sessionChangeEmitter = new vscode.EventEmitter();
+
+	/** @type {import('vscode').AuthenticationSession} */
+	const mockSession = {
+		id: 'mock-session-1',
+		accessToken: 'gho_mock_e2e_test_token_00000000000000000000',
+		account: {
+			id: 'e2e-test-user',
+			label: 'E2E Test User',
+		},
+		scopes: ['read:user', 'repo', 'workflow'],
+	};
+
+	/** @type {import('vscode').AuthenticationProvider} */
+	const provider = {
+		onDidChangeSessions: sessionChangeEmitter.event,
+		async getSessions(_scopes, _options) {
+			return [mockSession];
+		},
+		async createSession(_scopes, _options) {
+			sessionChangeEmitter.fire({ added: [mockSession], removed: [], changed: [] });
+			return mockSession;
+		},
+		async removeSession(_sessionId) {
+			sessionChangeEmitter.fire({ added: [], removed: [mockSession], changed: [] });
+		},
+	};
+
+	console.log('[sessions-e2e-mock] Registering mock GitHub auth provider');
+	return vscode.authentication.registerAuthenticationProvider('github', 'GitHub (Mock)', provider, {
+		supportsMultipleAccounts: false,
+	});
+}
+
+// ---------------------------------------------------------------------------
+// Mock Command Handlers (Code Review + PR Actions)
+// ---------------------------------------------------------------------------
+
+/**
+ * Registers mock command handlers that stand in for the real GitHub Copilot
+ * extension commands. These allow the Code Review and Create PR buttons to
+ * function in the e2e test environment.
+ *
+ * @param {typeof import('vscode')} vscode
+ * @returns {import('vscode').Disposable[]}
+ */
+function registerMockCommands(vscode) {
+	const disposables = [];
+
+	// Mock create PR — simulates successful PR creation
+	disposables.push(vscode.commands.registerCommand(
+		'github.copilot.chat.createPullRequestCopilotCLIAgentSession.createPR',
+		() => {
+			console.log('[sessions-e2e-mock] Mock Create PR invoked');
+			vscode.window.showInformationMessage('Mock: Pull request created successfully');
+		}
+	));
+
+	// Mock open PR — simulates opening a PR URL
+	disposables.push(vscode.commands.registerCommand(
+		'github.copilot.chat.openPullRequestCopilotCLIAgentSession.openPR',
+		() => {
+			console.log('[sessions-e2e-mock] Mock Open PR invoked');
+			vscode.window.showInformationMessage('Mock: Opening pull request');
+		}
+	));
+
+	// Mock merge — simulates merging changes
+	disposables.push(vscode.commands.registerCommand(
+		'github.copilot.chat.mergeCopilotCLIAgentSessionChanges.merge',
+		() => {
+			console.log('[sessions-e2e-mock] Mock Merge invoked');
+			vscode.window.showInformationMessage('Mock: Changes merged successfully');
+		}
+	));
+
+	// Mock merge and sync — simulates merging and syncing
+	disposables.push(vscode.commands.registerCommand(
+		'github.copilot.chat.mergeCopilotCLIAgentSessionChanges.mergeAndSync',
+		() => {
+			console.log('[sessions-e2e-mock] Mock Merge and Sync invoked');
+			vscode.window.showInformationMessage('Mock: Changes merged and synced successfully');
+		}
+	));
+
+	// Mock apply changes — simulates applying session changes
+	disposables.push(vscode.commands.registerCommand(
+		'github.copilot.chat.applyCopilotCLIAgentSessionChanges.apply',
+		() => {
+			console.log('[sessions-e2e-mock] Mock Apply Changes invoked');
+			vscode.window.showInformationMessage('Mock: Changes applied successfully');
+		}
+	));
+
+	// Mock checkout PR reroute — simulates checkout PR flow
+	disposables.push(vscode.commands.registerCommand(
+		'github.copilot.chat.checkoutPullRequestReroute',
+		() => {
+			console.log('[sessions-e2e-mock] Mock Checkout PR Reroute invoked');
+			vscode.window.showInformationMessage('Mock: Checking out pull request');
+		}
+	));
+
+	// Mock update changes — simulates updating session changes
+	disposables.push(vscode.commands.registerCommand(
+		'github.copilot.chat.updateCopilotCLIAgentSessionChanges.update',
+		() => {
+			console.log('[sessions-e2e-mock] Mock Update Changes invoked');
+			vscode.window.showInformationMessage('Mock: Changes updated successfully',);
+		}
+	));
+
+	console.log('[sessions-e2e-mock] Registered mock Code Review and PR command handlers');
+	return disposables;
+}
+
+// ---------------------------------------------------------------------------
+// Exports
+// ---------------------------------------------------------------------------
+
+module.exports = { activate };
diff --git a/src/vs/sessions/test/e2e/extensions/sessions-e2e-mock/package.json b/src/vs/sessions/test/e2e/extensions/sessions-e2e-mock/package.json
new file mode 100644
index 0000000000000..fa02ea6068b47
--- /dev/null
+++ b/src/vs/sessions/test/e2e/extensions/sessions-e2e-mock/package.json
@@ -0,0 +1,110 @@
+{
+	"name": "sessions-e2e-mock",
+	"displayName": "Sessions E2E Mock",
+	"description": "Mock auth, chat participant, and file system for E2E testing",
+	"version": "0.0.1",
+	"publisher": "vscode",
+	"engines": {
+		"vscode": "^1.100.0"
+	},
+	"extensionKind": ["ui", "workspace"],
+	"browser": "./extension.js",
+	"activationEvents": ["*"],
+	"enabledApiProposals": ["chatSessionsProvider"],
+	"capabilities": {
+		"virtualWorkspaces": true,
+		"untrustedWorkspaces": {
+			"supported": true
+		}
+	},
+	"contributes": {
+		"authentication": [
+			{
+				"id": "github",
+				"label": "GitHub (Mock)"
+			}
+		],
+		"commands": [
+			{
+				"command": "github.copilot.chat.applyCopilotCLIAgentSessionChanges.apply",
+				"title": "Apply Changes",
+				"icon": "$(check)"
+			},
+			{
+				"command": "github.copilot.chat.checkoutPullRequestReroute",
+				"title": "Checkout Pull Request",
+				"icon": "$(git-pull-request)"
+			},
+			{
+				"command": "github.copilot.chat.openPullRequestCopilotCLIAgentSession.openPR",
+				"title": "Open Pull Request",
+				"icon": "$(link-external)"
+			},
+			{
+				"command": "github.copilot.chat.mergeCopilotCLIAgentSessionChanges.merge",
+				"title": "Merge",
+				"icon": "$(git-merge)"
+			},
+			{
+				"command": "github.copilot.chat.mergeCopilotCLIAgentSessionChanges.mergeAndSync",
+				"title": "Merge and Sync",
+				"icon": "$(git-merge)"
+			},
+			{
+				"command": "github.copilot.chat.createPullRequestCopilotCLIAgentSession.createPR",
+				"title": "Create Pull Request",
+				"icon": "$(git-pull-request-create)"
+			},
+			{
+				"command": "github.copilot.chat.updateCopilotCLIAgentSessionChanges.update",
+				"title": "Update",
+				"icon": "$(cloud-upload)"
+			},
+			{
+				"command": "github.copilot.chat.codeReview.run",
+				"title": "Run Code Review"
+			}
+		],
+		"menus": {
+			"chat/input/editing/sessionToolbar": [
+				{
+					"command": "github.copilot.chat.applyCopilotCLIAgentSessionChanges.apply",
+					"when": "chatSessionType == copilotcli && workbenchState != empty && !isSessionsWindow",
+					"group": "navigation@0"
+				},
+				{
+					"command": "github.copilot.chat.checkoutPullRequestReroute",
+					"when": "chatSessionType == copilot-cloud-agent && !github.vscode-pull-request-github.activated && gitOpenRepositoryCount != 0",
+					"group": "navigation@0"
+				},
+				{
+					"command": "github.copilot.chat.openPullRequestCopilotCLIAgentSession.openPR",
+					"when": "chatSessionType == copilotcli && isSessionsWindow && sessions.hasOpenPullRequest",
+					"group": "navigation@1"
+				}
+			],
+			"chat/input/editing/sessionApplyActions": [
+				{
+					"command": "github.copilot.chat.mergeCopilotCLIAgentSessionChanges.merge",
+					"when": "chatSessionType == copilotcli && isSessionsWindow && !sessions.isMergeBaseBranchProtected",
+					"group": "merge@1"
+				},
+				{
+					"command": "github.copilot.chat.mergeCopilotCLIAgentSessionChanges.mergeAndSync",
+					"when": "chatSessionType == copilotcli && isSessionsWindow && !sessions.isMergeBaseBranchProtected",
+					"group": "merge@2"
+				},
+				{
+					"command": "github.copilot.chat.createPullRequestCopilotCLIAgentSession.createPR",
+					"when": "chatSessionType == copilotcli && isSessionsWindow && sessions.isMergeBaseBranchProtected && !sessions.hasOpenPullRequest",
+					"group": "pull_request@1"
+				},
+				{
+					"command": "github.copilot.chat.updateCopilotCLIAgentSessionChanges.update",
+					"when": "chatSessionType == copilotcli && isSessionsWindow",
+					"group": "update@1"
+				}
+			]
+		}
+	}
+}
diff --git a/src/vs/sessions/test/e2e/generate.cjs b/src/vs/sessions/test/e2e/generate.cjs
new file mode 100644
index 0000000000000..acff158998f55
--- /dev/null
+++ b/src/vs/sessions/test/e2e/generate.cjs
@@ -0,0 +1,243 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+// @ts-check
+
+/**
+ * Compile .scenario.md files into .commands.json using Copilot CLI.
+ *
+ * For each scenario, this script:
+ * 1. Starts the web server and opens the Sessions window in playwright-cli
+ * 2. Takes a snapshot of the current page state
+ * 3. Sends each step + snapshot to Copilot CLI to get the playwright-cli commands
+ * 4. Executes the commands (to advance UI state for the next step)
+ * 5. Writes the compiled commands to a .commands.json file
+ *
+ * Usage:
+ *   node generate.cjs                    # compile all scenarios
+ *   node generate.cjs 01-repo-picker     # compile matching scenario(s)
+ */
+
+const fs = require('fs');
+const path = require('path');
+const cp = require('child_process');
+const {
+	APP_ROOT,
+	discoverScenarios,
+	runPlaywrightCli,
+	getSnapshot,
+	startServer,
+	waitForServer,
+	commandsPathForScenario,
+} = require('./common.cjs');
+
+const PORT = 9100 + Math.floor(Math.random() * 900);
+const BASE_URL = `http://localhost:${PORT}/?skip-sessions-welcome`;
+
+const SYSTEM_PROMPT = [
+	'You are a test automation assistant. Given a snapshot of a web page\'s',
+	'accessibility tree and a test step written in natural language, output the',
+	'exact semantic commands needed to execute that step.',
+	'',
+	'Rules:',
+	'- Output ONLY the commands, one per line. No explanation, no markdown.',
+	'- Use SEMANTIC selectors with role and label, NOT element refs.',
+	'  Examples:',
+	'    click button "Send"',
+	'    click textbox "Chat input"',
+	'    click listitem "Today sessions section"',
+	'    click tab "Changes - 3 files changed"',
+	'    click treeitem "build.ts"',
+	'- The format is: <action> <role> "<label>"',
+	'- For typing text, use: type "the text here"',
+	'- For pressing keys, use: press Enter (or other key name)',
+	'- For assertions that something is visible, output: # ASSERT_VISIBLE: the text to check for',
+	'- For assertions that a button is disabled, output: # ASSERT_DISABLED: the button label',
+	'- For assertions that a button is enabled, output: # ASSERT_ENABLED: the button label',
+	'- Icon characters (like codicons from the Unicode Private Use Area) appear in labels.',
+	'  Strip them from your selectors — match by readable text only.',
+	'- For labels with leading/trailing whitespace or icon chars, use only the readable text portion.',
+	'- NEVER use element refs like e43, e155, etc. Always use role "label" selectors.',
+	'- NEVER include dates, times, or timestamps in selectors — they change between runs.',
+	'  Use only the stable portion of the label. For example, instead of:',
+	'    click listitem "Background session explain the code (Completed), created 3/5/2026, 8:48:50 PM"',
+	'  Use:',
+	'    click listitem "explain the code"',
+].join('\n');
+
+// ---------------------------------------------------------------------------
+// Ask Copilot CLI to translate a step
+// ---------------------------------------------------------------------------
+
+function askCopilot(step, snapshot) {
+	const prompt = `Snapshot:\n\`\`\`\n${snapshot}\n\`\`\`\n\nStep: ${step}\n\nOutput the semantic commands:`;
+
+	const result = cp.spawnSync('copilot', ['-p', `${SYSTEM_PROMPT}\n\n${prompt}`, '--model', 'claude-sonnet-4.6'], {
+		cwd: APP_ROOT,
+		stdio: ['ignore', 'pipe', 'pipe'],
+		timeout: 60_000,
+		env: { ...process.env },
+	});
+
+	const stdout = (result.stdout || '').toString().trim();
+	const stderr = (result.stderr || '').toString().trim();
+
+	if (result.status !== 0) {
+		throw new Error(`Copilot CLI failed: ${stderr || stdout}`);
+	}
+
+	return stdout.split('\n')
+		.map(l => l.trim())
+		.filter(l => l.length > 0);
+}
+
+// ---------------------------------------------------------------------------
+// Resolve a semantic command to a ref-based command using a snapshot
+// ---------------------------------------------------------------------------
+
+function resolveSemanticCommand(cmd, snapshotText) {
+	// Match: <action> <role> "<label>"
+	const match = cmd.match(/^(click|focus)\s+(\w+)\s+"([^"]+)"$/);
+	if (!match) { return cmd; }
+
+	const [, action, role, label] = match;
+	const needle = label.replace(/[\uE000-\uF8FF]/g, '').trim().toLowerCase();
+
+	for (const line of snapshotText.split('\n')) {
+		const refMatch = line.match(/\[ref=(e\d+)\]/);
+		if (!refMatch) { continue; }
+		if (!line.includes(role)) { continue; }
+		const labelMatch = line.match(/"([^"]+)"/);
+		if (!labelMatch) { continue; }
+		const lineLabel = labelMatch[1].replace(/[\uE000-\uF8FF]/g, '').trim().toLowerCase();
+		if (lineLabel.includes(needle) || needle.includes(lineLabel)) {
+			return `${action} ${refMatch[1]}`;
+		}
+	}
+
+	// Fallback: return as-is (will likely fail, but gives a clear error)
+	console.error(`    ⚠ Could not resolve: ${cmd}`);
+	return cmd;
+}
+
+// ---------------------------------------------------------------------------
+// Compile a single scenario
+// ---------------------------------------------------------------------------
+
+function compileScenario(scenario) {
+	console.log(`\n▶ Compiling: ${scenario.name}`);
+
+	const compiledSteps = [];
+	for (const [i, step] of scenario.steps.entries()) {
+		console.log(`  step ${i + 1}: ${step}`);
+
+		const snapshot = getSnapshot();
+		if (!snapshot.stdout) {
+			console.error(`    ⚠ Could not get snapshot, skipping step`);
+			compiledSteps.push({ description: step, commands: [], error: 'Failed to get snapshot' });
+			continue;
+		}
+
+		try {
+			const commands = askCopilot(step, snapshot.stdout);
+			console.log(`    → ${commands.join(' ; ')}`);
+
+			compiledSteps.push({ description: step, commands });
+
+			// Execute the commands to advance the UI state for the next step
+			// Resolve semantic selectors to refs using the current snapshot
+			for (const cmd of commands) {
+				if (cmd.startsWith('#')) { continue; }
+				const resolved = resolveSemanticCommand(cmd, snapshot.stdout);
+				if (resolved !== cmd) {
+					console.log(`      [resolve] ${cmd} → ${resolved}`);
+				}
+				const result = runPlaywrightCli(resolved);
+				if (!result.ok) {
+					console.error(`    ⚠ Command failed: ${resolved} — ${result.stderr}`);
+				}
+			}
+
+			cp.spawnSync('sleep', ['1']);
+		} catch (err) {
+			console.error(`    ✗ ${err.message}`);
+			compiledSteps.push({ description: step, commands: [], error: err.message });
+		}
+	}
+
+	return {
+		scenario: scenario.name,
+		generatedAt: new Date().toISOString(),
+		steps: compiledSteps,
+	};
+}
+
+// ---------------------------------------------------------------------------
+// Main
+// ---------------------------------------------------------------------------
+
+async function main() {
+	const filter = process.argv[2] || '';
+	let scenarios = discoverScenarios();
+
+	if (filter) {
+		scenarios = scenarios.filter(s =>
+			s.filePath.includes(filter) || s.name.toLowerCase().includes(filter.toLowerCase())
+		);
+	}
+
+	if (scenarios.length === 0) {
+		console.error('No scenarios found' + (filter ? ` matching "${filter}"` : ''));
+		process.exit(1);
+	}
+
+	console.log(`Found ${scenarios.length} scenario(s) to compile`);
+
+	// Start web server
+	console.log(`Starting sessions web server on port ${PORT}…`);
+	const server = startServer(PORT, { mock: true });
+	await waitForServer(`http://localhost:${PORT}/`, 30_000);
+	console.log('Server ready.');
+
+	// Open browser
+	const openResult = runPlaywrightCli(['open', '--headed']);
+	if (!openResult.ok) {
+		console.error('Failed to open browser:', openResult.stdout, openResult.stderr);
+		cleanup(server);
+		process.exit(1);
+	}
+	const gotoResult = runPlaywrightCli(['goto', BASE_URL]);
+	if (!gotoResult.ok) {
+		console.error('Failed to navigate:', gotoResult.stdout, gotoResult.stderr);
+		cleanup(server);
+		process.exit(1);
+	}
+
+	// Wait for workbench to render
+	cp.spawnSync('sleep', ['5']);
+
+	for (const scenario of scenarios) {
+		// Reset state between scenarios
+		runPlaywrightCli(['press', 'Escape']);
+		runPlaywrightCli(['goto', BASE_URL]);
+		cp.spawnSync('sleep', ['3']);
+
+		const compiled = compileScenario(scenario);
+		const outPath = commandsPathForScenario(scenario.filePath);
+		fs.mkdirSync(path.dirname(outPath), { recursive: true });
+		fs.writeFileSync(outPath, JSON.stringify(compiled, null, '\t') + '\n');
+		console.log(`  ✓ Saved: ${outPath}`);
+	}
+
+	cleanup(server);
+	console.log('\nDone.');
+}
+
+function cleanup(server) {
+	runPlaywrightCli('close');
+	server.kill('SIGTERM');
+}
+
+main();
diff --git a/src/vs/sessions/test/e2e/package-lock.json b/src/vs/sessions/test/e2e/package-lock.json
new file mode 100644
index 0000000000000..f2069d4311896
--- /dev/null
+++ b/src/vs/sessions/test/e2e/package-lock.json
@@ -0,0 +1,84 @@
+{
+	"name": "sessions-e2e-tests",
+	"version": "0.0.1",
+	"lockfileVersion": 3,
+	"requires": true,
+	"packages": {
+		"": {
+			"name": "sessions-e2e-tests",
+			"version": "0.0.1",
+			"dependencies": {
+				"@playwright/cli": "latest"
+			}
+		},
+		"node_modules/@playwright/cli": {
+			"version": "0.1.1",
+			"resolved": "https://registry.npmjs.org/@playwright/cli/-/cli-0.1.1.tgz",
+			"integrity": "sha512-9k11ZfDwAfMVDDIuEVW1Wvs8SoDNXIY1dNQ+9C9/SS8ZmElkcxesu5eoL7vNa96ntibUGaq1TM2qQoqvdl/I9g==",
+			"license": "Apache-2.0",
+			"dependencies": {
+				"minimist": "^1.2.5",
+				"playwright": "1.59.0-alpha-1771104257000"
+			},
+			"bin": {
+				"playwright-cli": "playwright-cli.js"
+			},
+			"engines": {
+				"node": ">=18"
+			}
+		},
+		"node_modules/fsevents": {
+			"version": "2.3.2",
+			"resolved": "https://registry.npmjs.org/fsevents/-/fsevents-2.3.2.tgz",
+			"integrity": "sha512-xiqMQR4xAeHTuB9uWm+fFRcIOgKBMiOBP+eXiyT7jsgVCq1bkVygt00oASowB7EdtpOHaaPgKt812P9ab+DDKA==",
+			"hasInstallScript": true,
+			"license": "MIT",
+			"optional": true,
+			"os": [
+				"darwin"
+			],
+			"engines": {
+				"node": "^8.16.0 || ^10.6.0 || >=11.0.0"
+			}
+		},
+		"node_modules/minimist": {
+			"version": "1.2.8",
+			"resolved": "https://registry.npmjs.org/minimist/-/minimist-1.2.8.tgz",
+			"integrity": "sha512-2yyAR8qBkN3YuheJanUpWC5U3bb5osDywNB8RzDVlDwDHbocAJveqqj1u8+SVD7jkWT4yvsHCpWqqWqAxb0zCA==",
+			"license": "MIT",
+			"funding": {
+				"url": "https://github.com/sponsors/ljharb"
+			}
+		},
+		"node_modules/playwright": {
+			"version": "1.59.0-alpha-1771104257000",
+			"resolved": "https://registry.npmjs.org/playwright/-/playwright-1.59.0-alpha-1771104257000.tgz",
+			"integrity": "sha512-6SCMMMJaDRsSqiKVLmb2nhtLES7iTYawTWWrQK6UdIGNzXi8lka4sLKRec3L4DnTWwddAvCuRn8035dhNiHzbg==",
+			"license": "Apache-2.0",
+			"dependencies": {
+				"playwright-core": "1.59.0-alpha-1771104257000"
+			},
+			"bin": {
+				"playwright": "cli.js"
+			},
+			"engines": {
+				"node": ">=18"
+			},
+			"optionalDependencies": {
+				"fsevents": "2.3.2"
+			}
+		},
+		"node_modules/playwright-core": {
+			"version": "1.59.0-alpha-1771104257000",
+			"resolved": "https://registry.npmjs.org/playwright-core/-/playwright-core-1.59.0-alpha-1771104257000.tgz",
+			"integrity": "sha512-YiXup3pnpQUCBMSIW5zx8CErwRx4K6O5Kojkw2BzJui8MazoMUDU6E3xGsb1kzFviEAE09LFQ+y1a0RhIJQ5SA==",
+			"license": "Apache-2.0",
+			"bin": {
+				"playwright-core": "cli.js"
+			},
+			"engines": {
+				"node": ">=18"
+			}
+		}
+	}
+}
diff --git a/src/vs/sessions/test/e2e/package.json b/src/vs/sessions/test/e2e/package.json
new file mode 100644
index 0000000000000..919efed18ba37
--- /dev/null
+++ b/src/vs/sessions/test/e2e/package.json
@@ -0,0 +1,14 @@
+{
+	"name": "sessions-e2e-tests",
+	"version": "0.0.1",
+	"private": true,
+	"description": "Automated E2E tests for the Agent Sessions window using playwright-cli",
+	"scripts": {
+		"serve": "node ../../../../../scripts/code-sessions-web.js --port 9222 --skip-welcome --mock",
+		"generate": "node generate.cjs",
+		"test": "node test.cjs"
+	},
+	"dependencies": {
+		"@playwright/cli": "latest"
+	}
+}
diff --git a/src/vs/sessions/test/e2e/scenarios/01-chat-response.scenario.md b/src/vs/sessions/test/e2e/scenarios/01-chat-response.scenario.md
new file mode 100644
index 0000000000000..5e40d95d04f6c
--- /dev/null
+++ b/src/vs/sessions/test/e2e/scenarios/01-chat-response.scenario.md
@@ -0,0 +1,6 @@
+# Scenario: Send a chat message and verify response
+
+## Steps
+1. Type "explain the code" in the chat input
+2. Press Enter to submit
+3. Verify there is a chat response
diff --git a/src/vs/sessions/test/e2e/scenarios/02-chat-with-changes.scenario.md b/src/vs/sessions/test/e2e/scenarios/02-chat-with-changes.scenario.md
new file mode 100644
index 0000000000000..3e25a5c3399e3
--- /dev/null
+++ b/src/vs/sessions/test/e2e/scenarios/02-chat-with-changes.scenario.md
@@ -0,0 +1,11 @@
+# Scenario: Chat message produces real file diffs in the changes view
+
+## Steps
+1. Type "build the project" in the chat input
+2. Press Enter to submit
+3. Verify there is a response in the chat
+4. Toggle the secondary side bar
+5. Verify the changes view shows modified files
+6. Click on "index.ts" in the changes list
+7. Verify a diff editor opens with the modified content
+8. Press Escape to close the diff editor
diff --git a/src/vs/sessions/test/e2e/scenarios/03-session-in-sidebar.scenario.md b/src/vs/sessions/test/e2e/scenarios/03-session-in-sidebar.scenario.md
new file mode 100644
index 0000000000000..aededc6ae0bfa
--- /dev/null
+++ b/src/vs/sessions/test/e2e/scenarios/03-session-in-sidebar.scenario.md
@@ -0,0 +1,9 @@
+# Scenario: Session appears in sidebar after sending a message
+
+## Steps
+1. Type "fix the bug" in the chat input
+2. Press Enter to submit
+3. Verify the session appears in the sessions list
+4. Toggle the secondary side bar
+5. Verify the changes view shows the modified file
+
diff --git a/src/vs/sessions/test/e2e/scenarios/04-local-cloud-toggle.scenario.md b/src/vs/sessions/test/e2e/scenarios/04-local-cloud-toggle.scenario.md
new file mode 100644
index 0000000000000..a45b41ea6631e
--- /dev/null
+++ b/src/vs/sessions/test/e2e/scenarios/04-local-cloud-toggle.scenario.md
@@ -0,0 +1,9 @@
+# Scenario: Switch between Local and Cloud mode
+
+## Steps
+1. Click button "Cloud"
+2. Write "hello world" and hit enter
+3. Make sure "Pick Repository" picker opens
+4. Press escape key
+5. Click on button "Local"
+6. Clear chat
diff --git a/src/vs/sessions/test/e2e/scenarios/05-navigate-sessions.scenario.md b/src/vs/sessions/test/e2e/scenarios/05-navigate-sessions.scenario.md
new file mode 100644
index 0000000000000..682fc80e9a301
--- /dev/null
+++ b/src/vs/sessions/test/e2e/scenarios/05-navigate-sessions.scenario.md
@@ -0,0 +1,12 @@
+# Scenario: Navigate between sessions and verify history loads
+
+## Steps
+1. Type "explain the code"
+2. Press Enter to submit
+3. Verify there is a chat response
+4. Click button "New Session"
+5. Type "build the project" in the chat input
+6. Press Enter to submit
+7. Verify there is a chat response
+8. Click on a different session in the sessions list
+9. Verify the session changed and the content in the chat is different
diff --git a/src/vs/sessions/test/e2e/scenarios/06-full-workflow.scenario.md b/src/vs/sessions/test/e2e/scenarios/06-full-workflow.scenario.md
new file mode 100644
index 0000000000000..321446d2af2a8
--- /dev/null
+++ b/src/vs/sessions/test/e2e/scenarios/06-full-workflow.scenario.md
@@ -0,0 +1,25 @@
+# Scenario: Full workflow
+
+## Steps
+1. Type "build the project" in the chat input
+2. Press Enter to submit
+3. Verify there is a response in the chat
+4. Toggle the secondary side bar
+5. Verify the changes view shows "CHANGES" with a badge
+6. Verify "package.json" is visible in the changes list
+7. Verify "build.ts" is visible in the changes list
+8. Verify "index.ts" is visible in the changes list
+9. Click on "index.ts" in the changes list
+10. Verify a diff editor opens with modified content
+11. Press Escape to close the diff editor
+12. Verify "Merge" button is visible in changes view header
+13. Verify the "Open Terminal" button is visible
+14. Click the "Open Terminal" button
+15. Verify the terminal panel becomes visible
+16. Verify the terminal tab shows "session-1" in its label
+17. Click "New Session" to create a new session
+18. Type "fix the bug" in the chat input
+19. Press Enter to submit
+20. Verify the terminal tab label changes to show "session-2"
+21. Click back on the first session in the sessions list
+22. Verify the terminal tab label changes back to show "session-1"
diff --git a/src/vs/sessions/test/e2e/scenarios/generated/.gitkeep b/src/vs/sessions/test/e2e/scenarios/generated/.gitkeep
new file mode 100644
index 0000000000000..e69de29bb2d1d
diff --git a/src/vs/sessions/test/e2e/scenarios/generated/01-chat-response.commands.json b/src/vs/sessions/test/e2e/scenarios/generated/01-chat-response.commands.json
new file mode 100644
index 0000000000000..114c1c5ffd641
--- /dev/null
+++ b/src/vs/sessions/test/e2e/scenarios/generated/01-chat-response.commands.json
@@ -0,0 +1,26 @@
+{
+	"scenario": "Scenario: Send a chat message and verify response",
+	"generatedAt": "2026-03-06T04:23:25.470Z",
+	"steps": [
+		{
+			"description": "Type \"explain the code\" in the chat input",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"type \"explain the code\""
+			]
+		},
+		{
+			"description": "Press Enter to submit",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"press Enter"
+			]
+		},
+		{
+			"description": "Verify there is a chat response",
+			"commands": [
+				"# ASSERT_VISIBLE: This project has a simple structure with a main entry point and utility functions."
+			]
+		}
+	]
+}
diff --git a/src/vs/sessions/test/e2e/scenarios/generated/02-chat-with-changes.commands.json b/src/vs/sessions/test/e2e/scenarios/generated/02-chat-with-changes.commands.json
new file mode 100644
index 0000000000000..a28fabe66896a
--- /dev/null
+++ b/src/vs/sessions/test/e2e/scenarios/generated/02-chat-with-changes.commands.json
@@ -0,0 +1,59 @@
+{
+	"scenario": "Scenario: Chat message produces real file diffs in the changes view",
+	"generatedAt": "2026-03-10T00:00:00.000Z",
+	"note": "Uses semantic selectors — regenerate with 'npm run generate' if UI labels change",
+	"steps": [
+		{
+			"description": "Type \"build the project\" in the chat input",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"type \"build the project\""
+			]
+		},
+		{
+			"description": "Press Enter to submit",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"press Enter"
+			]
+		},
+		{
+			"description": "Verify there is a response in the chat",
+			"commands": [
+				"# ASSERT_VISIBLE: I'll help you build the project. Here are the changes:"
+			]
+		},
+		{
+			"description": "Toggle the secondary side bar",
+			"commands": [
+				"click button \"Toggle Secondary Side Bar\""
+			]
+		},
+		{
+			"description": "Verify the changes view shows modified files",
+			"commands": [
+				"# ASSERT_VISIBLE: index.ts",
+				"# ASSERT_VISIBLE: build.ts",
+				"# ASSERT_VISIBLE: package.json"
+			]
+		},
+		{
+			"description": "Click on \"index.ts\" in the changes list",
+			"commands": [
+				"click treeitem \"index.ts\""
+			]
+		},
+		{
+			"description": "Verify a diff editor opens with the modified content",
+			"commands": [
+				"# ASSERT_VISIBLE: import { build } from"
+			]
+		},
+		{
+			"description": "Press Escape to close the diff editor",
+			"commands": [
+				"press Escape"
+			]
+		}
+	]
+}
diff --git a/src/vs/sessions/test/e2e/scenarios/generated/03-session-in-sidebar.commands.json b/src/vs/sessions/test/e2e/scenarios/generated/03-session-in-sidebar.commands.json
new file mode 100644
index 0000000000000..0013dbc8921a2
--- /dev/null
+++ b/src/vs/sessions/test/e2e/scenarios/generated/03-session-in-sidebar.commands.json
@@ -0,0 +1,39 @@
+{
+	"scenario": "Scenario: Session appears in sidebar after sending a message",
+	"generatedAt": "2026-03-10T00:00:00.000Z",
+	"note": "Uses semantic selectors — regenerate with 'npm run generate' if UI labels change",
+	"steps": [
+		{
+			"description": "Type \"fix the bug\" in the chat input",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"type \"fix the bug\""
+			]
+		},
+		{
+			"description": "Press Enter to submit",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"press Enter"
+			]
+		},
+		{
+			"description": "Verify the session appears in the sessions list",
+			"commands": [
+				"# ASSERT_VISIBLE: fix the bug"
+			]
+		},
+		{
+			"description": "Toggle the secondary side bar",
+			"commands": [
+				"click button \"Toggle Secondary Side Bar\""
+			]
+		},
+		{
+			"description": "Verify the changes view shows the modified file",
+			"commands": [
+				"# ASSERT_VISIBLE: utils.ts"
+			]
+		}
+	]
+}
diff --git a/src/vs/sessions/test/e2e/scenarios/generated/04-local-cloud-toggle.commands.json b/src/vs/sessions/test/e2e/scenarios/generated/04-local-cloud-toggle.commands.json
new file mode 100644
index 0000000000000..dd3d499af9d7c
--- /dev/null
+++ b/src/vs/sessions/test/e2e/scenarios/generated/04-local-cloud-toggle.commands.json
@@ -0,0 +1,47 @@
+{
+	"scenario": "Scenario: Switch between Local and Cloud mode",
+	"generatedAt": "2026-03-06T04:35:09.018Z",
+	"steps": [
+		{
+			"description": "Click button \"Cloud\"",
+			"commands": [
+				"click button \"Cloud\""
+			]
+		},
+		{
+			"description": "Write \"hello world\" and hit enter",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"type \"hello world\"",
+				"press Enter"
+			]
+		},
+		{
+			"description": "Make sure \"Pick Repository\" picker opens",
+			"commands": [
+				"# ASSERT_VISIBLE: Pick Repository",
+				"click listbox \"Repository Picker\""
+			]
+		},
+		{
+			"description": "Press escape key",
+			"commands": [
+				"press Escape"
+			]
+		},
+		{
+			"description": "Click on button \"Local\"",
+			"commands": [
+				"click button \"Local\""
+			]
+		},
+		{
+			"description": "Clear chat",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"press Meta+A",
+				"press Backspace"
+			]
+		}
+	]
+}
diff --git a/src/vs/sessions/test/e2e/scenarios/generated/05-navigate-sessions.commands.json b/src/vs/sessions/test/e2e/scenarios/generated/05-navigate-sessions.commands.json
new file mode 100644
index 0000000000000..95651b7470ce6
--- /dev/null
+++ b/src/vs/sessions/test/e2e/scenarios/generated/05-navigate-sessions.commands.json
@@ -0,0 +1,65 @@
+{
+	"scenario": "Scenario: Navigate between sessions and verify history loads",
+	"generatedAt": "2026-03-06T04:56:01.957Z",
+	"steps": [
+		{
+			"description": "Type \"explain the code\"",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"type \"explain the code\""
+			]
+		},
+		{
+			"description": "Press Enter to submit",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"press Enter"
+			]
+		},
+		{
+			"description": "Verify there is a chat response",
+			"commands": [
+				"# ASSERT_VISIBLE: This project has a simple structure with a main entry point and utility functions."
+			]
+		},
+		{
+			"description": "Click button \"New Session\"",
+			"commands": [
+				"click button \"New Session\""
+			]
+		},
+		{
+			"description": "Type \"build the project\" in the chat input",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"type \"build the project\""
+			]
+		},
+		{
+			"description": "Press Enter to submit",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"press Enter"
+			]
+		},
+		{
+			"description": "Verify there is a chat response",
+			"commands": [
+				"# ASSERT_VISIBLE: I'll help you build the project. Here are the changes:"
+			]
+		},
+		{
+			"description": "Click on a different session in the sessions list",
+			"commands": [
+				"click listitem \"explain the code\""
+			]
+		},
+		{
+			"description": "Verify the session changed and the content in the chat is different",
+			"commands": [
+				"# ASSERT_VISIBLE: explain the code",
+				"# ASSERT_VISIBLE: This project has a simple structure with a main entry point and utility functions."
+			]
+		}
+	]
+}
diff --git a/src/vs/sessions/test/e2e/scenarios/generated/06-full-workflow.commands.json b/src/vs/sessions/test/e2e/scenarios/generated/06-full-workflow.commands.json
new file mode 100644
index 0000000000000..5124b5d6d2d63
--- /dev/null
+++ b/src/vs/sessions/test/e2e/scenarios/generated/06-full-workflow.commands.json
@@ -0,0 +1,140 @@
+{
+	"scenario": "Scenario: Full workflow",
+	"generatedAt": "2026-03-12T22:48:50.725Z",
+	"steps": [
+		{
+			"description": "Type \"build the project\" in the chat input",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"type \"build the project\""
+			]
+		},
+		{
+			"description": "Press Enter to submit",
+			"commands": [
+				"press Enter"
+			]
+		},
+		{
+			"description": "Verify there is a response in the chat",
+			"commands": [
+				"# ASSERT_VISIBLE: I'll help you build the project. Here are the changes:"
+			]
+		},
+		{
+			"description": "Toggle the secondary side bar",
+			"commands": [
+				"click button \"Toggle Secondary Side Bar Visibility\""
+			]
+		},
+		{
+			"description": "Verify the changes view shows \"CHANGES\" with a badge",
+			"commands": [
+				"# ASSERT_VISIBLE: Changes - 3 files changed"
+			]
+		},
+		{
+			"description": "Verify \"package.json\" is visible in the changes list",
+			"commands": [
+				"# ASSERT_VISIBLE: package.json"
+			]
+		},
+		{
+			"description": "Verify \"build.ts\" is visible in the changes list",
+			"commands": [
+				"# ASSERT_VISIBLE: build.ts"
+			]
+		},
+		{
+			"description": "Verify \"index.ts\" is visible in the changes list",
+			"commands": [
+				"# ASSERT_VISIBLE: index.ts"
+			]
+		},
+		{
+			"description": "Click on \"index.ts\" in the changes list",
+			"commands": [
+				"click treeitem \"index.ts\""
+			]
+		},
+		{
+			"description": "Verify a diff editor opens with modified content",
+			"commands": [
+				"# ASSERT_VISIBLE: index.ts"
+			]
+		},
+		{
+			"description": "Press Escape to close the diff editor",
+			"commands": [
+				"press Escape"
+			]
+		},
+		{
+			"description": "Verify \"Merge\" button is visible in changes view header",
+			"commands": [
+				"# ASSERT_VISIBLE: Merge"
+			]
+		},
+		{
+			"description": "Verify the \"Open Terminal\" button is visible",
+			"commands": [
+				"# ASSERT_VISIBLE: Open Terminal"
+			]
+		},
+		{
+			"description": "Click the \"Open Terminal\" button",
+			"commands": [
+				"click button \"Open Terminal\""
+			]
+		},
+		{
+			"description": "Verify the terminal panel becomes visible",
+			"commands": [
+				"# ASSERT_VISIBLE: Terminal"
+			]
+		},
+		{
+			"description": "Verify the terminal tab shows \"session-1\" in its label",
+			"commands": [
+				"# ASSERT_VISIBLE: bash - session-1"
+			]
+		},
+		{
+			"description": "Click \"New Session\" to create a new session",
+			"commands": [
+				"click button \"New Session\""
+			]
+		},
+		{
+			"description": "Type \"fix the bug\" in the chat input",
+			"commands": [
+				"click textbox \"Chat input\"",
+				"type \"fix the bug\""
+			]
+		},
+		{
+			"description": "Press Enter to submit",
+			"commands": [
+				"press Enter"
+			]
+		},
+		{
+			"description": "Verify the terminal tab label changes to show \"session-2\"",
+			"commands": [
+				"# ASSERT_VISIBLE: bash - session-2"
+			]
+		},
+		{
+			"description": "Click back on the first session in the sessions list",
+			"commands": [
+				"click listitem \"build the project\""
+			]
+		},
+		{
+			"description": "Verify the terminal tab label changes back to show \"session-1\"",
+			"commands": [
+				"# ASSERT_VISIBLE: bash - session-1"
+			]
+		}
+	]
+}
diff --git a/src/vs/sessions/test/e2e/test.cjs b/src/vs/sessions/test/e2e/test.cjs
new file mode 100644
index 0000000000000..458c0c3653359
--- /dev/null
+++ b/src/vs/sessions/test/e2e/test.cjs
@@ -0,0 +1,297 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+// @ts-check
+
+/**
+ * Deterministic test runner — replays .commands.json files generated by generate.cjs.
+ *
+ * No LLM calls. Just sequential playwright-cli commands and assertions.
+ *
+ * Usage:
+ *   node test.cjs                    # run all compiled scenarios
+ *   node test.cjs 01-repo-picker     # run matching scenario(s)
+ */
+
+const fs = require('fs');
+const path = require('path');
+const cp = require('child_process');
+const {
+	APP_ROOT,
+	SCENARIOS_DIR,
+	runPlaywrightCli,
+	getSnapshot,
+	startServer,
+	waitForServer,
+} = require('./common.cjs');
+
+const PORT = 9100 + Math.floor(Math.random() * 900);
+const BASE_URL = `http://localhost:${PORT}/?skip-sessions-welcome`;
+
+// ---------------------------------------------------------------------------
+// Discover compiled command files
+// ---------------------------------------------------------------------------
+
+function discoverCommandFiles(filter) {
+	const compiledDir = path.join(SCENARIOS_DIR, 'generated');
+	if (!fs.existsSync(compiledDir)) { return []; }
+	return fs.readdirSync(compiledDir)
+		.filter(f => f.endsWith('.commands.json'))
+		.filter(f => !filter || f.includes(filter))
+		.sort()
+		.map(f => path.join(compiledDir, f));
+}
+
+// ---------------------------------------------------------------------------
+// Normalize label for assertion matching (strip codicons + trim + lowercase)
+// ---------------------------------------------------------------------------
+
+function normalizeLabel(text) {
+	return text.replace(/[\uE000-\uF8FF]/g, '').trim().toLowerCase();
+}
+
+// ---------------------------------------------------------------------------
+// Semantic command resolver — resolves role+label selectors to current refs
+// ---------------------------------------------------------------------------
+
+/**
+ * Resolve a semantic command like `click button "Send"` to a ref-based
+ * command like `click e170` using a fresh snapshot of the current page.
+ *
+ * Commands that don't match the semantic pattern (type, press, comments)
+ * are returned as-is.
+ */
+function resolveSemanticCommand(cmd, snapshotText) {
+	// Match: <action> <role> "<label>"
+	const match = cmd.match(/^(click|focus)\s+(\w+)\s+"([^"]+)"$/);
+	if (!match) { return { resolved: cmd, ok: true }; }
+
+	const [, action, role, label] = match;
+	const needle = normalizeLabel(label);
+
+	for (const line of snapshotText.split('\n')) {
+		const refMatch = line.match(/\[ref=(e\d+)\]/);
+		if (!refMatch) { continue; }
+		if (!line.includes(role)) { continue; }
+		const labelMatch = line.match(/"([^"]+)"/);
+		if (!labelMatch) { continue; }
+		const lineLabel = normalizeLabel(labelMatch[1]);
+		if (lineLabel.includes(needle) || needle.includes(lineLabel)) {
+			return { resolved: `${action} ${refMatch[1]}`, ok: true };
+		}
+	}
+
+	return { resolved: cmd, ok: false, message: `Could not find ${role} "${label}" in snapshot` };
+}
+
+// ---------------------------------------------------------------------------
+// Polling helper — retries a check function until it passes or times out
+// ---------------------------------------------------------------------------
+
+const ASSERT_TIMEOUT_MS = 10_000;
+const ASSERT_POLL_MS = 500;
+
+/**
+ * @param {() => { ok: boolean; message?: string }} checkFn
+ * @returns {{ ok: boolean; message?: string }}
+ */
+function pollAssertion(checkFn) {
+	const deadline = Date.now() + ASSERT_TIMEOUT_MS;
+	let lastResult = checkFn();
+	while (!lastResult.ok && Date.now() < deadline) {
+		cp.spawnSync('sleep', [(ASSERT_POLL_MS / 1000).toString()]);
+		lastResult = checkFn();
+	}
+	return lastResult;
+}
+
+// ---------------------------------------------------------------------------
+// Execute a single command line and handle assertions
+// ---------------------------------------------------------------------------
+
+function executeCommand(cmd) {
+	// Assertion comments — poll with retries to handle async rendering
+	if (cmd.startsWith('# ASSERT_VISIBLE:')) {
+		const text = cmd.slice('# ASSERT_VISIBLE:'.length).trim();
+		return pollAssertion(() => {
+			const snap = getSnapshot();
+			if (!snap.stdout) { return { ok: false, message: 'Failed to get snapshot for assertion' }; }
+			if (!snap.stdout.toLowerCase().includes(text.toLowerCase())) {
+				return { ok: false, message: `Expected "${text}" to be visible in snapshot` };
+			}
+			return { ok: true };
+		});
+	}
+
+	if (cmd.startsWith('# ASSERT_DISABLED:')) {
+		const label = cmd.slice('# ASSERT_DISABLED:'.length).trim();
+		return pollAssertion(() => {
+			const snap = getSnapshot();
+			if (!snap.stdout) { return { ok: false, message: 'Failed to get snapshot for assertion' }; }
+			const needle = normalizeLabel(label);
+			const buttonLine = snap.stdout.split('\n').find(l =>
+				l.includes('button') && l.match(/"([^"]+)"/) &&
+				normalizeLabel(l.match(/"([^"]+)"/)[1]) === needle
+			);
+			if (!buttonLine) { return { ok: false, message: `Button "${label}" not found in snapshot` }; }
+			if (!buttonLine.includes('[disabled]')) {
+				return { ok: false, message: `Expected button "${label}" to be disabled` };
+			}
+			return { ok: true };
+		});
+	}
+
+	if (cmd.startsWith('# ASSERT_ENABLED:')) {
+		const label = cmd.slice('# ASSERT_ENABLED:'.length).trim();
+		return pollAssertion(() => {
+			const snap = getSnapshot();
+			if (!snap.stdout) { return { ok: false, message: 'Failed to get snapshot for assertion' }; }
+			const needle = normalizeLabel(label);
+			const buttonLine = snap.stdout.split('\n').find(l =>
+				l.includes('button') && l.match(/"([^"]+)"/) &&
+				normalizeLabel(l.match(/"([^"]+)"/)[1]) === needle
+			);
+			if (!buttonLine) { return { ok: false, message: `Button "${label}" not found in snapshot` }; }
+			if (buttonLine.includes('[disabled]')) {
+				return { ok: false, message: `Expected button "${label}" to be enabled` };
+			}
+			return { ok: true };
+		});
+	}
+
+	// Skip other comments
+	if (cmd.startsWith('#')) { return { ok: true }; }
+
+	// Semantic commands (e.g. `click button "Send"`) — resolve to ref from live snapshot
+	const semanticMatch = cmd.match(/^(click|focus)\s+\w+\s+"[^"]+"$/);
+	if (semanticMatch) {
+		// Poll: the element might not be rendered yet
+		return pollAssertion(() => {
+			const snap = getSnapshot();
+			if (!snap.stdout) { return { ok: false, message: 'Failed to get snapshot for command resolution' }; }
+			const { resolved, ok, message } = resolveSemanticCommand(cmd, snap.stdout);
+			if (!ok) { return { ok: false, message: message || `Could not resolve: ${cmd}` }; }
+			console.log(`    [resolve] ${cmd} → ${resolved}`);
+			const result = runPlaywrightCli(resolved);
+			if (!result.ok) {
+				return { ok: false, message: `playwright-cli ${resolved} failed:\n${result.stderr || result.stdout}` };
+			}
+			return { ok: true };
+		});
+	}
+
+	// Regular playwright-cli command (type, press, snapshot, etc.)
+	const result = runPlaywrightCli(cmd);
+	if (!result.ok) {
+		return { ok: false, message: `playwright-cli ${cmd} failed:\n${result.stderr || result.stdout}` };
+	}
+	return { ok: true };
+}
+
+// ---------------------------------------------------------------------------
+// Main
+// ---------------------------------------------------------------------------
+
+async function main() {
+	const filter = process.argv[2] || '';
+	const commandFiles = discoverCommandFiles(filter);
+
+	if (commandFiles.length === 0) {
+		console.error('No .commands.json files found' + (filter ? ` matching "${filter}"` : ''));
+		console.error('Run "npm run generate" first to compile scenarios.');
+		process.exit(1);
+	}
+
+	console.log(`Found ${commandFiles.length} compiled scenario(s)\n`);
+
+	// Start web server
+	console.log(`Starting sessions web server on port ${PORT}…`);
+	const server = startServer(PORT, { mock: true });
+	await waitForServer(`http://localhost:${PORT}/`, 30_000);
+	console.log('Server ready.\n');
+
+	// Open browser
+	// --headed if you want to run the test locally and verify the UI interactions
+	// const openResult = runPlaywrightCli(['open', '--headed']);
+	const openResult = runPlaywrightCli(['open', '--headed']);
+	if (!openResult.ok) {
+		console.error('Failed to open browser:', openResult.stdout, openResult.stderr);
+		cleanup(server);
+		process.exit(1);
+	}
+	const gotoResult = runPlaywrightCli(['goto', BASE_URL]);
+	if (!gotoResult.ok) {
+		console.error('Failed to navigate:', gotoResult.stdout, gotoResult.stderr);
+		cleanup(server);
+		process.exit(1);
+	}
+
+	// Wait for workbench to render
+	cp.spawnSync('sleep', ['5']);
+
+	let totalPassed = 0;
+	let totalFailed = 0;
+
+	for (const filePath of commandFiles) {
+		const data = JSON.parse(fs.readFileSync(filePath, 'utf-8'));
+		console.log(`▶ ${data.scenario}`);
+
+		// Reset state between scenarios
+		runPlaywrightCli(['press', 'Escape']);
+		runPlaywrightCli(['goto', BASE_URL]);
+		cp.spawnSync('sleep', ['3']);
+
+		let scenarioPassed = true;
+
+		for (const [i, step] of data.steps.entries()) {
+			// Give the UI time to settle after each step (matches generate.cjs behavior)
+			cp.spawnSync('sleep', ['1']);
+			const label = `  step ${i + 1}: ${step.description}`;
+
+			if (step.error) {
+				console.error(`  ❌ ${label}`);
+				console.error(`     Compilation error: ${step.error}`);
+				totalFailed++;
+				scenarioPassed = false;
+				continue;
+			}
+
+			let stepPassed = true;
+			for (const cmd of step.commands) {
+				const result = executeCommand(cmd);
+				if (!result.ok) {
+					console.error(`  ❌ ${label}`);
+					console.error(`     ${result.message}`);
+					// Screenshot on failure
+					const basename = path.basename(filePath, '.commands.json');
+					runPlaywrightCli(`screenshot --filename=out/failure-${basename}-step${i + 1}.png`);
+					totalFailed++;
+					stepPassed = false;
+					scenarioPassed = false;
+					break;
+				}
+			}
+
+			if (stepPassed) {
+				console.log(`  ✅ ${label}`);
+				totalPassed++;
+			}
+		}
+
+		console.log();
+	}
+
+	cleanup(server);
+
+	console.log(`Results: ${totalPassed} passed, ${totalFailed} failed`);
+	process.exit(totalFailed > 0 ? 1 : 0);
+}
+
+function cleanup(server) {
+	runPlaywrightCli('close');
+	server.kill('SIGTERM');
+}
+
+main();
diff --git a/src/vs/sessions/test/sessions.web.test.internal.ts b/src/vs/sessions/test/sessions.web.test.internal.ts
new file mode 100644
index 0000000000000..7573c7421ebc2
--- /dev/null
+++ b/src/vs/sessions/test/sessions.web.test.internal.ts
@@ -0,0 +1,23 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+// Test entry point for the Sessions workbench with mock services.
+// Mirrors sessions.web.main.internal.ts but uses TestSessionsBrowserMain.
+
+import '../sessions.web.main.js';
+import { create } from './web.test.factory.js';
+import { URI } from '../../base/common/uri.js';
+import { Event, Emitter } from '../../base/common/event.js';
+import { Disposable } from '../../base/common/lifecycle.js';
+import { LogLevel } from '../../platform/log/common/log.js';
+
+export {
+	create,
+	URI,
+	Event,
+	Emitter,
+	Disposable,
+	LogLevel,
+};
diff --git a/src/vs/sessions/test/web.test.factory.ts b/src/vs/sessions/test/web.test.factory.ts
new file mode 100644
index 0000000000000..1889be32753da
--- /dev/null
+++ b/src/vs/sessions/test/web.test.factory.ts
@@ -0,0 +1,34 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { IWorkbench, IWorkbenchConstructionOptions } from '../../workbench/browser/web.api.js';
+import { TestSessionsBrowserMain } from './web.test.js';
+import { IDisposable, toDisposable } from '../../base/common/lifecycle.js';
+import { mark } from '../../base/common/performance.js';
+import { DeferredPromise } from '../../base/common/async.js';
+
+const workbenchPromise = new DeferredPromise<IWorkbench>();
+
+/**
+ * Creates the Sessions workbench with mock services for E2E testing.
+ */
+export function create(domElement: HTMLElement, options: IWorkbenchConstructionOptions): IDisposable {
+
+	mark('code/didLoadWorkbenchMain');
+
+	let instantiatedWorkbench: IWorkbench | undefined = undefined;
+	new TestSessionsBrowserMain(domElement, options).open().then(workbench => {
+		instantiatedWorkbench = workbench;
+		workbenchPromise.complete(workbench);
+	});
+
+	return toDisposable(() => {
+		if (instantiatedWorkbench) {
+			instantiatedWorkbench.shutdown();
+		} else {
+			workbenchPromise.p.then(w => w.shutdown());
+		}
+	});
+}
diff --git a/src/vs/sessions/test/web.test.ts b/src/vs/sessions/test/web.test.ts
new file mode 100644
index 0000000000000..760fd0000a05d
--- /dev/null
+++ b/src/vs/sessions/test/web.test.ts
@@ -0,0 +1,543 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { ServiceCollection } from '../../platform/instantiation/common/serviceCollection.js';
+import { ILogService } from '../../platform/log/common/log.js';
+import { IBrowserMainWorkbench } from '../../workbench/browser/web.main.js';
+import { Workbench as SessionsWorkbench } from '../browser/workbench.js';
+import { SessionsBrowserMain } from '../browser/web.main.js';
+import { Emitter, Event } from '../../base/common/event.js';
+import { CancellationToken } from '../../base/common/cancellation.js';
+import { IObservable, observableValue } from '../../base/common/observable.js';
+import { ChatEntitlement, IChatEntitlementService, IChatSentiment } from '../../workbench/services/chat/common/chatEntitlementService.js';
+import { IDefaultAccountService } from '../../platform/defaultAccount/common/defaultAccount.js';
+import { IDefaultAccount, IDefaultAccountAuthenticationProvider, ICopilotTokenInfo, IPolicyData } from '../../base/common/defaultAccount.js';
+import { IChatAgentService, IChatAgentData, IChatAgentImplementation } from '../../workbench/contrib/chat/common/participants/chatAgents.js';
+import { ChatAgentLocation, ChatModeKind } from '../../workbench/contrib/chat/common/constants.js';
+import { ExtensionIdentifier } from '../../platform/extensions/common/extensions.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../platform/storage/common/storage.js';
+import { URI } from '../../base/common/uri.js';
+import { Disposable } from '../../base/common/lifecycle.js';
+import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../workbench/common/contributions.js';
+import { IChatProgress } from '../../workbench/contrib/chat/common/chatService/chatService.js';
+import { IChatSessionsService, IChatSessionItem, IChatSessionFileChange, ChatSessionStatus, IChatSessionHistoryItem, IChatSessionItemsDelta } from '../../workbench/contrib/chat/common/chatSessionsService.js';
+import { IGitService, IGitExtensionDelegate, IGitRepository } from '../../workbench/contrib/git/common/gitService.js';
+import { IFileService } from '../../platform/files/common/files.js';
+import { ITerminalService } from '../../workbench/contrib/terminal/browser/terminal.js';
+import { ITerminalBackend, ITerminalBackendRegistry, IProcessReadyEvent, IProcessProperty, ProcessPropertyType, TerminalExtensions, ITerminalProcessOptions, IShellLaunchConfig } from '../../platform/terminal/common/terminal.js';
+import { IProcessEnvironment } from '../../base/common/platform.js';
+import { Registry } from '../../platform/registry/common/platform.js';
+import { InMemoryFileSystemProvider } from '../../platform/files/common/inMemoryFilesystemProvider.js';
+import { VSBuffer } from '../../base/common/buffer.js';
+
+/**
+ * Mock files pre-seeded in the in-memory file system. These match the
+ * paths in EXISTING_MOCK_FILES and are used by the ChatEditingService
+ * to compute before/after diffs.
+ */
+const MOCK_FS_FILES: Record<string, string> = {
+	'/mock-repo/src/index.ts': 'export function main() {\n\tconsole.log("Hello from mock repo");\n}\n',
+	'/mock-repo/src/utils.ts': 'export function add(a: number, b: number): number {\n\treturn a + b;\n}\n',
+	'/mock-repo/package.json': '{\n\t"name": "mock-repo",\n\t"version": "1.0.0"\n}\n',
+	'/mock-repo/README.md': '# Mock Repository\n\nThis is a mock repository for E2E testing.\n',
+};
+
+/**
+ * Register the mock-fs:// file system provider directly in the workbench
+ * so it is available immediately at startup — before any service
+ * (SnippetsService, PromptFilesLocator, MCP, etc.) tries to resolve
+ * files inside the workspace folder.
+ */
+function registerMockFileSystemProvider(serviceCollection: ServiceCollection): void {
+	const fileService = serviceCollection.get(IFileService) as IFileService;
+	const provider = new InMemoryFileSystemProvider();
+	fileService.registerProvider('mock-fs', provider);
+
+	// Pre-populate the files so ChatEditingService can read originals for diffs
+	for (const [filePath, content] of Object.entries(MOCK_FS_FILES)) {
+		const uri = URI.from({ scheme: 'mock-fs', authority: 'mock-repo', path: filePath });
+		fileService.writeFile(uri, VSBuffer.fromString(content));
+	}
+	console.log('[Sessions Web Test] Registered mock-fs:// provider with pre-seeded files');
+}
+
+const MOCK_ACCOUNT: IDefaultAccount = {
+	authenticationProvider: { id: 'github', name: 'GitHub (Mock)', enterprise: false },
+	accountName: 'e2e-test-user',
+	sessionId: 'mock-session-1',
+	enterprise: false,
+};
+
+/**
+ * Mock implementation of IChatEntitlementService that makes the Sessions
+ * window think the user is signed in with a Free Copilot plan.
+ */
+class MockChatEntitlementService implements IChatEntitlementService {
+
+	declare readonly _serviceBrand: undefined;
+
+	readonly onDidChangeEntitlement = Event.None;
+	readonly onDidChangeQuotaExceeded = Event.None;
+	readonly onDidChangeQuotaRemaining = Event.None;
+	readonly onDidChangeSentiment = Event.None;
+	readonly onDidChangeAnonymous = Event.None;
+
+	readonly entitlement = ChatEntitlement.Free;
+	readonly entitlementObs: IObservable<ChatEntitlement> = observableValue('entitlement', ChatEntitlement.Free);
+
+	readonly previewFeaturesDisabled = false;
+	readonly organisations: string[] | undefined = undefined;
+	readonly isInternal = false;
+	readonly sku = 'free';
+	readonly copilotTrackingId = 'mock-tracking-id';
+
+	readonly quotas = {};
+
+	readonly sentiment: IChatSentiment = { installed: true, registered: true };
+	readonly sentimentObs: IObservable<IChatSentiment> = observableValue('sentiment', { installed: true, registered: true });
+
+	readonly anonymous = false;
+	readonly anonymousObs: IObservable<boolean> = observableValue('anonymous', false);
+
+	markAnonymousRateLimited(): void { }
+	async update(_token: CancellationToken): Promise<void> { }
+}
+
+/**
+ * Mock implementation of IDefaultAccountService that returns a fake
+ * signed-in account so the "Sign In" button in the sidebar is hidden.
+ */
+class MockDefaultAccountService implements IDefaultAccountService {
+
+	declare readonly _serviceBrand: undefined;
+
+	readonly onDidChangeDefaultAccount = Event.None;
+	readonly onDidChangePolicyData = Event.None;
+	readonly policyData: IPolicyData | null = null;
+	readonly copilotTokenInfo: ICopilotTokenInfo | null = null;
+	readonly onDidChangeCopilotTokenInfo = Event.None;
+
+	async getDefaultAccount(): Promise<IDefaultAccount | null> { return MOCK_ACCOUNT; }
+	getDefaultAccountAuthenticationProvider(): IDefaultAccountAuthenticationProvider { return MOCK_ACCOUNT.authenticationProvider; }
+	setDefaultAccountProvider(): void { }
+	async refresh(): Promise<IDefaultAccount | null> { return MOCK_ACCOUNT; }
+	async signIn(): Promise<IDefaultAccount | null> { return MOCK_ACCOUNT; }
+	async signOut(): Promise<void> { }
+}
+
+// ---------------------------------------------------------------------------
+// Mock chat responses and file changes
+// ---------------------------------------------------------------------------
+
+/**
+ * Paths that exist in the mock-fs file store pre-seeded by the mock extension.
+ * Used to determine whether a textEdit should replace file content (existing)
+ * or insert into an empty buffer (new file), so the real ChatEditingService
+ * computes meaningful before/after diffs.
+ */
+const EXISTING_MOCK_FILES = new Set(['/mock-repo/src/index.ts', '/mock-repo/src/utils.ts', '/mock-repo/package.json', '/mock-repo/README.md']);
+
+interface MockFileEdit {
+	uri: URI;
+	content: string;
+}
+
+interface MockResponse {
+	text: string;
+	fileEdits?: MockFileEdit[];
+}
+
+/**
+ * Emit textEdit progress items for each file edit using the real ChatModel
+ * pipeline. Existing files use a full-file replacement range so the real
+ * ChatEditingService computes an accurate diff. New files use an
+ * insert-at-beginning range.
+ */
+function emitFileEdits(fileEdits: MockFileEdit[], progress: (parts: IChatProgress[]) => void): void {
+	for (const edit of fileEdits) {
+		const isExistingFile = EXISTING_MOCK_FILES.has(edit.uri.path);
+		const range = isExistingFile
+			? { startLineNumber: 1, startColumn: 1, endLineNumber: 99999, endColumn: 1 }
+			: { startLineNumber: 1, startColumn: 1, endLineNumber: 1, endColumn: 1 };
+		console.log(`[Sessions Web Test] Emitting textEdit for ${edit.uri.toString()} (existing: ${isExistingFile}, range: ${range.startLineNumber}-${range.endLineNumber})`);
+		progress([{
+			kind: 'textEdit',
+			uri: edit.uri,
+			edits: [{ range, text: edit.content }],
+			done: true,
+		}]);
+	}
+}
+
+/**
+ * Return canned response text and file edits keyed by user message keywords.
+ *
+ * File edits target URIs in the mock-fs:// filesystem. Edits for existing
+ * files produce real diffs (original content from mock-fs → new content here).
+ * Edits for new files produce "file created" entries.
+ */
+function getMockResponseWithEdits(message: string): MockResponse {
+	if (/build|compile|create/i.test(message)) {
+		return {
+			text: 'I\'ll help you build the project. Here are the changes:',
+			fileEdits: [
+				{
+					// Modify existing file — adds build import + call
+					uri: URI.from({ scheme: 'mock-fs', authority: 'mock-repo', path: '/mock-repo/src/index.ts' }),
+					content: 'import { build } from "./build";\n\nexport function main() {\n\tconsole.log("Hello from mock repo");\n\tbuild();\n}\n',
+				},
+				{
+					// New file — creates build script
+					uri: URI.from({ scheme: 'mock-fs', authority: 'mock-repo', path: '/mock-repo/src/build.ts' }),
+					content: 'export async function build() {\n\tconsole.log("Building...");\n\tconsole.log("Build complete!");\n}\n',
+				},
+				{
+					// Modify existing file — adds build script
+					uri: URI.from({ scheme: 'mock-fs', authority: 'mock-repo', path: '/mock-repo/package.json' }),
+					content: '{\n\t"name": "mock-repo",\n\t"version": "1.0.0",\n\t"scripts": {\n\t\t"build": "node src/build.ts"\n\t}\n}\n',
+				},
+			],
+		};
+	}
+	if (/fix|bug/i.test(message)) {
+		return {
+			text: 'I found the issue and applied the fix. The input validation has been added.',
+			fileEdits: [
+				{
+					// Modify existing file — adds input validation
+					uri: URI.from({ scheme: 'mock-fs', authority: 'mock-repo', path: '/mock-repo/src/utils.ts' }),
+					content: 'export function add(a: number, b: number): number {\n\tif (typeof a !== "number" || typeof b !== "number") {\n\t\tthrow new TypeError("Both arguments must be numbers");\n\t}\n\treturn a + b;\n}\n',
+				},
+			],
+		};
+	}
+	if (/explain|describe/i.test(message)) {
+		return {
+			text: 'This project has a simple structure with a main entry point and utility functions.',
+		};
+	}
+	return {
+		text: 'I understand your request. Let me work on that.\n\n1. Review the codebase\n2. Make changes\n3. Run tests',
+	};
+}
+
+// ---------------------------------------------------------------------------
+// Workbench contribution — registers mock chat agent and pre-seeds folder
+// ---------------------------------------------------------------------------
+
+class MockChatAgentContribution extends Disposable implements IWorkbenchContribution {
+
+	static readonly ID = 'sessions.test.mockChatAgent';
+
+	private readonly _sessionItems: IChatSessionItem[] = [];
+	private readonly _itemsChangedEmitter = new Emitter<IChatSessionItemsDelta>();
+	private readonly _sessionHistory = new Map<string, IChatSessionHistoryItem[]>();
+	private _worktreeCounter = 0;
+
+	constructor(
+		@IChatAgentService private readonly chatAgentService: IChatAgentService,
+		@IStorageService private readonly storageService: IStorageService,
+		@IChatSessionsService private readonly chatSessionsService: IChatSessionsService,
+		@ITerminalService private readonly terminalService: ITerminalService,
+	) {
+		super();
+		this._register(this._itemsChangedEmitter);
+		this.registerMockAgents();
+		this.registerMockSessionProvider();
+		this.registerMockTerminalBackend();
+		this.preseedFolder();
+	}
+
+	/**
+	 * Track a session for sidebar display and history re-opening.
+	 *
+	 * Populates `IChatSessionItem.changes` with file change metadata so the
+	 * ChangesViewPane can render them for background (copilotcli) sessions.
+	 * Background sessions read changes from `IAgentSessionsService.model`
+	 * which flows through from `IChatSessionItemController.items`.
+	 */
+	private addSessionItem(resource: URI, message: string, responseText: string, fileEdits?: MockFileEdit[]): void {
+		const key = resource.toString();
+		const now = Date.now();
+
+		// Store conversation history for this session (needed for re-opening)
+		if (!this._sessionHistory.has(key)) {
+			this._sessionHistory.set(key, []);
+		}
+		this._sessionHistory.get(key)!.push(
+			{ type: 'request', prompt: message, participant: 'copilot' },
+			{ type: 'response', parts: [{ kind: 'markdownContent', content: { value: responseText, isTrusted: false, supportThemeIcons: false, supportHtml: false } }], participant: 'copilot' },
+		);
+
+		// Build file changes for the session list (used by ChangesViewPane for background sessions)
+		const changes: IChatSessionFileChange[] | undefined = fileEdits?.map(edit => ({
+			modifiedUri: edit.uri,
+			insertions: edit.content.split('\n').length,
+			deletions: EXISTING_MOCK_FILES.has(edit.uri.path) ? 1 : 0,
+		}));
+
+		// Add or update session in list
+		const existing = this._sessionItems.find(s => s.resource.toString() === key);
+		let addedOrUpdated: IChatSessionItem | undefined = existing;
+		if (existing) {
+			existing.timing.lastRequestStarted = now;
+			existing.timing.lastRequestEnded = now;
+			if (changes) {
+				existing.changes = changes;
+			}
+		} else {
+			addedOrUpdated = {
+				resource,
+				label: message.slice(0, 50) || 'Mock Session',
+				status: ChatSessionStatus.Completed,
+				timing: { created: now, lastRequestStarted: now, lastRequestEnded: now },
+				metadata: { worktreePath: `/mock-worktrees/session-${++this._worktreeCounter}` },
+				...(changes ? { changes } : {}),
+			};
+			this._sessionItems.push(addedOrUpdated);
+		}
+
+		if (addedOrUpdated) {
+			this._itemsChangedEmitter.fire({ addedOrUpdated: [addedOrUpdated] });
+		}
+	}
+
+	private registerMockAgents(): void {
+		const agentIds = ['copilotcli', 'copilot-cloud-agent'];
+		const extensionId = new ExtensionIdentifier('vscode.sessions-e2e-mock');
+		const self = this;
+
+		for (const agentId of agentIds) {
+			const agentData: IChatAgentData = {
+				id: agentId,
+				name: agentId,
+				fullName: `Mock Agent (${agentId})`,
+				description: 'Mock chat agent for E2E testing',
+				extensionId,
+				extensionVersion: '0.0.1',
+				extensionPublisherId: 'vscode',
+				extensionDisplayName: 'Sessions E2E Mock',
+				isDefault: agentId === 'copilotcli',
+				metadata: {},
+				slashCommands: [],
+				locations: [ChatAgentLocation.Chat],
+				modes: [ChatModeKind.Agent],
+				disambiguation: [],
+			};
+
+			const agentImpl: IChatAgentImplementation = {
+				async invoke(request, progress: (parts: IChatProgress[]) => void, _history, _token) {
+					console.log(`[Sessions Web Test] Mock agent "${agentId}" invoked: "${request.message}"`);
+					const response = getMockResponseWithEdits(request.message);
+
+					// Stream the text response
+					progress([{
+						kind: 'markdownContent',
+						content: { value: response.text, isTrusted: false, supportThemeIcons: false, supportHtml: false },
+					}]);
+
+					// Emit file edits through the real ChatModel pipeline so
+					// ChatEditingService computes actual diffs
+					if (response.fileEdits) {
+						emitFileEdits(response.fileEdits, progress);
+						console.log(`[Sessions Web Test] Emitted ${response.fileEdits.length} file edits`);
+					}
+
+					self.addSessionItem(request.sessionResource, request.message, response.text, response.fileEdits);
+					return { metadata: { mock: true } };
+				},
+			};
+
+			try {
+				this._register(this.chatAgentService.registerDynamicAgent(agentData, agentImpl));
+				console.log(`[Sessions Web Test] Registered mock agent: ${agentId}`);
+			} catch (err) {
+				console.warn(`[Sessions Web Test] Failed to register agent ${agentId}:`, err);
+			}
+		}
+	}
+
+	private registerMockSessionProvider(): void {
+		const schemes = ['copilotcli', 'copilot-cloud-agent'];
+		const self = this;
+		for (const scheme of schemes) {
+			try {
+				this._register(this.chatSessionsService.registerChatSessionContentProvider(scheme, {
+					async provideChatSessionContent(sessionResource, _token) {
+						const key = sessionResource.toString();
+						const history = self._sessionHistory.get(key) ?? [];
+						console.log(`[Sessions Web Test] Opening session ${key} (${history.length} history items)`);
+						const disposeEmitter = new Emitter<void>();
+						const isComplete = observableValue('isComplete', history.length > 0);
+						return {
+							sessionResource,
+							history,
+							isCompleteObs: isComplete,
+							onWillDispose: disposeEmitter.event,
+							async requestHandler(request, progress, _history, _token) {
+								console.log(`[Sessions Web Test] Session request: "${request.message}"`);
+								const response = getMockResponseWithEdits(request.message);
+								progress([{
+									kind: 'markdownContent',
+									content: { value: response.text, isTrusted: false, supportThemeIcons: false, supportHtml: false },
+								}]);
+								if (response.fileEdits) {
+									emitFileEdits(response.fileEdits, progress);
+								}
+								isComplete.set(true, undefined);
+							},
+							dispose() { disposeEmitter.fire(); disposeEmitter.dispose(); },
+						};
+					},
+				}));
+
+				// Register an item controller so sessions appear in the sidebar list.
+				// Only copilotcli (Background) sessions need real items — the
+				// copilot-cloud-agent controller must return an empty array to
+				// prevent it from overwriting sessions with the wrong providerType
+				// during a full model resolve.
+				const controllerItems = scheme === 'copilotcli' ? this._sessionItems : [];
+				this._register(this.chatSessionsService.registerChatSessionItemController(scheme, {
+					onDidChangeChatSessionItems: this._itemsChangedEmitter.event,
+					get items() { return controllerItems; },
+					async refresh() { /* in-memory, no-op */ },
+				}));
+
+				console.log(`[Sessions Web Test] Registered session provider for scheme: ${scheme}`);
+			} catch (err) {
+				console.warn(`[Sessions Web Test] Failed to register session provider for ${scheme}:`, err);
+			}
+		}
+	}
+
+	private registerMockTerminalBackend(): void {
+		const terminalService = this.terminalService;
+		const backend = this.createMockTerminalBackend();
+		Registry.as<ITerminalBackendRegistry>(TerminalExtensions.Backend).registerTerminalBackend(backend);
+		terminalService.registerProcessSupport(true);
+		console.log('[Sessions Web Test] Registered mock terminal backend');
+	}
+
+	private createMockTerminalBackend(): ITerminalBackend {
+		return {
+			remoteAuthority: undefined,
+			isVirtualProcess: false,
+			onDidRequestDetach: Event.None,
+			attachToProcess: async () => { throw new Error('Not supported'); },
+			attachToRevivedProcess: async () => { throw new Error('Not supported'); },
+			listProcesses: async () => [],
+			getProfiles: async () => [],
+			getDefaultProfile: async () => undefined,
+			getDefaultSystemShell: async () => '/bin/mock-shell',
+			getShellEnvironment: async () => ({}),
+			setTerminalLayoutInfo: async () => { },
+			getTerminalLayoutInfo: async () => undefined,
+			reduceConnectionGraceTime: () => { },
+			requestDetachInstance: () => { },
+			acceptDetachInstanceReply: () => { },
+			persistTerminalState: () => { },
+			createProcess: async (_shellLaunchConfig: IShellLaunchConfig, _cwd: string | URI, _cols: number, _rows: number, _unicodeVersion: string, _env: IProcessEnvironment, _options: ITerminalProcessOptions, _shouldPersist: boolean) => {
+				const onProcessData = new Emitter<string>();
+				const onProcessReady = new Emitter<IProcessReadyEvent>();
+				const onProcessExit = new Emitter<number | undefined>();
+				const onDidChangeHasChildProcesses = new Emitter<boolean>();
+				const onDidChangeProperty = new Emitter<IProcessProperty<ProcessPropertyType>>();
+
+				// Resolve cwd from createProcess arg or shellLaunchConfig
+				const rawCwd = _cwd || _shellLaunchConfig.cwd;
+				const cwd = !rawCwd ? '/' : typeof rawCwd === 'string' ? rawCwd : rawCwd.path;
+				console.log(`[Sessions Web Test] Mock terminal createProcess cwd: '${cwd}' (raw _cwd: '${_cwd}', slc.cwd: '${_shellLaunchConfig.cwd}')`);
+
+				// Fire ready after a microtask so the terminal service can wire up listeners
+				setTimeout(() => {
+					onProcessReady.fire({ pid: 1, cwd, windowsPty: undefined });
+				}, 0);
+
+				return {
+					id: 0,
+					shouldPersist: false,
+					onProcessData: onProcessData.event,
+					onProcessReady: onProcessReady.event,
+					onDidChangeHasChildProcesses: onDidChangeHasChildProcesses.event,
+					onDidChangeProperty: onDidChangeProperty.event,
+					onProcessExit: onProcessExit.event,
+					start: async () => undefined,
+					shutdown: async () => { },
+					input: async () => { },
+					resize: () => { },
+					clearBuffer: () => { },
+					acknowledgeDataEvent: () => { },
+					setUnicodeVersion: async () => { },
+					getInitialCwd: async () => cwd,
+					getCwd: async () => cwd,
+					getLatency: async () => [],
+					processBinary: async () => { },
+					refreshProperty: async (property: ProcessPropertyType) => { throw new Error(`Not supported: ${property}`); },
+					updateProperty: async () => { },
+					clearUnrespondedRequest: () => { },
+				};
+			},
+			getWslPath: async (original: string, _direction: 'unix-to-win' | 'win-to-unix') => original,
+			getEnvironment: async () => ({}),
+			getPerformanceMarks: () => [],
+			onPtyHostUnresponsive: Event.None,
+			onPtyHostResponsive: Event.None,
+			onPtyHostRestart: Event.None,
+			onPtyHostConnected: Event.None,
+		} as unknown as ITerminalBackend;
+	}
+
+	private preseedFolder(): void {
+		const mockFolderUri = URI.from({ scheme: 'mock-fs', authority: 'mock-repo', path: '/mock-repo' }).toString();
+		this.storageService.store('agentSessions.lastPickedFolder', mockFolderUri, StorageScope.PROFILE, StorageTarget.MACHINE);
+		console.log(`[Sessions Web Test] Pre-seeded folder: ${mockFolderUri}`);
+	}
+}
+
+// Register the contribution so it runs during workbench startup
+registerWorkbenchContribution2(MockChatAgentContribution.ID, MockChatAgentContribution, WorkbenchPhase.BlockStartup);
+
+// ---------------------------------------------------------------------------
+// MockGitService — resolves immediately instead of waiting 10s for delegate
+// ---------------------------------------------------------------------------
+
+class MockGitService implements IGitService {
+	declare readonly _serviceBrand: undefined;
+	readonly repositories: Iterable<IGitRepository> = [];
+	setDelegate(_delegate: IGitExtensionDelegate) { return Disposable.None; }
+	async openRepository(_uri: URI) { return undefined; }
+}
+
+// ---------------------------------------------------------------------------
+// TestSessionsBrowserMain
+// ---------------------------------------------------------------------------
+
+/**
+ * Test variant of SessionsBrowserMain that injects mock services
+ * for E2E testing. Service overrides for entitlements and auth are set
+ * in createWorkbench(). The mock chat agent is registered via a
+ * workbench contribution (MockChatAgentContribution above).
+ */
+export class TestSessionsBrowserMain extends SessionsBrowserMain {
+
+	protected override createWorkbench(domElement: HTMLElement, serviceCollection: ServiceCollection, logService: ILogService): IBrowserMainWorkbench {
+		console.log('[Sessions Web Test] Injecting mock services');
+
+		// Register mock-fs:// provider FIRST so all services can resolve workspace files
+		registerMockFileSystemProvider(serviceCollection);
+
+		// Override entitlement service so Sessions thinks user is signed in
+		serviceCollection.set(IChatEntitlementService, new MockChatEntitlementService());
+
+		// Override default account service to hide the "Sign In" button
+		serviceCollection.set(IDefaultAccountService, new MockDefaultAccountService());
+
+		// Override git service so openRepository resolves instantly (no 10s barrier wait)
+		serviceCollection.set(IGitService, new MockGitService());
+
+		console.log('[Sessions Web Test] Creating Sessions workbench with mocks');
+		return new SessionsWorkbench(domElement, undefined, serviceCollection, logService);
+	}
+}
diff --git a/src/vs/workbench/api/browser/extensionHost.contribution.ts b/src/vs/workbench/api/browser/extensionHost.contribution.ts
index 051a9f6f85da2..b8ad97532e275 100644
--- a/src/vs/workbench/api/browser/extensionHost.contribution.ts
+++ b/src/vs/workbench/api/browser/extensionHost.contribution.ts
@@ -100,6 +100,7 @@ import './mainThreadChatSessions.js';
 import './mainThreadDataChannels.js';
 import './mainThreadMeteredConnection.js';
 import './mainThreadGitExtensionService.js';
+import './mainThreadBrowsers.js';
 
 export class ExtensionPoints implements IWorkbenchContribution {
 
diff --git a/src/vs/workbench/api/browser/mainThreadBrowsers.ts b/src/vs/workbench/api/browser/mainThreadBrowsers.ts
new file mode 100644
index 0000000000000..933fdc2e1ddbc
--- /dev/null
+++ b/src/vs/workbench/api/browser/mainThreadBrowsers.ts
@@ -0,0 +1,172 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Disposable, DisposableMap, DisposableStore, IDisposable, toDisposable } from '../../../base/common/lifecycle.js';
+import { IEditorService } from '../../services/editor/common/editorService.js';
+import { IExtHostContext, extHostNamedCustomer } from '../../services/extensions/common/extHostCustomers.js';
+import { BrowserTabDto, ExtHostBrowsersShape, ExtHostContext, MainContext, MainThreadBrowsersShape } from '../common/extHost.protocol.js';
+import { IBrowserViewCDPService } from '../../contrib/browserView/common/browserView.js';
+import { BrowserViewUri } from '../../../platform/browserView/common/browserViewUri.js';
+import { EditorGroupColumn, columnToEditorGroup } from '../../services/editor/common/editorGroupColumn.js';
+import { IEditorGroupsService } from '../../services/editor/common/editorGroupsService.js';
+import { IConfigurationService } from '../../../platform/configuration/common/configuration.js';
+import { IEditorOptions } from '../../../platform/editor/common/editor.js';
+import { CDPRequest } from '../../../platform/browserView/common/cdp/types.js';
+import { BrowserEditorInput } from '../../contrib/browserView/common/browserEditorInput.js';
+
+@extHostNamedCustomer(MainContext.MainThreadBrowsers)
+export class MainThreadBrowsers extends Disposable implements MainThreadBrowsersShape {
+
+	private readonly _proxy: ExtHostBrowsersShape;
+
+	private readonly _cdpSessions = this._register(new DisposableMap<string, { groupId: string } & IDisposable>());
+	private readonly _knownBrowsers = this._register(new DisposableMap<string, { input: BrowserEditorInput } & IDisposable>());
+
+	constructor(
+		extHostContext: IExtHostContext,
+		@IEditorService private readonly editorService: IEditorService,
+		@IBrowserViewCDPService private readonly cdpService: IBrowserViewCDPService,
+		@IEditorGroupsService private readonly editorGroupsService: IEditorGroupsService,
+		@IConfigurationService private readonly configurationService: IConfigurationService,
+	) {
+		super();
+		this._proxy = extHostContext.getProxy(ExtHostContext.ExtHostBrowsers);
+
+		// Track open browser editors
+		this._register(this.editorService.onWillOpenEditor((e) => {
+			if (e.editor instanceof BrowserEditorInput) {
+				this._track(e.editor);
+			}
+		}));
+		this._register(this.editorService.onDidCloseEditor(e => {
+			if (e.editor instanceof BrowserEditorInput) {
+				this._knownBrowsers.deleteAndDispose(e.editor.id);
+			}
+		}));
+		this._register(this.editorService.onDidActiveEditorChange(() => this._syncActiveBrowserTab()));
+
+		// Initial sync
+		for (const input of this.editorService.editors) {
+			if (input instanceof BrowserEditorInput) {
+				this._track(input);
+			}
+		}
+		this._syncActiveBrowserTab();
+	}
+
+	// #region Browser tab open
+
+	async $openBrowserTab(url: string, viewColumn?: EditorGroupColumn, options?: IEditorOptions): Promise<BrowserTabDto> {
+		const browserUri = BrowserViewUri.forUrl(url);
+		const parsed = BrowserViewUri.parse(browserUri)!;
+
+		await this.editorService.openEditor(
+			{
+				resource: browserUri,
+				options
+			},
+			columnToEditorGroup(this.editorGroupsService, this.configurationService, viewColumn),
+		);
+		const known = this._knownBrowsers.get(parsed.id);
+		if (!known) {
+			throw new Error('Failed to open browser tab');
+		}
+
+		return this._toDto(known.input);
+	}
+
+	// #endregion
+
+	// #region Browser tab tracking
+
+	private async _syncActiveBrowserTab(): Promise<void> {
+		const active = this.editorService.activeEditorPane?.input;
+		if (active instanceof BrowserEditorInput) {
+			this._proxy.$onDidChangeActiveBrowserTab(this._toDto(active));
+		} else {
+			this._proxy.$onDidChangeActiveBrowserTab(undefined);
+		}
+	}
+
+	private _track(input: BrowserEditorInput): void {
+		if (this._knownBrowsers.has(input.id)) {
+			return;
+		}
+		const disposables = new DisposableStore();
+
+		// Track property changes. Currently all the tracked properties are covered under the `onDidChangeLabel` event.
+		disposables.add(input.onDidChangeLabel(() => {
+			this._proxy.$onDidChangeBrowserTabState(input.id, this._toDto(input));
+		}));
+		disposables.add(input.onWillDispose(() => {
+			this._proxy.$onDidCloseBrowserTab(input.id);
+			this._knownBrowsers.deleteAndDispose(input.id);
+		}));
+
+		this._knownBrowsers.set(input.id, { input, dispose: () => disposables.dispose() });
+		this._proxy.$onDidOpenBrowserTab(this._toDto(input));
+	}
+
+	private _toDto(input: BrowserEditorInput): BrowserTabDto {
+		return {
+			id: input.id,
+			url: input.url || 'about:blank',
+			title: input.getTitle(),
+			favicon: input.favicon,
+		};
+	}
+
+	// #endregion
+
+	// #region CDP session management
+
+	async $startCDPSession(sessionId: string, browserId: string): Promise<void> {
+		const known = this._knownBrowsers.get(browserId);
+		if (!known) {
+			throw new Error(`Unknown browser id: ${browserId}`);
+		}
+
+		// Before starting a session, resolve the input to ensure the underlying web contents exist and can be attached.
+		await known.input.resolve();
+
+		const groupId = await this.cdpService.createSessionGroup(browserId);
+		const disposables = new DisposableStore();
+
+		// Wire CDP messages from main process back to ext host
+		disposables.add(this.cdpService.onCDPMessage(groupId)(message => {
+			this._proxy.$onCDPSessionMessage(sessionId, message);
+		}));
+		disposables.add(this.cdpService.onDidDestroy(groupId)(() => {
+			this._cdpSessions.deleteAndDispose(sessionId);
+		}));
+		disposables.add(toDisposable(() => {
+			this.cdpService.destroySessionGroup(groupId).catch(() => { });
+			this._proxy.$onCDPSessionClosed(sessionId);
+		}));
+
+		this._cdpSessions.set(sessionId, { groupId, dispose: () => disposables.dispose() });
+	}
+
+	async $closeCDPSession(sessionId: string): Promise<void> {
+		this._cdpSessions.deleteAndDispose(sessionId);
+	}
+
+	async $sendCDPMessage(sessionId: string, message: CDPRequest): Promise<void> {
+		const session = this._cdpSessions.get(sessionId);
+		if (session) {
+			await this.cdpService.sendCDPMessage(session.groupId, message);
+		}
+	}
+
+	async $closeBrowserTab(browserId: string): Promise<void> {
+		const known = this._knownBrowsers.get(browserId);
+		if (!known) {
+			throw new Error(`Unknown browser id: ${browserId}`);
+		}
+		known.input.dispose();
+	}
+
+	// #endregion
+}
diff --git a/src/vs/workbench/api/browser/mainThreadChatAgents2.ts b/src/vs/workbench/api/browser/mainThreadChatAgents2.ts
index a8089d43ed381..f40d952f33215 100644
--- a/src/vs/workbench/api/browser/mainThreadChatAgents2.ts
+++ b/src/vs/workbench/api/browser/mainThreadChatAgents2.ts
@@ -32,6 +32,7 @@ import { isValidPromptType } from '../../contrib/chat/common/promptSyntax/prompt
 import { IChatModel } from '../../contrib/chat/common/model/chatModel.js';
 import { ChatRequestAgentPart } from '../../contrib/chat/common/requestParser/chatParserTypes.js';
 import { ChatRequestParser } from '../../contrib/chat/common/requestParser/chatRequestParser.js';
+import { getDynamicVariablesForWidget, getSelectedToolAndToolSetsForWidget } from '../../contrib/chat/browser/attachments/chatVariables.js';
 import { IChatContentInlineReference, IChatContentReference, IChatFollowup, IChatNotebookEdit, IChatProgress, IChatService, IChatTask, IChatTaskSerialized, IChatWarningMessage } from '../../contrib/chat/common/chatService/chatService.js';
 import { IChatSessionsService } from '../../contrib/chat/common/chatSessionsService.js';
 import { ChatAgentLocation, ChatModeKind } from '../../contrib/chat/common/constants.js';
@@ -39,8 +40,9 @@ import { ILanguageModelToolsService } from '../../contrib/chat/common/tools/lang
 import { IExtHostContext, extHostNamedCustomer } from '../../services/extensions/common/extHostCustomers.js';
 import { IExtensionService } from '../../services/extensions/common/extensions.js';
 import { Dto } from '../../services/extensions/common/proxyIdentifier.js';
-import { ExtHostChatAgentsShape2, ExtHostContext, IChatNotebookEditDto, IChatParticipantMetadata, IChatProgressDto, IChatSessionContextDto, IDynamicChatAgentProps, IExtensionChatAgentMetadata, MainContext, MainThreadChatAgentsShape2 } from '../common/extHost.protocol.js';
+import { ExtHostChatAgentsShape2, ExtHostContext, IChatNotebookEditDto, IChatParticipantMetadata, IChatProgressDto, IChatSessionContextDto, ICustomAgentDto, IDynamicChatAgentProps, IExtensionChatAgentMetadata, IInstructionDto, ISkillDto, MainContext, MainThreadChatAgentsShape2 } from '../common/extHost.protocol.js';
 import { NotebookDto } from './mainThreadNotebookDto.js';
+import { isUntitledChatSession } from '../../contrib/chat/common/model/chatUri.js';
 
 interface AgentData {
 	dispose: () => void;
@@ -152,6 +154,24 @@ export class MainThreadChatAgents2 extends Disposable implements MainThreadChatA
 
 		// Push the initial active session if there is already a focused widget
 		this._acceptActiveChatSession(this._chatWidgetService.lastFocusedWidget);
+
+		// Push custom agents to ext host
+		void this._pushCustomAgents();
+		this._register(this._promptsService.onDidChangeCustomAgents(() => {
+			void this._pushCustomAgents();
+		}));
+
+		// Push instructions to ext host
+		void this._pushInstructions();
+		this._register(this._promptsService.onDidChangeInstructions(() => {
+			void this._pushInstructions();
+		}));
+
+		// Push skills to ext host
+		void this._pushSkills();
+		this._register(this._promptsService.onDidChangeSkills(() => {
+			void this._pushSkills();
+		}));
 	}
 
 	private _acceptActiveChatSession(widget: IChatWidget | undefined): void {
@@ -160,6 +180,36 @@ export class MainThreadChatAgents2 extends Disposable implements MainThreadChatA
 		this._proxy.$acceptActiveChatSession(isLocal ? sessionResource : undefined);
 	}
 
+	private async _pushCustomAgents(): Promise<void> {
+		try {
+			const customAgents = await this._promptsService.getCustomAgents(CancellationToken.None);
+			const dtos: ICustomAgentDto[] = customAgents.map(agent => ({ uri: agent.uri }));
+			this._proxy.$acceptCustomAgents(dtos);
+		} catch (error) {
+			this._logService.error('[chat] Failed to push custom agents to extension host', error);
+		}
+	}
+
+	private async _pushInstructions(): Promise<void> {
+		try {
+			const instructions = await this._promptsService.getInstructionFiles(CancellationToken.None);
+			const dtos: IInstructionDto[] = instructions.map(instruction => ({ uri: instruction.uri }));
+			this._proxy.$acceptInstructions(dtos);
+		} catch (error) {
+			this._logService.error('[chat] Failed to push instructions to extension host', error);
+		}
+	}
+
+	private async _pushSkills(): Promise<void> {
+		try {
+			const skills = await this._promptsService.findAgentSkills(CancellationToken.None) ?? [];
+			const dtos: ISkillDto[] = skills.map(skill => ({ uri: skill.uri }));
+			this._proxy.$acceptSkills(dtos);
+		} catch (error) {
+			this._logService.error('[chat] Failed to push skills to extension host', error);
+		}
+	}
+
 	$unregisterAgent(handle: number): void {
 		this._agents.deleteAndDispose(handle);
 	}
@@ -197,18 +247,8 @@ export class MainThreadChatAgents2 extends Disposable implements MainThreadChatA
 					const contributedSession = chatSession?.contributedChatSession;
 					let chatSessionContext: IChatSessionContextDto | undefined;
 					if (contributedSession) {
-						let chatSessionResource = contributedSession.chatSessionResource;
-						let isUntitled = contributedSession.isUntitled;
-
-						// For new untitled sessions, invoke the controller's newChatSessionItemHandler
-						// to let the extension create a proper session item before the first request.
-						if (isUntitled) {
-							const newItem = await this._chatSessionService.createNewChatSessionItem(contributedSession.chatSessionType, request, token);
-							if (newItem) {
-								chatSessionResource = newItem.resource;
-								isUntitled = false;
-							}
-						}
+						const chatSessionResource = contributedSession.chatSessionResource;
+						const isUntitled = isUntitledChatSession(chatSessionResource);
 
 						chatSessionContext = {
 							chatSessionResource,
@@ -346,6 +386,7 @@ export class MainThreadChatAgents2 extends Disposable implements MainThreadChatA
 						kind: 'usage',
 						promptTokens: progress.promptTokens,
 						completionTokens: progress.completionTokens,
+						outputBuffer: progress.outputBuffer,
 						promptTokenDetails: progress.promptTokenDetails
 					});
 				}
@@ -443,7 +484,7 @@ export class MainThreadChatAgents2 extends Disposable implements MainThreadChatA
 					return;
 				}
 
-				const parsedRequest = this._instantiationService.createInstance(ChatRequestParser).parseChatRequest(widget.viewModel.sessionResource, model.getValue()).parts;
+				const parsedRequest = this._instantiationService.createInstance(ChatRequestParser).parseChatRequestWithReferences(getDynamicVariablesForWidget(widget), getSelectedToolAndToolSetsForWidget(widget), model.getValue()).parts;
 				const agentPart = parsedRequest.find((part): part is ChatRequestAgentPart => part instanceof ChatRequestAgentPart);
 				const thisAgentId = this._agents.get(handle)?.id;
 				if (agentPart?.agent.id !== thisAgentId) {
diff --git a/src/vs/workbench/api/browser/mainThreadChatDebug.ts b/src/vs/workbench/api/browser/mainThreadChatDebug.ts
index d36be25864758..8daa3270c4aaf 100644
--- a/src/vs/workbench/api/browser/mainThreadChatDebug.ts
+++ b/src/vs/workbench/api/browser/mainThreadChatDebug.ts
@@ -3,9 +3,11 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { Disposable, DisposableStore } from '../../../base/common/lifecycle.js';
+import { Disposable, DisposableStore, MutableDisposable } from '../../../base/common/lifecycle.js';
 import { URI } from '../../../base/common/uri.js';
+import { VSBuffer } from '../../../base/common/buffer.js';
 import { ChatDebugLogLevel, IChatDebugEvent, IChatDebugService } from '../../contrib/chat/common/chatDebugService.js';
+import { IChatService } from '../../contrib/chat/common/chatService/chatService.js';
 import { extHostNamedCustomer, IExtHostContext } from '../../services/extensions/common/extHostCustomers.js';
 import { ExtHostChatDebugShape, ExtHostContext, IChatDebugEventDto, MainContext, MainThreadChatDebugShape } from '../common/extHost.protocol.js';
 import { Proxied } from '../../services/extensions/common/proxyIdentifier.js';
@@ -15,15 +17,29 @@ export class MainThreadChatDebug extends Disposable implements MainThreadChatDeb
 	private readonly _proxy: Proxied<ExtHostChatDebugShape>;
 	private readonly _providerDisposables = new Map<number, DisposableStore>();
 	private readonly _activeSessionResources = new Map<number, URI>();
+	private readonly _coreEventForwarder = this._register(new MutableDisposable());
 
 	constructor(
 		extHostContext: IExtHostContext,
 		@IChatDebugService private readonly _chatDebugService: IChatDebugService,
+		@IChatService private readonly _chatService: IChatService,
 	) {
 		super();
 		this._proxy = extHostContext.getProxy(ExtHostContext.ExtHostChatDebug);
 	}
 
+	$subscribeToCoreDebugEvents(): void {
+		this._coreEventForwarder.value = this._chatDebugService.onDidAddEvent(event => {
+			if (this._chatDebugService.isCoreEvent(event)) {
+				this._proxy.$onCoreDebugEvent(this._serializeEvent(event));
+			}
+		});
+	}
+
+	$unsubscribeFromCoreDebugEvents(): void {
+		this._coreEventForwarder.clear();
+	}
+
 	$registerChatDebugLogProvider(handle: number): void {
 		const disposables = new DisposableStore();
 		this._providerDisposables.set(handle, disposables);
@@ -36,6 +52,26 @@ export class MainThreadChatDebug extends Disposable implements MainThreadChatDeb
 			},
 			resolveChatDebugLogEvent: async (eventId, token) => {
 				return this._proxy.$resolveChatDebugLogEvent(handle, eventId, token);
+			},
+			provideChatDebugLogExport: async (sessionResource, token) => {
+				// Gather core events and session title to pass to the extension.
+				const coreEventDtos = this._chatDebugService.getEvents(sessionResource)
+					.filter(e => this._chatDebugService.isCoreEvent(e))
+					.map(e => this._serializeEvent(e));
+				const sessionTitle = this._chatService.getSessionTitle(sessionResource);
+				const result = await this._proxy.$exportChatDebugLog(handle, sessionResource, coreEventDtos, sessionTitle, token);
+				return result?.buffer;
+			},
+			resolveChatDebugLogImport: async (data, token) => {
+				const result = await this._proxy.$importChatDebugLog(handle, VSBuffer.wrap(data), token);
+				if (!result) {
+					return undefined;
+				}
+				const uri = URI.revive(result.uri);
+				if (result.sessionTitle) {
+					this._chatDebugService.setImportedSessionTitle(uri, result.sessionTitle);
+				}
+				return uri;
 			}
 		}));
 	}
@@ -58,6 +94,30 @@ export class MainThreadChatDebug extends Disposable implements MainThreadChatDeb
 		this._chatDebugService.addProviderEvent(revived);
 	}
 
+	private _serializeEvent(event: IChatDebugEvent): IChatDebugEventDto {
+		const base = {
+			id: event.id,
+			sessionResource: event.sessionResource,
+			created: event.created.getTime(),
+			parentEventId: event.parentEventId,
+		};
+
+		switch (event.kind) {
+			case 'toolCall':
+				return { ...base, kind: 'toolCall', toolName: event.toolName, toolCallId: event.toolCallId, input: event.input, output: event.output, result: event.result, durationInMillis: event.durationInMillis };
+			case 'modelTurn':
+				return { ...base, kind: 'modelTurn', model: event.model, requestName: event.requestName, inputTokens: event.inputTokens, outputTokens: event.outputTokens, totalTokens: event.totalTokens, durationInMillis: event.durationInMillis };
+			case 'generic':
+				return { ...base, kind: 'generic', name: event.name, details: event.details, level: event.level, category: event.category };
+			case 'subagentInvocation':
+				return { ...base, kind: 'subagentInvocation', agentName: event.agentName, description: event.description, status: event.status, durationInMillis: event.durationInMillis, toolCallCount: event.toolCallCount, modelTurnCount: event.modelTurnCount };
+			case 'userMessage':
+				return { ...base, kind: 'userMessage', message: event.message, sections: event.sections.map(s => ({ name: s.name, content: s.content })) };
+			case 'agentResponse':
+				return { ...base, kind: 'agentResponse', message: event.message, sections: event.sections.map(s => ({ name: s.name, content: s.content })) };
+		}
+	}
+
 	private _reviveEvent(dto: IChatDebugEventDto, sessionResource: URI): IChatDebugEvent {
 		const base = {
 			id: dto.id,
@@ -83,6 +143,7 @@ export class MainThreadChatDebug extends Disposable implements MainThreadChatDeb
 					...base,
 					kind: 'modelTurn',
 					model: dto.model,
+					requestName: dto.requestName,
 					inputTokens: dto.inputTokens,
 					outputTokens: dto.outputTokens,
 					totalTokens: dto.totalTokens,
diff --git a/src/vs/workbench/api/browser/mainThreadChatSessions.ts b/src/vs/workbench/api/browser/mainThreadChatSessions.ts
index 496430de9647f..63729a8388184 100644
--- a/src/vs/workbench/api/browser/mainThreadChatSessions.ts
+++ b/src/vs/workbench/api/browser/mainThreadChatSessions.ts
@@ -15,6 +15,7 @@ import { isEqual } from '../../../base/common/resources.js';
 import { URI, UriComponents } from '../../../base/common/uri.js';
 import { localize } from '../../../nls.js';
 import { IDialogService } from '../../../platform/dialogs/common/dialogs.js';
+import { IInstantiationService } from '../../../platform/instantiation/common/instantiation.js';
 import { ILogService } from '../../../platform/log/common/log.js';
 import { hasValidDiff, IAgentSession } from '../../contrib/chat/browser/agentSessions/agentSessionsModel.js';
 import { IAgentSessionsService } from '../../contrib/chat/browser/agentSessions/agentSessionsService.js';
@@ -24,16 +25,17 @@ import { ChatEditorInput } from '../../contrib/chat/browser/widgetHosts/editor/c
 import { IChatRequestVariableEntry } from '../../contrib/chat/common/attachments/chatVariableEntries.js';
 import { awaitStatsForSession } from '../../contrib/chat/common/chat.js';
 import { IChatContentInlineReference, IChatProgress, IChatService, ResponseModelState } from '../../contrib/chat/common/chatService/chatService.js';
-import { ChatSessionStatus, IChatSession, IChatSessionContentProvider, IChatSessionHistoryItem, IChatSessionItem, IChatSessionItemController, IChatSessionProviderOptionItem, IChatSessionsService } from '../../contrib/chat/common/chatSessionsService.js';
+import { ChatSessionStatus, IChatNewSessionRequest, IChatSession, IChatSessionContentProvider, IChatSessionHistoryItem, IChatSessionItem, IChatSessionItemController, IChatSessionItemsDelta, IChatSessionProviderOptionItem, IChatSessionsService } from '../../contrib/chat/common/chatSessionsService.js';
 import { ChatAgentLocation } from '../../contrib/chat/common/constants.js';
 import { IChatModel } from '../../contrib/chat/common/model/chatModel.js';
+import { isUntitledChatSession } from '../../contrib/chat/common/model/chatUri.js';
 import { IChatAgentRequest } from '../../contrib/chat/common/participants/chatAgents.js';
 import { IChatTodoListService } from '../../contrib/chat/common/tools/chatTodoListService.js';
 import { IEditorGroupsService } from '../../services/editor/common/editorGroupsService.js';
 import { IEditorService } from '../../services/editor/common/editorService.js';
 import { extHostNamedCustomer, IExtHostContext } from '../../services/extensions/common/extHostCustomers.js';
 import { Dto } from '../../services/extensions/common/proxyIdentifier.js';
-import { ExtHostChatSessionsShape, ExtHostContext, IChatProgressDto, IChatSessionHistoryItemDto, IChatSessionItemsChange, MainContext, MainThreadChatSessionsShape } from '../common/extHost.protocol.js';
+import { ChatSessionContentContextDto, ExtHostChatSessionsShape, ExtHostContext, IChatProgressDto, IChatSessionHistoryItemDto, IChatSessionItemsChange, MainContext, MainThreadChatSessionsShape } from '../common/extHost.protocol.js';
 
 export class ObservableChatSession extends Disposable implements IChatSession {
 
@@ -97,17 +99,17 @@ export class ObservableChatSession extends Disposable implements IChatSession {
 		this._dialogService = dialogService;
 	}
 
-	initialize(token: CancellationToken): Promise<void> {
+	initialize(token: CancellationToken, context: ChatSessionContentContextDto): Promise<void> {
 		if (!this._initializationPromise) {
-			this._initializationPromise = this._doInitializeContent(token);
+			this._initializationPromise = this._doInitializeContent(token, context);
 		}
 		return this._initializationPromise;
 	}
 
-	private async _doInitializeContent(token: CancellationToken): Promise<void> {
+	private async _doInitializeContent(token: CancellationToken, context: ChatSessionContentContextDto): Promise<void> {
 		try {
 			const sessionContent = await raceCancellationError(
-				this._proxy.$provideChatSessionContent(this._providerHandle, this.sessionResource, token),
+				this._proxy.$provideChatSessionContent(this._providerHandle, this.sessionResource, context, token),
 				token
 			);
 
@@ -328,16 +330,25 @@ class MainThreadChatSessionItemController extends Disposable implements IChatSes
 	private readonly _proxy: ExtHostChatSessionsShape;
 	private readonly _handle: number;
 
-	private readonly _onDidChangeChatSessionItems = this._register(new Emitter<void>());
+	private readonly _onDidChangeChatSessionItems = this._register(new Emitter<IChatSessionItemsDelta>());
 	public readonly onDidChangeChatSessionItems = this._onDidChangeChatSessionItems.event;
 
 	constructor(
 		proxy: ExtHostChatSessionsShape,
-		handle: number
+		chatSessionType: string,
+		handle: number,
+		@IChatService chatService: IChatService,
 	) {
 		super();
 		this._proxy = proxy;
 		this._handle = handle;
+
+		this._register(chatService.registerChatModelChangeListeners(chatSessionType, (sessionResource) => {
+			const item = this._items.get(sessionResource);
+			if (item) {
+				this._onDidChangeChatSessionItems.fire({ addedOrUpdated: [item] });
+			}
+		}));
 	}
 
 	private readonly _items = new ResourceMap<IChatSessionItem>();
@@ -349,7 +360,7 @@ class MainThreadChatSessionItemController extends Disposable implements IChatSes
 		return this._proxy.$refreshChatSessionItems(this._handle, token);
 	}
 
-	async newChatSessionItem(request: IChatAgentRequest, token: CancellationToken): Promise<IChatSessionItem | undefined> {
+	async newChatSessionItem(request: IChatNewSessionRequest, token: CancellationToken): Promise<IChatSessionItem | undefined> {
 		const dto = await raceCancellationError(this._proxy.$newChatSessionItem(this._handle, request, token), token);
 		if (!dto) {
 			return undefined;
@@ -360,30 +371,36 @@ class MainThreadChatSessionItemController extends Disposable implements IChatSes
 			changes: revive(dto.changes),
 		};
 		this._items.set(item.resource, item);
-		this._onDidChangeChatSessionItems.fire();
+		this._onDidChangeChatSessionItems.fire({
+			addedOrUpdated: [item],
+		});
 		return item;
 	}
 
 	acceptChange(change: { readonly addedOrUpdated: readonly IChatSessionItem[]; readonly removed: readonly URI[] }): void {
 		for (const item of change.addedOrUpdated) {
+			warnOnUntitledSessionResource(item.resource);
 			this._items.set(item.resource, item);
 		}
 		for (const uri of change.removed) {
 			this._items.delete(uri);
 		}
-		this._onDidChangeChatSessionItems.fire();
+		this._onDidChangeChatSessionItems.fire({
+			addedOrUpdated: change.addedOrUpdated,
+			removed: change.removed,
+		});
 	}
 
 	addOrUpdateItem(item: IChatSessionItem): void {
+		warnOnUntitledSessionResource(item.resource);
 		this._items.set(item.resource, item);
-		this._onDidChangeChatSessionItems.fire();
-	}
-
-	fireOnDidChangeChatSessionItems(): void {
-		this._onDidChangeChatSessionItems.fire();
+		this._onDidChangeChatSessionItems.fire({
+			addedOrUpdated: [item],
+		});
 	}
 }
 
+
 @extHostNamedCustomer(MainContext.MainThreadChatSessions)
 export class MainThreadChatSessions extends Disposable implements MainThreadChatSessionsShape {
 	private readonly _itemControllerRegistrations = this._register(new DisposableMap<number, IDisposable & {
@@ -409,12 +426,14 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 		@IEditorService private readonly _editorService: IEditorService,
 		@IEditorGroupsService private readonly editorGroupService: IEditorGroupsService,
 		@ILogService private readonly _logService: ILogService,
+		@IInstantiationService private readonly _instantiationService: IInstantiationService,
 	) {
 		super();
 
 		this._proxy = this._extHostContext.getProxy(ExtHostContext.ExtHostChatSessions);
 
 		this._register(this._chatSessionsService.onRequestNotifyExtension(({ sessionResource, updates, waitUntil }) => {
+			warnOnUntitledSessionResource(sessionResource);
 			const handle = this._getHandleForSessionType(sessionResource.scheme);
 			this._logService.trace(`[MainThreadChatSessions] onRequestNotifyExtension received: scheme '${sessionResource.scheme}', handle ${handle}, ${updates.length} update(s)`);
 			if (handle !== undefined) {
@@ -427,6 +446,7 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 		this._register(this._agentSessionsService.model.onDidChangeSessionArchivedState(session => {
 			for (const [handle, { chatSessionType }] of this._itemControllerRegistrations) {
 				if (chatSessionType === session.providerType) {
+					warnOnUntitledSessionResource(session.resource);
 					this._proxy.$onDidChangeChatSessionItemState(handle, session.resource, session.isArchived());
 				}
 			}
@@ -440,7 +460,7 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 	$registerChatSessionItemController(handle: number, chatSessionType: string): void {
 		const disposables = new DisposableStore();
 
-		const controller = disposables.add(new MainThreadChatSessionItemController(this._proxy, handle));
+		const controller = disposables.add(this._instantiationService.createInstance(MainThreadChatSessionItemController, this._proxy, chatSessionType, handle));
 		disposables.add(this._chatSessionsService.registerChatSessionItemController(chatSessionType, controller));
 
 		this._itemControllerRegistrations.set(handle, {
@@ -448,12 +468,6 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 			controller,
 			dispose: () => disposables.dispose(),
 		});
-
-		disposables.add(this._chatSessionsService.registerChatModelChangeListeners(
-			this._chatService,
-			chatSessionType,
-			() => controller.fireOnDidChangeChatSessionItems()
-		));
 	}
 
 	private getController(handle: number): MainThreadChatSessionItemController {
@@ -464,11 +478,6 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 		return registration.controller;
 	}
 
-	$onDidChangeChatSessionItems(handle: number): void {
-		const controller = this.getController(handle);
-		controller.fireOnDidChangeChatSessionItems();
-	}
-
 	private async _resolveSessionItem(item: Dto<IChatSessionItem>): Promise<IChatSessionItem> {
 		const uri = URI.revive(item.resource);
 		const model = this._chatService.getSession(uri);
@@ -516,6 +525,7 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 
 	$onDidChangeChatSessionOptions(handle: number, sessionResourceComponents: UriComponents, updates: ReadonlyArray<{ optionId: string; value: string }>): void {
 		const sessionResource = URI.revive(sessionResourceComponents);
+		warnOnUntitledSessionResource(sessionResource);
 		this._chatSessionsService.notifySessionOptionsChange(sessionResource, updates);
 	}
 
@@ -569,6 +579,9 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 						options,
 					},
 				}], originalGroup);
+
+				// Re-send queued requests from the original session on the committed session
+				this._resendPendingRequests(originalResource, modifiedResource);
 				return;
 			}
 
@@ -589,11 +602,21 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 				const ref = await this._chatService.acquireOrLoadSession(modifiedResource, ChatAgentLocation.Chat, CancellationToken.None);
 				ref?.dispose();
 			}
+
+			// Re-send queued requests from the original session on the committed session
+			this._resendPendingRequests(originalResource, modifiedResource);
 		} finally {
 			originalModel?.dispose();
 		}
 	}
 
+	/**
+	 * Re-sends pending and in-flight requests from the original session on the committed session.
+	 */
+	private _resendPendingRequests(originalResource: URI, modifiedResource: URI): void {
+		this._chatService.migrateRequests(originalResource, modifiedResource);
+	}
+
 	private async handleSessionModelOverrides(model: IChatModel, session: Dto<IChatSessionItem>): Promise<Dto<IChatSessionItem>> {
 		// Override desciription if there's an in-progress count
 		const inProgress = model.getRequests().filter(r => r.response && !r.response.isComplete);
@@ -623,6 +646,8 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 	}
 
 	private async _provideChatSessionContent(providerHandle: number, sessionResource: URI, token: CancellationToken): Promise<IChatSession> {
+		warnOnUntitledSessionResource(sessionResource);
+
 		let session = this._activeSessions.get(sessionResource);
 
 		if (!session) {
@@ -643,7 +668,10 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 		}
 
 		try {
-			await session.initialize(token);
+			const initialSessionOptions = this._chatSessionsService.getSessionOptions(sessionResource);
+			await session.initialize(token, {
+				initialSessionOptions: initialSessionOptions ? [...initialSessionOptions].map(([optionId, value]) => ({ optionId, value })) : undefined,
+			});
 			if (session.options) {
 				for (const [_, handle] of this._sessionTypeToHandle) {
 					if (handle === providerHandle) {
@@ -712,6 +740,8 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 
 	$handleProgressComplete(handle: number, sessionResource: UriComponents, requestId: string) {
 		const resource = URI.revive(sessionResource);
+		warnOnUntitledSessionResource(resource);
+
 		const observableSession = this._activeSessions.get(resource);
 		if (!observableSession) {
 			this._logService.warn(`No session found for progress completion: handle ${handle}, sessionResource ${resource}, requestId ${requestId}`);
@@ -753,6 +783,9 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 				}));
 				this._chatSessionsService.setOptionGroupsForSessionType(chatSessionScheme, handle, groupsWithCallbacks);
 			}
+			if (options?.newSessionOptions) {
+				this._chatSessionsService.setNewSessionOptionsForSessionType(chatSessionScheme, options.newSessionOptions);
+			}
 		}).catch(err => this._logService.error('Error fetching chat session options', err));
 	}
 
@@ -801,3 +834,9 @@ export class MainThreadChatSessions extends Disposable implements MainThreadChat
 		}
 	}
 }
+
+function warnOnUntitledSessionResource(resource: URI): void {
+	if (isUntitledChatSession(resource)) {
+		console.trace(`[MainThreadChatSessions] untitled-style sessionResource detected ${resource.toString()}`);
+	}
+}
diff --git a/src/vs/workbench/api/browser/mainThreadDownloadService.ts b/src/vs/workbench/api/browser/mainThreadDownloadService.ts
index 33d4e7989aed3..0b2cda8e6d620 100644
--- a/src/vs/workbench/api/browser/mainThreadDownloadService.ts
+++ b/src/vs/workbench/api/browser/mainThreadDownloadService.ts
@@ -20,7 +20,7 @@ export class MainThreadDownloadService extends Disposable implements MainThreadD
 	}
 
 	$download(uri: UriComponents, to: UriComponents): Promise<void> {
-		return this.downloadService.download(URI.revive(uri), URI.revive(to));
+		return this.downloadService.download(URI.revive(uri), URI.revive(to), 'mainThreadDownloadService.download');
 	}
 
 }
diff --git a/src/vs/workbench/api/browser/mainThreadGitExtensionService.ts b/src/vs/workbench/api/browser/mainThreadGitExtensionService.ts
index 6ed0a6d0acdd0..e9579b0a3ec80 100644
--- a/src/vs/workbench/api/browser/mainThreadGitExtensionService.ts
+++ b/src/vs/workbench/api/browser/mainThreadGitExtensionService.ts
@@ -8,9 +8,9 @@ import { Disposable } from '../../../base/common/lifecycle.js';
 import { ResourceMap } from '../../../base/common/map.js';
 import { URI } from '../../../base/common/uri.js';
 import { GitRepository } from '../../contrib/git/browser/gitService.js';
-import { IGitExtensionDelegate, IGitService, GitRef, GitRefQuery, GitRefType, GitRepositoryState, GitBranch, IGitRepository } from '../../contrib/git/common/gitService.js';
+import { IGitExtensionDelegate, IGitService, GitRef, GitRefQuery, GitRefType, GitRepositoryState, GitBranch, GitChange, GitDiffChange, IGitRepository } from '../../contrib/git/common/gitService.js';
 import { extHostNamedCustomer, IExtHostContext } from '../../services/extensions/common/extHostCustomers.js';
-import { ExtHostContext, ExtHostGitExtensionShape, GitRefTypeDto, GitRepositoryStateDto, MainContext, MainThreadGitExtensionShape } from '../common/extHost.protocol.js';
+import { ExtHostContext, ExtHostGitExtensionShape, GitDiffChangeDto, GitRefTypeDto, GitRepositoryStateDto, MainContext, MainThreadGitExtensionShape } from '../common/extHost.protocol.js';
 
 function toGitRefType(type: GitRefTypeDto): GitRefType {
 	switch (type) {
@@ -21,6 +21,16 @@ function toGitRefType(type: GitRefTypeDto): GitRefType {
 	}
 }
 
+function toGitDiffChange(dto: GitDiffChangeDto): GitDiffChange {
+	return {
+		uri: URI.revive(dto.uri),
+		originalUri: dto.originalUri ? URI.revive(dto.originalUri) : undefined,
+		modifiedUri: dto.modifiedUri ? URI.revive(dto.modifiedUri) : undefined,
+		insertions: dto.insertions,
+		deletions: dto.deletions,
+	};
+}
+
 function toGitRepositoryState(dto: GitRepositoryStateDto | undefined): GitRepositoryState {
 	return {
 		HEAD: dto?.HEAD ? {
@@ -28,10 +38,31 @@ function toGitRepositoryState(dto: GitRepositoryStateDto | undefined): GitReposi
 			name: dto.HEAD.name,
 			commit: dto.HEAD.commit,
 			remote: dto.HEAD.remote,
+			base: dto.HEAD.base,
 			upstream: dto.HEAD.upstream,
 			ahead: dto.HEAD.ahead,
 			behind: dto.HEAD.behind,
 		} satisfies GitBranch : undefined,
+		mergeChanges: dto?.mergeChanges?.map(c => ({
+			uri: URI.revive(c.uri),
+			originalUri: c.originalUri ? URI.revive(c.originalUri) : undefined,
+			modifiedUri: c.modifiedUri ? URI.revive(c.modifiedUri) : undefined,
+		} satisfies GitChange)) ?? [],
+		indexChanges: dto?.indexChanges?.map(c => ({
+			uri: URI.revive(c.uri),
+			originalUri: c.originalUri ? URI.revive(c.originalUri) : undefined,
+			modifiedUri: c.modifiedUri ? URI.revive(c.modifiedUri) : undefined,
+		} satisfies GitChange)) ?? [],
+		workingTreeChanges: dto?.workingTreeChanges?.map(c => ({
+			uri: URI.revive(c.uri),
+			originalUri: c.originalUri ? URI.revive(c.originalUri) : undefined,
+			modifiedUri: c.modifiedUri ? URI.revive(c.modifiedUri) : undefined,
+		} satisfies GitChange)) ?? [],
+		untrackedChanges: dto?.untrackedChanges?.map(c => ({
+			uri: URI.revive(c.uri),
+			originalUri: c.originalUri ? URI.revive(c.originalUri) : undefined,
+			modifiedUri: c.modifiedUri ? URI.revive(c.modifiedUri) : undefined,
+		} satisfies GitChange)) ?? [],
 	};
 }
 
@@ -124,6 +155,16 @@ export class MainThreadGitExtensionService extends Disposable implements MainThr
 		} satisfies GitRef));
 	}
 
+	async diffBetweenWithStats(root: URI, ref1: string, ref2: string, path?: string): Promise<GitDiffChange[]> {
+		const handle = this._repositoryHandles.get(root);
+		if (handle === undefined) {
+			return [];
+		}
+
+		const result = await this._proxy.$diffBetweenWithStats(handle, ref1, ref2, path);
+		return result.map(toGitDiffChange);
+	}
+
 	async $onDidChangeRepository(handle: number): Promise<void> {
 		const repository = this._repositories.get(handle);
 		if (!repository) {
diff --git a/src/vs/workbench/api/browser/mainThreadLanguageModelTools.ts b/src/vs/workbench/api/browser/mainThreadLanguageModelTools.ts
index 5059c608dae22..d4a4edb3cd4e6 100644
--- a/src/vs/workbench/api/browser/mainThreadLanguageModelTools.ts
+++ b/src/vs/workbench/api/browser/mainThreadLanguageModelTools.ts
@@ -10,6 +10,7 @@ import { ThemeIcon } from '../../../base/common/themables.js';
 import { isUriComponents, URI, UriComponents } from '../../../base/common/uri.js';
 import { ExtensionIdentifier } from '../../../platform/extensions/common/extensions.js';
 import { ILogService } from '../../../platform/log/common/log.js';
+import { IProductService } from '../../../platform/product/common/productService.js';
 import { toToolSetKey } from '../../contrib/chat/common/tools/languageModelToolsContribution.js';
 import { CountTokensCallback, ILanguageModelToolsService, IToolData, IToolInvocation, IToolProgressStep, IToolResult, ToolDataSource, ToolProgress, toolResultHasBuffers, ToolSet } from '../../contrib/chat/common/tools/languageModelToolsService.js';
 import { extHostNamedCustomer, IExtHostContext } from '../../services/extensions/common/extHostCustomers.js';
@@ -30,6 +31,7 @@ export class MainThreadLanguageModelTools extends Disposable implements MainThre
 		extHostContext: IExtHostContext,
 		@ILanguageModelToolsService private readonly _languageModelToolsService: ILanguageModelToolsService,
 		@ILogService private readonly _logService: ILogService,
+		@IProductService private readonly _productService: IProductService,
 	) {
 		super();
 		this._proxy = extHostContext.getProxy(ExtHostContext.ExtHostLanguageModelTools);
@@ -66,7 +68,8 @@ export class MainThreadLanguageModelTools extends Disposable implements MainThre
 		// Only return content and metadata to EH
 		const out: Dto<IToolResult> = {
 			content: result.content,
-			toolMetadata: result.toolMetadata
+			toolMetadata: result.toolMetadata,
+			toolResultError: result.toolResultError,
 		};
 		return toolResultHasBuffers(result) ? new SerializableObjectWithBuffers(out) : out;
 	}
@@ -117,8 +120,13 @@ export class MainThreadLanguageModelTools extends Disposable implements MainThre
 			}
 		}
 
-		// Convert source from DTO
-		const source = revive<ToolDataSource>(definition.source);
+		// Convert source from DTO, matching the isBuiltinTool logic from languageModelToolsContribution
+		const isBuiltinTool = this._productService.defaultChatAgent?.chatExtensionId
+			? ExtensionIdentifier.equals(extensionId, this._productService.defaultChatAgent.chatExtensionId)
+			: false;
+		const source: ToolDataSource = isBuiltinTool
+			? ToolDataSource.Internal
+			: revive<ToolDataSource>(definition.source);
 
 		// Create the tool data
 		const toolData: IToolData = {
diff --git a/src/vs/workbench/api/browser/mainThreadManagedSockets.ts b/src/vs/workbench/api/browser/mainThreadManagedSockets.ts
index 8bd8f02136aa6..7b22545502ef0 100644
--- a/src/vs/workbench/api/browser/mainThreadManagedSockets.ts
+++ b/src/vs/workbench/api/browser/mainThreadManagedSockets.ts
@@ -4,20 +4,20 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { VSBuffer } from '../../../base/common/buffer.js';
-import { Emitter } from '../../../base/common/event.js';
-import { Disposable, IDisposable } from '../../../base/common/lifecycle.js';
+import { Emitter, Event } from '../../../base/common/event.js';
+import { Disposable, DisposableMap, DisposableStore } from '../../../base/common/lifecycle.js';
 import { ISocket, SocketCloseEventType } from '../../../base/parts/ipc/common/ipc.net.js';
 import { ManagedSocket, RemoteSocketHalf, connectManagedSocket } from '../../../platform/remote/common/managedSocket.js';
 import { ManagedRemoteConnection, RemoteConnectionType } from '../../../platform/remote/common/remoteAuthorityResolver.js';
 import { IRemoteSocketFactoryService, ISocketFactory } from '../../../platform/remote/common/remoteSocketFactoryService.js';
-import { ExtHostContext, ExtHostManagedSocketsShape, MainContext, MainThreadManagedSocketsShape } from '../common/extHost.protocol.js';
 import { IExtHostContext, extHostNamedCustomer } from '../../services/extensions/common/extHostCustomers.js';
+import { ExtHostContext, ExtHostManagedSocketsShape, MainContext, MainThreadManagedSocketsShape } from '../common/extHost.protocol.js';
 
 @extHostNamedCustomer(MainContext.MainThreadManagedSockets)
 export class MainThreadManagedSockets extends Disposable implements MainThreadManagedSocketsShape {
 
 	private readonly _proxy: ExtHostManagedSocketsShape;
-	private readonly _registrations = new Map<number, IDisposable>();
+	private readonly _registrations = this._register(new DisposableMap<number>());
 	private readonly _remoteSockets = new Map<number, RemoteSocketHalf>();
 
 	constructor(
@@ -30,6 +30,7 @@ export class MainThreadManagedSockets extends Disposable implements MainThreadMa
 
 	async $registerSocketFactory(socketFactoryId: number): Promise<void> {
 		const that = this;
+		const store = new DisposableStore();
 		const socketFactory = new class implements ISocketFactory<RemoteConnectionType.Managed> {
 
 			supports(connectTo: ManagedRemoteConnection): boolean {
@@ -54,7 +55,7 @@ export class MainThreadManagedSockets extends Disposable implements MainThreadMa
 						MainThreadManagedSocket.connect(socketId, that._proxy, path, query, debugLabel, half)
 							.then(
 								socket => {
-									socket.onDidDispose(() => that._remoteSockets.delete(socketId));
+									store.add(Event.once(socket.onDidDispose)(() => that._remoteSockets.delete(socketId)));
 									resolve(socket);
 								},
 								err => {
@@ -65,12 +66,13 @@ export class MainThreadManagedSockets extends Disposable implements MainThreadMa
 				});
 			}
 		};
-		this._registrations.set(socketFactoryId, this._remoteSocketFactoryService.register(RemoteConnectionType.Managed, socketFactory));
+		store.add(this._remoteSocketFactoryService.register(RemoteConnectionType.Managed, socketFactory));
+		this._registrations.set(socketFactoryId, store);
 
 	}
 
 	async $unregisterSocketFactory(socketFactoryId: number): Promise<void> {
-		this._registrations.get(socketFactoryId)?.dispose();
+		this._registrations.deleteAndDispose(socketFactoryId);
 	}
 
 	$onDidManagedSocketHaveData(socketId: number, data: VSBuffer): void {
@@ -115,7 +117,7 @@ export class MainThreadManagedSocket extends ManagedSocket {
 		this.proxy.$remoteSocketWrite(this.socketId, buffer);
 	}
 
-	protected override  closeRemote(): void {
+	protected override closeRemote(): void {
 		this.proxy.$remoteSocketEnd(this.socketId);
 	}
 
diff --git a/src/vs/workbench/api/browser/mainThreadWorkspace.ts b/src/vs/workbench/api/browser/mainThreadWorkspace.ts
index 02a2e749a1cf0..d147675ff99c8 100644
--- a/src/vs/workbench/api/browser/mainThreadWorkspace.ts
+++ b/src/vs/workbench/api/browser/mainThreadWorkspace.ts
@@ -5,7 +5,7 @@
 
 import { CancellationToken, CancellationTokenSource } from '../../../base/common/cancellation.js';
 import { isCancellationError } from '../../../base/common/errors.js';
-import { DisposableStore, IDisposable } from '../../../base/common/lifecycle.js';
+import { Disposable, DisposableMap, IDisposable } from '../../../base/common/lifecycle.js';
 import { isNative } from '../../../base/common/platform.js';
 import { URI, UriComponents } from '../../../base/common/uri.js';
 import { localize } from '../../../nls.js';
@@ -16,7 +16,7 @@ import { ILabelService } from '../../../platform/label/common/label.js';
 import { INotificationService } from '../../../platform/notification/common/notification.js';
 import { AuthInfo, Credentials, IRequestService } from '../../../platform/request/common/request.js';
 import { WorkspaceTrustRequestOptions, IWorkspaceTrustManagementService, IWorkspaceTrustRequestService, ResourceTrustRequestOptions } from '../../../platform/workspace/common/workspaceTrust.js';
-import { IWorkspace, IWorkspaceContextService, WorkbenchState, isUntitledWorkspace, WorkspaceFolder } from '../../../platform/workspace/common/workspace.js';
+import { IWorkspace, IWorkspaceContextService, isUntitledWorkspace, WorkspaceFolder } from '../../../platform/workspace/common/workspace.js';
 import { extHostNamedCustomer, IExtHostContext } from '../../services/extensions/common/extHostCustomers.js';
 import { checkGlobFileExists } from '../../services/extensions/common/workspaceContains.js';
 import { IFileQueryBuilderOptions, ITextQueryBuilderOptions, QueryBuilder } from '../../services/search/common/queryBuilder.js';
@@ -32,9 +32,8 @@ import { revive } from '../../../base/common/marshalling.js';
 import { ITextFileService } from '../../services/textfile/common/textfiles.js';
 
 @extHostNamedCustomer(MainContext.MainThreadWorkspace)
-export class MainThreadWorkspace implements MainThreadWorkspaceShape {
+export class MainThreadWorkspace extends Disposable implements MainThreadWorkspaceShape {
 
-	private readonly _toDispose = new DisposableStore();
 	private readonly _activeCancelTokens: { [id: number]: CancellationTokenSource } = Object.create(null);
 	private readonly _proxy: ExtHostWorkspaceShape;
 	private readonly _queryBuilder: QueryBuilder;
@@ -57,6 +56,7 @@ export class MainThreadWorkspace implements MainThreadWorkspaceShape {
 		@IWorkspaceTrustRequestService private readonly _workspaceTrustRequestService: IWorkspaceTrustRequestService,
 		@ITextFileService private readonly _textFileService: ITextFileService,
 	) {
+		super();
 		this._queryBuilder = this._instantiationService.createInstance(QueryBuilder);
 		this._proxy = extHostContext.getProxy(ExtHostContext.ExtHostWorkspace);
 		const workspace = this._contextService.getWorkspace();
@@ -67,14 +67,14 @@ export class MainThreadWorkspace implements MainThreadWorkspaceShape {
 		} else {
 			this._contextService.getCompleteWorkspace().then(workspace => this._proxy.$initializeWorkspace(this.getWorkspaceData(workspace), this.isWorkspaceTrusted()));
 		}
-		this._contextService.onDidChangeWorkspaceFolders(this._onDidChangeWorkspace, this, this._toDispose);
-		this._contextService.onDidChangeWorkbenchState(this._onDidChangeWorkspace, this, this._toDispose);
-		this._workspaceTrustManagementService.onDidChangeTrust(this._onDidGrantWorkspaceTrust, this, this._toDispose);
-		this._workspaceTrustManagementService.onDidChangeTrustedFolders(this._onDidChangeWorkspaceTrustedFolders, this, this._toDispose);
+		this._register(this._contextService.onDidChangeWorkspaceFolders(this._onDidChangeWorkspace, this));
+		this._register(this._contextService.onDidChangeWorkbenchState(this._onDidChangeWorkspace, this));
+		this._register(this._workspaceTrustManagementService.onDidChangeTrust(this._onDidGrantWorkspaceTrust, this));
+		this._register(this._workspaceTrustManagementService.onDidChangeTrustedFolders(this._onDidChangeWorkspaceTrustedFolders, this));
 	}
 
-	dispose(): void {
-		this._toDispose.dispose();
+	override dispose(): void {
+		super.dispose();
 
 		for (const requestId in this._activeCancelTokens) {
 			const tokenSource = this._activeCancelTokens[requestId];
@@ -130,7 +130,7 @@ export class MainThreadWorkspace implements MainThreadWorkspaceShape {
 	}
 
 	private getWorkspaceData(workspace: IWorkspace): IWorkspaceData | null {
-		if (this._contextService.getWorkbenchState() === WorkbenchState.EMPTY) {
+		if (!this._contextService.hasWorkspaceData()) {
 			return null;
 		}
 		return {
@@ -270,7 +270,7 @@ export class MainThreadWorkspace implements MainThreadWorkspaceShape {
 	}
 
 	// --- edit sessions ---
-	private registeredEditSessionProviders = new Map<number, IDisposable>();
+	private registeredEditSessionProviders = this._register(new DisposableMap<number, IDisposable>());
 
 	$registerEditSessionIdentityProvider(handle: number, scheme: string) {
 		const disposable = this._editSessionIdentityService.registerEditSessionIdentityProvider({
@@ -284,17 +284,14 @@ export class MainThreadWorkspace implements MainThreadWorkspaceShape {
 		});
 
 		this.registeredEditSessionProviders.set(handle, disposable);
-		this._toDispose.add(disposable);
 	}
 
 	$unregisterEditSessionIdentityProvider(handle: number) {
-		const disposable = this.registeredEditSessionProviders.get(handle);
-		disposable?.dispose();
-		this.registeredEditSessionProviders.delete(handle);
+		this.registeredEditSessionProviders.deleteAndDispose(handle);
 	}
 
 	// --- canonical uri identities ---
-	private registeredCanonicalUriProviders = new Map<number, IDisposable>();
+	private registeredCanonicalUriProviders = this._register(new DisposableMap<number, IDisposable>());
 
 	$registerCanonicalUriProvider(handle: number, scheme: string) {
 		const disposable = this._canonicalUriService.registerCanonicalUriProvider({
@@ -309,13 +306,10 @@ export class MainThreadWorkspace implements MainThreadWorkspaceShape {
 		});
 
 		this.registeredCanonicalUriProviders.set(handle, disposable);
-		this._toDispose.add(disposable);
 	}
 
 	$unregisterCanonicalUriProvider(handle: number) {
-		const disposable = this.registeredCanonicalUriProviders.get(handle);
-		disposable?.dispose();
-		this.registeredCanonicalUriProviders.delete(handle);
+		this.registeredCanonicalUriProviders.deleteAndDispose(handle);
 	}
 
 	// --- encodings
diff --git a/src/vs/workbench/api/common/extHost.api.impl.ts b/src/vs/workbench/api/common/extHost.api.impl.ts
index b1b56427b5be9..2d2d7f8fce7df 100644
--- a/src/vs/workbench/api/common/extHost.api.impl.ts
+++ b/src/vs/workbench/api/common/extHost.api.impl.ts
@@ -92,6 +92,7 @@ import { IExtHostSearch } from './extHostSearch.js';
 import { IExtHostSecretState } from './extHostSecretState.js';
 import { ExtHostShare } from './extHostShare.js';
 import { ExtHostSpeech } from './extHostSpeech.js';
+import { ExtHostBrowsers } from './extHostBrowsers.js';
 import { ExtHostStatusBar } from './extHostStatusBar.js';
 import { IExtHostStorage } from './extHostStorage.js';
 import { IExtensionStoragePaths } from './extHostStoragePaths.js';
@@ -247,6 +248,7 @@ export function createApiFactoryAndRegisterActors(accessor: ServicesAccessor): I
 	const extHostStatusBar = rpcProtocol.set(ExtHostContext.ExtHostStatusBar, new ExtHostStatusBar(rpcProtocol, extHostCommands.converter));
 	const extHostSpeech = rpcProtocol.set(ExtHostContext.ExtHostSpeech, new ExtHostSpeech(rpcProtocol));
 	const extHostEmbeddings = rpcProtocol.set(ExtHostContext.ExtHostEmbeddings, new ExtHostEmbeddings(rpcProtocol));
+	const extHostBrowsers = rpcProtocol.set(ExtHostContext.ExtHostBrowsers, new ExtHostBrowsers(rpcProtocol));
 
 	rpcProtocol.set(ExtHostContext.ExtHostMcp, accessor.get(IExtHostMpcService));
 
@@ -351,11 +353,11 @@ export function createApiFactoryAndRegisterActors(accessor: ServicesAccessor): I
 
 		// namespace: commands
 		const commands: typeof vscode.commands = {
-			registerCommand(id: string, command: <T>(...args: any[]) => T | Thenable<T>, thisArgs?: any): vscode.Disposable {
+			registerCommand(id: string, command: <T>(...args: unknown[]) => T | Thenable<T>, thisArgs?: unknown): vscode.Disposable {
 				return extHostCommands.registerCommand(true, id, command, thisArgs, undefined, extension);
 			},
-			registerTextEditorCommand(id: string, callback: (textEditor: vscode.TextEditor, edit: vscode.TextEditorEdit, ...args: any[]) => void, thisArg?: any): vscode.Disposable {
-				return extHostCommands.registerCommand(true, id, (...args: any[]): any => {
+			registerTextEditorCommand(id: string, callback: (textEditor: vscode.TextEditor, edit: vscode.TextEditorEdit, ...args: unknown[]) => void, thisArg?: unknown): vscode.Disposable {
+				return extHostCommands.registerCommand(true, id, (...args: unknown[]): any => {
 					const activeTextEditor = extHostEditors.getActiveTextEditor();
 					if (!activeTextEditor) {
 						extHostLogService.warn('Cannot execute ' + id + ' because there is no active text editor.');
@@ -364,7 +366,6 @@ export function createApiFactoryAndRegisterActors(accessor: ServicesAccessor): I
 
 					return activeTextEditor.edit((edit: vscode.TextEditorEdit) => {
 						callback.apply(thisArg, [activeTextEditor, edit, ...args]);
-
 					}).then((result) => {
 						if (!result) {
 							extHostLogService.warn('Edits from command ' + id + ' were not applied.');
@@ -374,9 +375,9 @@ export function createApiFactoryAndRegisterActors(accessor: ServicesAccessor): I
 					});
 				}, undefined, undefined, extension);
 			},
-			registerDiffInformationCommand: (id: string, callback: (diff: vscode.LineChange[], ...args: any[]) => any, thisArg?: any): vscode.Disposable => {
+			registerDiffInformationCommand: (id: string, callback: (diff: vscode.LineChange[], ...args: unknown[]) => any, thisArg?: unknown): vscode.Disposable => {
 				checkProposedApiEnabled(extension, 'diffCommand');
-				return extHostCommands.registerCommand(true, id, async (...args: any[]): Promise<any> => {
+				return extHostCommands.registerCommand(true, id, async (...args: unknown[]): Promise<any> => {
 					const activeTextEditor = extHostDocumentsAndEditors.activeEditor(true);
 					if (!activeTextEditor) {
 						extHostLogService.warn('Cannot execute ' + id + ' because there is no active text editor.');
@@ -387,7 +388,7 @@ export function createApiFactoryAndRegisterActors(accessor: ServicesAccessor): I
 					callback.apply(thisArg, [diff, ...args]);
 				}, undefined, undefined, extension);
 			},
-			executeCommand<T>(id: string, ...args: any[]): Thenable<T> {
+			executeCommand<T>(id: string, ...args: unknown[]): Thenable<T> {
 				return extHostCommands.executeCommand<T>(id, ...args);
 			},
 			getCommands(filterInternal: boolean = false): Thenable<string[]> {
@@ -1059,6 +1060,34 @@ export function createApiFactoryAndRegisterActors(accessor: ServicesAccessor): I
 				checkProposedApiEnabled(extension, 'chatParticipantPrivate');
 				return _asExtensionEvent(extHostChatAgents2.onDidChangeActiveChatPanelSessionResource)(listeners, thisArgs, disposables);
 			},
+			get browserTabs() {
+				checkProposedApiEnabled(extension, 'browser');
+				return extHostBrowsers.browserTabs;
+			},
+			onDidOpenBrowserTab(listener, thisArg?, disposables?) {
+				checkProposedApiEnabled(extension, 'browser');
+				return _asExtensionEvent(extHostBrowsers.onDidOpenBrowserTab)(listener, thisArg, disposables);
+			},
+			onDidCloseBrowserTab(listener, thisArg?, disposables?) {
+				checkProposedApiEnabled(extension, 'browser');
+				return _asExtensionEvent(extHostBrowsers.onDidCloseBrowserTab)(listener, thisArg, disposables);
+			},
+			get activeBrowserTab() {
+				checkProposedApiEnabled(extension, 'browser');
+				return extHostBrowsers.activeBrowserTab;
+			},
+			onDidChangeActiveBrowserTab(listener, thisArg?, disposables?) {
+				checkProposedApiEnabled(extension, 'browser');
+				return _asExtensionEvent(extHostBrowsers.onDidChangeActiveBrowserTab)(listener, thisArg, disposables);
+			},
+			onDidChangeBrowserTabState(listener, thisArg?, disposables?) {
+				checkProposedApiEnabled(extension, 'browser');
+				return _asExtensionEvent(extHostBrowsers.onDidChangeBrowserTabState)(listener, thisArg, disposables);
+			},
+			openBrowserTab(url: string, options?: vscode.BrowserTabShowOptions) {
+				checkProposedApiEnabled(extension, 'browser');
+				return extHostBrowsers.openBrowserTab(url, options);
+			},
 		};
 
 		// namespace: workspace
@@ -1304,13 +1333,13 @@ export function createApiFactoryAndRegisterActors(accessor: ServicesAccessor): I
 			onDidRenameFiles: (listener, thisArg, disposables) => {
 				return _asExtensionEvent(extHostFileSystemEvent.onDidRenameFile)(listener, thisArg, disposables);
 			},
-			onWillCreateFiles: (listener: (e: vscode.FileWillCreateEvent) => any, thisArg?: any, disposables?: vscode.Disposable[]) => {
+			onWillCreateFiles: (listener: (e: vscode.FileWillCreateEvent) => any, thisArg?: unknown, disposables?: vscode.Disposable[]) => {
 				return _asExtensionEvent(extHostFileSystemEvent.getOnWillCreateFileEvent(extension))(listener, thisArg, disposables);
 			},
-			onWillDeleteFiles: (listener: (e: vscode.FileWillDeleteEvent) => any, thisArg?: any, disposables?: vscode.Disposable[]) => {
+			onWillDeleteFiles: (listener: (e: vscode.FileWillDeleteEvent) => any, thisArg?: unknown, disposables?: vscode.Disposable[]) => {
 				return _asExtensionEvent(extHostFileSystemEvent.getOnWillDeleteFileEvent(extension))(listener, thisArg, disposables);
 			},
-			onWillRenameFiles: (listener: (e: vscode.FileWillRenameEvent) => any, thisArg?: any, disposables?: vscode.Disposable[]) => {
+			onWillRenameFiles: (listener: (e: vscode.FileWillRenameEvent) => any, thisArg?: unknown, disposables?: vscode.Disposable[]) => {
 				return _asExtensionEvent(extHostFileSystemEvent.getOnWillRenameFileEvent(extension))(listener, thisArg, disposables);
 			},
 			openTunnel: (forward: vscode.TunnelOptions) => {
@@ -1626,6 +1655,9 @@ export function createApiFactoryAndRegisterActors(accessor: ServicesAccessor): I
 			},
 			registerChatSessionItemProvider: (chatSessionType: string, provider: vscode.ChatSessionItemProvider) => {
 				checkProposedApiEnabled(extension, 'chatSessionsProvider');
+				extHostApiDeprecation.report('chat.registerChatSessionItemProvider', extension, `Please migrate to the new chat session controller API`, {
+					usageId: chatSessionType
+				});
 				return extHostChatSessions.registerChatSessionItemProvider(extension, chatSessionType, provider);
 			},
 			createChatSessionItemController: (chatSessionType: string, refreshHandler: (token: vscode.CancellationToken) => Thenable<void>) => {
@@ -1677,6 +1709,34 @@ export function createApiFactoryAndRegisterActors(accessor: ServicesAccessor): I
 				checkProposedApiEnabled(extension, 'chatDebug');
 				return extHostChatDebug.registerChatDebugLogProvider(provider);
 			},
+			onDidReceiveChatDebugEvent: (listener, thisArgs?, disposables?) => {
+				checkProposedApiEnabled(extension, 'chatDebug');
+				return extHostChatDebug.onDidAddCoreEvent(listener, thisArgs, disposables);
+			},
+			get customAgents() {
+				checkProposedApiEnabled(extension, 'chatPromptFiles');
+				return extHostChatAgents2.customAgents as readonly vscode.ChatResource[];
+			},
+			onDidChangeCustomAgents: (listener, thisArgs?, disposables?) => {
+				checkProposedApiEnabled(extension, 'chatPromptFiles');
+				return extHostChatAgents2.onDidChangeCustomAgents(listener, thisArgs, disposables);
+			},
+			get instructions() {
+				checkProposedApiEnabled(extension, 'chatPromptFiles');
+				return extHostChatAgents2.instructions as readonly vscode.ChatResource[];
+			},
+			onDidChangeInstructions: (listener, thisArgs?, disposables?) => {
+				checkProposedApiEnabled(extension, 'chatPromptFiles');
+				return extHostChatAgents2.onDidChangeInstructions(listener, thisArgs, disposables);
+			},
+			get skills() {
+				checkProposedApiEnabled(extension, 'chatPromptFiles');
+				return extHostChatAgents2.skills as readonly vscode.ChatResource[];
+			},
+			onDidChangeSkills: (listener, thisArgs?, disposables?) => {
+				checkProposedApiEnabled(extension, 'chatPromptFiles');
+				return extHostChatAgents2.onDidChangeSkills(listener, thisArgs, disposables);
+			},
 		};
 
 		// namespace: lm
@@ -1915,6 +1975,7 @@ export function createApiFactoryAndRegisterActors(accessor: ServicesAccessor): I
 			TaskGroup: extHostTypes.TaskGroup,
 			TaskPanelKind: extHostTypes.TaskPanelKind,
 			TaskRevealKind: extHostTypes.TaskRevealKind,
+			TaskRunOn: extHostTypes.TaskRunOn,
 			TaskScope: extHostTypes.TaskScope,
 			TerminalLink: extHostTypes.TerminalLink,
 			TerminalQuickFixTerminalCommand: extHostTypes.TerminalQuickFixCommand,
@@ -2076,6 +2137,8 @@ export function createApiFactoryAndRegisterActors(accessor: ServicesAccessor): I
 			ChatDebugEventTextContent: extHostTypes.ChatDebugEventTextContent,
 			ChatDebugMessageContentType: extHostTypes.ChatDebugMessageContentType,
 			ChatDebugEventMessageContent: extHostTypes.ChatDebugEventMessageContent,
+			ChatDebugEventToolCallContent: extHostTypes.ChatDebugEventToolCallContent,
+			ChatDebugEventModelTurnContent: extHostTypes.ChatDebugEventModelTurnContent,
 			ChatRequestEditorData: extHostTypes.ChatRequestEditorData,
 			ChatRequestNotebookData: extHostTypes.ChatRequestNotebookData,
 			ChatReferenceBinaryData: extHostTypes.ChatReferenceBinaryData,
diff --git a/src/vs/workbench/api/common/extHost.protocol.ts b/src/vs/workbench/api/common/extHost.protocol.ts
index 05e77f2e3006c..66eebd6da507f 100644
--- a/src/vs/workbench/api/common/extHost.protocol.ts
+++ b/src/vs/workbench/api/common/extHost.protocol.ts
@@ -34,6 +34,7 @@ import { IAccessibilityInformation } from '../../../platform/accessibility/commo
 import { ILocalizedString } from '../../../platform/action/common/action.js';
 import { ConfigurationTarget, IConfigurationChange, IConfigurationData, IConfigurationOverrides } from '../../../platform/configuration/common/configuration.js';
 import { ConfigurationScope } from '../../../platform/configuration/common/configurationRegistry.js';
+import { IEditorOptions } from '../../../platform/editor/common/editor.js';
 import { IExtensionIdWithVersion } from '../../../platform/extensionManagement/common/extensionStorage.js';
 import { ExtensionIdentifier, IExtensionDescription } from '../../../platform/extensions/common/extensions.js';
 import * as files from '../../../platform/files/common/files.js';
@@ -59,7 +60,7 @@ import { ICodeMapperRequest, ICodeMapperResult } from '../../contrib/chat/common
 import { IChatContextItem } from '../../contrib/chat/common/contextContrib/chatContext.js';
 import { IChatProgressHistoryResponseContent, IChatRequestVariableData } from '../../contrib/chat/common/model/chatModel.js';
 import { ChatResponseClearToPreviousToolInvocationReason, IChatContentInlineReference, IChatExternalEditsDto, IChatFollowup, IChatMultiDiffData, IChatMultiDiffDataSerialized, IChatNotebookEdit, IChatProgress, IChatTask, IChatTaskDto, IChatUserActionEvent, IChatVoteAction } from '../../contrib/chat/common/chatService/chatService.js';
-import { IChatSessionItem, IChatSessionProviderOptionGroup, IChatSessionProviderOptionItem } from '../../contrib/chat/common/chatSessionsService.js';
+import { IChatNewSessionRequest, IChatSessionItem, IChatSessionProviderOptionGroup, IChatSessionProviderOptionItem } from '../../contrib/chat/common/chatSessionsService.js';
 import { IChatRequestVariableValue } from '../../contrib/chat/common/attachments/chatVariables.js';
 import { ChatAgentLocation } from '../../contrib/chat/common/constants.js';
 import { IChatMessage, IChatResponsePart, ILanguageModelChatInfoOptions, ILanguageModelChatMetadataAndIdentifier, ILanguageModelChatSelector } from '../../contrib/chat/common/languageModels.js';
@@ -99,6 +100,7 @@ import { IExtHostDocumentSaveDelegate } from './extHostDocumentData.js';
 import { TerminalShellExecutionCommandLineConfidence } from './extHostTypes.js';
 import * as tasks from './shared/tasks.js';
 import { PromptsType } from '../../contrib/chat/common/promptSyntax/promptTypes.js';
+import { CDPEvent, CDPRequest, CDPResponse } from '../../../platform/browserView/common/cdp/types.js';
 
 export type IconPathDto =
 	| UriComponents
@@ -1351,6 +1353,30 @@ export interface ExtHostSpeechShape {
 	$cancelKeywordRecognitionSession(session: number): Promise<void>;
 }
 
+export interface BrowserTabDto {
+	id: string;
+	url: string;
+	title: string;
+	favicon: string | undefined;
+}
+
+export interface MainThreadBrowsersShape extends IDisposable {
+	$openBrowserTab(url: string, viewColumn?: EditorGroupColumn, options?: IEditorOptions): Promise<BrowserTabDto>;
+	$closeBrowserTab(browserId: string): Promise<void>;
+	$startCDPSession(sessionId: string, browserId: string): Promise<void>;
+	$closeCDPSession(sessionId: string): Promise<void>;
+	$sendCDPMessage(sessionId: string, message: CDPRequest): Promise<void>;
+}
+
+export interface ExtHostBrowsersShape {
+	$onDidOpenBrowserTab(browser: BrowserTabDto): void;
+	$onDidCloseBrowserTab(browserId: string): void;
+	$onDidChangeActiveBrowserTab(browser: BrowserTabDto | undefined): void;
+	$onDidChangeBrowserTabState(browserId: string, data: BrowserTabDto): void;
+	$onCDPSessionMessage(sessionId: string, message: CDPResponse | CDPEvent): void;
+	$onCDPSessionClosed(sessionId: string): void;
+}
+
 export interface MainThreadLanguageModelsShape extends IDisposable {
 	$registerLanguageModelProvider(vendor: string): void;
 	$onLMProviderChange(vendor: string): void;
@@ -1368,7 +1394,7 @@ export interface MainThreadLanguageModelsShape extends IDisposable {
 export interface ExtHostLanguageModelsShape {
 	$provideLanguageModelChatInfo(vendor: string, options: ILanguageModelChatInfoOptions, token: CancellationToken): Promise<ILanguageModelChatMetadataAndIdentifier[]>;
 	$updateModelAccesslist(data: { from: ExtensionIdentifier; to: ExtensionIdentifier; enabled: boolean }[]): void;
-	$startChatRequest(modelId: string, requestId: number, from: ExtensionIdentifier, messages: SerializableObjectWithBuffers<IChatMessage[]>, options: { [name: string]: any }, token: CancellationToken): Promise<void>;
+	$startChatRequest(modelId: string, requestId: number, from: ExtensionIdentifier | undefined, messages: SerializableObjectWithBuffers<IChatMessage[]>, options: { [name: string]: any }, token: CancellationToken): Promise<void>;
 	$acceptResponsePart(requestId: number, chunk: SerializableObjectWithBuffers<IChatResponsePart | IChatResponsePart[]>): Promise<void>;
 	$acceptResponseDone(requestId: number, error: SerializedError | undefined): Promise<void>;
 	$provideTokenLength(modelId: string, value: string | IChatMessage, token: CancellationToken): Promise<number>;
@@ -1415,6 +1441,7 @@ export interface IChatDebugToolCallEventDto extends IChatDebugEventCommonDto {
 export interface IChatDebugModelTurnEventDto extends IChatDebugEventCommonDto {
 	readonly kind: 'modelTurn';
 	readonly model?: string;
+	readonly requestName?: string;
 	readonly inputTokens?: number;
 	readonly outputTokens?: number;
 	readonly totalTokens?: number;
@@ -1470,17 +1497,48 @@ export interface IChatDebugEventMessageContentDto {
 	readonly sections: readonly IChatDebugMessageSectionDto[];
 }
 
-export type IChatDebugResolvedEventContentDto = IChatDebugEventTextContentDto | IChatDebugEventMessageContentDto;
+export interface IChatDebugEventToolCallContentDto {
+	readonly kind: 'toolCall';
+	readonly toolName: string;
+	readonly result?: 'success' | 'error';
+	readonly durationInMillis?: number;
+	readonly input?: string;
+	readonly output?: string;
+}
+
+export interface IChatDebugEventModelTurnContentDto {
+	readonly kind: 'modelTurn';
+	readonly requestName: string;
+	readonly model?: string;
+	readonly status?: string;
+	readonly durationInMillis?: number;
+	readonly timeToFirstTokenInMillis?: number;
+	readonly maxInputTokens?: number;
+	readonly maxOutputTokens?: number;
+	readonly inputTokens?: number;
+	readonly outputTokens?: number;
+	readonly cachedTokens?: number;
+	readonly totalTokens?: number;
+	readonly errorMessage?: string;
+	readonly sections?: readonly IChatDebugMessageSectionDto[];
+}
+
+export type IChatDebugResolvedEventContentDto = IChatDebugEventTextContentDto | IChatDebugEventMessageContentDto | IChatDebugEventToolCallContentDto | IChatDebugEventModelTurnContentDto;
 
 export interface ExtHostChatDebugShape {
 	$provideChatDebugLog(handle: number, sessionResource: UriComponents, token: CancellationToken): Promise<IChatDebugEventDto[] | undefined>;
 	$resolveChatDebugLogEvent(handle: number, eventId: string, token: CancellationToken): Promise<IChatDebugResolvedEventContentDto | undefined>;
+	$exportChatDebugLog(handle: number, sessionResource: UriComponents, coreEvents: IChatDebugEventDto[], sessionTitle: string | undefined, token: CancellationToken): Promise<VSBuffer | undefined>;
+	$importChatDebugLog(handle: number, data: VSBuffer, token: CancellationToken): Promise<{ uri: UriComponents; sessionTitle?: string } | undefined>;
+	$onCoreDebugEvent(event: IChatDebugEventDto): void;
 }
 
 export interface MainThreadChatDebugShape extends IDisposable {
 	$registerChatDebugLogProvider(handle: number): void;
 	$unregisterChatDebugLogProvider(handle: number): void;
 	$acceptChatDebugEvent(handle: number, event: IChatDebugEventDto): void;
+	$subscribeToCoreDebugEvents(): void;
+	$unsubscribeFromCoreDebugEvents(): void;
 }
 
 export interface MainThreadEmbeddingsShape extends IDisposable {
@@ -1587,6 +1645,21 @@ export interface ExtHostChatAgentsShape2 {
 	$setRequestTools(requestId: string, tools: UserSelectedTools): void;
 	$setYieldRequested(requestId: string, value: boolean): void;
 	$acceptActiveChatSession(sessionResource: UriComponents | undefined): void;
+	$acceptCustomAgents(agents: ICustomAgentDto[]): void;
+	$acceptInstructions(instructions: IInstructionDto[]): void;
+	$acceptSkills(skills: ISkillDto[]): void;
+}
+
+export interface ICustomAgentDto {
+	uri: UriComponents;
+}
+
+export interface IInstructionDto {
+	uri: UriComponents;
+}
+
+export interface ISkillDto {
+	uri: UriComponents;
 }
 export interface IChatParticipantMetadata {
 	participant: string;
@@ -2072,7 +2145,7 @@ export interface ExtHostCodeMapperShape {
 }
 
 export interface ExtHostCommandsShape {
-	$executeContributedCommand(id: string, ...args: any[]): Promise<unknown>;
+	$executeContributedCommand(id: string, ...args: unknown[]): Promise<unknown>;
 	$getContributedCommandMetadata(): Promise<{ [id: string]: string | ICommandMetadataDto }>;
 }
 
@@ -2401,7 +2474,7 @@ export interface ISuggestDataDto {
 	// Command
 	[ISuggestDataDtoField.commandIdent]?: string;
 	[ISuggestDataDtoField.commandId]?: string;
-	[ISuggestDataDtoField.commandArguments]?: any[];
+	[ISuggestDataDtoField.commandArguments]?: unknown[];
 	// not-standard
 	x?: ChainedCacheId;
 }
@@ -2486,6 +2559,7 @@ export interface IChatUsageDto {
 	kind: 'usage';
 	promptTokens: number;
 	completionTokens: number;
+	outputBuffer?: number;
 	promptTokenDetails?: readonly { category: string; label: string; percentageOfPrompt: number }[];
 }
 
@@ -3513,6 +3587,10 @@ export interface ChatSessionOptionUpdateDto2 {
 	readonly value: string | IChatSessionProviderOptionItem;
 }
 
+export interface ChatSessionContentContextDto {
+	readonly initialSessionOptions?: ReadonlyArray<{ optionId: string; value: string }>;
+}
+
 export interface ChatSessionDto {
 	id: string;
 	resource: UriComponents;
@@ -3525,7 +3603,8 @@ export interface ChatSessionDto {
 }
 
 export interface IChatSessionProviderOptions {
-	optionGroups?: IChatSessionProviderOptionGroup[];
+	optionGroups?: readonly IChatSessionProviderOptionGroup[];
+	newSessionOptions?: Record<string, string | IChatSessionProviderOptionItem>;
 }
 
 export interface IChatSessionItemsChange {
@@ -3538,7 +3617,6 @@ export interface MainThreadChatSessionsShape extends IDisposable {
 	$unregisterChatSessionItemController(controllerHandle: number): void;
 	$updateChatSessionItems(controllerHandle: number, change: IChatSessionItemsChange): Promise<void>;
 	$addOrUpdateChatSessionItem(controllerHandle: number, item: Dto<IChatSessionItem>): Promise<void>;
-	$onDidChangeChatSessionItems(controllerHandle: number): void;
 	$onDidCommitChatSessionItem(controllerHandle: number, original: UriComponents, modified: UriComponents): void;
 	$registerChatSessionContentProvider(handle: number, chatSessionScheme: string): void;
 	$unregisterChatSessionContentProvider(handle: number): void;
@@ -3553,9 +3631,9 @@ export interface MainThreadChatSessionsShape extends IDisposable {
 export interface ExtHostChatSessionsShape {
 	$refreshChatSessionItems(providerHandle: number, token: CancellationToken): Promise<void>;
 	$onDidChangeChatSessionItemState(providerHandle: number, sessionResource: UriComponents, archived: boolean): void;
-	$newChatSessionItem(controllerHandle: number, request: Dto<IChatAgentRequest>, token: CancellationToken): Promise<Dto<IChatSessionItem> | undefined>;
+	$newChatSessionItem(controllerHandle: number, request: IChatNewSessionRequest, token: CancellationToken): Promise<Dto<IChatSessionItem> | undefined>;
 
-	$provideChatSessionContent(providerHandle: number, sessionResource: UriComponents, token: CancellationToken): Promise<ChatSessionDto>;
+	$provideChatSessionContent(providerHandle: number, sessionResource: UriComponents, context: ChatSessionContentContextDto, token: CancellationToken): Promise<ChatSessionDto>;
 	$interruptChatSessionActiveResponse(providerHandle: number, sessionResource: UriComponents, requestId: string): Promise<void>;
 	$disposeChatSessionContent(providerHandle: number, sessionResource: UriComponents): Promise<void>;
 	$invokeChatSessionRequestHandler(providerHandle: number, sessionResource: UriComponents, request: IChatAgentRequest, history: any[], token: CancellationToken): Promise<IChatAgentResult>;
@@ -3584,8 +3662,23 @@ export interface GitRefDto {
 	readonly revision: string;
 }
 
+export interface GitChangeDto {
+	readonly uri: UriComponents;
+	readonly originalUri: UriComponents | undefined;
+	readonly modifiedUri: UriComponents | undefined;
+}
+
+export interface GitDiffChangeDto extends GitChangeDto {
+	readonly insertions: number;
+	readonly deletions: number;
+}
+
 export interface GitRepositoryStateDto {
 	readonly HEAD?: GitBranchDto;
+	readonly mergeChanges: readonly GitChangeDto[];
+	readonly indexChanges: readonly GitChangeDto[];
+	readonly workingTreeChanges: readonly GitChangeDto[];
+	readonly untrackedChanges: readonly GitChangeDto[];
 }
 
 export interface GitBranchDto {
@@ -3593,11 +3686,17 @@ export interface GitBranchDto {
 	readonly commit?: string;
 	readonly type: GitRefTypeDto;
 	readonly remote?: string;
+	readonly base?: GitBaseRefDto;
 	readonly upstream?: GitUpstreamRefDto;
 	readonly ahead?: number;
 	readonly behind?: number;
 }
 
+export interface GitBaseRefDto {
+	readonly name: string;
+	readonly isProtected: boolean;
+}
+
 export interface GitUpstreamRefDto {
 	readonly remote: string;
 	readonly name: string;
@@ -3609,6 +3708,7 @@ export interface ExtHostGitExtensionShape {
 	$openRepository(root: UriComponents): Promise<{ handle: number; rootUri: UriComponents; state: GitRepositoryStateDto } | undefined>;
 	$getRefs(handle: number, query: GitRefQueryDto, token?: CancellationToken): Promise<GitRefDto[]>;
 	$getRepositoryState(handle: number): Promise<GitRepositoryStateDto | undefined>;
+	$diffBetweenWithStats(handle: number, ref1: string, ref2: string, path?: string): Promise<GitDiffChangeDto[]>;
 }
 
 // --- proxy identifiers
@@ -3695,6 +3795,7 @@ export const MainContext = {
 	MainThreadChatOutputRenderer: createProxyIdentifier<MainThreadChatOutputRendererShape>('MainThreadChatOutputRenderer'),
 	MainThreadChatContext: createProxyIdentifier<MainThreadChatContextShape>('MainThreadChatContext'),
 	MainThreadChatDebug: createProxyIdentifier<MainThreadChatDebugShape>('MainThreadChatDebug'),
+	MainThreadBrowsers: createProxyIdentifier<MainThreadBrowsersShape>('MainThreadBrowsers'),
 };
 
 export const ExtHostContext = {
@@ -3775,4 +3876,5 @@ export const ExtHostContext = {
 	ExtHostDataChannels: createProxyIdentifier<ExtHostDataChannelsShape>('ExtHostDataChannels'),
 	ExtHostChatSessions: createProxyIdentifier<ExtHostChatSessionsShape>('ExtHostChatSessions'),
 	ExtHostGitExtension: createProxyIdentifier<ExtHostGitExtensionShape>('ExtHostGitExtension'),
+	ExtHostBrowsers: createProxyIdentifier<ExtHostBrowsersShape>('ExtHostBrowsers'),
 };
diff --git a/src/vs/workbench/api/common/extHostApiDeprecationService.ts b/src/vs/workbench/api/common/extHostApiDeprecationService.ts
index 9a72ce444c028..da3efe1bad37f 100644
--- a/src/vs/workbench/api/common/extHostApiDeprecationService.ts
+++ b/src/vs/workbench/api/common/extHostApiDeprecationService.ts
@@ -12,7 +12,7 @@ import { IExtHostRpcService } from './extHostRpcService.js';
 export interface IExtHostApiDeprecationService {
 	readonly _serviceBrand: undefined;
 
-	report(apiId: string, extension: IExtensionDescription, migrationSuggestion: string): void;
+	report(apiId: string, extension: IExtensionDescription, migrationSuggestion: string, options?: { usageId?: string }): void;
 }
 
 export const IExtHostApiDeprecationService = createDecorator<IExtHostApiDeprecationService>('IExtHostApiDeprecationService');
@@ -31,8 +31,8 @@ export class ExtHostApiDeprecationService implements IExtHostApiDeprecationServi
 		this._telemetryShape = rpc.getProxy(extHostProtocol.MainContext.MainThreadTelemetry);
 	}
 
-	public report(apiId: string, extension: IExtensionDescription, migrationSuggestion: string): void {
-		const key = this.getUsageKey(apiId, extension);
+	public report(apiId: string, extension: IExtensionDescription, migrationSuggestion: string, options?: { usageId?: string }): void {
+		const key = this.getUsageKey(apiId, extension, options?.usageId);
 		if (this._reportedUsages.has(key)) {
 			return;
 		}
@@ -45,21 +45,25 @@ export class ExtHostApiDeprecationService implements IExtHostApiDeprecationServi
 		type DeprecationTelemetry = {
 			extensionId: string;
 			apiId: string;
+			usageId: string;
 		};
 		type DeprecationTelemetryMeta = {
 			extensionId: { classification: 'SystemMetaData'; purpose: 'PerformanceAndHealth'; comment: 'The id of the extension that is using the deprecated API' };
 			apiId: { classification: 'SystemMetaData'; purpose: 'PerformanceAndHealth'; comment: 'The id of the deprecated API' };
+			usageId: { classification: 'SystemMetaData'; purpose: 'PerformanceAndHealth'; comment: 'Id identifying the specific usage of the deprecated API' };
 			owner: 'mjbvz';
 			comment: 'Helps us gain insights on extensions using deprecated API so we can assist in migration to new API';
 		};
 		this._telemetryShape.$publicLog2<DeprecationTelemetry, DeprecationTelemetryMeta>('extHostDeprecatedApiUsage', {
 			extensionId: extension.identifier.value,
 			apiId: apiId,
+			usageId: options?.usageId ?? '',
 		});
 	}
 
-	private getUsageKey(apiId: string, extension: IExtensionDescription): string {
-		return `${apiId}-${extension.identifier.value}`;
+	private getUsageKey(apiId: string, extension: IExtensionDescription, usageId?: string): string {
+		const rootKey = `${apiId}-${extension.identifier.value}`;
+		return usageId ? `${rootKey}-${usageId}` : rootKey;
 	}
 }
 
diff --git a/src/vs/workbench/api/common/extHostBrowsers.ts b/src/vs/workbench/api/common/extHostBrowsers.ts
new file mode 100644
index 0000000000000..a66e311340977
--- /dev/null
+++ b/src/vs/workbench/api/common/extHostBrowsers.ts
@@ -0,0 +1,271 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Emitter, Event } from '../../../base/common/event.js';
+import { Disposable, DisposableMap } from '../../../base/common/lifecycle.js';
+import { URI } from '../../../base/common/uri.js';
+import { Codicon } from '../../../base/common/codicons.js';
+import type * as vscode from 'vscode';
+import { BrowserTabDto, ExtHostBrowsersShape, IMainContext, MainContext, MainThreadBrowsersShape } from './extHost.protocol.js';
+import { generateUuid } from '../../../base/common/uuid.js';
+import * as extHostTypes from './extHostTypes.js';
+import * as typeConverters from './extHostTypeConverters.js';
+import { CDPEvent, CDPRequest, CDPResponse } from '../../../platform/browserView/common/cdp/types.js';
+
+// #region Internal browser tab object
+
+class ExtHostBrowserTab {
+	private _url: string;
+	private _title: string;
+	private _favicon: string | undefined;
+
+	readonly value: vscode.BrowserTab;
+
+	constructor(
+		readonly id: string,
+		private readonly _proxy: MainThreadBrowsersShape,
+		private readonly _sessions: DisposableMap<string, ExtHostBrowserCDPSession>,
+		data: BrowserTabDto,
+	) {
+		this._url = data.url;
+		this._title = data.title;
+		this._favicon = data.favicon;
+
+		const that = this;
+		this.value = {
+			get url(): string { return that._url; },
+			get title(): string { return that._title; },
+			get icon(): vscode.IconPath {
+				return that._favicon
+					? URI.parse(that._favicon)
+					: new extHostTypes.ThemeIcon(Codicon.globe.id) as vscode.ThemeIcon;
+			},
+			startCDPSession(): Promise<vscode.BrowserCDPSession> {
+				return that._startCDPSession();
+			},
+			close(): Promise<void> {
+				return that._close();
+			}
+		};
+	}
+
+	update(data: BrowserTabDto): boolean {
+		let changed = false;
+		if (data.url !== this._url) {
+			this._url = data.url;
+			changed = true;
+		}
+		if (data.title !== this._title) {
+			this._title = data.title;
+			changed = true;
+		}
+		if (data.favicon !== this._favicon) {
+			this._favicon = data.favicon;
+			changed = true;
+		}
+		return changed;
+	}
+
+	private async _startCDPSession(): Promise<vscode.BrowserCDPSession> {
+		const sessionId = generateUuid();
+		await this._proxy.$startCDPSession(sessionId, this.id);
+		const session = new ExtHostBrowserCDPSession(sessionId, this._proxy);
+		this._sessions.set(sessionId, session);
+		return session.value;
+	}
+
+	private async _close(): Promise<void> {
+		await this._proxy.$closeBrowserTab(this.id);
+	}
+}
+
+// #endregion
+
+// #region CDP Session
+
+class ExtHostBrowserCDPSession {
+	private readonly _onDidReceiveMessage = new Emitter<unknown>();
+	private readonly _onDidClose = new Emitter<void>();
+
+	private _closed = false;
+
+	readonly value: vscode.BrowserCDPSession;
+
+	constructor(
+		readonly id: string,
+		private readonly _proxy: MainThreadBrowsersShape,
+	) {
+		const that = this;
+		this.value = {
+			get onDidReceiveMessage(): Event<unknown> { return that._onDidReceiveMessage.event; },
+			get onDidClose(): Event<void> { return that._onDidClose.event; },
+			sendMessage(message: unknown): Promise<void> {
+				return that._sendMessage(message as CDPRequest);
+			},
+			close(): Promise<void> {
+				return that._close();
+			}
+		};
+	}
+
+	dispose(): void {
+		this._onDidReceiveMessage.dispose();
+		this._onDidClose.dispose();
+	}
+
+	private async _sendMessage(message: CDPRequest): Promise<void> {
+		if (this._closed) {
+			throw new Error('Session is closed');
+		}
+		if (!message || typeof message !== 'object') {
+			throw new Error('Message must be an object');
+		}
+		if (typeof message.id !== 'number') {
+			throw new Error('Message must have a numeric id');
+		}
+		if (typeof message.method !== 'string') {
+			throw new Error('Message must have a method string');
+		}
+		if (message.params !== undefined && typeof message.params !== 'object') {
+			throw new Error('Message params must be an object');
+		}
+		if (message.sessionId !== undefined && typeof message.sessionId !== 'string') {
+			throw new Error('Message sessionId must be a string');
+		}
+		await this._proxy.$sendCDPMessage(this.id, { id: message.id, method: message.method, params: message.params, sessionId: message.sessionId });
+	}
+
+	private async _close(): Promise<void> {
+		this._closed = true;
+		await this._proxy.$closeCDPSession(this.id);
+	}
+
+	// Called from main thread
+	_acceptMessage(message: unknown): void {
+		this._onDidReceiveMessage.fire(message);
+	}
+
+	_acceptClosed(): void {
+		this._closed = true;
+		this._onDidClose.fire();
+	}
+}
+
+// #endregion
+
+export class ExtHostBrowsers extends Disposable implements ExtHostBrowsersShape {
+	private readonly _proxy: MainThreadBrowsersShape;
+	private readonly _browserTabs = new Map<string, ExtHostBrowserTab>();
+	private readonly _sessions = this._register(new DisposableMap<string, ExtHostBrowserCDPSession>());
+
+	private _activeBrowserTabId: string | undefined;
+
+	private readonly _onDidOpenBrowserTab = this._register(new Emitter<vscode.BrowserTab>());
+	readonly onDidOpenBrowserTab: Event<vscode.BrowserTab> = this._onDidOpenBrowserTab.event;
+
+	private readonly _onDidCloseBrowserTab = this._register(new Emitter<vscode.BrowserTab>());
+	readonly onDidCloseBrowserTab: Event<vscode.BrowserTab> = this._onDidCloseBrowserTab.event;
+
+	private readonly _onDidChangeActiveBrowserTab = this._register(new Emitter<vscode.BrowserTab | undefined>());
+	readonly onDidChangeActiveBrowserTab: Event<vscode.BrowserTab | undefined> = this._onDidChangeActiveBrowserTab.event;
+
+	private readonly _onDidChangeBrowserTabState = this._register(new Emitter<vscode.BrowserTab>());
+	readonly onDidChangeBrowserTabState: Event<vscode.BrowserTab> = this._onDidChangeBrowserTabState.event;
+
+	constructor(mainContext: IMainContext) {
+		super();
+		this._proxy = mainContext.getProxy(MainContext.MainThreadBrowsers);
+	}
+
+	// #region Public API (called from extension code)
+
+	get browserTabs(): readonly vscode.BrowserTab[] {
+		return [...this._browserTabs.values()].map(t => t.value);
+	}
+
+	get activeBrowserTab(): vscode.BrowserTab | undefined {
+		if (this._activeBrowserTabId) {
+			return this._browserTabs.get(this._activeBrowserTabId)?.value;
+		}
+		return undefined;
+	}
+
+	async openBrowserTab(url: string, options?: vscode.BrowserTabShowOptions): Promise<vscode.BrowserTab> {
+		const viewColumn = typeConverters.ViewColumn.from(options?.viewColumn);
+		const dto = await this._proxy.$openBrowserTab(url, viewColumn, {
+			preserveFocus: options?.preserveFocus,
+			inactive: options?.background,
+		});
+
+		return this._getOrCreateTab(dto).value;
+	}
+
+	// #endregion
+
+	// #region Internal helpers
+
+	private _getOrCreateTab(dto: BrowserTabDto): ExtHostBrowserTab {
+		let tab = this._browserTabs.get(dto.id);
+		if (!tab) {
+			tab = new ExtHostBrowserTab(dto.id, this._proxy, this._sessions, dto);
+			this._browserTabs.set(dto.id, tab);
+			this._onDidOpenBrowserTab.fire(tab.value);
+		} else {
+			tab.update(dto);
+		}
+		return tab;
+	}
+
+	// #endregion
+
+	// #region Main thread callbacks
+
+	$onDidOpenBrowserTab(dto: BrowserTabDto): void {
+		this._getOrCreateTab(dto);
+	}
+
+	$onDidCloseBrowserTab(browserId: string): void {
+		const tab = this._browserTabs.get(browserId);
+		if (tab) {
+			this._browserTabs.delete(browserId);
+			if (this._activeBrowserTabId === browserId) {
+				this._activeBrowserTabId = undefined;
+			}
+			this._onDidCloseBrowserTab.fire(tab.value);
+		}
+	}
+
+	$onDidChangeActiveBrowserTab(dto: BrowserTabDto | undefined): void {
+		this._activeBrowserTabId = dto?.id;
+		if (dto) {
+			this._getOrCreateTab(dto);
+		}
+		this._onDidChangeActiveBrowserTab.fire(this.activeBrowserTab);
+	}
+
+	$onDidChangeBrowserTabState(browserId: string, data: BrowserTabDto): void {
+		const tab = this._browserTabs.get(browserId);
+		if (tab && tab.update(data)) {
+			this._onDidChangeBrowserTabState.fire(tab.value);
+		}
+	}
+
+	$onCDPSessionMessage(sessionId: string, message: CDPResponse | CDPEvent): void {
+		const session = this._sessions.get(sessionId);
+		if (session) {
+			session._acceptMessage(message);
+		}
+	}
+
+	$onCDPSessionClosed(sessionId: string): void {
+		const session = this._sessions.get(sessionId);
+		if (session) {
+			session._acceptClosed();
+			this._sessions.deleteAndDispose(sessionId);
+		}
+	}
+
+	// #endregion
+}
diff --git a/src/vs/workbench/api/common/extHostChatAgents2.ts b/src/vs/workbench/api/common/extHostChatAgents2.ts
index 06553d2cb0fad..860c72777663f 100644
--- a/src/vs/workbench/api/common/extHostChatAgents2.ts
+++ b/src/vs/workbench/api/common/extHostChatAgents2.ts
@@ -22,12 +22,12 @@ import { ILogService } from '../../../platform/log/common/log.js';
 import { isChatViewTitleActionContext } from '../../contrib/chat/common/actions/chatActions.js';
 import { IChatAgentRequest, IChatAgentResult, IChatAgentResultTimings, UserSelectedTools } from '../../contrib/chat/common/participants/chatAgents.js';
 import { ChatAgentVoteDirection, IChatContentReference, IChatFollowup, IChatResponseErrorDetails, IChatUserActionEvent, IChatVoteAction } from '../../contrib/chat/common/chatService/chatService.js';
-import { IChatRequestHooks } from '../../contrib/chat/common/promptSyntax/hookSchema.js';
+import { ChatRequestHooks } from '../../contrib/chat/common/promptSyntax/hookSchema.js';
 import { LocalChatSessionUri } from '../../contrib/chat/common/model/chatUri.js';
 import { ChatAgentLocation } from '../../contrib/chat/common/constants.js';
 import { checkProposedApiEnabled, isProposedApiEnabled } from '../../services/extensions/common/extensions.js';
 import { Dto } from '../../services/extensions/common/proxyIdentifier.js';
-import { ExtHostChatAgentsShape2, IChatAgentCompletionItem, IChatAgentHistoryEntryDto, IChatAgentProgressShape, IChatProgressDto, IChatSessionContextDto, IExtensionChatAgentMetadata, IMainContext, MainContext, MainThreadChatAgentsShape2 } from './extHost.protocol.js';
+import { ExtHostChatAgentsShape2, IChatAgentCompletionItem, IChatAgentHistoryEntryDto, IChatAgentProgressShape, IChatProgressDto, IChatSessionContextDto, ICustomAgentDto, IExtensionChatAgentMetadata, IInstructionDto, IMainContext, ISkillDto, MainContext, MainThreadChatAgentsShape2 } from './extHost.protocol.js';
 import { CommandsConverter, ExtHostCommands } from './extHostCommands.js';
 import { ExtHostDiagnostics } from './extHostDiagnostics.js';
 import { ExtHostDocuments } from './extHostDocuments.js';
@@ -440,6 +440,7 @@ export class ChatAgentResponseStream {
 						kind: 'usage',
 						promptTokens: usage.promptTokens,
 						completionTokens: usage.completionTokens,
+						outputBuffer: usage.outputBuffer,
 						promptTokenDetails: usage.promptTokenDetails
 					};
 					_report(dto);
@@ -456,7 +457,7 @@ interface InFlightChatRequest {
 	requestId: string;
 	extRequest: vscode.ChatRequest;
 	extension: IRelaxedExtensionDescription;
-	hooks?: IChatRequestHooks;
+	hooks?: ChatRequestHooks;
 	yieldRequested: boolean;
 }
 
@@ -487,6 +488,17 @@ export class ExtHostChatAgents2 extends Disposable implements ExtHostChatAgentsS
 	private readonly _onDidDisposeChatSession = this._register(new Emitter<string>());
 	readonly onDidDisposeChatSession = this._onDidDisposeChatSession.event;
 
+	private readonly _onDidChangeCustomAgents = this._register(new Emitter<void>());
+	readonly onDidChangeCustomAgents = this._onDidChangeCustomAgents.event;
+	private readonly _onDidChangeInstructions = this._register(new Emitter<void>());
+	readonly onDidChangeInstructions = this._onDidChangeInstructions.event;
+	private readonly _onDidChangeSkills = this._register(new Emitter<void>());
+	readonly onDidChangeSkills = this._onDidChangeSkills.event;
+
+	private _customAgents: vscode.ChatResource[] = [];
+	private _instructions: vscode.ChatResource[] = [];
+	private _skills: vscode.ChatResource[] = [];
+
 	private _activeChatPanelSessionResource: URI | undefined;
 
 	private readonly _onDidChangeActiveChatPanelSessionResource = this._register(new Emitter<URI | undefined>());
@@ -496,6 +508,33 @@ export class ExtHostChatAgents2 extends Disposable implements ExtHostChatAgentsS
 		return this._activeChatPanelSessionResource;
 	}
 
+	get customAgents(): readonly vscode.ChatResource[] {
+		return this._customAgents;
+	}
+
+	get instructions(): readonly vscode.ChatResource[] {
+		return this._instructions;
+	}
+
+	get skills(): readonly vscode.ChatResource[] {
+		return this._skills;
+	}
+
+	$acceptCustomAgents(agents: ICustomAgentDto[]): void {
+		this._customAgents = agents.map(a => Object.freeze({ uri: URI.revive(a.uri) }));
+		this._onDidChangeCustomAgents.fire();
+	}
+
+	$acceptInstructions(instructions: IInstructionDto[]): void {
+		this._instructions = instructions.map(i => Object.freeze({ uri: URI.revive(i.uri) }));
+		this._onDidChangeInstructions.fire();
+	}
+
+	$acceptSkills(skills: ISkillDto[]): void {
+		this._skills = skills.map(s => Object.freeze({ uri: URI.revive(s.uri) }));
+		this._onDidChangeSkills.fire();
+	}
+
 	constructor(
 		mainContext: IMainContext,
 		private readonly _logService: ILogService,
@@ -1007,7 +1046,8 @@ export class ExtHostChatAgents2 extends Disposable implements ExtHostChatAgentsS
 		}
 
 		const history = await this.prepareHistoryTurns(agent.extension, agent.id, { history: context });
-		return await agent.provideTitle({ history, yieldRequested: false }, token);
+		const sessionResource = context[0]?.request.sessionResource ? URI.revive(context[0].request.sessionResource) : undefined;
+		return await agent.provideTitle({ history, sessionResource, yieldRequested: false }, token);
 	}
 
 	async $provideChatSummary(handle: number, context: IChatAgentHistoryEntryDto[], token: CancellationToken): Promise<string | undefined> {
@@ -1017,7 +1057,8 @@ export class ExtHostChatAgents2 extends Disposable implements ExtHostChatAgentsS
 		}
 
 		const history = await this.prepareHistoryTurns(agent.extension, agent.id, { history: context });
-		return await agent.provideSummary({ history, yieldRequested: false }, token);
+		const sessionResource = context[0]?.request.sessionResource ? URI.revive(context[0].request.sessionResource) : undefined;
+		return await agent.provideSummary({ history, sessionResource, yieldRequested: false }, token);
 	}
 }
 
diff --git a/src/vs/workbench/api/common/extHostChatDebug.ts b/src/vs/workbench/api/common/extHostChatDebug.ts
index bf9b6495b845e..44cccc60a61c9 100644
--- a/src/vs/workbench/api/common/extHostChatDebug.ts
+++ b/src/vs/workbench/api/common/extHostChatDebug.ts
@@ -4,12 +4,13 @@
  *--------------------------------------------------------------------------------------------*/
 
 import type * as vscode from 'vscode';
+import { VSBuffer } from '../../../base/common/buffer.js';
 import { CancellationToken } from '../../../base/common/cancellation.js';
 import { Emitter } from '../../../base/common/event.js';
 import { Disposable, DisposableStore, toDisposable } from '../../../base/common/lifecycle.js';
 import { URI, UriComponents } from '../../../base/common/uri.js';
 import { ExtHostChatDebugShape, IChatDebugEventDto, IChatDebugResolvedEventContentDto, MainContext, MainThreadChatDebugShape } from './extHost.protocol.js';
-import { ChatDebugMessageContentType, ChatDebugSubagentStatus, ChatDebugToolCallResult } from './extHostTypes.js';
+import { ChatDebugGenericEvent, ChatDebugLogLevel, ChatDebugMessageContentType, ChatDebugMessageSection, ChatDebugModelTurnEvent, ChatDebugSubagentInvocationEvent, ChatDebugSubagentStatus, ChatDebugToolCallEvent, ChatDebugToolCallResult, ChatDebugUserMessageEvent, ChatDebugAgentResponseEvent } from './extHostTypes.js';
 import { IExtHostRpcService } from './extHostRpcService.js';
 
 export class ExtHostChatDebug extends Disposable implements ExtHostChatDebugShape {
@@ -21,6 +22,12 @@ export class ExtHostChatDebug extends Disposable implements ExtHostChatDebugShap
 	/** Progress pipelines keyed by `${handle}:${sessionResource}` so multiple sessions can stream concurrently. */
 	private readonly _activeProgress = new Map<string, DisposableStore>();
 
+	private readonly _onDidAddCoreEvent = this._register(new Emitter<vscode.ChatDebugEvent>({
+		onWillAddFirstListener: () => this._proxy.$subscribeToCoreDebugEvents(),
+		onDidRemoveLastListener: () => this._proxy.$unsubscribeFromCoreDebugEvents(),
+	}));
+	readonly onDidAddCoreEvent = this._onDidAddCoreEvent.event;
+
 	constructor(
 		@IExtHostRpcService extHostRpc: IExtHostRpcService,
 	) {
@@ -145,6 +152,7 @@ export class ExtHostChatDebug extends Disposable implements ExtHostChatDebugShap
 					...base,
 					kind: 'modelTurn',
 					model: e.model,
+					requestName: e.requestName,
 					inputTokens: e.inputTokens,
 					outputTokens: e.outputTokens,
 					totalTokens: e.totalTokens,
@@ -197,13 +205,14 @@ export class ExtHostChatDebug extends Disposable implements ExtHostChatDebugShap
 				};
 			}
 			default: {
-				// Final fallback: treat as generic
 				const generic = event as vscode.ChatDebugGenericEvent;
+				const rawName = generic.name;
+				const rawDetails = generic.details;
 				return {
 					...base,
 					kind: 'generic',
-					name: generic.name ?? '',
-					details: generic.details,
+					name: typeof rawName === 'string' ? rawName : '',
+					details: typeof rawDetails === 'string' ? rawDetails : undefined,
 					level: generic.level ?? 1,
 					category: generic.category,
 				};
@@ -252,11 +261,150 @@ export class ExtHostChatDebug extends Disposable implements ExtHostChatDebugShap
 					sections: msg.sections.map(s => ({ name: s.name, content: s.content })),
 				};
 			}
+			case 'toolCallContent': {
+				const tc = result as vscode.ChatDebugEventToolCallContent;
+				return {
+					kind: 'toolCall',
+					toolName: tc.toolName,
+					result: tc.result === ChatDebugToolCallResult.Success ? 'success'
+						: tc.result === ChatDebugToolCallResult.Error ? 'error'
+							: undefined,
+					durationInMillis: tc.durationInMillis,
+					input: tc.input,
+					output: tc.output,
+				};
+			}
+			case 'modelTurnContent': {
+				const mt = result as vscode.ChatDebugEventModelTurnContent;
+				return {
+					kind: 'modelTurn',
+					requestName: mt.requestName,
+					model: mt.model,
+					status: mt.status,
+					durationInMillis: mt.durationInMillis,
+					timeToFirstTokenInMillis: mt.timeToFirstTokenInMillis,
+					maxInputTokens: mt.maxInputTokens,
+					maxOutputTokens: mt.maxOutputTokens,
+					inputTokens: mt.inputTokens,
+					outputTokens: mt.outputTokens,
+					cachedTokens: mt.cachedTokens,
+					totalTokens: mt.totalTokens,
+					errorMessage: mt.errorMessage,
+					sections: mt.sections?.map(s => ({ name: s.name, content: s.content })),
+				};
+			}
+			default:
+				return undefined;
+		}
+	}
+
+	private _deserializeEvent(dto: IChatDebugEventDto): vscode.ChatDebugEvent | undefined {
+		const created = new Date(dto.created);
+		const sessionResource = dto.sessionResource ? URI.revive(dto.sessionResource) : undefined;
+		switch (dto.kind) {
+			case 'toolCall': {
+				const evt = new ChatDebugToolCallEvent(dto.toolName, created);
+				evt.id = dto.id;
+				evt.sessionResource = sessionResource;
+				evt.parentEventId = dto.parentEventId;
+				evt.toolCallId = dto.toolCallId;
+				evt.input = dto.input;
+				evt.output = dto.output;
+				evt.result = dto.result === 'success' ? ChatDebugToolCallResult.Success
+					: dto.result === 'error' ? ChatDebugToolCallResult.Error
+						: undefined;
+				evt.durationInMillis = dto.durationInMillis;
+				return evt;
+			}
+			case 'modelTurn': {
+				const evt = new ChatDebugModelTurnEvent(created);
+				evt.id = dto.id;
+				evt.sessionResource = sessionResource;
+				evt.parentEventId = dto.parentEventId;
+				evt.model = dto.model;
+				evt.inputTokens = dto.inputTokens;
+				evt.outputTokens = dto.outputTokens;
+				evt.totalTokens = dto.totalTokens;
+				evt.durationInMillis = dto.durationInMillis;
+				return evt;
+			}
+			case 'generic': {
+				const evt = new ChatDebugGenericEvent(dto.name, dto.level as ChatDebugLogLevel, created);
+				evt.id = dto.id;
+				evt.sessionResource = sessionResource;
+				evt.parentEventId = dto.parentEventId;
+				evt.details = dto.details;
+				evt.category = dto.category;
+				return evt;
+			}
+			case 'subagentInvocation': {
+				const evt = new ChatDebugSubagentInvocationEvent(dto.agentName, created);
+				evt.id = dto.id;
+				evt.sessionResource = sessionResource;
+				evt.parentEventId = dto.parentEventId;
+				evt.description = dto.description;
+				evt.status = dto.status === 'running' ? ChatDebugSubagentStatus.Running
+					: dto.status === 'completed' ? ChatDebugSubagentStatus.Completed
+						: dto.status === 'failed' ? ChatDebugSubagentStatus.Failed
+							: undefined;
+				evt.durationInMillis = dto.durationInMillis;
+				evt.toolCallCount = dto.toolCallCount;
+				evt.modelTurnCount = dto.modelTurnCount;
+				return evt;
+			}
+			case 'userMessage': {
+				const evt = new ChatDebugUserMessageEvent(dto.message, created);
+				evt.id = dto.id;
+				evt.sessionResource = sessionResource;
+				evt.parentEventId = dto.parentEventId;
+				evt.sections = dto.sections.map(s => new ChatDebugMessageSection(s.name, s.content));
+				return evt;
+			}
+			case 'agentResponse': {
+				const evt = new ChatDebugAgentResponseEvent(dto.message, created);
+				evt.id = dto.id;
+				evt.sessionResource = sessionResource;
+				evt.parentEventId = dto.parentEventId;
+				evt.sections = dto.sections.map(s => new ChatDebugMessageSection(s.name, s.content));
+				return evt;
+			}
 			default:
 				return undefined;
 		}
 	}
 
+	$onCoreDebugEvent(dto: IChatDebugEventDto): void {
+		const event = this._deserializeEvent(dto);
+		if (event) {
+			this._onDidAddCoreEvent.fire(event);
+		}
+	}
+
+	async $exportChatDebugLog(_handle: number, sessionResource: UriComponents, coreEventDtos: IChatDebugEventDto[], sessionTitle: string | undefined, token: CancellationToken): Promise<VSBuffer | undefined> {
+		if (!this._provider?.provideChatDebugLogExport) {
+			return undefined;
+		}
+		const sessionUri = URI.revive(sessionResource);
+		const coreEvents = coreEventDtos.map(dto => this._deserializeEvent(dto)).filter((e): e is vscode.ChatDebugEvent => e !== undefined);
+		const options: vscode.ChatDebugLogExportOptions = { coreEvents, sessionTitle };
+		const result = await this._provider.provideChatDebugLogExport(sessionUri, options, token);
+		if (!result) {
+			return undefined;
+		}
+		return VSBuffer.wrap(result);
+	}
+
+	async $importChatDebugLog(_handle: number, data: VSBuffer, token: CancellationToken): Promise<{ uri: UriComponents; sessionTitle?: string } | undefined> {
+		if (!this._provider?.resolveChatDebugLogImport) {
+			return undefined;
+		}
+		const result = await this._provider.resolveChatDebugLogImport(data.buffer, token);
+		if (!result) {
+			return undefined;
+		}
+		return { uri: result.uri, sessionTitle: result.sessionTitle };
+	}
+
 	override dispose(): void {
 		for (const store of this._activeProgress.values()) {
 			store.dispose();
diff --git a/src/vs/workbench/api/common/extHostChatSessions.ts b/src/vs/workbench/api/common/extHostChatSessions.ts
index f884d985ddacf..62ff2c6c10204 100644
--- a/src/vs/workbench/api/common/extHostChatSessions.ts
+++ b/src/vs/workbench/api/common/extHostChatSessions.ts
@@ -13,17 +13,16 @@ import { Disposable, DisposableStore, toDisposable } from '../../../base/common/
 import { ResourceMap, ResourceSet } from '../../../base/common/map.js';
 import { MarshalledId } from '../../../base/common/marshallingIds.js';
 import * as objects from '../../../base/common/objects.js';
-import { basename } from '../../../base/common/resources.js';
 import { URI, UriComponents } from '../../../base/common/uri.js';
 import { SymbolKind, SymbolKinds } from '../../../editor/common/languages.js';
 import { IExtensionDescription } from '../../../platform/extensions/common/extensions.js';
 import { ILogService } from '../../../platform/log/common/log.js';
-import { IChatRequestVariableEntry, IDiagnosticVariableEntryFilterData, IPromptFileVariableEntry, ISymbolVariableEntry, PromptFileVariableKind } from '../../contrib/chat/common/attachments/chatVariableEntries.js';
-import { IChatSessionProviderOptionItem } from '../../contrib/chat/common/chatSessionsService.js';
+import { IChatRequestVariableEntry, IDiagnosticVariableEntryFilterData, ISymbolVariableEntry, PromptFileVariableKind, toPromptFileVariableEntry } from '../../contrib/chat/common/attachments/chatVariableEntries.js';
+import { IChatNewSessionRequest, IChatSessionProviderOptionItem } from '../../contrib/chat/common/chatSessionsService.js';
 import { ChatAgentLocation } from '../../contrib/chat/common/constants.js';
 import { IChatAgentRequest, IChatAgentResult } from '../../contrib/chat/common/participants/chatAgents.js';
 import { Proxied } from '../../services/extensions/common/proxyIdentifier.js';
-import { ChatSessionDto, ExtHostChatSessionsShape, IChatAgentProgressShape, IChatSessionProviderOptions, MainContext, MainThreadChatSessionsShape } from './extHost.protocol.js';
+import { ChatSessionContentContextDto, ChatSessionDto, ExtHostChatSessionsShape, IChatAgentProgressShape, IChatSessionProviderOptions, MainContext, MainThreadChatSessionsShape } from './extHost.protocol.js';
 import { ChatAgentResponseStream } from './extHostChatAgents2.js';
 import { CommandsConverter, ExtHostCommands } from './extHostCommands.js';
 import { ExtHostLanguageModels } from './extHostLanguageModels.js';
@@ -332,7 +331,7 @@ export class ExtHostChatSessions extends Disposable implements ExtHostChatSessio
 	/**
 	 * Store option groups with onSearch callbacks per provider handle
 	 */
-	private readonly _providerOptionGroups = new Map<number, vscode.ChatSessionProviderOptionGroup[]>();
+	private readonly _providerOptionGroups = new Map<number, readonly vscode.ChatSessionProviderOptionGroup[]>();
 
 	constructor(
 		private readonly commands: ExtHostCommands,
@@ -500,7 +499,7 @@ export class ExtHostChatSessions extends Disposable implements ExtHostChatSessio
 		});
 	}
 
-	async $provideChatSessionContent(handle: number, sessionResourceComponents: UriComponents, token: CancellationToken): Promise<ChatSessionDto> {
+	async $provideChatSessionContent(handle: number, sessionResourceComponents: UriComponents, context: ChatSessionContentContextDto, token: CancellationToken): Promise<ChatSessionDto> {
 		const provider = this._chatSessionContentProviders.get(handle);
 		if (!provider) {
 			throw new Error(`No provider for handle ${handle}`);
@@ -508,7 +507,9 @@ export class ExtHostChatSessions extends Disposable implements ExtHostChatSessio
 
 		const sessionResource = URI.revive(sessionResourceComponents);
 
-		const session = await provider.provider.provideChatSessionContent(sessionResource, token);
+		const session = await provider.provider.provideChatSessionContent(sessionResource, token, {
+			sessionOptions: context?.initialSessionOptions ?? []
+		});
 		if (token.isCancellationRequested) {
 			throw new CancellationError();
 		}
@@ -598,13 +599,17 @@ export class ExtHostChatSessions extends Disposable implements ExtHostChatSessio
 		}
 
 		try {
-			const { optionGroups } = await provider.provideChatSessionProviderOptions(token);
-			if (!optionGroups) {
+			const result = await provider.provideChatSessionProviderOptions(token);
+			if (!result) {
 				return;
 			}
-			this._providerOptionGroups.set(handle, optionGroups);
+			const { optionGroups, newSessionOptions } = result;
+			if (optionGroups) {
+				this._providerOptionGroups.set(handle, optionGroups);
+			}
 			return {
 				optionGroups,
+				newSessionOptions,
 			};
 		} catch (error) {
 			this._logService.error(`Error calling provideChatSessionProviderOptions for handle ${handle}:`, error);
@@ -705,19 +710,16 @@ export class ExtHostChatSessions extends Disposable implements ExtHostChatSessio
 			} satisfies ISymbolVariableEntry;
 		}
 
-		if (URI.isUri(value) && ref.name.startsWith(`prompt:`) &&
-			ref.id.startsWith(PromptFileVariableKind.PromptFile) &&
-			ref.id.endsWith(value.toString())) {
-			return {
-				id: ref.id,
-				name: `prompt:${basename(value)}`,
-				value,
-				kind: 'promptFile',
-				modelDescription: 'Prompt instructions file',
-				isRoot: true,
-				automaticallyAdded: false,
-				range,
-			} satisfies IPromptFileVariableEntry;
+		if (URI.isUri(value) && ref.name.startsWith(`prompt:`)) {
+			if (ref.id.startsWith(PromptFileVariableKind.Instruction)) {
+				return toPromptFileVariableEntry(value, PromptFileVariableKind.Instruction);
+			}
+			if (ref.id.startsWith(PromptFileVariableKind.InstructionReference)) {
+				return toPromptFileVariableEntry(value, PromptFileVariableKind.InstructionReference);
+			}
+			if (ref.id.startsWith(PromptFileVariableKind.PromptFile)) {
+				return toPromptFileVariableEntry(value, PromptFileVariableKind.PromptFile);
+			}
 		}
 
 		const isFile = URI.isUri(value) || (value && typeof value === 'object' && 'uri' in value);
@@ -773,7 +775,7 @@ export class ExtHostChatSessions extends Disposable implements ExtHostChatSessio
 		await controllerData.controller.refreshHandler(token);
 	}
 
-	async $newChatSessionItem(handle: number, request: IChatAgentRequest, token: CancellationToken): Promise<ReturnType<typeof typeConvert.ChatSessionItem.from> | undefined> {
+	async $newChatSessionItem(handle: number, request: IChatNewSessionRequest, token: CancellationToken): Promise<ReturnType<typeof typeConvert.ChatSessionItem.from> | undefined> {
 		const controllerData = this._chatSessionItemControllers.get(handle);
 		if (!controllerData) {
 			this._logService.warn(`No controller found for handle ${handle}`);
@@ -785,10 +787,13 @@ export class ExtHostChatSessions extends Disposable implements ExtHostChatSessio
 			return undefined;
 		}
 
-		const model = await this.getModelForRequest(request, controllerData.extension);
-		const chatRequest = typeConvert.ChatAgentRequest.to(request, undefined, model, [], new Map(), controllerData.extension, this._logService);
-
-		const item = await handler({ request: chatRequest }, token);
+		const item = await handler({
+			request: {
+				prompt: request.prompt,
+				command: request.command
+			},
+			sessionOptions: request.initialSessionOptions ?? [],
+		}, token);
 		if (!item) {
 			return undefined;
 		}
diff --git a/src/vs/workbench/api/common/extHostCommands.ts b/src/vs/workbench/api/common/extHostCommands.ts
index 15c769373b8e5..92e874dc6c91b 100644
--- a/src/vs/workbench/api/common/extHostCommands.ts
+++ b/src/vs/workbench/api/common/extHostCommands.ts
@@ -425,11 +425,11 @@ export class CommandsConverter implements extHostTypeConverter.Command.ICommands
 	}
 
 
-	getActualCommand(...args: any[]): vscode.Command | undefined {
-		return this._cache.get(args[0]);
+	getActualCommand(...args: unknown[]): vscode.Command | undefined {
+		return this._cache.get(args[0] as string);
 	}
 
-	private _executeConvertedCommand<R>(...args: any[]): Promise<R> {
+	private _executeConvertedCommand<R>(...args: unknown[]): Promise<R> {
 		const actualCmd = this.getActualCommand(...args);
 		this._logService.trace('CommandsConverter#EXECUTE', args[0], actualCmd ? actualCmd.command : 'MISSING');
 
diff --git a/src/vs/workbench/api/common/extHostConsoleForwarder.ts b/src/vs/workbench/api/common/extHostConsoleForwarder.ts
index 0255914990050..8bd7fc9a91288 100644
--- a/src/vs/workbench/api/common/extHostConsoleForwarder.ts
+++ b/src/vs/workbench/api/common/extHostConsoleForwarder.ts
@@ -46,13 +46,13 @@ export abstract class AbstractExtHostConsoleForwarder {
 
 		Object.defineProperty(console, method, {
 			set: () => { },
-			get: () => function () {
-				that._handleConsoleCall(method, severity, original, arguments);
+			get: () => (...args: unknown[]) => {
+				that._handleConsoleCall(method, severity, original, args);
 			},
 		});
 	}
 
-	private _handleConsoleCall(method: 'log' | 'info' | 'warn' | 'error' | 'debug', severity: 'log' | 'warn' | 'error' | 'debug', original: (...args: any[]) => void, args: IArguments): void {
+	private _handleConsoleCall(method: 'log' | 'info' | 'warn' | 'error' | 'debug', severity: 'log' | 'warn' | 'error' | 'debug', original: (...args: unknown[]) => void, args: unknown[]): void {
 		this._mainThreadConsole.$logExtensionHostMessage({
 			type: '__$console',
 			severity,
@@ -63,7 +63,7 @@ export abstract class AbstractExtHostConsoleForwarder {
 		}
 	}
 
-	protected abstract _nativeConsoleLogMessage(method: 'log' | 'info' | 'warn' | 'error' | 'debug', original: (...args: any[]) => void, args: IArguments): void;
+	protected abstract _nativeConsoleLogMessage(method: 'log' | 'info' | 'warn' | 'error' | 'debug', original: (...args: unknown[]) => void, args: unknown[]): void;
 
 }
 
@@ -72,7 +72,7 @@ const MAX_LENGTH = 100000;
 /**
  * Prevent circular stringify and convert arguments to real array
  */
-function safeStringifyArgumentsToArray(args: IArguments, includeStack: boolean): string {
+function safeStringifyArgumentsToArray(args: unknown[], includeStack: boolean): string {
 	const argsArray = [];
 
 	// Massage some arguments with special treatment
diff --git a/src/vs/workbench/api/common/extHostExtensionService.ts b/src/vs/workbench/api/common/extHostExtensionService.ts
index a0178f266d4a8..36cec4d29bc69 100644
--- a/src/vs/workbench/api/common/extHostExtensionService.ts
+++ b/src/vs/workbench/api/common/extHostExtensionService.ts
@@ -557,7 +557,7 @@ export abstract class AbstractExtHostExtensionService extends Disposable impleme
 							return undefined;
 						}
 
-						const onDidReceiveMessage = Event.buffer(Event.fromDOMEventEmitter(messagePort, 'message', e => e.data));
+						const onDidReceiveMessage = Event.buffer(Event.fromDOMEventEmitter(messagePort, 'message', e => e.data), 'onDidReceiveMessage');
 						messagePort.start();
 						messagePassingProtocol = {
 							onDidReceiveMessage,
diff --git a/src/vs/workbench/api/common/extHostGitExtensionService.ts b/src/vs/workbench/api/common/extHostGitExtensionService.ts
index 61a64e83bf375..4d1dd2e2acbf6 100644
--- a/src/vs/workbench/api/common/extHostGitExtensionService.ts
+++ b/src/vs/workbench/api/common/extHostGitExtensionService.ts
@@ -11,7 +11,7 @@ import { ExtensionIdentifier } from '../../../platform/extensions/common/extensi
 import { createDecorator } from '../../../platform/instantiation/common/instantiation.js';
 import { IExtHostExtensionService } from './extHostExtensionService.js';
 import { IExtHostRpcService } from './extHostRpcService.js';
-import { ExtHostGitExtensionShape, GitBranchDto, GitRefDto, GitRefQueryDto, GitRefTypeDto, GitRepositoryStateDto, GitUpstreamRefDto, MainContext, MainThreadGitExtensionShape } from './extHost.protocol.js';
+import { ExtHostGitExtensionShape, GitBaseRefDto, GitBranchDto, GitChangeDto, GitDiffChangeDto, GitRefDto, GitRefQueryDto, GitRefTypeDto, GitRepositoryStateDto, GitUpstreamRefDto, MainContext, MainThreadGitExtensionShape } from './extHost.protocol.js';
 import { ResourceMap } from '../../../base/common/map.js';
 
 const GIT_EXTENSION_ID = 'vscode.git';
@@ -31,6 +31,7 @@ function toGitBranchDto(branch: Branch): GitBranchDto {
 		commit: branch.commit,
 		type: toGitRefTypeDto(branch.type),
 		remote: branch.remote,
+		base: branch.base,
 		upstream: branch.upstream ? toGitUpstreamRefDto(branch.upstream) : undefined,
 		ahead: branch.ahead,
 		behind: branch.behind,
@@ -45,25 +46,86 @@ function toGitUpstreamRefDto(upstream: UpstreamRef): GitUpstreamRefDto {
 	};
 }
 
+// Status values from the git extension's const enum Status
+const enum GitStatus {
+	INDEX_ADDED = 1,
+	INDEX_DELETED = 2,
+	INDEX_RENAMED = 3,
+	MODIFIED = 5,
+	DELETED = 6,
+	UNTRACKED = 7,
+	INTENT_TO_ADD = 9,
+	INTENT_TO_RENAME = 10,
+}
+
+function toGitChangeDto(change: Change): GitChangeDto {
+	switch (change.status) {
+		// Added: no original
+		case GitStatus.INDEX_ADDED:
+		case GitStatus.UNTRACKED:
+		case GitStatus.INTENT_TO_ADD:
+			return { uri: change.uri, originalUri: undefined, modifiedUri: change.uri };
+
+		// Deleted: no modified
+		case GitStatus.INDEX_DELETED:
+		case GitStatus.DELETED:
+			return { uri: change.uri, originalUri: change.uri, modifiedUri: undefined };
+
+		// Renamed: original is old name, modified is new name
+		case GitStatus.INDEX_RENAMED:
+		case GitStatus.INTENT_TO_RENAME:
+			return { uri: change.uri, originalUri: change.originalUri, modifiedUri: change.renameUri };
+
+		// Modified and everything else: both original and modified
+		default:
+			return { uri: change.uri, originalUri: change.originalUri, modifiedUri: change.uri };
+	}
+}
+
+interface DiffChange extends Change {
+	readonly insertions: number;
+	readonly deletions: number;
+}
+
 interface Repository {
 	readonly rootUri: vscode.Uri;
 	readonly state: RepositoryState;
 
 	status(): Promise<void>;
+	getBranchBase(name: string): Promise<Branch | undefined>;
 	getRefs(query: GitRefQuery, token?: vscode.CancellationToken): Promise<GitRef[]>;
+	diffBetweenWithStats(ref1: string, ref2: string, path?: string): Promise<DiffChange[]>;
+	isBranchProtected(branch?: Branch): boolean;
+}
+
+interface Change {
+	readonly uri: vscode.Uri;
+	readonly originalUri: vscode.Uri;
+	readonly renameUri: vscode.Uri | undefined;
+	readonly status: number;
 }
 
 interface RepositoryState {
 	readonly HEAD: Branch | undefined;
+	readonly mergeChanges: Change[];
+	readonly indexChanges: Change[];
+	readonly workingTreeChanges: Change[];
+	readonly untrackedChanges: Change[];
 	readonly onDidChange: Event<void>;
 }
 
 interface Branch extends GitRef {
+	readonly base?: BaseRef;
 	readonly upstream?: UpstreamRef;
 	readonly ahead?: number;
 	readonly behind?: number;
 }
 
+interface BaseRef {
+	readonly name: string;
+	readonly isProtected: boolean;
+}
+
 interface UpstreamRef {
 	readonly remote: string;
 	readonly name: string;
@@ -145,13 +207,8 @@ export class ExtHostGitExtensionService extends Disposable implements IExtHostGi
 
 		const existingHandle = this._repositoryByUri.get(repository.rootUri);
 		if (existingHandle !== undefined) {
-			return {
-				handle: existingHandle,
-				rootUri: repository.rootUri,
-				state: {
-					HEAD: repository.state.HEAD ? toGitBranchDto(repository.state.HEAD) : undefined
-				}
-			};
+			const state = await this._getRepositoryState(repository);
+			return { handle: existingHandle, rootUri: repository.rootUri, state };
 		}
 
 		let repositoryState = repository.state;
@@ -175,15 +232,8 @@ export class ExtHostGitExtensionService extends Disposable implements IExtHostGi
 			this._proxy.$onDidChangeRepository(handle);
 		}));
 
-		return {
-			handle,
-			rootUri: repository.rootUri,
-			state: {
-				HEAD: repository.state.HEAD
-					? toGitBranchDto(repository.state.HEAD)
-					: undefined
-			}
-		};
+		const state = await this._getRepositoryState(repository);
+		return { handle, rootUri: repository.rootUri, state };
 	}
 
 	async $getRefs(handle: number, query: GitRefQueryDto, token?: vscode.CancellationToken): Promise<GitRefDto[]> {
@@ -225,8 +275,55 @@ export class ExtHostGitExtensionService extends Disposable implements IExtHostGi
 			return undefined;
 		}
 
+		return this._getRepositoryState(repository);
+	}
+
+	private async _getRepositoryState(repository: Repository): Promise<GitRepositoryStateDto> {
+		const state = repository.state;
+
+		// Base branch
+		const base = await this._getBranchBase(repository);
+
+		return {
+			HEAD: state.HEAD ? toGitBranchDto({ ...state.HEAD, base }) : undefined,
+			mergeChanges: state.mergeChanges.map(toGitChangeDto),
+			indexChanges: state.indexChanges.map(toGitChangeDto),
+			workingTreeChanges: state.workingTreeChanges.map(toGitChangeDto),
+			untrackedChanges: state.untrackedChanges.map(toGitChangeDto),
+		};
+	}
+
+	private async _getBranchBase(repository: Repository): Promise<GitBaseRefDto | undefined> {
 		const state = repository.state;
-		return { HEAD: state.HEAD ? toGitBranchDto(state.HEAD) : undefined };
+		if (!state.HEAD?.name) {
+			return undefined;
+		}
+
+		const baseBranch = await repository.getBranchBase(state.HEAD.name);
+		if (!baseBranch?.name) {
+			return undefined;
+		}
+
+		const isProtected = repository.isBranchProtected(baseBranch);
+		return { name: baseBranch.name, isProtected };
+	}
+
+	async $diffBetweenWithStats(handle: number, ref1: string, ref2: string, path?: string): Promise<GitDiffChangeDto[]> {
+		const repository = this._repositories.get(handle);
+		if (!repository) {
+			return [];
+		}
+
+		try {
+			const changes = await repository.diffBetweenWithStats(ref1, ref2, path);
+			return changes.map(c => ({
+				...toGitChangeDto(c),
+				insertions: c.insertions,
+				deletions: c.deletions,
+			}));
+		} catch {
+			return [];
+		}
 	}
 
 	private async _ensureGitApi(): Promise<GitExtensionAPI | undefined> {
diff --git a/src/vs/workbench/api/common/extHostLanguageModels.ts b/src/vs/workbench/api/common/extHostLanguageModels.ts
index 18c2045825c0d..cc76961ab1583 100644
--- a/src/vs/workbench/api/common/extHostLanguageModels.ts
+++ b/src/vs/workbench/api/common/extHostLanguageModels.ts
@@ -258,7 +258,7 @@ export class ExtHostLanguageModels implements ExtHostLanguageModelsShape {
 		return modelMetadataAndIdentifier;
 	}
 
-	async $startChatRequest(modelId: string, requestId: number, from: ExtensionIdentifier, messages: SerializableObjectWithBuffers<IChatMessage[]>, options: vscode.LanguageModelChatRequestOptions, token: CancellationToken): Promise<void> {
+	async $startChatRequest(modelId: string, requestId: number, from: ExtensionIdentifier | undefined, messages: SerializableObjectWithBuffers<IChatMessage[]>, options: vscode.LanguageModelChatRequestOptions, token: CancellationToken): Promise<void> {
 		const knownModel = this._localModels.get(modelId);
 		if (!knownModel) {
 			throw new Error('Model not found');
@@ -319,7 +319,8 @@ export class ExtHostLanguageModels implements ExtHostLanguageModelsShape {
 			value = data.provider.provideLanguageModelChatResponse(
 				knownModel.info,
 				messages.value.map(typeConvert.LanguageModelChatMessage2.to),
-				{ ...options, modelOptions: options.modelOptions ?? {}, requestInitiator: ExtensionIdentifier.toKey(from), toolMode: options.toolMode ?? extHostTypes.LanguageModelChatToolMode.Auto },
+				// todo@connor4312: move `core` -> `undefined` after 1.111 Insiders is out
+				{ ...options, modelOptions: options.modelOptions ?? {}, requestInitiator: from ? ExtensionIdentifier.toKey(from) : 'core', toolMode: options.toolMode ?? extHostTypes.LanguageModelChatToolMode.Auto },
 				progress,
 				token
 			);
@@ -363,7 +364,7 @@ export class ExtHostLanguageModels implements ExtHostLanguageModelsShape {
 		}
 
 		for (const [modelIdentifier, modelData] of this._localModels) {
-			if (modelData.metadata.isDefaultForLocation[ChatAgentLocation.Chat]) {
+			if (modelData.metadata.isDefaultForLocation[ChatAgentLocation.Chat] && modelData.metadata.vendor === 'copilot') {
 				defaultModelId = modelIdentifier;
 				break;
 			}
diff --git a/src/vs/workbench/api/common/extHostTask.ts b/src/vs/workbench/api/common/extHostTask.ts
index 5bf476c980a67..7191d7b5ac35d 100644
--- a/src/vs/workbench/api/common/extHostTask.ts
+++ b/src/vs/workbench/api/common/extHostTask.ts
@@ -332,6 +332,9 @@ export namespace TaskDTO {
 		if (value.presentationOptions) {
 			result.presentationOptions = TaskPresentationOptionsDTO.to(value.presentationOptions)!;
 		}
+		if (value.runOptions) {
+			result.runOptions = value.runOptions;
+		}
 		if (value._id) {
 			result._id = value._id;
 		}
diff --git a/src/vs/workbench/api/common/extHostTerminalService.ts b/src/vs/workbench/api/common/extHostTerminalService.ts
index b50811f77158f..a526f4df3231d 100644
--- a/src/vs/workbench/api/common/extHostTerminalService.ts
+++ b/src/vs/workbench/api/common/extHostTerminalService.ts
@@ -25,6 +25,7 @@ import { Promises } from '../../../base/common/async.js';
 import { EditorGroupColumn } from '../../services/editor/common/editorGroupColumn.js';
 import { TerminalCompletionList, TerminalQuickFix, ViewColumn } from './extHostTypeConverters.js';
 import { IExtHostCommands } from './extHostCommands.js';
+import { IExtHostInitDataService } from './extHostInitDataService.js';
 import { MarshalledId } from '../../../base/common/marshallingIds.js';
 import { ISerializedTerminalInstanceContext } from '../../contrib/terminal/common/terminal.js';
 import { isWindows } from '../../../base/common/platform.js';
@@ -1268,19 +1269,33 @@ class ScopedEnvironmentVariableCollection implements IEnvironmentVariableCollect
 }
 
 export class WorkerExtHostTerminalService extends BaseExtHostTerminalService {
+
+	private readonly _hasRemoteAuthority: boolean;
+
 	constructor(
 		@IExtHostCommands extHostCommands: IExtHostCommands,
-		@IExtHostRpcService extHostRpc: IExtHostRpcService
+		@IExtHostRpcService extHostRpc: IExtHostRpcService,
+		@IExtHostInitDataService initData: IExtHostInitDataService
 	) {
 		super(false, extHostCommands, extHostRpc);
+		this._hasRemoteAuthority = !!initData.remote.authority;
 	}
 
 	public createTerminal(name?: string, shellPath?: string, shellArgs?: string[] | string): vscode.Terminal {
-		throw new NotSupportedError();
+		if (!this._hasRemoteAuthority) {
+			throw new NotSupportedError();
+		}
+		return this.createTerminalFromOptions({ name, shellPath, shellArgs });
 	}
 
 	public createTerminalFromOptions(options: vscode.TerminalOptions, internalOptions?: ITerminalInternalOptions): vscode.Terminal {
-		throw new NotSupportedError();
+		if (!this._hasRemoteAuthority) {
+			throw new NotSupportedError();
+		}
+		const terminal = new ExtHostTerminal(this._proxy, generateUuid(), options, options.name);
+		this._terminals.push(terminal);
+		terminal.create(options, this._serializeParentTerminal(options, internalOptions));
+		return terminal.value;
 	}
 }
 
diff --git a/src/vs/workbench/api/common/extHostTreeViews.ts b/src/vs/workbench/api/common/extHostTreeViews.ts
index fce5e9d47db5a..c0d05cbb48633 100644
--- a/src/vs/workbench/api/common/extHostTreeViews.ts
+++ b/src/vs/workbench/api/common/extHostTreeViews.ts
@@ -3,7 +3,6 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { localize } from '../../../nls.js';
 import type * as vscode from 'vscode';
 import { basename } from '../../../base/common/resources.js';
 import { URI } from '../../../base/common/uri.js';
@@ -876,10 +875,14 @@ class ExtHostTreeView<T> extends Disposable {
 		if (duplicateHandle) {
 			const existingElement = this._elements.get(duplicateHandle);
 			if (existingElement) {
+				const existingNode = this._nodes.get(existingElement);
 				if (existingElement !== element) {
-					throw new Error(localize('treeView.duplicateElement', 'Element with id {0} is already registered', extTreeItem.id));
+					// A different element object was registered with the same ID.
+					// This can happen during concurrent tree operations (e.g., tree
+					// being switched to while data is updated). Clean up the stale
+					// element reference before re-registering with the new one.
+					this._nodes.delete(existingElement);
 				}
-				const existingNode = this._nodes.get(existingElement);
 				if (existingNode) {
 					const newNode = this._createTreeNode(element, extTreeItem, parentNode);
 					this._updateNodeCache(element, newNode, existingNode, parentNode);
diff --git a/src/vs/workbench/api/common/extHostTypeConverters.ts b/src/vs/workbench/api/common/extHostTypeConverters.ts
index d565aa7634c67..9cab65213338a 100644
--- a/src/vs/workbench/api/common/extHostTypeConverters.ts
+++ b/src/vs/workbench/api/common/extHostTypeConverters.ts
@@ -47,7 +47,7 @@ import { LocalChatSessionUri } from '../../contrib/chat/common/model/chatUri.js'
 import { ChatRequestToolReferenceEntry, IChatRequestVariableEntry, isImageVariableEntry, isPromptFileVariableEntry, isPromptTextVariableEntry } from '../../contrib/chat/common/attachments/chatVariableEntries.js';
 import { ChatSessionStatus, IChatSessionItem } from '../../contrib/chat/common/chatSessionsService.js';
 import { ChatAgentLocation } from '../../contrib/chat/common/constants.js';
-import { IChatRequestHooks, IHookCommand, resolveEffectiveCommand } from '../../contrib/chat/common/promptSyntax/hookSchema.js';
+import { ChatRequestHooks, IHookCommand, resolveEffectiveCommand } from '../../contrib/chat/common/promptSyntax/hookSchema.js';
 import { IToolInvocationContext, IToolResult, IToolResultInputOutputDetails, IToolResultOutputDetails, ToolDataSource, ToolInvocationPresentation } from '../../contrib/chat/common/tools/languageModelToolsService.js';
 import * as chatProvider from '../../contrib/chat/common/languageModels.js';
 import { IChatMessageDataPart, IChatResponseDataPart, IChatResponsePromptTsxPart, IChatResponseTextPart } from '../../contrib/chat/common/languageModels.js';
@@ -2671,7 +2671,7 @@ export namespace ChatResponseQuestionCarouselPart {
 				type: questionTypeToString(q.type),
 				title: q.title,
 				message: q.message ? MarkdownString.from(q.message) : undefined,
-				options: q.options,
+				options: q.options?.map(opt => ({ id: opt.id, label: opt.label, value: String(opt.value) })),
 				defaultValue: q.defaultValue,
 				allowFreeformInput: q.allowFreeformInput
 			})),
@@ -2934,6 +2934,7 @@ export namespace ChatToolInvocationPart {
 				pastTenseMessage: part.pastTenseMessage ? MarkdownString.from(part.pastTenseMessage) : undefined,
 				toolSpecificData,
 				subagentInvocationId: part.subAgentInvocationId,
+				resultDetails
 			};
 		}
 
@@ -3440,6 +3441,7 @@ export namespace ChatAgentRequest {
 			editedFileEvents: request.editedFileEvents,
 			modeInstructions: request.modeInstructions?.content,
 			modeInstructions2: ChatRequestModeInstructions.to(request.modeInstructions),
+			permissionLevel: request.permissionLevel,
 			subAgentInvocationId: request.subAgentInvocationId,
 			subAgentName: request.subAgentName,
 			parentRequestId: request.parentRequestId,
@@ -3606,10 +3608,12 @@ export namespace ChatRequestModeInstructions {
 	export function to(mode: IChatRequestModeInstructions | undefined): vscode.ChatRequestModeInstructions | undefined {
 		if (mode) {
 			return {
+				uri: URI.revive(mode.uri),
 				name: mode.name,
 				content: mode.content,
 				toolReferences: ChatLanguageModelToolReferences.to(mode.toolReferences),
-				metadata: mode.metadata
+				metadata: mode.metadata,
+				isBuiltin: mode.isBuiltin,
 			};
 		}
 		return undefined;
@@ -3873,6 +3877,9 @@ export namespace LanguageModelToolResult {
 		if (result.toolMetadata !== undefined) {
 			toolResult.toolMetadata = result.toolMetadata;
 		}
+		if (result.toolResultError) {
+			toolResult.hasError = !!result.toolResultError;
+		}
 		return toolResult;
 	}
 
@@ -3938,6 +3945,7 @@ export namespace LanguageModelToolResult {
 			toolResultMessage: MarkdownString.fromStrict(result.toolResultMessage),
 			toolResultDetails: detailsDto,
 			toolMetadata: result.toolMetadata,
+			toolResultError: result.hasError,
 		};
 
 		return hasBuffers ? new SerializableObjectWithBuffers(dto) : dto;
@@ -4047,6 +4055,7 @@ export namespace McpServerDefinition {
 					command: item.command,
 					env: item.env,
 					envFile: undefined,
+					sandbox: undefined
 				}
 		);
 	}
@@ -4093,7 +4102,7 @@ export namespace SourceControlInputBoxValidationType {
 }
 
 export namespace ChatRequestHooksConverter {
-	export function to(hooks: IChatRequestHooks): vscode.ChatRequestHooks {
+	export function to(hooks: ChatRequestHooks): vscode.ChatRequestHooks {
 		const result: Record<string, vscode.ChatHookCommand[]> = {};
 		for (const [hookType, commands] of Object.entries(hooks)) {
 			if (!commands || commands.length === 0) {
diff --git a/src/vs/workbench/api/common/extHostTypes.ts b/src/vs/workbench/api/common/extHostTypes.ts
index 890d4cfc677c6..e5b0761780205 100644
--- a/src/vs/workbench/api/common/extHostTypes.ts
+++ b/src/vs/workbench/api/common/extHostTypes.ts
@@ -30,7 +30,7 @@ import { SnippetString } from './extHostTypes/snippetString.js';
 import { SymbolKind, SymbolTag } from './extHostTypes/symbolInformation.js';
 import { TextEdit } from './extHostTypes/textEdit.js';
 import { WorkspaceEdit } from './extHostTypes/workspaceEdit.js';
-import { HookTypeValue } from '../../contrib/chat/common/promptSyntax/hookSchema.js';
+import { HookTypeValue } from '../../contrib/chat/common/promptSyntax/hookTypes.js';
 
 export { CodeActionKind } from './extHostTypes/codeActionKind.js';
 export {
@@ -1275,6 +1275,12 @@ export enum TaskScope {
 	Workspace = 2
 }
 
+export enum TaskRunOn {
+	Default = 1,
+	FolderOpen = 2,
+	WorktreeCreated = 3,
+}
+
 export class CustomExecution implements vscode.CustomExecution {
 	private _callback: (resolvedDefinition: vscode.TaskDefinition) => Thenable<vscode.Pseudoterminal>;
 	constructor(callback: (resolvedDefinition: vscode.TaskDefinition) => Thenable<vscode.Pseudoterminal>) {
@@ -3716,6 +3722,40 @@ export class ChatDebugEventMessageContent {
 	}
 }
 
+export class ChatDebugEventToolCallContent {
+	readonly _kind = 'toolCallContent';
+	toolName: string;
+	result?: ChatDebugToolCallResult;
+	durationInMillis?: number;
+	input?: string;
+	output?: string;
+
+	constructor(toolName: string) {
+		this.toolName = toolName;
+	}
+}
+
+export class ChatDebugEventModelTurnContent {
+	readonly _kind = 'modelTurnContent';
+	requestName: string;
+	model?: string;
+	status?: string;
+	durationInMillis?: number;
+	timeToFirstTokenInMillis?: number;
+	maxInputTokens?: number;
+	maxOutputTokens?: number;
+	inputTokens?: number;
+	outputTokens?: number;
+	cachedTokens?: number;
+	totalTokens?: number;
+	errorMessage?: string;
+	sections?: ChatDebugMessageSection[];
+
+	constructor(requestName: string) {
+		this.requestName = requestName;
+	}
+}
+
 export class ChatSessionChangedFile {
 	constructor(public readonly modifiedUri: vscode.Uri, public readonly insertions: number, public readonly deletions: number, public readonly originalUri?: vscode.Uri) { }
 }
diff --git a/src/vs/workbench/api/common/shared/tasks.ts b/src/vs/workbench/api/common/shared/tasks.ts
index a7e46e70ff8ad..e6ec0ec0987f3 100644
--- a/src/vs/workbench/api/common/shared/tasks.ts
+++ b/src/vs/workbench/api/common/shared/tasks.ts
@@ -26,6 +26,7 @@ export interface ITaskPresentationOptionsDTO {
 
 export interface IRunOptionsDTO {
 	reevaluateOnRerun?: boolean;
+	runOn?: number;
 }
 
 export interface IExecutionOptionsDTO {
diff --git a/src/vs/workbench/api/node/extHostCLIServer.ts b/src/vs/workbench/api/node/extHostCLIServer.ts
index 70b04f8fdde7a..14ed9e4f58646 100644
--- a/src/vs/workbench/api/node/extHostCLIServer.ts
+++ b/src/vs/workbench/api/node/extHostCLIServer.ts
@@ -47,7 +47,7 @@ export interface ExtensionManagementPipeArgs {
 export type PipeCommand = OpenCommandPipeArgs | StatusPipeArgs | OpenExternalCommandPipeArgs | ExtensionManagementPipeArgs;
 
 export interface ICommandsExecuter {
-	executeCommand<T>(id: string, ...args: any[]): Promise<T>;
+	executeCommand<T>(id: string, ...args: unknown[]): Promise<T>;
 }
 
 export class CLIServerBase {
diff --git a/src/vs/workbench/api/node/extHostConsoleForwarder.ts b/src/vs/workbench/api/node/extHostConsoleForwarder.ts
index d1568f2864222..69ce4029ca0fe 100644
--- a/src/vs/workbench/api/node/extHostConsoleForwarder.ts
+++ b/src/vs/workbench/api/node/extHostConsoleForwarder.ts
@@ -24,12 +24,11 @@ export class ExtHostConsoleForwarder extends AbstractExtHostConsoleForwarder {
 		this._wrapStream('stdout', 'log');
 	}
 
-	protected override _nativeConsoleLogMessage(method: 'log' | 'info' | 'warn' | 'error' | 'debug', original: (...args: any[]) => void, args: IArguments) {
+	protected override _nativeConsoleLogMessage(method: 'log' | 'info' | 'warn' | 'error' | 'debug', original: (...args: unknown[]) => void, args: unknown[]): void {
 		const stream = method === 'error' || method === 'warn' ? process.stderr : process.stdout;
 		this._isMakingConsoleCall = true;
 		stream.write(`\n${NativeLogMarkers.Start}\n`);
-		// eslint-disable-next-line local/code-no-any-casts
-		original.apply(console, args as any);
+		original.apply(console, args);
 		stream.write(`\n${NativeLogMarkers.End}\n`);
 		this._isMakingConsoleCall = false;
 	}
diff --git a/src/vs/workbench/api/node/extHostMcpNode.ts b/src/vs/workbench/api/node/extHostMcpNode.ts
index 1b961f66ae16b..c08fc0af221be 100644
--- a/src/vs/workbench/api/node/extHostMcpNode.ts
+++ b/src/vs/workbench/api/node/extHostMcpNode.ts
@@ -73,6 +73,11 @@ export class NodeExtHostMpcService extends ExtHostMcpService {
 			}
 		}
 		for (const [key, value] of Object.entries(launch.env)) {
+			// For PATH, we want to append to the existing PATH instead of overwriting it.
+			if (key.toUpperCase() === 'PATH' && value !== null) {
+				env[key] = env[key] ? `${env[key]}${path.delimiter}${String(value)}` : String(value);
+				continue;
+			}
 			env[key] = value === null ? undefined : String(value);
 		}
 
diff --git a/src/vs/workbench/api/node/extensionHostProcess.ts b/src/vs/workbench/api/node/extensionHostProcess.ts
index bb0fb8eec64c0..06a165e7ba921 100644
--- a/src/vs/workbench/api/node/extensionHostProcess.ts
+++ b/src/vs/workbench/api/node/extensionHostProcess.ts
@@ -118,7 +118,7 @@ function patchProcess(allowExit: boolean) {
 	process.env['ELECTRON_RUN_AS_NODE'] = '1';
 
 	// eslint-disable-next-line local/code-no-any-casts
-	process.on = <any>function (event: string, listener: (...args: any[]) => void) {
+	process.on = <any>function (event: string, listener: (...args: unknown[]) => void) {
 		if (event === 'uncaughtException') {
 			const actualListener = listener;
 			listener = function (...args: unknown[]) {
@@ -242,7 +242,7 @@ function _createExtHostProtocol(): Promise<IMessagePassingProtocol> {
 						clearTimeout(timer);
 						protocol = new PersistentProtocol({ socket, initialChunk: initialDataChunk });
 						protocol.sendResume();
-						protocol.onDidDispose(() => onTerminate('renderer disconnected'));
+						Event.once(protocol.onDidDispose)(() => onTerminate('renderer disconnected'));
 						resolve(protocol);
 
 						// Wait for rich client to reconnect
diff --git a/src/vs/workbench/api/node/proxyResolver.ts b/src/vs/workbench/api/node/proxyResolver.ts
index 48be84370399c..0a2d552624ded 100644
--- a/src/vs/workbench/api/node/proxyResolver.ts
+++ b/src/vs/workbench/api/node/proxyResolver.ts
@@ -52,6 +52,7 @@ export function connectProxyResolver(
 		getProxySupport: () => getExtHostConfigValue<ProxySupportSetting>(configProvider, isRemote, 'http.proxySupport') || 'off',
 		getNoProxyConfig: () => getExtHostConfigValue<string[]>(configProvider, isRemote, 'http.noProxy') || [],
 		isAdditionalFetchSupportEnabled: () => getExtHostConfigValue<boolean>(configProvider, isRemote, 'http.fetchAdditionalSupport', true),
+		isWebSocketPatchEnabled: () => getExtHostConfigValue<boolean>(configProvider, isRemote, 'http.webSocketAdditionalSupport', true),
 		addCertificatesV1: () => certSettingV1(configProvider, isRemote),
 		addCertificatesV2: () => certSettingV2(configProvider, isRemote),
 		loadSystemCertificatesFromNode: () => getExtHostConfigValue<boolean>(configProvider, isRemote, 'http.systemCertificatesNode', systemCertificatesNodeDefault),
@@ -122,6 +123,7 @@ export function connectProxyResolver(
 	target.resolveProxyURL = resolveProxyURL;
 
 	patchGlobalFetch(params, configProvider, mainThreadTelemetry, initData, resolveProxyURL, disposables);
+	patchGlobalWebSocket(params, resolveProxyURL);
 
 	const lookup = createPatchedModules(params, resolveProxyWithRequest);
 	return configureModuleLoading(extensionService, lookup);
@@ -204,6 +206,16 @@ function patchGlobalFetch(params: ProxyAgentParams, configProvider: ExtHostConfi
 	}
 }
 
+function patchGlobalWebSocket(params: ProxyAgentParams, resolveProxyURL: (url: string) => Promise<string | undefined>) {
+	// eslint-disable-next-line local/code-no-any-casts
+	if (!(globalThis as any).__vscodeOriginalWebSocket) {
+		const originalWebSocket = globalThis.WebSocket;
+		// eslint-disable-next-line local/code-no-any-casts
+		(globalThis as any).__vscodeOriginalWebSocket = originalWebSocket;
+		globalThis.WebSocket = proxyAgent.createWebSocketPatch(params, originalWebSocket, resolveProxyURL);
+	}
+}
+
 function monitorResponseProperties(mainThreadTelemetry: MainThreadTelemetryShape, response: Response, urlString: string) {
 	const originalUrl = response.url;
 	Object.defineProperty(response, 'url', {
diff --git a/src/vs/workbench/api/test/browser/extHostBrowsers.test.ts b/src/vs/workbench/api/test/browser/extHostBrowsers.test.ts
new file mode 100644
index 0000000000000..e05e040cf70b6
--- /dev/null
+++ b/src/vs/workbench/api/test/browser/extHostBrowsers.test.ts
@@ -0,0 +1,428 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import type * as vscode from 'vscode';
+import assert from 'assert';
+import { mock } from '../../../../base/test/common/mock.js';
+import { BrowserTabDto, MainThreadBrowsersShape } from '../../common/extHost.protocol.js';
+import { ExtHostBrowsers } from '../../common/extHostBrowsers.js';
+import { SingleProxyRPCProtocol } from '../common/testRPCProtocol.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../base/test/common/utils.js';
+
+suite('ExtHostBrowsers', () => {
+
+	const store = ensureNoDisposablesAreLeakedInTestSuite();
+
+	const defaultDto: BrowserTabDto = {
+		id: 'browser-1',
+		url: 'https://example.com',
+		title: 'Example',
+		favicon: undefined,
+	};
+
+	function createDto(overrides?: Partial<BrowserTabDto>): BrowserTabDto {
+		return { ...defaultDto, ...overrides };
+	}
+
+	function createExtHostBrowsers(overrides?: Partial<MainThreadBrowsersShape>): ExtHostBrowsers {
+		const proxy = new class extends mock<MainThreadBrowsersShape>() {
+			override $openBrowserTab(): Promise<BrowserTabDto> { return Promise.resolve(createDto()); }
+			override $startCDPSession(): Promise<void> { return Promise.resolve(); }
+			override $closeCDPSession(): Promise<void> { return Promise.resolve(); }
+			override $sendCDPMessage(): Promise<void> { return Promise.resolve(); }
+			override $closeBrowserTab(): Promise<void> { return Promise.resolve(); }
+		};
+		if (overrides) {
+			Object.assign(proxy, overrides);
+		}
+		return store.add(new ExtHostBrowsers(SingleProxyRPCProtocol(proxy)));
+	}
+
+	// #region browserTabs
+
+	test('browserTabs populates from $onDidOpenBrowserTab', () => {
+		const extHost = createExtHostBrowsers();
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1', url: 'https://one.com', title: 'One' }));
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b2', url: 'https://two.com', title: 'Two' }));
+
+		const tabs = extHost.browserTabs;
+		assert.strictEqual(tabs.length, 2);
+		assert.strictEqual(tabs[0].url, 'https://one.com');
+		assert.strictEqual(tabs[1].url, 'https://two.com');
+	});
+
+	test('browserTabs returns a snapshot, not a live array', () => {
+		const extHost = createExtHostBrowsers();
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1' }));
+		const snapshot1 = extHost.browserTabs;
+
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b2' }));
+		const snapshot2 = extHost.browserTabs;
+
+		assert.notStrictEqual(snapshot1, snapshot2);
+		assert.strictEqual(snapshot1.length, 1);
+		assert.strictEqual(snapshot2.length, 2);
+	});
+
+	// #endregion
+
+	// #region activeBrowserTab
+
+	test('activeBrowserTab updates via $onDidChangeActiveBrowserTab', () => {
+		const extHost = createExtHostBrowsers();
+		const dto = createDto({ id: 'b1', url: 'https://active.com' });
+		extHost.$onDidOpenBrowserTab(dto);
+		extHost.$onDidChangeActiveBrowserTab(dto);
+
+		assert.strictEqual(extHost.activeBrowserTab?.url, 'https://active.com');
+	});
+
+	test('activeBrowserTab becomes undefined when cleared', () => {
+		const extHost = createExtHostBrowsers();
+		const dto = createDto({ id: 'b1' });
+		extHost.$onDidOpenBrowserTab(dto);
+		extHost.$onDidChangeActiveBrowserTab(dto);
+		assert.ok(extHost.activeBrowserTab);
+
+		extHost.$onDidChangeActiveBrowserTab(undefined);
+		assert.strictEqual(extHost.activeBrowserTab, undefined);
+	});
+
+	test('$onDidChangeActiveBrowserTab with unknown tab creates it and fires open event', () => {
+		const extHost = createExtHostBrowsers();
+		const opened: vscode.BrowserTab[] = [];
+		store.add(extHost.onDidOpenBrowserTab(tab => opened.push(tab)));
+
+		extHost.$onDidChangeActiveBrowserTab(createDto({ id: 'new-tab', url: 'https://new.com' }));
+
+		assert.strictEqual(extHost.activeBrowserTab?.url, 'https://new.com');
+		assert.strictEqual(extHost.browserTabs.length, 1);
+		assert.strictEqual(opened.length, 1, 'onDidOpenBrowserTab should fire for the new tab');
+	});
+
+	// #endregion
+
+	// #region openBrowserTab
+
+	test('openBrowserTab returns a BrowserTab with correct properties', async () => {
+		const dto = createDto({ id: 'opened', url: 'https://opened.com', title: 'Opened' });
+		const extHost = createExtHostBrowsers({
+			$openBrowserTab: () => Promise.resolve(dto),
+		});
+
+		const tab = await extHost.openBrowserTab('https://opened.com');
+		assert.strictEqual(tab.url, 'https://opened.com');
+		assert.strictEqual(tab.title, 'Opened');
+	});
+
+	test('openBrowserTab fires onDidOpenBrowserTab for new tabs', async () => {
+		const extHost = createExtHostBrowsers({
+			$openBrowserTab: () => Promise.resolve(createDto({ id: 'new-tab' })),
+		});
+		const opened: vscode.BrowserTab[] = [];
+		store.add(extHost.onDidOpenBrowserTab(tab => opened.push(tab)));
+
+		await extHost.openBrowserTab('https://example.com');
+
+		assert.strictEqual(opened.length, 1);
+		assert.strictEqual(opened[0].url, 'https://example.com');
+	});
+
+	test('openBrowserTab reuses existing tab when IDs match', async () => {
+		const extHost = createExtHostBrowsers({
+			$openBrowserTab: () => Promise.resolve(createDto({ id: 'same', url: 'https://updated.com' })),
+		});
+
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'same', url: 'https://original.com' }));
+		const tab = await extHost.openBrowserTab('https://updated.com');
+
+		assert.strictEqual(extHost.browserTabs.length, 1);
+		assert.strictEqual(tab.url, 'https://updated.com');
+	});
+
+	test('openBrowserTab forwards options to proxy', async () => {
+		let capturedViewColumn: number | undefined;
+		let capturedOptions: { preserveFocus?: boolean; inactive?: boolean } | undefined;
+		const extHost = createExtHostBrowsers({
+			$openBrowserTab: (_url: string, viewColumn?: number, options?: { preserveFocus?: boolean; inactive?: boolean }) => {
+				capturedViewColumn = viewColumn;
+				capturedOptions = options;
+				return Promise.resolve(createDto({ id: 'opts' }));
+			},
+		});
+
+		await extHost.openBrowserTab('https://example.com', { viewColumn: 2, preserveFocus: true, background: true });
+
+		// ViewColumn.from converts API viewColumn (1-based) to EditorGroupColumn (0-based)
+		assert.strictEqual(capturedViewColumn, 1);
+		assert.strictEqual(capturedOptions?.preserveFocus, true);
+		assert.strictEqual(capturedOptions?.inactive, true);
+	});
+
+	// #endregion
+
+	// #region $onDidOpenBrowserTab
+
+	test('$onDidOpenBrowserTab fires event', () => {
+		const extHost = createExtHostBrowsers();
+		const opened: vscode.BrowserTab[] = [];
+		store.add(extHost.onDidOpenBrowserTab(tab => opened.push(tab)));
+
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1', url: 'https://opened.com' }));
+
+		assert.strictEqual(opened.length, 1);
+		assert.strictEqual(opened[0].url, 'https://opened.com');
+	});
+
+	// #endregion
+
+	// #region $onDidCloseBrowserTab
+
+	test('$onDidCloseBrowserTab removes tab and fires event', () => {
+		const extHost = createExtHostBrowsers();
+		const changes: vscode.BrowserTab[] = [];
+		store.add(extHost.onDidChangeBrowserTabState(tab => changes.push(tab)));
+
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1', url: 'https://old.com' }));
+		extHost.$onDidChangeBrowserTabState('b1', createDto({ id: 'b1', url: 'https://new.com' }));
+
+		assert.strictEqual(changes.length, 1);
+		assert.strictEqual(changes[0].url, 'https://new.com');
+	});
+
+	test('$onDidChangeBrowserTabState does not fire when data is unchanged', () => {
+		const extHost = createExtHostBrowsers();
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1', url: 'https://example.com', title: 'Old Title' }));
+
+		extHost.$onDidChangeBrowserTabState('b1', createDto({ id: 'b1', url: 'https://example.com', title: 'New Title' }));
+
+		assert.strictEqual(extHost.browserTabs[0].url, 'https://example.com');
+		assert.strictEqual(extHost.browserTabs[0].title, 'New Title');
+	});
+
+	// #endregion
+
+	// #region $onDidChangeActiveBrowserTab event
+
+	test('$onDidChangeActiveBrowserTab fires event', () => {
+		const extHost = createExtHostBrowsers();
+		const activeChanges: (string | undefined)[] = [];
+		store.add(extHost.onDidChangeActiveBrowserTab(tab => activeChanges.push(tab?.url)));
+
+		const dto = createDto({ id: 'b1' });
+		extHost.$onDidOpenBrowserTab(dto);
+		extHost.$onDidChangeActiveBrowserTab(dto);
+		extHost.$onDidChangeActiveBrowserTab(undefined);
+
+		assert.deepStrictEqual(activeChanges, ['https://example.com', undefined]);
+	});
+
+	// #endregion
+
+	// #region BrowserTab icon
+
+	test('icon is globe ThemeIcon when no favicon', () => {
+		const extHost = createExtHostBrowsers();
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1', favicon: undefined }));
+
+		assert.strictEqual((extHost.browserTabs[0].icon as { id: string }).id, 'globe');
+	});
+
+	test('icon is URI when favicon is provided', () => {
+		const extHost = createExtHostBrowsers();
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1', favicon: 'https://example.com/favicon.ico' }));
+
+		assert.strictEqual(String(extHost.browserTabs[0].icon), 'https://example.com/favicon.ico');
+	});
+
+	test('icon updates when favicon changes', () => {
+		const extHost = createExtHostBrowsers();
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1', favicon: undefined }));
+		assert.strictEqual((extHost.browserTabs[0].icon as { id: string }).id, 'globe');
+
+		extHost.$onDidChangeBrowserTabState('b1', createDto({ id: 'b1', favicon: 'https://example.com/new.ico' }));
+		assert.strictEqual(String(extHost.browserTabs[0].icon), 'https://example.com/new.ico');
+	});
+
+	test('icon reverts to globe when favicon is cleared', () => {
+		const extHost = createExtHostBrowsers();
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1', favicon: 'https://example.com/icon.ico' }));
+		assert.strictEqual(String(extHost.browserTabs[0].icon), 'https://example.com/icon.ico');
+
+		extHost.$onDidChangeBrowserTabState('b1', createDto({ id: 'b1', favicon: undefined }));
+		assert.strictEqual((extHost.browserTabs[0].icon as { id: string }).id, 'globe');
+	});
+
+	// #endregion
+
+	// #region BrowserTab readonly properties
+
+	test('tab properties are not directly writable', () => {
+		const extHost = createExtHostBrowsers();
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1', url: 'https://example.com', title: 'Title' }));
+		const tab = extHost.browserTabs[0];
+
+		// Attempting to assign to getter-only properties should either throw or be silently ignored
+		assert.throws(() => { (tab as unknown as Record<string, unknown>).url = 'https://hacked.com'; });
+		assert.throws(() => { (tab as unknown as Record<string, unknown>).title = 'Hacked'; });
+		assert.strictEqual(tab.url, 'https://example.com');
+		assert.strictEqual(tab.title, 'Title');
+	});
+
+	test('startCDPSession calls $startCDPSession on proxy', async () => {
+		let capturedBrowserId: string | undefined;
+		const extHost = createExtHostBrowsers({
+			$startCDPSession: (_sessionId: string, browserId: string) => {
+				capturedBrowserId = browserId;
+				return Promise.resolve();
+			},
+		});
+
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1' }));
+		const session = await extHost.browserTabs[0].startCDPSession();
+
+		assert.ok(session);
+		assert.strictEqual(capturedBrowserId, 'b1');
+	});
+
+	test('sendMessage validates message structure', async () => {
+		const extHost = createExtHostBrowsers();
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1' }));
+		const session = await extHost.browserTabs[0].startCDPSession();
+
+		// Valid message succeeds
+		await session.sendMessage({ id: 1, method: 'Page.enable' });
+
+		// Invalid messages are rejected
+		await assert.rejects(Promise.resolve().then(() => session.sendMessage(null as never)), /must be an object/);
+		await assert.rejects(Promise.resolve().then(() => session.sendMessage({ method: 'Foo' } as never)), /numeric id/);
+		await assert.rejects(Promise.resolve().then(() => session.sendMessage({ id: 1 } as never)), /method string/);
+	});
+
+	test('sendMessage forwards valid message to proxy', async () => {
+		const sentMessages: unknown[] = [];
+		const extHost = createExtHostBrowsers({
+			$sendCDPMessage: (_sid: string, message: unknown) => {
+				sentMessages.push(message);
+				return Promise.resolve();
+			},
+		});
+
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1' }));
+		const session = await extHost.browserTabs[0].startCDPSession();
+		await session.sendMessage({ id: 1, method: 'Page.enable', params: {} });
+
+		assert.strictEqual(sentMessages.length, 1);
+		assert.deepStrictEqual(sentMessages[0], { id: 1, method: 'Page.enable', params: {}, sessionId: undefined });
+	});
+
+	test('sendMessage rejects after session is closed', async () => {
+		const extHost = createExtHostBrowsers();
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1' }));
+		const session = await extHost.browserTabs[0].startCDPSession();
+
+		await session.close();
+		await assert.rejects(Promise.resolve().then(() => session.sendMessage({ id: 1, method: 'Foo' })), /closed/);
+	});
+
+	test('$onCDPSessionMessage delivers to correct session', async () => {
+		const capturedIds: string[] = [];
+		const extHost = createExtHostBrowsers({
+			$startCDPSession: (sessionId: string) => {
+				capturedIds.push(sessionId);
+				return Promise.resolve();
+			},
+		});
+
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1' }));
+		const session1 = await extHost.browserTabs[0].startCDPSession();
+		const session2 = await extHost.browserTabs[0].startCDPSession();
+
+		const received1: unknown[] = [];
+		const received2: unknown[] = [];
+		store.add(session1.onDidReceiveMessage(m => received1.push(m)));
+		store.add(session2.onDidReceiveMessage(m => received2.push(m)));
+
+		extHost.$onCDPSessionMessage(capturedIds[1], { id: 1, result: { data: 'hello' } });
+
+		assert.deepStrictEqual(received1, []);
+		assert.deepStrictEqual(received2, [{ id: 1, result: { data: 'hello' } }]);
+	});
+
+	test('$onCDPSessionClosed fires onDidClose', async () => {
+		const capturedIds: string[] = [];
+		const extHost = createExtHostBrowsers({
+			$startCDPSession: (sessionId: string) => {
+				capturedIds.push(sessionId);
+				return Promise.resolve();
+			},
+		});
+
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1' }));
+		const session = await extHost.browserTabs[0].startCDPSession();
+
+		let closeFired = false;
+		store.add(session.onDidClose(() => { closeFired = true; }));
+
+		extHost.$onCDPSessionClosed(capturedIds[0]);
+		assert.ok(closeFired);
+	});
+
+	// #endregion
+
+	// #region Reference stability
+
+	test('tab object reference is stable across updates', () => {
+		const extHost = createExtHostBrowsers();
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1', url: 'https://old.com', title: 'Old' }));
+		const tabBefore = extHost.browserTabs[0];
+
+		extHost.$onDidChangeBrowserTabState('b1', createDto({ id: 'b1', url: 'https://new.com', title: 'New' }));
+		const tabAfter = extHost.browserTabs[0];
+
+		assert.strictEqual(tabBefore, tabAfter);
+		assert.strictEqual(tabAfter.url, 'https://new.com');
+	});
+
+	test('openBrowserTab returns same reference as browserTabs entry', async () => {
+		const extHost = createExtHostBrowsers({
+			$openBrowserTab: () => Promise.resolve(createDto({ id: 'ref-test' })),
+		});
+
+		const returned = await extHost.openBrowserTab('https://example.com');
+		const fromArray = extHost.browserTabs[0];
+
+		assert.strictEqual(returned, fromArray);
+	});
+
+	// #endregion
+
+	// #region Multiple tabs tracked independently
+
+	test('closing one tab does not affect others', () => {
+		const extHost = createExtHostBrowsers();
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b1', url: 'https://one.com' }));
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b2', url: 'https://two.com' }));
+		extHost.$onDidOpenBrowserTab(createDto({ id: 'b3', url: 'https://three.com' }));
+
+		extHost.$onDidCloseBrowserTab('b2');
+
+		assert.strictEqual(extHost.browserTabs.length, 2);
+		assert.deepStrictEqual(extHost.browserTabs.map(t => t.url), ['https://one.com', 'https://three.com']);
+	});
+
+	test('closing active tab clears activeBrowserTab', () => {
+		const extHost = createExtHostBrowsers();
+		const dto = createDto({ id: 'b1' });
+		extHost.$onDidOpenBrowserTab(dto);
+		extHost.$onDidChangeActiveBrowserTab(dto);
+		assert.ok(extHost.activeBrowserTab);
+
+		extHost.$onDidCloseBrowserTab('b1');
+		assert.strictEqual(extHost.activeBrowserTab, undefined);
+	});
+
+	// #endregion
+});
diff --git a/src/vs/workbench/api/test/browser/extHostDocumentSaveParticipant.test.ts b/src/vs/workbench/api/test/browser/extHostDocumentSaveParticipant.test.ts
index 40614a76d685e..b13989ab91fcb 100644
--- a/src/vs/workbench/api/test/browser/extHostDocumentSaveParticipant.test.ts
+++ b/src/vs/workbench/api/test/browser/extHostDocumentSaveParticipant.test.ts
@@ -384,7 +384,7 @@ suite('ExtHostDocumentSaveParticipant', () => {
 	test('Log failing listener', function () {
 		let didLogSomething = false;
 		const participant = new ExtHostDocumentSaveParticipant(new class extends NullLogService {
-			override error(message: string | Error, ...args: any[]): void {
+			override error(message: string | Error, ...args: unknown[]): void {
 				didLogSomething = true;
 			}
 		}, documents, mainThreadBulkEdits);
diff --git a/src/vs/workbench/api/test/browser/extHostTreeViews.test.ts b/src/vs/workbench/api/test/browser/extHostTreeViews.test.ts
index 751a4ff73f9f7..2ca97fac8a80a 100644
--- a/src/vs/workbench/api/test/browser/extHostTreeViews.test.ts
+++ b/src/vs/workbench/api/test/browser/extHostTreeViews.test.ts
@@ -204,7 +204,7 @@ suite('ExtHostTreeView', function () {
 			});
 	});
 
-	test('error is thrown if id is not unique', (done) => {
+	test('duplicate id across siblings is handled gracefully', (done) => {
 		tree['a'] = {
 			'aa': {},
 		};
@@ -212,7 +212,6 @@ suite('ExtHostTreeView', function () {
 			'aa': {},
 			'ba': {}
 		};
-		let caughtExpectedError = false;
 		store.add(target.onRefresh.event(() => {
 			testObject.$getChildren('testNodeWithIdTreeProvider')
 				.then(elements => {
@@ -220,14 +219,54 @@ suite('ExtHostTreeView', function () {
 					assert.deepStrictEqual(actuals, ['1/a', '1/b']);
 					return testObject.$getChildren('testNodeWithIdTreeProvider', ['1/a'])
 						.then(() => testObject.$getChildren('testNodeWithIdTreeProvider', ['1/b']))
-						.then(() => assert.fail('Should fail with duplicate id'))
-						.catch(() => caughtExpectedError = true)
-						.finally(() => caughtExpectedError ? done() : assert.fail('Expected duplicate id error not thrown.'));
-				});
+						.then(elements => {
+							// Children of 'b' should include both 'aa' and 'ba'
+							const children = unBatchChildren(elements)?.map(e => e.handle);
+							assert.deepStrictEqual(children, ['1/aa', '1/ba']);
+							done();
+						});
+				}).catch(done);
 		}));
 		onDidChangeTreeNode.fire(undefined);
 	});
 
+	test('different element instances with same id are replaced gracefully', async () => {
+		// Simulates the race condition: two concurrent getChildren calls return
+		// different element objects that map to the same tree item ID. The second
+		// call should replace the first's registration without error.
+		let callCount = 0;
+		const element1 = { key: 'x' };
+		const element2 = { key: 'x' };
+
+		const treeView = testObject.createTreeView('testRaceProvider', {
+			treeDataProvider: {
+				getChildren: (): { key: string }[] => {
+					callCount++;
+					// Return a different object instance each time
+					return callCount === 1 ? [element1] : [element2];
+				},
+				getTreeItem: (element: { key: string }): TreeItem => {
+					return { label: { label: element.key }, id: 'same-id', collapsibleState: TreeItemCollapsibleState.None };
+				},
+				onDidChangeTreeData: onDidChangeTreeNode.event,
+			}
+		}, extensionsDescription);
+
+		store.add(treeView);
+
+		// First fetch — registers element1 with id 'same-id'
+		const first = await testObject.$getChildren('testRaceProvider');
+		const firstChildren = unBatchChildren(first);
+		assert.strictEqual(firstChildren?.length, 1);
+		assert.strictEqual(firstChildren![0].handle, '1/same-id');
+
+		// Second fetch — different element instance, same id. Should not throw.
+		const second = await testObject.$getChildren('testRaceProvider');
+		const secondChildren = unBatchChildren(second);
+		assert.strictEqual(secondChildren?.length, 1);
+		assert.strictEqual(secondChildren![0].handle, '1/same-id');
+	});
+
 	test('refresh root', function (done) {
 		store.add(target.onRefresh.event(actuals => {
 			assert.strictEqual(undefined, actuals);
diff --git a/src/vs/workbench/api/test/browser/mainThreadChatSessions.test.ts b/src/vs/workbench/api/test/browser/mainThreadChatSessions.test.ts
index 2e31054aa64b7..eeb2d197d829d 100644
--- a/src/vs/workbench/api/test/browser/mainThreadChatSessions.test.ts
+++ b/src/vs/workbench/api/test/browser/mainThreadChatSessions.test.ts
@@ -93,7 +93,7 @@ suite('ObservableChatSession', function () {
 		const resource = LocalChatSessionUri.forSession(sessionId);
 		const session = new ObservableChatSession(resource, 1, proxy, logService, dialogService);
 		(proxy.$provideChatSessionContent as sinon.SinonStub).resolves(sessionContent);
-		await session.initialize(CancellationToken.None);
+		await session.initialize(CancellationToken.None, { initialSessionOptions: [] });
 		return session;
 	}
 
@@ -130,7 +130,7 @@ suite('ObservableChatSession', function () {
 		// Initialize the session
 		const sessionContent = createSessionContent();
 		(proxy.$provideChatSessionContent as sinon.SinonStub).resolves(sessionContent);
-		await session.initialize(CancellationToken.None);
+		await session.initialize(CancellationToken.None, { initialSessionOptions: [] });
 
 		// Now progress should be visible
 		assert.strictEqual(session.progressObs.get().length, 2);
@@ -187,8 +187,8 @@ suite('ObservableChatSession', function () {
 		const sessionContent = createSessionContent();
 		(proxy.$provideChatSessionContent as sinon.SinonStub).resolves(sessionContent);
 
-		const promise1 = session.initialize(CancellationToken.None);
-		const promise2 = session.initialize(CancellationToken.None);
+		const promise1 = session.initialize(CancellationToken.None, { initialSessionOptions: [] });
+		const promise2 = session.initialize(CancellationToken.None, { initialSessionOptions: [] });
 
 		assert.strictEqual(promise1, promise2);
 		await promise1;
@@ -197,6 +197,25 @@ suite('ObservableChatSession', function () {
 		assert.ok((proxy.$provideChatSessionContent as sinon.SinonStub).calledOnce);
 	});
 
+	test('initialization forwards initial session options context', async function () {
+		const sessionId = 'test-id';
+		const resource = LocalChatSessionUri.forSession(sessionId);
+		const session = disposables.add(new ObservableChatSession(resource, 1, proxy, logService, dialogService));
+		const initialSessionOptions = [{ optionId: 'model', value: 'gpt-4.1' }];
+
+		const sessionContent = createSessionContent();
+		(proxy.$provideChatSessionContent as sinon.SinonStub).resolves(sessionContent);
+
+		await session.initialize(CancellationToken.None, { initialSessionOptions });
+
+		assert.ok((proxy.$provideChatSessionContent as sinon.SinonStub).calledOnceWith(
+			1,
+			resource,
+			{ initialSessionOptions },
+			CancellationToken.None
+		));
+	});
+
 	test('progress handling works correctly after initialization', async function () {
 		const sessionContent = createSessionContent();
 		const session = disposables.add(await createInitializedSession(sessionContent));
diff --git a/src/vs/workbench/api/worker/extHostConsoleForwarder.ts b/src/vs/workbench/api/worker/extHostConsoleForwarder.ts
index 01814a7d9695b..26eec2f9ad3c3 100644
--- a/src/vs/workbench/api/worker/extHostConsoleForwarder.ts
+++ b/src/vs/workbench/api/worker/extHostConsoleForwarder.ts
@@ -16,8 +16,7 @@ export class ExtHostConsoleForwarder extends AbstractExtHostConsoleForwarder {
 		super(extHostRpc, initData);
 	}
 
-	protected override _nativeConsoleLogMessage(_method: unknown, original: (...args: any[]) => void, args: IArguments) {
-		// eslint-disable-next-line local/code-no-any-casts
-		original.apply(console, args as any);
+	protected override _nativeConsoleLogMessage(_method: unknown, original: (...args: unknown[]) => void, args: unknown[]) {
+		original.apply(console, args);
 	}
 }
diff --git a/src/vs/workbench/browser/media/style.css b/src/vs/workbench/browser/media/style.css
index 7537f9316e05e..0d6a2da153bfa 100644
--- a/src/vs/workbench/browser/media/style.css
+++ b/src/vs/workbench/browser/media/style.css
@@ -53,6 +53,18 @@ body {
 	z-index: 1;
 	overflow: hidden;
 	color: var(--vscode-foreground);
+
+	/* Elevation shadows */
+	--vscode-shadow-sm: 0 0 4px rgba(0, 0, 0, 0.08);
+	--vscode-shadow-md: 0 0 6px rgba(0, 0, 0, 0.08);
+	--vscode-shadow-lg: 0 0 12px rgba(0, 0, 0, 0.14);
+	--vscode-shadow-xl: 0 0 20px rgba(0, 0, 0, 0.15);
+	--vscode-shadow-hover: 0 0 8px rgba(0, 0, 0, 0.12);
+	--vscode-shadow-active-tab: 0 8px 12px rgba(0, 0, 0, 0.02);
+
+	/* Panel depth shadows cast onto the editor surface */
+	--vscode-shadow-depth-x: 5px 0 10px -4px rgba(0, 0, 0, 0.05);
+	--vscode-shadow-depth-y: 0 5px 10px -4px rgba(0, 0, 0, 0.04);
 }
 
 .monaco-workbench.web {
diff --git a/src/vs/workbench/browser/parts/activitybar/media/activitybarpart.css b/src/vs/workbench/browser/parts/activitybar/media/activitybarpart.css
index d903883d10a85..568a721298088 100644
--- a/src/vs/workbench/browser/parts/activitybar/media/activitybarpart.css
+++ b/src/vs/workbench/browser/parts/activitybar/media/activitybarpart.css
@@ -8,6 +8,15 @@
 	height: 100%;
 }
 
+/* Activity Bar - shadow when sidebar is hidden or on the right */
+.monaco-workbench.nosidebar .part.activitybar {
+	box-shadow: var(--vscode-shadow-md);
+}
+
+.monaco-workbench.activitybar-right .part.activitybar {
+	box-shadow: var(--vscode-shadow-md);
+}
+
 .monaco-workbench .activitybar.bordered::before {
 	content: '';
 	float: left;
diff --git a/src/vs/workbench/browser/parts/dialogs/dialogHandler.ts b/src/vs/workbench/browser/parts/dialogs/dialogHandler.ts
index 16e11df36305b..5af4f540bac41 100644
--- a/src/vs/workbench/browser/parts/dialogs/dialogHandler.ts
+++ b/src/vs/workbench/browser/parts/dialogs/dialogHandler.ts
@@ -4,6 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { localize } from '../../../../nls.js';
+import { CancellationToken } from '../../../../base/common/cancellation.js';
 import { IConfirmation, IConfirmationResult, IInputResult, ICheckbox, IInputElement, ICustomDialogOptions, IInput, AbstractDialogHandler, DialogType, IPrompt, IAsyncPromptResult } from '../../../../platform/dialogs/common/dialogs.js';
 import { ILayoutService } from '../../../../platform/layout/browser/layoutService.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
@@ -47,7 +48,7 @@ export class BrowserDialogHandler extends AbstractDialogHandler {
 
 		const buttons = this.getPromptButtons(prompt);
 
-		const { button, checkboxChecked } = await this.doShow(prompt.type, prompt.message, buttons, prompt.detail, prompt.cancelButton ? buttons.length - 1 : -1 /* Disabled */, prompt.checkbox, undefined, typeof prompt?.custom === 'object' ? prompt.custom : undefined);
+		const { button, checkboxChecked } = await this.doShow(prompt.type, prompt.message, buttons, prompt.detail, prompt.cancelButton ? buttons.length - 1 : -1 /* Disabled */, prompt.checkbox, undefined, typeof prompt?.custom === 'object' ? prompt.custom : undefined, prompt.token);
 
 		return this.getPromptResult(prompt, button, checkboxChecked);
 	}
@@ -57,7 +58,7 @@ export class BrowserDialogHandler extends AbstractDialogHandler {
 
 		const buttons = this.getConfirmationButtons(confirmation);
 
-		const { button, checkboxChecked } = await this.doShow(confirmation.type ?? 'question', confirmation.message, buttons, confirmation.detail, buttons.length - 1, confirmation.checkbox, undefined, typeof confirmation?.custom === 'object' ? confirmation.custom : undefined);
+		const { button, checkboxChecked } = await this.doShow(confirmation.type ?? 'question', confirmation.message, buttons, confirmation.detail, buttons.length - 1, confirmation.checkbox, undefined, typeof confirmation?.custom === 'object' ? confirmation.custom : undefined, confirmation.token);
 
 		return { confirmed: button === 0, checkboxChecked };
 	}
@@ -67,7 +68,7 @@ export class BrowserDialogHandler extends AbstractDialogHandler {
 
 		const buttons = this.getInputButtons(input);
 
-		const { button, checkboxChecked, values } = await this.doShow(input.type ?? 'question', input.message, buttons, input.detail, buttons.length - 1, input?.checkbox, input.inputs, typeof input.custom === 'object' ? input.custom : undefined);
+		const { button, checkboxChecked, values } = await this.doShow(input.type ?? 'question', input.message, buttons, input.detail, buttons.length - 1, input?.checkbox, input.inputs, typeof input.custom === 'object' ? input.custom : undefined, input.token);
 
 		return { confirmed: button === 0, checkboxChecked, values };
 	}
@@ -90,7 +91,7 @@ export class BrowserDialogHandler extends AbstractDialogHandler {
 		}
 	}
 
-	private async doShow(type: Severity | DialogType | undefined, message: string, buttons?: string[], detail?: string, cancelId?: number, checkbox?: ICheckbox, inputs?: IInputElement[], customOptions?: ICustomDialogOptions): Promise<IDialogResult> {
+	private async doShow(type: Severity | DialogType | undefined, message: string, buttons?: string[], detail?: string, cancelId?: number, checkbox?: ICheckbox, inputs?: IInputElement[], customOptions?: ICustomDialogOptions, token?: CancellationToken): Promise<IDialogResult> {
 		const dialogDisposables = new DisposableStore();
 
 		const renderBody = customOptions ? (parent: HTMLElement) => {
@@ -126,6 +127,10 @@ export class BrowserDialogHandler extends AbstractDialogHandler {
 
 		dialogDisposables.add(dialog);
 
+		if (token) {
+			dialogDisposables.add(token.onCancellationRequested(() => dialogDisposables.dispose()));
+		}
+
 		const result = await dialog.show();
 		dialogDisposables.dispose();
 
diff --git a/src/vs/workbench/browser/parts/editor/breadcrumbsPicker.ts b/src/vs/workbench/browser/parts/editor/breadcrumbsPicker.ts
index 198f156d1969c..db602f7d37a5e 100644
--- a/src/vs/workbench/browser/parts/editor/breadcrumbsPicker.ts
+++ b/src/vs/workbench/browser/parts/editor/breadcrumbsPicker.ts
@@ -17,7 +17,7 @@ import { IConfigurationService } from '../../../../platform/configuration/common
 import { FileKind, FileSystemProviderCapabilities, IFileService, IFileStat } from '../../../../platform/files/common/files.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { WorkbenchDataTree, WorkbenchAsyncDataTree } from '../../../../platform/list/browser/listService.js';
-import { breadcrumbsPickerBackground, widgetBorder, widgetShadow } from '../../../../platform/theme/common/colorRegistry.js';
+import { breadcrumbsPickerBackground, widgetBorder } from '../../../../platform/theme/common/colorRegistry.js';
 import { isWorkspace, isWorkspaceFolder, IWorkspace, IWorkspaceContextService, IWorkspaceFolder } from '../../../../platform/workspace/common/workspace.js';
 import { ResourceLabels, IResourceLabel, DEFAULT_LABELS_CONTAINER } from '../../labels.js';
 import { BreadcrumbsConfig } from './breadcrumbs.js';
@@ -96,7 +96,7 @@ export abstract class BreadcrumbsPicker<TInput, TElement> {
 		this._treeContainer.style.background = color ? color.toString() : '';
 		this._treeContainer.style.paddingTop = '2px';
 		this._treeContainer.style.borderRadius = '3px';
-		this._treeContainer.style.boxShadow = `0 0 8px 2px ${this._themeService.getColorTheme().getColor(widgetShadow)}`;
+		this._treeContainer.style.boxShadow = 'var(--vscode-shadow-lg)';
 		this._treeContainer.style.border = `1px solid ${this._themeService.getColorTheme().getColor(widgetBorder)}`;
 		this._domNode.appendChild(this._treeContainer);
 
diff --git a/src/vs/workbench/browser/parts/editor/editor.contribution.ts b/src/vs/workbench/browser/parts/editor/editor.contribution.ts
index 14235489654b6..ffadc12ea9668 100644
--- a/src/vs/workbench/browser/parts/editor/editor.contribution.ts
+++ b/src/vs/workbench/browser/parts/editor/editor.contribution.ts
@@ -429,7 +429,7 @@ MenuRegistry.appendMenuItem(MenuId.EditorTitle, { command: { id: TOGGLE_MAXIMIZE
 MenuRegistry.appendMenuItem(MenuId.EditorTitle, { command: { id: TOGGLE_LOCK_GROUP_COMMAND_ID, title: localize('lockGroup', "Lock Group"), toggled: ActiveEditorGroupLockedContext }, group: '8_group_operations', order: 10, when: IsAuxiliaryWindowContext.toNegated() /* already a primary action for aux windows */ });
 MenuRegistry.appendMenuItem(MenuId.EditorTitle, { command: { id: ConfigureEditorAction.ID, title: localize('configureEditors', "Configure Editors") }, group: '9_configure', order: 10 });
 
-function appendEditorToolItem(primary: ICommandAction, when: ContextKeyExpression | undefined, order: number, alternative?: ICommandAction, precondition?: ContextKeyExpression | undefined, enableInCompactMode?: boolean): void {
+function appendEditorToolItem(primary: ICommandAction, when: ContextKeyExpression | undefined, order: number, alternative?: ICommandAction, precondition?: ContextKeyExpression | undefined, enableInCompactMode?: boolean, enableInModalMode?: boolean): void {
 	const item: IMenuItem = {
 		command: {
 			id: primary.id,
@@ -455,6 +455,9 @@ function appendEditorToolItem(primary: ICommandAction, when: ContextKeyExpressio
 	if (enableInCompactMode) {
 		MenuRegistry.appendMenuItem(MenuId.CompactWindowEditorTitle, item);
 	}
+	if (enableInModalMode) {
+		MenuRegistry.appendMenuItem(MenuId.ModalEditorEditorTitle, item);
+	}
 }
 
 const SPLIT_ORDER = 100000;  // towards the end
@@ -601,6 +604,7 @@ appendEditorToolItem(
 	10,
 	undefined,
 	EditorContextKeys.hasChanges,
+	true,
 	true
 );
 
@@ -616,6 +620,7 @@ appendEditorToolItem(
 	11,
 	undefined,
 	EditorContextKeys.hasChanges,
+	true,
 	true
 );
 
diff --git a/src/vs/workbench/browser/parts/editor/editorCommands.ts b/src/vs/workbench/browser/parts/editor/editorCommands.ts
index cedb8c9537371..df84193921256 100644
--- a/src/vs/workbench/browser/parts/editor/editorCommands.ts
+++ b/src/vs/workbench/browser/parts/editor/editorCommands.ts
@@ -1517,11 +1517,15 @@ function registerModalEditorCommands(): void {
 				f1: true,
 				icon: Codicon.close,
 				precondition: EditorPartModalContext,
-				keybinding: {
+				keybinding: [{
 					primary: KeyCode.Escape,
-					weight: KeybindingWeight.WorkbenchContrib + 10,
-					when: EditorPartModalContext
-				},
+					weight: KeybindingWeight.WorkbenchContrib + 10, // higher when no text editor is focused...
+					when: EditorContextKeys.focus.toNegated()
+				}, {
+					primary: KeyCode.Escape,
+					weight: KeybindingWeight.EditorContrib - 1, // ...lower to prevent accidental close when text editor is focused
+					when: EditorContextKeys.focus
+				}],
 				menu: {
 					id: MenuId.ModalEditorTitle,
 					group: 'navigation',
diff --git a/src/vs/workbench/browser/parts/editor/editorGroupWatermark.ts b/src/vs/workbench/browser/parts/editor/editorGroupWatermark.ts
index a5b6b341f20ac..03bfed510efa8 100644
--- a/src/vs/workbench/browser/parts/editor/editorGroupWatermark.ts
+++ b/src/vs/workbench/browser/parts/editor/editorGroupWatermark.ts
@@ -48,8 +48,8 @@ const baseEntries: WatermarkEntry[] = [
 
 const emptyWindowEntries: WatermarkEntry[] = coalesce([
 	...baseEntries,
-	...(isMacintosh && !isWeb ? [openFileOrFolder] : [openFile, openFolder]),
 	openRecent,
+	...(isMacintosh && !isWeb ? [openFileOrFolder] : [openFile, openFolder]),
 	isMacintosh && !isWeb ? newUntitledFile : undefined, // fill in one more on macOS to get to 5 entries
 ]);
 
diff --git a/src/vs/workbench/browser/parts/editor/editorPart.ts b/src/vs/workbench/browser/parts/editor/editorPart.ts
index ca2d962ea0dd6..31f83c70a1140 100644
--- a/src/vs/workbench/browser/parts/editor/editorPart.ts
+++ b/src/vs/workbench/browser/parts/editor/editorPart.ts
@@ -34,7 +34,7 @@ import { IBoundarySashes } from '../../../../base/browser/ui/sash/sash.js';
 import { IHostService } from '../../../services/host/browser/host.js';
 import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
 import { ServiceCollection } from '../../../../platform/instantiation/common/serviceCollection.js';
-import { EditorPartMaximizedEditorGroupContext, EditorPartMultipleEditorGroupsContext } from '../../../common/contextkeys.js';
+import { EditorPartMaximizedEditorGroupContext, EditorPartMultipleEditorGroupsContext, EditorTabsVisibleContext } from '../../../common/contextkeys.js';
 import { mainWindow } from '../../../../base/browser/window.js';
 
 export interface IEditorPartUIState {
@@ -168,7 +168,7 @@ export class EditorPart extends Part<IEditorPartMemento> implements IEditorPart,
 		readonly windowId: number,
 		@IInstantiationService private readonly instantiationService: IInstantiationService,
 		@IThemeService themeService: IThemeService,
-		@IConfigurationService private readonly configurationService: IConfigurationService,
+		@IConfigurationService protected readonly configurationService: IConfigurationService,
 		@IStorageService storageService: IStorageService,
 		@IWorkbenchLayoutService layoutService: IWorkbenchLayoutService,
 		@IHostService private readonly hostService: IHostService,
@@ -1039,6 +1039,7 @@ export class EditorPart extends Part<IEditorPartMemento> implements IEditorPart,
 	protected handleContextKeys(): void {
 		const multipleEditorGroupsContext = EditorPartMultipleEditorGroupsContext.bindTo(this.scopedContextKeyService);
 		const maximizedEditorGroupContext = EditorPartMaximizedEditorGroupContext.bindTo(this.scopedContextKeyService);
+		const editorTabsVisibleContext = EditorTabsVisibleContext.bindTo(this.scopedContextKeyService);
 
 		const updateContextKeys = () => {
 			const groupCount = this.count;
@@ -1055,11 +1056,17 @@ export class EditorPart extends Part<IEditorPartMemento> implements IEditorPart,
 			}
 		};
 
+		const updateEditorTabsVisibleContext = () => {
+			editorTabsVisibleContext.set(this.partOptions.showTabs === 'multiple');
+		};
+
 		updateContextKeys();
+		updateEditorTabsVisibleContext();
 
 		this._register(this.onDidAddGroup(() => updateContextKeys()));
 		this._register(this.onDidRemoveGroup(() => updateContextKeys()));
 		this._register(this.onDidChangeGroupMaximized(() => updateContextKeys()));
+		this._register(this.onDidChangeEditorPartOptions(() => updateEditorTabsVisibleContext()));
 	}
 
 	private setupDragAndDropSupport(parent: HTMLElement, container: HTMLElement): void {
diff --git a/src/vs/workbench/browser/parts/editor/editorParts.ts b/src/vs/workbench/browser/parts/editor/editorParts.ts
index c2ccf4a7316b0..0e9f70f8c2293 100644
--- a/src/vs/workbench/browser/parts/editor/editorParts.ts
+++ b/src/vs/workbench/browser/parts/editor/editorParts.ts
@@ -22,7 +22,7 @@ import { IThemeService } from '../../../../platform/theme/common/themeService.js
 import { IAuxiliaryWindowOpenOptions, IAuxiliaryWindowService } from '../../../services/auxiliaryWindow/browser/auxiliaryWindowService.js';
 import { generateUuid } from '../../../../base/common/uuid.js';
 import { ContextKeyValue, IContextKey, IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
-import { getActiveElement, isAncestor, isHTMLElement } from '../../../../base/browser/dom.js';
+import { getActiveElement, IDimension, isAncestor, isHTMLElement } from '../../../../base/browser/dom.js';
 import { ServiceCollection } from '../../../../platform/instantiation/common/serviceCollection.js';
 import { IEditorService } from '../../../services/editor/common/editorService.js';
 import { DeepPartial } from '../../../../base/common/types.js';
@@ -45,8 +45,15 @@ interface IEditorWorkingSetState extends IEditorWorkingSet {
 	readonly auxiliary: IEditorPartsUIState;
 }
 
+interface IModalEditorPartState {
+	readonly maximized: boolean;
+	readonly size?: { readonly width: number; readonly height: number };
+	readonly position?: { readonly left: number; readonly top: number };
+}
+
 interface IEditorPartsMemento {
 	'editorparts.state'?: IEditorPartsUIState;
+	'editorparts.modalState'?: IModalEditorPartState;
 }
 
 export class EditorParts extends MultiWindowParts<EditorPart, IEditorPartsMemento> implements IEditorGroupsService, IEditorPartsView {
@@ -75,6 +82,13 @@ export class EditorParts extends MultiWindowParts<EditorPart, IEditorPartsMement
 			return [];
 		})();
 
+		const modalState = this.profileMemento[EditorParts.MODAL_EDITOR_STATE_STORAGE_KEY];
+		if (modalState) {
+			this.modalEditorMaximized = modalState.maximized;
+			this.modalEditorSize = modalState.size;
+			this.modalEditorPosition = modalState.position;
+		}
+
 		this.mainPart = this._register(this.createMainEditorPart());
 		this._register(this.registerPart(this.mainPart));
 
@@ -158,6 +172,10 @@ export class EditorParts extends MultiWindowParts<EditorPart, IEditorPartsMement
 	private modalEditorPart: IModalEditorPart | undefined;
 	get activeModalEditorPart(): IModalEditorPart | undefined { return this.modalEditorPart; }
 
+	private modalEditorMaximized = false;
+	private modalEditorSize: IDimension | undefined;
+	private modalEditorPosition: { readonly left: number; readonly top: number } | undefined;
+
 	async createModalEditorPart(options?: IModalEditorPartOptions): Promise<IModalEditorPart> {
 
 		// Reuse existing modal editor part if it exists
@@ -167,12 +185,23 @@ export class EditorParts extends MultiWindowParts<EditorPart, IEditorPartsMement
 			return this.modalEditorPart;
 		}
 
-		const { part, instantiationService, disposables } = await this.instantiationService.createInstance(ModalEditorPart, this).create(options);
+		const { part, instantiationService, disposables } = await this.instantiationService.createInstance(ModalEditorPart, this).create({
+			...options,
+			maximized: options?.maximized ?? this.modalEditorMaximized,
+			size: options?.size ?? this.modalEditorSize,
+			position: options?.position ?? this.modalEditorPosition,
+		});
 
 		// Keep instantiation service and reference to reuse
 		this.modalEditorPart = part;
 		this.modalPartInstantiationService = instantiationService;
+
+		// Remember state on dispose to restore when opening next time
 		disposables.add(toDisposable(() => {
+			this.modalEditorMaximized = part.maximized;
+			this.modalEditorSize = part.size;
+			this.modalEditorPosition = part.position;
+
 			this.modalPartInstantiationService = undefined;
 			this.modalEditorPart = undefined;
 		}));
@@ -321,8 +350,10 @@ export class EditorParts extends MultiWindowParts<EditorPart, IEditorPartsMement
 	//#region Lifecycle / State
 
 	private static readonly EDITOR_PARTS_UI_STATE_STORAGE_KEY = 'editorparts.state';
+	private static readonly MODAL_EDITOR_STATE_STORAGE_KEY = 'editorparts.modalState';
 
 	private readonly workspaceMemento = this.getMemento(StorageScope.WORKSPACE, StorageTarget.USER);
+	private readonly profileMemento = this.getMemento(StorageScope.PROFILE, StorageTarget.MACHINE);
 
 	private _isReady = false;
 	get isReady(): boolean { return this._isReady; }
@@ -374,6 +405,32 @@ export class EditorParts extends MultiWindowParts<EditorPart, IEditorPartsMement
 		} else {
 			this.workspaceMemento[EditorParts.EDITOR_PARTS_UI_STATE_STORAGE_KEY] = state;
 		}
+
+		this.saveModalState();
+	}
+
+	private saveModalState(): void {
+
+		// Also capture state from any currently open modal editor part
+		if (this.modalEditorPart) {
+			this.modalEditorMaximized = this.modalEditorPart.maximized;
+			this.modalEditorSize = this.modalEditorPart.size;
+			this.modalEditorPosition = this.modalEditorPart.position;
+		}
+
+		// Only persist when there is meaningful state to restore.
+		// When all values are at their defaults (not maximized, no
+		// custom size or position), we delete the key to avoid
+		// storing unnecessary data.
+		if (this.modalEditorMaximized || this.modalEditorSize || this.modalEditorPosition) {
+			this.profileMemento[EditorParts.MODAL_EDITOR_STATE_STORAGE_KEY] = {
+				maximized: this.modalEditorMaximized,
+				size: this.modalEditorSize ? { width: this.modalEditorSize.width, height: this.modalEditorSize.height } : undefined,
+				position: this.modalEditorPosition,
+			};
+		} else {
+			delete this.profileMemento[EditorParts.MODAL_EDITOR_STATE_STORAGE_KEY];
+		}
 	}
 
 	private createState(): IEditorPartsUIState {
diff --git a/src/vs/workbench/browser/parts/editor/editorTitleControl.ts b/src/vs/workbench/browser/parts/editor/editorTitleControl.ts
index 00f7bf67590d6..132ca85f1656e 100644
--- a/src/vs/workbench/browser/parts/editor/editorTitleControl.ts
+++ b/src/vs/workbench/browser/parts/editor/editorTitleControl.ts
@@ -176,6 +176,7 @@ export class EditorTitleControl extends Themable {
 	}
 
 	updateOptions(oldOptions: IEditorPartOptions, newOptions: IEditorPartOptions): void {
+
 		// Update editor tabs control if options changed
 		if (
 			oldOptions.showTabs !== newOptions.showTabs ||
diff --git a/src/vs/workbench/browser/parts/editor/media/breadcrumbscontrol.css b/src/vs/workbench/browser/parts/editor/media/breadcrumbscontrol.css
index 4e4e923ad9b7e..a80a925d97ad7 100644
--- a/src/vs/workbench/browser/parts/editor/media/breadcrumbscontrol.css
+++ b/src/vs/workbench/browser/parts/editor/media/breadcrumbscontrol.css
@@ -3,6 +3,10 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+.monaco-workbench.vs .breadcrumbs-control {
+	border-bottom: 1px solid var(--vscode-editorWidget-border);
+}
+
 .monaco-workbench .part.editor > .content .editor-group-container .breadcrumbs-control.hidden {
 	display: none;
 }
diff --git a/src/vs/workbench/browser/parts/editor/media/editorgroupview.css b/src/vs/workbench/browser/parts/editor/media/editorgroupview.css
index 8eff5df9389e9..9f63f8390de56 100644
--- a/src/vs/workbench/browser/parts/editor/media/editorgroupview.css
+++ b/src/vs/workbench/browser/parts/editor/media/editorgroupview.css
@@ -5,6 +5,52 @@
 
 /* Container */
 
+/* Editor depth shadows - the ::after pseudo-element draws inset shadows on each edge,
+ * creating the illusion that sidebar, panel, and auxiliarybar float above it. */
+.monaco-workbench.vs .part.editor {
+	position: relative;
+}
+
+.monaco-workbench.vs .part.editor::after {
+	content: '';
+	position: absolute;
+	inset: 0;
+	pointer-events: none;
+	z-index: 10;
+	box-shadow:
+		inset var(--vscode-shadow-depth-x),
+		inset calc(-1 * 5px) 0 10px -4px rgba(0, 0, 0, 0.04),
+		inset 0 calc(-1 * 5px) 10px -4px rgba(0, 0, 0, 0.05);
+}
+
+/* When sidebar is on the right, flip the stronger shadow to the right edge */
+.monaco-workbench.sidebar-right.vs .part.editor::after {
+	box-shadow:
+		inset 5px 0 10px -4px rgba(0, 0, 0, 0.04),
+		inset calc(-1 * 5px) 0 10px -4px rgba(0, 0, 0, 0.05),
+		inset 0 calc(-1 * 5px) 10px -4px rgba(0, 0, 0, 0.05);
+}
+
+/* Panel positions: strengthen the shadow on whichever edge faces the panel */
+.monaco-workbench.panel-position-left.vs .part.editor::after {
+	box-shadow:
+		inset var(--vscode-shadow-depth-x),
+		inset calc(-1 * 5px) 0 10px -4px rgba(0, 0, 0, 0.04);
+}
+
+.monaco-workbench.panel-position-right.vs .part.editor::after {
+	box-shadow:
+		inset 5px 0 10px -4px rgba(0, 0, 0, 0.04),
+		inset calc(-1 * 5px) 0 10px -4px rgba(0, 0, 0, 0.05);
+}
+
+.monaco-workbench.panel-position-top.vs .part.editor::after {
+	box-shadow:
+		inset var(--vscode-shadow-depth-x),
+		inset calc(-1 * 5px) 0 10px -4px rgba(0, 0, 0, 0.04),
+		inset 0 var(--vscode-shadow-depth-y);
+}
+
 .monaco-workbench .part.editor > .content .editor-group-container {
 	height: 100%;
 }
diff --git a/src/vs/workbench/browser/parts/editor/media/modalEditorPart.css b/src/vs/workbench/browser/parts/editor/media/modalEditorPart.css
index 6be747356305d..b5b6e0efd741e 100644
--- a/src/vs/workbench/browser/parts/editor/media/modalEditorPart.css
+++ b/src/vs/workbench/browser/parts/editor/media/modalEditorPart.css
@@ -12,17 +12,20 @@
 	left: 0;
 	/* z-index for modal editors: above titlebar (2500) but below quick input (2550) and dialogs (2575) */
 	z-index: 2540;
-	display: flex;
-	justify-content: center;
-	align-items: center;
 	/* Never allow content to escape above the title bar */
 	overflow: hidden;
 	background: rgba(0, 0, 0, 0.3);
 
+	.modal-editor-resizable {
+		position: absolute;
+	}
+
 	.modal-editor-shadow {
-		box-shadow: 0 4px 32px var(--vscode-widget-shadow, rgba(0, 0, 0, 0.2));
+		box-shadow: var(--vscode-shadow-xl);
 		border-radius: 8px;
 		overflow: hidden;
+		width: 100%;
+		height: 100%;
 	}
 }
 
@@ -30,8 +33,8 @@
 .monaco-modal-editor-block .modal-editor-part {
 	display: flex;
 	flex-direction: column;
-	min-width: 400px;
-	min-height: 300px;
+	width: 100%;
+	height: 100%;
 	background-color: var(--vscode-editor-background);
 	border: 1px solid var(--vscode-editorWidget-border, var(--vscode-contrastBorder));
 	border-radius: 8px;
@@ -138,5 +141,13 @@
 				color: inherit;
 			}
 		}
+
+		.modal-editor-action-separator {
+			width: 1px;
+			height: 16px;
+			margin: 0 4px;
+			background-color: var(--vscode-titleBar-activeForeground);
+			opacity: 0.3;
+		}
 	}
 }
diff --git a/src/vs/workbench/browser/parts/editor/media/multieditortabscontrol.css b/src/vs/workbench/browser/parts/editor/media/multieditortabscontrol.css
index 924d9b336078e..4f9477d08657a 100644
--- a/src/vs/workbench/browser/parts/editor/media/multieditortabscontrol.css
+++ b/src/vs/workbench/browser/parts/editor/media/multieditortabscontrol.css
@@ -144,6 +144,14 @@
 	box-shadow: none;
 }
 
+.monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container > .tab.active {
+	box-shadow: inset var(--vscode-shadow-active-tab);
+}
+
+.monaco-workbench .part.editor > .content .editor-group-container > .title .tabs-container > .tab:hover:not(.active) {
+	box-shadow: var(--vscode-shadow-sm);
+}
+
 .monaco-workbench .part.editor > .content .editor-group-container > .title > .tabs-and-actions-container.wrapping .tabs-container > .tab:last-child {
 	margin-right: var(--last-tab-margin-right); /* when tabs wrap, we need a margin away from the absolute positioned editor actions */
 }
diff --git a/src/vs/workbench/browser/parts/editor/modalEditorPart.ts b/src/vs/workbench/browser/parts/editor/modalEditorPart.ts
index 3e3270d3ee67d..9bbb3c3b53e6e 100644
--- a/src/vs/workbench/browser/parts/editor/modalEditorPart.ts
+++ b/src/vs/workbench/browser/parts/editor/modalEditorPart.ts
@@ -4,14 +4,15 @@
  *--------------------------------------------------------------------------------------------*/
 
 import './media/modalEditorPart.css';
-import { $, addDisposableListener, append, EventHelper, EventType, hide, isHTMLElement, show } from '../../../../base/browser/dom.js';
+import { $, addDisposableListener, append, Dimension, EventHelper, EventType, hide, IDimension, isHTMLElement, setVisibility, show } from '../../../../base/browser/dom.js';
 import { StandardKeyboardEvent } from '../../../../base/browser/keyboardEvent.js';
+import { prepareActions } from '../../../../base/browser/ui/actionbar/actionbar.js';
 import { Button } from '../../../../base/browser/ui/button/button.js';
-import { KeyCode } from '../../../../base/common/keyCodes.js';
 import { Emitter, Event } from '../../../../base/common/event.js';
 import { DisposableStore, MutableDisposable, toDisposable } from '../../../../base/common/lifecycle.js';
+import { ResizableHTMLElement } from '../../../../base/browser/ui/resizable/resizable.js';
 import { MenuId } from '../../../../platform/actions/common/actions.js';
-import { HiddenItemStrategy, MenuWorkbenchToolBar } from '../../../../platform/actions/browser/toolbar.js';
+import { HiddenItemStrategy, MenuWorkbenchToolBar, WorkbenchToolBar } from '../../../../platform/actions/browser/toolbar.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
@@ -26,8 +27,8 @@ import { GroupDirection, GroupsOrder, IModalEditorPart, GroupActivationReason }
 import { IEditorService } from '../../../services/editor/common/editorService.js';
 import { EditorPartModalContext, EditorPartModalMaximizedContext, EditorPartModalNavigationContext } from '../../../common/contextkeys.js';
 import { EditorResourceAccessor, SideBySideEditor, Verbosity } from '../../../common/editor.js';
+import { EditorInput } from '../../../common/editor/editorInput.js';
 import { ResourceLabel } from '../../labels.js';
-import { IWorkbenchEnvironmentService } from '../../../services/environment/common/environmentService.js';
 import { IHostService } from '../../../services/host/browser/host.js';
 import { IWorkbenchLayoutService, Parts } from '../../../services/layout/browser/layoutService.js';
 import { mainWindow } from '../../../../base/browser/window.js';
@@ -36,13 +37,65 @@ import { Codicon } from '../../../../base/common/codicons.js';
 import { CLOSE_MODAL_EDITOR_COMMAND_ID, MOVE_MODAL_EDITOR_TO_MAIN_COMMAND_ID, MOVE_MODAL_EDITOR_TO_WINDOW_COMMAND_ID, NAVIGATE_MODAL_EDITOR_NEXT_COMMAND_ID, NAVIGATE_MODAL_EDITOR_PREVIOUS_COMMAND_ID, TOGGLE_MODAL_EDITOR_MAXIMIZED_COMMAND_ID } from './editorCommands.js';
 import { IModalEditorNavigation, IModalEditorPartOptions } from '../../../../platform/editor/common/editor.js';
 
+const MODAL_MIN_WIDTH = 400;
+const MODAL_MIN_HEIGHT = 300;
+const MODAL_MAX_DEFAULT_WIDTH = 1400;
+const MODAL_MAX_DEFAULT_HEIGHT = 900;
+const MODAL_BORDER_SIZE = 2; // 1px border on each side
+const MODAL_HEADER_HEIGHT = 33; // 32px header + 1px border bottom
+const MODAL_SNAP_THRESHOLD = 20;
+const MODAL_MAXIMIZED_PADDING = 16;
+
 const defaultModalEditorAllowableCommands = new Set([
+
+	// Application
 	'workbench.action.quit',
 	'workbench.action.reloadWindow',
-	'workbench.action.closeActiveEditor',
-	'workbench.action.closeAllEditors',
+	'workbench.action.toggleFullScreen',
+
+	// Quick access
+	'workbench.action.gotoSymbol',
+	'workbench.action.gotoLine',
+
+	// Zoom
+	'workbench.action.zoomIn',
+	'workbench.action.zoomOut',
+	'workbench.action.zoomReset',
+
+	// File operations
 	'workbench.action.files.save',
 	'workbench.action.files.saveAll',
+	'workbench.action.files.revert',
+
+	// Close editors
+	'workbench.action.closeActiveEditor',
+	'workbench.action.closeAllEditors',
+	'workbench.action.closeEditorsInGroup',
+	'workbench.action.closeUnmodifiedEditors',
+
+	// Settings
+	'workbench.action.openSettings',
+	'workbench.action.openSettings2',
+	'workbench.action.openSettingsJson',
+	'workbench.action.openGlobalSettings',
+	'workbench.action.openApplicationSettingsJson',
+	'workbench.action.openRawDefaultSettings',
+	'workbench.action.openWorkspaceSettings',
+	'workbench.action.openWorkspaceSettingsFile',
+	'workbench.action.openFolderSettings',
+	'workbench.action.openFolderSettingsFile',
+	'workbench.action.openRemoteSettings',
+	'workbench.action.openRemoteSettingsFile',
+	'workbench.action.openAccessibilitySettings',
+	'workbench.action.configureLanguageBasedSettings',
+
+	// Keybindings
+	'workbench.action.openGlobalKeybindings',
+	'workbench.action.openDefaultKeybindingsFile',
+	'workbench.action.openGlobalKeybindingsFile',
+	'workbench.action.openKeyboardLayoutPicker',
+
+	// Modal editor
 	CLOSE_MODAL_EDITOR_COMMAND_ID,
 	MOVE_MODAL_EDITOR_TO_MAIN_COMMAND_ID,
 	MOVE_MODAL_EDITOR_TO_WINDOW_COMMAND_ID,
@@ -51,6 +104,8 @@ const defaultModalEditorAllowableCommands = new Set([
 	NAVIGATE_MODAL_EDITOR_NEXT_COMMAND_ID,
 ]);
 
+const USE_MODAL_EDITOR_SETTING = 'workbench.editor.useModal';
+
 export interface ICreateModalEditorPartResult {
 	readonly part: ModalEditorPartImpl;
 	readonly instantiationService: IInstantiationService;
@@ -66,7 +121,7 @@ export class ModalEditorPart {
 		@IWorkbenchLayoutService private readonly layoutService: IWorkbenchLayoutService,
 		@IKeybindingService private readonly keybindingService: IKeybindingService,
 		@IHostService private readonly hostService: IHostService,
-		@IWorkbenchEnvironmentService private readonly environmentService: IWorkbenchEnvironmentService,
+		@IConfigurationService private readonly configurationService: IConfigurationService,
 	) {
 	}
 
@@ -87,18 +142,18 @@ export class ModalEditorPart {
 			}
 		}));
 
+		let useModalMode = this.configurationService.getValue<string>(USE_MODAL_EDITOR_SETTING);
+		disposables.add(this.configurationService.onDidChangeConfiguration(e => {
+			if (e.affectsConfiguration(USE_MODAL_EDITOR_SETTING)) {
+				useModalMode = this.configurationService.getValue<string>(USE_MODAL_EDITOR_SETTING);
+			}
+		}));
+
 		disposables.add(addDisposableListener(modalElement, EventType.KEY_DOWN, e => {
 			const event = new StandardKeyboardEvent(e);
 
-			// Close on Escape
-			if (event.equals(KeyCode.Escape)) {
-				EventHelper.stop(event, true);
-
-				editorPart.close();
-			}
-
-			// Prevent unsupported commands (not in sessions windows)
-			else if (!this.environmentService.isSessionsWindow) {
+			// Prevent unsupported commands unless all editors open in modal
+			if (useModalMode !== 'all') {
 				const resolved = this.keybindingService.softDispatch(event, this.layoutService.mainContainer);
 				if (resolved.kind === ResultKind.KbFound && resolved.commandId) {
 					if (
@@ -111,7 +166,14 @@ export class ModalEditorPart {
 			}
 		}));
 
-		const shadowElement = modalElement.appendChild($('.modal-editor-shadow'));
+		// Resizable wrapper
+		const resizableElement = new ResizableHTMLElement();
+		disposables.add(toDisposable(() => resizableElement.dispose()));
+		resizableElement.domNode.classList.add('modal-editor-resizable');
+		resizableElement.minSize = new Dimension(MODAL_MIN_WIDTH, MODAL_MIN_HEIGHT);
+		modalElement.appendChild(resizableElement.domNode);
+
+		const shadowElement = resizableElement.domNode.appendChild($('.modal-editor-shadow'));
 
 		// Editor part container
 		const titleId = 'modal-editor-title';
@@ -119,7 +181,6 @@ export class ModalEditorPart {
 			role: 'dialog',
 			'aria-modal': 'true',
 			'aria-labelledby': titleId,
-			tabIndex: -1
 		});
 		shadowElement.appendChild(editorPartContainer);
 
@@ -191,7 +252,31 @@ export class ModalEditorPart {
 			[IEditorService, modalEditorService]
 		)));
 
-		// Create toolbar
+		// Create editor toolbar
+		const editorActionsToolbarContainer = append(actionBarContainer, $('div.modal-editor-editor-actions'));
+		const editorActionsToolbar = disposables.add(scopedInstantiationService.createInstance(WorkbenchToolBar, editorActionsToolbarContainer, {
+			hiddenItemStrategy: HiddenItemStrategy.NoHide,
+			highlightToggledItems: true,
+		}));
+
+		const editorActionsSeparator = append(actionBarContainer, $('div.modal-editor-action-separator'));
+		const editorActionsDisposables = disposables.add(new DisposableStore());
+		const updateEditorActions = () => {
+			editorActionsDisposables.clear();
+
+			const editorActions = editorPart.activeGroup.createEditorActions(editorActionsDisposables, MenuId.ModalEditorEditorTitle);
+			editorActionsDisposables.add(editorActions.onDidChange(() => updateEditorActions()));
+
+			const { primary, secondary } = editorActions.actions;
+			editorActionsToolbar.setActions(prepareActions(primary), prepareActions(secondary));
+
+			const hasActions = primary.length > 0 || secondary.length > 0;
+			setVisibility(hasActions, editorActionsSeparator);
+		};
+		disposables.add(Event.runAndSubscribe(modalEditorService.onDidActiveEditorChange, () => updateEditorActions()));
+		disposables.add(modalEditorService.onDidEditorsChange(() => editorPart.enforceModalPartOptions()));
+
+		// Create global toolbar
 		disposables.add(scopedInstantiationService.createInstance(MenuWorkbenchToolBar, actionBarContainer, MenuId.ModalEditorTitle, {
 			hiddenItemStrategy: HiddenItemStrategy.NoHide,
 			highlightToggledItems: true,
@@ -200,7 +285,9 @@ export class ModalEditorPart {
 
 		// Create label
 		const label = disposables.add(scopedInstantiationService.createInstance(ResourceLabel, titleElement, {}));
-		disposables.add(Event.runAndSubscribe(modalEditorService.onDidActiveEditorChange, () => {
+		const labelChangeDisposable = disposables.add(new MutableDisposable());
+		let trackedEditor: EditorInput | undefined;
+		const updateLabel = () => {
 			const activeEditor = editorPart.activeGroup.activeEditor;
 			if (activeEditor) {
 				const { labelFormat } = editorPart.partOptions;
@@ -216,62 +303,249 @@ export class ModalEditorPart {
 						extraClasses: activeEditor.getLabelExtraClasses(),
 					}
 				);
+
+				// Only (re)subscribe when the active editor changes, not on every label update
+				if (trackedEditor !== activeEditor) {
+					trackedEditor = activeEditor;
+					labelChangeDisposable.value = activeEditor.onDidChangeLabel(() => updateLabel());
+				}
 			} else {
 				label.element.clear();
+				trackedEditor = undefined;
+				labelChangeDisposable.clear();
 			}
-
-			editorPart.notifyActiveEditorChanged();
-		}));
+		};
+		disposables.add(Event.runAndSubscribe(modalEditorService.onDidActiveEditorChange, updateLabel));
 
 		// Handle double-click on header to toggle maximize
 		disposables.add(addDisposableListener(headerElement, EventType.DBLCLICK, e => {
 			EventHelper.stop(e);
 
-			editorPart.toggleMaximized();
+			editorPart.handleHeaderDoubleClick();
 		}));
 
+		// Handle drag on header to move the modal
+		const dragDisposables = disposables.add(new DisposableStore());
+		let didDrag = false;
+		disposables.add(addDisposableListener(headerElement, EventType.MOUSE_DOWN, e => {
+			if (editorPart.maximized) {
+				return; // no drag when maximized
+			}
+
+			if (e.button !== 0) {
+				return; // only left button
+			}
+
+			// Ignore if target is a button or action
+			const target = e.target as HTMLElement;
+			if (target.closest('.monaco-button') || target.closest('.action-item')) {
+				return;
+			}
+
+			// Prevent text selection during drag
+			e.preventDefault();
+
+			dragDisposables.clear();
+
+			const startX = e.clientX;
+			const startY = e.clientY;
+			const startLeft = parseFloat(resizableElement.domNode.style.left) || 0;
+			const startTop = parseFloat(resizableElement.domNode.style.top) || 0;
+			didDrag = false;
+
+			const onMouseMove = (moveEvent: MouseEvent) => {
+				didDrag = true;
+				EventHelper.stop(moveEvent, true);
+
+				const containerDimension = this.layoutService.mainContainerDimension;
+				const titleBarOffset = this.layoutService.mainContainerOffset.top;
+				const dialogWidth = resizableElement.size.width;
+				const dialogHeight = resizableElement.size.height;
+
+				// Clamp to window bounds
+				const minLeft = 0;
+				const minTop = titleBarOffset;
+				const maxLeft = Math.max(minLeft, containerDimension.width - dialogWidth);
+				const maxTop = Math.max(minTop, containerDimension.height - dialogHeight);
+
+				let newLeft = Math.max(minLeft, Math.min(maxLeft, startLeft + (moveEvent.clientX - startX)));
+				let newTop = Math.max(minTop, Math.min(maxTop, startTop + (moveEvent.clientY - startY)));
+
+				// Snap to center position when close
+				const centerLeft = (containerDimension.width - dialogWidth) / 2;
+				const centerTop = Math.max(titleBarOffset, (containerDimension.height - dialogHeight) / 2);
+
+				if (Math.abs(newLeft - centerLeft) < MODAL_SNAP_THRESHOLD && Math.abs(newTop - centerTop) < MODAL_SNAP_THRESHOLD) {
+					newLeft = centerLeft;
+					newTop = centerTop;
+				}
+
+				resizableElement.domNode.style.left = `${newLeft}px`;
+				resizableElement.domNode.style.top = `${newTop}px`;
+			};
+
+			const onMouseUp = (upEvent: MouseEvent) => {
+				EventHelper.stop(upEvent, true);
+				dragDisposables.clear();
+
+				if (didDrag) {
+					const currentLeft = parseFloat(resizableElement.domNode.style.left) || 0;
+					const currentTop = parseFloat(resizableElement.domNode.style.top) || 0;
+
+					// Check if snapped to center — if so, clear custom position
+					const containerDimension = this.layoutService.mainContainerDimension;
+					const titleBarOffset = this.layoutService.mainContainerOffset.top;
+					const centerLeft = (containerDimension.width - resizableElement.size.width) / 2;
+					const centerTop = Math.max(titleBarOffset, (containerDimension.height - resizableElement.size.height) / 2);
+
+					if (Math.abs(currentLeft - centerLeft) < 1 && Math.abs(currentTop - centerTop) < 1) {
+						editorPart.position = undefined;
+					} else {
+						editorPart.position = { left: currentLeft, top: currentTop };
+					}
+				}
+			};
+
+			dragDisposables.add(addDisposableListener(mainWindow, EventType.MOUSE_MOVE, onMouseMove, true));
+			dragDisposables.add(addDisposableListener(mainWindow, EventType.MOUSE_UP, onMouseUp, true));
+		}));
+
+		// Focus active editor when clicking into the title area with no other click target
+		disposables.add(addDisposableListener(headerElement, EventType.CLICK, e => {
+			const wasDrag = didDrag;
+			didDrag = false;
+			if (wasDrag) {
+				return; // skip focus after drag
+			}
+
+			EventHelper.stop(e);
+
+			editorPart.activeGroup.focus();
+		}));
+
+		// Handle resize from sashes
+		let isResizing = false;
+		let resizeStartLeft = 0;
+		let resizeStartTop = 0;
+		let resizeStartSize = Dimension.None;
+
+		disposables.add(resizableElement.onDidWillResize(() => {
+			isResizing = true;
+			resizeStartLeft = parseFloat(resizableElement.domNode.style.left) || 0;
+			resizeStartTop = parseFloat(resizableElement.domNode.style.top) || 0;
+			resizeStartSize = new Dimension(resizableElement.size.width, resizableElement.size.height);
+		}));
+
+		disposables.add(resizableElement.onDidResize(e => {
+			const deltaWidth = e.dimension.width - resizeStartSize.width;
+			const deltaHeight = e.dimension.height - resizeStartSize.height;
+
+			// Adjust position to keep the opposite edge fixed
+			if (e.west) {
+				resizableElement.domNode.style.left = `${resizeStartLeft - deltaWidth}px`;
+			}
+			if (e.north) {
+				resizableElement.domNode.style.top = `${resizeStartTop - deltaHeight}px`;
+			}
+
+			// Update editor part layout during resize
+			editorPart.layout(e.dimension.width - MODAL_BORDER_SIZE, e.dimension.height - MODAL_BORDER_SIZE - MODAL_HEADER_HEIGHT, 0, 0);
+
+			if (e.done) {
+				isResizing = false;
+
+				// Check if size matches the default (from sash double-click reset)
+				const defaultSize = getDefaultSize();
+				if (e.dimension.width === defaultSize.width && e.dimension.height === defaultSize.height) {
+					editorPart.size = undefined;
+					editorPart.position = undefined;
+					layoutModal();
+				} else {
+					editorPart.size = new Dimension(e.dimension.width, e.dimension.height);
+					editorPart.position = {
+						left: parseFloat(resizableElement.domNode.style.left) || 0,
+						top: parseFloat(resizableElement.domNode.style.top) || 0,
+					};
+				}
+			}
+		}));
+
+		// Compute default (non-custom, non-maximized) modal size
+		const getDefaultSize = (): Dimension => {
+			const containerDimension = this.layoutService.mainContainerDimension;
+			const titleBarOffset = this.layoutService.mainContainerOffset.top;
+			const availableHeight = Math.max(containerDimension.height - titleBarOffset, 0);
+			const targetWidth = containerDimension.width * 0.8;
+			const targetHeight = availableHeight * 0.8;
+			const width = Math.min(targetWidth, MODAL_MAX_DEFAULT_WIDTH, containerDimension.width);
+			const height = Math.min(targetHeight, MODAL_MAX_DEFAULT_HEIGHT, availableHeight);
+
+			return new Dimension(width, height);
+		};
 
 		// Layout the modal editor part
 		const layoutModal = () => {
+			if (isResizing) {
+				return; // skip layout during interactive resize
+			}
+
 			const containerDimension = this.layoutService.mainContainerDimension;
 			const titleBarOffset = this.layoutService.mainContainerOffset.top;
 			const availableHeight = Math.max(containerDimension.height - titleBarOffset, 0);
 
+			const defaultSize = getDefaultSize();
+
 			let width: number;
 			let height: number;
 
 			if (editorPart.maximized) {
-				const horizontalPadding = 16;
-				const verticalPadding = Math.max(titleBarOffset /* keep away from title bar to prevent clipping issues with WCO */, 16);
-				width = Math.max(containerDimension.width - horizontalPadding, 0);
+				const verticalPadding = Math.max(titleBarOffset /* keep away from title bar to prevent clipping issues with WCO */, MODAL_MAXIMIZED_PADDING);
+				width = Math.max(containerDimension.width - MODAL_MAXIMIZED_PADDING, 0);
 				height = Math.max(availableHeight - verticalPadding, 0);
+			} else if (editorPart.size) {
+				width = Math.min(editorPart.size.width, containerDimension.width);
+				height = Math.min(editorPart.size.height, availableHeight);
 			} else {
-				const maxWidth = 1400;
-				const maxHeight = 900;
-				const targetWidth = containerDimension.width * 0.8;
-				const targetHeight = availableHeight * 0.8;
-				width = Math.min(targetWidth, maxWidth, containerDimension.width);
-				height = Math.min(targetHeight, maxHeight, availableHeight);
+				width = defaultSize.width;
+				height = defaultSize.height;
 			}
 
 			height = Math.min(height, availableHeight); // Ensure the modal never exceeds available height (below the title bar)
 
-			editorPartContainer.style.width = `${width}px`;
-			editorPartContainer.style.height = `${height}px`;
+			// Update resizable element size and constraints
+			resizableElement.maxSize = new Dimension(containerDimension.width, availableHeight);
+			resizableElement.preferredSize = defaultSize;
+			resizableElement.layout(height, width);
+
+			// Enable/disable sashes based on maximized state
+			const canResize = !editorPart.maximized;
+			resizableElement.enableSashes(canResize, canResize, canResize, canResize);
+
+			// Position: use custom position if available (clamped to bounds), otherwise center
+			if (!editorPart.maximized && editorPart.position) {
+				const clampedLeft = Math.max(0, Math.min(editorPart.position.left, containerDimension.width - width));
+				const clampedTop = Math.max(titleBarOffset, Math.min(editorPart.position.top, titleBarOffset + availableHeight - height));
+				resizableElement.domNode.style.left = `${clampedLeft}px`;
+				resizableElement.domNode.style.top = `${clampedTop}px`;
+			} else {
+				const left = (containerDimension.width - width) / 2;
+				const top = Math.max(titleBarOffset, (containerDimension.height - height) / 2); // center in full window, but clamp to stay below the title bar
+				resizableElement.domNode.style.left = `${left}px`;
+				resizableElement.domNode.style.top = `${top}px`;
+			}
 
-			const borderSize = 2; // Account for 1px border on all sides and modal header height
-			const headerHeight = 32 + 1 /* border bottom */;
-			editorPart.layout(width - borderSize, height - borderSize - headerHeight, 0, 0);
+			editorPart.layout(width - MODAL_BORDER_SIZE, height - MODAL_BORDER_SIZE - MODAL_HEADER_HEIGHT, 0, 0);
 		};
 		disposables.add(Event.runAndSubscribe(this.layoutService.onDidLayoutMainContainer, layoutModal));
 		disposables.add(editorPart.onDidChangeMaximized(() => layoutModal()));
+		disposables.add(editorPart.onDidRequestLayout(() => layoutModal()));
 
 		// Dim window controls to match the modal overlay
 		this.hostService.setWindowDimmed(mainWindow, true);
 		disposables.add(toDisposable(() => this.hostService.setWindowDimmed(mainWindow, false)));
 
-		// Focus the modal
-		editorPartContainer.focus();
+		// Focus
+		editorPart.activeGroup.focus();
 
 		return {
 			part: editorPart,
@@ -281,6 +555,11 @@ export class ModalEditorPart {
 	}
 }
 
+interface IPosition {
+	left: number;
+	top: number;
+}
+
 class ModalEditorPartImpl extends EditorPart implements IModalEditorPart {
 
 	private static COUNTER = 1;
@@ -291,12 +570,26 @@ class ModalEditorPartImpl extends EditorPart implements IModalEditorPart {
 	private readonly _onDidChangeMaximized = this._register(new Emitter<boolean>());
 	readonly onDidChangeMaximized = this._onDidChangeMaximized.event;
 
+	private readonly _onDidRequestLayout = this._register(new Emitter<void>());
+	readonly onDidRequestLayout = this._onDidRequestLayout.event;
+
 	private readonly _onDidChangeNavigation = this._register(new Emitter<IModalEditorNavigation | undefined>());
 	readonly onDidChangeNavigation = this._onDidChangeNavigation.event;
 
-	private _maximized = false;
+	private _maximized: boolean;
 	get maximized(): boolean { return this._maximized; }
 
+	private _size: IDimension | undefined;
+	get size(): IDimension | undefined { return this._size; }
+	set size(value: IDimension | undefined) { this._size = value; }
+
+	private _position: IPosition | undefined;
+	get position(): IPosition | undefined { return this._position; }
+	set position(value: IPosition | undefined) { this._position = value; }
+
+	private savedSize: IDimension | undefined;
+	private savedPosition: IPosition | undefined;
+
 	private _navigation: IModalEditorNavigation | undefined;
 	get navigation(): IModalEditorNavigation | undefined { return this._navigation; }
 
@@ -320,9 +613,25 @@ class ModalEditorPartImpl extends EditorPart implements IModalEditorPart {
 		const id = ModalEditorPartImpl.COUNTER++;
 		super(editorPartsView, `workbench.parts.modalEditor.${id}`, localize('modalEditorPart', "Modal Editor Area"), windowId, instantiationService, themeService, configurationService, storageService, layoutService, hostService, contextKeyService);
 
+		this._maximized = options?.maximized ?? false;
+		this._size = options?.size;
+		this._position = options?.position;
 		this._navigation = options?.navigation;
 
+		// When restoring a maximized state with custom layout,
+		// initialize saved state so un-maximize can restore it
+		if (this._maximized) {
+			this.savedSize = this._size;
+			this.savedPosition = this._position;
+		}
+
 		this.enforceModalPartOptions();
+
+		this._register(this.configurationService.onDidChangeConfiguration(e => {
+			if (e.affectsConfiguration(USE_MODAL_EDITOR_SETTING)) {
+				this.enforceModalPartOptions();
+			}
+		}));
 	}
 
 	override create(parent: HTMLElement, options?: object): void {
@@ -331,25 +640,28 @@ class ModalEditorPartImpl extends EditorPart implements IModalEditorPart {
 		super.create(parent, options);
 	}
 
-	private enforceModalPartOptions(): void {
+	enforceModalPartOptions(): void {
+		const useModalForAll = this.configurationService.getValue<string>(USE_MODAL_EDITOR_SETTING) === 'all';
 		const editorCount = this.groups.reduce((count, group) => count + group.count, 0);
+		const showTabs = useModalForAll && editorCount > 1 ? 'multiple' : 'none';
+
 		this.optionsDisposable.value = this.enforcePartOptions({
-			showTabs: editorCount > 1 ? 'multiple' : 'none',
+			showTabs,
 			enablePreview: true,
 			closeEmptyGroups: true,
-			tabActionCloseVisibility: editorCount > 1,
-			editorActionsLocation: 'default',
+			tabActionCloseVisibility: showTabs !== 'none',
+			editorActionsLocation: 'hidden',
 			tabHeight: 'default',
 			wrapTabs: false,
 			allowDropIntoGroup: false
 		});
 	}
 
-	notifyActiveEditorChanged(): void {
-		this.enforceModalPartOptions();
-	}
-
 	updateOptions(options?: IModalEditorPartOptions): void {
+		if (typeof options?.maximized === 'boolean' && options.maximized !== this._maximized) {
+			this.toggleMaximized();
+		}
+
 		this._navigation = options?.navigation;
 
 		this._onDidChangeNavigation.fire(options?.navigation);
@@ -358,9 +670,34 @@ class ModalEditorPartImpl extends EditorPart implements IModalEditorPart {
 	toggleMaximized(): void {
 		this._maximized = !this._maximized;
 
+		if (this._maximized) {
+			this.savedSize = this._size;
+			this.savedPosition = this._position;
+		} else {
+			this._size = this.savedSize;
+			this._position = this.savedPosition;
+			this.savedSize = undefined;
+			this.savedPosition = undefined;
+		}
+
 		this._onDidChangeMaximized.fire(this._maximized);
 	}
 
+	handleHeaderDoubleClick(): void {
+		if (this._maximized) {
+			// Clear saved state so that toggleMaximized restores to default
+			this.savedSize = undefined;
+			this.savedPosition = undefined;
+			this.toggleMaximized();
+		} else if (this._size) {
+			this._size = undefined;
+			this._position = undefined;
+			this._onDidRequestLayout.fire();
+		} else {
+			this.toggleMaximized(); // maximize
+		}
+	}
+
 	protected override handleContextKeys(): void {
 		const isModalEditorPartContext = EditorPartModalContext.bindTo(this.scopedContextKeyService);
 		isModalEditorPartContext.set(true);
diff --git a/src/vs/workbench/browser/parts/notifications/media/notificationsCenter.css b/src/vs/workbench/browser/parts/notifications/media/notificationsCenter.css
index 015f11afd5bde..ee7e8a6a64a0f 100644
--- a/src/vs/workbench/browser/parts/notifications/media/notificationsCenter.css
+++ b/src/vs/workbench/browser/parts/notifications/media/notificationsCenter.css
@@ -10,7 +10,9 @@
 	bottom: 29px; /* 22px status bar height + 7px (attempt to position at same location as a toast) */
 	display: none;
 	overflow: hidden;
-	border-radius: 4px;
+	border: 1px solid var(--vscode-editorWidget-border);
+	border-radius: var(--vscode-cornerRadius-small);
+	box-shadow: var(--vscode-shadow-lg);
 }
 
 .monaco-workbench.nostatusbar > .notifications-center {
@@ -59,7 +61,7 @@
 }
 
 .monaco-workbench > .notifications-center .notifications-list-container .monaco-list-row:last-child {
-	border-radius: 0px 0px 4px 4px; /* adopt the border radius at the end of the notifications center */
+	border-radius: 0px 0px var(--vscode-cornerRadius-small) var(--vscode-cornerRadius-small); /* adopt the border radius at the end of the notifications center */
 }
 
 /* Icons */
diff --git a/src/vs/workbench/browser/parts/notifications/media/notificationsToasts.css b/src/vs/workbench/browser/parts/notifications/media/notificationsToasts.css
index 0f5f3fdbfbab1..73764a1003e61 100644
--- a/src/vs/workbench/browser/parts/notifications/media/notificationsToasts.css
+++ b/src/vs/workbench/browser/parts/notifications/media/notificationsToasts.css
@@ -9,7 +9,7 @@
 	right: 3px;
 	bottom: 25px; /* 22px status bar height + 3px */
 	display: none;
-	overflow: hidden;
+	border-radius: var(--vscode-cornerRadius-small);
 }
 
 .monaco-workbench.nostatusbar > .notifications-toasts {
@@ -35,10 +35,6 @@
 	flex-direction: column;
 }
 
-.monaco-workbench > .notifications-toasts .notification-toast-container {
-	overflow: hidden; /* this ensures that the notification toast does not shine through */
-}
-
 .monaco-workbench > .notifications-toasts .notification-toast-container > .notification-toast {
 	margin: 4px; /* enables separation and drop shadows around toasts */
 	transform: translate3d(0px, 100%, 0px); /* move the notification 50px to the bottom (to prevent bleed through) */
@@ -46,6 +42,10 @@
 	transition:	transform 300ms ease-out, opacity 300ms ease-out;
 }
 
+.monaco-workbench > .notifications-toasts .notifications-list-container {
+	box-shadow: var(--vscode-shadow-lg);
+}
+
 .monaco-workbench > .notifications-toasts .notifications-list-container,
 .monaco-workbench > .notifications-toasts .notification-toast-container > .notification-toast,
 .monaco-workbench > .notifications-toasts .notification-toast-container > .notification-toast .monaco-scrollable-element,
diff --git a/src/vs/workbench/browser/parts/notifications/notificationsActions.ts b/src/vs/workbench/browser/parts/notifications/notificationsActions.ts
index 36ccd6f2af856..a97e459fe3c12 100644
--- a/src/vs/workbench/browser/parts/notifications/notificationsActions.ts
+++ b/src/vs/workbench/browser/parts/notifications/notificationsActions.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import './media/notificationsActions.css';
-import { INotificationViewItem } from '../../../common/notifications.js';
+import { INotificationViewItem, NotificationsPosition } from '../../../common/notifications.js';
 import { localize } from '../../../../nls.js';
 import { Action } from '../../../../base/common/actions.js';
 import { CLEAR_NOTIFICATION, EXPAND_NOTIFICATION, COLLAPSE_NOTIFICATION, CLEAR_ALL_NOTIFICATIONS, HIDE_NOTIFICATIONS_CENTER, TOGGLE_DO_NOT_DISTURB_MODE, TOGGLE_DO_NOT_DISTURB_MODE_BY_SOURCE } from './notificationsCommands.js';
@@ -19,11 +19,21 @@ const clearAllIcon = registerIcon('notifications-clear-all', Codicon.clearAll, l
 export const hideIcon = registerIcon('notifications-hide', Codicon.chevronDown, localize('hideIcon', 'Icon for the hide action in notifications.'));
 export const hideUpIcon = registerIcon('notifications-hide-up', Codicon.chevronUp, localize('hideUpIcon', 'Icon for the hide action in notifications when positioned at the top.'));
 const expandIcon = registerIcon('notifications-expand', Codicon.chevronUp, localize('expandIcon', 'Icon for the expand action in notifications.'));
+const expandDownIcon = registerIcon('notifications-expand-down', Codicon.chevronDown, localize('expandDownIcon', 'Icon for the expand action in notifications when the notification center is at the top.'));
 const collapseIcon = registerIcon('notifications-collapse', Codicon.chevronDown, localize('collapseIcon', 'Icon for the collapse action in notifications.'));
+const collapseUpIcon = registerIcon('notifications-collapse-up', Codicon.chevronUp, localize('collapseUpIcon', 'Icon for the collapse action in notifications when the notification center is at the top.'));
 const configureIcon = registerIcon('notifications-configure', Codicon.gear, localize('configureIcon', 'Icon for the configure action in notifications.'));
 const doNotDisturbIcon = registerIcon('notifications-do-not-disturb', Codicon.bellSlash, localize('doNotDisturbIcon', 'Icon for the mute all action in notifications.'));
 export const positionIcon = registerIcon('notifications-position', Codicon.arrowSwap, localize('positionIcon', 'Icon for the position action in notifications.'));
 
+export function getNotificationExpandIcon(position: NotificationsPosition): ThemeIcon {
+	return position === NotificationsPosition.TOP_RIGHT ? expandDownIcon : expandIcon;
+}
+
+export function getNotificationCollapseIcon(position: NotificationsPosition): ThemeIcon {
+	return position === NotificationsPosition.TOP_RIGHT ? collapseUpIcon : collapseIcon;
+}
+
 export class ClearNotificationAction extends Action {
 
 	static readonly ID = CLEAR_NOTIFICATION;
diff --git a/src/vs/workbench/browser/parts/notifications/notificationsCenter.ts b/src/vs/workbench/browser/parts/notifications/notificationsCenter.ts
index 76d5680b81f51..82f6975b6d86a 100644
--- a/src/vs/workbench/browser/parts/notifications/notificationsCenter.ts
+++ b/src/vs/workbench/browser/parts/notifications/notificationsCenter.ts
@@ -15,7 +15,6 @@ import { INotificationsCenterController, NotificationActionRunner } from './noti
 import { NotificationsList } from './notificationsList.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { $, Dimension, isAncestorOfActiveElement } from '../../../../base/browser/dom.js';
-import { widgetShadow } from '../../../../platform/theme/common/colorRegistry.js';
 import { IEditorGroupsService } from '../../../services/editor/common/editorGroupsService.js';
 import { localize } from '../../../../nls.js';
 import { ActionBar } from '../../../../base/browser/ui/actionbar/actionbar.js';
@@ -390,8 +389,6 @@ export class NotificationsCenter extends Themable implements INotificationsCente
 
 	override updateStyles(): void {
 		if (this.notificationsCenterContainer && this.notificationsCenterHeader) {
-			const widgetShadowColor = this.getColor(widgetShadow);
-			this.notificationsCenterContainer.style.boxShadow = widgetShadowColor ? `0 0 8px 2px ${widgetShadowColor}` : '';
 
 			const borderColor = this.getColor(NOTIFICATIONS_CENTER_BORDER);
 			this.notificationsCenterContainer.style.border = borderColor ? `1px solid ${borderColor}` : '';
diff --git a/src/vs/workbench/browser/parts/notifications/notificationsToasts.ts b/src/vs/workbench/browser/parts/notifications/notificationsToasts.ts
index 4aa6355a41b55..bd77caab75abb 100644
--- a/src/vs/workbench/browser/parts/notifications/notificationsToasts.ts
+++ b/src/vs/workbench/browser/parts/notifications/notificationsToasts.ts
@@ -14,7 +14,6 @@ import { Event, Emitter } from '../../../../base/common/event.js';
 import { IWorkbenchLayoutService, Parts } from '../../../services/layout/browser/layoutService.js';
 import { NOTIFICATIONS_TOAST_BORDER, NOTIFICATIONS_BACKGROUND } from '../../../common/theme.js';
 import { IThemeService, Themable } from '../../../../platform/theme/common/themeService.js';
-import { widgetShadow } from '../../../../platform/theme/common/colorRegistry.js';
 import { IEditorGroupsService } from '../../../services/editor/common/editorGroupsService.js';
 import { INotificationsToastController } from './notificationsCommands.js';
 import { IContextKey, IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
@@ -553,9 +552,6 @@ export class NotificationsToasts extends Themable implements INotificationsToast
 			const backgroundColor = this.getColor(NOTIFICATIONS_BACKGROUND);
 			toast.style.background = backgroundColor ? backgroundColor : '';
 
-			const widgetShadowColor = this.getColor(widgetShadow);
-			toast.style.boxShadow = widgetShadowColor ? `0 0 8px 2px ${widgetShadowColor}` : '';
-
 			const borderColor = this.getColor(NOTIFICATIONS_TOAST_BORDER);
 			toast.style.border = borderColor ? `1px solid ${borderColor}` : '';
 		});
diff --git a/src/vs/workbench/browser/parts/notifications/notificationsViewer.ts b/src/vs/workbench/browser/parts/notifications/notificationsViewer.ts
index 6512492cae4f4..7c01c6202c395 100644
--- a/src/vs/workbench/browser/parts/notifications/notificationsViewer.ts
+++ b/src/vs/workbench/browser/parts/notifications/notificationsViewer.ts
@@ -14,8 +14,8 @@ import { ActionRunner, IAction, IActionRunner, Separator, toAction } from '../..
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { dispose, DisposableStore, Disposable } from '../../../../base/common/lifecycle.js';
 import { IContextMenuService } from '../../../../platform/contextview/browser/contextView.js';
-import { INotificationViewItem, NotificationViewItem, NotificationViewItemContentChangeKind, INotificationMessage, ChoiceAction } from '../../../common/notifications.js';
-import { ClearNotificationAction, ExpandNotificationAction, CollapseNotificationAction, ConfigureNotificationAction } from './notificationsActions.js';
+import { INotificationViewItem, NotificationViewItem, NotificationViewItemContentChangeKind, INotificationMessage, ChoiceAction, NotificationsSettings, getNotificationsPosition } from '../../../common/notifications.js';
+import { ClearNotificationAction, ExpandNotificationAction, CollapseNotificationAction, ConfigureNotificationAction, getNotificationExpandIcon, getNotificationCollapseIcon } from './notificationsActions.js';
 import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
 import { ProgressBar } from '../../../../base/browser/ui/progressbar/progressbar.js';
 import { INotificationService, NotificationsFilter, Severity, isNotificationSource } from '../../../../platform/notification/common/notification.js';
@@ -32,6 +32,7 @@ import { StandardKeyboardEvent } from '../../../../base/browser/keyboardEvent.js
 import { getDefaultHoverDelegate } from '../../../../base/browser/ui/hover/hoverDelegateFactory.js';
 import type { IManagedHover } from '../../../../base/browser/ui/hover/hover.js';
 import { IHoverService } from '../../../../platform/hover/browser/hover.js';
+import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 
 export class NotificationsListDelegate implements IListVirtualDelegate<INotificationViewItem> {
 
@@ -316,6 +317,16 @@ export class NotificationTemplateRenderer extends Disposable {
 	private static expandNotificationAction: ExpandNotificationAction;
 	private static collapseNotificationAction: CollapseNotificationAction;
 
+	private static updateExpandCollapseIcons(configurationService: IConfigurationService): void {
+		if (!NotificationTemplateRenderer.expandNotificationAction) {
+			return;
+		}
+
+		const position = getNotificationsPosition(configurationService);
+		NotificationTemplateRenderer.expandNotificationAction.class = ThemeIcon.asClassName(getNotificationExpandIcon(position));
+		NotificationTemplateRenderer.collapseNotificationAction.class = ThemeIcon.asClassName(getNotificationCollapseIcon(position));
+	}
+
 	private static readonly SEVERITIES = [Severity.Info, Severity.Warning, Severity.Error];
 
 	private readonly inputDisposables = this._register(new DisposableStore());
@@ -328,6 +339,7 @@ export class NotificationTemplateRenderer extends Disposable {
 		@IKeybindingService private readonly keybindingService: IKeybindingService,
 		@IContextMenuService private readonly contextMenuService: IContextMenuService,
 		@IHoverService private readonly hoverService: IHoverService,
+		@IConfigurationService configurationService: IConfigurationService,
 	) {
 		super();
 
@@ -335,7 +347,14 @@ export class NotificationTemplateRenderer extends Disposable {
 			NotificationTemplateRenderer.closeNotificationAction = instantiationService.createInstance(ClearNotificationAction, ClearNotificationAction.ID, ClearNotificationAction.LABEL);
 			NotificationTemplateRenderer.expandNotificationAction = instantiationService.createInstance(ExpandNotificationAction, ExpandNotificationAction.ID, ExpandNotificationAction.LABEL);
 			NotificationTemplateRenderer.collapseNotificationAction = instantiationService.createInstance(CollapseNotificationAction, CollapseNotificationAction.ID, CollapseNotificationAction.LABEL);
+			NotificationTemplateRenderer.updateExpandCollapseIcons(configurationService);
 		}
+
+		this._register(configurationService.onDidChangeConfiguration(e => {
+			if (e.affectsConfiguration(NotificationsSettings.NOTIFICATIONS_POSITION)) {
+				NotificationTemplateRenderer.updateExpandCollapseIcons(configurationService);
+			}
+		}));
 	}
 
 	setInput(notification: INotificationViewItem): void {
diff --git a/src/vs/workbench/browser/parts/statusbar/media/statusbarpart.css b/src/vs/workbench/browser/parts/statusbar/media/statusbarpart.css
index 7faaf9e7f4b3f..1f3b102ebb13e 100644
--- a/src/vs/workbench/browser/parts/statusbar/media/statusbarpart.css
+++ b/src/vs/workbench/browser/parts/statusbar/media/statusbarpart.css
@@ -52,8 +52,7 @@
 }
 
 .monaco-workbench .part.statusbar > .left-items {
-	flex-grow: 1; /* left items push right items to the far right end */
-}
+	flex-grow: 1; /* left items push right items to the far right end */}
 
 .monaco-workbench .part.statusbar > .items-container > .statusbar-item {
 	display: inline-block;
@@ -85,9 +84,13 @@
 	border-right: 5px solid transparent;
 }
 
-.monaco-workbench .part.statusbar > .items-container > .statusbar-item.left.first-visible-item,
-.monaco-workbench .part.statusbar > .items-container > .statusbar-item.right.last-visible-item {
+.monaco-workbench .part.statusbar > .items-container > .statusbar-item.left.first-visible-item {
 	padding-right: 0;
+	padding-left: 2px;
+}
+
+.monaco-workbench .part.statusbar > .items-container > .statusbar-item.right.last-visible-item {
+	padding-right: 2px;
 	padding-left: 0;
 }
 
diff --git a/src/vs/workbench/browser/parts/titlebar/media/titlebarpart.css b/src/vs/workbench/browser/parts/titlebar/media/titlebarpart.css
index 454939c8afc4a..a2c1090f9d151 100644
--- a/src/vs/workbench/browser/parts/titlebar/media/titlebarpart.css
+++ b/src/vs/workbench/browser/parts/titlebar/media/titlebarpart.css
@@ -7,6 +7,7 @@
 .monaco-workbench .part.titlebar {
 	display: flex;
 	flex-direction: row;
+	box-shadow: var(--vscode-shadow-md);
 }
 
 .monaco-workbench.mac .part.titlebar {
@@ -172,10 +173,11 @@
 	border: 1px solid var(--vscode-commandCenter-border);
 	overflow: hidden;
 	margin: 0 6px;
-	border-radius: 4px;
+	border-radius: var(--vscode-cornerRadius-large);
 	height: 22px;
 	width: 38vw;
 	max-width: 600px;
+	box-shadow: inset var(--vscode-shadow-sm);
 }
 
 .monaco-workbench .part.titlebar > .titlebar-container > .titlebar-center > .window-title > .command-center .action-item.command-center-center .action-item.command-center-quick-pick {
diff --git a/src/vs/workbench/browser/web.main.ts b/src/vs/workbench/browser/web.main.ts
index fce64b1f33751..a7ba65b88629b 100644
--- a/src/vs/workbench/browser/web.main.ts
+++ b/src/vs/workbench/browser/web.main.ts
@@ -46,7 +46,8 @@ import { IRequestService } from '../../platform/request/common/request.js';
 import { IUserDataInitializationService, IUserDataInitializer, UserDataInitializationService } from '../services/userData/browser/userDataInit.js';
 import { UserDataSyncStoreManagementService } from '../../platform/userDataSync/common/userDataSyncStoreService.js';
 import { IUserDataSyncStoreManagementService } from '../../platform/userDataSync/common/userDataSync.js';
-import { ILifecycleService } from '../services/lifecycle/common/lifecycle.js';
+import { ILifecycleService, WillShutdownEvent } from '../services/lifecycle/common/lifecycle.js';
+import { Event } from '../../base/common/event.js';
 import { Action2, MenuId, registerAction2 } from '../../platform/actions/common/actions.js';
 import { IInstantiationService, ServicesAccessor } from '../../platform/instantiation/common/instantiation.js';
 import { localize, localize2 } from '../../nls.js';
@@ -99,6 +100,12 @@ import { IDefaultAccountService } from '../../platform/defaultAccount/common/def
 import { DefaultAccountService } from '../services/accounts/browser/defaultAccount.js';
 import { AccountPolicyService } from '../services/policies/common/accountPolicyService.js';
 
+export interface IBrowserMainWorkbench {
+	startup(): IInstantiationService;
+	readonly onWillShutdown: Event<WillShutdownEvent>;
+	readonly onDidShutdown: Event<void>;
+}
+
 export class BrowserMain extends Disposable {
 
 	private readonly onWillShutdownDisposables = this._register(new DisposableStore());
@@ -125,7 +132,7 @@ export class BrowserMain extends Disposable {
 		const [services] = await Promise.all([this.initServices(), domContentLoaded(getWindow(this.domElement))]);
 
 		// Create Workbench
-		const workbench = new Workbench(this.domElement, undefined, services.serviceCollection, services.logService);
+		const workbench = this.createWorkbench(this.domElement, services.serviceCollection, services.logService);
 
 		// Listeners
 		this.registerListeners(workbench);
@@ -247,7 +254,11 @@ export class BrowserMain extends Disposable {
 		});
 	}
 
-	private registerListeners(workbench: Workbench): void {
+	protected createWorkbench(domElement: HTMLElement, serviceCollection: ServiceCollection, logService: ILogService): IBrowserMainWorkbench {
+		return new Workbench(domElement, undefined, serviceCollection, logService);
+	}
+
+	private registerListeners(workbench: IBrowserMainWorkbench): void {
 
 		// Workbench Lifecycle
 		this._register(workbench.onWillShutdown(() => this.onWillShutdownDisposables.clear()));
diff --git a/src/vs/workbench/browser/workbench.contribution.ts b/src/vs/workbench/browser/workbench.contribution.ts
index 36923cbd8191f..058693c7cfdfa 100644
--- a/src/vs/workbench/browser/workbench.contribution.ts
+++ b/src/vs/workbench/browser/workbench.contribution.ts
@@ -359,7 +359,7 @@ const registry = Registry.as<IConfigurationRegistry>(ConfigurationExtensions.Con
 					localize('useModal.all', "All editors open in a centered modal overlay."),
 				],
 				'description': localize('useModal', "Controls whether editors open in a modal overlay."),
-				'default': 'off', // TODO@bpasero figure out the default
+				'default': product.quality !== 'stable' ? 'some' : 'off', // TODO@bpasero figure out the default
 				tags: ['experimental'],
 				experiment: {
 					mode: 'auto'
@@ -620,7 +620,7 @@ const registry = Registry.as<IConfigurationRegistry>(ConfigurationExtensions.Con
 			[NotificationsSettings.NOTIFICATIONS_POSITION]: {
 				'type': 'string',
 				'enum': [NotificationsPosition.BOTTOM_RIGHT, NotificationsPosition.BOTTOM_LEFT, NotificationsPosition.TOP_RIGHT],
-				'default': product.quality !== 'stable' ? NotificationsPosition.TOP_RIGHT : NotificationsPosition.BOTTOM_RIGHT,
+				'default': NotificationsPosition.BOTTOM_RIGHT,
 				'description': localize('notificationsPosition', "Controls the position of the notification toasts and notification center."),
 				'enumDescriptions': [
 					localize('workbench.notifications.position.bottom-right', "Show notifications in the bottom right corner."),
diff --git a/src/vs/workbench/common/editor.ts b/src/vs/workbench/common/editor.ts
index 2e535074002fa..e02204c16c429 100644
--- a/src/vs/workbench/common/editor.ts
+++ b/src/vs/workbench/common/editor.ts
@@ -849,7 +849,13 @@ export const enum EditorInputCapabilities {
 	 * Signals that the editor cannot be in a dirty state
 	 * and may still have unsaved changes
 	 */
-	Scratchpad = 1 << 9
+	Scratchpad = 1 << 9,
+
+	/**
+	 * Signals that the editor should be revealed when being
+	 * opened if it is already opened in any editor group.
+	 */
+	ForceReveal = 1 << 10
 }
 
 export type IUntypedEditorInput = IResourceEditorInput | ITextResourceEditorInput | IUntitledTextResourceEditorInput | IResourceDiffEditorInput | IResourceMultiDiffEditorInput | IResourceSideBySideEditorInput | IResourceMergeEditorInput;
diff --git a/src/vs/workbench/common/editor/sideBySideEditorInput.ts b/src/vs/workbench/common/editor/sideBySideEditorInput.ts
index 3a4cb208b3048..27175bf8714ff 100644
--- a/src/vs/workbench/common/editor/sideBySideEditorInput.ts
+++ b/src/vs/workbench/common/editor/sideBySideEditorInput.ts
@@ -43,6 +43,11 @@ export class SideBySideEditorInput extends EditorInput implements ISideBySideEdi
 			capabilities |= EditorInputCapabilities.Singleton;
 		}
 
+		// ForceReveal: should be considered for both sides
+		if (this.secondary.hasCapability(EditorInputCapabilities.ForceReveal)) {
+			capabilities |= EditorInputCapabilities.ForceReveal;
+		}
+
 		// Indicate we show more than one editor
 		capabilities |= EditorInputCapabilities.MultipleEditors;
 
diff --git a/src/vs/workbench/common/theme.ts b/src/vs/workbench/common/theme.ts
index 143a09c1bf17c..7c7df50fd3846 100644
--- a/src/vs/workbench/common/theme.ts
+++ b/src/vs/workbench/common/theme.ts
@@ -549,6 +549,11 @@ export const PANEL_STICKY_SCROLL_BORDER = registerColor('panelStickyScroll.borde
 export const PANEL_STICKY_SCROLL_SHADOW = registerColor('panelStickyScroll.shadow', scrollbarShadow, localize('panelStickyScrollShadow', "Shadow color of sticky scroll in the panel."));
 
 
+// < --- Browser --- >
+
+export const BROWSER_BORDER = registerColor('browser.border', TAB_BORDER, localize('browserBorder', "Border color for integrated browser pages."));
+
+
 // < --- Profiles --- >
 
 export const PROFILE_BADGE_BACKGROUND = registerColor('profileBadge.background', {
diff --git a/src/vs/workbench/contrib/accessibility/browser/accessibleView.ts b/src/vs/workbench/contrib/accessibility/browser/accessibleView.ts
index 6870246190f5b..8881c154f6044 100644
--- a/src/vs/workbench/contrib/accessibility/browser/accessibleView.ts
+++ b/src/vs/workbench/contrib/accessibility/browser/accessibleView.ts
@@ -53,7 +53,9 @@ import { AccessibilityVerbositySettingId, AccessibilityWorkbenchSettingId, acces
 import { resolveContentAndKeybindingItems } from './accessibleViewKeybindingResolver.js';
 
 const enum DIMENSIONS {
-	MAX_WIDTH = 600
+	MAX_WIDTH = 900,
+	WIDTH_RATIO = 0.75,
+	MAX_HEIGHT_RATIO = 0.6
 }
 
 export type AccesibleViewContentProvider = AccessibleContentProvider | ExtensionContentProvider;
@@ -291,7 +293,7 @@ export class AccessibleView extends Disposable {
 		}
 		provider.onOpen?.();
 		const delegate: IContextViewDelegate = {
-			getAnchor: () => { return { x: (getActiveWindow().innerWidth / 2) - ((Math.min(this._layoutService.activeContainerDimension.width * 0.62 /* golden cut */, DIMENSIONS.MAX_WIDTH)) / 2), y: this._layoutService.activeContainerOffset.quickPickTop }; },
+			getAnchor: () => { return { x: (getActiveWindow().innerWidth / 2) - ((Math.min(this._layoutService.activeContainerDimension.width * DIMENSIONS.WIDTH_RATIO, DIMENSIONS.MAX_WIDTH)) / 2), y: this._layoutService.activeContainerOffset.quickPickTop }; },
 			render: (container) => {
 				this._viewContainer = container;
 				this._viewContainer.classList.add('accessible-view-container');
@@ -741,9 +743,9 @@ export class AccessibleView extends Disposable {
 
 	private _layout(): void {
 		const dimension = this._layoutService.activeContainerDimension;
-		const maxHeight = dimension.height && dimension.height * .4;
+		const maxHeight = dimension.height && dimension.height * DIMENSIONS.MAX_HEIGHT_RATIO;
 		const height = Math.min(maxHeight, this._editorWidget.getContentHeight());
-		const width = Math.min(dimension.width * 0.62 /* golden cut */, DIMENSIONS.MAX_WIDTH);
+		const width = Math.min(dimension.width * DIMENSIONS.WIDTH_RATIO, DIMENSIONS.MAX_WIDTH);
 		this._editorWidget.layout({ width, height });
 	}
 
diff --git a/src/vs/workbench/contrib/browserView/browser/browserView.contribution.ts b/src/vs/workbench/contrib/browserView/browser/browserView.contribution.ts
new file mode 100644
index 0000000000000..a16c153f57eda
--- /dev/null
+++ b/src/vs/workbench/contrib/browserView/browser/browserView.contribution.ts
@@ -0,0 +1,47 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { registerSingleton, InstantiationType } from '../../../../platform/instantiation/common/extensions.js';
+import { IBrowserViewWorkbenchService, IBrowserViewCDPService, IBrowserViewModel } from '../common/browserView.js';
+import { Event } from '../../../../base/common/event.js';
+import { CDPEvent, CDPRequest, CDPResponse } from '../../../../platform/browserView/common/cdp/types.js';
+
+class WebBrowserViewWorkbenchService implements IBrowserViewWorkbenchService {
+	declare readonly _serviceBrand: undefined;
+
+	async getOrCreateBrowserViewModel(_id: string): Promise<IBrowserViewModel> {
+		throw new Error('Integrated Browser is not available in web.');
+	}
+
+	async getBrowserViewModel(_id: string): Promise<IBrowserViewModel> {
+		throw new Error('Integrated Browser is not available in web.');
+	}
+
+	async clearGlobalStorage(): Promise<void> { }
+	async clearWorkspaceStorage(): Promise<void> { }
+}
+
+class WebBrowserViewCDPService implements IBrowserViewCDPService {
+	declare readonly _serviceBrand: undefined;
+
+	async createSessionGroup(_browserId: string): Promise<string> {
+		throw new Error('Integrated Browser is not available in web.');
+	}
+
+	async destroySessionGroup(_groupId: string): Promise<void> { }
+
+	async sendCDPMessage(_groupId: string, _message: CDPRequest): Promise<void> { }
+
+	onCDPMessage(_groupId: string): Event<CDPResponse | CDPEvent> {
+		return Event.None;
+	}
+
+	onDidDestroy(_groupId: string): Event<void> {
+		return Event.None;
+	}
+}
+
+registerSingleton(IBrowserViewWorkbenchService, WebBrowserViewWorkbenchService, InstantiationType.Delayed);
+registerSingleton(IBrowserViewCDPService, WebBrowserViewCDPService, InstantiationType.Delayed);
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/browserEditorInput.ts b/src/vs/workbench/contrib/browserView/common/browserEditorInput.ts
similarity index 95%
rename from src/vs/workbench/contrib/browserView/electron-browser/browserEditorInput.ts
rename to src/vs/workbench/contrib/browserView/common/browserEditorInput.ts
index 8fdd335c19441..0bb4c51cbc697 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/browserEditorInput.ts
+++ b/src/vs/workbench/contrib/browserView/common/browserEditorInput.ts
@@ -18,7 +18,6 @@ import { IInstantiationService } from '../../../../platform/instantiation/common
 import { IBrowserViewWorkbenchService, IBrowserViewModel } from '../common/browserView.js';
 import { hasKey } from '../../../../base/common/types.js';
 import { ILifecycleService, ShutdownReason } from '../../../services/lifecycle/common/lifecycle.js';
-import { BrowserEditor } from './browserEditor.js';
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
 import { logBrowserOpen } from '../../../../platform/browserView/common/browserViewTelemetry.js';
 
@@ -48,6 +47,7 @@ export interface IBrowserEditorInputData {
 
 export class BrowserEditorInput extends EditorInput {
 	static readonly ID = 'workbench.editorinputs.browser';
+	static readonly EDITOR_ID = 'workbench.editor.browser';
 	private static readonly DEFAULT_LABEL = localize('browser.editorLabel', "Browser");
 
 	private readonly _id: string;
@@ -84,6 +84,16 @@ export class BrowserEditorInput extends EditorInput {
 		return this._id;
 	}
 
+	get url(): string | undefined {
+		// Use model URL if available, otherwise fall back to initial data
+		return this._model ? this._model.url : this._initialData.url;
+	}
+
+	get favicon(): string | undefined {
+		// Use model favicon if available, otherwise fall back to initial data
+		return this._model ? this._model.favicon : this._initialData.favicon;
+	}
+
 	override async resolve(): Promise<IBrowserViewModel> {
 		if (!this._model && !this._modelPromise) {
 			this._modelPromise = (async () => {
@@ -122,11 +132,11 @@ export class BrowserEditorInput extends EditorInput {
 	}
 
 	override get editorId(): string {
-		return BrowserEditor.ID;
+		return BrowserEditorInput.EDITOR_ID;
 	}
 
 	override get capabilities(): EditorInputCapabilities {
-		return EditorInputCapabilities.Singleton | EditorInputCapabilities.Readonly;
+		return EditorInputCapabilities.ForceReveal | EditorInputCapabilities.Readonly;
 	}
 
 	override get resource(): URI {
@@ -182,8 +192,7 @@ export class BrowserEditorInput extends EditorInput {
 	}
 
 	override getDescription(): string | undefined {
-		// Use model URL if available, otherwise fall back to initial data
-		return this._model ? this._model.url : this._initialData.url;
+		return this.url;
 	}
 
 	override canReopen(): boolean {
diff --git a/src/vs/workbench/contrib/browserView/common/browserView.ts b/src/vs/workbench/contrib/browserView/common/browserView.ts
index 76f04a67f829d..6b3804b5651e3 100644
--- a/src/vs/workbench/contrib/browserView/common/browserView.ts
+++ b/src/vs/workbench/contrib/browserView/common/browserView.ts
@@ -7,6 +7,7 @@ import { createDecorator } from '../../../../platform/instantiation/common/insta
 import { Emitter, Event } from '../../../../base/common/event.js';
 import { Disposable, IDisposable } from '../../../../base/common/lifecycle.js';
 import { VSBuffer } from '../../../../base/common/buffer.js';
+import { CDPEvent, CDPRequest, CDPResponse } from '../../../../platform/browserView/common/cdp/types.js';
 import { IPlaywrightService } from '../../../../platform/browserView/common/playwrightService.js';
 import { IDialogService } from '../../../../platform/dialogs/common/dialogs.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
@@ -27,13 +28,25 @@ import {
 	IBrowserViewCaptureScreenshotOptions,
 	IBrowserViewFindInPageOptions,
 	IBrowserViewFindInPageResult,
-	IBrowserViewVisibilityEvent
+	IBrowserViewVisibilityEvent,
+	browserZoomDefaultIndex,
+	browserZoomFactors
 } from '../../../../platform/browserView/common/browserView.js';
 import { IWorkspaceContextService, WorkbenchState } from '../../../../platform/workspace/common/workspace.js';
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
 import { isLocalhostAuthority } from '../../../../platform/url/common/trustedDomains.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { IWorkspaceTrustManagementService } from '../../../../platform/workspace/common/workspaceTrust.js';
+import { IBrowserZoomService } from './browserZoomService.js';
+
+/** Extracts the host from a URL string for zoom tracking purposes. */
+function parseZoomHost(url: string): string | undefined {
+	const parsed = URL.parse(url);
+	if (!parsed?.host || (parsed.protocol !== 'http:' && parsed.protocol !== 'https:')) {
+		return undefined;
+	}
+	return parsed.host;
+}
 
 type IntegratedBrowserNavigationEvent = {
 	navigationType: 'urlInput' | 'goBack' | 'goForward' | 'reload';
@@ -76,6 +89,14 @@ export interface IBrowserViewWorkbenchService {
 	 */
 	getOrCreateBrowserViewModel(id: string): Promise<IBrowserViewModel>;
 
+	/**
+	 * Get an existing browser view model for the given ID
+	 * @param id The browser view identifier
+	 * @returns A browser view model that proxies to the main process
+	 * @throws If no browser view exists for the given ID
+	 */
+	getBrowserViewModel(id: string): Promise<IBrowserViewModel>;
+
 	/**
 	 * Clear all storage data for the global browser session
 	 */
@@ -87,6 +108,36 @@ export interface IBrowserViewWorkbenchService {
 	clearWorkspaceStorage(): Promise<void>;
 }
 
+export const IBrowserViewCDPService = createDecorator<IBrowserViewCDPService>('browserViewCDPService');
+
+/**
+ * Workbench-level service for managing CDP (Chrome DevTools Protocol) sessions
+ * against browser views. Handles group lifecycle and window ID resolution.
+ */
+export interface IBrowserViewCDPService {
+	readonly _serviceBrand: undefined;
+
+	/**
+	 * Create a new CDP group for a browser view.
+	 * The window ID is resolved from the editor group containing the browser.
+	 * @param browserId The browser view identifier.
+	 * @returns The ID of the newly created group.
+	 */
+	createSessionGroup(browserId: string): Promise<string>;
+
+	/** Destroy a CDP group. */
+	destroySessionGroup(groupId: string): Promise<void>;
+
+	/** Send a CDP message to a group. */
+	sendCDPMessage(groupId: string, message: CDPRequest): Promise<void>;
+
+	/** Fires when a CDP message is received. */
+	onCDPMessage(groupId: string): Event<CDPResponse | CDPEvent>;
+
+	/** Fires when a CDP group is destroyed. */
+	onDidDestroy(groupId: string): Event<void>;
+}
+
 
 /**
  * A browser view model that represents a single browser view instance in the workbench.
@@ -105,11 +156,14 @@ export interface IBrowserViewModel extends IDisposable {
 	readonly isDevToolsOpen: boolean;
 	readonly canGoForward: boolean;
 	readonly error: IBrowserViewLoadError | undefined;
-
 	readonly storageScope: BrowserViewStorageScope;
 	readonly sharedWithAgent: boolean;
+	readonly zoomFactor: number;
+	readonly canZoomIn: boolean;
+	readonly canZoomOut: boolean;
 
 	readonly onDidChangeSharedWithAgent: Event<boolean>;
+	readonly onDidChangeZoom: Event<void>;
 	readonly onDidNavigate: Event<IBrowserViewNavigationEvent>;
 	readonly onDidChangeLoadingState: Event<IBrowserViewLoadingEvent>;
 	readonly onDidChangeFocus: Event<IBrowserViewFocusEvent>;
@@ -123,14 +177,14 @@ export interface IBrowserViewModel extends IDisposable {
 	readonly onDidClose: Event<void>;
 	readonly onWillDispose: Event<void>;
 
-	initialize(): Promise<void>;
+	initialize(create: boolean): Promise<void>;
 
 	layout(bounds: IBrowserViewBounds): Promise<void>;
 	setVisible(visible: boolean): Promise<void>;
 	loadURL(url: string): Promise<void>;
 	goBack(): Promise<void>;
 	goForward(): Promise<void>;
-	reload(): Promise<void>;
+	reload(hard?: boolean): Promise<void>;
 	toggleDevTools(): Promise<void>;
 	captureScreenshot(options?: IBrowserViewCaptureScreenshotOptions): Promise<VSBuffer>;
 	dispatchKeyEvent(keyEvent: IBrowserViewKeyDownEvent): Promise<void>;
@@ -140,6 +194,9 @@ export interface IBrowserViewModel extends IDisposable {
 	getSelectedText(): Promise<string>;
 	clearStorage(): Promise<void>;
 	setSharedWithAgent(shared: boolean): Promise<void>;
+	zoomIn(): Promise<void>;
+	zoomOut(): Promise<void>;
+	resetZoom(): Promise<void>;
 }
 
 export class BrowserViewModel extends Disposable implements IBrowserViewModel {
@@ -155,11 +212,17 @@ export class BrowserViewModel extends Disposable implements IBrowserViewModel {
 	private _canGoForward: boolean = false;
 	private _error: IBrowserViewLoadError | undefined = undefined;
 	private _storageScope: BrowserViewStorageScope = BrowserViewStorageScope.Ephemeral;
+	private _isEphemeral: boolean = false;
+	private _zoomHost: string | undefined = undefined;
 	private _sharedWithAgent: boolean = false;
+	private _browserZoomIndex: number = browserZoomDefaultIndex;
 
 	private readonly _onDidChangeSharedWithAgent = this._register(new Emitter<boolean>());
 	readonly onDidChangeSharedWithAgent: Event<boolean> = this._onDidChangeSharedWithAgent.event;
 
+	private readonly _onDidChangeZoom = this._register(new Emitter<void>());
+	readonly onDidChangeZoom: Event<void> = this._onDidChangeZoom.event;
+
 	private readonly _onWillDispose = this._register(new Emitter<void>());
 	readonly onWillDispose: Event<void> = this._onWillDispose.event;
 
@@ -173,6 +236,7 @@ export class BrowserViewModel extends Disposable implements IBrowserViewModel {
 		@IPlaywrightService private readonly playwrightService: IPlaywrightService,
 		@IDialogService private readonly dialogService: IDialogService,
 		@IStorageService private readonly storageService: IStorageService,
+		@IBrowserZoomService private readonly zoomService: IBrowserZoomService,
 	) {
 		super();
 	}
@@ -190,6 +254,9 @@ export class BrowserViewModel extends Disposable implements IBrowserViewModel {
 	get error(): IBrowserViewLoadError | undefined { return this._error; }
 	get storageScope(): BrowserViewStorageScope { return this._storageScope; }
 	get sharedWithAgent(): boolean { return this._sharedWithAgent; }
+	get zoomFactor(): number { return browserZoomFactors[this._browserZoomIndex]; }
+	get canZoomIn(): boolean { return this._browserZoomIndex < browserZoomFactors.length - 1; }
+	get canZoomOut(): boolean { return this._browserZoomIndex > 0; }
 
 	get onDidNavigate(): Event<IBrowserViewNavigationEvent> {
 		return this.browserViewService.onDynamicDidNavigate(this.id);
@@ -236,9 +303,11 @@ export class BrowserViewModel extends Disposable implements IBrowserViewModel {
 	}
 
 	/**
-	 * Initialize the model with the current state from the main process
+	 * Initialize the model with the current state from the main process.
+	 * @param create Whether to create the browser view if it doesn't already exist.
+	 * @throws If the browser view doesn't exist and `create` is false, or if initialization fails
 	 */
-	async initialize(): Promise<void> {
+	async initialize(create: boolean): Promise<void> {
 		const dataStorageSetting = this.configurationService.getValue<BrowserViewStorageScope>(
 			'workbench.browser.dataStorage'
 		) ?? BrowserViewStorageScope.Global;
@@ -253,7 +322,9 @@ export class BrowserViewModel extends Disposable implements IBrowserViewModel {
 		const dataStorage = isWorkspaceUntrusted ? BrowserViewStorageScope.Ephemeral : dataStorageSetting;
 
 		const workspaceId = this.workspaceContextService.getWorkspace().id;
-		const state = await this.browserViewService.getOrCreateBrowserView(this.id, dataStorage, workspaceId);
+		const state = create
+			? await this.browserViewService.getOrCreateBrowserView(this.id, dataStorage, workspaceId)
+			: await this.browserViewService.getState(this.id);
 
 		this._url = state.url;
 		this._title = state.title;
@@ -268,6 +339,26 @@ export class BrowserViewModel extends Disposable implements IBrowserViewModel {
 		this._error = state.lastError;
 		this._storageScope = state.storageScope;
 		this._sharedWithAgent = await this.playwrightService.isPageTracked(this.id);
+		this._browserZoomIndex = state.browserZoomIndex;
+
+		this._isEphemeral = this._storageScope === BrowserViewStorageScope.Ephemeral;
+		this._zoomHost = parseZoomHost(this._url);
+
+		const effectiveZoomIndex = this.zoomService.getEffectiveZoomIndex(this._zoomHost, this._isEphemeral);
+		if (effectiveZoomIndex !== this._browserZoomIndex) {
+			await this.setBrowserZoomIndex(effectiveZoomIndex);
+		}
+
+		this._register(this.zoomService.onDidChangeZoom(({ host, isEphemeralChange }) => {
+			if (isEphemeralChange && !this._isEphemeral) {
+				return;
+			}
+			if (host === undefined || host === this._zoomHost) {
+				void this.setBrowserZoomIndex(
+					this.zoomService.getEffectiveZoomIndex(this._zoomHost, this._isEphemeral)
+				);
+			}
+		}));
 
 		// Set up state synchronization
 
@@ -277,10 +368,18 @@ export class BrowserViewModel extends Disposable implements IBrowserViewModel {
 				this._favicon = undefined;
 			}
 
+			this._zoomHost = parseZoomHost(e.url);
 			this._url = e.url;
 			this._title = e.title;
 			this._canGoBack = e.canGoBack;
 			this._canGoForward = e.canGoForward;
+
+			// Always forceApply because Chromium resets zoom on cross-origin navigation,
+			// and an origin change may not correspond to a host change (e.g. http→https).
+			void this.setBrowserZoomIndex(
+				this.zoomService.getEffectiveZoomIndex(this._zoomHost, this._isEphemeral),
+				true
+			);
 		}));
 
 		this._register(this.onDidChangeLoadingState(e => {
@@ -337,9 +436,9 @@ export class BrowserViewModel extends Disposable implements IBrowserViewModel {
 		return this.browserViewService.goForward(this.id);
 	}
 
-	async reload(): Promise<void> {
+	async reload(hard?: boolean): Promise<void> {
 		this.logNavigationTelemetry('reload', this._url);
-		return this.browserViewService.reload(this.id);
+		return this.browserViewService.reload(this.id, hard);
 	}
 
 	async toggleDevTools(): Promise<void> {
@@ -379,6 +478,49 @@ export class BrowserViewModel extends Disposable implements IBrowserViewModel {
 		return this.browserViewService.clearStorage(this.id);
 	}
 
+	/**
+	 * @param forceApply When true, the IPC call is made even if the local cached zoom index
+	 * already matches the requested value. Pass true after cross-document navigation because
+	 * Chromium resets the zoom to its per-origin default, making the cache stale.
+	 */
+	private async setBrowserZoomIndex(zoomIndex: number, forceApply = false): Promise<void> {
+		const clamped = Math.max(0, Math.min(zoomIndex, browserZoomFactors.length - 1));
+		if (!forceApply && clamped === this._browserZoomIndex) {
+			return;
+		}
+		this._browserZoomIndex = clamped;
+		await this.browserViewService.setBrowserZoomIndex(this.id, this._browserZoomIndex);
+		this._onDidChangeZoom.fire();
+	}
+
+	async zoomIn(): Promise<void> {
+		if (!this.canZoomIn) {
+			return;
+		}
+		await this.setBrowserZoomIndex(this._browserZoomIndex + 1);
+		if (this._zoomHost) {
+			this.zoomService.setHostZoomIndex(this._zoomHost, this._browserZoomIndex, this._isEphemeral);
+		}
+	}
+
+	async zoomOut(): Promise<void> {
+		if (!this.canZoomOut) {
+			return;
+		}
+		await this.setBrowserZoomIndex(this._browserZoomIndex - 1);
+		if (this._zoomHost) {
+			this.zoomService.setHostZoomIndex(this._zoomHost, this._browserZoomIndex, this._isEphemeral);
+		}
+	}
+
+	async resetZoom(): Promise<void> {
+		const defaultIndex = this.zoomService.getEffectiveZoomIndex(undefined, false);
+		await this.setBrowserZoomIndex(defaultIndex);
+		if (this._zoomHost) {
+			this.zoomService.setHostZoomIndex(this._zoomHost, defaultIndex, this._isEphemeral);
+		}
+	}
+
 	private static readonly SHARE_DONT_ASK_KEY = 'browserView.shareWithAgent.dontAskAgain';
 
 	async setSharedWithAgent(shared: boolean): Promise<void> {
diff --git a/src/vs/workbench/contrib/browserView/common/browserZoomService.ts b/src/vs/workbench/contrib/browserView/common/browserZoomService.ts
new file mode 100644
index 0000000000000..c0e3cc5023a62
--- /dev/null
+++ b/src/vs/workbench/contrib/browserView/common/browserZoomService.ts
@@ -0,0 +1,271 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Emitter, Event } from '../../../../base/common/event.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { createDecorator } from '../../../../platform/instantiation/common/instantiation.js';
+import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
+import { browserZoomDefaultIndex, browserZoomFactors } from '../../../../platform/browserView/common/browserView.js';
+import { zoomLevelToZoomFactor } from '../../../../platform/window/common/window.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
+
+export const IBrowserZoomService = createDecorator<IBrowserZoomService>('browserZoomService');
+
+/** Storage key for the per-host persistent zoom map. */
+const BROWSER_ZOOM_PER_HOST_STORAGE_KEY = 'browserView.zoomPerHost';
+
+/**
+ * Special value for the default zoom level setting that instructs the browser view
+ * to dynamically match the closest zoom level to the application's current UI zoom.
+ */
+export const MATCH_WINDOW_ZOOM_LABEL = 'Match Window';
+
+export interface IBrowserZoomChangeEvent {
+	/**
+	 * The host (e.g. `"example.com"`) whose zoom changed, or `undefined`
+	 * when the global default zoom level changed.
+	 */
+	readonly host: string | undefined;
+
+	/**
+	 * Whether the change came from an ephemeral session.
+	 * - `true`  → only ephemeral views need to react.
+	 * - `false` → all views (ephemeral and non-ephemeral) for the host may be affected.
+	 */
+	readonly isEphemeralChange: boolean;
+}
+
+/**
+ * Manages two independent cascading zoom hierarchies for integrated browser views:
+ *
+ *  Normal views:    `persistent per-host override` ?? `configured default`
+ *  Ephemeral views: `ephemeral per-host override`  ?? `configured default`
+ *
+ * Ephemeral views never see persistent overrides directly. Instead, when a persistent
+ * value changes, it is copied into the ephemeral map so that ephemeral views
+ * immediately reflect the new level. Conversely, ephemeral changes never affect
+ * normal views.
+ *
+ * Per-host values that equal the current default are always removed (both persistent
+ * and ephemeral), so the view tracks the default going forward.
+ */
+export interface IBrowserZoomService {
+	readonly _serviceBrand: undefined;
+
+	/** Fired whenever the effective zoom for a host may have changed. */
+	readonly onDidChangeZoom: Event<IBrowserZoomChangeEvent>;
+
+	/**
+	 * Returns the effective zoom index for the given host and session type.
+	 * Pass `host = undefined` to obtain only the configured default zoom index.
+	 */
+	getEffectiveZoomIndex(host: string | undefined, isEphemeral: boolean): number;
+
+	/**
+	 * Set the zoom for a host.
+	 *
+	 * Non-ephemeral: persisted to storage. Also propagated into
+	 * the ephemeral map so ephemeral views immediately reflect the change.
+	 *
+	 * Ephemeral: stored in memory only, dropped on restart.
+	 *
+	 * In both cases, if the value equals the current default, the entry is removed so the
+	 * view tracks the default going forward.
+	 */
+	setHostZoomIndex(host: string, zoomIndex: number, isEphemeral: boolean): void;
+
+	/**
+	 * Notifies the service of the application's current UI zoom factor.
+	 * Must be called once on startup and again whenever the window zoom changes.
+	 * Only relevant when the default zoom level is set to `MATCH_WINDOW_LABEL`.
+	 */
+	notifyWindowZoomChanged(windowZoomFactor: number): void;
+}
+
+// ---------------------------------------------------------------------------
+// Implementation
+// ---------------------------------------------------------------------------
+
+/** Pre-computed map from percentage label (e.g. "125%") to index into browserZoomFactors. */
+const ZOOM_LABEL_TO_INDEX = new Map<string, number>(
+	browserZoomFactors.map((f, i) => [`${Math.round(f * 100)}%`, i])
+);
+
+export class BrowserZoomService extends Disposable implements IBrowserZoomService {
+	declare readonly _serviceBrand: undefined;
+
+	private readonly _onDidChangeZoom = this._register(new Emitter<IBrowserZoomChangeEvent>());
+	readonly onDidChangeZoom: Event<IBrowserZoomChangeEvent> = this._onDidChangeZoom.event;
+
+	/**
+	 * In-memory cache of the persistent per-host map.
+	 * Backed by IStorageService.
+	 */
+	private _persistentZoomMap: Record<string, number>;
+
+	/** In-memory only; dropped on restart. */
+	private readonly _ephemeralZoomMap = new Map<string, number>();
+
+	private _windowZoomFactor: number = zoomLevelToZoomFactor(0); // default: zoom level 0 → factor 1.0
+
+	constructor(
+		@IConfigurationService private readonly configurationService: IConfigurationService,
+		@IStorageService private readonly storageService: IStorageService,
+	) {
+		super();
+
+		this._persistentZoomMap = this._readPersistentZoomMap();
+
+		this._register(this.configurationService.onDidChangeConfiguration(e => {
+			if (e.affectsConfiguration('workbench.browser.pageZoom')) {
+				this._onDidChangeZoom.fire({ host: undefined, isEphemeralChange: false });
+			}
+		}));
+	}
+
+	getEffectiveZoomIndex(host: string | undefined, isEphemeral: boolean): number {
+		if (host !== undefined) {
+			if (isEphemeral) {
+				const ephemeralIndex = this._ephemeralZoomMap.get(host);
+				if (ephemeralIndex !== undefined) {
+					return this._clamp(ephemeralIndex);
+				}
+			} else {
+				const persistentIndex = this._persistentZoomMap[host];
+				if (persistentIndex !== undefined) {
+					return this._clamp(persistentIndex);
+				}
+			}
+		}
+
+		return this._getDefaultZoomIndex();
+	}
+
+	setHostZoomIndex(host: string, zoomIndex: number, isEphemeral: boolean): void {
+		const clamped = this._clamp(zoomIndex);
+		const defaultIndex = this._getDefaultZoomIndex();
+		const matchesDefault = clamped === defaultIndex;
+
+		if (isEphemeral) {
+			if (matchesDefault) {
+				if (!this._ephemeralZoomMap.has(host)) {
+					return;
+				}
+				this._ephemeralZoomMap.delete(host);
+			} else {
+				if (this._ephemeralZoomMap.get(host) === clamped) {
+					return;
+				}
+				this._ephemeralZoomMap.set(host, clamped);
+			}
+			this._onDidChangeZoom.fire({ host, isEphemeralChange: true });
+		} else {
+			let persistentChanged = false;
+			if (matchesDefault) {
+				if (Object.prototype.hasOwnProperty.call(this._persistentZoomMap, host)) {
+					delete this._persistentZoomMap[host];
+					persistentChanged = true;
+				}
+			} else if (this._persistentZoomMap[host] !== clamped) {
+				this._persistentZoomMap[host] = clamped;
+				persistentChanged = true;
+			}
+
+			// Propagate to ephemeral map so ephemeral views immediately reflect the new level.
+			let ephemeralChanged = false;
+			if (matchesDefault) {
+				ephemeralChanged = this._ephemeralZoomMap.delete(host);
+			} else if (this._ephemeralZoomMap.get(host) !== clamped) {
+				this._ephemeralZoomMap.set(host, clamped);
+				ephemeralChanged = true;
+			}
+
+			if (!persistentChanged && !ephemeralChanged) {
+				return;
+			}
+			if (persistentChanged) {
+				this._writePersistentZoomMap();
+			}
+			this._onDidChangeZoom.fire({ host, isEphemeralChange: false });
+		}
+	}
+
+	notifyWindowZoomChanged(windowZoomFactor: number): void {
+		this._windowZoomFactor = windowZoomFactor;
+		const label = this.configurationService.getValue<string>('workbench.browser.pageZoom');
+		if (label === MATCH_WINDOW_ZOOM_LABEL) {
+			this._onDidChangeZoom.fire({ host: undefined, isEphemeralChange: false });
+		}
+	}
+
+	// ---------------------------------------------------------------------------
+	// Helpers
+	// ---------------------------------------------------------------------------
+
+	private _getDefaultZoomIndex(): number {
+		const label = this.configurationService.getValue<string>('workbench.browser.pageZoom');
+		if (label === MATCH_WINDOW_ZOOM_LABEL) {
+			return this._getMatchWindowZoomIndex();
+		}
+		return ZOOM_LABEL_TO_INDEX.get(label) ?? browserZoomDefaultIndex;
+	}
+
+	/**
+	 * Finds the browser zoom index whose factor is closest to the application's current UI zoom
+	 * factor, measuring distance on a log scale (since window zoom levels are powers of 1.2).
+	 */
+	private _getMatchWindowZoomIndex(): number {
+		const windowFactor = this._windowZoomFactor;
+		let bestIndex = browserZoomDefaultIndex;
+		let bestDist = Infinity;
+		for (let i = 0; i < browserZoomFactors.length; i++) {
+			const dist = Math.abs(Math.log(browserZoomFactors[i]) - Math.log(windowFactor));
+			if (dist < bestDist) {
+				bestDist = dist;
+				bestIndex = i;
+			}
+		}
+		return bestIndex;
+	}
+
+	/**
+	 * Reads the persistent per-host zoom map from storage.
+	 * The stored format is a JSON object mapping host strings to zoom indices.
+	 */
+	private _readPersistentZoomMap(): Record<string, number> {
+		const raw = this.storageService.get(BROWSER_ZOOM_PER_HOST_STORAGE_KEY, StorageScope.PROFILE);
+		if (!raw) {
+			return {};
+		}
+		try {
+			const parsed = JSON.parse(raw);
+			if (typeof parsed !== 'object' || parsed === null || Array.isArray(parsed)) {
+				return {};
+			}
+			const result: Record<string, number> = {};
+			for (const [host, index] of Object.entries(parsed)) {
+				if (typeof index === 'number' && index >= 0 && index < browserZoomFactors.length) {
+					result[host] = index;
+				}
+			}
+			return result;
+		} catch {
+			return {};
+		}
+	}
+
+	private _writePersistentZoomMap(): void {
+		const hasEntries = Object.keys(this._persistentZoomMap).length > 0;
+		if (hasEntries) {
+			this.storageService.store(BROWSER_ZOOM_PER_HOST_STORAGE_KEY, JSON.stringify(this._persistentZoomMap), StorageScope.PROFILE, StorageTarget.MACHINE);
+		} else {
+			this.storageService.remove(BROWSER_ZOOM_PER_HOST_STORAGE_KEY, StorageScope.PROFILE);
+		}
+	}
+
+	private _clamp(index: number): number {
+		return Math.max(0, Math.min(Math.trunc(index), browserZoomFactors.length - 1));
+	}
+}
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/browserEditor.ts b/src/vs/workbench/contrib/browserView/electron-browser/browserEditor.ts
index 234991e440b54..662a7bb49be79 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/browserEditor.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/browserEditor.ts
@@ -16,13 +16,14 @@ import { ServiceCollection } from '../../../../platform/instantiation/common/ser
 import { AUX_WINDOW_GROUP, IEditorService } from '../../../services/editor/common/editorService.js';
 import { EditorPane } from '../../../browser/parts/editor/editorPane.js';
 import { IEditorOpenContext } from '../../../common/editor.js';
-import { BrowserEditorInput } from './browserEditorInput.js';
+import { BrowserEditorInput } from '../common/browserEditorInput.js';
 import { BrowserViewUri } from '../../../../platform/browserView/common/browserViewUri.js';
 import { IBrowserViewModel } from '../../browserView/common/browserView.js';
+import { IBrowserZoomService } from '../../browserView/common/browserZoomService.js';
 import { IThemeService } from '../../../../platform/theme/common/themeService.js';
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
 import { IStorageService } from '../../../../platform/storage/common/storage.js';
-import { IBrowserViewKeyDownEvent, IBrowserViewNavigationEvent, IBrowserViewLoadError, BrowserNewPageLocation } from '../../../../platform/browserView/common/browserView.js';
+import { IBrowserViewKeyDownEvent, IBrowserViewNavigationEvent, IBrowserViewLoadError, BrowserNewPageLocation, browserZoomFactors, browserZoomLabel, browserZoomAccessibilityLabel } from '../../../../platform/browserView/common/browserView.js';
 import { IEditorGroup } from '../../../services/editor/common/editorGroupsService.js';
 import { IEditorOptions } from '../../../../platform/editor/common/editor.js';
 import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
@@ -30,7 +31,8 @@ import { StandardKeyboardEvent } from '../../../../base/browser/keyboardEvent.js
 import { BrowserOverlayManager, BrowserOverlayType, IBrowserOverlayInfo } from './overlayManager.js';
 import { getZoomFactor, onDidChangeZoomLevel } from '../../../../base/browser/browser.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
-import { Disposable, DisposableStore, toDisposable } from '../../../../base/common/lifecycle.js';
+import { Disposable, DisposableStore, MutableDisposable, toDisposable } from '../../../../base/common/lifecycle.js';
+import { disposableTimeout } from '../../../../base/common/async.js';
 import { Lazy } from '../../../../base/common/lazy.js';
 import { WorkbenchHoverDelegate } from '../../../../platform/hover/browser/hover.js';
 import { HoverPosition } from '../../../../base/browser/ui/hover/hoverWidget.js';
@@ -49,6 +51,8 @@ import { logBrowserOpen } from '../../../../platform/browserView/common/browserV
 import { URI } from '../../../../base/common/uri.js';
 import { ChatConfiguration } from '../../chat/common/constants.js';
 import { Event } from '../../../../base/common/event.js';
+import { ILayoutService } from '../../../../platform/layout/browser/layoutService.js';
+import { IAccessibilityService } from '../../../../platform/accessibility/common/accessibility.js';
 
 export const CONTEXT_BROWSER_CAN_GO_BACK = new RawContextKey<boolean>('browserCanGoBack', false, localize('browser.canGoBack', "Whether the browser can go back"));
 export const CONTEXT_BROWSER_CAN_GO_FORWARD = new RawContextKey<boolean>('browserCanGoForward', false, localize('browser.canGoForward', "Whether the browser can go forward"));
@@ -58,6 +62,8 @@ export const CONTEXT_BROWSER_HAS_URL = new RawContextKey<boolean>('browserHasUrl
 export const CONTEXT_BROWSER_HAS_ERROR = new RawContextKey<boolean>('browserHasError', false, localize('browser.hasError', "Whether the browser has a load error"));
 export const CONTEXT_BROWSER_DEVTOOLS_OPEN = new RawContextKey<boolean>('browserDevToolsOpen', false, localize('browser.devToolsOpen', "Whether developer tools are open for the current browser view"));
 export const CONTEXT_BROWSER_ELEMENT_SELECTION_ACTIVE = new RawContextKey<boolean>('browserElementSelectionActive', false, localize('browser.elementSelectionActive', "Whether element selection is currently active"));
+export const CONTEXT_BROWSER_CAN_ZOOM_IN = new RawContextKey<boolean>('browserCanZoomIn', true, localize('browser.canZoomIn', "Whether the browser can zoom in further"));
+export const CONTEXT_BROWSER_CAN_ZOOM_OUT = new RawContextKey<boolean>('browserCanZoomOut', true, localize('browser.canZoomOut', "Whether the browser can zoom out further"));
 
 // Re-export find widget context keys for use in actions
 export { CONTEXT_BROWSER_FIND_WIDGET_FOCUSED, CONTEXT_BROWSER_FIND_WIDGET_VISIBLE };
@@ -78,10 +84,46 @@ function watchForAgentSharingContextChanges(contextKeyService: IContextKeyServic
  */
 const originalHtmlElementFocus = HTMLElement.prototype.focus;
 
+/**
+ * Transient zoom-level indicator that briefly appears inside the URL bar on zoom changes.
+ * All DOM construction, state, and auto-hide logic are self-contained here.
+ */
+class BrowserZoomPill extends Disposable {
+	readonly element: HTMLElement;
+	private readonly _icon: HTMLElement;
+	private readonly _label: HTMLElement;
+	private readonly _timeout = this._register(new MutableDisposable());
+
+	constructor() {
+		super();
+		this.element = $('.browser-zoom-pill');
+		// Don't announce this transient element; the zoom level is announced via IAccessibilityService.status() in showZoomPill()
+		this.element.setAttribute('aria-hidden', 'true');
+		this._icon = $('span');
+		this._label = $('span');
+		this.element.appendChild(this._icon);
+		this.element.appendChild(this._label);
+	}
+
+	/**
+	 * Briefly show the zoom level, then auto-hide after 750 ms.
+	 */
+	show(zoomLabel: string, isAtOrAboveDefault: boolean): void {
+		this._icon.className = ThemeIcon.asClassName(isAtOrAboveDefault ? Codicon.zoomIn : Codicon.zoomOut);
+		this._label.textContent = zoomLabel;
+		this.element.classList.add('visible');
+		// Reset auto-hide timer so rapid zoom actions extend the display
+		this._timeout.value = disposableTimeout(() => {
+			this.element.classList.remove('visible');
+		}, 750); // Chrome shows the zoom level for 1.5 seconds, but we show it for less because ours is non-interactive
+	}
+}
+
 class BrowserNavigationBar extends Disposable {
 	private readonly _urlInput: HTMLInputElement;
 	private readonly _shareButton: Button;
 	private readonly _shareButtonContainer: HTMLElement;
+	private readonly _zoomPill: BrowserZoomPill;
 
 	constructor(
 		editor: BrowserEditor,
@@ -139,7 +181,10 @@ class BrowserNavigationBar extends Disposable {
 		this._shareButton.element.classList.add('browser-share-toggle');
 		this._shareButton.label = '$(agent)';
 
+		this._zoomPill = this._register(new BrowserZoomPill());
+
 		urlContainer.appendChild(this._urlInput);
+		urlContainer.appendChild(this._zoomPill.element);
 		urlContainer.appendChild(this._shareButtonContainer);
 
 		// Create actions toolbar (right side) with scoped context
@@ -223,19 +268,25 @@ class BrowserNavigationBar extends Disposable {
 		this._urlInput.focus();
 	}
 
+	/**
+	 * Briefly show the zoom level indicator pill, then auto-hide.
+	 */
+	showZoomLevel(zoomLabel: string, isAtOrAboveDefault: boolean): void {
+		this._zoomPill.show(zoomLabel, isAtOrAboveDefault);
+	}
+
 	clear(): void {
 		this._urlInput.value = '';
 	}
 }
 
 export class BrowserEditor extends EditorPane {
-	static readonly ID = 'workbench.editor.browser';
-
 	private _overlayVisible = false;
 	private _editorVisible = false;
 	private _currentKeyDownEvent: IBrowserViewKeyDownEvent | undefined;
 
 	private _navigationBar!: BrowserNavigationBar;
+	private _browserContainerWrapper!: HTMLElement;
 	private _browserContainer!: HTMLElement;
 	private _placeholderScreenshot!: HTMLElement;
 	private _overlayPauseContainer!: HTMLElement;
@@ -252,6 +303,8 @@ export class BrowserEditor extends EditorPane {
 	private _hasErrorContext!: IContextKey<boolean>;
 	private _devToolsOpenContext!: IContextKey<boolean>;
 	private _elementSelectionActiveContext!: IContextKey<boolean>;
+	private _canZoomInContext!: IContextKey<boolean>;
+	private _canZoomOutContext!: IContextKey<boolean>;
 
 	private _model: IBrowserViewModel | undefined;
 	private readonly _inputDisposables = this._register(new DisposableStore());
@@ -272,9 +325,12 @@ export class BrowserEditor extends EditorPane {
 		@IEditorService private readonly editorService: IEditorService,
 		@IBrowserElementsService private readonly browserElementsService: IBrowserElementsService,
 		@IChatWidgetService private readonly chatWidgetService: IChatWidgetService,
-		@IConfigurationService private readonly configurationService: IConfigurationService
+		@IConfigurationService private readonly configurationService: IConfigurationService,
+		@ILayoutService private readonly layoutService: ILayoutService,
+		@IBrowserZoomService private readonly browserZoomService: IBrowserZoomService,
+		@IAccessibilityService private readonly accessibilityService: IAccessibilityService
 	) {
-		super(BrowserEditor.ID, group, telemetryService, themeService, storageService);
+		super(BrowserEditorInput.EDITOR_ID, group, telemetryService, themeService, storageService);
 	}
 
 	protected override createEditor(parent: HTMLElement): void {
@@ -292,6 +348,8 @@ export class BrowserEditor extends EditorPane {
 		this._hasErrorContext = CONTEXT_BROWSER_HAS_ERROR.bindTo(contextKeyService);
 		this._devToolsOpenContext = CONTEXT_BROWSER_DEVTOOLS_OPEN.bindTo(contextKeyService);
 		this._elementSelectionActiveContext = CONTEXT_BROWSER_ELEMENT_SELECTION_ACTIVE.bindTo(contextKeyService);
+		this._canZoomInContext = CONTEXT_BROWSER_CAN_ZOOM_IN.bindTo(contextKeyService);
+		this._canZoomOutContext = CONTEXT_BROWSER_CAN_ZOOM_OUT.bindTo(contextKeyService);
 
 		// Currently this is always true since it is scoped to the editor container
 		CONTEXT_BROWSER_FOCUSED.bindTo(contextKeyService);
@@ -321,18 +379,30 @@ export class BrowserEditor extends EditorPane {
 			if (this._model) {
 				findWidget.setModel(this._model);
 			}
+			findWidget.onDidChangeHeight(() => {
+				this.layoutBrowserContainer();
+			});
 			return findWidget;
 		});
 		this._register(toDisposable(() => this._findWidget.rawValue?.dispose()));
 
+		// Create browser container wrapper (flex item that fills remaining space)
+		this._browserContainerWrapper = $('.browser-container-wrapper');
+		this._browserContainerWrapper.style.setProperty('--zoom-factor', String(getZoomFactor(this.window)));
+		root.appendChild(this._browserContainerWrapper);
+
 		// Create browser container (stub element for positioning)
 		this._browserContainer = $('.browser-container');
 		this._browserContainer.tabIndex = 0; // make focusable
-		root.appendChild(this._browserContainer);
+		this._browserContainerWrapper.appendChild(this._browserContainer);
+
+		// Create additional wrapper around placeholder contents for applying border radius clipping.
+		const placeholderContents = $('.browser-placeholder-contents');
+		this._browserContainer.appendChild(placeholderContents);
 
 		// Create placeholder screenshot (background placeholder when WebContentsView is hidden)
 		this._placeholderScreenshot = $('.browser-placeholder-screenshot');
-		this._browserContainer.appendChild(this._placeholderScreenshot);
+		placeholderContents.appendChild(this._placeholderScreenshot);
 
 		// Create overlay pause container (hidden by default via CSS)
 		this._overlayPauseContainer = $('.browser-overlay-paused');
@@ -342,16 +412,16 @@ export class BrowserEditor extends EditorPane {
 		overlayPauseMessage.appendChild(this._overlayPauseHeading);
 		overlayPauseMessage.appendChild(this._overlayPauseDetail);
 		this._overlayPauseContainer.appendChild(overlayPauseMessage);
-		this._browserContainer.appendChild(this._overlayPauseContainer);
+		placeholderContents.appendChild(this._overlayPauseContainer);
 
 		// Create error container (hidden by default)
 		this._errorContainer = $('.browser-error-container');
 		this._errorContainer.style.display = 'none';
-		this._browserContainer.appendChild(this._errorContainer);
+		placeholderContents.appendChild(this._errorContainer);
 
 		// Create welcome container (shown when no URL is loaded)
 		this._welcomeContainer = this.createWelcomeContainer();
-		this._browserContainer.appendChild(this._welcomeContainer);
+		placeholderContents.appendChild(this._welcomeContainer);
 
 		this._register(addDisposableListener(this._browserContainer, EventType.FOCUS, (event) => {
 			// When the browser container gets focus, make sure the browser view also gets focused.
@@ -368,12 +438,6 @@ export class BrowserEditor extends EditorPane {
 			hasFocus: this._model?.focused ?? false,
 			window: this._model?.focused ? this.window : undefined
 		})));
-
-		// Automatically call layoutBrowserContainer() when the browser container changes size.
-		// Be careful to use `ResizeObserver` from the target window to avoid cross-window issues.
-		const resizeObserver = new this.window.ResizeObserver(() => this.layoutBrowserContainer());
-		resizeObserver.observe(this._browserContainer);
-		this._register(toDisposable(() => resizeObserver.disconnect()));
 	}
 
 	override async setInput(input: BrowserEditorInput, options: IEditorOptions | undefined, context: IEditorOpenContext, token: CancellationToken): Promise<void> {
@@ -385,14 +449,16 @@ export class BrowserEditor extends EditorPane {
 		this._inputDisposables.clear();
 
 		// Resolve the browser view model from the input
-		this._model = await input.resolve();
+		const model = await input.resolve();
+		this._model = model;
 		if (token.isCancellationRequested || this.input !== input) {
 			return;
 		}
 
 		this._storageScopeContext.set(this._model.storageScope);
 		this._devToolsOpenContext.set(this._model.isDevToolsOpen);
-		this._updateSharingState();
+		this.updateZoomContext();
+		this._updateSharingState(true);
 
 		// Update find widget with new model
 		this._findWidget.rawValue?.setModel(this._model);
@@ -404,10 +470,14 @@ export class BrowserEditor extends EditorPane {
 
 		// Listen for sharing state changes on the model
 		this._inputDisposables.add(this._model.onDidChangeSharedWithAgent(() => {
-			this._updateSharingState();
+			this._updateSharingState(false);
 		}));
 		this._inputDisposables.add(watchForAgentSharingContextChanges(this.contextKeyService)(() => {
-			this._updateSharingState();
+			this._updateSharingState(false);
+		}));
+
+		this._inputDisposables.add(this._model.onDidChangeZoom(() => {
+			this.updateZoomContext();
 		}));
 
 		// Initialize UI state and context keys from model
@@ -419,12 +489,16 @@ export class BrowserEditor extends EditorPane {
 		});
 		this.setBackgroundImage(this._model.screenshot);
 
-		if (context.newInGroup) {
-			if (this._model.url) {
-				this._browserContainer.focus();
-			} else {
-				this.focusUrlInput();
-			}
+		if (!options?.preserveFocus) {
+			setTimeout(() => {
+				if (this._model === model) {
+					if (this._model.url) {
+						this._browserContainer.focus();
+					} else {
+						this.focusUrlInput();
+					}
+				}
+			}, 0);
 		}
 
 		// Start / stop screenshots when the model visibility changes
@@ -494,15 +568,16 @@ export class BrowserEditor extends EditorPane {
 			this.checkOverlays();
 		}));
 
-		// Listen for zoom level changes and update browser view zoom factor
+		// Listen for workbench zoom level changes and update browser view placeholder screenshot's zoom factor
 		this._inputDisposables.add(onDidChangeZoomLevel(targetWindowId => {
 			if (targetWindowId === this.window.vscodeWindowId) {
-				this.layoutBrowserContainer();
+				// Update CSS variable for size calculations
+				this._browserContainerWrapper.style.setProperty('--zoom-factor', String(getZoomFactor(this.window)));
 			}
 		}));
 
 		this.updateErrorDisplay();
-		this.layoutBrowserContainer();
+		this.layout();
 		this.updateVisibility();
 		this.doScreenshot();
 
@@ -648,10 +723,11 @@ export class BrowserEditor extends EditorPane {
 		return this._model?.url;
 	}
 
-	private _updateSharingState(): void {
+	private _updateSharingState(isInitialState: boolean): void {
 		const sharingEnabled = this.contextKeyService.contextMatchesRules(canShareBrowserWithAgentContext);
 		const isShared = sharingEnabled && !!this._model && this._model.sharedWithAgent;
 
+		this._browserContainer.classList.toggle('animate', !isInitialState);
 		this._browserContainer.classList.toggle('shared', isShared);
 		this._navigationBar.setShared(isShared);
 	}
@@ -692,8 +768,8 @@ export class BrowserEditor extends EditorPane {
 		return this._model?.goForward();
 	}
 
-	async reload(): Promise<void> {
-		return this._model?.reload();
+	async reload(hard?: boolean): Promise<void> {
+		return this._model?.reload(hard);
 	}
 
 	async toggleDevTools(): Promise<void> {
@@ -704,12 +780,47 @@ export class BrowserEditor extends EditorPane {
 		return this._model?.clearStorage();
 	}
 
+	async zoomIn(): Promise<void> {
+		await this._model?.zoomIn();
+		this.showZoomPill();
+	}
+
+	async zoomOut(): Promise<void> {
+		await this._model?.zoomOut();
+		this.showZoomPill();
+	}
+
+	async resetZoom(): Promise<void> {
+		await this._model?.resetZoom();
+		this.showZoomPill();
+	}
+
+	private showZoomPill(): void {
+		if (!this._model) {
+			return;
+		}
+		const defaultIndex = this.browserZoomService.getEffectiveZoomIndex(undefined, false);
+		const defaultFactor = browserZoomFactors[defaultIndex];
+		const currentFactor = this._model.zoomFactor;
+		const label = browserZoomLabel(currentFactor);
+		this._navigationBar.showZoomLevel(label, currentFactor >= defaultFactor);
+		// Announce the new zoom level to screen readers (polite, non-interruptive).
+		this.accessibilityService.status(browserZoomAccessibilityLabel(currentFactor));
+	}
+
+	private updateZoomContext(): void {
+		if (this._model) {
+			this._canZoomInContext.set(this._model.canZoomIn);
+			this._canZoomOutContext.set(this._model.canZoomOut);
+		}
+	}
+
 	/**
 	 * Show the find widget, optionally pre-populated with selected text from the browser view
 	 */
 	async showFind(): Promise<void> {
 		// Get selected text from the browser view to pre-populate the search box.
-		const selectedText = await this._model?.getSelectedText();
+		const selectedText = (await this._model?.getSelectedText())?.trim();
 
 		// Only use the selected text if it doesn't contain newlines (single line selection)
 		const textToReveal = selectedText && !/[\r\n]/.test(selectedText) ? selectedText : undefined;
@@ -790,51 +901,7 @@ export class BrowserEditor extends EditorPane {
 				throw new Error('Element data not found');
 			}
 
-			const bounds = elementData.bounds;
-			const toAttach: IChatRequestVariableEntry[] = [];
-
-			// Prepare HTML/CSS context
-			const displayName = getDisplayNameFromOuterHTML(elementData.outerHTML);
-			const attachCss = this.configurationService.getValue<boolean>('chat.sendElementsToChat.attachCSS');
-			const value = this.createElementContextValue(elementData, displayName, attachCss);
-
-			toAttach.push({
-				id: 'element-' + Date.now(),
-				name: displayName,
-				fullName: displayName,
-				value: value,
-				modelDescription: attachCss
-					? 'Structured browser element context with HTML path, attributes, and computed styles.'
-					: 'Structured browser element context with HTML path and attributes.',
-				kind: 'element',
-				icon: ThemeIcon.fromId(Codicon.layout.id),
-				ancestors: elementData.ancestors,
-				attributes: elementData.attributes,
-				computedStyles: attachCss ? elementData.computedStyles : undefined,
-				dimensions: elementData.dimensions,
-				innerText: elementData.innerText,
-			});
-
-			// Attach screenshot if enabled
-			const attachImages = this.configurationService.getValue<boolean>('chat.sendElementsToChat.attachImages');
-			if (attachImages && this._model) {
-				const screenshotBuffer = await this._model.captureScreenshot({
-					quality: 90,
-					rect: bounds
-				});
-
-				toAttach.push({
-					id: 'element-screenshot-' + Date.now(),
-					name: 'Element Screenshot',
-					fullName: 'Element Screenshot',
-					kind: 'image',
-					value: screenshotBuffer.buffer
-				});
-			}
-
-			// Attach to chat widget
-			const widget = await this.chatWidgetService.revealWidget() ?? this.chatWidgetService.lastFocusedWidget;
-			widget?.attachmentModel?.addContext(...toAttach);
+			const { attachCss, attachImages } = await this.attachElementDataToChat(elementData);
 
 			type IntegratedBrowserAddElementToChatAddedEvent = {
 				attachCss: boolean;
@@ -979,6 +1046,53 @@ export class BrowserEditor extends EditorPane {
 		return sections.join('\n\n');
 	}
 
+	private async attachElementDataToChat(elementData: IElementData): Promise<{ attachCss: boolean; attachImages: boolean }> {
+		const bounds = elementData.bounds;
+		const toAttach: IChatRequestVariableEntry[] = [];
+
+		const displayName = getDisplayNameFromOuterHTML(elementData.outerHTML);
+		const attachCss = this.configurationService.getValue<boolean>('chat.sendElementsToChat.attachCSS');
+		const value = this.createElementContextValue(elementData, displayName, attachCss);
+
+		toAttach.push({
+			id: 'element-' + Date.now(),
+			name: displayName,
+			fullName: displayName,
+			value: value,
+			modelDescription: attachCss
+				? 'Structured browser element context with HTML path, attributes, and computed styles.'
+				: 'Structured browser element context with HTML path and attributes.',
+			kind: 'element',
+			icon: ThemeIcon.fromId(Codicon.layout.id),
+			ancestors: elementData.ancestors,
+			attributes: elementData.attributes,
+			computedStyles: attachCss ? elementData.computedStyles : undefined,
+			dimensions: elementData.dimensions,
+			innerText: elementData.innerText,
+		});
+
+		const attachImages = this.configurationService.getValue<boolean>('chat.sendElementsToChat.attachImages');
+		if (attachImages && this._model) {
+			const screenshotBuffer = await this._model.captureScreenshot({
+				quality: 90,
+				rect: bounds
+			});
+
+			toAttach.push({
+				id: 'element-screenshot-' + Date.now(),
+				name: 'Element Screenshot',
+				fullName: 'Element Screenshot',
+				kind: 'image',
+				value: screenshotBuffer.buffer
+			});
+		}
+
+		const widget = await this.chatWidgetService.revealWidget() ?? this.chatWidgetService.lastFocusedWidget;
+		widget?.attachmentModel?.addContext(...toAttach);
+
+		return { attachCss, attachImages };
+	}
+
 	private formatElementPath(ancestors: readonly IElementAncestor[] | undefined): string | undefined {
 		if (!ancestors || ancestors.length === 0) {
 			return undefined;
@@ -1136,6 +1250,34 @@ export class BrowserEditor extends EditorPane {
 		this._currentKeyDownEvent = keyEvent;
 
 		try {
+			const isEnterKey =
+				keyEvent.code === 'Enter' ||
+				keyEvent.code === 'NumpadEnter' ||
+				keyEvent.key === 'Enter' ||
+				keyEvent.key === 'Return';
+			if (this._elementSelectionCts && isEnterKey) {
+				const cts = this._elementSelectionCts;
+				const resourceUri = this.input?.resource;
+				if (!resourceUri) {
+					return;
+				}
+
+				const locator: IBrowserTargetLocator = { browserViewId: BrowserViewUri.getId(resourceUri) };
+				const { width, height } = this._browserContainer.getBoundingClientRect();
+				const elementData = await this.browserElementsService.getFocusedElementData({ x: 0, y: 0, width, height }, cts.token, locator);
+				if (!elementData) {
+					return;
+				}
+
+				await this.attachElementDataToChat(elementData);
+				cts.dispose();
+				if (this._elementSelectionCts === cts) {
+					this._elementSelectionCts = undefined;
+					this._elementSelectionActiveContext.set(false);
+				}
+				return;
+			}
+
 			const syntheticEvent = new KeyboardEvent('keydown', keyEvent);
 			const standardEvent = new StandardKeyboardEvent(syntheticEvent);
 
@@ -1150,32 +1292,42 @@ export class BrowserEditor extends EditorPane {
 		}
 	}
 
-	override layout(dimension: Dimension, _position?: IDomPosition): void {
+	override layout(dimension?: Dimension, _position?: IDomPosition): void {
 		// Layout find widget if it exists
-		this._findWidget.rawValue?.layout(dimension.width);
+		if (dimension && this._findWidget.rawValue) {
+			this._findWidget.rawValue.layout(dimension.width);
+		}
+
+		const whenContainerStylesLoaded = this.layoutService.whenContainerStylesLoaded(this.window);
+		if (whenContainerStylesLoaded) {
+			// In floating windows, we need to ensure that the
+			// container is ready for us to compute certain
+			// layout related properties.
+			whenContainerStylesLoaded.then(() => this.layoutBrowserContainer());
+		} else {
+			this.layoutBrowserContainer();
+		}
 	}
 
 	/**
-	 * This should be called whenever .browser-container changes in size, or when
-	 * there could be any elements, such as the command palette, overlapping with it.
-	 *
-	 * Note that we don't call layoutBrowserContainer() from layout() but instead rely on using a ResizeObserver and on
-	 * making direct calls to it. This is because we have seen cases where the getBoundingClientRect() values of
-	 * the .browser-container element are not correct during layout() calls, especially during "Move into New Window"
-	 * and "Copy into New Window" operations into a different monitor.
+	 * Recompute the layout of the browser container and update the model with the new bounds.
+	 * This should generally only be called via layout() to ensure that the container is ready and all necessary styles are loaded.
 	 */
-	layoutBrowserContainer(): void {
+	private layoutBrowserContainer(): void {
 		if (this._model) {
 			this.checkOverlays();
 
 			const containerRect = this._browserContainer.getBoundingClientRect();
+			const cornerRadius = this.window.getComputedStyle(this._browserContainer).borderTopLeftRadius ?? '0';
+
 			void this._model.layout({
 				windowId: this.group.windowId,
 				x: containerRect.left,
 				y: containerRect.top,
 				width: containerRect.width,
 				height: containerRect.height,
-				zoomFactor: getZoomFactor(this.window)
+				zoomFactor: getZoomFactor(this.window),
+				cornerRadius: parseFloat(cornerRadius)
 			});
 		}
 	}
@@ -1209,6 +1361,8 @@ export class BrowserEditor extends EditorPane {
 		this._storageScopeContext.reset();
 		this._devToolsOpenContext.reset();
 		this._elementSelectionActiveContext.reset();
+		this._canZoomInContext.reset();
+		this._canZoomOutContext.reset();
 
 		this._navigationBar.clear();
 		this.setBackgroundImage(undefined);
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/browserFindWidget.ts b/src/vs/workbench/contrib/browserView/electron-browser/browserFindWidget.ts
index ea918e0428f7c..dc4aba47e858c 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/browserFindWidget.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/browserFindWidget.ts
@@ -11,8 +11,11 @@ import { IKeybindingService } from '../../../../platform/keybinding/common/keybi
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { IAccessibilityService } from '../../../../platform/accessibility/common/accessibility.js';
 import { IBrowserViewModel } from '../common/browserView.js';
+import { BrowserViewCommandId } from '../../../../platform/browserView/common/browserView.js';
 import { localize } from '../../../../nls.js';
-import { DisposableStore } from '../../../../base/common/lifecycle.js';
+import { DisposableStore, toDisposable } from '../../../../base/common/lifecycle.js';
+import { Emitter, Event } from '../../../../base/common/event.js';
+import { getWindow } from '../../../../base/browser/dom.js';
 
 export const CONTEXT_BROWSER_FIND_WIDGET_VISIBLE = new RawContextKey<boolean>('browserFindWidgetVisible', false, localize('browser.findWidgetVisible', "Whether the browser find widget is visible"));
 export const CONTEXT_BROWSER_FIND_WIDGET_FOCUSED = new RawContextKey<boolean>('browserFindWidgetFocused', false, localize('browser.findWidgetFocused', "Whether the browser find widget is focused"));
@@ -30,6 +33,9 @@ export class BrowserFindWidget extends SimpleFindWidget {
 	private _lastFindResult: { resultIndex: number; resultCount: number } | undefined;
 	private _hasFoundMatch = false;
 
+	private readonly _onDidChangeHeight = this._register(new Emitter<void>());
+	readonly onDidChangeHeight: Event<void> = this._onDidChangeHeight.event;
+
 	constructor(
 		private readonly container: HTMLElement,
 		@IContextViewService contextViewService: IContextViewService,
@@ -45,15 +51,27 @@ export class BrowserFindWidget extends SimpleFindWidget {
 			showResultCount: true,
 			enableSash: true,
 			initialWidth: 350,
-			previousMatchActionId: 'workbench.action.browser.findPrevious',
-			nextMatchActionId: 'workbench.action.browser.findNext',
-			closeWidgetActionId: 'workbench.action.browser.hideFind'
+			previousMatchActionId: BrowserViewCommandId.FindPrevious,
+			nextMatchActionId: BrowserViewCommandId.FindNext,
+			closeWidgetActionId: BrowserViewCommandId.HideFind
 		}, contextViewService, contextKeyService, hoverService, keybindingService, configurationService, accessibilityService);
 
 		this._findWidgetVisible = CONTEXT_BROWSER_FIND_WIDGET_VISIBLE.bindTo(contextKeyService);
 		this._findWidgetFocused = CONTEXT_BROWSER_FIND_WIDGET_FOCUSED.bindTo(contextKeyService);
 
-		container.appendChild(this.getDomNode());
+		const domNode = this.getDomNode();
+		container.appendChild(domNode);
+
+		let lastHeight = domNode.offsetHeight;
+		const resizeObserver = new (getWindow(container).ResizeObserver)(() => {
+			const newHeight = domNode.offsetHeight;
+			if (newHeight !== lastHeight) {
+				lastHeight = newHeight;
+				this._onDidChangeHeight.fire();
+			}
+		});
+		resizeObserver.observe(domNode);
+		this._register(toDisposable(() => resizeObserver.disconnect()));
 	}
 
 	/**
@@ -105,6 +123,7 @@ export class BrowserFindWidget extends SimpleFindWidget {
 
 		// Stop find and clear highlights in the browser view
 		this._model?.stopFindInPage(true);
+		this._model?.focus();
 		this._lastFindResult = undefined;
 		this._hasFoundMatch = false;
 	}
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/browserView.contribution.ts b/src/vs/workbench/contrib/browserView/electron-browser/browserView.contribution.ts
index 359ef56102026..3af273caf7a86 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/browserView.contribution.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/browserView.contribution.ts
@@ -9,7 +9,7 @@ import { Registry } from '../../../../platform/registry/common/platform.js';
 import { EditorPaneDescriptor, IEditorPaneRegistry } from '../../../browser/editor.js';
 import { EditorExtensions, IEditorFactoryRegistry } from '../../../common/editor.js';
 import { BrowserEditor } from './browserEditor.js';
-import { BrowserEditorInput, BrowserEditorSerializer } from './browserEditorInput.js';
+import { BrowserEditorInput, BrowserEditorSerializer } from '../common/browserEditorInput.js';
 import { BrowserViewUri } from '../../../../platform/browserView/common/browserViewUri.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { registerSingleton, InstantiationType } from '../../../../platform/instantiation/common/extensions.js';
@@ -18,14 +18,21 @@ import { workbenchConfigurationNodeBase } from '../../../common/configuration.js
 import { IEditorResolverService, RegisteredEditorPriority } from '../../../services/editor/common/editorResolverService.js';
 import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../common/contributions.js';
 import { Schemas } from '../../../../base/common/network.js';
-import { IBrowserViewWorkbenchService } from '../common/browserView.js';
+import { IBrowserViewWorkbenchService, IBrowserViewCDPService } from '../common/browserView.js';
 import { BrowserViewWorkbenchService } from './browserViewWorkbenchService.js';
-import { BrowserViewStorageScope } from '../../../../platform/browserView/common/browserView.js';
-import { IOpenerService, IOpener, OpenInternalOptions, OpenExternalOptions } from '../../../../platform/opener/common/opener.js';
+import { BrowserViewCDPService } from './browserViewCDPService.js';
+import { BrowserZoomService, IBrowserZoomService, MATCH_WINDOW_ZOOM_LABEL } from '../common/browserZoomService.js';
+import { browserZoomFactors, BrowserViewStorageScope } from '../../../../platform/browserView/common/browserView.js';
+import { IExternalOpener, IOpenerService } from '../../../../platform/opener/common/opener.js';
 import { isLocalhostAuthority } from '../../../../platform/url/common/trustedDomains.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { IEditorService } from '../../../services/editor/common/editorService.js';
 import { Disposable } from '../../../../base/common/lifecycle.js';
+import { PolicyCategory } from '../../../../base/common/policy.js';
+import { getZoomLevel, onDidChangeZoomLevel } from '../../../../base/browser/browser.js';
+import { mainWindow } from '../../../../base/browser/window.js';
+import { zoomLevelToZoomFactor } from '../../../../platform/window/common/window.js';
+import { CancellationToken } from '../../../../base/common/cancellation.js';
 import { URI } from '../../../../base/common/uri.js';
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
 import { logBrowserOpen } from '../../../../platform/browserView/common/browserViewTelemetry.js';
@@ -37,7 +44,7 @@ import './tools/browserTools.contribution.js';
 Registry.as<IEditorPaneRegistry>(EditorExtensions.EditorPane).registerEditorPane(
 	EditorPaneDescriptor.create(
 		BrowserEditor,
-		BrowserEditor.ID,
+		BrowserEditorInput.EDITOR_ID,
 		localize('browser.editorLabel', "Browser")
 	),
 	[
@@ -102,7 +109,7 @@ registerWorkbenchContribution2(BrowserEditorResolverContribution.ID, BrowserEdit
 /**
  * Opens localhost URLs in the Integrated Browser when the setting is enabled.
  */
-class LocalhostLinkOpenerContribution extends Disposable implements IWorkbenchContribution, IOpener {
+class LocalhostLinkOpenerContribution extends Disposable implements IWorkbenchContribution, IExternalOpener {
 	static readonly ID = 'workbench.contrib.localhostLinkOpener';
 
 	constructor(
@@ -113,17 +120,16 @@ class LocalhostLinkOpenerContribution extends Disposable implements IWorkbenchCo
 	) {
 		super();
 
-		this._register(openerService.registerOpener(this));
+		this._register(openerService.registerExternalOpener(this));
 	}
 
-	async open(resource: URI | string, _options?: OpenInternalOptions | OpenExternalOptions): Promise<boolean> {
+	async openExternal(href: string, _ctx: { sourceUri: URI; preferredOpenerId?: string }, _token: CancellationToken): Promise<boolean> {
 		if (!this.configurationService.getValue<boolean>('workbench.browser.openLocalhostLinks')) {
 			return false;
 		}
 
-		const url = typeof resource === 'string' ? resource : resource.toString(true);
 		try {
-			const parsed = new URL(url);
+			const parsed = new URL(href);
 			if (parsed.protocol !== 'http:' && parsed.protocol !== 'https:') {
 				return false;
 			}
@@ -136,7 +142,7 @@ class LocalhostLinkOpenerContribution extends Disposable implements IWorkbenchCo
 
 		logBrowserOpen(this.telemetryService, 'localhostLinkOpener');
 
-		const browserUri = BrowserViewUri.forUrl(url);
+		const browserUri = BrowserViewUri.forUrl(href);
 		await this.editorService.openEditor({ resource: browserUri, options: { pinned: true } });
 		return true;
 	}
@@ -144,11 +150,40 @@ class LocalhostLinkOpenerContribution extends Disposable implements IWorkbenchCo
 
 registerWorkbenchContribution2(LocalhostLinkOpenerContribution.ID, LocalhostLinkOpenerContribution, WorkbenchPhase.BlockStartup);
 
+/**
+ * Bridges the application's UI zoom level changes into IBrowserZoomService so that
+ * views using the 'Match Window' default zoom level stay in sync.
+ */
+class WindowZoomSynchronizer extends Disposable implements IWorkbenchContribution {
+	static readonly ID = 'workbench.contrib.browserView.windowZoomSynchronizer';
+
+	constructor(@IBrowserZoomService browserZoomService: IBrowserZoomService) {
+		super();
+		browserZoomService.notifyWindowZoomChanged(zoomLevelToZoomFactor(getZoomLevel(mainWindow)));
+		this._register(onDidChangeZoomLevel(() => {
+			browserZoomService.notifyWindowZoomChanged(zoomLevelToZoomFactor(getZoomLevel(mainWindow)));
+		}));
+	}
+}
+
+registerWorkbenchContribution2(WindowZoomSynchronizer.ID, WindowZoomSynchronizer, WorkbenchPhase.BlockRestore);
+
 registerSingleton(IBrowserViewWorkbenchService, BrowserViewWorkbenchService, InstantiationType.Delayed);
+registerSingleton(IBrowserViewCDPService, BrowserViewCDPService, InstantiationType.Delayed);
+registerSingleton(IBrowserZoomService, BrowserZoomService, InstantiationType.Delayed);
 
 Registry.as<IConfigurationRegistry>(ConfigurationExtensions.Configuration).registerConfiguration({
 	...workbenchConfigurationNodeBase,
 	properties: {
+		'workbench.browser.showInTitleBar': {
+			type: 'boolean',
+			default: false,
+			experiment: { mode: 'startup' },
+			description: localize(
+				{ comment: ['This is the description for a setting.'], key: 'browser.showInTitleBar' },
+				'Controls whether the Integrated Browser button is shown in the title bar.'
+			)
+		},
 		'workbench.browser.openLocalhostLinks': {
 			type: 'boolean',
 			default: false,
@@ -165,7 +200,37 @@ Registry.as<IConfigurationRegistry>(ConfigurationExtensions.Configuration).regis
 			markdownDescription: localize(
 				{ comment: ['This is the description for a setting.'], key: 'browser.enableChatTools' },
 				'When enabled, chat agents can use browser tools to open and interact with pages in the Integrated Browser.'
-			)
+			),
+			policy: {
+				name: 'BrowserChatTools',
+				category: PolicyCategory.InteractiveSession,
+				minimumVersion: '1.110',
+				value: (policyData) => policyData.chat_preview_features_enabled === false ? false : undefined,
+				localization: {
+					description: {
+						key: 'browser.enableChatTools',
+						value: localize('browser.enableChatTools', 'When enabled, chat agents can use browser tools to open and interact with pages in the Integrated Browser.')
+					}
+				},
+			}
+		},
+		'workbench.browser.pageZoom': {
+			type: 'string',
+			enum: [MATCH_WINDOW_ZOOM_LABEL, ...browserZoomFactors.map(f => `${Math.round(f * 100)}%`)],
+			markdownEnumDescriptions: [
+				localize(
+					{ comment: ['This is the description for a setting enum value.'], key: 'browser.defaultZoomLevel.matchWindow' },
+					'Matches the application\'s current UI zoom level.'
+				),
+				...browserZoomFactors.map(() => ''),
+			],
+			default: MATCH_WINDOW_ZOOM_LABEL,
+			markdownDescription: localize(
+				{ comment: ['This is the description for a setting.'], key: 'browser.pageZoom' },
+				'Default zoom level for all sites in the Integrated Browser.'
+			),
+			// Zoom can change from machine to machine, so we don't need the workspace-level nor syncing that WINDOW has.
+			scope: ConfigurationScope.MACHINE
 		},
 		'workbench.browser.dataStorage': {
 			type: 'string',
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/browserViewActions.ts b/src/vs/workbench/contrib/browserView/electron-browser/browserViewActions.ts
index 66f0f46827704..9764793b826a5 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/browserViewActions.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/browserViewActions.ts
@@ -3,7 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { localize2 } from '../../../../nls.js';
+import { localize, localize2 } from '../../../../nls.js';
 import { ContextKeyExpr } from '../../../../platform/contextkey/common/contextkey.js';
 import { Action2, registerAction2, MenuId } from '../../../../platform/actions/common/actions.js';
 import { ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
@@ -11,23 +11,26 @@ import { KeybindingWeight } from '../../../../platform/keybinding/common/keybind
 import { KeyMod, KeyCode } from '../../../../base/common/keyCodes.js';
 import { ACTIVE_GROUP, IEditorService, SIDE_GROUP } from '../../../services/editor/common/editorService.js';
 import { Codicon } from '../../../../base/common/codicons.js';
-import { BrowserEditor, CONTEXT_BROWSER_CAN_GO_BACK, CONTEXT_BROWSER_CAN_GO_FORWARD, CONTEXT_BROWSER_DEVTOOLS_OPEN, CONTEXT_BROWSER_FOCUSED, CONTEXT_BROWSER_HAS_ERROR, CONTEXT_BROWSER_HAS_URL, CONTEXT_BROWSER_STORAGE_SCOPE, CONTEXT_BROWSER_ELEMENT_SELECTION_ACTIVE, CONTEXT_BROWSER_FIND_WIDGET_FOCUSED, CONTEXT_BROWSER_FIND_WIDGET_VISIBLE } from './browserEditor.js';
+import { BrowserEditor, CONTEXT_BROWSER_CAN_GO_BACK, CONTEXT_BROWSER_CAN_GO_FORWARD, CONTEXT_BROWSER_CAN_ZOOM_IN, CONTEXT_BROWSER_CAN_ZOOM_OUT, CONTEXT_BROWSER_DEVTOOLS_OPEN, CONTEXT_BROWSER_FOCUSED, CONTEXT_BROWSER_HAS_ERROR, CONTEXT_BROWSER_HAS_URL, CONTEXT_BROWSER_STORAGE_SCOPE, CONTEXT_BROWSER_ELEMENT_SELECTION_ACTIVE, CONTEXT_BROWSER_FIND_WIDGET_FOCUSED, CONTEXT_BROWSER_FIND_WIDGET_VISIBLE } from './browserEditor.js';
 import { BrowserViewUri } from '../../../../platform/browserView/common/browserViewUri.js';
 import { IBrowserViewWorkbenchService } from '../common/browserView.js';
-import { BrowserViewStorageScope } from '../../../../platform/browserView/common/browserView.js';
+import { BrowserViewCommandId, BrowserViewStorageScope } from '../../../../platform/browserView/common/browserView.js';
 import { ChatContextKeys } from '../../chat/common/actions/chatContextKeys.js';
 import { IOpenerService } from '../../../../platform/opener/common/opener.js';
 import { IPreferencesService } from '../../../services/preferences/common/preferences.js';
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
 import { logBrowserOpen } from '../../../../platform/browserView/common/browserViewTelemetry.js';
+import { BrowserEditorInput } from '../common/browserEditorInput.js';
+import { ToggleTitleBarConfigAction } from '../../../browser/parts/titlebar/titlebarActions.js';
 
 // Context key expression to check if browser editor is active
-const BROWSER_EDITOR_ACTIVE = ContextKeyExpr.equals('activeEditor', BrowserEditor.ID);
+const BROWSER_EDITOR_ACTIVE = ContextKeyExpr.equals('activeEditor', BrowserEditorInput.EDITOR_ID);
 
 const BrowserCategory = localize2('browserCategory', "Browser");
 const ActionGroupTabs = '1_tabs';
-const ActionGroupPage = '2_page';
-const ActionGroupSettings = '3_settings';
+const ActionGroupZoom = '2_zoom';
+const ActionGroupPage = '3_page';
+const ActionGroupSettings = '4_settings';
 
 interface IOpenBrowserOptions {
 	url?: string;
@@ -37,10 +40,17 @@ interface IOpenBrowserOptions {
 class OpenIntegratedBrowserAction extends Action2 {
 	constructor() {
 		super({
-			id: 'workbench.action.browser.open',
+			id: BrowserViewCommandId.Open,
 			title: localize2('browser.openAction', "Open Integrated Browser"),
 			category: BrowserCategory,
-			f1: true
+			icon: Codicon.globe,
+			f1: true,
+			menu: {
+				id: MenuId.TitleBar,
+				group: 'navigation',
+				order: 10,
+				when: ContextKeyExpr.equals('config.workbench.browser.showInTitleBar', true)
+			}
 		});
 	}
 
@@ -67,7 +77,7 @@ class OpenIntegratedBrowserAction extends Action2 {
 class NewTabAction extends Action2 {
 	constructor() {
 		super({
-			id: 'workbench.action.browser.newTab',
+			id: BrowserViewCommandId.NewTab,
 			title: localize2('browser.newTabAction', "New Tab"),
 			category: BrowserCategory,
 			f1: true,
@@ -97,7 +107,7 @@ class NewTabAction extends Action2 {
 }
 
 class GoBackAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.goBack';
+	static readonly ID = BrowserViewCommandId.GoBack;
 
 	constructor() {
 		super({
@@ -129,7 +139,7 @@ class GoBackAction extends Action2 {
 }
 
 class GoForwardAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.goForward';
+	static readonly ID = BrowserViewCommandId.GoForward;
 
 	constructor() {
 		super({
@@ -161,7 +171,7 @@ class GoForwardAction extends Action2 {
 }
 
 class ReloadAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.reload';
+	static readonly ID = BrowserViewCommandId.Reload;
 
 	constructor() {
 		super({
@@ -175,6 +185,11 @@ class ReloadAction extends Action2 {
 				id: MenuId.BrowserNavigationToolbar,
 				group: 'navigation',
 				order: 3,
+				alt: {
+					id: HardReloadAction.ID,
+					title: localize2('browser.hardReloadAction', 'Hard Reload'),
+					icon: Codicon.refresh,
+				}
 			},
 			keybinding: {
 				when: CONTEXT_BROWSER_FOCUSED,
@@ -193,8 +208,36 @@ class ReloadAction extends Action2 {
 	}
 }
 
+class HardReloadAction extends Action2 {
+	static readonly ID = BrowserViewCommandId.HardReload;
+
+	constructor() {
+		super({
+			id: HardReloadAction.ID,
+			title: localize2('browser.hardReloadAction', 'Hard Reload'),
+			category: BrowserCategory,
+			icon: Codicon.refresh,
+			f1: true,
+			precondition: BROWSER_EDITOR_ACTIVE,
+			keybinding: {
+				when: CONTEXT_BROWSER_FOCUSED,
+				weight: KeybindingWeight.WorkbenchContrib + 75, // Priority over debug and reload workbench
+				primary: KeyMod.CtrlCmd | KeyMod.Shift | KeyCode.KeyR,
+				secondary: [KeyMod.CtrlCmd | KeyCode.F5],
+				mac: { primary: KeyMod.CtrlCmd | KeyMod.Shift | KeyCode.KeyR, secondary: [] }
+			}
+		});
+	}
+
+	async run(accessor: ServicesAccessor, browserEditor = accessor.get(IEditorService).activeEditorPane): Promise<void> {
+		if (browserEditor instanceof BrowserEditor) {
+			await browserEditor.reload(true);
+		}
+	}
+}
+
 class FocusUrlInputAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.focusUrlInput';
+	static readonly ID = BrowserViewCommandId.FocusUrlInput;
 
 	constructor() {
 		super({
@@ -218,7 +261,7 @@ class FocusUrlInputAction extends Action2 {
 }
 
 class AddElementToChatAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.addElementToChat';
+	static readonly ID = BrowserViewCommandId.AddElementToChat;
 
 	constructor() {
 		const enabled = ContextKeyExpr.and(ChatContextKeys.enabled, ContextKeyExpr.equals('config.chat.sendElementsToChat.enabled', true));
@@ -255,7 +298,7 @@ class AddElementToChatAction extends Action2 {
 }
 
 class AddConsoleLogsToChatAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.addConsoleLogsToChat';
+	static readonly ID = BrowserViewCommandId.AddConsoleLogsToChat;
 
 	constructor() {
 		const enabled = ContextKeyExpr.and(ChatContextKeys.enabled, ContextKeyExpr.equals('config.chat.sendElementsToChat.enabled', true));
@@ -283,7 +326,7 @@ class AddConsoleLogsToChatAction extends Action2 {
 }
 
 class ToggleDevToolsAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.toggleDevTools';
+	static readonly ID = BrowserViewCommandId.ToggleDevTools;
 
 	constructor() {
 		super({
@@ -314,7 +357,7 @@ class ToggleDevToolsAction extends Action2 {
 }
 
 class OpenInExternalBrowserAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.openExternal';
+	static readonly ID = BrowserViewCommandId.OpenExternal;
 
 	constructor() {
 		super({
@@ -338,14 +381,19 @@ class OpenInExternalBrowserAction extends Action2 {
 			const url = browserEditor.getUrl();
 			if (url) {
 				const openerService = accessor.get(IOpenerService);
-				await openerService.open(url, { openExternal: true });
+				await openerService.open(url, {
+					// ensures that VS Code itself doesn't try to open the URL, even for non-"http(s):" scheme URLs.
+					openExternal: true,
+					// ensures that the link isn't opened in Integrated Browser or other contributed external openers. False is the default, but just being explicit here.
+					allowContributedOpeners: false
+				});
 			}
 		}
 	}
 }
 
 class ClearGlobalBrowserStorageAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.clearGlobalStorage';
+	static readonly ID = BrowserViewCommandId.ClearGlobalStorage;
 
 	constructor() {
 		super({
@@ -370,7 +418,7 @@ class ClearGlobalBrowserStorageAction extends Action2 {
 }
 
 class ClearWorkspaceBrowserStorageAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.clearWorkspaceStorage';
+	static readonly ID = BrowserViewCommandId.ClearWorkspaceStorage;
 
 	constructor() {
 		super({
@@ -395,7 +443,7 @@ class ClearWorkspaceBrowserStorageAction extends Action2 {
 }
 
 class ClearEphemeralBrowserStorageAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.clearEphemeralStorage';
+	static readonly ID = BrowserViewCommandId.ClearEphemeralStorage;
 
 	constructor() {
 		super({
@@ -407,7 +455,7 @@ class ClearEphemeralBrowserStorageAction extends Action2 {
 			precondition: ContextKeyExpr.equals(CONTEXT_BROWSER_STORAGE_SCOPE.key, BrowserViewStorageScope.Ephemeral),
 			menu: {
 				id: MenuId.BrowserActionsToolbar,
-				group: '3_settings',
+				group: ActionGroupSettings,
 				order: 1,
 				when: ContextKeyExpr.equals(CONTEXT_BROWSER_STORAGE_SCOPE.key, BrowserViewStorageScope.Ephemeral)
 			}
@@ -422,7 +470,7 @@ class ClearEphemeralBrowserStorageAction extends Action2 {
 }
 
 class OpenBrowserSettingsAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.openSettings';
+	static readonly ID = BrowserViewCommandId.OpenSettings;
 
 	constructor() {
 		super({
@@ -445,10 +493,117 @@ class OpenBrowserSettingsAction extends Action2 {
 	}
 }
 
+// Zoom actions
+
+class ZoomInAction extends Action2 {
+	static readonly ID = 'workbench.action.browser.zoomIn';
+
+	constructor() {
+		super({
+			id: ZoomInAction.ID,
+			title: localize2('browser.zoomInAction', 'Zoom In'),
+			category: BrowserCategory,
+			icon: Codicon.zoomIn,
+			f1: true,
+			precondition: ContextKeyExpr.and(BROWSER_EDITOR_ACTIVE, CONTEXT_BROWSER_HAS_URL, CONTEXT_BROWSER_HAS_ERROR.negate()),
+			menu: {
+				id: MenuId.BrowserActionsToolbar,
+				group: ActionGroupZoom,
+				order: 1,
+				when: CONTEXT_BROWSER_CAN_ZOOM_IN,
+			},
+			keybinding: {
+				when: CONTEXT_BROWSER_FOCUSED,
+				weight: KeybindingWeight.WorkbenchContrib + 75,
+				// Same shortcuts as 'workbench.action.zoomIn'
+				primary: KeyMod.CtrlCmd | KeyCode.Equal,
+				secondary: [KeyMod.CtrlCmd | KeyMod.Shift | KeyCode.Equal, KeyMod.CtrlCmd | KeyCode.NumpadAdd],
+			},
+		});
+	}
+
+	async run(accessor: ServicesAccessor, browserEditor = accessor.get(IEditorService).activeEditorPane): Promise<void> {
+		if (browserEditor instanceof BrowserEditor) {
+			await browserEditor.zoomIn();
+		}
+	}
+}
+
+class ZoomOutAction extends Action2 {
+	static readonly ID = 'workbench.action.browser.zoomOut';
+
+	constructor() {
+		super({
+			id: ZoomOutAction.ID,
+			title: localize2('browser.zoomOutAction', 'Zoom Out'),
+			category: BrowserCategory,
+			icon: Codicon.zoomOut,
+			f1: true,
+			precondition: ContextKeyExpr.and(BROWSER_EDITOR_ACTIVE, CONTEXT_BROWSER_HAS_URL, CONTEXT_BROWSER_HAS_ERROR.negate()),
+			menu: {
+				id: MenuId.BrowserActionsToolbar,
+				group: ActionGroupZoom,
+				order: 2,
+				when: CONTEXT_BROWSER_CAN_ZOOM_OUT,
+			},
+			keybinding: {
+				when: CONTEXT_BROWSER_FOCUSED,
+				weight: KeybindingWeight.WorkbenchContrib + 75,
+				// Same shortcuts as 'workbench.action.zoomOut'
+				primary: KeyMod.CtrlCmd | KeyCode.Minus,
+				secondary: [KeyMod.CtrlCmd | KeyMod.Shift | KeyCode.Minus, KeyMod.CtrlCmd | KeyCode.NumpadSubtract],
+				linux: {
+					primary: KeyMod.CtrlCmd | KeyCode.Minus,
+					secondary: [KeyMod.CtrlCmd | KeyCode.NumpadSubtract]
+				}
+			},
+		});
+	}
+
+	async run(accessor: ServicesAccessor, browserEditor = accessor.get(IEditorService).activeEditorPane): Promise<void> {
+		if (browserEditor instanceof BrowserEditor) {
+			await browserEditor.zoomOut();
+		}
+	}
+}
+
+class ResetZoomAction extends Action2 {
+	static readonly ID = 'workbench.action.browser.resetZoom';
+
+	constructor() {
+		super({
+			id: ResetZoomAction.ID,
+			title: localize2('browser.resetZoomAction', 'Reset Zoom'),
+			category: BrowserCategory,
+			icon: Codicon.screenNormal,
+			f1: true,
+			precondition: ContextKeyExpr.and(BROWSER_EDITOR_ACTIVE, CONTEXT_BROWSER_HAS_URL, CONTEXT_BROWSER_HAS_ERROR.negate()),
+			menu: {
+				id: MenuId.BrowserActionsToolbar,
+				group: ActionGroupZoom,
+				order: 3,
+			},
+			keybinding: {
+				when: CONTEXT_BROWSER_FOCUSED,
+				weight: KeybindingWeight.WorkbenchContrib + 75,
+				// Same shortcuts as 'workbench.action.zoomReset'
+				// (note: both workbench and here use Numpad0 instead of Digit0 to avoid conflicts with keybinding to focus sidebar.)
+				primary: KeyMod.CtrlCmd | KeyCode.Numpad0,
+			},
+		});
+	}
+
+	async run(accessor: ServicesAccessor, browserEditor = accessor.get(IEditorService).activeEditorPane): Promise<void> {
+		if (browserEditor instanceof BrowserEditor) {
+			await browserEditor.resetZoom();
+		}
+	}
+}
+
 // Find actions
 
 class ShowBrowserFindAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.showFind';
+	static readonly ID = BrowserViewCommandId.ShowFind;
 
 	constructor() {
 		super({
@@ -477,7 +632,7 @@ class ShowBrowserFindAction extends Action2 {
 }
 
 class HideBrowserFindAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.hideFind';
+	static readonly ID = BrowserViewCommandId.HideFind;
 
 	constructor() {
 		super({
@@ -502,7 +657,7 @@ class HideBrowserFindAction extends Action2 {
 }
 
 class BrowserFindNextAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.findNext';
+	static readonly ID = BrowserViewCommandId.FindNext;
 
 	constructor() {
 		super({
@@ -533,7 +688,7 @@ class BrowserFindNextAction extends Action2 {
 }
 
 class BrowserFindPreviousAction extends Action2 {
-	static readonly ID = 'workbench.action.browser.findPrevious';
+	static readonly ID = BrowserViewCommandId.FindPrevious;
 
 	constructor() {
 		super({
@@ -569,6 +724,7 @@ registerAction2(NewTabAction);
 registerAction2(GoBackAction);
 registerAction2(GoForwardAction);
 registerAction2(ReloadAction);
+registerAction2(HardReloadAction);
 registerAction2(FocusUrlInputAction);
 registerAction2(AddElementToChatAction);
 registerAction2(AddConsoleLogsToChatAction);
@@ -578,7 +734,16 @@ registerAction2(ClearGlobalBrowserStorageAction);
 registerAction2(ClearWorkspaceBrowserStorageAction);
 registerAction2(ClearEphemeralBrowserStorageAction);
 registerAction2(OpenBrowserSettingsAction);
+registerAction2(ZoomInAction);
+registerAction2(ZoomOutAction);
+registerAction2(ResetZoomAction);
 registerAction2(ShowBrowserFindAction);
 registerAction2(HideBrowserFindAction);
 registerAction2(BrowserFindNextAction);
 registerAction2(BrowserFindPreviousAction);
+
+registerAction2(class ToggleBrowserTitleBarButton extends ToggleTitleBarConfigAction {
+	constructor() {
+		super('workbench.browser.showInTitleBar', localize('toggle.browser', 'Integrated Browser'), localize('toggle.browserDescription', "Toggle visibility of the Integrated Browser button in title bar"), 8);
+	}
+});
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/browserViewCDPService.ts b/src/vs/workbench/contrib/browserView/electron-browser/browserViewCDPService.ts
new file mode 100644
index 0000000000000..7770b21efb4c6
--- /dev/null
+++ b/src/vs/workbench/contrib/browserView/electron-browser/browserViewCDPService.ts
@@ -0,0 +1,67 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Event } from '../../../../base/common/event.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { ProxyChannel } from '../../../../base/parts/ipc/common/ipc.js';
+import { CDPEvent, CDPRequest, CDPResponse } from '../../../../platform/browserView/common/cdp/types.js';
+import { IBrowserViewGroupService, ipcBrowserViewGroupChannelName } from '../../../../platform/browserView/common/browserViewGroup.js';
+import { BrowserViewUri } from '../../../../platform/browserView/common/browserViewUri.js';
+import { IMainProcessService } from '../../../../platform/ipc/common/mainProcessService.js';
+import { IBrowserViewCDPService } from '../common/browserView.js';
+import { IEditorService } from '../../../services/editor/common/editorService.js';
+import { IEditorGroupsService } from '../../../services/editor/common/editorGroupsService.js';
+
+export class BrowserViewCDPService extends Disposable implements IBrowserViewCDPService {
+	declare readonly _serviceBrand: undefined;
+
+	private readonly _groupService: IBrowserViewGroupService;
+
+	constructor(
+		@IMainProcessService mainProcessService: IMainProcessService,
+		@IEditorService private readonly editorService: IEditorService,
+		@IEditorGroupsService private readonly editorGroupsService: IEditorGroupsService,
+	) {
+		super();
+		const channel = mainProcessService.getChannel(ipcBrowserViewGroupChannelName);
+		this._groupService = ProxyChannel.toService<IBrowserViewGroupService>(channel);
+	}
+
+	async createSessionGroup(browserId: string): Promise<string> {
+		const windowId = this._getWindowIdForBrowser(browserId);
+		const groupId = await this._groupService.createGroup(windowId);
+		await this._groupService.addViewToGroup(groupId, browserId);
+		return groupId;
+	}
+
+	async destroySessionGroup(groupId: string): Promise<void> {
+		await this._groupService.destroyGroup(groupId);
+	}
+
+	async sendCDPMessage(groupId: string, message: CDPRequest): Promise<void> {
+		await this._groupService.sendCDPMessage(groupId, message);
+	}
+
+	onCDPMessage(groupId: string): Event<CDPResponse | CDPEvent> {
+		return this._groupService.onDynamicCDPMessage(groupId);
+	}
+
+	onDidDestroy(groupId: string): Event<void> {
+		return this._groupService.onDynamicDidDestroy(groupId);
+	}
+
+	private _getWindowIdForBrowser(browserId: string): number {
+		const browserUri = BrowserViewUri.forUrl(undefined, browserId);
+		const editors = this.editorService.findEditors(browserUri);
+		if (editors.length > 0) {
+			const group = this.editorGroupsService.getGroup(editors[0].groupId);
+			if (group) {
+				return group.windowId;
+			}
+		}
+		// Fall back to main window
+		return this.editorGroupsService.mainPart.windowId;
+	}
+}
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/browserViewWorkbenchService.ts b/src/vs/workbench/contrib/browserView/electron-browser/browserViewWorkbenchService.ts
index 68d2376c587d1..d189013b3adb7 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/browserViewWorkbenchService.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/browserViewWorkbenchService.ts
@@ -3,15 +3,24 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { IBrowserViewService, ipcBrowserViewChannelName } from '../../../../platform/browserView/common/browserView.js';
+import { BrowserViewCommandId, IBrowserViewService, ipcBrowserViewChannelName } from '../../../../platform/browserView/common/browserView.js';
 import { IBrowserViewWorkbenchService, IBrowserViewModel, BrowserViewModel } from '../common/browserView.js';
 import { IMainProcessService } from '../../../../platform/ipc/common/mainProcessService.js';
 import { ProxyChannel } from '../../../../base/parts/ipc/common/ipc.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { IWorkspaceContextService } from '../../../../platform/workspace/common/workspace.js';
 import { Event } from '../../../../base/common/event.js';
+import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
 
-export class BrowserViewWorkbenchService implements IBrowserViewWorkbenchService {
+/** Command IDs whose accelerators are shown in browser view context menus. */
+const browserViewContextMenuCommands = [
+	BrowserViewCommandId.GoBack,
+	BrowserViewCommandId.GoForward,
+	BrowserViewCommandId.Reload,
+];
+
+export class BrowserViewWorkbenchService extends Disposable implements IBrowserViewWorkbenchService {
 	declare readonly _serviceBrand: undefined;
 
 	private readonly _browserViewService: IBrowserViewService;
@@ -20,13 +29,35 @@ export class BrowserViewWorkbenchService implements IBrowserViewWorkbenchService
 	constructor(
 		@IMainProcessService mainProcessService: IMainProcessService,
 		@IInstantiationService private readonly instantiationService: IInstantiationService,
-		@IWorkspaceContextService private readonly workspaceContextService: IWorkspaceContextService
+		@IWorkspaceContextService private readonly workspaceContextService: IWorkspaceContextService,
+		@IKeybindingService private readonly keybindingService: IKeybindingService
 	) {
+		super();
 		const channel = mainProcessService.getChannel(ipcBrowserViewChannelName);
 		this._browserViewService = ProxyChannel.toService<IBrowserViewService>(channel);
+
+		this.sendKeybindings();
+		this._register(this.keybindingService.onDidUpdateKeybindings(() => this.sendKeybindings()));
 	}
 
 	async getOrCreateBrowserViewModel(id: string): Promise<IBrowserViewModel> {
+		return this._getBrowserViewModel(id, true);
+	}
+
+	async getBrowserViewModel(id: string): Promise<IBrowserViewModel> {
+		return this._getBrowserViewModel(id, false);
+	}
+
+	async clearGlobalStorage(): Promise<void> {
+		return this._browserViewService.clearGlobalStorage();
+	}
+
+	async clearWorkspaceStorage(): Promise<void> {
+		const workspaceId = this.workspaceContextService.getWorkspace().id;
+		return this._browserViewService.clearWorkspaceStorage(workspaceId);
+	}
+
+	private async _getBrowserViewModel(id: string, create: boolean): Promise<IBrowserViewModel> {
 		let model = this._models.get(id);
 		if (model) {
 			return model;
@@ -36,7 +67,12 @@ export class BrowserViewWorkbenchService implements IBrowserViewWorkbenchService
 		this._models.set(id, model);
 
 		// Initialize the model with current state
-		await model.initialize();
+		try {
+			await model.initialize(create);
+		} catch (e) {
+			this._models.delete(id);
+			throw e;
+		}
 
 		// Clean up model when disposed
 		Event.once(model.onWillDispose)(() => {
@@ -46,12 +82,15 @@ export class BrowserViewWorkbenchService implements IBrowserViewWorkbenchService
 		return model;
 	}
 
-	async clearGlobalStorage(): Promise<void> {
-		return this._browserViewService.clearGlobalStorage();
-	}
-
-	async clearWorkspaceStorage(): Promise<void> {
-		const workspaceId = this.workspaceContextService.getWorkspace().id;
-		return this._browserViewService.clearWorkspaceStorage(workspaceId);
+	private sendKeybindings(): void {
+		const keybindings: { [commandId: string]: string } = Object.create(null);
+		for (const commandId of browserViewContextMenuCommands) {
+			const binding = this.keybindingService.lookupKeybinding(commandId);
+			const accelerator = binding?.getElectronAccelerator();
+			if (accelerator) {
+				keybindings[commandId] = accelerator;
+			}
+		}
+		void this._browserViewService.updateKeybindings(keybindings);
 	}
 }
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/media/browser.css b/src/vs/workbench/contrib/browserView/electron-browser/media/browser.css
index 958e00af4ab0b..7d9d68e205458 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/media/browser.css
+++ b/src/vs/workbench/contrib/browserView/electron-browser/media/browser.css
@@ -3,6 +3,27 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+@property --animation-angle {
+	syntax: '<angle>';
+	inherits: false;
+	initial-value: 135deg;
+}
+
+@property --animation-opacity {
+	syntax: '<percentage>';
+	inherits: false;
+	initial-value: 0%;
+}
+
+@keyframes browser-shared-border-spin {
+	from {
+		--animation-angle: 135deg;
+	}
+	to {
+		--animation-angle: 495deg;
+	}
+}
+
 .browser-root {
 	display: flex;
 	flex-direction: column;
@@ -13,7 +34,6 @@
 		display: flex;
 		align-items: center;
 		padding: 6px 8px;
-		border-bottom: 1px solid var(--vscode-widget-border);
 		background-color: var(--vscode-editor-background);
 		flex-shrink: 0;
 		gap: 8px;
@@ -27,10 +47,13 @@
 
 		.actions-container {
 			gap: 4px;
-			margin-right: 4px;
 		}
 	}
 
+	.browser-actions-toolbar {
+		margin-right: 4px;
+	}
+
 	.browser-url-container {
 		flex: 1;
 		display: flex;
@@ -46,6 +69,7 @@
 
 	.browser-url-input {
 		flex: 1;
+		min-width: 0;
 		padding: 4px 8px;
 		background-color: transparent;
 		color: var(--vscode-input-foreground);
@@ -53,6 +77,32 @@
 		border-radius: var(--vscode-cornerRadius-small);
 		outline: none !important;
 		font-size: 13px;
+		text-overflow: ellipsis;
+		overflow: hidden;
+		white-space: nowrap;
+	}
+
+	.browser-zoom-pill {
+		display: none;
+		align-items: center;
+		gap: 2px;
+		margin: 0 2px;
+		padding: 0 2px;
+		flex-shrink: 0;
+		border-radius: var(--vscode-cornerRadius-small);
+		color: var(--vscode-descriptionForeground);
+		font-size: 13px;
+		line-height: 1;
+		white-space: nowrap;
+		pointer-events: none;
+
+		&.visible {
+			display: flex;
+		}
+
+		.codicon {
+			font-size: 14px;
+		}
 	}
 
 	.browser-share-toggle-container {
@@ -68,6 +118,12 @@
 			color: var(--vscode-descriptionForeground);
 			white-space: nowrap;
 			gap: 4px;
+			outline: none !important;
+
+			&:focus-visible {
+				outline: 1px solid var(--vscode-focusBorder) !important;
+				outline-offset: 0px !important;
+			}
 
 			.codicon {
 				margin: 0;
@@ -97,45 +153,94 @@
 		}
 	}
 
-	.browser-container {
+	.browser-container-wrapper {
 		flex: 1;
 		min-height: 0;
-		margin: 0 2px 2px;
+		position: relative;
+		margin-top: 1px;
+	}
+
+	.browser-container {
+		/*
+		 * Snap dimensions to multiples of 1/zoomFactor CSS pixels so that
+		 * width*zoomFactor and height*zoomFactor are always integers. This
+		 * avoids sub-pixel mismatches between the WebContentsView
+		 * (whose bounds are rounded to integer DIPs) and this CSS container,
+		 * which would cause visible shifts when swapping between the live
+		 * view and the placeholder screenshot.
+		 */
+		width: round(down, 100% - 8px, calc(1px / var(--zoom-factor, 1)));
+		height: round(down, 100% - 4px, calc(1px / var(--zoom-factor, 1)));
+		margin: 0 auto;
 		overflow: visible;
+		border-radius: var(--vscode-cornerRadius-medium);
 		position: relative;
-		z-index: 0; /* Important: creates a new stacking context for the gradient border trick */
 		outline: none !important;
-		border-radius: 2px;
-
-		&.shared {
-			&::before {
-				content: '';
-				position: absolute;
-				top: -2px;
-				left: -2px;
-				right: -2px;
-				bottom: -2px;
-				z-index: -2;
-				background: linear-gradient(135deg in lab,
-					color-mix(in srgb, #51a2ff 100%, transparent),
-					color-mix(in srgb, #4af0c0 100%, transparent),
-					color-mix(in srgb, #b44aff 100%, transparent)
-				) !important;
-				pointer-events: none;
-			}
+		z-index: 0; /* Important: creates a new stacking context for the gradient border trick */
 
-			&::after {
-				content: '';
-				position: absolute;
-				top: 0;
-				left: 0;
-				right: 0;
-				bottom: 0;
-				z-index: -1;
-				background-color: var(--vscode-editor-background);
-				pointer-events: none;
-			}
+		&::before {
+			content: '';
+			position: absolute;
+			--animation-angle: 135deg;
+			--animation-opacity: 0%;
+			top: -1px;
+			left: -1px;
+			right: -1px;
+			bottom: -1px;
+			z-index: -2;
+			border-radius: var(--vscode-cornerRadius-medium);
+			background: conic-gradient(from var(--animation-angle),
+				color-mix(in srgb, #b44aff var(--animation-opacity), var(--vscode-browser-border, transparent)),
+				color-mix(in srgb, #4af0c0 var(--animation-opacity), var(--vscode-browser-border, transparent)),
+				color-mix(in srgb, #51a2ff var(--animation-opacity), var(--vscode-browser-border, transparent)),
+				color-mix(in srgb, #4af0c0 var(--animation-opacity), var(--vscode-browser-border, transparent)),
+				color-mix(in srgb, #b44aff var(--animation-opacity), var(--vscode-browser-border, transparent))
+			);
+			pointer-events: none;
 		}
+
+		&.shared::before {
+			top: -3px;
+			left: -3px;
+			right: -3px;
+			bottom: -3px;
+			--animation-angle: 495deg;
+			--animation-opacity: 100%;
+		}
+
+		&.animate::before {
+			transition: top 350ms cubic-bezier(0.2, 0, 0, 1),
+				left 350ms cubic-bezier(0.2, 0, 0, 1),
+				right 350ms cubic-bezier(0.2, 0, 0, 1),
+				bottom 350ms cubic-bezier(0.2, 0, 0, 1),
+				--animation-opacity 350ms cubic-bezier(0.2, 0, 0, 1);
+		}
+
+		&.shared.animate::before {
+			animation: browser-shared-border-spin 1500ms cubic-bezier(0, 0.2, 0, 1) 1 forwards,
+				browser-shared-border-spin 45s linear 1500ms infinite;
+		}
+
+		&::after {
+			content: '';
+			position: absolute;
+			top: 1px;
+			left: 1px;
+			right: 1px;
+			bottom: 1px;
+			z-index: -1;
+			border-radius: var(--vscode-cornerRadius-medium);
+			background-color: var(--vscode-editor-background);
+			pointer-events: none;
+		}
+	}
+
+	.browser-placeholder-contents {
+		width: 100%;
+		height: 100%;
+		position: relative;
+		overflow: hidden;
+		border-radius: var(--vscode-cornerRadius-medium);
 	}
 
 	.browser-placeholder-screenshot {
@@ -180,7 +285,7 @@
 		border-radius: 4px;
 		border: 1px solid var(--vscode-editorWidget-border);
 		background-color: var(--vscode-editor-background);
-		box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+		box-shadow: var(--vscode-shadow-lg);
 		max-width: 80%;
 		text-align: center;
 		display: none;
@@ -269,8 +374,9 @@
 			border-radius: 0;
 			border: none;
 			top: 0 !important;
-			padding: 6px 8px 6px 12px;
+			padding: 2px 8px 6px 12px;
 			transition: none;
+			background: none !important;
 
 			&:not(.visible) {
 				display: none;
@@ -278,11 +384,13 @@
 
 			.monaco-sash {
 				width: 2px !important;
-				border-radius: 0;
+				height: calc(100% - 4px);
+				border-radius: var(--vscode-cornerRadius-circle);
 
 				&::before {
 					width: var(--vscode-sash-hover-size);
 					left: calc(50% - (var(--vscode-sash-hover-size) / 2));
+					border-radius: var(--vscode-cornerRadius-circle);
 				}
 			}
 
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/browserToolHelpers.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/browserToolHelpers.ts
index e6981287fe2f1..04e48f2bab5c1 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/tools/browserToolHelpers.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/browserToolHelpers.ts
@@ -9,6 +9,18 @@ import { IToolResult } from '../../../chat/common/tools/languageModelToolsServic
 // eslint-disable-next-line local/code-import-patterns
 import type { Page } from 'playwright-core';
 
+/**
+ * Shared helper for running a Playwright function against a page and returning its result.
+ */
+export async function playwrightInvokeRaw<TArgs extends unknown[], TReturn>(
+	playwrightService: IPlaywrightService,
+	pageId: string,
+	fn: (page: Page, ...args: TArgs) => Promise<TReturn>,
+	...args: TArgs
+): Promise<TReturn> {
+	return playwrightService.invokeFunctionRaw(pageId, fn.toString(), ...args);
+}
+
 /**
  * Shared helper for running a Playwright function against a page and returning
  * a tool result. Handles success/error formatting.
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/browserTools.contribution.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/browserTools.contribution.ts
index 340a48a10c1e9..b113304a284b5 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/tools/browserTools.contribution.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/browserTools.contribution.ts
@@ -12,14 +12,15 @@ import { IInstantiationService } from '../../../../../platform/instantiation/com
 import { registerWorkbenchContribution2, WorkbenchPhase, type IWorkbenchContribution } from '../../../../common/contributions.js';
 import { IEditorService } from '../../../../services/editor/common/editorService.js';
 import { IChatContextService } from '../../../chat/browser/contextContrib/chatContextService.js';
-import { ILanguageModelToolsService, ToolDataSource } from '../../../chat/common/tools/languageModelToolsService.js';
-import { BrowserEditorInput } from '../browserEditorInput.js';
+import { ILanguageModelToolsService, ToolDataSource, ToolSet } from '../../../chat/common/tools/languageModelToolsService.js';
+import { BrowserEditorInput } from '../../common/browserEditorInput.js';
 import { ClickBrowserTool, ClickBrowserToolData } from './clickBrowserTool.js';
 import { DragElementTool, DragElementToolData } from './dragElementTool.js';
 import { HandleDialogBrowserTool, HandleDialogBrowserToolData } from './handleDialogBrowserTool.js';
 import { HoverElementTool, HoverElementToolData } from './hoverElementTool.js';
 import { NavigateBrowserTool, NavigateBrowserToolData } from './navigateBrowserTool.js';
 import { OpenBrowserTool, OpenBrowserToolData } from './openBrowserTool.js';
+import { OpenBrowserToolNonAgentic, OpenBrowserToolNonAgenticData } from './openBrowserToolNonAgentic.js';
 import { ReadBrowserTool, ReadBrowserToolData } from './readBrowserTool.js';
 import { RunPlaywrightCodeTool, RunPlaywrightCodeToolData } from './runPlaywrightCodeTool.js';
 import { ScreenshotBrowserTool, ScreenshotBrowserToolData } from './screenshotBrowserTool.js';
@@ -31,6 +32,7 @@ class BrowserChatAgentToolsContribution extends Disposable implements IWorkbench
 	private static readonly CONTEXT_ID = 'browserView.trackedPages';
 
 	private readonly _toolsStore = this._register(new DisposableStore());
+	private readonly _browserToolSet: ToolSet;
 
 	private _trackedIds: ReadonlySet<string> = new Set();
 
@@ -44,6 +46,16 @@ class BrowserChatAgentToolsContribution extends Disposable implements IWorkbench
 	) {
 		super();
 
+		this._browserToolSet = this._register(this.toolsService.createToolSet(
+			ToolDataSource.Internal,
+			'browser',
+			'browser',
+			{
+				icon: Codicon.globe,
+				description: localize('browserToolSet.description', 'Open and interact with integrated browser pages'),
+			}
+		));
+
 		this._updateToolRegistrations();
 
 		this._register(configurationService.onDidChangeConfiguration(e => {
@@ -57,20 +69,14 @@ class BrowserChatAgentToolsContribution extends Disposable implements IWorkbench
 		this._toolsStore.clear();
 
 		if (!this.configurationService.getValue<boolean>('workbench.browser.enableChatTools')) {
+			// If chat tools are disabled, we only register the non-agentic open tool,
+			// which allows opening browser pages without granting access to their contents.
+			this._toolsStore.add(this.toolsService.registerTool(OpenBrowserToolNonAgenticData, this.instantiationService.createInstance(OpenBrowserToolNonAgentic)));
+			this._toolsStore.add(this._browserToolSet.addTool(OpenBrowserToolNonAgenticData));
 			this.chatContextService.updateWorkspaceContextItems(BrowserChatAgentToolsContribution.CONTEXT_ID, []);
 			return;
 		}
 
-		const browserToolSet = this._toolsStore.add(this.toolsService.createToolSet(
-			ToolDataSource.Internal,
-			'browser',
-			'browser',
-			{
-				icon: Codicon.globe,
-				description: localize('browserToolSet.description', 'Open and interact with integrated browser pages'),
-			}
-		));
-
 		this._toolsStore.add(this.toolsService.registerTool(OpenBrowserToolData, this.instantiationService.createInstance(OpenBrowserTool)));
 		this._toolsStore.add(this.toolsService.registerTool(ReadBrowserToolData, this.instantiationService.createInstance(ReadBrowserTool)));
 		this._toolsStore.add(this.toolsService.registerTool(ScreenshotBrowserToolData, this.instantiationService.createInstance(ScreenshotBrowserTool)));
@@ -82,16 +88,16 @@ class BrowserChatAgentToolsContribution extends Disposable implements IWorkbench
 		this._toolsStore.add(this.toolsService.registerTool(RunPlaywrightCodeToolData, this.instantiationService.createInstance(RunPlaywrightCodeTool)));
 		this._toolsStore.add(this.toolsService.registerTool(HandleDialogBrowserToolData, this.instantiationService.createInstance(HandleDialogBrowserTool)));
 
-		this._toolsStore.add(browserToolSet.addTool(OpenBrowserToolData));
-		this._toolsStore.add(browserToolSet.addTool(ReadBrowserToolData));
-		this._toolsStore.add(browserToolSet.addTool(ScreenshotBrowserToolData));
-		this._toolsStore.add(browserToolSet.addTool(NavigateBrowserToolData));
-		this._toolsStore.add(browserToolSet.addTool(ClickBrowserToolData));
-		this._toolsStore.add(browserToolSet.addTool(DragElementToolData));
-		this._toolsStore.add(browserToolSet.addTool(HoverElementToolData));
-		this._toolsStore.add(browserToolSet.addTool(TypeBrowserToolData));
-		this._toolsStore.add(browserToolSet.addTool(RunPlaywrightCodeToolData));
-		this._toolsStore.add(browserToolSet.addTool(HandleDialogBrowserToolData));
+		this._toolsStore.add(this._browserToolSet.addTool(OpenBrowserToolData));
+		this._toolsStore.add(this._browserToolSet.addTool(ReadBrowserToolData));
+		this._toolsStore.add(this._browserToolSet.addTool(ScreenshotBrowserToolData));
+		this._toolsStore.add(this._browserToolSet.addTool(NavigateBrowserToolData));
+		this._toolsStore.add(this._browserToolSet.addTool(ClickBrowserToolData));
+		this._toolsStore.add(this._browserToolSet.addTool(DragElementToolData));
+		this._toolsStore.add(this._browserToolSet.addTool(HoverElementToolData));
+		this._toolsStore.add(this._browserToolSet.addTool(TypeBrowserToolData));
+		this._toolsStore.add(this._browserToolSet.addTool(RunPlaywrightCodeToolData));
+		this._toolsStore.add(this._browserToolSet.addTool(HandleDialogBrowserToolData));
 
 		// Publish tracked browser pages as workspace context for chat requests
 		this.playwrightService.getTrackedPages().then(ids => {
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/clickBrowserTool.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/clickBrowserTool.ts
index bd911b192fada..aaa19f44e2577 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/tools/clickBrowserTool.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/clickBrowserTool.ts
@@ -24,7 +24,7 @@ export const ClickBrowserToolData: IToolData = {
 		properties: {
 			pageId: {
 				type: 'string',
-				description: `The browser page ID, acquired from context or ${OpenPageToolId}.`
+				description: `The browser page ID, acquired from context or the open tool.`
 			},
 			selector: {
 				type: 'string',
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/dragElementTool.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/dragElementTool.ts
index 15feb72f5ae86..b9288091fd568 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/tools/dragElementTool.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/dragElementTool.ts
@@ -24,7 +24,7 @@ export const DragElementToolData: IToolData = {
 		properties: {
 			pageId: {
 				type: 'string',
-				description: `The browser page ID, acquired from context or ${OpenPageToolId}.`
+				description: `The browser page ID, acquired from context or the open tool.`
 			},
 			fromSelector: {
 				type: 'string',
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/handleDialogBrowserTool.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/handleDialogBrowserTool.ts
index 34d8798bc72f9..6e118343190ed 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/tools/handleDialogBrowserTool.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/handleDialogBrowserTool.ts
@@ -16,7 +16,7 @@ export const HandleDialogBrowserToolData: IToolData = {
 	toolReferenceName: 'handleDialog',
 	displayName: localize('handleDialogBrowserTool.displayName', 'Handle Dialog'),
 	userDescription: localize('handleDialogBrowserTool.userDescription', 'Respond to a dialog in a browser page'),
-	modelDescription: 'Respond to a pending dialog (alert, confirm, prompt) or file chooser dialog on a browser page.',
+	modelDescription: 'Respond to a pending modal (alert, confirm, prompt) or file chooser dialog on a browser page.',
 	icon: Codicon.comment,
 	source: ToolDataSource.Internal,
 	inputSchema: {
@@ -24,31 +24,31 @@ export const HandleDialogBrowserToolData: IToolData = {
 		properties: {
 			pageId: {
 				type: 'string',
-				description: `The browser page ID, acquired from context or ${OpenPageToolId}.`
+				description: `The browser page ID, acquired from context or the open tool.`
 			},
-			accept: {
+			acceptModal: {
 				type: 'boolean',
-				description: 'Whether to accept (true) or dismiss (false) the dialog.'
+				description: 'Whether to accept (true) or dismiss (false) a modal dialog.'
 			},
 			promptText: {
 				type: 'string',
-				description: 'Text to enter into a prompt dialog. Only applicable for prompt dialogs.'
+				description: 'Text to enter into a prompt dialog.'
 			},
-			files: {
+			selectFiles: {
 				type: 'array',
 				items: { type: 'string' },
-				description: 'Absolute paths of files to select. Required for file chooser dialogs.'
+				description: 'Absolute paths of files to select, or empty to dismiss. Required for file chooser dialogs.'
 			},
 		},
-		required: ['pageId', 'accept'],
+		required: ['pageId'],
 	},
 };
 
 interface IHandleDialogBrowserToolParams {
 	pageId: string;
-	accept: boolean;
+	acceptModal: boolean;
 	promptText?: string;
-	files?: string[];
+	selectFiles?: string[];
 }
 
 export class HandleDialogBrowserTool implements IToolImpl {
@@ -70,12 +70,20 @@ export class HandleDialogBrowserTool implements IToolImpl {
 			return errorResult(`No page ID provided. Use '${OpenPageToolId}' first.`);
 		}
 
+		if (params.selectFiles !== undefined && (params.acceptModal !== undefined || params.promptText !== undefined)) {
+			return errorResult(`Invalid parameters. 'selectFiles' cannot be used with 'acceptModal' or 'promptText'.`);
+		}
+
+		if (!Array.isArray(params.selectFiles) && (params.acceptModal === undefined || params.acceptModal === null)) {
+			return errorResult(`Invalid parameters. Either 'selectFiles' or 'acceptModal' must be provided.`);
+		}
+
 		try {
 			let result;
-			if (params.files !== undefined) {
-				result = await this.playwrightService.replyToFileChooser(params.pageId, params.accept ? params.files : []);
+			if (params.selectFiles !== undefined) {
+				result = await this.playwrightService.replyToFileChooser(params.pageId, params.selectFiles);
 			} else {
-				result = await this.playwrightService.replyToDialog(params.pageId, params.accept, params.promptText);
+				result = await this.playwrightService.replyToDialog(params.pageId, params.acceptModal, params.promptText);
 			}
 			return { content: [{ kind: 'text', value: result.summary }] };
 		} catch (e) {
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/hoverElementTool.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/hoverElementTool.ts
index 16c3ed50c9ee6..46e4b65488de4 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/tools/hoverElementTool.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/hoverElementTool.ts
@@ -24,7 +24,7 @@ export const HoverElementToolData: IToolData = {
 		properties: {
 			pageId: {
 				type: 'string',
-				description: `The browser page ID, acquired from context or ${OpenPageToolId}.`
+				description: `The browser page ID, acquired from context or the open tool.`
 			},
 			selector: {
 				type: 'string',
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/navigateBrowserTool.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/navigateBrowserTool.ts
index dbad2b31af63f..aea84f61e5e25 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/tools/navigateBrowserTool.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/navigateBrowserTool.ts
@@ -24,7 +24,7 @@ export const NavigateBrowserToolData: IToolData = {
 		properties: {
 			pageId: {
 				type: 'string',
-				description: `The browser page ID to navigate, acquired from context or ${OpenPageToolId}.`
+				description: `The browser page ID to navigate, acquired from context or the open tool.`
 			},
 			type: {
 				type: 'string',
@@ -69,16 +69,25 @@ export class NavigateBrowserTool implements IToolImpl {
 					invocationMessage: localize('browser.goForward.invocation', "Going forward in browser history"),
 					pastTenseMessage: localize('browser.goForward.past', "Went forward in browser history"),
 				};
-			default:
+			default: {
+				if (!params.url) {
+					throw new Error('The "url" parameter is required when type is "url".');
+				}
+				const parsed = URL.parse(params.url);
+				if (!parsed) {
+					throw new Error('You must provide a complete, valid URL.');
+				}
+
 				return {
-					invocationMessage: localize('browser.navigate.invocation', "Navigating browser to {0}", params.url),
-					pastTenseMessage: localize('browser.navigate.past', "Navigated browser to {0}", params.url),
+					invocationMessage: localize('browser.navigate.invocation', "Navigating browser to {0}", parsed.href),
+					pastTenseMessage: localize('browser.navigate.past', "Navigated browser to {0}", parsed.href),
 					confirmationMessages: {
 						title: localize('browser.navigate.confirmTitle', 'Navigate Browser?'),
-						message: localize('browser.navigate.confirmMessage', 'This will navigate the browser to {0} and allow the agent to access its contents.', params.url),
+						message: localize('browser.navigate.confirmMessage', 'This will navigate the browser to {0} and allow the agent to access its contents.', parsed.href),
 						allowAutoConfirm: true,
 					},
 				};
+			}
 		}
 	}
 
@@ -97,12 +106,9 @@ export class NavigateBrowserTool implements IToolImpl {
 			case 'forward':
 				return playwrightInvoke(this.playwrightService, params.pageId, (page) => page.goForward({ waitUntil: 'domcontentloaded' }));
 			default: {
-				if (!params.url) {
-					return errorResult('The "url" parameter is required when type is "url".');
-				}
 				return playwrightInvoke(this.playwrightService, params.pageId, (page, url) => {
 					return page.goto(url, { waitUntil: 'domcontentloaded' });
-				}, params.url);
+				}, params.url!);
 			}
 		}
 	}
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/openBrowserTool.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/openBrowserTool.ts
index f0b215e0d5d97..97e764cda78ef 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/tools/openBrowserTool.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/openBrowserTool.ts
@@ -8,7 +8,6 @@ import { Codicon } from '../../../../../base/common/codicons.js';
 import { localize } from '../../../../../nls.js';
 import { IPlaywrightService } from '../../../../../platform/browserView/common/playwrightService.js';
 import { ToolDataSource, type CountTokensCallback, type IPreparedToolInvocation, type IToolData, type IToolImpl, type IToolInvocation, type IToolInvocationPreparationContext, type IToolResult, type ToolProgress } from '../../../chat/common/tools/languageModelToolsService.js';
-import { errorResult } from './browserToolHelpers.js';
 
 export const OpenPageToolId = 'open_browser_page';
 
@@ -25,14 +24,14 @@ export const OpenBrowserToolData: IToolData = {
 		properties: {
 			url: {
 				type: 'string',
-				description: 'The URL to open in the browser.'
+				description: 'The full URL to open in the browser.'
 			},
 		},
 		required: ['url'],
 	},
 };
 
-interface IOpenBrowserToolParams {
+export interface IOpenBrowserToolParams {
 	url: string;
 }
 
@@ -43,12 +42,21 @@ export class OpenBrowserTool implements IToolImpl {
 
 	async prepareToolInvocation(context: IToolInvocationPreparationContext, _token: CancellationToken): Promise<IPreparedToolInvocation | undefined> {
 		const params = context.parameters as IOpenBrowserToolParams;
+
+		if (!params.url) {
+			throw new Error('The "url" parameter is required.');
+		}
+		const parsed = URL.parse(params.url);
+		if (!parsed) {
+			throw new Error('You must provide a complete, valid URL.');
+		}
+
 		return {
-			invocationMessage: localize('browser.open.invocation', "Opening browser page at {0}", params.url ?? 'about:blank'),
-			pastTenseMessage: localize('browser.open.past', "Opened browser page at {0}", params.url ?? 'about:blank'),
+			invocationMessage: localize('browser.open.invocation', "Opening browser page at {0}", parsed.href),
+			pastTenseMessage: localize('browser.open.past', "Opened browser page at {0}", parsed.href),
 			confirmationMessages: {
 				title: localize('browser.open.confirmTitle', 'Open Browser Page?'),
-				message: localize('browser.open.confirmMessage', 'This will open {0} in the integrated browser. The agent will be able to read and interact with its contents.', params.url ?? 'about:blank'),
+				message: localize('browser.open.confirmMessage', 'This will open {0} in the integrated browser. The agent will be able to read and interact with its contents.', parsed.href),
 				allowAutoConfirm: true,
 			},
 		};
@@ -56,11 +64,6 @@ export class OpenBrowserTool implements IToolImpl {
 
 	async invoke(invocation: IToolInvocation, _countTokens: CountTokensCallback, _progress: ToolProgress, _token: CancellationToken): Promise<IToolResult> {
 		const params = invocation.parameters as IOpenBrowserToolParams;
-
-		if (!params.url) {
-			return errorResult('The "url" parameter is required.');
-		}
-
 		const { pageId, summary } = await this.playwrightService.openPage(params.url);
 
 		return {
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/openBrowserToolNonAgentic.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/openBrowserToolNonAgentic.ts
new file mode 100644
index 0000000000000..d9c819f7ca967
--- /dev/null
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/openBrowserToolNonAgentic.ts
@@ -0,0 +1,63 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import type { CancellationToken } from '../../../../../base/common/cancellation.js';
+import { localize } from '../../../../../nls.js';
+import { logBrowserOpen } from '../../../../../platform/browserView/common/browserViewTelemetry.js';
+import { BrowserViewUri } from '../../../../../platform/browserView/common/browserViewUri.js';
+import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
+import { IEditorService } from '../../../../services/editor/common/editorService.js';
+import { type CountTokensCallback, type IPreparedToolInvocation, type IToolData, type IToolImpl, type IToolInvocation, type IToolInvocationPreparationContext, type IToolResult, type ToolProgress } from '../../../chat/common/tools/languageModelToolsService.js';
+import { IOpenBrowserToolParams, OpenBrowserToolData } from './openBrowserTool.js';
+
+export const OpenBrowserToolNonAgenticData: IToolData = {
+	...OpenBrowserToolData,
+	modelDescription: 'Open a new browser page in the integrated browser at the given URL.',
+};
+
+export class OpenBrowserToolNonAgentic implements IToolImpl {
+	constructor(
+		@ITelemetryService private readonly telemetryService: ITelemetryService,
+		@IEditorService private readonly editorService: IEditorService,
+	) { }
+
+	async prepareToolInvocation(context: IToolInvocationPreparationContext, _token: CancellationToken): Promise<IPreparedToolInvocation | undefined> {
+		const params = context.parameters as IOpenBrowserToolParams;
+
+		if (!params.url) {
+			throw new Error('The "url" parameter is required.');
+		}
+		const parsed = URL.parse(params.url);
+		if (!parsed) {
+			throw new Error('You must provide a complete, valid URL.');
+		}
+
+		return {
+			invocationMessage: localize('browser.open.nonAgentic.invocation', "Opening browser page at {0}", parsed.href),
+			pastTenseMessage: localize('browser.open.nonAgentic.past', "Opened browser page at {0}", parsed.href),
+			confirmationMessages: {
+				title: localize('browser.open.nonAgentic.confirmTitle', 'Open Browser Page?'),
+				message: localize('browser.open.nonAgentic.confirmMessage', 'This will open {0} in the integrated browser. The agent will not be able to read its contents.', parsed.href),
+				allowAutoConfirm: true,
+			},
+		};
+	}
+
+	async invoke(invocation: IToolInvocation, _countTokens: CountTokensCallback, _progress: ToolProgress, _token: CancellationToken): Promise<IToolResult> {
+		const params = invocation.parameters as IOpenBrowserToolParams;
+
+		logBrowserOpen(this.telemetryService, 'chatTool');
+
+		const browserUri = BrowserViewUri.forUrl(params.url);
+		await this.editorService.openEditor({ resource: browserUri, options: { pinned: true } });
+
+		return {
+			content: [{
+				kind: 'text',
+				value: `Page opened successfully. Note that you do not have access to the page contents unless the user enables agentic tools via the \`workbench.browser.enableChatTools\` setting.`,
+			}]
+		};
+	}
+}
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/readBrowserTool.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/readBrowserTool.ts
index f7b379e926fdd..63aa66cc7075d 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/tools/readBrowserTool.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/readBrowserTool.ts
@@ -26,7 +26,7 @@ export const ReadBrowserToolData: IToolData = {
 		properties: {
 			pageId: {
 				type: 'string',
-				description: `The browser page ID to read, acquired from context or ${OpenPageToolId}.`
+				description: `The browser page ID to read, acquired from context or the open tool.`
 			},
 		},
 		required: ['pageId'],
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/runPlaywrightCodeTool.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/runPlaywrightCodeTool.ts
index 0e3d46a1b8adb..e07efe6265d93 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/tools/runPlaywrightCodeTool.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/runPlaywrightCodeTool.ts
@@ -25,7 +25,7 @@ export const RunPlaywrightCodeToolData: IToolData = {
 		properties: {
 			pageId: {
 				type: 'string',
-				description: `The browser page ID, acquired from context or ${OpenPageToolId}.`
+				description: `The browser page ID, acquired from context or the open tool.`
 			},
 			code: {
 				type: 'string',
@@ -97,6 +97,7 @@ export class RunPlaywrightCodeTool implements IToolImpl {
 			],
 			toolResultDetails: {
 				input: params.code.trim(),
+				inputLanguage: 'javascript',
 				output: result.result
 					? [{ type: 'embed', isText: true, value: JSON.stringify(result.result, null, 2) }]
 					: [],
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/screenshotBrowserTool.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/screenshotBrowserTool.ts
index e0664e36a32f4..b2bb1f9a3fed7 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/tools/screenshotBrowserTool.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/screenshotBrowserTool.ts
@@ -8,7 +8,8 @@ import { Codicon } from '../../../../../base/common/codicons.js';
 import { localize } from '../../../../../nls.js';
 import { IPlaywrightService } from '../../../../../platform/browserView/common/playwrightService.js';
 import { ToolDataSource, type CountTokensCallback, type IPreparedToolInvocation, type IToolData, type IToolImpl, type IToolInvocation, type IToolInvocationPreparationContext, type IToolResult, type ToolProgress } from '../../../chat/common/tools/languageModelToolsService.js';
-import { errorResult } from './browserToolHelpers.js';
+import { IBrowserViewWorkbenchService } from '../../common/browserView.js';
+import { errorResult, playwrightInvokeRaw } from './browserToolHelpers.js';
 import { OpenPageToolId } from './openBrowserTool.js';
 import { ReadBrowserToolData } from './readBrowserTool.js';
 
@@ -25,20 +26,20 @@ export const ScreenshotBrowserToolData: IToolData = {
 		properties: {
 			pageId: {
 				type: 'string',
-				description: `The browser page ID to capture, acquired from context or ${OpenPageToolId}.`
+				description: `The browser page ID to capture, acquired from context or the open tool.`
 			},
 			selector: {
 				type: 'string',
-				description: 'Playwright selector of an element to capture. If omitted, captures the whole page.'
+				description: 'Playwright selector of an element to capture. If omitted, captures the whole viewport.'
 			},
 			ref: {
 				type: 'string',
-				description: 'Element reference to capture. If omitted, captures the whole page.'
+				description: 'Element reference to capture. If omitted, captures the whole viewport.'
 			},
-			fullPage: {
+			scrollIntoViewIfNeeded: {
 				type: 'boolean',
-				description: 'Set to true to capture the full scrollable page instead of just the viewport. Incompatible with selector/ref.'
-			},
+				description: 'Whether to scroll the element into view before capturing. Defaults to false.',
+			}
 		},
 		required: ['pageId'],
 	},
@@ -48,11 +49,12 @@ interface IScreenshotBrowserToolParams {
 	pageId: string;
 	selector?: string;
 	ref?: string;
-	fullPage?: boolean;
+	scrollIntoViewIfNeeded?: boolean;
 }
 
 export class ScreenshotBrowserTool implements IToolImpl {
 	constructor(
+		@IBrowserViewWorkbenchService private readonly browserViewWorkbenchService: IBrowserViewWorkbenchService,
 		@IPlaywrightService private readonly playwrightService: IPlaywrightService,
 	) { }
 
@@ -75,7 +77,24 @@ export class ScreenshotBrowserTool implements IToolImpl {
 			selector = `aria-ref=${params.ref}`;
 		}
 
-		const screenshot = await this.playwrightService.captureScreenshot(params.pageId, selector, params.fullPage);
+		// Note that we don't use Playwright's screenshot methods because they cause brief flashing on the page,
+		// and also doesn't handle zooming well.
+		const browserViewModel = await this.browserViewWorkbenchService.getBrowserViewModel(params.pageId); // Throws if the given pageId doesn't exist
+		const bounds = selector && await playwrightInvokeRaw(this.playwrightService, params.pageId, async (page, selector, scrollIntoViewIfNeeded) => {
+			const locator = page.locator(selector);
+			if (scrollIntoViewIfNeeded) {
+				await locator.scrollIntoViewIfNeeded();
+			}
+			return locator.boundingBox();
+		}, selector, params.scrollIntoViewIfNeeded) || undefined;
+		const zoomFactor = browserViewModel.zoomFactor;
+		if (bounds) {
+			bounds.x *= zoomFactor;
+			bounds.y *= zoomFactor;
+			bounds.width *= zoomFactor;
+			bounds.height *= zoomFactor;
+		}
+		const screenshot = await browserViewModel.captureScreenshot({ rect: bounds });
 
 		return {
 			content: [
diff --git a/src/vs/workbench/contrib/browserView/electron-browser/tools/typeBrowserTool.ts b/src/vs/workbench/contrib/browserView/electron-browser/tools/typeBrowserTool.ts
index a6e156e91a5ef..c3e8300c1b06b 100644
--- a/src/vs/workbench/contrib/browserView/electron-browser/tools/typeBrowserTool.ts
+++ b/src/vs/workbench/contrib/browserView/electron-browser/tools/typeBrowserTool.ts
@@ -24,7 +24,7 @@ export const TypeBrowserToolData: IToolData = {
 		properties: {
 			pageId: {
 				type: 'string',
-				description: `The browser page ID, acquired from context or ${OpenPageToolId}.`
+				description: `The browser page ID, acquired from context or the open tool.`
 			},
 			text: {
 				type: 'string',
diff --git a/src/vs/workbench/contrib/chat/browser/accessibility/chatAccessibilityProvider.ts b/src/vs/workbench/contrib/chat/browser/accessibility/chatAccessibilityProvider.ts
index 90397262b5d92..5b9b0e488d7d2 100644
--- a/src/vs/workbench/contrib/chat/browser/accessibility/chatAccessibilityProvider.ts
+++ b/src/vs/workbench/contrib/chat/browser/accessibility/chatAccessibilityProvider.ts
@@ -54,6 +54,8 @@ export const getToolConfirmationAlert = (accessor: ServicesAccessor, toolInvocat
 				input = JSON.stringify(v.toolSpecificData.extensions);
 			} else if (v.toolSpecificData.kind === 'input') {
 				input = JSON.stringify(v.toolSpecificData.rawInput);
+			} else if (v.toolSpecificData.kind === 'modifiedFilesConfirmation') {
+				input = localize('modifiedFilesConfirmationInput', '{0} files', v.toolSpecificData.modifiedFiles.length);
 			}
 		}
 		const titleObj = state.confirmationMessages?.title;
diff --git a/src/vs/workbench/contrib/chat/browser/accessibility/chatResponseAccessibleView.ts b/src/vs/workbench/contrib/chat/browser/accessibility/chatResponseAccessibleView.ts
index 6cad0431d35bf..f20aabab9961d 100644
--- a/src/vs/workbench/contrib/chat/browser/accessibility/chatResponseAccessibleView.ts
+++ b/src/vs/workbench/contrib/chat/browser/accessibility/chatResponseAccessibleView.ts
@@ -17,7 +17,7 @@ import { IStorageService, StorageScope } from '../../../../../platform/storage/c
 import { AccessibilityVerbositySettingId } from '../../../accessibility/browser/accessibilityConfiguration.js';
 import { migrateLegacyTerminalToolSpecificData } from '../../common/chat.js';
 import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
-import { IChatExtensionsContent, IChatPullRequestContent, IChatSimpleToolInvocationData, IChatSubagentToolInvocationData, IChatTerminalToolInvocationData, IChatTodoListContent, IChatToolInputInvocationData, IChatToolInvocation, IChatToolResourcesInvocationData, ILegacyChatTerminalToolInvocationData, IToolResultOutputDetailsSerialized, isLegacyChatTerminalToolInvocationData } from '../../common/chatService/chatService.js';
+import { IChatExtensionsContent, IChatModifiedFilesConfirmationData, IChatPullRequestContent, IChatSimpleToolInvocationData, IChatSubagentToolInvocationData, IChatTerminalToolInvocationData, IChatTodoListContent, IChatToolInputInvocationData, IChatToolInvocation, IChatToolResourcesInvocationData, ILegacyChatTerminalToolInvocationData, IToolResultOutputDetailsSerialized, isLegacyChatTerminalToolInvocationData } from '../../common/chatService/chatService.js';
 import { isResponseVM } from '../../common/model/chatViewModel.js';
 import { IToolResultInputOutputDetails, IToolResultOutputDetails, isToolResultInputOutputDetails, isToolResultOutputDetails, toolContentToA11yString } from '../../common/tools/languageModelToolsService.js';
 import { ChatTreeItem, IChatWidget, IChatWidgetService } from '../chat.js';
@@ -59,7 +59,7 @@ export class ChatResponseAccessibleView implements IAccessibleViewImplementation
 	}
 }
 
-type ToolSpecificData = IChatTerminalToolInvocationData | ILegacyChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatPullRequestContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatSimpleToolInvocationData | IChatToolResourcesInvocationData;
+type ToolSpecificData = IChatTerminalToolInvocationData | ILegacyChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatPullRequestContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatSimpleToolInvocationData | IChatToolResourcesInvocationData | IChatModifiedFilesConfirmationData;
 type ResultDetails = Array<URI | Location> | IToolResultInputOutputDetails | IToolResultOutputDetails | IToolResultOutputDetailsSerialized;
 
 export const CHAT_ACCESSIBLE_VIEW_INCLUDE_THINKING_STORAGE_KEY = 'chat.accessibleView.includeThinking';
@@ -141,6 +141,16 @@ export function getToolSpecificDataDescription(toolSpecificData: ToolSpecificDat
 			const outputText = toolSpecificData.output;
 			return localize('simpleToolInvocation', "Input: {0}, Output: {1}", inputText, outputText);
 		}
+		case 'modifiedFilesConfirmation': {
+			if (toolSpecificData.modifiedFiles.length === 0) {
+				return '';
+			}
+
+			return localize('modifiedFilesConfirmation', "Modified files: {0}", toolSpecificData.modifiedFiles.map(file => {
+				const revivedUri = URI.revive(file.uri);
+				return revivedUri.fsPath || revivedUri.path;
+			}).join(', '));
+		}
 		default:
 			return '';
 	}
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatAccessibilityHelp.ts b/src/vs/workbench/contrib/chat/browser/actions/chatAccessibilityHelp.ts
index a2a71e17376aa..b21a1e21048d5 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatAccessibilityHelp.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatAccessibilityHelp.ts
@@ -115,6 +115,7 @@ export function getAccessibilityHelpText(type: 'panelChat' | 'inlineChat' | 'age
 		}
 		content.push(localize('chatEditing.helpfulCommands', 'Some helpful commands include:'));
 		content.push(localize('workbench.action.chat.undoEdits', '- Undo Edits{0}.', '<keybinding:workbench.action.chat.undoEdits>'));
+		content.push(localize('workbench.action.chat.restoreLastCheckpoint', '- Restore to Last Checkpoint{0}.', '<keybinding:workbench.action.chat.restoreLastCheckpoint>'));
 		content.push(localize('workbench.action.chat.editing.attachFiles', '- Attach Files{0}.', '<keybinding:workbench.action.chat.editing.attachFiles>'));
 		content.push(localize('chatEditing.removeFileFromWorkingSet', '- Remove File from Working Set{0}.', '<keybinding:chatEditing.removeFileFromWorkingSet>'));
 		content.push(localize('chatEditing.acceptFile', '- Keep{0} and Undo File{1}.', '<keybinding:chatEditing.acceptFile>', '<keybinding:chatEditing.discardFile>'));
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatActions.ts b/src/vs/workbench/contrib/chat/browser/actions/chatActions.ts
index 4903908dd4997..19984144472e4 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatActions.ts
@@ -55,7 +55,7 @@ import { ElicitationState, IChatService, IChatToolInvocation } from '../../commo
 import { ISCMHistoryItemChangeRangeVariableEntry, ISCMHistoryItemChangeVariableEntry } from '../../common/attachments/chatVariableEntries.js';
 import { IChatRequestViewModel, IChatResponseViewModel, isRequestVM } from '../../common/model/chatViewModel.js';
 import { IChatWidgetHistoryService } from '../../common/widget/chatWidgetHistoryService.js';
-import { AgentsControlClickBehavior, ChatAgentLocation, ChatConfiguration, ChatModeKind } from '../../common/constants.js';
+import { ChatAgentLocation, ChatConfiguration, ChatModeKind } from '../../common/constants.js';
 import { ILanguageModelChatSelector, ILanguageModelsService } from '../../common/languageModels.js';
 import { CopilotUsageExtensionFeatureId } from '../../common/languageModelStats.js';
 import { ILanguageModelToolsConfirmationService } from '../../common/tools/languageModelToolsConfirmationService.js';
@@ -79,12 +79,14 @@ export const CHAT_SETUP_ACTION_ID = 'workbench.action.chat.triggerSetup';
 export const CHAT_SETUP_SUPPORT_ANONYMOUS_ACTION_ID = 'workbench.action.chat.triggerSetupSupportAnonymousAction';
 const TOGGLE_CHAT_ACTION_ID = 'workbench.action.chat.toggle';
 
-export const GENERATE_INSTRUCTIONS_COMMAND_ID = 'workbench.action.chat.generateInstructions';
-export const GENERATE_INSTRUCTION_COMMAND_ID = 'workbench.action.chat.generateInstruction';
+export const GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID = 'workbench.action.chat.generateAgentInstructions';
+export const GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID = 'workbench.action.chat.generateOnDemandInstructions';
 export const GENERATE_PROMPT_COMMAND_ID = 'workbench.action.chat.generatePrompt';
 export const GENERATE_SKILL_COMMAND_ID = 'workbench.action.chat.generateSkill';
 export const GENERATE_AGENT_COMMAND_ID = 'workbench.action.chat.generateAgent';
 export const GENERATE_HOOK_COMMAND_ID = 'workbench.action.chat.generateHook';
+export const INSERT_FORK_CONVERSATION_COMMAND_ID = 'workbench.action.chat.insertForkConversationCommand';
+export const INSERT_TROUBLESHOOT_COMMAND_ID = 'workbench.action.chat.insertTroubleshootCommand';
 
 const defaultChat = {
 	manageSettingsUrl: product.defaultChatAgent?.manageSettingsUrl ?? '',
@@ -367,6 +369,7 @@ abstract class OpenChatGlobalAction extends Action2 {
 		if (opts?.query) {
 
 			if (opts.isPartialQuery) {
+				chatWidget.input.showScrollbarUntilAccept();
 				chatWidget.setInput(opts.query);
 			} else {
 				if (!chatWidget.viewModel) {
@@ -600,36 +603,14 @@ export function registerChatActions() {
 			const viewsService = accessor.get(IViewsService);
 			const viewDescriptorService = accessor.get(IViewDescriptorService);
 			const widgetService = accessor.get(IChatWidgetService);
-			const configurationService = accessor.get(IConfigurationService);
 
 			const chatLocation = viewDescriptorService.getViewLocationById(ChatViewId);
 			const chatVisible = viewsService.isViewVisible(ChatViewId);
-			const clickBehavior = configurationService.getValue<AgentsControlClickBehavior>(ChatConfiguration.AgentsControlClickBehavior);
-			switch (clickBehavior) {
-				case AgentsControlClickBehavior.Cycle:
-					if (chatVisible) {
-						if (
-							chatLocation === ViewContainerLocation.AuxiliaryBar &&
-							!layoutService.isAuxiliaryBarMaximized()
-						) {
-							layoutService.setAuxiliaryBarMaximized(true);
-							(await widgetService.revealWidget())?.focusInput();
-						} else {
-							this.updatePartVisibility(layoutService, chatLocation, false);
-						}
-					} else {
-						this.updatePartVisibility(layoutService, chatLocation, true);
-						(await widgetService.revealWidget())?.focusInput();
-					}
-					break;
-				default:
-					if (chatVisible) {
-						this.updatePartVisibility(layoutService, chatLocation, false);
-					} else {
-						this.updatePartVisibility(layoutService, chatLocation, true);
-						(await widgetService.revealWidget())?.focusInput();
-					}
-					break;
+			if (chatVisible) {
+				this.updatePartVisibility(layoutService, chatLocation, false);
+			} else {
+				this.updatePartVisibility(layoutService, chatLocation, true);
+				(await widgetService.revealWidget())?.focusInput();
 			}
 		}
 
@@ -679,7 +660,79 @@ export function registerChatActions() {
 				}, {
 					id: MenuId.EditorTitle,
 					group: 'navigation',
-					when: ActiveEditorContext.isEqualTo(ChatEditorInput.EditorID),
+					when: ContextKeyExpr.and(ActiveEditorContext.isEqualTo(ChatEditorInput.EditorID), ChatContextKeys.newChatButtonExperimentIcon.notEqualsTo('copilot'), ChatContextKeys.newChatButtonExperimentIcon.notEqualsTo('new-session'), ChatContextKeys.newChatButtonExperimentIcon.notEqualsTo('comment')),
+					order: 1
+				}],
+			});
+		}
+
+		async run(accessor: ServicesAccessor) {
+			const widgetService = accessor.get(IChatWidgetService);
+			await widgetService.openSession(LocalChatSessionUri.getNewSessionUri(), ACTIVE_GROUP, { pinned: true } satisfies IChatEditorOptions);
+		}
+	});
+
+	registerAction2(class NewChatEditorCopilotIconAction extends Action2 {
+		constructor() {
+			super({
+				id: ACTION_ID_OPEN_CHAT + '.copilotIcon',
+				title: localize2('interactiveSession.open', "New Chat Editor"),
+				icon: Codicon.copilot,
+				f1: false,
+				category: CHAT_CATEGORY,
+				precondition: ChatContextKeys.enabled,
+				menu: [{
+					id: MenuId.EditorTitle,
+					group: 'navigation',
+					when: ContextKeyExpr.and(ActiveEditorContext.isEqualTo(ChatEditorInput.EditorID), ChatContextKeys.newChatButtonExperimentIcon.isEqualTo('copilot')),
+					order: 1
+				}],
+			});
+		}
+
+		async run(accessor: ServicesAccessor) {
+			const widgetService = accessor.get(IChatWidgetService);
+			await widgetService.openSession(LocalChatSessionUri.getNewSessionUri(), ACTIVE_GROUP, { pinned: true } satisfies IChatEditorOptions);
+		}
+	});
+
+	registerAction2(class NewChatEditorNewSessionIconAction extends Action2 {
+		constructor() {
+			super({
+				id: ACTION_ID_OPEN_CHAT + '.newSessionIcon',
+				title: localize2('interactiveSession.open', "New Chat Editor"),
+				icon: Codicon.newSession,
+				f1: false,
+				category: CHAT_CATEGORY,
+				precondition: ChatContextKeys.enabled,
+				menu: [{
+					id: MenuId.EditorTitle,
+					group: 'navigation',
+					when: ContextKeyExpr.and(ActiveEditorContext.isEqualTo(ChatEditorInput.EditorID), ChatContextKeys.newChatButtonExperimentIcon.isEqualTo('new-session')),
+					order: 1
+				}],
+			});
+		}
+
+		async run(accessor: ServicesAccessor) {
+			const widgetService = accessor.get(IChatWidgetService);
+			await widgetService.openSession(LocalChatSessionUri.getNewSessionUri(), ACTIVE_GROUP, { pinned: true } satisfies IChatEditorOptions);
+		}
+	});
+
+	registerAction2(class NewChatEditorCommentIconAction extends Action2 {
+		constructor() {
+			super({
+				id: ACTION_ID_OPEN_CHAT + '.commentIcon',
+				title: localize2('interactiveSession.open', "New Chat Editor"),
+				icon: Codicon.comment,
+				f1: false,
+				category: CHAT_CATEGORY,
+				precondition: ChatContextKeys.enabled,
+				menu: [{
+					id: MenuId.EditorTitle,
+					group: 'navigation',
+					when: ContextKeyExpr.and(ActiveEditorContext.isEqualTo(ChatEditorInput.EditorID), ChatContextKeys.newChatButtonExperimentIcon.isEqualTo('comment')),
 					order: 1
 				}],
 			});
@@ -1187,9 +1240,8 @@ export function registerChatActions() {
 	registerAction2(class GenerateInstructionsAction extends Action2 {
 		constructor() {
 			super({
-				id: GENERATE_INSTRUCTIONS_COMMAND_ID,
-				title: localize2('generateInstructions', "Generate Workspace Instructions with Agent"),
-				shortTitle: localize2('generateInstructions.short', "Generate Instructions with Agent"),
+				id: GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID,
+				title: localize2('generateInstructions', "Generate Agent Instructions"),
 				category: CHAT_CATEGORY,
 				icon: Codicon.sparkle,
 				f1: true,
@@ -1210,9 +1262,8 @@ export function registerChatActions() {
 	registerAction2(class GenerateInstructionAction extends Action2 {
 		constructor() {
 			super({
-				id: GENERATE_INSTRUCTION_COMMAND_ID,
-				title: localize2('generateInstruction', "Generate On-demand Instruction with Agent"),
-				shortTitle: localize2('generateInstruction.short', "Generate Instruction with Agent"),
+				id: GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID,
+				title: localize2('generateOnDemandInstructions', "Generate On-Demand Instructions"),
 				category: CHAT_CATEGORY,
 				icon: Codicon.sparkle,
 				f1: true,
@@ -1224,7 +1275,7 @@ export function registerChatActions() {
 			const commandService = accessor.get(ICommandService);
 			await commandService.executeCommand('workbench.action.chat.open', {
 				mode: 'agent',
-				query: '/create-instruction ',
+				query: '/create-instructions ',
 				isPartialQuery: true,
 			});
 		}
@@ -1234,8 +1285,8 @@ export function registerChatActions() {
 		constructor() {
 			super({
 				id: GENERATE_PROMPT_COMMAND_ID,
-				title: localize2('generatePrompt', "Generate Prompt File with Agent"),
-				shortTitle: localize2('generatePrompt.short', "Generate Prompt with Agent"),
+				title: localize2('generatePrompt', "Generate Prompt File"),
+				shortTitle: localize2('generatePrompt.short', "Generate Prompt"),
 				category: CHAT_CATEGORY,
 				icon: Codicon.sparkle,
 				f1: true,
@@ -1257,8 +1308,8 @@ export function registerChatActions() {
 		constructor() {
 			super({
 				id: GENERATE_SKILL_COMMAND_ID,
-				title: localize2('generateSkill', "Generate Skill with Agent"),
-				shortTitle: localize2('generateSkill.short', "Generate Skill with Agent"),
+				title: localize2('generateSkill', "Generate Skill"),
+				shortTitle: localize2('generateSkill.short', "Generate Skill"),
 				category: CHAT_CATEGORY,
 				icon: Codicon.sparkle,
 				f1: true,
@@ -1280,8 +1331,8 @@ export function registerChatActions() {
 		constructor() {
 			super({
 				id: GENERATE_AGENT_COMMAND_ID,
-				title: localize2('generateAgent', "Generate Custom Agent with Agent"),
-				shortTitle: localize2('generateAgent.short', "Generate Agent with Agent"),
+				title: localize2('generateAgent', "Generate Custom Agent"),
+				shortTitle: localize2('generateAgent.short', "Generate Agent"),
 				category: CHAT_CATEGORY,
 				icon: Codicon.sparkle,
 				f1: true,
@@ -1303,8 +1354,8 @@ export function registerChatActions() {
 		constructor() {
 			super({
 				id: GENERATE_HOOK_COMMAND_ID,
-				title: localize2('generateHook', "Generate Hook with Agent"),
-				shortTitle: localize2('generateHook.short', "Generate Hook with Agent"),
+				title: localize2('generateHook', "Generate Hook"),
+				shortTitle: localize2('generateHook.short', "Generate Hook"),
 				category: CHAT_CATEGORY,
 				icon: Codicon.sparkle,
 				f1: true,
@@ -1322,6 +1373,49 @@ export function registerChatActions() {
 		}
 	});
 
+	registerAction2(class InsertForkConversationSlashCommandAction extends Action2 {
+		constructor() {
+			super({
+				id: INSERT_FORK_CONVERSATION_COMMAND_ID,
+				title: localize2('insertForkConversationSlashCommand', "Insert Fork Command"),
+				shortTitle: localize2('insertForkConversationSlashCommand.short', "Insert /fork"),
+				category: CHAT_CATEGORY,
+				icon: Codicon.repoForked,
+				f1: true,
+				precondition: ChatContextKeys.enabled
+			});
+		}
+
+		async run(accessor: ServicesAccessor): Promise<void> {
+			const commandService = accessor.get(ICommandService);
+			await commandService.executeCommand('workbench.action.chat.open', {
+				query: '/fork ',
+				isPartialQuery: true,
+			});
+		}
+	});
+
+	registerAction2(class InsertTroubleshootSlashCommandAction extends Action2 {
+		constructor() {
+			super({
+				id: INSERT_TROUBLESHOOT_COMMAND_ID,
+				title: localize2('insertTroubleshootSlashCommand', "Insert Troubleshoot Command"),
+				shortTitle: localize2('insertTroubleshootSlashCommand.short', "Insert /troubleshoot"),
+				category: CHAT_CATEGORY,
+				f1: true,
+				precondition: ChatContextKeys.enabled
+			});
+		}
+
+		async run(accessor: ServicesAccessor): Promise<void> {
+			const commandService = accessor.get(ICommandService);
+			await commandService.executeCommand('workbench.action.chat.open', {
+				query: '/troubleshoot ',
+				isPartialQuery: true,
+			});
+		}
+	});
+
 	registerAction2(class OpenChatFeatureSettingsAction extends Action2 {
 		constructor() {
 			super({
@@ -1552,11 +1646,10 @@ export async function handleModeSwitch(
 		return { needToClearSession: false };
 	}
 
-	const configurationService = accessor.get(IConfigurationService);
 	const dialogService = accessor.get(IDialogService);
-	const needToClearEdits = (!configurationService.getValue(ChatConfiguration.Edits2Enabled) && (fromMode === ChatModeKind.Edit || toMode === ChatModeKind.Edit)) && requestCount > 0;
+	const needToClearEdits = (fromMode === ChatModeKind.Edit || toMode === ChatModeKind.Edit) && requestCount > 0;
 	if (needToClearEdits) {
-		// If not using edits2 and switching into or out of edit mode, ask to discard the session
+		// Switching into or out of edit mode, ask to discard the session
 		const phrase = localize('switchMode.confirmPhrase', "Switching agents will end your current edit session.");
 
 		const currentEdits = model.editingSession.entries.get();
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatContext.ts b/src/vs/workbench/contrib/chat/browser/actions/chatContext.ts
index fb17967129bef..e4aeffebcaf0a 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatContext.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatContext.ts
@@ -21,15 +21,26 @@ import { FileEditorInput } from '../../../files/browser/editors/fileEditorInput.
 import { NotebookEditorInput } from '../../../notebook/common/notebookEditorInput.js';
 import { IChatContextPickService, IChatContextValueItem, IChatContextPickerItem, IChatContextPickerPickItem, IChatContextPicker } from '../attachments/chatContextPickService.js';
 import { IChatRequestToolEntry, IChatRequestToolSetEntry, IChatRequestVariableEntry, IImageVariableEntry, toToolSetVariableEntry, toToolVariableEntry } from '../../common/attachments/chatVariableEntries.js';
-import { isToolSet, ToolDataSource } from '../../common/tools/languageModelToolsService.js';
-import { IChatWidget } from '../chat.js';
+import { ILanguageModelToolsService, isToolSet, ToolDataSource } from '../../common/tools/languageModelToolsService.js';
+import { IChatWidget, IChatWidgetService } from '../chat.js';
 import { imageToHash, isImage } from '../widget/input/editor/chatPasteProviders.js';
 import { convertBufferToScreenshotVariable } from '../attachments/chatScreenshotContext.js';
 import { ChatInstructionsPickerPick } from '../promptSyntax/attachInstructionsAction.js';
+import { createDebugEventsAttachment } from '../chatDebug/chatDebugAttachment.js';
+import { IChatDebugService } from '../../common/chatDebugService.js';
+import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
+import { IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
 import { ITerminalService } from '../../../terminal/browser/terminal.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { ITerminalCommand, TerminalCapability } from '../../../../../platform/terminal/common/capabilities/capabilities.js';
+import { CommandsRegistry } from '../../../../../platform/commands/common/commands.js';
 
+/**
+ * Command ID that extensions can call to enable debug tools for the current
+ * chat session. Sets the context key and immediately flushes tool updates so
+ * that newly-enabled tools are visible on the next `vscode.lm.tools` read.
+ */
+export const EnableChatDebugToolsCommandId = 'chat.enableDebugTools';
 
 export class ChatContextContributions extends Disposable implements IWorkbenchContribution {
 
@@ -38,9 +49,37 @@ export class ChatContextContributions extends Disposable implements IWorkbenchCo
 	constructor(
 		@IInstantiationService instantiationService: IInstantiationService,
 		@IChatContextPickService contextPickService: IChatContextPickService,
+		@IChatDebugService chatDebugService: IChatDebugService,
+		@IContextKeyService contextKeyService: IContextKeyService,
+		@ILanguageModelToolsService languageModelToolsService: ILanguageModelToolsService,
+		@IChatWidgetService chatWidgetService: IChatWidgetService,
 	) {
 		super();
 
+		// Bind at the global context key service level so the tools service can evaluate it.
+		// Widget-scoped keys are not reliably visible to singleton services during async request processing.
+		const hasDebugToolsKey = ChatContextKeys.chatSessionHasDebugTools.bindTo(contextKeyService);
+		this._store.add(chatWidgetService.onDidChangeFocusedSession(() => {
+			const sessionResource = chatWidgetService.lastFocusedWidget?.viewModel?.sessionResource;
+			hasDebugToolsKey.set(!!sessionResource && chatDebugService.hasAttachedDebugData(sessionResource));
+			languageModelToolsService.flushToolUpdates();
+		}));
+		this._store.add(chatDebugService.onDidAttachDebugData(sessionResource => {
+			const focusedSession = chatWidgetService.lastFocusedWidget?.viewModel?.sessionResource;
+			if (focusedSession && focusedSession.toString() === sessionResource.toString()) {
+				hasDebugToolsKey.set(true);
+				languageModelToolsService.flushToolUpdates();
+			}
+		}));
+
+		// Register a command that extensions can call to enable debug tools
+		// for the current session. This sets the context key AND flushes the
+		// tools service synchronously so the change is visible immediately.
+		this._store.add(CommandsRegistry.registerCommand(EnableChatDebugToolsCommandId, () => {
+			hasDebugToolsKey.set(true);
+			languageModelToolsService.flushToolUpdates();
+		}));
+
 		// ###############################################################################################
 		//
 		// Default context picks/values which are "native" to chat. This is NOT the complete list
@@ -54,6 +93,7 @@ export class ChatContextContributions extends Disposable implements IWorkbenchCo
 		this._store.add(contextPickService.registerChatContextItem(instantiationService.createInstance(OpenEditorContextValuePick)));
 		this._store.add(contextPickService.registerChatContextItem(instantiationService.createInstance(ClipboardImageContextValuePick)));
 		this._store.add(contextPickService.registerChatContextItem(instantiationService.createInstance(ScreenshotContextValuePick)));
+		this._store.add(contextPickService.registerChatContextItem(instantiationService.createInstance(DebugEventsSnapshotContextValuePick)));
 	}
 }
 
@@ -285,3 +325,28 @@ class ScreenshotContextValuePick implements IChatContextValueItem {
 		return blob && convertBufferToScreenshotVariable(blob);
 	}
 }
+
+class DebugEventsSnapshotContextValuePick implements IChatContextValueItem {
+
+	readonly type = 'valuePick';
+	readonly icon = Codicon.output;
+	readonly label = localize('chatContext.debugEventsSnapshot', 'Debug Events Snapshot');
+	readonly ordinal = -600;
+
+	constructor(
+		@IChatDebugService private readonly _chatDebugService: IChatDebugService,
+	) { }
+
+	isEnabled(widget: IChatWidget): boolean {
+		const sessionResource = widget.viewModel?.sessionResource;
+		return !!sessionResource && this._chatDebugService.getEvents(sessionResource).length > 0;
+	}
+
+	async asAttachment(widget: IChatWidget): Promise<IChatRequestVariableEntry | undefined> {
+		const sessionResource = widget.viewModel?.sessionResource;
+		if (!sessionResource) {
+			return undefined;
+		}
+		return createDebugEventsAttachment(sessionResource, this._chatDebugService);
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatContinueInAction.ts b/src/vs/workbench/contrib/chat/browser/actions/chatContinueInAction.ts
index f5d589353f4e6..90c35553eb1f1 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatContinueInAction.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatContinueInAction.ts
@@ -7,6 +7,7 @@ import { Codicon } from '../../../../../base/common/codicons.js';
 import { h } from '../../../../../base/browser/dom.js';
 import { Disposable, IDisposable, markAsSingleton } from '../../../../../base/common/lifecycle.js';
 import { Schemas } from '../../../../../base/common/network.js';
+import { isAbsolute } from '../../../../../base/common/path.js';
 import { basename } from '../../../../../base/common/resources.js';
 import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { URI } from '../../../../../base/common/uri.js';
@@ -25,23 +26,85 @@ import { IKeybindingService } from '../../../../../platform/keybinding/common/ke
 import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
 import { IOpenerService } from '../../../../../platform/opener/common/opener.js';
 import { IWorkbenchContribution } from '../../../../common/contributions.js';
-import { ResourceContextKey } from '../../../../common/contextkeys.js';
+import { IsSessionsWindowContext, ResourceContextKey } from '../../../../common/contextkeys.js';
 import { IEditorService } from '../../../../services/editor/common/editorService.js';
+import { IFileService } from '../../../../../platform/files/common/files.js';
 import { IChatAgentService } from '../../common/participants/chatAgents.js';
 import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
 import { chatEditingWidgetFileStateContextKey, ModifiedFileEntryState } from '../../common/editing/chatEditingService.js';
 import { ChatModel } from '../../common/model/chatModel.js';
 import { ChatRequestParser } from '../../common/requestParser/chatRequestParser.js';
+import { getDynamicVariablesForWidget, getSelectedToolAndToolSetsForWidget } from '../attachments/chatVariables.js';
 import { ChatSendResult, IChatService } from '../../common/chatService/chatService.js';
-import { IChatSessionsExtensionPoint, IChatSessionsService } from '../../common/chatSessionsService.js';
+import { ResolvedChatSessionsExtensionPoint, IChatSessionsService } from '../../common/chatSessionsService.js';
 import { ChatAgentLocation } from '../../common/constants.js';
 import { PROMPT_LANGUAGE_ID } from '../../common/promptSyntax/promptTypes.js';
-import { AgentSessionProviders, getAgentSessionProviderIcon, getAgentSessionProviderName } from '../agentSessions/agentSessions.js';
-import { IChatWidget, IChatWidgetService } from '../chat.js';
+import { AgentSessionProviders, getAgentSessionProvider, getAgentSessionProviderIcon, getAgentSessionProviderName } from '../agentSessions/agentSessions.js';
+import { IAgentSessionsService } from '../agentSessions/agentSessionsService.js';
+import { IChatWidget, IChatWidgetService, isIChatViewViewContext } from '../chat.js';
 import { ctxHasEditorModification } from '../chatEditing/chatEditingEditorContextKeys.js';
 import { CHAT_SETUP_ACTION_ID } from './chatActions.js';
 import { PromptFileVariableKind, toPromptFileVariableEntry } from '../../common/attachments/chatVariableEntries.js';
 
+/**
+ * Extracts the "owner/repo" name-with-owner from a git remote URL.
+ * Supports HTTPS (https://github.com/owner/repo.git) and SSH (git@github.com:owner/repo.git) formats.
+ */
+function extractNwoFromRemoteUrl(remoteUrl: string): string | undefined {
+	const match = remoteUrl.match(/(?:github\.com)[/:](?<owner>[^/]+)\/(?<repo>[^/.]+)/);
+	if (match?.groups) {
+		return `${match.groups.owner}/${match.groups.repo}`;
+	}
+	return undefined;
+}
+
+/**
+ * Resolves GitHub NWO from a local git repository path by reading `.git/config`.
+ * Handles both regular repos and git worktrees.
+ */
+async function resolveGitRemoteNwo(repoPath: string, fileService: IFileService): Promise<string | undefined> {
+	try {
+		const gitPath = `${repoPath}/.git`;
+		const gitUri = URI.file(gitPath);
+
+		let configUri: URI;
+		try {
+			const stat = await fileService.stat(gitUri);
+			if (stat.isDirectory) {
+				// Regular git repo
+				configUri = URI.file(`${gitPath}/config`);
+			} else {
+				// Git worktree — .git is a file with "gitdir: <path>"
+				const gitFile = await fileService.readFile(gitUri);
+				const gitDir = gitFile.value.toString().trim().replace(/^gitdir:\s*/, '');
+				// Resolve relative paths
+				const resolvedGitDir = gitDir.startsWith('/')
+					? gitDir
+					: `${repoPath}/${gitDir}`;
+				// The config is in the common dir (parent of worktree git dirs)
+				// e.g., gitdir points to /repo/.git/worktrees/name, config is at /repo/.git/config
+				const commonDir = resolvedGitDir.replace(/\/worktrees\/[^/]+$/, '');
+				configUri = URI.file(`${commonDir}/config`);
+			}
+		} catch {
+			// .git doesn't exist
+			return undefined;
+		}
+
+		const content = await fileService.readFile(configUri);
+		const configText = content.value.toString();
+
+		// Parse remote "origin" URL from git config
+		const remoteMatch = configText.match(/\[remote\s+"origin"\][^[]*url\s*=\s*(.+)/m);
+		if (remoteMatch?.[1]) {
+			return extractNwoFromRemoteUrl(remoteMatch[1].trim());
+		}
+	} catch {
+		// File not found or not readable
+	}
+	return undefined;
+}
+
 export const enum ActionLocation {
 	ChatWidget = 'chatWidget',
 	Editor = 'editor'
@@ -152,7 +215,7 @@ export class ChatContinueInSessionActionItem extends ActionWidgetDropdownActionV
 		};
 	}
 
-	private static toAction(provider: AgentSessionProviders, contrib: IChatSessionsExtensionPoint, instantiationService: IInstantiationService, location: ActionLocation): IActionWidgetDropdownAction {
+	private static toAction(provider: AgentSessionProviders, contrib: ResolvedChatSessionsExtensionPoint, instantiationService: IInstantiationService, location: ActionLocation): IActionWidgetDropdownAction {
 		return {
 			id: contrib.type,
 			enabled: true,
@@ -208,17 +271,112 @@ const NEW_CHAT_SESSION_ACTION_ID = 'workbench.action.chat.openNewSessionEditor';
 export class CreateRemoteAgentJobAction {
 	constructor() { }
 
-	private openUntitledEditor(commandService: ICommandService, continuationTarget: IChatSessionsExtensionPoint) {
+	private openUntitledEditor(commandService: ICommandService, continuationTarget: ResolvedChatSessionsExtensionPoint) {
 		commandService.executeCommand(`${NEW_CHAT_SESSION_ACTION_ID}.${continuationTarget.type}`);
 	}
 
-	async run(accessor: ServicesAccessor, continuationTarget: IChatSessionsExtensionPoint, _widget?: IChatWidget) {
+	/**
+	 * Extracts the GitHub "owner/repo" NWO from the source session by checking
+	 * multiple data sources: chat model repoData, session metadata, and session options.
+	 */
+	private async extractRepoNwoFromSession(agentSessionsService: IAgentSessionsService, chatSessionsService: IChatSessionsService, fileService: IFileService, sessionResource: URI, chatModel: ChatModel): Promise<string | undefined> {
+		// 1. Try chat model's repoData (populated when local git repo exists)
+		const repoData = chatModel.repoData;
+		if (repoData?.remoteUrl) {
+			const nwo = extractNwoFromRemoteUrl(repoData.remoteUrl);
+			if (nwo) {
+				return nwo;
+			}
+		}
+
+		// 2. Try agent session metadata (populated by session providers)
+		const agentSession = agentSessionsService.getSession(sessionResource);
+		if (agentSession?.metadata) {
+			const metadata = agentSession.metadata;
+
+			// Cloud sessions set name/owner in metadata
+			const owner = metadata.owner as string | undefined;
+			const name = metadata.name as string | undefined;
+			if (owner && name) {
+				return `${owner}/${name}`;
+			}
+
+			// Background sessions may set repositoryNwo directly
+			const repositoryNwo = metadata.repositoryNwo as string | undefined;
+			if (repositoryNwo?.includes('/')) {
+				return repositoryNwo;
+			}
+
+			// Background sessions may set repositoryUrl
+			const repositoryUrl = metadata.repositoryUrl as string | undefined;
+			if (repositoryUrl) {
+				const nwo = extractNwoFromRemoteUrl(repositoryUrl);
+				if (nwo) {
+					return nwo;
+				}
+			}
+
+			// Background sessions set workingDirectoryPath — resolve git remote from it
+			const workingDir = (metadata.workingDirectoryPath ?? metadata.repositoryPath ?? metadata.worktreePath) as string | undefined;
+			if (workingDir) {
+				const nwo = await resolveGitRemoteNwo(workingDir, fileService);
+				if (nwo) {
+					return nwo;
+				}
+			}
+		}
+
+		// 3. Try session options (repository picker selection)
+		// Cloud sessions use 'repositories', sessions window uses 'repository'
+		for (const optionId of ['repositories', 'repository']) {
+			const repoOption = chatSessionsService.getSessionOption(sessionResource, optionId);
+			if (repoOption) {
+				const optionValue = typeof repoOption === 'string' ? repoOption : (repoOption as { id: string }).id;
+				if (optionValue) {
+					// Check if it's already a "owner/repo" NWO (exactly two segments)
+					const segments = optionValue.split('/').filter(Boolean);
+					if (segments.length === 2) {
+						return optionValue;
+					}
+					// Try extracting NWO from a URL
+					const nwo = extractNwoFromRemoteUrl(optionValue);
+					if (nwo) {
+						return nwo;
+					}
+					// Try parsing as URI (e.g. github-remote-file://github/owner/repo/...)
+					try {
+						const uri = URI.parse(optionValue);
+						if (uri.authority === 'github') {
+							const parts = uri.path.split('/').filter(Boolean);
+							if (parts.length >= 2) {
+								return `${parts[0]}/${parts[1]}`;
+							}
+						}
+					} catch { /* ignore */ }
+					// Local filesystem path — resolve git remote
+					if (isAbsolute(optionValue)) {
+						const nwoFromGit = await resolveGitRemoteNwo(optionValue, fileService);
+						if (nwoFromGit) {
+							return nwoFromGit;
+						}
+					}
+				}
+			}
+		}
+
+		return undefined;
+	}
+
+	async run(accessor: ServicesAccessor, continuationTarget: ResolvedChatSessionsExtensionPoint, _widget?: IChatWidget) {
 		const contextKeyService = accessor.get(IContextKeyService);
 		const commandService = accessor.get(ICommandService);
 		const widgetService = accessor.get(IChatWidgetService);
 		const chatAgentService = accessor.get(IChatAgentService);
 		const chatService = accessor.get(IChatService);
 		const editorService = accessor.get(IEditorService);
+		const agentSessionsService = accessor.get(IAgentSessionsService);
+		const chatSessionsService = accessor.get(IChatSessionsService);
+		const fileService = accessor.get(IFileService);
 
 		const remoteJobCreatingKey = ChatContextKeys.remoteJobCreating.bindTo(contextKeyService);
 
@@ -246,7 +404,7 @@ export class CreateRemoteAgentJobAction {
 				userPrompt = 'implement this.';
 			}
 
-			const attachedContext = widget.input.getAttachedAndImplicitContext(sessionResource);
+			const attachedContext = widget.input.getAttachedAndImplicitContext();
 			widget.input.acceptInput(true);
 
 			// For inline editor mode, add selection or cursor information
@@ -273,13 +431,56 @@ export class CreateRemoteAgentJobAction {
 				}
 			}
 
+			const continuationTargetType = continuationTarget.type;
+
+			// When source and target session types differ in the sessions window,
+			// open a new session of the target type with the prompt and context
+			// instead of sending to the current (incompatible) session resource.
+			const isSessionsWindow = IsSessionsWindowContext.getValue(contextKeyService);
+			const sourceProvider = getAgentSessionProvider(sessionResource);
+			if (isSessionsWindow && sourceProvider && sourceProvider !== continuationTargetType) {
+				const isSidebar = isIChatViewViewContext(widget.viewContext);
+				const actionId = isSidebar
+					? `workbench.action.chat.openNewSessionSidebar.${continuationTargetType}`
+					: `${NEW_CHAT_SESSION_ACTION_ID}.${continuationTargetType}`;
+
+				// Build conversation transcript from the source session to preserve context.
+				// Truncate to avoid exceeding token limits of the target model.
+				const maxTranscriptLength = 20_000;
+				let transcript = chatRequests.map(req => {
+					const userMsg = `User: ${req.message.text}`;
+					const respMsg = req.response?.response ? `Assistant: ${req.response.response.getMarkdown()}` : '';
+					return respMsg ? `${userMsg}\n${respMsg}` : userMsg;
+				}).join('\n\n');
+				if (transcript.length > maxTranscriptLength) {
+					transcript = transcript.substring(transcript.length - maxTranscriptLength);
+				}
+
+				const delegationPrompt = transcript
+					? `The following is the conversation history from a previous ${getAgentSessionProviderName(sourceProvider)} session. Continue working on it.\n\n${transcript}\n\nUser: ${userPrompt}`
+					: userPrompt;
+
+				// Extract repository info from the source session to pass to the target session
+				const initialSessionOptions: { optionId: string; value: string }[] = [];
+				const repoNwo = await this.extractRepoNwoFromSession(agentSessionsService, chatSessionsService, fileService, sessionResource, chatModel);
+				if (repoNwo) {
+					initialSessionOptions.push({ optionId: 'repositories', value: repoNwo });
+				}
+
+				await commandService.executeCommand(actionId, {
+					prompt: delegationPrompt,
+					attachedContext: attachedContext.asArray(),
+					initialSessionOptions: initialSessionOptions.length > 0 ? initialSessionOptions : undefined,
+				});
+				return;
+			}
+
 			const defaultAgent = chatAgentService.getDefaultAgent(ChatAgentLocation.Chat);
 			const instantiationService = accessor.get(IInstantiationService);
 			const requestParser = instantiationService.createInstance(ChatRequestParser);
-			const continuationTargetType = continuationTarget.type;
 
 			// Add the request to the model first
-			const parsedRequest = requestParser.parseChatRequest(sessionResource, userPrompt, ChatAgentLocation.Chat);
+			const parsedRequest = requestParser.parseChatRequestWithReferences(getDynamicVariablesForWidget(widget), getSelectedToolAndToolSetsForWidget(widget), userPrompt, ChatAgentLocation.Chat);
 			const addedRequest = chatModel.addRequest(
 				parsedRequest,
 				{ variables: attachedContext.asArray() },
@@ -300,7 +501,7 @@ export class CreateRemoteAgentJobAction {
 				await widget.handleDelegationExitIfNeeded(defaultAgent, sendResult.data.agent);
 			}
 		} catch (e) {
-			console.error('Error creating remote coding agent job', e);
+			console.error('[Delegation] Error creating remote coding agent job', e);
 			throw e;
 		} finally {
 			remoteJobCreatingKey.set(false);
@@ -311,7 +512,7 @@ export class CreateRemoteAgentJobAction {
 class CreateRemoteAgentJobFromEditorAction {
 	constructor() { }
 
-	async run(accessor: ServicesAccessor, continuationTarget: IChatSessionsExtensionPoint) {
+	async run(accessor: ServicesAccessor, continuationTarget: ResolvedChatSessionsExtensionPoint) {
 
 		try {
 			const editorService = accessor.get(IEditorService);
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatCopyActions.ts b/src/vs/workbench/contrib/chat/browser/actions/chatCopyActions.ts
index e0647b11c4af6..42d67d3b3a579 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatCopyActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatCopyActions.ts
@@ -4,10 +4,12 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as dom from '../../../../../base/browser/dom.js';
+import { Codicon } from '../../../../../base/common/codicons.js';
 import { ServicesAccessor } from '../../../../../editor/browser/editorExtensions.js';
 import { localize2 } from '../../../../../nls.js';
 import { Action2, MenuId, registerAction2 } from '../../../../../platform/actions/common/actions.js';
 import { IClipboardService } from '../../../../../platform/clipboard/common/clipboardService.js';
+import { ContextKeyExpr } from '../../../../../platform/contextkey/common/contextkey.js';
 import { katexContainerClassName, katexContainerLatexAttributeName } from '../../../markdown/common/markedKatexExtension.js';
 import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
 import { IChatRequestViewModel, IChatResponseViewModel, isChatTreeItem, isRequestVM, isResponseVM } from '../../common/model/chatViewModel.js';
@@ -54,11 +56,20 @@ export function registerChatCopyActions() {
 				title: localize2('interactive.copyItem.label', "Copy"),
 				f1: false,
 				category: CHAT_CATEGORY,
-				menu: {
-					id: MenuId.ChatContext,
-					when: ChatContextKeys.responseIsFiltered.negate(),
-					group: 'copy',
-				}
+				icon: Codicon.copy,
+				menu: [
+					{
+						id: MenuId.ChatContext,
+						when: ChatContextKeys.responseIsFiltered.negate(),
+						group: 'copy',
+					},
+					{
+						id: MenuId.ChatMessageFooter,
+						group: 'navigation',
+						order: 1,
+						when: ContextKeyExpr.and(ChatContextKeys.isResponse, ChatContextKeys.responseIsFiltered.negate()),
+					}
+				]
 			});
 		}
 
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatExecuteActions.ts b/src/vs/workbench/contrib/chat/browser/actions/chatExecuteActions.ts
index 7e505aa90765c..c49e5c69c32ab 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatExecuteActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatExecuteActions.ts
@@ -22,15 +22,16 @@ import { KeybindingWeight } from '../../../../../platform/keybinding/common/keyb
 import { ILogService } from '../../../../../platform/log/common/log.js';
 import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
 import { IViewsService } from '../../../../services/views/common/viewsService.js';
+import { IsSessionsWindowContext } from '../../../../common/contextkeys.js';
 import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
 import { getModeNameForTelemetry, IChatMode, IChatModeService } from '../../common/chatModes.js';
 import { chatVariableLeader } from '../../common/requestParser/chatParserTypes.js';
 import { ChatStopCancellationNoopClassification, ChatStopCancellationNoopEvent, ChatStopCancellationNoopEventName, IChatService } from '../../common/chatService/chatService.js';
-import { ChatAgentLocation, ChatConfiguration, ChatModeKind, } from '../../common/constants.js';
+import { ChatAgentLocation, ChatConfiguration, ChatModeKind } from '../../common/constants.js';
 import { ILanguageModelChatMetadata } from '../../common/languageModels.js';
 import { ILanguageModelToolsService } from '../../common/tools/languageModelToolsService.js';
 import { isInClaudeAgentsFolder } from '../../common/promptSyntax/config/promptFileLocations.js';
-import { IChatSessionsService } from '../../common/chatSessionsService.js';
+import { IChatSessionsService, localChatSessionType } from '../../common/chatSessionsService.js';
 import { IChatWidget, IChatWidgetService } from '../chat.js';
 import { getAgentSessionProvider, AgentSessionProviders } from '../agentSessions/agentSessions.js';
 import { getEditingSessionContext } from '../chatEditing/chatEditingActions.js';
@@ -185,6 +186,18 @@ const requestInProgressOrPendingToolCall = ContextKeyExpr.or(
 	ChatContextKeys.Editing.hasToolConfirmation,
 	ChatContextKeys.Editing.hasQuestionCarousel,
 );
+const requestInProgressWithoutInput = ContextKeyExpr.and(
+	ChatContextKeys.requestInProgress,
+	ChatContextKeys.inputHasText.negate(),
+);
+const pendingToolCall = ContextKeyExpr.or(
+	ChatContextKeys.Editing.hasToolConfirmation,
+	ContextKeyExpr.and(ChatContextKeys.Editing.hasQuestionCarousel, ChatContextKeys.inputHasText.negate()),
+);
+const noQuestionCarouselOrHasInput = ContextKeyExpr.or(
+	ChatContextKeys.Editing.hasQuestionCarousel.negate(),
+	ChatContextKeys.inputHasText,
+);
 const whenNotInProgress = ChatContextKeys.requestInProgress.negate();
 
 export class ChatSubmitAction extends SubmitAction {
@@ -226,6 +239,7 @@ export class ChatSubmitAction extends SubmitAction {
 						whenNotInProgress,
 						menuCondition,
 						ChatContextKeys.withinEditSessionDiff.negate(),
+						noQuestionCarouselOrHasInput,
 					),
 					group: 'navigation',
 					alt: {
@@ -298,7 +312,6 @@ class ToggleChatModeAction extends Action2 {
 
 	async run(accessor: ServicesAccessor, ...args: unknown[]) {
 		const commandService = accessor.get(ICommandService);
-		const configurationService = accessor.get(IConfigurationService);
 		const instaService = accessor.get(IInstantiationService);
 		const modeService = accessor.get(IChatModeService);
 		const telemetryService = accessor.get(ITelemetryService);
@@ -318,7 +331,7 @@ class ToggleChatModeAction extends Action2 {
 
 		const chatSession = widget.viewModel?.model;
 		const requestCount = chatSession?.getRequests().length ?? 0;
-		const switchToMode = (arg && (modeService.findModeById(arg.modeId) || modeService.findModeByName(arg.modeId))) ?? this.getNextMode(widget, requestCount, configurationService, modeService);
+		const switchToMode = (arg && (modeService.findModeById(arg.modeId) || modeService.findModeByName(arg.modeId))) ?? this.getNextMode(widget, requestCount, modeService);
 
 		const currentMode = widget.input.currentModeObs.get();
 		if (switchToMode.id === currentMode.id) {
@@ -357,11 +370,11 @@ class ToggleChatModeAction extends Action2 {
 		}
 	}
 
-	private getNextMode(chatWidget: IChatWidget, requestCount: number, configurationService: IConfigurationService, modeService: IChatModeService): IChatMode {
+	private getNextMode(chatWidget: IChatWidget, requestCount: number, modeService: IChatModeService): IChatMode {
 		const modes = modeService.getModes();
 		const flat = [
 			...modes.builtin.filter(mode => {
-				return mode.kind !== ChatModeKind.Edit || configurationService.getValue(ChatConfiguration.Edits2Enabled) || requestCount === 0;
+				return mode.kind !== ChatModeKind.Edit || requestCount === 0;
 			}),
 			...(modes.custom ?? []),
 		];
@@ -440,6 +453,46 @@ export class OpenModelPickerAction extends Action2 {
 		}
 	}
 }
+
+export class OpenPermissionPickerAction extends Action2 {
+	static readonly ID = 'workbench.action.chat.openPermissionPicker';
+
+	constructor() {
+		super({
+			id: OpenPermissionPickerAction.ID,
+			title: localize2('interactive.openPermissionPicker.label', "Open Permission Picker"),
+			tooltip: localize('setPermissionLevel', "Set Permissions"),
+			category: CHAT_CATEGORY,
+			f1: false,
+			precondition: ChatContextKeys.enabled,
+			menu: {
+				id: MenuId.ChatInputSecondary,
+				order: 10,
+				group: 'navigation',
+				when:
+					ContextKeyExpr.and(
+						ChatContextKeys.enabled,
+						ChatContextKeys.location.isEqualTo(ChatAgentLocation.Chat),
+						ChatContextKeys.chatModeKind.notEqualsTo(ChatModeKind.Ask),
+						ChatContextKeys.inQuickChat.negate(),
+						ContextKeyExpr.or(
+							ChatContextKeys.lockedToCodingAgent.negate(),
+							ChatContextKeys.lockedCodingAgentId.isEqualTo(AgentSessionProviders.Background),
+						),
+					)
+			}
+		});
+	}
+
+	override async run(accessor: ServicesAccessor): Promise<void> {
+		const widgetService = accessor.get(IChatWidgetService);
+		const widget = widgetService.lastFocusedWidget;
+		if (widget) {
+			widget.input.openPermissionPicker();
+		}
+	}
+}
+
 export class OpenModePickerAction extends Action2 {
 	static readonly ID = 'workbench.action.chat.openModePicker';
 
@@ -469,9 +522,10 @@ export class OpenModePickerAction extends Action2 {
 						ContextKeyExpr.or(
 							ChatContextKeys.lockedToCodingAgent.negate(),
 							ChatContextKeys.chatSessionHasCustomAgentTarget),
-						// Hide in welcome view when session type is not local
+						// Show in welcome view for local sessions or sessions with custom agent target
 						ContextKeyExpr.or(
 							ChatContextKeys.inAgentSessionsWelcome.negate(),
+							ChatContextKeys.chatSessionHasCustomAgentTarget,
 							ChatContextKeys.agentSessionType.isEqualTo(AgentSessionProviders.Local))),
 					group: 'navigation',
 				},
@@ -507,6 +561,18 @@ export class OpenSessionTargetPickerAction extends Action2 {
 						ChatContextKeys.enabled,
 						ChatContextKeys.location.isEqualTo(ChatAgentLocation.Chat),
 						ChatContextKeys.inQuickChat.negate(),
+						ChatContextKeys.chatSessionIsEmpty,
+						IsSessionsWindowContext),
+					group: 'navigation',
+				},
+				{
+					id: MenuId.ChatInputSecondary,
+					order: 0,
+					when: ContextKeyExpr.and(
+						ChatContextKeys.enabled,
+						ChatContextKeys.location.isEqualTo(ChatAgentLocation.Chat),
+						ChatContextKeys.inQuickChat.negate(),
+						IsSessionsWindowContext.negate(),
 						ChatContextKeys.chatSessionIsEmpty),
 					group: 'navigation',
 				},
@@ -536,13 +602,14 @@ export class OpenDelegationPickerAction extends Action2 {
 			precondition: ContextKeyExpr.and(ChatContextKeys.enabled, ChatContextKeys.chatSessionIsEmpty.negate(), ChatContextKeys.currentlyEditingInput.negate(), ChatContextKeys.currentlyEditing.negate()),
 			menu: [
 				{
-					id: MenuId.ChatInput,
+					id: MenuId.ChatInputSecondary,
 					order: 0.5,
 					when: ContextKeyExpr.and(
 						ChatContextKeys.enabled,
 						ChatContextKeys.location.isEqualTo(ChatAgentLocation.Chat),
 						ChatContextKeys.inQuickChat.negate(),
-						ChatContextKeys.chatSessionIsEmpty.negate()),
+						ChatContextKeys.chatSessionIsEmpty.negate()
+					),
 					group: 'navigation',
 				},
 			]
@@ -575,7 +642,18 @@ export class OpenWorkspacePickerAction extends Action2 {
 					order: 0.6,
 					when: ContextKeyExpr.and(
 						ChatContextKeys.inAgentSessionsWelcome,
-						ChatContextKeys.chatSessionType.isEqualTo('local')
+						ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+						IsSessionsWindowContext
+					),
+					group: 'navigation',
+				},
+				{
+					id: MenuId.ChatInputSecondary,
+					order: 0.6,
+					when: ContextKeyExpr.and(
+						ChatContextKeys.inAgentSessionsWelcome,
+						ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+						IsSessionsWindowContext.negate()
 					),
 					group: 'navigation',
 				},
@@ -593,7 +671,7 @@ export class ChatSessionPrimaryPickerAction extends Action2 {
 	constructor() {
 		super({
 			id: ChatSessionPrimaryPickerAction.ID,
-			title: localize2('interactive.openChatSessionPrimaryPicker.label', "Open Model Picker"),
+			title: localize2('interactive.openChatSessionPrimaryPicker.label', "Open Primary Session Picker"),
 			category: CHAT_CATEGORY,
 			f1: false,
 			precondition: ChatContextKeys.enabled,
@@ -657,7 +735,8 @@ export class ChatEditingSessionSubmitAction extends SubmitAction {
 	constructor() {
 		const notInProgressOrEditing = ContextKeyExpr.and(
 			ContextKeyExpr.or(whenNotInProgress, ChatContextKeys.editingRequestType.isEqualTo(ChatContextKeys.EditingRequestType.Sent)),
-			ChatContextKeys.editingRequestType.notEqualsTo(ChatContextKeys.EditingRequestType.QueueOrSteer)
+			ChatContextKeys.editingRequestType.notEqualsTo(ChatContextKeys.EditingRequestType.Queue),
+			ChatContextKeys.editingRequestType.notEqualsTo(ChatContextKeys.EditingRequestType.Steer)
 		);
 
 		const menuCondition = ChatContextKeys.chatModeKind.notEqualsTo(ChatModeKind.Ask);
@@ -680,7 +759,8 @@ export class ChatEditingSessionSubmitAction extends SubmitAction {
 					order: 4,
 					when: ContextKeyExpr.and(
 						notInProgressOrEditing,
-						menuCondition),
+						menuCondition,
+						noQuestionCarouselOrHasInput),
 					group: 'navigation',
 					alt: {
 						id: 'workbench.action.chat.sendToNewChat',
@@ -807,7 +887,7 @@ class SendToNewChatAction extends Action2 {
 
 		// Cancel any in-progress request before clearing
 		if (widget.viewModel) {
-			chatService.cancelCurrentRequestForSession(widget.viewModel.sessionResource);
+			await chatService.cancelCurrentRequestForSession(widget.viewModel.sessionResource, 'newSessionAction');
 		}
 
 		if (widget.viewModel?.model) {
@@ -838,7 +918,7 @@ export class CancelAction extends Action2 {
 			menu: [{
 				id: MenuId.ChatExecute,
 				when: ContextKeyExpr.and(
-					requestInProgressOrPendingToolCall,
+					ContextKeyExpr.or(requestInProgressWithoutInput, pendingToolCall),
 					ChatContextKeys.remoteJobCreating.negate(),
 					ChatContextKeys.currentlyEditing.negate(),
 				),
@@ -867,7 +947,7 @@ export class CancelAction extends Action2 {
 		});
 	}
 
-	run(accessor: ServicesAccessor, ...args: unknown[]) {
+	async run(accessor: ServicesAccessor, ...args: unknown[]) {
 		const context = args[0] as IChatExecuteActionContext | undefined;
 		const widgetService = accessor.get(IChatWidgetService);
 		const logService = accessor.get(ILogService);
@@ -886,7 +966,7 @@ export class CancelAction extends Action2 {
 
 		const chatService = accessor.get(IChatService);
 		if (widget.viewModel) {
-			chatService.cancelCurrentRequestForSession(widget.viewModel.sessionResource);
+			await chatService.cancelCurrentRequestForSession(widget.viewModel.sessionResource, 'cancelAction');
 		} else {
 			telemetryService.publicLog2<ChatStopCancellationNoopEvent, ChatStopCancellationNoopClassification>(ChatStopCancellationNoopEventName, {
 				source: 'cancelAction',
@@ -952,6 +1032,7 @@ export function registerChatExecuteActions() {
 	registerAction2(ToggleChatModeAction);
 	registerAction2(SwitchToNextModelAction);
 	registerAction2(OpenModelPickerAction);
+	registerAction2(OpenPermissionPickerAction);
 	registerAction2(OpenModePickerAction);
 	registerAction2(OpenSessionTargetPickerAction);
 	registerAction2(OpenDelegationPickerAction);
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatNewActions.ts b/src/vs/workbench/contrib/chat/browser/actions/chatNewActions.ts
index febdbc539f7fb..271e82b2baf41 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatNewActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatNewActions.ts
@@ -108,6 +108,11 @@ export function registerNewChatActions() {
 						id: MenuId.ChatNewMenu,
 						group: '1_open',
 						order: 1,
+						when: ContextKeyExpr.and(
+							ChatContextKeys.newChatButtonExperimentIcon.notEqualsTo('copilot'),
+							ChatContextKeys.newChatButtonExperimentIcon.notEqualsTo('new-session'),
+							ChatContextKeys.newChatButtonExperimentIcon.notEqualsTo('comment')
+						)
 					}
 				],
 				keybinding: {
@@ -132,6 +137,40 @@ export function registerNewChatActions() {
 		}
 	}
 	);
+
+	const iconVariants = [
+		{ idSuffix: '.copilotIcon', iconValue: 'copilot', icon: Codicon.copilot },
+		{ idSuffix: '.newSessionIcon', iconValue: 'new-session', icon: Codicon.newSession },
+		{ idSuffix: '.commentIcon', iconValue: 'comment', icon: Codicon.comment },
+	] as const;
+
+	for (const variant of iconVariants) {
+		registerAction2(class extends Action2 {
+			constructor() {
+				super({
+					id: ACTION_ID_NEW_CHAT + variant.idSuffix,
+					title: localize2('chat.newEdits.label', "New Chat"),
+					category: CHAT_CATEGORY,
+					icon: variant.icon,
+					precondition: ContextKeyExpr.and(ChatContextKeys.enabled, ChatContextKeys.location.isEqualTo(ChatAgentLocation.Chat)),
+					f1: false,
+					menu: [{
+						id: MenuId.ChatNewMenu,
+						group: '1_open',
+						order: 1,
+						when: ChatContextKeys.newChatButtonExperimentIcon.isEqualTo(variant.iconValue)
+					}]
+				});
+			}
+
+			async run(accessor: ServicesAccessor, ...args: unknown[]) {
+				const executeCommandContext = isNewEditSessionActionContext(args[0]) ? args[0] : undefined;
+				const context = getEditingSessionContext(accessor, args);
+				await runNewChatAction(accessor, context, executeCommandContext);
+			}
+		});
+	}
+
 	CommandsRegistry.registerCommandAlias(ACTION_ID_NEW_EDIT_SESSION, ACTION_ID_NEW_CHAT);
 
 	registerAction2(class NewLocalChatAction extends Action2 {
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatOpenAgentDebugPanelAction.ts b/src/vs/workbench/contrib/chat/browser/actions/chatOpenAgentDebugPanelAction.ts
new file mode 100644
index 0000000000000..6b4d5af68e8fd
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatOpenAgentDebugPanelAction.ts
@@ -0,0 +1,253 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { VSBuffer } from '../../../../../base/common/buffer.js';
+import { joinPath } from '../../../../../base/common/resources.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { ServicesAccessor } from '../../../../../editor/browser/editorExtensions.js';
+import { localize, localize2 } from '../../../../../nls.js';
+import { Action2, MenuId, registerAction2 } from '../../../../../platform/actions/common/actions.js';
+import { Categories } from '../../../../../platform/action/common/actionCommonCategories.js';
+import { ContextKeyExpr } from '../../../../../platform/contextkey/common/contextkey.js';
+import { IDialogService, IFileDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
+import { IFileService } from '../../../../../platform/files/common/files.js';
+import { INotificationService, Severity } from '../../../../../platform/notification/common/notification.js';
+import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
+import { ActiveEditorContext } from '../../../../common/contextkeys.js';
+import { IEditorService } from '../../../../services/editor/common/editorService.js';
+import { isChatViewTitleActionContext } from '../../common/actions/chatActions.js';
+import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
+import { IChatDebugService } from '../../common/chatDebugService.js';
+import { ChatViewId, IChatWidgetService } from '../chat.js';
+import { CHAT_CATEGORY, CHAT_CONFIG_MENU_ID } from './chatActions.js';
+import { ChatDebugEditorInput } from '../chatDebug/chatDebugEditorInput.js';
+import { Codicon } from '../../../../../base/common/codicons.js';
+import { IChatDebugEditorOptions } from '../chatDebug/chatDebugTypes.js';
+
+/**
+ * Registers the Open Agent Debug Logs and Show Agent Debug Logs actions.
+ */
+export function registerChatOpenAgentDebugPanelAction() {
+	registerAction2(class OpenAgentDebugPanelAction extends Action2 {
+		constructor() {
+			super({
+				id: 'workbench.action.chat.openAgentDebugPanel',
+				title: localize2('chat.openAgentDebugPanel.label', "Open Agent Debug Logs"),
+				f1: true,
+				category: Categories.Developer,
+				precondition: ChatContextKeys.enabled,
+			});
+		}
+
+		async run(accessor: ServicesAccessor): Promise<void> {
+			const editorService = accessor.get(IEditorService);
+			const chatDebugService = accessor.get(IChatDebugService);
+
+			// Clear active session so the editor shows the home view
+			chatDebugService.activeSessionResource = undefined;
+
+			const options: IChatDebugEditorOptions = { pinned: true, viewHint: 'home' };
+			await editorService.openEditor(ChatDebugEditorInput.instance, options);
+		}
+	});
+
+	registerAction2(class OpenAgentDebugPanelForSessionAction extends Action2 {
+		constructor() {
+			super({
+				id: 'workbench.action.chat.openAgentDebugPanelForSession',
+				title: localize2('chat.openAgentDebugPanelForSession.label', "Show Agent Debug Logs"),
+				f1: false,
+				category: CHAT_CATEGORY,
+				precondition: ContextKeyExpr.and(ChatContextKeys.enabled, ChatContextKeys.chatSessionHasDebugData),
+				menu: [{
+					id: CHAT_CONFIG_MENU_ID,
+					when: ContextKeyExpr.and(ChatContextKeys.enabled, ContextKeyExpr.equals('view', ChatViewId)),
+					order: 0,
+					group: '4_logs'
+				}, {
+					id: MenuId.ChatWelcomeContext,
+					group: '2_settings',
+					order: 0,
+					when: ChatContextKeys.inChatEditor.negate()
+				}]
+			});
+		}
+
+		async run(accessor: ServicesAccessor, context?: URI | unknown, filter?: string): Promise<void> {
+			const editorService = accessor.get(IEditorService);
+			const chatWidgetService = accessor.get(IChatWidgetService);
+			const chatDebugService = accessor.get(IChatDebugService);
+
+			// Extract session resource from context — may be a URI directly
+			// or an IChatViewTitleActionContext from the chat config menu
+			let sessionResource: URI | undefined;
+			if (URI.isUri(context)) {
+				sessionResource = context;
+			} else if (isChatViewTitleActionContext(context)) {
+				sessionResource = context.sessionResource;
+			}
+
+			// Fall back to the last focused widget
+			if (!sessionResource) {
+				const widget = chatWidgetService.lastFocusedWidget;
+				sessionResource = widget?.viewModel?.sessionResource;
+			}
+			chatDebugService.activeSessionResource = sessionResource;
+
+			const options: IChatDebugEditorOptions = { pinned: true, sessionResource, viewHint: 'logs', filter };
+			await editorService.openEditor(ChatDebugEditorInput.instance, options);
+		}
+	});
+
+	const defaultDebugLogFileName = 'agent-debug-log.json';
+	const debugLogFilters = [{ name: localize('chatDebugLog.file.label', "Agent Debug Log"), extensions: ['json'] }];
+
+	registerAction2(class ExportAgentDebugLogAction extends Action2 {
+		constructor() {
+			super({
+				id: 'workbench.action.chat.exportAgentDebugLog',
+				title: localize2('chat.exportAgentDebugLog.label', "Export Agent Debug Log..."),
+				icon: Codicon.desktopDownload,
+				f1: true,
+				category: Categories.Developer,
+				precondition: ChatContextKeys.enabled,
+				menu: [{
+					id: MenuId.EditorTitle,
+					group: 'navigation',
+					when: ActiveEditorContext.isEqualTo(ChatDebugEditorInput.ID),
+					order: 10
+				}],
+			});
+		}
+
+		async run(accessor: ServicesAccessor): Promise<void> {
+			const chatDebugService = accessor.get(IChatDebugService);
+			const fileDialogService = accessor.get(IFileDialogService);
+			const fileService = accessor.get(IFileService);
+			const notificationService = accessor.get(INotificationService);
+			const telemetryService = accessor.get(ITelemetryService);
+
+			const sessionResource = chatDebugService.activeSessionResource;
+			if (!sessionResource) {
+				notificationService.notify({ severity: Severity.Info, message: localize('chatDebugLog.noSession', "No active debug session to export. Navigate to a session first.") });
+				return;
+			}
+
+			const defaultUri = joinPath(await fileDialogService.defaultFilePath(), defaultDebugLogFileName);
+			const outputPath = await fileDialogService.showSaveDialog({ defaultUri, filters: debugLogFilters });
+			if (!outputPath) {
+				return;
+			}
+
+			const data = await chatDebugService.exportLog(sessionResource);
+			if (!data) {
+				notificationService.notify({ severity: Severity.Warning, message: localize('chatDebugLog.exportFailed', "Export is not supported by the current provider.") });
+				return;
+			}
+
+			await fileService.writeFile(outputPath, VSBuffer.wrap(data));
+
+			telemetryService.publicLog2<ChatDebugExportEvent, ChatDebugExportClassification>('chatDebugLogExported', {
+				fileSizeBytes: data.byteLength,
+			});
+		}
+	});
+
+	registerAction2(class ImportAgentDebugLogAction extends Action2 {
+		constructor() {
+			super({
+				id: 'workbench.action.chat.importAgentDebugLog',
+				title: localize2('chat.importAgentDebugLog.label', "Import Agent Debug Log..."),
+				icon: Codicon.cloudUpload,
+				f1: true,
+				category: Categories.Developer,
+				precondition: ChatContextKeys.enabled,
+				menu: [{
+					id: MenuId.EditorTitle,
+					group: 'navigation',
+					when: ActiveEditorContext.isEqualTo(ChatDebugEditorInput.ID),
+					order: 11
+				}],
+			});
+		}
+
+		async run(accessor: ServicesAccessor): Promise<void> {
+			const chatDebugService = accessor.get(IChatDebugService);
+			const dialogService = accessor.get(IDialogService);
+			const editorService = accessor.get(IEditorService);
+			const fileDialogService = accessor.get(IFileDialogService);
+			const fileService = accessor.get(IFileService);
+			const notificationService = accessor.get(INotificationService);
+			const telemetryService = accessor.get(ITelemetryService);
+
+			const defaultUri = joinPath(await fileDialogService.defaultFilePath(), defaultDebugLogFileName);
+			const result = await fileDialogService.showOpenDialog({
+				defaultUri,
+				canSelectFiles: true,
+				filters: debugLogFilters
+			});
+			if (!result) {
+				return;
+			}
+
+			const maxImportSize = 50 * 1024 * 1024; // 50 MB
+			const stat = await fileService.stat(result[0]);
+			if (stat.size !== undefined && stat.size > maxImportSize) {
+				telemetryService.publicLog2<ChatDebugImportEvent, ChatDebugImportClassification>('chatDebugLogImported', {
+					fileSizeBytes: stat.size,
+					result: 'fileTooLarge',
+				});
+				await dialogService.warn(
+					localize('chatDebugLog.fileTooLargeTitle', "File Too Large"),
+					localize('chatDebugLog.fileTooLargeDetail', "The selected file ({0} MB) exceeds the 50 MB size limit for debug log imports.", (stat.size / (1024 * 1024)).toFixed(1))
+				);
+				return;
+			}
+
+			const content = await fileService.readFile(result[0]);
+			const sessionUri = await chatDebugService.importLog(content.value.buffer);
+			if (!sessionUri) {
+				telemetryService.publicLog2<ChatDebugImportEvent, ChatDebugImportClassification>('chatDebugLogImported', {
+					fileSizeBytes: content.value.byteLength,
+					result: 'providerFailed',
+				});
+				notificationService.notify({ severity: Severity.Warning, message: localize('chatDebugLog.importFailed', "Import is not supported by the current provider.") });
+				return;
+			}
+
+			telemetryService.publicLog2<ChatDebugImportEvent, ChatDebugImportClassification>('chatDebugLogImported', {
+				fileSizeBytes: content.value.byteLength,
+				result: 'success',
+			});
+
+			const options: IChatDebugEditorOptions = { pinned: true, sessionResource: sessionUri, viewHint: 'overview' };
+			await editorService.openEditor(ChatDebugEditorInput.instance, options);
+		}
+	});
+}
+
+// Telemetry types
+
+type ChatDebugExportEvent = {
+	fileSizeBytes: number;
+};
+
+type ChatDebugExportClassification = {
+	fileSizeBytes: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'Size of the exported chat debug log file in bytes.' };
+	owner: 'vijayu';
+	comment: 'Tracks usage of the Agent Debug Logs export feature.';
+};
+
+type ChatDebugImportEvent = {
+	fileSizeBytes: number;
+	result: 'success' | 'fileTooLarge' | 'providerFailed';
+};
+
+type ChatDebugImportClassification = {
+	fileSizeBytes: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'Size of the imported chat debug log file in bytes.' };
+	result: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Outcome of the chat debug file import: success, fileTooLarge, or providerFailed.' };
+	owner: 'vijayu';
+	comment: 'Tracks usage of the Agent Debug Logs import feature and failure modes.';
+};
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatOpenDebugPanelAction.ts b/src/vs/workbench/contrib/chat/browser/actions/chatOpenDebugPanelAction.ts
deleted file mode 100644
index 17860ac6b1f3b..0000000000000
--- a/src/vs/workbench/contrib/chat/browser/actions/chatOpenDebugPanelAction.ts
+++ /dev/null
@@ -1,85 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-import { ServicesAccessor } from '../../../../../editor/browser/editorExtensions.js';
-import { localize2 } from '../../../../../nls.js';
-import { Action2, MenuId, registerAction2 } from '../../../../../platform/actions/common/actions.js';
-import { ContextKeyExpr } from '../../../../../platform/contextkey/common/contextkey.js';
-import { IEditorService } from '../../../../services/editor/common/editorService.js';
-import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
-import { IChatDebugService } from '../../common/chatDebugService.js';
-import { ChatViewId, IChatWidgetService } from '../chat.js';
-import { CHAT_CATEGORY, CHAT_CONFIG_MENU_ID } from './chatActions.js';
-import { ChatDebugEditorInput } from '../chatDebug/chatDebugEditorInput.js';
-import { IChatDebugEditorOptions } from '../chatDebug/chatDebugTypes.js';
-
-/**
- * Registers the Open Debug Panel and View Logs actions.
- */
-export function registerChatOpenDebugPanelAction() {
-	registerAction2(class OpenDebugViewAction extends Action2 {
-		constructor() {
-			super({
-				id: 'workbench.action.chat.openDebugView',
-				title: localize2('chat.openDebugView.label', "Open Debug Panel"),
-				f1: true,
-				category: CHAT_CATEGORY,
-				precondition: ChatContextKeys.enabled,
-			});
-		}
-
-		async run(accessor: ServicesAccessor): Promise<void> {
-			const editorService = accessor.get(IEditorService);
-			const chatDebugService = accessor.get(IChatDebugService);
-
-			// Clear active session so the editor shows the home view
-			chatDebugService.activeSessionResource = undefined;
-
-			const options: IChatDebugEditorOptions = { pinned: true, viewHint: 'home' };
-			await editorService.openEditor(ChatDebugEditorInput.instance, options);
-		}
-	});
-
-	registerAction2(class TroubleshootAction extends Action2 {
-		constructor() {
-			super({
-				id: 'workbench.action.chat.troubleshoot',
-				title: localize2('chat.troubleshoot.label', "View Logs"),
-				f1: false,
-				category: CHAT_CATEGORY,
-				menu: [{
-					id: MenuId.ChatContext,
-					group: 'z_clear',
-					order: -1,
-					when: ChatContextKeys.chatSessionHasDebugData
-				}, {
-					id: CHAT_CONFIG_MENU_ID,
-					when: ContextKeyExpr.and(ChatContextKeys.enabled, ContextKeyExpr.equals('view', ChatViewId), ChatContextKeys.chatSessionHasDebugData),
-					order: 14,
-					group: '3_configure'
-				}, {
-					id: MenuId.ChatWelcomeContext,
-					group: '2_settings',
-					order: 0,
-					when: ContextKeyExpr.and(ChatContextKeys.inChatEditor.negate(), ChatContextKeys.chatSessionHasDebugData)
-				}]
-			});
-		}
-
-		async run(accessor: ServicesAccessor): Promise<void> {
-			const editorService = accessor.get(IEditorService);
-			const chatWidgetService = accessor.get(IChatWidgetService);
-			const chatDebugService = accessor.get(IChatDebugService);
-
-			// Get the active chat session resource from the last focused widget
-			const widget = chatWidgetService.lastFocusedWidget;
-			const sessionResource = widget?.viewModel?.sessionResource;
-			chatDebugService.activeSessionResource = sessionResource;
-
-			const options: IChatDebugEditorOptions = { pinned: true, sessionResource, viewHint: 'logs' };
-			await editorService.openEditor(ChatDebugEditorInput.instance, options);
-		}
-	});
-}
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatPluginActions.ts b/src/vs/workbench/contrib/chat/browser/actions/chatPluginActions.ts
index 8dc3610a23e31..734bc935c0e41 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatPluginActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatPluginActions.ts
@@ -3,247 +3,81 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { Codicon } from '../../../../../base/common/codicons.js';
 import { localize, localize2 } from '../../../../../nls.js';
-import { Action2, registerAction2 } from '../../../../../platform/actions/common/actions.js';
+import { Action2, MenuId, registerAction2 } from '../../../../../platform/actions/common/actions.js';
+import { ContextKeyExpr } from '../../../../../platform/contextkey/common/contextkey.js';
 import { ServicesAccessor } from '../../../../../platform/instantiation/common/instantiation.js';
-import { IQuickInputService, IQuickPickItem, QuickPickInput } from '../../../../../platform/quickinput/common/quickInput.js';
-import { DisposableStore } from '../../../../../base/common/lifecycle.js';
-import { ILabelService } from '../../../../../platform/label/common/label.js';
-import { IDialogService, IFileDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
-import { IWorkspaceContextService } from '../../../../../platform/workspace/common/workspace.js';
-import { dirname } from '../../../../../base/common/resources.js';
+import { IQuickInputService } from '../../../../../platform/quickinput/common/quickInput.js';
 import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
-import { IAgentPlugin, IAgentPluginService } from '../../common/plugins/agentPluginService.js';
+import { IPluginInstallService } from '../../common/plugins/pluginInstallService.js';
 import { CHAT_CATEGORY, CHAT_CONFIG_MENU_ID } from './chatActions.js';
-import { ResourceSet } from '../../../../../base/common/map.js';
-import { ChatConfiguration } from '../../common/constants.js';
-import { IConfigurationService, ConfigurationTarget } from '../../../../../platform/configuration/common/configuration.js';
-import { IPaneCompositePartService } from '../../../../services/panecomposite/browser/panecomposite.js';
-import { IExtensionsViewPaneContainer, VIEWLET_ID } from '../../../extensions/common/extensions.js';
-import { ViewContainerLocation } from '../../../../common/views.js';
+import { IExtensionsWorkbenchService } from '../../../extensions/common/extensions.js';
+import { InstalledAgentPluginsViewId } from '../agentPluginsView.js';
 
-const enum ManagePluginItemKind {
-	Plugin = 'plugin',
-	FindMore = 'findMore',
-	AddFromFolder = 'addFromFolder',
-}
-
-interface IPluginPickItem extends IQuickPickItem {
-	readonly kind: ManagePluginItemKind.Plugin;
-	plugin: IAgentPlugin;
-}
-
-interface IFindMorePickItem extends IQuickPickItem {
-	readonly kind: ManagePluginItemKind.FindMore;
-}
-
-interface IAddFromFolderPickItem extends IQuickPickItem {
-	readonly kind: ManagePluginItemKind.AddFromFolder;
-}
-
-interface IManagePluginsPickResult {
-	action: 'apply' | 'findMore' | 'addFromFolder';
-	selectedPluginItems: IPluginPickItem[];
-}
-
-class ManagePluginsAction extends Action2 {
+export class ManagePluginsAction extends Action2 {
 	static readonly ID = 'workbench.action.chat.managePlugins';
 
 	constructor() {
 		super({
 			id: ManagePluginsAction.ID,
-			title: localize2('managePlugins', 'Manage Plugins...'),
+			title: localize2('plugins', 'Plugins'),
 			category: CHAT_CATEGORY,
 			precondition: ChatContextKeys.enabled,
 			menu: [{
 				id: CHAT_CONFIG_MENU_ID,
+				group: '2_plugins',
 			}],
 			f1: true
 		});
 	}
 
 	async run(accessor: ServicesAccessor): Promise<void> {
-		const agentPluginService = accessor.get(IAgentPluginService);
-		const quickInputService = accessor.get(IQuickInputService);
-		const labelService = accessor.get(ILabelService);
-		const dialogService = accessor.get(IDialogService);
-		const fileDialogService = accessor.get(IFileDialogService);
-		const configurationService = accessor.get(IConfigurationService);
-		const workspaceContextService = accessor.get(IWorkspaceContextService);
-		const paneCompositeService = accessor.get(IPaneCompositePartService);
-
-		const allPlugins = agentPluginService.allPlugins.get();
-		const hasWorkspace = workspaceContextService.getWorkspace().folders.length > 0;
-
-		// Group plugins by parent directory label
-		const groups = new Map<string, IAgentPlugin[]>();
-		for (const plugin of allPlugins) {
-			const groupLabel = labelService.getUriLabel(dirname(plugin.uri), { relative: true });
-			let group = groups.get(groupLabel);
-			if (!group) {
-				group = [];
-				groups.set(groupLabel, group);
-			}
-			group.push(plugin);
-		}
-
-		const items: QuickPickInput<IPluginPickItem | IFindMorePickItem | IAddFromFolderPickItem>[] = [];
-		const preselectedPluginItems: IPluginPickItem[] = [];
-		for (const [groupLabel, plugins] of groups) {
-			items.push({ type: 'separator', label: groupLabel });
-			for (const plugin of plugins) {
-				const pluginName = plugin.uri.path.split('/').at(-1) ?? '';
-				const item: IPluginPickItem = {
-					kind: ManagePluginItemKind.Plugin,
-					label: pluginName,
-					plugin,
-					picked: plugin.enabled.get(),
-				};
-				if (item.picked) {
-					preselectedPluginItems.push(item);
-				}
-				items.push(item);
-			}
-		}
-
-		if (items.length > 0 || hasWorkspace) {
-			items.push({ type: 'separator' });
-		}
-
-		if (hasWorkspace) {
-			items.push({
-				kind: ManagePluginItemKind.FindMore,
-				label: localize('findMorePlugins', 'Find More Plugins...'),
-				pickable: false,
-			} satisfies IFindMorePickItem);
-		}
-
-		items.push({
-			kind: ManagePluginItemKind.AddFromFolder,
-			label: localize('addFromFolder', 'Add from Folder...'),
-			pickable: false,
-		} satisfies IAddFromFolderPickItem);
-
-		const result = await showManagePluginsQuickPick(quickInputService, items, preselectedPluginItems);
-
-		if (!result) {
-			return;
-		}
+		accessor.get(IExtensionsWorkbenchService).openSearch('@agentPlugins ');
+	}
+}
 
-		if (result.action === 'findMore') {
-			const viewlet = await paneCompositeService.openPaneComposite(VIEWLET_ID, ViewContainerLocation.Sidebar, true);
-			const view = viewlet?.getViewPaneContainer() as IExtensionsViewPaneContainer | undefined;
-			view?.search('@agentPlugins ');
-			return;
-		}
+class InstallFromSourceAction extends Action2 {
+	static readonly ID = 'workbench.action.chat.installPluginFromSource';
 
-		if (result.action === 'addFromFolder') {
-			const selectedUris = await fileDialogService.showOpenDialog({
-				title: localize('pickPluginFolderTitle', 'Pick Plugin Folder'),
-				canSelectFiles: false,
-				canSelectFolders: true,
-				canSelectMany: false,
-				defaultUri: workspaceContextService.getWorkspace().folders[0]?.uri,
-			});
+	constructor() {
+		super({
+			id: InstallFromSourceAction.ID,
+			title: localize2('installPluginFromSource', 'Install Plugin from Source'),
+			category: CHAT_CATEGORY,
+			icon: Codicon.add,
+			precondition: ChatContextKeys.enabled,
+			f1: true,
+			menu: [{
+				id: MenuId.ViewTitle,
+				when: ContextKeyExpr.and(
+					ContextKeyExpr.equals('view', InstalledAgentPluginsViewId),
+					ChatContextKeys.Setup.hidden.negate(),
+				),
+				group: 'navigation',
+				order: 1,
+			}],
+		});
+	}
 
-			const folderUri = selectedUris?.[0];
-			if (!folderUri) {
-				return;
-			}
+	async run(accessor: ServicesAccessor): Promise<void> {
+		const quickInputService = accessor.get(IQuickInputService);
+		const pluginInstallService = accessor.get(IPluginInstallService);
 
-			const currentPaths = configurationService.getValue<Record<string, boolean>>(ChatConfiguration.PluginPaths) ?? {};
-			const nextPath = folderUri.fsPath;
-			if (!Object.prototype.hasOwnProperty.call(currentPaths, nextPath)) {
-				await configurationService.updateValue(ChatConfiguration.PluginPaths, { ...currentPaths, [nextPath]: true }, ConfigurationTarget.USER_LOCAL);
-			}
-			return;
-		}
+		const source = await quickInputService.input({
+			placeHolder: localize('pluginSourcePlaceholder', "owner/repo or git clone URL"),
+			prompt: localize('pluginSourcePrompt', "Enter a GitHub repository or git URL to install a plugin from"),
+		});
 
-		if (allPlugins.length === 0) {
-			dialogService.info(
-				localize('noPlugins', 'No plugins found.'),
-				localize('noPluginsDetail', 'There are currently no agent plugins discovered in this workspace.')
-			);
+		if (!source) {
 			return;
 		}
 
-		const enabledUris = new ResourceSet(result.selectedPluginItems.map(i => i.plugin.uri));
-		for (const plugin of allPlugins) {
-			const wasEnabled = plugin.enabled.get();
-			const isNowEnabled = enabledUris.has(plugin.uri);
-
-			if (!wasEnabled && isNowEnabled) {
-				plugin.setEnabled(true);
-			} else if (wasEnabled && !isNowEnabled) {
-				plugin.setEnabled(false);
-			}
-		}
+		await pluginInstallService.installPluginFromSource(source.trim());
 	}
 }
 
-async function showManagePluginsQuickPick(
-	quickInputService: IQuickInputService,
-	items: QuickPickInput<IPluginPickItem | IFindMorePickItem | IAddFromFolderPickItem>[],
-	preselectedPluginItems: IPluginPickItem[]
-): Promise<IManagePluginsPickResult | undefined> {
-	const quickPick = quickInputService.createQuickPick<IPluginPickItem | IFindMorePickItem | IAddFromFolderPickItem>({ useSeparators: true });
-	const disposables = new DisposableStore();
-	disposables.add(quickPick);
-
-	quickPick.canSelectMany = true;
-	quickPick.title = localize('managePluginsTitle', 'Manage Plugins');
-	quickPick.placeholder = localize('managePluginsPlaceholder', 'Choose which plugins are enabled');
-	quickPick.items = items;
-	quickPick.selectedItems = preselectedPluginItems;
-
-	const result = await new Promise<IManagePluginsPickResult | undefined>(resolve => {
-		let resolved = false;
-
-		const complete = (value: IManagePluginsPickResult | undefined) => {
-			if (resolved) {
-				return;
-			}
-			resolved = true;
-			resolve(value);
-		};
-
-		disposables.add(quickPick.onDidAccept(() => {
-			const activeItem = quickPick.activeItems[0];
-			if (activeItem?.kind === ManagePluginItemKind.FindMore) {
-				complete({
-					action: 'findMore',
-					selectedPluginItems: [],
-				});
-				quickPick.hide();
-				return;
-			}
-
-			if (activeItem?.kind === ManagePluginItemKind.AddFromFolder) {
-				complete({
-					action: 'addFromFolder',
-					selectedPluginItems: [],
-				});
-				quickPick.hide();
-				return;
-			}
-
-			complete({
-				action: 'apply',
-				selectedPluginItems: quickPick.selectedItems.filter((item): item is IPluginPickItem => item.kind === ManagePluginItemKind.Plugin),
-			});
-			quickPick.hide();
-		}));
-
-		disposables.add(quickPick.onDidHide(() => {
-			complete(undefined);
-			disposables.dispose();
-		}));
-
-		quickPick.show();
-	});
-	return result;
-}
-
 export function registerChatPluginActions() {
 	registerAction2(ManagePluginsAction);
+	registerAction2(InstallFromSourceAction);
 }
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatQueueActions.ts b/src/vs/workbench/contrib/chat/browser/actions/chatQueueActions.ts
index a8d166e68f7d2..ed1b2f3689a9d 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatQueueActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatQueueActions.ts
@@ -13,15 +13,34 @@ import { ContextKeyExpr } from '../../../../../platform/contextkey/common/contex
 import { KeybindingWeight } from '../../../../../platform/keybinding/common/keybindingsRegistry.js';
 import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
 import { ChatRequestQueueKind, IChatService } from '../../common/chatService/chatService.js';
+import { ChatConfiguration } from '../../common/constants.js';
 import { isRequestVM } from '../../common/model/chatViewModel.js';
 import { IChatWidgetService } from '../chat.js';
 import { CHAT_CATEGORY } from './chatActions.js';
 
+const editingQueue = ChatContextKeys.editingRequestType.isEqualTo(ChatContextKeys.EditingRequestType.Queue);
+const editingSteer = ChatContextKeys.editingRequestType.isEqualTo(ChatContextKeys.EditingRequestType.Steer);
+const editingQueueOrSteer = ContextKeyExpr.or(editingQueue, editingSteer)!;
+
 const queuingActionsPresent = ContextKeyExpr.and(
-	ContextKeyExpr.or(ChatContextKeys.requestInProgress, ChatContextKeys.editingRequestType.isEqualTo(ChatContextKeys.EditingRequestType.QueueOrSteer)),
+	ContextKeyExpr.or(ChatContextKeys.requestInProgress, editingQueueOrSteer),
 	ChatContextKeys.editingRequestType.notEqualsTo(ChatContextKeys.EditingRequestType.Sent),
 );
 
+const steerIsDefault = ContextKeyExpr.equals(`config.${ChatConfiguration.RequestQueueingDefaultAction}`, 'steer');
+const queueIsDefault = steerIsDefault.negate();
+
+// The effective default respects the editing context: when editing a queued/steer
+// message, the default matches that message type regardless of the config setting.
+const effectiveDefaultIsQueue = ContextKeyExpr.or(
+	ContextKeyExpr.and(queueIsDefault, editingQueueOrSteer.negate()),
+	editingQueue
+);
+const effectiveDefaultIsSteer = ContextKeyExpr.or(
+	ContextKeyExpr.and(steerIsDefault, editingQueueOrSteer.negate()),
+	editingSteer
+);
+
 export interface IChatRemovePendingRequestContext {
 	sessionResource: URI;
 	pendingRequestId: string;
@@ -52,14 +71,23 @@ export class ChatQueueMessageAction extends Action2 {
 				queuingActionsPresent,
 				ChatContextKeys.inputHasText,
 			),
-			keybinding: {
+			keybinding: [{
 				when: ContextKeyExpr.and(
 					ChatContextKeys.inChatInput,
 					queuingActionsPresent,
+					effectiveDefaultIsSteer,
 				),
 				primary: KeyMod.Alt | KeyCode.Enter,
 				weight: KeybindingWeight.EditorContrib + 1
-			},
+			}, {
+				when: ContextKeyExpr.and(
+					ChatContextKeys.inChatInput,
+					queuingActionsPresent,
+					effectiveDefaultIsQueue,
+				),
+				primary: KeyCode.Enter,
+				weight: KeybindingWeight.EditorContrib + 1
+			}],
 		});
 	}
 
@@ -87,21 +115,30 @@ export class ChatSteerWithMessageAction extends Action2 {
 			id: ChatSteerWithMessageAction.ID,
 			title: localize2('chat.steerWithMessage', "Steer with Message"),
 			tooltip: localize('chat.steerWithMessage.tooltip', "Send this message at the next opportunity, signaling the current request to yield"),
-			icon: Codicon.arrowRight,
+			icon: Codicon.arrowUp,
 			f1: false,
 			category: CHAT_CATEGORY,
 			precondition: ContextKeyExpr.and(
 				queuingActionsPresent,
 				ChatContextKeys.inputHasText,
 			),
-			keybinding: {
+			keybinding: [{
 				when: ContextKeyExpr.and(
 					ChatContextKeys.inChatInput,
 					queuingActionsPresent,
+					effectiveDefaultIsSteer,
 				),
 				primary: KeyCode.Enter,
 				weight: KeybindingWeight.EditorContrib + 1
-			},
+			}, {
+				when: ContextKeyExpr.and(
+					ChatContextKeys.inChatInput,
+					queuingActionsPresent,
+					effectiveDefaultIsQueue,
+				),
+				primary: KeyMod.Alt | KeyCode.Enter,
+				weight: KeybindingWeight.EditorContrib + 1
+			}],
 		});
 	}
 
@@ -182,7 +219,7 @@ export class ChatSendPendingImmediatelyAction extends Action2 {
 		});
 	}
 
-	override run(accessor: ServicesAccessor, ...args: unknown[]): void {
+	override async run(accessor: ServicesAccessor, ...args: unknown[]): Promise<void> {
 		const chatService = accessor.get(IChatService);
 		const widgetService = accessor.get(IChatWidgetService);
 		const [context] = args;
@@ -213,7 +250,7 @@ export class ChatSendPendingImmediatelyAction extends Action2 {
 		];
 
 		chatService.setPendingRequests(context.sessionResource, reordered);
-		chatService.cancelCurrentRequestForSession(context.sessionResource);
+		await chatService.cancelCurrentRequestForSession(context.sessionResource, 'queueRunNext');
 		chatService.processPendingRequests(context.sessionResource);
 	}
 }
@@ -271,7 +308,7 @@ export function registerChatQueueActions(): void {
 		order: 1,
 	});
 	MenuRegistry.appendMenuItem(MenuId.ChatExecuteQueue, {
-		command: { id: ChatSteerWithMessageAction.ID, title: localize2('chat.steerWithMessage', "Steer with Message"), icon: Codicon.arrowRight },
+		command: { id: ChatSteerWithMessageAction.ID, title: localize2('chat.steerWithMessage', "Steer with Message"), icon: Codicon.arrowUp },
 		group: 'navigation',
 		order: 2,
 	});
@@ -280,7 +317,10 @@ export function registerChatQueueActions(): void {
 		submenu: MenuId.ChatExecuteQueue,
 		title: localize2('chat.queueSubmenu', "Queue"),
 		icon: Codicon.listOrdered,
-		when: queuingActionsPresent,
+		when: ContextKeyExpr.and(
+			queuingActionsPresent,
+			ChatContextKeys.inputHasText,
+		),
 		group: 'navigation',
 		order: 4,
 	});
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatToolActions.ts b/src/vs/workbench/contrib/chat/browser/actions/chatToolActions.ts
index 7afcbdd62aa07..a144b6178534d 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatToolActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatToolActions.ts
@@ -121,7 +121,7 @@ export class ConfigureToolsAction extends Action2 {
 		super({
 			id: ConfigureToolsAction.ID,
 			title: localize('label', "Configure Tools..."),
-			icon: Codicon.tools,
+			icon: Codicon.settings,
 			f1: false,
 			category: CHAT_CATEGORY,
 			precondition: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
diff --git a/src/vs/workbench/contrib/chat/browser/actions/chatToolPicker.ts b/src/vs/workbench/contrib/chat/browser/actions/chatToolPicker.ts
index 91e60f599dee2..7d8e0512eafb1 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/chatToolPicker.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/chatToolPicker.ts
@@ -22,6 +22,7 @@ import { IMcpRegistry } from '../../../mcp/common/mcpRegistryTypes.js';
 import { IMcpServer, IMcpService, IMcpWorkbenchService, McpConnectionState, McpServerCacheState, McpServerEditorTab } from '../../../mcp/common/mcpTypes.js';
 import { startServerAndWaitForLiveTools } from '../../../mcp/common/mcpTypesUtils.js';
 import { ILanguageModelChatMetadata } from '../../common/languageModels.js';
+import { ILanguageModelToolsConfirmationService } from '../../common/tools/languageModelToolsConfirmationService.js';
 import { ILanguageModelToolsService, IToolData, IToolSet, ToolDataSource, ToolSet } from '../../common/tools/languageModelToolsService.js';
 import { ConfigureToolSets } from '../tools/toolSetsContribution.js';
 
@@ -31,7 +32,7 @@ const enum BucketOrdinal { User, BuiltIn, Mcp, Extension }
 type BucketPick = IQuickPickItem & { picked: boolean; ordinal: BucketOrdinal; status?: string; toolset?: ToolSet; children: (ToolPick | ToolSetPick)[] };
 type ToolSetPick = IQuickPickItem & { picked: boolean; toolset: ToolSet; parent: BucketPick };
 type ToolPick = IQuickPickItem & { picked: boolean; tool: IToolData; parent: BucketPick };
-type ActionableButton = IQuickInputButton & { action: () => void };
+type ActionableButton = IQuickInputButton & { action: () => void; keepOpen?: boolean };
 
 // New QuickTree types for tree-based implementation
 
@@ -77,6 +78,7 @@ interface IToolSetTreeItem extends IToolTreeItem {
 interface IToolTreeItemData extends IToolTreeItem {
 	readonly itemType: 'tool';
 	readonly tool: IToolData;
+	buttons?: ActionableButton[];
 	checked: boolean;
 }
 
@@ -205,6 +207,7 @@ export async function showToolsPicker(
 	const editorService = accessor.get(IEditorService);
 	const mcpWorkbenchService = accessor.get(IMcpWorkbenchService);
 	const toolsService = accessor.get(ILanguageModelToolsService);
+	const confirmationService = accessor.get(ILanguageModelToolsConfirmationService);
 	const telemetryService = accessor.get(ITelemetryService);
 
 	const mcpServerByTool = new Map<string, IMcpServer>();
@@ -451,6 +454,38 @@ export async function showToolsPicker(
 				}
 			}
 		}
+		// Add approval management buttons to tool items that support confirmation
+		for (const bucket of sortedBuckets) {
+			const isMcpBucket = bucket.ordinal === BucketOrdinal.Mcp;
+			const addConfirmationButton = (toolItem: IToolTreeItemData) => {
+				if (!confirmationService.toolCanManageConfirmation(toolItem.tool)) {
+					return;
+				}
+				const tool = toolItem.tool;
+				const manageTools = isMcpBucket ? bucket.children.flatMap(c => isToolTreeItem(c) ? [c.tool] : isToolSetTreeItem(c) && c.children ? c.children.filter(isToolTreeItem).map(gc => gc.tool) : []) : [tool];
+				const buttons: ActionableButton[] = toolItem.buttons ? [...toolItem.buttons] : [];
+				buttons.push({
+					iconClass: ThemeIcon.asClassName(Codicon.pass),
+					tooltip: localize('manageToolApproval', "Manage Approval"),
+					keepOpen: true,
+					action: () => confirmationService.manageConfirmationPreferences(manageTools, { focusToolId: tool.id })
+				});
+				toolItem.buttons = buttons;
+			};
+
+			for (const child of bucket.children) {
+				if (isToolTreeItem(child)) {
+					addConfirmationButton(child);
+				} else if (isToolSetTreeItem(child) && child.children) {
+					for (const grandchild of child.children) {
+						if (isToolTreeItem(grandchild)) {
+							addConfirmationButton(grandchild);
+						}
+					}
+				}
+			}
+		}
+
 		if (treeItems.length === 0) {
 			treePicker.placeholder = localize('noTools', "Add tools to chat");
 		} else {
@@ -474,7 +509,8 @@ export async function showToolsPicker(
 	// Handle button triggers
 	store.add(treePicker.onDidTriggerItemButton(e => {
 		if (e.button && typeof (e.button as ActionableButton).action === 'function') {
-			(e.button as ActionableButton).action();
+			const actionableButton = e.button as ActionableButton;
+			actionableButton.action();
 			store.dispose();
 		}
 	}));
diff --git a/src/vs/workbench/contrib/chat/browser/actions/codeBlockOperations.ts b/src/vs/workbench/contrib/chat/browser/actions/codeBlockOperations.ts
index 0baba0ac0dc69..df32c865dff3b 100644
--- a/src/vs/workbench/contrib/chat/browser/actions/codeBlockOperations.ts
+++ b/src/vs/workbench/contrib/chat/browser/actions/codeBlockOperations.ts
@@ -117,7 +117,7 @@ export class InsertCodeBlockOperation {
 
 		const edits = [new ResourceTextEdit(activeModel.uri, { range, text })];
 		await this.bulkEditService.apply(edits);
-		this.codeEditorService.listCodeEditors().find(editor => editor.getModel()?.uri.toString() === activeModel.uri.toString())?.focus();
+		this.codeEditorService.listCodeEditors().find(editor => isEqual(editor.getModel()?.uri, activeModel.uri))?.focus();
 		return true;
 	}
 
diff --git a/src/vs/workbench/contrib/chat/browser/agentPluginActions.ts b/src/vs/workbench/contrib/chat/browser/agentPluginActions.ts
new file mode 100644
index 0000000000000..29d788865e8a0
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/agentPluginActions.ts
@@ -0,0 +1,276 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Action, IAction, IActionChangeEvent } from '../../../../base/common/actions.js';
+import { Emitter } from '../../../../base/common/event.js';
+import { IActionViewItemOptions } from '../../../../base/browser/ui/actionbar/actionViewItems.js';
+import { ActionWithDropdownActionViewItem, IActionWithDropdownActionViewItemOptions } from '../../../../base/browser/ui/dropdown/dropdownActionViewItem.js';
+import { IContextMenuProvider } from '../../../../base/browser/contextmenu.js';
+import { localize } from '../../../../nls.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IOpenerService } from '../../../../platform/opener/common/opener.js';
+import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
+import { IWorkspaceContextService, WorkbenchState } from '../../../../platform/workspace/common/workspace.js';
+import { dirname, joinPath } from '../../../../base/common/resources.js';
+import { ContributionEnablementState, IEnablementModel, isContributionDisabled, isContributionEnabled } from '../common/enablement.js';
+import { IAgentPlugin, IAgentPluginService } from '../common/plugins/agentPluginService.js';
+import { IPluginInstallService } from '../common/plugins/pluginInstallService.js';
+import { IMarketplacePluginItem } from './agentPluginEditor/agentPluginItems.js';
+import { buildEnablementContextMenuGroup } from './enablementActions.js';
+import { hasKey } from '../../../../base/common/types.js';
+
+//#region Simple actions
+
+export class InstallPluginAction extends Action {
+	constructor(
+		item: IMarketplacePluginItem,
+		@IPluginInstallService pluginInstallService: IPluginInstallService,
+	) {
+		super('agentPlugin.install', localize('install', "Install"), 'extension-action label prominent install', true,
+			() => pluginInstallService.installPlugin({
+				name: item.name,
+				description: item.description,
+				version: '',
+				source: item.source,
+				sourceDescriptor: item.sourceDescriptor,
+				marketplace: item.marketplace,
+				marketplaceReference: item.marketplaceReference,
+				marketplaceType: item.marketplaceType,
+				readmeUri: item.readmeUri,
+			}));
+	}
+}
+
+export class UninstallPluginAction extends Action {
+	constructor(plugin: IAgentPlugin) {
+		super('agentPlugin.uninstall', localize('uninstall', "Uninstall"), 'extension-action label uninstall', true,
+			() => { plugin.remove(); return Promise.resolve(); });
+	}
+}
+
+export class OpenPluginFolderAction extends Action {
+	constructor(
+		plugin: IAgentPlugin,
+		@ICommandService commandService: ICommandService,
+		@IOpenerService openerService: IOpenerService,
+	) {
+		super('agentPlugin.openFolder', localize('openPluginFolder', "Open Plugin Folder"), undefined, true,
+			async () => {
+				try {
+					await commandService.executeCommand('revealFileInOS', plugin.uri);
+				} catch {
+					await openerService.open(dirname(plugin.uri));
+				}
+			});
+	}
+}
+
+export class OpenPluginReadmeAction extends Action {
+	constructor(
+		readmeUri: import('../../../../base/common/uri.js').URI,
+		@IOpenerService openerService: IOpenerService,
+	) {
+		super('agentPlugin.openReadme', localize('openReadme', "Open README"), undefined, true,
+			() => openerService.open(readmeUri));
+	}
+}
+
+//#endregion
+
+//#region Context menu
+
+/**
+ * Builds the standard context menu action groups for an installed plugin.
+ */
+export function getInstalledPluginContextMenuActions(plugin: IAgentPlugin, instantiationService: IInstantiationService): IAction[][] {
+	return instantiationService.invokeFunction(accessor => {
+		const agentPluginService = accessor.get(IAgentPluginService);
+		const workspaceService = accessor.get(IWorkspaceContextService);
+		const groups: IAction[][] = [];
+		groups.push(buildEnablementContextMenuGroup(
+			plugin.enablement.get(),
+			plugin.uri.toString(),
+			agentPluginService.enablementModel,
+			workspaceService,
+			'agentPlugin',
+		));
+		groups.push([
+			instantiationService.createInstance(OpenPluginFolderAction, plugin),
+			instantiationService.createInstance(OpenPluginReadmeAction, joinPath(plugin.uri, 'README.md')),
+		]);
+		if (plugin.fromMarketplace) {
+			groups.push([new UninstallPluginAction(plugin)]);
+		}
+		return groups;
+	});
+}
+
+//#endregion
+
+//#region Dropdown enablement actions for editor-style action bars
+
+/**
+ * Sub-action base class that auto-hides when disabled, for use inside
+ * {@link EnablementDropDownAction}.
+ */
+class EnablementSubAction extends Action {
+	private _hidden: boolean;
+	get hidden(): boolean { return this._hidden; }
+	set hidden(v: boolean) { this._hidden = v; }
+
+	constructor(id: string, label: string, cssClass: string, enabled: boolean, actionCallback: () => Promise<void>) {
+		super(id, label, cssClass, enabled, actionCallback);
+		this._hidden = !enabled;
+	}
+
+	protected override _setEnabled(value: boolean): void {
+		super._setEnabled(value);
+		this.hidden = !value;
+	}
+}
+
+interface IEnablementActionChangeEvent extends IActionChangeEvent {
+	readonly menuActions?: IAction[];
+}
+
+/**
+ * Dropdown action that aggregates enablement sub-actions and shows the
+ * first visible one as the primary button, with others in the dropdown.
+ * Hides itself entirely when all sub-actions are hidden.
+ */
+export class EnablementDropDownAction extends Action {
+	readonly menuActionClassNames = ['extension-action', 'label', 'action-dropdown'];
+	private _menuActions: IAction[] = [];
+	get menuActions(): IAction[] { return [...this._menuActions]; }
+
+	private _isHidden = false;
+	get isHidden(): boolean { return this._isHidden; }
+
+	protected override readonly _onDidChange = new Emitter<IEnablementActionChangeEvent>();
+	override get onDidChange() { return this._onDidChange.event; }
+
+	private readonly subActions: EnablementSubAction[];
+
+	constructor(id: string, subActions: EnablementSubAction[]) {
+		super(id, undefined, 'extension-action label action-dropdown');
+		this.subActions = subActions;
+		for (const a of subActions) {
+			a.onDidChange(() => this._updateDropdown());
+		}
+		this._updateDropdown();
+	}
+
+	private _updateDropdown(): void {
+		const visible = this.subActions.filter(a => !a.hidden);
+		const primary = visible[0];
+		this._menuActions = visible.length > 1 ? [...visible] : [];
+
+		if (primary) {
+			this._isHidden = false;
+			this.enabled = true;
+			this.label = primary.label;
+			this.tooltip = primary.tooltip;
+		} else {
+			this._isHidden = true;
+			this.enabled = false;
+		}
+		this._onDidChange.fire({ menuActions: this._menuActions });
+	}
+
+	override async run(): Promise<void> {
+		const primary = this.subActions.find(a => !a.hidden);
+		await primary?.run();
+	}
+
+	override dispose(): void {
+		for (const a of this.subActions) {
+			a.dispose();
+		}
+		super.dispose();
+	}
+}
+
+/**
+ * View item for {@link EnablementDropDownAction} that properly hides
+ * the dropdown chevron when there are no secondary actions.
+ */
+export class EnablementDropdownActionViewItem extends ActionWithDropdownActionViewItem {
+	constructor(
+		action: EnablementDropDownAction,
+		options: IActionViewItemOptions & IActionWithDropdownActionViewItemOptions,
+		contextMenuProvider: IContextMenuProvider,
+	) {
+		super(null, action, options, contextMenuProvider);
+		this._register(action.onDidChange(e => {
+			if (hasKey(e, { menuActions: true })) {
+				this.updateClass();
+			}
+		}));
+	}
+
+	override render(container: HTMLElement): void {
+		super.render(container);
+		this.updateClass();
+	}
+
+	protected override updateClass(): void {
+		super.updateClass();
+		if (this.element && this.dropdownMenuActionViewItem?.element) {
+			const action = this._action as EnablementDropDownAction;
+			this.element.classList.toggle('hide', action.isHidden);
+			const isMenuEmpty = action.menuActions.length === 0;
+			this.element.classList.toggle('empty', isMenuEmpty);
+			this.dropdownMenuActionViewItem.element.classList.toggle('hide', isMenuEmpty);
+		}
+	}
+}
+
+/**
+ * Creates the enable dropdown action for a plugin, containing Enable
+ * and Enable (Workspace) sub-actions.
+ */
+export function createEnablePluginDropDown(
+	plugin: IAgentPlugin,
+	enablementModel: IEnablementModel,
+	workspaceContextService: IWorkspaceContextService,
+): EnablementDropDownAction {
+	const key = plugin.uri.toString();
+	const hasWorkspace = workspaceContextService.getWorkbenchState() !== WorkbenchState.EMPTY;
+
+	const enable = new EnablementSubAction('agentPlugin.enable', localize('enable', "Enable"), 'extension-action label prominent',
+		isContributionDisabled(plugin.enablement.get()),
+		() => { enablementModel.setEnabled(key, ContributionEnablementState.EnabledProfile); return Promise.resolve(); });
+
+	const enableWorkspace = new EnablementSubAction('agentPlugin.enableForWorkspace', localize('enableForWorkspace', "Enable (Workspace)"), 'extension-action label',
+		isContributionDisabled(plugin.enablement.get()) && hasWorkspace,
+		() => { enablementModel.setEnabled(key, ContributionEnablementState.EnabledWorkspace); return Promise.resolve(); });
+
+	return new EnablementDropDownAction('agentPlugin.enableDropdown', [enable, enableWorkspace]);
+}
+
+/**
+ * Creates the disable dropdown action for a plugin, containing Disable
+ * and Disable (Workspace) sub-actions.
+ */
+export function createDisablePluginDropDown(
+	plugin: IAgentPlugin,
+	enablementModel: IEnablementModel,
+	workspaceContextService: IWorkspaceContextService,
+): EnablementDropDownAction {
+	const key = plugin.uri.toString();
+	const hasWorkspace = workspaceContextService.getWorkbenchState() !== WorkbenchState.EMPTY;
+
+	const disable = new EnablementSubAction('agentPlugin.disable', localize('disable', "Disable"), 'extension-action label disable',
+		isContributionEnabled(plugin.enablement.get()),
+		() => { enablementModel.setEnabled(key, ContributionEnablementState.DisabledProfile); return Promise.resolve(); });
+
+	const disableWorkspace = new EnablementSubAction('agentPlugin.disableForWorkspace', localize('disableForWorkspace', "Disable (Workspace)"), 'extension-action label disable',
+		isContributionEnabled(plugin.enablement.get()) && hasWorkspace,
+		() => { enablementModel.setEnabled(key, ContributionEnablementState.DisabledWorkspace); return Promise.resolve(); });
+
+	return new EnablementDropDownAction('agentPlugin.disableDropdown', [disable, disableWorkspace]);
+}
+
+//#endregion
diff --git a/src/vs/workbench/contrib/chat/browser/agentPluginEditor/agentPluginEditor.ts b/src/vs/workbench/contrib/chat/browser/agentPluginEditor/agentPluginEditor.ts
new file mode 100644
index 0000000000000..7618325ea959d
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/agentPluginEditor/agentPluginEditor.ts
@@ -0,0 +1,592 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { $, Dimension, EventType, addDisposableListener, append, reset, setParentFlowTo } from '../../../../../base/browser/dom.js';
+import { ActionBar } from '../../../../../base/browser/ui/actionbar/actionbar.js';
+import { IActionViewItemOptions } from '../../../../../base/browser/ui/actionbar/actionViewItems.js';
+import { Action, IAction } from '../../../../../base/common/actions.js';
+import * as arrays from '../../../../../base/common/arrays.js';
+import { Cache, CacheResult } from '../../../../../base/common/cache.js';
+import { CancellationToken, CancellationTokenSource } from '../../../../../base/common/cancellation.js';
+import { DisposableStore, toDisposable } from '../../../../../base/common/lifecycle.js';
+import { Schemas, matchesScheme } from '../../../../../base/common/network.js';
+import { autorun, derived } from '../../../../../base/common/observable.js';
+import { dirname, joinPath } from '../../../../../base/common/resources.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { generateUuid } from '../../../../../base/common/uuid.js';
+import { TokenizationRegistry } from '../../../../../editor/common/languages.js';
+import { ILanguageService } from '../../../../../editor/common/languages/language.js';
+import { generateTokensCSSForColorMap } from '../../../../../editor/common/languages/supports/tokenization.js';
+import { localize } from '../../../../../nls.js';
+import { IFileService } from '../../../../../platform/files/common/files.js';
+import { IInstantiationService } from '../../../../../platform/instantiation/common/instantiation.js';
+import { IContextMenuService } from '../../../../../platform/contextview/browser/contextView.js';
+import { ILabelService } from '../../../../../platform/label/common/label.js';
+import { IOpenerService } from '../../../../../platform/opener/common/opener.js';
+import { IRequestService, asText } from '../../../../../platform/request/common/request.js';
+import { IStorageService } from '../../../../../platform/storage/common/storage.js';
+import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
+import { IThemeService } from '../../../../../platform/theme/common/themeService.js';
+import { EditorPane } from '../../../../browser/parts/editor/editorPane.js';
+import { IEditorOpenContext } from '../../../../common/editor.js';
+import { IEditorGroup } from '../../../../services/editor/common/editorGroupsService.js';
+import { IExtensionService } from '../../../../services/extensions/common/extensions.js';
+import { DEFAULT_MARKDOWN_STYLES, renderMarkdownDocument } from '../../../markdown/browser/markdownDocumentRenderer.js';
+import { IWebview, IWebviewService } from '../../../webview/browser/webview.js';
+import { IAgentPlugin, IAgentPluginService } from '../../common/plugins/agentPluginService.js';
+import { IPluginInstallService } from '../../common/plugins/pluginInstallService.js';
+import { hasSourceChanged, IMarketplacePlugin, IPluginMarketplaceService } from '../../common/plugins/pluginMarketplaceService.js';
+import { AgentPluginEditorInput } from './agentPluginEditorInput.js';
+import { AgentPluginItemKind, IAgentPluginItem, IInstalledPluginItem } from './agentPluginItems.js';
+import { IWorkspaceContextService } from '../../../../../platform/workspace/common/workspace.js';
+import { EnablementStatusWidget, pluginEnablementLabels } from '../enablementStatusWidget.js';
+import { InstallPluginAction, UninstallPluginAction, createEnablePluginDropDown, createDisablePluginDropDown, EnablementDropDownAction, EnablementDropdownActionViewItem } from '../agentPluginActions.js';
+import './media/agentPluginEditor.css';
+
+interface IAgentPluginEditorTemplate {
+	name: HTMLElement;
+	description: HTMLElement;
+	marketplace: HTMLElement;
+	actionBar: ActionBar;
+	statusContainer: HTMLElement;
+	content: HTMLElement;
+	header: HTMLElement;
+}
+
+interface ILayoutParticipant {
+	layout(): void;
+}
+
+interface IActiveElement {
+	focus(): void;
+}
+
+const enum WebviewIndex {
+	Readme,
+}
+
+export class AgentPluginEditor extends EditorPane {
+
+	static readonly ID: string = 'workbench.editor.agentPlugin';
+
+	private template: IAgentPluginEditorTemplate | undefined;
+
+	private pluginReadme: Cache<string> | null = null;
+
+	private initialScrollProgress: Map<WebviewIndex, number> = new Map();
+	private currentIdentifier: string = '';
+
+	private layoutParticipants: ILayoutParticipant[] = [];
+	private readonly contentDisposables = this._register(new DisposableStore());
+	private readonly transientDisposables = this._register(new DisposableStore());
+	private activeElement: IActiveElement | null = null;
+	private dimension: Dimension | undefined;
+
+	constructor(
+		group: IEditorGroup,
+		@ITelemetryService telemetryService: ITelemetryService,
+		@IInstantiationService private readonly instantiationService: IInstantiationService,
+		@IThemeService themeService: IThemeService,
+		@IOpenerService private readonly openerService: IOpenerService,
+		@IStorageService storageService: IStorageService,
+		@IExtensionService private readonly extensionService: IExtensionService,
+		@IWebviewService private readonly webviewService: IWebviewService,
+		@ILanguageService private readonly languageService: ILanguageService,
+		@IFileService private readonly fileService: IFileService,
+		@IRequestService private readonly requestService: IRequestService,
+		@IAgentPluginService private readonly agentPluginService: IAgentPluginService,
+		@IPluginInstallService private readonly pluginInstallService: IPluginInstallService,
+		@IPluginMarketplaceService private readonly pluginMarketplaceService: IPluginMarketplaceService,
+		@ILabelService private readonly labelService: ILabelService,
+		@IContextMenuService private readonly contextMenuService: IContextMenuService,
+	) {
+		super(AgentPluginEditor.ID, group, telemetryService, themeService, storageService);
+	}
+
+	protected createEditor(parent: HTMLElement): void {
+		const root = append(parent, $('.extension-editor.agent-plugin-editor'));
+
+		root.tabIndex = 0;
+		root.style.outline = 'none';
+		root.setAttribute('role', 'document');
+		const header = append(root, $('.header'));
+
+		const iconContainer = append(header, $('.icon-container'));
+		const icon = append(iconContainer, $('span.codicon.codicon-extensions'));
+		icon.style.fontSize = '64px';
+
+		const details = append(header, $('.details'));
+		const title = append(details, $('.title'));
+		const name = append(title, $('span.name', { role: 'heading', tabIndex: 0 }));
+
+		const description = append(details, $('.description'));
+
+		const subtitle = append(details, $('.subtitle'));
+		const marketplace = append(subtitle, $('span.subtitle-entry'));
+
+		const actionsAndStatusContainer = append(details, $('.actions-status-container'));
+		const actionBar = this._register(new ActionBar(actionsAndStatusContainer, {
+			actionViewItemProvider: (action: IAction, options: IActionViewItemOptions) => {
+				if (action instanceof EnablementDropDownAction) {
+					return new EnablementDropdownActionViewItem(
+						action,
+						{
+							...options,
+							icon: true,
+							label: true,
+							menuActionsOrProvider: { getActions: () => action.menuActions },
+							menuActionClassNames: action.menuActionClassNames,
+						},
+						this.contextMenuService,
+					);
+				}
+				return undefined;
+			},
+			focusOnlyEnabledItems: true
+		}));
+		actionBar.setFocusable(true);
+
+		const statusContainer = append(actionsAndStatusContainer, $('.status'));
+
+		const body = append(root, $('.body'));
+		const content = append(body, $('.content'));
+		content.id = generateUuid();
+
+		this.template = {
+			content,
+			description,
+			header,
+			name,
+			marketplace,
+			actionBar,
+			statusContainer,
+		};
+	}
+
+	override async setInput(input: AgentPluginEditorInput, options: undefined, context: IEditorOpenContext, token: CancellationToken): Promise<void> {
+		await super.setInput(input, options, context, token);
+		if (this.template) {
+			await this.render(input.item, this.template);
+		}
+	}
+
+	private async render(item: IAgentPluginItem, template: IAgentPluginEditorTemplate): Promise<void> {
+		this.activeElement = null;
+		this.transientDisposables.clear();
+		this.contentDisposables.clear();
+		template.content.innerText = '';
+
+		const cts = new CancellationTokenSource();
+		this.transientDisposables.add(toDisposable(() => cts.dispose(true)));
+		const token = cts.token;
+
+		const itemId = item.kind === AgentPluginItemKind.Installed ? item.plugin.uri.toString() : `${item.marketplaceReference.canonicalId}/${item.source}`;
+
+		if (this.currentIdentifier !== itemId) {
+			this.initialScrollProgress.clear();
+			this.currentIdentifier = itemId;
+		}
+
+		this.pluginReadme = new Cache(() => this.fetchReadme(item, token));
+
+		template.name.textContent = item.name;
+		template.description.textContent = item.description;
+
+		// Set up marketplace link
+		const marketplaceLabel = item.marketplace ?? '';
+		const githubRepo = item.kind === AgentPluginItemKind.Marketplace
+			? item.marketplaceReference.githubRepo
+			: item.plugin.fromMarketplace?.marketplaceReference.githubRepo;
+		if (marketplaceLabel && githubRepo) {
+			const url = `https://github.com/${githubRepo}`;
+			const link = $('a.marketplace-link', { href: url }, marketplaceLabel);
+			this.transientDisposables.add(addDisposableListener(link, EventType.CLICK, (e) => {
+				e.preventDefault();
+				e.stopPropagation();
+				this.openerService.open(URI.parse(url));
+			}));
+			reset(template.marketplace, link);
+		} else {
+			reset(template.marketplace, marketplaceLabel);
+		}
+
+		const currentItem = derived(reader => {
+			// Read observables to subscribe to changes
+			const allPlugins = this.agentPluginService.plugins.read(reader);
+
+			let currentItem = item;
+
+			// If this was a marketplace item, check if it got installed
+			if (item.kind === AgentPluginItemKind.Marketplace) {
+				const expectedUri = this.pluginInstallService.getPluginInstallUri({
+					name: item.name,
+					description: item.description,
+					version: '',
+					source: item.source,
+					sourceDescriptor: item.sourceDescriptor,
+					marketplace: item.marketplace,
+					marketplaceReference: item.marketplaceReference,
+					marketplaceType: item.marketplaceType,
+				});
+				const installedPlugin = allPlugins.find(p => p.uri.toString() === expectedUri.toString());
+				if (installedPlugin) {
+					currentItem = this.installedPluginToItem(installedPlugin);
+				}
+			} else {
+				// If this was an installed item, check if it got uninstalled
+				const stillInstalled = allPlugins.find(p => p.uri.toString() === item.plugin.uri.toString());
+				if (!stillInstalled) {
+					// Plugin was uninstalled — show as marketplace if we have the info
+					if (item.plugin.fromMarketplace) {
+						const mp = item.plugin.fromMarketplace;
+						currentItem = {
+							kind: AgentPluginItemKind.Marketplace,
+							name: item.name,
+							description: mp.description,
+							source: mp.source,
+							sourceDescriptor: mp.sourceDescriptor,
+							marketplace: mp.marketplace,
+							marketplaceReference: mp.marketplaceReference,
+							marketplaceType: mp.marketplaceType,
+							readmeUri: mp.readmeUri,
+						};
+					} else {
+						// Non-marketplace plugin was uninstalled — no actions to show
+						return;
+					}
+				} else {
+					// Read enablement state for reactivity
+					stillInstalled.enablement.read(reader);
+					currentItem = this.installedPluginToItem(stillInstalled);
+				}
+			}
+
+			return currentItem;
+		});
+
+		const storedPlugin = currentItem.map((item, r) => {
+			if (!item || item.kind === AgentPluginItemKind.Marketplace) {
+				return undefined;
+			}
+
+			return this.pluginMarketplaceService.installedPlugins.read(r)
+				.find(e => e.pluginUri.toString() === item.plugin.uri.toString())?.plugin
+				?? item.plugin.fromMarketplace;
+		});
+
+		// Set up actions reactively
+		const actionDisposables = this.transientDisposables.add(new DisposableStore());
+		this.transientDisposables.add(autorun(reader => {
+			actionDisposables.clear();
+			template.actionBar.clear();
+
+			const current = currentItem.read(reader);
+			if (!current) {
+				return;
+			}
+
+			this.pluginMarketplaceService.lastFetchedPlugins.read(reader);
+
+			const actions = this.getItemActions(current, storedPlugin.read(reader));
+			if (actions.length > 0) {
+				template.actionBar.push(actions, { icon: true, label: true });
+			}
+			for (const action of actions) {
+				actionDisposables.add(action);
+			}
+
+			// Update enablement status widget
+			if (current.kind === AgentPluginItemKind.Installed) {
+				actionDisposables.add(this.instantiationService.createInstance(
+					EnablementStatusWidget,
+					template.statusContainer,
+					current.plugin.enablement,
+					pluginEnablementLabels,
+				));
+			}
+		}));
+
+		// Open readme
+		this.activeElement = await this.openDetails(item, template, token);
+	}
+
+	private getItemActions(item: IAgentPluginItem, storedPlugin: IMarketplacePlugin | undefined): Action[] {
+		if (item.kind === AgentPluginItemKind.Marketplace) {
+			return [this.instantiationService.createInstance(InstallPluginAction, item)];
+		}
+
+		const workspaceService = this.instantiationService.invokeFunction(a => a.get(IWorkspaceContextService));
+		const actions: Action[] = [];
+
+		if (storedPlugin) {
+			const cachedMarketplace = this.pluginMarketplaceService.lastFetchedPlugins.get();
+			const key = `${storedPlugin.marketplaceReference.canonicalId}::${storedPlugin.name}`;
+			const livePlugin = cachedMarketplace.find(mp =>
+				`${mp.marketplaceReference.canonicalId}::${mp.name}` === key
+			);
+			if (livePlugin && hasSourceChanged(storedPlugin.sourceDescriptor, livePlugin.sourceDescriptor)) {
+				actions.push(this.instantiationService.createInstance(UpdatePluginEditorAction, item.plugin, livePlugin));
+			}
+		}
+
+		actions.push(createEnablePluginDropDown(item.plugin, this.agentPluginService.enablementModel, workspaceService));
+		actions.push(createDisablePluginDropDown(item.plugin, this.agentPluginService.enablementModel, workspaceService));
+		actions.push(new UninstallPluginAction(item.plugin));
+		return actions;
+	}
+
+	private installedPluginToItem(plugin: IAgentPlugin): IInstalledPluginItem {
+		const name = plugin.label;
+		const description = plugin.fromMarketplace?.description ?? this.labelService.getUriLabel(dirname(plugin.uri), { relative: true });
+		const marketplace = plugin.fromMarketplace?.marketplace;
+		return { kind: AgentPluginItemKind.Installed, name, description, marketplace, plugin };
+	}
+
+	private async fetchReadme(item: IAgentPluginItem, token: CancellationToken): Promise<string> {
+		let readmeUri: URI | undefined;
+		if (item.kind === AgentPluginItemKind.Installed) {
+			readmeUri = joinPath(item.plugin.uri, 'README.md');
+		} else {
+			readmeUri = item.readmeUri;
+		}
+
+		if (!readmeUri) {
+			return '';
+		}
+
+		if (readmeUri.scheme === Schemas.file || readmeUri.scheme === Schemas.vscodeRemote) {
+			try {
+				const content = await this.fileService.readFile(readmeUri);
+				return content.value.toString();
+			} catch {
+				return '';
+			}
+		}
+
+		// For https GitHub URLs, convert blob URL to raw URL
+		if (readmeUri.scheme === Schemas.https) {
+			let rawUrl = readmeUri.toString();
+			const githubBlobMatch = rawUrl.match(/^https:\/\/github\.com\/(?<owner>[^/]+)\/(?<repo>[^/]+)\/blob\/(?<rest>.+)$/);
+			if (githubBlobMatch?.groups) {
+				rawUrl = `https://raw.githubusercontent.com/${githubBlobMatch.groups['owner']}/${githubBlobMatch.groups['repo']}/${githubBlobMatch.groups['rest']}`;
+			}
+			try {
+				const context = await this.requestService.request({ type: 'GET', url: rawUrl, callSite: 'agentPluginEditor.fetchReadme' }, token);
+				const text = await asText(context);
+				return text ?? '';
+			} catch {
+				return '';
+			}
+		}
+
+		return '';
+	}
+
+	private async openDetails(item: IAgentPluginItem, template: IAgentPluginEditorTemplate, token: CancellationToken): Promise<IActiveElement | null> {
+		const details = append(template.content, $('.details'));
+		const readmeContainer = append(details, $('.content-container'));
+
+		const layout = () => details.classList.toggle('narrow', this.dimension !== undefined && this.dimension.width < 500);
+		layout();
+		this.contentDisposables.add(toDisposable(arrays.insert(this.layoutParticipants, { layout })));
+
+		return this.openMarkdown(this.pluginReadme!.get(), localize('noReadme', "No README available."), readmeContainer, WebviewIndex.Readme, localize('Readme title', "Readme"), token);
+	}
+
+	private async openMarkdown(cacheResult: CacheResult<string>, noContentCopy: string, container: HTMLElement, webviewIndex: WebviewIndex, title: string, token: CancellationToken): Promise<IActiveElement | null> {
+		try {
+			const body = await this.renderMarkdown(cacheResult, container, token);
+			if (token.isCancellationRequested) {
+				return null;
+			}
+
+			const webview = this.contentDisposables.add(this.webviewService.createWebviewOverlay({
+				title,
+				options: {
+					enableFindWidget: true,
+					tryRestoreScrollPosition: true,
+					disableServiceWorker: true,
+				},
+				contentOptions: {},
+				extension: undefined,
+			}));
+
+			webview.initialScrollProgress = this.initialScrollProgress.get(webviewIndex) || 0;
+
+			webview.claim(this, this.window, undefined);
+			setParentFlowTo(webview.container, container);
+			webview.layoutWebviewOverElement(container);
+
+			webview.setHtml(body);
+			webview.claim(this, this.window, undefined);
+
+			this.contentDisposables.add(webview.onDidFocus(() => this._onDidFocus?.fire()));
+
+			this.contentDisposables.add(webview.onDidScroll(() => this.initialScrollProgress.set(webviewIndex, webview.initialScrollProgress)));
+
+			const removeLayoutParticipant = arrays.insert(this.layoutParticipants, {
+				layout: () => {
+					webview.layoutWebviewOverElement(container);
+				}
+			});
+			this.contentDisposables.add(toDisposable(removeLayoutParticipant));
+
+			let isDisposed = false;
+			this.contentDisposables.add(toDisposable(() => { isDisposed = true; }));
+
+			this.contentDisposables.add(this.themeService.onDidColorThemeChange(async () => {
+				const body = await this.renderMarkdown(cacheResult, container);
+				if (!isDisposed) {
+					webview.setHtml(body);
+				}
+			}));
+
+			this.contentDisposables.add(webview.onDidClickLink(link => {
+				if (!link) {
+					return;
+				}
+				if (matchesScheme(link, Schemas.http) || matchesScheme(link, Schemas.https) || matchesScheme(link, Schemas.mailto)) {
+					this.openerService.open(link);
+				}
+			}));
+
+			return webview;
+		} catch (e) {
+			const p = append(container, $('p.nocontent'));
+			p.textContent = noContentCopy;
+			return p;
+		}
+	}
+
+	private async renderMarkdown(cacheResult: CacheResult<string>, container: HTMLElement, token?: CancellationToken): Promise<string> {
+		const contents = await this.loadContents(() => cacheResult, container);
+		if (token?.isCancellationRequested) {
+			return '';
+		}
+
+		const content = await renderMarkdownDocument(contents, this.extensionService, this.languageService, {}, token);
+		if (token?.isCancellationRequested) {
+			return '';
+		}
+
+		return this.renderBody(content);
+	}
+
+	private renderBody(body: TrustedHTML): string {
+		const nonce = generateUuid();
+		const colorMap = TokenizationRegistry.getColorMap();
+		const css = colorMap ? generateTokensCSSForColorMap(colorMap) : '';
+		return `<!DOCTYPE html>
+		<html>
+			<head>
+				<meta http-equiv="Content-type" content="text/html;charset=UTF-8">
+				<meta http-equiv="Content-Security-Policy" content="default-src 'none'; img-src https: data:; media-src https:; script-src 'none'; style-src 'nonce-${nonce}';">
+				<style nonce="${nonce}">
+					${DEFAULT_MARKDOWN_STYLES}
+
+					body {
+						padding-bottom: 75px;
+					}
+
+					#scroll-to-top {
+						position: fixed;
+						width: 32px;
+						height: 32px;
+						right: 25px;
+						bottom: 25px;
+						background-color: var(--vscode-button-secondaryBackground);
+						border-color: var(--vscode-button-border);
+						border-radius: 50%;
+						cursor: pointer;
+						box-shadow: 1px 1px 1px rgba(0,0,0,.25);
+						outline: none;
+						display: flex;
+						justify-content: center;
+						align-items: center;
+					}
+
+					#scroll-to-top:hover {
+						background-color: var(--vscode-button-secondaryHoverBackground);
+						box-shadow: 2px 2px 2px rgba(0,0,0,.25);
+					}
+
+					body.vscode-high-contrast #scroll-to-top {
+						border-width: 2px;
+						border-style: solid;
+						box-shadow: none;
+					}
+
+					#scroll-to-top span.icon::before {
+						content: "";
+						display: block;
+						background: var(--vscode-button-secondaryForeground);
+						-webkit-mask-image: url('data:image/svg+xml;base64,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');
+						width: 16px;
+						height: 16px;
+					}
+					${css}
+				</style>
+			</head>
+			<body>
+				<a id="scroll-to-top" role="button" aria-label="scroll to top" href="#"><span class="icon"></span></a>
+				${body}
+			</body>
+		</html>`;
+	}
+
+	private loadContents<T>(loadingTask: () => CacheResult<T>, container: HTMLElement): Promise<T> {
+		container.classList.add('loading');
+
+		const result = this.contentDisposables.add(loadingTask());
+		const onDone = () => container.classList.remove('loading');
+		result.promise.then(onDone, onDone);
+
+		return result.promise;
+	}
+
+	override clearInput(): void {
+		this.contentDisposables.clear();
+		this.transientDisposables.clear();
+		super.clearInput();
+	}
+
+	override focus(): void {
+		super.focus();
+		this.activeElement?.focus();
+	}
+
+	public get activeWebview(): IWebview | undefined {
+		if (!this.activeElement || !(this.activeElement as IWebview).runFindAction) {
+			return undefined;
+		}
+		return this.activeElement as IWebview;
+	}
+
+	layout(dimension: Dimension): void {
+		this.dimension = dimension;
+		this.layoutParticipants.forEach(p => p.layout());
+	}
+}
+
+class UpdatePluginEditorAction extends Action {
+	static readonly ID = 'agentPlugin.editor.update';
+
+	constructor(
+		private readonly plugin: IAgentPlugin,
+		private readonly liveMarketplacePlugin: IMarketplacePlugin,
+		@IPluginInstallService private readonly pluginInstallService: IPluginInstallService,
+		@IPluginMarketplaceService private readonly pluginMarketplaceService: IPluginMarketplaceService,
+	) {
+		super(UpdatePluginEditorAction.ID, localize('update', "Update"), 'extension-action label prominent install');
+	}
+
+	override async run(): Promise<void> {
+		if (await this.pluginInstallService.updatePlugin(this.liveMarketplacePlugin)) {
+			this.pluginMarketplaceService.addInstalledPlugin(this.plugin.uri, this.liveMarketplacePlugin);
+		}
+	}
+}
+
+//#endregion
diff --git a/src/vs/workbench/contrib/chat/browser/agentPluginEditor/agentPluginEditorInput.ts b/src/vs/workbench/contrib/chat/browser/agentPluginEditor/agentPluginEditorInput.ts
new file mode 100644
index 0000000000000..d2acd9f94f757
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/agentPluginEditor/agentPluginEditorInput.ts
@@ -0,0 +1,65 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Codicon } from '../../../../../base/common/codicons.js';
+import { Schemas } from '../../../../../base/common/network.js';
+import { ThemeIcon } from '../../../../../base/common/themables.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { localize } from '../../../../../nls.js';
+import { registerIcon } from '../../../../../platform/theme/common/iconRegistry.js';
+import { EditorInputCapabilities, IUntypedEditorInput } from '../../../../common/editor.js';
+import { EditorInput } from '../../../../common/editor/editorInput.js';
+import { AgentPluginItemKind, IAgentPluginItem } from './agentPluginItems.js';
+
+const AgentPluginEditorIcon = registerIcon('agent-plugin-editor-icon', Codicon.extensions, localize('agentPluginEditorLabelIcon', 'Icon of the Agent Plugin editor.'));
+
+function getPluginId(item: IAgentPluginItem): string {
+	if (item.kind === AgentPluginItemKind.Installed) {
+		return item.plugin.uri.toString();
+	}
+	return `${item.marketplaceReference.canonicalId}/${item.source}`;
+}
+
+export class AgentPluginEditorInput extends EditorInput {
+
+	static readonly ID = 'workbench.agentPlugin.input';
+
+	override get typeId(): string {
+		return AgentPluginEditorInput.ID;
+	}
+
+	override get capabilities(): EditorInputCapabilities {
+		return EditorInputCapabilities.Readonly | EditorInputCapabilities.Singleton;
+	}
+
+	override get resource() {
+		return URI.from({
+			scheme: Schemas.extension,
+			path: `/agentPlugin/${encodeURIComponent(getPluginId(this._item))}`
+		});
+	}
+
+	constructor(private _item: IAgentPluginItem) {
+		super();
+	}
+
+	get item(): IAgentPluginItem { return this._item; }
+
+	override getName(): string {
+		return localize('agentPluginInputName', "Plugin: {0}", this._item.name);
+	}
+
+	override getIcon(): ThemeIcon | undefined {
+		return AgentPluginEditorIcon;
+	}
+
+	override matches(other: EditorInput | IUntypedEditorInput): boolean {
+		if (super.matches(other)) {
+			return true;
+		}
+
+		return other instanceof AgentPluginEditorInput && getPluginId(this._item) === getPluginId(other._item);
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/agentPluginEditor/agentPluginItems.ts b/src/vs/workbench/contrib/chat/browser/agentPluginEditor/agentPluginItems.ts
new file mode 100644
index 0000000000000..612cea9bb6201
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/agentPluginEditor/agentPluginItems.ts
@@ -0,0 +1,37 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { IObservable } from '../../../../../base/common/observable.js'; import { URI } from '../../../../../base/common/uri.js';
+import type { IAgentPlugin } from '../../common/plugins/agentPluginService.js';
+import type { IMarketplacePlugin, IMarketplaceReference, IPluginSourceDescriptor, MarketplaceType } from '../../common/plugins/pluginMarketplaceService.js';
+
+export const enum AgentPluginItemKind {
+	Installed = 'installed',
+	Marketplace = 'marketplace',
+}
+
+export interface IInstalledPluginItem {
+	readonly kind: AgentPluginItemKind.Installed;
+	readonly name: string;
+	readonly description: string;
+	readonly marketplace?: string;
+	readonly plugin: IAgentPlugin;
+	/** When set, indicates the plugin has a newer version in the marketplace. */
+	readonly outdated?: IObservable<IMarketplacePlugin | undefined>;
+}
+
+export interface IMarketplacePluginItem {
+	readonly kind: AgentPluginItemKind.Marketplace;
+	readonly name: string;
+	readonly description: string;
+	readonly source: string;
+	readonly sourceDescriptor: IPluginSourceDescriptor;
+	readonly marketplace: string;
+	readonly marketplaceReference: IMarketplaceReference;
+	readonly marketplaceType: MarketplaceType;
+	readonly readmeUri?: URI;
+}
+
+export type IAgentPluginItem = IInstalledPluginItem | IMarketplacePluginItem;
diff --git a/src/vs/workbench/contrib/chat/browser/agentPluginEditor/media/agentPluginEditor.css b/src/vs/workbench/contrib/chat/browser/agentPluginEditor/media/agentPluginEditor.css
new file mode 100644
index 0000000000000..27ce848b8d3db
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/agentPluginEditor/media/agentPluginEditor.css
@@ -0,0 +1,32 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+.agent-plugin-editor {
+	& .marketplace-link {
+		color: var(--vscode-textLink-foreground);
+		text-decoration: none;
+		cursor: pointer;
+
+		&:hover {
+			text-decoration: underline;
+			color: var(--vscode-textLink-activeForeground);
+		}
+	}
+
+	& > .body > .content > .details {
+		display: flex;
+		height: 100%;
+
+		&.narrow {
+			flex-direction: column;
+		}
+
+		& > .content-container {
+			flex: 1;
+			min-width: 0;
+			height: 100%;
+		}
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/agentPluginRepositoryService.ts b/src/vs/workbench/contrib/chat/browser/agentPluginRepositoryService.ts
new file mode 100644
index 0000000000000..92d569bc9bef6
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/agentPluginRepositoryService.ts
@@ -0,0 +1,340 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Action } from '../../../../base/common/actions.js';
+import { SequencerByKey } from '../../../../base/common/async.js';
+import { Lazy } from '../../../../base/common/lazy.js';
+import { revive } from '../../../../base/common/marshalling.js';
+import { dirname, isEqual, isEqualOrParent, joinPath } from '../../../../base/common/resources.js';
+import { URI } from '../../../../base/common/uri.js';
+import { localize } from '../../../../nls.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IEnvironmentService } from '../../../../platform/environment/common/environment.js';
+import { IFileService } from '../../../../platform/files/common/files.js';
+import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
+import { INotificationService, Severity } from '../../../../platform/notification/common/notification.js';
+import { IProgressService, ProgressLocation } from '../../../../platform/progress/common/progress.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
+import type { Dto } from '../../../services/extensions/common/proxyIdentifier.js';
+import { IAgentPluginRepositoryService, IEnsureRepositoryOptions, IPullRepositoryOptions } from '../common/plugins/agentPluginRepositoryService.js';
+import { IMarketplacePlugin, IMarketplaceReference, IPluginSourceDescriptor, MarketplaceReferenceKind, MarketplaceType, PluginSourceKind } from '../common/plugins/pluginMarketplaceService.js';
+import { IPluginSource } from '../common/plugins/pluginSource.js';
+import { GitHubPluginSource, GitUrlPluginSource, NpmPluginSource, PipPluginSource, RelativePathPluginSource } from './pluginSources.js';
+
+const MARKETPLACE_INDEX_STORAGE_KEY = 'chat.plugins.marketplaces.index.v1';
+
+interface IMarketplaceIndexEntry {
+	repositoryUri: URI;
+	marketplaceType?: MarketplaceType;
+}
+
+type IStoredMarketplaceIndex = Dto<Record<string, IMarketplaceIndexEntry>>;
+
+export class AgentPluginRepositoryService implements IAgentPluginRepositoryService {
+	declare readonly _serviceBrand: undefined;
+
+	private readonly _cacheRoot: URI;
+	private readonly _marketplaceIndex = new Lazy<Map<string, IMarketplaceIndexEntry>>(() => this._loadMarketplaceIndex());
+	private readonly _pluginSources: ReadonlyMap<PluginSourceKind, IPluginSource>;
+	private readonly _cloneSequencer = new SequencerByKey<string>();
+
+	constructor(
+		@ICommandService private readonly _commandService: ICommandService,
+		@IEnvironmentService environmentService: IEnvironmentService,
+		@IFileService private readonly _fileService: IFileService,
+		@IInstantiationService instantiationService: IInstantiationService,
+		@ILogService private readonly _logService: ILogService,
+		@INotificationService private readonly _notificationService: INotificationService,
+		@IProgressService private readonly _progressService: IProgressService,
+		@IStorageService private readonly _storageService: IStorageService,
+	) {
+		this._cacheRoot = joinPath(environmentService.cacheHome, 'agentPlugins');
+
+		// Build per-kind source repository map via instantiation service so
+		// each repository can inject its own dependencies.
+		this._pluginSources = new Map<PluginSourceKind, IPluginSource>([
+			[PluginSourceKind.RelativePath, new RelativePathPluginSource()],
+			[PluginSourceKind.GitHub, instantiationService.createInstance(GitHubPluginSource)],
+			[PluginSourceKind.GitUrl, instantiationService.createInstance(GitUrlPluginSource)],
+			[PluginSourceKind.Npm, instantiationService.createInstance(NpmPluginSource)],
+			[PluginSourceKind.Pip, instantiationService.createInstance(PipPluginSource)],
+		]);
+	}
+
+	getPluginSource(kind: PluginSourceKind): IPluginSource {
+		const repo = this._pluginSources.get(kind);
+		if (!repo) {
+			throw new Error(`No source repository registered for kind '${kind}'`);
+		}
+		return repo;
+	}
+
+	getRepositoryUri(marketplace: IMarketplaceReference, marketplaceType?: MarketplaceType): URI {
+		if (marketplace.kind === MarketplaceReferenceKind.LocalFileUri && marketplace.localRepositoryUri) {
+			return marketplace.localRepositoryUri;
+		}
+
+		const indexed = this._marketplaceIndex.value.get(marketplace.canonicalId);
+		if (indexed?.repositoryUri) {
+			return indexed.repositoryUri;
+		}
+
+		return this._getRepoCacheDirForReference(marketplace);
+	}
+
+	getPluginInstallUri(plugin: IMarketplacePlugin): URI {
+		const repoDir = this.getRepositoryUri(plugin.marketplaceReference, plugin.marketplaceType);
+		return this._getPluginDir(repoDir, plugin.source);
+	}
+
+	async ensureRepository(marketplace: IMarketplaceReference, options?: IEnsureRepositoryOptions): Promise<URI> {
+		const repoDir = this.getRepositoryUri(marketplace, options?.marketplaceType);
+		return this._cloneSequencer.queue(repoDir.fsPath, async () => {
+			const repoExists = await this._fileService.exists(repoDir);
+			if (repoExists) {
+				this._updateMarketplaceIndex(marketplace, repoDir, options?.marketplaceType);
+				return repoDir;
+			}
+
+			if (marketplace.kind === MarketplaceReferenceKind.LocalFileUri) {
+				throw new Error(`Local marketplace repository does not exist: ${repoDir.fsPath}`);
+			}
+
+			const progressTitle = options?.progressTitle ?? localize('preparingMarketplace', "Preparing plugin marketplace '{0}'...", marketplace.displayLabel);
+			const failureLabel = options?.failureLabel ?? marketplace.displayLabel;
+			await this._cloneRepository(repoDir, marketplace.cloneUrl, progressTitle, failureLabel);
+			this._updateMarketplaceIndex(marketplace, repoDir, options?.marketplaceType);
+			return repoDir;
+		});
+	}
+
+	async pullRepository(marketplace: IMarketplaceReference, options?: IPullRepositoryOptions): Promise<boolean> {
+		const repoDir = this.getRepositoryUri(marketplace, options?.marketplaceType);
+		const repoExists = await this._fileService.exists(repoDir);
+		if (!repoExists) {
+			this._logService.warn(`[AgentPluginRepositoryService] Cannot update plugin '${options?.pluginName ?? marketplace.displayLabel}': repository not cloned`);
+			return false;
+		}
+
+		const updateLabel = options?.pluginName ?? marketplace.displayLabel;
+
+		try {
+			const doPull = async () => {
+				return !!(await this._commandService.executeCommand<boolean>('_git.pull', repoDir.fsPath));
+			};
+
+			if (options?.silent) {
+				return await doPull();
+			}
+
+			return await this._progressService.withProgress(
+				{
+					location: ProgressLocation.Notification,
+					title: localize('updatingPlugin', "Updating plugin '{0}'...", updateLabel),
+					cancellable: false,
+				},
+				doPull,
+			);
+		} catch (err) {
+			this._logService.error(`[AgentPluginRepositoryService] Failed to update ${marketplace.displayLabel}:`, err);
+			if (!options?.silent) {
+				this._notificationService.notify({
+					severity: Severity.Error,
+					message: localize('pullFailed', "Failed to update plugin '{0}': {1}", options?.failureLabel ?? updateLabel, err?.message ?? String(err)),
+					actions: {
+						primary: [new Action('showGitOutput', localize('showGitOutput', "Show Git Output"), undefined, true, () => {
+							this._commandService.executeCommand('git.showOutput');
+						})],
+					},
+				});
+			}
+			throw err;
+		}
+	}
+
+	private _getRepoCacheDirForReference(reference: IMarketplaceReference): URI {
+		return joinPath(this._cacheRoot, ...reference.cacheSegments);
+	}
+
+	private _loadMarketplaceIndex(): Map<string, IMarketplaceIndexEntry> {
+		const result = new Map<string, IMarketplaceIndexEntry>();
+		const stored = this._storageService.getObject<IStoredMarketplaceIndex>(MARKETPLACE_INDEX_STORAGE_KEY, StorageScope.APPLICATION);
+		if (!stored) {
+			return result;
+		}
+
+		const revived = revive<IStoredMarketplaceIndex>(stored);
+		for (const [canonicalId, entry] of Object.entries(revived)) {
+			if (!entry || !entry.repositoryUri) {
+				continue;
+			}
+
+			result.set(canonicalId, {
+				repositoryUri: entry.repositoryUri,
+				marketplaceType: entry.marketplaceType,
+			});
+		}
+
+		return result;
+	}
+
+	private _updateMarketplaceIndex(marketplace: IMarketplaceReference, repositoryUri: URI, marketplaceType?: MarketplaceType): void {
+		if (marketplace.kind === MarketplaceReferenceKind.LocalFileUri) {
+			return;
+		}
+
+		const previous = this._marketplaceIndex.value.get(marketplace.canonicalId);
+		if (previous && previous.repositoryUri.toString() === repositoryUri.toString() && previous.marketplaceType === marketplaceType) {
+			return;
+		}
+
+		this._marketplaceIndex.value.set(marketplace.canonicalId, { repositoryUri, marketplaceType });
+		this._saveMarketplaceIndex();
+	}
+
+	private _saveMarketplaceIndex(): void {
+		const serialized: IStoredMarketplaceIndex = {};
+		for (const [canonicalId, entry] of this._marketplaceIndex.value) {
+			serialized[canonicalId] = JSON.parse(JSON.stringify({
+				repositoryUri: entry.repositoryUri,
+				marketplaceType: entry.marketplaceType,
+			}));
+		}
+
+		if (Object.keys(serialized).length === 0) {
+			this._storageService.remove(MARKETPLACE_INDEX_STORAGE_KEY, StorageScope.APPLICATION);
+			return;
+		}
+
+		this._storageService.store(MARKETPLACE_INDEX_STORAGE_KEY, JSON.stringify(serialized), StorageScope.APPLICATION, StorageTarget.MACHINE);
+	}
+
+	private async _cloneRepository(repoDir: URI, cloneUrl: string, progressTitle: string, failureLabel: string, ref?: string): Promise<void> {
+		try {
+			await this._progressService.withProgress(
+				{
+					location: ProgressLocation.Notification,
+					title: progressTitle,
+					cancellable: false,
+				},
+				async () => {
+					await this._fileService.createFolder(dirname(repoDir));
+					await this._commandService.executeCommand('_git.cloneRepository', cloneUrl, repoDir.fsPath, ref);
+				}
+			);
+		} catch (err) {
+			this._logService.error(`[AgentPluginRepositoryService] Failed to clone ${cloneUrl}:`, err);
+			this._notificationService.notify({
+				severity: Severity.Error,
+				message: localize('cloneFailed', "Failed to install plugin '{0}': {1}", failureLabel, err?.message ?? String(err)),
+				actions: {
+					primary: [new Action('showGitOutput', localize('showGitOutput', "Show Git Output"), undefined, true, () => {
+						this._commandService.executeCommand('git.showOutput');
+					})],
+				},
+			});
+			throw err;
+		}
+	}
+
+	private _getPluginDir(repoDir: URI, source: string): URI {
+		const normalizedSource = source.trim().replace(/^\.?\/+|\/+$/g, '');
+		const pluginDir = normalizedSource ? joinPath(repoDir, normalizedSource) : repoDir;
+		if (!isEqualOrParent(pluginDir, repoDir)) {
+			throw new Error(`Invalid plugin source path '${source}'`);
+		}
+		return pluginDir;
+	}
+
+	getPluginSourceInstallUri(sourceDescriptor: IPluginSourceDescriptor): URI {
+		return this.getPluginSource(sourceDescriptor.kind).getInstallUri(this._cacheRoot, sourceDescriptor);
+	}
+
+	async ensurePluginSource(plugin: IMarketplacePlugin, options?: IEnsureRepositoryOptions): Promise<URI> {
+		const repo = this.getPluginSource(plugin.sourceDescriptor.kind);
+		if (plugin.sourceDescriptor.kind === PluginSourceKind.RelativePath) {
+			return this.ensureRepository(plugin.marketplaceReference, options);
+		}
+		return repo.ensure(this._cacheRoot, plugin, options);
+	}
+
+	async updatePluginSource(plugin: IMarketplacePlugin, options?: IPullRepositoryOptions): Promise<boolean> {
+		const repo = this.getPluginSource(plugin.sourceDescriptor.kind);
+		if (plugin.sourceDescriptor.kind === PluginSourceKind.RelativePath) {
+			return this.pullRepository(plugin.marketplaceReference, options);
+		}
+		return repo.update(this._cacheRoot, plugin, options);
+	}
+
+	async fetchRepository(marketplace: IMarketplaceReference): Promise<boolean> {
+		const repoDir = this.getRepositoryUri(marketplace);
+		const repoExists = await this._fileService.exists(repoDir);
+		if (!repoExists) {
+			return false;
+		}
+
+		try {
+			await this._commandService.executeCommand('_git.fetchRepository', repoDir.fsPath);
+			const behindCount = await this._commandService.executeCommand<number>('_git.revListCount', repoDir.fsPath, 'HEAD', '@{u}') ?? 0;
+			return behindCount > 0;
+		} catch (err) {
+			this._logService.debug(`[AgentPluginRepositoryService] Silent fetch failed for ${marketplace.displayLabel}:`, err);
+			return false;
+		}
+	}
+
+	async cleanupPluginSource(plugin: IMarketplacePlugin): Promise<void> {
+		const repo = this.getPluginSource(plugin.sourceDescriptor.kind);
+		const cleanupDir = repo.getCleanupTarget(this._cacheRoot, plugin.sourceDescriptor);
+		if (!cleanupDir) {
+			return;
+		}
+
+		try {
+			const exists = await this._fileService.exists(cleanupDir);
+			if (exists) {
+				await this._fileService.del(cleanupDir, { recursive: true });
+				this._logService.info(`[${plugin.sourceDescriptor.kind}] Removed plugin cache: ${cleanupDir.toString()}`);
+			}
+		} catch (err) {
+			this._logService.warn(`[${plugin.sourceDescriptor.kind}] Failed to remove plugin cache '${cleanupDir.toString()}':`, err);
+		}
+
+		try {
+			// Prune empty parent directories up to (but not including) the cache root
+			// so we don't leave dangling owner/authority folders behind.
+			await this._pruneEmptyParents(cleanupDir);
+		} catch (err) {
+			this._logService.warn(`[${plugin.sourceDescriptor.kind}] Failed to cleanup plugin source:`, err);
+		}
+	}
+
+	/**
+	 * Walk from {@link child}'s parent toward {@link _cacheRoot}, removing
+	 * each directory that is empty. Stops as soon as a non-empty directory
+	 * is found or the cache root is reached. Only operates on descendants
+	 * of the cache root — returns immediately for paths outside it.
+	 */
+	private async _pruneEmptyParents(child: URI): Promise<void> {
+		if (!isEqualOrParent(child, this._cacheRoot)) {
+			return;
+		}
+		let current = dirname(child);
+		while (isEqualOrParent(current, this._cacheRoot) && !isEqual(current, this._cacheRoot)) {
+			try {
+				const stat = await this._fileService.resolve(current);
+				if (stat.children && stat.children.length > 0) {
+					break;
+				}
+				await this._fileService.del(current);
+			} catch {
+				break;
+			}
+			current = dirname(current);
+		}
+	}
+
+}
diff --git a/src/vs/workbench/contrib/chat/browser/agentPluginsView.ts b/src/vs/workbench/contrib/chat/browser/agentPluginsView.ts
index 1f8a8d05b212e..e234adc4d484c 100644
--- a/src/vs/workbench/contrib/chat/browser/agentPluginsView.ts
+++ b/src/vs/workbench/contrib/chat/browser/agentPluginsView.ts
@@ -5,23 +5,27 @@
 
 import * as dom from '../../../../base/browser/dom.js';
 import { ActionBar } from '../../../../base/browser/ui/actionbar/actionbar.js';
+import { ActionViewItem, IActionViewItemOptions } from '../../../../base/browser/ui/actionbar/actionViewItems.js';
 import { IListContextMenuEvent } from '../../../../base/browser/ui/list/list.js';
 import { IPagedRenderer } from '../../../../base/browser/ui/list/listPaging.js';
 import { Action, IAction, Separator } from '../../../../base/common/actions.js';
 import { RunOnceScheduler } from '../../../../base/common/async.js';
-import { CancellationTokenSource } from '../../../../base/common/cancellation.js';
-import { Disposable, DisposableStore, IDisposable, isDisposable, MutableDisposable } from '../../../../base/common/lifecycle.js';
-import { autorun } from '../../../../base/common/observable.js';
+import { CancellationToken, CancellationTokenSource } from '../../../../base/common/cancellation.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { Event } from '../../../../base/common/event.js';
+import { Disposable, DisposableStore, disposeIfDisposable, IDisposable, isDisposable, MutableDisposable } from '../../../../base/common/lifecycle.js';
+import { ThemeIcon } from '../../../../base/common/themables.js';
+import { autorun, derived, IObservable, IReaderWithStore } from '../../../../base/common/observable.js';
 import { IPagedModel, PagedModel } from '../../../../base/common/paging.js';
-import { basename, dirname, joinPath } from '../../../../base/common/resources.js';
-import { URI } from '../../../../base/common/uri.js';
+import { dirname } from '../../../../base/common/resources.js';
 import { localize, localize2 } from '../../../../nls.js';
+import { Action2, MenuId, registerAction2 } from '../../../../platform/actions/common/actions.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { ContextKeyExpr, IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
 import { IContextMenuService } from '../../../../platform/contextview/browser/contextView.js';
 import { IHoverService } from '../../../../platform/hover/browser/hover.js';
 import { SyncDescriptor } from '../../../../platform/instantiation/common/descriptors.js';
-import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
+import { IInstantiationService, ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
 import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
 import { ILabelService } from '../../../../platform/label/common/label.js';
 import { WorkbenchPagedList } from '../../../../platform/list/browser/listService.js';
@@ -32,48 +36,30 @@ import { getLocationBasedViewColors } from '../../../browser/parts/views/viewPan
 import { IViewletViewOptions } from '../../../browser/parts/views/viewsViewlet.js';
 import { IWorkbenchContribution } from '../../../common/contributions.js';
 import { IViewDescriptorService, IViewsRegistry, Extensions as ViewExtensions } from '../../../common/views.js';
+import { IEditorService, MODAL_GROUP } from '../../../services/editor/common/editorService.js';
 import { VIEW_CONTAINER } from '../../extensions/browser/extensions.contribution.js';
+import { manageExtensionIcon } from '../../extensions/browser/extensionsIcons.js';
 import { AbstractExtensionsListView } from '../../extensions/browser/extensionsViews.js';
-import { DefaultViewsContext, SearchAgentPluginsContext } from '../../extensions/common/extensions.js';
+import { DefaultViewsContext, extensionsFilterSubMenu, IExtensionsWorkbenchService, SearchAgentPluginsContext } from '../../extensions/common/extensions.js';
 import { ChatContextKeys } from '../common/actions/chatContextKeys.js';
 import { IAgentPlugin, IAgentPluginService } from '../common/plugins/agentPluginService.js';
+import { isContributionEnabled } from '../common/enablement.js';
 import { IPluginInstallService } from '../common/plugins/pluginInstallService.js';
-import { IMarketplacePlugin, IPluginMarketplaceService, MarketplaceType } from '../common/plugins/pluginMarketplaceService.js';
+import { hasSourceChanged, IMarketplacePlugin, IPluginMarketplaceService } from '../common/plugins/pluginMarketplaceService.js';
+import { AgentPluginEditorInput } from './agentPluginEditor/agentPluginEditorInput.js';
+import { AgentPluginItemKind, IAgentPluginItem, IInstalledPluginItem, IMarketplacePluginItem } from './agentPluginEditor/agentPluginItems.js';
+import { getInstalledPluginContextMenuActions, InstallPluginAction, OpenPluginReadmeAction } from './agentPluginActions.js';
 
 export const HasInstalledAgentPluginsContext = new RawContextKey<boolean>('hasInstalledAgentPlugins', false);
+export const InstalledAgentPluginsViewId = 'workbench.views.agentPlugins.installed';
 
 //#region Item model
 
-const enum AgentPluginItemKind {
-	Installed = 'installed',
-	Marketplace = 'marketplace',
-}
-
-interface IInstalledPluginItem {
-	readonly kind: AgentPluginItemKind.Installed;
-	readonly name: string;
-	readonly description: string;
-	readonly marketplace?: string;
-	readonly plugin: IAgentPlugin;
-}
-
-interface IMarketplacePluginItem {
-	readonly kind: AgentPluginItemKind.Marketplace;
-	readonly name: string;
-	readonly description: string;
-	readonly source: string;
-	readonly marketplace: string;
-	readonly marketplaceType: MarketplaceType;
-	readonly readmeUri?: URI;
-}
-
-type IAgentPluginItem = IInstalledPluginItem | IMarketplacePluginItem;
-
-function installedPluginToItem(plugin: IAgentPlugin, labelService: ILabelService): IInstalledPluginItem {
-	const name = basename(plugin.uri);
+function installedPluginToItem(plugin: IAgentPlugin, labelService: ILabelService, outdated?: IObservable<IMarketplacePlugin | undefined>): IInstalledPluginItem {
+	const name = plugin.label;
 	const description = plugin.fromMarketplace?.description ?? labelService.getUriLabel(dirname(plugin.uri), { relative: true });
 	const marketplace = plugin.fromMarketplace?.marketplace;
-	return { kind: AgentPluginItemKind.Installed, name, description, marketplace, plugin };
+	return { kind: AgentPluginItemKind.Installed, name, description, marketplace, plugin, outdated };
 }
 
 function marketplacePluginToItem(plugin: IMarketplacePlugin): IMarketplacePluginItem {
@@ -82,7 +68,9 @@ function marketplacePluginToItem(plugin: IMarketplacePlugin): IMarketplacePlugin
 		name: plugin.name,
 		description: plugin.description,
 		source: plugin.source,
+		sourceDescriptor: plugin.sourceDescriptor,
 		marketplace: plugin.marketplace,
+		marketplaceReference: plugin.marketplaceReference,
 		marketplaceType: plugin.marketplaceType,
 		readmeUri: plugin.readmeUri,
 	};
@@ -92,101 +80,74 @@ function marketplacePluginToItem(plugin: IMarketplacePlugin): IMarketplacePlugin
 
 //#region Actions
 
-class InstallPluginAction extends Action {
-	static readonly ID = 'agentPlugin.install';
-
-	constructor(
-		private readonly item: IMarketplacePluginItem,
-		@IPluginInstallService private readonly pluginInstallService: IPluginInstallService,
-	) {
-		super(InstallPluginAction.ID, localize('install', "Install"), 'extension-action label prominent install');
-	}
-
-	override async run(): Promise<void> {
-		await this.pluginInstallService.installPlugin({
-			name: this.item.name,
-			description: this.item.description,
-			version: '',
-			source: this.item.source,
-			marketplace: this.item.marketplace,
-			marketplaceType: this.item.marketplaceType,
-			readmeUri: this.item.readmeUri,
-		});
-	}
-}
+//#region Actions
 
-class EnablePluginAction extends Action {
-	static readonly ID = 'agentPlugin.enable';
+class UpdatePluginAction extends Action {
+	static readonly ID = 'agentPlugin.update';
 
 	constructor(
 		private readonly plugin: IAgentPlugin,
-		@IAgentPluginService private readonly agentPluginService: IAgentPluginService,
+		private readonly liveMarketplacePlugin: IMarketplacePlugin,
+		@IPluginInstallService private readonly pluginInstallService: IPluginInstallService,
+		@IPluginMarketplaceService private readonly pluginMarketplaceService: IPluginMarketplaceService,
 	) {
-		super(EnablePluginAction.ID, localize('enable', "Enable"));
+		super(UpdatePluginAction.ID, localize('update', "Update"), 'extension-action label prominent install');
 	}
 
 	override async run(): Promise<void> {
-		this.agentPluginService.setPluginEnabled(this.plugin.uri, true);
+		if (await this.pluginInstallService.updatePlugin(this.liveMarketplacePlugin)) {
+			this.pluginMarketplaceService.addInstalledPlugin(this.plugin.uri, this.liveMarketplacePlugin);
+		}
 	}
 }
 
-class DisablePluginAction extends Action {
-	static readonly ID = 'agentPlugin.disable';
-
-	constructor(
-		private readonly plugin: IAgentPlugin,
-		@IAgentPluginService private readonly agentPluginService: IAgentPluginService,
-	) {
-		super(DisablePluginAction.ID, localize('disable', "Disable"));
-	}
-
-	override async run(): Promise<void> {
-		this.agentPluginService.setPluginEnabled(this.plugin.uri, false);
-	}
-}
+class ManagePluginAction extends Action {
+	static readonly ID = 'agentPlugin.manage';
+	static readonly CLASS = `extension-action icon manage ${ThemeIcon.asClassName(manageExtensionIcon)}`;
 
-class UninstallPluginAction extends Action {
-	static readonly ID = 'agentPlugin.uninstall';
+	private _actionViewItem: DropDownActionViewItem | null = null;
 
 	constructor(
-		private readonly plugin: IAgentPlugin,
-		@IPluginInstallService private readonly pluginInstallService: IPluginInstallService,
+		private readonly getActionGroups: () => IAction[][],
+		@IInstantiationService private readonly instantiationService: IInstantiationService,
 	) {
-		super(UninstallPluginAction.ID, localize('uninstall', "Uninstall"));
+		super(ManagePluginAction.ID, '', ManagePluginAction.CLASS, true);
+		this.tooltip = localize('manage', "Manage");
 	}
 
-	override async run(): Promise<void> {
-		this.pluginInstallService.uninstallPlugin(this.plugin.uri);
-	}
-}
-
-class OpenPluginFolderAction extends Action {
-	static readonly ID = 'agentPlugin.openFolder';
-
-	constructor(
-		private readonly plugin: IAgentPlugin,
-		@IOpenerService private readonly openerService: IOpenerService,
-	) {
-		super(OpenPluginFolderAction.ID, localize('openContainingFolder', "Open Containing Folder"));
+	createActionViewItem(options: IActionViewItemOptions): DropDownActionViewItem {
+		this._actionViewItem = this.instantiationService.createInstance(DropDownActionViewItem, this, options);
+		return this._actionViewItem;
 	}
 
 	override async run(): Promise<void> {
-		await this.openerService.open(dirname(this.plugin.uri));
+		this._actionViewItem?.showMenu(this.getActionGroups());
 	}
 }
 
-class OpenPluginReadmeAction extends Action {
-	static readonly ID = 'agentPlugin.openReadme';
-
+class DropDownActionViewItem extends ActionViewItem {
 	constructor(
-		private readonly readmeUri: URI,
-		@IOpenerService private readonly openerService: IOpenerService,
+		action: IAction,
+		options: IActionViewItemOptions,
+		@IContextMenuService private readonly contextMenuService: IContextMenuService,
 	) {
-		super(OpenPluginReadmeAction.ID, localize('openReadme', "Open README"));
+		super(null, action, { ...options, icon: true, label: false });
 	}
 
-	override async run(): Promise<void> {
-		await this.openerService.open(this.readmeUri);
+	showMenu(actionGroups: IAction[][]): void {
+		if (!this.element) {
+			return;
+		}
+		const actions = actionGroups.flatMap(group => [...group, new Separator()]);
+		if (actions.length > 0) {
+			actions.pop();
+		}
+		const { left, top, height } = dom.getDomNodePagePosition(this.element);
+		this.contextMenuService.showContextMenu({
+			getAnchor: () => ({ x: left, y: top + height + 10 }),
+			getActions: () => actions,
+			onHide: () => disposeIfDisposable(actions),
+		});
 	}
 }
 
@@ -223,7 +184,15 @@ class AgentPluginRenderer implements IPagedRenderer<IAgentPluginItem, IAgentPlug
 		const footer = dom.append(details, dom.$('.footer'));
 		const detailContainer = dom.append(footer, dom.$('.publisher-container'));
 		const detail = dom.append(detailContainer, dom.$('span.publisher-name'));
-		const actionbar = new ActionBar(footer, { focusOnlyEnabledItems: true });
+		const actionbar = new ActionBar(footer, {
+			focusOnlyEnabledItems: true,
+			actionViewItemProvider: (action: IAction, options: IActionViewItemOptions) => {
+				if (action instanceof ManagePluginAction) {
+					return action.createActionViewItem(options);
+				}
+				return undefined;
+			}
+		});
 		actionbar.setFocusable(false);
 		return { root, name, description, detail, actionbar, disposables: [actionbar], elementDisposables: [] };
 	}
@@ -243,18 +212,34 @@ class AgentPluginRenderer implements IPagedRenderer<IAgentPluginItem, IAgentPlug
 		data.description.textContent = element.description;
 
 		data.elementDisposables.push(autorun(reader => {
-			data.root.classList.toggle('disabled', element.kind === AgentPluginItemKind.Installed && !element.plugin.enabled.read(reader));
+			data.root.classList.toggle('disabled', element.kind === AgentPluginItemKind.Installed && !isContributionEnabled(element.plugin.enablement.read(reader)));
 		}));
 
-		data.actionbar.clear();
-		if (element.kind === AgentPluginItemKind.Marketplace) {
-			data.detail.textContent = element.marketplace;
-			const installAction = this.instantiationService.createInstance(InstallPluginAction, element);
-			data.elementDisposables.push(installAction);
-			data.actionbar.push([installAction], { icon: true, label: true });
-		} else {
-			data.detail.textContent = element.marketplace ?? '';
-		}
+		const updateActions = (reader: IReaderWithStore) => {
+			data.actionbar.clear();
+			if (element.kind === AgentPluginItemKind.Marketplace) {
+				data.detail.textContent = element.marketplace;
+				const installAction = this.instantiationService.createInstance(InstallPluginAction, element);
+				reader.store.add(installAction);
+				data.actionbar.push([installAction], { icon: true, label: true });
+			} else {
+				data.detail.textContent = element.marketplace ?? '';
+				const actions: Action[] = [];
+				const livePlugin = element.outdated?.read(reader);
+				if (livePlugin) {
+					const updateAction = this.instantiationService.createInstance(UpdatePluginAction, element.plugin, livePlugin);
+					reader.store.add(updateAction);
+					actions.push(updateAction);
+				}
+				const manageAction = this.instantiationService.createInstance(ManagePluginAction,
+					() => getInstalledPluginContextMenuActions(element.plugin, this.instantiationService));
+				reader.store.add(manageAction);
+				actions.push(manageAction);
+				data.actionbar.push(actions, { icon: true, label: true });
+			}
+		};
+
+		data.elementDisposables.push(autorun(updateActions));
 	}
 
 	disposeElement(_element: IAgentPluginItem | undefined, _index: number, data: IAgentPluginTemplateData): void {
@@ -276,6 +261,10 @@ class AgentPluginRenderer implements IPagedRenderer<IAgentPluginItem, IAgentPlug
 
 //#region List View
 
+interface IAgentPluginsListViewOptions {
+	installedOnly?: boolean;
+}
+
 export class AgentPluginsListView extends AbstractExtensionsListView<IAgentPluginItem> {
 
 	private readonly actionStore = this._register(new DisposableStore());
@@ -295,6 +284,7 @@ export class AgentPluginsListView extends AbstractExtensionsListView<IAgentPlugi
 	} | undefined;
 
 	constructor(
+		private readonly listOptions: IAgentPluginsListViewOptions,
 		options: IViewletViewOptions,
 		@IKeybindingService keybindingService: IKeybindingService,
 		@IContextMenuService contextMenuService: IContextMenuService,
@@ -309,11 +299,21 @@ export class AgentPluginsListView extends AbstractExtensionsListView<IAgentPlugi
 		@IPluginMarketplaceService private readonly pluginMarketplaceService: IPluginMarketplaceService,
 		@IPluginInstallService private readonly pluginInstallService: IPluginInstallService,
 		@ILabelService private readonly labelService: ILabelService,
+		@IEditorService private readonly editorService: IEditorService,
 	) {
 		super(options, keybindingService, contextMenuService, configurationService, contextKeyService, viewDescriptorService, instantiationService, openerService, themeService, hoverService);
 
 		this._register(autorun(reader => {
-			this.agentPluginService.plugins.read(reader);
+			const plugins = this.agentPluginService.plugins.read(reader);
+			for (const plugin of plugins) {
+				plugin.enablement.read(reader);
+			}
+			if (this.list && this.isBodyVisible()) {
+				this.refreshOnPluginsChangedScheduler.schedule();
+			}
+		}));
+
+		this._register(this.pluginMarketplaceService.onDidChangeMarketplaces(() => {
 			if (this.list && this.isBodyVisible()) {
 				this.refreshOnPluginsChangedScheduler.schedule();
 			}
@@ -354,6 +354,14 @@ export class AgentPluginsListView extends AbstractExtensionsListView<IAgentPlugi
 			}) as WorkbenchPagedList<IAgentPluginItem>);
 
 		this._register(this.list.onContextMenu(e => this.onContextMenu(e), this));
+
+		this._register(Event.debounce(Event.filter(this.list.onDidOpen, e => e.element !== null), (_, event) => event, 75, true)(options => {
+			this.editorService.openEditor(
+				this.instantiationService.createInstance(AgentPluginEditorInput, options.element!),
+				options.editorOptions,
+				MODAL_GROUP
+			);
+		}));
 	}
 
 	private onContextMenu(e: IListContextMenuEvent<IAgentPluginItem>): void {
@@ -373,20 +381,15 @@ export class AgentPluginsListView extends AbstractExtensionsListView<IAgentPlugi
 	}
 
 	private getContextMenuActions(item: IAgentPluginItem): IAction[] {
-		const actions: IAction[] = [];
+		let actions: IAction[];
 		if (item.kind === AgentPluginItemKind.Installed) {
-			if (item.plugin.enabled.get()) {
-				actions.push(this.instantiationService.createInstance(DisablePluginAction, item.plugin));
-			} else {
-				actions.push(this.instantiationService.createInstance(EnablePluginAction, item.plugin));
+			const groups = getInstalledPluginContextMenuActions(item.plugin, this.instantiationService);
+			actions = groups.flatMap(group => [...group, new Separator()]);
+			if (actions.length > 0) {
+				actions.pop();
 			}
-
-			actions.push(new Separator());
-			actions.push(this.instantiationService.createInstance(OpenPluginFolderAction, item.plugin));
-			actions.push(this.instantiationService.createInstance(OpenPluginReadmeAction, joinPath(item.plugin.uri, 'README.md')));
-			actions.push(new Separator());
-			actions.push(this.instantiationService.createInstance(UninstallPluginAction, item.plugin));
 		} else {
+			actions = [];
 			if (item.readmeUri) {
 				actions.push(this.instantiationService.createInstance(OpenPluginReadmeAction, item.readmeUri));
 			}
@@ -410,28 +413,71 @@ export class AgentPluginsListView extends AbstractExtensionsListView<IAgentPlugi
 
 	async show(query: string): Promise<IPagedModel<IAgentPluginItem>> {
 		this.currentQuery = query;
-		const text = query.replace(/@agentPlugins/i, '').trim();
-
-		const [installed, marketplace] = await Promise.all([
-			this.queryInstalled(),
-			this.queryMarketplace(text),
-		]);
-
-		// Filter out marketplace items that are already installed
-		const installedPaths = new Set(installed.map(i => i.plugin.uri.toString()));
-		const filteredMarketplace = marketplace.filter(m => {
-			const expectedUri = this.pluginInstallService.getPluginInstallUri({
-				name: m.name,
-				description: m.description,
-				version: '',
-				source: m.source,
-				marketplace: m.marketplace,
-				marketplaceType: m.marketplaceType,
+		const stripped = query.replace(/@agentPlugins/i, '').trim();
+		const isRecommended = /^@recommended$/i.test(stripped);
+		const text = isRecommended ? '' : stripped.toLowerCase();
+
+		let installed = this.queryInstalled();
+		if (text) {
+			installed = installed.filter(p =>
+				p.name.toLowerCase().includes(text) ||
+				p.description.toLowerCase().includes(text)
+			);
+		}
+
+		// When @recommended, filter to plugins listed in workspace recommendations.
+		if (isRecommended) {
+			const recommended = this.pluginMarketplaceService.recommendedPlugins.get();
+			installed = installed.filter(p => {
+				const marketplace = p.plugin.fromMarketplace;
+				if (!marketplace) {
+					return false;
+				}
+				const key = `${marketplace.name}@${marketplace.marketplace}`;
+				return recommended.has(key);
 			});
-			return !installedPaths.has(expectedUri.toString());
-		});
+		}
+
+		let items: IAgentPluginItem[] = installed;
+
+		if (!this.listOptions.installedOnly) {
+			const marketplacePlugins = await this.queryMarketplacePlugins();
+			let filteredMp = marketplacePlugins;
+
+			if (isRecommended) {
+				// When @recommended, filter marketplace plugins to those in recommendations.
+				const recommended = this.pluginMarketplaceService.recommendedPlugins.get();
+				filteredMp = filteredMp.filter(p => {
+					const key = `${p.name}@${p.marketplace}`;
+					return recommended.has(key);
+				});
+			} else {
+				const lowerText = text.toLowerCase();
+				filteredMp = filteredMp.filter(p => p.name.toLowerCase().includes(lowerText) || p.description.toLowerCase().includes(lowerText));
+			}
+
+			const marketplace = filteredMp.map(marketplacePluginToItem);
+
+			// Filter out marketplace items that are already installed
+			const installedPaths = new Set(installed.map(i => i.plugin.uri.toString()));
+			const filteredMarketplace = marketplace.filter(m => {
+				const expectedUri = this.pluginInstallService.getPluginInstallUri({
+					name: m.name,
+					description: m.description,
+					version: '',
+					source: m.source,
+					sourceDescriptor: m.sourceDescriptor,
+					marketplace: m.marketplace,
+					marketplaceReference: m.marketplaceReference,
+					marketplaceType: m.marketplaceType,
+				});
+				return !installedPaths.has(expectedUri.toString());
+			});
+
+			items = [...installed, ...filteredMarketplace];
+		}
 
-		const model = new PagedModel([...installed, ...filteredMarketplace]);
+		const model = new PagedModel(items);
 		if (this.list) {
 			this.list.model = model;
 		}
@@ -439,22 +485,58 @@ export class AgentPluginsListView extends AbstractExtensionsListView<IAgentPlugi
 		return model;
 	}
 
+	/**
+	 * Builds the installed plugin list using only cached marketplace data
+	 * (no IO). The cached data is populated by {@link fetchMarketplacePlugins}
+	 * and exposed via the {@link IPluginMarketplaceService.lastFetchedPlugins}
+	 * observable, which the view's autorun subscribes to for reactivity.
+	 */
 	private queryInstalled(): IInstalledPluginItem[] {
-		const allPlugins = this.agentPluginService.allPlugins.get();
-		return allPlugins.map(p => installedPluginToItem(p, this.labelService));
+		const marketplaceObs = derived(reader => {
+			const cachedMarketplace = this.pluginMarketplaceService.lastFetchedPlugins.read(reader);
+			const marketplaceByKey = new Map<string, IMarketplacePlugin>();
+			for (const mp of cachedMarketplace) {
+				marketplaceByKey.set(`${mp.marketplaceReference.canonicalId}::${mp.name}`, mp);
+			}
+
+
+			// Read fresh installed plugin metadata from the store (not from
+			// IAgentPlugin.fromMarketplace which may be stale after an update).
+			const installedByUri = new Map<string, IMarketplacePlugin>();
+			for (const entry of this.pluginMarketplaceService.installedPlugins.read(reader)) {
+				installedByUri.set(entry.pluginUri.toString(), entry.plugin);
+			}
+
+			return { marketplaceByKey, installedByUri };
+		});
+
+
+		const plugins = this.agentPluginService.plugins.get();
+		return plugins.map(p => {
+			const isOutdated = derived(reader => {
+				const { marketplaceByKey, installedByUri } = marketplaceObs.read(reader);
+				const storedPlugin = installedByUri.get(p.uri.toString()) ?? p.fromMarketplace;
+				if (storedPlugin) {
+					const key = `${storedPlugin.marketplaceReference.canonicalId}::${storedPlugin.name}`;
+					const live = marketplaceByKey.get(key);
+					if (live && hasSourceChanged(storedPlugin.sourceDescriptor, live.sourceDescriptor)) {
+						return live;
+					}
+				}
+
+				return undefined;
+			});
+			return installedPluginToItem(p, this.labelService, isOutdated);
+		});
 	}
 
-	private async queryMarketplace(text: string): Promise<IMarketplacePluginItem[]> {
+	private async queryMarketplacePlugins(): Promise<IMarketplacePlugin[]> {
 		this.queryCts.value?.cancel();
 		const cts = new CancellationTokenSource();
 		this.queryCts.value = cts;
 
 		try {
-			const plugins = await this.pluginMarketplaceService.fetchMarketplacePlugins(cts.token);
-			const lowerText = text.toLowerCase();
-			return plugins
-				.filter(p => p.name.toLowerCase().includes(lowerText) || p.description.toLowerCase().includes(lowerText))
-				.map(marketplacePluginToItem);
+			return await this.pluginMarketplaceService.fetchMarketplacePlugins(cts.token);
 		} catch {
 			return [];
 		}
@@ -473,16 +555,67 @@ export class AgentPluginsListView extends AbstractExtensionsListView<IAgentPlugi
 
 //#endregion
 
-//#region Default browse view
+//#region Browse command
+
+class AgentPluginsBrowseCommand extends Action2 {
+	constructor() {
+		super({
+			id: 'workbench.agentPlugins.browse',
+			title: localize2('agentPlugins.browse', "Agent Plugins"),
+			tooltip: localize2('agentPlugins.browse.tooltip', "Browse Agent Plugins"),
+			icon: Codicon.search,
+			precondition: ChatContextKeys.Setup.hidden.negate(),
+			menu: [{
+				id: extensionsFilterSubMenu,
+				group: '1_predefined',
+				order: 2,
+				when: ChatContextKeys.Setup.hidden.negate(),
+			}, {
+				id: MenuId.ViewTitle,
+				when: ContextKeyExpr.and(ContextKeyExpr.equals('view', InstalledAgentPluginsViewId), ChatContextKeys.Setup.hidden.negate()),
+				group: 'navigation',
+			}],
+		});
+	}
+
+	async run(accessor: ServicesAccessor) {
+		accessor.get(IExtensionsWorkbenchService).openSearch('@agentPlugins ');
+	}
+}
 
-class DefaultBrowseAgentPluginsView extends AgentPluginsListView {
-	override async show(_query: string): Promise<IPagedModel<IAgentPluginItem>> {
-		return super.show('@agentPlugins');
+class CheckForPluginUpdatesCommand extends Action2 {
+	constructor() {
+		super({
+			id: 'workbench.agentPlugins.checkForUpdates',
+			title: localize2('agentPlugins.checkForUpdates', "Update Plugins"),
+			category: localize2('chat.category', "Chat"),
+			precondition: ChatContextKeys.enabled,
+			f1: true,
+		});
+	}
+
+	async run(accessor: ServicesAccessor) {
+		await accessor.get(IPluginInstallService).updateAllPlugins({}, CancellationToken.None);
 	}
 }
 
-//#endregion
+class ForceUpdatePluginsCommand extends Action2 {
+	constructor() {
+		super({
+			id: 'workbench.agentPlugins.forceUpdate',
+			title: localize2('agentPlugins.forceUpdate', "Update Plugins (Force)"),
+			category: localize2('chat.category', "Chat"),
+			precondition: ChatContextKeys.enabled,
+			f1: true,
+		});
+	}
 
+	async run(accessor: ServicesAccessor) {
+		await accessor.get(IPluginInstallService).updateAllPlugins({ force: true }, CancellationToken.None);
+	}
+}
+
+//#endregion
 //#region Views contribution
 
 export class AgentPluginsViewsContribution extends Disposable implements IWorkbenchContribution {
@@ -497,14 +630,18 @@ export class AgentPluginsViewsContribution extends Disposable implements IWorkbe
 
 		const hasInstalledKey = HasInstalledAgentPluginsContext.bindTo(contextKeyService);
 		this._register(autorun(reader => {
-			hasInstalledKey.set(agentPluginService.allPlugins.read(reader).length > 0);
+			hasInstalledKey.set(agentPluginService.plugins.read(reader).length > 0);
 		}));
 
+		registerAction2(AgentPluginsBrowseCommand);
+		registerAction2(CheckForPluginUpdatesCommand);
+		registerAction2(ForceUpdatePluginsCommand);
+
 		Registry.as<IViewsRegistry>(ViewExtensions.ViewsRegistry).registerViews([
 			{
-				id: 'workbench.views.agentPlugins.installed',
+				id: InstalledAgentPluginsViewId,
 				name: localize2('agent-plugins-installed', "Agent Plugins - Installed"),
-				ctorDescriptor: new SyncDescriptor(AgentPluginsListView),
+				ctorDescriptor: new SyncDescriptor(AgentPluginsListView, [{ installedOnly: true }]),
 				when: ContextKeyExpr.and(DefaultViewsContext, HasInstalledAgentPluginsContext, ChatContextKeys.Setup.hidden.negate()),
 				weight: 30,
 				order: 5,
@@ -513,7 +650,7 @@ export class AgentPluginsViewsContribution extends Disposable implements IWorkbe
 			{
 				id: 'workbench.views.agentPlugins.default.marketplace',
 				name: localize2('agent-plugins', "Agent Plugins"),
-				ctorDescriptor: new SyncDescriptor(DefaultBrowseAgentPluginsView),
+				ctorDescriptor: new SyncDescriptor(AgentPluginsListView, [{}]),
 				when: ContextKeyExpr.and(DefaultViewsContext, HasInstalledAgentPluginsContext.toNegated(), ChatContextKeys.Setup.hidden.negate()),
 				weight: 30,
 				order: 5,
@@ -523,7 +660,7 @@ export class AgentPluginsViewsContribution extends Disposable implements IWorkbe
 			{
 				id: 'workbench.views.agentPlugins.marketplace',
 				name: localize2('agent-plugins', "Agent Plugins"),
-				ctorDescriptor: new SyncDescriptor(AgentPluginsListView),
+				ctorDescriptor: new SyncDescriptor(AgentPluginsListView, [{}]),
 				when: ContextKeyExpr.and(SearchAgentPluginsContext, ChatContextKeys.Setup.hidden.negate()),
 			},
 		], VIEW_CONTAINER);
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionApprovalModel.ts b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionApprovalModel.ts
new file mode 100644
index 0000000000000..5b2aa56855a12
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionApprovalModel.ts
@@ -0,0 +1,124 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { renderAsPlaintext } from '../../../../../base/browser/markdownRenderer.js';
+import { Disposable, DisposableResourceMap, IDisposable } from '../../../../../base/common/lifecycle.js';
+import { autorun, autorunIterableDelta, IObservable, ISettableObservable, observableValue } from '../../../../../base/common/observable.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { migrateLegacyTerminalToolSpecificData } from '../../common/chat.js';
+import { IChatModel } from '../../common/model/chatModel.js';
+import { IChatService, IChatToolInvocation, ToolConfirmKind } from '../../common/chatService/chatService.js';
+import { ILanguageService } from '../../../../../editor/common/languages/language.js';
+
+export interface IAgentSessionApprovalInfo {
+	readonly label: string;
+	readonly languageId: string | undefined;
+	confirm(): void;
+}
+
+/**
+ * Tracks approval state for all live chat sessions. For each session,
+ * exposes an observable that emits {@link IAgentSessionApprovalInfo}
+ * when a tool invocation is waiting for user confirmation, or `undefined`
+ * when no approval is needed.
+ */
+export class AgentSessionApprovalModel extends Disposable {
+
+	private readonly _approvals = new Map<string, ISettableObservable<IAgentSessionApprovalInfo | undefined>>();
+	private readonly _modelTrackers = this._register(new DisposableResourceMap());
+
+	constructor(
+		@IChatService private readonly _chatService: IChatService,
+		@ILanguageService private readonly _languageService: ILanguageService,
+	) {
+		super();
+
+		this._register(autorunIterableDelta(
+			reader => this._chatService.chatModels.read(reader),
+			({ addedValues, removedValues }) => {
+				for (const model of addedValues) {
+					this._modelTrackers.set(model.sessionResource, this._trackModel(model));
+				}
+				for (const model of removedValues) {
+					this._modelTrackers.deleteAndDispose(model.sessionResource);
+					this._approvals.get(model.sessionResource.toString())?.set(undefined, undefined);
+				}
+			}
+		));
+	}
+
+	getApproval(sessionResource: URI): IObservable<IAgentSessionApprovalInfo | undefined> {
+		return this._getOrCreateApproval(sessionResource.toString());
+	}
+
+	private _getOrCreateApproval(key: string): ISettableObservable<IAgentSessionApprovalInfo | undefined> {
+		let obs = this._approvals.get(key);
+		if (!obs) {
+			obs = observableValue<IAgentSessionApprovalInfo | undefined>(`sessionApproval.${key}`, undefined);
+			this._approvals.set(key, obs);
+		}
+		return obs;
+	}
+
+	private _trackModel(model: IChatModel): IDisposable {
+		const settable = this._getOrCreateApproval(model.sessionResource.toString());
+
+		const setIfChanged = (value: IAgentSessionApprovalInfo | undefined) => {
+			const current = settable.get();
+			if (current === value) {
+				return;
+			}
+			if (current !== undefined && value !== undefined && current.label === value.label && current.languageId === value.languageId) {
+				return;
+			}
+			settable.set(value, undefined);
+		};
+
+		return autorun(reader => {
+			const needsInput = model.requestNeedsInput.read(reader);
+			if (!needsInput) {
+				setIfChanged(undefined);
+				return;
+			}
+
+			const lastResponse = model.lastRequest?.response;
+			if (!lastResponse?.response?.value) {
+				setIfChanged(undefined);
+				return;
+			}
+
+			for (const part of lastResponse.response.value) {
+				if (part.kind !== 'toolInvocation') {
+					continue;
+				}
+				const state = part.state.read(reader);
+				if (state.type === IChatToolInvocation.StateKind.WaitingForConfirmation || state.type === IChatToolInvocation.StateKind.WaitingForPostApproval) {
+					let label: string;
+					let languageId: string | undefined;
+					if (part.toolSpecificData?.kind === 'terminal') {
+						const terminalData = migrateLegacyTerminalToolSpecificData(part.toolSpecificData);
+						label = terminalData.presentationOverrides?.commandLine ?? terminalData.commandLine.forDisplay ?? terminalData.commandLine.userEdited ?? terminalData.commandLine.toolEdited ?? terminalData.commandLine.original;
+						languageId = this._languageService.getLanguageIdByLanguageName(terminalData.presentationOverrides?.language ?? terminalData.language) ?? undefined;
+					} else if (needsInput.detail) {
+						label = needsInput.detail;
+					} else {
+						const msg = part.invocationMessage;
+						label = typeof msg === 'string' ? msg : renderAsPlaintext(msg);
+					}
+
+					const confirmState = state;
+					setIfChanged({
+						label,
+						languageId,
+						confirm: () => confirmState.confirm({ type: ToolConfirmKind.UserAction }),
+					});
+					return;
+				}
+			}
+
+			setIfChanged(undefined);
+		});
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessions.ts b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessions.ts
index a8be72f98ff29..f7662aa69144b 100644
--- a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessions.ts
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessions.ts
@@ -7,7 +7,7 @@ import { localize } from '../../../../../nls.js';
 import { Codicon } from '../../../../../base/common/codicons.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { ThemeIcon } from '../../../../../base/common/themables.js';
-import { observableValue } from '../../../../../base/common/observable.js';
+
 import { IChatSessionTiming } from '../../common/chatService/chatService.js';
 import { foreground, listActiveSelectionForeground, registerColor, transparent } from '../../../../../platform/theme/common/colorRegistry.js';
 import { getChatSessionType } from '../../common/model/chatUri.js';
@@ -42,18 +42,12 @@ export function getAgentSessionProvider(sessionResource: URI | string): AgentSes
 	}
 }
 
-/**
- * Observable holding the display name for the background agent session provider.
- * Updated via experiment treatment to allow A/B testing of the display name.
- */
-export const backgroundAgentDisplayName = observableValue<string>('backgroundAgentDisplayName', localize('chat.session.providerLabel.background', "Background"));
-
 export function getAgentSessionProviderName(provider: AgentSessionProviders): string {
 	switch (provider) {
 		case AgentSessionProviders.Local:
 			return localize('chat.session.providerLabel.local', "Local");
 		case AgentSessionProviders.Background:
-			return backgroundAgentDisplayName.get();
+			return localize('chat.session.providerLabel.background', "Copilot CLI");
 		case AgentSessionProviders.Cloud:
 			return localize('chat.session.providerLabel.cloud', "Cloud");
 		case AgentSessionProviders.Claude:
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsActions.ts b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsActions.ts
index 3150acc6c23cf..950fea0381ea2 100644
--- a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsActions.ts
@@ -28,7 +28,7 @@ import { ChatViewPane } from '../widgetHosts/viewPane/chatViewPane.js';
 import { ICommandService } from '../../../../../platform/commands/common/commands.js';
 import { IInstantiationService } from '../../../../../platform/instantiation/common/instantiation.js';
 import { AgentSessionsPicker } from './agentSessionsPicker.js';
-import { ActiveEditorContext } from '../../../../common/contextkeys.js';
+import { ActiveEditorContext, IsSessionsWindowContext } from '../../../../common/contextkeys.js';
 import { IQuickInputService } from '../../../../../platform/quickinput/common/quickInput.js';
 import { KeybindingWeight } from '../../../../../platform/keybinding/common/keybindingsRegistry.js';
 import { KeyCode, KeyMod } from '../../../../../base/common/keyCodes.js';
@@ -708,10 +708,11 @@ export class OpenAgentSessionInEditorGroupAction extends BaseOpenAgentSessionAct
 					primary: KeyMod.WinCtrl | KeyCode.Enter
 				},
 				weight: KeybindingWeight.WorkbenchContrib + 1,
-				when: ChatContextKeys.agentSessionsViewerFocused,
+				when: ContextKeyExpr.and(ChatContextKeys.agentSessionsViewerFocused, IsSessionsWindowContext.negate()),
 			},
 			menu: {
 				id: MenuId.AgentSessionsContext,
+				when: IsSessionsWindowContext.negate(),
 				order: 1,
 				group: 'navigation'
 			}
@@ -741,10 +742,11 @@ export class OpenAgentSessionInNewEditorGroupAction extends BaseOpenAgentSession
 					primary: KeyMod.WinCtrl | KeyMod.Alt | KeyCode.Enter
 				},
 				weight: KeybindingWeight.WorkbenchContrib + 1,
-				when: ChatContextKeys.agentSessionsViewerFocused,
+				when: ContextKeyExpr.and(ChatContextKeys.agentSessionsViewerFocused, IsSessionsWindowContext.negate()),
 			},
 			menu: {
 				id: MenuId.AgentSessionsContext,
+				when: IsSessionsWindowContext.negate(),
 				order: 2,
 				group: 'navigation'
 			}
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsControl.ts b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsControl.ts
index 384baff52d4e3..97260bb9db337 100644
--- a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsControl.ts
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsControl.ts
@@ -8,9 +8,14 @@ import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
 import { IContextMenuService } from '../../../../../platform/contextview/browser/contextView.js';
 import { IInstantiationService } from '../../../../../platform/instantiation/common/instantiation.js';
 import { IOpenEvent, WorkbenchCompressibleAsyncDataTree } from '../../../../../platform/list/browser/listService.js';
-import { $, append, EventHelper } from '../../../../../base/browser/dom.js';
+import { $, append, EventHelper, addDisposableListener, EventType, hide, setVisibility } from '../../../../../base/browser/dom.js';
+import { StandardKeyboardEvent } from '../../../../../base/browser/keyboardEvent.js';
+import { KeyCode } from '../../../../../base/common/keyCodes.js';
+import { localize } from '../../../../../nls.js';
 import { AgentSessionSection, IAgentSession, IAgentSessionSection, IAgentSessionsModel, IMarshalledAgentSessionContext, isAgentSession, isAgentSessionSection } from './agentSessionsModel.js';
 import { AgentSessionListItem, AgentSessionRenderer, AgentSessionsAccessibilityProvider, AgentSessionsCompressionDelegate, AgentSessionsDataSource, AgentSessionsDragAndDrop, AgentSessionsIdentityProvider, AgentSessionsKeyboardNavigationLabelProvider, AgentSessionsListDelegate, AgentSessionSectionRenderer, AgentSessionsSorter, IAgentSessionsFilter, IAgentSessionsSorterOptions } from './agentSessionsViewer.js';
+import { AgentSessionsGrouping } from './agentSessionsFilter.js';
+import { AgentSessionApprovalModel } from './agentSessionApprovalModel.js';
 import { FuzzyScore } from '../../../../../base/common/filters.js';
 import { IMenuService, MenuId } from '../../../../../platform/actions/common/actions.js';
 import { IChatSessionsService } from '../../common/chatSessionsService.js';
@@ -19,6 +24,7 @@ import { ACTION_ID_NEW_CHAT } from '../actions/chatActions.js';
 import { Emitter, Event } from '../../../../../base/common/event.js';
 import { Disposable } from '../../../../../base/common/lifecycle.js';
 import { Throttler } from '../../../../../base/common/async.js';
+import { observableValue } from '../../../../../base/common/observable.js';
 import { ITreeContextMenuEvent } from '../../../../../base/browser/ui/tree/tree.js';
 import { MarshalledId } from '../../../../../base/common/marshallingIds.js';
 import { Separator } from '../../../../../base/common/actions.js';
@@ -35,12 +41,16 @@ import { IEditorService } from '../../../../services/editor/common/editorService
 import { ChatEditorInput } from '../widgetHosts/editor/chatEditorInput.js';
 import { IMouseEvent } from '../../../../../base/browser/mouseEvent.js';
 import { IChatWidget } from '../chat.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../../platform/storage/common/storage.js';
+import { ILogService } from '../../../../../platform/log/common/log.js';
 
 export interface IAgentSessionsControlOptions extends IAgentSessionsSorterOptions {
 	readonly overrideStyles: IStyleOverride<IListStyles>;
 	readonly filter: IAgentSessionsFilter;
 	readonly source: string;
 	readonly disableHover?: boolean;
+	readonly showIsolationIcon?: boolean;
+	readonly enableApprovalRow?: boolean;
 
 	getHoverPosition(): HoverPosition;
 	trackActiveEditorSession(): boolean;
@@ -68,8 +78,11 @@ export class AgentSessionsControl extends Disposable implements IAgentSessionsCo
 	private sessionsContainer: HTMLElement | undefined;
 	get element(): HTMLElement | undefined { return this.sessionsContainer; }
 
+	private emptyFilterMessage: HTMLElement | undefined;
+
 	private sessionsList: WorkbenchCompressibleAsyncDataTree<IAgentSessionsModel, AgentSessionListItem, FuzzyScore> | undefined;
 	private sessionsListFindIsOpen = false;
+	private _isProgrammaticCollapseChange = false;
 
 	private readonly updateSessionsListThrottler = this._register(new Throttler());
 
@@ -95,6 +108,8 @@ export class AgentSessionsControl extends Disposable implements IAgentSessionsCo
 		@IAgentSessionsService private readonly agentSessionsService: IAgentSessionsService,
 		@ITelemetryService private readonly telemetryService: ITelemetryService,
 		@IEditorService private readonly editorService: IEditorService,
+		@IStorageService private readonly storageService: IStorageService,
+		@ILogService private readonly logService: ILogService,
 	) {
 		super();
 
@@ -103,7 +118,7 @@ export class AgentSessionsControl extends Disposable implements IAgentSessionsCo
 		this.focusedAgentSessionTypeContextKey = ChatContextKeys.agentSessionType.bindTo(this.contextKeyService);
 		this.hasMultipleAgentSessionsSelectedContextKey = ChatContextKeys.hasMultipleAgentSessionsSelected.bindTo(this.contextKeyService);
 
-		this.createList(this.container);
+		this.create(this.container);
 
 		this.registerListeners();
 	}
@@ -137,11 +152,77 @@ export class AgentSessionsControl extends Disposable implements IAgentSessionsCo
 		}
 	}
 
-	private createList(container: HTMLElement): void {
+	private create(container: HTMLElement): void {
 		this.sessionsContainer = append(container, $('.agent-sessions-viewer'));
 
+		this.createEmptyFilterMessage(this.sessionsContainer);
+		this.createList(this.sessionsContainer);
+	}
+
+	private createEmptyFilterMessage(container: HTMLElement): void {
+		this.emptyFilterMessage = append(container, $('.agent-sessions-empty-filter-message'));
+		hide(this.emptyFilterMessage);
+
+		const span = append(this.emptyFilterMessage, $('span'));
+		span.textContent = `${localize('agentSessions.noFilterResults', "No matching sessions")} - `;
+
+		const link = append(this.emptyFilterMessage, $('span.reset-filter-link'));
+		link.textContent = localize('agentSessions.resetFilter', "Reset Filter");
+		link.tabIndex = 0;
+		link.setAttribute('role', 'button');
+		this._register(addDisposableListener(link, EventType.CLICK, () => this.options.filter.reset()));
+		this._register(addDisposableListener(link, EventType.KEY_DOWN, (e) => {
+			const event = new StandardKeyboardEvent(e);
+			if (event.keyCode === KeyCode.Enter || event.keyCode === KeyCode.Space) {
+				EventHelper.stop(e, true);
+				this.options.filter.reset();
+			}
+		}));
+	}
+
+	private static readonly SECTION_COLLAPSE_STATE_KEY = 'agentSessions.sectionCollapseState';
+
+	private getSavedCollapseState(section: AgentSessionSection): boolean | undefined {
+		const raw = this.storageService.get(AgentSessionsControl.SECTION_COLLAPSE_STATE_KEY, StorageScope.PROFILE);
+		if (raw) {
+			try {
+				const state: Record<string, boolean> = JSON.parse(raw);
+				if (typeof state[section] === 'boolean') {
+					return state[section];
+				}
+			} catch {
+				// ignore corrupt data
+			}
+		}
+		return undefined;
+	}
+
+	private saveSectionCollapseState(section: AgentSessionSection, collapsed: boolean): void {
+		let state: Record<string, boolean> = {};
+		const raw = this.storageService.get(AgentSessionsControl.SECTION_COLLAPSE_STATE_KEY, StorageScope.PROFILE);
+		if (raw) {
+			try {
+				const parsed = JSON.parse(raw);
+				if (typeof parsed === 'object' && parsed !== null && !Array.isArray(parsed)) {
+					state = parsed;
+				}
+			} catch {
+				// ignore corrupt data
+			}
+		}
+		state[section] = collapsed;
+		this.storageService.store(AgentSessionsControl.SECTION_COLLAPSE_STATE_KEY, JSON.stringify(state), StorageScope.PROFILE, StorageTarget.USER);
+	}
+
+	private createList(container: HTMLElement): void {
 		const collapseByDefault = (element: unknown) => {
 			if (isAgentSessionSection(element)) {
+				// Check for persisted user preference first
+				const saved = this.getSavedCollapseState(element.section);
+				if (saved !== undefined) {
+					return saved;
+				}
+
 				if (element.section === AgentSessionSection.More && !this.options.filter.getExcludes().read) {
 					return true; // More section is always collapsed unless only showing unread
 				}
@@ -163,16 +244,23 @@ export class AgentSessionsControl extends Disposable implements IAgentSessionsCo
 		};
 
 		const sorter = new AgentSessionsSorter(this.options);
+		const approvalModel = this.options.enableApprovalRow ? this._register(this.instantiationService.createInstance(AgentSessionApprovalModel)) : undefined;
+		const activeSessionResource = observableValue<URI | undefined>(this, undefined);
+		const sessionRenderer = this._register(this.instantiationService.createInstance(AgentSessionRenderer, {
+			...this.options,
+			isGroupedByRepository: () => this.options.filter.groupResults?.() === AgentSessionsGrouping.Repository,
+		}, approvalModel, activeSessionResource));
+		const sessionFilter = this._register(new AgentSessionsDataSource(this.options.filter, sorter, this.logService));
 		const list = this.sessionsList = this._register(this.instantiationService.createInstance(WorkbenchCompressibleAsyncDataTree,
 			'AgentSessionsView',
-			this.sessionsContainer,
-			new AgentSessionsListDelegate(),
+			container,
+			new AgentSessionsListDelegate(approvalModel),
 			new AgentSessionsCompressionDelegate(),
 			[
-				this._register(this.instantiationService.createInstance(AgentSessionRenderer, this.options)),
+				sessionRenderer,
 				this.instantiationService.createInstance(AgentSessionSectionRenderer),
 			],
-			new AgentSessionsDataSource(this.options.filter, sorter),
+			sessionFilter,
 			{
 				accessibilityProvider: new AgentSessionsAccessibilityProvider(),
 				dnd: this.instantiationService.createInstance(AgentSessionsDragAndDrop),
@@ -191,6 +279,16 @@ export class AgentSessionsControl extends Disposable implements IAgentSessionsCo
 
 		ChatContextKeys.agentSessionsViewerFocused.bindTo(list.contextKeyService);
 
+		this._register(sessionRenderer.onDidChangeItemHeight(session => {
+			if (list.hasNode(session)) {
+				list.updateElementHeight(session, undefined);
+			}
+		}));
+
+		this._register(sessionFilter.onDidGetChildren(count => {
+			this.updateEmpty(count === 0);
+		}));
+
 		const model = this.agentSessionsService.model;
 
 		this._register(this.options.filter.onDidChange(async () => {
@@ -223,10 +321,12 @@ export class AgentSessionsControl extends Disposable implements IAgentSessionsCo
 				this.focusedAgentSessionArchivedContextKey.set(focused.isArchived());
 				this.focusedAgentSessionReadContextKey.set(focused.isRead());
 				this.focusedAgentSessionTypeContextKey.set(focused.providerType);
+				activeSessionResource.set(focused.resource, undefined);
 			} else {
 				this.focusedAgentSessionArchivedContextKey.reset();
 				this.focusedAgentSessionReadContextKey.reset();
 				this.focusedAgentSessionTypeContextKey.reset();
+				activeSessionResource.set(undefined, undefined);
 			}
 
 			const selection = list.getSelection().filter(isAgentSession);
@@ -238,6 +338,30 @@ export class AgentSessionsControl extends Disposable implements IAgentSessionsCo
 
 			this.updateSectionCollapseStates();
 		}));
+
+		this._register(list.onDidChangeCollapseState(e => {
+			if (this._isProgrammaticCollapseChange) {
+				return;
+			}
+			const element = e.node.element?.element;
+			if (element && isAgentSessionSection(element)) {
+				this.saveSectionCollapseState(element.section, e.node.collapsed);
+			}
+		}));
+	}
+
+	private updateEmpty(isEmpty: boolean): void {
+		if (!this.emptyFilterMessage || !this.sessionsList) {
+			return;
+		}
+
+		const model = this.agentSessionsService.model;
+		const hasSessionsInModel = model.sessions.length > 0;
+		const isFilterActive = !this.options.filter.isDefault();
+
+		const showEmpty = hasSessionsInModel && isEmpty && isFilterActive;
+		setVisibility(showEmpty, this.emptyFilterMessage);
+		setVisibility(!showEmpty, this.sessionsList.getHTMLElement());
 	}
 
 	private hasTodaySessions(): boolean {
@@ -335,6 +459,19 @@ export class AgentSessionsControl extends Disposable implements IAgentSessionsCo
 			return;
 		}
 
+		this._isProgrammaticCollapseChange = true;
+		try {
+			this._updateSectionCollapseStatesCore();
+		} finally {
+			this._isProgrammaticCollapseChange = false;
+		}
+	}
+
+	private _updateSectionCollapseStatesCore(): void {
+		if (!this.sessionsList) {
+			return;
+		}
+
 		const model = this.agentSessionsService.model;
 		for (const child of this.sessionsList.getNode(model).children) {
 			if (!isAgentSessionSection(child.element)) {
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsFilter.ts b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsFilter.ts
index 65bfc186494c9..5cb399a6c875f 100644
--- a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsFilter.ts
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsFilter.ts
@@ -17,7 +17,8 @@ import { IAgentSessionsFilter, IAgentSessionsFilterExcludes } from './agentSessi
 
 export enum AgentSessionsGrouping {
 	Capped = 'capped',
-	Date = 'date'
+	Date = 'date',
+	Repository = 'repository'
 }
 
 export interface IAgentSessionsFilterOptions extends Partial<IAgentSessionsFilter> {
@@ -287,7 +288,7 @@ export class AgentSessionsFilter extends Disposable implements Required<IAgentSe
 				});
 			}
 			run(): void {
-				that.storeExcludes({ ...DEFAULT_EXCLUDES });
+				that.reset();
 			}
 		}));
 	}
@@ -332,4 +333,8 @@ export class AgentSessionsFilter extends Disposable implements Required<IAgentSe
 	notifyResults(count: number): void {
 		this.options.notifyResults?.(count);
 	}
+
+	reset(): void {
+		this.storeExcludes({ ...DEFAULT_EXCLUDES });
+	}
 }
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsModel.ts b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsModel.ts
index 218dad8cb8f26..ca12cdfc84694 100644
--- a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsModel.ts
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsModel.ts
@@ -22,10 +22,12 @@ import { IProductService } from '../../../../../platform/product/common/productS
 import { Registry } from '../../../../../platform/registry/common/platform.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../../platform/storage/common/storage.js';
 import { IWorkspaceContextService } from '../../../../../platform/workspace/common/workspace.js';
+import { IWorkspaceTrustManagementService } from '../../../../../platform/workspace/common/workspaceTrust.js';
 import { IChatEntitlementService } from '../../../../services/chat/common/chatEntitlementService.js';
 import { ILifecycleService } from '../../../../services/lifecycle/common/lifecycle.js';
 import { Extensions, IOutputChannelRegistry, IOutputService } from '../../../../services/output/common/output.js';
-import { ChatSessionStatus as AgentSessionStatus, IChatSessionFileChange, IChatSessionFileChange2, IChatSessionItem, IChatSessionsExtensionPoint, IChatSessionsService } from '../../common/chatSessionsService.js';
+import { ChatSessionStatus as AgentSessionStatus, IChatSessionFileChange, IChatSessionFileChange2, IChatSessionItem, IChatSessionsService, ResolvedChatSessionsExtensionPoint } from '../../common/chatSessionsService.js';
+import { getChatSessionType } from '../../common/model/chatUri.js';
 import { IChatWidgetService } from '../chat.js';
 import { AgentSessionProviders, getAgentSessionProvider, getAgentSessionProviderIcon, getAgentSessionProviderName, isBuiltInAgentSessionProvider } from './agentSessions.js';
 
@@ -161,6 +163,9 @@ export const enum AgentSessionSection {
 
 	// Capped Grouping
 	More = 'more',
+
+	// Repository Grouping
+	Repository = 'repository',
 }
 
 export interface IAgentSessionSection {
@@ -398,6 +403,7 @@ export class AgentSessionsModel extends Disposable implements IAgentSessionsMode
 		@IProductService private readonly productService: IProductService,
 		@IChatWidgetService private readonly chatWidgetService: IChatWidgetService,
 		@IWorkspaceContextService private readonly workspaceContextService: IWorkspaceContextService,
+		@IWorkspaceTrustManagementService private readonly workspaceTrustManagementService: IWorkspaceTrustManagementService,
 	) {
 		super();
 
@@ -426,19 +432,24 @@ export class AgentSessionsModel extends Disposable implements IAgentSessionsMode
 
 	private registerListeners(): void {
 
-		// Sessions changes
-		this._register(this.chatSessionsService.onDidChangeItemsProviders(({ chatSessionType }) => {
-			this.resolve(chatSessionType);
-		}));
-		this._register(this.chatSessionsService.onDidChangeAvailability(() => {
-			this.resolve(undefined);
-		}));
-		this._register(this.chatSessionsService.onDidChangeSessionItems(({ chatSessionType }) => {
-			this.updateItems([chatSessionType], CancellationToken.None);
-		}));
-		this._register(this.workspaceContextService.onDidChangeWorkspaceFolders(() => {
-			this.resolve(undefined);
+		// Sessions updates
+		this._register(this.chatSessionsService.onDidChangeItemsProviders(({ chatSessionType }) => this.resolve(chatSessionType)));
+		this._register(this.chatSessionsService.onDidChangeAvailability(() => this.resolve(undefined)));
+		this._register(this.chatSessionsService.onDidChangeSessionItems((delta) => {
+			const changedChatSessionTypes = new Set<string>();
+
+			for (const resource of delta.addedOrUpdated ?? []) {
+				changedChatSessionTypes.add(getChatSessionType(resource.resource));
+			}
+
+			for (const resource of delta.removed ?? []) {
+				changedChatSessionTypes.add(getChatSessionType(resource));
+			}
+
+			this.updateItems(Array.from(changedChatSessionTypes), CancellationToken.None);
 		}));
+		this._register(this.workspaceContextService.onDidChangeWorkspaceFolders(() => this.resolve(undefined)));
+		this._register(this.workspaceTrustManagementService.onDidChangeTrust(() => this.resolve(undefined)));
 
 		// State
 		this._register(this.storageService.onWillSaveState(() => {
@@ -488,17 +499,17 @@ export class AgentSessionsModel extends Disposable implements IAgentSessionsMode
 	 * Update the sessions by fetching from the service. This does not trigger an explicit refresh
 	 */
 	private async updateItems(providerFilter: readonly string[] | undefined, token: CancellationToken): Promise<void> {
-		const mapSessionContributionToType = new Map<string, IChatSessionsExtensionPoint>();
+		const mapSessionContributionToType = new Map<string, ResolvedChatSessionsExtensionPoint>();
 		for (const contribution of this.chatSessionsService.getAllChatSessionContributions()) {
 			mapSessionContributionToType.set(contribution.type, contribution);
 		}
 
-		const providerResults = await this.chatSessionsService.getChatSessionItems(providerFilter, token);
+		const providerResults = this.chatSessionsService.getChatSessionItems(providerFilter, token);
 
 		const resolvedProviders = new Set<string>();
 		const sessions = new ResourceMap<IInternalAgentSession>();
 
-		for (const { chatSessionType, items: providerSessions } of providerResults) {
+		for await (const { chatSessionType, items: providerSessions } of providerResults) {
 			resolvedProviders.add(chatSessionType);
 
 			if (token.isCancellationRequested) {
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsOpener.ts b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsOpener.ts
index be01ac3973c42..52b0707f567ba 100644
--- a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsOpener.ts
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsOpener.ts
@@ -103,7 +103,7 @@ async function openSessionDefault(accessor: ServicesAccessor, session: IAgentSes
 		}
 
 		const isLocalChatSession = session.resource.scheme === Schemas.vscodeChatEditor || session.resource.scheme === Schemas.vscodeLocalChatSession;
-		if (!isLocalChatSession && !(await chatSessionsService.canResolveChatSession(session.resource))) {
+		if (!isLocalChatSession && !(await chatSessionsService.canResolveChatSession(session.resource.scheme))) {
 			target = openOptions?.sideBySide ? SIDE_GROUP : ACTIVE_GROUP; // force to open in editor if session cannot be resolved in panel
 			options = { ...options, revealIfOpened: true };
 		}
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsService.ts b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsService.ts
index efdfc49fa93be..3bce41c7d028a 100644
--- a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsService.ts
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsService.ts
@@ -3,6 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { Emitter, Event } from '../../../../../base/common/event.js';
 import { Disposable } from '../../../../../base/common/lifecycle.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { createDecorator, IInstantiationService } from '../../../../../platform/instantiation/common/instantiation.js';
@@ -13,6 +14,7 @@ export interface IAgentSessionsService {
 	readonly _serviceBrand: undefined;
 
 	readonly model: IAgentSessionsModel;
+	readonly onDidChangeSessionArchivedState: Event<IAgentSession>;
 
 	getSession(resource: URI): IAgentSession | undefined;
 }
@@ -20,11 +22,14 @@ export interface IAgentSessionsService {
 export class AgentSessionsService extends Disposable implements IAgentSessionsService {
 
 	declare readonly _serviceBrand: undefined;
+	private readonly _onDidChangeSessionArchivedState = this._register(new Emitter<IAgentSession>());
+	readonly onDidChangeSessionArchivedState = this._onDidChangeSessionArchivedState.event;
 
 	private _model: IAgentSessionsModel | undefined;
 	get model(): IAgentSessionsModel {
 		if (!this._model) {
 			this._model = this._register(this.instantiationService.createInstance(AgentSessionsModel));
+			this._register(this._model.onDidChangeSessionArchivedState(session => this._onDidChangeSessionArchivedState.fire(session)));
 			this._model.resolve(undefined /* all providers */);
 		}
 
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsViewer.ts b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsViewer.ts
index be63965253746..bcb46c65c155c 100644
--- a/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsViewer.ts
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/agentSessionsViewer.ts
@@ -37,12 +37,20 @@ import { MenuId } from '../../../../../platform/actions/common/actions.js';
 import { IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
 import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
 import { ServiceCollection } from '../../../../../platform/instantiation/common/serviceCollection.js';
-import { Event } from '../../../../../base/common/event.js';
+import { Emitter, Event } from '../../../../../base/common/event.js';
 import { renderAsPlaintext } from '../../../../../base/browser/markdownRenderer.js';
 import { MarkdownString, IMarkdownString } from '../../../../../base/common/htmlContent.js';
 import { AgentSessionHoverWidget } from './agentSessionHoverWidget.js';
 import { AgentSessionProviders, getAgentSessionTime } from './agentSessions.js';
 import { AgentSessionsGrouping } from './agentSessionsFilter.js';
+import { autorun, IObservable } from '../../../../../base/common/observable.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { Button } from '../../../../../base/browser/ui/button/button.js';
+import { defaultButtonStyles } from '../../../../../platform/theme/browser/defaultStyles.js';
+import { AgentSessionApprovalModel } from './agentSessionApprovalModel.js';
+import { BugIndicatingError } from '../../../../../base/common/errors.js';
+import { ILogService } from '../../../../../platform/log/common/log.js';
+
 
 export type AgentSessionListItem = IAgentSession | IAgentSessionSection;
 
@@ -70,6 +78,11 @@ interface IAgentSessionItemTemplate {
 	readonly separator: HTMLElement;
 	readonly description: HTMLElement;
 
+	// Approval row
+	readonly approvalRow: HTMLElement;
+	readonly approvalLabel: HTMLElement;
+	readonly approvalButtonContainer: HTMLElement;
+
 	readonly contextKeyService: IContextKeyService;
 	readonly elementDisposable: DisposableStore;
 	readonly disposables: IDisposable;
@@ -77,19 +90,35 @@ interface IAgentSessionItemTemplate {
 
 export interface IAgentSessionRendererOptions {
 	readonly disableHover?: boolean;
+	readonly showIsolationIcon?: boolean;
 	getHoverPosition(): HoverPosition;
+	isGroupedByRepository?(): boolean;
 }
 
 export class AgentSessionRenderer extends Disposable implements ICompressibleTreeRenderer<IAgentSession, FuzzyScore, IAgentSessionItemTemplate> {
 
 	static readonly TEMPLATE_ID = 'agent-session';
 
+	static readonly APPROVAL_ROW_MAX_LINES = 3;
+	private static readonly _APPROVAL_ROW_LINE_HEIGHT = 18;
+	private static readonly _APPROVAL_ROW_OVERHEAD = 14; // 4px margin-top + 4px padding-top + 4px padding-bottom + 2px border
+
+	static getApprovalRowHeight(label: string): number {
+		const lineCount = Math.min(label.split(/\r?\n/).length, AgentSessionRenderer.APPROVAL_ROW_MAX_LINES);
+		return lineCount * AgentSessionRenderer._APPROVAL_ROW_LINE_HEIGHT + AgentSessionRenderer._APPROVAL_ROW_OVERHEAD;
+	}
+
 	readonly templateId = AgentSessionRenderer.TEMPLATE_ID;
 
 	private readonly sessionHover = this._register(new MutableDisposable<AgentSessionHoverWidget>());
 
+	private readonly _onDidChangeItemHeight = this._register(new Emitter<IAgentSession>());
+	readonly onDidChangeItemHeight: Event<IAgentSession> = this._onDidChangeItemHeight.event;
+
 	constructor(
 		private readonly options: IAgentSessionRendererOptions,
+		private readonly _approvalModel: AgentSessionApprovalModel | undefined,
+		private readonly _activeSessionResource: IObservable<URI | undefined>,
 		@IMarkdownRendererService private readonly markdownRendererService: IMarkdownRendererService,
 		@IProductService private readonly productService: IProductService,
 		@IHoverService private readonly hoverService: IHoverService,
@@ -129,6 +158,10 @@ export class AgentSessionRenderer extends Disposable implements ICompressibleTre
 								h('span.agent-session-status-time@statusTime')
 							]),
 						]),
+					]),
+					h('div.agent-session-approval-row@approvalRow', [
+						h('span.agent-session-approval-label@approvalLabel'),
+						h('div.agent-session-approval-button@approvalButtonContainer'),
 					])
 				])
 			]
@@ -156,6 +189,9 @@ export class AgentSessionRenderer extends Disposable implements ICompressibleTre
 			statusContainer: elements.statusContainer,
 			statusProviderIcon: elements.statusProviderIcon,
 			statusTime: elements.statusTime,
+			approvalRow: elements.approvalRow,
+			approvalLabel: elements.approvalLabel,
+			approvalButtonContainer: elements.approvalButtonContainer,
 			contextKeyService,
 			elementDisposable,
 			disposables
@@ -229,15 +265,38 @@ export class AgentSessionRenderer extends Disposable implements ICompressibleTre
 
 		// Hover
 		this.renderHover(session, template);
+
+		// Approval row
+		if (this._approvalModel) {
+			this.renderApprovalRow(session, template);
+		}
 	}
 
 	private renderBadge(session: ITreeNode<IAgentSession, FuzzyScore>, template: IAgentSessionItemTemplate): boolean {
 		const badge = session.element.badge;
-		if (badge) {
-			this.renderMarkdownOrText(badge, template.badge, template.elementDisposable);
+		if (!badge) {
+			return false;
 		}
 
-		return !!badge;
+		// When grouped by repository, hide the badge only if the name it shows
+		// matches the section header (i.e. the repository name for this session).
+		// Badges with a different name (e.g. worktree name) are still shown.
+		// Archived sessions always keep their badge since they are grouped under
+		// the "Archived" section, not a repository section.
+		if (this.options.isGroupedByRepository?.() && !session.element.isArchived()) {
+			const raw = typeof badge === 'string' ? badge : badge.value;
+			const match = raw.match(/^\$\((?:repo|folder|worktree)\)\s*(.+)/);
+			if (match) {
+				const badgeName = match[1].trim();
+				const repoName = getRepositoryName(session.element);
+				if (badgeName === repoName) {
+					return false;
+				}
+			}
+		}
+
+		this.renderMarkdownOrText(badge, template.badge, template.elementDisposable);
+		return true;
 	}
 
 	private renderMarkdownOrText(content: string | IMarkdownString, container: HTMLElement, disposables: DisposableStore): void {
@@ -353,8 +412,17 @@ export class AgentSessionRenderer extends Disposable implements ICompressibleTre
 		};
 
 		// Provider icon (only shown for non-local sessions)
+		// When showIsolationIcon is enabled for background sessions, show worktree/folder icon instead
 		const isLocal = session.element.providerType === AgentSessionProviders.Local;
-		template.statusProviderIcon.className = isLocal ? '' : `agent-session-status-provider-icon ${ThemeIcon.asClassName(session.element.icon)}`;
+		if (isLocal) {
+			template.statusProviderIcon.className = '';
+		} else if (this.options.showIsolationIcon && session.element.providerType === AgentSessionProviders.Background) {
+			const hasWorktree = typeof session.element.metadata?.worktreePath === 'string';
+			const isolationIcon = hasWorktree ? Codicon.worktree : Codicon.folder;
+			template.statusProviderIcon.className = `agent-session-status-provider-icon ${ThemeIcon.asClassName(isolationIcon)}`;
+		} else {
+			template.statusProviderIcon.className = `agent-session-status-provider-icon ${ThemeIcon.asClassName(session.element.icon)}`;
+		}
 
 		// Time label
 		template.statusTime.textContent = getTimeLabel(session.element);
@@ -396,6 +464,68 @@ export class AgentSessionRenderer extends Disposable implements ICompressibleTre
 		};
 	}
 
+	private renderApprovalRow(session: ITreeNode<IAgentSession, FuzzyScore>, template: IAgentSessionItemTemplate): void {
+		if (this._approvalModel === undefined) {
+			throw new BugIndicatingError('Approval model is required to render approval row');
+		}
+
+		const approvalModel = this._approvalModel;
+		// Initialize from current model state to avoid unnecessary height changes on first render
+		const initialInfo = approvalModel.getApproval(session.element.resource).get();
+		let wasVisible = !!initialInfo;
+		template.approvalRow.classList.toggle('visible', wasVisible);
+
+		const buttonStore = template.elementDisposable.add(new DisposableStore());
+
+		template.elementDisposable.add(autorun(reader => {
+			buttonStore.clear();
+
+			const info = approvalModel.getApproval(session.element.resource).read(reader);
+			const visible = !!info;
+
+			template.approvalRow.classList.toggle('visible', visible);
+
+			if (info) {
+				// Render up to 3 lines, each as a separate code block so CSS can truncate per-line
+				const lines = info.label.split('\n');
+				const maxLines = AgentSessionRenderer.APPROVAL_ROW_MAX_LINES;
+				const visibleLines = lines.slice(0, maxLines);
+				if (lines.length > maxLines) {
+					visibleLines[maxLines - 1] = `${visibleLines[maxLines - 1]} \u2026`;
+				}
+				const langId = info.languageId ?? 'json';
+				const labelContent = new MarkdownString();
+				for (const line of visibleLines) {
+					labelContent.appendCodeblock(langId, line);
+				}
+				this.renderMarkdownOrText(labelContent, template.approvalLabel, buttonStore);
+
+				// Hover with full content as a code block
+				const fullContent = new MarkdownString().appendCodeblock(info.languageId ?? 'json', info.label);
+				buttonStore.add(this.hoverService.setupDelayedHover(template.approvalLabel, {
+					content: fullContent,
+					style: HoverStyle.Pointer,
+					position: { hoverPosition: HoverPosition.BELOW },
+				}));
+
+				template.approvalButtonContainer.textContent = '';
+				const isActive = this._activeSessionResource.read(reader)?.toString() === session.element.resource.toString();
+				const button = buttonStore.add(new Button(template.approvalButtonContainer, {
+					title: localize('allowActionOnce', "Allow once"),
+					secondary: isActive,
+					...defaultButtonStyles
+				}));
+				button.label = localize('allowAction', "Allow");
+				buttonStore.add(button.onDidClick(() => info.confirm()));
+			}
+
+			if (wasVisible !== visible) {
+				wasVisible = visible;
+				this._onDidChangeItemHeight.fire(session.element);
+			}
+		}));
+	}
+
 	renderCompressedElements(node: ITreeNode<ICompressedTreeNode<IAgentSession>, FuzzyScore>, index: number, templateData: IAgentSessionItemTemplate, details?: ITreeElementRenderDetails): void {
 		throw new Error('Should never happen since session is incompressible');
 	}
@@ -509,12 +639,23 @@ export class AgentSessionsListDelegate implements IListVirtualDelegate<AgentSess
 	static readonly ITEM_HEIGHT = 54;
 	static readonly SECTION_HEIGHT = 26;
 
+	constructor(private readonly _approvalModel?: AgentSessionApprovalModel) { }
+
 	getHeight(element: AgentSessionListItem): number {
 		if (isAgentSessionSection(element)) {
 			return AgentSessionsListDelegate.SECTION_HEIGHT;
 		}
 
-		return AgentSessionsListDelegate.ITEM_HEIGHT;
+		let height = AgentSessionsListDelegate.ITEM_HEIGHT;
+		const approval = this._approvalModel?.getApproval(element.resource).get();
+		if (approval) {
+			height += AgentSessionRenderer.getApprovalRowHeight(approval.label);
+		}
+		return height;
+	}
+
+	hasDynamicHeight(element: AgentSessionListItem): boolean {
+		return !!this._approvalModel && isAgentSession(element);
 	}
 
 	getTemplateId(element: AgentSessionListItem): string {
@@ -591,16 +732,32 @@ export interface IAgentSessionsFilter {
 	 * Get the current filter excludes for display in the UI.
 	 */
 	getExcludes(): IAgentSessionsFilterExcludes;
+
+	/**
+	 * Whether the filter is at its default state (no custom filters applied).
+	 */
+	isDefault(): boolean;
+
+	/**
+	 * Reset the filter to its default state.
+	 */
+	reset(): void;
 }
 
-export class AgentSessionsDataSource implements IAsyncDataSource<IAgentSessionsModel, AgentSessionListItem> {
+export class AgentSessionsDataSource extends Disposable implements IAsyncDataSource<IAgentSessionsModel, AgentSessionListItem> {
 
 	private static readonly CAPPED_SESSIONS_LIMIT = 3;
 
+	private readonly _onDidGetChildren = this._register(new Emitter<number>());
+	readonly onDidGetChildren: Event<number> = this._onDidGetChildren.event;
+
 	constructor(
 		private readonly filter: IAgentSessionsFilter | undefined,
 		private readonly sorter: ITreeSorter<IAgentSession>,
-	) { }
+		private readonly logService?: ILogService,
+	) {
+		super();
+	}
 
 	hasChildren(element: IAgentSessionsModel | AgentSessionListItem): boolean {
 
@@ -641,6 +798,7 @@ export class AgentSessionsDataSource implements IAsyncDataSource<IAgentSessionsM
 
 			// Callback results count
 			this.filter?.notifyResults?.(filteredSessions.length);
+			this._onDidGetChildren.fire(filteredSessions.length);
 
 			// Group sessions into sections if enabled
 			if (this.filter?.groupResults?.()) {
@@ -671,6 +829,8 @@ export class AgentSessionsDataSource implements IAsyncDataSource<IAgentSessionsM
 			}
 
 			return this.groupSessionsCapped(sortedSessions);
+		} else if (this.filter?.groupResults?.() === AgentSessionsGrouping.Repository) {
+			return this.groupSessionsByRepository(sortedSessions);
 		} else {
 			return this.groupSessionsByDate(sortedSessions);
 		}
@@ -714,6 +874,200 @@ export class AgentSessionsDataSource implements IAsyncDataSource<IAgentSessionsM
 
 		return result;
 	}
+
+	private groupSessionsByRepository(sortedSessions: IAgentSession[]): AgentSessionListItem[] {
+		const repoMap = new Map<string, { label: string; sessions: IAgentSession[] }>();
+		const archivedSessions: IAgentSession[] = [];
+		const unknownKey = '\x00unknown';
+		const unknownLabel = localize('agentSessions.noRepository', "Other");
+
+		for (const session of sortedSessions) {
+			if (session.isArchived()) {
+				archivedSessions.push(session);
+				continue;
+			}
+
+			const repoName = this.getRepositoryName(session);
+			if (!repoName) {
+				this.logService?.warn('[AgentSessions] Could not determine repository name for session, categorizing as "Other"', JSON.stringify(session));
+			}
+			const repoId = repoName || unknownKey;
+			const repoLabel = repoName || unknownLabel;
+
+			let group = repoMap.get(repoId);
+			if (!group) {
+				group = { label: repoLabel, sessions: [] };
+				repoMap.set(repoId, group);
+			}
+			group.sessions.push(session);
+		}
+
+		const result: AgentSessionListItem[] = [];
+		for (const [, { label, sessions }] of repoMap) {
+			result.push({
+				section: AgentSessionSection.Repository,
+				label,
+				sessions,
+			});
+		}
+
+		if (archivedSessions.length > 0) {
+			result.push({
+				section: AgentSessionSection.Archived,
+				label: AgentSessionSectionLabels[AgentSessionSection.Archived],
+				sessions: archivedSessions,
+			});
+		}
+
+		return result;
+	}
+
+	private getRepositoryName(session: IAgentSession): string | undefined {
+		return getRepositoryName(session);
+	}
+}
+
+/**
+ * Extracts the repository name for an agent session from its metadata or badge.
+ * Used for grouping sessions by repository and for determining whether a badge
+ * is redundant with the section header.
+ */
+export function getRepositoryName(session: IAgentSession): string | undefined {
+	const metadata = session.metadata;
+	if (metadata) {
+		// Cloud sessions: metadata.owner + metadata.name
+		const owner = metadata.owner as string | undefined;
+		const name = metadata.name as string | undefined;
+		if (owner && name) {
+			return name;
+		}
+
+		// repositoryNwo: "owner/repo"
+		const nwo = metadata.repositoryNwo as string | undefined;
+		if (nwo && nwo.includes('/')) {
+			return nwo.split('/').pop()!;
+		}
+
+		// repository: could be "owner/repo", a URL, or git@host:owner/repo.git
+		const repository = metadata.repository as string | undefined;
+		if (repository) {
+			const repoName = parseRepositoryName(repository);
+			if (repoName) {
+				return repoName;
+			}
+		}
+
+		// repositoryUrl: "https://github.com/owner/repo"
+		const repositoryUrl = metadata.repositoryUrl as string | undefined;
+		if (repositoryUrl) {
+			const repoName = parseRepositoryName(repositoryUrl);
+			if (repoName) {
+				return repoName;
+			}
+		}
+
+		// repositoryPath: extract repo name from the directory path basename
+		const repositoryPath = metadata.repositoryPath as string | undefined;
+		if (repositoryPath) {
+			const repoName = extractRepoNameFromPath(repositoryPath);
+			if (repoName) {
+				return repoName;
+			}
+		}
+
+		// worktreePath: extract repo name from the worktree path
+		const worktreePath = metadata.worktreePath as string | undefined;
+		if (worktreePath) {
+			const repoName = extractRepoNameFromPath(worktreePath);
+			if (repoName) {
+				return repoName;
+			}
+		}
+
+		// workingDirectoryPath: fallback to extract name from the working directory
+		const workingDirectoryPath = metadata.workingDirectoryPath as string | undefined;
+		if (workingDirectoryPath) {
+			const repoName = extractRepoNameFromPath(workingDirectoryPath);
+			if (repoName) {
+				return repoName;
+			}
+		}
+	}
+
+	// Fallback: extract repo/folder name from badge
+	const badge = session.badge;
+	if (badge) {
+		const raw = typeof badge === 'string' ? badge : badge.value;
+		const badgeMatch = raw.match(/\$\((?:repo|folder|worktree)\)\s*(.+)/);
+		if (badgeMatch) {
+			return badgeMatch[1].trim();
+		}
+	}
+
+	return undefined;
+}
+
+/**
+ * Parses a repository name from various formats: "owner/repo", URLs,
+ * and git@host:owner/repo.git style references.
+ */
+function parseRepositoryName(value: string): string | undefined {
+	// Direct "owner/repo" style (no scheme, no git@ prefix)
+	if (value.includes('/') && !value.includes('://') && !value.startsWith('git@')) {
+		let repoSegment = value.split('/').filter(Boolean).pop();
+		if (repoSegment?.endsWith('.git')) {
+			repoSegment = repoSegment.slice(0, -4);
+		}
+		return repoSegment || undefined;
+	}
+
+	// Standard URL formats (https://..., ssh://..., etc.)
+	try {
+		const url = new URL(value);
+		const parts = url.pathname.split('/').filter(Boolean);
+		if (parts.length >= 2) {
+			let repoSegment = parts[1];
+			if (repoSegment.endsWith('.git')) {
+				repoSegment = repoSegment.slice(0, -4);
+			}
+			return repoSegment || undefined;
+		}
+	} catch {
+		// not a standard URL
+	}
+
+	// git@host:owner/repo(.git) style URLs
+	if (value.startsWith('git@')) {
+		const colonIndex = value.indexOf(':');
+		if (colonIndex !== -1 && colonIndex < value.length - 1) {
+			const pathPart = value.substring(colonIndex + 1);
+			let repoSegment = pathPart.split('/').filter(Boolean).pop();
+			if (repoSegment?.endsWith('.git')) {
+				repoSegment = repoSegment.slice(0, -4);
+			}
+			return repoSegment || undefined;
+		}
+	}
+
+	return undefined;
+}
+
+/**
+ * Extracts the repository name from a filesystem path, handling git worktree
+ * conventions where paths follow `<repo>.worktrees/<worktree-name>`.
+ */
+function extractRepoNameFromPath(dirPath: string): string | undefined {
+	const segments = dirPath.split(/[/\\]/).filter(Boolean);
+	if (segments.length < 2) {
+		return segments[0];
+	}
+
+	const parent = segments[segments.length - 2];
+	if (parent.endsWith('.worktrees')) {
+		return parent.slice(0, -'.worktrees'.length) || undefined;
+	}
+
+	return segments[segments.length - 1];
 }
 
 export const AgentSessionSectionLabels = {
@@ -793,7 +1147,7 @@ export class AgentSessionsIdentityProvider implements IIdentityProvider<IAgentSe
 
 	getId(element: IAgentSessionsModel | AgentSessionListItem): string {
 		if (isAgentSessionSection(element)) {
-			return `section-${element.section}`;
+			return `section-${element.section}-${element.label}`;
 		}
 
 		if (isAgentSession(element)) {
@@ -839,17 +1193,6 @@ export class AgentSessionsSorter implements ITreeSorter<IAgentSession> {
 			return 1; // a (other) comes after b (needs input)
 		}
 
-		// In Progress
-		const aInProgress = sessionA.status === AgentSessionStatus.InProgress;
-		const bInProgress = sessionB.status === AgentSessionStatus.InProgress;
-
-		if (aInProgress && !bInProgress) {
-			return -1; // a (in-progress) comes before b (finished)
-		}
-		if (!aInProgress && bInProgress) {
-			return 1; // a (finished) comes after b (in-progress)
-		}
-
 		// Archived
 		const aArchived = sessionA.isArchived();
 		const bArchived = sessionB.isArchived();
@@ -867,7 +1210,7 @@ export class AgentSessionsSorter implements ITreeSorter<IAgentSession> {
 			return override;
 		}
 
-		//Sort by end or start time (most recent first)
+		// Sort by end or start time (most recent first)
 		const timeA = getAgentSessionTime(sessionA.timing);
 		const timeB = getAgentSessionTime(sessionB.timing);
 		return timeB - timeA;
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/experiments/agentTitleBarStatusWidget.ts b/src/vs/workbench/contrib/chat/browser/agentSessions/experiments/agentTitleBarStatusWidget.ts
index 9b9ea511fdf93..86ec453b950af 100644
--- a/src/vs/workbench/contrib/chat/browser/agentSessions/experiments/agentTitleBarStatusWidget.ts
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/experiments/agentTitleBarStatusWidget.ts
@@ -432,7 +432,7 @@ export class AgentTitleBarStatusWidget extends BaseActionViewItem {
 			label.classList.add('has-progress');
 		}
 
-		const hoverLabel = localize('askAnythingPlaceholder', "Ask anything or describe what to build next");
+		const hoverLabel = localize('askAnythingPlaceholder', "Ask anything or describe what to build");
 
 		label.textContent = defaultLabel;
 		pill.appendChild(label);
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/localAgentSessionsController.ts b/src/vs/workbench/contrib/chat/browser/agentSessions/localAgentSessionsController.ts
index 18d0bcb1c29f0..c2eed78bfbfa7 100644
--- a/src/vs/workbench/contrib/chat/browser/agentSessions/localAgentSessionsController.ts
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/localAgentSessionsController.ts
@@ -10,12 +10,14 @@ import { Emitter } from '../../../../../base/common/event.js';
 import { Disposable } from '../../../../../base/common/lifecycle.js';
 import { ResourceSet } from '../../../../../base/common/map.js';
 import { Schemas } from '../../../../../base/common/network.js';
+import { isEqual } from '../../../../../base/common/resources.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { ILogService } from '../../../../../platform/log/common/log.js';
 import { IWorkbenchContribution } from '../../../../common/contributions.js';
-import { IChatModel } from '../../common/model/chatModel.js';
 import { convertLegacyChatSessionTiming, IChatDetail, IChatService, ResponseModelState } from '../../common/chatService/chatService.js';
-import { ChatSessionStatus, IChatSessionItem, IChatSessionItemController, IChatSessionsService, localChatSessionType } from '../../common/chatSessionsService.js';
+import { ChatSessionStatus, IChatSessionItem, IChatSessionItemController, IChatSessionItemsDelta, IChatSessionsService, localChatSessionType } from '../../common/chatSessionsService.js';
+import { IChatModel } from '../../common/model/chatModel.js';
 import { getChatSessionType } from '../../common/model/chatUri.js';
-import { ILogService } from '../../../../../platform/log/common/log.js';
 
 export class LocalAgentsSessionsController extends Disposable implements IChatSessionItemController, IWorkbenchContribution {
 
@@ -26,7 +28,7 @@ export class LocalAgentsSessionsController extends Disposable implements IChatSe
 	private readonly _onDidChange = this._register(new Emitter<void>());
 	readonly onDidChange = this._onDidChange.event;
 
-	readonly _onDidChangeChatSessionItems = this._register(new Emitter<void>());
+	readonly _onDidChangeChatSessionItems = this._register(new Emitter<IChatSessionItemsDelta>());
 	readonly onDidChangeChatSessionItems = this._onDidChangeChatSessionItems.event;
 
 	constructor(
@@ -51,22 +53,32 @@ export class LocalAgentsSessionsController extends Disposable implements IChatSe
 	}
 
 	private registerListeners(): void {
-		const refreshItems = async () => {
-			this._onDidChangeChatSessionItems.fire();
+		this._register(this.chatService.registerChatModelChangeListeners(Schemas.vscodeLocalChatSession, async sessionResource => {
+			if (getChatSessionType(sessionResource) !== this.chatSessionType) {
+				return;
+			}
+
+			// TODO: This gets fired too often
 			await this.refresh(CancellationToken.None);
-			this._onDidChangeChatSessionItems.fire();
-		};
+			const item = this.getItem(sessionResource);
 
-		this._register(this.chatSessionsService.registerChatModelChangeListeners(this.chatService, Schemas.vscodeLocalChatSession, refreshItems));
+			if (item) {
+				this._onDidChangeChatSessionItems.fire({ addedOrUpdated: [item] });
+			}
+		}));
 
 		this._register(this.chatService.onDidDisposeSession(e => {
-			const session = e.sessionResource.filter(resource => getChatSessionType(resource) === this.chatSessionType);
-			if (session.length > 0) {
-				refreshItems();
+			const removedSessionResources = e.sessionResource.filter(resource => getChatSessionType(resource) === this.chatSessionType);
+			if (removedSessionResources.length) {
+				this._onDidChangeChatSessionItems.fire({ removed: removedSessionResources });
 			}
 		}));
 	}
 
+	private getItem(sessionResource: URI): IChatSessionItem | undefined {
+		return this._items.find(item => isEqual(item.resource, sessionResource));
+	}
+
 	private async provideChatSessionItems(token: CancellationToken): Promise<IChatSessionItem[]> {
 		const sessions: IChatSessionItem[] = [];
 		const sessionsByResource = new ResourceSet();
diff --git a/src/vs/workbench/contrib/chat/browser/agentSessions/media/agentsessionsviewer.css b/src/vs/workbench/contrib/chat/browser/agentSessions/media/agentsessionsviewer.css
index 8edec5cccc335..913a82d0e3972 100644
--- a/src/vs/workbench/contrib/chat/browser/agentSessions/media/agentsessionsviewer.css
+++ b/src/vs/workbench/contrib/chat/browser/agentSessions/media/agentsessionsviewer.css
@@ -99,8 +99,7 @@
 			.agent-session-icon {
 				flex-shrink: 0;
 				font-size: 12px;
-				width: 14px;
-				height: 14px;
+				height: 16px;
 				display: flex;
 				align-items: center;
 				justify-content: center;
@@ -139,7 +138,7 @@
 
 		.agent-session-title-row {
 			line-height: 17px;
-			padding-bottom: 6px;
+			padding-bottom: 4px;
 		}
 
 		.agent-session-details-row {
@@ -252,6 +251,53 @@
 				}
 			}
 		}
+		.agent-session-approval-row {
+			display: none;
+			align-items: flex-end;
+			gap: 8px;
+			margin-top: 4px;
+			padding: 4px 8px;
+			box-sizing: border-box;
+			border: 1px solid var(--vscode-contrastBorder, var(--vscode-widget-border, transparent));
+			border-radius: 4px;
+			background-color: var(--vscode-editor-background);
+			color: var(--vscode-editor-foreground);
+
+			&.visible {
+				display: flex;
+			}
+
+			.agent-session-approval-label {
+				flex: 1;
+				overflow: hidden;
+				min-width: 0;
+
+				& > .rendered-markdown,
+				& > .rendered-markdown > .code,
+				& > .rendered-markdown > .code > span {
+					display: block;
+					overflow: hidden;
+				}
+
+				.monaco-tokenized-source {
+					display: block;
+					overflow: hidden;
+					white-space: nowrap;
+					text-overflow: ellipsis;
+					font-size: 12px;
+				}
+			}
+
+			.agent-session-approval-button {
+				flex-shrink: 0;
+
+				.monaco-button {
+					padding: 2px 10px;
+					font-size: 12px;
+					white-space: nowrap;
+				}
+			}
+		}
 	}
 
 	.agent-session-section {
@@ -298,4 +344,26 @@
 	.monaco-list:not(:focus) .monaco-list-row.selected .agent-session-section-label {
 		color: var(--vscode-list-inactiveSelectionForeground);
 	}
+
+	.agent-sessions-empty-filter-message {
+		padding: 8px 12px;
+		font-size: 12px;
+		color: var(--vscode-descriptionForeground);
+
+		.reset-filter-link {
+			color: var(--vscode-textLink-foreground);
+			cursor: pointer;
+			text-decoration: none;
+
+			&:hover {
+				text-decoration: underline;
+			}
+
+			&:focus-visible {
+				text-decoration: underline;
+				outline: 1px solid var(--vscode-focusBorder);
+				outline-offset: 1px;
+			}
+		}
+	}
 }
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationDebugPanel.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationDebugPanel.ts
new file mode 100644
index 0000000000000..e4ed34928ff12
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationDebugPanel.ts
@@ -0,0 +1,202 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { CancellationToken } from '../../../../../base/common/cancellation.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { IPromptsService, PromptsStorage, IPromptPath } from '../../common/promptSyntax/service/promptsService.js';
+import { PromptsType } from '../../common/promptSyntax/promptTypes.js';
+import { IAICustomizationWorkspaceService, applyStorageSourceFilter, IStorageSourceFilter } from '../../common/aiCustomizationWorkspaceService.js';
+import { AICustomizationManagementSection } from './aiCustomizationManagement.js';
+
+/**
+ * Maps section ID to prompt type. Duplicated from aiCustomizationListWidget
+ * to avoid a circular dependency.
+ */
+function sectionToPromptType(section: AICustomizationManagementSection): PromptsType {
+	switch (section) {
+		case AICustomizationManagementSection.Agents:
+			return PromptsType.agent;
+		case AICustomizationManagementSection.Skills:
+			return PromptsType.skill;
+		case AICustomizationManagementSection.Instructions:
+			return PromptsType.instructions;
+		case AICustomizationManagementSection.Hooks:
+			return PromptsType.hook;
+		case AICustomizationManagementSection.Prompts:
+		default:
+			return PromptsType.prompt;
+	}
+}
+
+/**
+ * Snapshot of the list widget's internal state, passed in to avoid coupling.
+ */
+export interface IDebugWidgetState {
+	readonly allItems: readonly { readonly storage: PromptsStorage }[];
+	readonly displayEntries: readonly { type: string; label?: string; count?: number; collapsed?: boolean }[];
+}
+
+/**
+ * Generates a debug diagnostics report for the AI Customization list widget.
+ * Returns the report as a string suitable for opening in an editor.
+ */
+export async function generateCustomizationDebugReport(
+	section: AICustomizationManagementSection,
+	promptsService: IPromptsService,
+	workspaceService: IAICustomizationWorkspaceService,
+	widgetState: IDebugWidgetState,
+): Promise<string> {
+	const promptType = sectionToPromptType(section);
+	const filter = workspaceService.getStorageSourceFilter(promptType);
+	const lines: string[] = [];
+
+	lines.push(`== Customization Debug: ${section} (${promptType}) ==`);
+	lines.push(`Window: ${workspaceService.isSessionsWindow ? 'Sessions' : 'Core VS Code'}`);
+	lines.push(`Active root: ${workspaceService.getActiveProjectRoot()?.fsPath ?? '(none)'}`);
+	lines.push(`Sections: [${workspaceService.managementSections.join(', ')}]`);
+	lines.push(`Filter sources: [${filter.sources.join(', ')}]`);
+	if (filter.includedUserFileRoots) {
+		lines.push(`Filter includedUserFileRoots:`);
+		for (const r of filter.includedUserFileRoots) {
+			lines.push(`  ${r.fsPath}`);
+		}
+	} else {
+		lines.push(`Filter includedUserFileRoots: (all)`);
+	}
+	lines.push('');
+
+	await appendRawServiceData(lines, promptsService, promptType);
+	await appendFilteredData(lines, promptsService, promptType, filter);
+	appendWidgetState(lines, widgetState);
+	await appendSourceFolders(lines, promptsService, promptType);
+
+	return lines.join('\n');
+}
+
+async function appendRawServiceData(lines: string[], promptsService: IPromptsService, promptType: PromptsType): Promise<void> {
+	lines.push('--- Stage 1: Raw PromptsService Data ---');
+
+	const [localFiles, userFiles, extensionFiles] = await Promise.all([
+		promptsService.listPromptFilesForStorage(promptType, PromptsStorage.local, CancellationToken.None),
+		promptsService.listPromptFilesForStorage(promptType, PromptsStorage.user, CancellationToken.None),
+		promptsService.listPromptFilesForStorage(promptType, PromptsStorage.extension, CancellationToken.None),
+	]);
+
+	lines.push(`  listPromptFilesForStorage(local):  ${localFiles.length} files`);
+	appendFileList(lines, localFiles);
+
+	lines.push(`  listPromptFilesForStorage(user):   ${userFiles.length} files`);
+	appendFileList(lines, userFiles);
+
+	lines.push(`  listPromptFilesForStorage(ext):    ${extensionFiles.length} files`);
+	appendFileList(lines, extensionFiles);
+
+	const allFiles = await promptsService.listPromptFiles(promptType, CancellationToken.None);
+	lines.push(`  listPromptFiles (merged):          ${allFiles.length} files`);
+
+	if (promptType === PromptsType.instructions) {
+		const agentInstructions = await promptsService.listAgentInstructions(CancellationToken.None, undefined);
+		lines.push(`  listAgentInstructions (extra):     ${agentInstructions.length} files`);
+		appendFileList(lines, agentInstructions);
+	}
+
+	if (promptType === PromptsType.skill) {
+		const skills = await promptsService.findAgentSkills(CancellationToken.None);
+		lines.push(`  findAgentSkills:                   ${skills?.length ?? 0} skills`);
+		for (const s of skills ?? []) {
+			lines.push(`    ${s.name ?? '?'} [${s.storage}] ${s.uri.fsPath}`);
+		}
+	}
+
+	if (promptType === PromptsType.agent) {
+		const agents = await promptsService.getCustomAgents(CancellationToken.None);
+		lines.push(`  getCustomAgents:                   ${agents.length} agents`);
+		for (const a of agents) {
+			lines.push(`    ${a.name} [${a.source.storage}] ${a.uri.fsPath}`);
+		}
+	}
+
+	if (promptType === PromptsType.prompt) {
+		const commands = await promptsService.getPromptSlashCommands(CancellationToken.None);
+		lines.push(`  getPromptSlashCommands:            ${commands.length} commands`);
+		for (const c of commands) {
+			lines.push(`    /${c.name} [${c.promptPath.storage}] ${c.promptPath.uri.fsPath} (type=${c.promptPath.type})`);
+		}
+	}
+
+	lines.push('');
+}
+
+async function appendFilteredData(lines: string[], promptsService: IPromptsService, promptType: PromptsType, filter: IStorageSourceFilter): Promise<void> {
+	lines.push('--- Stage 2: After applyStorageSourceFilter ---');
+
+	const [localFiles, userFiles, extensionFiles] = await Promise.all([
+		promptsService.listPromptFilesForStorage(promptType, PromptsStorage.local, CancellationToken.None),
+		promptsService.listPromptFilesForStorage(promptType, PromptsStorage.user, CancellationToken.None),
+		promptsService.listPromptFilesForStorage(promptType, PromptsStorage.extension, CancellationToken.None),
+	]);
+
+	const all: IPromptPath[] = [...localFiles, ...userFiles, ...extensionFiles];
+	const filtered = applyStorageSourceFilter(all, filter);
+	lines.push(`  Input: ${all.length} → Filtered: ${filtered.length}`);
+	lines.push(`    local:     ${filtered.filter(f => f.storage === PromptsStorage.local).length}`);
+	lines.push(`    user:      ${filtered.filter(f => f.storage === PromptsStorage.user).length}`);
+	lines.push(`    extension: ${filtered.filter(f => f.storage === PromptsStorage.extension).length}`);
+
+	const removedCount = all.length - filtered.length;
+	if (removedCount > 0) {
+		const filteredUris = new Set(filtered.map(f => f.uri.toString()));
+		const removed = all.filter(f => !filteredUris.has(f.uri.toString()));
+		lines.push(`  Removed (${removedCount}):`);
+		for (const f of removed) {
+			lines.push(`    [${f.storage}] ${f.uri.fsPath}`);
+		}
+	}
+
+	lines.push('');
+}
+
+function appendWidgetState(lines: string[], state: IDebugWidgetState): void {
+	lines.push('--- Stage 3: Widget State (loadItems → filterItems) ---');
+	lines.push(`  allItems (after loadItems): ${state.allItems.length}`);
+	lines.push(`    local:     ${state.allItems.filter(i => i.storage === PromptsStorage.local).length}`);
+	lines.push(`    user:      ${state.allItems.filter(i => i.storage === PromptsStorage.user).length}`);
+	lines.push(`    extension: ${state.allItems.filter(i => i.storage === PromptsStorage.extension).length}`);
+	lines.push(`    plugin:    ${state.allItems.filter(i => i.storage === PromptsStorage.plugin).length}`);
+
+	lines.push(`  displayEntries (after filterItems): ${state.displayEntries.length}`);
+	const fileEntries = state.displayEntries.filter(e => e.type === 'file-item');
+	lines.push(`    file items shown: ${fileEntries.length}`);
+	const groupEntries = state.displayEntries.filter(e => e.type === 'group-header');
+	for (const g of groupEntries) {
+		lines.push(`    group "${g.label}": count=${g.count}, collapsed=${g.collapsed}`);
+	}
+	lines.push('');
+}
+
+async function appendSourceFolders(lines: string[], promptsService: IPromptsService, promptType: PromptsType): Promise<void> {
+	lines.push('--- Source Folders (creation targets) ---');
+	const sourceFolders = await promptsService.getSourceFolders(promptType);
+	for (const sf of sourceFolders) {
+		lines.push(`  [${sf.storage}] ${sf.uri.fsPath}`);
+	}
+
+	try {
+		const resolvedFolders = await promptsService.getResolvedSourceFolders(promptType);
+		lines.push('');
+		lines.push('--- Resolved Source Folders (discovery order) ---');
+		for (const rf of resolvedFolders) {
+			lines.push(`  [${rf.storage}] ${rf.uri.fsPath} (source=${rf.source})`);
+		}
+	} catch {
+		// getResolvedSourceFolders may not exist for all types
+	}
+}
+
+function appendFileList(lines: string[], files: readonly { uri: URI }[]): void {
+	for (const f of files) {
+		lines.push(`    ${f.uri.fsPath}`);
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationIcons.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationIcons.ts
index f3e775e42a5d8..2d2d087fac375 100644
--- a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationIcons.ts
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationIcons.ts
@@ -61,3 +61,18 @@ export const userIcon = registerIcon('ai-customization-user', Codicon.account, l
  * Icon for extension storage.
  */
 export const extensionIcon = registerIcon('ai-customization-extension', Codicon.extensions, localize('aiCustomizationExtensionIcon', "Icon for extension-contributed items."));
+
+/**
+ * Icon for plugin storage.
+ */
+export const pluginIcon = registerIcon('ai-customization-plugin', Codicon.plug, localize('aiCustomizationPluginIcon', "Icon for plugin-contributed items."));
+
+/**
+ * Icon for built-in storage.
+ */
+export const builtinIcon = registerIcon('ai-customization-builtin', Codicon.starFull, localize('aiCustomizationBuiltinIcon', "Icon for built-in items."));
+
+/**
+ * Icon for MCP servers.
+ */
+export const mcpServerIcon = registerIcon('ai-customization-mcp-server', Codicon.server, localize('aiCustomizationMcpServerIcon', "Icon for MCP servers."));
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationListWidget.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationListWidget.ts
index 89a0cd78d0466..00b3c2fbd52fd 100644
--- a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationListWidget.ts
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationListWidget.ts
@@ -5,11 +5,12 @@
 
 import './media/aiCustomizationManagement.css';
 import * as DOM from '../../../../../base/browser/dom.js';
+import { ActionBar } from '../../../../../base/browser/ui/actionbar/actionbar.js';
 import { Disposable, DisposableStore } from '../../../../../base/common/lifecycle.js';
 import { Emitter, Event } from '../../../../../base/common/event.js';
 import { CancellationToken } from '../../../../../base/common/cancellation.js';
 import { autorun } from '../../../../../base/common/observable.js';
-import { basename, dirname } from '../../../../../base/common/resources.js';
+import { basename, dirname, isEqualOrParent } from '../../../../../base/common/resources.js';
 import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { Codicon } from '../../../../../base/common/codicons.js';
@@ -19,8 +20,9 @@ import { WorkbenchList } from '../../../../../platform/list/browser/listService.
 import { IListVirtualDelegate, IListRenderer, IListContextMenuEvent } from '../../../../../base/browser/ui/list/list.js';
 import { IPromptsService, PromptsStorage, IPromptPath } from '../../common/promptSyntax/service/promptsService.js';
 import { PromptsType } from '../../common/promptSyntax/promptTypes.js';
-import { agentIcon, instructionsIcon, promptIcon, skillIcon, hookIcon, userIcon, workspaceIcon, extensionIcon } from './aiCustomizationIcons.js';
-import { AICustomizationManagementItemMenuId, AICustomizationManagementSection } from './aiCustomizationManagement.js';
+import { AGENT_MD_FILENAME } from '../../common/promptSyntax/config/promptFileLocations.js';
+import { agentIcon, instructionsIcon, promptIcon, skillIcon, hookIcon, userIcon, workspaceIcon, extensionIcon, pluginIcon, builtinIcon } from './aiCustomizationIcons.js';
+import { AI_CUSTOMIZATION_ITEM_STORAGE_KEY, AI_CUSTOMIZATION_ITEM_TYPE_KEY, AI_CUSTOMIZATION_ITEM_URI_KEY, AICustomizationManagementItemMenuId, AICustomizationManagementSection, BUILTIN_STORAGE } from './aiCustomizationManagement.js';
 import { InputBox } from '../../../../../base/browser/ui/inputbox/inputBox.js';
 import { defaultButtonStyles, defaultInputBoxStyles } from '../../../../../platform/theme/browser/defaultStyles.js';
 import { Delayer } from '../../../../../base/common/async.js';
@@ -28,28 +30,50 @@ import { IContextMenuService, IContextViewService } from '../../../../../platfor
 import { HighlightedLabel } from '../../../../../base/browser/ui/highlightedlabel/highlightedLabel.js';
 import { matchesContiguousSubString, IMatch } from '../../../../../base/common/filters.js';
 import { IOpenerService } from '../../../../../platform/opener/common/opener.js';
-import { ButtonWithDropdown } from '../../../../../base/browser/ui/button/button.js';
+import { Button, ButtonWithDropdown } from '../../../../../base/browser/ui/button/button.js';
 import { IMenuService } from '../../../../../platform/actions/common/actions.js';
 import { IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
-import { getFlatContextMenuActions } from '../../../../../platform/actions/browser/menuEntryActionViewItem.js';
-import { IFileService } from '../../../../../platform/files/common/files.js';
+import { createActionViewItem, getContextMenuActions } from '../../../../../platform/actions/browser/menuEntryActionViewItem.js';
 import { IWorkspaceContextService } from '../../../../../platform/workspace/common/workspace.js';
-import { IPathService } from '../../../../services/path/common/pathService.js';
 import { ILabelService } from '../../../../../platform/label/common/label.js';
-import { parseAllHookFiles } from '../promptSyntax/hookUtils.js';
-import { OS } from '../../../../../base/common/platform.js';
-import { IRemoteAgentService } from '../../../../services/remote/common/remoteAgentService.js';
-import { IAICustomizationWorkspaceService } from '../../common/aiCustomizationWorkspaceService.js';
-import { ILogService } from '../../../../../platform/log/common/log.js';
+import { IAICustomizationWorkspaceService, applyStorageSourceFilter } from '../../common/aiCustomizationWorkspaceService.js';
 import { Action, Separator } from '../../../../../base/common/actions.js';
 import { IClipboardService } from '../../../../../platform/clipboard/common/clipboardService.js';
-import { ISCMService } from '../../../scm/common/scm.js';
 import { IHoverService } from '../../../../../platform/hover/browser/hover.js';
+import { IFileService } from '../../../../../platform/files/common/files.js';
+import { IPathService } from '../../../../services/path/common/pathService.js';
+import { generateCustomizationDebugReport } from './aiCustomizationDebugPanel.js';
+import { getCustomizationSecondaryText } from './aiCustomizationListWidgetUtils.js';
+import { parseHooksFromFile } from '../../common/promptSyntax/hookCompatibility.js';
+import { formatHookCommandLabel } from '../../common/promptSyntax/hookSchema.js';
+import { HookType, HOOK_METADATA } from '../../common/promptSyntax/hookTypes.js';
+import { parse as parseJSONC } from '../../../../../base/common/json.js';
+import { Schemas } from '../../../../../base/common/network.js';
+import { OS } from '../../../../../base/common/platform.js';
+import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
+
+export { truncateToFirstSentence } from './aiCustomizationListWidgetUtils.js';
 
 const $ = DOM.$;
 
+//#region Telemetry
+
+type CustomizationEditorSearchEvent = {
+	section: string;
+	resultCount: number;
+};
+
+type CustomizationEditorSearchClassification = {
+	section: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The active section when the search was performed.' };
+	resultCount: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'The number of items matching the search query.' };
+	owner: 'joshspicer';
+	comment: 'Tracks search usage in the Chat Customizations editor.';
+};
+
+//#endregion
+
 const ITEM_HEIGHT = 44;
-const GROUP_HEADER_HEIGHT = 32;
+const GROUP_HEADER_HEIGHT = 36;
 const GROUP_HEADER_HEIGHT_WITH_SEPARATOR = 40;
 
 /**
@@ -63,7 +87,8 @@ export interface IAICustomizationListItem {
 	readonly description?: string;
 	readonly storage: PromptsStorage;
 	readonly promptType: PromptsType;
-	gitStatus?: 'uncommitted' | 'committed';
+	/** When set, overrides `storage` for display grouping purposes. */
+	readonly groupKey?: string;
 	nameMatches?: IMatch[];
 	descriptionMatches?: IMatch[];
 }
@@ -74,7 +99,7 @@ export interface IAICustomizationListItem {
 interface IGroupHeaderEntry {
 	readonly type: 'group-header';
 	readonly id: string;
-	readonly storage: PromptsStorage;
+	readonly groupKey: string;
 	readonly label: string;
 	readonly icon: ThemeIcon;
 	readonly count: number;
@@ -112,10 +137,10 @@ class AICustomizationListDelegate implements IListVirtualDelegate<IListEntry> {
 interface IAICustomizationItemTemplateData {
 	readonly container: HTMLElement;
 	readonly actionsContainer: HTMLElement;
+	readonly actionBar: ActionBar;
+	readonly typeIcon: HTMLElement;
 	readonly nameLabel: HighlightedLabel;
 	readonly description: HighlightedLabel;
-	readonly storageBadge: HTMLElement;
-	readonly gitStatusBadge: HTMLElement;
 	readonly disposables: DisposableStore;
 	readonly elementDisposables: DisposableStore;
 }
@@ -193,12 +218,47 @@ class GroupHeaderRenderer implements IListRenderer<IGroupHeaderEntry, IGroupHead
 	}
 }
 
+/**
+ * Returns the icon for a given prompt type.
+ */
+function promptTypeToIcon(type: PromptsType): ThemeIcon {
+	switch (type) {
+		case PromptsType.agent: return agentIcon;
+		case PromptsType.skill: return skillIcon;
+		case PromptsType.instructions: return instructionsIcon;
+		case PromptsType.prompt: return promptIcon;
+		case PromptsType.hook: return hookIcon;
+		default: return promptIcon;
+	}
+}
+
+/**
+ * Formats a name for display: strips a trailing .md extension, converts dashes/underscores
+ * to spaces and applies title case.
+ * Note: callers that pass IMatch highlight ranges must compute those ranges against the
+ * formatted string (not the raw input), since .md stripping changes string length.
+ */
+export function formatDisplayName(name: string): string {
+	return name
+		.replace(/\.md$/i, '')
+		.replace(/[-_]/g, ' ')
+		.replace(/\b\w/g, c => c.toUpperCase());
+}
+
 /**
  * Renderer for AI customization list items.
  */
 class AICustomizationItemRenderer implements IListRenderer<IFileItemEntry, IAICustomizationItemTemplateData> {
 	readonly templateId = 'aiCustomizationItem';
 
+	constructor(
+		@IHoverService private readonly hoverService: IHoverService,
+		@ILabelService private readonly labelService: ILabelService,
+		@IMenuService private readonly menuService: IMenuService,
+		@IContextKeyService private readonly contextKeyService: IContextKeyService,
+		@IInstantiationService private readonly instantiationService: IInstantiationService,
+	) { }
+
 	renderTemplate(container: HTMLElement): IAICustomizationItemTemplateData {
 		const disposables = new DisposableStore();
 		const elementDisposables = new DisposableStore();
@@ -206,25 +266,24 @@ class AICustomizationItemRenderer implements IListRenderer<IFileItemEntry, IAICu
 		container.classList.add('ai-customization-list-item');
 
 		const leftSection = DOM.append(container, $('.item-left'));
-		// Storage badge on left (shows workspace/user/extension)
-		const storageBadge = DOM.append(leftSection, $('.storage-badge'));
+		const typeIcon = DOM.append(leftSection, $('.item-type-icon'));
 		const textContainer = DOM.append(leftSection, $('.item-text'));
 		const nameLabel = disposables.add(new HighlightedLabel(DOM.append(textContainer, $('.item-name'))));
 		const description = disposables.add(new HighlightedLabel(DOM.append(textContainer, $('.item-description'))));
 
-		// Git status badge (always visible, outside item-right hover container)
-		const gitStatusBadge = DOM.append(container, $('.git-status-badge'));
-
 		// Right section for actions (hover-visible)
 		const actionsContainer = DOM.append(container, $('.item-right'));
+		const actionBar = disposables.add(new ActionBar(actionsContainer, {
+			actionViewItemProvider: createActionViewItem.bind(undefined, this.instantiationService),
+		}));
 
 		return {
 			container,
 			actionsContainer,
+			actionBar,
+			typeIcon,
 			nameLabel,
 			description,
-			storageBadge,
-			gitStatusBadge,
 			disposables,
 			elementDisposables,
 		};
@@ -234,13 +293,50 @@ class AICustomizationItemRenderer implements IListRenderer<IFileItemEntry, IAICu
 		templateData.elementDisposables.clear();
 		const element = entry.item;
 
-		// Name with highlights
-		templateData.nameLabel.set(element.name, element.nameMatches);
+		// Type icon based on prompt type
+		templateData.typeIcon.className = 'item-type-icon';
+		templateData.typeIcon.classList.add(...ThemeIcon.asClassNameArray(promptTypeToIcon(element.promptType)));
+
+		// Hover tooltip: name + full path
+		templateData.elementDisposables.add(this.hoverService.setupDelayedHover(templateData.container, () => {
+			const uriLabel = this.labelService.getUriLabel(element.uri, { relative: false });
+			return {
+				content: `${element.name}\n${uriLabel}`,
+				appearance: {
+					compact: true,
+					skipFadeInAnimation: true,
+				}
+			};
+		}));
 
-		// Description - show either description or filename as secondary text
-		const secondaryText = element.description || element.filename;
+		// Name with highlights — nameMatches are pre-computed against the formatted display name
+		const displayName = formatDisplayName(element.name);
+		templateData.nameLabel.set(displayName, element.nameMatches);
+
+		// Hooks show shell commands here, so keep the full text instead of truncating to the first sentence.
+		const secondaryText = getCustomizationSecondaryText(element.description, element.filename, element.promptType);
+		let secondaryTextMatches: IMatch[] | undefined;
+		if (secondaryText && element.description && element.descriptionMatches) {
+			if (secondaryText === element.description) {
+				// No truncation, matches can be used as-is.
+				secondaryTextMatches = element.descriptionMatches;
+			} else {
+				// Description was truncated for display; clamp matches to the visible range.
+				const maxLength = secondaryText.length;
+				const clampedMatches = element.descriptionMatches.map(match => {
+					// Discard matches that are entirely outside the visible portion.
+					if (match.start >= maxLength || match.end <= 0) {
+						return undefined;
+					}
+					const clampedStart = Math.max(0, match.start);
+					const clampedEnd = Math.min(match.end, maxLength);
+					return clampedEnd > clampedStart ? { start: clampedStart, end: clampedEnd } : undefined;
+				}).filter((match): match is IMatch => !!match);
+				secondaryTextMatches = clampedMatches.length ? clampedMatches : undefined;
+			}
+		}
 		if (secondaryText) {
-			templateData.description.set(secondaryText, element.description ? element.descriptionMatches : undefined);
+			templateData.description.set(secondaryText, secondaryTextMatches);
 			templateData.description.element.style.display = '';
 			// Style differently for filename vs description
 			templateData.description.element.classList.toggle('is-filename', !element.description);
@@ -249,40 +345,35 @@ class AICustomizationItemRenderer implements IListRenderer<IFileItemEntry, IAICu
 			templateData.description.element.style.display = 'none';
 		}
 
-		// Storage badge
-		let storageBadgeIcon: ThemeIcon;
-		let storageBadgeLabel: string;
-		switch (element.storage) {
-			case PromptsStorage.local:
-				storageBadgeIcon = workspaceIcon;
-				storageBadgeLabel = localize('workspace', "Workspace");
-				break;
-			case PromptsStorage.user:
-				storageBadgeIcon = userIcon;
-				storageBadgeLabel = localize('user', "User");
-				break;
-			case PromptsStorage.extension:
-				storageBadgeIcon = extensionIcon;
-				storageBadgeLabel = localize('extension', "Extension");
-				break;
-		}
+		// Inline action bar from menu
+		const context = {
+			uri: element.uri.toString(),
+			name: element.name,
+			promptType: element.promptType,
+			storage: element.storage,
+		};
 
-		templateData.storageBadge.className = 'storage-badge';
-		templateData.storageBadge.classList.add(...ThemeIcon.asClassNameArray(storageBadgeIcon));
-		templateData.storageBadge.title = storageBadgeLabel;
-
-		// Git status badge
-		const gitBadge = templateData.gitStatusBadge;
-		gitBadge.className = 'git-status-badge';
-		if (element.gitStatus === 'committed') {
-			gitBadge.classList.add(...ThemeIcon.asClassNameArray(Codicon.check));
-			gitBadge.classList.add('committed');
-			gitBadge.textContent = '';
-			gitBadge.title = localize('committedStatus', "Committed");
-			gitBadge.style.display = '';
-		} else {
-			gitBadge.style.display = 'none';
-		}
+		// Create scoped context key service with item-specific keys for when-clause filtering
+		const overlay = this.contextKeyService.createOverlay([
+			[AI_CUSTOMIZATION_ITEM_TYPE_KEY, element.promptType],
+			[AI_CUSTOMIZATION_ITEM_STORAGE_KEY, element.storage],
+			[AI_CUSTOMIZATION_ITEM_URI_KEY, element.uri.toString()],
+		]);
+
+		const menu = templateData.elementDisposables.add(
+			this.menuService.createMenu(AICustomizationManagementItemMenuId, overlay)
+		);
+
+		const updateActions = () => {
+			const actions = menu.getActions({ arg: context, shouldForwardArgs: true });
+			const { primary } = getContextMenuActions(actions, 'inline');
+			templateData.actionBar.clear();
+			templateData.actionBar.push(primary, { icon: true, label: false });
+		};
+		updateActions();
+		templateData.elementDisposables.add(menu.onDidChange(updateActions));
+
+		templateData.actionBar.context = context;
 	}
 
 	disposeTemplate(templateData: IAICustomizationItemTemplateData): void {
@@ -323,7 +414,9 @@ export class AICustomizationListWidget extends Disposable {
 	private searchAndButtonContainer!: HTMLElement;
 	private searchContainer!: HTMLElement;
 	private searchInput!: InputBox;
+	private addButtonContainer!: HTMLElement;
 	private addButton!: ButtonWithDropdown;
+	private addButtonSimple!: Button;
 	private listContainer!: HTMLElement;
 	private list!: WorkbenchList<IListEntry>;
 	private emptyStateContainer!: HTMLElement;
@@ -335,7 +428,7 @@ export class AICustomizationListWidget extends Disposable {
 	private allItems: IAICustomizationListItem[] = [];
 	private displayEntries: IListEntry[] = [];
 	private searchQuery: string = '';
-	private readonly collapsedGroups = new Set<PromptsStorage>();
+	private readonly collapsedGroups = new Set<string>();
 	private readonly dropdownActionDisposables = this._register(new DisposableStore());
 
 	private readonly delayedFilter = new Delayer<void>(200);
@@ -349,8 +442,8 @@ export class AICustomizationListWidget extends Disposable {
 	private readonly _onDidRequestCreate = this._register(new Emitter<PromptsType>());
 	readonly onDidRequestCreate: Event<PromptsType> = this._onDidRequestCreate.event;
 
-	private readonly _onDidRequestCreateManual = this._register(new Emitter<{ type: PromptsType; target: 'workspace' | 'user' }>());
-	readonly onDidRequestCreateManual: Event<{ type: PromptsType; target: 'workspace' | 'user' }> = this._onDidRequestCreateManual.event;
+	private readonly _onDidRequestCreateManual = this._register(new Emitter<{ type: PromptsType; target: 'workspace' | 'user' | 'workspace-root' }>());
+	readonly onDidRequestCreateManual: Event<{ type: PromptsType; target: 'workspace' | 'user' | 'workspace-root' }> = this._onDidRequestCreateManual.event;
 
 	constructor(
 		@IInstantiationService private readonly instantiationService: IInstantiationService,
@@ -360,16 +453,14 @@ export class AICustomizationListWidget extends Disposable {
 		@IContextMenuService private readonly contextMenuService: IContextMenuService,
 		@IMenuService private readonly menuService: IMenuService,
 		@IContextKeyService private readonly contextKeyService: IContextKeyService,
-		@IFileService private readonly fileService: IFileService,
 		@IWorkspaceContextService private readonly workspaceContextService: IWorkspaceContextService,
-		@IPathService private readonly pathService: IPathService,
 		@ILabelService private readonly labelService: ILabelService,
-		@IRemoteAgentService private readonly remoteAgentService: IRemoteAgentService,
 		@IAICustomizationWorkspaceService private readonly workspaceService: IAICustomizationWorkspaceService,
-		@ILogService private readonly logService: ILogService,
 		@IClipboardService private readonly clipboardService: IClipboardService,
-		@ISCMService private readonly scmService: ISCMService,
 		@IHoverService private readonly hoverService: IHoverService,
+		@IFileService private readonly fileService: IFileService,
+		@IPathService private readonly pathService: IPathService,
+		@ITelemetryService private readonly telemetryService: ITelemetryService,
 	) {
 		super();
 		this.element = $('.ai-customization-list-widget');
@@ -382,18 +473,6 @@ export class AICustomizationListWidget extends Disposable {
 			this.refresh();
 		}));
 
-		// Re-filter when SCM repositories change (updates git status badges after commits)
-		const trackRepoChanges = (repo: { provider: { onDidChangeResources: Event<void> } }) => {
-			this._register(repo.provider.onDidChangeResources(() => {
-				this.updateGitStatus(this.allItems);
-				this.filterItems();
-			}));
-		};
-		for (const repo of [...this.scmService.repositories]) {
-			trackRepoChanges(repo);
-		}
-		this._register(this.scmService.onDidAddRepository(repo => trackRepoChanges(repo)));
-
 	}
 
 	private create(): void {
@@ -409,12 +488,30 @@ export class AICustomizationListWidget extends Disposable {
 
 		this._register(this.searchInput.onDidChange(() => {
 			this.searchQuery = this.searchInput.value;
-			this.delayedFilter.trigger(() => this.filterItems());
+			this.delayedFilter.trigger(() => {
+				const matchCount = this.filterItems();
+				if (this.searchQuery.trim()) {
+					this.telemetryService.publicLog2<CustomizationEditorSearchEvent, CustomizationEditorSearchClassification>('chatCustomizationEditor.search', {
+						section: this.currentSection,
+						resultCount: matchCount,
+					});
+				}
+			});
 		}));
 
-		// Add button with dropdown next to search
-		const addButtonContainer = DOM.append(this.searchAndButtonContainer, $('.list-add-button-container'));
-		this.addButton = this._register(new ButtonWithDropdown(addButtonContainer, {
+		// Add button container next to search
+		this.addButtonContainer = DOM.append(this.searchAndButtonContainer, $('.list-add-button-container'));
+
+		// Simple button (for single-action case, no dropdown)
+		this.addButtonSimple = this._register(new Button(this.addButtonContainer, {
+			...defaultButtonStyles,
+			supportIcons: true,
+		}));
+		this.addButtonSimple.element.classList.add('list-add-button');
+		this._register(this.addButtonSimple.onDidClick(() => this.executePrimaryCreateAction()));
+
+		// Button with dropdown (for multi-action case)
+		this.addButton = this._register(new ButtonWithDropdown(this.addButtonContainer, {
 			...defaultButtonStyles,
 			supportIcons: true,
 			contextMenuProvider: this.contextMenuService,
@@ -486,6 +583,13 @@ export class AICustomizationListWidget extends Disposable {
 		this._register(this.promptsService.onDidChangeCustomAgents(() => this.refresh()));
 		this._register(this.promptsService.onDidChangeSlashCommands(() => this.refresh()));
 
+		// Refresh on file deletions so the list updates after inline delete actions
+		this._register(this.fileService.onDidFilesChange(e => {
+			if (e.gotDeleted()) {
+				this.refresh();
+			}
+		}));
+
 		// Section footer at bottom with description and link
 		this.sectionHeader = DOM.append(this.element, $('.section-footer'));
 		this.sectionDescription = DOM.append(this.sectionHeader, $('p.section-footer-description'));
@@ -518,13 +622,20 @@ export class AICustomizationListWidget extends Disposable {
 			storage: item.storage,
 		};
 
-		// Get menu actions
-		const actions = this.menuService.getMenuActions(AICustomizationManagementItemMenuId, this.contextKeyService, {
+		// Create scoped context key service with item-specific keys for when-clause filtering
+		const overlay = this.contextKeyService.createOverlay([
+			[AI_CUSTOMIZATION_ITEM_TYPE_KEY, item.promptType],
+			[AI_CUSTOMIZATION_ITEM_STORAGE_KEY, item.storage],
+			[AI_CUSTOMIZATION_ITEM_URI_KEY, item.uri.toString()],
+		]);
+
+		// Get menu actions, excluding inline actions to avoid duplicates
+		const actions = this.menuService.getMenuActions(AICustomizationManagementItemMenuId, overlay, {
 			arg: context,
 			shouldForwardArgs: true,
 		});
 
-		const flatActions = getFlatContextMenuActions(actions);
+		const { secondary } = getContextMenuActions(actions, 'inline');
 
 		// Add copy path actions
 		const copyActions = [
@@ -547,7 +658,7 @@ export class AICustomizationListWidget extends Disposable {
 
 		this.contextMenuService.showContextMenu({
 			getAnchor: () => e.anchor,
-			getActions: () => [...flatActions, ...copyActions],
+			getActions: () => [...secondary, ...copyActions],
 		});
 	}
 
@@ -606,22 +717,50 @@ export class AICustomizationListWidget extends Disposable {
 	 */
 	private updateAddButton(): void {
 		const typeLabel = this.getTypeLabel();
-		this.addButton.primaryButton.setTitle('');
-		this.addButton.dropdownButton.setTitle('');
-		this.addButton.enabled = true;
-		if (this.workspaceService.preferManualCreation) {
+		const dropdownActions = this.getDropdownActions();
+		const hasDropdown = dropdownActions.length > 0;
+
+		// Toggle which button is visible
+		this.addButton.element.style.display = hasDropdown ? '' : 'none';
+		this.addButtonSimple.element.style.display = hasDropdown ? 'none' : '';
+
+		if (this.workspaceService.isSessionsWindow) {
 			// Sessions: primary is workspace creation
 			const hasWorkspace = this.hasActiveWorkspace();
-			this.addButton.label = `$(${Codicon.add.id}) New ${typeLabel} (Workspace)`;
-			this.addButton.enabled = hasWorkspace;
-			if (!hasWorkspace) {
-				const disabledTitle = localize('createDisabled', "Open a workspace folder to create customizations.");
-				this.addButton.primaryButton.setTitle(disabledTitle);
-				this.addButton.dropdownButton.setTitle(disabledTitle);
+			const label = `$(${Codicon.add.id}) New ${typeLabel} (Workspace)`;
+
+			if (hasDropdown) {
+				this.addButton.label = label;
+				this.addButton.enabled = hasWorkspace;
+				this.addButton.primaryButton.setTitle('');
+				this.addButton.dropdownButton.setTitle('');
+				if (!hasWorkspace) {
+					const disabledTitle = localize('createDisabled', "Open a workspace folder to create customizations.");
+					this.addButton.primaryButton.setTitle(disabledTitle);
+					this.addButton.dropdownButton.setTitle(disabledTitle);
+				}
+			} else {
+				this.addButtonSimple.label = label;
+				this.addButtonSimple.enabled = hasWorkspace;
+				if (!hasWorkspace) {
+					this.addButtonSimple.setTitle(localize('createDisabled', "Open a workspace folder to create customizations."));
+				} else {
+					this.addButtonSimple.setTitle('');
+				}
 			}
 		} else {
 			// Core: primary is AI generation
-			this.addButton.label = `$(${Codicon.sparkle.id}) Generate ${typeLabel}`;
+			const label = `$(${Codicon.sparkle.id}) Generate ${typeLabel}`;
+			if (hasDropdown) {
+				this.addButton.label = label;
+				this.addButton.enabled = true;
+				this.addButton.primaryButton.setTitle('');
+				this.addButton.dropdownButton.setTitle('');
+			} else {
+				this.addButtonSimple.label = label;
+				this.addButtonSimple.enabled = true;
+				this.addButtonSimple.setTitle('');
+			}
 		}
 	}
 
@@ -636,7 +775,7 @@ export class AICustomizationListWidget extends Disposable {
 
 		// Hooks: no user-scoped creation
 		if (promptType === PromptsType.hook) {
-			if (this.workspaceService.preferManualCreation) {
+			if (this.workspaceService.isSessionsWindow) {
 				// Sessions: no dropdown for hooks
 			} else {
 				// Core: primary is generate, dropdown has configure quick pick
@@ -649,11 +788,17 @@ export class AICustomizationListWidget extends Disposable {
 			return actions;
 		}
 
-		if (this.workspaceService.preferManualCreation) {
+		if (this.workspaceService.isSessionsWindow) {
 			// Sessions: primary is workspace, dropdown has user
 			actions.push(this.dropdownActionDisposables.add(new Action('createUser', `$(${Codicon.account.id}) New ${typeLabel} (User)`, undefined, true, () => {
 				this._onDidRequestCreateManual.fire({ type: promptType, target: 'user' });
 			})));
+			// For instructions: offer AGENTS.md at workspace root
+			if (promptType === PromptsType.instructions && this.hasActiveWorkspace()) {
+				actions.push(this.dropdownActionDisposables.add(new Action('createAgentsMd', `$(${Codicon.file.id}) New ${AGENT_MD_FILENAME}`, undefined, true, () => {
+					this._onDidRequestCreateManual.fire({ type: promptType, target: 'workspace-root' });
+				})));
+			}
 		} else {
 			// Core: primary is generate, dropdown has workspace + user
 			if (this.hasActiveWorkspace()) {
@@ -681,7 +826,7 @@ export class AICustomizationListWidget extends Disposable {
 	 */
 	private executePrimaryCreateAction(): void {
 		const promptType = sectionToPromptType(this.currentSection);
-		if (this.workspaceService.preferManualCreation) {
+		if (this.workspaceService.isSessionsWindow) {
 			// Sessions: primary creates in workspace
 			if (!this.hasActiveWorkspace()) {
 				return;
@@ -724,13 +869,10 @@ export class AICustomizationListWidget extends Disposable {
 	 * Loads items for the current section.
 	 */
 	private async loadItems(): Promise<void> {
-		const promptType = sectionToPromptType(this.currentSection);
+		const section = this.currentSection;
+		const promptType = sectionToPromptType(section);
 		const items: IAICustomizationListItem[] = [];
 
-		const folders = this.workspaceContextService.getWorkspace().folders;
-		const activeRepo = this.workspaceService.getActiveProjectRoot();
-		this.logService.info(`[AICustomizationListWidget] loadItems: section=${this.currentSection}, promptType=${promptType}, workspaceFolders=[${folders.map(f => f.uri.toString()).join(', ')}], activeRepo=${activeRepo?.toString() ?? 'none'}`);
-
 
 		if (promptType === PromptsType.agent) {
 			// Use getCustomAgents which has parsed name/description from frontmatter
@@ -765,8 +907,12 @@ export class AICustomizationListWidget extends Disposable {
 			}
 		} else if (promptType === PromptsType.prompt) {
 			// Use getPromptSlashCommands which has parsed name/description from frontmatter
+			// Filter out skills since they have their own section
 			const commands = await this.promptsService.getPromptSlashCommands(CancellationToken.None);
 			for (const command of commands) {
+				if (command.promptPath.type === PromptsType.skill) {
+					continue;
+				}
 				const filename = basename(command.promptPath.uri);
 				items.push({
 					id: command.promptPath.uri.toString(),
@@ -779,44 +925,115 @@ export class AICustomizationListWidget extends Disposable {
 				});
 			}
 		} else if (promptType === PromptsType.hook) {
-			// Parse hook files and display individual hooks
-			const workspaceFolder = this.workspaceContextService.getWorkspace().folders[0];
-			const workspaceRootUri = workspaceFolder?.uri;
+			// Try to parse individual hooks from each file; fall back to showing the file itself
+			const hookFiles = await this.promptsService.listPromptFiles(PromptsType.hook, CancellationToken.None);
+			const activeRoot = this.workspaceService.getActiveProjectRoot();
 			const userHomeUri = await this.pathService.userHome();
-			const userHome = userHomeUri.fsPath ?? userHomeUri.path;
-			const remoteEnv = await this.remoteAgentService.getEnvironment();
-			const targetOS = remoteEnv?.os ?? OS;
-
-			const parsedHooks = await parseAllHookFiles(
-				this.promptsService,
-				this.fileService,
-				this.labelService,
-				workspaceRootUri,
-				userHome,
-				targetOS,
-				CancellationToken.None
-			);
-
-			for (const hook of parsedHooks) {
-				// Determine storage from the file path
-				const storage = hook.filePath.startsWith('~') ? PromptsStorage.user : PromptsStorage.local;
+			const userHome = userHomeUri.scheme === Schemas.file ? userHomeUri.fsPath : userHomeUri.path;
+
+			for (const hookFile of hookFiles) {
+				let parsedHooks = false;
+				try {
+					const content = await this.fileService.readFile(hookFile.uri);
+					const json = parseJSONC(content.value.toString());
+					const { hooks } = parseHooksFromFile(hookFile.uri, json, activeRoot, userHome);
+
+					if (hooks.size > 0) {
+						parsedHooks = true;
+						for (const [hookType, entry] of hooks) {
+							const hookMeta = HOOK_METADATA[hookType];
+							for (let i = 0; i < entry.hooks.length; i++) {
+								const hook = entry.hooks[i];
+								const cmdLabel = formatHookCommandLabel(hook, OS);
+								const truncatedCmd = cmdLabel.length > 60 ? cmdLabel.substring(0, 57) + '...' : cmdLabel;
+								items.push({
+									id: `${hookFile.uri.toString()}#${entry.originalId}[${i}]`,
+									uri: hookFile.uri,
+									name: hookMeta?.label ?? entry.originalId,
+									filename: basename(hookFile.uri),
+									description: truncatedCmd || localize('hookUnset', "(unset)"),
+									storage: hookFile.storage,
+									promptType,
+								});
+							}
+						}
+					}
+				} catch {
+					// Parse failed — fall through to show raw file
+				}
 
-				items.push({
-					id: `${hook.fileUri.toString()}#${hook.hookType}-${hook.index}`,
-					uri: hook.fileUri,
-					name: `${hook.hookTypeLabel}: ${hook.commandLabel}`,
-					filename: basename(hook.fileUri),
-					description: hook.filePath,
-					storage,
-					promptType,
-				});
+				if (!parsedHooks) {
+					const filename = basename(hookFile.uri);
+					items.push({
+						id: hookFile.uri.toString(),
+						uri: hookFile.uri,
+						name: this.getFriendlyName(filename),
+						filename,
+						storage: hookFile.storage,
+						promptType,
+					});
+				}
+			}
+
+			// Also include hooks defined in agent frontmatter (not in sessions window)
+			// TODO: add this back when Copilot CLI supports this
+			const agents = !this.workspaceService.isSessionsWindow ? await this.promptsService.getCustomAgents(CancellationToken.None) : [];
+			for (const agent of agents) {
+				if (!agent.hooks) {
+					continue;
+				}
+				for (const hookType of Object.values(HookType)) {
+					const hookCommands = agent.hooks[hookType];
+					if (!hookCommands || hookCommands.length === 0) {
+						continue;
+					}
+					const hookMeta = HOOK_METADATA[hookType];
+					for (let i = 0; i < hookCommands.length; i++) {
+						const hook = hookCommands[i];
+						const cmdLabel = formatHookCommandLabel(hook, OS);
+						const truncatedCmd = cmdLabel.length > 60 ? cmdLabel.substring(0, 57) + '...' : cmdLabel;
+						items.push({
+							id: `${agent.uri.toString()}#hook:${hookType}[${i}]`,
+							uri: agent.uri,
+							name: hookMeta?.label ?? hookType,
+							filename: basename(agent.uri),
+							description: `${agent.name}: ${truncatedCmd || localize('hookUnset', "(unset)")}`,
+							storage: agent.source.storage,
+							groupKey: 'agents',
+							promptType,
+						});
+					}
+				}
 			}
 		} else {
-			// For instructions, fetch once and group by storage
-			const allItems = await this.promptsService.listPromptFiles(promptType, CancellationToken.None);
+			// For instructions, fetch prompt files and group by storage
+			const promptFiles = await this.promptsService.listPromptFiles(promptType, CancellationToken.None);
+			const allItems: IPromptPath[] = [...promptFiles];
+
+			// Also include agent instruction files (AGENTS.md, CLAUDE.md, copilot-instructions.md)
+			if (promptType === PromptsType.instructions) {
+				const agentInstructions = await this.promptsService.listAgentInstructions(CancellationToken.None, undefined);
+				const workspaceFolderUris = this.workspaceContextService.getWorkspace().folders.map(f => f.uri);
+				const activeRoot = this.workspaceService.getActiveProjectRoot();
+				if (activeRoot) {
+					workspaceFolderUris.push(activeRoot);
+				}
+				for (const file of agentInstructions) {
+					const isWorkspaceFile = workspaceFolderUris.some(root => isEqualOrParent(file.uri, root));
+					allItems.push({
+						uri: file.uri,
+						storage: isWorkspaceFile ? PromptsStorage.local : PromptsStorage.user,
+						type: PromptsType.instructions,
+						name: basename(file.uri),
+					});
+				}
+			}
+
 			const workspaceItems = allItems.filter(item => item.storage === PromptsStorage.local);
 			const userItems = allItems.filter(item => item.storage === PromptsStorage.user);
 			const extensionItems = allItems.filter(item => item.storage === PromptsStorage.extension);
+			const pluginItems = allItems.filter(item => item.storage === PromptsStorage.plugin);
+			const builtinItems = allItems.filter(item => item.storage === BUILTIN_STORAGE);
 
 			const mapToListItem = (item: IPromptPath): IAICustomizationListItem => {
 				const filename = basename(item.uri);
@@ -836,43 +1053,28 @@ export class AICustomizationListWidget extends Disposable {
 			items.push(...workspaceItems.map(mapToListItem));
 			items.push(...userItems.map(mapToListItem));
 			items.push(...extensionItems.map(mapToListItem));
+			items.push(...pluginItems.map(mapToListItem));
+			items.push(...builtinItems.map(mapToListItem));
 		}
 
+		// Apply storage source filter (removes items not in visible sources or excluded user roots)
+		const filter = this.workspaceService.getStorageSourceFilter(promptType);
+		const filteredItems = applyStorageSourceFilter(items, filter);
+		items.length = 0;
+		items.push(...filteredItems);
+
 		// Sort items by name
 		items.sort((a, b) => a.name.localeCompare(b.name));
 
-		// Set git status for workspace (local) items
-		this.updateGitStatus(items);
-
-		this.logService.info(`[AICustomizationListWidget] loadItems complete: ${items.length} items loaded [${items.map(i => `${i.name}(${i.storage}:${i.uri.toString()})`).join(', ')}]`);
+		if (this.currentSection !== section) {
+			return; // section changed while loading
+		}
 
 		this.allItems = items;
 		this.filterItems();
 		this._onDidChangeItemCount.fire(items.length);
 	}
 
-	/**
-	 * Updates git status on local workspace items by checking SCM resource groups.
-	 * Files found in resource groups have uncommitted changes; others are committed.
-	 */
-	private updateGitStatus(items: IAICustomizationListItem[]): void {
-		// Build a set of URIs that have uncommitted changes in SCM
-		const uncommittedUris = new Set<string>();
-		for (const repo of [...this.scmService.repositories]) {
-			for (const group of repo.provider.groups) {
-				for (const resource of group.resources) {
-					uncommittedUris.add(resource.sourceUri.toString());
-				}
-			}
-		}
-
-		for (const item of items) {
-			if (item.storage === PromptsStorage.local) {
-				item.gitStatus = uncommittedUris.has(item.uri.toString()) ? 'uncommitted' : 'committed';
-			}
-		}
-	}
-
 	/**
 	 * Derives a friendly name from a filename by removing extension suffixes.
 	 */
@@ -895,7 +1097,7 @@ export class AICustomizationListWidget extends Disposable {
 	/**
 	 * Filters items based on the current search query and builds grouped display entries.
 	 */
-	private filterItems(): void {
+	private filterItems(): number {
 		let matchedItems: IAICustomizationListItem[];
 
 		if (!this.searchQuery.trim()) {
@@ -905,7 +1107,10 @@ export class AICustomizationListWidget extends Disposable {
 			matchedItems = [];
 
 			for (const item of this.allItems) {
-				const nameMatches = matchesContiguousSubString(query, item.name);
+				// Compute matches against the formatted display name so highlight positions
+				// are correct even after .md stripping and title-casing.
+				const displayName = formatDisplayName(item.name);
+				const nameMatches = matchesContiguousSubString(query, displayName);
 				const descriptionMatches = item.description ? matchesContiguousSubString(query, item.description) : null;
 				const filenameMatches = matchesContiguousSubString(query, item.filename);
 
@@ -919,18 +1124,21 @@ export class AICustomizationListWidget extends Disposable {
 			}
 		}
 
-		const totalBeforeFilter = matchedItems.length;
-		this.logService.info(`[AICustomizationListWidget] filterItems: allItems=${this.allItems.length}, matched=${totalBeforeFilter}`);
-
 		// Group items by storage
-		const groups: { storage: PromptsStorage; label: string; icon: ThemeIcon; description: string; items: IAICustomizationListItem[] }[] = [
-			{ storage: PromptsStorage.local, label: localize('workspaceGroup', "Workspace"), icon: workspaceIcon, description: localize('workspaceGroupDescription', "Customizations stored as files in your project folder and shared with your team via version control."), items: [] },
-			{ storage: PromptsStorage.user, label: localize('userGroup', "User"), icon: userIcon, description: localize('userGroupDescription', "Customizations stored locally on your machine in a central location. Private to you and available across all projects."), items: [] },
-			{ storage: PromptsStorage.extension, label: localize('extensionGroup', "Extensions"), icon: extensionIcon, description: localize('extensionGroupDescription', "Read-only customizations provided by installed extensions."), items: [] },
-		];
+		const promptType = sectionToPromptType(this.currentSection);
+		const visibleSources = new Set(this.workspaceService.getStorageSourceFilter(promptType).sources);
+		const groups: { groupKey: string; label: string; icon: ThemeIcon; description: string; items: IAICustomizationListItem[] }[] = [
+			{ groupKey: PromptsStorage.local, label: localize('workspaceGroup', "Workspace"), icon: workspaceIcon, description: localize('workspaceGroupDescription', "Customizations stored as files in your project folder and shared with your team via version control."), items: [] },
+			{ groupKey: PromptsStorage.user, label: localize('userGroup', "User"), icon: userIcon, description: localize('userGroupDescription', "Customizations stored locally on your machine in a central location. Private to you and available across all projects."), items: [] },
+			{ groupKey: PromptsStorage.extension, label: localize('extensionGroup', "Extensions"), icon: extensionIcon, description: localize('extensionGroupDescription', "Read-only customizations provided by installed extensions."), items: [] },
+			{ groupKey: PromptsStorage.plugin, label: localize('pluginGroup', "Plugins"), icon: pluginIcon, description: localize('pluginGroupDescription', "Read-only customizations provided by installed plugins."), items: [] },
+			{ groupKey: BUILTIN_STORAGE, label: localize('builtinGroup', "Built-in"), icon: builtinIcon, description: localize('builtinGroupDescription', "Built-in customizations shipped with the application."), items: [] },
+			{ groupKey: 'agents', label: localize('agentsGroup', "Agents"), icon: agentIcon, description: localize('agentsGroupDescription', "Hooks defined in agent files."), items: [] },
+		].filter(g => visibleSources.has(g.groupKey as PromptsStorage) || g.groupKey === 'agents');
 
 		for (const item of matchedItems) {
-			const group = groups.find(g => g.storage === item.storage);
+			const key = item.groupKey ?? item.storage;
+			const group = groups.find(g => g.groupKey === key);
 			if (group) {
 				group.items.push(item);
 			}
@@ -949,12 +1157,12 @@ export class AICustomizationListWidget extends Disposable {
 				continue;
 			}
 
-			const collapsed = this.collapsedGroups.has(group.storage);
+			const collapsed = this.collapsedGroups.has(group.groupKey);
 
 			this.displayEntries.push({
 				type: 'group-header',
-				id: `group-${group.storage}`,
-				storage: group.storage,
+				id: `group-${group.groupKey}`,
+				groupKey: group.groupKey,
 				label: group.label,
 				icon: group.icon,
 				count: group.items.length,
@@ -972,18 +1180,18 @@ export class AICustomizationListWidget extends Disposable {
 		}
 
 		this.list.splice(0, this.list.length, this.displayEntries);
-		this.logService.info(`[AICustomizationListWidget] filterItems complete: ${this.displayEntries.length} display entries spliced into list`);
 		this.updateEmptyState();
+		return matchedItems.length;
 	}
 
 	/**
 	 * Toggles the collapsed state of a group.
 	 */
 	private toggleGroup(entry: IGroupHeaderEntry): void {
-		if (this.collapsedGroups.has(entry.storage)) {
-			this.collapsedGroups.delete(entry.storage);
+		if (this.collapsedGroups.has(entry.groupKey)) {
+			this.collapsedGroups.delete(entry.groupKey);
 		} else {
-			this.collapsedGroups.add(entry.storage);
+			this.collapsedGroups.add(entry.groupKey);
 		}
 		this.filterItems();
 	}
@@ -1097,14 +1305,28 @@ export class AICustomizationListWidget extends Disposable {
 	 * Layouts the widget.
 	 */
 	layout(height: number, width: number): void {
-		const sectionFooterHeight = this.sectionHeader.offsetHeight || 100;
-		const searchBarHeight = this.searchAndButtonContainer.offsetHeight || 40;
-		const margins = 12; // search margin (6+6), not included in offsetHeight
-		const listHeight = height - sectionFooterHeight - searchBarHeight - margins;
+		const sectionFooterHeight = this.sectionHeader.offsetHeight || 0;
+		const searchBarHeight = this.searchAndButtonContainer.offsetHeight || 52;
+		const listHeight = height - sectionFooterHeight - searchBarHeight;
 
 		this.searchInput.layout();
 		this.listContainer.style.height = `${Math.max(0, listHeight)}px`;
 		this.list.layout(Math.max(0, listHeight), width);
+
+		// Re-layout once after footer renders if we used a zero fallback
+		if (sectionFooterHeight === 0) {
+			DOM.getWindow(this.listContainer).requestAnimationFrame(() => {
+				if (this._store.isDisposed) {
+					return;
+				}
+				const actualFooterHeight = this.sectionHeader.offsetHeight;
+				if (actualFooterHeight > 0) {
+					const correctedHeight = height - actualFooterHeight - searchBarHeight;
+					this.listContainer.style.height = `${Math.max(0, correctedHeight)}px`;
+					this.list.layout(Math.max(0, correctedHeight), width);
+				}
+			});
+		}
 	}
 
 	/**
@@ -1113,4 +1335,16 @@ export class AICustomizationListWidget extends Disposable {
 	get itemCount(): number {
 		return this.allItems.length;
 	}
+
+	/**
+	 * Generates a debug report for the current section.
+	 */
+	async generateDebugReport(): Promise<string> {
+		return generateCustomizationDebugReport(
+			this.currentSection,
+			this.promptsService,
+			this.workspaceService,
+			{ allItems: this.allItems, displayEntries: this.displayEntries },
+		);
+	}
 }
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationListWidgetUtils.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationListWidgetUtils.ts
new file mode 100644
index 0000000000000..dbe55af4e7785
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationListWidgetUtils.ts
@@ -0,0 +1,31 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { PromptsType } from '../../common/promptSyntax/promptTypes.js';
+
+/**
+ * Truncates a description string to the first sentence, with a maximum character fallback.
+ */
+export function truncateToFirstSentence(text: string, maxChars = 120): string {
+	const match = text.match(/^[^.!?]*[.!?]/);
+	if (match && match[0].length <= maxChars) {
+		return match[0];
+	}
+	if (text.length > maxChars) {
+		return text.substring(0, maxChars).trimEnd() + '\u2026';
+	}
+	return text;
+}
+
+/**
+ * Returns the secondary text shown for a customization item.
+ */
+export function getCustomizationSecondaryText(description: string | undefined, filename: string, promptType: PromptsType): string {
+	if (!description) {
+		return filename;
+	}
+
+	return promptType === PromptsType.hook ? description : truncateToFirstSentence(description);
+}
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.contribution.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.contribution.ts
index a841c81fe99ff..d9c682145d103 100644
--- a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.contribution.ts
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.contribution.ts
@@ -5,7 +5,7 @@
 
 import { Disposable } from '../../../../../base/common/lifecycle.js';
 import { localize, localize2 } from '../../../../../nls.js';
-import { Action2, MenuId, MenuRegistry, registerAction2 } from '../../../../../platform/actions/common/actions.js';
+import { Action2, MenuRegistry, registerAction2 } from '../../../../../platform/actions/common/actions.js';
 import { SyncDescriptor } from '../../../../../platform/instantiation/common/descriptors.js';
 import { IInstantiationService, ServicesAccessor } from '../../../../../platform/instantiation/common/instantiation.js';
 import { Registry } from '../../../../../platform/registry/common/platform.js';
@@ -20,23 +20,46 @@ import { AICustomizationManagementEditorInput } from './aiCustomizationManagemen
 import {
 	AI_CUSTOMIZATION_MANAGEMENT_EDITOR_ID,
 	AI_CUSTOMIZATION_MANAGEMENT_EDITOR_INPUT_ID,
+	AI_CUSTOMIZATION_ITEM_STORAGE_KEY,
+	AI_CUSTOMIZATION_ITEM_TYPE_KEY,
+	AI_CUSTOMIZATION_ITEM_URI_KEY,
 	AICustomizationManagementCommands,
 	AICustomizationManagementItemMenuId,
+	AICustomizationManagementSection,
+	BUILTIN_STORAGE,
 } from './aiCustomizationManagement.js';
 import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../../common/contributions.js';
 import { Codicon } from '../../../../../base/common/codicons.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { ICommandService } from '../../../../../platform/commands/common/commands.js';
-import { PROMPT_LANGUAGE_ID, INSTRUCTIONS_LANGUAGE_ID, AGENT_LANGUAGE_ID, SKILL_LANGUAGE_ID, PromptsType } from '../../common/promptSyntax/promptTypes.js';
+import { PromptsType } from '../../common/promptSyntax/promptTypes.js';
 import { PromptsStorage } from '../../common/promptSyntax/service/promptsService.js';
+import { IAICustomizationWorkspaceService } from '../../common/aiCustomizationWorkspaceService.js';
 import { ContextKeyExpr } from '../../../../../platform/contextkey/common/contextkey.js';
 import { ChatConfiguration } from '../../common/constants.js';
-import { IFileService } from '../../../../../platform/files/common/files.js';
+import { IFileService, FileSystemProviderCapabilities } from '../../../../../platform/files/common/files.js';
 import { IDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
-import { basename } from '../../../../../base/common/resources.js';
+import { basename, dirname } from '../../../../../base/common/resources.js';
 import { Schemas } from '../../../../../base/common/network.js';
 import { isWindows, isMacintosh } from '../../../../../base/common/platform.js';
-import { ResourceContextKey } from '../../../../common/contextkeys.js';
+import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
+import { IClipboardService } from '../../../../../platform/clipboard/common/clipboardService.js';
+
+//#region Telemetry
+
+type CustomizationEditorDeleteItemEvent = {
+	promptType: string;
+	storage: string;
+};
+
+type CustomizationEditorDeleteItemClassification = {
+	promptType: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The type of customization being deleted.' };
+	storage: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The storage location of the deleted item.' };
+	owner: 'joshspicer';
+	comment: 'Tracks item deletion in the Chat Customizations editor.';
+};
+
+//#endregion
 
 //#region Editor Registration
 
@@ -118,6 +141,16 @@ function extractStorage(context: AICustomizationContext): PromptsStorage | undef
 	return context.storage;
 }
 
+/**
+ * Extracts prompt type from context.
+ */
+function extractPromptType(context: AICustomizationContext): PromptsType | undefined {
+	if (URI.isUri(context) || typeof context === 'string') {
+		return undefined;
+	}
+	return context.promptType;
+}
+
 // Open file action
 const OPEN_AI_CUSTOMIZATION_MGMT_FILE_ID = 'aiCustomizationManagement.openFile';
 registerAction2(class extends Action2 {
@@ -192,11 +225,14 @@ registerAction2(class extends Action2 {
 		const dialogService = accessor.get(IDialogService);
 
 		const uri = extractURI(context);
-		const fileName = basename(uri);
 		const storage = extractStorage(context);
+		const promptType = extractPromptType(context);
+		const isSkill = promptType === PromptsType.skill;
+		// For skills, use the parent folder name since skills are structured as <skillname>/SKILL.md.
+		const fileName = isSkill ? basename(dirname(uri)) : basename(uri);
 
-		// Extension files cannot be deleted
-		if (storage === PromptsStorage.extension) {
+		// Extension, plugin, and built-in files cannot be deleted
+		if (storage === PromptsStorage.extension || storage === PromptsStorage.plugin || storage === BUILTIN_STORAGE) {
 			await dialogService.info(
 				localize('cannotDeleteExtension', "Cannot Delete Extension File"),
 				localize('cannotDeleteExtensionDetail', "Files provided by extensions cannot be deleted. You can disable the extension if you no longer want to use this customization.")
@@ -205,23 +241,89 @@ registerAction2(class extends Action2 {
 		}
 
 		// Confirm deletion
+		const message = isSkill
+			? localize('confirmDeleteSkill', "Are you sure you want to delete skill '{0}' and its folder?", fileName)
+			: localize('confirmDelete', "Are you sure you want to delete '{0}'?", fileName);
 		const confirmation = await dialogService.confirm({
-			message: localize('confirmDelete', "Are you sure you want to delete '{0}'?", fileName),
+			message,
 			detail: localize('confirmDeleteDetail', "This action cannot be undone."),
 			primaryButton: localize('delete', "Delete"),
 			type: 'warning',
 		});
 
 		if (confirmation.confirmed) {
-			await fileService.del(uri, { useTrash: true });
+			try {
+				const telemetryService = accessor.get(ITelemetryService);
+				telemetryService.publicLog2<CustomizationEditorDeleteItemEvent, CustomizationEditorDeleteItemClassification>('chatCustomizationEditor.deleteItem', {
+					promptType: promptType ?? '',
+					storage: storage ?? '',
+				});
+			} catch {
+				// Telemetry must not block deletion
+			}
+
+			// For skills, delete the parent folder (e.g. .github/skills/my-skill/)
+			// since each skill is a folder containing SKILL.md.
+			const deleteTarget = isSkill ? dirname(uri) : uri;
+			const useTrash = fileService.hasCapability(deleteTarget, FileSystemProviderCapabilities.Trash);
+			await fileService.del(deleteTarget, { useTrash, recursive: isSkill });
+
+			// Commit the deletion to git (sessions: main repo + worktree)
+			if (storage === PromptsStorage.local) {
+				const workspaceService = accessor.get(IAICustomizationWorkspaceService);
+				const projectRoot = workspaceService.getActiveProjectRoot();
+				if (projectRoot) {
+					await workspaceService.deleteFiles(projectRoot, [deleteTarget]);
+				}
+			}
 		}
 	}
 });
 
-// Context Key for prompt type to conditionally show "Run Prompt"
-const AI_CUSTOMIZATION_ITEM_TYPE_KEY = 'aiCustomizationManagementItemType';
+// Copy path action
+const COPY_AI_CUSTOMIZATION_PATH_ID = 'aiCustomizationManagement.copyPath';
+registerAction2(class extends Action2 {
+	constructor() {
+		super({
+			id: COPY_AI_CUSTOMIZATION_PATH_ID,
+			title: localize2('copyPath', "Copy Path"),
+			icon: Codicon.clippy,
+		});
+	}
+	async run(accessor: ServicesAccessor, context: AICustomizationContext): Promise<void> {
+		const clipboardService = accessor.get(IClipboardService);
+		const uri = extractURI(context);
+		const textToCopy = uri.scheme === 'file' ? uri.fsPath : uri.toString(true);
+		await clipboardService.writeText(textToCopy);
+	}
+});
+
+/**
+ * When clause that hides an action for read-only (extension, plugin, built-in) items.
+ */
+const WHEN_ITEM_IS_DELETABLE = ContextKeyExpr.and(
+	ContextKeyExpr.notEquals(AI_CUSTOMIZATION_ITEM_STORAGE_KEY, PromptsStorage.extension),
+	ContextKeyExpr.notEquals(AI_CUSTOMIZATION_ITEM_STORAGE_KEY, PromptsStorage.plugin),
+	ContextKeyExpr.notEquals(AI_CUSTOMIZATION_ITEM_STORAGE_KEY, BUILTIN_STORAGE),
+);
 
 // Register context menu items
+
+// Inline hover actions (shown as icon buttons on hover)
+MenuRegistry.appendMenuItem(AICustomizationManagementItemMenuId, {
+	command: { id: COPY_AI_CUSTOMIZATION_PATH_ID, title: localize('copyPath', "Copy Path"), icon: Codicon.clippy },
+	group: 'inline',
+	order: 1,
+});
+
+MenuRegistry.appendMenuItem(AICustomizationManagementItemMenuId, {
+	command: { id: DELETE_AI_CUSTOMIZATION_ID, title: localize('delete', "Delete"), icon: Codicon.trash },
+	group: 'inline',
+	order: 10,
+	when: WHEN_ITEM_IS_DELETABLE,
+});
+
+// Context menu items (shown on right-click)
 MenuRegistry.appendMenuItem(AICustomizationManagementItemMenuId, {
 	command: { id: OPEN_AI_CUSTOMIZATION_MGMT_FILE_ID, title: localize('open', "Open") },
 	group: '1_open',
@@ -240,8 +342,8 @@ MenuRegistry.appendMenuItem(AICustomizationManagementItemMenuId, {
 	group: '3_file',
 	order: 1,
 	when: ContextKeyExpr.or(
-		ContextKeyExpr.regex('aiCustomizationManagementItemUri', new RegExp(`^${Schemas.file}:`)),
-		ContextKeyExpr.regex('aiCustomizationManagementItemUri', new RegExp(`^${Schemas.vscodeUserData}:`))
+		ContextKeyExpr.regex(AI_CUSTOMIZATION_ITEM_URI_KEY, new RegExp(`^${Schemas.file}:`)),
+		ContextKeyExpr.regex(AI_CUSTOMIZATION_ITEM_URI_KEY, new RegExp(`^${Schemas.vscodeUserData}:`))
 	),
 });
 
@@ -249,6 +351,7 @@ MenuRegistry.appendMenuItem(AICustomizationManagementItemMenuId, {
 	command: { id: DELETE_AI_CUSTOMIZATION_ID, title: localize('delete', "Delete") },
 	group: '4_modify',
 	order: 1,
+	when: WHEN_ITEM_IS_DELETABLE,
 });
 
 //#endregion
@@ -270,39 +373,24 @@ class AICustomizationManagementActionsContribution extends Disposable implements
 			constructor() {
 				super({
 					id: AICustomizationManagementCommands.OpenEditor,
-					title: localize2('openAICustomizations', "Open Chat Customizations"),
-					shortTitle: localize2('aiCustomizations', "Chat Customizations"),
+					title: localize2('openAICustomizations', "Open Customizations (Preview)"),
+					shortTitle: localize2('aiCustomizations', "Customizations (Preview)"),
 					category: CHAT_CATEGORY,
 					precondition: ContextKeyExpr.and(ChatContextKeys.enabled, ContextKeyExpr.has(`config.${ChatConfiguration.ChatCustomizationMenuEnabled}`)),
 					f1: true,
-					menu: [
-						{
-							id: MenuId.GlobalActivity,
-							when: ContextKeyExpr.and(ChatContextKeys.enabled, ContextKeyExpr.has(`config.${ChatConfiguration.ChatCustomizationMenuEnabled}`)),
-							group: '2_configuration',
-							order: 4,
-						},
-						{
-							id: MenuId.EditorContent,
-							when: ContextKeyExpr.and(
-								ChatContextKeys.enabled,
-								ContextKeyExpr.or(
-									ContextKeyExpr.equals(ResourceContextKey.LangId.key, PROMPT_LANGUAGE_ID),
-									ContextKeyExpr.equals(ResourceContextKey.LangId.key, INSTRUCTIONS_LANGUAGE_ID),
-									ContextKeyExpr.equals(ResourceContextKey.LangId.key, AGENT_LANGUAGE_ID),
-									ContextKeyExpr.equals(ResourceContextKey.LangId.key, SKILL_LANGUAGE_ID),
-								),
-							),
-						}],
 				});
 			}
 
-			async run(accessor: ServicesAccessor): Promise<void> {
+			async run(accessor: ServicesAccessor, section?: AICustomizationManagementSection): Promise<void> {
 				const editorService = accessor.get(IEditorService);
 				const input = AICustomizationManagementEditorInput.getOrCreate();
-				await editorService.openEditor(input, { pinned: true }, MODAL_GROUP);
+				const pane = await editorService.openEditor(input, { pinned: true }, MODAL_GROUP);
+				if (section && pane instanceof AICustomizationManagementEditor) {
+					pane.selectSectionById(section);
+				}
 			}
 		}));
+
 	}
 }
 
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.ts
index 6aa4d4ba4d467..254aef807e8ab 100644
--- a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.ts
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagement.ts
@@ -5,12 +5,24 @@
 
 import { RawContextKey } from '../../../../../platform/contextkey/common/contextkey.js';
 import { AICustomizationManagementSection } from '../../common/aiCustomizationWorkspaceService.js';
+import { PromptsStorage } from '../../common/promptSyntax/service/promptsService.js';
 import { localize } from '../../../../../nls.js';
 import { MenuId } from '../../../../../platform/actions/common/actions.js';
 
 // Re-export for convenience — consumers import from this file
 export { AICustomizationManagementSection } from '../../common/aiCustomizationWorkspaceService.js';
 
+/**
+ * Extended storage type for AI Customization that includes built-in prompts
+ * shipped with the application, alongside the core `PromptsStorage` values.
+ */
+export type AICustomizationPromptsStorage = PromptsStorage | 'builtin';
+
+/**
+ * Storage type discriminator for built-in prompts shipped with the application.
+ */
+export const BUILTIN_STORAGE: AICustomizationPromptsStorage = 'builtin';
+
 /**
  * Editor pane ID for the AI Customizations Management Editor.
  */
@@ -60,6 +72,21 @@ export const AICustomizationManagementTitleMenuId = MenuId.for('AICustomizationM
  */
 export const AICustomizationManagementItemMenuId = MenuId.for('AICustomizationManagementEditorItem');
 
+/**
+ * Context key for the item prompt type (e.g. 'prompt', 'agent') used in when-clause filtering.
+ */
+export const AI_CUSTOMIZATION_ITEM_TYPE_KEY = 'aiCustomizationManagementItemType';
+
+/**
+ * Context key for the item storage type (e.g. 'local', 'user', 'extension') used in when-clause filtering.
+ */
+export const AI_CUSTOMIZATION_ITEM_STORAGE_KEY = 'aiCustomizationManagementItemStorage';
+
+/**
+ * Context key for the item URI used in when-clause filtering.
+ */
+export const AI_CUSTOMIZATION_ITEM_URI_KEY = 'aiCustomizationManagementItemUri';
+
 /**
  * Storage key for persisting the selected section.
  */
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagementEditor.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagementEditor.ts
index b5fd79c2fbeab..c89929e32b3c4 100644
--- a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagementEditor.ts
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagementEditor.ts
@@ -6,11 +6,13 @@
 import './media/aiCustomizationManagement.css';
 import * as DOM from '../../../../../base/browser/dom.js';
 import { CancellationToken } from '../../../../../base/common/cancellation.js';
+import { VSBuffer } from '../../../../../base/common/buffer.js';
 import { DisposableStore, IReference, toDisposable } from '../../../../../base/common/lifecycle.js';
 import { Event } from '../../../../../base/common/event.js';
 import { autorun } from '../../../../../base/common/observable.js';
 import { Orientation, Sizing, SplitView } from '../../../../../base/browser/ui/splitview/splitview.js';
 import { localize } from '../../../../../nls.js';
+import { generateUuid } from '../../../../../base/common/uuid.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../../platform/storage/common/storage.js';
 import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
 import { IThemeService } from '../../../../../platform/theme/common/themeService.js';
@@ -25,18 +27,21 @@ import { IListVirtualDelegate, IListRenderer } from '../../../../../base/browser
 import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { Codicon } from '../../../../../base/common/codicons.js';
 import { IOpenerService } from '../../../../../platform/opener/common/opener.js';
-import { basename, isEqual } from '../../../../../base/common/resources.js';
+import { basename, dirname, isEqual, isEqualOrParent } from '../../../../../base/common/resources.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { registerColor } from '../../../../../platform/theme/common/colorRegistry.js';
 import { PANEL_BORDER } from '../../../../common/theme.js';
 import { AICustomizationManagementEditorInput } from './aiCustomizationManagementEditorInput.js';
 import { AICustomizationListWidget } from './aiCustomizationListWidget.js';
 import { McpListWidget } from './mcpListWidget.js';
+import { PluginListWidget } from './pluginListWidget.js';
 import {
 	AI_CUSTOMIZATION_MANAGEMENT_EDITOR_ID,
 	AI_CUSTOMIZATION_MANAGEMENT_SIDEBAR_WIDTH_KEY,
 	AI_CUSTOMIZATION_MANAGEMENT_SELECTED_SECTION_KEY,
 	AICustomizationManagementSection,
+	AICustomizationPromptsStorage,
+	BUILTIN_STORAGE,
 	CONTEXT_AI_CUSTOMIZATION_MANAGEMENT_EDITOR,
 	CONTEXT_AI_CUSTOMIZATION_MANAGEMENT_SECTION,
 	SIDEBAR_DEFAULT_WIDTH,
@@ -44,28 +49,107 @@ import {
 	SIDEBAR_MAX_WIDTH,
 	CONTENT_MIN_WIDTH,
 } from './aiCustomizationManagement.js';
-import { agentIcon, instructionsIcon, promptIcon, skillIcon, hookIcon } from './aiCustomizationIcons.js';
+import { agentIcon, instructionsIcon, promptIcon, skillIcon, hookIcon, pluginIcon } from './aiCustomizationIcons.js';
 import { ChatModelsWidget } from '../chatManagement/chatModelsWidget.js';
-import { PromptsType } from '../../common/promptSyntax/promptTypes.js';
+import { PromptsType, Target } from '../../common/promptSyntax/promptTypes.js';
 import { IPromptsService, PromptsStorage } from '../../common/promptSyntax/service/promptsService.js';
+import { AGENT_MD_FILENAME } from '../../common/promptSyntax/config/promptFileLocations.js';
 import { INewPromptOptions, NEW_PROMPT_COMMAND_ID, NEW_INSTRUCTIONS_COMMAND_ID, NEW_AGENT_COMMAND_ID, NEW_SKILL_COMMAND_ID } from '../promptSyntax/newPromptFileActions.js';
 import { showConfigureHooksQuickPick } from '../promptSyntax/hookActions.js';
 import { resolveWorkspaceTargetDirectory, resolveUserTargetDirectory } from './customizationCreatorService.js';
 import { ICommandService } from '../../../../../platform/commands/common/commands.js';
 import { IAICustomizationWorkspaceService } from '../../common/aiCustomizationWorkspaceService.js';
-import { IEditorService } from '../../../../services/editor/common/editorService.js';
 import { CodeEditorWidget } from '../../../../../editor/browser/widget/codeEditor/codeEditorWidget.js';
+import { ITextModel } from '../../../../../editor/common/model.js';
+import { createTextBufferFactoryFromSnapshot } from '../../../../../editor/common/model/textModel.js';
+import { IModelService } from '../../../../../editor/common/services/model.js';
 import { IResolvedTextEditorModel, ITextModelService } from '../../../../../editor/common/services/resolverService.js';
 import { IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
-import { ILayoutService } from '../../../../../platform/layout/browser/layoutService.js';
 import { getSimpleEditorOptions } from '../../../codeEditor/browser/simpleEditorOptions.js';
 import { IWorkingCopyService } from '../../../../services/workingCopy/common/workingCopyService.js';
+import { IFileDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
+import { IHoverService } from '../../../../../platform/hover/browser/hover.js';
+import { IFileService } from '../../../../../platform/files/common/files.js';
+import { INotificationService } from '../../../../../platform/notification/common/notification.js';
+import { IQuickInputService, IQuickPickItem } from '../../../../../platform/quickinput/common/quickInput.js';
 import { McpServerEditorInput } from '../../../mcp/browser/mcpServerEditorInput.js';
 import { McpServerEditor } from '../../../mcp/browser/mcpServerEditor.js';
+import { getDefaultHoverDelegate } from '../../../../../base/browser/ui/hover/hoverDelegateFactory.js';
 import { IWorkbenchMcpServer } from '../../../mcp/common/mcpTypes.js';
+import { AgentPluginEditor } from '../agentPluginEditor/agentPluginEditor.js';
+import { AgentPluginEditorInput } from '../agentPluginEditor/agentPluginEditorInput.js';
+import { IAgentPluginItem } from '../agentPluginEditor/agentPluginItems.js';
 
 const $ = DOM.$;
 
+//#region Telemetry
+
+type CustomizationEditorOpenedEvent = {
+	section: string;
+};
+
+type CustomizationEditorOpenedClassification = {
+	section: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The initially selected section when the editor opens.' };
+	owner: 'joshspicer';
+	comment: 'Tracks when the Chat Customizations editor is opened.';
+};
+
+type CustomizationEditorSectionChangedEvent = {
+	section: string;
+};
+
+type CustomizationEditorSectionChangedClassification = {
+	section: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The section the user navigated to.' };
+	owner: 'joshspicer';
+	comment: 'Tracks section navigation within the Chat Customizations editor.';
+};
+
+type CustomizationEditorItemSelectedEvent = {
+	section: string;
+	promptType: string;
+	storage: string;
+};
+
+type CustomizationEditorItemSelectedClassification = {
+	section: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The active section when the item was selected.' };
+	promptType: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The prompt type of the selected item.' };
+	storage: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The storage location of the selected item (local, user, extension, plugin, builtin).' };
+	owner: 'joshspicer';
+	comment: 'Tracks item selection in the Chat Customizations editor.';
+};
+
+type CustomizationEditorCreateItemEvent = {
+	section: string;
+	promptType: string;
+	creationMode: 'ai' | 'manual';
+	target: string;
+};
+
+type CustomizationEditorCreateItemClassification = {
+	section: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The active section when the item was created.' };
+	promptType: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The type of customization being created.' };
+	creationMode: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Whether the item was created via AI-guided flow or manual creation.' };
+	target: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The target storage for the new item (workspace, user).' };
+	owner: 'joshspicer';
+	comment: 'Tracks customization creation in the Chat Customizations editor.';
+};
+
+type CustomizationEditorSaveItemEvent = {
+	promptType: string;
+	storage: string;
+	saveTarget: string;
+};
+
+type CustomizationEditorSaveItemClassification = {
+	promptType: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The type of customization being saved.' };
+	storage: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The original storage location of the item.' };
+	saveTarget: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The target storage for the save (workspace, user, existing).' };
+	owner: 'joshspicer';
+	comment: 'Tracks save actions in the Chat Customizations editor.';
+};
+
+//#endregion
+
 export const aiCustomizationManagementSashBorder = registerColor(
 	'aiCustomizationManagement.sashBorder',
 	PANEL_BORDER,
@@ -80,6 +164,26 @@ interface ISectionItem {
 	readonly icon: ThemeIcon;
 }
 
+interface ISaveTargetQuickPickItem extends IQuickPickItem {
+	readonly target: 'workspace' | 'user' | 'cancel';
+	readonly folder?: URI;
+}
+
+interface IBuiltinPromptSaveRequest {
+	readonly target: 'workspace' | 'user';
+	readonly folder: URI;
+	readonly sourceUri: URI;
+	readonly content: string;
+	readonly promptType: PromptsType;
+	readonly projectRoot?: URI;
+}
+
+interface IExistingCustomizationSaveRequest {
+	readonly fileUri: URI;
+	readonly content: string;
+	readonly projectRoot?: URI;
+}
+
 class SectionItemDelegate implements IListVirtualDelegate<ISectionItem> {
 	getHeight(): number {
 		return 26;
@@ -134,34 +238,53 @@ export class AICustomizationManagementEditor extends EditorPane {
 	private contentContainer!: HTMLElement;
 	private listWidget!: AICustomizationListWidget;
 	private mcpListWidget: McpListWidget | undefined;
+	private pluginListWidget: PluginListWidget | undefined;
 	private modelsWidget: ChatModelsWidget | undefined;
 	private promptsContentContainer!: HTMLElement;
 	private mcpContentContainer: HTMLElement | undefined;
+	private pluginContentContainer: HTMLElement | undefined;
 	private modelsContentContainer: HTMLElement | undefined;
 	private modelsFooterElement: HTMLElement | undefined;
 
-	// Embedded editor state (sessions only — preferManualCreation)
+	// Embedded editor state
 	private editorContentContainer: HTMLElement | undefined;
 	private embeddedEditor: CodeEditorWidget | undefined;
+	private editorActionButton!: HTMLButtonElement;
+	private editorActionButtonIcon!: HTMLElement;
+	private editorActionButtonInProgress = false;
 	private editorItemNameElement!: HTMLElement;
 	private editorItemPathElement!: HTMLElement;
 	private editorSaveIndicator!: HTMLElement;
 	private readonly editorModelChangeDisposables = this._register(new DisposableStore());
+	private readonly builtinEditingSessions = new Map<string, { model: ITextModel; originalContent: string }>();
 	private currentEditingUri: URI | undefined;
 	private currentEditingProjectRoot: URI | undefined;
+	private currentEditingStorage: AICustomizationPromptsStorage | undefined;
+	private currentEditingPromptType: PromptsType | undefined;
 	private currentModelRef: IReference<IResolvedTextEditorModel> | undefined;
-	private viewMode: 'list' | 'editor' | 'mcpDetail' = 'list';
+	private viewMode: 'list' | 'editor' | 'mcpDetail' | 'pluginDetail' = 'list';
 
 	// Embedded MCP server detail view
 	private mcpDetailContainer: HTMLElement | undefined;
 	private embeddedMcpEditor: McpServerEditor | undefined;
 	private readonly mcpDetailDisposables = this._register(new DisposableStore());
 
+	// Embedded plugin detail view
+	private pluginDetailContainer: HTMLElement | undefined;
+	private embeddedPluginEditor: AgentPluginEditor | undefined;
+	private readonly pluginDetailDisposables = this._register(new DisposableStore());
+
 	private dimension: DOM.Dimension | undefined;
 	private readonly sections: ISectionItem[] = [];
 	private selectedSection: AICustomizationManagementSection = AICustomizationManagementSection.Agents;
 
 	private readonly editorDisposables = this._register(new DisposableStore());
+	private _editorContentChanged = false;
+
+	// Folder picker (sessions window only)
+	private folderPickerContainer: HTMLElement | undefined;
+	private folderPickerLabel: HTMLElement | undefined;
+	private folderPickerClearButton: HTMLElement | undefined;
 
 	private readonly inEditorContextKey: IContextKey<boolean>;
 	private readonly sectionContextKey: IContextKey<string>;
@@ -176,31 +299,34 @@ export class AICustomizationManagementEditor extends EditorPane {
 		@IOpenerService private readonly openerService: IOpenerService,
 		@ICommandService private readonly commandService: ICommandService,
 		@IAICustomizationWorkspaceService private readonly workspaceService: IAICustomizationWorkspaceService,
-		@IEditorService private readonly editorService: IEditorService,
 		@IPromptsService private readonly promptsService: IPromptsService,
 		@ITextModelService private readonly textModelService: ITextModelService,
 		@IConfigurationService private readonly configurationService: IConfigurationService,
-		@ILayoutService private readonly layoutService: ILayoutService,
 		@IWorkingCopyService private readonly workingCopyService: IWorkingCopyService,
+		@IFileDialogService private readonly fileDialogService: IFileDialogService,
+		@IHoverService private readonly hoverService: IHoverService,
+		@IModelService private readonly modelService: IModelService,
+		@IQuickInputService private readonly quickInputService: IQuickInputService,
+		@IFileService private readonly fileService: IFileService,
+		@INotificationService private readonly notificationService: INotificationService,
 	) {
 		super(AICustomizationManagementEditor.ID, group, telemetryService, themeService, storageService);
 
 		this.inEditorContextKey = CONTEXT_AI_CUSTOMIZATION_MANAGEMENT_EDITOR.bindTo(contextKeyService);
 		this.sectionContextKey = CONTEXT_AI_CUSTOMIZATION_MANAGEMENT_SECTION.bindTo(contextKeyService);
 
-		// Track workspace changes for embedded editor (sessions only)
-		if (this.workspaceService.preferManualCreation) {
-			this._register(autorun(reader => {
-				this.workspaceService.activeProjectRoot.read(reader);
-				if (this.viewMode === 'editor') {
-					this.currentEditingProjectRoot = this.workspaceService.getActiveProjectRoot();
-				}
-			}));
-			this._register(toDisposable(() => {
-				this.currentModelRef?.dispose();
-				this.currentModelRef = undefined;
-			}));
-		}
+		// Track workspace changes for embedded editor
+		this._register(autorun(reader => {
+			this.workspaceService.activeProjectRoot.read(reader);
+			if (this.viewMode === 'editor') {
+				this.currentEditingProjectRoot = this.workspaceService.getActiveProjectRoot();
+			}
+		}));
+		this._register(toDisposable(() => {
+			this.currentModelRef?.dispose();
+			this.currentModelRef = undefined;
+		}));
+		this._register(toDisposable(() => this.disposeBuiltinEditingSessions()));
 
 		// Build sections from the workspace service configuration
 		const sectionInfo: Record<string, { label: string; icon: ThemeIcon }> = {
@@ -210,6 +336,7 @@ export class AICustomizationManagementEditor extends EditorPane {
 			[AICustomizationManagementSection.Prompts]: { label: localize('prompts', "Prompts"), icon: promptIcon },
 			[AICustomizationManagementSection.Hooks]: { label: localize('hooks', "Hooks"), icon: hookIcon },
 			[AICustomizationManagementSection.McpServers]: { label: localize('mcpServers', "MCP Servers"), icon: Codicon.server },
+			[AICustomizationManagementSection.Plugins]: { label: localize('plugins', "Plugins"), icon: pluginIcon },
 			[AICustomizationManagementSection.Models]: { label: localize('models', "Models"), icon: Codicon.vm },
 		};
 		for (const id of this.workspaceService.managementSections) {
@@ -261,7 +388,8 @@ export class AICustomizationManagementEditor extends EditorPane {
 			layout: (width, _, height) => {
 				this.sidebarContainer.style.width = `${width}px`;
 				if (height !== undefined) {
-					const listHeight = height - 8;
+					const footerHeight = this.folderPickerContainer?.offsetHeight ?? 0;
+					const listHeight = height - 8 - footerHeight;
 					this.sectionsList.layout(listHeight, width);
 				}
 			},
@@ -278,6 +406,7 @@ export class AICustomizationManagementEditor extends EditorPane {
 				if (height !== undefined) {
 					this.listWidget.layout(height - 16, width - 24);
 					this.mcpListWidget?.layout(height - 16, width - 24);
+					this.pluginListWidget?.layout(height - 16, width - 24);
 					const modelsFooterHeight = this.modelsFooterElement?.offsetHeight || 80;
 					this.modelsWidget?.layout(height - 16 - modelsFooterHeight, width);
 					if (this.viewMode === 'editor' && this.embeddedEditor) {
@@ -289,6 +418,10 @@ export class AICustomizationManagementEditor extends EditorPane {
 						const backHeaderHeight = 40;
 						this.embeddedMcpEditor.layout(new DOM.Dimension(width, Math.max(0, height - backHeaderHeight)));
 					}
+					if (this.viewMode === 'pluginDetail' && this.embeddedPluginEditor) {
+						const backHeaderHeight = 40;
+						this.embeddedPluginEditor.layout(new DOM.Dimension(width, Math.max(0, height - backHeaderHeight)));
+					}
 				}
 			},
 		}, Sizing.Distribute, undefined, true);
@@ -335,18 +468,81 @@ export class AICustomizationManagementEditor extends EditorPane {
 		));
 
 		this.sectionsList.splice(0, this.sectionsList.length, this.sections);
-
-		// Select the saved section
-		const selectedIndex = this.sections.findIndex(s => s.id === this.selectedSection);
-		if (selectedIndex >= 0) {
-			this.sectionsList.setSelection([selectedIndex]);
-		}
+		this.ensureSectionsListReflectsActiveSection();
 
 		this.editorDisposables.add(this.sectionsList.onDidChangeSelection(e => {
-			if (e.elements.length > 0) {
-				this.selectSection(e.elements[0].id);
+			if (e.elements.length === 0) {
+				this.ensureSectionsListReflectsActiveSection();
+				return;
 			}
+			this.selectSection(e.elements[0].id);
 		}));
+
+		// Folder picker (sessions window only)
+		if (this.workspaceService.isSessionsWindow) {
+			this.createFolderPicker(sidebarContent);
+		}
+	}
+
+	private createFolderPicker(sidebarContent: HTMLElement): void {
+		const footer = this.folderPickerContainer = DOM.append(sidebarContent, $('.sidebar-folder-picker'));
+
+		const button = DOM.append(footer, $('button.folder-picker-button'));
+		button.setAttribute('aria-label', localize('browseFolder', "Browse folder"));
+
+		const folderIcon = DOM.append(button, $(`.codicon.codicon-${Codicon.folder.id}`));
+		folderIcon.classList.add('folder-picker-icon');
+
+		this.folderPickerLabel = DOM.append(button, $('span.folder-picker-label'));
+
+		this.folderPickerClearButton = DOM.append(footer, $('button.folder-picker-clear'));
+		this.folderPickerClearButton.setAttribute('aria-label', localize('clearFolderOverride', "Reset to session folder"));
+		DOM.append(this.folderPickerClearButton, $(`.codicon.codicon-${Codicon.close.id}`));
+
+		// Clicking the main button opens the folder dialog
+		this.editorDisposables.add(DOM.addDisposableListener(button, 'click', () => {
+			this.browseForFolder();
+		}));
+
+		// Clear button resets to session default
+		this.editorDisposables.add(DOM.addDisposableListener(this.folderPickerClearButton, 'click', () => {
+			this.workspaceService.clearOverrideProjectRoot();
+		}));
+
+		// Hover showing full path
+		this.editorDisposables.add(this.hoverService.setupManagedHover(getDefaultHoverDelegate('element'), button, () => {
+			const root = this.workspaceService.getActiveProjectRoot();
+			return root?.fsPath ?? '';
+		}));
+
+		// Keep label and clear button in sync with the active root
+		this.editorDisposables.add(autorun(reader => {
+			const root = this.workspaceService.activeProjectRoot.read(reader);
+			const hasOverride = this.workspaceService.hasOverrideProjectRoot.read(reader);
+			this.updateFolderPickerLabel(root, hasOverride);
+		}));
+	}
+
+	private updateFolderPickerLabel(root: URI | undefined, hasOverride: boolean): void {
+		if (this.folderPickerLabel) {
+			this.folderPickerLabel.textContent = root ? basename(root) : localize('noFolder', "No folder");
+		}
+		if (this.folderPickerClearButton) {
+			this.folderPickerClearButton.style.display = hasOverride ? '' : 'none';
+		}
+	}
+
+	private async browseForFolder(): Promise<void> {
+		const result = await this.fileDialogService.showOpenDialog({
+			canSelectFolders: true,
+			canSelectFiles: false,
+			canSelectMany: false,
+			title: localize('selectFolder', "Select Folder to Explore"),
+			defaultUri: this.workspaceService.getActiveProjectRoot(),
+		});
+		if (result?.[0]) {
+			this.workspaceService.setOverrideProjectRoot(result[0]);
+		}
 	}
 
 	private createContent(): void {
@@ -359,13 +555,14 @@ export class AICustomizationManagementEditor extends EditorPane {
 
 		// Handle item selection
 		this.editorDisposables.add(this.listWidget.onDidSelectItem(item => {
-			if (this.workspaceService.preferManualCreation) {
-				const isWorkspaceFile = item.storage === PromptsStorage.local;
-				const isReadOnly = item.storage === PromptsStorage.extension;
-				this.showEmbeddedEditor(item.uri, item.name, isWorkspaceFile, isReadOnly);
-			} else {
-				this.editorService.openEditor({ resource: item.uri });
-			}
+			this.telemetryService.publicLog2<CustomizationEditorItemSelectedEvent, CustomizationEditorItemSelectedClassification>('chatCustomizationEditor.itemSelected', {
+				section: this.selectedSection,
+				promptType: item.promptType,
+				storage: item.storage,
+			});
+			const isWorkspaceFile = item.storage === PromptsStorage.local;
+			const isReadOnly = item.storage === PromptsStorage.extension || item.storage === PromptsStorage.plugin || item.storage === BUILTIN_STORAGE;
+			this.showEmbeddedEditor(item.uri, item.name, item.promptType, item.storage, isWorkspaceFile, isReadOnly);
 		}));
 
 		// Handle create actions - AI-guided creation
@@ -412,12 +609,25 @@ export class AICustomizationManagementEditor extends EditorPane {
 			}));
 		}
 
-		// Embedded editor container (sessions only)
-		if (this.workspaceService.preferManualCreation) {
-			this.editorContentContainer = DOM.append(contentInner, $('.editor-content-container'));
-			this.createEmbeddedEditor();
+		// Container for Plugins content
+		if (hasSections.has(AICustomizationManagementSection.Plugins)) {
+			this.pluginContentContainer = DOM.append(contentInner, $('.plugin-content-container'));
+			this.pluginListWidget = this.editorDisposables.add(this.instantiationService.createInstance(PluginListWidget));
+			this.pluginContentContainer.appendChild(this.pluginListWidget.element);
+
+			// Embedded plugin detail view
+			this.pluginDetailContainer = DOM.append(contentInner, $('.plugin-detail-container'));
+			this.createEmbeddedPluginDetail();
+
+			this.editorDisposables.add(this.pluginListWidget.onDidSelectPlugin(item => {
+				this.showEmbeddedPluginDetail(item);
+			}));
 		}
 
+		// Embedded editor container
+		this.editorContentContainer = DOM.append(contentInner, $('.editor-content-container'));
+		this.createEmbeddedEditor();
+
 		// Set initial visibility based on selected section
 		this.updateContentVisibility();
 
@@ -437,15 +647,23 @@ export class AICustomizationManagementEditor extends EditorPane {
 
 	private selectSection(section: AICustomizationManagementSection): void {
 		if (this.selectedSection === section) {
+			this.ensureSectionsListReflectsActiveSection(section);
 			return;
 		}
 
+		this.telemetryService.publicLog2<CustomizationEditorSectionChangedEvent, CustomizationEditorSectionChangedClassification>('chatCustomizationEditor.sectionChanged', {
+			section,
+		});
+
 		if (this.viewMode === 'editor') {
 			this.goBackToList();
 		}
 		if (this.viewMode === 'mcpDetail') {
 			this.goBackFromMcpDetail();
 		}
+		if (this.viewMode === 'pluginDetail') {
+			this.goBackFromPluginDetail();
+		}
 
 		this.selectedSection = section;
 		this.sectionContextKey.set(section);
@@ -453,9 +671,6 @@ export class AICustomizationManagementEditor extends EditorPane {
 		// Persist selection
 		this.storageService.store(AI_CUSTOMIZATION_MANAGEMENT_SELECTED_SECTION_KEY, section, StorageScope.PROFILE, StorageTarget.USER);
 
-		// Update editor tab title
-		this.updateEditorTitle();
-
 		// Update content visibility
 		this.updateContentVisibility();
 
@@ -463,32 +678,57 @@ export class AICustomizationManagementEditor extends EditorPane {
 		if (this.isPromptsSection(section)) {
 			void this.listWidget.setSection(section);
 		}
+
+		this.ensureSectionsListReflectsActiveSection(section);
 	}
 
-	private updateEditorTitle(): void {
-		const sectionItem = this.sections.find(s => s.id === this.selectedSection);
-		if (sectionItem && this.input instanceof AICustomizationManagementEditorInput) {
-			this.input.setSectionLabel(sectionItem.label);
+	private ensureSectionsListReflectsActiveSection(section: AICustomizationManagementSection = this.selectedSection): void {
+		if (!this.sectionsList) {
+			return;
+		}
+
+		const index = this.sections.findIndex(s => s.id === section);
+		if (index < 0) {
+			return;
+		}
+
+		const selection = this.sectionsList.getSelection();
+		if (selection.length !== 1 || selection[0] !== index) {
+			this.sectionsList.setSelection([index]);
+		}
+
+		const focus = this.sectionsList.getFocus();
+		if (focus.length !== 1 || focus[0] !== index) {
+			this.sectionsList.setFocus([index]);
 		}
 	}
 
 	private updateContentVisibility(): void {
 		const isEditorMode = this.viewMode === 'editor';
 		const isMcpDetailMode = this.viewMode === 'mcpDetail';
+		const isPluginDetailMode = this.viewMode === 'pluginDetail';
+		const isDetailMode = isMcpDetailMode || isPluginDetailMode;
 		const isPromptsSection = this.isPromptsSection(this.selectedSection);
 		const isModelsSection = this.selectedSection === AICustomizationManagementSection.Models;
 		const isMcpSection = this.selectedSection === AICustomizationManagementSection.McpServers;
+		const isPluginsSection = this.selectedSection === AICustomizationManagementSection.Plugins;
 
-		this.promptsContentContainer.style.display = !isEditorMode && !isMcpDetailMode && isPromptsSection ? '' : 'none';
+		this.promptsContentContainer.style.display = !isEditorMode && !isDetailMode && isPromptsSection ? '' : 'none';
 		if (this.modelsContentContainer) {
-			this.modelsContentContainer.style.display = !isEditorMode && !isMcpDetailMode && isModelsSection ? '' : 'none';
+			this.modelsContentContainer.style.display = !isEditorMode && !isDetailMode && isModelsSection ? '' : 'none';
 		}
 		if (this.mcpContentContainer) {
-			this.mcpContentContainer.style.display = !isEditorMode && !isMcpDetailMode && isMcpSection ? '' : 'none';
+			this.mcpContentContainer.style.display = !isEditorMode && !isDetailMode && isMcpSection ? '' : 'none';
 		}
 		if (this.mcpDetailContainer) {
 			this.mcpDetailContainer.style.display = isMcpDetailMode ? '' : 'none';
 		}
+		if (this.pluginContentContainer) {
+			this.pluginContentContainer.style.display = !isEditorMode && !isDetailMode && isPluginsSection ? '' : 'none';
+		}
+		if (this.pluginDetailContainer) {
+			this.pluginDetailContainer.style.display = isPluginDetailMode ? '' : 'none';
+		}
 		if (this.editorContentContainer) {
 			this.editorContentContainer.style.display = isEditorMode ? '' : 'none';
 		}
@@ -506,49 +746,85 @@ export class AICustomizationManagementEditor extends EditorPane {
 	 * Creates a new customization using the AI-guided flow.
 	 */
 	private async createNewItemWithAI(type: PromptsType): Promise<void> {
-		this.close();
+		this.telemetryService.publicLog2<CustomizationEditorCreateItemEvent, CustomizationEditorCreateItemClassification>('chatCustomizationEditor.createItem', {
+			section: this.selectedSection,
+			promptType: type,
+			creationMode: 'ai',
+			target: 'workspace',
+		});
+		if (this.input) {
+			this.group.closeEditor(this.input);
+		}
 		await this.workspaceService.generateCustomization(type);
 	}
 
 	/**
-	 * Creates a new prompt file and opens it.
-	 * In sessions (preferManualCreation), uses the embedded editor with commit-on-close.
-	 * In core, opens in a regular editor tab.
+	 * Creates a new prompt file and opens it in the embedded editor.
 	 */
-	private async createNewItemManual(type: PromptsType, target: 'workspace' | 'user'): Promise<void> {
-		const useEmbeddedEditor = this.workspaceService.preferManualCreation;
+	private async createNewItemManual(type: PromptsType, target: 'workspace' | 'user' | 'workspace-root'): Promise<void> {
+		this.telemetryService.publicLog2<CustomizationEditorCreateItemEvent, CustomizationEditorCreateItemClassification>('chatCustomizationEditor.createItem', {
+			section: this.selectedSection,
+			promptType: type,
+			creationMode: 'manual',
+			target: target === 'workspace-root' ? 'workspace' : target,
+		});
+
+		// Handle workspace-root files (e.g. AGENTS.md at project root)
+		if (target === 'workspace-root') {
+			const projectRoot = this.workspaceService.getActiveProjectRoot();
+			if (!projectRoot) {
+				return;
+			}
+			const fileUri = URI.joinPath(projectRoot, AGENT_MD_FILENAME);
+			if (await this.fileService.exists(fileUri)) {
+				// File already exists — just open it
+				await this.showEmbeddedEditor(fileUri, AGENT_MD_FILENAME, PromptsType.instructions, PromptsStorage.local, true);
+			} else {
+				await this.fileService.createFile(fileUri);
+				await this.showEmbeddedEditor(fileUri, AGENT_MD_FILENAME, PromptsType.instructions, PromptsStorage.local, true);
+			}
+			void this.listWidget.refresh();
+			return;
+		}
 
 		if (type === PromptsType.hook) {
-			const isWorkspace = target === 'workspace';
-			await this.instantiationService.invokeFunction(showConfigureHooksQuickPick, {
-				openEditor: async (resource) => {
-					if (useEmbeddedEditor) {
-						await this.showEmbeddedEditor(resource, basename(resource), isWorkspace);
-					} else {
-						await this.editorService.openEditor({ resource });
+			if (this.workspaceService.isSessionsWindow) {
+				// Sessions: show hooks filtered to Copilot CLI (GitHub Copilot) hook types
+				await this.instantiationService.invokeFunction(showConfigureHooksQuickPick, {
+					openEditor: async (resource) => {
+						await this.showEmbeddedEditor(resource, basename(resource), PromptsType.hook, PromptsStorage.local, true);
+						return;
+					},
+					target: Target.GitHubCopilot,
+				});
+			} else {
+				// Core: use the default core behaviour
+				await this.instantiationService.invokeFunction(showConfigureHooksQuickPick, {
+					openEditor: async (resource) => {
+						await this.showEmbeddedEditor(resource, basename(resource), PromptsType.hook, PromptsStorage.local, true);
+						return;
 					}
-					return;
-				},
-			});
+				});
+			}
 			return;
 		}
 
-		const targetDir = target === 'workspace'
-			? resolveWorkspaceTargetDirectory(this.workspaceService, type)
-			: await resolveUserTargetDirectory(this.promptsService, type);
+		const targetDir = await this.resolveTargetDirectoryWithPicker(type, target);
+		if (targetDir === null) {
+			return; // User cancelled the picker
+		}
+		// targetDir may be undefined when no matching folder exists for the
+		// requested storage type (e.g. skills have no user-storage folder).
+		// Pass it through — the command handles undefined by showing its own
+		// folder picker via askForPromptSourceFolder.
 
 		const options: INewPromptOptions = {
 			targetFolder: targetDir,
 			targetStorage: target === 'user' ? PromptsStorage.user : PromptsStorage.local,
 			openFile: async (uri) => {
-				if (useEmbeddedEditor) {
-					const isWorkspace = target === 'workspace';
-					await this.showEmbeddedEditor(uri, basename(uri), isWorkspace);
-					return this.embeddedEditor;
-				} else {
-					await this.editorService.openEditor({ resource: uri });
-					return undefined;
-				}
+				const isWorkspace = target === 'workspace';
+				await this.showEmbeddedEditor(uri, basename(uri), type, target === 'user' ? PromptsStorage.user : PromptsStorage.local, isWorkspace);
+				return this.embeddedEditor;
 			},
 		};
 
@@ -565,6 +841,69 @@ export class AICustomizationManagementEditor extends EditorPane {
 		void this.listWidget.refresh();
 	}
 
+	/**
+	 * Resolves the target directory for creating a new customization file.
+	 * If multiple source folders exist for the given storage type, shows a
+	 * picker to let the user choose. Otherwise, returns the single match.
+	 *
+	 * @returns the resolved URI, `undefined` when no folder is available,
+	 *          or `null` when the user cancelled the picker.
+	 */
+	private async resolveTargetDirectoryWithPicker(type: PromptsType, target: 'workspace' | 'user'): Promise<URI | undefined | null> {
+		const allFolders = await this.promptsService.getSourceFolders(type);
+		const projectRoot = this.workspaceService.getActiveProjectRoot();
+
+		// Partition folders by whether they're under the active project root.
+		// The storage tags from getSourceFolders() are unreliable (tilde-expanded
+		// user paths like ~/.copilot/skills get tagged PromptsStorage.local),
+		// so we use the project root as the authoritative boundary.
+		let matchingFolders;
+		if (target === 'workspace') {
+			matchingFolders = projectRoot
+				? allFolders.filter(f => isEqualOrParent(f.uri, projectRoot))
+				: [];
+		} else {
+			matchingFolders = projectRoot
+				? allFolders.filter(f => !isEqualOrParent(f.uri, projectRoot))
+				: allFolders;
+		}
+
+		// Deduplicate by URI (getSourceFolders may return the same path
+		// from both config-based discovery and the AgenticPromptsService override)
+		const seen = new Set<string>();
+		matchingFolders = matchingFolders.filter(f => {
+			const key = f.uri.toString();
+			if (seen.has(key)) {
+				return false;
+			}
+			seen.add(key);
+			return true;
+		});
+
+		if (matchingFolders.length === 0) {
+			// No matching folders — return undefined so the command can fall
+			// back to askForPromptSourceFolder (not null which means cancellation)
+			return undefined;
+		}
+
+		if (matchingFolders.length === 1) {
+			return matchingFolders[0].uri;
+		}
+
+		// Multiple directories — ask the user which one to use
+		const items: (IQuickPickItem & { uri: URI })[] = matchingFolders.map(folder => ({
+			label: this.promptsService.getPromptLocationLabel(folder),
+			description: folder.uri.fsPath,
+			uri: folder.uri,
+		}));
+
+		const picked = await this.quickInputService.pick(items, {
+			placeHolder: localize('selectTargetDirectory', "Select a directory for the new customization file"),
+		});
+
+		return picked?.uri ?? null;
+	}
+
 	override updateStyles(): void {
 		const borderColor = this.theme.getColor(aiCustomizationManagementSashBorder);
 		if (borderColor) {
@@ -573,13 +912,17 @@ export class AICustomizationManagementEditor extends EditorPane {
 	}
 
 	override async setInput(input: AICustomizationManagementEditorInput, options: IEditorOptions | undefined, context: IEditorOpenContext, token: CancellationToken): Promise<void> {
+		// On (re)open, clear any override so the root comes from the default source
+		this.workspaceService.clearOverrideProjectRoot();
+
 		this.inEditorContextKey.set(true);
 		this.sectionContextKey.set(this.selectedSection);
 
-		await super.setInput(input, options, context, token);
+		this.telemetryService.publicLog2<CustomizationEditorOpenedEvent, CustomizationEditorOpenedClassification>('chatCustomizationEditor.opened', {
+			section: this.selectedSection,
+		});
 
-		// Set initial editor tab title
-		this.updateEditorTitle();
+		await super.setInput(input, options, context, token);
 
 		if (this.dimension) {
 			this.layout(this.dimension);
@@ -594,6 +937,12 @@ export class AICustomizationManagementEditor extends EditorPane {
 		if (this.viewMode === 'mcpDetail') {
 			this.goBackFromMcpDetail();
 		}
+		if (this.viewMode === 'pluginDetail') {
+			this.goBackFromPluginDetail();
+		}
+		// Clear transient folder override on close
+		this.workspaceService.clearOverrideProjectRoot();
+		this.disposeBuiltinEditingSessions();
 		super.clearInput();
 	}
 
@@ -614,6 +963,8 @@ export class AICustomizationManagementEditor extends EditorPane {
 		}
 		if (this.selectedSection === AICustomizationManagementSection.McpServers) {
 			this.mcpListWidget?.focusSearch();
+		} else if (this.selectedSection === AICustomizationManagementSection.Plugins) {
+			this.pluginListWidget?.focusSearch();
 		} else if (this.selectedSection === AICustomizationManagementSection.Models) {
 			this.modelsWidget?.focusSearch();
 		} else {
@@ -627,8 +978,26 @@ export class AICustomizationManagementEditor extends EditorPane {
 	public selectSectionById(sectionId: AICustomizationManagementSection): void {
 		const index = this.sections.findIndex(s => s.id === sectionId);
 		if (index >= 0) {
-			this.sectionsList.setFocus([index]);
-			this.sectionsList.setSelection([index]);
+			// Directly update state and UI, bypassing the early-return guard in selectSection
+			// to handle the case where the editor just opened with a persisted section that
+			// matches the requested one (content might not be loaded yet).
+			if (this.viewMode === 'editor') {
+				this.goBackToList();
+			}
+			if (this.viewMode === 'mcpDetail') {
+				this.goBackFromMcpDetail();
+			}
+			if (this.viewMode === 'pluginDetail') {
+				this.goBackFromPluginDetail();
+			}
+			this.selectedSection = sectionId;
+			this.sectionContextKey.set(sectionId);
+			this.storageService.store(AI_CUSTOMIZATION_MANAGEMENT_SELECTED_SECTION_KEY, sectionId, StorageScope.PROFILE, StorageTarget.USER);
+			this.updateContentVisibility();
+			if (this.isPromptsSection(sectionId)) {
+				void this.listWidget.setSection(sectionId);
+			}
+			this.ensureSectionsListReflectsActiveSection(sectionId);
 		}
 	}
 
@@ -639,13 +1008,14 @@ export class AICustomizationManagementEditor extends EditorPane {
 		void this.listWidget.refresh();
 	}
 
-	private close(): void {
-		if (!this.workspaceService.preferManualCreation && this.input) {
-			this.group.closeEditor(this.input);
-		}
+	/**
+	 * Generates a debug report for the current section.
+	 */
+	public async generateDebugReport(): Promise<string> {
+		return this.listWidget.generateDebugReport();
 	}
 
-	//#region Embedded Editor (sessions only)
+	//#region Embedded Editor
 
 	private createEmbeddedEditor(): void {
 		if (!this.editorContentContainer) {
@@ -654,21 +1024,25 @@ export class AICustomizationManagementEditor extends EditorPane {
 
 		const editorHeader = DOM.append(this.editorContentContainer, $('.editor-header'));
 
-		const backButton = DOM.append(editorHeader, $('button.editor-back-button'));
-		backButton.setAttribute('aria-label', localize('backToList', "Back to list"));
-		const backIcon = DOM.append(backButton, $(`.codicon.codicon-${Codicon.arrowLeft.id}`));
-		backIcon.setAttribute('aria-hidden', 'true');
-		this.editorDisposables.add(DOM.addDisposableListener(backButton, 'click', () => {
-			this.goBackToList();
+		this.editorActionButton = DOM.append(editorHeader, $('button.editor-back-button'));
+		this.editorActionButton.setAttribute('aria-label', localize('backToList', "Back to list"));
+		this.editorActionButtonIcon = DOM.append(this.editorActionButton, $(`.codicon.codicon-${Codicon.arrowLeft.id}.editor-action-button-icon`));
+		this.editorActionButtonIcon.setAttribute('aria-hidden', 'true');
+		this.editorDisposables.add(DOM.addDisposableListener(this.editorActionButton, 'click', () => {
+			void this.handleEditorActionButton().catch(error => {
+				console.error('Failed to handle editor back action:', error);
+				this.notificationService.error(localize('editorActionButtonFailed', "Failed to finish the prompt action."));
+			});
 		}));
 
 		const itemInfo = DOM.append(editorHeader, $('.editor-item-info'));
 		this.editorItemNameElement = DOM.append(itemInfo, $('.editor-item-name'));
 		this.editorItemPathElement = DOM.append(itemInfo, $('.editor-item-path'));
+
 		this.editorSaveIndicator = DOM.append(editorHeader, $('.editor-save-indicator'));
 
 		const embeddedEditorContainer = DOM.append(this.editorContentContainer, $('.embedded-editor-container'));
-		const overflowWidgetsDomNode = this.layoutService.getContainer(DOM.getWindow(embeddedEditorContainer)).appendChild($('.embedded-editor-overflow-widgets.monaco-editor'));
+		const overflowWidgetsDomNode = DOM.append(this.editorContentContainer, $('.embedded-editor-overflow-widgets.monaco-editor'));
 		this.editorDisposables.add(toDisposable(() => overflowWidgetsDomNode.remove()));
 
 		this.embeddedEditor = this.editorDisposables.add(this.instantiationService.createInstance(
@@ -691,19 +1065,55 @@ export class AICustomizationManagementEditor extends EditorPane {
 		));
 	}
 
-	private async showEmbeddedEditor(uri: URI, displayName: string, isWorkspaceFile = false, isReadOnly = false): Promise<void> {
+	private async showEmbeddedEditor(uri: URI, displayName: string, promptType: PromptsType, storage: AICustomizationPromptsStorage, isWorkspaceFile = false, isReadOnly = false): Promise<void> {
 		this.currentModelRef?.dispose();
 		this.currentModelRef = undefined;
+		this.editorModelChangeDisposables.clear();
 		this.currentEditingUri = uri;
 		this.currentEditingProjectRoot = isWorkspaceFile ? this.workspaceService.getActiveProjectRoot() : undefined;
+		this.currentEditingStorage = storage;
+		this.currentEditingPromptType = promptType;
 		this.viewMode = 'editor';
 
 		this.editorItemNameElement.textContent = displayName;
 		this.editorItemPathElement.textContent = basename(uri);
+		this._editorContentChanged = false;
+		this.resetEditorSaveIndicator();
+		this.updateEditorActionButton();
 		this.updateContentVisibility();
 
 		try {
+			if (storage === BUILTIN_STORAGE && (promptType === PromptsType.prompt || promptType === PromptsType.skill)) {
+				const session = await this.getOrCreateBuiltinEditingSession(uri);
+
+				if (!isEqual(this.currentEditingUri, uri)) {
+					return;
+				}
+
+				this.embeddedEditor!.setModel(session.model);
+				this.embeddedEditor!.updateOptions({ readOnly: false });
+				this._editorContentChanged = session.model.getValue() !== session.originalContent;
+				this.updateEditorActionButton();
+
+				if (this.dimension) {
+					this.layout(this.dimension);
+				}
+				this.embeddedEditor!.focus();
+
+				this.editorModelChangeDisposables.add(session.model.onDidChangeContent(() => {
+					this._editorContentChanged = session.model.getValue() !== session.originalContent;
+					this.updateEditorActionButton();
+				}));
+				return;
+			}
+
 			const ref = await this.textModelService.createModelReference(uri);
+
+			if (!isEqual(this.currentEditingUri, uri)) {
+				ref.dispose();
+				return; // another item was selected while loading
+			}
+
 			this.currentModelRef = ref;
 			this.embeddedEditor!.setModel(ref.object.textEditorModel);
 			this.embeddedEditor!.updateOptions({ readOnly: isReadOnly });
@@ -713,14 +1123,14 @@ export class AICustomizationManagementEditor extends EditorPane {
 			}
 			this.embeddedEditor!.focus();
 
-			this.editorModelChangeDisposables.clear();
+			this._editorContentChanged = this.workingCopyService.isDirty(uri);
 			this.editorModelChangeDisposables.add(ref.object.textEditorModel.onDidChangeContent(() => {
-				this.editorSaveIndicator.className = 'editor-save-indicator visible';
-				this.editorSaveIndicator.classList.add(...ThemeIcon.asClassNameArray(Codicon.loading), 'codicon-modifier-spin');
-				this.editorSaveIndicator.title = localize('saving', "Saving...");
+				this._editorContentChanged = true;
+				this.resetEditorSaveIndicator();
 			}));
 			this.editorModelChangeDisposables.add(this.workingCopyService.onDidSave(e => {
 				if (isEqual(e.workingCopy.resource, uri)) {
+					this._editorContentChanged = this.workingCopyService.isDirty(uri);
 					this.editorSaveIndicator.className = 'editor-save-indicator visible saved';
 					this.editorSaveIndicator.classList.add(...ThemeIcon.asClassNameArray(Codicon.check));
 					this.editorSaveIndicator.title = localize('saved', "Saved");
@@ -728,37 +1138,271 @@ export class AICustomizationManagementEditor extends EditorPane {
 			}));
 		} catch (error) {
 			console.error('Failed to load model for embedded editor:', error);
-			this.goBackToList();
+			if (isEqual(this.currentEditingUri, uri)) {
+				this.goBackToList();
+			}
 		}
 	}
 
 	private goBackToList(): void {
-		// Auto-commit workspace files when leaving the embedded editor
 		const fileUri = this.currentEditingUri;
-		const projectRoot = this.currentEditingProjectRoot;
-		if (fileUri && projectRoot) {
-			this.workspaceService.commitFiles(projectRoot, [fileUri]);
+		const backgroundSaveRequest = this.createExistingCustomizationSaveRequest();
+		if (backgroundSaveRequest) {
+			this.telemetryService.publicLog2<CustomizationEditorSaveItemEvent, CustomizationEditorSaveItemClassification>('chatCustomizationEditor.saveItem', {
+				promptType: this.currentEditingPromptType ?? '',
+				storage: String(this.currentEditingStorage ?? ''),
+				saveTarget: 'existing',
+			});
+		}
+		if (fileUri && this.currentEditingStorage === BUILTIN_STORAGE) {
+			this.disposeBuiltinEditingSession(fileUri);
 		}
 
 		this.currentModelRef?.dispose();
 		this.currentModelRef = undefined;
 		this.currentEditingUri = undefined;
 		this.currentEditingProjectRoot = undefined;
+		this.currentEditingStorage = undefined;
+		this.currentEditingPromptType = undefined;
+		this._editorContentChanged = false;
 		this.editorModelChangeDisposables.clear();
-		this.editorSaveIndicator.className = 'editor-save-indicator';
-		this.editorSaveIndicator.title = '';
+		this.resetEditorSaveIndicator();
+		this.updateEditorActionButton();
 		this.embeddedEditor?.setModel(null);
 		this.viewMode = 'list';
 		this.updateContentVisibility();
 
+		// Refresh the list to pick up newly created/edited files
+		void this.listWidget?.refresh();
+
 		if (this.dimension) {
 			this.layout(this.dimension);
 		}
 		this.listWidget?.focusSearch();
+
+		if (backgroundSaveRequest) {
+			const saveRequest = backgroundSaveRequest;
+			void this.saveExistingCustomization(saveRequest).catch(error => {
+				console.error('Failed to save customization changes on exit:', error);
+				this.notificationService.warn(localize('saveCustomizationOnExitFailed', "Could not save changes to {0}.", basename(saveRequest.fileUri)));
+			});
+		}
 	}
 
 	//#endregion
 
+	private async getOrCreateBuiltinEditingSession(uri: URI): Promise<{ model: ITextModel; originalContent: string }> {
+		const key = uri.toString();
+		const existing = this.builtinEditingSessions.get(key);
+		if (existing && !existing.model.isDisposed()) {
+			return existing;
+		}
+
+		const ref = await this.textModelService.createModelReference(uri);
+		try {
+			const session = {
+				model: this.modelService.createModel(
+					createTextBufferFactoryFromSnapshot(ref.object.textEditorModel.createSnapshot()),
+					{ languageId: ref.object.textEditorModel.getLanguageId(), onDidChange: Event.None },
+					URI.from({ scheme: 'ai-customization-builtin', path: uri.path, query: generateUuid() }),
+					false
+				),
+				originalContent: ref.object.textEditorModel.getValue(),
+			};
+			this.builtinEditingSessions.set(key, session);
+			return session;
+		} finally {
+			ref.dispose();
+		}
+	}
+
+	private createBuiltinPromptSaveRequest(target: ISaveTargetQuickPickItem): IBuiltinPromptSaveRequest | undefined {
+		const sourceUri = this.currentEditingUri;
+		const promptType = this.currentEditingPromptType;
+		if (!sourceUri || this.currentEditingStorage !== BUILTIN_STORAGE || (promptType !== PromptsType.prompt && promptType !== PromptsType.skill) || !target.folder || target.target === 'cancel') {
+			return;
+		}
+
+		const session = this.builtinEditingSessions.get(sourceUri.toString());
+		if (!session || !this._editorContentChanged) {
+			return;
+		}
+
+		return {
+			target: target.target,
+			folder: target.folder,
+			sourceUri,
+			content: session.model.getValue(),
+			promptType,
+			projectRoot: target.target === 'workspace' ? this.workspaceService.getActiveProjectRoot() : undefined,
+		};
+	}
+
+	private createExistingCustomizationSaveRequest(): IExistingCustomizationSaveRequest | undefined {
+		if (!this._editorContentChanged || this.currentEditingStorage === BUILTIN_STORAGE || !this.currentEditingUri) {
+			return undefined;
+		}
+
+		const model = this.currentModelRef?.object.textEditorModel;
+		if (!model) {
+			return undefined;
+		}
+
+		return {
+			fileUri: this.currentEditingUri,
+			content: model.getValue(),
+			projectRoot: this.currentEditingProjectRoot,
+		};
+	}
+
+	private async saveBuiltinPromptCopy(request: IBuiltinPromptSaveRequest): Promise<void> {
+		let targetUri: URI;
+		if (request.promptType === PromptsType.skill) {
+			// Skills use {skillName}/SKILL.md directory structure
+			const skillFolderName = basename(dirname(request.sourceUri));
+			targetUri = URI.joinPath(request.folder, skillFolderName, basename(request.sourceUri));
+		} else {
+			targetUri = URI.joinPath(request.folder, basename(request.sourceUri));
+		}
+		await this.fileService.createFolder(dirname(targetUri));
+		await this.fileService.writeFile(targetUri, VSBuffer.fromString(request.content));
+		if (request.target === 'workspace' && request.projectRoot) {
+			await this.workspaceService.commitFiles(request.projectRoot, [targetUri]);
+		}
+	}
+
+	private async saveExistingCustomization(request: IExistingCustomizationSaveRequest): Promise<void> {
+		await this.fileService.writeFile(request.fileUri, VSBuffer.fromString(request.content));
+		if (request.projectRoot) {
+			await this.workspaceService.commitFiles(request.projectRoot, [request.fileUri]);
+		}
+	}
+
+	private async pickBuiltinPromptSaveTarget(): Promise<ISaveTargetQuickPickItem | undefined> {
+		const items: ISaveTargetQuickPickItem[] = [];
+		const promptType = this.currentEditingPromptType ?? PromptsType.prompt;
+
+		const workspaceFolder = resolveWorkspaceTargetDirectory(this.workspaceService, promptType);
+		if (workspaceFolder) {
+			items.push({
+				label: localize('workspaceSaveTarget', "Workspace"),
+				description: workspaceFolder.fsPath,
+				target: 'workspace',
+				folder: workspaceFolder,
+			});
+		}
+
+		const userFolder = await resolveUserTargetDirectory(this.promptsService, promptType);
+		if (userFolder) {
+			items.push({
+				label: localize('userSaveTarget', "User"),
+				description: userFolder.fsPath,
+				target: 'user',
+				folder: userFolder,
+			});
+		}
+
+		items.push({
+			label: localize('cancelSaveTarget', "Cancel"),
+			target: 'cancel',
+		});
+
+		return this.quickInputService.pick(items, {
+			canPickMany: false,
+			placeHolder: localize('saveBuiltinCopyPlaceholder', "Select Workspace, User, or Cancel"),
+			matchOnDescription: true,
+		});
+	}
+
+	private async handleEditorActionButton(): Promise<void> {
+		if (this.editorActionButtonInProgress) {
+			return;
+		}
+
+		this.editorActionButtonInProgress = true;
+		this.updateEditorActionButton();
+
+		let backgroundSaveRequest: IBuiltinPromptSaveRequest | undefined;
+		try {
+			if (this.shouldShowBuiltinSaveAction()) {
+				const selection = await this.pickBuiltinPromptSaveTarget();
+				if (!selection || selection.target === 'cancel') {
+					return;
+				}
+
+				backgroundSaveRequest = this.createBuiltinPromptSaveRequest(selection);
+				if (backgroundSaveRequest) {
+					this.telemetryService.publicLog2<CustomizationEditorSaveItemEvent, CustomizationEditorSaveItemClassification>('chatCustomizationEditor.saveItem', {
+						promptType: this.currentEditingPromptType ?? '',
+						storage: String(this.currentEditingStorage ?? ''),
+						saveTarget: selection.target,
+					});
+				}
+			}
+
+			this.goBackToList();
+			if (backgroundSaveRequest) {
+				const saveRequest = backgroundSaveRequest;
+				void this.saveBuiltinPromptCopy(saveRequest).then(() => {
+					void this.listWidget?.refresh();
+				}, error => {
+					console.error('Failed to save built-in override:', error);
+					this.notificationService.warn(saveRequest.target === 'workspace'
+						? localize('saveBuiltinCopyFailedWorkspace', "Could not save the override to the workspace.")
+						: localize('saveBuiltinCopyFailedUser', "Could not save the override to your user folder."));
+				});
+			}
+		} finally {
+			this.editorActionButtonInProgress = false;
+			this.updateEditorActionButton();
+		}
+	}
+
+	private updateEditorActionButton(): void {
+		if (!this.editorActionButton || !this.editorActionButtonIcon) {
+			return;
+		}
+
+		const shouldShowBuiltinSaveAction = this.shouldShowBuiltinSaveAction();
+		this.editorActionButtonIcon.className = `codicon codicon-${shouldShowBuiltinSaveAction ? Codicon.save.id : Codicon.arrowLeft.id} editor-action-button-icon`;
+		this.editorActionButton.disabled = this.editorActionButtonInProgress;
+		this.editorActionButton.setAttribute('aria-label', shouldShowBuiltinSaveAction
+			? localize('saveBuiltinCopyAndChooseLocation', "Save override")
+			: localize('backToList', "Back to list"));
+		this.editorActionButton.title = shouldShowBuiltinSaveAction
+			? localize('saveBuiltinCopyAndChooseLocationTooltip', "Save override (choose Workspace, User, or Cancel)")
+			: localize('backToList', "Back to list");
+	}
+
+	private shouldShowBuiltinSaveAction(): boolean {
+		return this._editorContentChanged
+			&& this.currentEditingStorage === BUILTIN_STORAGE
+			&& (this.currentEditingPromptType === PromptsType.prompt || this.currentEditingPromptType === PromptsType.skill);
+	}
+
+	private resetEditorSaveIndicator(): void {
+		this.editorSaveIndicator.className = 'editor-save-indicator';
+		this.editorSaveIndicator.title = '';
+	}
+
+	private disposeBuiltinEditingSessions(): void {
+		for (const session of this.builtinEditingSessions.values()) {
+			session.model.dispose();
+		}
+		this.builtinEditingSessions.clear();
+	}
+
+	private disposeBuiltinEditingSession(uri: URI): void {
+		const key = uri.toString();
+		const session = this.builtinEditingSessions.get(key);
+		if (!session) {
+			return;
+		}
+
+		session.model.dispose();
+		this.builtinEditingSessions.delete(key);
+	}
+
 	//#region Embedded MCP Server Detail
 
 	private createEmbeddedMcpDetail(): void {
@@ -821,4 +1465,67 @@ export class AICustomizationManagementEditor extends EditorPane {
 	}
 
 	//#endregion
+
+	//#region Embedded Plugin Detail
+
+	private createEmbeddedPluginDetail(): void {
+		if (!this.pluginDetailContainer) {
+			return;
+		}
+
+		// Back button header
+		const detailHeader = DOM.append(this.pluginDetailContainer, $('.editor-header'));
+		const backButton = DOM.append(detailHeader, $('button.editor-back-button'));
+		backButton.setAttribute('aria-label', localize('backToPluginList', "Back to plugins"));
+		const backIconEl = DOM.append(backButton, $(`.codicon.codicon-${Codicon.arrowLeft.id}`));
+		backIconEl.setAttribute('aria-hidden', 'true');
+		this.editorDisposables.add(DOM.addDisposableListener(backButton, 'click', () => {
+			this.goBackFromPluginDetail();
+		}));
+
+		// Container for the plugin editor
+		const editorContainer = DOM.append(this.pluginDetailContainer, $('.plugin-detail-editor-container'));
+
+		// Create the embedded plugin editor pane
+		this.embeddedPluginEditor = this.editorDisposables.add(this.instantiationService.createInstance(AgentPluginEditor, this.group));
+		this.embeddedPluginEditor.create(editorContainer);
+	}
+
+	private async showEmbeddedPluginDetail(item: IAgentPluginItem): Promise<void> {
+		if (!this.embeddedPluginEditor) {
+			return;
+		}
+
+		this.viewMode = 'pluginDetail';
+		this.updateContentVisibility();
+
+		const input = new AgentPluginEditorInput(item);
+		this.pluginDetailDisposables.clear();
+		this.pluginDetailDisposables.add(input);
+
+		try {
+			await this.embeddedPluginEditor.setInput(input, undefined, {}, CancellationToken.None);
+		} catch {
+			this.goBackFromPluginDetail();
+			return;
+		}
+
+		if (this.dimension) {
+			this.layout(this.dimension);
+		}
+	}
+
+	private goBackFromPluginDetail(): void {
+		this.pluginDetailDisposables.clear();
+		this.embeddedPluginEditor?.clearInput();
+		this.viewMode = 'list';
+		this.updateContentVisibility();
+
+		if (this.dimension) {
+			this.layout(this.dimension);
+		}
+		this.pluginListWidget?.focusSearch();
+	}
+
+	//#endregion
 }
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagementEditorInput.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagementEditorInput.ts
index 1ee4543ddacc1..819107dfcebda 100644
--- a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagementEditorInput.ts
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationManagementEditorInput.ts
@@ -22,8 +22,6 @@ export class AICustomizationManagementEditorInput extends EditorInput {
 
 	private static _instance: AICustomizationManagementEditorInput | undefined;
 
-	private _sectionLabel: string | undefined;
-
 	/**
 	 * Gets or creates the singleton instance of this input.
 	 */
@@ -47,20 +45,7 @@ export class AICustomizationManagementEditorInput extends EditorInput {
 	}
 
 	override getName(): string {
-		if (this._sectionLabel) {
-			return localize('aiCustomizationManagementEditorNameWithSection', "Customizations: {0}", this._sectionLabel);
-		}
-		return localize('aiCustomizationManagementEditorName', "Customizations");
-	}
-
-	/**
-	 * Updates the section label shown in the editor tab title.
-	 */
-	setSectionLabel(label: string): void {
-		if (this._sectionLabel !== label) {
-			this._sectionLabel = label;
-			this._onDidChangeLabel.fire();
-		}
+		return localize('aiCustomizationManagementEditorName', "Chat Customizations");
 	}
 
 	override getIcon(): ThemeIcon {
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationWorkspaceService.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationWorkspaceService.ts
index 450961e960144..dea000c208606 100644
--- a/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationWorkspaceService.ts
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/aiCustomizationWorkspaceService.ts
@@ -3,17 +3,19 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { derived, IObservable, observableFromEventOpts } from '../../../../../base/common/observable.js';
+import { constObservable, derived, IObservable, observableFromEventOpts } from '../../../../../base/common/observable.js';
 import { URI } from '../../../../../base/common/uri.js';
+import { CancellationToken } from '../../../../../base/common/cancellation.js';
 import { IWorkspaceContextService } from '../../../../../platform/workspace/common/workspace.js';
-import { IAICustomizationWorkspaceService, AICustomizationManagementSection } from '../../common/aiCustomizationWorkspaceService.js';
+import { IAICustomizationWorkspaceService, AICustomizationManagementSection, IStorageSourceFilter } from '../../common/aiCustomizationWorkspaceService.js';
 import { InstantiationType, registerSingleton } from '../../../../../platform/instantiation/common/extensions.js';
+import { IChatPromptSlashCommand, IPromptsService, PromptsStorage } from '../../common/promptSyntax/service/promptsService.js';
 import { ICommandService } from '../../../../../platform/commands/common/commands.js';
 import { PromptsType } from '../../common/promptSyntax/promptTypes.js';
 import {
 	GENERATE_AGENT_COMMAND_ID,
 	GENERATE_HOOK_COMMAND_ID,
-	GENERATE_INSTRUCTION_COMMAND_ID,
+	GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID,
 	GENERATE_PROMPT_COMMAND_ID,
 	GENERATE_SKILL_COMMAND_ID,
 } from '../actions/chatActions.js';
@@ -26,6 +28,7 @@ class AICustomizationWorkspaceService implements IAICustomizationWorkspaceServic
 	constructor(
 		@IWorkspaceContextService private readonly workspaceContextService: IWorkspaceContextService,
 		@ICommandService private readonly commandService: ICommandService,
+		@IPromptsService private readonly promptsService: IPromptsService,
 	) {
 		const workspaceFolders = observableFromEventOpts(
 			{ owner: this },
@@ -50,19 +53,36 @@ class AICustomizationWorkspaceService implements IAICustomizationWorkspaceServic
 		AICustomizationManagementSection.Prompts,
 		AICustomizationManagementSection.Hooks,
 		AICustomizationManagementSection.McpServers,
+		AICustomizationManagementSection.Plugins,
 	];
 
-	readonly preferManualCreation = false;
+	private static readonly _defaultFilter: IStorageSourceFilter = {
+		sources: [PromptsStorage.local, PromptsStorage.user, PromptsStorage.extension, PromptsStorage.plugin],
+	};
+
+	getStorageSourceFilter(_type: PromptsType): IStorageSourceFilter {
+		return AICustomizationWorkspaceService._defaultFilter;
+	}
+
+	readonly isSessionsWindow = false;
+
+	readonly hasOverrideProjectRoot = constObservable(false);
+	setOverrideProjectRoot(_root: URI): void { }
+	clearOverrideProjectRoot(): void { }
 
 	async commitFiles(_projectRoot: URI, _fileUris: URI[]): Promise<void> {
 		// No-op in core VS Code.
 	}
 
+	async deleteFiles(_projectRoot: URI, _fileUris: URI[]): Promise<void> {
+		// No-op in core VS Code.
+	}
+
 	async generateCustomization(type: PromptsType): Promise<void> {
 		const commandIds: Partial<Record<PromptsType, string>> = {
 			[PromptsType.agent]: GENERATE_AGENT_COMMAND_ID,
 			[PromptsType.skill]: GENERATE_SKILL_COMMAND_ID,
-			[PromptsType.instructions]: GENERATE_INSTRUCTION_COMMAND_ID,
+			[PromptsType.instructions]: GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID,
 			[PromptsType.prompt]: GENERATE_PROMPT_COMMAND_ID,
 			[PromptsType.hook]: GENERATE_HOOK_COMMAND_ID,
 		};
@@ -71,6 +91,10 @@ class AICustomizationWorkspaceService implements IAICustomizationWorkspaceServic
 			await this.commandService.executeCommand(commandId);
 		}
 	}
+
+	async getFilteredPromptSlashCommands(token: CancellationToken): Promise<readonly IChatPromptSlashCommand[]> {
+		return this.promptsService.getPromptSlashCommands(token);
+	}
 }
 
 registerSingleton(IAICustomizationWorkspaceService, AICustomizationWorkspaceService, InstantiationType.Delayed);
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/customizationCreatorService.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/customizationCreatorService.ts
index e8188abf63b04..9971aed24d069 100644
--- a/src/vs/workbench/contrib/chat/browser/aiCustomization/customizationCreatorService.ts
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/customizationCreatorService.ts
@@ -11,6 +11,7 @@ import { PromptsType } from '../../common/promptSyntax/promptTypes.js';
 import { getPromptFileDefaultLocations } from '../../common/promptSyntax/config/promptFileLocations.js';
 import { IPromptsService, PromptsStorage } from '../../common/promptSyntax/service/promptsService.js';
 import { URI } from '../../../../../base/common/uri.js';
+import { isEqualOrParent } from '../../../../../base/common/resources.js';
 import { ICommandService } from '../../../../../platform/commands/common/commands.js';
 import { IQuickInputService } from '../../../../../platform/quickinput/common/quickInput.js';
 import { localize } from '../../../../../nls.js';
@@ -58,7 +59,10 @@ export class CustomizationCreatorService {
 		// directory and have those changes tracked.
 
 		// Capture project root BEFORE opening new chat (which may change active session)
-		const targetDir = this.resolveTargetDirectory(type);
+		const targetDir = await this.resolveTargetDirectoryWithPicker(type);
+		if (targetDir === null) {
+			return; // User cancelled the picker
+		}
 		const systemInstructions = buildAgentInstructions(type, targetDir, trimmedName);
 		const userMessage = buildUserMessage(type, targetDir, trimmedName);
 
@@ -95,6 +99,58 @@ export class CustomizationCreatorService {
 		return resolveWorkspaceTargetDirectory(this.workspaceService, type);
 	}
 
+	/**
+	 * Resolves the workspace directory for a new customization file.
+	 * If multiple local source folders exist, shows a picker to let the user choose.
+	 *
+	 * @returns the resolved URI, `undefined` when no folder is available,
+	 *          or `null` when the user cancelled the picker.
+	 */
+	private async resolveTargetDirectoryWithPicker(type: PromptsType): Promise<URI | undefined | null> {
+		const allFolders = await this.promptsService.getSourceFolders(type);
+		const projectRoot = this.workspaceService.getActiveProjectRoot();
+
+		// Filter to only workspace-scoped folders (under the active project root).
+		// Don't rely on storage tags — tilde-expanded user paths can be tagged local.
+		// Deduplicate by URI to avoid inflated counts and duplicate picker entries.
+		const seen = new Set<string>();
+		const workspaceFolders = projectRoot
+			? allFolders.filter(f => {
+				if (!isEqualOrParent(f.uri, projectRoot)) {
+					return false;
+				}
+				const key = f.uri.toString();
+				if (seen.has(key)) {
+					return false;
+				}
+				seen.add(key);
+				return true;
+			})
+			: [];
+
+		if (workspaceFolders.length === 0) {
+			// No workspace folders — fall back to the existing resolution logic
+			return this.resolveTargetDirectory(type);
+		}
+
+		if (workspaceFolders.length === 1) {
+			return workspaceFolders[0].uri;
+		}
+
+		// Multiple directories — ask the user which one to use
+		const items = workspaceFolders.map(folder => ({
+			label: this.promptsService.getPromptLocationLabel(folder),
+			description: folder.uri.fsPath,
+			uri: folder.uri,
+		}));
+
+		const picked = await this.quickInputService.pick(items, {
+			placeHolder: localize('selectTargetDirectory', "Select a directory for the new customization file"),
+		});
+
+		return picked?.uri ?? null;
+	}
+
 	/**
 	 * Resolves the user-level directory for a new customization file.
 	 */
@@ -121,8 +177,13 @@ export function resolveWorkspaceTargetDirectory(workspaceService: IAICustomizati
 
 /**
  * Resolves the user-level directory for a new customization file.
+ * Delegates to IPromptsService.getSourceFolders() which returns the appropriate
+ * user root (VS Code profile in core, ~/.copilot in sessions).
  */
-export async function resolveUserTargetDirectory(promptsService: IPromptsService, type: PromptsType): Promise<URI | undefined> {
+export async function resolveUserTargetDirectory(
+	promptsService: IPromptsService,
+	type: PromptsType,
+): Promise<URI | undefined> {
 	const folders = await promptsService.getSourceFolders(type);
 	const userFolder = folders.find(f => f.storage === PromptsStorage.user);
 	return userFolder?.uri;
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/customizationGroupHeaderRenderer.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/customizationGroupHeaderRenderer.ts
new file mode 100644
index 0000000000000..2ad6d9934473b
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/customizationGroupHeaderRenderer.ts
@@ -0,0 +1,99 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as DOM from '../../../../../base/browser/dom.js';
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { Codicon } from '../../../../../base/common/codicons.js';
+import { ThemeIcon } from '../../../../../base/common/themables.js';
+import { IListRenderer } from '../../../../../base/browser/ui/list/list.js';
+import { IHoverService } from '../../../../../platform/hover/browser/hover.js';
+
+const $ = DOM.$;
+
+export const CUSTOMIZATION_GROUP_HEADER_HEIGHT = 36;
+export const CUSTOMIZATION_GROUP_HEADER_HEIGHT_WITH_SEPARATOR = 40;
+
+/**
+ * Common shape for a collapsible group header entry used in the
+ * MCP-server and plugin list widgets.
+ */
+export interface ICustomizationGroupHeaderEntry {
+	readonly type: 'group-header';
+	readonly id: string;
+	readonly label: string;
+	readonly icon: ThemeIcon;
+	readonly count: number;
+	readonly isFirst: boolean;
+	readonly description: string;
+	collapsed: boolean;
+}
+
+interface ICustomizationGroupHeaderTemplateData {
+	readonly container: HTMLElement;
+	readonly chevron: HTMLElement;
+	readonly icon: HTMLElement;
+	readonly label: HTMLElement;
+	readonly count: HTMLElement;
+	readonly infoIcon: HTMLElement;
+	readonly disposables: DisposableStore;
+	readonly elementDisposables: DisposableStore;
+}
+
+/**
+ * Shared renderer for collapsible group headers in the AI Customization
+ * list widgets (MCP servers, plugins, etc.).
+ */
+export class CustomizationGroupHeaderRenderer<T extends ICustomizationGroupHeaderEntry> implements IListRenderer<T, ICustomizationGroupHeaderTemplateData> {
+
+	constructor(
+		readonly templateId: string,
+		private readonly hoverService: IHoverService,
+	) { }
+
+	renderTemplate(container: HTMLElement): ICustomizationGroupHeaderTemplateData {
+		const disposables = new DisposableStore();
+		const elementDisposables = new DisposableStore();
+		container.classList.add('ai-customization-group-header');
+
+		const chevron = DOM.append(container, $('.group-chevron'));
+		const icon = DOM.append(container, $('.group-icon'));
+		const labelGroup = DOM.append(container, $('.group-label-group'));
+		const label = DOM.append(labelGroup, $('.group-label'));
+		const infoIcon = DOM.append(labelGroup, $('.group-info'));
+		infoIcon.classList.add(...ThemeIcon.asClassNameArray(Codicon.info));
+		const count = DOM.append(container, $('.group-count'));
+
+		return { container, chevron, icon, label, count, infoIcon, disposables, elementDisposables };
+	}
+
+	renderElement(element: T, _index: number, templateData: ICustomizationGroupHeaderTemplateData): void {
+		templateData.elementDisposables.clear();
+
+		templateData.chevron.className = 'group-chevron';
+		templateData.chevron.classList.add(...ThemeIcon.asClassNameArray(element.collapsed ? Codicon.chevronRight : Codicon.chevronDown));
+
+		templateData.icon.className = 'group-icon';
+		templateData.icon.classList.add(...ThemeIcon.asClassNameArray(element.icon));
+
+		templateData.label.textContent = element.label;
+		templateData.count.textContent = `${element.count}`;
+
+		templateData.elementDisposables.add(this.hoverService.setupDelayedHover(templateData.infoIcon, () => ({
+			content: element.description,
+			appearance: {
+				compact: true,
+				skipFadeInAnimation: true,
+			}
+		})));
+
+		templateData.container.classList.toggle('collapsed', element.collapsed);
+		templateData.container.classList.toggle('has-previous-group', !element.isFirst);
+	}
+
+	disposeTemplate(templateData: ICustomizationGroupHeaderTemplateData): void {
+		templateData.elementDisposables.dispose();
+		templateData.disposables.dispose();
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/mcpListWidget.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/mcpListWidget.ts
index 6e6ed17aabefc..ffaecde844331 100644
--- a/src/vs/workbench/contrib/chat/browser/aiCustomization/mcpListWidget.ts
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/mcpListWidget.ts
@@ -17,6 +17,7 @@ import { Button } from '../../../../../base/browser/ui/button/button.js';
 import { defaultButtonStyles, defaultInputBoxStyles } from '../../../../../platform/theme/browser/defaultStyles.js';
 import { ICommandService } from '../../../../../platform/commands/common/commands.js';
 import { IMcpWorkbenchService, IWorkbenchMcpServer, McpConnectionState, McpServerInstallState, IMcpService } from '../../../../contrib/mcp/common/mcpTypes.js';
+import { isContributionDisabled } from '../../common/enablement.js';
 import { McpCommandIds } from '../../../../contrib/mcp/common/mcpCommandIds.js';
 import { autorun } from '../../../../../base/common/observable.js';
 import { IOpenerService } from '../../../../../platform/opener/common/opener.js';
@@ -28,28 +29,21 @@ import { Delayer } from '../../../../../base/common/async.js';
 import { IAction, Separator } from '../../../../../base/common/actions.js';
 import { getContextMenuActions } from '../../../../contrib/mcp/browser/mcpServerActions.js';
 import { LocalMcpServerScope } from '../../../../services/mcp/common/mcpWorkbenchManagementService.js';
-import { workspaceIcon, userIcon } from './aiCustomizationIcons.js';
+import { workspaceIcon, userIcon, mcpServerIcon, builtinIcon } from './aiCustomizationIcons.js';
+import { formatDisplayName, truncateToFirstSentence } from './aiCustomizationListWidget.js';
 import { IHoverService } from '../../../../../platform/hover/browser/hover.js';
+import { IAICustomizationWorkspaceService } from '../../common/aiCustomizationWorkspaceService.js';
+import { CustomizationGroupHeaderRenderer, ICustomizationGroupHeaderEntry, CUSTOMIZATION_GROUP_HEADER_HEIGHT, CUSTOMIZATION_GROUP_HEADER_HEIGHT_WITH_SEPARATOR } from './customizationGroupHeaderRenderer.js';
 
 const $ = DOM.$;
 
-const MCP_ITEM_HEIGHT = 60;
-const MCP_GROUP_HEADER_HEIGHT = 32;
-const MCP_GROUP_HEADER_HEIGHT_WITH_SEPARATOR = 40;
+const MCP_ITEM_HEIGHT = 36;
 
 /**
  * Represents a collapsible group header in the MCP server list.
  */
-interface IMcpGroupHeaderEntry {
-	readonly type: 'group-header';
-	readonly id: string;
-	readonly scope: LocalMcpServerScope;
-	readonly label: string;
-	readonly icon: ThemeIcon;
-	readonly count: number;
-	readonly isFirst: boolean;
-	readonly description: string;
-	collapsed: boolean;
+interface IMcpGroupHeaderEntry extends ICustomizationGroupHeaderEntry {
+	readonly scope: LocalMcpServerScope | 'builtin';
 }
 
 /**
@@ -60,7 +54,17 @@ interface IMcpServerItemEntry {
 	readonly server: IWorkbenchMcpServer;
 }
 
-type IMcpListEntry = IMcpGroupHeaderEntry | IMcpServerItemEntry;
+/**
+ * Represents a built-in MCP server provided by an extension.
+ */
+interface IMcpBuiltinItemEntry {
+	readonly type: 'builtin-item';
+	readonly id: string;
+	readonly label: string;
+	readonly description: string;
+}
+
+type IMcpListEntry = IMcpGroupHeaderEntry | IMcpServerItemEntry | IMcpBuiltinItemEntry;
 
 /**
  * Delegate for the MCP server list.
@@ -68,7 +72,10 @@ type IMcpListEntry = IMcpGroupHeaderEntry | IMcpServerItemEntry;
 class McpServerItemDelegate implements IListVirtualDelegate<IMcpListEntry> {
 	getHeight(element: IMcpListEntry): number {
 		if (element.type === 'group-header') {
-			return element.isFirst ? MCP_GROUP_HEADER_HEIGHT : MCP_GROUP_HEADER_HEIGHT_WITH_SEPARATOR;
+			return element.isFirst ? CUSTOMIZATION_GROUP_HEADER_HEIGHT : CUSTOMIZATION_GROUP_HEADER_HEIGHT_WITH_SEPARATOR;
+		}
+		if (element.type === 'server-item' && element.server.gallery && !element.server.local) {
+			return 62;
 		}
 		return MCP_ITEM_HEIGHT;
 	}
@@ -77,81 +84,17 @@ class McpServerItemDelegate implements IListVirtualDelegate<IMcpListEntry> {
 		if (element.type === 'group-header') {
 			return 'mcpGroupHeader';
 		}
+		if (element.type === 'builtin-item') {
+			return 'mcpServerItem';
+		}
 		const server = element.server;
 		return server.gallery && !server.local ? 'mcpGalleryItem' : 'mcpServerItem';
 	}
 }
 
-interface IMcpGroupHeaderTemplateData {
-	readonly container: HTMLElement;
-	readonly chevron: HTMLElement;
-	readonly icon: HTMLElement;
-	readonly label: HTMLElement;
-	readonly count: HTMLElement;
-	readonly infoIcon: HTMLElement;
-	readonly disposables: DisposableStore;
-	readonly elementDisposables: DisposableStore;
-}
-
-/**
- * Renderer for collapsible group headers (Workspace, User).
- */
-class McpGroupHeaderRenderer implements IListRenderer<IMcpGroupHeaderEntry, IMcpGroupHeaderTemplateData> {
-	readonly templateId = 'mcpGroupHeader';
-
-	constructor(
-		private readonly hoverService: IHoverService,
-	) { }
-
-	renderTemplate(container: HTMLElement): IMcpGroupHeaderTemplateData {
-		const disposables = new DisposableStore();
-		const elementDisposables = new DisposableStore();
-		container.classList.add('ai-customization-group-header');
-
-		const chevron = DOM.append(container, $('.group-chevron'));
-		const icon = DOM.append(container, $('.group-icon'));
-		const labelGroup = DOM.append(container, $('.group-label-group'));
-		const label = DOM.append(labelGroup, $('.group-label'));
-		const infoIcon = DOM.append(labelGroup, $('.group-info'));
-		infoIcon.classList.add(...ThemeIcon.asClassNameArray(Codicon.info));
-		const count = DOM.append(container, $('.group-count'));
-
-		return { container, chevron, icon, label, count, infoIcon, disposables, elementDisposables };
-	}
-
-	renderElement(element: IMcpGroupHeaderEntry, _index: number, templateData: IMcpGroupHeaderTemplateData): void {
-		templateData.elementDisposables.clear();
-
-		templateData.chevron.className = 'group-chevron';
-		templateData.chevron.classList.add(...ThemeIcon.asClassNameArray(element.collapsed ? Codicon.chevronRight : Codicon.chevronDown));
-
-		templateData.icon.className = 'group-icon';
-		templateData.icon.classList.add(...ThemeIcon.asClassNameArray(element.icon));
-
-		templateData.label.textContent = element.label;
-		templateData.count.textContent = `${element.count}`;
-
-		templateData.elementDisposables.add(this.hoverService.setupDelayedHover(templateData.infoIcon, () => ({
-			content: element.description,
-			appearance: {
-				compact: true,
-				skipFadeInAnimation: true,
-			}
-		})));
-
-		templateData.container.classList.toggle('collapsed', element.collapsed);
-		templateData.container.classList.toggle('has-previous-group', !element.isFirst);
-	}
-
-	disposeTemplate(templateData: IMcpGroupHeaderTemplateData): void {
-		templateData.elementDisposables.dispose();
-		templateData.disposables.dispose();
-	}
-}
-
 interface IMcpServerItemTemplateData {
 	readonly container: HTMLElement;
-	readonly icon: HTMLElement;
+	readonly typeIcon: HTMLElement;
 	readonly name: HTMLElement;
 	readonly description: HTMLElement;
 	readonly status: HTMLElement;
@@ -161,18 +104,19 @@ interface IMcpServerItemTemplateData {
 /**
  * Renderer for local MCP server list items.
  */
-class McpServerItemRenderer implements IListRenderer<IMcpServerItemEntry, IMcpServerItemTemplateData> {
+class McpServerItemRenderer implements IListRenderer<IMcpServerItemEntry | IMcpBuiltinItemEntry, IMcpServerItemTemplateData> {
 	readonly templateId = 'mcpServerItem';
 
 	constructor(
 		@IMcpService private readonly mcpService: IMcpService,
+		@IAICustomizationWorkspaceService private readonly workspaceService: IAICustomizationWorkspaceService,
 	) { }
 
 	renderTemplate(container: HTMLElement): IMcpServerItemTemplateData {
 		container.classList.add('mcp-server-item');
 
-		const icon = DOM.append(container, $('.mcp-server-icon'));
-		icon.classList.add(...ThemeIcon.asClassNameArray(Codicon.server));
+		const typeIcon = DOM.append(container, $('.mcp-server-icon'));
+		typeIcon.classList.add(...ThemeIcon.asClassNameArray(mcpServerIcon));
 
 		const details = DOM.append(container, $('.mcp-server-details'));
 		const name = DOM.append(details, $('.mcp-server-name'));
@@ -180,26 +124,59 @@ class McpServerItemRenderer implements IListRenderer<IMcpServerItemEntry, IMcpSe
 
 		const status = DOM.append(container, $('.mcp-server-status'));
 
-		return { container, icon, name, description, status, disposables: new DisposableStore() };
+		return { container, typeIcon, name, description, status, disposables: new DisposableStore() };
 	}
 
-	renderElement(element: IMcpServerItemEntry, index: number, templateData: IMcpServerItemTemplateData): void {
+	renderElement(element: IMcpServerItemEntry | IMcpBuiltinItemEntry, index: number, templateData: IMcpServerItemTemplateData): void {
 		templateData.disposables.clear();
 
-		templateData.name.textContent = element.server.label;
-		templateData.description.textContent = element.server.description || '';
+		if (element.type === 'builtin-item') {
+			templateData.container.classList.add('builtin');
+			templateData.name.textContent = formatDisplayName(element.label);
+			if (element.description) {
+				templateData.description.textContent = truncateToFirstSentence(element.description);
+				templateData.description.style.display = '';
+			} else {
+				templateData.description.style.display = 'none';
+			}
+			templateData.status.style.display = 'none';
+			return;
+		}
+
+		templateData.container.classList.remove('builtin');
+		templateData.name.textContent = formatDisplayName(element.server.label);
+		if (element.server.description) {
+			templateData.description.textContent = truncateToFirstSentence(element.server.description);
+			templateData.description.style.display = '';
+		} else {
+			templateData.description.style.display = 'none';
+		}
 
 		// Find the server from IMcpService to get connection state
 		const server = this.mcpService.servers.get().find(s => s.definition.id === element.server.id);
 		templateData.disposables.add(autorun(reader => {
+			const disabled = server ? isContributionDisabled(server.enablement.read(reader)) : false;
 			const connectionState = server?.connectionState.read(reader);
-			this.updateStatus(templateData.status, connectionState?.state);
+			templateData.container.classList.toggle('disabled', disabled);
+			this.updateStatus(templateData.status, disabled ? 'disabled' : connectionState?.state);
 		}));
 	}
 
-	private updateStatus(statusElement: HTMLElement, state: McpConnectionState.Kind | undefined): void {
+	private updateStatus(statusElement: HTMLElement, state: McpConnectionState.Kind | 'disabled' | undefined): void {
 		statusElement.className = 'mcp-server-status';
 
+		if (this.workspaceService.isSessionsWindow) {
+			// In sessions window, CLI manages MCP servers — hide status
+			statusElement.style.display = 'none';
+			return;
+		}
+
+		statusElement.style.display = '';
+		if (state === 'disabled') {
+			statusElement.textContent = localize('disabled', "Disabled");
+			statusElement.classList.add('disabled');
+			return;
+		}
 		switch (state) {
 			case McpConnectionState.Kind.Running:
 				statusElement.textContent = localize('running', "Running");
@@ -228,7 +205,6 @@ class McpServerItemRenderer implements IListRenderer<IMcpServerItemEntry, IMcpSe
 
 interface IMcpGalleryItemTemplateData {
 	readonly container: HTMLElement;
-	readonly icon: HTMLElement;
 	readonly name: HTMLElement;
 	readonly publisher: HTMLElement;
 	readonly description: HTMLElement;
@@ -248,25 +224,23 @@ class McpGalleryItemRenderer implements IListRenderer<IMcpServerItemEntry, IMcpG
 	) { }
 
 	renderTemplate(container: HTMLElement): IMcpGalleryItemTemplateData {
-		container.classList.add('mcp-server-item', 'mcp-gallery-item');
-
-		const icon = DOM.append(container, $('.mcp-server-icon'));
-		icon.classList.add(...ThemeIcon.asClassNameArray(Codicon.server));
-
-		const details = DOM.append(container, $('.mcp-server-details'));
-		const nameRow = DOM.append(details, $('.mcp-gallery-name-row'));
-		const name = DOM.append(nameRow, $('.mcp-server-name'));
-		const publisher = DOM.append(nameRow, $('.mcp-gallery-publisher'));
-		const description = DOM.append(details, $('.mcp-server-description'));
-
-		const actionContainer = DOM.append(container, $('.mcp-gallery-action'));
+		container.classList.add('mcp-server-item', 'mcp-gallery-item', 'extension-list-item');
+		const details = DOM.append(container, $('.details'));
+		const headerContainer = DOM.append(details, $('.header-container'));
+		const header = DOM.append(headerContainer, $('.header'));
+		const name = DOM.append(header, $('span.name'));
+		const description = DOM.append(details, $('.description.ellipsis'));
+		const footer = DOM.append(details, $('.footer'));
+		const publisherContainer = DOM.append(footer, $('.publisher-container'));
+		const publisher = DOM.append(publisherContainer, $('span.publisher-name'));
+		const actionContainer = DOM.append(footer, $('.mcp-gallery-action'));
 		const installButton = new Button(actionContainer, { ...defaultButtonStyles, supportIcons: true });
 		installButton.element.classList.add('mcp-gallery-install-button');
 
 		const templateDisposables = new DisposableStore();
 		templateDisposables.add(installButton);
 
-		return { container, icon, name, publisher, description, installButton, elementDisposables: new DisposableStore(), templateDisposables };
+		return { container, name, publisher, description, installButton, elementDisposables: new DisposableStore(), templateDisposables };
 	}
 
 	renderElement(element: IMcpServerItemEntry, _index: number, templateData: IMcpGalleryItemTemplateData): void {
@@ -346,7 +320,7 @@ export class McpListWidget extends Disposable {
 	private galleryServers: IWorkbenchMcpServer[] = [];
 	private searchQuery: string = '';
 	private browseMode: boolean = false;
-	private readonly collapsedGroups = new Set<LocalMcpServerScope>();
+	private readonly collapsedGroups = new Set<string>();
 	private galleryCts: CancellationTokenSource | undefined;
 	private readonly delayedFilter = new Delayer<void>(200);
 	private readonly delayedGallerySearch = new Delayer<void>(400);
@@ -458,7 +432,7 @@ export class McpListWidget extends Disposable {
 
 		// Create list
 		const delegate = new McpServerItemDelegate();
-		const groupHeaderRenderer = new McpGroupHeaderRenderer(this.hoverService);
+		const groupHeaderRenderer = new CustomizationGroupHeaderRenderer<IMcpGroupHeaderEntry>('mcpGroupHeader', this.hoverService);
 		const localRenderer = this.instantiationService.createInstance(McpServerItemRenderer);
 		const galleryRenderer = new McpGalleryItemRenderer(this.mcpWorkbenchService);
 
@@ -477,6 +451,9 @@ export class McpListWidget extends Disposable {
 						if (element.type === 'group-header') {
 							return localize('mcpGroupAriaLabel', "{0}, {1} items, {2}", element.label, element.count, element.collapsed ? localize('collapsed', "collapsed") : localize('expanded', "expanded"));
 						}
+						if (element.type === 'builtin-item') {
+							return element.label;
+						}
 						return element.server.label;
 					},
 					getWidgetAriaLabel() {
@@ -486,7 +463,13 @@ export class McpListWidget extends Disposable {
 				openOnSingleClick: true,
 				identityProvider: {
 					getId(element: IMcpListEntry) {
-						return element.type === 'group-header' ? element.id : element.server.id;
+						if (element.type === 'group-header') {
+							return element.id;
+						}
+						if (element.type === 'builtin-item') {
+							return element.id;
+						}
+						return element.server.id;
 					}
 				}
 			}
@@ -496,9 +479,10 @@ export class McpListWidget extends Disposable {
 			if (e.element) {
 				if (e.element.type === 'group-header') {
 					this.toggleGroup(e.element);
-				} else {
+				} else if (e.element.type === 'server-item') {
 					this._onDidSelectServer.fire(e.element.server);
 				}
+				// builtin-item: no action on click (read-only)
 			}
 		}));
 
@@ -619,8 +603,14 @@ export class McpListWidget extends Disposable {
 			this.filteredServers = [...this.mcpWorkbenchService.local];
 		}
 
+		// Find extension-provided servers not in the local list (e.g. GitHub MCP)
+		const localIds = new Set(this.filteredServers.map(s => s.id));
+		const builtinServers = this.mcpService.servers.get()
+			.filter(s => !localIds.has(s.definition.id))
+			.filter(s => !query || s.definition.label.toLowerCase().includes(query));
+
 		// Show empty state only when there are no servers at all (not when filtered to empty)
-		if (this.filteredServers.length === 0) {
+		if (this.filteredServers.length === 0 && builtinServers.length === 0) {
 			this.emptyContainer.style.display = 'flex';
 			this.listContainer.style.display = 'none';
 
@@ -681,6 +671,32 @@ export class McpListWidget extends Disposable {
 			isFirst = false;
 		}
 
+		// Add built-in / extension-provided servers
+		if (builtinServers.length > 0) {
+			const collapsed = this.collapsedGroups.has('builtin');
+			entries.push({
+				type: 'group-header',
+				id: 'mcp-group-builtin',
+				scope: 'builtin',
+				label: localize('builtInGroup', "Built-in"),
+				icon: builtinIcon,
+				count: builtinServers.length,
+				isFirst,
+				description: localize('builtInGroupDescription', "MCP servers built into VS Code. These are available automatically."),
+				collapsed,
+			});
+			if (!collapsed) {
+				for (const server of builtinServers) {
+					entries.push({
+						type: 'builtin-item',
+						id: `builtin-${server.definition.id}`,
+						label: server.definition.label,
+						description: '',
+					});
+				}
+			}
+		}
+
 		this.displayEntries = entries;
 		this.list.splice(0, this.list.length, this.displayEntries);
 	}
@@ -701,14 +717,28 @@ export class McpListWidget extends Disposable {
 	 * Layouts the widget.
 	 */
 	layout(height: number, width: number): void {
-		const sectionFooterHeight = this.sectionHeader.offsetHeight || 100;
-		const searchBarHeight = this.searchAndButtonContainer.offsetHeight || 40;
+		const sectionFooterHeight = this.sectionHeader.offsetHeight || 0;
+		const searchBarHeight = this.searchAndButtonContainer.offsetHeight || 52;
 		const backLinkHeight = this.browseMode ? (this.backLink.offsetHeight || 28) : 0;
-		const margins = 12;
-		const listHeight = height - sectionFooterHeight - searchBarHeight - backLinkHeight - margins;
+		const listHeight = height - sectionFooterHeight - searchBarHeight - backLinkHeight;
 
 		this.listContainer.style.height = `${Math.max(0, listHeight)}px`;
 		this.list.layout(Math.max(0, listHeight), width);
+
+		// Re-layout once after footer renders if we used a zero fallback
+		if (sectionFooterHeight === 0) {
+			DOM.getWindow(this.listContainer).requestAnimationFrame(() => {
+				if (this._store.isDisposed) {
+					return;
+				}
+				const actualFooterHeight = this.sectionHeader.offsetHeight;
+				if (actualFooterHeight > 0) {
+					const correctedHeight = height - actualFooterHeight - searchBarHeight - backLinkHeight;
+					this.listContainer.style.height = `${Math.max(0, correctedHeight)}px`;
+					this.list.layout(Math.max(0, correctedHeight), width);
+				}
+			});
+		}
 	}
 
 	/**
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/media/aiCustomizationManagement.css b/src/vs/workbench/contrib/chat/browser/aiCustomization/media/aiCustomizationManagement.css
index eb634aa456255..938c539fb4e5d 100644
--- a/src/vs/workbench/contrib/chat/browser/aiCustomization/media/aiCustomizationManagement.css
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/media/aiCustomizationManagement.css
@@ -31,7 +31,65 @@
 	overflow: hidden;
 }
 
+/* Folder picker footer (sessions window only) */
+.ai-customization-management-editor .sidebar-folder-picker {
+	flex-shrink: 0;
+	display: flex;
+	align-items: center;
+	gap: 2px;
+	padding: 6px 4px;
+	border-top: 1px solid var(--vscode-sideBarSectionHeader-border, transparent);
+}
+
+.ai-customization-management-editor .folder-picker-button {
+	display: flex;
+	align-items: center;
+	gap: 6px;
+	flex: 1;
+	min-width: 0;
+	padding: 4px 6px;
+	border: none;
+	border-radius: 4px;
+	background: transparent;
+	color: var(--vscode-descriptionForeground);
+	cursor: pointer;
+	font-size: 11px;
+}
+
+.ai-customization-management-editor .folder-picker-button:hover {
+	background-color: var(--vscode-list-hoverBackground);
+}
+
+.ai-customization-management-editor .folder-picker-icon {
+	flex-shrink: 0;
+	font-size: 14px;
+}
+
+.ai-customization-management-editor .folder-picker-label {
+	overflow: hidden;
+	text-overflow: ellipsis;
+	white-space: nowrap;
+}
 
+.ai-customization-management-editor .folder-picker-clear {
+	flex-shrink: 0;
+	display: flex;
+	align-items: center;
+	justify-content: center;
+	width: 22px;
+	height: 22px;
+	padding: 0;
+	border: none;
+	border-radius: 4px;
+	background: transparent;
+	color: var(--vscode-descriptionForeground);
+	cursor: pointer;
+	font-size: 12px;
+}
+
+.ai-customization-management-editor .folder-picker-clear:hover {
+	background-color: var(--vscode-list-hoverBackground);
+}
 
 /* Section list items */
 .ai-customization-management-editor .section-list-item {
@@ -108,7 +166,7 @@
 	align-items: center;
 	gap: 8px;
 	flex-shrink: 0;
-	margin: 6px 0px;
+	padding: 6px 0;
 }
 
 .ai-customization-list-widget .list-search-container,
@@ -137,7 +195,8 @@
 
 .ai-customization-list-widget .list-container {
 	flex: 1;
-	overflow: hidden;
+	min-height: 0;
+	overflow: auto;
 }
 
 .ai-customization-list-widget .list-empty-message {
@@ -193,10 +252,8 @@
 	border-radius: 4px;
 }
 
-/* Separator line above non-first group headers */
+/* Spacing above non-first group headers */
 .ai-customization-group-header.has-previous-group {
-	border-top: 1px solid var(--vscode-sideBarSectionHeader-border, var(--vscode-panel-border));
-	margin-top: 4px;
 	padding-top: 12px;
 }
 
@@ -249,8 +306,8 @@
 	flex-shrink: 0;
 	font-size: 10px;
 	font-weight: 500;
-	background-color: var(--vscode-badge-background);
-	color: var(--vscode-badge-foreground);
+	background-color: var(--vscode-list-inactiveSelectionBackground);
+	color: var(--vscode-list-inactiveSelectionForeground, var(--vscode-foreground));
 	padding: 0 5px;
 	border-radius: 8px;
 	min-width: 14px;
@@ -290,7 +347,6 @@
 	padding: 6px 8px 6px 24px;
 	cursor: pointer;
 	border-radius: 4px;
-	margin: 2px 0;
 	min-height: 32px;
 }
 
@@ -340,6 +396,17 @@
 	opacity: 0.6;
 }
 
+.ai-customization-list-item .item-type-icon {
+	flex-shrink: 0;
+	width: 16px;
+	height: 16px;
+	display: flex;
+	align-items: center;
+	justify-content: center;
+	opacity: 0.8;
+	font-size: 14px;
+}
+
 .ai-customization-list-item .item-text {
 	display: flex;
 	flex-direction: column;
@@ -486,12 +553,11 @@
 .ai-customization-overview .overview-section .section-count {
 	flex-shrink: 0;
 	font-size: 9px;
-	font-weight: 600;
+	font-weight: 500;
 	padding: 1px 5px;
-	background-color: var(--vscode-badge-background);
-	color: var(--vscode-badge-foreground);
+	background-color: var(--vscode-list-inactiveSelectionBackground);
+	color: var(--vscode-list-inactiveSelectionForeground, var(--vscode-foreground));
 	border-radius: 8px;
-	border: 1px solid transparent;
 	min-width: 14px;
 	text-align: center;
 }
@@ -499,6 +565,7 @@
 /* Content container visibility */
 .ai-customization-management-editor .prompts-content-container,
 .ai-customization-management-editor .mcp-content-container,
+.ai-customization-management-editor .plugin-content-container,
 .ai-customization-management-editor .models-content-container {
 	height: 100%;
 	display: flex;
@@ -517,6 +584,18 @@
 	overflow: hidden;
 }
 
+/* Embedded plugin detail view */
+.ai-customization-management-editor .plugin-detail-container {
+	height: 100%;
+	display: flex;
+	flex-direction: column;
+}
+
+.ai-customization-management-editor .plugin-detail-editor-container {
+	flex: 1;
+	overflow: hidden;
+}
+
 /* Models section footer */
 .ai-customization-management-editor .models-content-container .section-footer {
 	flex-shrink: 0;
@@ -590,7 +669,8 @@
 
 .mcp-list-widget .mcp-list-container {
 	flex: 1;
-	overflow: hidden;
+	min-height: 0;
+	overflow: auto;
 }
 
 /* MCP Empty State */
@@ -632,17 +712,22 @@
 .mcp-server-item {
 	display: flex;
 	align-items: center;
-	padding: 8px 12px;
+	padding: 6px 8px;
 	cursor: pointer;
 	border-radius: 4px;
-	margin: 2px 0;
-	gap: 12px;
+	min-height: 32px;
+	gap: 10px;
 }
 
 .mcp-server-item:hover {
 	background-color: var(--vscode-list-hoverBackground);
 }
 
+.mcp-server-item.builtin {
+	cursor: default;
+	opacity: 0.85;
+}
+
 .mcp-server-item .mcp-server-icon {
 	flex-shrink: 0;
 	width: 24px;
@@ -663,10 +748,10 @@
 
 .mcp-server-item .mcp-server-name {
 	font-size: 13px;
-	font-weight: 500;
 	overflow: hidden;
 	text-overflow: ellipsis;
 	white-space: nowrap;
+	line-height: 18px;
 }
 
 .mcp-server-item .mcp-server-description {
@@ -675,6 +760,7 @@
 	overflow: hidden;
 	text-overflow: ellipsis;
 	white-space: nowrap;
+	line-height: 14px;
 }
 
 .mcp-server-item .mcp-server-status {
@@ -705,6 +791,15 @@
 	color: var(--vscode-badge-foreground);
 }
 
+.mcp-server-item.disabled {
+	opacity: 0.5;
+}
+
+.mcp-server-item .mcp-server-status.disabled {
+	background-color: var(--vscode-badge-background);
+	color: var(--vscode-badge-foreground);
+}
+
 /* Button group for Add Server + Browse Marketplace */
 .mcp-list-widget .list-button-group {
 	display: flex;
@@ -752,6 +847,19 @@
 	flex-shrink: 0;
 }
 
+.mcp-gallery-item.extension-list-item {
+	padding: 6px 8px 6px 16px;
+}
+
+.mcp-gallery-item.extension-list-item > .details > .footer {
+	display: flex;
+	align-items: center;
+}
+
+.mcp-gallery-item.extension-list-item .mcp-gallery-action {
+	margin-left: auto;
+}
+
 .mcp-gallery-item .mcp-gallery-install-button {
 	font-size: 11px;
 	padding: 2px 10px;
@@ -788,15 +896,25 @@
 	transition: background-color 0.1s ease, opacity 0.1s ease;
 }
 
-.ai-customization-management-editor .editor-back-button:hover {
+.ai-customization-management-editor .editor-back-button:hover:not(:disabled) {
 	background-color: var(--vscode-toolbar-hoverBackground);
 	opacity: 1;
 }
 
-.ai-customization-management-editor .editor-back-button:active {
+.ai-customization-management-editor .editor-back-button:active:not(:disabled) {
 	background-color: var(--vscode-toolbar-activeBackground);
 }
 
+.ai-customization-management-editor .editor-back-button:disabled {
+	cursor: default;
+	opacity: 0.45;
+}
+
+.ai-customization-management-editor .editor-action-button-icon {
+	font-size: 14px;
+	line-height: 14px;
+}
+
 .ai-customization-management-editor .editor-item-info {
 	display: flex;
 	flex-direction: column;
diff --git a/src/vs/workbench/contrib/chat/browser/aiCustomization/pluginListWidget.ts b/src/vs/workbench/contrib/chat/browser/aiCustomization/pluginListWidget.ts
new file mode 100644
index 0000000000000..63f41bcea3433
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/aiCustomization/pluginListWidget.ts
@@ -0,0 +1,734 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import './media/aiCustomizationManagement.css';
+import * as DOM from '../../../../../base/browser/dom.js';
+import { Disposable, DisposableStore, isDisposable } from '../../../../../base/common/lifecycle.js';
+import { Emitter } from '../../../../../base/common/event.js';
+import { localize } from '../../../../../nls.js';
+import { IInstantiationService } from '../../../../../platform/instantiation/common/instantiation.js';
+import { WorkbenchList } from '../../../../../platform/list/browser/listService.js';
+import { IListVirtualDelegate, IListRenderer, IListContextMenuEvent } from '../../../../../base/browser/ui/list/list.js';
+import { ThemeIcon } from '../../../../../base/common/themables.js';
+import { Codicon } from '../../../../../base/common/codicons.js';
+import { Button } from '../../../../../base/browser/ui/button/button.js';
+import { defaultButtonStyles, defaultInputBoxStyles } from '../../../../../platform/theme/browser/defaultStyles.js';
+import { autorun } from '../../../../../base/common/observable.js';
+import { IOpenerService } from '../../../../../platform/opener/common/opener.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { InputBox } from '../../../../../base/browser/ui/inputbox/inputBox.js';
+import { IContextMenuService, IContextViewService } from '../../../../../platform/contextview/browser/contextView.js';
+import { ICommandService } from '../../../../../platform/commands/common/commands.js';
+import { CancellationTokenSource } from '../../../../../base/common/cancellation.js';
+import { Delayer } from '../../../../../base/common/async.js';
+import { IAction, Separator } from '../../../../../base/common/actions.js';
+import { basename, dirname } from '../../../../../base/common/resources.js';
+import { getDefaultHoverDelegate } from '../../../../../base/browser/ui/hover/hoverDelegateFactory.js';
+import { IHoverService } from '../../../../../platform/hover/browser/hover.js';
+import { IAgentPlugin, IAgentPluginService } from '../../common/plugins/agentPluginService.js';
+import { isContributionEnabled } from '../../common/enablement.js';
+import { getInstalledPluginContextMenuActions } from '../agentPluginActions.js';
+import { IMarketplacePlugin, IPluginMarketplaceService } from '../../common/plugins/pluginMarketplaceService.js';
+import { IPluginInstallService } from '../../common/plugins/pluginInstallService.js';
+import { AgentPluginItemKind, IAgentPluginItem, IInstalledPluginItem, IMarketplacePluginItem } from '../agentPluginEditor/agentPluginItems.js';
+import { pluginIcon } from './aiCustomizationIcons.js';
+import { formatDisplayName, truncateToFirstSentence } from './aiCustomizationListWidget.js';
+import { ILabelService } from '../../../../../platform/label/common/label.js';
+import { CustomizationGroupHeaderRenderer, ICustomizationGroupHeaderEntry, CUSTOMIZATION_GROUP_HEADER_HEIGHT, CUSTOMIZATION_GROUP_HEADER_HEIGHT_WITH_SEPARATOR } from './customizationGroupHeaderRenderer.js';
+
+const $ = DOM.$;
+
+const PLUGIN_ITEM_HEIGHT = 36;
+
+//#region Entry types
+
+/**
+ * Represents a collapsible group header in the plugin list.
+ */
+interface IPluginGroupHeaderEntry extends ICustomizationGroupHeaderEntry {
+	readonly group: 'enabled' | 'disabled';
+}
+
+/**
+ * Represents an installed plugin item in the list.
+ */
+interface IPluginInstalledItemEntry {
+	readonly type: 'plugin-item';
+	readonly item: IInstalledPluginItem;
+}
+
+/**
+ * Represents a marketplace plugin item in the list (browse mode).
+ */
+interface IPluginMarketplaceItemEntry {
+	readonly type: 'marketplace-item';
+	readonly item: IMarketplacePluginItem;
+}
+
+type IPluginListEntry = IPluginGroupHeaderEntry | IPluginInstalledItemEntry | IPluginMarketplaceItemEntry;
+
+//#endregion
+
+//#region Delegate
+
+class PluginItemDelegate implements IListVirtualDelegate<IPluginListEntry> {
+	getHeight(element: IPluginListEntry): number {
+		if (element.type === 'group-header') {
+			return element.isFirst ? CUSTOMIZATION_GROUP_HEADER_HEIGHT : CUSTOMIZATION_GROUP_HEADER_HEIGHT_WITH_SEPARATOR;
+		}
+		if (element.type === 'marketplace-item') {
+			return 62;
+		}
+		return PLUGIN_ITEM_HEIGHT;
+	}
+
+	getTemplateId(element: IPluginListEntry): string {
+		if (element.type === 'group-header') {
+			return 'pluginGroupHeader';
+		}
+		if (element.type === 'marketplace-item') {
+			return 'pluginMarketplaceItem';
+		}
+		return 'pluginInstalledItem';
+	}
+}
+
+//#endregion
+
+//#endregion
+
+//#region Installed Plugin Renderer (reuses .mcp-server-item CSS)
+
+interface IPluginInstalledItemTemplateData {
+	readonly container: HTMLElement;
+	readonly typeIcon: HTMLElement;
+	readonly name: HTMLElement;
+	readonly description: HTMLElement;
+	readonly status: HTMLElement;
+	readonly disposables: DisposableStore;
+}
+
+class PluginInstalledItemRenderer implements IListRenderer<IPluginInstalledItemEntry, IPluginInstalledItemTemplateData> {
+	readonly templateId = 'pluginInstalledItem';
+
+	renderTemplate(container: HTMLElement): IPluginInstalledItemTemplateData {
+		container.classList.add('mcp-server-item');
+
+		const typeIcon = DOM.append(container, $('.mcp-server-icon'));
+		typeIcon.classList.add(...ThemeIcon.asClassNameArray(pluginIcon));
+
+		const details = DOM.append(container, $('.mcp-server-details'));
+		const name = DOM.append(details, $('.mcp-server-name'));
+		const description = DOM.append(details, $('.mcp-server-description'));
+		const status = DOM.append(container, $('.mcp-server-status'));
+
+		return { container, typeIcon, name, description, status, disposables: new DisposableStore() };
+	}
+
+	renderElement(element: IPluginInstalledItemEntry, _index: number, templateData: IPluginInstalledItemTemplateData): void {
+		templateData.disposables.clear();
+
+		templateData.name.textContent = formatDisplayName(element.item.name);
+
+		if (element.item.description) {
+			templateData.description.textContent = truncateToFirstSentence(element.item.description);
+			templateData.description.style.display = '';
+		} else {
+			templateData.description.style.display = 'none';
+		}
+
+		// Show enabled/disabled status
+		templateData.disposables.add(autorun(reader => {
+			const enabled = isContributionEnabled(element.item.plugin.enablement.read(reader));
+			templateData.container.classList.toggle('disabled', !enabled);
+			templateData.status.className = 'mcp-server-status';
+			if (enabled) {
+				templateData.status.textContent = localize('enabled', "Enabled");
+				templateData.status.classList.add('running');
+			} else {
+				templateData.status.textContent = localize('disabled', "Disabled");
+				templateData.status.classList.add('disabled');
+			}
+		}));
+	}
+
+	disposeTemplate(templateData: IPluginInstalledItemTemplateData): void {
+		templateData.disposables.dispose();
+	}
+}
+
+//#endregion
+
+//#region Marketplace Plugin Renderer (reuses .mcp-gallery-item CSS)
+
+interface IPluginMarketplaceItemTemplateData {
+	readonly container: HTMLElement;
+	readonly name: HTMLElement;
+	readonly publisher: HTMLElement;
+	readonly description: HTMLElement;
+	readonly installButton: Button;
+	readonly elementDisposables: DisposableStore;
+	readonly templateDisposables: DisposableStore;
+}
+
+class PluginMarketplaceItemRenderer implements IListRenderer<IPluginMarketplaceItemEntry, IPluginMarketplaceItemTemplateData> {
+	readonly templateId = 'pluginMarketplaceItem';
+
+	constructor(
+		private readonly pluginInstallService: IPluginInstallService,
+	) { }
+
+	renderTemplate(container: HTMLElement): IPluginMarketplaceItemTemplateData {
+		container.classList.add('mcp-server-item', 'mcp-gallery-item', 'extension-list-item');
+		const details = DOM.append(container, $('.details'));
+		const headerContainer = DOM.append(details, $('.header-container'));
+		const header = DOM.append(headerContainer, $('.header'));
+		const name = DOM.append(header, $('span.name'));
+		const description = DOM.append(details, $('.description.ellipsis'));
+		const footer = DOM.append(details, $('.footer'));
+		const publisherContainer = DOM.append(footer, $('.publisher-container'));
+		const publisher = DOM.append(publisherContainer, $('span.publisher-name'));
+		const actionContainer = DOM.append(footer, $('.mcp-gallery-action'));
+		const installButton = new Button(actionContainer, { ...defaultButtonStyles, supportIcons: true });
+		installButton.element.classList.add('mcp-gallery-install-button');
+
+		const templateDisposables = new DisposableStore();
+		templateDisposables.add(installButton);
+
+		return { container, name, publisher, description, installButton, elementDisposables: new DisposableStore(), templateDisposables };
+	}
+
+	renderElement(element: IPluginMarketplaceItemEntry, _index: number, templateData: IPluginMarketplaceItemTemplateData): void {
+		templateData.elementDisposables.clear();
+
+		templateData.name.textContent = element.item.name;
+		templateData.publisher.textContent = element.item.marketplace ? localize('byPublisher', "by {0}", element.item.marketplace) : '';
+		templateData.description.textContent = element.item.description || '';
+
+		templateData.installButton.label = localize('install', "Install");
+		templateData.installButton.enabled = true;
+
+		templateData.elementDisposables.add(templateData.installButton.onDidClick(async () => {
+			templateData.installButton.label = localize('installing', "Installing...");
+			templateData.installButton.enabled = false;
+			try {
+				await this.pluginInstallService.installPlugin({
+					name: element.item.name,
+					description: element.item.description,
+					version: '',
+					sourceDescriptor: element.item.sourceDescriptor,
+					source: element.item.source,
+					marketplace: element.item.marketplace,
+					marketplaceReference: element.item.marketplaceReference,
+					marketplaceType: element.item.marketplaceType,
+					readmeUri: element.item.readmeUri,
+				});
+				templateData.installButton.label = localize('installed', "Installed");
+			} catch (_e) {
+				templateData.installButton.label = localize('install', "Install");
+				templateData.installButton.enabled = true;
+			}
+		}));
+	}
+
+	disposeTemplate(templateData: IPluginMarketplaceItemTemplateData): void {
+		templateData.elementDisposables.dispose();
+		templateData.templateDisposables.dispose();
+	}
+}
+
+//#endregion
+
+//#region Helpers
+
+function installedPluginToItem(plugin: IAgentPlugin, labelService: ILabelService): IInstalledPluginItem {
+	const name = plugin.label ?? basename(plugin.uri);
+	const description = plugin.fromMarketplace?.description ?? labelService.getUriLabel(dirname(plugin.uri), { relative: true });
+	const marketplace = plugin.fromMarketplace?.marketplace;
+	return { kind: AgentPluginItemKind.Installed, name, description, marketplace, plugin };
+}
+
+function marketplacePluginToItem(plugin: IMarketplacePlugin): IMarketplacePluginItem {
+	return {
+		kind: AgentPluginItemKind.Marketplace,
+		name: plugin.name,
+		description: plugin.description,
+		source: plugin.source,
+		sourceDescriptor: plugin.sourceDescriptor,
+		marketplace: plugin.marketplace,
+		marketplaceReference: plugin.marketplaceReference,
+		marketplaceType: plugin.marketplaceType,
+		readmeUri: plugin.readmeUri,
+	};
+}
+
+//#endregion
+
+/**
+ * Widget that displays a list of agent plugins with marketplace browsing.
+ * Follows the same patterns as {@link McpListWidget}.
+ */
+export class PluginListWidget extends Disposable {
+
+	readonly element: HTMLElement;
+
+	private readonly _onDidSelectPlugin = this._register(new Emitter<IAgentPluginItem>());
+	readonly onDidSelectPlugin = this._onDidSelectPlugin.event;
+
+	private sectionHeader!: HTMLElement;
+	private sectionDescription!: HTMLElement;
+	private sectionLink!: HTMLAnchorElement;
+	private searchAndButtonContainer!: HTMLElement;
+	private searchInput!: InputBox;
+	private listContainer!: HTMLElement;
+	private list!: WorkbenchList<IPluginListEntry>;
+	private emptyContainer!: HTMLElement;
+	private emptyText!: HTMLElement;
+	private emptySubtext!: HTMLElement;
+	private browseButton!: Button;
+	private backLink!: HTMLElement;
+
+	private installedItems: IInstalledPluginItem[] = [];
+	private displayEntries: IPluginListEntry[] = [];
+	private marketplaceItems: IMarketplacePluginItem[] = [];
+	private searchQuery: string = '';
+	private browseMode: boolean = false;
+	private readonly collapsedGroups = new Set<string>();
+	private marketplaceCts: CancellationTokenSource | undefined;
+	private readonly delayedFilter = new Delayer<void>(200);
+	private readonly delayedMarketplaceSearch = new Delayer<void>(400);
+
+	constructor(
+		@IInstantiationService private readonly instantiationService: IInstantiationService,
+		@IAgentPluginService private readonly agentPluginService: IAgentPluginService,
+		@IPluginMarketplaceService private readonly pluginMarketplaceService: IPluginMarketplaceService,
+		@IPluginInstallService private readonly pluginInstallService: IPluginInstallService,
+		@IOpenerService private readonly openerService: IOpenerService,
+		@IContextViewService private readonly contextViewService: IContextViewService,
+		@IContextMenuService private readonly contextMenuService: IContextMenuService,
+		@IHoverService private readonly hoverService: IHoverService,
+		@ILabelService private readonly labelService: ILabelService,
+		@ICommandService private readonly commandService: ICommandService,
+	) {
+		super();
+		this.element = $('.mcp-list-widget'); // reuse MCP list widget CSS
+		this.create();
+		this._register({
+			dispose: () => {
+				this.marketplaceCts?.dispose();
+			}
+		});
+	}
+
+	private create(): void {
+		// Search and button container
+		this.searchAndButtonContainer = DOM.append(this.element, $('.list-search-and-button-container'));
+
+		// Search container
+		const searchContainer = DOM.append(this.searchAndButtonContainer, $('.list-search-container'));
+		this.searchInput = this._register(new InputBox(searchContainer, this.contextViewService, {
+			placeholder: localize('searchPluginsPlaceholder', "Type to search..."),
+			inputBoxStyles: defaultInputBoxStyles,
+		}));
+
+		this._register(this.searchInput.onDidChange(() => {
+			this.searchQuery = this.searchInput.value;
+			if (this.browseMode) {
+				this.delayedMarketplaceSearch.trigger(() => this.queryMarketplace());
+			} else {
+				this.delayedFilter.trigger(() => this.filterPlugins());
+			}
+		}));
+
+		// Button container (Browse Marketplace + Install from Source)
+		const buttonContainer = DOM.append(this.searchAndButtonContainer, $('.list-button-group'));
+
+		const browseButtonContainer = DOM.append(buttonContainer, $('.list-add-button-container'));
+		this.browseButton = this._register(new Button(browseButtonContainer, { ...defaultButtonStyles, secondary: true, supportIcons: true }));
+		this.browseButton.label = `$(${Codicon.library.id}) ${localize('browseMarketplace', "Browse Marketplace")}`;
+		this.browseButton.element.classList.add('list-add-button');
+		this._register(this.browseButton.onDidClick(() => {
+			this.toggleBrowseMode(!this.browseMode);
+		}));
+
+		const installFromSourceButton = this._register(new Button(buttonContainer, { ...defaultButtonStyles, secondary: true, supportIcons: true }));
+		installFromSourceButton.label = `$(${Codicon.add.id})`;
+		installFromSourceButton.setTitle(localize('installFromSource', "Install Plugin from Source"));
+		installFromSourceButton.element.classList.add('list-icon-button');
+		this._register(this.hoverService.setupManagedHover(getDefaultHoverDelegate('element'), installFromSourceButton.element, localize('installFromSourceTooltip', "Install Plugin from Source")));
+		this._register(installFromSourceButton.onDidClick(() => {
+			this.commandService.executeCommand('workbench.action.chat.installPluginFromSource');
+		}));
+
+		// Back to installed link (shown only in browse mode)
+		this.backLink = DOM.append(this.element, $('.mcp-back-link'));
+		this.backLink.setAttribute('role', 'button');
+		this.backLink.tabIndex = 0;
+		this.backLink.setAttribute('aria-label', localize('backToInstalledPluginsAriaLabel', "Back to installed plugins"));
+		const backIcon = DOM.append(this.backLink, $('span'));
+		backIcon.classList.add(...ThemeIcon.asClassNameArray(Codicon.arrowLeft));
+		const backText = DOM.append(this.backLink, $('span'));
+		backText.textContent = localize('backToInstalledPlugins', "Back to installed plugins");
+		this._register(DOM.addDisposableListener(this.backLink, 'click', () => {
+			this.toggleBrowseMode(false);
+		}));
+		this._register(DOM.addDisposableListener(this.backLink, 'keydown', (e: KeyboardEvent) => {
+			if (e.key === 'Enter' || e.key === ' ') {
+				e.preventDefault();
+				this.toggleBrowseMode(false);
+			}
+		}));
+		this.backLink.style.display = 'none';
+
+		// Empty state
+		this.emptyContainer = DOM.append(this.element, $('.mcp-empty-state'));
+		const emptyIcon = DOM.append(this.emptyContainer, $('.empty-icon'));
+		emptyIcon.classList.add(...ThemeIcon.asClassNameArray(pluginIcon));
+		this.emptyText = DOM.append(this.emptyContainer, $('.empty-text'));
+		this.emptySubtext = DOM.append(this.emptyContainer, $('.empty-subtext'));
+
+		// List container
+		this.listContainer = DOM.append(this.element, $('.mcp-list-container'));
+
+		// Section footer
+		this.sectionHeader = DOM.append(this.element, $('.section-footer'));
+		this.sectionDescription = DOM.append(this.sectionHeader, $('p.section-footer-description'));
+		this.sectionDescription.textContent = localize('pluginsDescription', "Extend your AI agent with plugins that add commands, skills, agents, hooks, and MCP servers from reusable packages.");
+		this.sectionLink = DOM.append(this.sectionHeader, $('a.section-footer-link')) as HTMLAnchorElement;
+		this.sectionLink.textContent = localize('learnMorePlugins', "Learn more about agent plugins");
+		this.sectionLink.href = 'https://code.visualstudio.com/docs/copilot/chat/agent-plugins';
+		this._register(DOM.addDisposableListener(this.sectionLink, 'click', (e) => {
+			e.preventDefault();
+			const href = this.sectionLink.href;
+			if (href) {
+				this.openerService.open(URI.parse(href));
+			}
+		}));
+
+		// Create list
+		const delegate = new PluginItemDelegate();
+		const groupHeaderRenderer = new CustomizationGroupHeaderRenderer<IPluginGroupHeaderEntry>('pluginGroupHeader', this.hoverService);
+		const installedRenderer = new PluginInstalledItemRenderer();
+		const marketplaceRenderer = new PluginMarketplaceItemRenderer(this.pluginInstallService);
+
+		this.list = this._register(this.instantiationService.createInstance(
+			WorkbenchList<IPluginListEntry>,
+			'PluginManagementList',
+			this.listContainer,
+			delegate,
+			[groupHeaderRenderer, installedRenderer, marketplaceRenderer],
+			{
+				multipleSelectionSupport: false,
+				setRowLineHeight: false,
+				horizontalScrolling: false,
+				accessibilityProvider: {
+					getAriaLabel(element: IPluginListEntry) {
+						if (element.type === 'group-header') {
+							return localize('pluginGroupAriaLabel', "{0}, {1} items, {2}", element.label, element.count, element.collapsed ? localize('collapsed', "collapsed") : localize('expanded', "expanded"));
+						}
+						if (element.type === 'marketplace-item') {
+							return element.item.name;
+						}
+						return element.item.name;
+					},
+					getWidgetAriaLabel() {
+						return localize('pluginsListAriaLabel', "Plugins");
+					}
+				},
+				openOnSingleClick: true,
+				identityProvider: {
+					getId(element: IPluginListEntry) {
+						if (element.type === 'group-header') {
+							return element.id;
+						}
+						if (element.type === 'marketplace-item') {
+							return `marketplace-${element.item.marketplaceReference.canonicalId}/${element.item.source}`;
+						}
+						return element.item.plugin.uri.toString();
+					}
+				}
+			}
+		));
+
+		this._register(this.list.onDidOpen(e => {
+			if (e.element) {
+				if (e.element.type === 'group-header') {
+					this.toggleGroup(e.element);
+				} else if (e.element.type === 'plugin-item') {
+					this._onDidSelectPlugin.fire(e.element.item);
+				} else if (e.element.type === 'marketplace-item') {
+					this._onDidSelectPlugin.fire(e.element.item);
+				}
+			}
+		}));
+
+		// Handle context menu
+		this._register(this.list.onContextMenu(e => this.onContextMenu(e as IListContextMenuEvent<IPluginListEntry>)));
+
+		// Listen to plugin service changes
+		this._register(autorun(reader => {
+			const plugins = this.agentPluginService.plugins.read(reader);
+			for (const plugin of plugins) {
+				plugin.enablement.read(reader);
+			}
+			if (!this.browseMode) {
+				this.refresh();
+			}
+		}));
+		this._register(this.pluginMarketplaceService.onDidChangeMarketplaces(() => {
+			if (!this.browseMode) {
+				this.refresh();
+			}
+		}));
+
+		// Initial refresh
+		void this.refresh();
+	}
+
+	private async refresh(): Promise<void> {
+		if (this.browseMode) {
+			await this.queryMarketplace();
+		} else {
+			this.filterPlugins();
+		}
+	}
+
+	private toggleBrowseMode(browse: boolean): void {
+		this.browseMode = browse;
+		this.searchInput.value = '';
+		this.searchQuery = '';
+
+		this.backLink.style.display = browse ? '' : 'none';
+		this.browseButton.element.parentElement!.style.display = browse ? 'none' : '';
+
+		this.searchInput.setPlaceHolder(browse
+			? localize('searchMarketplacePlaceholder', "Search plugin marketplace...")
+			: localize('searchPluginsPlaceholder', "Type to search...")
+		);
+
+		if (browse) {
+			void this.queryMarketplace();
+		} else {
+			this.marketplaceCts?.dispose(true);
+			this.marketplaceItems = [];
+			this.filterPlugins();
+		}
+	}
+
+	private async queryMarketplace(): Promise<void> {
+		this.marketplaceCts?.dispose(true);
+		const cts = this.marketplaceCts = new CancellationTokenSource();
+
+		// Show loading state
+		this.emptyContainer.style.display = 'flex';
+		this.listContainer.style.display = 'none';
+		this.emptyText.textContent = localize('loadingMarketplace', "Loading marketplace...");
+		this.emptySubtext.textContent = '';
+
+		try {
+			const plugins = await this.pluginMarketplaceService.fetchMarketplacePlugins(cts.token);
+
+			if (cts.token.isCancellationRequested) {
+				return;
+			}
+
+			const query = this.searchQuery.toLowerCase().trim();
+			const filtered = query
+				? plugins.filter(p => p.name.toLowerCase().includes(query) || p.description.toLowerCase().includes(query))
+				: plugins;
+
+			// Filter out already-installed plugins
+			const installedUris = new Set(this.agentPluginService.plugins.get().map(p => p.uri.toString()));
+			this.marketplaceItems = filtered
+				.filter(p => {
+					const expectedUri = this.pluginInstallService.getPluginInstallUri(p);
+					return !installedUris.has(expectedUri.toString());
+				})
+				.map(marketplacePluginToItem);
+
+			this.updateMarketplaceList();
+		} catch {
+			if (!cts.token.isCancellationRequested) {
+				this.marketplaceItems = [];
+				this.emptyContainer.style.display = 'flex';
+				this.listContainer.style.display = 'none';
+				this.emptyText.textContent = localize('marketplaceError', "Unable to load marketplace");
+				this.emptySubtext.textContent = localize('tryAgainLater', "Check your connection and try again");
+			}
+		}
+	}
+
+	private updateMarketplaceList(): void {
+		if (this.marketplaceItems.length === 0) {
+			this.emptyContainer.style.display = 'flex';
+			this.listContainer.style.display = 'none';
+			if (this.searchQuery.trim()) {
+				this.emptyText.textContent = localize('noMarketplaceResults', "No plugins match '{0}'", this.searchQuery);
+				this.emptySubtext.textContent = localize('tryDifferentSearch', "Try a different search term");
+			} else {
+				this.emptyText.textContent = localize('emptyMarketplace', "No plugins available");
+				this.emptySubtext.textContent = '';
+			}
+		} else {
+			this.emptyContainer.style.display = 'none';
+			this.listContainer.style.display = '';
+		}
+
+		const entries: IPluginListEntry[] = this.marketplaceItems.map(item => ({ type: 'marketplace-item' as const, item }));
+		this.list.splice(0, this.list.length, entries);
+	}
+
+	private filterPlugins(): void {
+		const query = this.searchQuery.toLowerCase().trim();
+		const allPlugins = this.agentPluginService.plugins.get();
+
+		this.installedItems = allPlugins
+			.map(p => installedPluginToItem(p, this.labelService))
+			.filter(item => !query ||
+				item.name.toLowerCase().includes(query) ||
+				item.description.toLowerCase().includes(query)
+			);
+
+		if (this.installedItems.length === 0) {
+			this.emptyContainer.style.display = 'flex';
+			this.listContainer.style.display = 'none';
+
+			if (this.searchQuery.trim()) {
+				this.emptyText.textContent = localize('noMatchingPlugins', "No plugins match '{0}'", this.searchQuery);
+				this.emptySubtext.textContent = localize('tryDifferentSearch', "Try a different search term");
+			} else {
+				this.emptyText.textContent = localize('noPlugins', "No plugins installed");
+				this.emptySubtext.textContent = localize('browseToAdd', "Browse the marketplace to discover and install plugins");
+			}
+		} else {
+			this.emptyContainer.style.display = 'none';
+			this.listContainer.style.display = '';
+		}
+
+		// Group plugins: enabled vs disabled
+		const enabledPlugins = this.installedItems.filter(item => isContributionEnabled(item.plugin.enablement.get()));
+		const disabledPlugins = this.installedItems.filter(item => !isContributionEnabled(item.plugin.enablement.get()));
+
+		const entries: IPluginListEntry[] = [];
+		let isFirst = true;
+
+		if (enabledPlugins.length > 0) {
+			const collapsed = this.collapsedGroups.has('enabled');
+			entries.push({
+				type: 'group-header',
+				id: 'plugin-group-enabled',
+				group: 'enabled',
+				label: localize('enabledGroup', "Enabled"),
+				icon: pluginIcon,
+				count: enabledPlugins.length,
+				isFirst,
+				description: localize('enabledGroupDescription', "Plugins that are currently active and providing commands, skills, agents, and other capabilities."),
+				collapsed,
+			});
+			if (!collapsed) {
+				for (const item of enabledPlugins) {
+					entries.push({ type: 'plugin-item', item });
+				}
+			}
+			isFirst = false;
+		}
+
+		if (disabledPlugins.length > 0) {
+			const collapsed = this.collapsedGroups.has('disabled');
+			entries.push({
+				type: 'group-header',
+				id: 'plugin-group-disabled',
+				group: 'disabled',
+				label: localize('disabledGroup', "Disabled"),
+				icon: pluginIcon,
+				count: disabledPlugins.length,
+				isFirst,
+				description: localize('disabledGroupDescription', "Plugins that are installed but currently disabled. Enable them to use their capabilities."),
+				collapsed,
+			});
+			if (!collapsed) {
+				for (const item of disabledPlugins) {
+					entries.push({ type: 'plugin-item', item });
+				}
+			}
+		}
+
+		this.displayEntries = entries;
+		this.list.splice(0, this.list.length, this.displayEntries);
+	}
+
+	private toggleGroup(entry: IPluginGroupHeaderEntry): void {
+		if (this.collapsedGroups.has(entry.group)) {
+			this.collapsedGroups.delete(entry.group);
+		} else {
+			this.collapsedGroups.add(entry.group);
+		}
+		this.filterPlugins();
+	}
+
+	layout(height: number, width: number): void {
+		const sectionFooterHeight = this.sectionHeader.offsetHeight || 0;
+		const searchBarHeight = this.searchAndButtonContainer.offsetHeight || 52;
+		const backLinkHeight = this.browseMode ? (this.backLink.offsetHeight || 28) : 0;
+		const listHeight = height - sectionFooterHeight - searchBarHeight - backLinkHeight;
+
+		this.listContainer.style.height = `${Math.max(0, listHeight)}px`;
+		this.list.layout(Math.max(0, listHeight), width);
+
+		if (sectionFooterHeight === 0) {
+			DOM.getWindow(this.listContainer).requestAnimationFrame(() => {
+				if (this._store.isDisposed) {
+					return;
+				}
+				const actualFooterHeight = this.sectionHeader.offsetHeight;
+				if (actualFooterHeight > 0) {
+					const correctedHeight = height - actualFooterHeight - searchBarHeight - backLinkHeight;
+					this.listContainer.style.height = `${Math.max(0, correctedHeight)}px`;
+					this.list.layout(Math.max(0, correctedHeight), width);
+				}
+			});
+		}
+	}
+
+	focusSearch(): void {
+		this.searchInput.focus();
+	}
+
+	focus(): void {
+		this.list.domFocus();
+		if (this.list.length > 0) {
+			this.list.setFocus([0]);
+		}
+	}
+
+	private onContextMenu(e: IListContextMenuEvent<IPluginListEntry>): void {
+		if (!e.element || e.element.type !== 'plugin-item') {
+			return;
+		}
+
+		const entry = e.element;
+		const disposables = new DisposableStore();
+		const groups: IAction[][] = getInstalledPluginContextMenuActions(entry.item.plugin, this.instantiationService);
+		const actions: IAction[] = [];
+		for (const menuActions of groups) {
+			for (const menuAction of menuActions) {
+				actions.push(menuAction);
+				if (isDisposable(menuAction)) {
+					disposables.add(menuAction);
+				}
+			}
+			actions.push(new Separator());
+		}
+		if (actions.length > 0 && actions[actions.length - 1] instanceof Separator) {
+			actions.pop();
+		}
+
+		this.contextMenuService.showContextMenu({
+			getAnchor: () => e.anchor,
+			getActions: () => actions,
+			onHide: () => disposables.dispose()
+		});
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentResolveService.ts b/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentResolveService.ts
index e5fb7e719a9d4..f57fcb7154123 100644
--- a/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentResolveService.ts
+++ b/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentResolveService.ts
@@ -10,7 +10,6 @@ import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { IRange } from '../../../../../editor/common/core/range.js';
 import { SymbolKinds } from '../../../../../editor/common/languages.js';
-import { ITextModelService } from '../../../../../editor/common/services/resolverService.js';
 import { localize } from '../../../../../nls.js';
 import { IDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
 import { IDraggedResourceEditorInput, MarkerTransferData, DocumentSymbolTransferData, NotebookCellOutputTransferData } from '../../../../../platform/dnd/browser/dnd.js';
@@ -27,8 +26,7 @@ import { getOutputViewModelFromId } from '../../../notebook/browser/controller/c
 import { getNotebookEditorFromEditorPane } from '../../../notebook/browser/notebookBrowser.js';
 import { SCMHistoryItemTransferData } from '../../../scm/browser/scmHistoryChatContext.js';
 import { CHAT_ATTACHABLE_IMAGE_MIME_TYPES, getAttachableImageExtension } from '../../common/model/chatModel.js';
-import { IChatRequestVariableEntry, OmittedState, IDiagnosticVariableEntry, IDiagnosticVariableEntryFilterData, ISymbolVariableEntry, toPromptFileVariableEntry, PromptFileVariableKind, ISCMHistoryItemVariableEntry } from '../../common/attachments/chatVariableEntries.js';
-import { getPromptsTypeForLanguageId, PromptsType } from '../../common/promptSyntax/promptTypes.js';
+import { IChatRequestVariableEntry, OmittedState, IDiagnosticVariableEntry, IDiagnosticVariableEntryFilterData, ISymbolVariableEntry, ISCMHistoryItemVariableEntry } from '../../common/attachments/chatVariableEntries.js';
 import { imageToHash } from '../widget/input/editor/chatPasteProviders.js';
 import { resizeImage } from '../chatImageUtils.js';
 
@@ -56,7 +54,6 @@ export class ChatAttachmentResolveService implements IChatAttachmentResolveServi
 	constructor(
 		@IFileService private fileService: IFileService,
 		@IEditorService private editorService: IEditorService,
-		@ITextModelService private textModelService: ITextModelService,
 		@IExtensionService private extensionService: IExtensionService,
 		@IDialogService private dialogService: IDialogService
 	) { }
@@ -115,27 +112,9 @@ export class ChatAttachmentResolveService implements IChatAttachmentResolveServi
 		let omittedState = OmittedState.NotOmitted;
 
 		if (!isDirectory) {
-
-			let languageId: string | undefined;
-			try {
-				const createdModel = await this.textModelService.createModelReference(resource);
-				languageId = createdModel.object.getLanguageId();
-				createdModel.dispose();
-			} catch {
-				omittedState = OmittedState.Full;
-			}
-
 			if (/\.(svg)$/i.test(resource.path)) {
 				omittedState = OmittedState.Full;
 			}
-			if (languageId) {
-				const promptsType = getPromptsTypeForLanguageId(languageId);
-				if (promptsType === PromptsType.prompt) {
-					return toPromptFileVariableEntry(resource, PromptFileVariableKind.PromptFile);
-				} else if (promptsType === PromptsType.instructions) {
-					return toPromptFileVariableEntry(resource, PromptFileVariableKind.Instruction);
-				}
-			}
 		}
 
 		return {
diff --git a/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentWidgetRegistry.ts b/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentWidgetRegistry.ts
index e4cb7c0fc57e6..404a3ae6bc877 100644
--- a/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentWidgetRegistry.ts
+++ b/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentWidgetRegistry.ts
@@ -15,6 +15,8 @@ export interface IChatAttachmentWidgetInstance extends IDisposable {
 	readonly element: HTMLElement;
 	readonly onDidDelete: event.Event<Event>;
 	readonly onDidOpen: event.Event<void>;
+	/** Optional label element, used for applying warning styles on omitted attachments. */
+	readonly label?: { readonly element: HTMLElement };
 }
 
 /**
diff --git a/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentWidgets.ts b/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentWidgets.ts
index eb154e0b96f6a..ab219b9bd1e81 100644
--- a/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentWidgets.ts
+++ b/src/vs/workbench/contrib/chat/browser/attachments/chatAttachmentWidgets.ts
@@ -51,7 +51,7 @@ import { IOpenerService, OpenInternalOptions } from '../../../../../platform/ope
 import { FolderThemeIcon, IThemeService } from '../../../../../platform/theme/common/themeService.js';
 import { fillEditorsDragData } from '../../../../browser/dnd.js';
 import { IFileLabelOptions, IResourceLabel, ResourceLabels } from '../../../../browser/labels.js';
-import { ResourceContextKey } from '../../../../common/contextkeys.js';
+import { StaticResourceContextKey } from '../../../../common/contextkeys.js';
 import { IEditorService, SIDE_GROUP } from '../../../../services/editor/common/editorService.js';
 import { IPreferencesService } from '../../../../services/preferences/common/preferences.js';
 import { revealInSideBarCommand } from '../../../files/browser/fileActions.contribution.js';
@@ -61,12 +61,15 @@ import { toHistoryItemHoverContent } from '../../../scm/browser/scmHistory.js';
 import { getHistoryItemEditorTitle } from '../../../scm/browser/util.js';
 import { ITerminalService } from '../../../terminal/browser/terminal.js';
 import { IChatContentReference } from '../../common/chatService/chatService.js';
+import { coerceImageBuffer } from '../../common/chatImageExtraction.js';
+import { ChatConfiguration } from '../../common/constants.js';
 import { IChatRequestPasteVariableEntry, IChatRequestVariableEntry, IElementVariableEntry, INotebookOutputVariableEntry, IPromptFileVariableEntry, IPromptTextVariableEntry, ISCMHistoryItemVariableEntry, OmittedState, PromptFileVariableKind, ChatRequestToolReferenceEntry, ISCMHistoryItemChangeVariableEntry, ISCMHistoryItemChangeRangeVariableEntry, ITerminalVariableEntry, isStringVariableEntry } from '../../common/attachments/chatVariableEntries.js';
 import { ILanguageModelChatMetadataAndIdentifier, ILanguageModelsService } from '../../common/languageModels.js';
 import { IChatEntitlementService } from '../../../../services/chat/common/chatEntitlementService.js';
 import { ILanguageModelToolsService, isToolSet } from '../../common/tools/languageModelToolsService.js';
 import { getCleanPromptName } from '../../common/promptSyntax/config/promptFileLocations.js';
 import { IChatContextService } from '../contextContrib/chatContextService.js';
+import { IChatImageCarouselService } from '../chatImageCarouselService.js';
 
 const commonHoverOptions: Partial<IHoverOptions> = {
 	style: HoverStyle.Pointer,
@@ -137,6 +140,15 @@ abstract class AbstractChatAttachmentWidget extends Disposable {
 		return modelSupportsVision(this.currentLanguageModel);
 	}
 
+	private _hasClearButton = false;
+
+	protected appendDeletionHint(ariaLabel: string): string {
+		if (!this._hasClearButton) {
+			return ariaLabel;
+		}
+		return localize('chat.attachment.withDeleteHint', "{0} (Delete)", ariaLabel);
+	}
+
 	protected attachClearButton() {
 
 		if (this.attachment.range || !this.options.supportsDeletion) {
@@ -145,6 +157,8 @@ abstract class AbstractChatAttachmentWidget extends Disposable {
 			return;
 		}
 
+		this._hasClearButton = true;
+
 		const clearButton = new Button(this.element, {
 			supportIcons: true,
 			hoverDelegate: createInstantHoverDelegate(),
@@ -158,6 +172,8 @@ abstract class AbstractChatAttachmentWidget extends Disposable {
 		}));
 		this._register(dom.addStandardDisposableListener(this.element, dom.EventType.KEY_DOWN, e => {
 			if (e.keyCode === KeyCode.Backspace || e.keyCode === KeyCode.Delete) {
+				e.preventDefault();
+				e.stopPropagation();
 				this._onDidDelete.fire(e.browserEvent);
 			}
 		}));
@@ -253,7 +269,7 @@ export class FileAttachmentWidget extends AbstractChatAttachmentWidget {
 			});
 		}
 
-		this.element.ariaLabel = ariaLabel;
+		this.element.ariaLabel = this.appendDeletionHint(ariaLabel);
 
 		this.instantiationService.invokeFunction(accessor => {
 			this._register(hookUpResourceAttachmentDragAndContextMenu(accessor, this.element, resource));
@@ -308,6 +324,8 @@ export class TerminalCommandAttachmentWidget extends AbstractChatAttachmentWidge
 				await clickHandler();
 			}
 		}));
+
+		this.element.ariaLabel = this.appendDeletionHint(ariaLabel);
 	}
 }
 
@@ -405,6 +423,7 @@ export class ImageAttachmentWidget extends AbstractChatAttachmentWidget {
 		@IInstantiationService instantiationService: IInstantiationService,
 		@ILabelService private readonly labelService: ILabelService,
 		@IChatEntitlementService private readonly chatEntitlementService: IChatEntitlementService,
+		@IChatImageCarouselService private readonly chatImageCarouselService: IChatImageCarouselService,
 	) {
 		super(attachment, options, container, contextResourceLabels, currentLanguageModel, commandService, openerService, configurationService);
 
@@ -419,8 +438,11 @@ export class ImageAttachmentWidget extends AbstractChatAttachmentWidget {
 
 		const ref = attachment.references?.[0]?.reference;
 		resource = ref && URI.isUri(ref) ? ref : undefined;
+		const imageData = coerceImageBuffer(attachment.value);
 		const clickHandler = async () => {
-			if (resource) {
+			if ((resource || imageData) && configurationService.getValue<boolean>(ChatConfiguration.ImageCarouselEnabled)) {
+				await this.openInCarousel(attachment.name, imageData, resource);
+			} else if (resource) {
 				await this.openResource(resource, { editorOptions: { preserveFocus: true } }, false, undefined);
 			}
 		};
@@ -428,15 +450,29 @@ export class ImageAttachmentWidget extends AbstractChatAttachmentWidget {
 		const currentLanguageModelName = this.currentLanguageModel ? this.languageModelsService.lookupLanguageModel(this.currentLanguageModel.identifier)?.name ?? this.currentLanguageModel.identifier : 'Current model';
 
 		const fullName = resource ? this.labelService.getUriLabel(resource) : (attachment.fullName || attachment.name);
-		this._register(createImageElements(resource, attachment.name, fullName, this.element, attachment.value as Uint8Array, this.hoverService, ariaLabel, currentLanguageModelName, clickHandler, this.currentLanguageModel, attachment.omittedState, this.chatEntitlementService.previewFeaturesDisabled));
+		this._register(createImageElements(resource, attachment.name, fullName, this.element, imageData ?? (attachment.value as Uint8Array), this.hoverService, ariaLabel, currentLanguageModelName, clickHandler, this.currentLanguageModel, attachment.omittedState, this.chatEntitlementService.previewFeaturesDisabled));
+		this.element.ariaLabel = this.appendDeletionHint(ariaLabel);
+
+		// Wire up click + keyboard (Enter/Space) open handlers
+		const canOpenCarousel = attachment.value instanceof Uint8Array && configurationService.getValue<boolean>(ChatConfiguration.ImageCarouselEnabled);
+		if ((imageData && canOpenCarousel) || resource) {
+			this.element.style.cursor = 'pointer';
+			this._register(registerOpenEditorListeners(this.element, async () => {
+				await clickHandler();
+			}));
+		}
 
 		if (resource) {
-			this.addResourceOpenHandlers(resource, undefined);
 			instantiationService.invokeFunction(accessor => {
 				this._register(hookUpResourceAttachmentDragAndContextMenu(accessor, this.element, resource));
 			});
 		}
 	}
+
+	private async openInCarousel(name: string, data: Uint8Array | undefined, referenceUri: URI | undefined): Promise<void> {
+		const resource = referenceUri ?? URI.from({ scheme: 'data', path: name });
+		await this.chatImageCarouselService.openCarouselAtResource(resource, data);
+	}
 }
 
 function createImageElements(resource: URI | undefined, name: string, fullName: string,
@@ -459,7 +495,6 @@ function createImageElements(resource: URI | undefined, name: string, fullName:
 
 	if (resource) {
 		element.style.cursor = 'pointer';
-		disposable.add(dom.addDisposableListener(element, 'click', clickHandler));
 	}
 	const supportsVision = modelSupportsVision(currentLanguageModel);
 	const pillIcon = dom.$('div.chat-attached-context-pill', {}, dom.$((supportsVision && !previewFeaturesDisabled) ? 'span.codicon.codicon-file-media' : 'span.codicon.codicon-warning'));
@@ -544,7 +579,7 @@ export class PasteAttachmentWidget extends AbstractChatAttachmentWidget {
 		super(attachment, options, container, contextResourceLabels, currentLanguageModel, commandService, openerService, configurationService);
 
 		const ariaLabel = localize('chat.attachment', "Attached context, {0}", attachment.name);
-		this.element.ariaLabel = ariaLabel;
+		this.element.ariaLabel = this.appendDeletionHint(ariaLabel);
 
 		const classNames = ['file-icon', `${attachment.language}-lang-file-icon`];
 		let resource: URI | undefined;
@@ -612,7 +647,7 @@ export class DefaultChatAttachmentWidget extends AbstractChatAttachmentWidget {
 			const withIcon = attachment.icon?.id ? `$(${attachment.icon.id})\u00A0${attachmentLabel}` : attachmentLabel;
 			this.label.setLabel(withIcon, correspondingContentReference?.options?.status?.description);
 		}
-		this.element.ariaLabel = localize('chat.attachment', "Attached context, {0}", attachment.name);
+		this.element.ariaLabel = this.appendDeletionHint(localize('chat.attachment', "Attached context, {0}", attachment.name));
 
 		if (attachment.kind === 'diagnostic') {
 			if (attachment.filterUri) {
@@ -640,6 +675,16 @@ export class DefaultChatAttachmentWidget extends AbstractChatAttachmentWidget {
 			}));
 		}
 
+		// Handle click for debug events attachments
+		if (attachment.kind === 'debugEvents') {
+			this.element.style.cursor = 'pointer';
+			this._register(dom.addDisposableListener(this.element, dom.EventType.CLICK, () => {
+				const d = new Date(attachment.snapshotTime);
+				const filter = `before:${d.getFullYear()}-${String(d.getMonth() + 1).padStart(2, '0')}-${String(d.getDate()).padStart(2, '0')}T${String(d.getHours()).padStart(2, '0')}:${String(d.getMinutes()).padStart(2, '0')}:${String(d.getSeconds()).padStart(2, '0')}`;
+				this.commandService.executeCommand('workbench.action.chat.openAgentDebugPanelForSession', attachment.sessionResource, filter);
+			}));
+		}
+
 		// Setup tooltip hover for string context attachments
 		if ((isStringVariableEntry(attachment) || attachment.kind === 'generic') && attachment.tooltip) {
 			this._setupTooltipHover(attachment.tooltip);
@@ -734,7 +779,7 @@ export class PromptFileAttachmentWidget extends AbstractChatAttachmentWidget {
 		this.hintElement.innerText = typeLabel;
 
 
-		this.element.ariaLabel = ariaLabel;
+		this.element.ariaLabel = this.appendDeletionHint(ariaLabel);
 	}
 }
 
@@ -772,6 +817,7 @@ export class PromptTextAttachmentWidget extends AbstractChatAttachmentWidget {
 			}));
 		}
 		this.label.setLabel(localize('instructions.label', 'Additional Instructions'), undefined, undefined);
+		this.element.ariaLabel = this.appendDeletionHint(localize('chat.attachment', "Attached context, {0}", attachment.name));
 
 		this._register(hoverService.setupDelayedHover(this.element, {
 			...commonHoverOptions,
@@ -811,7 +857,7 @@ export class ToolSetOrToolItemAttachmentWidget extends AbstractChatAttachmentWid
 		this.label.setLabel(`$(${icon.id})\u00A0${name}`, undefined);
 
 		this.element.style.cursor = 'pointer';
-		this.element.ariaLabel = localize('chat.attachment', "Attached context, {0}", name);
+		this.element.ariaLabel = this.appendDeletionHint(localize('chat.attachment', "Attached context, {0}", name));
 
 		let hoverContent: string | undefined;
 
@@ -889,10 +935,10 @@ export class NotebookCellOutputChatAttachmentWidget extends AbstractChatAttachme
 			//
 		}
 		this.label.setLabel(withIcon, undefined, { title });
-		this.element.ariaLabel = this.getAriaLabel(attachment);
+		this.element.ariaLabel = this.appendDeletionHint(this.getAriaLabel(attachment));
 	}
 	private renderGenericOutput(resource: URI, attachment: INotebookOutputVariableEntry) {
-		this.element.ariaLabel = this.getAriaLabel(attachment);
+		this.element.ariaLabel = this.appendDeletionHint(this.getAriaLabel(attachment));
 		this.label.setFile(resource, { hidePath: true, icon: ThemeIcon.fromId('output') });
 	}
 	private renderImageOutput(resource: URI, attachment: INotebookOutputVariableEntry) {
@@ -909,6 +955,7 @@ export class NotebookCellOutputChatAttachmentWidget extends AbstractChatAttachme
 		const currentLanguageModelName = this.currentLanguageModel ? this.languageModelsService.lookupLanguageModel(this.currentLanguageModel.identifier)?.name ?? this.currentLanguageModel.identifier : undefined;
 		const buffer = this.getOutputItem(resource, attachment)?.data.buffer ?? new Uint8Array();
 		this._register(createImageElements(resource, attachment.name, attachment.name, this.element, buffer, this.hoverService, ariaLabel, currentLanguageModelName, clickHandler, this.currentLanguageModel, attachment.omittedState, this.chatEntitlementService.previewFeaturesDisabled));
+		this.element.ariaLabel = this.appendDeletionHint(ariaLabel);
 	}
 
 	private getOutputItem(resource: URI, attachment: INotebookOutputVariableEntry) {
@@ -946,7 +993,7 @@ export class ElementChatAttachmentWidget extends AbstractChatAttachmentWidget {
 		super(attachment, options, container, contextResourceLabels, currentLanguageModel, commandService, openerService, configurationService);
 
 		const ariaLabel = localize('chat.elementAttachment', "Attached element, {0}", attachment.name);
-		this.element.ariaLabel = ariaLabel;
+		this.element.ariaLabel = this.appendDeletionHint(ariaLabel);
 
 		this.element.style.position = 'relative';
 		this.element.style.cursor = 'pointer';
@@ -1252,7 +1299,7 @@ export class SCMHistoryItemAttachmentWidget extends AbstractChatAttachmentWidget
 		this.label.setLabel(attachment.name, undefined);
 
 		this.element.style.cursor = 'pointer';
-		this.element.ariaLabel = localize('chat.attachment', "Attached context, {0}", attachment.name);
+		this.element.ariaLabel = this.appendDeletionHint(localize('chat.attachment', "Attached context, {0}", attachment.name));
 
 		const { content, disposables } = toHistoryItemHoverContent(markdownRendererService, attachment.historyItem, false);
 		this._store.add(hoverService.setupDelayedHover(this.element, {
@@ -1302,7 +1349,7 @@ export class SCMHistoryItemChangeAttachmentWidget extends AbstractChatAttachment
 		const nameSuffix = `\u00A0$(${Codicon.gitCommit.id})${attachment.historyItem.displayId ?? attachment.historyItem.id}`;
 		this.label.setFile(attachment.value, { fileKind: FileKind.FILE, hidePath: true, nameSuffix });
 
-		this.element.ariaLabel = localize('chat.attachment', "Attached context, {0}", attachment.name);
+		this.element.ariaLabel = this.appendDeletionHint(localize('chat.attachment', "Attached context, {0}", attachment.name));
 
 		const { content, disposables } = toHistoryItemHoverContent(markdownRendererService, attachment.historyItem, false);
 		this._store.add(hoverService.setupDelayedHover(this.element, {
@@ -1347,7 +1394,7 @@ export class SCMHistoryItemChangeRangeAttachmentWidget extends AbstractChatAttac
 		const nameSuffix = `\u00A0$(${Codicon.gitCommit.id})${historyItemStartId}..${historyItemEndId}`;
 		this.label.setFile(attachment.value, { fileKind: FileKind.FILE, hidePath: true, nameSuffix });
 
-		this.element.ariaLabel = localize('chat.attachment', "Attached context, {0}", attachment.name);
+		this.element.ariaLabel = this.appendDeletionHint(localize('chat.attachment', "Attached context, {0}", attachment.name));
 
 		this.addResourceOpenHandlers(attachment.value, undefined);
 	}
@@ -1379,7 +1426,7 @@ export function hookUpResourceAttachmentDragAndContextMenu(accessor: ServicesAcc
 
 	// Context
 	const scopedContextKeyService = store.add(contextKeyService.createScoped(widget));
-	store.add(setResourceContext(accessor, scopedContextKeyService, resource));
+	setResourceContext(accessor, scopedContextKeyService, resource);
 
 	// Drag and drop
 	widget.draggable = true;
@@ -1418,21 +1465,27 @@ export function hookUpSymbolAttachmentDragAndContextMenu(accessor: ServicesAcces
 		e.dataTransfer?.setDragImage(widget, 0, 0);
 	}));
 
-	// Context menu (context key service created eagerly for keybinding preconditions,
-	// but resource context and provider contexts are initialized lazily on first use)
-	const scopedContextKeyService = store.add(parentContextKeyService.createScoped(widget));
-	chatAttachmentResourceContextKey.bindTo(scopedContextKeyService).set(attachment.value.uri.toString());
-	store.add(setResourceContext(accessor, scopedContextKeyService, attachment.value.uri));
-
+	// Context menu (context key service and resource contexts are initialized lazily on first context menu open)
+	let scopedContextKeyService: IScopedContextKeyService | undefined;
 	let providerContexts: ReadonlyArray<[IContextKey<boolean>, LanguageFeatureRegistry<unknown>]> | undefined;
 
+	const ensureContextKeyService = () => {
+		if (!scopedContextKeyService) {
+			scopedContextKeyService = store.add(parentContextKeyService.createScoped(widget));
+			chatAttachmentResourceContextKey.bindTo(scopedContextKeyService).set(attachment.value.uri.toString());
+			setResourceContext(accessor, scopedContextKeyService, attachment.value.uri);
+		}
+		return scopedContextKeyService;
+	};
+
 	const ensureProviderContexts = () => {
+		const cks = ensureContextKeyService();
 		if (!providerContexts) {
 			providerContexts = [
-				[EditorContextKeys.hasDefinitionProvider.bindTo(scopedContextKeyService), languageFeaturesService.definitionProvider],
-				[EditorContextKeys.hasReferenceProvider.bindTo(scopedContextKeyService), languageFeaturesService.referenceProvider],
-				[EditorContextKeys.hasImplementationProvider.bindTo(scopedContextKeyService), languageFeaturesService.implementationProvider],
-				[EditorContextKeys.hasTypeDefinitionProvider.bindTo(scopedContextKeyService), languageFeaturesService.typeDefinitionProvider],
+				[EditorContextKeys.hasDefinitionProvider.bindTo(cks), languageFeaturesService.definitionProvider],
+				[EditorContextKeys.hasReferenceProvider.bindTo(cks), languageFeaturesService.referenceProvider],
+				[EditorContextKeys.hasImplementationProvider.bindTo(cks), languageFeaturesService.implementationProvider],
+				[EditorContextKeys.hasTypeDefinitionProvider.bindTo(cks), languageFeaturesService.typeDefinitionProvider],
 			];
 		}
 	};
@@ -1454,6 +1507,8 @@ export function hookUpSymbolAttachmentDragAndContextMenu(accessor: ServicesAcces
 		const event = new StandardMouseEvent(dom.getWindow(domEvent), domEvent);
 		dom.EventHelper.stop(domEvent, true);
 
+		const cks = ensureContextKeyService();
+
 		try {
 			await updateContextKeys();
 		} catch (e) {
@@ -1461,10 +1516,10 @@ export function hookUpSymbolAttachmentDragAndContextMenu(accessor: ServicesAcces
 		}
 
 		contextMenuService.showContextMenu({
-			contextKeyService: scopedContextKeyService,
+			contextKeyService: cks,
 			getAnchor: () => event,
 			getActions: () => {
-				const menu = menuService.getMenuActions(contextMenuId, scopedContextKeyService, { arg: attachment.value });
+				const menu = menuService.getMenuActions(contextMenuId, cks, { arg: attachment.value });
 				return getFlatContextMenuActions(menu);
 			},
 		});
@@ -1473,14 +1528,13 @@ export function hookUpSymbolAttachmentDragAndContextMenu(accessor: ServicesAcces
 	return store;
 }
 
-function setResourceContext(accessor: ServicesAccessor, scopedContextKeyService: IScopedContextKeyService, resource: URI) {
+function setResourceContext(accessor: ServicesAccessor, scopedContextKeyService: IScopedContextKeyService, resource: URI): void {
 	const fileService = accessor.get(IFileService);
 	const languageService = accessor.get(ILanguageService);
 	const modelService = accessor.get(IModelService);
 
-	const resourceContextKey = new ResourceContextKey(scopedContextKeyService, fileService, languageService, modelService);
+	const resourceContextKey = new StaticResourceContextKey(scopedContextKeyService, fileService, languageService, modelService);
 	resourceContextKey.set(resource);
-	return resourceContextKey;
 }
 
 function addBasicContextMenu(accessor: ServicesAccessor, widget: HTMLElement, scopedContextKeyService: IScopedContextKeyService, menuId: MenuId, arg: unknown, updateContextKeys?: () => Promise<void>): IDisposable {
diff --git a/src/vs/workbench/contrib/chat/browser/attachments/chatImplicitContext.ts b/src/vs/workbench/contrib/chat/browser/attachments/chatImplicitContext.ts
index 111f7d09b7cb5..5846de6f5ca1d 100644
--- a/src/vs/workbench/contrib/chat/browser/attachments/chatImplicitContext.ts
+++ b/src/vs/workbench/contrib/chat/browser/attachments/chatImplicitContext.ts
@@ -26,7 +26,6 @@ import { IChatService } from '../../common/chatService/chatService.js';
 import { IChatRequestImplicitVariableEntry, IChatRequestVariableEntry, isStringImplicitContextValue, StringChatContextValue } from '../../common/attachments/chatVariableEntries.js';
 import { ChatAgentLocation } from '../../common/constants.js';
 import { ILanguageModelIgnoredFilesService } from '../../common/ignoredFiles.js';
-import { getPromptsTypeForLanguageId } from '../../common/promptSyntax/promptTypes.js';
 import { IChatWidget, IChatWidgetService } from '../chat.js';
 import { IChatContextService } from '../contextContrib/chatContextService.js';
 import { ITextModel } from '../../../../../editor/common/model.js';
@@ -258,8 +257,6 @@ export class ChatImplicitContextContribution extends Disposable implements IWork
 			return;
 		}
 
-		const isPromptFile = languageId && getPromptsTypeForLanguageId(languageId) !== undefined;
-
 		const widgets = updateWidget ? [updateWidget] : [...this.chatWidgetService.getWidgetsByLocations(ChatAgentLocation.Chat), ...this.chatWidgetService.getWidgetsByLocations(ChatAgentLocation.EditorInline)];
 		for (const widget of widgets) {
 			if (!widget.input.implicitContext) {
@@ -267,7 +264,7 @@ export class ChatImplicitContextContribution extends Disposable implements IWork
 			}
 			const setting = this._implicitContextEnablement[widget.location];
 			const isFirstInteraction = widget.viewModel?.getItems().length === 0;
-			if ((setting === 'always' || setting === 'first' && isFirstInteraction) && !isPromptFile) { // disable implicit context for prompt files
+			if ((setting === 'always' || setting === 'first' && isFirstInteraction)) {
 				// When there's a non-code active editor (e.g. Settings is open), preserve
 				// existing values so the attachment bar stays visible.
 				// But when there's no active editor at all, clear the values.
diff --git a/src/vs/workbench/contrib/chat/browser/attachments/chatVariables.ts b/src/vs/workbench/contrib/chat/browser/attachments/chatVariables.ts
index 47e1491204420..ffdb625d5c9f1 100644
--- a/src/vs/workbench/contrib/chat/browser/attachments/chatVariables.ts
+++ b/src/vs/workbench/contrib/chat/browser/attachments/chatVariables.ts
@@ -5,11 +5,72 @@
 
 import { IChatVariablesService, IDynamicVariable } from '../../common/attachments/chatVariables.js';
 import { IToolAndToolSetEnablementMap } from '../../common/tools/languageModelToolsService.js';
-import { IChatWidgetService } from '../chat.js';
+import { IChatWidget, IChatWidgetService } from '../chat.js';
 import { ChatDynamicVariableModel } from './chatDynamicVariables.js';
 import { Range } from '../../../../../editor/common/core/range.js';
 import { URI } from '../../../../../base/common/uri.js';
 
+export function getDynamicVariablesForWidget(widget: IChatWidget): ReadonlyArray<IDynamicVariable> {
+	if (!widget.viewModel || !widget.supportsFileReferences) {
+		return [];
+	}
+
+	const model = widget.getContrib<ChatDynamicVariableModel>(ChatDynamicVariableModel.ID);
+	if (!model) {
+		return [];
+	}
+
+	// track for editing state
+	if (widget.viewModel.editing && model.variables.length > 0) {
+		return model.variables;
+	}
+
+	if (widget.input.attachmentModel.attachments.length > 0 && widget.viewModel.editing) {
+		const references: IDynamicVariable[] = [];
+		const editorModel = widget.inputEditor.getModel();
+		const modelTextLength = editorModel?.getValueLength() ?? 0;
+		for (const attachment of widget.input.attachmentModel.attachments) {
+			// If the attachment has a range, it is a dynamic variable
+			if (attachment.range) {
+				if (attachment.range.start >= attachment.range.endExclusive) {
+					continue;
+				}
+
+				if (attachment.range.start < 0 || attachment.range.endExclusive > modelTextLength) {
+					continue;
+				}
+
+				if (!editorModel) {
+					continue;
+				}
+
+				const startPos = editorModel.getPositionAt(attachment.range.start);
+				const endPos = editorModel.getPositionAt(attachment.range.endExclusive);
+
+				const referenceObj: IDynamicVariable = {
+					id: attachment.id,
+					fullName: attachment.name,
+					modelDescription: attachment.modelDescription,
+					range: new Range(startPos.lineNumber, startPos.column, endPos.lineNumber, endPos.column),
+					icon: attachment.icon,
+					isFile: attachment.kind === 'file',
+					isDirectory: attachment.kind === 'directory',
+					data: attachment.value
+				};
+				references.push(referenceObj);
+			}
+		}
+
+		return references.length > 0 ? references : model.variables;
+	}
+
+	return model.variables;
+}
+
+export function getSelectedToolAndToolSetsForWidget(widget: IChatWidget): IToolAndToolSetEnablementMap {
+	return widget.input.selectedToolsModel.entriesMap.get();
+}
+
 export class ChatVariablesService implements IChatVariablesService {
 	declare _serviceBrand: undefined;
 
@@ -18,65 +79,11 @@ export class ChatVariablesService implements IChatVariablesService {
 	) { }
 
 	getDynamicVariables(sessionResource: URI): ReadonlyArray<IDynamicVariable> {
-		// This is slightly wrong... the parser pulls dynamic references from the input widget, but there is no guarantee that message came from the input here.
-		// Need to ...
-		// - Parser takes list of dynamic references (annoying)
-		// - Or the parser is known to implicitly act on the input widget, and we need to call it before calling the chat service (maybe incompatible with the future, but easy)
 		const widget = this.chatWidgetService.getWidgetBySessionResource(sessionResource);
-		if (!widget || !widget.viewModel || !widget.supportsFileReferences) {
-			return [];
-		}
-
-		const model = widget.getContrib<ChatDynamicVariableModel>(ChatDynamicVariableModel.ID);
-		if (!model) {
+		if (!widget) {
 			return [];
 		}
-
-		// track for editing state
-		if (widget.viewModel.editing && model.variables.length > 0) {
-			return model.variables;
-		}
-
-		if (widget.input.attachmentModel.attachments.length > 0 && widget.viewModel.editing) {
-			const references: IDynamicVariable[] = [];
-			const editorModel = widget.inputEditor.getModel();
-			const modelTextLength = editorModel?.getValueLength() ?? 0;
-			for (const attachment of widget.input.attachmentModel.attachments) {
-				// If the attachment has a range, it is a dynamic variable
-				if (attachment.range) {
-					if (attachment.range.start >= attachment.range.endExclusive) {
-						continue;
-					}
-
-					if (attachment.range.start < 0 || attachment.range.endExclusive > modelTextLength) {
-						continue;
-					}
-
-					if (!editorModel) {
-						continue;
-					}
-
-					const startPos = editorModel.getPositionAt(attachment.range.start);
-					const endPos = editorModel.getPositionAt(attachment.range.endExclusive);
-
-					const referenceObj: IDynamicVariable = {
-						id: attachment.id,
-						fullName: attachment.name,
-						modelDescription: attachment.modelDescription,
-						range: new Range(startPos.lineNumber, startPos.column, endPos.lineNumber, endPos.column),
-						icon: attachment.icon,
-						isFile: attachment.kind === 'file',
-						isDirectory: attachment.kind === 'directory',
-						data: attachment.value
-					};
-					references.push(referenceObj);
-				}
-			}
-
-			return references.length > 0 ? references : model.variables;
-		}
-
-		return model.variables;
+		return getDynamicVariablesForWidget(widget);
 	}
 
 	getSelectedToolAndToolSets(sessionResource: URI): IToolAndToolSetEnablementMap {
@@ -84,7 +91,6 @@ export class ChatVariablesService implements IChatVariablesService {
 		if (!widget) {
 			return new Map();
 		}
-		return widget.input.selectedToolsModel.entriesMap.get();
-
+		return getSelectedToolAndToolSetsForWidget(widget);
 	}
 }
diff --git a/src/vs/workbench/contrib/chat/browser/chat.contribution.ts b/src/vs/workbench/contrib/chat/browser/chat.contribution.ts
index 1f0c66b25c4be..ae0171f8dbb39 100644
--- a/src/vs/workbench/contrib/chat/browser/chat.contribution.ts
+++ b/src/vs/workbench/contrib/chat/browser/chat.contribution.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Event } from '../../../../base/common/event.js';
-import { Disposable, DisposableMap } from '../../../../base/common/lifecycle.js';
+import { Disposable, DisposableMap, DisposableStore } from '../../../../base/common/lifecycle.js';
 import { Schemas } from '../../../../base/common/network.js';
 import { isMacintosh } from '../../../../base/common/platform.js';
 import { PolicyCategory } from '../../../../base/common/policy.js';
@@ -16,6 +16,7 @@ import { Extensions as ConfigurationExtensions, ConfigurationScope, IConfigurati
 import { SyncDescriptor } from '../../../../platform/instantiation/common/descriptors.js';
 import { InstantiationType, registerSingleton } from '../../../../platform/instantiation/common/extensions.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
+import { IContextKey, IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
 import { McpAccessValue, McpAutoStartValue, mcpAccessConfig, mcpAutoStartConfig, mcpGalleryServiceEnablementConfig, mcpGalleryServiceUrlConfig, mcpAppsEnabledConfig } from '../../../../platform/mcp/common/mcpManagement.js';
 import product from '../../../../platform/product/common/product.js';
 import { Registry } from '../../../../platform/registry/common/platform.js';
@@ -25,7 +26,10 @@ import { IWorkbenchContribution, WorkbenchPhase, registerWorkbenchContribution2
 import { EditorExtensions, IEditorFactoryRegistry } from '../../../common/editor.js';
 import { IWorkbenchAssignmentService } from '../../../services/assignment/common/assignmentService.js';
 import { ChatEntitlement, IChatEntitlementService } from '../../../services/chat/common/chatEntitlementService.js';
+import { IEditorService } from '../../../services/editor/common/editorService.js';
 import { IEditorResolverService, RegisteredEditorPriority } from '../../../services/editor/common/editorResolverService.js';
+import { IPathService } from '../../../services/path/common/pathService.js';
+import { IViewsService } from '../../../services/views/common/viewsService.js';
 import { AddConfigurationType, AssistedTypes } from '../../mcp/browser/mcpCommandsAddConfiguration.js';
 import { allDiscoverySources, discoverySourceSettingsLabel, mcpDiscoverySection, mcpServerSamplingSection } from '../../mcp/common/mcpConfiguration.js';
 import { ChatAgentNameService, ChatAgentService, IChatAgentNameService, IChatAgentService } from '../common/participants/chatAgents.js';
@@ -34,7 +38,7 @@ import '../common/widget/chatColors.js';
 import { IChatEditingService } from '../common/editing/chatEditingService.js';
 import { IChatLayoutService } from '../common/widget/chatLayoutService.js';
 import { ChatModeService, IChatMode, IChatModeService } from '../common/chatModes.js';
-import { ChatResponseResourceFileSystemProvider } from '../common/widget/chatResponseResourceFileSystemProvider.js';
+import { ChatResponseResourceFileSystemProvider, ChatResponseResourceWorkbenchContribution, IChatResponseResourceFileSystemProvider } from '../common/widget/chatResponseResourceFileSystemProvider.js';
 import { IChatService } from '../common/chatService/chatService.js';
 import { ChatService } from '../common/chatService/chatServiceImpl.js';
 import { IChatSessionsService } from '../common/chatSessionsService.js';
@@ -43,7 +47,7 @@ import { ChatTodoListService, IChatTodoListService } from '../common/tools/chatT
 import { ChatTransferService, IChatTransferService } from '../common/model/chatTransferService.js';
 import { IChatVariablesService } from '../common/attachments/chatVariables.js';
 import { ChatWidgetHistoryService, IChatWidgetHistoryService } from '../common/widget/chatWidgetHistoryService.js';
-import { AgentsControlClickBehavior, ChatConfiguration, ChatNotificationMode } from '../common/constants.js';
+import { ChatAgentLocation, ChatConfiguration, ChatNotificationMode } from '../common/constants.js';
 import { ILanguageModelIgnoredFilesService, LanguageModelIgnoredFilesService } from '../common/ignoredFiles.js';
 import { ILanguageModelsService, LanguageModelsService } from '../common/languageModels.js';
 import { ILanguageModelStatsService, LanguageModelStatsService } from '../common/languageModelStats.js';
@@ -51,11 +55,12 @@ import { ILanguageModelToolsConfirmationService } from '../common/tools/language
 import { ILanguageModelToolsService } from '../common/tools/languageModelToolsService.js';
 import { agentPluginDiscoveryRegistry, IAgentPluginService } from '../common/plugins/agentPluginService.js';
 import { ChatPromptFilesExtensionPointHandler } from '../common/promptSyntax/chatPromptFilesContribution.js';
-import { PromptsConfig } from '../common/promptSyntax/config/config.js';
-import { INSTRUCTIONS_DEFAULT_SOURCE_FOLDER, INSTRUCTION_FILE_EXTENSION, LEGACY_MODE_DEFAULT_SOURCE_FOLDER, LEGACY_MODE_FILE_EXTENSION, PROMPT_DEFAULT_SOURCE_FOLDER, PROMPT_FILE_EXTENSION, DEFAULT_SKILL_SOURCE_FOLDERS, AGENTS_SOURCE_FOLDER, AGENT_FILE_EXTENSION, SKILL_FILENAME, CLAUDE_AGENTS_SOURCE_FOLDER, DEFAULT_HOOK_FILE_PATHS, DEFAULT_INSTRUCTIONS_SOURCE_FOLDERS } from '../common/promptSyntax/config/promptFileLocations.js';
+import { isTildePath, PromptsConfig } from '../common/promptSyntax/config/config.js';
+import { INSTRUCTIONS_DEFAULT_SOURCE_FOLDER, INSTRUCTION_FILE_EXTENSION, LEGACY_MODE_DEFAULT_SOURCE_FOLDER, LEGACY_MODE_FILE_EXTENSION, PROMPT_DEFAULT_SOURCE_FOLDER, PROMPT_FILE_EXTENSION, DEFAULT_SKILL_SOURCE_FOLDERS, AGENTS_SOURCE_FOLDER, AGENT_FILE_EXTENSION, SKILL_FILENAME, CLAUDE_AGENTS_SOURCE_FOLDER, DEFAULT_HOOK_FILE_PATHS, DEFAULT_INSTRUCTIONS_SOURCE_FOLDERS, PromptFileSource, COPILOT_USER_AGENTS_SOURCE_FOLDER } from '../common/promptSyntax/config/promptFileLocations.js';
 import { PromptLanguageFeaturesProvider } from '../common/promptSyntax/promptFileContributions.js';
-import { AGENT_DOCUMENTATION_URL, INSTRUCTIONS_DOCUMENTATION_URL, PROMPT_DOCUMENTATION_URL, SKILL_DOCUMENTATION_URL, HOOK_DOCUMENTATION_URL } from '../common/promptSyntax/promptTypes.js';
-import { hookFileSchema, HOOK_SCHEMA_URI, HOOK_FILE_GLOB } from '../common/promptSyntax/hookSchema.js';
+import { AGENT_DOCUMENTATION_URL, INSTRUCTIONS_DOCUMENTATION_URL, PROMPT_DOCUMENTATION_URL, SKILL_DOCUMENTATION_URL, HOOK_DOCUMENTATION_URL, PromptsType } from '../common/promptSyntax/promptTypes.js';
+import { hookFileSchema, HOOK_SCHEMA_URI } from '../common/promptSyntax/hookSchema.js';
+import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { Extensions as JSONExtensions, IJSONContributionRegistry } from '../../../../platform/jsonschemas/common/jsonContributionRegistry.js';
 import { IPromptsService } from '../common/promptSyntax/service/promptsService.js';
 import { PromptsService } from '../common/promptSyntax/service/promptsServiceImpl.js';
@@ -89,16 +94,18 @@ import { registerChatTitleActions } from './actions/chatTitleActions.js';
 import { registerChatElicitationActions } from './actions/chatElicitationActions.js';
 import { registerChatToolActions } from './actions/chatToolActions.js';
 import { ChatTransferContribution } from './actions/chatTransfer.js';
-import { registerChatOpenDebugPanelAction } from './actions/chatOpenDebugPanelAction.js';
+import { registerChatOpenAgentDebugPanelAction } from './actions/chatOpenAgentDebugPanelAction.js';
 import { IChatDebugService } from '../common/chatDebugService.js';
 import { ChatDebugServiceImpl } from '../common/chatDebugServiceImpl.js';
+import { ChatImageCarouselService, IChatImageCarouselService } from './chatImageCarouselService.js';
 import { ChatDebugEditor } from './chatDebug/chatDebugEditor.js';
 import { PromptsDebugContribution } from './promptsDebugContribution.js';
 import { ChatDebugEditorInput, ChatDebugEditorInputSerializer } from './chatDebug/chatDebugEditorInput.js';
 import './agentSessions/agentSessions.contribution.js';
-import { backgroundAgentDisplayName } from './agentSessions/agentSessions.js';
 
-import { IChatAccessibilityService, IChatCodeBlockContextProviderService, IChatWidgetService, IQuickChatService } from './chat.js';
+import { ChatContextKeys } from '../common/actions/chatContextKeys.js';
+
+import { ChatViewId, IChatAccessibilityService, IChatCodeBlockContextProviderService, IChatWidgetService, IQuickChatService, isIChatResourceViewContext, isIChatViewViewContext } from './chat.js';
 import { ChatAccessibilityService } from './accessibility/chatAccessibilityService.js';
 import './attachments/chatAttachmentModel.js';
 import './widget/input/chatStatusWidget.js';
@@ -140,10 +147,16 @@ import './widget/input/editor/chatInputEditorContrib.js';
 import './widget/input/editor/chatInputEditorHover.js';
 import { LanguageModelToolsConfirmationService } from './tools/languageModelToolsConfirmationService.js';
 import { LanguageModelToolsService, globalAutoApproveDescription } from './tools/languageModelToolsService.js';
-import { AgentPluginService, ConfiguredAgentPluginDiscovery } from '../common/plugins/agentPluginServiceImpl.js';
+import { AgentPluginService, ConfiguredAgentPluginDiscovery, MarketplaceAgentPluginDiscovery } from '../common/plugins/agentPluginServiceImpl.js';
+import { IAgentPluginRepositoryService } from '../common/plugins/agentPluginRepositoryService.js';
 import { IPluginInstallService } from '../common/plugins/pluginInstallService.js';
 import { IPluginMarketplaceService, PluginMarketplaceService } from '../common/plugins/pluginMarketplaceService.js';
+import { WorkspacePluginSettingsService, IWorkspacePluginSettingsService } from '../common/plugins/workspacePluginSettingsService.js';
 import { AgentPluginsViewsContribution } from './agentPluginsView.js';
+import { AgentPluginRecommendations } from './claudePluginRecommendations.js';
+import { AgentPluginEditor } from './agentPluginEditor/agentPluginEditor.js';
+import { AgentPluginEditorInput } from './agentPluginEditor/agentPluginEditorInput.js';
+import { AgentPluginRepositoryService } from './agentPluginRepositoryService.js';
 import { PluginInstallService } from './pluginInstallService.js';
 import './promptSyntax/promptCodingAgentActionContribution.js';
 import './promptSyntax/promptToolsCodeLensProvider.js';
@@ -167,7 +180,6 @@ const toolReferenceNameEnumDescriptions: string[] = [];
 // Register JSON schema for hook files
 const jsonContributionRegistry = Registry.as<IJSONContributionRegistry>(JSONExtensions.JSONContribution);
 jsonContributionRegistry.registerSchema(HOOK_SCHEMA_URI, hookFileSchema);
-jsonContributionRegistry.registerSchemaAssociation(HOOK_SCHEMA_URI, HOOK_FILE_GLOB);
 
 // Register configuration
 const configurationRegistry = Registry.as<IConfigurationRegistry>(ConfigurationExtensions.Configuration);
@@ -176,6 +188,12 @@ configurationRegistry.registerConfiguration({
 	title: nls.localize('interactiveSessionConfigurationTitle', "Chat"),
 	type: 'object',
 	properties: {
+		'chat.experimentalSessionsWindowOverride': {
+			type: 'boolean',
+			description: nls.localize('chat.experimentalSessionsWindowOverride', "When true, enables sessions-window-specific behavior for extensions."),
+			default: false,
+			tags: ['experimental'],
+		},
 		'chat.fontSize': {
 			type: 'number',
 			description: nls.localize('chat.fontSize', "Controls the font size in pixels in chat messages."),
@@ -214,20 +232,6 @@ configurationRegistry.registerConfiguration({
 			description: nls.localize('interactiveSession.editor.lineHeight', "Controls the line height in pixels in chat codeblocks. Use 0 to compute the line height from the font size."),
 			default: 0
 		},
-		[ChatConfiguration.AgentsControlClickBehavior]: {
-			type: 'string',
-			enum: [AgentsControlClickBehavior.Default, AgentsControlClickBehavior.Cycle],
-			enumDescriptions: [
-				nls.localize('chat.agentsControl.clickBehavior.default', "Clicking chat icon toggles chat visibility."),
-				nls.localize('chat.agentsControl.clickBehavior.cycle', "Clicking chat icon cycles through: show chat, maximize chat, hide chat. This requires chat to be contained in the secondary sidebar."),
-			],
-			markdownDescription: nls.localize('chat.agentsControl.clickBehavior', "Controls the behavior when clicking on the chat icon in the command center."),
-			default: AgentsControlClickBehavior.Default, // TODO@bpasero figure out the default
-			tags: ['experimental'],
-			experiment: {
-				mode: 'auto'
-			}
-		},
 		[ChatConfiguration.AgentStatusEnabled]: {
 			type: 'boolean',
 			markdownDescription: nls.localize('chat.agentsControl.enabled', "Controls whether the 'Agent Status' indicator is shown in the title bar command center. Enabling this setting will automatically enable {0}. The unread/in-progress session indicators require {1} to be enabled.", '`#window.commandCenter#`', '`#chat.viewSessions.enabled#`'),
@@ -261,6 +265,10 @@ configurationRegistry.registerConfiguration({
 			},
 			default: {
 				'panel': 'always',
+			},
+			tags: ['experimental'],
+			experiment: {
+				mode: 'startup'
 			}
 		},
 		'chat.implicitContext.suggestedContext': {
@@ -362,11 +370,17 @@ configurationRegistry.registerConfiguration({
 		},
 		[ChatConfiguration.AutoReply]: {
 			default: false,
-			markdownDescription: nls.localize('chat.autoReply.description', "Automatically answer chat question carousels using the current model. This is an advanced setting and can lead to unintended choices or actions based on incomplete context."),
+			markdownDescription: nls.localize('chat.autoReply.description', "Automatically skip question carousels by telling the agent that the user is not available and to use its best judgment. This is an advanced setting and can lead to unintended choices or actions based on incomplete context."),
 			type: 'boolean',
 			scope: ConfigurationScope.APPLICATION_MACHINE,
 			tags: ['experimental', 'advanced'],
 		},
+		[ChatConfiguration.AutopilotEnabled]: {
+			type: 'boolean',
+			markdownDescription: nls.localize('chat.autopilot.enabled', "Controls whether the Autopilot mode is available in the permissions picker. When enabled, Autopilot auto-approves all tool calls and continues until the task is done."),
+			default: true,
+			tags: ['experimental'],
+		},
 		[ChatConfiguration.GlobalAutoApprove]: {
 			default: false,
 			markdownDescription: globalAutoApproveDescription.value,
@@ -403,7 +417,10 @@ configurationRegistry.registerConfiguration({
 			}
 		},
 		[ChatConfiguration.AutoApprovedUrls]: {
-			default: {},
+			default: {
+				'https://code.visualstudio.com': true,
+				'https://github.com/microsoft/vscode/wiki/*': true,
+			},
 			markdownDescription: nls.localize('chat.tools.fetchPage.approvedUrls', "Controls which URLs are automatically approved when requested by chat tools. Keys are URL patterns and values can be `true` to approve both requests and responses, `false` to deny, or an object with `approveRequest` and `approveResponse` properties for granular control.\n\nExamples:\n- `\"https://example.com\": true` - Approve all requests to example.com\n- `\"https://*.example.com\": true` - Approve all requests to any subdomain of example.com\n- `\"https://example.com/api/*\": { \"approveRequest\": true, \"approveResponse\": false }` - Approve requests but not responses for example.com/api paths"),
 			type: 'object',
 			additionalProperties: {
@@ -466,6 +483,12 @@ configurationRegistry.registerConfiguration({
 			type: 'boolean',
 			tags: ['experimental']
 		},
+		[ChatConfiguration.ImageCarouselEnabled]: {
+			default: false,
+			description: nls.localize('chat.imageCarousel.enabled', "Controls whether clicking an image attachment in chat opens the image carousel viewer."),
+			type: 'boolean',
+			tags: ['experimental']
+		},
 		'chat.undoRequests.restoreInput': {
 			default: true,
 			markdownDescription: nls.localize('chat.undoRequests.restoreInput', "Controls whether the input of the chat should be restored when an undo request is made. The input will be filled with the text of the request that was restored."),
@@ -627,11 +650,6 @@ configurationRegistry.registerConfiguration({
 				mode: 'startup'
 			}
 		},
-		[ChatConfiguration.Edits2Enabled]: {
-			type: 'boolean',
-			description: nls.localize('chat.edits2Enabled', "Enable the new Edits mode that is based on tool-calling. When this is enabled, models that don't support tool-calling are unavailable for Edits mode."),
-			default: false,
-		},
 		[ChatConfiguration.ExtensionToolsEnabled]: {
 			type: 'boolean',
 			description: nls.localize('chat.extensionToolsEnabled', "Enable using tools contributed by third-party extensions."),
@@ -648,12 +666,17 @@ configurationRegistry.registerConfiguration({
 				},
 			}
 		},
-		[ChatConfiguration.PluginPaths]: {
+		[ChatConfiguration.PluginsEnabled]: {
+			type: 'boolean',
+			description: nls.localize('chat.plugins.enabled', "Enable agent plugin integration in chat."),
+			default: true,
+			tags: ['preview'],
+		},
+		[ChatConfiguration.PluginLocations]: {
 			type: 'object',
 			additionalProperties: { type: 'boolean' },
 			restricted: true,
-			markdownDescription: nls.localize('chat.plugins.paths', "Plugin directories to discover. Each key is a path that points directly to a plugin folder, and the value enables (`true`) or disables (`false`) it. Paths can be absolute or relative to the workspace root."),
-			default: {},
+			markdownDescription: nls.localize('chat.pluginLocations', "Plugin directories to discover. Each key is a path that points directly to a plugin folder, and the value enables (`true`) or disables (`false`) it. Paths can be absolute, relative to the workspace root, or start with `~/` for the user's home directory."),
 			scope: ConfigurationScope.MACHINE,
 			tags: ['experimental'],
 		},
@@ -662,7 +685,7 @@ configurationRegistry.registerConfiguration({
 			items: {
 				type: 'string',
 			},
-			markdownDescription: nls.localize('chat.plugins.marketplaces', "GitHub repositories to use as plugin marketplaces. Each entry should be in `owner/repo` format."),
+			markdownDescription: nls.localize('chat.plugins.marketplaces', "Plugin marketplaces to query. Entries may be GitHub shorthand (`owner/repo`), direct Git repository URIs (`https://...git`, `ssh://...git`, or `git@host:path.git`), or local repository URIs (`file:///...`). Equivalent GitHub shorthand and URI entries are deduplicated."),
 			default: ['github/copilot-plugins', 'github/awesome-copilot'],
 			scope: ConfigurationScope.APPLICATION,
 			tags: ['experimental'],
@@ -718,6 +741,17 @@ configurationRegistry.registerConfiguration({
 			tags: ['experimental'],
 			experiment: {
 				mode: 'auto'
+			},
+			policy: {
+				name: 'DeprecatedEditModeHidden',
+				category: PolicyCategory.InteractiveSession,
+				minimumVersion: '1.112',
+				localization: {
+					description: {
+						key: 'chat.editMode.hidden',
+						value: nls.localize('chat.editMode.hidden', "When enabled, hides the Edit mode from the chat mode picker."),
+					}
+				}
 			}
 		},
 		[ChatConfiguration.EnableMath]: {
@@ -884,6 +918,7 @@ configurationRegistry.registerConfiguration({
 			default: {
 				[AGENTS_SOURCE_FOLDER]: true,
 				[CLAUDE_AGENTS_SOURCE_FOLDER]: true,
+				[COPILOT_USER_AGENTS_SOURCE_FOLDER]: true,
 			},
 			additionalProperties: { type: 'boolean' },
 			propertyNames: {
@@ -970,6 +1005,15 @@ configurationRegistry.registerConfiguration({
 			disallowConfigurationDefault: true,
 			tags: ['prompts', 'reusable prompts', 'prompt snippets', 'instructions']
 		},
+		[PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS]: {
+			type: 'boolean',
+			title: nls.localize('chat.useCustomizationsInParentRepos.title', "Use Customizations in Parent Repositories",),
+			markdownDescription: nls.localize('chat.useCustomizationsInParentRepos.description', "Controls whether to use chat customization files in parent repositories.",),
+			default: false,
+			restricted: true,
+			disallowConfigurationDefault: true,
+			tags: ['prompts', 'reusable prompts', 'prompt snippets', 'instructions']
+		},
 		[PromptsConfig.SKILLS_LOCATION_KEY]: {
 			type: 'object',
 			title: nls.localize('chat.agentSkillsLocations.title', "Agent Skills Locations",),
@@ -1059,6 +1103,15 @@ configurationRegistry.registerConfiguration({
 			disallowConfigurationDefault: true,
 			tags: ['preview', 'prompts', 'hooks', 'agent']
 		},
+		[PromptsConfig.USE_CUSTOM_AGENT_HOOKS]: {
+			type: 'boolean',
+			title: nls.localize('chat.useCustomAgentHooks.title', "Use Custom Agent Hooks",),
+			markdownDescription: nls.localize('chat.useCustomAgentHooks.description', "Controls whether hooks defined in custom agent frontmatter are parsed and executed. When disabled, hooks from agent files are ignored.",),
+			default: false,
+			restricted: true,
+			disallowConfigurationDefault: true,
+			tags: ['preview', 'prompts', 'hooks', 'agent']
+		},
 		[PromptsConfig.PROMPT_FILES_SUGGEST_KEY]: {
 			type: 'object',
 			scope: ConfigurationScope.RESOURCE,
@@ -1129,7 +1182,7 @@ configurationRegistry.registerConfiguration({
 		},
 		[ChatConfiguration.SimpleTerminalCollapsible]: {
 			type: 'boolean',
-			default: product.quality !== 'stable',
+			default: true,
 			markdownDescription: nls.localize('chat.tools.terminal.simpleCollapsible', "When enabled, terminal tool calls are always displayed in a collapsible container with a simplified view."),
 			tags: ['experimental'],
 		},
@@ -1227,17 +1280,17 @@ configurationRegistry.registerConfiguration({
 		[ChatConfiguration.SubagentToolCustomAgents]: {
 			type: 'boolean',
 			description: nls.localize('chat.subagentTool.customAgents', "Whether the runSubagent tool is able to use custom agents. When enabled, the tool can take the name of a custom agent, but it must be given the exact name of the agent."),
-			default: false,
-			tags: ['experimental'],
+			default: true,
 			experiment: {
 				mode: 'auto'
 			}
 		},
 		[ChatConfiguration.ChatCustomizationMenuEnabled]: {
 			type: 'boolean',
-			description: nls.localize('chat.aiCustomizationMenu.enabled', "Controls whether the Chat Customization Menu is shown in the Manage menu and Command Palette. When disabled, the Chat Customizations editor and related commands are hidden."),
+			tags: ['preview'],
+			description: nls.localize('chat.aiCustomizationMenu.enabled', "Controls whether the Chat Customizations editor is available in the Command Palette. When disabled, the Chat Customizations editor and related commands are hidden."),
 			default: true,
-		}
+		},
 	}
 });
 Registry.as<IEditorPaneRegistry>(EditorExtensions.EditorPane).registerEditorPane(
@@ -1260,6 +1313,16 @@ Registry.as<IEditorPaneRegistry>(EditorExtensions.EditorPane).registerEditorPane
 		new SyncDescriptor(ChatDebugEditorInput)
 	]
 );
+Registry.as<IEditorPaneRegistry>(EditorExtensions.EditorPane).registerEditorPane(
+	EditorPaneDescriptor.create(
+		AgentPluginEditor,
+		AgentPluginEditor.ID,
+		nls.localize('agentPlugin', "Agent Plugin")
+	),
+	[
+		new SyncDescriptor(AgentPluginEditorInput)
+	]
+);
 Registry.as<IConfigurationMigrationRegistry>(Extensions.ConfigurationMigration).registerConfigurationMigrations([
 	{
 		key: 'chat.experimental.detectParticipant.enabled',
@@ -1307,6 +1370,13 @@ Registry.as<IConfigurationMigrationRegistry>(Extensions.ConfigurationMigration).
 			return [];
 		}
 	},
+	{
+		key: 'chat.plugins.paths',
+		migrateFn: (value: unknown, _accessor) => ([
+			['chat.plugins.paths', { value: undefined }],
+			[ChatConfiguration.PluginLocations, { value }]
+		])
+	},
 ]);
 
 class ChatResolverContribution extends Disposable {
@@ -1395,14 +1465,17 @@ class ChatDebugResolverContribution implements IWorkbenchContribution {
 class ChatAgentSettingContribution extends Disposable implements IWorkbenchContribution {
 
 	static readonly ID = 'workbench.contrib.chatAgentSetting';
+	private readonly newChatButtonExperimentIcon;
 
 	constructor(
 		@IWorkbenchAssignmentService private readonly experimentService: IWorkbenchAssignmentService,
 		@IChatEntitlementService private readonly entitlementService: IChatEntitlementService,
+		@IContextKeyService private readonly contextKeyService: IContextKeyService,
 	) {
 		super();
+		this.newChatButtonExperimentIcon = ChatContextKeys.newChatButtonExperimentIcon.bindTo(this.contextKeyService);
 		this.registerMaxRequestsSetting();
-		this.registerBackgroundAgentDisplayName();
+		this.registerNewChatButtonIcon();
 	}
 
 
@@ -1413,7 +1486,6 @@ class ChatAgentSettingContribution extends Disposable implements IWorkbenchContr
 				'chatAgentMaxRequestsFree' :
 				'chatAgentMaxRequestsPro';
 			this.experimentService.getTreatment<number>(treatmentId).then((value) => {
-				const defaultValue = value ?? (this.entitlementService.entitlement === ChatEntitlement.Free ? 25 : 25);
 				const node: IConfigurationNode = {
 					id: 'chatSidebar',
 					title: nls.localize('interactiveSessionConfigurationTitle', "Chat"),
@@ -1422,7 +1494,7 @@ class ChatAgentSettingContribution extends Disposable implements IWorkbenchContr
 						'chat.agent.maxRequests': {
 							type: 'number',
 							markdownDescription: nls.localize('chat.agent.maxRequests', "The maximum number of requests to allow per-turn when using an agent. When the limit is reached, will ask to confirm to continue."),
-							default: defaultValue,
+							default: value ?? 50,
 							order: 2,
 						},
 					}
@@ -1434,15 +1506,71 @@ class ChatAgentSettingContribution extends Disposable implements IWorkbenchContr
 		this._register(Event.runAndSubscribe(Event.debounce(this.entitlementService.onDidChangeEntitlement, () => { }, 1000), () => registerMaxRequestsSetting()));
 	}
 
-	private registerBackgroundAgentDisplayName(): void {
-		this.experimentService.getTreatment<string>('backgroundAgentDisplayName').then((value) => {
-			if (value) {
-				backgroundAgentDisplayName.set(value, undefined);
+	private registerNewChatButtonIcon(): void {
+		this.experimentService.getTreatment<string>('chatNewButtonIcon').then((value) => {
+			const supportedValues = ['copilot', 'new-session', 'comment'];
+			if (typeof value === 'string' && supportedValues.includes(value)) {
+				this.newChatButtonExperimentIcon.set(value);
+			} else {
+				this.newChatButtonExperimentIcon.reset();
 			}
 		});
 	}
 }
 
+class ChatForegroundSessionCountContribution extends Disposable implements IWorkbenchContribution {
+
+	static readonly ID = 'workbench.contrib.chatForegroundSessionCount';
+
+	private readonly foregroundSessionCountContextKey: IContextKey<number>;
+
+	constructor(
+		@IContextKeyService private readonly contextKeyService: IContextKeyService,
+		@IChatWidgetService private readonly chatWidgetService: IChatWidgetService,
+		@IViewsService private readonly viewsService: IViewsService,
+		@IEditorService private readonly editorService: IEditorService,
+	) {
+		super();
+		this.foregroundSessionCountContextKey = ChatContextKeys.foregroundSessionCount.bindTo(this.contextKeyService);
+
+		this._register(this.chatWidgetService.onDidAddWidget(() => {
+			this.updateForegroundSessionCount();
+		}));
+
+		this._register(this.editorService.onDidVisibleEditorsChange(() => {
+			this.updateForegroundSessionCount();
+		}));
+
+		this._register(Event.filter(this.viewsService.onDidChangeViewVisibility, e => e.id === ChatViewId)(() => {
+			this.updateForegroundSessionCount();
+		}));
+
+		this.updateForegroundSessionCount();
+	}
+
+	private updateForegroundSessionCount(): void {
+		let count = this.viewsService.isViewVisible(ChatViewId) ? 1 : 0;
+
+		for (const widget of this.chatWidgetService.getWidgetsByLocations(ChatAgentLocation.Chat)) {
+			if (widget.domNode.offsetParent === null) {
+				continue;
+			}
+
+			if (isIChatViewViewContext(widget.viewContext)) {
+				continue;
+			}
+
+			if (isIChatResourceViewContext(widget.viewContext) && widget.viewContext.isQuickChat) {
+				continue;
+			}
+
+			count++;
+		}
+
+		this.foregroundSessionCountContextKey.set(count);
+	}
+}
+
 
 /**
  * Given builtin and custom modes, returns only the custom mode IDs that should have actions registered.
@@ -1530,6 +1658,55 @@ class ChatAgentActionsContribution extends Disposable implements IWorkbenchContr
 	}
 }
 
+class HookSchemaAssociationContribution extends Disposable implements IWorkbenchContribution {
+
+	static readonly ID = 'workbench.contrib.hookSchemaAssociation';
+
+	private readonly _registrations = this._register(new DisposableStore());
+
+	constructor(
+		@IConfigurationService private readonly _configurationService: IConfigurationService,
+		@IPathService private readonly _pathService: IPathService,
+	) {
+		super();
+		this._updateAssociations();
+		this._register(this._configurationService.onDidChangeConfiguration(e => {
+			if (e.affectsConfiguration(PromptsConfig.HOOKS_LOCATION_KEY)) {
+				this._updateAssociations();
+			}
+		}));
+	}
+
+	private async _updateAssociations(): Promise<void> {
+		this._registrations.clear();
+
+		const folders = PromptsConfig.promptSourceFolders(this._configurationService, PromptsType.hook);
+		const userHomeUri = await this._pathService.userHome();
+		const userHome = userHomeUri.fsPath ?? userHomeUri.path;
+
+		for (const folder of folders) {
+			// Skip Claude settings files — they use a different schema format
+			if (folder.source === PromptFileSource.ClaudeWorkspace || folder.source === PromptFileSource.ClaudeWorkspaceLocal || folder.source === PromptFileSource.ClaudePersonal) {
+				continue;
+			}
+
+			// Expand tilde paths to absolute paths so the JSON language service can match them
+			const resolvedPath = isTildePath(folder.path)
+				? userHome + folder.path.substring(1)
+				: folder.path;
+
+			// If it's a specific .json file, use it directly; otherwise treat as directory
+			const glob = resolvedPath.toLowerCase().endsWith('.json')
+				? resolvedPath
+				: `${resolvedPath}/*.json`;
+
+			this._registrations.add(
+				jsonContributionRegistry.registerSchemaAssociation(HOOK_SCHEMA_URI, glob)
+			);
+		}
+	}
+}
+
 class ToolReferenceNamesContribution extends Disposable implements IWorkbenchContribution {
 
 	static readonly ID = 'workbench.contrib.toolReferenceNames';
@@ -1599,7 +1776,9 @@ registerWorkbenchContribution2(BuiltinToolsContribution.ID, BuiltinToolsContribu
 registerWorkbenchContribution2(UsagesToolContribution.ID, UsagesToolContribution, WorkbenchPhase.BlockRestore);
 registerWorkbenchContribution2(RenameToolContribution.ID, RenameToolContribution, WorkbenchPhase.BlockRestore);
 registerWorkbenchContribution2(ChatAgentSettingContribution.ID, ChatAgentSettingContribution, WorkbenchPhase.AfterRestored);
+registerWorkbenchContribution2(ChatForegroundSessionCountContribution.ID, ChatForegroundSessionCountContribution, WorkbenchPhase.AfterRestored);
 registerWorkbenchContribution2(ChatAgentActionsContribution.ID, ChatAgentActionsContribution, WorkbenchPhase.Eventually);
+registerWorkbenchContribution2(HookSchemaAssociationContribution.ID, HookSchemaAssociationContribution, WorkbenchPhase.AfterRestored);
 registerWorkbenchContribution2(ToolReferenceNamesContribution.ID, ToolReferenceNamesContribution, WorkbenchPhase.AfterRestored);
 registerWorkbenchContribution2(ChatAgentRecommendation.ID, ChatAgentRecommendation, WorkbenchPhase.Eventually);
 registerWorkbenchContribution2(ChatEditingEditorAccessibility.ID, ChatEditingEditorAccessibility, WorkbenchPhase.AfterRestored);
@@ -1609,19 +1788,20 @@ registerWorkbenchContribution2(SimpleBrowserOverlay.ID, SimpleBrowserOverlay, Wo
 registerWorkbenchContribution2(ChatEditingEditorContextKeys.ID, ChatEditingEditorContextKeys, WorkbenchPhase.AfterRestored);
 registerWorkbenchContribution2(ChatTransferContribution.ID, ChatTransferContribution, WorkbenchPhase.BlockRestore);
 registerWorkbenchContribution2(ChatContextContributions.ID, ChatContextContributions, WorkbenchPhase.AfterRestored);
-registerWorkbenchContribution2(ChatResponseResourceFileSystemProvider.ID, ChatResponseResourceFileSystemProvider, WorkbenchPhase.AfterRestored);
 registerWorkbenchContribution2(PromptUrlHandler.ID, PromptUrlHandler, WorkbenchPhase.BlockRestore);
 registerWorkbenchContribution2(ChatEditingNotebookFileSystemProviderContrib.ID, ChatEditingNotebookFileSystemProviderContrib, WorkbenchPhase.BlockStartup);
+registerWorkbenchContribution2(ChatResponseResourceWorkbenchContribution.ID, ChatResponseResourceWorkbenchContribution, WorkbenchPhase.AfterRestored);
 registerWorkbenchContribution2(UserToolSetsContributions.ID, UserToolSetsContributions, WorkbenchPhase.Eventually);
 registerWorkbenchContribution2(PromptLanguageFeaturesProvider.ID, PromptLanguageFeaturesProvider, WorkbenchPhase.Eventually);
 registerWorkbenchContribution2(ChatWindowNotifier.ID, ChatWindowNotifier, WorkbenchPhase.AfterRestored);
 registerWorkbenchContribution2(ChatRepoInfoContribution.ID, ChatRepoInfoContribution, WorkbenchPhase.Eventually);
 registerWorkbenchContribution2(AgentPluginsViewsContribution.ID, AgentPluginsViewsContribution, WorkbenchPhase.AfterRestored);
+registerWorkbenchContribution2(AgentPluginRecommendations.ID, AgentPluginRecommendations, WorkbenchPhase.Eventually);
 
 registerChatActions();
 registerChatAccessibilityActions();
 registerChatCopyActions();
-registerChatOpenDebugPanelAction();
+registerChatOpenAgentDebugPanelAction();
 registerChatCodeBlockActions();
 registerChatCodeCompareBlockActions();
 registerChatFileTreeActions();
@@ -1645,7 +1825,9 @@ registerAction2(ConfigureToolSets);
 registerEditorFeature(ChatPasteProvidersFeature);
 
 agentPluginDiscoveryRegistry.register(new SyncDescriptor(ConfiguredAgentPluginDiscovery));
+agentPluginDiscoveryRegistry.register(new SyncDescriptor(MarketplaceAgentPluginDiscovery));
 
+registerSingleton(IChatResponseResourceFileSystemProvider, ChatResponseResourceFileSystemProvider, InstantiationType.Delayed);
 registerSingleton(IChatTransferService, ChatTransferService, InstantiationType.Delayed);
 registerSingleton(IChatService, ChatService, InstantiationType.Delayed);
 registerSingleton(IChatWidgetService, ChatWidgetService, InstantiationType.Delayed);
@@ -1661,6 +1843,8 @@ registerSingleton(IChatAgentNameService, ChatAgentNameService, InstantiationType
 registerSingleton(IChatVariablesService, ChatVariablesService, InstantiationType.Delayed);
 registerSingleton(IAgentPluginService, AgentPluginService, InstantiationType.Delayed);
 registerSingleton(IPluginMarketplaceService, PluginMarketplaceService, InstantiationType.Delayed);
+registerSingleton(IWorkspacePluginSettingsService, WorkspacePluginSettingsService, InstantiationType.Delayed);
+registerSingleton(IAgentPluginRepositoryService, AgentPluginRepositoryService, InstantiationType.Delayed);
 registerSingleton(IPluginInstallService, PluginInstallService, InstantiationType.Delayed);
 registerSingleton(ILanguageModelToolsService, LanguageModelToolsService, InstantiationType.Delayed);
 registerSingleton(ILanguageModelToolsConfirmationService, LanguageModelToolsConfirmationService, InstantiationType.Delayed);
@@ -1680,5 +1864,6 @@ registerSingleton(IChatOutputRendererService, ChatOutputRendererService, Instant
 registerSingleton(IChatLayoutService, ChatLayoutService, InstantiationType.Delayed);
 registerSingleton(IChatTipService, ChatTipService, InstantiationType.Delayed);
 registerSingleton(IChatDebugService, ChatDebugServiceImpl, InstantiationType.Delayed);
+registerSingleton(IChatImageCarouselService, ChatImageCarouselService, InstantiationType.Delayed);
 
 ChatWidget.CONTRIBS.push(ChatDynamicVariableModel);
diff --git a/src/vs/workbench/contrib/chat/browser/chat.ts b/src/vs/workbench/contrib/chat/browser/chat.ts
index ed040379d2a54..9b3fc446d6c13 100644
--- a/src/vs/workbench/contrib/chat/browser/chat.ts
+++ b/src/vs/workbench/contrib/chat/browser/chat.ts
@@ -263,6 +263,7 @@ export interface IChatWidgetViewOptions {
 	enableWorkingSet?: 'explicit' | 'implicit';
 	supportsChangingModes?: boolean;
 	dndContainer?: HTMLElement;
+	inputEditorMinLines?: number;
 	defaultMode?: IChatMode;
 	/**
 	 * Optional delegate for the session target picker.
@@ -288,6 +289,12 @@ export interface IChatWidgetViewOptions {
 	 * redirect to a different workspace rather than executing locally.
 	 */
 	submitHandler?: (query: string, mode: ChatModeKind) => Promise<boolean>;
+
+	/**
+	 * Whether we are running in the sessions window.
+	 * When true, the secondary toolbar (permissions picker) is hidden.
+	 */
+	isSessionsWindow?: boolean;
 }
 
 export interface IChatViewViewContext {
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFileListRenderer.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatCustomizationDiscoveryRenderer.ts
similarity index 66%
rename from src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFileListRenderer.ts
rename to src/vs/workbench/contrib/chat/browser/chatDebug/chatCustomizationDiscoveryRenderer.ts
index d1d1756523b55..1e5a41c1ea38c 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFileListRenderer.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatCustomizationDiscoveryRenderer.ts
@@ -22,7 +22,7 @@ import { ILabelService } from '../../../../../platform/label/common/label.js';
 import { IOpenerService } from '../../../../../platform/opener/common/opener.js';
 import { IChatDebugEventFileListContent } from '../../common/chatDebugService.js';
 import { InlineAnchorWidget } from '../widget/chatContentParts/chatInlineAnchorWidget.js';
-import { setupCollapsibleToggle } from './chatDebugMessageContentRenderer.js';
+import { setupCollapsibleToggle } from './chatDebugCollapsible.js';
 
 const $ = DOM.$;
 
@@ -45,11 +45,14 @@ function getSettingsKeyForDiscoveryType(discoveryType: string): string | undefin
  * Extension files show the extension ID,
  * all other files show the relative (or tildified) parent folder path.
  */
-function getFileLocationLabel(file: { uri: URI; storage?: string; extensionId?: string }, labelService: ILabelService): string {
+function getFileLocationLabel(file: { uri: URI; storage?: string; extensionId?: string }, labelService: ILabelService, discoveryType?: string): string {
 	if (file.extensionId) {
 		return file.extensionId;
 	}
-	return labelService.getUriLabel(dirname(file.uri), { relative: true });
+	// Skills live inside individual skill folders (e.g. .github/skills/foo/SKILL.md),
+	// so group by the parent of the skill folder for a more useful label.
+	const parentDir = discoveryType === 'skill' ? dirname(dirname(file.uri)) : dirname(file.uri);
+	return labelService.getUriLabel(parentDir, { relative: true });
 }
 
 /**
@@ -130,30 +133,10 @@ function setupFileListNavigation(listEl: HTMLElement, rows: { element: HTMLEleme
 	}));
 }
 
-/**
- * Append a location badge to a row. If the file comes from an extension,
- * the badge is a clickable link that opens the extension in the marketplace.
- */
-function appendLocationBadge(row: HTMLElement, file: { extensionId?: string }, badgeText: string, cssClass: string, openerService: IOpenerService, hoverService: IHoverService, disposables: DisposableStore): void {
-	if (file.extensionId) {
-		const link = DOM.append(row, $(`a.${cssClass}.chat-debug-file-list-badge-link`));
-		link.textContent = badgeText;
-		link.tabIndex = -1;
-		disposables.add(hoverService.setupManagedHover(getDefaultHoverDelegate('element'), link, localize('chatDebug.openExtension', "Open {0} in Extensions", file.extensionId)));
-		disposables.add(DOM.addDisposableListener(link, DOM.EventType.CLICK, (e) => {
-			e.preventDefault();
-			e.stopPropagation();
-			openerService.open(URI.parse(`command:extension.open?${encodeURIComponent(JSON.stringify([file.extensionId]))}`), { allowCommands: true });
-		}));
-	} else {
-		DOM.append(row, $(`span.${cssClass}`, undefined, badgeText));
-	}
-}
-
 /**
  * Render a file list resolved content as a rich HTML element.
  */
-export function renderFileListContent(content: IChatDebugEventFileListContent, openerService: IOpenerService, modelService: IModelService, languageService: ILanguageService, hoverService: IHoverService, labelService: ILabelService): { element: HTMLElement; disposables: DisposableStore } {
+export function renderCustomizationDiscoveryContent(content: IChatDebugEventFileListContent, openerService: IOpenerService, modelService: IModelService, languageService: ILanguageService, hoverService: IHoverService, labelService: ILabelService): { element: HTMLElement; disposables: DisposableStore } {
 	const disposables = new DisposableStore();
 	const container = $('div.chat-debug-file-list');
 	container.tabIndex = 0;
@@ -162,66 +145,115 @@ export function renderFileListContent(content: IChatDebugEventFileListContent, o
 	DOM.append(container, $('div.chat-debug-file-list-title', undefined, localize('chatDebug.discoveryResults', "{0} Discovery Results", capitalizedType)));
 	DOM.append(container, $('div.chat-debug-file-list-summary', undefined, localize('chatDebug.totalFiles', "Total files: {0}", content.files.length)));
 
-	// Loaded files
+	// Loaded files - grouped by source location
 	const loaded = content.files.filter(f => f.status === 'loaded');
 	if (loaded.length > 0) {
 		const section = DOM.append(container, $('div.chat-debug-file-list-section'));
 		DOM.append(section, $('div.chat-debug-file-list-section-title', undefined,
 			localize('chatDebug.loadedFiles', "Loaded ({0})", loaded.length)));
 
+		// Group files by location label (extension ID or folder path)
+		const groups = new Map<string, typeof loaded>();
+		for (const file of loaded) {
+			const key = getFileLocationLabel(file, labelService, content.discoveryType);
+			let group = groups.get(key);
+			if (!group) {
+				group = [];
+				groups.set(key, group);
+			}
+			group.push(file);
+		}
+
 		const listEl = DOM.append(section, $('div.chat-debug-file-list-rows'));
 		listEl.setAttribute('role', 'list');
 		listEl.setAttribute('aria-label', localize('chatDebug.loadedFilesList', "Loaded files"));
 
 		const rows: { element: HTMLElement; activate: () => void }[] = [];
-		for (const file of loaded) {
-			const row = DOM.append(listEl, $('div.chat-debug-file-list-row'));
-			DOM.append(row, $(`span.chat-debug-file-list-icon${ThemeIcon.asCSSSelector(Codicon.check)}`));
-			const locationBadgeText = localize('chatDebug.locationBadge', " ({0})", getFileLocationLabel(file, labelService));
-			// Only include location in tooltip when it's an extension ID (path would be redundant)
-			const hoverSuffix = file.extensionId ? locationBadgeText.trim() : undefined;
-			row.appendChild(createInlineFileLink(file.uri, file.name ?? file.uri.path, FileKind.FILE, openerService, modelService, languageService, hoverService, labelService, disposables, hoverSuffix));
-			appendLocationBadge(row, file, locationBadgeText, 'chat-debug-file-list-badge', openerService, hoverService, disposables);
-			const relativeLabel = labelService.getUriLabel(file.uri, { relative: true });
-			row.setAttribute('aria-label', relativeLabel);
-			const uri = file.uri;
-			rows.push({ element: row, activate: () => openerService.open(uri) });
+		for (const [locationLabel, files] of groups) {
+			// Group header - show the source location
+			const groupHeader = DOM.append(listEl, $('div.chat-debug-file-list-group-header'));
+			const firstFile = files[0];
+			if (firstFile.extensionId) {
+				const link = DOM.append(groupHeader, $('a.chat-debug-file-list-group-label.chat-debug-file-list-badge-link'));
+				link.textContent = locationLabel;
+				link.tabIndex = -1;
+				disposables.add(hoverService.setupManagedHover(getDefaultHoverDelegate('element'), link, localize('chatDebug.openExtension', "Open {0} in Extensions", firstFile.extensionId)));
+				disposables.add(DOM.addDisposableListener(link, DOM.EventType.CLICK, (e) => {
+					e.preventDefault();
+					e.stopPropagation();
+					openerService.open(URI.parse(`command:extension.open?${encodeURIComponent(JSON.stringify([firstFile.extensionId]))}`), { allowCommands: true });
+				}));
+			} else {
+				DOM.append(groupHeader, $('span.chat-debug-file-list-group-label', undefined, locationLabel));
+			}
+
+			for (const file of files) {
+				const row = DOM.append(listEl, $('div.chat-debug-file-list-row'));
+				DOM.append(row, $(`span.chat-debug-file-list-icon${ThemeIcon.asCSSSelector(Codicon.check)}`));
+				row.appendChild(createInlineFileLink(file.uri, file.name ?? file.uri.path, FileKind.FILE, openerService, modelService, languageService, hoverService, labelService, disposables));
+				const relativeLabel = labelService.getUriLabel(file.uri, { relative: true });
+				row.setAttribute('aria-label', relativeLabel);
+				const uri = file.uri;
+				rows.push({ element: row, activate: () => openerService.open(uri) });
+			}
 		}
 		setupFileListNavigation(listEl, rows, disposables);
 	}
 
-	// Skipped files
+	// Skipped files - grouped by skip reason
 	const skipped = content.files.filter(f => f.status === 'skipped');
 	if (skipped.length > 0) {
 		const section = DOM.append(container, $('div.chat-debug-file-list-section'));
 		DOM.append(section, $('div.chat-debug-file-list-section-title', undefined,
 			localize('chatDebug.skippedFiles', "Skipped ({0})", skipped.length)));
 
+		// Group files by skip reason
+		const groups = new Map<string, typeof skipped>();
+		for (const file of skipped) {
+			const key = file.skipReason ?? localize('chatDebug.unknown', "unknown");
+			let group = groups.get(key);
+			if (!group) {
+				group = [];
+				groups.set(key, group);
+			}
+			group.push(file);
+		}
+
 		const listEl = DOM.append(section, $('div.chat-debug-file-list-rows'));
 		listEl.setAttribute('role', 'list');
 		listEl.setAttribute('aria-label', localize('chatDebug.skippedFilesList', "Skipped files"));
 
 		const rows: { element: HTMLElement; activate: () => void }[] = [];
-		for (const file of skipped) {
-			const row = DOM.append(listEl, $('div.chat-debug-file-list-row'));
-			DOM.append(row, $(`span.chat-debug-file-list-icon${ThemeIcon.asCSSSelector(Codicon.close)}`));
+		for (const [reasonLabel, files] of groups) {
+			// Group header - show the skip reason
+			const groupHeader = DOM.append(listEl, $('div.chat-debug-file-list-group-header'));
+			DOM.append(groupHeader, $('span.chat-debug-file-list-group-label', undefined, reasonLabel));
+
+			for (const file of files) {
+				const row = DOM.append(listEl, $('div.chat-debug-file-list-row'));
+				DOM.append(row, $(`span.chat-debug-file-list-icon${ThemeIcon.asCSSSelector(Codicon.close)}`));
+
+				// Build per-file detail (error message / duplicate info)
+				let detail = '';
+				if (file.errorMessage) {
+					detail += file.errorMessage;
+				}
+				if (file.duplicateOf) {
+					if (detail) {
+						detail += ', ';
+					}
+					detail += localize('chatDebug.duplicateOf', "duplicate of {0}", file.duplicateOf.path);
+				}
 
-			let reasonText = ` (${file.skipReason ?? localize('chatDebug.unknown', "unknown")}`;
-			if (file.errorMessage) {
-				reasonText += `: ${file.errorMessage}`;
-			}
-			if (file.duplicateOf) {
-				reasonText += localize('chatDebug.duplicateOf', ", duplicate of {0}", file.duplicateOf.path);
+				row.appendChild(createInlineFileLink(file.uri, file.name ?? file.uri.path, FileKind.FILE, openerService, modelService, languageService, hoverService, labelService, disposables));
+				if (detail) {
+					DOM.append(row, $('span.chat-debug-file-list-detail', undefined, ` (${detail})`));
+				}
+				const relativeLabel = labelService.getUriLabel(file.uri, { relative: true });
+				row.setAttribute('aria-label', relativeLabel);
+				const uri = file.uri;
+				rows.push({ element: row, activate: () => openerService.open(uri) });
 			}
-			reasonText += ')';
-			// Only include reason in tooltip when it's an extension file (path-based location is redundant)
-			const skippedHoverSuffix = file.extensionId ? reasonText.trim() : undefined;
-			row.appendChild(createInlineFileLink(file.uri, file.name ?? file.uri.path, FileKind.FILE, openerService, modelService, languageService, hoverService, labelService, disposables, skippedHoverSuffix));
-			appendLocationBadge(row, file, reasonText, 'chat-debug-file-list-detail', openerService, hoverService, disposables);
-			const relativeLabel = labelService.getUriLabel(file.uri, { relative: true });
-			row.setAttribute('aria-label', relativeLabel);
-			const uri = file.uri;
-			rows.push({ element: row, activate: () => openerService.open(uri) });
 		}
 		setupFileListNavigation(listEl, rows, disposables);
 	}
@@ -297,28 +329,58 @@ export function fileListToPlainText(content: IChatDebugEventFileListContent): st
 
 	if (loaded.length > 0) {
 		lines.push(localize('chatDebug.plainText.loaded', "Loaded ({0})", loaded.length));
+		// Group by location
+		const groups = new Map<string, typeof loaded>();
 		for (const f of loaded) {
-			const label = f.name ?? f.uri.path;
-			const locationLabel = f.extensionId ?? dirname(f.uri).path;
-			lines.push(`  \u2713 ${label} - ${f.uri.path} (${locationLabel})`);
+			const parentDir = content.discoveryType === 'skill' ? dirname(dirname(f.uri)) : dirname(f.uri);
+			const key = f.extensionId ?? parentDir.path;
+			let group = groups.get(key);
+			if (!group) {
+				group = [];
+				groups.set(key, group);
+			}
+			group.push(f);
+		}
+		for (const [locationLabel, files] of groups) {
+			lines.push(`  ${locationLabel}`);
+			for (const f of files) {
+				const label = f.name ?? f.uri.path;
+				lines.push(`    \u2713 ${label}`);
+			}
 		}
 		lines.push('');
 	}
 
 	if (skipped.length > 0) {
 		lines.push(localize('chatDebug.plainText.skipped', "Skipped ({0})", skipped.length));
+		// Group by skip reason
+		const skippedGroups = new Map<string, typeof skipped>();
 		for (const f of skipped) {
-			const label = f.name ?? f.uri.path;
-			const reason = f.skipReason ?? localize('chatDebug.plainText.unknown', "unknown");
-			let detail = `  \u2717 ${label} (${reason}`;
-			if (f.errorMessage) {
-				detail += `: ${f.errorMessage}`;
+			const key = f.skipReason ?? localize('chatDebug.plainText.unknown', "unknown");
+			let group = skippedGroups.get(key);
+			if (!group) {
+				group = [];
+				skippedGroups.set(key, group);
 			}
-			if (f.duplicateOf) {
-				detail += localize('chatDebug.plainText.duplicateOf', ", duplicate of {0}", f.duplicateOf.path);
+			group.push(f);
+		}
+		for (const [reasonLabel, files] of skippedGroups) {
+			lines.push(`  ${reasonLabel}`);
+			for (const f of files) {
+				const label = f.name ?? f.uri.path;
+				let detail = `    \u2717 ${label}`;
+				if (f.errorMessage || f.duplicateOf) {
+					const parts: string[] = [];
+					if (f.errorMessage) {
+						parts.push(f.errorMessage);
+					}
+					if (f.duplicateOf) {
+						parts.push(localize('chatDebug.plainText.duplicateOf', "duplicate of {0}", f.duplicateOf.path));
+					}
+					detail += ` (${parts.join(', ')})`;
+				}
+				lines.push(detail);
 			}
-			detail += ')';
-			lines.push(detail);
 		}
 	}
 
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugAttachment.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugAttachment.ts
new file mode 100644
index 0000000000000..cede789e8df3f
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugAttachment.ts
@@ -0,0 +1,40 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Codicon } from '../../../../../base/common/codicons.js';
+import { URI } from '../../../../../base/common/uri.js';
+import * as nls from '../../../../../nls.js';
+import { IChatDebugService } from '../../common/chatDebugService.js';
+import { formatDebugEventsForContext, getDebugEventsModelDescription } from '../../common/chatDebugEvents.js';
+import { IChatRequestVariableEntry } from '../../common/attachments/chatVariableEntries.js';
+
+/**
+ * Creates a debug events attachment for a chat session.
+ * This can be used to attach debug logs to a chat request.
+ */
+export async function createDebugEventsAttachment(
+	sessionResource: URI,
+	chatDebugService: IChatDebugService
+): Promise<IChatRequestVariableEntry> {
+	chatDebugService.markDebugDataAttached(sessionResource);
+	if (!chatDebugService.hasInvokedProviders(sessionResource)) {
+		await chatDebugService.invokeProviders(sessionResource);
+	}
+	const events = chatDebugService.getEvents(sessionResource);
+	const summary = events.length > 0
+		? formatDebugEventsForContext(events)
+		: nls.localize('debugEventsSnapshot.noEvents', "No debug events found for this conversation.");
+
+	return {
+		id: 'chatDebugEvents',
+		name: nls.localize('debugEventsSnapshot.contextName', "Debug Events Snapshot"),
+		icon: Codicon.output,
+		kind: 'debugEvents',
+		snapshotTime: Date.now(),
+		sessionResource,
+		value: summary,
+		modelDescription: getDebugEventsModelDescription(),
+	};
+}
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugCollapsible.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugCollapsible.ts
new file mode 100644
index 0000000000000..b2226d30fca1f
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugCollapsible.ts
@@ -0,0 +1,46 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as DOM from '../../../../../base/browser/dom.js';
+import { Codicon } from '../../../../../base/common/codicons.js';
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { ThemeIcon } from '../../../../../base/common/themables.js';
+
+/**
+ * Wire up a collapsible toggle on a chevron+header+content triple.
+ * Handles icon switching and display toggling.
+ */
+export function setupCollapsibleToggle(chevron: HTMLElement, header: HTMLElement, contentEl: HTMLElement, disposables: DisposableStore, initiallyCollapsed: boolean = false): void {
+	let collapsed = initiallyCollapsed;
+
+	// Accessibility: make header keyboard-focusable and expose toggle semantics
+	header.tabIndex = 0;
+	header.role = 'button';
+	chevron.setAttribute('aria-hidden', 'true');
+
+	const updateState = () => {
+		DOM.clearNode(chevron);
+		const icon = collapsed ? Codicon.chevronRight : Codicon.chevronDown;
+		chevron.classList.add(...ThemeIcon.asClassName(icon).split(' '));
+		contentEl.style.display = collapsed ? 'none' : 'block';
+		header.style.borderRadius = collapsed ? '' : '3px 3px 0 0';
+		header.setAttribute('aria-expanded', String(!collapsed));
+	};
+
+	updateState();
+
+	disposables.add(DOM.addDisposableListener(header, DOM.EventType.CLICK, () => {
+		collapsed = !collapsed;
+		chevron.className = 'chat-debug-message-section-chevron';
+		updateState();
+	}));
+
+	disposables.add(DOM.addDisposableListener(header, DOM.EventType.KEY_DOWN, (e: KeyboardEvent) => {
+		if (e.key === 'Enter' || e.key === ' ') {
+			e.preventDefault();
+			header.click();
+		}
+	}));
+}
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugDetailPanel.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugDetailPanel.ts
index 70ab35f071ec7..1aa182e75a951 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugDetailPanel.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugDetailPanel.ts
@@ -5,6 +5,9 @@
 
 import * as DOM from '../../../../../base/browser/dom.js';
 import { Button } from '../../../../../base/browser/ui/button/button.js';
+import { Orientation, Sash, SashState } from '../../../../../base/browser/ui/sash/sash.js';
+import { DomScrollableElement } from '../../../../../base/browser/ui/scrollbar/scrollableElement.js';
+import { ScrollbarVisibility } from '../../../../../base/common/scrollable.js';
 import { Codicon } from '../../../../../base/common/codicons.js';
 import { Emitter } from '../../../../../base/common/event.js';
 import { Disposable, DisposableStore } from '../../../../../base/common/lifecycle.js';
@@ -20,11 +23,17 @@ import { IUntitledTextResourceEditorInput } from '../../../../common/editor.js';
 import { IEditorService } from '../../../../services/editor/common/editorService.js';
 import { IChatDebugEvent, IChatDebugService } from '../../common/chatDebugService.js';
 import { formatEventDetail } from './chatDebugEventDetailRenderer.js';
-import { renderFileListContent, fileListToPlainText } from './chatDebugFileListRenderer.js';
+import { renderCustomizationDiscoveryContent, fileListToPlainText } from './chatCustomizationDiscoveryRenderer.js';
 import { renderUserMessageContent, renderAgentResponseContent, messageEventToPlainText, renderResolvedMessageContent, resolvedMessageToPlainText } from './chatDebugMessageContentRenderer.js';
+import { renderToolCallContent, toolCallContentToPlainText } from './chatDebugToolCallContentRenderer.js';
+import { renderModelTurnContent, modelTurnContentToPlainText } from './chatDebugModelTurnContentRenderer.js';
 
 const $ = DOM.$;
 
+const DETAIL_PANEL_DEFAULT_WIDTH = 350;
+const DETAIL_PANEL_MIN_WIDTH = 200;
+const DETAIL_PANEL_MAX_WIDTH = 800;
+
 /**
  * Reusable detail panel that resolves and displays the content of a
  * single {@link IChatDebugEvent}. Used by both the logs view and the
@@ -35,10 +44,23 @@ export class ChatDebugDetailPanel extends Disposable {
 	private readonly _onDidHide = this._register(new Emitter<void>());
 	readonly onDidHide = this._onDidHide.event;
 
+	private readonly _onDidChangeWidth = this._register(new Emitter<number>());
+	readonly onDidChangeWidth = this._onDidChangeWidth.event;
+
 	readonly element: HTMLElement;
+	private readonly contentContainer: HTMLElement;
+	private readonly scrollable: DomScrollableElement;
+	private readonly sash: Sash;
+	private headerElement: HTMLElement | undefined;
 	private readonly detailDisposables = this._register(new DisposableStore());
 	private currentDetailText: string = '';
 	private currentDetailEventId: string | undefined;
+	private firstFocusableElement: HTMLElement | undefined;
+	private _width: number = DETAIL_PANEL_DEFAULT_WIDTH;
+
+	get width(): number {
+		return this._width;
+	}
 
 	constructor(
 		parent: HTMLElement,
@@ -48,11 +70,43 @@ export class ChatDebugDetailPanel extends Disposable {
 		@IClipboardService private readonly clipboardService: IClipboardService,
 		@IHoverService private readonly hoverService: IHoverService,
 		@IOpenerService private readonly openerService: IOpenerService,
+		@ILanguageService private readonly languageService: ILanguageService,
 	) {
 		super();
 		this.element = DOM.append(parent, $('.chat-debug-detail-panel'));
+		this.contentContainer = $('.chat-debug-detail-content');
+		this.scrollable = this._register(new DomScrollableElement(this.contentContainer, {
+			horizontal: ScrollbarVisibility.Hidden,
+			vertical: ScrollbarVisibility.Auto,
+		}));
+		this.element.style.width = `${this._width}px`;
 		DOM.hide(this.element);
 
+		// Sash on the parent container, positioned at the left edge of the detail panel
+		this.sash = this._register(new Sash(parent, {
+			getVerticalSashLeft: () => parent.offsetWidth - this._width,
+		}, { orientation: Orientation.VERTICAL }));
+		this.sash.state = SashState.Disabled;
+
+		let sashStartWidth: number | undefined;
+		this._register(this.sash.onDidStart(() => sashStartWidth = this._width));
+		this._register(this.sash.onDidEnd(() => {
+			sashStartWidth = undefined;
+			this.sash.layout();
+		}));
+		this._register(this.sash.onDidChange(e => {
+			if (sashStartWidth === undefined) {
+				return;
+			}
+			// Dragging left (negative currentX delta) should increase width
+			const delta = e.startX - e.currentX;
+			const newWidth = Math.max(DETAIL_PANEL_MIN_WIDTH, Math.min(DETAIL_PANEL_MAX_WIDTH, sashStartWidth + delta));
+			this._width = newWidth;
+			this.element.style.width = `${newWidth}px`;
+			this.sash.layout();
+			this._onDidChangeWidth.fire(newWidth);
+		}));
+
 		// Handle Ctrl+A / Cmd+A to select all within the detail panel
 		this._register(DOM.addDisposableListener(this.element, DOM.EventType.KEY_DOWN, (e: KeyboardEvent) => {
 			if ((e.ctrlKey || e.metaKey) && e.key === 'a') {
@@ -82,15 +136,21 @@ export class ChatDebugDetailPanel extends Disposable {
 		const resolved = event.id ? await this.chatDebugService.resolveEvent(event.id) : undefined;
 
 		DOM.show(this.element);
+		this.sash.state = SashState.Enabled;
+		this.sash.layout();
 		DOM.clearNode(this.element);
+		DOM.clearNode(this.contentContainer);
 		this.detailDisposables.clear();
 
 		// Header with action buttons
 		const header = DOM.append(this.element, $('.chat-debug-detail-header'));
+		this.headerElement = header;
+		this.element.appendChild(this.scrollable.getDomNode());
 
 		const fullScreenButton = this.detailDisposables.add(new Button(header, { ariaLabel: localize('chatDebug.openInEditor', "Open in Editor"), title: localize('chatDebug.openInEditor', "Open in Editor") }));
 		fullScreenButton.element.classList.add('chat-debug-detail-button');
 		fullScreenButton.icon = Codicon.goToFile;
+		this.firstFocusableElement = fullScreenButton.element;
 		this.detailDisposables.add(fullScreenButton.onDidClick(() => {
 			this.editorService.openEditor({ contents: this.currentDetailText, resource: undefined } satisfies IUntitledTextResourceEditorInput);
 		}));
@@ -112,27 +172,59 @@ export class ChatDebugDetailPanel extends Disposable {
 		if (resolved && resolved.kind === 'fileList') {
 			this.currentDetailText = fileListToPlainText(resolved);
 			const { element: contentEl, disposables: contentDisposables } = this.instantiationService.invokeFunction(accessor =>
-				renderFileListContent(resolved, this.openerService, accessor.get(IModelService), accessor.get(ILanguageService), this.hoverService, accessor.get(ILabelService))
+				renderCustomizationDiscoveryContent(resolved, this.openerService, accessor.get(IModelService), this.languageService, this.hoverService, accessor.get(ILabelService))
 			);
 			this.detailDisposables.add(contentDisposables);
-			this.element.appendChild(contentEl);
+			this.contentContainer.appendChild(contentEl);
+		} else if (resolved && resolved.kind === 'toolCall') {
+			this.currentDetailText = toolCallContentToPlainText(resolved);
+			const { element: contentEl, disposables: contentDisposables } = await renderToolCallContent(resolved, this.languageService, this.clipboardService);
+			if (this.currentDetailEventId !== event.id) {
+				// Another event was selected while we were rendering
+				contentDisposables.dispose();
+				return;
+			}
+			this.detailDisposables.add(contentDisposables);
+			this.contentContainer.appendChild(contentEl);
 		} else if (resolved && resolved.kind === 'message') {
 			this.currentDetailText = resolvedMessageToPlainText(resolved);
-			const { element: contentEl, disposables: contentDisposables } = renderResolvedMessageContent(resolved);
+			const { element: contentEl, disposables: contentDisposables } = await renderResolvedMessageContent(resolved, this.languageService, this.clipboardService);
+			if (this.currentDetailEventId !== event.id) {
+				contentDisposables.dispose();
+				return;
+			}
+			this.detailDisposables.add(contentDisposables);
+			this.contentContainer.appendChild(contentEl);
+		} else if (resolved && resolved.kind === 'modelTurn') {
+			this.currentDetailText = modelTurnContentToPlainText(resolved);
+			const { element: contentEl, disposables: contentDisposables } = await renderModelTurnContent(resolved, this.languageService, this.clipboardService);
+			if (this.currentDetailEventId !== event.id) {
+				// Another event was selected while we were rendering
+				contentDisposables.dispose();
+				return;
+			}
 			this.detailDisposables.add(contentDisposables);
-			this.element.appendChild(contentEl);
+			this.contentContainer.appendChild(contentEl);
 		} else if (event.kind === 'userMessage') {
 			this.currentDetailText = messageEventToPlainText(event);
-			const { element: contentEl, disposables: contentDisposables } = renderUserMessageContent(event);
+			const { element: contentEl, disposables: contentDisposables } = await renderUserMessageContent(event, this.languageService, this.clipboardService);
+			if (this.currentDetailEventId !== event.id) {
+				contentDisposables.dispose();
+				return;
+			}
 			this.detailDisposables.add(contentDisposables);
-			this.element.appendChild(contentEl);
+			this.contentContainer.appendChild(contentEl);
 		} else if (event.kind === 'agentResponse') {
 			this.currentDetailText = messageEventToPlainText(event);
-			const { element: contentEl, disposables: contentDisposables } = renderAgentResponseContent(event);
+			const { element: contentEl, disposables: contentDisposables } = await renderAgentResponseContent(event, this.languageService, this.clipboardService);
+			if (this.currentDetailEventId !== event.id) {
+				contentDisposables.dispose();
+				return;
+			}
 			this.detailDisposables.add(contentDisposables);
-			this.element.appendChild(contentEl);
+			this.contentContainer.appendChild(contentEl);
 		} else {
-			const pre = DOM.append(this.element, $('pre'));
+			const pre = DOM.append(this.contentContainer, $('pre'));
 			pre.tabIndex = 0;
 			if (resolved) {
 				this.currentDetailText = resolved.value;
@@ -141,12 +233,50 @@ export class ChatDebugDetailPanel extends Disposable {
 			}
 			pre.textContent = this.currentDetailText;
 		}
+
+		// Compute height from the parent container and set explicit
+		// dimensions so the scrollable element can show proper scrollbars.
+		const parentHeight = this.element.parentElement?.clientHeight ?? 0;
+		if (parentHeight > 0) {
+			this.layout(parentHeight);
+		} else {
+			this.scrollable.scanDomNode();
+		}
+	}
+
+	get isVisible(): boolean {
+		return this.element.style.display !== 'none';
+	}
+
+	focus(): void {
+		this.firstFocusableElement?.focus();
+	}
+
+	/**
+	 * Set explicit dimensions on the scrollable element so the scrollbar
+	 * can compute its size. Call after the panel is shown and whenever
+	 * the available space changes.
+	 */
+	layout(height: number): void {
+		const headerHeight = this.headerElement?.offsetHeight ?? 0;
+		const scrollableHeight = Math.max(0, height - headerHeight);
+		this.contentContainer.style.height = `${scrollableHeight}px`;
+		this.scrollable.scanDomNode();
+		this.sash.layout();
+	}
+
+	layoutSash(): void {
+		this.sash.layout();
 	}
 
 	hide(): void {
 		this.currentDetailEventId = undefined;
+		this.firstFocusableElement = undefined;
+		this.headerElement = undefined;
 		DOM.hide(this.element);
+		this.sash.state = SashState.Disabled;
 		DOM.clearNode(this.element);
+		DOM.clearNode(this.contentContainer);
 		this.detailDisposables.clear();
 		this._onDidHide.fire();
 	}
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEditor.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEditor.ts
index 772e96585a257..80fb8635e65e0 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEditor.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEditor.ts
@@ -7,17 +7,23 @@ import './media/chatDebug.css';
 
 import * as DOM from '../../../../../base/browser/dom.js';
 import { Dimension } from '../../../../../base/browser/dom.js';
+import { CancellationToken } from '../../../../../base/common/cancellation.js';
 import { DisposableMap, MutableDisposable } from '../../../../../base/common/lifecycle.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
+import { IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
 import { IInstantiationService } from '../../../../../platform/instantiation/common/instantiation.js';
 import { IStorageService } from '../../../../../platform/storage/common/storage.js';
 import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
 import { IThemeService } from '../../../../../platform/theme/common/themeService.js';
+import { IEditorOptions } from '../../../../../platform/editor/common/editor.js';
 import { EditorPane } from '../../../../browser/parts/editor/editorPane.js';
+import { IEditorOpenContext } from '../../../../common/editor.js';
+import { EditorInput } from '../../../../common/editor/editorInput.js';
 import { IEditorGroup } from '../../../../services/editor/common/editorGroupsService.js';
 import { IChatDebugService } from '../../common/chatDebugService.js';
 import { IChatService } from '../../common/chatService/chatService.js';
+import { AGENT_DEBUG_LOG_ENABLED_SETTING } from '../../common/promptSyntax/promptTypes.js';
 import { IChatWidgetService } from '../chat.js';
 import { ViewState, IChatDebugEditorOptions } from './chatDebugTypes.js';
 import { ChatDebugFilterState, registerFilterMenuItems } from './chatDebugFilters.js';
@@ -30,7 +36,7 @@ const $ = DOM.$;
 
 type ChatDebugPanelOpenedClassification = {
 	owner: 'vijayu';
-	comment: 'Event fired when the chat debug panel is opened';
+	comment: 'Event fired when the agent debug logs panel is opened';
 };
 
 type ChatDebugViewSwitchedEvent = {
@@ -40,7 +46,7 @@ type ChatDebugViewSwitchedEvent = {
 type ChatDebugViewSwitchedClassification = {
 	viewState: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The view the user navigated to (home, overview, logs, flowchart).' };
 	owner: 'vijayu';
-	comment: 'Tracks which views users navigate to in the debug panel.';
+	comment: 'Tracks which views users navigate to in the Agent Debug Logs.';
 };
 
 export class ChatDebugEditor extends EditorPane {
@@ -61,9 +67,6 @@ export class ChatDebugEditor extends EditorPane {
 	private readonly sessionModelListener = this._register(new MutableDisposable());
 	private readonly modelChangeListeners = this._register(new DisposableMap<string>());
 
-	/** Saved session resource so we can restore it after the editor is re-shown. */
-	private savedSessionResource: URI | undefined;
-
 	/**
 	 * Stops the streaming pipeline and clears cached events for the
 	 * active session. Called when navigating away from a session or
@@ -87,6 +90,7 @@ export class ChatDebugEditor extends EditorPane {
 		@IChatWidgetService private readonly chatWidgetService: IChatWidgetService,
 		@IChatService private readonly chatService: IChatService,
 		@IContextKeyService private readonly contextKeyService: IContextKeyService,
+		@IConfigurationService private readonly configurationService: IConfigurationService,
 	) {
 		super(ChatDebugEditor.ID, group, telemetryService, themeService, storageService);
 	}
@@ -170,10 +174,6 @@ export class ChatDebugEditor extends EditorPane {
 		}));
 
 		this._register(this.chatService.onDidCreateModel(model => {
-			if (this.viewState === ViewState.Home) {
-				this.homeView?.render();
-			}
-
 			// Track title changes per model, disposing the previous listener
 			// for the same model URI to avoid leaks.
 			const key = model.sessionResource.toString();
@@ -246,7 +246,9 @@ export class ChatDebugEditor extends EditorPane {
 		}
 
 		this.chatDebugService.activeSessionResource = sessionResource;
-		this.chatDebugService.invokeProviders(sessionResource);
+		if (!this.chatDebugService.hasInvokedProviders(sessionResource)) {
+			this.chatDebugService.invokeProviders(sessionResource);
+		}
 		this.trackSessionModelChanges(sessionResource);
 
 		this.overviewView?.setSession(sessionResource);
@@ -283,6 +285,13 @@ export class ChatDebugEditor extends EditorPane {
 		}
 	}
 
+	override async setInput(input: EditorInput, options: IEditorOptions | undefined, context: IEditorOpenContext, token: CancellationToken): Promise<void> {
+		await super.setInput(input, options, context, token);
+		if (options) {
+			this._applyNavigationOptions(options as IChatDebugEditorOptions);
+		}
+	}
+
 	override setOptions(options: IChatDebugEditorOptions | undefined): void {
 		super.setOptions(options);
 		if (options) {
@@ -294,40 +303,29 @@ export class ChatDebugEditor extends EditorPane {
 		super.setEditorVisible(visible);
 		if (visible) {
 			this.telemetryService.publicLog2<{}, ChatDebugPanelOpenedClassification>('chatDebugPanelOpened');
-			const options = this.options as IChatDebugEditorOptions | undefined;
-			if (options) {
-				this._applyNavigationOptions(options);
-			} else if (this.viewState === ViewState.Home) {
-				// Restore the saved session resource if the editor was temporarily hidden
-				const sessionResource = this.chatDebugService.activeSessionResource ?? this.savedSessionResource;
-				this.savedSessionResource = undefined;
-				if (sessionResource) {
-					this.navigateToSession(sessionResource, 'overview');
-				} else {
-					this.showView(ViewState.Home);
-				}
-			} else {
-				// Re-activate the streaming pipeline for the current session,
-				// restoring the saved session resource if the editor was temporarily hidden.
-				const sessionResource = this.chatDebugService.activeSessionResource ?? this.savedSessionResource;
-				this.savedSessionResource = undefined;
-				if (sessionResource) {
-					this.chatDebugService.activeSessionResource = sessionResource;
-					this.chatDebugService.invokeProviders(sessionResource);
-				} else {
-					this.showView(ViewState.Home);
-				}
+			// If the feature flag is disabled, always reset to the home view
+			if (!this.configurationService.getValue<boolean>(AGENT_DEBUG_LOG_ENABLED_SETTING)) {
+				this.endActiveSession();
+				this.showView(ViewState.Home);
+				return;
 			}
-		} else {
-			// Remember the active session so we can restore when re-shown
-			this.savedSessionResource = this.chatDebugService.activeSessionResource;
-			// Stop the streaming pipeline when the editor is hidden
-			this.endActiveSession();
+			// Re-show the current view so it reloads events from scratch,
+			// ensuring correct ordering and no stale duplicates.
+			// Navigation from new openEditor() options is handled by
+			// setOptions → _applyNavigationOptions (fires after this).
+			this.showView(this.viewState);
 		}
 	}
 
 	private _applyNavigationOptions(options: IChatDebugEditorOptions): void {
-		const { sessionResource, viewHint } = options;
+		// If the feature flag is disabled, always show the home view
+		if (!this.configurationService.getValue<boolean>(AGENT_DEBUG_LOG_ENABLED_SETTING)) {
+			this.endActiveSession();
+			this.showView(ViewState.Home);
+			return;
+		}
+
+		const { sessionResource, viewHint, filter } = options;
 		if (viewHint === 'logs' && sessionResource) {
 			this.navigateToSession(sessionResource, 'logs');
 		} else if (viewHint === 'flowchart' && sessionResource) {
@@ -342,6 +340,12 @@ export class ChatDebugEditor extends EditorPane {
 		} else if (this.viewState === ViewState.Home) {
 			this.showView(ViewState.Home);
 		}
+
+		// Apply filter text if provided (e.g. from debug events snapshot)
+		if (filter !== undefined && this.filterState) {
+			this.filterState.setTextFilter(filter);
+			this.logsView?.setFilterText(filter);
+		}
 	}
 
 	override layout(dimension: Dimension): void {
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEditorInput.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEditorInput.ts
index fb7ab5d0020b2..a7659363f4f92 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEditorInput.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEditorInput.ts
@@ -41,7 +41,7 @@ export class ChatDebugEditorInput extends EditorInput {
 	readonly resource = ChatDebugEditorInput.RESOURCE;
 
 	override getName(): string {
-		return localize('chatDebugInputName', "Chat Debug Panel");
+		return localize('chatDebugInputName', "Agent Debug Logs");
 	}
 
 	override getIcon(): ThemeIcon {
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEventDetailRenderer.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEventDetailRenderer.ts
index be68f3d757e06..5f7fd3267aa7b 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEventDetailRenderer.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEventDetailRenderer.ts
@@ -5,6 +5,9 @@
 
 import { localize } from '../../../../../nls.js';
 import { IChatDebugEvent } from '../../common/chatDebugService.js';
+import { safeIntl } from '../../../../../base/common/date.js';
+
+const numberFormatter = safeIntl.NumberFormat();
 
 /**
  * Format the detail text for a debug event (used when no resolved content is available).
@@ -15,17 +18,17 @@ export function formatEventDetail(event: IChatDebugEvent): string {
 			const parts = [localize('chatDebug.detail.tool', "Tool: {0}", event.toolName)];
 			if (event.toolCallId) { parts.push(localize('chatDebug.detail.callId', "Call ID: {0}", event.toolCallId)); }
 			if (event.result) { parts.push(localize('chatDebug.detail.result', "Result: {0}", event.result)); }
-			if (event.durationInMillis !== undefined) { parts.push(localize('chatDebug.detail.durationMs', "Duration: {0}ms", event.durationInMillis)); }
+			if (event.durationInMillis !== undefined) { parts.push(localize('chatDebug.detail.durationMs', "Duration: {0}ms", numberFormatter.value.format(event.durationInMillis))); }
 			if (event.input) { parts.push(`\n${localize('chatDebug.detail.input', "Input:")}\n${event.input}`); }
 			if (event.output) { parts.push(`\n${localize('chatDebug.detail.output', "Output:")}\n${event.output}`); }
 			return parts.join('\n');
 		}
 		case 'modelTurn': {
 			const parts = [event.model ?? localize('chatDebug.detail.modelTurn', "Model Turn")];
-			if (event.inputTokens !== undefined) { parts.push(localize('chatDebug.detail.inputTokens', "Input tokens: {0}", event.inputTokens)); }
-			if (event.outputTokens !== undefined) { parts.push(localize('chatDebug.detail.outputTokens', "Output tokens: {0}", event.outputTokens)); }
-			if (event.totalTokens !== undefined) { parts.push(localize('chatDebug.detail.totalTokens', "Total tokens: {0}", event.totalTokens)); }
-			if (event.durationInMillis !== undefined) { parts.push(localize('chatDebug.detail.durationMs', "Duration: {0}ms", event.durationInMillis)); }
+			if (event.inputTokens !== undefined) { parts.push(localize('chatDebug.detail.inputTokens', "Input tokens: {0}", numberFormatter.value.format(event.inputTokens))); }
+			if (event.outputTokens !== undefined) { parts.push(localize('chatDebug.detail.outputTokens', "Output tokens: {0}", numberFormatter.value.format(event.outputTokens))); }
+			if (event.totalTokens !== undefined) { parts.push(localize('chatDebug.detail.totalTokens', "Total tokens: {0}", numberFormatter.value.format(event.totalTokens))); }
+			if (event.durationInMillis !== undefined) { parts.push(localize('chatDebug.detail.durationMs', "Duration: {0}ms", numberFormatter.value.format(event.durationInMillis))); }
 			return parts.join('\n');
 		}
 		case 'generic':
@@ -34,9 +37,9 @@ export function formatEventDetail(event: IChatDebugEvent): string {
 			const parts = [localize('chatDebug.detail.agent', "Agent: {0}", event.agentName)];
 			if (event.description) { parts.push(localize('chatDebug.detail.description', "Description: {0}", event.description)); }
 			if (event.status) { parts.push(localize('chatDebug.detail.status', "Status: {0}", event.status)); }
-			if (event.durationInMillis !== undefined) { parts.push(localize('chatDebug.detail.durationMs', "Duration: {0}ms", event.durationInMillis)); }
-			if (event.toolCallCount !== undefined) { parts.push(localize('chatDebug.detail.toolCallCount', "Tool calls: {0}", event.toolCallCount)); }
-			if (event.modelTurnCount !== undefined) { parts.push(localize('chatDebug.detail.modelTurnCount', "Model turns: {0}", event.modelTurnCount)); }
+			if (event.durationInMillis !== undefined) { parts.push(localize('chatDebug.detail.durationMs', "Duration: {0}ms", numberFormatter.value.format(event.durationInMillis))); }
+			if (event.toolCallCount !== undefined) { parts.push(localize('chatDebug.detail.toolCallCount', "Tool calls: {0}", numberFormatter.value.format(event.toolCallCount))); }
+			if (event.modelTurnCount !== undefined) { parts.push(localize('chatDebug.detail.modelTurnCount', "Model turns: {0}", numberFormatter.value.format(event.modelTurnCount))); }
 			return parts.join('\n');
 		}
 		case 'userMessage': {
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEventList.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEventList.ts
index 7ae85ffa0f88b..11ea6f766016c 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEventList.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugEventList.ts
@@ -12,6 +12,14 @@ import { safeIntl } from '../../../../../base/common/date.js';
 
 const $ = DOM.$;
 
+/** Coerce a value to a string, returning a fallback for null/undefined/non-strings. */
+function safeStr(value: string | undefined | null, fallback: string = ''): string {
+	if (value === null || value === undefined || typeof value !== 'string') {
+		return fallback;
+	}
+	return value;
+}
+
 const dateFormatter = safeIntl.DateTimeFormat(undefined, {
 	month: 'short',
 	day: 'numeric',
@@ -20,6 +28,8 @@ const dateFormatter = safeIntl.DateTimeFormat(undefined, {
 	second: '2-digit',
 });
 
+const numberFormatter = safeIntl.NumberFormat();
+
 export interface IChatDebugEventTemplate {
 	readonly container: HTMLElement;
 	readonly created: HTMLElement;
@@ -27,37 +37,42 @@ export interface IChatDebugEventTemplate {
 	readonly details: HTMLElement;
 }
 
-function renderEventToTemplate(element: IChatDebugEvent, templateData: IChatDebugEventTemplate): void {
-	templateData.created.textContent = dateFormatter.value.format(element.created);
+/** Returns the formatted creation timestamp for a debug event. */
+export function getEventCreatedText(element: IChatDebugEvent): string {
+	return dateFormatter.value.format(element.created);
+}
 
+/** Returns the display name for a debug event. */
+export function getEventNameText(element: IChatDebugEvent): string {
 	switch (element.kind) {
-		case 'toolCall':
-			templateData.name.textContent = element.toolName;
-			templateData.details.textContent = element.result ?? '';
-			break;
-		case 'modelTurn':
-			templateData.name.textContent = element.model ?? localize('chatDebug.modelTurn', "Model Turn");
-			templateData.details.textContent = element.totalTokens !== undefined
-				? localize('chatDebug.tokens', "{0} tokens", element.totalTokens)
-				: '';
-			break;
-		case 'generic':
-			templateData.name.textContent = element.name;
-			templateData.details.textContent = element.details ?? '';
-			break;
-		case 'subagentInvocation':
-			templateData.name.textContent = element.agentName;
-			templateData.details.textContent = element.description ?? (element.status ?? '');
-			break;
-		case 'userMessage':
-			templateData.name.textContent = localize('chatDebug.userMessage', "User Message");
-			templateData.details.textContent = element.message;
-			break;
-		case 'agentResponse':
-			templateData.name.textContent = localize('chatDebug.agentResponse', "Agent Response");
-			templateData.details.textContent = element.message;
-			break;
+		case 'toolCall': return safeStr(element.toolName, localize('chatDebug.unknownEvent', "(unknown)"));
+		case 'modelTurn': return safeStr(element.model) || localize('chatDebug.modelTurn', "Model Turn");
+		case 'generic': return safeStr(element.name, localize('chatDebug.unknownEvent', "(unknown)"));
+		case 'subagentInvocation': return safeStr(element.agentName, localize('chatDebug.unknownEvent', "(unknown)"));
+		case 'userMessage': return localize('chatDebug.userMessage', "User Message");
+		case 'agentResponse': return localize('chatDebug.agentResponse', "Agent Response");
 	}
+}
+
+/** Returns the details text for a debug event. */
+export function getEventDetailsText(element: IChatDebugEvent): string {
+	switch (element.kind) {
+		case 'toolCall': return safeStr(element.result);
+		case 'modelTurn': return [
+			safeStr(element.requestName),
+			element.totalTokens !== undefined ? localize('chatDebug.tokens', "{0} tokens", numberFormatter.value.format(element.totalTokens)) : '',
+		].filter(Boolean).join(' \u00b7 ');
+		case 'generic': return safeStr(element.details);
+		case 'subagentInvocation': return safeStr(element.description) || safeStr(element.status);
+		case 'userMessage': return safeStr(element.message);
+		case 'agentResponse': return safeStr(element.message);
+	}
+}
+
+function renderEventToTemplate(element: IChatDebugEvent, templateData: IChatDebugEventTemplate): void {
+	templateData.created.textContent = getEventCreatedText(element);
+	templateData.name.textContent = getEventNameText(element);
+	templateData.details.textContent = getEventDetailsText(element);
 
 	const isError = element.kind === 'generic' && element.level === ChatDebugLogLevel.Error
 		|| element.kind === 'toolCall' && element.result === 'error';
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFilters.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFilters.ts
index 50ce745c94fe7..f3c86fa542717 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFilters.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFilters.ts
@@ -10,18 +10,16 @@ import { IContextKey, IContextKeyService, RawContextKey } from '../../../../../p
 import { MenuRegistry } from '../../../../../platform/actions/common/actions.js';
 import { CommandsRegistry } from '../../../../../platform/commands/common/commands.js';
 import { viewFilterSubmenu } from '../../../../browser/parts/views/viewFilter.js';
+import { parseTimeToken, stripTimestampTokens } from '../../common/chatDebugEvents.js';
 import {
 	CHAT_DEBUG_FILTER_ACTIVE,
-	CHAT_DEBUG_KIND_TOOL_CALL, CHAT_DEBUG_KIND_MODEL_TURN, CHAT_DEBUG_KIND_GENERIC, CHAT_DEBUG_KIND_SUBAGENT,
-	CHAT_DEBUG_KIND_USER_MESSAGE, CHAT_DEBUG_KIND_AGENT_RESPONSE,
-	CHAT_DEBUG_LEVEL_TRACE, CHAT_DEBUG_LEVEL_INFO, CHAT_DEBUG_LEVEL_WARNING, CHAT_DEBUG_LEVEL_ERROR,
-	CHAT_DEBUG_CMD_TOGGLE_TOOL_CALL, CHAT_DEBUG_CMD_TOGGLE_MODEL_TURN, CHAT_DEBUG_CMD_TOGGLE_GENERIC,
-	CHAT_DEBUG_CMD_TOGGLE_SUBAGENT, CHAT_DEBUG_CMD_TOGGLE_USER_MESSAGE, CHAT_DEBUG_CMD_TOGGLE_AGENT_RESPONSE,
-	CHAT_DEBUG_CMD_TOGGLE_TRACE, CHAT_DEBUG_CMD_TOGGLE_INFO, CHAT_DEBUG_CMD_TOGGLE_WARNING, CHAT_DEBUG_CMD_TOGGLE_ERROR,
+	CHAT_DEBUG_KIND_TOOL_CALL, CHAT_DEBUG_KIND_MODEL_TURN, CHAT_DEBUG_KIND_PROMPT_DISCOVERY, CHAT_DEBUG_KIND_SUBAGENT,
+	CHAT_DEBUG_CMD_TOGGLE_TOOL_CALL, CHAT_DEBUG_CMD_TOGGLE_MODEL_TURN, CHAT_DEBUG_CMD_TOGGLE_PROMPT_DISCOVERY,
+	CHAT_DEBUG_CMD_TOGGLE_SUBAGENT,
 } from './chatDebugTypes.js';
 
 /**
- * Shared filter state for the Chat Debug Panel.
+ * Shared filter state for the Agent Debug Logs.
  *
  * Both the Logs view and the Flow Chart view read from this single source of
  * truth. Toggle commands modify the state and fire `onDidChange` so every
@@ -35,55 +33,70 @@ export class ChatDebugFilterState extends Disposable {
 	// Kind visibility
 	filterKindToolCall: boolean = true;
 	filterKindModelTurn: boolean = true;
-	filterKindGeneric: boolean = true;
+	filterKindPromptDiscovery: boolean = true;
 	filterKindSubagent: boolean = true;
-	filterKindUserMessage: boolean = true;
-	filterKindAgentResponse: boolean = true;
-
-	// Level visibility
-	filterLevelTrace: boolean = true;
-	filterLevelInfo: boolean = true;
-	filterLevelWarning: boolean = true;
-	filterLevelError: boolean = true;
 
 	// Text filter
 	textFilter: string = '';
 
-	isKindVisible(kind: string): boolean {
+	// Parsed timestamp filters (epoch ms)
+	beforeTimestamp: number | undefined;
+	afterTimestamp: number | undefined;
+
+	isKindVisible(kind: string, category?: string): boolean {
 		switch (kind) {
 			case 'toolCall': return this.filterKindToolCall;
 			case 'modelTurn': return this.filterKindModelTurn;
-			case 'generic': return this.filterKindGeneric;
+			case 'generic':
+				// The "Prompt Discovery" toggle only hides events produced by
+				// the prompt discovery pipeline (category === 'discovery').
+				// Other generic events (e.g. from external providers) are
+				// always visible and are not affected by this toggle.
+				if (category !== 'discovery') {
+					return true;
+				}
+				return this.filterKindPromptDiscovery;
 			case 'subagentInvocation': return this.filterKindSubagent;
-			case 'userMessage': return this.filterKindUserMessage;
-			case 'agentResponse': return this.filterKindAgentResponse;
+
 			default: return true;
 		}
 	}
 
 	isAllKindsVisible(): boolean {
 		return this.filterKindToolCall && this.filterKindModelTurn &&
-			this.filterKindGeneric && this.filterKindSubagent &&
-			this.filterKindUserMessage && this.filterKindAgentResponse;
-	}
-
-	isAllLevelsVisible(): boolean {
-		return this.filterLevelTrace && this.filterLevelInfo &&
-			this.filterLevelWarning && this.filterLevelError;
+			this.filterKindPromptDiscovery && this.filterKindSubagent;
 	}
 
 	isAllFiltersDefault(): boolean {
-		return this.isAllKindsVisible() && this.isAllLevelsVisible();
+		return this.isAllKindsVisible();
 	}
 
 	setTextFilter(text: string): void {
 		const normalized = text.toLowerCase();
 		if (this.textFilter !== normalized) {
 			this.textFilter = normalized;
+			this.beforeTimestamp = parseTimeToken(normalized, 'before');
+			this.afterTimestamp = parseTimeToken(normalized, 'after');
 			this._onDidChange.fire();
 		}
 	}
 
+	/** Returns the text filter with before:/after: tokens removed. */
+	get textFilterWithoutTimestamps(): string {
+		return stripTimestampTokens(this.textFilter);
+	}
+
+	isTimestampVisible(created: Date): boolean {
+		const time = created.getTime();
+		if (this.beforeTimestamp !== undefined && time > this.beforeTimestamp) {
+			return false;
+		}
+		if (this.afterTimestamp !== undefined && time < this.afterTimestamp) {
+			return false;
+		}
+		return true;
+	}
+
 	fire(): void {
 		this._onDidChange.fire();
 	}
@@ -106,23 +119,10 @@ export function registerFilterMenuItems(
 	kindToolCallKey.set(true);
 	const kindModelTurnKey = CHAT_DEBUG_KIND_MODEL_TURN.bindTo(scopedContextKeyService);
 	kindModelTurnKey.set(true);
-	const kindGenericKey = CHAT_DEBUG_KIND_GENERIC.bindTo(scopedContextKeyService);
-	kindGenericKey.set(true);
+	const kindPromptDiscoveryKey = CHAT_DEBUG_KIND_PROMPT_DISCOVERY.bindTo(scopedContextKeyService);
+	kindPromptDiscoveryKey.set(true);
 	const kindSubagentKey = CHAT_DEBUG_KIND_SUBAGENT.bindTo(scopedContextKeyService);
 	kindSubagentKey.set(true);
-	const kindUserMessageKey = CHAT_DEBUG_KIND_USER_MESSAGE.bindTo(scopedContextKeyService);
-	kindUserMessageKey.set(true);
-	const kindAgentResponseKey = CHAT_DEBUG_KIND_AGENT_RESPONSE.bindTo(scopedContextKeyService);
-	kindAgentResponseKey.set(true);
-	const levelTraceKey = CHAT_DEBUG_LEVEL_TRACE.bindTo(scopedContextKeyService);
-	levelTraceKey.set(true);
-	const levelInfoKey = CHAT_DEBUG_LEVEL_INFO.bindTo(scopedContextKeyService);
-	levelInfoKey.set(true);
-	const levelWarningKey = CHAT_DEBUG_LEVEL_WARNING.bindTo(scopedContextKeyService);
-	levelWarningKey.set(true);
-	const levelErrorKey = CHAT_DEBUG_LEVEL_ERROR.bindTo(scopedContextKeyService);
-	levelErrorKey.set(true);
-
 	const registerToggle = (
 		id: string, title: string, key: RawContextKey<boolean>, group: string,
 		getter: () => boolean, setter: (v: boolean) => void, ctxKey: IContextKey<boolean>,
@@ -142,15 +142,8 @@ export function registerFilterMenuItems(
 
 	registerToggle(CHAT_DEBUG_CMD_TOGGLE_TOOL_CALL, localize('chatDebug.filter.toolCall', "Tool Calls"), CHAT_DEBUG_KIND_TOOL_CALL, '1_kind', () => state.filterKindToolCall, v => { state.filterKindToolCall = v; }, kindToolCallKey);
 	registerToggle(CHAT_DEBUG_CMD_TOGGLE_MODEL_TURN, localize('chatDebug.filter.modelTurn', "Model Turns"), CHAT_DEBUG_KIND_MODEL_TURN, '1_kind', () => state.filterKindModelTurn, v => { state.filterKindModelTurn = v; }, kindModelTurnKey);
-	registerToggle(CHAT_DEBUG_CMD_TOGGLE_GENERIC, localize('chatDebug.filter.generic', "Generic"), CHAT_DEBUG_KIND_GENERIC, '1_kind', () => state.filterKindGeneric, v => { state.filterKindGeneric = v; }, kindGenericKey);
+	registerToggle(CHAT_DEBUG_CMD_TOGGLE_PROMPT_DISCOVERY, localize('chatDebug.filter.promptDiscovery', "Chat Customization"), CHAT_DEBUG_KIND_PROMPT_DISCOVERY, '1_kind', () => state.filterKindPromptDiscovery, v => { state.filterKindPromptDiscovery = v; }, kindPromptDiscoveryKey);
 	registerToggle(CHAT_DEBUG_CMD_TOGGLE_SUBAGENT, localize('chatDebug.filter.subagent', "Subagent Invocations"), CHAT_DEBUG_KIND_SUBAGENT, '1_kind', () => state.filterKindSubagent, v => { state.filterKindSubagent = v; }, kindSubagentKey);
-	registerToggle(CHAT_DEBUG_CMD_TOGGLE_USER_MESSAGE, localize('chatDebug.filter.userMessage', "User Messages"), CHAT_DEBUG_KIND_USER_MESSAGE, '1_kind', () => state.filterKindUserMessage, v => { state.filterKindUserMessage = v; }, kindUserMessageKey);
-	registerToggle(CHAT_DEBUG_CMD_TOGGLE_AGENT_RESPONSE, localize('chatDebug.filter.agentResponse', "Agent Responses"), CHAT_DEBUG_KIND_AGENT_RESPONSE, '1_kind', () => state.filterKindAgentResponse, v => { state.filterKindAgentResponse = v; }, kindAgentResponseKey);
-
-	registerToggle(CHAT_DEBUG_CMD_TOGGLE_TRACE, localize('chatDebug.filter.trace', "Trace"), CHAT_DEBUG_LEVEL_TRACE, '2_level', () => state.filterLevelTrace, v => { state.filterLevelTrace = v; }, levelTraceKey);
-	registerToggle(CHAT_DEBUG_CMD_TOGGLE_INFO, localize('chatDebug.filter.info', "Info"), CHAT_DEBUG_LEVEL_INFO, '2_level', () => state.filterLevelInfo, v => { state.filterLevelInfo = v; }, levelInfoKey);
-	registerToggle(CHAT_DEBUG_CMD_TOGGLE_WARNING, localize('chatDebug.filter.warning', "Warning"), CHAT_DEBUG_LEVEL_WARNING, '2_level', () => state.filterLevelWarning, v => { state.filterLevelWarning = v; }, levelWarningKey);
-	registerToggle(CHAT_DEBUG_CMD_TOGGLE_ERROR, localize('chatDebug.filter.error', "Error"), CHAT_DEBUG_LEVEL_ERROR, '2_level', () => state.filterLevelError, v => { state.filterLevelError = v; }, levelErrorKey);
 
 	return store;
 }
@@ -166,25 +159,12 @@ export function bindFilterContextKeys(
 	CHAT_DEBUG_FILTER_ACTIVE.bindTo(scopedContextKeyService).set(true);
 	const kindToolCallKey = CHAT_DEBUG_KIND_TOOL_CALL.bindTo(scopedContextKeyService);
 	const kindModelTurnKey = CHAT_DEBUG_KIND_MODEL_TURN.bindTo(scopedContextKeyService);
-	const kindGenericKey = CHAT_DEBUG_KIND_GENERIC.bindTo(scopedContextKeyService);
+	const kindPromptDiscoveryKey = CHAT_DEBUG_KIND_PROMPT_DISCOVERY.bindTo(scopedContextKeyService);
 	const kindSubagentKey = CHAT_DEBUG_KIND_SUBAGENT.bindTo(scopedContextKeyService);
-	const kindUserMessageKey = CHAT_DEBUG_KIND_USER_MESSAGE.bindTo(scopedContextKeyService);
-	const kindAgentResponseKey = CHAT_DEBUG_KIND_AGENT_RESPONSE.bindTo(scopedContextKeyService);
-	const levelTraceKey = CHAT_DEBUG_LEVEL_TRACE.bindTo(scopedContextKeyService);
-	const levelInfoKey = CHAT_DEBUG_LEVEL_INFO.bindTo(scopedContextKeyService);
-	const levelWarningKey = CHAT_DEBUG_LEVEL_WARNING.bindTo(scopedContextKeyService);
-	const levelErrorKey = CHAT_DEBUG_LEVEL_ERROR.bindTo(scopedContextKeyService);
-
 	return () => {
 		kindToolCallKey.set(state.filterKindToolCall);
 		kindModelTurnKey.set(state.filterKindModelTurn);
-		kindGenericKey.set(state.filterKindGeneric);
+		kindPromptDiscoveryKey.set(state.filterKindPromptDiscovery);
 		kindSubagentKey.set(state.filterKindSubagent);
-		kindUserMessageKey.set(state.filterKindUserMessage);
-		kindAgentResponseKey.set(state.filterKindAgentResponse);
-		levelTraceKey.set(state.filterLevelTrace);
-		levelInfoKey.set(state.filterLevelInfo);
-		levelWarningKey.set(state.filterLevelWarning);
-		levelErrorKey.set(state.filterLevelError);
 	};
 }
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowChart.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowChart.ts
index b7dfe35052eb1..976da3108506b 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowChart.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowChart.ts
@@ -5,7 +5,7 @@
 
 // Barrel re-export — keeps existing imports stable.
 // Data model + graph building (stable):
-export { buildFlowGraph, filterFlowNodes, sliceFlowNodes } from './chatDebugFlowGraph.js';
+export { buildFlowGraph, filterFlowNodes, sliceFlowNodes, mergeDiscoveryNodes, mergeToolCallNodes } from './chatDebugFlowGraph.js';
 export type { FlowNode, FlowFilterOptions, FlowSliceResult, FlowLayout, FlowChartRenderResult, LayoutNode, LayoutEdge, SubgraphRect } from './chatDebugFlowGraph.js';
 // Layout + rendering
 export { layoutFlowGraph, renderFlowChartSVG } from './chatDebugFlowLayout.js';
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowChartView.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowChartView.ts
index a61f134a9a8f3..7f8997efa5724 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowChartView.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowChartView.ts
@@ -9,6 +9,7 @@ import { BreadcrumbsWidget } from '../../../../../base/browser/ui/breadcrumbs/br
 import { Codicon } from '../../../../../base/common/codicons.js';
 import { Emitter } from '../../../../../base/common/event.js';
 import { Disposable, DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { RunOnceScheduler } from '../../../../../base/common/async.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { localize } from '../../../../../nls.js';
 import { IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
@@ -21,7 +22,7 @@ import { IChatService } from '../../common/chatService/chatService.js';
 import { LocalChatSessionUri } from '../../common/model/chatUri.js';
 import { setupBreadcrumbKeyboardNavigation, TextBreadcrumbItem } from './chatDebugTypes.js';
 import { ChatDebugFilterState, bindFilterContextKeys } from './chatDebugFilters.js';
-import { buildFlowGraph, filterFlowNodes, sliceFlowNodes, layoutFlowGraph, renderFlowChartSVG, FlowChartRenderResult } from './chatDebugFlowChart.js';
+import { buildFlowGraph, filterFlowNodes, sliceFlowNodes, mergeDiscoveryNodes, mergeToolCallNodes, layoutFlowGraph, renderFlowChartSVG, FlowChartRenderResult } from './chatDebugFlowChart.js';
 import { ChatDebugDetailPanel } from './chatDebugDetailPanel.js';
 
 const $ = DOM.$;
@@ -47,6 +48,7 @@ export class ChatDebugFlowChartView extends Disposable {
 	private readonly content: HTMLElement;
 	private readonly breadcrumbWidget: BreadcrumbsWidget;
 	private readonly filterWidget: FilterWidget;
+	private readonly headerContainer: HTMLElement;
 	private readonly loadDisposables = this._register(new DisposableStore());
 
 	// Pan/zoom state
@@ -76,12 +78,16 @@ export class ChatDebugFlowChartView extends Disposable {
 	// Collapse state — persists across refreshes, resets on session change
 	private readonly collapsedNodeIds = new Set<string>();
 
+	// Expanded merged-discovery nodes — persists across refreshes, resets on session change
+	private readonly expandedMergedIds = new Set<string>();
+
 	// Pagination state
 	private visibleLimit: number = PAGE_SIZE;
 
 	// Detail panel
 	private readonly detailPanel: ChatDebugDetailPanel;
 	private eventById = new Map<string, IChatDebugEvent>();
+	private readonly refreshScheduler: RunOnceScheduler;
 
 	constructor(
 		parent: HTMLElement,
@@ -113,7 +119,8 @@ export class ChatDebugFlowChartView extends Disposable {
 		}));
 
 		// Header with FilterWidget
-		const headerContainer = DOM.append(this.container, $('.chat-debug-editor-header'));
+		this.headerContainer = DOM.append(this.container, $('.chat-debug-editor-header'));
+		const headerContainer = this.headerContainer;
 		const scopedContextKeyService = this._register(this.contextKeyService.createScoped(headerContainer));
 		const syncContextKeys = bindFilterContextKeys(this.filterState, scopedContextKeyService);
 		syncContextKeys();
@@ -153,6 +160,8 @@ export class ChatDebugFlowChartView extends Disposable {
 		// Set up pan/zoom event listeners and keyboard handling
 		this.setupPanZoom();
 		this.setupKeyboard();
+
+		this.refreshScheduler = this._register(new RunOnceScheduler(() => this.load(), 100));
 	}
 
 	setSession(sessionResource: URI): void {
@@ -165,6 +174,7 @@ export class ChatDebugFlowChartView extends Disposable {
 			this.hasUserPanned = false;
 			this.focusedElementId = undefined;
 			this.collapsedNodeIds.clear();
+			this.expandedMergedIds.clear();
 			this.visibleLimit = PAGE_SIZE;
 			this.detailPanel.hide();
 		}
@@ -178,11 +188,14 @@ export class ChatDebugFlowChartView extends Disposable {
 
 	hide(): void {
 		DOM.hide(this.container);
+		this.refreshScheduler.cancel();
 	}
 
 	refresh(): void {
 		if (this.container.style.display !== 'none') {
-			this.load();
+			if (!this.refreshScheduler.isScheduled()) {
+				this.refreshScheduler.schedule();
+			}
 		}
 	}
 
@@ -192,13 +205,17 @@ export class ChatDebugFlowChartView extends Disposable {
 		}
 		const sessionTitle = this.chatService.getSessionTitle(this.currentSessionResource) || LocalChatSessionUri.parseLocalSessionId(this.currentSessionResource) || this.currentSessionResource.toString();
 		this.breadcrumbWidget.setItems([
-			new TextBreadcrumbItem(localize('chatDebug.title', "Chat Debug Panel"), true),
+			new TextBreadcrumbItem(localize('chatDebug.title', "Agent Debug Logs"), true),
 			new TextBreadcrumbItem(sessionTitle, true),
 			new TextBreadcrumbItem(localize('chatDebug.flowChart', "Agent Flow Chart")),
 		]);
 	}
 
 	private load(): void {
+		// Check whether the chart content currently has focus before clearing it,
+		// so we only restore focus if it was taken away by the re-render.
+		const hadFocus = DOM.isAncestorOfActiveElement(this.content);
+
 		DOM.clearNode(this.content);
 		this.loadDisposables.clear();
 		this.updateBreadcrumb();
@@ -224,7 +241,7 @@ export class ChatDebugFlowChartView extends Disposable {
 		// Build, filter, slice, and render the flow chart
 		const flowNodes = buildFlowGraph(events);
 		const filtered = filterFlowNodes(flowNodes, {
-			isKindVisible: kind => this.filterState.isKindVisible(kind),
+			isKindVisible: (kind, category) => this.filterState.isKindVisible(kind, category),
 			textFilter: this.filterState.textFilter,
 		});
 
@@ -235,7 +252,8 @@ export class ChatDebugFlowChartView extends Disposable {
 		}
 
 		const slice = sliceFlowNodes(filtered, this.visibleLimit);
-		const layout = layoutFlowGraph(slice.nodes, { collapsedIds: this.collapsedNodeIds });
+		const merged = mergeToolCallNodes(mergeDiscoveryNodes(slice.nodes));
+		const layout = layoutFlowGraph(merged, { collapsedIds: this.collapsedNodeIds, expandedMergedIds: this.expandedMergedIds });
 		this.renderResult = renderFlowChartSVG(layout);
 
 		this.svgWrapper = DOM.append(this.content, $('.chat-debug-flowchart-svg-wrapper'));
@@ -264,8 +282,11 @@ export class ChatDebugFlowChartView extends Disposable {
 			this.applyTransform();
 		}
 
-		// Restore focus after re-render (e.g. after collapse toggle)
-		if (this.focusedElementId) {
+		// Restore focus after re-render only when the chart itself had focus
+		// before clearNode removed it (e.g. after collapse toggle). Skip when
+		// focus was elsewhere (detail panel, filter, or outside the chart)
+		// so that new events arriving don't steal focus.
+		if (this.focusedElementId && hadFocus && !DOM.isAncestorOfActiveElement(this.headerContainer)) {
 			this.restoreFocus(this.focusedElementId);
 		}
 	}
@@ -307,10 +328,23 @@ export class ChatDebugFlowChartView extends Disposable {
 
 			switch (e.key) {
 				case 'Tab': {
-					e.preventDefault();
+					// Navigate between flow chart nodes. When at the boundary,
+					// explicitly move focus to the detail panel (forward) or
+					// let it leave the chart (backward). We cannot rely on
+					// natural tab-out because DOM order of SVG elements does
+					// not match the visual sorted order, which would cause
+					// focus to jump to a random chart node instead of leaving.
 					if (this.focusedElementId) {
-						this.focusAdjacentElement(this.focusedElementId, e.shiftKey ? -1 : 1);
-					} else {
+						const moved = this.focusAdjacentElement(this.focusedElementId, e.shiftKey ? -1 : 1);
+						if (moved) {
+							e.preventDefault();
+						} else if (!e.shiftKey && this.detailPanel.isVisible) {
+							// Forward Tab at end of chart: move to the detail panel
+							e.preventDefault();
+							this.detailPanel.focus();
+						}
+					} else if (!e.shiftKey) {
+						e.preventDefault();
 						this.focusFirstElement();
 					}
 					break;
@@ -320,36 +354,85 @@ export class ChatDebugFlowChartView extends Disposable {
 					if (subgraphId) {
 						e.preventDefault();
 						e.stopPropagation();
+						this.detailPanel.hide();
 						this.toggleSubgraph(subgraphId);
 					} else {
 						const nodeId = target.getAttribute?.('data-node-id');
 						if (nodeId) {
 							e.preventDefault();
-							const event = this.eventById.get(nodeId);
-							if (event) {
-								this.detailPanel.show(event);
+							if (target.getAttribute?.('data-is-toggle')) {
+								this.detailPanel.hide();
+								this.toggleMergedDiscovery(nodeId);
+							} else {
+								const event = this.eventById.get(nodeId);
+								if (event) {
+									this.detailPanel.show(event);
+								}
 							}
 						}
 					}
 					break;
 				case 'ArrowDown':
+					e.preventDefault();
+					if (this.focusedElementId) {
+						this.focusEdgeNeighbor(this.focusedElementId, 'next');
+					} else {
+						this.focusFirstElement();
+					}
+					break;
 				case 'ArrowRight':
 					e.preventDefault();
 					if (this.focusedElementId) {
-						this.focusAdjacentElement(this.focusedElementId, 1);
+						// Expand collapsed subgraph or merged discovery node,
+						// then jump focus to the first revealed child.
+						if (subgraphId && this.collapsedNodeIds.has(subgraphId)) {
+							this.detailPanel.hide();
+							this.collapsedNodeIds.delete(subgraphId);
+							this.focusedElementId = `sg:${subgraphId}`;
+							this.load();
+							this.focusFirstChildOf(`sg:${subgraphId}`);
+						} else if (target.getAttribute?.('data-is-toggle')) {
+							if (!this.expandedMergedIds.has(this.focusedElementId)) {
+								// Expand and jump to the first child
+								this.detailPanel.hide();
+								const mergedId = this.focusedElementId;
+								this.expandedMergedIds.add(mergedId);
+								this.focusedElementId = mergedId;
+								this.load();
+								this.focusFirstChildOf(mergedId);
+							} else {
+								// Already expanded: jump to the first child
+								this.focusFirstChildOf(this.focusedElementId);
+							}
+						}
 					} else {
 						this.focusFirstElement();
 					}
 					break;
 				case 'ArrowUp':
-				case 'ArrowLeft':
 					e.preventDefault();
 					if (this.focusedElementId) {
-						this.focusAdjacentElement(this.focusedElementId, -1);
+						this.focusEdgeNeighbor(this.focusedElementId, 'prev');
 					} else {
 						this.focusFirstElement();
 					}
 					break;
+				case 'ArrowLeft':
+					e.preventDefault();
+					if (this.focusedElementId) {
+						// Collapse expanded subgraph or merged discovery node
+						if (subgraphId && !this.collapsedNodeIds.has(subgraphId)) {
+							this.detailPanel.hide();
+							this.toggleSubgraph(subgraphId);
+						} else if (target.getAttribute?.('data-is-toggle') && this.expandedMergedIds.has(this.focusedElementId)) {
+							this.detailPanel.hide();
+							this.toggleMergedDiscovery(this.focusedElementId);
+						} else {
+							// Navigate back to parent (follow edge backward)
+							this.focusEdgeNeighbor(this.focusedElementId, 'prev');
+						}
+					}
+					break;
 				case 'Home':
 					e.preventDefault();
 					this.focusFirstElement();
@@ -385,6 +468,16 @@ export class ChatDebugFlowChartView extends Disposable {
 		this.load();
 	}
 
+	private toggleMergedDiscovery(mergedId: string): void {
+		if (this.expandedMergedIds.has(mergedId)) {
+			this.expandedMergedIds.delete(mergedId);
+		} else {
+			this.expandedMergedIds.add(mergedId);
+		}
+		this.focusedElementId = mergedId;
+		this.load();
+	}
+
 	private focusFirstElement(): void {
 		if (!this.renderResult) {
 			return;
@@ -405,22 +498,80 @@ export class ChatDebugFlowChartView extends Disposable {
 		}
 	}
 
-	private focusAdjacentElement(currentMapKey: string, direction: 1 | -1): void {
+	private focusAdjacentElement(currentMapKey: string, direction: 1 | -1): boolean {
 		if (!this.renderResult) {
-			return;
+			return false;
 		}
 		const keys = [...this.renderResult.focusableElements.keys()];
 		const idx = keys.indexOf(currentMapKey);
 		if (idx === -1) {
-			return;
+			return false;
 		}
 		const nextIdx = idx + direction;
 		if (nextIdx < 0 || nextIdx >= keys.length) {
-			return;
+			return false;
 		}
 		const el = this.renderResult.focusableElements.get(keys[nextIdx]);
 		if (el) {
 			(el as SVGElement).focus();
+			return true;
+		}
+		return false;
+	}
+
+	private focusEdgeNeighbor(currentId: string, direction: 'next' | 'prev'): boolean {
+		if (!this.renderResult) {
+			return false;
+		}
+		const entry = this.renderResult.adjacency.get(currentId);
+		const neighbors = entry?.[direction];
+		if (!neighbors || neighbors.length === 0) {
+			return false;
+		}
+		// Focus the first neighbor that has a focusable element
+		for (const id of neighbors) {
+			const el = this.renderResult.focusableElements.get(id);
+			if (el) {
+				(el as SVGElement).focus();
+				return true;
+			}
+		}
+		return false;
+	}
+
+	private focusFirstChildOf(parentId: string): void {
+		if (!this.renderResult) {
+			return;
+		}
+		const entry = this.renderResult.adjacency.get(parentId);
+		if (!entry?.next || entry.next.length === 0) {
+			return;
+		}
+		// Prefer a neighbor positioned to the right of the parent
+		// (expanded child) over one below (next in main flow).
+		const parentPos = this.renderResult.positions.get(parentId);
+		let bestId: string | undefined;
+		for (const id of entry.next) {
+			if (!this.renderResult.focusableElements.has(id)) {
+				continue;
+			}
+			if (!bestId) {
+				bestId = id;
+			}
+			if (parentPos) {
+				const pos = this.renderResult.positions.get(id);
+				if (pos && pos.x > parentPos.x) {
+					bestId = id;
+					break;
+				}
+			}
+		}
+		if (bestId) {
+			const el = this.renderResult.focusableElements.get(bestId);
+			if (el) {
+				this.focusedElementId = bestId;
+				(el as SVGElement).focus();
+			}
 		}
 	}
 
@@ -489,17 +640,30 @@ export class ChatDebugFlowChartView extends Disposable {
 		// Walk up from the click target to find a focusable element
 		let target = e.target as Element | null;
 		while (target && target !== this.content) {
+			// Merged-discovery expand toggle
+			const mergedId = target.getAttribute?.('data-merged-id');
+			if (mergedId) {
+				this.detailPanel.hide();
+				this.toggleMergedDiscovery(mergedId);
+				return;
+			}
 			const subgraphId = target.getAttribute?.('data-subgraph-id');
 			if (subgraphId) {
+				this.detailPanel.hide();
 				this.toggleSubgraph(subgraphId);
 				return;
 			}
 			const nodeId = target.getAttribute?.('data-node-id');
 			if (nodeId) {
 				(target as HTMLElement).focus();
-				const event = this.eventById.get(nodeId);
-				if (event) {
-					this.detailPanel.show(event);
+				if (target.getAttribute?.('data-is-toggle')) {
+					this.detailPanel.hide();
+					this.toggleMergedDiscovery(nodeId);
+				} else {
+					const event = this.eventById.get(nodeId);
+					if (event) {
+						this.detailPanel.show(event);
+					}
 				}
 				return;
 			}
@@ -541,9 +705,17 @@ export class ChatDebugFlowChartView extends Disposable {
 		}
 		const svgWidth = parseFloat(this.svgElement.getAttribute('width') || '0');
 		const svgHeight = parseFloat(this.svgElement.getAttribute('height') || '0');
+		if (svgWidth <= 0 || svgHeight <= 0) {
+			return;
+		}
 
-		this.translateX = (containerRect.width - svgWidth) / 2;
-		this.translateY = Math.max(20, (containerRect.height - svgHeight) / 2);
+		const PADDING = 20;
+		// Pin the top of the diagram near the top of the viewport so the start
+		// of the flow is immediately visible. Center horizontally when the
+		// diagram fits; otherwise align to the left edge with padding so
+		// nothing is clipped behind overflow:hidden.
+		this.translateX = Math.max(PADDING, (containerRect.width - svgWidth) / 2);
+		this.translateY = PADDING;
 		this.applyTransform();
 	}
 }
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowGraph.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowGraph.ts
index 41125ffd836a5..48e5ce0dced81 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowGraph.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowGraph.ts
@@ -3,6 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { localize } from '../../../../../nls.js';
 import { IChatDebugEvent } from '../../common/chatDebugService.js';
 
 // ---- Data model ----
@@ -10,6 +11,8 @@ import { IChatDebugEvent } from '../../common/chatDebugService.js';
 export interface FlowNode {
 	readonly id: string;
 	readonly kind: IChatDebugEvent['kind'];
+	/** For `generic` nodes: the event category (e.g. `'discovery'`). Used to narrow filtering. */
+	readonly category?: string;
 	readonly label: string;
 	readonly sublabel?: string;
 	readonly description?: string;
@@ -17,10 +20,12 @@ export interface FlowNode {
 	readonly isError?: boolean;
 	readonly created: number;
 	readonly children: FlowNode[];
+	/** Present on merged discovery nodes: the individual nodes that were merged. */
+	readonly mergedNodes?: FlowNode[];
 }
 
 export interface FlowFilterOptions {
-	readonly isKindVisible: (kind: string) => boolean;
+	readonly isKindVisible: (kind: string, category?: string) => boolean;
 	readonly textFilter: string;
 }
 
@@ -35,9 +40,15 @@ export interface LayoutNode {
 	readonly y: number;
 	readonly width: number;
 	readonly height: number;
+	/** Number of individual nodes merged into this one (for discovery merging). */
+	readonly mergedCount?: number;
+	/** Whether the merged node is currently expanded (individual nodes shown to the right). */
+	readonly isMergedExpanded?: boolean;
 }
 
 export interface LayoutEdge {
+	readonly fromId?: string;
+	readonly toId?: string;
 	readonly fromX: number;
 	readonly fromY: number;
 	readonly toX: number;
@@ -67,6 +78,10 @@ export interface FlowChartRenderResult {
 	readonly svg: SVGElement;
 	/** Map from node/subgraph ID to its focusable SVG element. */
 	readonly focusableElements: Map<string, SVGElement>;
+	/** Adjacency lists derived from graph edges: successors and predecessors per node ID. */
+	readonly adjacency: Map<string, { next: string[]; prev: string[] }>;
+	/** Map from node/subgraph ID to its layout position. */
+	readonly positions: Map<string, { x: number; y: number }>;
 }
 
 // ---- Build flow graph from debug events ----
@@ -158,15 +173,24 @@ export function buildFlowGraph(events: readonly IChatDebugEvent[]): FlowNode[] {
 	function toFlowNode(event: IChatDebugEvent): FlowNode {
 		const children = event.id ? idToChildren.get(event.id) : undefined;
 
+		// Remap generic events with well-known names to their proper kind
+		// so they get correct styling and sublabel treatment.
+		const effectiveKind = getEffectiveKind(event);
+
 		// For subagent invocations, enrich with description from the
 		// filtered-out completion sibling, or fall back to the event's own field.
-		let sublabel = getEventSublabel(event);
+		let label = getEventLabel(event, effectiveKind);
+		const sublabel = getEventSublabel(event, effectiveKind);
 		let tooltip = getEventTooltip(event);
 		let description: string | undefined;
-		if (event.kind === 'subagentInvocation') {
+		if (effectiveKind === 'subagentInvocation') {
 			description = getSubagentDescription(event);
+			// Show "Subagent: <description>" as the label so users can identify
+			// these nodes and see what task they perform.
+			label = description
+				? localize('subagentWithDesc', "Subagent: {0}", truncateLabel(description, 30))
+				: localize('subagentLabel', "Subagent");
 			if (description) {
-				sublabel = truncateLabel(description, 30) + (sublabel ? ` \u00b7 ${sublabel}` : '');
 				// Ensure description appears in tooltip if not already present
 				if (tooltip && !tooltip.includes(description)) {
 					const lines = tooltip.split('\n');
@@ -178,8 +202,9 @@ export function buildFlowGraph(events: readonly IChatDebugEvent[]): FlowNode[] {
 
 		return {
 			id: event.id ?? `event-${events.indexOf(event)}`,
-			kind: event.kind,
-			label: getEventLabel(event),
+			kind: effectiveKind,
+			category: event.kind === 'generic' ? event.category : undefined,
+			label,
 			sublabel,
 			description,
 			tooltip,
@@ -189,70 +214,7 @@ export function buildFlowGraph(events: readonly IChatDebugEvent[]): FlowNode[] {
 		};
 	}
 
-	return mergeModelTurns(roots.map(toFlowNode));
-}
-
-/**
- * Absorbs model turn nodes into the subsequent sibling node.
- *
- * Each model turn represents an LLM call that decides what to do next
- * (call tools, respond, etc.). Rather than showing model turns as separate
- * boxes, we merge their metadata (token count, LLM latency) into the next
- * node's sublabel and tooltip so the diagram stays compact while
- * preserving the correlation.
- */
-function mergeModelTurns(nodes: FlowNode[]): FlowNode[] {
-	const result: FlowNode[] = [];
-	let pendingModelTurn: FlowNode | undefined;
-
-	for (const node of nodes) {
-		if (node.kind === 'modelTurn') {
-			pendingModelTurn = node;
-			continue;
-		}
-
-		const merged = applyModelTurnInfo(node, pendingModelTurn);
-		pendingModelTurn = undefined;
-		result.push(merged);
-	}
-
-	// If the last node was a model turn with no successor, keep it
-	if (pendingModelTurn) {
-		result.push(pendingModelTurn);
-	}
-
-	return result;
-}
-
-/**
- * Enriches a node with model turn metadata and recursively
- * merges model turns within its children.
- */
-function applyModelTurnInfo(node: FlowNode, modelTurn: FlowNode | undefined): FlowNode {
-	const mergedChildren = node.children.length > 0 ? mergeModelTurns(node.children) : node.children;
-
-	if (!modelTurn) {
-		return mergedChildren !== node.children ? { ...node, children: mergedChildren } : node;
-	}
-
-	// Build compact annotation from model turn info (e.g. "500 tok · LLM 2.3s")
-	const annotation = modelTurn.sublabel;
-	const newSublabel = annotation
-		? (node.sublabel ? `${node.sublabel} \u00b7 ${annotation}` : annotation)
-		: node.sublabel;
-
-	// Enrich tooltip with model turn details
-	const modelTooltip = modelTurn.tooltip ?? (modelTurn.label !== 'Model Turn' ? modelTurn.label : undefined);
-	const newTooltip = modelTooltip
-		? (node.tooltip ? `${node.tooltip}\n\nModel: ${modelTooltip}` : `Model: ${modelTooltip}`)
-		: node.tooltip;
-
-	return {
-		...node,
-		sublabel: newSublabel,
-		tooltip: newTooltip,
-		children: mergedChildren,
-	};
+	return roots.map(toFlowNode);
 }
 
 // ---- Flow node filtering ----
@@ -277,11 +239,11 @@ export function filterFlowNodes(nodes: FlowNode[], options: FlowFilterOptions):
 	return result;
 }
 
-function filterByKind(nodes: FlowNode[], isKindVisible: (kind: string) => boolean): FlowNode[] {
+function filterByKind(nodes: FlowNode[], isKindVisible: (kind: string, category?: string) => boolean): FlowNode[] {
 	const result: FlowNode[] = [];
 	let changed = false;
 	for (const node of nodes) {
-		if (!isKindVisible(node.kind)) {
+		if (!isKindVisible(node.kind, node.category)) {
 			changed = true;
 			// For subagents, drop the entire subgraph
 			if (node.kind === 'subagentInvocation') {
@@ -302,6 +264,7 @@ function filterByKind(nodes: FlowNode[], isKindVisible: (kind: string) => boolea
 	return changed ? result : nodes;
 }
 
+
 function nodeMatchesText(node: FlowNode, text: string): boolean {
 	return node.label.toLowerCase().includes(text) ||
 		(node.sublabel?.toLowerCase().includes(text) ?? false) ||
@@ -382,59 +345,273 @@ export function sliceFlowNodes(nodes: readonly FlowNode[], maxCount: number): Fl
 	return { nodes: sliced, totalCount, shownCount };
 }
 
+// ---- Discovery node merging ----
+
+function isDiscoveryNode(node: FlowNode): boolean {
+	return node.kind === 'generic' && node.category === 'discovery';
+}
+
+/**
+ * Merges consecutive prompt-discovery nodes (generic events with
+ * `category === 'discovery'`) into a single summary node.
+ *
+ * The merged node always stays in the graph and carries the individual
+ * nodes in `mergedNodes`.  Expansion (showing the individual nodes to the
+ * right) is handled at the layout level.
+ *
+ * Operates recursively on children.
+ */
+export function mergeDiscoveryNodes(
+	nodes: readonly FlowNode[],
+): FlowNode[] {
+	const result: FlowNode[] = [];
+
+	let i = 0;
+	while (i < nodes.length) {
+		const node = nodes[i];
+
+		// Non-discovery node: recurse into children and pass through.
+		if (!isDiscoveryNode(node)) {
+			const mergedChildren = mergeDiscoveryNodes(node.children);
+			result.push(mergedChildren !== node.children ? { ...node, children: mergedChildren } : node);
+			i++;
+			continue;
+		}
+
+		// Accumulate a run of consecutive discovery nodes.
+		const run: FlowNode[] = [node];
+		let j = i + 1;
+		while (j < nodes.length && isDiscoveryNode(nodes[j])) {
+			run.push(nodes[j]);
+			j++;
+		}
+
+		if (run.length < 2) {
+			// Single discovery node — nothing to merge.
+			result.push(node);
+			i = j;
+			continue;
+		}
+
+		// Build a stable id from the first node so the expand state persists.
+		const mergedId = `merged-discovery:${run[0].id}`;
+
+		// Build a merged summary node.
+		const labels = run.map(n => n.label);
+		const uniqueLabels = [...new Set(labels)];
+		const summaryLabel = uniqueLabels.length <= 2
+			? uniqueLabels.join(', ')
+			: localize('discoveryMergedLabel', "{0} +{1} more", uniqueLabels[0], run.length - 1);
+
+		result.push({
+			id: mergedId,
+			kind: 'generic',
+			category: 'discovery',
+			label: summaryLabel,
+			sublabel: localize('discoveryStepsCount', "{0} discovery steps", run.length),
+			tooltip: run.map(n => n.label + (n.sublabel ? `: ${n.sublabel}` : '')).join('\n'),
+			created: run[0].created,
+			children: [],
+			mergedNodes: run,
+		});
+		i = j;
+	}
+
+	return result;
+}
+
+// ---- Tool call node merging ----
+
+function isToolCallNode(node: FlowNode): boolean {
+	return node.kind === 'toolCall';
+}
+
+/**
+ * Returns the tool name from a tool-call node's label.
+ * Tool call labels are set to `event.toolName` (possibly with a leading
+ * emoji prefix stripped), so the label itself is the canonical tool name.
+ */
+function getToolName(node: FlowNode): string {
+	return node.label;
+}
+
+/**
+ * Merges consecutive tool-call nodes that invoke the same tool into a
+ * single summary node.
+ *
+ * This mirrors `mergeDiscoveryNodes`: the merged node carries the
+ * individual nodes in `mergedNodes` and expansion is handled at the
+ * layout level.
+ *
+ * Operates recursively on children.
+ */
+export function mergeToolCallNodes(
+	nodes: readonly FlowNode[],
+): FlowNode[] {
+	const result: FlowNode[] = [];
+
+	let i = 0;
+	while (i < nodes.length) {
+		const node = nodes[i];
+
+		// Non-tool-call node: recurse into children and pass through.
+		if (!isToolCallNode(node)) {
+			const mergedChildren = mergeToolCallNodes(node.children);
+			result.push(mergedChildren !== node.children ? { ...node, children: mergedChildren } : node);
+			i++;
+			continue;
+		}
+
+		// Accumulate a run of consecutive tool-call nodes with the same tool name.
+		const toolName = getToolName(node);
+		const run: FlowNode[] = [node];
+		let j = i + 1;
+		while (j < nodes.length && isToolCallNode(nodes[j]) && getToolName(nodes[j]) === toolName) {
+			run.push(nodes[j]);
+			j++;
+		}
+
+		if (run.length < 2) {
+			// Single tool call — recurse into children, nothing to merge.
+			const mergedChildren = mergeToolCallNodes(node.children);
+			result.push(mergedChildren !== node.children ? { ...node, children: mergedChildren } : node);
+			i = j;
+			continue;
+		}
+
+		// Build a stable id from the first node so the expand state persists.
+		const mergedId = `merged-toolCall:${run[0].id}`;
+
+		result.push({
+			id: mergedId,
+			kind: 'toolCall',
+			label: toolName,
+			sublabel: localize('toolCallsCount', "{0} calls", run.length),
+			tooltip: run.map(n => n.label + (n.sublabel ? `: ${n.sublabel}` : '')).join('\n'),
+			created: run[0].created,
+			children: [],
+			mergedNodes: run,
+		});
+		i = j;
+	}
+
+	return result;
+}
+
 // ---- Event helpers ----
 
-function getEventLabel(event: IChatDebugEvent): string {
-	switch (event.kind) {
-		case 'userMessage': {
-			const firstLine = event.message.split('\n')[0];
-			return firstLine.length > 40 ? firstLine.substring(0, 37) + '...' : firstLine;
+/**
+ * Remaps generic events with well-known names (e.g. "User message",
+ * "Agent response") to their proper typed kind so they receive
+ * correct colors, labels, and sublabel treatment in the flow chart.
+ */
+function getEffectiveKind(event: IChatDebugEvent): IChatDebugEvent['kind'] {
+	if (event.kind === 'generic') {
+		const name = event.name.toLowerCase().replace(/[\s_-]+/g, '');
+		if (name === 'usermessage' || name === 'userprompt' || name === 'user' || name.startsWith('usermessage')) {
+			return 'userMessage';
+		}
+		if (name === 'response' || name.startsWith('agentresponse') || name.startsWith('assistantresponse') || name.startsWith('modelresponse')) {
+			return 'agentResponse';
+		}
+		const cat = event.category?.toLowerCase();
+		if (cat === 'user' || cat === 'usermessage') {
+			return 'userMessage';
+		}
+		if (cat === 'response' || cat === 'agentresponse') {
+			return 'agentResponse';
 		}
+	}
+	return event.kind;
+}
+
+function getEventLabel(event: IChatDebugEvent, effectiveKind?: IChatDebugEvent['kind']): string {
+	const kind = effectiveKind ?? event.kind;
+	switch (kind) {
+		case 'userMessage':
+			return localize('userLabel', "User Message");
 		case 'modelTurn':
-			return event.model ?? 'Model Turn';
+			return event.kind === 'modelTurn' ? (event.model ?? localize('modelTurnLabel', "Model Turn")) : localize('modelTurnLabel', "Model Turn");
 		case 'toolCall':
-			return event.toolName;
+			return event.kind === 'toolCall' ? event.toolName : event.kind === 'generic' ? event.name : localize('toolCallLabel', "Tool Call");
 		case 'subagentInvocation':
-			return event.agentName;
+			return event.kind === 'subagentInvocation' ? event.agentName : localize('subagentFallback', "Subagent");
 		case 'agentResponse':
-			return 'Response';
+			return localize('agentResponseLabel', "Agent Response");
 		case 'generic':
-			return event.name;
+			return event.kind === 'generic' ? event.name : localize('genericLabel', "Event");
 	}
 }
 
-function getEventSublabel(event: IChatDebugEvent): string | undefined {
-	switch (event.kind) {
+function getEventSublabel(event: IChatDebugEvent, effectiveKind?: IChatDebugEvent['kind']): string | undefined {
+	const kind = effectiveKind ?? event.kind;
+	switch (kind) {
 		case 'modelTurn': {
 			const parts: string[] = [];
-			if (event.totalTokens) {
-				parts.push(`${event.totalTokens} tokens`);
+			if (event.kind === 'modelTurn' && event.requestName) {
+				parts.push(event.requestName);
 			}
-			if (event.durationInMillis) {
+			if (event.kind === 'modelTurn' && event.totalTokens) {
+				parts.push(localize('tokenCount', "{0} tokens", event.totalTokens));
+			}
+			if (event.kind === 'modelTurn' && event.durationInMillis) {
 				parts.push(formatDuration(event.durationInMillis));
 			}
 			return parts.length > 0 ? parts.join(' \u00b7 ') : undefined;
 		}
 		case 'toolCall': {
 			const parts: string[] = [];
-			if (event.result) {
+			if (event.kind === 'toolCall' && event.result) {
 				parts.push(event.result);
 			}
-			if (event.durationInMillis) {
+			if (event.kind === 'toolCall' && event.durationInMillis) {
 				parts.push(formatDuration(event.durationInMillis));
 			}
 			return parts.length > 0 ? parts.join(' \u00b7 ') : undefined;
 		}
 		case 'subagentInvocation': {
 			const parts: string[] = [];
-			if (event.status) {
+			if (event.kind === 'subagentInvocation' && event.status) {
 				parts.push(event.status);
 			}
-			if (event.durationInMillis) {
+			if (event.kind === 'subagentInvocation' && event.durationInMillis) {
 				parts.push(formatDuration(event.durationInMillis));
 			}
 			return parts.length > 0 ? parts.join(' \u00b7 ') : undefined;
 		}
+		case 'userMessage':
+		case 'agentResponse': {
+			// Use the message summary as the sublabel. For remapped generic
+			// events, use the details property.
+			let text: string | undefined;
+			if (event.kind === 'userMessage' || event.kind === 'agentResponse') {
+				text = event.message;
+			} else if (event.kind === 'generic') {
+				text = event.details;
+			}
+			if (!text) {
+				return undefined;
+			}
+			// Find the first meaningful line, skipping trivial lines like
+			// lone brackets/braces that appear when the message is JSON.
+			const lines = text.split('\n');
+			let firstLine = '';
+			for (const line of lines) {
+				const trimmed = line.trim();
+				if (trimmed && trimmed.length > 2) {
+					firstLine = trimmed;
+					break;
+				}
+			}
+			if (!firstLine) {
+				// Fall back to the full text collapsed to a single line
+				firstLine = text.replace(/\s+/g, ' ').trim();
+			}
+			if (!firstLine) {
+				return undefined;
+			}
+			return firstLine.length > 60 ? firstLine.substring(0, 57) + '...' : firstLine;
+		}
 		default:
 			return undefined;
 	}
@@ -468,14 +645,14 @@ function getEventTooltip(event: IChatDebugEvent): string | undefined {
 			const parts: string[] = [event.toolName];
 			if (event.input) {
 				const input = event.input.trim();
-				parts.push(`Input: ${input.length > TOOLTIP_MAX_LENGTH ? input.substring(0, TOOLTIP_MAX_LENGTH) + '\u2026' : input}`);
+				parts.push(localize('tooltipInput', "Input: {0}", input.length > TOOLTIP_MAX_LENGTH ? input.substring(0, TOOLTIP_MAX_LENGTH) + '\u2026' : input));
 			}
 			if (event.output) {
 				const output = event.output.trim();
-				parts.push(`Output: ${output.length > TOOLTIP_MAX_LENGTH ? output.substring(0, TOOLTIP_MAX_LENGTH) + '\u2026' : output}`);
+				parts.push(localize('tooltipOutput', "Output: {0}", output.length > TOOLTIP_MAX_LENGTH ? output.substring(0, TOOLTIP_MAX_LENGTH) + '\u2026' : output));
 			}
 			if (event.result) {
-				parts.push(`Result: ${event.result}`);
+				parts.push(localize('tooltipResult', "Result: {0}", event.result));
 			}
 			return parts.join('\n');
 		}
@@ -485,13 +662,13 @@ function getEventTooltip(event: IChatDebugEvent): string | undefined {
 				parts.push(event.description);
 			}
 			if (event.status) {
-				parts.push(`Status: ${event.status}`);
+				parts.push(localize('tooltipStatus', "Status: {0}", event.status));
 			}
 			if (event.toolCallCount !== undefined) {
-				parts.push(`Tool calls: ${event.toolCallCount}`);
+				parts.push(localize('tooltipToolCalls', "Tool calls: {0}", event.toolCallCount));
 			}
 			if (event.modelTurnCount !== undefined) {
-				parts.push(`Model turns: ${event.modelTurnCount}`);
+				parts.push(localize('tooltipModelTurns', "Model turns: {0}", event.modelTurnCount));
 			}
 			return parts.join('\n');
 		}
@@ -508,16 +685,16 @@ function getEventTooltip(event: IChatDebugEvent): string | undefined {
 				parts.push(event.model);
 			}
 			if (event.totalTokens) {
-				parts.push(`Tokens: ${event.totalTokens}`);
+				parts.push(localize('tooltipTokens', "Tokens: {0}", event.totalTokens));
 			}
 			if (event.inputTokens) {
-				parts.push(`Input tokens: ${event.inputTokens}`);
+				parts.push(localize('tooltipInputTokens', "Input tokens: {0}", event.inputTokens));
 			}
 			if (event.outputTokens) {
-				parts.push(`Output tokens: ${event.outputTokens}`);
+				parts.push(localize('tooltipOutputTokens', "Output tokens: {0}", event.outputTokens));
 			}
 			if (event.durationInMillis) {
-				parts.push(`Duration: ${formatDuration(event.durationInMillis)}`);
+				parts.push(localize('tooltipDuration', "Duration: {0}", formatDuration(event.durationInMillis)));
 			}
 			return parts.length > 0 ? parts.join('\n') : undefined;
 		}
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowLayout.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowLayout.ts
index 5e730d0309c2e..403003e62bd6d 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowLayout.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugFlowLayout.ts
@@ -9,6 +9,7 @@ import { FlowLayout, FlowNode, LayoutEdge, LayoutNode, SubgraphRect, FlowChartRe
 // ---- Layout constants ----
 
 const NODE_HEIGHT = 36;
+const MESSAGE_NODE_HEIGHT = 52;
 const NODE_MIN_WIDTH = 140;
 const NODE_MAX_WIDTH = 320;
 const NODE_PADDING_H = 16;
@@ -23,6 +24,7 @@ const CANVAS_PADDING = 24;
 const PARALLEL_GAP_X = 40;
 const SUBGRAPH_HEADER_HEIGHT = 22;
 const GUTTER_WIDTH = 3;
+const MERGED_TOGGLE_WIDTH = 36;
 
 // ---- Layout internals ----
 
@@ -41,6 +43,14 @@ interface ChildGroup {
 	readonly children: FlowNode[];
 }
 
+/** Deferred expansion of a merged-discovery node, resolved in pass 2. */
+interface PendingExpansion {
+	/** The merged summary LayoutNode (already placed). */
+	readonly mergedNode: LayoutNode;
+	/** The individual FlowNodes to expand to the right. */
+	readonly children: readonly FlowNode[];
+}
+
 // ---- Parallel detection ----
 
 /** Max time gap (ms) between subagent `created` timestamps to consider them parallel. */
@@ -137,6 +147,10 @@ function groupChildren(children: FlowNode[]): ChildGroup[] {
 
 // ---- Layout engine ----
 
+function isMessageKind(kind: IChatDebugEvent['kind']): boolean {
+	return kind === 'userMessage' || kind === 'agentResponse';
+}
+
 function measureNodeWidth(label: string, sublabel?: string): number {
 	const charWidth = 7;
 	const labelWidth = label.length * charWidth + NODE_PADDING_H * 2;
@@ -145,7 +159,15 @@ function measureNodeWidth(label: string, sublabel?: string): number {
 }
 
 function subgraphHeaderLabel(node: FlowNode): string {
-	return node.description ? `${node.label}: ${node.description}` : node.label;
+	// For subagent nodes, the label already includes the description
+	// (e.g. "Subagent: Count markdown files"), so don't append it again.
+	if (node.kind === 'subagentInvocation') {
+		return node.label;
+	}
+	if (node.description && node.description !== node.label) {
+		return `${node.label}: ${node.description}`;
+	}
+	return node.label;
 }
 
 function measureSubgraphHeaderWidth(headerLabel: string): number {
@@ -174,6 +196,8 @@ function layoutGroups(
 	prevExitNodes: LayoutNode[],
 	result: { nodes: LayoutNode[]; edges: LayoutEdge[]; subgraphs: SubgraphRect[] },
 	collapsedIds?: ReadonlySet<string>,
+	expandedMergedIds?: ReadonlySet<string>,
+	pendingExpansions?: PendingExpansion[],
 ): { exitNodes: LayoutNode[]; maxWidth: number; endY: number } {
 	let currentY = startY;
 	let maxWidth = 0;
@@ -181,7 +205,7 @@ function layoutGroups(
 
 	for (const group of groups) {
 		if (group.type === 'parallel') {
-			const pg = layoutParallelGroup(group.children, startX, currentY, depth, collapsedIds);
+			const pg = layoutParallelGroup(group.children, startX, currentY, depth, collapsedIds, expandedMergedIds, pendingExpansions);
 			result.nodes.push(...pg.nodes);
 			result.edges.push(...pg.edges);
 			result.subgraphs.push(...pg.subgraphs);
@@ -196,7 +220,7 @@ function layoutGroups(
 			currentY += pg.height + NODE_GAP_Y;
 		} else {
 			for (const child of group.children) {
-				const sub = layoutSubtree(child, startX, currentY, depth, collapsedIds);
+				const sub = layoutSubtree(child, startX, currentY, depth, collapsedIds, expandedMergedIds, pendingExpansions);
 				result.nodes.push(...sub.nodes);
 				result.edges.push(...sub.edges);
 				result.subgraphs.push(...sub.subgraphs);
@@ -215,6 +239,8 @@ function layoutGroups(
 
 function makeEdge(from: LayoutNode, to: LayoutNode): LayoutEdge {
 	return {
+		fromId: from.id,
+		toId: to.id,
 		fromX: from.x + from.width / 2,
 		fromY: from.y + from.height,
 		toX: to.x + to.width / 2,
@@ -226,32 +252,125 @@ function makeEdge(from: LayoutNode, to: LayoutNode): LayoutEdge {
  * Lays out a list of flow nodes in a top-down vertical flow.
  * Parallel subagent invocations are arranged side by side.
  */
-export function layoutFlowGraph(roots: FlowNode[], options?: { collapsedIds?: ReadonlySet<string> }): FlowLayout {
+export function layoutFlowGraph(roots: FlowNode[], options?: { collapsedIds?: ReadonlySet<string>; expandedMergedIds?: ReadonlySet<string> }): FlowLayout {
 	if (roots.length === 0) {
 		return { nodes: [], edges: [], subgraphs: [], width: 0, height: 0 };
 	}
 
 	const collapsedIds = options?.collapsedIds;
+	const expandedMergedIds = options?.expandedMergedIds;
 	const groups = groupChildren(roots);
+	const pendingExpansions: PendingExpansion[] = [];
 	const result: { nodes: LayoutNode[]; edges: LayoutEdge[]; subgraphs: SubgraphRect[] } = {
 		nodes: [],
 		edges: [],
 		subgraphs: [],
 	};
 
-	const { maxWidth, endY } = layoutGroups(groups, CANVAS_PADDING, CANVAS_PADDING, 0, [], result, collapsedIds);
-	const width = maxWidth + CANVAS_PADDING * 2;
-	const height = endY - NODE_GAP_Y + CANVAS_PADDING;
+	// Pass 1: layout the main vertical flow; expanded merged nodes only
+	// place their summary node and defer children to pendingExpansions.
+	const { maxWidth, endY } = layoutGroups(groups, CANVAS_PADDING, CANVAS_PADDING, 0, [], result, collapsedIds, expandedMergedIds, pendingExpansions);
+
+	// Pass 2: resolve deferred expansions — place children to the right,
+	// far enough to clear all existing nodes/subgraphs in the Y range.
+	resolvePendingExpansions(pendingExpansions, result);
+
+	let width = maxWidth + CANVAS_PADDING * 2;
+	let height = endY - NODE_GAP_Y + CANVAS_PADDING;
+
+	// Expand canvas to cover any nodes that float outside the main flow.
+	for (const n of result.nodes) {
+		width = Math.max(width, n.x + n.width + CANVAS_PADDING);
+		height = Math.max(height, n.y + n.height + CANVAS_PADDING);
+	}
 
 	centerLayout(result as FlowLayout & { nodes: LayoutNode[]; edges: LayoutEdge[]; subgraphs: SubgraphRect[] }, width / 2);
 
 	return { nodes: result.nodes, edges: result.edges, subgraphs: result.subgraphs, width, height };
 }
 
-function layoutSubtree(node: FlowNode, startX: number, y: number, depth: number, collapsedIds?: ReadonlySet<string>): SubtreeLayout {
-	const nodeWidth = measureNodeWidth(node.label, node.sublabel);
+/**
+ * Pass 2: For each pending expansion, compute the Y range the children
+ * will occupy, scan all already-placed nodes and subgraphs for the max
+ * right edge overlapping that range, and place the entire column of
+ * children to the right of that edge.
+ */
+function resolvePendingExpansions(
+	pendingExpansions: PendingExpansion[],
+	result: { nodes: LayoutNode[]; edges: LayoutEdge[]; subgraphs: SubgraphRect[] },
+): void {
+	for (const expansion of pendingExpansions) {
+		const { mergedNode, children } = expansion;
+
+		// Compute the Y range the children will occupy.
+		const childrenTotalHeight = children.length * NODE_HEIGHT + (children.length - 1) * NODE_GAP_Y;
+		const rangeTop = mergedNode.y;
+		const rangeBottom = mergedNode.y + childrenTotalHeight;
+
+		// Find the max right edge of any existing node or subgraph
+		// that overlaps this Y range.
+		let maxRightX = mergedNode.x + mergedNode.width;
+		for (const n of result.nodes) {
+			if (n.y + n.height > rangeTop && n.y < rangeBottom) {
+				maxRightX = Math.max(maxRightX, n.x + n.width);
+			}
+		}
+		for (const sg of result.subgraphs) {
+			if (sg.y + sg.height > rangeTop && sg.y < rangeBottom) {
+				maxRightX = Math.max(maxRightX, sg.x + sg.width);
+			}
+		}
+
+		const expandX = maxRightX + PARALLEL_GAP_X;
+		let expandY = mergedNode.y;
+		let expandMaxWidth = 0;
+
+		const childNodes: LayoutNode[] = [];
+		for (const child of children) {
+			const childWidth = measureNodeWidth(child.label, child.sublabel);
+			const childNode: LayoutNode = {
+				id: child.id,
+				kind: child.kind,
+				label: child.label,
+				sublabel: child.sublabel,
+				tooltip: child.tooltip,
+				isError: child.isError,
+				x: expandX,
+				y: expandY,
+				width: childWidth,
+				height: NODE_HEIGHT,
+			};
+			childNodes.push(childNode);
+			result.nodes.push(childNode);
+			expandMaxWidth = Math.max(expandMaxWidth, childWidth);
+			expandY += NODE_HEIGHT + NODE_GAP_Y;
+		}
+
+		// Horizontal edge from merged node to first child
+		result.edges.push({
+			fromId: mergedNode.id,
+			toId: childNodes[0].id,
+			fromX: mergedNode.x + mergedNode.width,
+			fromY: mergedNode.y + mergedNode.height / 2,
+			toX: expandX,
+			toY: childNodes[0].y + childNodes[0].height / 2,
+		});
+
+		// Vertical edges between consecutive children
+		for (let k = 0; k < childNodes.length - 1; k++) {
+			result.edges.push(makeEdge(childNodes[k], childNodes[k + 1]));
+		}
+	}
+}
+
+function layoutSubtree(node: FlowNode, startX: number, y: number, depth: number, collapsedIds?: ReadonlySet<string>, expandedMergedIds?: ReadonlySet<string>, pendingExpansions?: PendingExpansion[]): SubtreeLayout {
+	const isMerged = (node.mergedNodes?.length ?? 0) >= 2;
+	const isMergedExpanded = isMerged && expandedMergedIds?.has(node.id);
+	const mergedExtra = isMerged ? MERGED_TOGGLE_WIDTH : 0;
+	const nodeWidth = measureNodeWidth(node.label, node.sublabel) + mergedExtra;
 	const isSubagent = node.kind === 'subagentInvocation';
 	const isCollapsed = isSubagent && collapsedIds?.has(node.id);
+	const nodeHeight = isMessageKind(node.kind) && node.sublabel ? MESSAGE_NODE_HEIGHT : NODE_HEIGHT;
 
 	const layoutNode: LayoutNode = {
 		id: node.id,
@@ -263,7 +382,9 @@ function layoutSubtree(node: FlowNode, startX: number, y: number, depth: number,
 		x: startX,
 		y: y,
 		width: nodeWidth,
-		height: NODE_HEIGHT,
+		height: nodeHeight,
+		mergedCount: isMerged ? node.mergedNodes!.length : undefined,
+		isMergedExpanded,
 	};
 
 	const result: SubtreeLayout = {
@@ -271,11 +392,19 @@ function layoutSubtree(node: FlowNode, startX: number, y: number, depth: number,
 		edges: [],
 		subgraphs: [],
 		width: nodeWidth,
-		height: NODE_HEIGHT,
+		height: nodeHeight,
 		entryNode: layoutNode,
 		exitNodes: [layoutNode],
 	};
 
+	// Expanded merged discovery: defer child placement to pass 2.
+	// Only emit the merged summary node now; children will be placed
+	// to the right after all main-flow nodes have been positioned.
+	if (isMergedExpanded && pendingExpansions) {
+		pendingExpansions.push({ mergedNode: layoutNode, children: node.mergedNodes! });
+		return result;
+	}
+
 	if (node.children.length === 0 && !isCollapsed) {
 		return result;
 	}
@@ -284,7 +413,7 @@ function layoutSubtree(node: FlowNode, startX: number, y: number, depth: number,
 	if (isCollapsed) {
 		const collapsedHeight = SUBGRAPH_HEADER_HEIGHT + SUBGRAPH_PADDING * 2;
 		const totalChildCount = countDescendants(node);
-		const sgY = (y + NODE_HEIGHT + NODE_GAP_Y) - NODE_GAP_Y / 2;
+		const sgY = (y + nodeHeight + NODE_GAP_Y) - NODE_GAP_Y / 2;
 		const headerLabel = subgraphHeaderLabel(node);
 		const sgWidth = Math.max(NODE_MIN_WIDTH, measureSubgraphHeaderWidth(headerLabel)) + SUBGRAPH_PADDING * 2;
 		result.subgraphs.push({
@@ -300,12 +429,12 @@ function layoutSubtree(node: FlowNode, startX: number, y: number, depth: number,
 		// Draw a connecting edge from the node to the collapsed subgraph
 		result.edges.push({
 			fromX: startX + nodeWidth / 2,
-			fromY: y + NODE_HEIGHT,
+			fromY: y + nodeHeight,
 			toX: startX - SUBGRAPH_PADDING + sgWidth / 2,
 			toY: sgY,
 		});
 		result.width = Math.max(nodeWidth, sgWidth);
-		result.height = NODE_HEIGHT + NODE_GAP_Y + collapsedHeight;
+		result.height = nodeHeight + NODE_GAP_Y + collapsedHeight;
 		return result;
 	}
 
@@ -317,13 +446,13 @@ function layoutSubtree(node: FlowNode, startX: number, y: number, depth: number,
 	const indentX = isSubagent ? SUBGRAPH_PADDING : 0;
 	const groups = groupChildren(node.children);
 
-	let childStartY = y + NODE_HEIGHT + NODE_GAP_Y;
+	let childStartY = y + nodeHeight + NODE_GAP_Y;
 	if (isSubagent) {
 		childStartY += SUBGRAPH_HEADER_HEIGHT;
 	}
 
 	const { exitNodes, maxWidth, endY } = layoutGroups(
-		groups, startX + indentX, childStartY, childDepth, [layoutNode], result, collapsedIds,
+		groups, startX + indentX, childStartY, childDepth, [layoutNode], result, collapsedIds, expandedMergedIds, pendingExpansions,
 	);
 
 	const totalChildrenHeight = endY - childStartY - NODE_GAP_Y;
@@ -335,7 +464,7 @@ function layoutSubtree(node: FlowNode, startX: number, y: number, depth: number,
 		result.subgraphs.push({
 			label: headerLabel,
 			x: startX - SUBGRAPH_PADDING,
-			y: (y + NODE_HEIGHT + NODE_GAP_Y) - NODE_GAP_Y / 2,
+			y: (y + nodeHeight + NODE_GAP_Y) - NODE_GAP_Y / 2,
 			width: sgContentWidth + SUBGRAPH_PADDING * 2,
 			height: totalChildrenHeight + SUBGRAPH_HEADER_HEIGHT + NODE_GAP_Y,
 			depth,
@@ -344,13 +473,13 @@ function layoutSubtree(node: FlowNode, startX: number, y: number, depth: number,
 	}
 
 	result.width = Math.max(nodeWidth, maxWidth + indentX * 2, isSubagent ? sgContentWidth + indentX * 2 : 0);
-	result.height = NODE_HEIGHT + NODE_GAP_Y + totalChildrenHeight + (isSubagent ? SUBGRAPH_HEADER_HEIGHT : 0);
+	result.height = nodeHeight + NODE_GAP_Y + totalChildrenHeight + (isSubagent ? SUBGRAPH_HEADER_HEIGHT : 0);
 	result.exitNodes = exitNodes;
 
 	return result;
 }
 
-function layoutParallelGroup(children: FlowNode[], startX: number, y: number, depth: number, collapsedIds?: ReadonlySet<string>): {
+function layoutParallelGroup(children: FlowNode[], startX: number, y: number, depth: number, collapsedIds?: ReadonlySet<string>, expandedMergedIds?: ReadonlySet<string>, pendingExpansions?: PendingExpansion[]): {
 	nodes: LayoutNode[];
 	edges: LayoutEdge[];
 	subgraphs: SubgraphRect[];
@@ -364,7 +493,7 @@ function layoutParallelGroup(children: FlowNode[], startX: number, y: number, de
 	let maxHeight = 0;
 
 	for (const child of children) {
-		const subtree = layoutSubtree(child, 0, y, depth, collapsedIds);
+		const subtree = layoutSubtree(child, 0, y, depth, collapsedIds, expandedMergedIds, pendingExpansions);
 		subtreeLayouts.push(subtree);
 		totalWidth += subtree.width;
 		maxHeight = Math.max(maxHeight, subtree.height);
@@ -382,6 +511,7 @@ function layoutParallelGroup(children: FlowNode[], startX: number, y: number, de
 		const dx = currentX;
 		const offsetNodes = subtree.nodes.map(n => ({ ...n, x: n.x + dx }));
 		const offsetEdges = subtree.edges.map(e => ({
+			fromId: e.fromId, toId: e.toId,
 			fromX: e.fromX + dx, fromY: e.fromY,
 			toX: e.toX + dx, toY: e.toY,
 		}));
@@ -419,7 +549,7 @@ function centerLayout(layout: { nodes: LayoutNode[]; edges: LayoutEdge[]; subgra
 	}
 	for (let i = 0; i < layout.edges.length; i++) {
 		const e = layout.edges[i];
-		(layout.edges as LayoutEdge[])[i] = { fromX: e.fromX + dx, fromY: e.fromY, toX: e.toX + dx, toY: e.toY };
+		(layout.edges as LayoutEdge[])[i] = { fromId: e.fromId, toId: e.toId, fromX: e.fromX + dx, fromY: e.fromY, toX: e.toX + dx, toY: e.toY };
 	}
 	for (let i = 0; i < layout.subgraphs.length; i++) {
 		const s = layout.subgraphs[i];
@@ -501,7 +631,28 @@ export function renderFlowChartSVG(layout: FlowLayout): FlowChartRenderResult {
 		})
 	);
 
-	return { svg, focusableElements: sortedFocusable };
+	// Build adjacency map from edges so keyboard navigation can follow
+	// graph directionality instead of visual sort order.
+	const adjacency = new Map<string, { next: string[]; prev: string[] }>();
+	for (const edge of layout.edges) {
+		if (edge.fromId && edge.toId) {
+			let fromEntry = adjacency.get(edge.fromId);
+			if (!fromEntry) {
+				fromEntry = { next: [], prev: [] };
+				adjacency.set(edge.fromId, fromEntry);
+			}
+			fromEntry.next.push(edge.toId);
+
+			let toEntry = adjacency.get(edge.toId);
+			if (!toEntry) {
+				toEntry = { next: [], prev: [] };
+				adjacency.set(edge.toId, toEntry);
+			}
+			toEntry.prev.push(edge.fromId);
+		}
+	}
+
+	return { svg, focusableElements: sortedFocusable, adjacency, positions: positionByKey };
 }
 
 function renderSubgraphs(svg: SVGElement, subgraphs: readonly SubgraphRect[], focusableElements: Map<string, SVGElement>): void {
@@ -577,19 +728,58 @@ function renderSubgraphs(svg: SVGElement, subgraphs: readonly SubgraphRect[], fo
 
 function renderEdges(svg: SVGElement, edges: readonly LayoutEdge[]): void {
 	const strokeAttrs = { fill: 'none', stroke: 'var(--vscode-descriptionForeground)', 'stroke-width': EDGE_STROKE_WIDTH, 'stroke-linecap': 'round' };
+	// allow-any-unicode-next-line
+	const r = 6; // corner radius for 90° bends
 
 	for (const edge of edges) {
 		const midY = (edge.fromY + edge.toY) / 2;
-		svg.appendChild(svgEl('path', {
-			...strokeAttrs,
-			d: `M ${edge.fromX} ${edge.fromY} C ${edge.fromX} ${midY}, ${edge.toX} ${midY}, ${edge.toX} ${edge.toY}`,
-		}));
+		let d: string;
+		const isHorizontal = edge.fromY === edge.toY;
+
+		if (isHorizontal) {
+			// Horizontally aligned: straight line (used by expanded merged nodes)
+			d = `M ${edge.fromX} ${edge.fromY} L ${edge.toX} ${edge.toY}`;
+		} else if (edge.fromX === edge.toX) {
+			// Vertically aligned: straight line
+			d = `M ${edge.fromX} ${edge.fromY} L ${edge.toX} ${edge.toY}`;
+		} else {
+			// allow-any-unicode-next-line
+			// Orthogonal routing: down, 90° horizontal, 90° down
+			const dx = edge.toX - edge.fromX;
+			const signX = dx > 0 ? 1 : -1;
+			const absDx = Math.abs(dx);
+			const cr = Math.min(r, absDx / 2, (edge.toY - edge.fromY) / 4);
+
+			d = `M ${edge.fromX} ${edge.fromY}`
+				// Down to first bend
+				+ ` L ${edge.fromX} ${midY - cr}`
+				// allow-any-unicode-next-line
+				// 90° arc turning horizontal
+				+ ` Q ${edge.fromX} ${midY}, ${edge.fromX + signX * cr} ${midY}`
+				// Horizontal to second bend
+				+ ` L ${edge.toX - signX * cr} ${midY}`
+				// allow-any-unicode-next-line
+				// 90° arc turning down
+				+ ` Q ${edge.toX} ${midY}, ${edge.toX} ${midY + cr}`
+				// Down to target
+				+ ` L ${edge.toX} ${edge.toY}`;
+		}
+
+		svg.appendChild(svgEl('path', { ...strokeAttrs, d }));
 
-		const a = 5; // arrowhead size
+		// Arrowhead: right-pointing for horizontal edges, down-pointing otherwise
+		const a = 5;
+		let arrowD: string;
+		if (isHorizontal) {
+			const signX = edge.toX > edge.fromX ? 1 : -1;
+			arrowD = `M ${edge.toX - signX * a * 1.5} ${edge.toY - a} L ${edge.toX} ${edge.toY} L ${edge.toX - signX * a * 1.5} ${edge.toY + a}`;
+		} else {
+			arrowD = `M ${edge.toX - a} ${edge.toY - a * 1.5} L ${edge.toX} ${edge.toY} L ${edge.toX + a} ${edge.toY - a * 1.5}`;
+		}
 		svg.appendChild(svgEl('path', {
 			...strokeAttrs,
 			'stroke-linejoin': 'round',
-			d: `M ${edge.toX - a} ${edge.toY - a * 1.5} L ${edge.toX} ${edge.toY} L ${edge.toX + a} ${edge.toY - a * 1.5}`,
+			d: arrowD,
 		}));
 	}
 }
@@ -625,6 +815,21 @@ function renderNodes(svg: SVGElement, nodes: readonly LayoutNode[], focusableEle
 		clipPath.appendChild(svgEl('rect', rectAttrs));
 		svg.appendChild(clipPath);
 
+		// Focus ring (hidden by default, shown on :focus via CSS)
+		const focusOffset = 3;
+		g.appendChild(svgEl('rect', {
+			class: 'chat-debug-flowchart-focus-ring',
+			x: node.x - focusOffset,
+			y: node.y - focusOffset,
+			width: node.width + focusOffset * 2,
+			height: node.height + focusOffset * 2,
+			rx: NODE_BORDER_RADIUS + focusOffset,
+			ry: NODE_BORDER_RADIUS + focusOffset,
+			fill: 'none',
+			stroke: 'var(--vscode-focusBorder)',
+			'stroke-width': 2,
+		}));
+
 		// Node rectangle
 		g.appendChild(svgEl('rect', { ...rectAttrs, fill: nodeFill, stroke: color, 'stroke-width': node.isError ? 2 : 1.5 }));
 
@@ -633,20 +838,81 @@ function renderNodes(svg: SVGElement, nodes: readonly LayoutNode[], focusableEle
 
 		// Label text
 		const textX = node.x + NODE_PADDING_H;
-		if (node.sublabel) {
+		const isMessage = isMessageKind(node.kind);
+		if (isMessage && node.sublabel) {
+			// Message nodes: small header label + larger message text
+			const header = svgEl('text', { x: textX, y: node.y + NODE_PADDING_V + SUBLABEL_FONT_SIZE, 'font-size': SUBLABEL_FONT_SIZE, fill: 'var(--vscode-descriptionForeground)', 'font-family': fontFamily, 'clip-path': `url(#${clipId})` });
+			header.textContent = node.label;
+			g.appendChild(header);
+
+			const msg = svgEl('text', { x: textX, y: node.y + node.height - NODE_PADDING_V - 2, 'font-size': FONT_SIZE, fill: 'var(--vscode-foreground)', 'font-family': fontFamily, 'clip-path': `url(#${clipId})` });
+			msg.textContent = node.sublabel;
+			g.appendChild(msg);
+		} else if (node.sublabel) {
 			const label = svgEl('text', { x: textX, y: node.y + NODE_PADDING_V + FONT_SIZE, 'font-size': FONT_SIZE, fill: 'var(--vscode-foreground)', 'font-family': fontFamily, 'clip-path': `url(#${clipId})` });
 			label.textContent = node.label;
 			g.appendChild(label);
 
-			const sub = svgEl('text', { x: textX, y: node.y + NODE_HEIGHT - NODE_PADDING_V, 'font-size': SUBLABEL_FONT_SIZE, fill: 'var(--vscode-descriptionForeground)', 'font-family': fontFamily, 'clip-path': `url(#${clipId})` });
+			const sub = svgEl('text', { x: textX, y: node.y + node.height - NODE_PADDING_V, 'font-size': SUBLABEL_FONT_SIZE, fill: 'var(--vscode-descriptionForeground)', 'font-family': fontFamily, 'clip-path': `url(#${clipId})` });
 			sub.textContent = node.sublabel;
 			g.appendChild(sub);
 		} else {
-			const label = svgEl('text', { x: textX, y: node.y + NODE_HEIGHT / 2 + FONT_SIZE / 2 - 1, 'font-size': FONT_SIZE, fill: 'var(--vscode-foreground)', 'font-family': fontFamily, 'clip-path': `url(#${clipId})` });
+			const label = svgEl('text', { x: textX, y: node.y + node.height / 2 + FONT_SIZE / 2 - 1, 'font-size': FONT_SIZE, fill: 'var(--vscode-foreground)', 'font-family': fontFamily, 'clip-path': `url(#${clipId})` });
 			label.textContent = node.label;
 			g.appendChild(label);
 		}
 
+		// Merged-discovery expand/collapse toggle on the right side
+		if (node.mergedCount) {
+			g.setAttribute('data-is-toggle', 'true');
+			renderMergedToggle(g, node, color, fontFamily);
+		}
+
 		svg.appendChild(g);
 	}
 }
+
+function renderMergedToggle(g: Element, node: LayoutNode, color: string, fontFamily: string): void {
+	const toggleX = node.x + node.width - MERGED_TOGGLE_WIDTH;
+	const toggleGroup = document.createElementNS(SVG_NS, 'g');
+	toggleGroup.classList.add('chat-debug-flowchart-merged-toggle');
+	toggleGroup.setAttribute('data-merged-id', node.id);
+
+	// Separator line
+	toggleGroup.appendChild(svgEl('line', {
+		x1: toggleX, y1: node.y + 4,
+		x2: toggleX, y2: node.y + node.height - 4,
+		stroke: 'var(--vscode-descriptionForeground)',
+		'stroke-width': 0.5,
+		opacity: 0.4,
+	}));
+
+	// allow-any-unicode-next-line
+	// Expand chevron (▶ collapsed, ◀ expanded)
+	const chevronX = toggleX + MERGED_TOGGLE_WIDTH / 2;
+	const chevronY = node.y + node.height / 2;
+	const chevron = svgEl('text', {
+		x: chevronX,
+		y: chevronY + 4,
+		'font-size': 9,
+		fill: color,
+		'font-family': fontFamily,
+		'text-anchor': 'middle',
+		cursor: 'pointer',
+	});
+	// allow-any-unicode-next-line
+	chevron.textContent = node.isMergedExpanded ? '\u25C0' : '\u25B6'; // ◀ or ▶
+	toggleGroup.appendChild(chevron);
+
+	// Hit area for the toggle — invisible rect covering the toggle zone
+	toggleGroup.appendChild(svgEl('rect', {
+		x: toggleX,
+		y: node.y,
+		width: MERGED_TOGGLE_WIDTH,
+		height: node.height,
+		fill: 'transparent',
+		cursor: 'pointer',
+	}));
+
+	g.appendChild(toggleGroup);
+}
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugHomeView.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugHomeView.ts
index 802ca0183afcc..c6120c62749c9 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugHomeView.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugHomeView.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as DOM from '../../../../../base/browser/dom.js';
-import { DomScrollableElement } from '../../../../../base/browser/ui/scrollbar/scrollableElement.js';
+import { Button } from '../../../../../base/browser/ui/button/button.js';
 import { Codicon } from '../../../../../base/common/codicons.js';
 import { Emitter } from '../../../../../base/common/event.js';
 import { Disposable, DisposableStore } from '../../../../../base/common/lifecycle.js';
@@ -12,10 +12,14 @@ import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { isUUID } from '../../../../../base/common/uuid.js';
 import { localize } from '../../../../../nls.js';
+import { IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
+import { defaultButtonStyles } from '../../../../../platform/theme/browser/defaultStyles.js';
 import { IChatDebugService } from '../../common/chatDebugService.js';
 import { IChatService } from '../../common/chatService/chatService.js';
+import { AGENT_DEBUG_LOG_ENABLED_SETTING } from '../../common/promptSyntax/promptTypes.js';
 import { LocalChatSessionUri } from '../../common/model/chatUri.js';
 import { IChatWidgetService } from '../chat.js';
+import { IPreferencesService } from '../../../../services/preferences/common/preferences.js';
 
 const $ = DOM.$;
 
@@ -26,7 +30,6 @@ export class ChatDebugHomeView extends Disposable {
 
 	readonly container: HTMLElement;
 	private readonly scrollContent: HTMLElement;
-	private readonly scrollable: DomScrollableElement;
 	private readonly renderDisposables = this._register(new DisposableStore());
 
 	constructor(
@@ -34,12 +37,18 @@ export class ChatDebugHomeView extends Disposable {
 		@IChatService private readonly chatService: IChatService,
 		@IChatDebugService private readonly chatDebugService: IChatDebugService,
 		@IChatWidgetService private readonly chatWidgetService: IChatWidgetService,
+		@IConfigurationService private readonly configurationService: IConfigurationService,
+		@IPreferencesService private readonly preferencesService: IPreferencesService,
 	) {
 		super();
 		this.container = DOM.append(parent, $('.chat-debug-home'));
-		this.scrollContent = $('div.chat-debug-home-content');
-		this.scrollable = this._register(new DomScrollableElement(this.scrollContent, {}));
-		DOM.append(this.container, this.scrollable.getDomNode());
+		this.scrollContent = DOM.append(this.container, $('div.chat-debug-home-content'));
+
+		this._register(this.configurationService.onDidChangeConfiguration(e => {
+			if (e.affectsConfiguration(AGENT_DEBUG_LOG_ENABLED_SETTING)) {
+				this.render();
+			}
+		}));
 	}
 
 	show(): void {
@@ -55,7 +64,22 @@ export class ChatDebugHomeView extends Disposable {
 		DOM.clearNode(this.scrollContent);
 		this.renderDisposables.clear();
 
-		DOM.append(this.scrollContent, $('h2.chat-debug-home-title', undefined, localize('chatDebug.title', "Chat Debug Panel")));
+		DOM.append(this.scrollContent, $('h2.chat-debug-home-title', undefined, localize('chatDebug.title', "Agent Debug Logs")));
+
+		const isEnabled = this.configurationService.getValue<boolean>(AGENT_DEBUG_LOG_ENABLED_SETTING);
+		if (!isEnabled) {
+			DOM.append(this.scrollContent, $('p.chat-debug-home-subtitle', undefined,
+				localize('chatDebug.disabled', "Enable to view debug logs and investigate chat issues with /troubleshoot.")
+			));
+
+			const enableButton = this.renderDisposables.add(new Button(this.scrollContent, { ...defaultButtonStyles, secondary: true }));
+			enableButton.element.style.width = 'auto';
+			enableButton.label = localize('chatDebug.openSetting', "Enable in Settings");
+			this.renderDisposables.add(enableButton.onDidClick(() => {
+				this.preferencesService.openSettings({ jsonEditor: false, query: AGENT_DEBUG_LOG_ENABLED_SETTING });
+			}));
+			return;
+		}
 
 		// Determine the active session resource
 		const activeWidget = this.chatWidgetService.lastFocusedWidget;
@@ -89,7 +113,24 @@ export class ChatDebugHomeView extends Disposable {
 			const items: HTMLButtonElement[] = [];
 
 			for (const sessionResource of sessionResources) {
-				const sessionTitle = this.chatService.getSessionTitle(sessionResource) || LocalChatSessionUri.parseLocalSessionId(sessionResource) || sessionResource.toString();
+				const rawTitle = this.chatService.getSessionTitle(sessionResource);
+				let sessionTitle: string;
+				if (rawTitle && !isUUID(rawTitle)) {
+					sessionTitle = rawTitle;
+				} else if (LocalChatSessionUri.isLocalSession(sessionResource)) {
+					sessionTitle = localize('chatDebug.newSession', "New Chat");
+				} else {
+					// For imported/external sessions, use the stored title if available
+					const importedTitle = this.chatDebugService.getImportedSessionTitle(sessionResource);
+					if (importedTitle) {
+						sessionTitle = localize('chatDebug.importedSession', "Imported: {0}", importedTitle);
+					} else {
+						// Fall back to URI segment
+						const uriLabel = sessionResource.path || sessionResource.fragment || sessionResource.toString();
+						const segment = uriLabel.replace(/^\/+/, '').split('/').pop() || uriLabel;
+						sessionTitle = localize('chatDebug.importedSession', "Imported: {0}", segment);
+					}
+				}
 				const isActive = activeSessionResource !== undefined && sessionResource.toString() === activeSessionResource.toString();
 
 				const item = DOM.append(sessionList, $<HTMLButtonElement>('button.chat-debug-home-session-item'));
@@ -102,30 +143,20 @@ export class ChatDebugHomeView extends Disposable {
 				DOM.append(item, $(`span${ThemeIcon.asCSSSelector(Codicon.comment)}`));
 
 				const titleSpan = DOM.append(item, $('span.chat-debug-home-session-item-title'));
-				const isShimmering = isUUID(sessionTitle);
-				if (isShimmering) {
-					titleSpan.classList.add('chat-debug-home-session-item-shimmer');
-					item.disabled = true;
-					item.setAttribute('aria-busy', 'true');
-					item.setAttribute('aria-label', localize('chatDebug.loadingSession', "Loading session…"));
-				} else {
-					titleSpan.textContent = sessionTitle;
-					const ariaLabel = isActive
-						? localize('chatDebug.sessionItemActive', "{0} (active)", sessionTitle)
-						: sessionTitle;
-					item.setAttribute('aria-label', ariaLabel);
-				}
+				titleSpan.textContent = sessionTitle;
+				const ariaLabel = isActive
+					? localize('chatDebug.sessionItemActive', "{0} (active)", sessionTitle)
+					: sessionTitle;
+				item.setAttribute('aria-label', ariaLabel);
 
 				if (isActive) {
 					DOM.append(item, $('span.chat-debug-home-session-badge', undefined, localize('chatDebug.active', "Active")));
 				}
 
-				if (!isShimmering) {
-					this.renderDisposables.add(DOM.addDisposableListener(item, DOM.EventType.CLICK, () => {
-						this._onNavigateToSession.fire(sessionResource);
-					}));
-					items.push(item);
-				}
+				this.renderDisposables.add(DOM.addDisposableListener(item, DOM.EventType.CLICK, () => {
+					this._onNavigateToSession.fire(sessionResource);
+				}));
+				items.push(item);
 			}
 
 			// Arrow key navigation between session items
@@ -159,7 +190,5 @@ export class ChatDebugHomeView extends Disposable {
 				}
 			}));
 		}
-
-		this.scrollable.scanDomNode();
 	}
 }
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugLogsView.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugLogsView.ts
index 5a260445faefa..269ce660fb2ef 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugLogsView.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugLogsView.ts
@@ -10,8 +10,9 @@ import { Button } from '../../../../../base/browser/ui/button/button.js';
 import { IObjectTreeElement } from '../../../../../base/browser/ui/tree/tree.js';
 import { Codicon } from '../../../../../base/common/codicons.js';
 import { Emitter } from '../../../../../base/common/event.js';
-import { Disposable, MutableDisposable } from '../../../../../base/common/lifecycle.js';
+import { combinedDisposable, Disposable, MutableDisposable } from '../../../../../base/common/lifecycle.js';
 import { autorun } from '../../../../../base/common/observable.js';
+import { RunOnceScheduler } from '../../../../../base/common/async.js';
 import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { localize } from '../../../../../nls.js';
@@ -21,13 +22,20 @@ import { ServiceCollection } from '../../../../../platform/instantiation/common/
 import { WorkbenchList, WorkbenchObjectTree } from '../../../../../platform/list/browser/listService.js';
 import { defaultBreadcrumbsWidgetStyles, defaultButtonStyles } from '../../../../../platform/theme/browser/defaultStyles.js';
 import { FilterWidget } from '../../../../browser/parts/views/viewFilter.js';
-import { ChatDebugLogLevel, IChatDebugEvent, IChatDebugService } from '../../common/chatDebugService.js';
+import { IChatDebugEvent, IChatDebugService } from '../../common/chatDebugService.js';
+import { filterDebugEventsByText } from '../../common/chatDebugEvents.js';
 import { IChatService } from '../../common/chatService/chatService.js';
 import { LocalChatSessionUri } from '../../common/model/chatUri.js';
-import { ChatDebugEventRenderer, ChatDebugEventDelegate, ChatDebugEventTreeRenderer } from './chatDebugEventList.js';
+import { ChatDebugEventRenderer, ChatDebugEventDelegate, ChatDebugEventTreeRenderer, getEventCreatedText, getEventNameText, getEventDetailsText } from './chatDebugEventList.js';
 import { setupBreadcrumbKeyboardNavigation, TextBreadcrumbItem, LogsViewMode } from './chatDebugTypes.js';
 import { ChatDebugFilterState, bindFilterContextKeys } from './chatDebugFilters.js';
 import { ChatDebugDetailPanel } from './chatDebugDetailPanel.js';
+import { IChatWidgetService } from '../chat.js';
+import { createDebugEventsAttachment } from './chatDebugAttachment.js';
+import { IClipboardService } from '../../../../../platform/clipboard/common/clipboardService.js';
+import { IContextMenuService } from '../../../../../platform/contextview/browser/contextView.js';
+import { Action, Separator } from '../../../../../base/common/actions.js';
+import { StandardMouseEvent } from '../../../../../base/browser/mouseEvent.js';
 
 const $ = DOM.$;
 
@@ -56,11 +64,12 @@ export class ChatDebugLogsView extends Disposable {
 	private tree: WorkbenchObjectTree<IChatDebugEvent, void>;
 
 	private currentSessionResource: URI | undefined;
-	private logsViewMode: LogsViewMode = LogsViewMode.List;
+	private logsViewMode: LogsViewMode = LogsViewMode.Tree;
 	private events: IChatDebugEvent[] = [];
 	private currentDimension: Dimension | undefined;
 	private readonly eventListener = this._register(new MutableDisposable());
 	private readonly sessionStateDisposable = this._register(new MutableDisposable());
+	private readonly refreshScheduler: RunOnceScheduler;
 	private shimmerRow!: HTMLElement;
 
 	constructor(
@@ -70,8 +79,12 @@ export class ChatDebugLogsView extends Disposable {
 		@IChatDebugService private readonly chatDebugService: IChatDebugService,
 		@IInstantiationService private readonly instantiationService: IInstantiationService,
 		@IContextKeyService private readonly contextKeyService: IContextKeyService,
+		@IChatWidgetService private readonly chatWidgetService: IChatWidgetService,
+		@IClipboardService private readonly clipboardService: IClipboardService,
+		@IContextMenuService private readonly contextMenuService: IContextMenuService,
 	) {
 		super();
+		this.refreshScheduler = this._register(new RunOnceScheduler(() => this.refreshList(), 50));
 		this.container = DOM.append(parent, $('.chat-debug-logs'));
 		DOM.hide(this.container);
 
@@ -104,13 +117,13 @@ export class ChatDebugLogsView extends Disposable {
 			new ServiceCollection([IContextKeyService, scopedContextKeyService])
 		));
 		this.filterWidget = this._register(childInstantiationService.createInstance(FilterWidget, {
-			placeholder: localize('chatDebug.search', "Filter (e.g. text, !exclude)"),
+			placeholder: localize('chatDebug.search', "Filter (e.g. text, !exclude, before:YYYY-MM-DDTHH:MM:SS)"),
 			ariaLabel: localize('chatDebug.filterAriaLabel', "Filter debug events"),
 		}));
 
 		// View mode toggle
 		this.viewModeToggle = this._register(new Button(this.headerContainer, { ...defaultButtonStyles, secondary: true, title: localize('chatDebug.toggleViewMode', "Toggle between list and tree view") }));
-		this.viewModeToggle.element.classList.add('chat-debug-view-mode-toggle');
+		this.viewModeToggle.element.classList.add('chat-debug-view-mode-toggle', 'monaco-text-button');
 		this.updateViewModeToggle();
 		this._register(this.viewModeToggle.onDidClick(() => {
 			this.toggleViewMode();
@@ -119,6 +132,22 @@ export class ChatDebugLogsView extends Disposable {
 		const filterContainer = DOM.append(this.headerContainer, $('.viewpane-filter-container'));
 		filterContainer.appendChild(this.filterWidget.element);
 
+		// Troubleshoot button
+		const troubleshootButton = this._register(new Button(this.headerContainer, { ...defaultButtonStyles, secondary: true, title: localize('chatDebug.troubleshoot', "Add snapshot to Chat") }));
+		troubleshootButton.element.classList.add('chat-debug-troubleshoot-button', 'monaco-text-button');
+		DOM.append(troubleshootButton.element, $(`span${ThemeIcon.asCSSSelector(Codicon.chatSparkle)}`));
+		this._register(troubleshootButton.onDidClick(async () => {
+			if (!this.currentSessionResource) {
+				return;
+			}
+			const widget = await this.chatWidgetService.openSession(this.currentSessionResource);
+			if (widget) {
+				const attachment = await createDebugEventsAttachment(this.currentSessionResource, this.chatDebugService);
+				widget.attachmentModel.addContext(attachment);
+				widget.focusInput();
+			}
+		}));
+
 		this._register(this.filterWidget.onDidChangeFilterText(text => {
 			this.filterState.setTextFilter(text);
 		}));
@@ -145,8 +174,9 @@ export class ChatDebugLogsView extends Disposable {
 		// Body container
 		this.bodyContainer = DOM.append(mainColumn, $('.chat-debug-logs-body'));
 
-		// List container
+		// List container (initially hidden — tree view is default)
 		this.listContainer = DOM.append(this.bodyContainer, $('.chat-debug-list-container'));
+		DOM.hide(this.listContainer);
 
 		const accessibilityProvider = {
 			getAriaLabel: (e: IChatDebugEvent) => {
@@ -186,9 +216,8 @@ export class ChatDebugLogsView extends Disposable {
 			{ identityProvider, accessibilityProvider }
 		));
 
-		// Tree container (initially hidden)
+		// Tree container (default view)
 		this.treeContainer = DOM.append(this.bodyContainer, $('.chat-debug-list-container'));
-		DOM.hide(this.treeContainer);
 
 		this.tree = this._register(this.instantiationService.createInstance(
 			WorkbenchObjectTree<IChatDebugEvent, void>,
@@ -208,6 +237,11 @@ export class ChatDebugLogsView extends Disposable {
 
 		// Detail panel (sibling of main column so it aligns with table header)
 		this.detailPanel = this._register(this.instantiationService.createInstance(ChatDebugDetailPanel, contentContainer));
+		this._register(this.detailPanel.onDidChangeWidth(() => {
+			if (this.currentDimension) {
+				this.layout(this.currentDimension);
+			}
+		}));
 		this._register(this.detailPanel.onDidHide(() => {
 			if (this.list.getSelection().length > 0) {
 				this.list.setSelection([]);
@@ -215,6 +249,21 @@ export class ChatDebugLogsView extends Disposable {
 			if (this.tree.getSelection().length > 0) {
 				this.tree.setSelection([]);
 			}
+			if (this.currentDimension) {
+				this.layout(this.currentDimension);
+			}
+		}));
+
+		// Context menu
+		this._register(this.list.onContextMenu(e => {
+			if (e.element) {
+				this.showEventContextMenu(e.element, e.browserEvent);
+			}
+		}));
+		this._register(this.tree.onContextMenu(e => {
+			if (e.element) {
+				this.showEventContextMenu(e.element, e.browserEvent);
+			}
 		}));
 
 		// Resolve event details on selection
@@ -241,6 +290,10 @@ export class ChatDebugLogsView extends Disposable {
 		this.currentSessionResource = sessionResource;
 	}
 
+	setFilterText(text: string): void {
+		this.filterWidget.setFilterText(text);
+	}
+
 	show(): void {
 		DOM.show(this.container);
 		this.loadEvents();
@@ -265,7 +318,7 @@ export class ChatDebugLogsView extends Disposable {
 		}
 		const sessionTitle = this.chatService.getSessionTitle(this.currentSessionResource) || LocalChatSessionUri.parseLocalSessionId(this.currentSessionResource) || this.currentSessionResource.toString();
 		this.breadcrumbWidget.setItems([
-			new TextBreadcrumbItem(localize('chatDebug.title', "Chat Debug Panel"), true),
+			new TextBreadcrumbItem(localize('chatDebug.title', "Agent Debug Logs"), true),
 			new TextBreadcrumbItem(sessionTitle, true),
 			new TextBreadcrumbItem(localize('chatDebug.logs', "Logs")),
 		]);
@@ -276,8 +329,8 @@ export class ChatDebugLogsView extends Disposable {
 		const breadcrumbHeight = 22;
 		const headerHeight = this.headerContainer.offsetHeight;
 		const tableHeaderHeight = this.tableHeader.offsetHeight;
-		const detailVisible = this.detailPanel.element.style.display !== 'none';
-		const detailWidth = detailVisible ? this.detailPanel.element.offsetWidth : 0;
+		const detailVisible = this.detailPanel.isVisible;
+		const detailWidth = detailVisible ? this.detailPanel.width : 0;
 		const listHeight = dimension.height - breadcrumbHeight - headerHeight - tableHeaderHeight;
 		const listWidth = dimension.width - detailWidth;
 		if (this.logsViewMode === LogsViewMode.Tree) {
@@ -285,75 +338,27 @@ export class ChatDebugLogsView extends Disposable {
 		} else {
 			this.list.layout(listHeight, listWidth);
 		}
+		if (this.detailPanel.isVisible) {
+			this.detailPanel.layout(listHeight);
+		}
+		this.detailPanel.layoutSash();
 	}
 
 	refreshList(): void {
-		let filtered = this.events;
+		let filtered: readonly IChatDebugEvent[] = this.events;
 
-		// Filter by kind toggles
-		filtered = filtered.filter(e => this.filterState.isKindVisible(e.kind));
-
-		// Filter by level toggles
+		// Filter by kind toggles (pass category for generic events so only
+		// discovery-category events are affected by the Prompt Discovery toggle)
 		filtered = filtered.filter(e => {
-			if (e.kind === 'generic') {
-				switch (e.level) {
-					case ChatDebugLogLevel.Trace: return this.filterState.filterLevelTrace;
-					case ChatDebugLogLevel.Info: return this.filterState.filterLevelInfo;
-					case ChatDebugLogLevel.Warning: return this.filterState.filterLevelWarning;
-					case ChatDebugLogLevel.Error: return this.filterState.filterLevelError;
-				}
-			}
-			if (e.kind === 'toolCall' && e.result === 'error') {
-				return this.filterState.filterLevelError;
-			}
-			return true;
+			const category = e.kind === 'generic' ? e.category : undefined;
+			return this.filterState.isKindVisible(e.kind, category);
 		});
 
-		// Filter by text search
+		// Filter by text search and timestamp (before:/after: syntax is handled
+		// inside filterDebugEventsByText)
 		const filterText = this.filterState.textFilter;
 		if (filterText) {
-			const terms = filterText.split(/\s*,\s*/).filter(t => t.length > 0);
-			const includeTerms = terms.filter(t => !t.startsWith('!')).map(t => t.trim());
-			const excludeTerms = terms.filter(t => t.startsWith('!')).map(t => t.slice(1).trim()).filter(t => t.length > 0);
-
-			filtered = filtered.filter(e => {
-				const matchesText = (term: string): boolean => {
-					if (e.kind.toLowerCase().includes(term)) {
-						return true;
-					}
-					switch (e.kind) {
-						case 'toolCall':
-							return e.toolName.toLowerCase().includes(term) ||
-								(e.input?.toLowerCase().includes(term) ?? false) ||
-								(e.output?.toLowerCase().includes(term) ?? false);
-						case 'modelTurn':
-							return (e.model?.toLowerCase().includes(term) ?? false);
-						case 'generic':
-							return e.name.toLowerCase().includes(term) ||
-								(e.details?.toLowerCase().includes(term) ?? false) ||
-								(e.category?.toLowerCase().includes(term) ?? false);
-						case 'subagentInvocation':
-							return e.agentName.toLowerCase().includes(term) ||
-								(e.description?.toLowerCase().includes(term) ?? false);
-						case 'userMessage':
-							return e.message.toLowerCase().includes(term) ||
-								e.sections.some(s => s.name.toLowerCase().includes(term) || s.content.toLowerCase().includes(term));
-						case 'agentResponse':
-							return e.message.toLowerCase().includes(term) ||
-								e.sections.some(s => s.name.toLowerCase().includes(term) || s.content.toLowerCase().includes(term));
-					}
-				};
-
-				// Exclude terms: if any exclude term matches, filter out the event
-				if (excludeTerms.some(term => matchesText(term))) {
-					return false;
-				}
-				// Include terms: if present, at least one must match
-				if (includeTerms.length > 0) {
-					return includeTerms.some(term => matchesText(term));
-				}
-				return true;
-			});
+			filtered = filterDebugEventsByText(filtered, filterText);
 		}
 
 		if (this.logsViewMode === LogsViewMode.List) {
@@ -369,18 +374,52 @@ export class ChatDebugLogsView extends Disposable {
 	}
 
 	addEvent(event: IChatDebugEvent): void {
-		this.events.push(event);
-		this.refreshList();
+		// Binary-insert to maintain chronological order without a full sort.
+		// Events almost always arrive in order, so the insertion point is
+		// typically at the end (O(log n) comparison, O(1) splice).
+		const time = event.created.getTime();
+		let lo = 0;
+		let hi = this.events.length;
+		while (lo < hi) {
+			const mid = (lo + hi) >>> 1;
+			if (this.events[mid].created.getTime() <= time) {
+				lo = mid + 1;
+			} else {
+				hi = mid;
+			}
+		}
+		if (lo === this.events.length) {
+			this.events.push(event);
+		} else {
+			this.events.splice(lo, 0, event);
+		}
+		this.scheduleRefresh();
+	}
+
+	private scheduleRefresh(): void {
+		if (!this.refreshScheduler.isScheduled()) {
+			this.refreshScheduler.schedule();
+		}
 	}
 
 	private loadEvents(): void {
 		this.events = [...this.chatDebugService.getEvents(this.currentSessionResource || undefined)];
-		this.eventListener.value = this.chatDebugService.onDidAddEvent(e => {
+
+		const addEventDisposable = this.chatDebugService.onDidAddEvent(e => {
 			if (!this.currentSessionResource || e.sessionResource.toString() === this.currentSessionResource.toString()) {
-				this.events.push(e);
+				this.addEvent(e);
+			}
+		});
+
+		// Reload events when provider events are cleared (before re-invoking providers)
+		const clearEventsDisposable = this.chatDebugService.onDidClearProviderEvents(sessionResource => {
+			if (!this.currentSessionResource || sessionResource.toString() === this.currentSessionResource.toString()) {
+				this.events = [...this.chatDebugService.getEvents(this.currentSessionResource || undefined)];
 				this.refreshList();
 			}
 		});
+
+		this.eventListener.value = combinedDisposable(addEventDisposable, clearEventsDisposable);
 		this.updateBreadcrumb();
 		this.trackSessionState();
 	}
@@ -409,12 +448,12 @@ export class ChatDebugLogsView extends Disposable {
 		});
 	}
 
-	private refreshTree(filtered: IChatDebugEvent[]): void {
+	private refreshTree(filtered: readonly IChatDebugEvent[]): void {
 		const treeElements = this.buildTreeHierarchy(filtered);
 		this.tree.setChildren(null, treeElements);
 	}
 
-	private buildTreeHierarchy(events: IChatDebugEvent[]): IObjectTreeElement<IChatDebugEvent>[] {
+	private buildTreeHierarchy(events: readonly IChatDebugEvent[]): IObjectTreeElement<IChatDebugEvent>[] {
 		const idToEvent = new Map<string, IChatDebugEvent>();
 		const idToChildren = new Map<string, IChatDebugEvent[]>();
 		const roots: IChatDebugEvent[] = [];
@@ -497,5 +536,29 @@ export class ChatDebugLogsView extends Disposable {
 		this.filterWidget.checkMoreFilters(!this.filterState.isAllFiltersDefault());
 	}
 
+	private showEventContextMenu(event: IChatDebugEvent, browserEvent: UIEvent): void {
+		const d = event.created;
+		const pad = (n: number) => String(n).padStart(2, '0');
+		const timestamp = `${d.getFullYear()}-${pad(d.getMonth() + 1)}-${pad(d.getDate())}T${pad(d.getHours())}:${pad(d.getMinutes())}:${pad(d.getSeconds())}`;
+		const row = [getEventCreatedText(event), getEventNameText(event), getEventDetailsText(event)].filter(Boolean).join('\t');
+		const name = getEventNameText(event);
+		this.contextMenuService.showContextMenu({
+			getAnchor: () => DOM.isMouseEvent(browserEvent)
+				? new StandardMouseEvent(DOM.getWindow(this.container), browserEvent)
+				: this.container,
+			getActions: () => [
+				new Action('chatDebug.copyTimestamp', localize('chatDebug.copyTimestamp', "Copy Timestamp"), undefined, true, () => this.clipboardService.writeText(timestamp)),
+				new Action('chatDebug.copyRow', localize('chatDebug.copyRow', "Copy Row"), undefined, true, () => this.clipboardService.writeText(row)),
+				new Separator(),
+				new Action('chatDebug.filterBefore', localize('chatDebug.filterBefore', "Filter Before Timestamp"), undefined, true, () => this.applyFilterToken(`before:${timestamp}`)),
+				new Action('chatDebug.filterAfter', localize('chatDebug.filterAfter', "Filter After Timestamp"), undefined, true, () => this.applyFilterToken(`after:${timestamp}`)),
+				new Action('chatDebug.filterName', localize('chatDebug.filterName', "Filter Name"), undefined, !!name, () => this.applyFilterToken(name)),
+			],
+		});
+	}
+
+	private applyFilterToken(token: string): void {
+		this.filterWidget.setFilterText(token);
+	}
 
 }
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugMessageContentRenderer.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugMessageContentRenderer.ts
index 9d2b717a8e098..1f7664cdcd6de 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugMessageContentRenderer.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugMessageContentRenderer.ts
@@ -4,86 +4,20 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as DOM from '../../../../../base/browser/dom.js';
-import { DomScrollableElement } from '../../../../../base/browser/ui/scrollbar/scrollableElement.js';
-import { Codicon } from '../../../../../base/common/codicons.js';
 import { DisposableStore } from '../../../../../base/common/lifecycle.js';
-import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { localize } from '../../../../../nls.js';
-import { IChatDebugMessageSection, IChatDebugUserMessageEvent, IChatDebugAgentResponseEvent, IChatDebugEventMessageContent } from '../../common/chatDebugService.js';
+import { IClipboardService } from '../../../../../platform/clipboard/common/clipboardService.js';
+import { ILanguageService } from '../../../../../editor/common/languages/language.js';
+import { IChatDebugUserMessageEvent, IChatDebugAgentResponseEvent, IChatDebugEventMessageContent } from '../../common/chatDebugService.js';
+import { renderSection, tokenizeContent } from './chatDebugToolCallContentRenderer.js';
 
 const $ = DOM.$;
 
-/**
- * Wire up a collapsible toggle on a chevron+header+content triple.
- * Handles icon switching and display toggling.
- */
-export function setupCollapsibleToggle(chevron: HTMLElement, header: HTMLElement, contentEl: HTMLElement, disposables: DisposableStore, initiallyCollapsed: boolean = false): void {
-	let collapsed = initiallyCollapsed;
-
-	// Accessibility: make header keyboard-focusable and expose toggle semantics
-	header.tabIndex = 0;
-	header.role = 'button';
-	chevron.setAttribute('aria-hidden', 'true');
-
-	const updateState = () => {
-		DOM.clearNode(chevron);
-		const icon = collapsed ? Codicon.chevronRight : Codicon.chevronDown;
-		chevron.classList.add(...ThemeIcon.asClassName(icon).split(' '));
-		contentEl.style.display = collapsed ? 'none' : 'block';
-		header.style.borderRadius = collapsed ? '' : '3px 3px 0 0';
-		header.setAttribute('aria-expanded', String(!collapsed));
-	};
-
-	updateState();
-
-	disposables.add(DOM.addDisposableListener(header, DOM.EventType.CLICK, () => {
-		collapsed = !collapsed;
-		chevron.className = 'chat-debug-message-section-chevron';
-		updateState();
-	}));
-
-	disposables.add(DOM.addDisposableListener(header, DOM.EventType.KEY_DOWN, (e: KeyboardEvent) => {
-		if (e.key === 'Enter' || e.key === ' ') {
-			e.preventDefault();
-			header.click();
-		}
-	}));
-}
-
-/**
- * Render a collapsible section with a clickable header and pre-formatted content.
- */
-function renderCollapsibleSection(parent: HTMLElement, section: IChatDebugMessageSection, disposables: DisposableStore, initiallyCollapsed: boolean = false): void {
-	const sectionEl = DOM.append(parent, $('div.chat-debug-message-section'));
-
-	const header = DOM.append(sectionEl, $('div.chat-debug-message-section-header'));
-
-	const chevron = DOM.append(header, $(`span.chat-debug-message-section-chevron`));
-	DOM.append(header, $('span.chat-debug-message-section-title', undefined, section.name));
-
-	const contentEl = $('pre.chat-debug-message-section-content');
-	contentEl.textContent = section.content;
-	contentEl.tabIndex = 0;
-
-	const scrollable = new DomScrollableElement(contentEl, {});
-	disposables.add(scrollable);
-
-	const wrapper = scrollable.getDomNode();
-	wrapper.classList.add('chat-debug-message-section-content-wrapper');
-	DOM.append(sectionEl, wrapper);
-
-	setupCollapsibleToggle(chevron, header, wrapper, disposables, initiallyCollapsed);
-
-	// Scan after toggle so scrollbar dimensions are correct when expanded
-	disposables.add(DOM.addDisposableListener(header, DOM.EventType.CLICK, () => {
-		scrollable.scanDomNode();
-	}));
-}
-
 /**
  * Render a user message event with collapsible prompt sections.
+ * JSON content in sections is syntax-highlighted.
  */
-export function renderUserMessageContent(event: IChatDebugUserMessageEvent): { element: HTMLElement; disposables: DisposableStore } {
+export async function renderUserMessageContent(event: IChatDebugUserMessageEvent, languageService: ILanguageService, clipboardService?: IClipboardService): Promise<{ element: HTMLElement; disposables: DisposableStore }> {
 	const disposables = new DisposableStore();
 	const container = $('div.chat-debug-message-content');
 	container.tabIndex = 0;
@@ -97,7 +31,8 @@ export function renderUserMessageContent(event: IChatDebugUserMessageEvent): { e
 			localize('chatDebug.promptSections', "Prompt Sections ({0})", event.sections.length)));
 
 		for (const section of event.sections) {
-			renderCollapsibleSection(sectionsContainer, section, disposables);
+			const { plainText, tokenizedHtml } = await tokenizeContent(section.content, languageService);
+			renderSection(sectionsContainer, section.name, plainText, tokenizedHtml, disposables, false, clipboardService);
 		}
 	}
 
@@ -106,8 +41,9 @@ export function renderUserMessageContent(event: IChatDebugUserMessageEvent): { e
 
 /**
  * Render an agent response event with collapsible response sections.
+ * JSON content in sections is syntax-highlighted.
  */
-export function renderAgentResponseContent(event: IChatDebugAgentResponseEvent): { element: HTMLElement; disposables: DisposableStore } {
+export async function renderAgentResponseContent(event: IChatDebugAgentResponseEvent, languageService: ILanguageService, clipboardService?: IClipboardService): Promise<{ element: HTMLElement; disposables: DisposableStore }> {
 	const disposables = new DisposableStore();
 	const container = $('div.chat-debug-message-content');
 	container.tabIndex = 0;
@@ -121,7 +57,8 @@ export function renderAgentResponseContent(event: IChatDebugAgentResponseEvent):
 			localize('chatDebug.responseSections', "Response Sections ({0})", event.sections.length)));
 
 		for (const section of event.sections) {
-			renderCollapsibleSection(sectionsContainer, section, disposables);
+			const { plainText, tokenizedHtml } = await tokenizeContent(section.content, languageService);
+			renderSection(sectionsContainer, section.name, plainText, tokenizedHtml, disposables, false, clipboardService);
 		}
 	}
 
@@ -148,8 +85,9 @@ export function messageEventToPlainText(event: IChatDebugUserMessageEvent | ICha
 
 /**
  * Render a resolved message content (from resolveChatDebugLogEvent) with collapsible sections.
+ * JSON content in sections is syntax-highlighted.
  */
-export function renderResolvedMessageContent(content: IChatDebugEventMessageContent): { element: HTMLElement; disposables: DisposableStore } {
+export async function renderResolvedMessageContent(content: IChatDebugEventMessageContent, languageService: ILanguageService, clipboardService?: IClipboardService): Promise<{ element: HTMLElement; disposables: DisposableStore }> {
 	const disposables = new DisposableStore();
 	const container = $('div.chat-debug-message-content');
 	container.tabIndex = 0;
@@ -168,7 +106,8 @@ export function renderResolvedMessageContent(content: IChatDebugEventMessageCont
 		DOM.append(sectionsContainer, $('div.chat-debug-message-sections-label', undefined, label));
 
 		for (const section of content.sections) {
-			renderCollapsibleSection(sectionsContainer, section, disposables);
+			const { plainText, tokenizedHtml } = await tokenizeContent(section.content, languageService);
+			renderSection(sectionsContainer, section.name, plainText, tokenizedHtml, disposables, false, clipboardService);
 		}
 	}
 
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugModelTurnContentRenderer.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugModelTurnContentRenderer.ts
new file mode 100644
index 0000000000000..4627913380716
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugModelTurnContentRenderer.ts
@@ -0,0 +1,143 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as DOM from '../../../../../base/browser/dom.js';
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { localize } from '../../../../../nls.js';
+import { IClipboardService } from '../../../../../platform/clipboard/common/clipboardService.js';
+import { ILanguageService } from '../../../../../editor/common/languages/language.js';
+import { IChatDebugEventModelTurnContent } from '../../common/chatDebugService.js';
+import { renderSection, tokenizeContent } from './chatDebugToolCallContentRenderer.js';
+import { safeIntl } from '../../../../../base/common/date.js';
+
+const $ = DOM.$;
+const numberFormatter = safeIntl.NumberFormat();
+
+/**
+ * Render a resolved model turn content with structured display of
+ * request metadata, token usage, and timing.
+ * When JSON is detected in section content, renders it with syntax highlighting.
+ */
+export async function renderModelTurnContent(content: IChatDebugEventModelTurnContent, languageService: ILanguageService, clipboardService?: IClipboardService): Promise<{ element: HTMLElement; disposables: DisposableStore }> {
+	const disposables = new DisposableStore();
+	const container = $('div.chat-debug-message-content');
+	container.tabIndex = 0;
+
+	// Header: Model Turn
+	DOM.append(container, $('div.chat-debug-message-content-title', undefined, localize('chatDebug.modelTurn.title', "Model Turn")));
+
+	// Status summary line
+	const statusParts: string[] = [];
+	if (content.requestName) {
+		statusParts.push(content.requestName);
+	}
+	if (content.model) {
+		statusParts.push(content.model);
+	}
+	if (content.status && content.status !== 'unknown') {
+		statusParts.push(content.status);
+	}
+	if (content.durationInMillis !== undefined) {
+		statusParts.push(localize('chatDebug.modelTurn.duration', "{0}ms", numberFormatter.value.format(content.durationInMillis)));
+	}
+	if (statusParts.length > 0) {
+		DOM.append(container, $('div.chat-debug-message-content-summary', undefined, statusParts.join(' \u00b7 ')));
+	}
+
+	// Token usage details
+	const detailsContainer = DOM.append(container, $('div.chat-debug-model-turn-details'));
+
+	if (content.inputTokens !== undefined) {
+		DOM.append(detailsContainer, $('div', undefined, localize('chatDebug.modelTurn.inputTokens', "Input tokens: {0}", numberFormatter.value.format(content.inputTokens))));
+	}
+	if (content.outputTokens !== undefined) {
+		DOM.append(detailsContainer, $('div', undefined, localize('chatDebug.modelTurn.outputTokens', "Output tokens: {0}", numberFormatter.value.format(content.outputTokens))));
+	}
+	if (content.cachedTokens !== undefined) {
+		DOM.append(detailsContainer, $('div', undefined, localize('chatDebug.modelTurn.cachedTokens', "Cached tokens: {0}", numberFormatter.value.format(content.cachedTokens))));
+	}
+	if (content.totalTokens !== undefined) {
+		DOM.append(detailsContainer, $('div', undefined, localize('chatDebug.modelTurn.totalTokens', "Total tokens: {0}", numberFormatter.value.format(content.totalTokens))));
+	}
+	if (content.timeToFirstTokenInMillis !== undefined) {
+		DOM.append(detailsContainer, $('div', undefined, localize('chatDebug.modelTurn.ttft', "Time to first token: {0}ms", numberFormatter.value.format(content.timeToFirstTokenInMillis))));
+	}
+	if (content.maxInputTokens !== undefined) {
+		DOM.append(detailsContainer, $('div', undefined, localize('chatDebug.modelTurn.maxInputTokens', "Max input tokens: {0}", numberFormatter.value.format(content.maxInputTokens))));
+	}
+	if (content.maxOutputTokens !== undefined) {
+		DOM.append(detailsContainer, $('div', undefined, localize('chatDebug.modelTurn.maxOutputTokens', "Max output tokens: {0}", numberFormatter.value.format(content.maxOutputTokens))));
+	}
+	if (content.errorMessage) {
+		DOM.append(detailsContainer, $('div.chat-debug-model-turn-error', undefined, localize('chatDebug.modelTurn.error', "Error: {0}", content.errorMessage)));
+	}
+
+	// Collapsible sections (e.g., system prompt, user prompt, tools, response)
+	if (content.sections && content.sections.length > 0) {
+		const sectionsContainer = DOM.append(container, $('div.chat-debug-message-sections'));
+		DOM.append(sectionsContainer, $('div.chat-debug-message-sections-label', undefined,
+			localize('chatDebug.modelTurn.sections', "Sections ({0})", content.sections.length)));
+
+		for (const section of content.sections) {
+			const { plainText, tokenizedHtml } = await tokenizeContent(section.content, languageService);
+			renderSection(sectionsContainer, section.name, plainText, tokenizedHtml, disposables, false, clipboardService);
+		}
+	}
+
+	return { element: container, disposables };
+}
+
+/**
+ * Convert a resolved model turn content to plain text for clipboard / editor output.
+ */
+export function modelTurnContentToPlainText(content: IChatDebugEventModelTurnContent): string {
+	const lines: string[] = [];
+	lines.push(localize('chatDebug.modelTurn.requestLabel', "Request: {0}", content.requestName));
+
+	if (content.model) {
+		lines.push(localize('chatDebug.modelTurn.modelLabel', "Model: {0}", content.model));
+	}
+	if (content.status && content.status !== 'unknown') {
+		lines.push(localize('chatDebug.modelTurn.statusLabel', "Status: {0}", content.status));
+	}
+	if (content.durationInMillis !== undefined) {
+		lines.push(localize('chatDebug.modelTurn.durationLabel', "Duration: {0}ms", numberFormatter.value.format(content.durationInMillis)));
+	}
+	if (content.timeToFirstTokenInMillis !== undefined) {
+		lines.push(localize('chatDebug.modelTurn.ttftLabel', "Time to first token: {0}ms", numberFormatter.value.format(content.timeToFirstTokenInMillis)));
+	}
+	if (content.inputTokens !== undefined) {
+		lines.push(localize('chatDebug.modelTurn.inputTokensLabel', "Input tokens: {0}", numberFormatter.value.format(content.inputTokens)));
+	}
+	if (content.outputTokens !== undefined) {
+		lines.push(localize('chatDebug.modelTurn.outputTokensLabel', "Output tokens: {0}", numberFormatter.value.format(content.outputTokens)));
+	}
+	if (content.cachedTokens !== undefined) {
+		lines.push(localize('chatDebug.modelTurn.cachedTokensLabel', "Cached tokens: {0}", numberFormatter.value.format(content.cachedTokens)));
+	}
+	if (content.totalTokens !== undefined) {
+		lines.push(localize('chatDebug.modelTurn.totalTokensLabel', "Total tokens: {0}", numberFormatter.value.format(content.totalTokens)));
+	}
+	if (content.maxInputTokens !== undefined) {
+		lines.push(localize('chatDebug.modelTurn.maxInputTokensLabel', "Max input tokens: {0}", numberFormatter.value.format(content.maxInputTokens)));
+	}
+	if (content.maxOutputTokens !== undefined) {
+		lines.push(localize('chatDebug.modelTurn.maxOutputTokensLabel', "Max output tokens: {0}", numberFormatter.value.format(content.maxOutputTokens)));
+	}
+	if (content.errorMessage) {
+		lines.push(localize('chatDebug.modelTurn.errorLabel', "Error: {0}", content.errorMessage));
+	}
+
+	if (content.sections && content.sections.length > 0) {
+		lines.push('');
+		for (const section of content.sections) {
+			lines.push(`--- ${section.name} ---`);
+			lines.push(section.content);
+			lines.push('');
+		}
+	}
+
+	return lines.join('\n');
+}
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugOverviewView.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugOverviewView.ts
index 87a59577dc1ec..dfe3405b4b344 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugOverviewView.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugOverviewView.ts
@@ -6,7 +6,7 @@
 import * as DOM from '../../../../../base/browser/dom.js';
 import { BreadcrumbsWidget } from '../../../../../base/browser/ui/breadcrumbs/breadcrumbsWidget.js';
 import { Button } from '../../../../../base/browser/ui/button/button.js';
-import { DomScrollableElement } from '../../../../../base/browser/ui/scrollbar/scrollableElement.js';
+import { RunOnceScheduler } from '../../../../../base/common/async.js';
 import { Codicon } from '../../../../../base/common/codicons.js';
 import { Emitter } from '../../../../../base/common/event.js';
 import { Disposable, DisposableStore } from '../../../../../base/common/lifecycle.js';
@@ -15,14 +15,16 @@ import { URI } from '../../../../../base/common/uri.js';
 import { localize } from '../../../../../nls.js';
 import { defaultBreadcrumbsWidgetStyles, defaultButtonStyles } from '../../../../../platform/theme/browser/defaultStyles.js';
 import { ChatDebugLogLevel, IChatDebugEvent, IChatDebugService } from '../../common/chatDebugService.js';
+import { safeIntl } from '../../../../../base/common/date.js';
 import { IChatService } from '../../common/chatService/chatService.js';
 import { ChatAgentLocation } from '../../common/constants.js';
-import { IChatSessionsService } from '../../common/chatSessionsService.js';
+import { IChatSessionsService, localChatSessionType } from '../../common/chatSessionsService.js';
 import { getChatSessionType, LocalChatSessionUri } from '../../common/model/chatUri.js';
 import { IChatWidgetService } from '../chat.js';
 import { setupBreadcrumbKeyboardNavigation, TextBreadcrumbItem } from './chatDebugTypes.js';
 
 const $ = DOM.$;
+const numberFormatter = safeIntl.NumberFormat();
 
 export const enum OverviewNavigation {
 	Home = 'home',
@@ -37,13 +39,13 @@ export class ChatDebugOverviewView extends Disposable {
 
 	readonly container: HTMLElement;
 	private readonly content: HTMLElement;
-	private readonly scrollable: DomScrollableElement;
 	private readonly breadcrumbWidget: BreadcrumbsWidget;
 	private readonly loadDisposables = this._register(new DisposableStore());
 
 	private currentSessionResource: URI | undefined;
 	private metricsContainer: HTMLElement | undefined;
 	private isFirstLoad: boolean = true;
+	private readonly refreshScheduler: RunOnceScheduler;
 
 	constructor(
 		parent: HTMLElement,
@@ -56,6 +58,8 @@ export class ChatDebugOverviewView extends Disposable {
 		this.container = DOM.append(parent, $('.chat-debug-overview'));
 		DOM.hide(this.container);
 
+		this.refreshScheduler = this._register(new RunOnceScheduler(() => this.doRefresh(), 100));
+
 		// Breadcrumb
 		const breadcrumbContainer = DOM.append(this.container, $('.chat-debug-breadcrumb'));
 		this.breadcrumbWidget = this._register(new BreadcrumbsWidget(breadcrumbContainer, 3, undefined, Codicon.chevronRight, defaultBreadcrumbsWidgetStyles));
@@ -71,12 +75,7 @@ export class ChatDebugOverviewView extends Disposable {
 			}
 		}));
 
-		this.content = $('.chat-debug-overview-content');
-		this.scrollable = this._register(new DomScrollableElement(this.content, {}));
-		const scrollDom = this.scrollable.getDomNode();
-		scrollDom.style.flex = '1';
-		scrollDom.style.minHeight = '0';
-		DOM.append(this.container, scrollDom);
+		this.content = DOM.append(this.container, $('.chat-debug-overview-content'));
 	}
 
 	setSession(sessionResource: URI): void {
@@ -91,29 +90,36 @@ export class ChatDebugOverviewView extends Disposable {
 
 	hide(): void {
 		DOM.hide(this.container);
+		this.refreshScheduler.cancel();
 	}
 
 	refresh(): void {
 		if (this.container.style.display !== 'none') {
-			// On refresh, only update the metrics section in-place
-			if (this.metricsContainer && this.currentSessionResource) {
-				DOM.clearNode(this.metricsContainer);
-				const events = this.chatDebugService.getEvents(this.currentSessionResource);
-				this.renderMetricsContent(this.metricsContainer, events);
-				this.isFirstLoad = false;
-			} else {
-				this.load();
+			if (!this.refreshScheduler.isScheduled()) {
+				this.refreshScheduler.schedule();
 			}
 		}
 	}
 
+	private doRefresh(): void {
+		// On refresh, only update the metrics section in-place
+		if (this.metricsContainer && this.currentSessionResource) {
+			DOM.clearNode(this.metricsContainer);
+			const events = this.chatDebugService.getEvents(this.currentSessionResource);
+			this.renderMetricsContent(this.metricsContainer, events);
+			this.isFirstLoad = false;
+		} else {
+			this.load();
+		}
+	}
+
 	updateBreadcrumb(): void {
 		if (!this.currentSessionResource) {
 			return;
 		}
 		const sessionTitle = this.chatService.getSessionTitle(this.currentSessionResource) || LocalChatSessionUri.parseLocalSessionId(this.currentSessionResource) || this.currentSessionResource.toString();
 		this.breadcrumbWidget.setItems([
-			new TextBreadcrumbItem(localize('chatDebug.title', "Chat Debug Panel"), true),
+			new TextBreadcrumbItem(localize('chatDebug.title', "Agent Debug Logs"), true),
 			new TextBreadcrumbItem(sessionTitle),
 		]);
 	}
@@ -148,11 +154,13 @@ export class ChatDebugOverviewView extends Disposable {
 		// Session details section
 		this.renderSessionDetails(this.currentSessionResource);
 
-		// Derived overview metrics
+		// Derived overview metrics — show shimmer only on the very first load
+		// AND when there are no events yet. If events were already streamed
+		// (e.g. while viewing logs), render them immediately so the shimmer
+		// doesn't get stuck forever waiting for an event that already fired.
 		const events = this.chatDebugService.getEvents(this.currentSessionResource);
-		this.renderDerivedOverview(events, this.isFirstLoad);
+		this.renderDerivedOverview(events, this.isFirstLoad && events.length === 0);
 		this.isFirstLoad = false;
-		this.scrollable.scanDomNode();
 	}
 
 	private renderSessionDetails(sessionUri: URI): void {
@@ -164,7 +172,7 @@ export class ChatDebugOverviewView extends Disposable {
 		// Session type
 		const sessionType = getChatSessionType(sessionUri);
 		const contribution = this.chatSessionsService.getChatSessionContribution(sessionType);
-		const sessionTypeName = contribution?.displayName || (sessionType === 'local'
+		const sessionTypeName = contribution?.displayName || (sessionType === localChatSessionType
 			? localize('chatDebug.sessionType.local', "Local")
 			: sessionType);
 		details.push({ label: localize('chatDebug.detail.sessionType', "Session Type"), value: sessionTypeName });
@@ -278,7 +286,7 @@ export class ChatDebugOverviewView extends Disposable {
 		const metrics: OverviewMetric[] = [
 			{ label: localize('chatDebug.metric.modelTurns', "Model Turns"), value: String(modelTurns.length) },
 			{ label: localize('chatDebug.metric.toolCalls', "Tool Calls"), value: String(toolCalls.length) },
-			{ label: localize('chatDebug.metric.totalTokens', "Total Tokens"), value: totalTokens.toLocaleString() },
+			{ label: localize('chatDebug.metric.totalTokens', "Total Tokens"), value: numberFormatter.value.format(totalTokens) },
 			{ label: localize('chatDebug.metric.errors', "Errors"), value: String(errors.length) },
 			{ label: localize('chatDebug.metric.totalEvents', "Total Events"), value: String(events.length) },
 		];
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugToolCallContentRenderer.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugToolCallContentRenderer.ts
new file mode 100644
index 0000000000000..e87fdd087332f
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugToolCallContentRenderer.ts
@@ -0,0 +1,185 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as DOM from '../../../../../base/browser/dom.js';
+import { Button } from '../../../../../base/browser/ui/button/button.js';
+import { getDefaultHoverDelegate } from '../../../../../base/browser/ui/hover/hoverDelegateFactory.js';
+import { createTrustedTypesPolicy } from '../../../../../base/browser/trustedTypes.js';
+import { Codicon } from '../../../../../base/common/codicons.js';
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { localize } from '../../../../../nls.js';
+import { IClipboardService } from '../../../../../platform/clipboard/common/clipboardService.js';
+import { ILanguageService } from '../../../../../editor/common/languages/language.js';
+import { tokenizeToString } from '../../../../../editor/common/languages/textToHtmlTokenizer.js';
+import { IChatDebugEventToolCallContent } from '../../common/chatDebugService.js';
+import { setupCollapsibleToggle } from './chatDebugCollapsible.js';
+
+const $ = DOM.$;
+
+const _ttpPolicy = createTrustedTypesPolicy('chatDebugTokenizer', {
+	createHTML(html: string) {
+		return html;
+	}
+});
+
+export function tryParseJSON(text: string): { parsed: unknown; isJSON: true } | { isJSON: false } {
+	try {
+		return { parsed: JSON.parse(text), isJSON: true };
+	} catch {
+		return { isJSON: false };
+	}
+}
+
+/**
+ * Format and syntax-highlight a content string.
+ * When the content is valid JSON it is pretty-printed and tokenized as JSON;
+ * otherwise it is tokenized as markdown.
+ */
+export async function tokenizeContent(text: string, languageService: ILanguageService): Promise<{ plainText: string; tokenizedHtml: string }> {
+	const result = tryParseJSON(text);
+	const plainText = result.isJSON ? JSON.stringify(result.parsed, null, 2) : text;
+	const language = result.isJSON ? 'json' : 'markdown';
+	const tokenizedHtml = await tokenizeToString(languageService, plainText, language);
+	return { plainText, tokenizedHtml };
+}
+
+/**
+ * Render a collapsible section. When `tokenizedHtml` is provided the content
+ * is rendered as syntax-highlighted HTML; otherwise plain-text is used.
+ * Optionally adds a copy button when `clipboardService` is provided.
+ */
+export function renderSection(
+	parent: HTMLElement,
+	label: string,
+	plainText: string,
+	tokenizedHtml: string | undefined,
+	disposables: DisposableStore,
+	initiallyCollapsed: boolean = false,
+	clipboardService?: IClipboardService,
+): void {
+	const sectionEl = DOM.append(parent, $('div.chat-debug-message-section'));
+	const header = DOM.append(sectionEl, $('div.chat-debug-message-section-header'));
+	const chevron = DOM.append(header, $('span.chat-debug-message-section-chevron'));
+	DOM.append(header, $('span.chat-debug-message-section-title', undefined, label));
+
+	if (clipboardService) {
+		const copyBtn = disposables.add(new Button(header, {
+			title: localize('chatDebug.section.copy', "Copy"),
+			ariaLabel: localize('chatDebug.section.copy', "Copy"),
+			hoverDelegate: getDefaultHoverDelegate('mouse'),
+		}));
+		copyBtn.icon = Codicon.copy;
+		copyBtn.element.classList.add('chat-debug-section-copy-btn');
+		disposables.add(DOM.addDisposableListener(copyBtn.element, DOM.EventType.MOUSE_ENTER, () => {
+			header.classList.add('chat-debug-section-copy-header-passthrough');
+		}));
+		disposables.add(DOM.addDisposableListener(copyBtn.element, DOM.EventType.MOUSE_LEAVE, () => {
+			header.classList.remove('chat-debug-section-copy-header-passthrough');
+		}));
+		disposables.add(copyBtn.onDidClick(e => {
+			if (e) {
+				DOM.EventHelper.stop(e, true);
+			}
+			clipboardService.writeText(plainText);
+		}));
+	}
+
+	const wrapper = DOM.append(sectionEl, $('div.chat-debug-message-section-content-wrapper'));
+	const contentEl = DOM.append(wrapper, $('pre.chat-debug-message-section-content'));
+	contentEl.tabIndex = 0;
+
+	if (tokenizedHtml) {
+		const trustedHtml = _ttpPolicy?.createHTML(tokenizedHtml) ?? tokenizedHtml;
+		contentEl.innerHTML = trustedHtml as string;
+	} else {
+		contentEl.textContent = plainText;
+	}
+
+	setupCollapsibleToggle(chevron, header, wrapper, disposables, initiallyCollapsed);
+}
+
+/**
+ * Render a resolved tool call content with structured sections for
+ * tool name, status, duration, arguments, and output.
+ * Reuses the existing message content and collapsible section components.
+ * When JSON is detected in input/output, renders it with syntax highlighting
+ * using the editor's tokenization.
+ */
+export async function renderToolCallContent(content: IChatDebugEventToolCallContent, languageService: ILanguageService, clipboardService?: IClipboardService): Promise<{ element: HTMLElement; disposables: DisposableStore }> {
+	const disposables = new DisposableStore();
+	const container = $('div.chat-debug-message-content');
+	container.tabIndex = 0;
+
+	// Header: tool name
+	DOM.append(container, $('div.chat-debug-message-content-title', undefined, content.toolName));
+
+	// Status summary line
+	const statusParts: string[] = [];
+	if (content.result) {
+		statusParts.push(content.result === 'success'
+			? localize('chatDebug.toolCall.success', "Success")
+			: localize('chatDebug.toolCall.error', "Error"));
+	}
+	if (content.durationInMillis !== undefined) {
+		statusParts.push(localize('chatDebug.toolCall.duration', "{0}ms", content.durationInMillis));
+	}
+	if (statusParts.length > 0) {
+		DOM.append(container, $('div.chat-debug-message-content-summary', undefined, statusParts.join(' \u00b7 ')));
+	}
+
+	// Build collapsible sections for arguments and output
+	const sectionsContainer = DOM.append(container, $('div.chat-debug-message-sections'));
+
+	if (content.input) {
+		const { plainText, tokenizedHtml } = await tokenizeContent(content.input, languageService);
+		renderSection(sectionsContainer, localize('chatDebug.toolCall.arguments', "Arguments"), plainText, tokenizedHtml, disposables, false, clipboardService);
+	}
+
+	if (content.output) {
+		const { plainText, tokenizedHtml } = await tokenizeContent(content.output, languageService);
+		renderSection(sectionsContainer, localize('chatDebug.toolCall.output', "Output"), plainText, tokenizedHtml, disposables, false, clipboardService);
+	}
+
+	return { element: container, disposables };
+}
+
+/**
+ * Convert a resolved tool call content to plain text for clipboard / editor output.
+ */
+export function toolCallContentToPlainText(content: IChatDebugEventToolCallContent): string {
+	const lines: string[] = [];
+	lines.push(localize('chatDebug.toolCall.toolLabel', "Tool: {0}", content.toolName));
+
+	if (content.result) {
+		lines.push(localize('chatDebug.toolCall.statusLabel', "Status: {0}", content.result));
+	}
+	if (content.durationInMillis !== undefined) {
+		lines.push(localize('chatDebug.toolCall.durationLabel', "Duration: {0}ms", content.durationInMillis));
+	}
+
+	if (content.input) {
+		lines.push('');
+		lines.push(`[${localize('chatDebug.toolCall.arguments', "Arguments")}]`);
+		try {
+			const parsed = JSON.parse(content.input);
+			lines.push(JSON.stringify(parsed, null, 2));
+		} catch {
+			lines.push(content.input);
+		}
+	}
+
+	if (content.output) {
+		lines.push('');
+		lines.push(`[${localize('chatDebug.toolCall.output', "Output")}]`);
+		try {
+			const parsed = JSON.parse(content.output);
+			lines.push(JSON.stringify(parsed, null, 2));
+		} catch {
+			lines.push(content.output);
+		}
+	}
+
+	return lines.join('\n');
+}
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugTypes.ts b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugTypes.ts
index aab9e46a9383c..a6ac1bc979972 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugTypes.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/chatDebugTypes.ts
@@ -19,6 +19,8 @@ const $ = DOM.$;
 export interface IChatDebugEditorOptions extends IEditorOptions {
 	readonly sessionResource?: URI;
 	readonly viewHint?: 'home' | 'overview' | 'logs' | 'flowchart';
+	/** When set, automatically applies this text as the log filter. */
+	readonly filter?: string;
 }
 
 export const enum ViewState {
@@ -36,26 +38,14 @@ export const enum LogsViewMode {
 export const CHAT_DEBUG_FILTER_ACTIVE = new RawContextKey<boolean>('chatDebugFilterActive', false);
 export const CHAT_DEBUG_KIND_TOOL_CALL = new RawContextKey<boolean>('chatDebug.kindToolCall', true);
 export const CHAT_DEBUG_KIND_MODEL_TURN = new RawContextKey<boolean>('chatDebug.kindModelTurn', true);
-export const CHAT_DEBUG_KIND_GENERIC = new RawContextKey<boolean>('chatDebug.kindGeneric', true);
+export const CHAT_DEBUG_KIND_PROMPT_DISCOVERY = new RawContextKey<boolean>('chatDebug.kindPromptDiscovery', true);
 export const CHAT_DEBUG_KIND_SUBAGENT = new RawContextKey<boolean>('chatDebug.kindSubagent', true);
-export const CHAT_DEBUG_KIND_USER_MESSAGE = new RawContextKey<boolean>('chatDebug.kindUserMessage', true);
-export const CHAT_DEBUG_KIND_AGENT_RESPONSE = new RawContextKey<boolean>('chatDebug.kindAgentResponse', true);
-export const CHAT_DEBUG_LEVEL_TRACE = new RawContextKey<boolean>('chatDebug.levelTrace', true);
-export const CHAT_DEBUG_LEVEL_INFO = new RawContextKey<boolean>('chatDebug.levelInfo', true);
-export const CHAT_DEBUG_LEVEL_WARNING = new RawContextKey<boolean>('chatDebug.levelWarning', true);
-export const CHAT_DEBUG_LEVEL_ERROR = new RawContextKey<boolean>('chatDebug.levelError', true);
 
 // Filter toggle command IDs
 export const CHAT_DEBUG_CMD_TOGGLE_TOOL_CALL = 'chatDebug.filter.toggleToolCall';
 export const CHAT_DEBUG_CMD_TOGGLE_MODEL_TURN = 'chatDebug.filter.toggleModelTurn';
-export const CHAT_DEBUG_CMD_TOGGLE_GENERIC = 'chatDebug.filter.toggleGeneric';
+export const CHAT_DEBUG_CMD_TOGGLE_PROMPT_DISCOVERY = 'chatDebug.filter.togglePromptDiscovery';
 export const CHAT_DEBUG_CMD_TOGGLE_SUBAGENT = 'chatDebug.filter.toggleSubagent';
-export const CHAT_DEBUG_CMD_TOGGLE_USER_MESSAGE = 'chatDebug.filter.toggleUserMessage';
-export const CHAT_DEBUG_CMD_TOGGLE_AGENT_RESPONSE = 'chatDebug.filter.toggleAgentResponse';
-export const CHAT_DEBUG_CMD_TOGGLE_TRACE = 'chatDebug.filter.toggleTrace';
-export const CHAT_DEBUG_CMD_TOGGLE_INFO = 'chatDebug.filter.toggleInfo';
-export const CHAT_DEBUG_CMD_TOGGLE_WARNING = 'chatDebug.filter.toggleWarning';
-export const CHAT_DEBUG_CMD_TOGGLE_ERROR = 'chatDebug.filter.toggleError';
 
 export class TextBreadcrumbItem extends BreadcrumbsItem {
 	constructor(
diff --git a/src/vs/workbench/contrib/chat/browser/chatDebug/media/chatDebug.css b/src/vs/workbench/contrib/chat/browser/chatDebug/media/chatDebug.css
index 8eee2975cf60b..eade72c676f6b 100644
--- a/src/vs/workbench/contrib/chat/browser/chatDebug/media/chatDebug.css
+++ b/src/vs/workbench/contrib/chat/browser/chatDebug/media/chatDebug.css
@@ -21,6 +21,9 @@
 	flex-direction: column;
 	align-items: center;
 	padding: 48px 24px;
+	flex: 1;
+	min-height: 0;
+	overflow-y: auto;
 }
 .chat-debug-home-title {
 	font-size: 18px;
@@ -61,6 +64,13 @@
 .chat-debug-home-session-item:hover {
 	background: var(--vscode-list-hoverBackground);
 }
+.chat-debug-home-session-item:disabled {
+	cursor: default;
+	opacity: 0.7;
+}
+.chat-debug-home-session-item:disabled:hover {
+	background: transparent;
+}
 .chat-debug-home-session-item-title {
 	flex: 1;
 	overflow: hidden;
@@ -132,6 +142,9 @@
 }
 .chat-debug-overview-content {
 	padding: 16px 24px;
+	flex: 1;
+	min-height: 0;
+	overflow-y: auto;
 }
 .chat-debug-overview-title-row {
 	display: flex;
@@ -270,19 +283,22 @@
 .chat-debug-editor-header .viewpane-filter-container {
 	flex: 1;
 	max-width: 500px;
+	margin-right: auto;
+}
+.chat-debug-editor-header .viewpane-filter-container .monaco-inputbox {
+	border-color: var(--vscode-panelInput-border, transparent) !important;
 }
 .chat-debug-view-mode-toggle.monaco-button {
 	width: auto;
 	display: inline-flex;
 	align-items: center;
 	gap: 6px;
-	padding: 4px 8px;
-	border-radius: 2px;
-	font-size: 12px;
-	cursor: pointer;
 }
-.chat-debug-view-mode-toggle.monaco-button:focus {
-	border-color: var(--vscode-focusBorder);
+.chat-debug-troubleshoot-button.monaco-button {
+	width: auto;
+	display: inline-flex;
+	align-items: center;
+	flex-shrink: 0;
 }
 .chat-debug-view-mode-labels {
 	display: grid;
@@ -320,6 +336,7 @@
 	flex-direction: row;
 	flex: 1;
 	overflow: hidden;
+	position: relative;
 }
 .chat-debug-logs-main {
 	display: flex;
@@ -343,7 +360,6 @@
 	align-items: center;
 	padding: 0 16px;
 	height: 28px;
-	border-bottom: 1px solid var(--vscode-widget-border, transparent);
 	font-size: 12px;
 }
 .chat-debug-log-row .chat-debug-log-created {
@@ -351,6 +367,10 @@
 	flex-shrink: 0;
 	color: var(--vscode-descriptionForeground);
 }
+.monaco-list:focus .monaco-list-row.selected .chat-debug-log-created,
+.monaco-list:focus .monaco-list-row.focused .chat-debug-log-created {
+	color: inherit;
+}
 .chat-debug-log-row .chat-debug-log-name {
 	width: 200px;
 	flex-shrink: 0;
@@ -409,13 +429,12 @@
 }
 .chat-debug-detail-panel {
 	flex-shrink: 0;
-	width: 350px;
 	display: flex;
 	flex-direction: column;
 	border-left: 1px solid var(--vscode-widget-border, var(--vscode-panel-border));
 	border-top: 1px solid var(--vscode-widget-border, var(--vscode-panel-border));
 	box-shadow: -6px 0 6px -6px var(--vscode-widget-shadow);
-	background: var(--vscode-editorWidget-background);
+	background: var(--vscode-panel-background);
 	font-size: 12px;
 	position: relative;
 	overflow: hidden;
@@ -442,10 +461,6 @@
 	opacity: 1;
 	background: var(--vscode-toolbar-hoverBackground);
 }
-.chat-debug-detail-panel > pre {
-	flex: 1;
-	min-height: 0;
-}
 .chat-debug-detail-panel pre {
 	margin: 0;
 	padding: 8px 16px;
@@ -462,10 +477,6 @@
 }
 
 /* ---- File List Content ---- */
-.chat-debug-detail-panel > .chat-debug-file-list {
-	flex: 1;
-	min-height: 0;
-}
 .chat-debug-file-list {
 	padding: 8px 16px;
 	font-size: 12px;
@@ -518,6 +529,18 @@
 	white-space: nowrap;
 	flex-shrink: 0;
 }
+.chat-debug-file-list-group-header {
+	margin-top: 4px;
+	padding: 2px 4px;
+	color: var(--vscode-descriptionForeground);
+}
+.chat-debug-file-list-group-header:first-child {
+	margin-top: 0;
+}
+.chat-debug-file-list-group-label {
+	font-weight: 600;
+	font-size: 11px;
+}
 .chat-debug-file-list-icon {
 	flex-shrink: 0;
 	width: 16px;
@@ -553,10 +576,6 @@
 }
 
 /* ---- Message Content (User Message / Agent Response) ---- */
-.chat-debug-detail-panel > .chat-debug-message-content {
-	flex: 1;
-	min-height: 0;
-}
 .chat-debug-message-content {
 	padding: 8px 16px;
 	font-size: 12px;
@@ -619,8 +638,6 @@
 }
 .chat-debug-message-section-content-wrapper {
 	border-top: 1px solid var(--vscode-widget-border, transparent);
-	max-height: 300px;
-	overflow: hidden;
 }
 .chat-debug-message-section-content {
 	margin: 0;
@@ -642,7 +659,8 @@
 }
 
 /* ---- File list: settings gear button ---- */
-.chat-debug-settings-gear.monaco-button {
+.chat-debug-settings-gear.monaco-button,
+.chat-debug-section-copy-btn.monaco-button {
 	flex-shrink: 0;
 	opacity: 0.7;
 	border-radius: 3px;
@@ -652,14 +670,17 @@
 	color: inherit;
 	min-width: auto;
 }
-.chat-debug-settings-gear.monaco-button:hover {
+.chat-debug-settings-gear.monaco-button:hover,
+.chat-debug-section-copy-btn.monaco-button:hover {
 	opacity: 1;
 	background: var(--vscode-toolbar-hoverBackground);
 }
-.chat-debug-settings-gear-header-passthrough {
+.chat-debug-settings-gear-header-passthrough,
+.chat-debug-section-copy-header-passthrough {
 	pointer-events: none;
 }
-.chat-debug-settings-gear-header-passthrough .chat-debug-settings-gear {
+.chat-debug-settings-gear-header-passthrough .chat-debug-settings-gear,
+.chat-debug-section-copy-header-passthrough .chat-debug-section-copy-btn {
 	pointer-events: auto;
 }
 
@@ -703,6 +724,14 @@
 	display: flex;
 	flex: 1;
 	overflow: hidden;
+	position: relative;
+}
+.chat-debug-flowchart-content-wrapper > .chat-debug-detail-panel {
+	position: absolute;
+	top: 0;
+	right: 0;
+	bottom: 0;
+	z-index: 10;
 }
 .chat-debug-flowchart-content {
 	flex: 1;
@@ -735,14 +764,19 @@
 .chat-debug-flowchart-subgraph:hover rect.chat-debug-flowchart-subgraph-header {
 	opacity: 0.25;
 }
-.chat-debug-flowchart-node:focus {
-	outline: 2px solid var(--vscode-focusBorder);
-	outline-offset: 2px;
-	border-radius: 6px;
+.chat-debug-flowchart-focus-ring {
+	display: none;
+}
+.chat-debug-flowchart-node:focus,
+.chat-debug-flowchart-node:focus-visible {
+	outline: none !important;
+}
+.chat-debug-flowchart-node:focus .chat-debug-flowchart-focus-ring {
+	display: inline;
 }
 .chat-debug-flowchart-subgraph-header:focus {
 	outline: 2px solid var(--vscode-focusBorder);
-	outline-offset: 1px;
+	outline-offset: 2px;
 }
 .chat-debug-flowchart-empty {
 	display: flex;
diff --git a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingActions.ts b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingActions.ts
index 488358e0c902e..1f021914c0b2e 100644
--- a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingActions.ts
@@ -6,6 +6,7 @@
 import { CancellationToken } from '../../../../../base/common/cancellation.js';
 import { Codicon } from '../../../../../base/common/codicons.js';
 import { KeyCode, KeyMod } from '../../../../../base/common/keyCodes.js';
+import { alert } from '../../../../../base/browser/ui/aria/aria.js';
 import { basename } from '../../../../../base/common/resources.js';
 import { URI, UriComponents } from '../../../../../base/common/uri.js';
 import { isCodeEditor } from '../../../../../editor/browser/editorBrowser.js';
@@ -37,6 +38,7 @@ import { CHAT_CATEGORY } from '../actions/chatActions.js';
 import { ChatTreeItem, IChatWidget, IChatWidgetService } from '../chat.js';
 import { IAgentSession, isAgentSession } from '../agentSessions/agentSessionsModel.js';
 import { AgentSessionProviders } from '../agentSessions/agentSessions.js';
+import { IsSessionsWindowContext } from '../../../../common/contextkeys.js';
 
 export abstract class EditingSessionAction extends Action2 {
 
@@ -361,7 +363,7 @@ export class ViewAllSessionChangesAction extends Action2 {
 					id: MenuId.AgentSessionItemToolbar,
 					group: 'navigation',
 					order: 0,
-					when: ChatContextKeys.hasAgentSessionChanges
+					when: ContextKeyExpr.and(ChatContextKeys.hasAgentSessionChanges, IsSessionsWindowContext.negate())
 				}
 			],
 		});
@@ -513,7 +515,7 @@ registerAction2(class RemoveAction extends Action2 {
 				mac: {
 					primary: KeyMod.CtrlCmd | KeyCode.Backspace,
 				},
-				when: ContextKeyExpr.and(ChatContextKeys.inChatSession, EditorContextKeys.textInputFocus.negate()),
+				when: ContextKeyExpr.and(ChatContextKeys.inChatSession, EditorContextKeys.textInputFocus.negate(), ChatContextKeys.inChatQuestionCarousel.negate()),
 				weight: KeybindingWeight.WorkbenchContrib,
 			},
 			menu: [
@@ -562,7 +564,7 @@ registerAction2(class RestoreCheckpointAction extends Action2 {
 				mac: {
 					primary: KeyMod.CtrlCmd | KeyCode.Backspace,
 				},
-				when: ContextKeyExpr.and(ChatContextKeys.inChatSession, EditorContextKeys.textInputFocus.negate()),
+				when: ContextKeyExpr.and(ChatContextKeys.inChatSession, EditorContextKeys.textInputFocus.negate(), ChatContextKeys.inChatQuestionCarousel.negate()),
 				weight: KeybindingWeight.WorkbenchContrib,
 			},
 			menu: [
@@ -598,6 +600,55 @@ registerAction2(class RestoreCheckpointAction extends Action2 {
 	}
 });
 
+registerAction2(class RestoreLastCheckpoint extends Action2 {
+	constructor() {
+		super({
+			id: 'workbench.action.chat.restoreLastCheckpoint',
+			title: localize2('chat.restoreLastCheckpoint.label', "Restore to Last Checkpoint"),
+			f1: true,
+			category: CHAT_CATEGORY,
+			icon: Codicon.discard,
+			precondition: ContextKeyExpr.and(
+				ChatContextKeys.inChatSession,
+				ContextKeyExpr.equals(`config.${ChatConfiguration.CheckpointsEnabled}`, true),
+				ChatContextKeys.lockedToCodingAgent.negate()
+			)
+		});
+	}
+
+	async run(accessor: ServicesAccessor, ...args: unknown[]) {
+		let item = args[0] as ChatTreeItem | undefined;
+		const chatWidgetService = accessor.get(IChatWidgetService);
+		const chatService = accessor.get(IChatService);
+		const widget = (isChatTreeItem(item) && chatWidgetService.getWidgetBySessionResource(item.sessionResource)) || chatWidgetService.lastFocusedWidget;
+		if (!isResponseVM(item) && !isRequestVM(item)) {
+			item = widget?.getFocus();
+		}
+
+		const sessionResource = widget?.viewModel?.sessionResource ?? (isChatTreeItem(item) ? item.sessionResource : undefined);
+		if (!sessionResource) {
+			return;
+		}
+
+		const chatModel = chatService.getSession(sessionResource);
+		if (!chatModel?.editingSession) {
+			return;
+		}
+
+		const checkpointRequest = chatModel.checkpoint;
+		if (!checkpointRequest) {
+			alert(localize('chat.restoreCheckpoint.none', 'There is no checkpoint to restore.'));
+			return;
+		}
+
+		widget?.viewModel?.model.setCheckpoint(checkpointRequest.id);
+		widget?.focusInput();
+		widget?.input.setValue(checkpointRequest.message.text, false);
+
+		await restoreSnapshotWithConfirmationByRequestId(accessor, sessionResource, checkpointRequest.id);
+	}
+});
+
 registerAction2(class EditAction extends Action2 {
 	constructor() {
 		super({
diff --git a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingCheckpointTimelineImpl.ts b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingCheckpointTimelineImpl.ts
index 342560fae04cb..500774bfeb898 100644
--- a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingCheckpointTimelineImpl.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingCheckpointTimelineImpl.ts
@@ -16,14 +16,13 @@ import { isEqual } from '../../../../../base/common/resources.js';
 import { isDefined, Mutable } from '../../../../../base/common/types.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { generateUuid } from '../../../../../base/common/uuid.js';
+import { Range } from '../../../../../editor/common/core/range.js';
 import { TextEdit } from '../../../../../editor/common/languages.js';
-import { ITextModel } from '../../../../../editor/common/model.js';
-import { TextModel } from '../../../../../editor/common/model/textModel.js';
+import { DefaultEndOfLine, EndOfLinePreference, ITextModel, ValidAnnotatedEditOperation } from '../../../../../editor/common/model.js';
+import { createTextBuffer } from '../../../../../editor/common/model/textModel.js';
 import { IEditorWorkerService } from '../../../../../editor/common/services/editorWorker.js';
-import { IModelService } from '../../../../../editor/common/services/model.js';
 import { ITextModelService } from '../../../../../editor/common/services/resolverService.js';
 import { IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
-import { IInstantiationService } from '../../../../../platform/instantiation/common/instantiation.js';
 import { CellEditType, CellUri, INotebookTextModel } from '../../../notebook/common/notebookCommon.js';
 import { INotebookEditorModelResolverService } from '../../../notebook/common/notebookEditorModelResolverService.js';
 import { INotebookService } from '../../../notebook/common/notebookService.js';
@@ -71,6 +70,7 @@ export class ChatEditingCheckpointTimelineImpl implements IChatEditingCheckpoint
 	private readonly _operations = observableValueOpts<FileOperation[]>({ equalsFn: () => false }, []); // mutable
 	private readonly _fileBaselines = new Map<string, IFileBaseline>(); // key: `${uri}::${requestId}`
 	private readonly _refCountedDiffs = new Map<string, IObservable<IEditSessionEntryDiff | undefined>>();
+	private readonly _finalizedDiffCache = new Map<string, IEditSessionEntryDiff>();
 
 	/** Gets the checkpoint, if any, we can 'undo' to. */
 	private readonly _willUndoToCheckpoint = derived(reader => {
@@ -123,7 +123,19 @@ export class ChatEditingCheckpointTimelineImpl implements IChatEditingCheckpoint
 
 		// Find the next edit operation that would be applied...
 		const nextOperation = operations.find(op => op.epoch >= currentEpoch);
-		const nextCheckpoint = nextOperation && checkpoints.find(op => op.epoch > nextOperation.epoch);
+
+		// When there are no more operations, advance one request at a time
+		// by finding the next request-start checkpoint boundary.
+		if (!nextOperation) {
+			const nextRequestStart = checkpoints.find(cp => cp.epoch >= currentEpoch && cp.undoStopId === undefined);
+			if (!nextRequestStart) {
+				return maxEncounteredEpoch + 1;
+			}
+			const requestAfter = checkpoints.find(cp => cp.epoch > nextRequestStart.epoch && cp.undoStopId === undefined);
+			return requestAfter ? requestAfter.epoch : (maxEncounteredEpoch + 1);
+		}
+
+		const nextCheckpoint = checkpoints.find(op => op.epoch > nextOperation.epoch);
 
 		// And figure out where we're going if we're navigating across request
 		// 1. If there is no next request or if the next target checkpoint is in
@@ -192,8 +204,6 @@ export class ChatEditingCheckpointTimelineImpl implements IChatEditingCheckpoint
 		private readonly _delegate: IChatEditingTimelineFsDelegate,
 		@INotebookEditorModelResolverService private readonly _notebookEditorModelResolverService: INotebookEditorModelResolverService,
 		@INotebookService private readonly _notebookService: INotebookService,
-		@IInstantiationService private readonly _instantiationService: IInstantiationService,
-		@IModelService private readonly _modelService: IModelService,
 		@ITextModelService private readonly _textModelService: ITextModelService,
 		@IEditorWorkerService private readonly _editorWorkerService: IEditorWorkerService,
 		@IConfigurationService private readonly _configurationService: IConfigurationService
@@ -711,28 +721,15 @@ export class ChatEditingCheckpointTimelineImpl implements IChatEditingCheckpoint
 	}
 
 	private _applyTextEditsToContent(content: string, edits: readonly TextEdit[]): string {
-		// Use the example pattern provided by the user
-		const makeModel = (uri: URI, contents: string) => this._instantiationService.createInstance(TextModel, contents, '', this._modelService.getCreationOptions('', uri, true), uri);
-
-		// Create a temporary URI for the model
-		const tempUri = URI.from({ scheme: 'temp', path: `/temp-${Date.now()}.txt` });
-		const model = makeModel(tempUri, content);
-
+		const { textBuffer, disposable } = createTextBuffer(content, DefaultEndOfLine.LF);
 		try {
-			// Apply edits
-			model.applyEdits(edits.map(edit => ({
-				range: {
-					startLineNumber: edit.range.startLineNumber,
-					startColumn: edit.range.startColumn,
-					endLineNumber: edit.range.endLineNumber,
-					endColumn: edit.range.endColumn
-				},
-				text: edit.text
-			})));
-
-			return model.getValue();
+			textBuffer.applyEdits(edits.map(edit =>
+				new ValidAnnotatedEditOperation(null, Range.lift(edit.range), edit.text, false, false, false)
+			), false, false);
+			const fullRange = textBuffer.getRangeAt(0, textBuffer.getLength());
+			return textBuffer.getValueInRange(fullRange, EndOfLinePreference.TextDefined);
 		} finally {
-			model.dispose();
+			disposable.dispose();
 		}
 	}
 
@@ -772,11 +769,18 @@ export class ChatEditingCheckpointTimelineImpl implements IChatEditingCheckpoint
 
 	private _getEntryDiffBetweenEpochs(uri: URI, cacheKey: string, epochs: IObservable<{ start: ICheckpoint | undefined; end: ICheckpoint | undefined }>): IObservable<IEditSessionEntryDiff | undefined> {
 		const key = `${uri.toString()}\0${cacheKey}`;
+
+		const cached = this._finalizedDiffCache.get(key);
+		if (cached) {
+			return constObservable(cached);
+		}
+
 		let obs = this._refCountedDiffs.get(key);
 
 		if (!obs) {
 			obs = this._getEntryDiffBetweenEpochsInner(
 				uri,
+				key,
 				epochs,
 				() => this._refCountedDiffs.delete(key),
 			);
@@ -788,6 +792,7 @@ export class ChatEditingCheckpointTimelineImpl implements IChatEditingCheckpoint
 
 	private _getEntryDiffBetweenEpochsInner(
 		uri: URI,
+		cacheKey: string,
 		epochs: IObservable<{ start: ICheckpoint | undefined; end: ICheckpoint | undefined }>,
 		onLastObserverRemoved: () => void,
 	): IObservable<IEditSessionEntryDiff | undefined> {
@@ -859,6 +864,9 @@ export class ChatEditingCheckpointTimelineImpl implements IChatEditingCheckpoint
 
 			const promised = result.promise?.promiseResult.read(reader);
 			if (promised?.data) {
+				if (promised.data.isFinal) {
+					this._finalizedDiffCache.set(cacheKey, promised.data);
+				}
 				return promised.data;
 			}
 
diff --git a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingDeletedFileEntry.ts b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingDeletedFileEntry.ts
index 2e14eb81176bb..eeb4a37a52ff7 100644
--- a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingDeletedFileEntry.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingDeletedFileEntry.ts
@@ -5,6 +5,7 @@
 
 import { VSBuffer } from '../../../../../base/common/buffer.js';
 import { constObservable, IObservable, ITransaction, observableValue, transaction } from '../../../../../base/common/observable.js';
+import { isEqual } from '../../../../../base/common/resources.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { LineRange } from '../../../../../editor/common/core/ranges/lineRange.js';
 import { IDocumentDiff } from '../../../../../editor/common/diff/documentDiffProvider.js';
@@ -164,7 +165,7 @@ export class ChatEditingDeletedFileEntry extends AbstractChatEditingModifiedFile
 
 	equalsSnapshot(snapshot: ISnapshotEntry | undefined): boolean {
 		return !!snapshot &&
-			this.modifiedURI.toString() === snapshot.resource.toString() &&
+			isEqual(this.modifiedURI, snapshot.resource) &&
 			this._languageId === snapshot.languageId &&
 			this._originalContent === snapshot.original &&
 			snapshot.current === '' &&
diff --git a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingExplanationModelManager.ts b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingExplanationModelManager.ts
index b26f5ced875aa..e752209f42896 100644
--- a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingExplanationModelManager.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingExplanationModelManager.ts
@@ -14,7 +14,6 @@ import { DetailedLineRangeMapping, LineRangeMapping } from '../../../../../edito
 import { createDecorator } from '../../../../../platform/instantiation/common/instantiation.js';
 import { InstantiationType, registerSingleton } from '../../../../../platform/instantiation/common/extensions.js';
 import { ChatMessageRole, ILanguageModelsService } from '../../common/languageModels.js';
-import { ExtensionIdentifier } from '../../../../../platform/extensions/common/extensions.js';
 import * as nls from '../../../../../nls.js';
 
 /**
@@ -284,7 +283,7 @@ Example response format:
 
 			const response = await this._languageModelsService.sendChatRequest(
 				models[0],
-				new ExtensionIdentifier('core'),
+				undefined,
 				[{ role: ChatMessageRole.User, content: [{ type: 'text', value: prompt }] }],
 				{},
 				cancellationToken
diff --git a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingModifiedDocumentEntry.ts b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingModifiedDocumentEntry.ts
index 59f48b3ca0652..d7e1b62bb3c24 100644
--- a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingModifiedDocumentEntry.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingModifiedDocumentEntry.ts
@@ -6,6 +6,7 @@
 import { IReference, MutableDisposable } from '../../../../../base/common/lifecycle.js';
 import { Schemas } from '../../../../../base/common/network.js';
 import { ITransaction, autorun, transaction } from '../../../../../base/common/observable.js';
+import { isEqual } from '../../../../../base/common/resources.js';
 import { assertType } from '../../../../../base/common/types.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { getCodeEditor } from '../../../../../editor/browser/editorBrowser.js';
@@ -186,7 +187,7 @@ export class ChatEditingModifiedDocumentEntry extends AbstractChatEditingModifie
 
 	equalsSnapshot(snapshot: ISnapshotEntry | undefined): boolean {
 		return !!snapshot &&
-			this.modifiedURI.toString() === snapshot.resource.toString() &&
+			isEqual(this.modifiedURI, snapshot.resource) &&
 			this.modifiedModel.getLanguageId() === snapshot.languageId &&
 			this.originalModel.getValue() === snapshot.original &&
 			this.modifiedModel.getValue() === snapshot.current &&
diff --git a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingServiceImpl.ts b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingServiceImpl.ts
index 371bd071268e7..11a6ce23b97dc 100644
--- a/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingServiceImpl.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatEditing/chatEditingServiceImpl.ts
@@ -410,7 +410,7 @@ class ChatDecorationsProvider extends Disposable implements IDecorationsProvider
 	}
 
 	provideDecorations(uri: URI, _token: CancellationToken): IDecorationData | undefined {
-		const isCurrentlyBeingModified = this._currentlyEditingUris.get().some(e => e.toString() === uri.toString());
+		const isCurrentlyBeingModified = this._currentlyEditingUris.get().some(e => isEqual(e, uri));
 		if (isCurrentlyBeingModified) {
 			return {
 				weight: 1000,
@@ -418,7 +418,7 @@ class ChatDecorationsProvider extends Disposable implements IDecorationsProvider
 				bubble: false
 			};
 		}
-		const isModified = this._modifiedUris.get().some(e => e.toString() === uri.toString());
+		const isModified = this._modifiedUris.get().some(e => isEqual(e, uri));
 		if (isModified) {
 			return {
 				weight: 1000,
diff --git a/src/vs/workbench/contrib/chat/browser/chatEditing/media/chatEditingEditorOverlay.css b/src/vs/workbench/contrib/chat/browser/chatEditing/media/chatEditingEditorOverlay.css
index a29b827631234..fc44d44f42fad 100644
--- a/src/vs/workbench/contrib/chat/browser/chatEditing/media/chatEditingEditorOverlay.css
+++ b/src/vs/workbench/contrib/chat/browser/chatEditing/media/chatEditingEditorOverlay.css
@@ -8,25 +8,25 @@
 	color: var(--vscode-foreground);
 	background-color: var(--vscode-editorWidget-background);
 	border-radius: 6px;
-	border: 1px solid var(--vscode-contrastBorder);
+	border: 1px solid var(--vscode-editorWidget-border);
 	display: flex;
 	align-items: center;
 	justify-content: center;
 	gap: 4px;
 	z-index: 10;
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-md);
 	overflow: hidden;
 }
 
 @keyframes pulse {
 	0% {
-		box-shadow: 0 2px 8px 0 var(--vscode-widget-shadow);
+		box-shadow: var(--vscode-shadow-md);
 	}
 	50% {
-		box-shadow: 0 2px 8px 4px var(--vscode-widget-shadow);
+		box-shadow: var(--vscode-shadow-lg);
 	}
 	100% {
-		box-shadow: 0 2px 8px 0 var(--vscode-widget-shadow);
+		box-shadow: var(--vscode-shadow-md);
 	}
 }
 
diff --git a/src/vs/workbench/contrib/chat/browser/chatEditing/media/chatEditingExplanationWidget.css b/src/vs/workbench/contrib/chat/browser/chatEditing/media/chatEditingExplanationWidget.css
index 7bfca698ff817..71dbdf0a6d7eb 100644
--- a/src/vs/workbench/contrib/chat/browser/chatEditing/media/chatEditingExplanationWidget.css
+++ b/src/vs/workbench/contrib/chat/browser/chatEditing/media/chatEditingExplanationWidget.css
@@ -11,7 +11,7 @@
 	background-color: var(--vscode-editorWidget-background);
 	border: 1px solid var(--vscode-editorWidget-border, var(--vscode-contrastBorder));
 	border-radius: 8px;
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	font-size: 12px;
 	line-height: 1.4;
 	opacity: 0;
diff --git a/src/vs/workbench/contrib/chat/browser/chatEditing/media/chatEditorController.css b/src/vs/workbench/contrib/chat/browser/chatEditing/media/chatEditorController.css
index 402bd4b6b0b73..5e5b64f1fcdcb 100644
--- a/src/vs/workbench/contrib/chat/browser/chatEditing/media/chatEditorController.css
+++ b/src/vs/workbench/contrib/chat/browser/chatEditing/media/chatEditorController.css
@@ -7,7 +7,7 @@
 	opacity: 0;
 	transition: opacity 0.2s ease-in-out;
 	display: flex;
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-md);
 	border-radius: 6px;
 	overflow: hidden;
 }
@@ -21,7 +21,7 @@
 	border-radius: 6px;
 	background-color: var(--vscode-editorWidget-background);
 	color: var(--vscode-foreground);
-	border: 1px solid var(--vscode-contrastBorder);
+	border: 1px solid var(--vscode-editorWidget-border);
 	overflow: hidden;
 }
 
diff --git a/src/vs/workbench/contrib/chat/browser/chatImageCarouselService.ts b/src/vs/workbench/contrib/chat/browser/chatImageCarouselService.ts
new file mode 100644
index 0000000000000..3da4065348431
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/chatImageCarouselService.ts
@@ -0,0 +1,257 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { getMediaMime } from '../../../../base/common/mime.js';
+import { isEqual } from '../../../../base/common/resources.js';
+import { URI } from '../../../../base/common/uri.js';
+import { VSBuffer } from '../../../../base/common/buffer.js';
+import { localize } from '../../../../nls.js';
+import { createDecorator } from '../../../../platform/instantiation/common/instantiation.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IFileService } from '../../../../platform/files/common/files.js';
+import { extractImagesFromChatRequest, extractImagesFromChatResponse } from '../common/chatImageExtraction.js';
+import { IChatRequestViewModel, IChatResponseViewModel, isRequestVM, isResponseVM } from '../common/model/chatViewModel.js';
+import { IChatWidgetService } from './chat.js';
+
+export const IChatImageCarouselService = createDecorator<IChatImageCarouselService>('chatImageCarouselService');
+
+export interface IChatImageCarouselService {
+	readonly _serviceBrand: undefined;
+
+	/**
+	 * Opens the image carousel for the given resource URI, collecting all images
+	 * from the focused chat widget's responses to populate the carousel.
+	 *
+	 * @param resource The URI of the clicked image to start the carousel at.
+	 * @param data Optional raw image data (e.g. for input attachment images that are Uint8Arrays).
+	 */
+	openCarouselAtResource(resource: URI, data?: Uint8Array): Promise<void>;
+}
+
+//#region Carousel data types
+
+export interface ICarouselImage {
+	readonly id: string;
+	readonly name: string;
+	readonly mimeType: string;
+	readonly data: Uint8Array;
+}
+
+export interface ICarouselSection {
+	readonly title: string;
+	readonly images: ICarouselImage[];
+}
+
+export interface ICarouselCollectionArgs {
+	readonly collection: {
+		readonly id: string;
+		readonly title: string;
+		readonly sections: ICarouselSection[];
+	};
+	readonly startIndex: number;
+}
+
+export interface ICarouselSingleImageArgs {
+	readonly name: string;
+	readonly mimeType: string;
+	readonly data: Uint8Array;
+	readonly title: string;
+}
+
+//#endregion
+
+//#region Testable helper functions
+
+/**
+ * Collects all carousel image sections from chat items.
+ * Each request/response pair with images becomes one section containing
+ * user attachment images, tool invocation images, and inline reference images.
+ */
+export async function collectCarouselSections(
+	items: (IChatRequestViewModel | IChatResponseViewModel)[],
+	readFile: (uri: URI) => Promise<Uint8Array>,
+): Promise<ICarouselSection[]> {
+	const sections: ICarouselSection[] = [];
+
+	// Build a map from request id to request VM for pairing
+	const requestMap = new Map<string, IChatRequestViewModel>();
+	for (const item of items) {
+		if (isRequestVM(item)) {
+			requestMap.set(item.id, item);
+		}
+	}
+
+	for (const item of items) {
+		if (!isResponseVM(item)) {
+			continue;
+		}
+
+		const { title: extractedTitle, images: responseImages } = await extractImagesFromChatResponse(item, async uri => VSBuffer.wrap(await readFile(uri)));
+
+		// Also collect images from the corresponding user request
+		const request = requestMap.get(item.requestId);
+		const requestImages = request ? extractImagesFromChatRequest(request) : [];
+
+		const allImages = [...requestImages, ...responseImages];
+		if (allImages.length > 0) {
+			sections.push({
+				title: request?.messageText ?? extractedTitle,
+				images: allImages.map(({ id, name, mimeType, data }) => ({ id, name, mimeType, data: data.buffer }))
+			});
+		}
+	}
+
+	// Handle requests that have no response yet (e.g. pending requests with image attachments)
+	const respondedRequestIds = new Set(
+		items.filter(isResponseVM).map(r => r.requestId)
+	);
+	for (const item of items) {
+		if (!isRequestVM(item) || respondedRequestIds.has(item.id)) {
+			continue;
+		}
+		const requestImages = extractImagesFromChatRequest(item);
+		if (requestImages.length > 0) {
+			sections.push({
+				title: item.messageText,
+				images: requestImages.map(({ id, name, mimeType, data }) => ({ id, name, mimeType, data: data.buffer }))
+			});
+		}
+	}
+
+	return sections;
+}
+
+/**
+ * Finds the global index of the clicked image across all carousel sections.
+ * Tries URI string match, then parsed URI equality, then data buffer equality.
+ */
+export function findClickedImageIndex(
+	sections: ICarouselSection[],
+	resource: URI,
+	data?: Uint8Array,
+): number {
+	let globalOffset = 0;
+
+	for (const section of sections) {
+		const localIndex = findImageInList(section.images, resource, data);
+		if (localIndex >= 0) {
+			return globalOffset + localIndex;
+		}
+		globalOffset += section.images.length;
+	}
+
+	return -1;
+}
+
+function findImageInList(
+	images: ICarouselImage[],
+	resource: URI,
+	data?: Uint8Array,
+): number {
+	// Try matching by URI string (for inline references and tool images with URIs)
+	const uriStr = resource.toString();
+	const byUri = images.findIndex(img => img.id === uriStr);
+	if (byUri >= 0) {
+		return byUri;
+	}
+
+	// Try matching by parsed URI equality (for tool invocation images with generated URIs)
+	const byParsedUri = images.findIndex(img => {
+		try {
+			return isEqual(URI.parse(img.id), resource);
+		} catch {
+			return false;
+		}
+	});
+	if (byParsedUri >= 0) {
+		return byParsedUri;
+	}
+
+	// Fall back to matching by data buffer equality
+	if (data) {
+		const wrapped = VSBuffer.wrap(data);
+		return images.findIndex(img => VSBuffer.wrap(img.data).equals(wrapped));
+	}
+
+	return -1;
+}
+
+/**
+ * Builds the collection arguments for the carousel command.
+ */
+export function buildCollectionArgs(
+	sections: ICarouselSection[],
+	clickedGlobalIndex: number,
+	sessionResource: URI,
+): ICarouselCollectionArgs {
+	const collectionId = sessionResource.toString() + '_carousel';
+	return {
+		collection: {
+			id: collectionId,
+			title: sections.length === 1
+				? sections[0].title
+				: localize('chatImageCarousel.allImages', "Conversation Images"),
+			sections,
+		},
+		startIndex: clickedGlobalIndex,
+	};
+}
+
+/**
+ * Builds the single-image arguments for the carousel command.
+ */
+export function buildSingleImageArgs(resource: URI, data: Uint8Array): ICarouselSingleImageArgs {
+	const name = resource.path.split('/').pop() ?? 'image';
+	const mimeType = getMediaMime(resource.path) ?? getMediaMime(name) ?? 'image/png';
+	return { name, mimeType, data, title: name };
+}
+
+//#endregion
+
+const CAROUSEL_COMMAND = 'workbench.action.chat.openImageInCarousel';
+
+export class ChatImageCarouselService implements IChatImageCarouselService {
+
+	declare readonly _serviceBrand: undefined;
+
+	constructor(
+		@IChatWidgetService private readonly chatWidgetService: IChatWidgetService,
+		@ICommandService private readonly commandService: ICommandService,
+		@IFileService private readonly fileService: IFileService,
+	) { }
+
+	async openCarouselAtResource(resource: URI, data?: Uint8Array): Promise<void> {
+		const widget = this.chatWidgetService.lastFocusedWidget;
+		if (!widget?.viewModel) {
+			await this.openSingleImage(resource, data);
+			return;
+		}
+
+		const items = widget.viewModel.getItems().filter(
+			(item): item is IChatRequestViewModel | IChatResponseViewModel => isRequestVM(item) || isResponseVM(item)
+		);
+		const readFile = async (uri: URI) => (await this.fileService.readFile(uri)).value.buffer;
+		const sections = await collectCarouselSections(items, readFile);
+		const clickedGlobalIndex = findClickedImageIndex(sections, resource, data);
+
+		if (clickedGlobalIndex === -1 || sections.length === 0) {
+			await this.openSingleImage(resource, data);
+			return;
+		}
+
+		const args = buildCollectionArgs(sections, clickedGlobalIndex, widget.viewModel.sessionResource);
+		await this.commandService.executeCommand(CAROUSEL_COMMAND, args);
+	}
+
+	private async openSingleImage(resource: URI, data?: Uint8Array): Promise<void> {
+		if (!data) {
+			const content = await this.fileService.readFile(resource);
+			data = content.value.buffer;
+		}
+
+		const args = buildSingleImageArgs(resource, data);
+		await this.commandService.executeCommand(CAROUSEL_COMMAND, args);
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/chatImageUtils.ts b/src/vs/workbench/contrib/chat/browser/chatImageUtils.ts
index 89f1ecb122528..62f7c38ec2408 100644
--- a/src/vs/workbench/contrib/chat/browser/chatImageUtils.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatImageUtils.ts
@@ -8,6 +8,7 @@ import { joinPath } from '../../../../base/common/resources.js';
 import { URI } from '../../../../base/common/uri.js';
 import { IFileService } from '../../../../platform/files/common/files.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
+import { CommandsRegistry } from '../../../../platform/commands/common/commands.js';
 
 /**
  * Resizes an image provided as a UInt8Array string. Resizing is based on Open AI's algorithm for tokenzing images.
@@ -160,3 +161,10 @@ function getTimestampFromFilename(filename: string): number | undefined {
 	}
 	return undefined;
 }
+
+CommandsRegistry.registerCommand('_chat.resizeImage', async (_accessor, data: Uint8Array | VSBuffer, mimeType?: string): Promise<Uint8Array> => {
+	if (data instanceof VSBuffer) {
+		data = data.buffer;
+	}
+	return resizeImage(data, mimeType);
+});
diff --git a/src/vs/workbench/contrib/chat/browser/chatManagement/chatUsageWidget.ts b/src/vs/workbench/contrib/chat/browser/chatManagement/chatUsageWidget.ts
index d33b5a1524c9f..c49f770db150b 100644
--- a/src/vs/workbench/contrib/chat/browser/chatManagement/chatUsageWidget.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatManagement/chatUsageWidget.ts
@@ -68,12 +68,14 @@ export class ChatUsageWidget extends Disposable {
 
 			// Premium requests
 			if (premiumChatQuota) {
-				this.renderQuotaItem(this.usageSection, localize('plan.premiumRequests', 'Premium requests'), premiumChatQuota);
+				const premiumLabel = premiumChatQuota.overageEnabled ? localize('plan.includedPremiumRequests', 'Included premium requests') : localize('plan.premiumRequests', 'Premium requests');
+				this.renderQuotaItem(this.usageSection, premiumLabel, premiumChatQuota, premiumChatQuota.overageEnabled);
 
-				// Additional overage message
-				if (premiumChatQuota.overageEnabled) {
+				if (premiumChatQuota.overageEnabled && !premiumChatQuota.unlimited) {
 					const overageMessage = DOM.append(this.usageSection, $('.overage-message'));
-					overageMessage.textContent = localize('plan.additionalPaidEnabled', 'Additional paid premium requests enabled.');
+					overageMessage.append(localize('plan.overageApprovedLine1', "Additional premium requests approved."));
+					DOM.append(overageMessage, $('br'));
+					overageMessage.append(localize('plan.overageApprovedLine2', "You can continue after included premium requests limit reaches 100%."));
 				}
 			}
 
@@ -89,7 +91,7 @@ export class ChatUsageWidget extends Disposable {
 		this._onDidChangeContentHeight.fire(height);
 	}
 
-	private renderQuotaItem(container: HTMLElement, label: string, quota: IQuotaSnapshot): void {
+	private renderQuotaItem(container: HTMLElement, label: string, quota: IQuotaSnapshot, overageEnabled: boolean = false): void {
 		const quotaItem = DOM.append(container, $('.quota-item'));
 
 		const quotaItemHeader = DOM.append(quotaItem, $('.quota-item-header'));
@@ -109,10 +111,10 @@ export class ChatUsageWidget extends Disposable {
 		const percentageUsed = this.getQuotaPercentageUsed(quota);
 		progressBar.style.width = percentageUsed + '%';
 
-		// Apply warning/error classes based on usage
-		if (percentageUsed >= 90) {
+		// Apply warning/error classes based on usage (don't show error/warning if overage is enabled)
+		if (percentageUsed >= 90 && !overageEnabled) {
 			quotaItem.classList.add('error');
-		} else if (percentageUsed >= 75) {
+		} else if (percentageUsed >= 75 && !overageEnabled) {
 			quotaItem.classList.add('warning');
 		}
 	}
diff --git a/src/vs/workbench/contrib/chat/browser/chatRepoInfo.ts b/src/vs/workbench/contrib/chat/browser/chatRepoInfo.ts
index 494c639a67a38..b027ff798b967 100644
--- a/src/vs/workbench/contrib/chat/browser/chatRepoInfo.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatRepoInfo.ts
@@ -109,7 +109,7 @@ function determineChangeType(resource: ISCMResource, groupId: string): 'added' |
  * files is the presence/absence of a trailing newline (content otherwise identical),
  * no diff will be generated because VS Code's diff algorithm treats the lines as equal.
  */
-async function generateUnifiedDiff(
+export async function generateUnifiedDiff(
 	fileService: IFileService,
 	relPath: string,
 	originalUri: URI | undefined,
diff --git a/src/vs/workbench/contrib/chat/browser/chatSessions/chatSessionPickerActionItem.ts b/src/vs/workbench/contrib/chat/browser/chatSessions/chatSessionPickerActionItem.ts
index a21e2483b8d28..241eeb90adfcb 100644
--- a/src/vs/workbench/contrib/chat/browser/chatSessions/chatSessionPickerActionItem.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatSessions/chatSessionPickerActionItem.ts
@@ -7,6 +7,7 @@ import './media/chatSessionPickerActionItem.css';
 import { IAction } from '../../../../../base/common/actions.js';
 import { Event } from '../../../../../base/common/event.js';
 import * as dom from '../../../../../base/browser/dom.js';
+import { getActiveWindow } from '../../../../../base/browser/dom.js';
 import { IActionWidgetService } from '../../../../../platform/actionWidget/browser/actionWidget.js';
 import { IActionWidgetDropdownAction, IActionWidgetDropdownOptions } from '../../../../../platform/actionWidget/browser/actionWidgetDropdown.js';
 import { IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
@@ -19,6 +20,7 @@ import { IDisposable } from '../../../../../base/common/lifecycle.js';
 import { renderLabelWithIcons, renderIcon } from '../../../../../base/browser/ui/iconLabel/iconLabels.js';
 import { localize } from '../../../../../nls.js';
 import { URI } from '../../../../../base/common/uri.js';
+import { IChatInputPickerOptions } from '../widget/input/chatInputPickerActionItem.js';
 
 
 export interface IChatSessionPickerDelegate {
@@ -41,6 +43,7 @@ export class ChatSessionPickerActionItem extends ActionWidgetDropdownActionViewI
 		action: IAction,
 		initialState: { group: IChatSessionProviderOptionGroup; item: IChatSessionProviderOptionItem | undefined },
 		protected readonly delegate: IChatSessionPickerDelegate,
+		protected readonly _pickerOptions: IChatInputPickerOptions | undefined,
 		@IActionWidgetService actionWidgetService: IActionWidgetService,
 		@IContextKeyService contextKeyService: IContextKeyService,
 		@IKeybindingService keybindingService: IKeybindingService,
@@ -61,6 +64,7 @@ export class ChatSessionPickerActionItem extends ActionWidgetDropdownActionViewI
 			},
 			actionBarActionProvider: undefined,
 			reporter: { id: group.id, name: `ChatSession:${group.name}`, includeOptions: false },
+			getAnchor: () => this._getAnchorElement(),
 		};
 
 		super(actionWithLabel, sessionPickerActionWidgetOptions, actionWidgetService, keybindingService, contextKeyService, telemetryService);
@@ -153,6 +157,17 @@ export class ChatSessionPickerActionItem extends ActionWidgetDropdownActionViewI
 		};
 	}
 
+	/**
+	 * Returns the anchor element for the dropdown.
+	 * Falls back to the overflow anchor if this element is not in the DOM.
+	 */
+	private _getAnchorElement(): HTMLElement {
+		if (this.element && getActiveWindow().document.contains(this.element)) {
+			return this.element;
+		}
+		return this._pickerOptions?.getOverflowAnchor?.() ?? this.element!;
+	}
+
 	protected override renderLabel(element: HTMLElement): IDisposable | null {
 		const domChildren = [];
 		element.classList.add('chat-session-option-picker');
diff --git a/src/vs/workbench/contrib/chat/browser/chatSessions/chatSessions.contribution.ts b/src/vs/workbench/contrib/chat/browser/chatSessions/chatSessions.contribution.ts
index deff82e869367..ee72554e7de8d 100644
--- a/src/vs/workbench/contrib/chat/browser/chatSessions/chatSessions.contribution.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatSessions/chatSessions.contribution.ts
@@ -4,12 +4,12 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { sep } from '../../../../../base/common/path.js';
-import { raceCancellationError } from '../../../../../base/common/async.js';
+import { AsyncIterableProducer, raceCancellationError } from '../../../../../base/common/async.js';
 import { CancellationToken, CancellationTokenSource } from '../../../../../base/common/cancellation.js';
 import { Codicon } from '../../../../../base/common/codicons.js';
 import { AsyncEmitter, Emitter, Event } from '../../../../../base/common/event.js';
-import { combinedDisposable, Disposable, DisposableMap, DisposableStore, IDisposable, toDisposable } from '../../../../../base/common/lifecycle.js';
-import { ResourceMap } from '../../../../../base/common/map.js';
+import { combinedDisposable, Disposable, DisposableMap, DisposableStore, IDisposable } from '../../../../../base/common/lifecycle.js';
+import { ResourceMap, ResourceSet } from '../../../../../base/common/map.js';
 import { Schemas } from '../../../../../base/common/network.js';
 import * as resources from '../../../../../base/common/resources.js';
 import { ThemeIcon } from '../../../../../base/common/themables.js';
@@ -29,28 +29,28 @@ import { IEditorService } from '../../../../services/editor/common/editorService
 import { IExtensionService, isProposedApiEnabled } from '../../../../services/extensions/common/extensions.js';
 import { ExtensionsRegistry } from '../../../../services/extensions/common/extensionsRegistry.js';
 import { ChatEditorInput } from '../widgetHosts/editor/chatEditorInput.js';
-import { IChatAgentAttachmentCapabilities, IChatAgentData, IChatAgentRequest, IChatAgentService } from '../../common/participants/chatAgents.js';
+import { IChatAgentAttachmentCapabilities, IChatAgentData, IChatAgentService } from '../../common/participants/chatAgents.js';
 import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
-import { IChatSession, IChatSessionContentProvider, IChatSessionItem, IChatSessionItemController, IChatSessionOptionsWillNotifyExtensionEvent, IChatSessionProviderOptionGroup, IChatSessionProviderOptionItem, IChatSessionsExtensionPoint, IChatSessionsService, isSessionInProgressStatus } from '../../common/chatSessionsService.js';
+import { IChatNewSessionRequest, IChatSession, IChatSessionContentProvider, IChatSessionItem, IChatSessionItemController, IChatSessionItemsDelta, IChatSessionOptionsWillNotifyExtensionEvent, IChatSessionProviderOptionGroup, IChatSessionProviderOptionItem, IChatSessionsExtensionPoint, IChatSessionsService, isSessionInProgressStatus, ResolvedChatSessionsExtensionPoint } from '../../common/chatSessionsService.js';
 import { ChatAgentLocation, ChatModeKind } from '../../common/constants.js';
 import { CHAT_CATEGORY } from '../actions/chatActions.js';
 import { IChatEditorOptions } from '../widgetHosts/editor/chatEditor.js';
 import { IChatModel } from '../../common/model/chatModel.js';
 import { IChatService, IChatToolInvocation } from '../../common/chatService/chatService.js';
-import { autorun, autorunIterableDelta, observableFromEvent, observableSignalFromEvent } from '../../../../../base/common/observable.js';
+import { autorun, observableFromEvent } from '../../../../../base/common/observable.js';
 import { IChatRequestVariableEntry } from '../../common/attachments/chatVariableEntries.js';
 import { renderAsPlaintext } from '../../../../../base/browser/markdownRenderer.js';
 import { IMarkdownString } from '../../../../../base/common/htmlContent.js';
 import { IViewsService } from '../../../../services/views/common/viewsService.js';
 import { ChatViewId } from '../chat.js';
 import { ChatViewPane } from '../widgetHosts/viewPane/chatViewPane.js';
-import { AgentSessionProviders, backgroundAgentDisplayName, getAgentSessionProviderName } from '../agentSessions/agentSessions.js';
+import { AgentSessionProviders, getAgentSessionProviderName } from '../agentSessions/agentSessions.js';
 import { BugIndicatingError, isCancellationError } from '../../../../../base/common/errors.js';
 import { IEditorGroupsService } from '../../../../services/editor/common/editorGroupsService.js';
-import { LocalChatSessionUri } from '../../common/model/chatUri.js';
+import { getChatSessionType, isUntitledChatSession, LocalChatSessionUri } from '../../common/model/chatUri.js';
 import { assertNever } from '../../../../../base/common/assert.js';
 import { ICommandService } from '../../../../../platform/commands/common/commands.js';
-import { Target } from '../../common/promptSyntax/service/promptsService.js';
+import { Target } from '../../common/promptSyntax/promptTypes.js';
 
 const extensionPoint = ExtensionsRegistry.registerExtensionPoint<IChatSessionsExtensionPoint[]>({
 	extensionPoint: 'chatSessions',
@@ -172,6 +172,10 @@ const extensionPoint = ExtensionsRegistry.registerExtensionPoint<IChatSessionsEx
 						supportsPromptAttachments: {
 							description: localize('chatSessionsExtPoint.supportsPromptAttachments', 'Whether this chat session supports attaching prompts.'),
 							type: 'boolean'
+						},
+						supportsHandOffs: {
+							description: localize('chatSessionsExtPoint.supportsHandOffs', 'Whether this chat session supports hand-off prompts.'),
+							type: 'boolean'
 						}
 					}
 				},
@@ -230,6 +234,9 @@ class ContributedChatSessionData extends Disposable {
 	public getOption(optionId: string): string | IChatSessionProviderOptionItem | undefined {
 		return this._optionsCache.get(optionId);
 	}
+	public getAllOptions(): IterableIterator<[string, string | IChatSessionProviderOptionItem]> {
+		return this._optionsCache.entries();
+	}
 	public setOption(optionId: string, value: string | IChatSessionProviderOptionItem): void {
 		this._optionsCache.set(optionId, value);
 	}
@@ -272,7 +279,7 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 	private readonly _onDidChangeItemsProviders = this._register(new Emitter<{ readonly chatSessionType: string }>());
 	readonly onDidChangeItemsProviders = this._onDidChangeItemsProviders.event;
 
-	private readonly _onDidChangeSessionItems = this._register(new Emitter<{ readonly chatSessionType: string }>());
+	private readonly _onDidChangeSessionItems = this._register(new Emitter<IChatSessionItemsDelta>());
 	readonly onDidChangeSessionItems = this._onDidChangeSessionItems.event;
 
 	private readonly _onDidChangeAvailability = this._register(new Emitter<void>());
@@ -292,13 +299,10 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 
 	private readonly inProgressMap: Map<string, number> = new Map();
 	private readonly _sessionTypeOptions: Map<string, IChatSessionProviderOptionGroup[]> = new Map();
-	private readonly _sessionTypeIcons: Map<string, ThemeIcon | { light: URI; dark: URI }> = new Map();
-	private readonly _sessionTypeWelcomeTitles: Map<string, string> = new Map();
-	private readonly _sessionTypeWelcomeMessages: Map<string, string> = new Map();
-	private readonly _sessionTypeWelcomeTips: Map<string, string> = new Map();
-	private readonly _sessionTypeInputPlaceholders: Map<string, string> = new Map();
+	private readonly _sessionTypeNewSessionOptions: Map<string, Record<string, string | IChatSessionProviderOptionItem>> = new Map();
 
 	private readonly _sessions = new ResourceMap<ContributedChatSessionData>();
+	private readonly _resourceAliases = new ResourceMap<URI>(); // real resource -> untitled resource
 
 	private readonly _hasCanDelegateProvidersKey: IContextKey<boolean>;
 
@@ -341,7 +345,6 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 		).recomputeInitiallyAndOnChange(this._store);
 
 		this._register(autorun(reader => {
-			backgroundAgentDisplayName.read(reader);
 			const activatedProviders = [...builtinSessionProviders, ...contributedSessionProviders.read(reader)];
 			for (const provider of Object.values(AgentSessionProviders)) {
 				if (activatedProviders.includes(provider)) {
@@ -350,10 +353,21 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 			}
 		}));
 
-		this._register(this.onDidChangeSessionItems(({ chatSessionType }) => {
-			this.updateInProgressStatus(chatSessionType).catch(error => {
-				this._logService.warn(`Failed to update progress status for '${chatSessionType}':`, error);
-			});
+		this._register(this.onDidChangeSessionItems((delta) => {
+			const changedChatSessionTypes = new Set<string>();
+			for (const session of delta.addedOrUpdated ?? []) {
+				changedChatSessionTypes.add(getChatSessionType(session.resource));
+			}
+
+			for (const resource of delta.removed ?? []) {
+				changedChatSessionTypes.add(getChatSessionType(resource));
+			}
+
+			for (const chatSessionType of changedChatSessionTypes) {
+				this.updateInProgressStatus(chatSessionType).catch(error => {
+					this._logService.warn(`Failed to update progress status for '${chatSessionType}':`, error);
+				});
+			}
 		}));
 
 		this._register(this._labelService.registerFormatter({
@@ -391,8 +405,10 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 
 	private async updateInProgressStatus(chatSessionType: string): Promise<void> {
 		try {
-			const results = await this.getChatSessionItems([chatSessionType], CancellationToken.None);
-			const items = results.flatMap(r => r.items);
+			const items: IChatSessionItem[] = [];
+			for await (const result of this.getChatSessionItems([chatSessionType], CancellationToken.None)) {
+				items.push(...result.items);
+			}
 			const inProgress = items.filter(item => item.status && isSessionInProgressStatus(item.status));
 			this.reportInProgress(chatSessionType, inProgress.length);
 		} catch (error) {
@@ -401,8 +417,10 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 	}
 
 	private registerContribution(contribution: IChatSessionsExtensionPoint, ext: IRelaxedExtensionDescription): IDisposable {
+		this._logService.info(`[ChatSessionsService] registerContribution called for type='${contribution.type}', canDelegate=${contribution.canDelegate}, when='${contribution.when}', extension='${ext.identifier.value}'`);
 		if (this._contributions.has(contribution.type)) {
-			return { dispose: () => { } };
+			this._logService.info(`[ChatSessionsService] registerContribution: type='${contribution.type}' already registered, skipping`);
+			return Disposable.None;
 		}
 
 		// Track context keys from the when condition
@@ -427,41 +445,6 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 			}
 		}
 
-		// Store icon mapping if provided
-		let icon: ThemeIcon | { dark: URI; light: URI } | undefined;
-
-		if (contribution.icon) {
-			// Parse icon string - support ThemeIcon format or file path from extension
-			if (typeof contribution.icon === 'string') {
-				icon = contribution.icon.startsWith('$(') && contribution.icon.endsWith(')')
-					? ThemeIcon.fromString(contribution.icon)
-					: ThemeIcon.fromId(contribution.icon);
-			} else {
-				icon = {
-					dark: resources.joinPath(ext.extensionLocation, contribution.icon.dark),
-					light: resources.joinPath(ext.extensionLocation, contribution.icon.light)
-				};
-			}
-		}
-
-		if (icon) {
-			this._sessionTypeIcons.set(contribution.type, icon);
-		}
-
-		// Store welcome title, message, tips, and input placeholder if provided
-		if (contribution.welcomeTitle) {
-			this._sessionTypeWelcomeTitles.set(contribution.type, contribution.welcomeTitle);
-		}
-		if (contribution.welcomeMessage) {
-			this._sessionTypeWelcomeMessages.set(contribution.type, contribution.welcomeMessage);
-		}
-		if (contribution.welcomeTips) {
-			this._sessionTypeWelcomeTips.set(contribution.type, contribution.welcomeTips);
-		}
-		if (contribution.inputPlaceholder) {
-			this._sessionTypeInputPlaceholders.set(contribution.type, contribution.inputPlaceholder);
-		}
-
 		this._evaluateAvailability();
 
 		return {
@@ -475,11 +458,6 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 						}
 					}
 				}
-				this._sessionTypeIcons.delete(contribution.type);
-				this._sessionTypeWelcomeTitles.delete(contribution.type);
-				this._sessionTypeWelcomeMessages.delete(contribution.type);
-				this._sessionTypeWelcomeTips.delete(contribution.type);
-				this._sessionTypeInputPlaceholders.delete(contribution.type);
 				this._contributionDisposables.deleteAndDispose(contribution.type);
 				this._updateHasCanDelegateProvidersContextKey();
 			}
@@ -633,36 +611,46 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 	}
 
 	private _evaluateAvailability(): void {
-		let hasChanges = false;
+		const newlyEnabledChatSessionTypes = new Set<string>();
+		const newlyDisabledChatSessionTypes = new Set<string>();
+
+		const disposedChatSessions = new ResourceSet();
+
 		for (const { contribution, extension } of this._contributions.values()) {
 			const isCurrentlyRegistered = this._contributionDisposables.has(contribution.type);
 			const shouldBeRegistered = this._isContributionAvailable(contribution);
+			this._logService.trace(`[ChatSessionsService] _evaluateAvailability: type='${contribution.type}', isCurrentlyRegistered=${isCurrentlyRegistered}, shouldBeRegistered=${shouldBeRegistered}, when='${contribution.when}'`);
 			if (isCurrentlyRegistered && !shouldBeRegistered) {
 				// Disable the contribution by disposing its disposable store
 				this._contributionDisposables.deleteAndDispose(contribution.type);
 
 				// Also dispose any cached sessions for this contribution
-				this._disposeSessionsForContribution(contribution.type);
-				hasChanges = true;
+				for (const sessionResource of this._disposeSessionsForContribution(contribution.type)) {
+					disposedChatSessions.add(sessionResource);
+				}
+
+				newlyDisabledChatSessionTypes.add(contribution.type);
 			} else if (!isCurrentlyRegistered && shouldBeRegistered) {
 				// Enable the contribution by registering it
 				this._enableContribution(contribution, extension);
-				hasChanges = true;
+				newlyEnabledChatSessionTypes.add(contribution.type);
 			}
 		}
-		if (hasChanges) {
+		if (newlyEnabledChatSessionTypes.size > 0 || newlyDisabledChatSessionTypes.size > 0) {
 			this._onDidChangeAvailability.fire();
-			for (const chatSessionType of this._itemControllers.keys()) {
+			for (const chatSessionType of [...newlyEnabledChatSessionTypes, ...newlyDisabledChatSessionTypes]) {
 				this._onDidChangeItemsProviders.fire({ chatSessionType });
 			}
-			for (const { contribution } of this._contributions.values()) {
-				this._onDidChangeSessionItems.fire({ chatSessionType: contribution.type });
+
+			if (disposedChatSessions.size > 0) {
+				this._onDidChangeSessionItems.fire({ removed: Array.from(disposedChatSessions) });
 			}
 		}
 		this._updateHasCanDelegateProvidersContextKey();
 	}
 
 	private _enableContribution(contribution: IChatSessionsExtensionPoint, ext: IRelaxedExtensionDescription): void {
+		this._logService.info(`[ChatSessionsService] _enableContribution: type='${contribution.type}', canDelegate=${contribution.canDelegate}`);
 		const disposableStore = new DisposableStore();
 		this._contributionDisposables.set(contribution.type, disposableStore);
 		if (contribution.canDelegate) {
@@ -672,7 +660,12 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 		disposableStore.add(this._registerMenuItems(contribution, ext));
 	}
 
-	private _disposeSessionsForContribution(contributionId: string): void {
+	/**
+	 * Disposes of all sessions that belong to a contribution
+	 *
+	 * @returns List of session resources that were disposed.
+	 */
+	private _disposeSessionsForContribution(contributionId: string): URI[] {
 		// Find and dispose all sessions that belong to this contribution
 		const sessionsToDispose: URI[] = [];
 		for (const [sessionResource, sessionData] of this._sessions) {
@@ -691,22 +684,23 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 				sessionData.dispose(); // This will call _onWillDisposeSession and clean up
 			}
 		}
+		return sessionsToDispose;
 	}
 
 	private _registerAgent(contribution: IChatSessionsExtensionPoint, ext: IRelaxedExtensionDescription): IDisposable {
-		const { type: id, name, displayName, description } = contribution;
-		const storedIcon = this._sessionTypeIcons.get(id);
+		const storedIcon = this.getContributionIcon(ext, contribution);
 		const icons = ThemeIcon.isThemeIcon(storedIcon)
 			? { themeIcon: storedIcon, icon: undefined, iconDark: undefined }
 			: storedIcon
 				? { icon: storedIcon.light, iconDark: storedIcon.dark }
 				: { themeIcon: Codicon.sendToRemoteAgent };
 
+		const id = contribution.type;
 		const agentData: IChatAgentData = {
 			id,
-			name,
-			fullName: displayName,
-			description: description,
+			name: contribution.name,
+			fullName: contribution.displayName,
+			description: contribution.description,
 			isDefault: false,
 			isCore: false,
 			isDynamic: true,
@@ -728,9 +722,10 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 		return this._chatAgentService.registerAgent(id, agentData);
 	}
 
-	getAllChatSessionContributions(): IChatSessionsExtensionPoint[] {
-		return Array.from(this._contributions.values(), x => x.contribution)
-			.filter(contribution => this._isContributionAvailable(contribution));
+	getAllChatSessionContributions(): ResolvedChatSessionsExtensionPoint[] {
+		return Array.from(this._contributions.values())
+			.filter(entry => this._isContributionAvailable(entry.contribution))
+			.map(entry => this.resolveChatSessionContribution(entry.extension, entry.contribution));
 	}
 
 	private _updateHasCanDelegateProvidersContextKey(): void {
@@ -740,15 +735,56 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 		this._hasCanDelegateProvidersKey.set(canDelegateEnabled);
 	}
 
-	getChatSessionContribution(chatSessionType: string): IChatSessionsExtensionPoint | undefined {
-		const contribution = this._contributions.get(chatSessionType)?.contribution;
-		if (!contribution) {
+	getChatSessionContribution(chatSessionType: string): ResolvedChatSessionsExtensionPoint | undefined {
+		const entry = this._contributions.get(chatSessionType);
+		if (!entry) {
+			return undefined;
+		}
+
+		if (!this._isContributionAvailable(entry.contribution)) {
+			return undefined;
+		}
+
+		return this.resolveChatSessionContribution(entry.extension, entry.contribution);
+	}
+
+	private resolveChatSessionContribution(ext: IRelaxedExtensionDescription, contribution: IChatSessionsExtensionPoint) {
+		return {
+			...contribution,
+			icon: this.resolveIconForCurrentColorTheme(this.getContributionIcon(ext, contribution)),
+		};
+	}
+
+	private getContributionIcon(ext: IRelaxedExtensionDescription, contribution: IChatSessionsExtensionPoint): ThemeIcon | { light: URI; dark: URI } | undefined {
+		if (!contribution.icon) {
+			return undefined;
+		}
+		if (typeof contribution.icon === 'string') {
+			return contribution.icon.startsWith('$(') && contribution.icon.endsWith(')')
+				? ThemeIcon.fromString(contribution.icon)
+				: ThemeIcon.fromId(contribution.icon);
+		}
+		return {
+			dark: resources.joinPath(ext.extensionLocation, contribution.icon.dark),
+			light: resources.joinPath(ext.extensionLocation, contribution.icon.light)
+		};
+	}
+
+	private resolveIconForCurrentColorTheme(rawIcon: ThemeIcon | { light: URI; dark: URI } | undefined) {
+		if (!rawIcon) {
 			return undefined;
 		}
 
-		return this._isContributionAvailable(contribution) ? contribution : undefined;
+		if (ThemeIcon.isThemeIcon(rawIcon)) {
+			return rawIcon;
+		} else if (isDark(this._themeService.getColorTheme().type)) {
+			return rawIcon.dark;
+		} else {
+			return rawIcon.light;
+		}
 	}
 
+
 	async activateChatSessionItemProvider(chatViewType: string): Promise<void> {
 		await this.doActivateChatSessionItemController(chatViewType);
 	}
@@ -775,20 +811,20 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 		return !!controller;
 	}
 
-	async canResolveChatSession(chatSessionResource: URI) {
+	async canResolveChatSession(sessionType: string) {
 		await this._extensionService.whenInstalledExtensionsRegistered();
-		const resolvedType = this._resolveToPrimaryType(chatSessionResource.scheme) || chatSessionResource.scheme;
+		const resolvedType = this._resolveToPrimaryType(sessionType) || sessionType;
 		const contribution = this._contributions.get(resolvedType)?.contribution;
 		if (contribution && !this._isContributionAvailable(contribution)) {
 			return false;
 		}
 
-		if (this._contentProviders.has(chatSessionResource.scheme)) {
+		if (this._contentProviders.has(sessionType)) {
 			return true;
 		}
 
-		await this._extensionService.activateByEvent(`onChatSession:${chatSessionResource.scheme}`);
-		return this._contentProviders.has(chatSessionResource.scheme);
+		await this._extensionService.activateByEvent(`onChatSession:${sessionType}`);
+		return this._contentProviders.has(sessionType);
 	}
 
 	private async tryActivateControllers(providersToResolve: readonly string[] | undefined): Promise<void> {
@@ -806,33 +842,32 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 		}));
 	}
 
-	public async getChatSessionItems(providersToResolve: readonly string[] | undefined, token: CancellationToken): Promise<Array<{ readonly chatSessionType: string; readonly items: readonly IChatSessionItem[] }>> {
-		// First, make sure contributed controller are active
-		await this.tryActivateControllers(providersToResolve);
+	public getChatSessionItems(providersToResolve: readonly string[] | undefined, token: CancellationToken): AsyncIterable<{ readonly chatSessionType: string; readonly items: readonly IChatSessionItem[] }> {
+		return new AsyncIterableProducer(async writer => {
+			// First, make sure contributed controller are active
+			await raceCancellationError(this.tryActivateControllers(providersToResolve), token);
 
-		// Then actually resolve items for all active controllers
-		const results: Array<{ readonly chatSessionType: string; readonly items: readonly IChatSessionItem[] }> = [];
-		await Promise.all(Array.from(this._itemControllers).map(async ([chatSessionType, controllerEntry]) => {
-			const resolvedType = this._resolveToPrimaryType(chatSessionType) ?? chatSessionType;
-			if (providersToResolve && !providersToResolve.includes(resolvedType)) {
-				return; // skip: not considered for resolving
-			}
+			// Then actually resolve items for all active controllers
+			await Promise.all(Array.from(this._itemControllers, async ([chatSessionType, controllerEntry]) => {
+				const resolvedType = this._resolveToPrimaryType(chatSessionType) ?? chatSessionType;
+				if (providersToResolve && !providersToResolve.includes(resolvedType)) {
+					return; // skip: not considered for resolving
+				}
 
-			try {
-				await controllerEntry.initialRefresh; // Ensure initial refresh is complete before accessing items
+				try {
+					await raceCancellationError(controllerEntry.initialRefresh, token); // Ensure initial refresh is complete before accessing items
 
-				const providerSessions = controllerEntry.controller.items;
-				this._logService.trace(`[ChatSessionsService] Resolved ${providerSessions.length} sessions for provider ${resolvedType}`);
-				results.push({ chatSessionType: resolvedType, items: providerSessions });
-			} catch (err) {
-				if (!isCancellationError(err)) {
-					// Log error but continue with other providers
-					this._logService.error(`[ChatSessionsService] Failed to resolve sessions for provider ${resolvedType}`, err);
+					const providerSessions = controllerEntry.controller.items;
+					this._logService.trace(`[ChatSessionsService] Resolved ${providerSessions.length} sessions for provider ${resolvedType}`);
+					writer.emitOne({ chatSessionType: resolvedType, items: providerSessions });
+				} catch (err) {
+					if (!isCancellationError(err)) {
+						// Log error but continue with other providers
+						this._logService.error(`[ChatSessionsService] Failed to resolve sessions for provider ${resolvedType}`, err);
+					}
 				}
-			}
-		}));
-
-		return results;
+			}));
+		});
 	}
 
 	public async refreshChatSessionItems(providersToResolve: readonly string[] | undefined, token: CancellationToken): Promise<void> {
@@ -859,8 +894,8 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 		this._itemControllers.set(chatSessionType, { controller, initialRefresh: controller.refresh(initialRefreshCts.token) });
 		this._onDidChangeItemsProviders.fire({ chatSessionType });
 
-		disposables.add(controller.onDidChangeChatSessionItems(() => {
-			this._onDidChangeSessionItems.fire({ chatSessionType });
+		disposables.add(controller.onDidChangeChatSessionItems(e => {
+			this._onDidChangeSessionItems.fire(e);
 		}));
 
 		this.updateInProgressStatus(chatSessionType).catch(error => {
@@ -906,46 +941,6 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 		};
 	}
 
-	public registerChatModelChangeListeners(
-		chatService: IChatService,
-		chatSessionType: string,
-		onChange: () => void
-	): IDisposable {
-		const disposableStore = new DisposableStore();
-		const chatModelsICareAbout = chatService.chatModels.map(models =>
-			Array.from(models).filter((model: IChatModel) => model.sessionResource.scheme === chatSessionType)
-		);
-
-		const listeners = new ResourceMap<IDisposable>();
-		const autoRunDisposable = autorunIterableDelta(
-			reader => chatModelsICareAbout.read(reader),
-			({ addedValues, removedValues }) => {
-				removedValues.forEach((removed) => {
-					const listener = listeners.get(removed.sessionResource);
-					if (listener) {
-						listeners.delete(removed.sessionResource);
-						listener.dispose();
-					}
-				});
-				addedValues.forEach((added) => {
-					const requestChangeListener = added.lastRequestObs.map(last => last?.response && observableSignalFromEvent('chatSessions.modelRequestChangeListener', last.response.onDidChange));
-					const modelChangeListener = observableSignalFromEvent('chatSessions.modelChangeListener', added.onDidChange);
-					listeners.set(added.sessionResource, autorun(reader => {
-						requestChangeListener.read(reader)?.read(reader);
-						modelChangeListener.read(reader);
-						onChange();
-					}));
-				});
-			}
-		);
-		disposableStore.add(toDisposable(() => {
-			for (const listener of listeners.values()) { listener.dispose(); }
-		}));
-		disposableStore.add(autoRunDisposable);
-		return disposableStore;
-	}
-
-
 	public getInProgressSessionDescription(chatModel: IChatModel): string | undefined {
 		const requests = chatModel.getRequests();
 		if (requests.length === 0) {
@@ -1000,7 +995,7 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 		return description ? renderAsPlaintext(description, { useLinkFormatter: true }) : '';
 	}
 
-	async createNewChatSessionItem(chatSessionType: string, request: IChatAgentRequest, token: CancellationToken): Promise<IChatSessionItem | undefined> {
+	async createNewChatSessionItem(chatSessionType: string, request: IChatNewSessionRequest, token: CancellationToken): Promise<IChatSessionItem | undefined> {
 		const controllerData = this._itemControllers.get(chatSessionType);
 		if (!controllerData) {
 			return undefined;
@@ -1018,7 +1013,7 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 			}
 		}
 
-		if (!(await raceCancellationError(this.canResolveChatSession(sessionResource), token))) {
+		if (!(await raceCancellationError(this.canResolveChatSession(sessionResource.scheme), token))) {
 			throw Error(`Can not find provider for ${sessionResource}`);
 		}
 
@@ -1036,7 +1031,23 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 			throw Error(`Can not find provider for ${sessionResource}`);
 		}
 
-		const session = await raceCancellationError(provider.provideChatSessionContent(sessionResource, token), token);
+		let session: IChatSession;
+		const newSessionOptions = this.getNewSessionOptionsForSessionType(resolvedType);
+		if (isUntitledChatSession(sessionResource) && newSessionOptions) {
+			session = {
+				sessionResource: sessionResource,
+				onWillDispose: Event.None,
+				history: [],
+				options: newSessionOptions ?? {},
+				dispose: () => { }
+			};
+		} else {
+			session = await raceCancellationError(provider.provideChatSessionContent(sessionResource, token), token);
+		}
+
+		for (const [optionId, value] of Object.entries(session.options ?? {})) {
+			this.setSessionOption(sessionResource, optionId, value);
+		}
 
 		// Make sure another session wasn't created while we were awaiting the provider
 		{
@@ -1061,20 +1072,45 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 	}
 
 	public hasAnySessionOptions(sessionResource: URI): boolean {
-		const session = this._sessions.get(sessionResource);
+		const session = this._sessions.get(this._resolveResource(sessionResource));
 		return !!session && !!session.options && Object.keys(session.options).length > 0;
 	}
 
+	public getSessionOptions(sessionResource: URI): Map<string, string> | undefined {
+		const session = this._sessions.get(this._resolveResource(sessionResource));
+		if (!session) {
+			return undefined;
+		}
+		const result = new Map<string, string>();
+		for (const [key, value] of session.getAllOptions()) {
+			result.set(key, typeof value === 'string' ? value : value.id);
+		}
+		return result.size > 0 ? result : undefined;
+	}
+
 	public getSessionOption(sessionResource: URI, optionId: string): string | IChatSessionProviderOptionItem | undefined {
-		const session = this._sessions.get(sessionResource);
+		const session = this._sessions.get(this._resolveResource(sessionResource));
 		return session?.getOption(optionId);
 	}
 
 	public setSessionOption(sessionResource: URI, optionId: string, value: string | IChatSessionProviderOptionItem): boolean {
-		const session = this._sessions.get(sessionResource);
+		const session = this._sessions.get(this._resolveResource(sessionResource));
 		return !!session?.setOption(optionId, value);
 	}
 
+	/**
+	 * Resolve a resource through the alias map. If the resource is a real
+	 * resource that has been aliased to an untitled resource, return the
+	 * untitled resource (the canonical key in {@link _sessions}).
+	 */
+	private _resolveResource(resource: URI): URI {
+		return this._resourceAliases.get(resource) ?? resource;
+	}
+
+	public registerSessionResourceAlias(untitledResource: URI, realResource: URI): void {
+		this._resourceAliases.set(realResource, untitledResource);
+	}
+
 	/**
 	 * Store option groups for a session type
 	 */
@@ -1094,6 +1130,14 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 		return this._sessionTypeOptions.get(chatSessionType);
 	}
 
+	public getNewSessionOptionsForSessionType(chatSessionType: string): Record<string, string | IChatSessionProviderOptionItem> | undefined {
+		return this._sessionTypeNewSessionOptions.get(chatSessionType);
+	}
+
+	public setNewSessionOptionsForSessionType(chatSessionType: string, options: Record<string, string | IChatSessionProviderOptionItem>): void {
+		this._sessionTypeNewSessionOptions.set(chatSessionType, options);
+	}
+
 	/**
 	 * Notify extension about option changes for a session
 	 */
@@ -1109,48 +1153,10 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 		for (const u of updates) {
 			this.setSessionOption(sessionResource, u.optionId, u.value);
 		}
-		this._onDidChangeSessionOptions.fire(sessionResource);
+		this._onDidChangeSessionOptions.fire(this._resolveResource(sessionResource));
 		this._logService.trace(`[ChatSessionsService] notifySessionOptionsChange: finished for ${sessionResource}`);
 	}
 
-	/**
-	 * Get the icon for a specific session type
-	 */
-	public getIconForSessionType(chatSessionType: string): ThemeIcon | URI | undefined {
-		const sessionTypeIcon = this._sessionTypeIcons.get(chatSessionType);
-
-		if (ThemeIcon.isThemeIcon(sessionTypeIcon)) {
-			return sessionTypeIcon;
-		}
-
-		if (isDark(this._themeService.getColorTheme().type)) {
-			return sessionTypeIcon?.dark;
-		} else {
-			return sessionTypeIcon?.light;
-		}
-	}
-
-	/**
-	 * Get the welcome title for a specific session type
-	 */
-	public getWelcomeTitleForSessionType(chatSessionType: string): string | undefined {
-		return this._sessionTypeWelcomeTitles.get(chatSessionType);
-	}
-
-	/**
-	 * Get the welcome message for a specific session type
-	 */
-	public getWelcomeMessageForSessionType(chatSessionType: string): string | undefined {
-		return this._sessionTypeWelcomeMessages.get(chatSessionType);
-	}
-
-	/**
-	 * Get the input placeholder for a specific session type
-	 */
-	public getInputPlaceholderForSessionType(chatSessionType: string): string | undefined {
-		return this._sessionTypeInputPlaceholders.get(chatSessionType);
-	}
-
 	/**
 	 * Get the capabilities for a specific session type
 	 */
@@ -1180,6 +1186,8 @@ export class ChatSessionsService extends Disposable implements IChatSessionsServ
 
 registerSingleton(IChatSessionsService, ChatSessionsService, InstantiationType.Delayed);
 
+
+
 function registerNewSessionInPlaceAction(type: string, displayName: string): IDisposable {
 	return registerAction2(class NewChatSessionInPlaceAction extends Action2 {
 		constructor() {
@@ -1234,13 +1242,13 @@ export enum ChatSessionPosition {
 type NewChatSessionSendOptions = {
 	readonly prompt: string;
 	readonly attachedContext?: IChatRequestVariableEntry[];
+	readonly initialSessionOptions?: ReadonlyArray<{ optionId: string; value: string | { id: string; name: string } }>;
 };
 
 export type NewChatSessionOpenOptions = {
 	readonly type: string;
 	readonly position: ChatSessionPosition;
 	readonly displayName: string;
-	readonly chatResource?: UriComponents;
 	readonly replaceEditor?: boolean;
 };
 
@@ -1297,6 +1305,17 @@ async function openChatSession(accessor: ServicesAccessor, openOptions: NewChatS
 	// Send initial prompt if provided
 	if (chatSendOptions) {
 		try {
+			// Set initial session options on the model before sending the request,
+			// so that the contributed session provider can read them.
+			if (chatSendOptions.initialSessionOptions) {
+				const model = chatService.getSession(resource);
+				if (model?.contributedChatSession) {
+					model.setContributedChatSession({
+						...model.contributedChatSession,
+						initialSessionOptions: chatSendOptions.initialSessionOptions,
+					});
+				}
+			}
 			await chatService.sendRequest(resource, chatSendOptions.prompt, { agentIdSilent: openOptions.type, attachedContext: chatSendOptions.attachedContext });
 		} catch (e) {
 			logService.error(`Failed to send initial request to '${openOptions.type}' chat session with contextOptions: ${JSON.stringify(chatSendOptions)}`, e);
@@ -1305,10 +1324,6 @@ async function openChatSession(accessor: ServicesAccessor, openOptions: NewChatS
 }
 
 export function getResourceForNewChatSession(options: NewChatSessionOpenOptions): URI {
-	if (options.chatResource) {
-		return URI.revive(options.chatResource);
-	}
-
 	const isRemoteSession = options.type !== AgentSessionProviders.Local;
 	if (isRemoteSession) {
 		return URI.from({
@@ -1322,9 +1337,10 @@ export function getResourceForNewChatSession(options: NewChatSessionOpenOptions)
 		return ChatEditorInput.getNewEditorUri();
 	}
 
-	return LocalChatSessionUri.forSession(generateUuid());
+	return LocalChatSessionUri.getNewSessionUri();
 }
 
 function isAgentSessionProviderType(type: string): boolean {
 	return Object.values(AgentSessionProviders).includes(type as AgentSessionProviders);
 }
+
diff --git a/src/vs/workbench/contrib/chat/browser/chatSessions/searchableOptionPickerActionItem.ts b/src/vs/workbench/contrib/chat/browser/chatSessions/searchableOptionPickerActionItem.ts
index 9d22269371fe2..fd19654bcefdf 100644
--- a/src/vs/workbench/contrib/chat/browser/chatSessions/searchableOptionPickerActionItem.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatSessions/searchableOptionPickerActionItem.ts
@@ -22,6 +22,7 @@ import { ChatSessionPickerActionItem, IChatSessionPickerDelegate } from './chatS
 import { ILogService } from '../../../../../platform/log/common/log.js';
 import { ICommandService } from '../../../../../platform/commands/common/commands.js';
 import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
+import { IChatInputPickerOptions } from '../widget/input/chatInputPickerActionItem.js';
 
 interface ISearchableOptionQuickPickItem extends IQuickPickItem {
 	readonly optionItem: IChatSessionProviderOptionItem;
@@ -43,6 +44,7 @@ export class SearchableOptionPickerActionItem extends ChatSessionPickerActionIte
 		action: IAction,
 		initialState: { group: IChatSessionProviderOptionGroup; item: IChatSessionProviderOptionItem | undefined },
 		delegate: IChatSessionPickerDelegate,
+		pickerOptions: IChatInputPickerOptions | undefined,
 		@IActionWidgetService actionWidgetService: IActionWidgetService,
 		@IContextKeyService contextKeyService: IContextKeyService,
 		@IKeybindingService keybindingService: IKeybindingService,
@@ -51,7 +53,7 @@ export class SearchableOptionPickerActionItem extends ChatSessionPickerActionIte
 		@ICommandService commandService: ICommandService,
 		@ITelemetryService telemetryService: ITelemetryService,
 	) {
-		super(action, initialState, delegate, actionWidgetService, contextKeyService, keybindingService, commandService, telemetryService);
+		super(action, initialState, delegate, pickerOptions, actionWidgetService, contextKeyService, keybindingService, commandService, telemetryService);
 	}
 
 	protected override getDropdownActions(): IActionWidgetDropdownAction[] {
diff --git a/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupContributions.ts b/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupContributions.ts
index 587713e58b667..4a7157945ccd9 100644
--- a/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupContributions.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupContributions.ts
@@ -9,6 +9,7 @@ import { Lazy } from '../../../../../base/common/lazy.js';
 import { Disposable, DisposableStore, markAsSingleton, MutableDisposable } from '../../../../../base/common/lifecycle.js';
 import Severity from '../../../../../base/common/severity.js';
 import { equalsIgnoreCase } from '../../../../../base/common/strings.js';
+import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { ServicesAccessor } from '../../../../../editor/browser/editorExtensions.js';
 import { ICodeEditorService } from '../../../../../editor/browser/services/codeEditorService.js';
@@ -231,7 +232,7 @@ export class ChatSetupContribution extends Disposable implements IWorkbenchContr
 				});
 			}
 
-			override async run(accessor: ServicesAccessor, mode?: ChatModeKind | string, options?: { forceSignInDialog?: boolean; additionalScopes?: readonly string[]; forceAnonymous?: ChatSetupAnonymous; inputValue?: string }): Promise<boolean> {
+			override async run(accessor: ServicesAccessor, mode?: ChatModeKind | string, options?: { forceSignInDialog?: boolean; additionalScopes?: readonly string[]; forceAnonymous?: ChatSetupAnonymous; inputValue?: string; dialogIcon?: ThemeIcon; dialogTitle?: string; dialogHideSkip?: boolean }): Promise<boolean> {
 				const widgetService = accessor.get(IChatWidgetService);
 				const instantiationService = accessor.get(IInstantiationService);
 				const dialogService = accessor.get(IDialogService);
@@ -249,6 +250,7 @@ export class ChatSetupContribution extends Disposable implements IWorkbenchContr
 
 				if (options?.inputValue) {
 					const chatWidget = await widgetService.revealWidget();
+					chatWidget?.input.showScrollbarUntilAccept();
 					chatWidget?.setInput(options.inputValue);
 				}
 
@@ -279,7 +281,7 @@ export class ChatSetupContribution extends Disposable implements IWorkbenchContr
 				});
 			}
 
-			override async run(accessor: ServicesAccessor): Promise<unknown> {
+			override async run(accessor: ServicesAccessor, options?: { dialogIcon?: ThemeIcon; dialogTitle?: string; dialogHideSkip?: boolean }): Promise<unknown> {
 				const commandService = accessor.get(ICommandService);
 				const telemetryService = accessor.get(ITelemetryService);
 				const chatEntitlementService = accessor.get(IChatEntitlementService);
@@ -287,7 +289,8 @@ export class ChatSetupContribution extends Disposable implements IWorkbenchContr
 				telemetryService.publicLog2<WorkbenchActionExecutedEvent, WorkbenchActionExecutedClassification>('workbenchActionExecuted', { id: CHAT_SETUP_ACTION_ID, from: 'api' });
 
 				return commandService.executeCommand(CHAT_SETUP_ACTION_ID, undefined, {
-					forceAnonymous: chatEntitlementService.anonymous ? ChatSetupAnonymous.EnabledWithDialog : undefined
+					forceAnonymous: chatEntitlementService.anonymous ? ChatSetupAnonymous.EnabledWithDialog : undefined,
+					...options
 				});
 			}
 		}
@@ -465,9 +468,9 @@ export class ChatSetupContribution extends Disposable implements IWorkbenchContr
 
 		//#region Editor Context Menu
 
-		function registerGenerateCodeCommand(coreCommand: 'chat.internal.explain' | 'chat.internal.fix' | 'chat.internal.review', actualCommand: string): void {
+		function registerGenerateCodeCommand(coreCommand: 'chat.internal.explain' | 'chat.internal.fix' | 'chat.internal.review' | 'chat.internal.codeReview.run', actualCommand: string): void {
 
-			CommandsRegistry.registerCommand(coreCommand, async accessor => {
+			CommandsRegistry.registerCommand(coreCommand, async (accessor, ...args) => {
 				const commandService = accessor.get(ICommandService);
 				const codeEditorService = accessor.get(ICodeEditorService);
 				const markerService = accessor.get(IMarkerService);
@@ -497,6 +500,10 @@ export class ChatSetupContribution extends Disposable implements IWorkbenchContr
 						if (result) {
 							await commandService.executeCommand(actualCommand);
 						}
+						break;
+					}
+					case 'chat.internal.codeReview.run': {
+						return commandService.executeCommand(actualCommand, ...args);
 					}
 				}
 			});
@@ -504,6 +511,7 @@ export class ChatSetupContribution extends Disposable implements IWorkbenchContr
 		registerGenerateCodeCommand('chat.internal.explain', 'github.copilot.chat.explain');
 		registerGenerateCodeCommand('chat.internal.fix', 'github.copilot.chat.fix');
 		registerGenerateCodeCommand('chat.internal.review', 'github.copilot.chat.review');
+		registerGenerateCodeCommand('chat.internal.codeReview.run', 'github.copilot.chat.codeReview.run');
 
 		const internalGenerateCodeContext = ContextKeyExpr.and(
 			ChatContextKeys.Setup.hidden.negate(),
diff --git a/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupGrowthSession.ts b/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupGrowthSession.ts
index 1563924cdb3ea..1382c23832e5e 100644
--- a/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupGrowthSession.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupGrowthSession.ts
@@ -14,7 +14,7 @@ import { ICommandService } from '../../../../../platform/commands/common/command
 import { ILogService } from '../../../../../platform/log/common/log.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../../platform/storage/common/storage.js';
 import { ILifecycleService, LifecyclePhase } from '../../../../services/lifecycle/common/lifecycle.js';
-import { ChatSessionStatus, IChatSessionItem, IChatSessionItemController, IChatSessionsService } from '../../common/chatSessionsService.js';
+import { ChatSessionStatus, IChatSessionItem, IChatSessionItemController, IChatSessionItemsDelta, IChatSessionsService } from '../../common/chatSessionsService.js';
 import { AgentSessionProviders } from '../agentSessions/agentSessions.js';
 import { IAgentSession } from '../agentSessions/agentSessionsModel.js';
 import { ISessionOpenerParticipant, ISessionOpenOptions, sessionOpenerRegistry } from '../agentSessions/agentSessionsOpener.js';
@@ -36,8 +36,8 @@ export class GrowthSessionController extends Disposable implements IChatSessionI
 
 	private static readonly SESSION_URI = URI.from({ scheme: AgentSessionProviders.Growth, path: '/growth-welcome' });
 
-	private readonly _onDidChangeChatSessionItems = this._register(new Emitter<void>());
-	readonly onDidChangeChatSessionItems: Event<void> = this._onDidChangeChatSessionItems.event;
+	private readonly _onDidChangeChatSessionItems = this._register(new Emitter<IChatSessionItemsDelta>());
+	readonly onDidChangeChatSessionItems = this._onDidChangeChatSessionItems.event;
 
 	private readonly _onDidDismiss = this._register(new Emitter<void>());
 	readonly onDidDismiss: Event<void> = this._onDidDismiss.event;
@@ -103,7 +103,9 @@ export class GrowthSessionController extends Disposable implements IChatSessionI
 		this.storageService.store(GrowthSessionController.STORAGE_KEY, true, StorageScope.APPLICATION, StorageTarget.USER);
 
 		// Fire change event first so that listeners (like the model) see empty items
-		this._onDidChangeChatSessionItems.fire();
+		this._onDidChangeChatSessionItems.fire({
+			removed: [GrowthSessionController.SESSION_URI],
+		});
 		// Then fire dismiss event which triggers unregistration of the controller.
 		this._onDidDismiss.fire();
 	}
diff --git a/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupProviders.ts b/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupProviders.ts
index 1ff128a1f679f..193681944b8fa 100644
--- a/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupProviders.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupProviders.ts
@@ -511,6 +511,9 @@ export class SetupAgent extends Disposable implements IChatAgentImplementation {
 							}
 						});
 					} else {
+						this.logService.warn(defaultChat.outputChannelId
+							? `[chat setup] No output channel found for id '${defaultChat.outputChannelId}' to show details about chat setup timeout. Please ensure the ${defaultChat.chatExtensionId} extension is activated.`
+							: '[chat setup] No output channel provided via product.json to show details about chat setup timeout.');
 						progress({
 							kind: 'command',
 							command: {
diff --git a/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupRunner.ts b/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupRunner.ts
index 8922f2cbf35d3..7e77a64f55ee3 100644
--- a/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupRunner.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatSetup/chatSetupRunner.ts
@@ -9,6 +9,7 @@ import { IButton } from '../../../../../base/browser/ui/button/button.js';
 import { Dialog, DialogContentsAlignment } from '../../../../../base/browser/ui/dialog/dialog.js';
 import { coalesce } from '../../../../../base/common/arrays.js';
 import { Codicon } from '../../../../../base/common/codicons.js';
+import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { toErrorMessage } from '../../../../../base/common/errorMessage.js';
 import { MarkdownString } from '../../../../../base/common/htmlContent.js';
 import { Lazy } from '../../../../../base/common/lazy.js';
@@ -81,7 +82,7 @@ export class ChatSetup {
 		this.skipDialogOnce = true;
 	}
 
-	async run(options?: { disableChatViewReveal?: boolean; forceSignInDialog?: boolean; additionalScopes?: readonly string[]; forceAnonymous?: ChatSetupAnonymous }): Promise<IChatSetupResult> {
+	async run(options?: { disableChatViewReveal?: boolean; forceSignInDialog?: boolean; additionalScopes?: readonly string[]; forceAnonymous?: ChatSetupAnonymous; dialogIcon?: ThemeIcon; dialogTitle?: string; dialogHideSkip?: boolean }): Promise<IChatSetupResult> {
 		if (this.pendingRun) {
 			return this.pendingRun;
 		}
@@ -95,7 +96,7 @@ export class ChatSetup {
 		}
 	}
 
-	private async doRun(options?: { disableChatViewReveal?: boolean; forceSignInDialog?: boolean; additionalScopes?: readonly string[]; forceAnonymous?: ChatSetupAnonymous }): Promise<IChatSetupResult> {
+	private async doRun(options?: { disableChatViewReveal?: boolean; forceSignInDialog?: boolean; additionalScopes?: readonly string[]; forceAnonymous?: ChatSetupAnonymous; dialogIcon?: ThemeIcon; dialogTitle?: string; dialogHideSkip?: boolean }): Promise<IChatSetupResult> {
 		this.context.update({ later: false });
 
 		const dialogSkipped = this.skipDialogOnce;
@@ -161,10 +162,10 @@ export class ChatSetup {
 		return { success, dialogSkipped };
 	}
 
-	private async showDialog(options?: { forceSignInDialog?: boolean; forceAnonymous?: ChatSetupAnonymous }): Promise<ChatSetupStrategy> {
+	private async showDialog(options?: { forceSignInDialog?: boolean; forceAnonymous?: ChatSetupAnonymous; dialogIcon?: ThemeIcon; dialogTitle?: string; dialogHideSkip?: boolean }): Promise<ChatSetupStrategy> {
 		const disposables = new DisposableStore();
 
-		const useCloseButton = await this.experimentService.getTreatment<boolean>('chatSetupDialogCloseButton');
+		const useCloseButton = options?.dialogHideSkip || await this.experimentService.getTreatment<boolean>('chatSetupDialogCloseButton');
 		const buttons = this.getButtons(options, useCloseButton);
 
 		const dialog = disposables.add(new Dialog(
@@ -175,7 +176,7 @@ export class ChatSetup {
 				type: 'none',
 				extraClasses: ['chat-setup-dialog'],
 				detail: ' ', // workaround allowing us to render the message in large
-				icon: Codicon.copilotLarge,
+				icon: options?.dialogIcon ?? Codicon.copilotLarge,
 				alignment: DialogContentsAlignment.Vertical,
 				cancelId: useCloseButton ? buttons.length : buttons.length - 1,
 				disableCloseButton: !useCloseButton,
@@ -231,7 +232,11 @@ export class ChatSetup {
 		return buttons;
 	}
 
-	private getDialogTitle(options?: { forceSignInDialog?: boolean; forceAnonymous?: ChatSetupAnonymous }): string {
+	private getDialogTitle(options?: { forceSignInDialog?: boolean; forceAnonymous?: ChatSetupAnonymous; dialogTitle?: string }): string {
+		if (options?.dialogTitle) {
+			return options.dialogTitle;
+		}
+
 		if (this.chatEntitlementService.anonymous) {
 			if (options?.forceAnonymous) {
 				return localize('startUsing', "Start using AI Features");
diff --git a/src/vs/workbench/contrib/chat/browser/chatSlashCommands.ts b/src/vs/workbench/contrib/chat/browser/chatSlashCommands.ts
index 7e1830cee3505..646aa86dc5a53 100644
--- a/src/vs/workbench/contrib/chat/browser/chatSlashCommands.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatSlashCommands.ts
@@ -10,25 +10,24 @@ import { URI } from '../../../../base/common/uri.js';
 import * as nls from '../../../../nls.js';
 import { ICommandService } from '../../../../platform/commands/common/commands.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
-import { IDialogService } from '../../../../platform/dialogs/common/dialogs.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
-import { INotificationService, Severity } from '../../../../platform/notification/common/notification.js';
-import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
 import { IChatAgentService } from '../common/participants/chatAgents.js';
 import { IChatSlashCommandService } from '../common/participants/chatSlashCommands.js';
 import { IChatService } from '../common/chatService/chatService.js';
-import { ChatAgentLocation, ChatConfiguration, ChatModeKind } from '../common/constants.js';
+import { ChatAgentLocation, ChatConfiguration, ChatModeKind, ChatPermissionLevel } from '../common/constants.js';
 import { ACTION_ID_NEW_CHAT } from './actions/chatActions.js';
 import { ChatSubmitAction, OpenModePickerAction, OpenModelPickerAction } from './actions/chatExecuteActions.js';
+import { ManagePluginsAction } from './actions/chatPluginActions.js';
 import { ConfigureToolsAction } from './actions/chatToolActions.js';
 import { IAgentSessionsService } from './agentSessions/agentSessionsService.js';
-import { IChatWidgetService } from './chat.js';
 import { CONFIGURE_INSTRUCTIONS_ACTION_ID } from './promptSyntax/attachInstructionsAction.js';
 import { showConfigureHooksQuickPick } from './promptSyntax/hookActions.js';
 import { CONFIGURE_PROMPTS_ACTION_ID } from './promptSyntax/runPromptAction.js';
 import { CONFIGURE_SKILLS_ACTION_ID } from './promptSyntax/skillActions.js';
-import { globalAutoApproveDescription } from './tools/languageModelToolsService.js';
+import { IChatWidgetService } from './chat.js';
 import { agentSlashCommandToMarkdown, agentToMarkdown } from './widget/chatContentParts/chatMarkdownDecorationsRenderer.js';
+import { Target } from '../common/promptSyntax/promptTypes.js';
+import { IWorkbenchEnvironmentService } from '../../../services/environment/common/environmentService.js';
 
 export class ChatSlashCommandsContribution extends Disposable {
 
@@ -38,16 +37,15 @@ export class ChatSlashCommandsContribution extends Disposable {
 		@IChatSlashCommandService slashCommandService: IChatSlashCommandService,
 		@ICommandService commandService: ICommandService,
 		@IChatAgentService chatAgentService: IChatAgentService,
-		@IChatWidgetService chatWidgetService: IChatWidgetService,
 		@IInstantiationService instantiationService: IInstantiationService,
 		@IAgentSessionsService agentSessionsService: IAgentSessionsService,
 		@IChatService chatService: IChatService,
 		@IConfigurationService configurationService: IConfigurationService,
-		@IDialogService dialogService: IDialogService,
-		@INotificationService notificationService: INotificationService,
-		@IStorageService storageService: IStorageService,
+		@IChatWidgetService chatWidgetService: IChatWidgetService,
+		@IWorkbenchEnvironmentService private readonly environmentService: IWorkbenchEnvironmentService,
 	) {
 		super();
+
 		this._store.add(slashCommandService.registerSlashCommand({
 			command: 'clear',
 			detail: nls.localize('clear', "Start a new chat and archive the current one"),
@@ -64,7 +62,8 @@ export class ChatSlashCommandsContribution extends Disposable {
 			sortText: 'z3_hooks',
 			executeImmediately: true,
 			silent: true,
-			locations: [ChatAgentLocation.Chat]
+			locations: [ChatAgentLocation.Chat],
+			target: Target.VSCode
 		}, async () => {
 			await instantiationService.invokeFunction(showConfigureHooksQuickPick);
 		}));
@@ -74,7 +73,8 @@ export class ChatSlashCommandsContribution extends Disposable {
 			sortText: 'z3_models',
 			executeImmediately: true,
 			silent: true,
-			locations: [ChatAgentLocation.Chat]
+			locations: [ChatAgentLocation.Chat],
+			target: Target.VSCode
 		}, async () => {
 			await commandService.executeCommand(OpenModelPickerAction.ID);
 		}));
@@ -84,27 +84,42 @@ export class ChatSlashCommandsContribution extends Disposable {
 			sortText: 'z3_tools',
 			executeImmediately: true,
 			silent: true,
-			locations: [ChatAgentLocation.Chat]
+			locations: [ChatAgentLocation.Chat],
+			target: Target.VSCode
 		}, async () => {
 			await commandService.executeCommand(ConfigureToolsAction.ID);
 		}));
 		this._store.add(slashCommandService.registerSlashCommand({
-			command: 'debug',
-			detail: nls.localize('debug', "Show Chat Debug View"),
-			sortText: 'z3_debug',
+			command: 'plugins',
+			detail: nls.localize('plugins', "Manage plugins"),
+			sortText: 'z3_plugins',
 			executeImmediately: true,
 			silent: true,
-			locations: [ChatAgentLocation.Chat]
+			locations: [ChatAgentLocation.Chat],
+			target: Target.VSCode
 		}, async () => {
-			await commandService.executeCommand('github.copilot.debug.showChatLogView');
+			await commandService.executeCommand(ManagePluginsAction.ID);
 		}));
+		if (!this.environmentService.isSessionsWindow) {
+			this._store.add(slashCommandService.registerSlashCommand({
+				command: 'debug',
+				detail: nls.localize('debug', "Show Chat Debug View"),
+				sortText: 'z3_debug',
+				executeImmediately: true,
+				silent: true,
+				locations: [ChatAgentLocation.Chat],
+			}, async () => {
+				await commandService.executeCommand('github.copilot.debug.showChatLogView');
+			}));
+		}
 		this._store.add(slashCommandService.registerSlashCommand({
 			command: 'agents',
 			detail: nls.localize('agents', "Configure custom agents"),
 			sortText: 'z3_agents',
 			executeImmediately: true,
 			silent: true,
-			locations: [ChatAgentLocation.Chat]
+			locations: [ChatAgentLocation.Chat],
+			target: Target.VSCode
 		}, async () => {
 			await commandService.executeCommand(OpenModePickerAction.ID);
 		}));
@@ -114,7 +129,8 @@ export class ChatSlashCommandsContribution extends Disposable {
 			sortText: 'z3_skills',
 			executeImmediately: true,
 			silent: true,
-			locations: [ChatAgentLocation.Chat]
+			locations: [ChatAgentLocation.Chat],
+			target: Target.VSCode
 		}, async () => {
 			await commandService.executeCommand(CONFIGURE_SKILLS_ACTION_ID);
 		}));
@@ -124,7 +140,8 @@ export class ChatSlashCommandsContribution extends Disposable {
 			sortText: 'z3_instructions',
 			executeImmediately: true,
 			silent: true,
-			locations: [ChatAgentLocation.Chat]
+			locations: [ChatAgentLocation.Chat],
+			target: Target.VSCode
 		}, async () => {
 			await commandService.executeCommand(CONFIGURE_INSTRUCTIONS_ACTION_ID);
 		}));
@@ -134,7 +151,8 @@ export class ChatSlashCommandsContribution extends Disposable {
 			sortText: 'z3_prompts',
 			executeImmediately: true,
 			silent: true,
-			locations: [ChatAgentLocation.Chat]
+			locations: [ChatAgentLocation.Chat],
+			target: Target.VSCode
 		}, async () => {
 			await commandService.executeCommand(CONFIGURE_PROMPTS_ACTION_ID);
 		}));
@@ -144,7 +162,8 @@ export class ChatSlashCommandsContribution extends Disposable {
 			sortText: 'z2_fork',
 			executeImmediately: true,
 			silent: true,
-			locations: [ChatAgentLocation.Chat]
+			locations: [ChatAgentLocation.Chat],
+			target: Target.VSCode
 		}, async (_prompt, _progress, _history, _location, sessionResource) => {
 			await commandService.executeCommand('workbench.action.chat.forkConversation', sessionResource);
 		}));
@@ -154,80 +173,93 @@ export class ChatSlashCommandsContribution extends Disposable {
 			sortText: 'z2_rename',
 			executeImmediately: false,
 			silent: true,
-			locations: [ChatAgentLocation.Chat]
+			locations: [ChatAgentLocation.Chat],
+			target: Target.VSCode
 		}, async (prompt, _progress, _history, _location, sessionResource) => {
 			const title = prompt.trim();
 			if (title) {
 				chatService.setChatSessionTitle(sessionResource, title);
 			}
 		}));
-		const enableAutoApprove = async (): Promise<boolean> => {
-			const alreadyOptedIn = storageService.getBoolean('chat.tools.global.autoApprove.optIn', StorageScope.APPLICATION, false);
-			if (!alreadyOptedIn) {
-				const result = await dialogService.prompt({
-					type: Severity.Warning,
-					message: nls.localize('autoApprove.enable.title', 'Enable global auto approve?'),
-					buttons: [
-						{ label: nls.localize('autoApprove.enable.button', 'Enable'), run: () => true },
-						{ label: nls.localize('autoApprove.cancel.button', 'Cancel'), run: () => false },
-					],
-					custom: {
-						disableCloseAction: true,
-						markdownDetails: [{ markdown: new MarkdownString(globalAutoApproveDescription.value) }],
-					}
-				});
-				if (result.result !== true) {
-					return false;
-				}
-				storageService.store('chat.tools.global.autoApprove.optIn', true, StorageScope.APPLICATION, StorageTarget.USER);
+		const setPermissionLevelForSession = (sessionResource: URI, level: ChatPermissionLevel) => {
+			const widget = chatWidgetService.getWidgetBySessionResource(sessionResource) ?? chatWidgetService.lastFocusedWidget;
+			if (widget) {
+				widget.input.setPermissionLevel(level);
 			}
-			await configurationService.updateValue(ChatConfiguration.GlobalAutoApprove, true);
-			return true;
 		};
-		const handleAutoApprove = async (prompt: string, _progress: unknown, _history: unknown, _location: unknown, sessionResource: URI) => {
-			const trimmed = prompt.trim();
-			if (trimmed) {
-				// /autoApprove <request> — prompt to enable, then submit the request
-				if (await enableAutoApprove()) {
-					const widget = chatWidgetService.getWidgetBySessionResource(sessionResource);
-					if (widget) {
-						widget.acceptInput(trimmed);
-					}
-				}
-			} else {
-				// /autoApprove — toggle
-				const isEnabled = configurationService.getValue<boolean>(ChatConfiguration.GlobalAutoApprove);
-				if (isEnabled) {
-					await configurationService.updateValue(ChatConfiguration.GlobalAutoApprove, false);
-					notificationService.info(nls.localize('autoApprove.disabled', "Global auto-approve disabled — tools will require approval"));
-				} else {
-					await enableAutoApprove();
-				}
+		const autoApprovePolicyValue = configurationService.inspect<boolean>(ChatConfiguration.GlobalAutoApprove).policyValue;
+		if (autoApprovePolicyValue !== false) {
+			this._store.add(slashCommandService.registerSlashCommand({
+				command: 'autoApprove',
+				detail: nls.localize('autoApprove', "Set permissions to bypass approvals"),
+				sortText: 'z1_autoApprove',
+				executeImmediately: true,
+				silent: true,
+				locations: [ChatAgentLocation.Chat]
+			}, async (_prompt, _progress, _history, _location, sessionResource) => {
+				setPermissionLevelForSession(sessionResource, ChatPermissionLevel.AutoApprove);
+			}));
+			this._store.add(slashCommandService.registerSlashCommand({
+				command: 'disableAutoApprove',
+				detail: nls.localize('disableAutoApprove', "Set permissions back to default"),
+				sortText: 'z1_disableAutoApprove',
+				executeImmediately: true,
+				silent: true,
+				locations: [ChatAgentLocation.Chat]
+			}, async (_prompt, _progress, _history, _location, sessionResource) => {
+				setPermissionLevelForSession(sessionResource, ChatPermissionLevel.Default);
+			}));
+			this._store.add(slashCommandService.registerSlashCommand({
+				command: 'yolo',
+				detail: nls.localize('yolo', "Set permissions to bypass approvals"),
+				sortText: 'z1_yolo',
+				executeImmediately: true,
+				silent: true,
+				locations: [ChatAgentLocation.Chat]
+			}, async (_prompt, _progress, _history, _location, sessionResource) => {
+				setPermissionLevelForSession(sessionResource, ChatPermissionLevel.AutoApprove);
+			}));
+			this._store.add(slashCommandService.registerSlashCommand({
+				command: 'disableYolo',
+				detail: nls.localize('disableYolo', "Set permissions back to default"),
+				sortText: 'z1_disableYolo',
+				executeImmediately: true,
+				silent: true,
+				locations: [ChatAgentLocation.Chat]
+			}, async (_prompt, _progress, _history, _location, sessionResource) => {
+				setPermissionLevelForSession(sessionResource, ChatPermissionLevel.Default);
+			}));
+			if (configurationService.getValue<boolean>(ChatConfiguration.AutopilotEnabled) !== false) {
+				this._store.add(slashCommandService.registerSlashCommand({
+					command: 'autopilot',
+					detail: nls.localize('autopilot', "Set permissions to autopilot mode"),
+					sortText: 'z1_autopilot',
+					executeImmediately: true,
+					silent: true,
+					locations: [ChatAgentLocation.Chat]
+				}, async (_prompt, _progress, _history, _location, sessionResource) => {
+					setPermissionLevelForSession(sessionResource, ChatPermissionLevel.Autopilot);
+				}));
+				this._store.add(slashCommandService.registerSlashCommand({
+					command: 'exitAutopilot',
+					detail: nls.localize('exitAutopilot', "Set permissions back to default"),
+					sortText: 'z1_exitAutopilot',
+					executeImmediately: true,
+					silent: true,
+					locations: [ChatAgentLocation.Chat]
+				}, async (_prompt, _progress, _history, _location, sessionResource) => {
+					setPermissionLevelForSession(sessionResource, ChatPermissionLevel.Default);
+				}));
 			}
-		};
-		this._store.add(slashCommandService.registerSlashCommand({
-			command: 'autoApprove',
-			detail: nls.localize('autoApprove', "Toggle global auto-approval of all tool calls"),
-			sortText: 'z1_autoApprove',
-			executeImmediately: false,
-			silent: true,
-			locations: [ChatAgentLocation.Chat]
-		}, handleAutoApprove));
-		this._store.add(slashCommandService.registerSlashCommand({
-			command: 'yolo',
-			detail: nls.localize('yolo', "Toggle global auto-approval of all tool calls"),
-			sortText: 'z1_yolo',
-			executeImmediately: false,
-			silent: true,
-			locations: [ChatAgentLocation.Chat]
-		}, handleAutoApprove));
+		}
 		this._store.add(slashCommandService.registerSlashCommand({
 			command: 'help',
 			detail: '',
 			sortText: 'z1_help',
 			executeImmediately: true,
 			locations: [ChatAgentLocation.Chat],
-			modes: [ChatModeKind.Ask]
+			modes: [ChatModeKind.Ask],
+			target: Target.VSCode
 		}, async (prompt, progress, _history, _location, sessionResource) => {
 			const defaultAgent = chatAgentService.getDefaultAgent(ChatAgentLocation.Chat);
 			const agents = chatAgentService.getAgents();
diff --git a/src/vs/workbench/contrib/chat/browser/chatStatus/chatStatusDashboard.ts b/src/vs/workbench/contrib/chat/browser/chatStatus/chatStatusDashboard.ts
index 4cc80cb99f8a5..ad2cb70765e27 100644
--- a/src/vs/workbench/contrib/chat/browser/chatStatus/chatStatusDashboard.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatStatus/chatStatusDashboard.ts
@@ -179,7 +179,8 @@ export class ChatStatusDashboard extends DomWidget {
 
 			const completionsQuotaIndicator = completionsQuota && (completionsQuota.total > 0 || completionsQuota.unlimited) ? this.createQuotaIndicator(this.element, this._store, completionsQuota, localize('completionsLabel', "Inline Suggestions"), false) : undefined;
 			const chatQuotaIndicator = chatQuota && (chatQuota.total > 0 || chatQuota.unlimited) ? this.createQuotaIndicator(this.element, this._store, chatQuota, localize('chatsLabel', "Chat messages"), false) : undefined;
-			const premiumChatQuotaIndicator = premiumChatQuota && (premiumChatQuota.total > 0 || premiumChatQuota.unlimited) ? this.createQuotaIndicator(this.element, this._store, premiumChatQuota, localize('premiumChatsLabel', "Premium requests"), true) : undefined;
+			const premiumChatLabel = premiumChatQuota?.overageEnabled && !premiumChatQuota?.unlimited ? localize('includedPremiumChatsLabel', "Included premium requests") : localize('premiumChatsLabel', "Premium requests");
+			const premiumChatQuotaIndicator = premiumChatQuota && (premiumChatQuota.total > 0 || premiumChatQuota.unlimited) ? this.createQuotaIndicator(this.element, this._store, premiumChatQuota, premiumChatLabel, true) : undefined;
 
 			if (resetDate) {
 				this.element.appendChild($('div.description', undefined, localize('limitQuota', "Allowance resets {0}.", resetDateHasTime ? this.dateTimeFormatter.value.format(new Date(resetDate)) : this.dateFormatter.value.format(new Date(resetDate)))));
@@ -528,15 +529,22 @@ export class ChatStatusDashboard extends DomWidget {
 
 			quotaBit.style.width = `${usedPercentage}%`;
 
-			if (usedPercentage >= 90) {
+			const overageEnabled = supportsOverage && typeof quota !== 'string' && quota?.overageEnabled;
+			if (usedPercentage >= 90 && !overageEnabled) {
 				quotaIndicator.classList.add('error');
-			} else if (usedPercentage >= 75) {
+			} else if (usedPercentage >= 75 && !overageEnabled) {
 				quotaIndicator.classList.add('warning');
 			}
 
 			if (supportsOverage) {
-				if (typeof quota !== 'string' && quota?.overageEnabled) {
-					overageLabel.textContent = localize('additionalUsageEnabled', "Additional paid premium requests enabled.");
+				if (typeof quota !== 'string' && quota.unlimited) {
+					overageLabel.textContent = '';
+				} else if (typeof quota !== 'string' && quota?.overageEnabled) {
+					overageLabel.replaceChildren(
+						localize('additionalUsageApprovedLine1', "Additional premium requests approved."),
+						$('br'),
+						localize('additionalUsageApprovedLine2', "You can continue after the included premium requests limit reaches 100%.")
+					);
 				} else {
 					overageLabel.textContent = localize('additionalUsageDisabled', "Additional paid premium requests disabled.");
 				}
diff --git a/src/vs/workbench/contrib/chat/browser/chatTipCatalog.ts b/src/vs/workbench/contrib/chat/browser/chatTipCatalog.ts
new file mode 100644
index 0000000000000..ceb7f5b720336
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/chatTipCatalog.ts
@@ -0,0 +1,394 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { MarkdownString } from '../../../../base/common/htmlContent.js';
+import { localize } from '../../../../nls.js';
+import { ContextKeyExpr, ContextKeyExpression } from '../../../../platform/contextkey/common/contextkey.js';
+import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
+import { MenuRegistry } from '../../../../platform/actions/common/actions.js';
+import { ChatContextKeys } from '../common/actions/chatContextKeys.js';
+import { ChatConfiguration, ChatModeKind } from '../common/constants.js';
+import { localChatSessionType } from '../common/chatSessionsService.js';
+import { ITipExclusionConfig } from './chatTipEligibilityTracker.js';
+import { TipTrackingCommands } from './chatTipStorageKeys.js';
+import {
+	GENERATE_AGENT_COMMAND_ID,
+	GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID,
+	GENERATE_PROMPT_COMMAND_ID,
+	GENERATE_SKILL_COMMAND_ID,
+	INSERT_FORK_CONVERSATION_COMMAND_ID,
+	INSERT_TROUBLESHOOT_COMMAND_ID,
+} from './actions/chatActions.js';
+
+export const enum ChatTipTier {
+	Foundational = 'foundational',
+	Qol = 'qol',
+}
+
+/**
+ * Context provided to tip builders for dynamic message construction.
+ */
+export interface ITipBuildContext {
+	/**
+	 * Keybinding service for looking up keyboard shortcuts.
+	 */
+	readonly keybindingService: IKeybindingService;
+}
+
+/**
+ * Gets the display label for a command, looking it up from MenuRegistry.
+ * Falls back to extracting a readable name from the command ID.
+ */
+export function getCommandLabel(commandId: string): string {
+	const command = MenuRegistry.getCommand(commandId);
+	if (command?.title) {
+		// Handle both string and ILocalizedString formats
+		return typeof command.title === 'string' ? command.title : command.title.value;
+	}
+	// Fallback: extract readable name from command ID
+	// e.g., 'workbench.action.chat.openEditSession' -> 'openEditSession'
+	const parts = commandId.split('.');
+	return parts[parts.length - 1];
+}
+
+/**
+ * Formats a keybinding for display in a tip message.
+ * Returns empty string if no keybinding is bound.
+ */
+function formatKeybinding(ctx: ITipBuildContext, commandId: string): string {
+	const kb = ctx.keybindingService.lookupKeybinding(commandId);
+	return kb ? ` (${kb.getLabel()})` : '';
+}
+
+/**
+ * Extracts command IDs from command: links in a markdown string.
+ * Used to automatically populate enabledCommands for trusted markdown.
+ */
+export function extractCommandIds(markdown: string): string[] {
+	const commandPattern = /\[.*?\]\(command:([^?\s)]+)/g;
+	const commands = new Set<string>();
+	let match;
+	while ((match = commandPattern.exec(markdown)) !== null) {
+		commands.add(match[1]);
+	}
+	return [...commands];
+}
+
+/**
+ * Interface for tip definitions in the catalog.
+ */
+export interface ITipDefinition extends ITipExclusionConfig {
+	readonly id: string;
+	readonly tier: ChatTipTier;
+	/**
+	 * Optional priority for ordering tips within the same tier.
+	 * Lower values are shown first.
+	 */
+	readonly priority?: number;
+	/**
+	 * Builds the tip message dynamically at runtime.
+	 * This enables keybindings and command labels to be looked up fresh.
+	 * The returned MarkdownString should NOT include the "Tip:" prefix.
+	 */
+	buildMessage(ctx: ITipBuildContext): MarkdownString;
+	/**
+	 * When clause expression that determines if this tip is eligible to be shown.
+	 */
+	readonly when?: ContextKeyExpression;
+	/**
+	 * Chat model IDs for which this tip is eligible (lowercase).
+	 */
+	readonly onlyWhenModelIds?: readonly string[];
+	/**
+	 * Setting keys that, if changed from default, make this tip ineligible.
+	 */
+	readonly excludeWhenSettingsChanged?: readonly string[];
+	/**
+	 * Command IDs that dismiss this tip when clicked from the tip markdown.
+	 */
+	readonly dismissWhenCommandsClicked?: readonly string[];
+}
+
+// -----------------------------------------------------------------------------
+// Tip Catalog
+// -----------------------------------------------------------------------------
+
+/**
+ * Static catalog of tips. Tips are built dynamically at runtime to enable
+ * keybindings and command labels to be resolved fresh.
+ */
+export const TIP_CATALOG: readonly ITipDefinition[] = [
+	{
+		id: 'tip.switchToAuto',
+		tier: ChatTipTier.Foundational,
+		priority: 0,
+		buildMessage(_ctx) {
+			return new MarkdownString(
+				localize(
+					'tip.switchToAuto',
+					"Using GPT-4.1? Try switching to [Auto](command:workbench.action.chat.openModelPicker \"Open Model Picker\") in the model picker for better coding performance."
+				)
+			);
+		},
+		onlyWhenModelIds: ['gpt-4.1'],
+	},
+	{
+		id: 'tip.init',
+		tier: ChatTipTier.Foundational,
+		priority: 50,
+		buildMessage(ctx) {
+			const kb = formatKeybinding(ctx, GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID);
+			return new MarkdownString(
+				localize(
+					'tip.init',
+					"Use [{0}](command:{1} \"Run /init\"){2} to generate or update a workspace instructions file for AI coding agents.",
+					'/init',
+					GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID,
+					kb
+				)
+			);
+		},
+		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+		excludeWhenCommandsExecuted: [
+			GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID,
+			TipTrackingCommands.CreateAgentInstructionsUsed,
+		],
+	},
+	{
+		id: 'tip.createPrompt',
+		tier: ChatTipTier.Foundational,
+		buildMessage(ctx) {
+			const kb = formatKeybinding(ctx, GENERATE_PROMPT_COMMAND_ID);
+			return new MarkdownString(
+				localize(
+					'tip.createPrompt',
+					"Use [{0}](command:{1} \"Run /create-prompt\"){2} to generate a reusable prompt file with the agent.",
+					'/create-prompt',
+					GENERATE_PROMPT_COMMAND_ID,
+					kb
+				)
+			);
+		},
+		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+		excludeWhenCommandsExecuted: [
+			GENERATE_PROMPT_COMMAND_ID,
+			TipTrackingCommands.CreatePromptUsed,
+		],
+	},
+	{
+		id: 'tip.createAgent',
+		tier: ChatTipTier.Foundational,
+		priority: 30,
+		buildMessage(ctx) {
+			const kb = formatKeybinding(ctx, GENERATE_AGENT_COMMAND_ID);
+			return new MarkdownString(
+				localize(
+					'tip.createAgent',
+					"Use [{0}](command:{1} \"Run /create-agent\"){2} to scaffold a custom agent for your workflow.",
+					'/create-agent',
+					GENERATE_AGENT_COMMAND_ID,
+					kb
+				)
+			);
+		},
+		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+		excludeWhenCommandsExecuted: [
+			GENERATE_AGENT_COMMAND_ID,
+			TipTrackingCommands.CreateAgentUsed,
+		],
+	},
+	{
+		id: 'tip.createSkill',
+		tier: ChatTipTier.Foundational,
+		priority: 40,
+		buildMessage(ctx) {
+			const kb = formatKeybinding(ctx, GENERATE_SKILL_COMMAND_ID);
+			return new MarkdownString(
+				localize(
+					'tip.createSkill',
+					"Use [{0}](command:{1} \"Run /create-skill\"){2} to create a skill the agent can load when relevant.",
+					'/create-skill',
+					GENERATE_SKILL_COMMAND_ID,
+					kb
+				)
+			);
+		},
+		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+		excludeWhenCommandsExecuted: [
+			GENERATE_SKILL_COMMAND_ID,
+			TipTrackingCommands.CreateSkillUsed,
+		],
+	},
+	{
+		id: 'tip.planMode',
+		tier: ChatTipTier.Foundational,
+		priority: 20,
+		buildMessage(ctx) {
+			const kb = formatKeybinding(ctx, 'workbench.action.chat.openPlan');
+			return new MarkdownString(
+				localize(
+					'tip.planMode',
+					"Try the [{0}](command:workbench.action.chat.openPlan \"Start Plan Mode\"){1} to research and plan before implementing changes.",
+					'Plan agent',
+					kb
+				)
+			);
+		},
+		when: ChatContextKeys.chatModeName.notEqualsTo('Plan'),
+		excludeWhenCommandsExecuted: ['workbench.action.chat.openPlan'],
+		excludeWhenModesUsed: ['Plan'],
+	},
+	{
+		id: 'tip.attachFiles',
+		tier: ChatTipTier.Qol,
+		buildMessage() {
+			return new MarkdownString(
+				localize('tip.attachFiles', "Reference files or folders with # to give the agent more context about the task.")
+			);
+		},
+		excludeWhenCommandsExecuted: [
+			'workbench.action.chat.attachContext',
+			'workbench.action.chat.attachFile',
+			'workbench.action.chat.attachFolder',
+			'workbench.action.chat.attachSelection',
+			TipTrackingCommands.AttachFilesReferenceUsed,
+		],
+	},
+	{
+		id: 'tip.codeActions',
+		tier: ChatTipTier.Qol,
+		buildMessage() {
+			return new MarkdownString(
+				localize('tip.codeActions', "Select a code block in the editor and right-click to access more AI actions.")
+			);
+		},
+		excludeWhenCommandsExecuted: ['inlineChat.start'],
+	},
+	{
+		id: 'tip.undoChanges',
+		tier: ChatTipTier.Qol,
+		buildMessage() {
+			return new MarkdownString(
+				localize('tip.undoChanges', "Hover a previous request and select \"Restore Checkpoint\" to undo changes after that point in the chat conversation.")
+			);
+		},
+		when: ContextKeyExpr.and(
+			ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+			ContextKeyExpr.or(
+				ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+				ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Edit),
+			),
+		),
+		excludeWhenCommandsExecuted: ['workbench.action.chat.restoreCheckpoint', 'workbench.action.chat.restoreLastCheckpoint'],
+	},
+	{
+		id: 'tip.messageQueueing',
+		tier: ChatTipTier.Qol,
+		buildMessage() {
+			return new MarkdownString(
+				localize('tip.messageQueueing', "Steer the agent mid-task by sending follow-up messages. They queue and apply in order.")
+			);
+		},
+		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+		excludeWhenCommandsExecuted: ['workbench.action.chat.queueMessage', 'workbench.action.chat.steerWithMessage'],
+	},
+	{
+		id: 'tip.forkConversation',
+		tier: ChatTipTier.Qol,
+		buildMessage(ctx) {
+			const kb = formatKeybinding(ctx, INSERT_FORK_CONVERSATION_COMMAND_ID);
+			return new MarkdownString(
+				localize(
+					'tip.forkConversation',
+					"Use [{0}](command:{1} \"Run /fork\"){2} to branch the conversation. Explore a different approach without losing the original context.",
+					'/fork',
+					INSERT_FORK_CONVERSATION_COMMAND_ID,
+					kb
+				)
+			);
+		},
+		excludeWhenCommandsExecuted: [
+			INSERT_FORK_CONVERSATION_COMMAND_ID,
+			'workbench.action.chat.forkConversation',
+			TipTrackingCommands.ForkConversationUsed,
+		],
+	},
+	{
+		id: 'tip.agenticBrowser',
+		tier: ChatTipTier.Qol,
+		buildMessage() {
+			return new MarkdownString(
+				localize(
+					'tip.agenticBrowser',
+					"Enable [{0}](command:workbench.action.openSettings?%5B%22workbench.browser.enableChatTools%22%5D \"Open Settings\") to let the agent open and interact with pages in the Integrated Browser.",
+					'agentic browser integration'
+				)
+			);
+		},
+		when: ContextKeyExpr.and(
+			ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+			ContextKeyExpr.notEquals('config.workbench.browser.enableChatTools', true),
+		),
+		excludeWhenSettingsChanged: ['workbench.browser.enableChatTools'],
+		dismissWhenCommandsClicked: ['workbench.action.openSettings'],
+	},
+	{
+		id: 'tip.mermaid',
+		tier: ChatTipTier.Qol,
+		buildMessage() {
+			return new MarkdownString(
+				localize('tip.mermaid', "Ask the agent to draw an architectural diagram or flow chart. It can render Mermaid diagrams directly in chat.")
+			);
+		},
+		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+		excludeWhenToolsInvoked: ['renderMermaidDiagram'],
+	},
+	{
+		id: 'tip.subagents',
+		tier: ChatTipTier.Qol,
+		buildMessage() {
+			return new MarkdownString(
+				localize('tip.subagents', "Have another task to work on? Start a new session to run multiple agents at once.")
+			);
+		},
+		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+		excludeWhenToolsInvoked: ['runSubagent'],
+	},
+	{
+		id: 'tip.thinkingPhrases',
+		tier: ChatTipTier.Qol,
+		buildMessage() {
+			return new MarkdownString(
+				localize(
+					'tip.thinkingPhrases',
+					"Customize the loading messages shown while the agent works with [{0}](command:workbench.action.openSettings?%5B%22{1}%22%5D \"Open Settings\").",
+					'thinking phrases',
+					ChatConfiguration.ThinkingPhrases
+				)
+			);
+		},
+		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
+		excludeWhenSettingsChanged: [ChatConfiguration.ThinkingPhrases],
+		dismissWhenCommandsClicked: ['workbench.action.openSettings'],
+	},
+	{
+		id: 'tip.troubleshoot',
+		tier: ChatTipTier.Qol,
+		buildMessage(ctx) {
+			const kb = formatKeybinding(ctx, INSERT_TROUBLESHOOT_COMMAND_ID);
+			return new MarkdownString(
+				localize(
+					'tip.troubleshoot',
+					"Something not working? Type [{0}](command:{1} \"Run /troubleshoot\"){2} <question> to diagnose issues from debug logs.",
+					'/troubleshoot',
+					INSERT_TROUBLESHOOT_COMMAND_ID,
+					kb
+				)
+			);
+		},
+		when: ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
+		excludeWhenToolsInvoked: ['listDebugEvents'],
+	},
+];
diff --git a/src/vs/workbench/contrib/chat/browser/chatTipEligibilityTracker.ts b/src/vs/workbench/contrib/chat/browser/chatTipEligibilityTracker.ts
new file mode 100644
index 0000000000000..df72fa41ab419
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/chatTipEligibilityTracker.ts
@@ -0,0 +1,327 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { Disposable, MutableDisposable } from '../../../../base/common/lifecycle.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
+import { ChatContextKeys } from '../common/actions/chatContextKeys.js';
+import { AgentFileType, IPromptsService } from '../common/promptSyntax/service/promptsService.js';
+import { PromptsType } from '../common/promptSyntax/promptTypes.js';
+import { ILanguageModelToolsService } from '../common/tools/languageModelToolsService.js';
+import { TipEligibilityStorageKeys } from './chatTipStorageKeys.js';
+
+/**
+ * Interface for tip definitions that have exclusion criteria tracked by this class.
+ * This subset is all TipEligibilityTracker needs to know about tip definitions.
+ */
+export interface ITipExclusionConfig {
+	readonly id: string;
+	/** Command IDs that, if ever executed, make this tip ineligible. */
+	readonly excludeWhenCommandsExecuted?: readonly string[];
+	/** Chat mode names that, if ever used, make this tip ineligible. */
+	readonly excludeWhenModesUsed?: readonly string[];
+	/** Tool IDs that, if ever invoked, make this tip ineligible. */
+	readonly excludeWhenToolsInvoked?: readonly string[];
+	/** File-based exclusion configuration. */
+	readonly excludeWhenPromptFilesExist?: {
+		readonly promptType: PromptsType;
+		readonly agentFileType?: AgentFileType;
+		readonly excludeUntilChecked?: boolean;
+	};
+}
+
+/**
+ * Tracks user-level signals that determine whether certain tips should be
+ * excluded. Persists state to application storage and disposes listeners once all
+ * signals of interest have been observed.
+ */
+export class TipEligibilityTracker extends Disposable {
+
+	private readonly _executedCommands: Set<string>;
+	private readonly _usedModes: Set<string>;
+	private readonly _invokedTools: Set<string>;
+
+	private readonly _pendingCommands: Set<string>;
+	private readonly _pendingModes: Set<string>;
+	private readonly _pendingTools: Set<string>;
+
+	private readonly _commandListener = this._register(new MutableDisposable());
+	private readonly _toolListener = this._register(new MutableDisposable());
+
+	/**
+	 * Tip IDs excluded because prompt files of the required type exist in the workspace.
+	 * Tips with `excludeUntilChecked` are pre-added and removed if no files are found.
+	 */
+	private readonly _excludedByFiles = new Set<string>();
+
+	/** Tips that have file-based exclusions, kept for re-checks. */
+	private readonly _tipsWithFileExclusions: readonly ITipExclusionConfig[];
+
+	/** Generation counter per tip ID to discard stale async file-check results. */
+	private readonly _fileCheckGeneration = new Map<string, number>();
+	private readonly _fileChecksInFlight = new Map<string, Promise<void>>();
+
+	constructor(
+		tips: readonly ITipExclusionConfig[],
+		@ICommandService commandService: ICommandService,
+		@IStorageService private readonly _storageService: IStorageService,
+		@IPromptsService private readonly _promptsService: IPromptsService,
+		@ILanguageModelToolsService private readonly _languageModelToolsService: ILanguageModelToolsService,
+		@ILogService private readonly _logService: ILogService,
+	) {
+		super();
+
+		// --- Restore persisted state -------------------------------------------
+
+		const storedCmds = this._readApplicationWithProfileFallback(TipEligibilityStorageKeys.ExecutedCommands);
+		this._executedCommands = new Set<string>(storedCmds ? JSON.parse(storedCmds) : []);
+
+		const storedModes = this._readApplicationWithProfileFallback(TipEligibilityStorageKeys.UsedModes);
+		this._usedModes = new Set<string>(storedModes ? JSON.parse(storedModes) : []);
+
+		const storedTools = this._readApplicationWithProfileFallback(TipEligibilityStorageKeys.InvokedTools);
+		this._invokedTools = new Set<string>(storedTools ? JSON.parse(storedTools) : []);
+
+		// --- Derive what still needs tracking ----------------------------------
+
+		this._pendingCommands = new Set<string>();
+		for (const tip of tips) {
+			for (const cmd of tip.excludeWhenCommandsExecuted ?? []) {
+				if (!this._executedCommands.has(cmd)) {
+					this._pendingCommands.add(cmd);
+				}
+			}
+		}
+
+		this._pendingModes = new Set<string>();
+		for (const tip of tips) {
+			for (const mode of tip.excludeWhenModesUsed ?? []) {
+				if (!this._usedModes.has(mode)) {
+					this._pendingModes.add(mode);
+				}
+			}
+		}
+
+		this._pendingTools = new Set<string>();
+		for (const tip of tips) {
+			for (const toolId of tip.excludeWhenToolsInvoked ?? []) {
+				if (!this._invokedTools.has(toolId)) {
+					this._pendingTools.add(toolId);
+				}
+			}
+		}
+
+		// --- Set up command listener (auto-disposes when all seen) --------------
+
+		if (this._pendingCommands.size > 0) {
+			this._commandListener.value = commandService.onDidExecuteCommand(e => {
+				this.recordCommandExecuted(e.commandId);
+			});
+		}
+
+		// --- Set up tool listener (auto-disposes when all seen) -----------------
+
+		if (this._pendingTools.size > 0) {
+			this._toolListener.value = this._languageModelToolsService.onDidInvokeTool(e => {
+				// Track explicit tool IDs
+				if (this._pendingTools.has(e.toolId)) {
+					this._invokedTools.add(e.toolId);
+					this._pendingTools.delete(e.toolId);
+
+					this._persistSet(TipEligibilityStorageKeys.InvokedTools, this._invokedTools);
+				}
+
+				if (this._pendingTools.size === 0) {
+					this._toolListener.clear();
+				}
+			});
+		}
+
+		// --- Async file checks -------------------------------------------------
+
+		this._tipsWithFileExclusions = tips.filter(t => t.excludeWhenPromptFilesExist);
+		for (const tip of this._tipsWithFileExclusions) {
+			if (tip.excludeWhenPromptFilesExist!.excludeUntilChecked) {
+				this._excludedByFiles.add(tip.id);
+			}
+			this._checkForPromptFiles(tip);
+		}
+
+		// Re-check agent file exclusions when custom agents change (covers late discovery)
+		this._register(this._promptsService.onDidChangeCustomAgents(() => {
+			for (const tip of this._tipsWithFileExclusions) {
+				if (tip.excludeWhenPromptFilesExist!.promptType === PromptsType.agent) {
+					this._checkForPromptFiles(tip);
+				}
+			}
+		}));
+	}
+
+	recordCommandExecuted(commandId: string): void {
+		if (!this._pendingCommands.has(commandId)) {
+			return;
+		}
+
+		this._executedCommands.add(commandId);
+		this._persistSet(TipEligibilityStorageKeys.ExecutedCommands, this._executedCommands);
+		this._pendingCommands.delete(commandId);
+
+		if (this._pendingCommands.size === 0) {
+			this._commandListener.clear();
+		}
+	}
+
+	/**
+	 * Records the current chat mode (kind + name) so future tip eligibility
+	 * checks can exclude mode-related tips. No-ops once all tracked modes
+	 * have been observed.
+	 */
+	recordCurrentMode(contextKeyService: IContextKeyService): void {
+		if (this._pendingModes.size === 0) {
+			return;
+		}
+
+		let changed = false;
+		const kind = contextKeyService.getContextKeyValue<string>(ChatContextKeys.chatModeKind.key);
+		if (kind && !this._usedModes.has(kind)) {
+			this._usedModes.add(kind);
+			this._pendingModes.delete(kind);
+			changed = true;
+		}
+		const name = contextKeyService.getContextKeyValue<string>(ChatContextKeys.chatModeName.key);
+		if (name && !this._usedModes.has(name)) {
+			this._usedModes.add(name);
+			this._pendingModes.delete(name);
+			changed = true;
+		}
+		if (changed) {
+			this._persistSet(TipEligibilityStorageKeys.UsedModes, this._usedModes);
+		}
+	}
+
+	/**
+	 * Returns `true` when the tip should be **excluded** from the eligible set.
+	 */
+	isExcluded(tip: ITipExclusionConfig): boolean {
+		if (tip.excludeWhenCommandsExecuted) {
+			for (const cmd of tip.excludeWhenCommandsExecuted) {
+				if (this._executedCommands.has(cmd)) {
+					this._logService.debug('#ChatTips: tip excluded because command was executed', tip.id, cmd);
+					return true;
+				}
+			}
+		}
+		if (tip.excludeWhenModesUsed) {
+			for (const mode of tip.excludeWhenModesUsed) {
+				if (this._usedModes.has(mode)) {
+					this._logService.debug('#ChatTips: tip excluded because mode was used', tip.id, mode);
+					return true;
+				}
+			}
+		}
+		if (tip.excludeWhenToolsInvoked) {
+			for (const toolId of tip.excludeWhenToolsInvoked) {
+				if (this._invokedTools.has(toolId)) {
+					this._logService.debug('#ChatTips: tip excluded because tool was invoked', tip.id, toolId);
+					return true;
+				}
+			}
+		}
+		if (tip.excludeWhenPromptFilesExist && this._excludedByFiles.has(tip.id)) {
+			this._logService.debug('#ChatTips: tip excluded because prompt files exist', tip.id);
+			return true;
+		}
+		return false;
+	}
+
+	/**
+	 * Revalidates all file-based tip exclusions. Tips with `excludeUntilChecked`
+	 * are conservatively hidden until the re-check completes.
+	 */
+	refreshPromptFileExclusions(): void {
+		for (const tip of this._tipsWithFileExclusions) {
+			if (tip.excludeWhenPromptFilesExist!.excludeUntilChecked) {
+				this._excludedByFiles.add(tip.id);
+			}
+			this._checkForPromptFiles(tip);
+		}
+	}
+
+	private async _checkForPromptFiles(tip: ITipExclusionConfig): Promise<void> {
+		const inFlight = this._fileChecksInFlight.get(tip.id);
+		if (inFlight) {
+			await inFlight;
+			return;
+		}
+
+		const checkPromise = this._doCheckForPromptFiles(tip);
+		this._fileChecksInFlight.set(tip.id, checkPromise);
+		try {
+			await checkPromise;
+		} finally {
+			if (this._fileChecksInFlight.get(tip.id) === checkPromise) {
+				this._fileChecksInFlight.delete(tip.id);
+			}
+		}
+	}
+
+	private async _doCheckForPromptFiles(tip: ITipExclusionConfig): Promise<void> {
+		const config = tip.excludeWhenPromptFilesExist!;
+		const generation = (this._fileCheckGeneration.get(tip.id) ?? 0) + 1;
+		this._fileCheckGeneration.set(tip.id, generation);
+
+		try {
+			const [promptFiles, agentInstructions] = await Promise.all([
+				this._promptsService.listPromptFiles(config.promptType, CancellationToken.None),
+				config.agentFileType ? this._promptsService.listAgentInstructions(CancellationToken.None) : Promise.resolve([]),
+			]);
+
+			// Discard stale result if a newer check was started while we were awaiting
+			if (this._fileCheckGeneration.get(tip.id) !== generation) {
+				return;
+			}
+
+			const hasPromptFiles = promptFiles.length > 0;
+			const hasAgentFile = config.agentFileType
+				? agentInstructions.some(f => f.type === config.agentFileType)
+				: false;
+			const hasPromptFilesOrAgentFile = hasPromptFiles || hasAgentFile;
+
+			if (hasPromptFilesOrAgentFile) {
+				this._excludedByFiles.add(tip.id);
+			} else {
+				this._excludedByFiles.delete(tip.id);
+			}
+		} catch {
+			if (this._fileCheckGeneration.get(tip.id) !== generation) {
+				return;
+			}
+			if (config.excludeUntilChecked) {
+				this._excludedByFiles.add(tip.id);
+			}
+		}
+	}
+
+	private _persistSet(key: string, set: Set<string>): void {
+		this._storageService.store(key, JSON.stringify([...set]), StorageScope.APPLICATION, StorageTarget.MACHINE);
+	}
+
+	private _readApplicationWithProfileFallback(key: string): string | undefined {
+		const applicationValue = this._storageService.get(key, StorageScope.APPLICATION);
+		if (applicationValue) {
+			return applicationValue;
+		}
+
+		const profileValue = this._storageService.get(key, StorageScope.PROFILE);
+		if (profileValue) {
+			this._storageService.store(key, profileValue, StorageScope.APPLICATION, StorageTarget.MACHINE);
+		}
+
+		return profileValue;
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/chatTipService.ts b/src/vs/workbench/contrib/chat/browser/chatTipService.ts
index 9c78ef90cd9a5..fc596d0a73280 100644
--- a/src/vs/workbench/contrib/chat/browser/chatTipService.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatTipService.ts
@@ -5,26 +5,26 @@
 
 import { Emitter, Event } from '../../../../base/common/event.js';
 import { MarkdownString } from '../../../../base/common/htmlContent.js';
-import { ContextKeyExpr, ContextKeyExpression, IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
+import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
 import { createDecorator, IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { IProductService } from '../../../../platform/product/common/productService.js';
 import { ChatContextKeys } from '../common/actions/chatContextKeys.js';
-import { ChatAgentLocation, ChatConfiguration, ChatModeKind } from '../common/constants.js';
+import { ChatAgentLocation, ChatConfiguration } from '../common/constants.js';
 import { ConfigurationTarget, IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { Disposable, MutableDisposable } from '../../../../base/common/lifecycle.js';
 import { ICommandService } from '../../../../platform/commands/common/commands.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
-import { AgentFileType, IPromptsService } from '../common/promptSyntax/service/promptsService.js';
-import { PromptsType } from '../common/promptSyntax/promptTypes.js';
-import { CancellationToken } from '../../../../base/common/cancellation.js';
 import { localize } from '../../../../nls.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
-import { ILanguageModelToolsService } from '../common/tools/languageModelToolsService.js';
-import { localChatSessionType } from '../common/chatSessionsService.js';
 import { IChatService } from '../common/chatService/chatService.js';
 import { CreateSlashCommandsUsageTracker } from './createSlashCommandsUsageTracker.js';
 import { ChatEntitlement, IChatEntitlementService } from '../../../services/chat/common/chatEntitlementService.js';
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
+import { ChatRequestAgentSubcommandPart, ChatRequestDynamicVariablePart, ChatRequestSlashCommandPart, IParsedChatRequest } from '../common/requestParser/chatParserTypes.js';
+import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
+import { TipEligibilityTracker } from './chatTipEligibilityTracker.js';
+import { ChatTipTier, extractCommandIds, ITipBuildContext, ITipDefinition, TIP_CATALOG } from './chatTipCatalog.js';
+import { ChatTipStorageKeys, TipTrackingCommands } from './chatTipStorageKeys.js';
 
 type ChatTipEvent = {
 	tipId: string;
@@ -40,6 +40,21 @@ type ChatTipClassification = {
 	comment: 'Tracks user interactions with chat tips to understand which tips resonate and which are dismissed.';
 };
 
+// Re-export tracking commands for backwards compatibility
+export { TipTrackingCommands };
+/** @deprecated Use TipTrackingCommands.AttachFilesReferenceUsed */
+export const ATTACH_FILES_REFERENCE_TRACKING_COMMAND = TipTrackingCommands.AttachFilesReferenceUsed;
+/** @deprecated Use TipTrackingCommands.CreateAgentInstructionsUsed */
+export const CREATE_AGENT_INSTRUCTIONS_TRACKING_COMMAND = TipTrackingCommands.CreateAgentInstructionsUsed;
+/** @deprecated Use TipTrackingCommands.CreatePromptUsed */
+export const CREATE_PROMPT_TRACKING_COMMAND = TipTrackingCommands.CreatePromptUsed;
+/** @deprecated Use TipTrackingCommands.CreateAgentUsed */
+export const CREATE_AGENT_TRACKING_COMMAND = TipTrackingCommands.CreateAgentUsed;
+/** @deprecated Use TipTrackingCommands.CreateSkillUsed */
+export const CREATE_SKILL_TRACKING_COMMAND = TipTrackingCommands.CreateSkillUsed;
+/** @deprecated Use TipTrackingCommands.ForkConversationUsed */
+export const FORK_CONVERSATION_TRACKING_COMMAND = TipTrackingCommands.ForkConversationUsed;
+
 export const IChatTipService = createDecorator<IChatTipService>('chatTipService');
 
 export interface IChatTip {
@@ -89,12 +104,22 @@ export interface IChatTipService {
 	 */
 	dismissTip(): void;
 
+	/**
+	 * Dismisses the current tip and hides all tips for the rest of the current chat session.
+	 */
+	dismissTipForSession(): void;
+
 	/**
 	 * Hides the tip widget without permanently dismissing the tip.
 	 * The tip may be shown again in a future session.
 	 */
 	hideTip(): void;
 
+	/**
+	 * Hides all tips for the rest of the current chat session.
+	 */
+	hideTipsForSession(): void;
+
 	/**
 	 * Disables tips permanently by setting the `chat.tips.enabled` configuration to false.
 	 */
@@ -111,517 +136,32 @@ export interface IChatTipService {
 	navigateToPreviousTip(): IChatTip | undefined;
 
 	/**
-	 * Clears all dismissed tips so they can be shown again.
-	 */
-	clearDismissedTips(): void;
-}
-
-export interface ITipDefinition {
-	readonly id: string;
-	readonly message: string;
-	/**
-	 * When clause expression that determines if this tip is eligible to be shown.
-	 * If undefined, the tip is always eligible.
-	 */
-	readonly when?: ContextKeyExpression;
-	/**
-	 * Command IDs that are allowed to be executed from this tip's markdown.
-	 */
-	readonly enabledCommands?: string[];
-	/**
-	 * Chat model IDs for which this tip is eligible.
-	 * Compared against the lowercased `chatModelId` context key.
-	 */
-	readonly onlyWhenModelIds?: readonly string[];
-	/**
-	 * Command IDs that, if ever executed in this workspace, make this tip ineligible.
-	 * The tip won't be shown if the user has already performed the action it suggests.
-	 */
-	readonly excludeWhenCommandsExecuted?: string[];
-	/**
-	 * Chat mode names that, if ever used in this workspace, make this tip ineligible.
-	 * The tip won't be shown if the user has already used the mode it suggests.
-	 * Matches against both mode kind (e.g. 'agent') and mode name (e.g. 'Plan').
-	 */
-	readonly excludeWhenModesUsed?: string[];
-	/**
-	 * Tool IDs that, if ever invoked in this workspace, make this tip ineligible.
-	 * The tip won't be shown if the tool it describes has already been used.
-	 */
-	readonly excludeWhenToolsInvoked?: string[];
-	/**
-	 * If set, exclude this tip when prompt files of the specified type exist in the workspace.
-	 */
-	readonly excludeWhenPromptFilesExist?: {
-		readonly promptType: PromptsType;
-		/** Also check for this specific agent instruction file type. */
-		readonly agentFileType?: AgentFileType;
-		/** If true, exclude the tip until the async file check completes. Default: false. */
-		readonly excludeUntilChecked?: boolean;
-	};
-	/**
-	 * Setting keys that, if changed from their default value, make this tip ineligible.
-	 * The tip won't be shown if the user has already customized the setting it describes.
-	 */
-	readonly excludeWhenSettingsChanged?: string[];
-	/**
-	 * Command IDs that dismiss this tip when clicked from the tip markdown
-	 * while the tip is currently shown.
-	 */
-	readonly dismissWhenCommandsClicked?: string[];
-}
-
-/**
- * Static catalog of tips. Each tip has an optional when clause for eligibility.
- */
-const TIP_CATALOG: ITipDefinition[] = [
-	{
-		id: 'tip.switchToAuto',
-		message: localize('tip.switchToAuto', "Tip: Using gpt-4.1? Try switching to [Auto](command:workbench.action.chat.openModelPicker) in the model picker for better coding performance."),
-		enabledCommands: ['workbench.action.chat.openModelPicker'],
-		onlyWhenModelIds: ['gpt-4.1'],
-	},
-	{
-		id: 'tip.createSlashCommands',
-		message: localize(
-			'tip.createSlashCommands',
-			"Tip: Use [/create-instruction](command:workbench.action.chat.generateInstruction), [/create-prompt](command:workbench.action.chat.generatePrompt), [/create-agent](command:workbench.action.chat.generateAgent), or [/create-skill](command:workbench.action.chat.generateSkill) to generate reusable agent customization files."
-		),
-		when: ContextKeyExpr.and(
-			ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
-			ChatContextKeys.hasUsedCreateSlashCommands.negate(),
-		),
-		enabledCommands: [
-			'workbench.action.chat.generateInstruction',
-			'workbench.action.chat.generatePrompt',
-			'workbench.action.chat.generateAgent',
-			'workbench.action.chat.generateSkill',
-		],
-		excludeWhenCommandsExecuted: [
-			'workbench.action.chat.generateInstruction',
-			'workbench.action.chat.generatePrompt',
-			'workbench.action.chat.generateAgent',
-			'workbench.action.chat.generateSkill',
-		],
-	},
-	{
-		id: 'tip.agentMode',
-		message: localize('tip.agentMode', "Tip: Try [Agents](command:workbench.action.chat.openEditSession) to make edits across your project and run commands."),
-		when: ChatContextKeys.chatModeKind.notEqualsTo(ChatModeKind.Agent),
-		enabledCommands: ['workbench.action.chat.openEditSession'],
-		excludeWhenModesUsed: [ChatModeKind.Agent],
-	},
-	{
-		id: 'tip.planMode',
-		message: localize('tip.planMode', "Tip: Try the [Plan agent](command:workbench.action.chat.openPlan) to research and plan before implementing changes."),
-		when: ChatContextKeys.chatModeName.notEqualsTo('Plan'),
-		enabledCommands: ['workbench.action.chat.openPlan'],
-		excludeWhenCommandsExecuted: ['workbench.action.chat.openPlan'],
-		excludeWhenModesUsed: ['Plan'],
-	},
-	{
-		id: 'tip.attachFiles',
-		message: localize('tip.attachFiles', "Tip: Reference files or folders with # to give the agent more context about the task."),
-		excludeWhenCommandsExecuted: ['workbench.action.chat.attachContext', 'workbench.action.chat.attachFile', 'workbench.action.chat.attachFolder', 'workbench.action.chat.attachSelection'],
-	},
-	{
-		id: 'tip.codeActions',
-		message: localize('tip.codeActions', "Tip: Select a code block in the editor and right-click to access more AI actions."),
-		excludeWhenCommandsExecuted: ['inlineChat.start'],
-	},
-	{
-		id: 'tip.undoChanges',
-		message: localize('tip.undoChanges', "Tip: Select \"Restore Checkpoint\" to undo changes after that point in the chat conversation."),
-		when: ContextKeyExpr.and(
-			ChatContextKeys.chatSessionType.isEqualTo(localChatSessionType),
-			ContextKeyExpr.or(
-				ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-				ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Edit),
-			),
-		),
-		excludeWhenCommandsExecuted: ['workbench.action.chat.restoreCheckpoint'],
-	},
-	{
-		id: 'tip.customInstructions',
-		message: localize('tip.customInstructions', "Tip: [Generate workspace instructions](command:workbench.action.chat.generateInstructions) apply coding conventions across all agent sessions."),
-		enabledCommands: ['workbench.action.chat.generateInstructions'],
-		excludeWhenCommandsExecuted: ['workbench.action.chat.generateInstructions'],
-		excludeWhenPromptFilesExist: { promptType: PromptsType.instructions, agentFileType: AgentFileType.copilotInstructionsMd, excludeUntilChecked: true },
-	},
-	{
-		id: 'tip.customAgent',
-		message: localize('tip.customAgent', "Tip: [Create a custom agent](command:workbench.command.new.agent) to define reusable personas with tailored instructions and tools for your workflow."),
-		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-		enabledCommands: ['workbench.command.new.agent'],
-		excludeWhenCommandsExecuted: ['workbench.command.new.agent'],
-		excludeWhenPromptFilesExist: { promptType: PromptsType.agent, excludeUntilChecked: true },
-	},
-	{
-		id: 'tip.skill',
-		message: localize('tip.skill', "Tip: [Create a skill](command:workbench.command.new.skill) to teach the agent specialized workflows, loaded only when relevant."),
-		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-		enabledCommands: ['workbench.command.new.skill'],
-		excludeWhenCommandsExecuted: ['workbench.command.new.skill'],
-		excludeWhenPromptFilesExist: { promptType: PromptsType.skill, excludeUntilChecked: true },
-	},
-	{
-		id: 'tip.messageQueueing',
-		message: localize('tip.messageQueueing', "Tip: Steer the agent mid-task by sending follow-up messages. They queue and apply in order."),
-		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-		excludeWhenCommandsExecuted: ['workbench.action.chat.queueMessage', 'workbench.action.chat.steerWithMessage'],
-	},
-	{
-		id: 'tip.yoloMode',
-		message: localize('tip.yoloMode', "Tip: Enable [auto approve](command:workbench.action.openSettings?%5B%22chat.tools.global.autoApprove%22%5D) to give the agent full control without manual confirmation."),
-		when: ContextKeyExpr.and(
-			ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-			ContextKeyExpr.notEquals('config.chat.tools.global.autoApprove', true),
-		),
-		enabledCommands: ['workbench.action.openSettings'],
-		excludeWhenSettingsChanged: [ChatConfiguration.GlobalAutoApprove],
-		dismissWhenCommandsClicked: ['workbench.action.openSettings'],
-	},
-	{
-		id: 'tip.agenticBrowser',
-		message: localize('tip.agenticBrowser', "Tip: Enable [agentic browser integration](command:workbench.action.openSettings?%5B%22workbench.browser.enableChatTools%22%5D) to let the agent open and interact with pages in the Integrated Browser."),
-		when: ContextKeyExpr.and(
-			ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-			ContextKeyExpr.notEquals('config.workbench.browser.enableChatTools', true),
-		),
-		enabledCommands: ['workbench.action.openSettings'],
-		excludeWhenSettingsChanged: ['workbench.browser.enableChatTools'],
-		dismissWhenCommandsClicked: ['workbench.action.openSettings'],
-	},
-	{
-		id: 'tip.mermaid',
-		message: localize('tip.mermaid', "Tip: Ask the agent to draw an architectural diagram or flow chart; it can render Mermaid diagrams directly in chat."),
-		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-		excludeWhenToolsInvoked: ['renderMermaidDiagram'],
-	},
-	{
-		id: 'tip.subagents',
-		message: localize('tip.subagents', "Tip: Ask the agent to work in parallel to complete large tasks faster."),
-		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-		excludeWhenToolsInvoked: ['runSubagent'],
-	},
-	{
-		id: 'tip.thinkingPhrases',
-		message: localize('tip.thinkingPhrases', "Tip: Customize the loading messages shown while the agent works with [thinking phrases](command:workbench.action.openSettings?%5B%22chat.agent.thinking.phrases%22%5D)."),
-		when: ChatContextKeys.chatModeKind.isEqualTo(ChatModeKind.Agent),
-		enabledCommands: ['workbench.action.openSettings'],
-		excludeWhenSettingsChanged: ['chat.agent.thinking.phrases'],
-		dismissWhenCommandsClicked: ['workbench.action.openSettings'],
-	},
-];
-
-/**
- * Tracks user-level signals that determine whether certain tips should be
- * excluded. Persists state to application storage and disposes listeners once all
- * signals of interest have been observed.
- */
-export class TipEligibilityTracker extends Disposable {
-
-	private static readonly _COMMANDS_STORAGE_KEY = 'chat.tips.executedCommands';
-	private static readonly _MODES_STORAGE_KEY = 'chat.tips.usedModes';
-	private static readonly _TOOLS_STORAGE_KEY = 'chat.tips.invokedTools';
-	private static readonly _INSTRUCTION_FILES_EVER_DETECTED_KEY = 'chat.tips.instructionFilesEverDetected';
-
-	private readonly _executedCommands: Set<string>;
-	private readonly _usedModes: Set<string>;
-	private readonly _invokedTools: Set<string>;
-
-	private readonly _pendingCommands: Set<string>;
-	private readonly _pendingModes: Set<string>;
-	private readonly _pendingTools: Set<string>;
-
-	private readonly _commandListener = this._register(new MutableDisposable());
-	private readonly _toolListener = this._register(new MutableDisposable());
-
-	/**
-	 * Tip IDs excluded because prompt files of the required type exist in the workspace.
-	 * Tips with `excludeUntilChecked` are pre-added and removed if no files are found.
+	 * Gets the next eligible tip after the current one, without requiring multiple tips.
+	 * Used after dismissing a tip to show the next available tip (even if it's the only one left).
 	 */
-	private readonly _excludedByFiles = new Set<string>();
-
-	/** Tips that have file-based exclusions, kept for re-checks. */
-	private readonly _tipsWithFileExclusions: readonly ITipDefinition[];
-
-	/** Generation counter per tip ID to discard stale async file-check results. */
-	private readonly _fileCheckGeneration = new Map<string, number>();
-	private readonly _fileChecksInFlight = new Map<string, Promise<void>>();
-	private _instructionFilesEverDetected: boolean;
-
-	constructor(
-		tips: readonly ITipDefinition[],
-		@ICommandService commandService: ICommandService,
-		@IStorageService private readonly _storageService: IStorageService,
-		@IPromptsService private readonly _promptsService: IPromptsService,
-		@ILanguageModelToolsService private readonly _languageModelToolsService: ILanguageModelToolsService,
-		@ILogService private readonly _logService: ILogService,
-	) {
-		super();
-
-		// --- Restore persisted state -------------------------------------------
-
-		const storedCmds = this._readApplicationWithProfileFallback(TipEligibilityTracker._COMMANDS_STORAGE_KEY);
-		this._executedCommands = new Set<string>(storedCmds ? JSON.parse(storedCmds) : []);
-
-		const storedModes = this._readApplicationWithProfileFallback(TipEligibilityTracker._MODES_STORAGE_KEY);
-		this._usedModes = new Set<string>(storedModes ? JSON.parse(storedModes) : []);
-
-		const storedTools = this._readApplicationWithProfileFallback(TipEligibilityTracker._TOOLS_STORAGE_KEY);
-		this._invokedTools = new Set<string>(storedTools ? JSON.parse(storedTools) : []);
-
-		this._instructionFilesEverDetected = this._storageService.getBoolean(TipEligibilityTracker._INSTRUCTION_FILES_EVER_DETECTED_KEY, StorageScope.APPLICATION, false);
-
-		// --- Derive what still needs tracking ----------------------------------
-
-		this._pendingCommands = new Set<string>();
-		for (const tip of tips) {
-			for (const cmd of tip.excludeWhenCommandsExecuted ?? []) {
-				if (!this._executedCommands.has(cmd)) {
-					this._pendingCommands.add(cmd);
-				}
-			}
-		}
-
-		this._pendingModes = new Set<string>();
-		for (const tip of tips) {
-			for (const mode of tip.excludeWhenModesUsed ?? []) {
-				if (!this._usedModes.has(mode)) {
-					this._pendingModes.add(mode);
-				}
-			}
-		}
-
-		this._pendingTools = new Set<string>();
-		for (const tip of tips) {
-			for (const toolId of tip.excludeWhenToolsInvoked ?? []) {
-				if (!this._invokedTools.has(toolId)) {
-					this._pendingTools.add(toolId);
-				}
-			}
-		}
-
-		// --- Set up command listener (auto-disposes when all seen) --------------
-
-		if (this._pendingCommands.size > 0) {
-			this._commandListener.value = commandService.onDidExecuteCommand(e => {
-				if (this._pendingCommands.has(e.commandId)) {
-					this._executedCommands.add(e.commandId);
-					this._persistSet(TipEligibilityTracker._COMMANDS_STORAGE_KEY, this._executedCommands);
-					this._pendingCommands.delete(e.commandId);
-
-					if (this._pendingCommands.size === 0) {
-						this._commandListener.clear();
-					}
-				}
-			});
-		}
-
-		// --- Set up tool listener (auto-disposes when all seen) -----------------
-
-		if (this._pendingTools.size > 0) {
-			this._toolListener.value = this._languageModelToolsService.onDidInvokeTool(e => {
-				// Track explicit tool IDs
-				if (this._pendingTools.has(e.toolId)) {
-					this._invokedTools.add(e.toolId);
-					this._pendingTools.delete(e.toolId);
-
-					this._persistSet(TipEligibilityTracker._TOOLS_STORAGE_KEY, this._invokedTools);
-				}
-
-				if (this._pendingTools.size === 0) {
-					this._toolListener.clear();
-				}
-			});
-		}
-
-		// --- Async file checks -------------------------------------------------
-
-		this._tipsWithFileExclusions = tips.filter(t => t.excludeWhenPromptFilesExist);
-		for (const tip of this._tipsWithFileExclusions) {
-			if (this._instructionFilesEverDetected && tip.id === 'tip.customInstructions') {
-				this._excludedByFiles.add(tip.id);
-				continue;
-			}
-
-			if (tip.excludeWhenPromptFilesExist!.excludeUntilChecked) {
-				this._excludedByFiles.add(tip.id);
-			}
-			this._checkForPromptFiles(tip);
-		}
-
-		// Re-check agent file exclusions when custom agents change (covers late discovery)
-		this._register(this._promptsService.onDidChangeCustomAgents(() => {
-			for (const tip of this._tipsWithFileExclusions) {
-				if (tip.excludeWhenPromptFilesExist!.promptType === PromptsType.agent) {
-					this._checkForPromptFiles(tip);
-				}
-			}
-		}));
-	}
+	getNextEligibleTip(): IChatTip | undefined;
 
 	/**
-	 * Records the current chat mode (kind + name) so future tip eligibility
-	 * checks can exclude mode-related tips. No-ops once all tracked modes
-	 * have been observed.
+	 * Returns whether there are multiple eligible tips for navigation.
 	 */
-	recordCurrentMode(contextKeyService: IContextKeyService): void {
-		if (this._pendingModes.size === 0) {
-			return;
-		}
-
-		let changed = false;
-		const kind = contextKeyService.getContextKeyValue<string>(ChatContextKeys.chatModeKind.key);
-		if (kind && !this._usedModes.has(kind)) {
-			this._usedModes.add(kind);
-			this._pendingModes.delete(kind);
-			changed = true;
-		}
-		const name = contextKeyService.getContextKeyValue<string>(ChatContextKeys.chatModeName.key);
-		if (name && !this._usedModes.has(name)) {
-			this._usedModes.add(name);
-			this._pendingModes.delete(name);
-			changed = true;
-		}
-		if (changed) {
-			this._persistSet(TipEligibilityTracker._MODES_STORAGE_KEY, this._usedModes);
-		}
-	}
+	hasMultipleTips(): boolean;
 
 	/**
-	 * Returns `true` when the tip should be **excluded** from the eligible set.
+	 * Records usage of a slash command to update tip eligibility for flows where
+	 * the slash command text is transformed before request submission.
 	 */
-	isExcluded(tip: ITipDefinition): boolean {
-		if (tip.excludeWhenCommandsExecuted) {
-			for (const cmd of tip.excludeWhenCommandsExecuted) {
-				if (this._executedCommands.has(cmd)) {
-					this._logService.debug('#ChatTips: tip excluded because command was executed', tip.id, cmd);
-					return true;
-				}
-			}
-		}
-		if (tip.excludeWhenModesUsed) {
-			for (const mode of tip.excludeWhenModesUsed) {
-				if (this._usedModes.has(mode)) {
-					this._logService.debug('#ChatTips: tip excluded because mode was used', tip.id, mode);
-					return true;
-				}
-			}
-		}
-		if (tip.excludeWhenToolsInvoked) {
-			for (const toolId of tip.excludeWhenToolsInvoked) {
-				if (this._invokedTools.has(toolId)) {
-					this._logService.debug('#ChatTips: tip excluded because tool was invoked', tip.id, toolId);
-					return true;
-				}
-			}
-		}
-		if (tip.excludeWhenPromptFilesExist && this._excludedByFiles.has(tip.id)) {
-			this._logService.debug('#ChatTips: tip excluded because prompt files exist', tip.id);
-			return true;
-		}
-		return false;
-	}
+	recordSlashCommandUsage(command: string): void;
 
 	/**
-	 * Revalidates all file-based tip exclusions. Tips with `excludeUntilChecked`
-	 * are conservatively hidden until the re-check completes.
+	 * Clears all dismissed tips so they can be shown again.
 	 */
-	refreshPromptFileExclusions(): void {
-		for (const tip of this._tipsWithFileExclusions) {
-			if (this._instructionFilesEverDetected && tip.id === 'tip.customInstructions') {
-				this._excludedByFiles.add(tip.id);
-				continue;
-			}
-
-			if (tip.excludeWhenPromptFilesExist!.excludeUntilChecked) {
-				this._excludedByFiles.add(tip.id);
-			}
-			this._checkForPromptFiles(tip);
-		}
-	}
-
-	private async _checkForPromptFiles(tip: ITipDefinition): Promise<void> {
-		const inFlight = this._fileChecksInFlight.get(tip.id);
-		if (inFlight) {
-			await inFlight;
-			return;
-		}
-
-		const checkPromise = this._doCheckForPromptFiles(tip);
-		this._fileChecksInFlight.set(tip.id, checkPromise);
-		try {
-			await checkPromise;
-		} finally {
-			if (this._fileChecksInFlight.get(tip.id) === checkPromise) {
-				this._fileChecksInFlight.delete(tip.id);
-			}
-		}
-	}
-
-	private async _doCheckForPromptFiles(tip: ITipDefinition): Promise<void> {
-		const config = tip.excludeWhenPromptFilesExist!;
-		const generation = (this._fileCheckGeneration.get(tip.id) ?? 0) + 1;
-		this._fileCheckGeneration.set(tip.id, generation);
-
-		try {
-			const [promptFiles, agentInstructions] = await Promise.all([
-				this._promptsService.listPromptFiles(config.promptType, CancellationToken.None),
-				config.agentFileType ? this._promptsService.listAgentInstructions(CancellationToken.None) : Promise.resolve([]),
-			]);
-
-			// Discard stale result if a newer check was started while we were awaiting
-			if (this._fileCheckGeneration.get(tip.id) !== generation) {
-				return;
-			}
-
-			const hasPromptFiles = promptFiles.length > 0;
-			const hasAgentFile = config.agentFileType
-				? agentInstructions.some(f => f.type === config.agentFileType)
-				: false;
-			const hasPromptFilesOrAgentFile = hasPromptFiles || hasAgentFile;
-
-			if (tip.id === 'tip.customInstructions' && hasPromptFilesOrAgentFile) {
-				this._instructionFilesEverDetected = true;
-				this._storageService.store(TipEligibilityTracker._INSTRUCTION_FILES_EVER_DETECTED_KEY, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
-			}
-
-			if (hasPromptFilesOrAgentFile) {
-				this._excludedByFiles.add(tip.id);
-			} else {
-				this._excludedByFiles.delete(tip.id);
-			}
-		} catch {
-			if (this._fileCheckGeneration.get(tip.id) !== generation) {
-				return;
-			}
-			if (config.excludeUntilChecked) {
-				this._excludedByFiles.add(tip.id);
-			}
-		}
-	}
-
-	private _persistSet(key: string, set: Set<string>): void {
-		this._storageService.store(key, JSON.stringify([...set]), StorageScope.APPLICATION, StorageTarget.MACHINE);
-	}
-
-	private _readApplicationWithProfileFallback(key: string): string | undefined {
-		const applicationValue = this._storageService.get(key, StorageScope.APPLICATION);
-		if (applicationValue) {
-			return applicationValue;
-		}
-
-		const profileValue = this._storageService.get(key, StorageScope.PROFILE);
-		if (profileValue) {
-			this._storageService.store(key, profileValue, StorageScope.APPLICATION, StorageTarget.MACHINE);
-		}
-
-		return profileValue;
-	}
+	clearDismissedTips(): void;
 }
 
+// Re-export types for backwards compatibility
+export type { ITipDefinition } from './chatTipCatalog.js';
+export { TipEligibilityTracker } from './chatTipEligibilityTracker.js';
+
 export class ChatTipService extends Disposable implements IChatTipService {
 	readonly _serviceBrand: undefined;
 
@@ -654,14 +194,11 @@ export class ChatTipService extends Disposable implements IChatTipService {
 	 */
 	private _contextKeyService: IContextKeyService | undefined;
 
-	private static readonly _DISMISSED_TIP_KEY = 'chat.tip.dismissed';
-	private static readonly _LAST_TIP_ID_KEY = 'chat.tip.lastTipId';
-	private static readonly _YOLO_EVER_ENABLED_KEY = 'chat.tip.yoloModeEverEnabled';
-	private static readonly _THINKING_PHRASES_EVER_MODIFIED_KEY = 'chat.tip.thinkingPhrasesEverModified';
+
 	private readonly _tracker: TipEligibilityTracker;
 	private readonly _createSlashCommandsUsageTracker: CreateSlashCommandsUsageTracker;
-	private _yoloModeEverEnabled: boolean;
 	private _thinkingPhrasesEverModified: boolean;
+	private _tipsHiddenForSession = false;
 	private readonly _tipCommandListener = this._register(new MutableDisposable());
 
 	constructor(
@@ -674,6 +211,7 @@ export class ChatTipService extends Disposable implements IChatTipService {
 		@IChatEntitlementService private readonly _chatEntitlementService: IChatEntitlementService,
 		@ICommandService private readonly _commandService: ICommandService,
 		@ITelemetryService private readonly _telemetryService: ITelemetryService,
+		@IKeybindingService private readonly _keybindingService: IKeybindingService,
 	) {
 		super();
 		this._tracker = this._register(instantiationService.createInstance(TipEligibilityTracker, TIP_CATALOG));
@@ -684,44 +222,101 @@ export class ChatTipService extends Disposable implements IChatTipService {
 			}
 		}));
 
-		// Track whether yolo mode was ever enabled
-		this._yoloModeEverEnabled = this._storageService.getBoolean(ChatTipService._YOLO_EVER_ENABLED_KEY, StorageScope.APPLICATION, false);
-		if (!this._yoloModeEverEnabled && this._configurationService.getValue<boolean>(ChatConfiguration.GlobalAutoApprove)) {
-			this._yoloModeEverEnabled = true;
-			this._storageService.store(ChatTipService._YOLO_EVER_ENABLED_KEY, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
-		}
-		if (!this._yoloModeEverEnabled) {
-			const configListener = this._register(new MutableDisposable());
-			configListener.value = this._configurationService.onDidChangeConfiguration(e => {
-				if (e.affectsConfiguration(ChatConfiguration.GlobalAutoApprove)) {
-					if (this._configurationService.getValue<boolean>(ChatConfiguration.GlobalAutoApprove)) {
-						this._yoloModeEverEnabled = true;
-						this._storageService.store(ChatTipService._YOLO_EVER_ENABLED_KEY, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
-						configListener.clear();
-					}
-				}
-			});
-		}
+		this._register(this._chatService.onDidSubmitRequest(e => {
+			const message = e.message ?? this._chatService.getSession(e.chatSessionResource)?.lastRequest?.message;
+			if (!message) {
+				return;
+			}
+
+			if (this._hasFileOrFolderReference(message)) {
+				this._tracker.recordCommandExecuted(TipTrackingCommands.AttachFilesReferenceUsed);
+			}
 
-		this._thinkingPhrasesEverModified = this._storageService.getBoolean(ChatTipService._THINKING_PHRASES_EVER_MODIFIED_KEY, StorageScope.APPLICATION, false);
+			const slashCommandTrackingId = this._getSlashCommandTrackingId(message);
+			if (slashCommandTrackingId) {
+				this._tracker.recordCommandExecuted(slashCommandTrackingId);
+			}
+
+			this._hideShownTipIfNowIneligible();
+		}));
+
+		this._thinkingPhrasesEverModified = this._storageService.getBoolean(ChatTipStorageKeys.ThinkingPhrasesEverModified, StorageScope.APPLICATION, false);
 		if (!this._thinkingPhrasesEverModified && this._isSettingModified(ChatConfiguration.ThinkingPhrases)) {
 			this._thinkingPhrasesEverModified = true;
-			this._storageService.store(ChatTipService._THINKING_PHRASES_EVER_MODIFIED_KEY, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
+			this._storageService.store(ChatTipStorageKeys.ThinkingPhrasesEverModified, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
 		}
 		if (!this._thinkingPhrasesEverModified) {
 			this._register(this._configurationService.onDidChangeConfiguration(e => {
 				if (e.affectsConfiguration(ChatConfiguration.ThinkingPhrases)) {
 					this._thinkingPhrasesEverModified = true;
-					this._storageService.store(ChatTipService._THINKING_PHRASES_EVER_MODIFIED_KEY, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
+					this._storageService.store(ChatTipStorageKeys.ThinkingPhrasesEverModified, true, StorageScope.APPLICATION, StorageTarget.MACHINE);
 				}
 			}));
 		}
 	}
 
+	private _hasFileOrFolderReference(message: IParsedChatRequest): boolean {
+		return message.parts.some(part => {
+			if (part.kind !== ChatRequestDynamicVariablePart.Kind) {
+				return false;
+			}
+
+			const dynamicPart = part as ChatRequestDynamicVariablePart;
+			return dynamicPart.isFile === true || dynamicPart.isDirectory === true;
+		});
+	}
+
+	private _getSlashCommandTrackingId(message: IParsedChatRequest): string | undefined {
+		for (const part of message.parts) {
+			if (part.kind === ChatRequestSlashCommandPart.Kind) {
+				const slashCommand = (part as ChatRequestSlashCommandPart).slashCommand.command;
+				return this._toSlashCommandTrackingId(slashCommand);
+			}
+
+			if (part.kind === ChatRequestAgentSubcommandPart.Kind) {
+				const subCommand = (part as ChatRequestAgentSubcommandPart).command.name;
+				return this._toSlashCommandTrackingId(subCommand);
+			}
+		}
+
+		const trimmed = message.text.trimStart();
+		const match = /^(?:@\S+\s+)?\/(init|create-(?:instructions|prompt|agent|skill)|fork)(?:\s|$)/.exec(trimmed);
+		return match ? this._toSlashCommandTrackingId(match[1]) : undefined;
+	}
+
+	private _toSlashCommandTrackingId(command: string): string | undefined {
+		switch (command) {
+			case 'init':
+			case 'create-instructions':
+				return CREATE_AGENT_INSTRUCTIONS_TRACKING_COMMAND;
+			case 'create-prompt':
+				return CREATE_PROMPT_TRACKING_COMMAND;
+			case 'create-agent':
+				return CREATE_AGENT_TRACKING_COMMAND;
+			case 'create-skill':
+				return CREATE_SKILL_TRACKING_COMMAND;
+			case 'fork':
+				return FORK_CONVERSATION_TRACKING_COMMAND;
+			default:
+				return undefined;
+		}
+	}
+
+	recordSlashCommandUsage(command: string): void {
+		const trackingId = this._toSlashCommandTrackingId(command);
+		if (!trackingId) {
+			return;
+		}
+
+		this._tracker.recordCommandExecuted(trackingId);
+		this._hideShownTipIfNowIneligible();
+	}
+
 	resetSession(): void {
 		this._shownTip = undefined;
 		this._tipRequestId = undefined;
 		this._contextKeyService = undefined;
+		this._tipsHiddenForSession = false;
 	}
 
 	dismissTip(): void {
@@ -729,7 +324,7 @@ export class ChatTipService extends Disposable implements IChatTipService {
 			this._logTipTelemetry(this._shownTip.id, 'dismissed');
 			const dismissed = new Set(this._getDismissedTipIds());
 			dismissed.add(this._shownTip.id);
-			this._storageService.store(ChatTipService._DISMISSED_TIP_KEY, JSON.stringify([...dismissed]), StorageScope.APPLICATION, StorageTarget.MACHINE);
+			this._storageService.store(ChatTipStorageKeys.DismissedTips, JSON.stringify([...dismissed]), StorageScope.APPLICATION, StorageTarget.MACHINE);
 		}
 		// Keep the current tip reference so callers can navigate relative to it
 		// (for example, dismiss -> next should mirror next/previous behavior).
@@ -737,17 +332,23 @@ export class ChatTipService extends Disposable implements IChatTipService {
 		this._onDidDismissTip.fire();
 	}
 
+	dismissTipForSession(): void {
+		this.dismissTip();
+		this.hideTipsForSession();
+	}
+
 	clearDismissedTips(): void {
-		this._storageService.remove(ChatTipService._DISMISSED_TIP_KEY, StorageScope.APPLICATION);
-		this._storageService.remove(ChatTipService._DISMISSED_TIP_KEY, StorageScope.PROFILE);
+		this._storageService.remove(ChatTipStorageKeys.DismissedTips, StorageScope.APPLICATION);
+		this._storageService.remove(ChatTipStorageKeys.DismissedTips, StorageScope.PROFILE);
 		this._shownTip = undefined;
 		this._tipRequestId = undefined;
 		this._contextKeyService = undefined;
+		this._tipsHiddenForSession = false;
 		this._onDidDismissTip.fire();
 	}
 
 	private _getDismissedTipIds(): string[] {
-		const raw = this._readApplicationWithProfileFallback(ChatTipService._DISMISSED_TIP_KEY);
+		const raw = this._readApplicationWithProfileFallback(ChatTipStorageKeys.DismissedTips);
 		if (!raw) {
 			return [];
 		}
@@ -781,6 +382,17 @@ export class ChatTipService extends Disposable implements IChatTipService {
 		this._onDidHideTip.fire();
 	}
 
+	hideTipsForSession(): void {
+		if (this._tipsHiddenForSession) {
+			return;
+		}
+
+		this._tipsHiddenForSession = true;
+		this._shownTip = undefined;
+		this._tipRequestId = undefined;
+		this._onDidHideTip.fire();
+	}
+
 	async disableTips(): Promise<void> {
 		if (this._shownTip) {
 			this._logTipTelemetry(this._shownTip.id, 'disabled');
@@ -804,6 +416,10 @@ export class ChatTipService extends Disposable implements IChatTipService {
 			return undefined;
 		}
 
+		if (this._tipsHiddenForSession) {
+			return undefined;
+		}
+
 		// Store the scoped context key service for later navigation calls
 		this._contextKeyService = contextKeyService;
 
@@ -822,6 +438,12 @@ export class ChatTipService extends Disposable implements IChatTipService {
 			return undefined;
 		}
 
+		// Only show tips when there is exactly one foreground chat session visible.
+		const foregroundSessionCount = contextKeyService.getContextKeyValue<number>(ChatContextKeys.foregroundSessionCount.key);
+		if (foregroundSessionCount !== 1) {
+			return undefined;
+		}
+
 		// Don't show tips when chat quota is exceeded, the upgrade widget is more relevant
 		if (this._isChatQuotaExceeded(contextKeyService)) {
 			return undefined;
@@ -829,15 +451,39 @@ export class ChatTipService extends Disposable implements IChatTipService {
 
 		// Return the already-shown tip for stable rerenders
 		if (this._tipRequestId === 'welcome' && this._shownTip) {
+			if (this._shownTip.id !== 'tip.switchToAuto') {
+				const switchToAutoTip = TIP_CATALOG.find(tip => tip.id === 'tip.switchToAuto');
+				if (switchToAutoTip) {
+					const dismissedIds = new Set(this._getDismissedTipIds());
+					if (!dismissedIds.has(switchToAutoTip.id) && this._isEligible(switchToAutoTip, contextKeyService)) {
+						this._shownTip = switchToAutoTip;
+						this._storageService.store(ChatTipStorageKeys.LastTipId, switchToAutoTip.id, StorageScope.APPLICATION, StorageTarget.USER);
+						const tip = this._createTip(switchToAutoTip);
+						this._logTipTelemetry(switchToAutoTip.id, 'shown');
+						this._trackTipCommandClicks(switchToAutoTip);
+						this._onDidNavigateTip.fire(tip);
+						return tip;
+					}
+				}
+			}
+
 			if (!this._isEligible(this._shownTip, contextKeyService)) {
+				if (this._tracker.isExcluded(this._shownTip)) {
+					this.hideTip();
+					return undefined;
+				}
+
 				const nextTip = this._findNextEligibleTip(this._shownTip.id, contextKeyService);
 				if (nextTip) {
 					this._shownTip = nextTip;
-					this._storageService.store(ChatTipService._LAST_TIP_ID_KEY, nextTip.id, StorageScope.APPLICATION, StorageTarget.USER);
+					this._storageService.store(ChatTipStorageKeys.LastTipId, nextTip.id, StorageScope.APPLICATION, StorageTarget.USER);
 					const tip = this._createTip(nextTip);
 					this._onDidNavigateTip.fire(tip);
 					return tip;
 				}
+
+				this.hideTip();
+				return undefined;
 			}
 			return this._createTip(this._shownTip);
 		}
@@ -866,36 +512,38 @@ export class ChatTipService extends Disposable implements IChatTipService {
 		return undefined;
 	}
 
+	private _hideShownTipIfNowIneligible(): void {
+		if (!this._shownTip || !this._contextKeyService) {
+			return;
+		}
+
+		if (this._tipsHiddenForSession) {
+			return;
+		}
+
+		if (this._isEligible(this._shownTip, this._contextKeyService)) {
+			return;
+		}
+
+		this.hideTip();
+	}
+
 	private _pickTip(sourceId: string, contextKeyService: IContextKeyService): IChatTip | undefined {
 		this._createSlashCommandsUsageTracker.syncContextKey(contextKeyService);
 		// Record the current mode for future eligibility decisions.
 		this._tracker.recordCurrentMode(contextKeyService);
 
 		const dismissedIds = new Set(this._getDismissedTipIds());
-		let selectedTip: ITipDefinition | undefined;
+		const eligibleTips = TIP_CATALOG.filter(tip => !dismissedIds.has(tip.id) && this._isEligible(tip, contextKeyService));
 
-		// Determine where to start in the catalog based on the last-shown tip.
-		const lastTipId = this._readApplicationWithProfileFallback(ChatTipService._LAST_TIP_ID_KEY);
-		const lastCatalogIndex = lastTipId ? TIP_CATALOG.findIndex(tip => tip.id === lastTipId) : -1;
-		const startIndex = lastCatalogIndex === -1 ? 0 : (lastCatalogIndex + 1) % TIP_CATALOG.length;
-
-		// Pass 1: walk TIP_CATALOG in a ring, picking the first tip that is both
-		// not dismissed and eligible for the current context.
-		for (let i = 0; i < TIP_CATALOG.length; i++) {
-			const idx = (startIndex + i) % TIP_CATALOG.length;
-			const candidate = TIP_CATALOG[idx];
-			if (!dismissedIds.has(candidate.id) && this._isEligible(candidate, contextKeyService)) {
-				selectedTip = candidate;
-				break;
-			}
-		}
+		const selectedTip = this._selectTipByTier(eligibleTips);
 
 		if (!selectedTip) {
 			return undefined;
 		}
 
-		// Persist the selected tip id so the next use advances to the following one.
-		this._storageService.store(ChatTipService._LAST_TIP_ID_KEY, selectedTip.id, StorageScope.APPLICATION, StorageTarget.USER);
+		// Persist the selected tip ID for compatibility with existing storage consumers.
+		this._storageService.store(ChatTipStorageKeys.LastTipId, selectedTip.id, StorageScope.APPLICATION, StorageTarget.USER);
 
 		// Record that we've shown a tip this session
 		this._tipRequestId = sourceId;
@@ -907,6 +555,21 @@ export class ChatTipService extends Disposable implements IChatTipService {
 		return this._createTip(selectedTip);
 	}
 
+	private _selectTipByTier(eligibleTips: readonly ITipDefinition[]): ITipDefinition | undefined {
+		const foundationalTips = eligibleTips.filter(tip => tip.tier === ChatTipTier.Foundational);
+		if (foundationalTips.length) {
+			return this._sortByPriorityAndCatalogOrder(foundationalTips)[0];
+		}
+
+		const qolTips = eligibleTips.filter(tip => tip.tier === ChatTipTier.Qol);
+		if (!qolTips.length) {
+			return undefined;
+		}
+
+		const randomIndex = Math.floor(Math.random() * qolTips.length);
+		return qolTips[randomIndex];
+	}
+
 	navigateToNextTip(): IChatTip | undefined {
 		if (!this._contextKeyService) {
 			return undefined;
@@ -921,37 +584,144 @@ export class ChatTipService extends Disposable implements IChatTipService {
 		return this._navigateTip(-1, this._contextKeyService);
 	}
 
+	getNextEligibleTip(): IChatTip | undefined {
+		if (!this._contextKeyService || !this._shownTip) {
+			return undefined;
+		}
+
+		const contextKeyService = this._contextKeyService;
+		this._createSlashCommandsUsageTracker.syncContextKey(contextKeyService);
+		const currentTipId = this._shownTip.id;
+		const orderedTips = this._getOrderedEligibleTips(contextKeyService, { includeTipId: currentTipId });
+		if (!orderedTips.length) {
+			return undefined;
+		}
+
+		const currentIndex = orderedTips.findIndex(tip => tip.id === currentTipId);
+		const candidate = this._getNextTipFromOrderedList(orderedTips, currentIndex, currentTipId);
+		if (candidate) {
+			// Found the next eligible tip - update state and return it
+			this._shownTip = candidate;
+			this._tipRequestId = 'welcome';
+			this._storageService.store(ChatTipStorageKeys.LastTipId, candidate.id, StorageScope.APPLICATION, StorageTarget.USER);
+			this._logTipTelemetry(candidate.id, 'shown');
+			this._trackTipCommandClicks(candidate);
+			return this._createTip(candidate);
+		}
+
+		return undefined;
+	}
+
+	private _getNextTipFromOrderedList(orderedTips: readonly ITipDefinition[], startIndex: number, currentTipId: string): ITipDefinition | undefined {
+		if (!orderedTips.length) {
+			return undefined;
+		}
+
+		const fallbackIndex = 0;
+		const normalizedStartIndex = startIndex === -1 ? fallbackIndex : startIndex;
+		for (let i = 1; i <= orderedTips.length; i++) {
+			const index = (normalizedStartIndex + i) % orderedTips.length;
+			const candidate = orderedTips[index];
+			if (candidate.id !== currentTipId) {
+				return candidate;
+			}
+		}
+
+		return undefined;
+	}
+
+	hasMultipleTips(): boolean {
+		if (!this._contextKeyService) {
+			return false;
+		}
+
+		this._createSlashCommandsUsageTracker.syncContextKey(this._contextKeyService);
+		return this._hasNavigableTip(this._contextKeyService);
+	}
+
 	private _navigateTip(direction: 1 | -1, contextKeyService: IContextKeyService): IChatTip | undefined {
 		this._createSlashCommandsUsageTracker.syncContextKey(contextKeyService);
 		if (!this._shownTip) {
 			return undefined;
 		}
+		const orderedTips = this._getOrderedEligibleTips(contextKeyService);
+		if (!orderedTips.length) {
+			return undefined;
+		}
 
-		const currentIndex = TIP_CATALOG.findIndex(t => t.id === this._shownTip!.id);
-		if (currentIndex === -1) {
+		const currentIndex = orderedTips.findIndex(tip => tip.id === this._shownTip!.id);
+		if (orderedTips.length === 1 && currentIndex !== -1) {
 			return undefined;
 		}
 
-		const dismissedIds = new Set(this._getDismissedTipIds());
-		for (let i = 1; i < TIP_CATALOG.length; i++) {
-			const idx = ((currentIndex + direction * i) % TIP_CATALOG.length + TIP_CATALOG.length) % TIP_CATALOG.length;
-			const candidate = TIP_CATALOG[idx];
-			if (!dismissedIds.has(candidate.id) && this._isEligible(candidate, contextKeyService)) {
-				this._logTipTelemetry(this._shownTip.id, direction === 1 ? 'navigateNext' : 'navigatePrevious');
-				this._shownTip = candidate;
-				this._tipRequestId = 'welcome';
-				this._storageService.store(ChatTipService._LAST_TIP_ID_KEY, candidate.id, StorageScope.APPLICATION, StorageTarget.USER);
-				this._logTipTelemetry(candidate.id, 'shown');
-				this._trackTipCommandClicks(candidate);
-				const tip = this._createTip(candidate);
-				this._onDidNavigateTip.fire(tip);
-				return tip;
-			}
+		const fallbackIndex = direction === 1 ? 0 : orderedTips.length - 1;
+		const nextIndex = currentIndex === -1
+			? fallbackIndex
+			: (currentIndex + direction + orderedTips.length) % orderedTips.length;
+		const candidate = orderedTips[nextIndex];
+		if (candidate) {
+			this._logTipTelemetry(this._shownTip.id, direction === 1 ? 'navigateNext' : 'navigatePrevious');
+			this._shownTip = candidate;
+			this._tipRequestId = 'welcome';
+			this._storageService.store(ChatTipStorageKeys.LastTipId, candidate.id, StorageScope.APPLICATION, StorageTarget.USER);
+			this._logTipTelemetry(candidate.id, 'shown');
+			this._trackTipCommandClicks(candidate);
+			const tip = this._createTip(candidate);
+			this._onDidNavigateTip.fire(tip);
+			return tip;
 		}
 
 		return undefined;
 	}
 
+	private _hasNavigableTip(contextKeyService: IContextKeyService): boolean {
+		const orderedTips = this._getOrderedEligibleTips(contextKeyService);
+		if (!orderedTips.length) {
+			return false;
+		}
+
+		if (!this._shownTip) {
+			return orderedTips.length > 1;
+		}
+
+		if (orderedTips.length > 1) {
+			return true;
+		}
+
+		return orderedTips[0].id !== this._shownTip.id;
+	}
+
+	private _getOrderedEligibleTips(contextKeyService: IContextKeyService, options?: { excludeShownTip?: boolean; includeTipId?: string }): ITipDefinition[] {
+		const dismissedIds = new Set(this._getDismissedTipIds());
+		const eligibleTips = TIP_CATALOG.filter(tip => {
+			if (options?.includeTipId && tip.id === options.includeTipId) {
+				return true;
+			}
+			if (options?.excludeShownTip && this._shownTip && tip.id === this._shownTip.id) {
+				return false;
+			}
+			return !dismissedIds.has(tip.id) && this._isEligible(tip, contextKeyService);
+		});
+
+		const foundationalTips = this._sortByPriorityAndCatalogOrder(eligibleTips.filter(tip => tip.tier === ChatTipTier.Foundational));
+		const qolTips = this._sortByPriorityAndCatalogOrder(eligibleTips.filter(tip => tip.tier === ChatTipTier.Qol));
+		return [...foundationalTips, ...qolTips];
+	}
+
+	private _sortByPriorityAndCatalogOrder(tips: readonly ITipDefinition[]): ITipDefinition[] {
+		return [...tips].sort((a, b) => {
+			const aPriority = a.priority ?? Number.POSITIVE_INFINITY;
+			const bPriority = b.priority ?? Number.POSITIVE_INFINITY;
+			if (aPriority !== bPriority) {
+				return aPriority - bPriority;
+			}
+
+			const aCatalogIndex = TIP_CATALOG.findIndex(tip => tip.id === a.id);
+			const bCatalogIndex = TIP_CATALOG.findIndex(tip => tip.id === b.id);
+			return aCatalogIndex - bCatalogIndex;
+		});
+	}
+
 	private _isEligible(tip: ITipDefinition, contextKeyService: IContextKeyService): boolean {
 		if (tip.onlyWhenModelIds?.length) {
 			const currentModelId = this._getCurrentChatModelId(contextKeyService);
@@ -971,17 +741,6 @@ export class ChatTipService extends Disposable implements IChatTipService {
 		if (this._tracker.isExcluded(tip)) {
 			return false;
 		}
-		if (tip.id === 'tip.yoloMode') {
-			if (this._yoloModeEverEnabled) {
-				this._logService.debug('#ChatTips: tip excluded because yolo mode was previously enabled', tip.id);
-				return false;
-			}
-			const inspected = this._configurationService.inspect<boolean>(ChatConfiguration.GlobalAutoApprove);
-			if (inspected.policyValue === false) {
-				this._logService.debug('#ChatTips: tip excluded because policy restricts auto-approve', tip.id);
-				return false;
-			}
-		}
 		if (tip.id === 'tip.thinkingPhrases' && this._thinkingPhrasesEverModified) {
 			this._logService.debug('#ChatTips: tip excluded because thinking phrases setting was previously modified', tip.id);
 			return false;
@@ -1050,13 +809,23 @@ export class ChatTipService extends Disposable implements IChatTipService {
 	}
 
 	private _createTip(tipDef: ITipDefinition): IChatTip {
-		const markdown = new MarkdownString(tipDef.message, {
-			isTrusted: tipDef.enabledCommands ? { enabledCommands: tipDef.enabledCommands } : false,
+		// Build the tip message with dynamic keybindings and command labels
+		const ctx: ITipBuildContext = { keybindingService: this._keybindingService };
+		const rawMessage = tipDef.buildMessage(ctx);
+
+		// Add "Tip:" prefix once here, avoiding duplication in individual tip definitions
+		const prefixedMessage = localize('tipPrefix', "**Tip:** {0}", rawMessage.value);
+
+		// Auto-extract enabled commands from the built message
+		const enabledCommands = extractCommandIds(prefixedMessage);
+
+		const markdown = new MarkdownString(prefixedMessage, {
+			isTrusted: enabledCommands.length > 0 ? { enabledCommands } : false,
 		});
 		return {
 			id: tipDef.id,
 			content: markdown,
-			enabledCommands: tipDef.enabledCommands,
+			enabledCommands,
 		};
 	}
 
@@ -1070,10 +839,16 @@ export class ChatTipService extends Disposable implements IChatTipService {
 
 	private _trackTipCommandClicks(tip: ITipDefinition): void {
 		this._tipCommandListener.clear();
-		if (!tip.enabledCommands?.length) {
+
+		// Build message to extract enabled commands dynamically
+		const ctx: ITipBuildContext = { keybindingService: this._keybindingService };
+		const rawMessage = tip.buildMessage(ctx);
+		const enabledCommands = extractCommandIds(rawMessage.value);
+
+		if (!enabledCommands.length) {
 			return;
 		}
-		const enabledCommandSet = new Set(tip.enabledCommands);
+		const enabledCommandSet = new Set(enabledCommands);
 		const dismissCommandSet = new Set(tip.dismissWhenCommandsClicked);
 		this._tipCommandListener.value = this._commandService.onDidExecuteCommand(e => {
 			if (enabledCommandSet.has(e.commandId) && this._shownTip?.id === tip.id) {
@@ -1081,6 +856,7 @@ export class ChatTipService extends Disposable implements IChatTipService {
 				if (dismissCommandSet.has(e.commandId)) {
 					this.dismissTip();
 				}
+				this.hideTipsForSession();
 			}
 		});
 	}
diff --git a/src/vs/workbench/contrib/chat/browser/chatTipStorageKeys.ts b/src/vs/workbench/contrib/chat/browser/chatTipStorageKeys.ts
new file mode 100644
index 0000000000000..f16af0caf0d8f
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/chatTipStorageKeys.ts
@@ -0,0 +1,48 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+/**
+ * Storage keys used by ChatTipService for persisting tip state.
+ */
+export const ChatTipStorageKeys = {
+	/** IDs of tips that have been permanently dismissed by the user. */
+	DismissedTips: 'chat.tip.dismissed',
+	/** The ID of the last tip that was shown, for round-robin selection. */
+	LastTipId: 'chat.tip.lastTipId',
+	/** Whether the user has ever modified the thinking phrases setting. */
+	ThinkingPhrasesEverModified: 'chat.tip.thinkingPhrasesEverModified',
+};
+
+/**
+ * Storage keys used by TipEligibilityTracker for tracking user signals.
+ */
+export const TipEligibilityStorageKeys = {
+	/** Command IDs that have been executed (for excludeWhenCommandsExecuted). */
+	ExecutedCommands: 'chat.tips.executedCommands',
+	/** Chat modes that have been used (for excludeWhenModesUsed). */
+	UsedModes: 'chat.tips.usedModes',
+	/** Tool IDs that have been invoked (for excludeWhenToolsInvoked). */
+	InvokedTools: 'chat.tips.invokedTools',
+};
+
+/**
+ * Synthetic command IDs used to track user actions that don't have real commands.
+ * These are recorded when the user performs the action, allowing tips to be excluded
+ * via excludeWhenCommandsExecuted.
+ */
+export const TipTrackingCommands = {
+	/** Tracked when user attaches a file/folder reference with #. */
+	AttachFilesReferenceUsed: 'chat.tips.attachFiles.referenceUsed',
+	/** Tracked when user executes /init or /create-instructions. */
+	CreateAgentInstructionsUsed: 'chat.tips.createAgentInstructions.commandUsed',
+	/** Tracked when user executes /create-prompt. */
+	CreatePromptUsed: 'chat.tips.createPrompt.commandUsed',
+	/** Tracked when user executes /create-agent. */
+	CreateAgentUsed: 'chat.tips.createAgent.commandUsed',
+	/** Tracked when user executes /create-skill. */
+	CreateSkillUsed: 'chat.tips.createSkill.commandUsed',
+	/** Tracked when user executes /fork. */
+	ForkConversationUsed: 'chat.tips.forkConversation.commandUsed',
+} as const;
diff --git a/src/vs/workbench/contrib/chat/browser/chatWindowNotifier.ts b/src/vs/workbench/contrib/chat/browser/chatWindowNotifier.ts
index abece4b0a87a0..1360bc61881af 100644
--- a/src/vs/workbench/contrib/chat/browser/chatWindowNotifier.ts
+++ b/src/vs/workbench/contrib/chat/browser/chatWindowNotifier.ts
@@ -11,15 +11,14 @@ import { autorunDelta, autorunIterableDelta } from '../../../../base/common/obse
 import { URI } from '../../../../base/common/uri.js';
 import { localize } from '../../../../nls.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
-import { ICommandService } from '../../../../platform/commands/common/commands.js';
 import { FocusMode } from '../../../../platform/native/common/native.js';
 import { IWorkbenchContribution } from '../../../common/contributions.js';
 import { IHostService } from '../../../services/host/browser/host.js';
 import { IChatModel, IChatRequestNeedsInputInfo } from '../common/model/chatModel.js';
-import { IChatService } from '../common/chatService/chatService.js';
+import { IChatService, IChatToolInvocation, ToolConfirmKind } from '../common/chatService/chatService.js';
+import { migrateLegacyTerminalToolSpecificData } from '../common/chat.js';
 import { ChatConfiguration, ChatNotificationMode } from '../common/constants.js';
 import { IChatWidgetService } from './chat.js';
-import { AcceptToolConfirmationActionId, IToolConfirmationActionContext } from './actions/chatToolActions.js';
 
 /**
  * Observes all live chat models and triggers OS notifications when any model
@@ -36,7 +35,6 @@ export class ChatWindowNotifier extends Disposable implements IWorkbenchContribu
 		@IChatWidgetService private readonly _chatWidgetService: IChatWidgetService,
 		@IHostService private readonly _hostService: IHostService,
 		@IConfigurationService private readonly _configurationService: IConfigurationService,
-		@ICommandService private readonly _commandService: ICommandService,
 	) {
 		super();
 
@@ -95,7 +93,7 @@ export class ChatWindowNotifier extends Disposable implements IWorkbenchContribu
 		}
 
 		// Create OS notification
-		const notificationTitle = info.title ? localize('chatTitle', "Chat: {0}", info.title) : localize('chat.untitledChat', "Untitled Chat");
+		const notificationTitle = info.title ? localize('chatTitle', "Session: {0}", info.title) : localize('chat.untitledChat', "Untitled Session");
 
 		const cts = new CancellationTokenSource();
 		this._activeNotifications.set(sessionResource, toDisposable(() => cts.dispose(true)));
@@ -105,35 +103,75 @@ export class ChatWindowNotifier extends Disposable implements IWorkbenchContribu
 
 		try {
 			const actionLabel = isQuestionCarousel
-				? localize('openChatAction', "Open Chat")
+				? localize('openChatAction', "Open Session")
 				: localize('allowAction', "Allow");
-			const body = info.detail
-				? this._sanitizeOSToastText(info.detail)
-				: isQuestionCarousel
-					? localize('questionCarouselDetail', "Questions need your input.")
-					: localize('notificationDetail', "Approval needed to continue.");
 
 			const result = await this._hostService.showToast({
 				title: this._sanitizeOSToastText(notificationTitle),
-				body,
+				body: this._getNotificationBody(sessionResource, info, isQuestionCarousel),
 				actions: [actionLabel],
 			}, cts.token);
 
+			if (result.actionIndex === 0 && !isQuestionCarousel && this._confirmAllow(sessionResource)) {
+				return; // skip focusing/opening chat if we successfully confirmed the tool invocation from the toast action
+			}
+
 			if (result.clicked || typeof result.actionIndex === 'number') {
 				await this._hostService.focus(targetWindow, { mode: FocusMode.Force });
 
 				const widget = await this._chatWidgetService.openSession(sessionResource);
 				widget?.focusInput();
-
-				if (result.actionIndex === 0 && !isQuestionCarousel) {
-					await this._commandService.executeCommand(AcceptToolConfirmationActionId, { sessionResource } satisfies IToolConfirmationActionContext);
-				}
 			}
 		} finally {
 			this._clearNotification(sessionResource);
 		}
 	}
 
+	private _confirmAllow(sessionResource: URI): boolean {
+		const model = this._chatService.getSession(sessionResource);
+		const lastResponse = model?.lastRequest?.response;
+		if (!lastResponse) {
+			return false;
+		}
+		for (const part of lastResponse.response.value) {
+			const state = part.kind === 'toolInvocation' ? part.state.get() : undefined;
+			if (state?.type === IChatToolInvocation.StateKind.WaitingForConfirmation || state?.type === IChatToolInvocation.StateKind.WaitingForPostApproval) {
+				state.confirm({ type: ToolConfirmKind.UserAction });
+				return true;
+			}
+		}
+		return false;
+	}
+
+	private _getNotificationBody(sessionResource: URI, info: IChatRequestNeedsInputInfo, isQuestionCarousel: boolean): string {
+		if (isQuestionCarousel) {
+			return localize('questionCarouselDetail', "Questions need your input.");
+		}
+		const terminalCommand = this._getPendingTerminalCommand(sessionResource);
+		if (terminalCommand) {
+			return this._sanitizeOSToastText(terminalCommand);
+		}
+		if (info.detail) {
+			return this._sanitizeOSToastText(info.detail);
+		}
+		return localize('notificationDetail', "Approval needed to continue.");
+	}
+
+	private _getPendingTerminalCommand(sessionResource: URI): string | undefined {
+		const model = this._chatService.getSession(sessionResource);
+		const lastResponse = model?.lastRequest?.response;
+		if (!lastResponse?.response?.value) {
+			return undefined;
+		}
+		for (const part of lastResponse.response.value) {
+			if (part.kind === 'toolInvocation' && part.toolSpecificData?.kind === 'terminal') {
+				const terminalData = migrateLegacyTerminalToolSpecificData(part.toolSpecificData);
+				return terminalData.commandLine.forDisplay ?? terminalData.commandLine.userEdited ?? terminalData.commandLine.toolEdited ?? terminalData.commandLine.original;
+			}
+		}
+		return undefined;
+	}
+
 	private _isQuestionCarouselPending(sessionResource: URI): boolean {
 		const model = this._chatService.getSession(sessionResource);
 		const lastResponse = model?.lastRequest?.response;
diff --git a/src/vs/workbench/contrib/chat/browser/claudePluginRecommendations.ts b/src/vs/workbench/contrib/chat/browser/claudePluginRecommendations.ts
new file mode 100644
index 0000000000000..959895bdf1085
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/claudePluginRecommendations.ts
@@ -0,0 +1,80 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { localize } from '../../../../nls.js';
+import { INotificationService, NeverShowAgainScope, Severity } from '../../../../platform/notification/common/notification.js';
+import { IWorkbenchContribution } from '../../../common/contributions.js';
+import { IExtensionsWorkbenchService } from '../../extensions/common/extensions.js';
+import { IChatService } from '../common/chatService/chatService.js';
+import { IPluginMarketplaceService } from '../common/plugins/pluginMarketplaceService.js';
+
+export class AgentPluginRecommendations extends Disposable implements IWorkbenchContribution {
+	static readonly ID = 'workbench.contrib.agentPluginRecommendations';
+
+	private _hasNotified = false;
+
+	constructor(
+		@IChatService private readonly _chatService: IChatService,
+		@IPluginMarketplaceService private readonly _pluginMarketplaceService: IPluginMarketplaceService,
+		@INotificationService private readonly _notificationService: INotificationService,
+		@IExtensionsWorkbenchService private readonly _extensionsWorkbenchService: IExtensionsWorkbenchService,
+	) {
+		super();
+
+		this._register(this._chatService.onDidSubmitRequest(() => {
+			if (!this._hasNotified) {
+				this._hasNotified = true;
+				this._checkForRecommendedPlugins();
+			}
+		}));
+	}
+
+	private _checkForRecommendedPlugins(): void {
+		const recommended = this._pluginMarketplaceService.recommendedPlugins.get();
+		if (recommended.size === 0) {
+			return;
+		}
+
+		// Build a set of installed plugin keys ("name@marketplace") from
+		// storage without triggering any network fetch.
+		const installedKeys = new Set<string>();
+		for (const entry of this._pluginMarketplaceService.installedPlugins.get()) {
+			const key = `${entry.plugin.name}@${entry.plugin.marketplace}`;
+			installedKeys.add(key);
+		}
+
+		let uninstalledCount = 0;
+		for (const key of recommended) {
+			if (!installedKeys.has(key)) {
+				uninstalledCount++;
+			}
+		}
+
+		if (uninstalledCount === 0) {
+			return;
+		}
+
+		this._notificationService.prompt(
+			Severity.Info,
+			uninstalledCount === 1
+				? localize('agentPluginRecommendation.one', "This workspace recommends 1 agent plugin.")
+				: localize('agentPluginRecommendation.many', "This workspace recommends {0} agent plugins.", uninstalledCount),
+			[{
+				label: localize('showPlugins', "Show Plugins"),
+				run: () => {
+					this._extensionsWorkbenchService.openSearch('@agentPlugins @recommended');
+				}
+			}],
+			{
+				neverShowAgain: {
+					id: 'agentPluginRecommendations.dismissed',
+					scope: NeverShowAgainScope.WORKSPACE,
+					isSecondary: true,
+				}
+			}
+		);
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/createSlashCommandsUsageTracker.ts b/src/vs/workbench/contrib/chat/browser/createSlashCommandsUsageTracker.ts
index 0ad8f07e43c24..eea1a645a61ed 100644
--- a/src/vs/workbench/contrib/chat/browser/createSlashCommandsUsageTracker.ts
+++ b/src/vs/workbench/contrib/chat/browser/createSlashCommandsUsageTracker.ts
@@ -21,13 +21,12 @@ export class CreateSlashCommandsUsageTracker extends Disposable {
 		super();
 
 		this._register(this._chatService.onDidSubmitRequest(e => {
-			const model = this._chatService.getSession(e.chatSessionResource);
-			const lastRequest = model?.lastRequest;
-			if (!lastRequest) {
+			const message = e.message ?? this._chatService.getSession(e.chatSessionResource)?.lastRequest?.message;
+			if (!message) {
 				return;
 			}
 
-			for (const part of lastRequest.message.parts) {
+			for (const part of message.parts) {
 				if (part.kind === ChatRequestSlashCommandPart.Kind) {
 					const slash = part as ChatRequestSlashCommandPart;
 					if (CreateSlashCommandsUsageTracker._isCreateSlashCommand(slash.slashCommand.command)) {
@@ -38,8 +37,8 @@ export class CreateSlashCommandsUsageTracker extends Disposable {
 			}
 
 			// Fallback when parsing doesn't produce a slash command part.
-			const trimmed = lastRequest.message.text.trimStart();
-			const match = /^\/(create-(?:instruction|prompt|agent|skill))(?:\s|$)/.exec(trimmed);
+			const trimmed = message.text.trimStart();
+			const match = /^\/(create-(?:instructions|prompt|agent|skill))(?:\s|$)/.exec(trimmed);
 			if (match && CreateSlashCommandsUsageTracker._isCreateSlashCommand(match[1])) {
 				this._markUsed();
 			}
@@ -66,7 +65,7 @@ export class CreateSlashCommandsUsageTracker extends Disposable {
 
 	private static _isCreateSlashCommand(command: string): boolean {
 		switch (command) {
-			case 'create-instruction':
+			case 'create-instructions':
 			case 'create-prompt':
 			case 'create-agent':
 			case 'create-skill':
diff --git a/src/vs/workbench/contrib/chat/browser/enablementActions.ts b/src/vs/workbench/contrib/chat/browser/enablementActions.ts
new file mode 100644
index 0000000000000..4b49ed7b42605
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/enablementActions.ts
@@ -0,0 +1,60 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Action, IAction } from '../../../../base/common/actions.js';
+import { localize } from '../../../../nls.js';
+import { IWorkspaceContextService, WorkbenchState } from '../../../../platform/workspace/common/workspace.js';
+import { ContributionEnablementState, IEnablementModel, isContributionDisabled } from '../common/enablement.js';
+
+/**
+ * Creates the four standard enablement actions (Enable, Enable Workspace,
+ * Disable, Disable Workspace) for a contribution identified by a string key.
+ */
+export function createEnablementActions(
+	key: string,
+	enablementModel: IEnablementModel,
+	idPrefix: string,
+): [enable: Action, enableWorkspace: Action, disable: Action, disableWorkspace: Action] {
+	return [
+		new Action(`${idPrefix}.enable`, localize('enable', "Enable"), undefined, true,
+			() => { enablementModel.setEnabled(key, ContributionEnablementState.EnabledProfile); return Promise.resolve(); }),
+		new Action(`${idPrefix}.enableForWorkspace`, localize('enableForWorkspace', "Enable (Workspace)"), undefined, true,
+			() => { enablementModel.setEnabled(key, ContributionEnablementState.EnabledWorkspace); return Promise.resolve(); }),
+		new Action(`${idPrefix}.disable`, localize('disable', "Disable"), undefined, true,
+			() => { enablementModel.setEnabled(key, ContributionEnablementState.DisabledProfile); return Promise.resolve(); }),
+		new Action(`${idPrefix}.disableForWorkspace`, localize('disableForWorkspace', "Disable (Workspace)"), undefined, true,
+			() => { enablementModel.setEnabled(key, ContributionEnablementState.DisabledWorkspace); return Promise.resolve(); }),
+	];
+}
+
+/**
+ * Builds the standard enablement context-menu action group for a
+ * contribution. Returns either the enable or disable actions depending
+ * on the current state, with workspace variants included only when a
+ * workspace is open.
+ */
+export function buildEnablementContextMenuGroup(
+	enablementState: ContributionEnablementState,
+	key: string,
+	enablementModel: IEnablementModel,
+	workspaceContextService: IWorkspaceContextService,
+	idPrefix: string,
+): IAction[] {
+	const hasWorkspace = workspaceContextService.getWorkbenchState() !== WorkbenchState.EMPTY;
+	const [enable, enableWorkspace, disable, disableWorkspace] = createEnablementActions(key, enablementModel, idPrefix);
+	const actions: IAction[] = [];
+	if (isContributionDisabled(enablementState)) {
+		actions.push(enable);
+		if (hasWorkspace) {
+			actions.push(enableWorkspace);
+		}
+	} else {
+		actions.push(disable);
+		if (hasWorkspace) {
+			actions.push(disableWorkspace);
+		}
+	}
+	return actions;
+}
diff --git a/src/vs/workbench/contrib/chat/browser/enablementStatusWidget.ts b/src/vs/workbench/contrib/chat/browser/enablementStatusWidget.ts
new file mode 100644
index 0000000000000..fae6918b782a9
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/enablementStatusWidget.ts
@@ -0,0 +1,74 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { reset } from '../../../../base/browser/dom.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { MarkdownString } from '../../../../base/common/htmlContent.js';
+import { Disposable, MutableDisposable } from '../../../../base/common/lifecycle.js';
+import { IObservable, autorun } from '../../../../base/common/observable.js';
+import { localize } from '../../../../nls.js';
+import { IMarkdownRendererService } from '../../../../platform/markdown/browser/markdownRenderer.js';
+import { ContributionEnablementState } from '../common/enablement.js';
+
+/**
+ * A small reusable widget that renders an enablement status message inside
+ * a `.status` container, matching the style used by the extension and MCP
+ * server editors. The message is shown only when the contribution is
+ * disabled and is rendered as markdown with a theme icon prefix.
+ */
+export class EnablementStatusWidget extends Disposable {
+
+	private readonly _renderDisposables = this._register(new MutableDisposable());
+
+	constructor(
+		private readonly _container: HTMLElement,
+		enablement: IObservable<ContributionEnablementState>,
+		private readonly _labels: {
+			disabledProfile: string;
+			disabledWorkspace: string;
+		},
+		@IMarkdownRendererService private readonly _markdownRendererService: IMarkdownRendererService,
+	) {
+		super();
+		this._register(autorun(reader => {
+			this._render(enablement.read(reader));
+		}));
+	}
+
+	private _render(state: ContributionEnablementState): void {
+		reset(this._container);
+		this._renderDisposables.value = undefined;
+
+		let message: string | undefined;
+		if (state === ContributionEnablementState.DisabledProfile) {
+			message = this._labels.disabledProfile;
+		} else if (state === ContributionEnablementState.DisabledWorkspace) {
+			message = this._labels.disabledWorkspace;
+		}
+
+		if (!message) {
+			return;
+		}
+
+		const markdown = new MarkdownString('', { isTrusted: true, supportThemeIcons: true });
+		markdown.appendMarkdown(`$(${Codicon.info.id})&nbsp;`);
+		markdown.appendText(message);
+		const rendered = this._markdownRendererService.render(markdown);
+		this._renderDisposables.value = rendered;
+		this._container.appendChild(rendered.element);
+	}
+}
+
+/** Default labels for plugin enablement status. */
+export const pluginEnablementLabels = {
+	disabledProfile: localize('pluginDisabled', "This plugin is disabled."),
+	disabledWorkspace: localize('pluginDisabledWorkspace', "This plugin is disabled for this workspace."),
+};
+
+/** Default labels for MCP server enablement status. */
+export const mcpServerEnablementLabels = {
+	disabledProfile: localize('mcpServerDisabled', "This MCP server is disabled."),
+	disabledWorkspace: localize('mcpServerDisabledWorkspace', "This MCP server is disabled for this workspace."),
+};
diff --git a/src/vs/workbench/contrib/chat/browser/pluginInstallService.ts b/src/vs/workbench/contrib/chat/browser/pluginInstallService.ts
index 6679481ea06d2..723f6087915cc 100644
--- a/src/vs/workbench/contrib/chat/browser/pluginInstallService.ts
+++ b/src/vs/workbench/contrib/chat/browser/pluginInstallService.ts
@@ -4,185 +4,451 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { Action } from '../../../../base/common/actions.js';
-import { dirname, isEqualOrParent, joinPath } from '../../../../base/common/resources.js';
+import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { basename } from '../../../../base/common/resources.js';
 import { URI } from '../../../../base/common/uri.js';
 import { localize } from '../../../../nls.js';
 import { ICommandService } from '../../../../platform/commands/common/commands.js';
-import { ConfigurationTarget, IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
-import { IEnvironmentService } from '../../../../platform/environment/common/environment.js';
+import { IDialogService } from '../../../../platform/dialogs/common/dialogs.js';
 import { IFileService } from '../../../../platform/files/common/files.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
 import { INotificationService, Severity } from '../../../../platform/notification/common/notification.js';
 import { IProgressService, ProgressLocation } from '../../../../platform/progress/common/progress.js';
-import { ChatConfiguration } from '../common/constants.js';
-import { IPluginInstallService } from '../common/plugins/pluginInstallService.js';
-import { IMarketplacePlugin, MarketplaceType } from '../common/plugins/pluginMarketplaceService.js';
+import { IQuickInputService, IQuickPickItem } from '../../../../platform/quickinput/common/quickInput.js';
+import { IAgentPluginRepositoryService } from '../common/plugins/agentPluginRepositoryService.js';
+import { IPluginInstallService, IUpdateAllPluginsOptions, IUpdateAllPluginsResult } from '../common/plugins/pluginInstallService.js';
+import { IMarketplacePlugin, IPluginMarketplaceService, MarketplaceReferenceKind, MarketplaceType, hasSourceChanged, parseMarketplaceReference, PluginSourceKind } from '../common/plugins/pluginMarketplaceService.js';
 
 export class PluginInstallService implements IPluginInstallService {
 	declare readonly _serviceBrand: undefined;
 
-	private readonly _cacheRoot: URI;
-
 	constructor(
-		@ICommandService private readonly _commandService: ICommandService,
-		@IConfigurationService private readonly _configurationService: IConfigurationService,
-		@IEnvironmentService environmentService: IEnvironmentService,
+		@IAgentPluginRepositoryService private readonly _pluginRepositoryService: IAgentPluginRepositoryService,
+		@IPluginMarketplaceService private readonly _pluginMarketplaceService: IPluginMarketplaceService,
 		@IFileService private readonly _fileService: IFileService,
-		@ILogService private readonly _logService: ILogService,
 		@INotificationService private readonly _notificationService: INotificationService,
+		@IDialogService private readonly _dialogService: IDialogService,
+		@ILogService private readonly _logService: ILogService,
 		@IProgressService private readonly _progressService: IProgressService,
-	) {
-		this._cacheRoot = joinPath(environmentService.cacheHome, 'agentPlugins');
-	}
+		@ICommandService private readonly _commandService: ICommandService,
+		@IQuickInputService private readonly _quickInputService: IQuickInputService,
+	) { }
 
 	async installPlugin(plugin: IMarketplacePlugin): Promise<void> {
-		const repoDir = this._getRepoCacheDir(plugin.marketplaceType, plugin.marketplace);
-		const repoExists = await this._fileService.exists(repoDir);
+		if (!await this._ensureMarketplaceTrusted(plugin)) {
+			return;
+		}
 
-		if (!repoExists) {
-			const repoUrl = `https://github.com/${plugin.marketplace}.git`;
-			try {
-				await this._progressService.withProgress(
-					{
-						location: ProgressLocation.Notification,
-						title: localize('installingPlugin', "Installing plugin '{0}'...", plugin.name),
-						cancellable: false,
-					},
-					async () => {
-						await this._commandService.executeCommand('_git.cloneRepository', repoUrl, dirname(repoDir).fsPath);
-					}
-				);
-			} catch (err) {
-				this._logService.error(`[PluginInstallService] Failed to clone ${repoUrl}:`, err);
-				this._notificationService.notify({
-					severity: Severity.Error,
-					message: localize('cloneFailed', "Failed to install plugin '{0}': {1}", plugin.name, err?.message ?? String(err)),
-					actions: {
-						primary: [new Action('showGitOutput', localize('showGitOutput', "Show Git Output"), undefined, true, () => {
-							this._commandService.executeCommand('git.showOutput');
-						})],
-					},
-				});
-				return;
-			}
+		const kind = plugin.sourceDescriptor.kind;
+
+		if (kind === PluginSourceKind.RelativePath) {
+			return this._installRelativePathPlugin(plugin);
 		}
 
-		let pluginDir: URI;
-		try {
-			pluginDir = this._getPluginDir(repoDir, plugin.source);
-		} catch {
+		if (kind === PluginSourceKind.Npm || kind === PluginSourceKind.Pip) {
+			await this._installPackagePlugin(plugin);
+			return;
+		}
+
+		// GitHub / GitUrl
+		return this._installGitPlugin(plugin);
+	}
+
+	async installPluginFromSource(source: string): Promise<void> {
+		const reference = parseMarketplaceReference(source);
+		if (!reference) {
 			this._notificationService.notify({
 				severity: Severity.Error,
-				message: localize('pluginDirInvalid', "Plugin source directory '{0}' is invalid for repository '{1}'.", plugin.source, plugin.marketplace),
+				message: localize('invalidSource', "'{0}' is not a valid plugin source. Enter a GitHub repository (owner/repo) or a git clone URL.", source),
 			});
 			return;
 		}
 
-		const pluginExists = await this._fileService.exists(pluginDir);
-		if (!pluginExists) {
+		if (reference.kind === MarketplaceReferenceKind.LocalFileUri) {
 			this._notificationService.notify({
 				severity: Severity.Error,
-				message: localize('pluginDirNotFound', "Plugin source directory '{0}' not found in repository '{1}'.", plugin.source, plugin.marketplace),
+				message: localize('localSourceNotSupported', "Local file paths are not supported. Enter a GitHub repository (owner/repo) or a git clone URL."),
 			});
 			return;
 		}
 
-		this._addPluginPath(pluginDir.fsPath);
-	}
+		// Build a source descriptor for the git clone.
+		const sourceDescriptor = reference.kind === MarketplaceReferenceKind.GitHubShorthand
+			? { kind: PluginSourceKind.GitHub as const, repo: reference.githubRepo! }
+			: { kind: PluginSourceKind.GitUrl as const, url: reference.cloneUrl };
+
+		// Build a temporary plugin object for the trust gate and clone step.
+		const tempPlugin: IMarketplacePlugin = {
+			name: reference.displayLabel,
+			description: '',
+			version: '',
+			source: '',
+			sourceDescriptor,
+			marketplace: reference.displayLabel,
+			marketplaceReference: reference,
+			marketplaceType: MarketplaceType.OpenPlugin,
+		};
+
+		if (!await this._ensureMarketplaceTrusted(tempPlugin)) {
+			return;
+		}
+
+		// Clone the repository.
+		let repoDir: URI;
+		try {
+			repoDir = await this._pluginRepositoryService.ensurePluginSource(tempPlugin, {
+				progressTitle: localize('cloningSource', "Cloning plugin source '{0}'...", reference.displayLabel),
+				failureLabel: reference.displayLabel,
+				marketplaceType: MarketplaceType.OpenPlugin,
+			});
+		} catch {
+			return;
+		}
 
-	async updatePlugin(plugin: IMarketplacePlugin): Promise<void> {
-		const repoDir = this._getRepoCacheDir(plugin.marketplaceType, plugin.marketplace);
 		const repoExists = await this._fileService.exists(repoDir);
 		if (!repoExists) {
-			this._logService.warn(`[PluginInstallService] Cannot update plugin '${plugin.name}': repository not cloned`);
+			this._notificationService.notify({
+				severity: Severity.Error,
+				message: localize('cloneFailed', "Failed to clone plugin source '{0}'.", reference.displayLabel),
+			});
 			return;
 		}
 
-		try {
+		// Scan for marketplace.json to discover plugins.
+		const discoveredPlugins = await this._pluginMarketplaceService.readPluginsFromDirectory(repoDir, reference);
+
+		if (discoveredPlugins.length === 0) {
+			// No marketplace.json — treat the repo root as a single plugin.
+			const repoName = basename(URI.parse(reference.cloneUrl));
+			const plugin: IMarketplacePlugin = {
+				name: repoName.replace(/\.git$/i, ''),
+				description: '',
+				version: '',
+				source: '',
+				sourceDescriptor,
+				marketplace: reference.displayLabel,
+				marketplaceReference: reference,
+				marketplaceType: MarketplaceType.OpenPlugin,
+			};
+			this._pluginMarketplaceService.addInstalledPlugin(repoDir, plugin);
+			return;
+		}
+
+		if (discoveredPlugins.length === 1) {
+			const plugin = discoveredPlugins[0];
+			const pluginDir = plugin.source ? URI.joinPath(repoDir, plugin.source) : repoDir;
+			this._pluginMarketplaceService.addInstalledPlugin(pluginDir, plugin);
+			return;
+		}
+
+		// Multiple plugins — let the user choose.
+		const picks: (IQuickPickItem & { plugin: IMarketplacePlugin })[] = discoveredPlugins.map(p => ({
+			label: p.name,
+			description: p.description,
+			plugin: p,
+		}));
+
+		const selected = await this._quickInputService.pick(picks, {
+			placeHolder: localize('selectPlugin', "Select a plugin to install from '{0}'", reference.displayLabel),
+			canPickMany: false,
+		});
+
+		if (!selected) {
+			return;
+		}
+
+		const plugin = selected.plugin;
+		const pluginDir = plugin.source ? URI.joinPath(repoDir, plugin.source) : repoDir;
+		this._pluginMarketplaceService.addInstalledPlugin(pluginDir, plugin);
+	}
+
+	async updatePlugin(plugin: IMarketplacePlugin, silent?: boolean): Promise<boolean> {
+		const kind = plugin.sourceDescriptor.kind;
+
+		if (kind === PluginSourceKind.Npm || kind === PluginSourceKind.Pip) {
+			// Package-manager "update" re-runs install via terminal
+			return this._installPackagePlugin(plugin, silent);
+		}
+
+		// For relative-path and git sources, delegate to repository service
+		return this._pluginRepositoryService.updatePluginSource(plugin, {
+			pluginName: plugin.name,
+			failureLabel: plugin.name,
+			marketplaceType: plugin.marketplaceType,
+		});
+	}
+
+	async updateAllPlugins(options: IUpdateAllPluginsOptions, token: CancellationToken): Promise<IUpdateAllPluginsResult> {
+		const installed = this._pluginMarketplaceService.installedPlugins.get().filter(e => e.enabled);
+		if (installed.length === 0) {
+			return { updatedNames: [], failedNames: [] };
+		}
+
+		const updatedNames: string[] = [];
+		const failedNames: string[] = [];
+
+		const doUpdate = async () => {
+			const gitTasks: Promise<void>[] = [];
+			const packagePlugins: { installed: IMarketplacePlugin; marketplace: IMarketplacePlugin }[] = [];
+
+			// 1. Pull each unique marketplace repository first (handles all
+			//    relative-path plugins and ensures the marketplace index on
+			//    disk is up-to-date before we re-read it).
+			const seenMarketplaces = new Set<string>();
+			for (const entry of installed) {
+				const ref = entry.plugin.marketplaceReference;
+				if (seenMarketplaces.has(ref.canonicalId)) {
+					continue;
+				}
+				seenMarketplaces.add(ref.canonicalId);
+				gitTasks.push((async () => {
+					if (token.isCancellationRequested) {
+						return;
+					}
+
+					try {
+						const changed = await this._pluginRepositoryService.pullRepository(ref, {
+							pluginName: ref.displayLabel,
+							failureLabel: ref.displayLabel,
+							marketplaceType: entry.plugin.marketplaceType,
+							silent: options.silent,
+						});
+						if (changed) {
+							updatedNames.push(ref.displayLabel);
+						}
+					} catch (err) {
+						this._logService.error(`[PluginInstallService] Failed to pull marketplace '${ref.displayLabel}':`, err);
+						failedNames.push(ref.displayLabel);
+					}
+				})());
+			}
+
+			await Promise.all(gitTasks);
+
+			// 2. Re-fetch marketplace data *after* pulling so we see any
+			//    updated plugin descriptors (new versions, refs, etc.).
+			const marketplacePlugins = await this._pluginMarketplaceService.fetchMarketplacePlugins(token);
+			const marketplaceByKey = new Map<string, IMarketplacePlugin>();
+			for (const mp of marketplacePlugins) {
+				marketplaceByKey.set(`${mp.marketplaceReference.canonicalId}::${mp.name}`, mp);
+			}
+
+			// 3. Update non-relative-path plugins individually.
+			const independentGitTasks: Promise<void>[] = [];
+			for (const entry of installed) {
+				if (entry.plugin.sourceDescriptor.kind === PluginSourceKind.RelativePath) {
+					continue;
+				}
+
+				const livePlugin = marketplaceByKey.get(`${entry.plugin.marketplaceReference.canonicalId}::${entry.plugin.name}`);
+				if (!livePlugin || !hasSourceChanged(entry.plugin.sourceDescriptor, livePlugin.sourceDescriptor)) {
+					continue;
+				}
+
+				const desc = livePlugin.sourceDescriptor;
+				if (desc.kind === PluginSourceKind.Npm || desc.kind === PluginSourceKind.Pip) {
+					if (!options.force && !desc.version) {
+						continue;
+					}
+					packagePlugins.push({ installed: entry.plugin, marketplace: livePlugin });
+					continue;
+				}
+
+				independentGitTasks.push((async () => {
+					if (token.isCancellationRequested) {
+						return;
+					}
+
+					try {
+						const changed = await this._pluginRepositoryService.updatePluginSource(livePlugin, {
+							pluginName: livePlugin.name,
+							failureLabel: livePlugin.name,
+							marketplaceType: livePlugin.marketplaceType,
+							silent: options.silent,
+						});
+						if (changed) {
+							updatedNames.push(livePlugin.name);
+							this._pluginMarketplaceService.addInstalledPlugin(entry.pluginUri, livePlugin);
+						}
+					} catch (err) {
+						this._logService.error(`[PluginInstallService] Failed to update plugin '${livePlugin.name}':`, err);
+						failedNames.push(livePlugin.name);
+					}
+				})());
+			}
+
+			await Promise.all(independentGitTasks);
+
+			for (const { installed: _installed, marketplace } of packagePlugins) {
+				if (token.isCancellationRequested) {
+					return;
+				}
+
+				try {
+					const changed = await this.updatePlugin(marketplace, options?.silent);
+					if (changed) {
+						updatedNames.push(marketplace.name);
+						const pluginUri = this._pluginRepositoryService.getPluginSourceInstallUri(marketplace.sourceDescriptor);
+						this._pluginMarketplaceService.addInstalledPlugin(pluginUri, marketplace);
+					}
+				} catch (err) {
+					this._logService.error(`[PluginInstallService] Failed to update plugin '${marketplace.name}':`, err);
+					failedNames.push(marketplace.name);
+				}
+			}
+		};
+
+		if (options.silent) {
+			await doUpdate();
+		} else {
 			await this._progressService.withProgress(
 				{
 					location: ProgressLocation.Notification,
-					title: localize('updatingPlugin', "Updating plugin '{0}'...", plugin.name),
-					cancellable: false,
+					title: localize('updatingAllPlugins', "Updating plugins..."),
 				},
-				async () => {
-					await this._commandService.executeCommand('_git.pull', repoDir.fsPath);
-				}
+				doUpdate,
 			);
-		} catch (err) {
-			this._logService.error(`[PluginInstallService] Failed to update ${plugin.marketplace}:`, err);
+		}
+
+		if (failedNames.length > 0) {
 			this._notificationService.notify({
 				severity: Severity.Error,
-				message: localize('pullFailed', "Failed to update plugin '{0}': {1}", plugin.name, err?.message ?? String(err)),
+				message: localize('updateAllFailed', "Failed to update: {0}", failedNames.join(', ')),
 				actions: {
-					primary: [new Action('showGitOutput', localize('showGitOutput', "Show Git Output"), undefined, true, () => {
+					primary: [new Action('showGitOutput', localize('showOutput', "Show Output"), undefined, true, () => {
 						this._commandService.executeCommand('git.showOutput');
 					})],
 				},
 			});
+		} else if (updatedNames.length > 0) {
+			this._pluginMarketplaceService.clearUpdatesAvailable();
+			this._notificationService.notify({
+				severity: Severity.Info,
+				message: localize('updateAllSuccess', "Updated plugins: {0}", updatedNames.join(', ')),
+			});
+		} else if (!token.isCancellationRequested) {
+			this._pluginMarketplaceService.clearUpdatesAvailable();
 		}
-	}
 
-	/**
-	 * Computes the cache directory for a marketplace repository.
-	 * Structure: `cacheRoot/{type}/{owner}/{repo}`
-	 */
-	private _getRepoCacheDir(type: MarketplaceType, marketplace: string): URI {
-		const [owner, repo] = marketplace.split('/');
-		return joinPath(this._cacheRoot, type, owner, repo);
+		return { updatedNames, failedNames };
 	}
 
-	/**
-	 * Computes the plugin directory within a cloned repository using the
-	 * marketplace plugin's `source` field (the subdirectory path within the repo).
-	 */
-	private _getPluginDir(repoDir: URI, source: string): URI {
-		const normalizedSource = source.trim().replace(/^\.?\/+|\/+$/g, '');
-		const pluginDir = normalizedSource ? joinPath(repoDir, normalizedSource) : repoDir;
-		if (!isEqualOrParent(pluginDir, repoDir)) {
-			throw new Error(`Invalid plugin source path '${source}'`);
-		}
-		return pluginDir;
+	getPluginInstallUri(plugin: IMarketplacePlugin): URI {
+		if (plugin.sourceDescriptor.kind === PluginSourceKind.RelativePath) {
+			return this._pluginRepositoryService.getPluginInstallUri(plugin);
+		}
+		return this._pluginRepositoryService.getPluginSourceInstallUri(plugin.sourceDescriptor);
 	}
 
-	async uninstallPlugin(pluginUri: URI): Promise<void> {
-		await this._removePluginPath(pluginUri.fsPath);
-	}
+	// --- Trust gate -------------------------------------------------------------
 
-	getPluginInstallUri(plugin: IMarketplacePlugin): URI {
-		const repoDir = this._getRepoCacheDir(plugin.marketplaceType, plugin.marketplace);
-		return this._getPluginDir(repoDir, plugin.source);
+	private async _ensureMarketplaceTrusted(plugin: IMarketplacePlugin): Promise<boolean> {
+		if (this._pluginMarketplaceService.isMarketplaceTrusted(plugin.marketplaceReference)) {
+			return true;
+		}
+
+		const { confirmed } = await this._dialogService.confirm({
+			type: 'question',
+			message: localize('trustMarketplace', "Trust Plugins from '{0}'?", plugin.marketplaceReference.displayLabel),
+			detail: localize('trustMarketplaceDetail', "Plugins can run code on your machine. Only install plugins from sources you trust.\n\nSource: {0}", plugin.marketplaceReference.rawValue),
+			primaryButton: localize({ key: 'trustAndInstall', comment: ['&& denotes a mnemonic'] }, "&&Trust"),
+			custom: {
+				icon: Codicon.shield,
+			},
+		});
+
+		if (!confirmed) {
+			return false;
+		}
+
+		this._pluginMarketplaceService.trustMarketplace(plugin.marketplaceReference);
+		return true;
 	}
 
-	/**
-	 * Adds the given file-system path to `chat.plugins.paths` in user-local config.
-	 */
-	private _addPluginPath(fsPath: string): void {
-		const current = this._configurationService.getValue<Record<string, boolean>>(ChatConfiguration.PluginPaths) ?? {};
-		if (Object.prototype.hasOwnProperty.call(current, fsPath)) {
+	// --- Relative-path source (existing git-based flow) -----------------------
+
+	private async _installRelativePathPlugin(plugin: IMarketplacePlugin): Promise<void> {
+		try {
+			await this._pluginRepositoryService.ensureRepository(plugin.marketplaceReference, {
+				progressTitle: localize('installingPlugin', "Installing plugin '{0}'...", plugin.name),
+				failureLabel: plugin.name,
+				marketplaceType: plugin.marketplaceType,
+			});
+		} catch {
+			return;
+		}
+
+		let pluginDir: URI;
+		try {
+			pluginDir = this._pluginRepositoryService.getPluginInstallUri(plugin);
+		} catch {
+			this._notificationService.notify({
+				severity: Severity.Error,
+				message: localize('pluginDirInvalid', "Plugin source directory '{0}' is invalid for repository '{1}'.", plugin.source, plugin.marketplace),
+			});
+			return;
+		}
+
+		const pluginExists = await this._fileService.exists(pluginDir);
+		if (!pluginExists) {
+			this._notificationService.notify({
+				severity: Severity.Error,
+				message: localize('pluginDirNotFound', "Plugin source directory '{0}' not found in repository '{1}'.", plugin.source, plugin.marketplace),
+			});
 			return;
 		}
-		this._configurationService.updateValue(
-			ChatConfiguration.PluginPaths,
-			{ ...current, [fsPath]: true },
-			ConfigurationTarget.USER_LOCAL,
-		);
+
+		this._pluginMarketplaceService.addInstalledPlugin(pluginDir, plugin);
 	}
 
-	/**
-	 * Removes the given file-system path from `chat.plugins.paths` in user-local config.
-	 */
-	private _removePluginPath(fsPath: string) {
-		const current = this._configurationService.getValue<Record<string, boolean>>(ChatConfiguration.PluginPaths) ?? {};
-		if (!Object.prototype.hasOwnProperty.call(current, fsPath)) {
+	// --- GitHub / Git URL source (independent clone) --------------------------
+
+	private async _installGitPlugin(plugin: IMarketplacePlugin): Promise<void> {
+		const repo = this._pluginRepositoryService.getPluginSource(plugin.sourceDescriptor.kind);
+		let pluginDir: URI;
+		try {
+			pluginDir = await this._pluginRepositoryService.ensurePluginSource(plugin, {
+				progressTitle: localize('installingPlugin', "Installing plugin '{0}'...", plugin.name),
+				failureLabel: plugin.name,
+				marketplaceType: plugin.marketplaceType,
+			});
+		} catch {
+			return;
+		}
+
+		const pluginExists = await this._fileService.exists(pluginDir);
+		if (!pluginExists) {
+			this._notificationService.notify({
+				severity: Severity.Error,
+				message: localize('pluginSourceNotFound', "Plugin source '{0}' not found after cloning.", repo.getLabel(plugin.sourceDescriptor)),
+			});
 			return;
 		}
-		const updated = { ...current };
-		delete updated[fsPath];
-		return this._configurationService.updateValue(
-			ChatConfiguration.PluginPaths,
-			updated,
-			ConfigurationTarget.USER_LOCAL,
-		);
+
+		this._pluginMarketplaceService.addInstalledPlugin(pluginDir, plugin);
+	}
+
+	// --- Package-manager sources (npm / pip) ----------------------------------
+
+	private async _installPackagePlugin(plugin: IMarketplacePlugin, silent?: boolean): Promise<boolean> {
+		const repo = this._pluginRepositoryService.getPluginSource(plugin.sourceDescriptor.kind);
+		if (!repo.runInstall) {
+			this._logService.error(`[PluginInstallService] Expected package repository for kind '${plugin.sourceDescriptor.kind}'`);
+			return false;
+		}
+
+		// Ensure the parent cache directory exists (returns npm/<pkg> or pip/<pkg>)
+		const installDir = await this._pluginRepositoryService.ensurePluginSource(plugin);
+		// The actual plugin content location (e.g. npm/<pkg>/node_modules/<pkg>)
+		const pluginDir = this._pluginRepositoryService.getPluginSourceInstallUri(plugin.sourceDescriptor);
+
+		const result = await repo.runInstall(installDir, pluginDir, plugin, { silent });
+		if (!result) {
+			return false;
+		}
+
+		this._pluginMarketplaceService.addInstalledPlugin(result.pluginDir, plugin);
+		return true;
 	}
 }
diff --git a/src/vs/workbench/contrib/chat/browser/pluginSources.ts b/src/vs/workbench/contrib/chat/browser/pluginSources.ts
new file mode 100644
index 0000000000000..8ea0f30210d8d
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/pluginSources.ts
@@ -0,0 +1,551 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Action } from '../../../../base/common/actions.js';
+import { CancelablePromise, timeout } from '../../../../base/common/async.js';
+import { Event } from '../../../../base/common/event.js';
+import { DisposableStore, toDisposable } from '../../../../base/common/lifecycle.js';
+import { isWindows } from '../../../../base/common/platform.js';
+import { dirname, joinPath } from '../../../../base/common/resources.js';
+import { URI } from '../../../../base/common/uri.js';
+import { localize } from '../../../../nls.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IDialogService } from '../../../../platform/dialogs/common/dialogs.js';
+import { IFileService } from '../../../../platform/files/common/files.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
+import { INotificationService, Severity } from '../../../../platform/notification/common/notification.js';
+import { IProgressService, ProgressLocation } from '../../../../platform/progress/common/progress.js';
+import { TerminalCapability, type ITerminalCommand } from '../../../../platform/terminal/common/capabilities/capabilities.js';
+import { ITerminalInstance, ITerminalService } from '../../terminal/browser/terminal.js';
+import { IEnsureRepositoryOptions, IPullRepositoryOptions } from '../common/plugins/agentPluginRepositoryService.js';
+import { IGitHubPluginSource, IGitUrlPluginSource, IMarketplacePlugin, INpmPluginSource, IPipPluginSource, IPluginSourceDescriptor, PluginSourceKind } from '../common/plugins/pluginMarketplaceService.js';
+import { IPluginSource } from '../common/plugins/pluginSource.js';
+
+// ---------------------------------------------------------------------------
+// Shared helpers
+// ---------------------------------------------------------------------------
+
+function sanitizeCacheSegment(name: string): string {
+	return name.replace(/[\\/:*?"<>|]/g, '_');
+}
+
+function gitRevisionCacheSuffix(ref?: string, sha?: string): string[] {
+	if (sha) {
+		return [`sha_${sanitizeCacheSegment(sha)}`];
+	}
+	if (ref) {
+		return [`ref_${sanitizeCacheSegment(ref)}`];
+	}
+	return [];
+}
+
+function showGitOutputAction(commandService: ICommandService): Action {
+	return new Action('showGitOutput', localize('showGitOutput', "Show Git Output"), undefined, true, () => {
+		commandService.executeCommand('git.showOutput');
+	});
+}
+
+function shellEscapeArg(value: string): string {
+	if (isWindows) {
+		return `"${value.replace(/[`$"]/g, '`$&')}"`;
+	}
+	return `'${value.replace(/'/g, `'\\''`)}'`;
+}
+
+function formatShellCommand(args: readonly string[]): string {
+	const [command, ...rest] = args;
+	return [command, ...rest.map(arg => shellEscapeArg(arg))].join(' ');
+}
+
+// ---------------------------------------------------------------------------
+// Base for git-based sources (GitHub shorthand & arbitrary Git URL)
+// ---------------------------------------------------------------------------
+
+abstract class AbstractGitPluginSource implements IPluginSource {
+	abstract readonly kind: PluginSourceKind;
+	constructor(
+		@ICommandService protected readonly _commandService: ICommandService,
+		@IFileService protected readonly _fileService: IFileService,
+		@ILogService protected readonly _logService: ILogService,
+		@INotificationService protected readonly _notificationService: INotificationService,
+		@IProgressService protected readonly _progressService: IProgressService,
+	) { }
+
+	abstract getInstallUri(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI;
+	abstract getLabel(descriptor: IPluginSourceDescriptor): string;
+	protected abstract _cloneUrl(descriptor: IPluginSourceDescriptor): string;
+	protected abstract _displayLabel(descriptor: IPluginSourceDescriptor): string;
+
+	getCleanupTarget(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI | undefined {
+		return this.getInstallUri(cacheRoot, descriptor);
+	}
+
+	async ensure(cacheRoot: URI, plugin: IMarketplacePlugin, options?: IEnsureRepositoryOptions): Promise<URI> {
+		const descriptor = plugin.sourceDescriptor;
+		const repoDir = this.getInstallUri(cacheRoot, descriptor);
+		const repoExists = await this._fileService.exists(repoDir);
+		const label = this._displayLabel(descriptor);
+
+		if (repoExists) {
+			await this._checkoutRevision(repoDir, descriptor, options?.failureLabel ?? label);
+			return repoDir;
+		}
+
+		const progressTitle = options?.progressTitle ?? localize('cloningPluginSource', "Cloning plugin source '{0}'...", label);
+		const failureLabel = options?.failureLabel ?? label;
+		const ref = (descriptor as IGitHubPluginSource | IGitUrlPluginSource).ref;
+
+		await this._cloneRepository(repoDir, this._cloneUrl(descriptor), progressTitle, failureLabel, ref);
+		await this._checkoutRevision(repoDir, descriptor, failureLabel);
+		return repoDir;
+	}
+
+	async update(cacheRoot: URI, plugin: IMarketplacePlugin, options?: IPullRepositoryOptions): Promise<boolean> {
+		const descriptor = plugin.sourceDescriptor;
+		const repoDir = this.getInstallUri(cacheRoot, descriptor);
+		const repoExists = await this._fileService.exists(repoDir);
+		if (!repoExists) {
+			this._logService.warn(`[${this.kind}] Cannot update plugin '${options?.pluginName ?? plugin.name}': source repository not cloned`);
+			return false;
+		}
+
+		const updateLabel = options?.pluginName ?? plugin.name;
+		const failureLabel = options?.failureLabel ?? updateLabel;
+
+		try {
+			const doUpdate = async () => {
+				await this._commandService.executeCommand('git.openRepository', repoDir.fsPath);
+				const git = descriptor as IGitHubPluginSource | IGitUrlPluginSource;
+				let changed: boolean;
+				if (git.sha) {
+					const headBefore = await this._commandService.executeCommand<string>('_git.revParse', repoDir.fsPath, 'HEAD').catch(() => undefined);
+					await this._commandService.executeCommand('git.fetch', repoDir.fsPath);
+					await this._checkoutRevision(repoDir, descriptor, failureLabel);
+					const headAfter = await this._commandService.executeCommand<string>('_git.revParse', repoDir.fsPath, 'HEAD').catch(() => undefined);
+					changed = headBefore !== headAfter;
+				} else {
+					changed = !!(await this._commandService.executeCommand<boolean>('_git.pull', repoDir.fsPath));
+					await this._checkoutRevision(repoDir, descriptor, failureLabel);
+				}
+				return changed;
+			};
+
+			if (options?.silent) {
+				return await doUpdate();
+			}
+
+			return await this._progressService.withProgress(
+				{
+					location: ProgressLocation.Notification,
+					title: localize('updatingPluginSource', "Updating plugin '{0}'...", updateLabel),
+					cancellable: false,
+				},
+				doUpdate,
+			);
+		} catch (err) {
+			this._logService.error(`[${this.kind}] Failed to update plugin source '${updateLabel}':`, err);
+			if (!options?.silent) {
+				this._notificationService.notify({
+					severity: Severity.Error,
+					message: localize('pullPluginSourceFailed', "Failed to update plugin '{0}': {1}", failureLabel, err?.message ?? String(err)),
+					actions: { primary: [showGitOutputAction(this._commandService)] },
+				});
+			}
+			throw err;
+		}
+	}
+
+	// -- internal helpers ---
+
+	private async _cloneRepository(repoDir: URI, cloneUrl: string, progressTitle: string, failureLabel: string, ref?: string): Promise<void> {
+		try {
+			await this._progressService.withProgress(
+				{
+					location: ProgressLocation.Notification,
+					title: progressTitle,
+					cancellable: false,
+				},
+				async () => {
+					await this._fileService.createFolder(dirname(repoDir));
+					await this._commandService.executeCommand('_git.cloneRepository', cloneUrl, repoDir.fsPath, ref);
+				}
+			);
+		} catch (err) {
+			this._logService.error(`[${this.kind}] Failed to clone ${cloneUrl}:`, err);
+			this._notificationService.notify({
+				severity: Severity.Error,
+				message: localize('cloneFailed', "Failed to install plugin '{0}': {1}", failureLabel, err?.message ?? String(err)),
+				actions: { primary: [showGitOutputAction(this._commandService)] },
+			});
+			throw err;
+		}
+	}
+
+	private async _checkoutRevision(repoDir: URI, descriptor: IPluginSourceDescriptor, failureLabel: string): Promise<void> {
+		const git = descriptor as IGitHubPluginSource | IGitUrlPluginSource;
+		if (!git.sha && !git.ref) {
+			return;
+		}
+
+		try {
+			if (git.sha) {
+				await this._commandService.executeCommand('_git.checkout', repoDir.fsPath, git.sha, true);
+				return;
+			}
+			await this._commandService.executeCommand('_git.checkout', repoDir.fsPath, git.ref);
+		} catch (err) {
+			this._logService.error(`[${this.kind}] Failed to checkout revision for '${failureLabel}':`, err);
+			this._notificationService.notify({
+				severity: Severity.Error,
+				message: localize('checkoutPluginSourceFailed', "Failed to checkout plugin '{0}' to requested revision: {1}", failureLabel, err?.message ?? String(err)),
+				actions: { primary: [showGitOutputAction(this._commandService)] },
+			});
+			throw err;
+		}
+	}
+}
+
+// ---------------------------------------------------------------------------
+// RelativePath — plugin lives inside a shared marketplace repository
+// ---------------------------------------------------------------------------
+
+export class RelativePathPluginSource implements IPluginSource {
+	readonly kind = PluginSourceKind.RelativePath;
+
+	getInstallUri(_cacheRoot: URI, _descriptor: IPluginSourceDescriptor): URI {
+		throw new Error('Use getPluginInstallUri() for relative-path sources');
+	}
+
+	async ensure(_cacheRoot: URI, _plugin: IMarketplacePlugin, _options?: IEnsureRepositoryOptions): Promise<URI> {
+		throw new Error('Use ensureRepository() for relative-path sources');
+	}
+
+	async update(_cacheRoot: URI, _plugin: IMarketplacePlugin, _options?: IPullRepositoryOptions): Promise<boolean> {
+		throw new Error('Use pullRepository() for relative-path sources');
+	}
+
+	getCleanupTarget(_cacheRoot: URI, _descriptor: IPluginSourceDescriptor): URI | undefined {
+		return undefined;
+	}
+
+	getLabel(descriptor: IPluginSourceDescriptor): string {
+		return (descriptor as { path: string }).path || '.';
+	}
+}
+
+// ---------------------------------------------------------------------------
+// GitHub — `{ source: "github", repo: "owner/repo" }`
+// ---------------------------------------------------------------------------
+
+export class GitHubPluginSource extends AbstractGitPluginSource {
+	readonly kind = PluginSourceKind.GitHub;
+
+	getInstallUri(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI {
+		const gh = descriptor as IGitHubPluginSource;
+		const [owner, repo] = gh.repo.split('/');
+		return joinPath(cacheRoot, 'github.com', owner, repo, ...gitRevisionCacheSuffix(gh.ref, gh.sha));
+	}
+
+	getLabel(descriptor: IPluginSourceDescriptor): string {
+		return (descriptor as IGitHubPluginSource).repo;
+	}
+
+	protected _cloneUrl(descriptor: IPluginSourceDescriptor): string {
+		return `https://github.com/${(descriptor as IGitHubPluginSource).repo}.git`;
+	}
+
+	protected _displayLabel(descriptor: IPluginSourceDescriptor): string {
+		return (descriptor as IGitHubPluginSource).repo;
+	}
+}
+
+// ---------------------------------------------------------------------------
+// GitUrl — `{ source: "url", url: "https://…/repo.git" }`
+// ---------------------------------------------------------------------------
+
+export class GitUrlPluginSource extends AbstractGitPluginSource {
+	readonly kind = PluginSourceKind.GitUrl;
+
+	getInstallUri(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI {
+		const git = descriptor as IGitUrlPluginSource;
+		const segments = this._gitUrlCacheSegments(git.url, git.ref, git.sha);
+		return joinPath(cacheRoot, ...segments);
+	}
+
+	getLabel(descriptor: IPluginSourceDescriptor): string {
+		return (descriptor as IGitUrlPluginSource).url;
+	}
+
+	protected _cloneUrl(descriptor: IPluginSourceDescriptor): string {
+		return (descriptor as IGitUrlPluginSource).url;
+	}
+
+	protected _displayLabel(descriptor: IPluginSourceDescriptor): string {
+		return (descriptor as IGitUrlPluginSource).url;
+	}
+
+	private _gitUrlCacheSegments(url: string, ref?: string, sha?: string): string[] {
+		try {
+			const parsed = URI.parse(url);
+			const authority = (parsed.authority || 'unknown').replace(/[\\/:*?"<>|]/g, '_').toLowerCase();
+			const pathPart = parsed.path.replace(/^\/+/, '').replace(/\.git$/i, '').replace(/\/+$/g, '');
+			const segments = pathPart.split('/').map(s => s.replace(/[\\/:*?"<>|]/g, '_'));
+			return [authority, ...segments, ...gitRevisionCacheSuffix(ref, sha)];
+		} catch {
+			return ['git', url.replace(/[\\/:*?"<>|]/g, '_'), ...gitRevisionCacheSuffix(ref, sha)];
+		}
+	}
+}
+
+// ---------------------------------------------------------------------------
+// Base for package-manager-based sources (npm, pip)
+// ---------------------------------------------------------------------------
+
+export abstract class AbstractPackagePluginSource implements IPluginSource {
+	abstract readonly kind: PluginSourceKind;
+	constructor(
+		@IDialogService protected readonly _dialogService: IDialogService,
+		@IFileService protected readonly _fileService: IFileService,
+		@ILogService protected readonly _logService: ILogService,
+		@INotificationService protected readonly _notificationService: INotificationService,
+		@IProgressService protected readonly _progressService: IProgressService,
+		@ITerminalService protected readonly _terminalService: ITerminalService,
+	) { }
+
+	abstract getInstallUri(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI;
+	abstract getLabel(descriptor: IPluginSourceDescriptor): string;
+
+	getCleanupTarget(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI | undefined {
+		return this._getCacheDir(cacheRoot, descriptor);
+	}
+
+	/**
+	 * Return the parent directory (prefix / target) where the package
+	 * manager installs into. This is above the actual plugin content dir.
+	 */
+	protected abstract _getCacheDir(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI;
+
+	/** Build the terminal command args for install. */
+	protected abstract _buildInstallArgs(installDir: URI, plugin: IMarketplacePlugin): string[];
+
+	/** Human-readable package manager name for messages. */
+	protected abstract get _managerName(): string;
+
+	async ensure(cacheRoot: URI, plugin: IMarketplacePlugin, _options?: IEnsureRepositoryOptions): Promise<URI> {
+		const cacheDir = this._getCacheDir(cacheRoot, plugin.sourceDescriptor);
+		await this._fileService.createFolder(cacheDir);
+		return cacheDir;
+	}
+
+	async update(cacheRoot: URI, plugin: IMarketplacePlugin, _options?: IPullRepositoryOptions): Promise<boolean> {
+		// For package-manager sources, "update" re-runs install.
+		const installDir = this._getCacheDir(cacheRoot, plugin.sourceDescriptor);
+		const pluginDir = this.getInstallUri(cacheRoot, plugin.sourceDescriptor);
+		await this.runInstall(installDir, pluginDir, plugin, { silent: _options?.silent });
+		return true;
+	}
+
+	async runInstall(installDir: URI, pluginDir: URI, plugin: IMarketplacePlugin, options?: { silent?: boolean }): Promise<{ pluginDir: URI } | undefined> {
+		const args = this._buildInstallArgs(installDir, plugin);
+		const command = formatShellCommand(args);
+		const confirmed = await this._confirmTerminalCommand(plugin.name, command, options?.silent);
+		if (!confirmed) {
+			return undefined;
+		}
+
+		const progressTitle = localize('installingPackagePlugin', "Installing {0} plugin '{1}'...", this._managerName, plugin.name);
+		const { success, terminal } = await this._runTerminalCommand(command, progressTitle);
+		if (!success) {
+			return undefined;
+		}
+
+		const exists = await this._fileService.exists(pluginDir);
+		if (!exists) {
+			this._notificationService.notify({
+				severity: Severity.Error,
+				message: localize('packagePluginNotFound', "{0} package '{1}' was not found after installation.", this._managerName, this.getLabel(plugin.sourceDescriptor)),
+			});
+			return undefined;
+		}
+
+		terminal?.dispose();
+		return { pluginDir };
+	}
+
+	// -- terminal helpers (moved from PluginInstallService) ---
+
+	private async _confirmTerminalCommand(pluginName: string, command: string, silent?: boolean): Promise<boolean> {
+		if (silent) {
+			return new Promise<boolean>(resolve => {
+				const n = this._notificationService.notify({
+					severity: Severity.Info,
+					message: localize('confirmPluginInstallNotification', "Plugin '{0}' wants to run: {1}", pluginName, command),
+					actions: {
+						primary: [
+							new Action('installPlugin', localize('install', "Install"), undefined, true, async () => resolve(true)),
+						],
+					},
+				});
+
+				Event.once(n.onDidClose)(() => resolve(false));
+			});
+		}
+
+		const { confirmed } = await this._dialogService.confirm({
+			type: 'question',
+			message: localize('confirmPluginInstall', "Install Plugin '{0}'?", pluginName),
+			detail: localize('confirmPluginInstallDetail', "This will run the following command in a terminal:\n\n{0}", command),
+			primaryButton: localize({ key: 'confirmInstall', comment: ['&& denotes a mnemonic'] }, "&&Install"),
+		});
+		return confirmed;
+	}
+
+	private async _runTerminalCommand(command: string, progressTitle: string) {
+		let terminal: ITerminalInstance | undefined;
+		try {
+			await this._progressService.withProgress(
+				{
+					location: ProgressLocation.Notification,
+					title: progressTitle,
+					cancellable: false,
+				},
+				async () => {
+					terminal = await this._terminalService.createTerminal({
+						config: {
+							name: localize('pluginInstallTerminal', "Plugin Install"),
+							forceShellIntegration: true,
+							isTransient: true,
+							isFeatureTerminal: true,
+						},
+					});
+					await terminal.processReady;
+					this._terminalService.setActiveInstance(terminal);
+
+					const commandResultPromise = this._waitForTerminalCommandCompletion(terminal);
+					await terminal.runCommand(command, true);
+					const exitCode = await commandResultPromise;
+					if (exitCode !== 0) {
+						throw new Error(localize('terminalCommandExitCode', "Command exited with code {0}", exitCode));
+					}
+				}
+			);
+			return { success: true, terminal };
+		} catch (err) {
+			this._logService.error(`[${this.kind}] Terminal command failed:`, err);
+			this._notificationService.notify({
+				severity: Severity.Error,
+				message: localize('terminalCommandFailed', "Plugin installation command failed: {0}", err?.message ?? String(err)),
+			});
+			return { success: false, terminal };
+		}
+	}
+
+	private _waitForTerminalCommandCompletion(terminal: ITerminalInstance): Promise<number | undefined> {
+		return new Promise<number | undefined>(resolve => {
+			const disposables = new DisposableStore();
+			let isResolved = false;
+
+			const resolveAndDispose = (exitCode: number | undefined): void => {
+				if (isResolved) {
+					return;
+				}
+				isResolved = true;
+				disposables.dispose();
+				resolve(exitCode);
+			};
+
+			const attachCommandFinishedListener = (): void => {
+				const commandDetection = terminal.capabilities.get(TerminalCapability.CommandDetection);
+				if (!commandDetection) {
+					return;
+				}
+				disposables.add(commandDetection.onCommandFinished((command: ITerminalCommand) => {
+					resolveAndDispose(command.exitCode ?? 0);
+				}));
+			};
+
+			attachCommandFinishedListener();
+			disposables.add(terminal.capabilities.onDidAddCommandDetectionCapability(() => attachCommandFinishedListener()));
+
+			const timeoutHandle: CancelablePromise<void> = timeout(120_000);
+			disposables.add(toDisposable(() => timeoutHandle.cancel()));
+			void timeoutHandle.then(() => {
+				if (isResolved) {
+					return;
+				}
+				this._logService.warn(`[${this.kind}] Terminal command completion timed out`);
+				resolveAndDispose(undefined);
+			});
+		});
+	}
+}
+
+// ---------------------------------------------------------------------------
+// npm — `{ source: "npm", package: "@org/plugin" }`
+// ---------------------------------------------------------------------------
+
+export class NpmPluginSource extends AbstractPackagePluginSource {
+	readonly kind = PluginSourceKind.Npm;
+	protected readonly _managerName = 'npm';
+
+	getInstallUri(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI {
+		const npm = descriptor as INpmPluginSource;
+		return joinPath(cacheRoot, 'npm', sanitizeCacheSegment(npm.package), 'node_modules', npm.package);
+	}
+
+	getLabel(descriptor: IPluginSourceDescriptor): string {
+		const npm = descriptor as INpmPluginSource;
+		return npm.version ? `${npm.package}@${npm.version}` : npm.package;
+	}
+
+	protected _getCacheDir(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI {
+		const npm = descriptor as INpmPluginSource;
+		return joinPath(cacheRoot, 'npm', sanitizeCacheSegment(npm.package));
+	}
+
+	protected _buildInstallArgs(installDir: URI, plugin: IMarketplacePlugin): string[] {
+		const npm = plugin.sourceDescriptor as INpmPluginSource;
+		const packageSpec = npm.version ? `${npm.package}@${npm.version}` : npm.package;
+		const args = ['npm', 'install', '--prefix', installDir.fsPath, packageSpec];
+		if (npm.registry) {
+			args.push('--registry', npm.registry);
+		}
+		return args;
+	}
+}
+
+// ---------------------------------------------------------------------------
+// pip — `{ source: "pip", package: "my-plugin" }`
+// ---------------------------------------------------------------------------
+
+export class PipPluginSource extends AbstractPackagePluginSource {
+	readonly kind = PluginSourceKind.Pip;
+	protected readonly _managerName = 'pip';
+
+	getInstallUri(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI {
+		const pip = descriptor as IPipPluginSource;
+		return joinPath(cacheRoot, 'pip', sanitizeCacheSegment(pip.package));
+	}
+
+	getLabel(descriptor: IPluginSourceDescriptor): string {
+		const pip = descriptor as IPipPluginSource;
+		return pip.version ? `${pip.package}==${pip.version}` : pip.package;
+	}
+
+	protected _getCacheDir(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI {
+		const pip = descriptor as IPipPluginSource;
+		return joinPath(cacheRoot, 'pip', sanitizeCacheSegment(pip.package));
+	}
+
+	protected _buildInstallArgs(installDir: URI, plugin: IMarketplacePlugin): string[] {
+		const pip = plugin.sourceDescriptor as IPipPluginSource;
+		const packageSpec = pip.version ? `${pip.package}==${pip.version}` : pip.package;
+		const args = ['pip', 'install', '--target', installDir.fsPath, packageSpec];
+		if (pip.registry) {
+			args.push('--index-url', pip.registry);
+		}
+		return args;
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/promptSyntax/hookActions.ts b/src/vs/workbench/contrib/chat/browser/promptSyntax/hookActions.ts
index 00255f745086a..244bf9498ef52 100644
--- a/src/vs/workbench/contrib/chat/browser/promptSyntax/hookActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/promptSyntax/hookActions.ts
@@ -19,18 +19,19 @@ import { Action2, registerAction2 } from '../../../../../platform/actions/common
 import { Codicon } from '../../../../../base/common/codicons.js';
 import { ContextKeyExpr } from '../../../../../platform/contextkey/common/contextkey.js';
 import { IPromptsService, PromptsStorage } from '../../common/promptSyntax/service/promptsService.js';
-import { PromptsType } from '../../common/promptSyntax/promptTypes.js';
+import { PromptsType, Target } from '../../common/promptSyntax/promptTypes.js';
 import { CancellationToken } from '../../../../../base/common/cancellation.js';
 import { IQuickInputButton, IQuickInputService, IQuickPick, IQuickPickItem, IQuickPickSeparator } from '../../../../../platform/quickinput/common/quickInput.js';
 import { IFileService } from '../../../../../platform/files/common/files.js';
-import { HOOK_TYPES, HookType, getEffectiveCommandFieldKey } from '../../common/promptSyntax/hookSchema.js';
+import { HOOK_METADATA, HOOKS_BY_TARGET, HookType, IHookTypeMeta } from '../../common/promptSyntax/hookTypes.js';
+import { formatHookCommandLabel, getEffectiveCommandFieldKey } from '../../common/promptSyntax/hookSchema.js';
 import { getCopilotCliHookTypeName, resolveCopilotCliHookType } from '../../common/promptSyntax/hookCopilotCliCompat.js';
 import { getHookSourceFormat, HookSourceFormat, buildNewHookEntry } from '../../common/promptSyntax/hookCompatibility.js';
 import { getClaudeHookTypeName, resolveClaudeHookType } from '../../common/promptSyntax/hookClaudeCompat.js';
 import { ILabelService } from '../../../../../platform/label/common/label.js';
 import { IEditorService } from '../../../../services/editor/common/editorService.js';
 import { ITextEditorSelection } from '../../../../../platform/editor/common/editor.js';
-import { findHookCommandSelection, parseAllHookFiles, IParsedHook } from './hookUtils.js';
+import { findHookCommandSelection, findHookCommandInYaml, parseAllHookFiles, IParsedHook } from './hookUtils.js';
 import { IWorkspaceContextService } from '../../../../../platform/workspace/common/workspace.js';
 import { IPathService } from '../../../../services/path/common/pathService.js';
 import { INotificationService } from '../../../../../platform/notification/common/notification.js';
@@ -38,7 +39,7 @@ import { IBulkEditService, ResourceTextEdit } from '../../../../../editor/browse
 import { Range } from '../../../../../editor/common/core/range.js';
 import { getCodeEditor } from '../../../../../editor/browser/editorBrowser.js';
 import { IRemoteAgentService } from '../../../../services/remote/common/remoteAgentService.js';
-import { OS } from '../../../../../base/common/platform.js';
+import { OperatingSystem, OS } from '../../../../../base/common/platform.js';
 
 /**
  * Action ID for the `Configure Hooks` action.
@@ -46,7 +47,8 @@ import { OS } from '../../../../../base/common/platform.js';
 const CONFIGURE_HOOKS_ACTION_ID = 'workbench.action.chat.configure.hooks';
 
 interface IHookTypeQuickPickItem extends IQuickPickItem {
-	readonly hookType: typeof HOOK_TYPES[number];
+	readonly hookType: HookType;
+	readonly hookTypeMeta: IHookTypeMeta;
 }
 
 interface IHookQuickPickItem extends IQuickPickItem {
@@ -296,15 +298,17 @@ const enum Step {
 }
 
 /**
- * Optional callbacks for customizing the hook creation and opening behaviour.
+ * Optional callbacks and settings for customizing the hook creation and opening behaviour.
  * The agentic editor passes these to open hooks in the embedded editor and
  * track worktree files for auto-commit.
  */
-export interface IHookQuickPickCallbacks {
+export interface IHookQuickPickOptions {
 	/** Override how the hook file is opened. If not provided, uses editorService.openEditor. */
 	readonly openEditor?: (resource: URI, options?: { selection?: ITextEditorSelection }) => Promise<void>;
 	/** Called after a new hook file is created on disk. */
 	readonly onHookFileCreated?: (uri: URI) => void;
+	/** Filter the displayed hook types to those supported by the given target. */
+	readonly target?: Target;
 }
 
 /**
@@ -313,7 +317,7 @@ export interface IHookQuickPickCallbacks {
  */
 export async function showConfigureHooksQuickPick(
 	accessor: ServicesAccessor,
-	callbacks?: IHookQuickPickCallbacks,
+	options?: IHookQuickPickOptions,
 ): Promise<void> {
 	const promptsService = accessor.get(IPromptsService);
 	const quickInputService = accessor.get(IQuickInputService);
@@ -344,7 +348,8 @@ export async function showConfigureHooksQuickPick(
 		workspaceRootUri,
 		userHome,
 		targetOS,
-		CancellationToken.None
+		CancellationToken.None,
+		{ includeAgentHooks: true }
 	);
 
 	// Count hooks per type
@@ -357,12 +362,6 @@ export async function showConfigureHooksQuickPick(
 	const store = new DisposableStore();
 	const picker = store.add(quickInputService.createQuickPick<IQuickPickItem>({ useSeparators: true }));
 	const backButton = quickInputService.backButton;
-	let suppressHideDispose = false;
-	store.add(picker.onDidHide(() => {
-		if (!suppressHideDispose) {
-			store.dispose();
-		}
-	}));
 	picker.show();
 
 	let step = Step.SelectHookType;
@@ -376,379 +375,452 @@ export async function showConfigureHooksQuickPick(
 	const stepHistory: Step[] = [];
 	const goBack = (): Step | undefined => stepHistory.pop();
 
-	while (true) {
-		switch (step) {
-			case Step.SelectHookType: {
-				// Step 1: Show all lifecycle events with hook counts
-				const hookTypeItems: IHookTypeQuickPickItem[] = HOOK_TYPES.map(hookType => {
-					const count = hookCountByType.get(hookType.id) ?? 0;
-					const countLabel = count > 0 ? ` (${count})` : '';
-					return {
-						label: `${hookType.label}${countLabel}`,
-						description: hookType.description,
-						hookType
+	try {
+		while (true) {
+			switch (step) {
+				case Step.SelectHookType: {
+					// Step 1: Show lifecycle events with hook counts, filtered by target
+					const makeItem = ([hookType, meta]: [HookType, IHookTypeMeta]): IHookTypeQuickPickItem => {
+						const count = hookCountByType.get(hookType) ?? 0;
+						const countLabel = count > 0 ? ` (${count})` : '';
+						return {
+							label: `${meta.label}${countLabel}`,
+							description: meta.description,
+							hookType,
+							hookTypeMeta: meta
+						};
 					};
-				});
 
-				picker.items = hookTypeItems;
-				picker.value = '';
-				picker.placeholder = localize('commands.hooks.selectEvent.placeholder', 'Select a lifecycle event');
-				picker.title = localize('commands.hooks.title', 'Hooks');
-				picker.buttons = [];
+					let pickerItems: (IHookTypeQuickPickItem | IQuickPickSeparator)[];
 
-				const result = await awaitPick<IHookTypeQuickPickItem>(picker, backButton);
+					if (options?.target) {
+						// Filtered to a specific target
+						const targetHookTypes = new Set(Object.values(HOOKS_BY_TARGET[options.target]));
+						pickerItems = (Object.entries(HOOK_METADATA) as [HookType, IHookTypeMeta][])
+							.filter(([hookType]) => targetHookTypes.has(hookType))
+							.map(makeItem);
+					} else {
+						// No target: group into Default (shared), VS Code Only, Copilot CLI Only
+						const vscodeTypes = new Set(Object.values(HOOKS_BY_TARGET[Target.VSCode]));
+						const copilotTypes = new Set(Object.values(HOOKS_BY_TARGET[Target.GitHubCopilot]));
+						const allEntries = Object.entries(HOOK_METADATA) as [HookType, IHookTypeMeta][];
+
+						const shared = allEntries.filter(([h]) => vscodeTypes.has(h) && copilotTypes.has(h));
+						const vscodeOnly = allEntries.filter(([h]) => vscodeTypes.has(h) && !copilotTypes.has(h));
+						const copilotOnly = allEntries.filter(([h]) => !vscodeTypes.has(h) && copilotTypes.has(h));
+
+						pickerItems = [];
+						if (shared.length > 0) {
+							pickerItems.push({ type: 'separator', label: localize('hookSection.default', "Local/Copilot CLI Agents") });
+							pickerItems.push(...shared.map(makeItem));
+						}
+						if (vscodeOnly.length > 0) {
+							pickerItems.push({ type: 'separator', label: localize('hookSection.vscodeOnly', "Local Agents") });
+							pickerItems.push(...vscodeOnly.map(makeItem));
+						}
+						if (copilotOnly.length > 0) {
+							pickerItems.push({ type: 'separator', label: localize('hookSection.copilotCliOnly', "Copilot CLI Agents") });
+							pickerItems.push(...copilotOnly.map(makeItem));
+						}
+					}
 
-				if (!result || result === 'back') {
-					picker.hide();
-					return;
-				}
+					picker.items = pickerItems;
+					picker.value = '';
+					picker.placeholder = localize('commands.hooks.selectEvent.placeholder', 'Select a lifecycle event');
+					picker.title = localize('commands.hooks.title', 'Hooks');
+					picker.buttons = [];
 
-				selectedHookType = result;
-				stepHistory.push(Step.SelectHookType);
-				step = Step.SelectHook;
-				break;
-			}
+					const result = await awaitPick<IHookTypeQuickPickItem>(picker, backButton);
 
-			case Step.SelectHook: {
-				// Filter hooks by the selected type
-				const hooksOfType = hookEntries.filter(h => h.hookType === selectedHookType!.hookType.id);
+					if (!result || result === 'back') {
+						return;
+					}
 
-				// Step 2: Show "Add new hook" + existing hooks of this type
-				const hookItems: (IHookQuickPickItem | IQuickPickSeparator)[] = [];
+					selectedHookType = result;
+					stepHistory.push(Step.SelectHookType);
+					step = Step.SelectHook;
+					break;
+				}
 
-				// Add "Add new hook" option at the top
-				hookItems.push({
-					label: `$(plus) ${localize('commands.addNewHook.label', 'Add new hook...')}`,
-					isAddNewHook: true,
-					alwaysShow: true
-				});
+				case Step.SelectHook: {
+					// Filter hooks by the selected type
+					const hooksOfType = hookEntries.filter(h => h.hookType === selectedHookType!.hookType);
+
+					// Separate hooks by source
+					const fileHooks = hooksOfType.filter(h => !h.agentName);
+					const agentHooks = hooksOfType.filter(h => h.agentName);
+
+					// Step 2: Show "Add new hook" + existing hooks of this type
+					const hookItems: (IHookQuickPickItem | IQuickPickSeparator)[] = [];
 
-				// Add existing hooks
-				if (hooksOfType.length > 0) {
+					// Add "Add new hook" option at the top
 					hookItems.push({
-						type: 'separator',
-						label: localize('existingHooks', "Existing Hooks")
+						label: `$(plus) ${localize('commands.addNewHook.label', 'Add new hook...')}`,
+						isAddNewHook: true,
+						alwaysShow: true
 					});
 
-					for (const entry of hooksOfType) {
-						const description = labelService.getUriLabel(entry.fileUri, { relative: true });
+					// Add existing file-based hooks
+					if (fileHooks.length > 0) {
 						hookItems.push({
-							label: entry.commandLabel,
-							description,
-							hookEntry: entry
+							type: 'separator',
+							label: localize('existingHooks', "Existing Hooks")
 						});
+
+						for (const entry of fileHooks) {
+							const description = labelService.getUriLabel(entry.fileUri, { relative: true });
+							hookItems.push({
+								label: entry.commandLabel,
+								description,
+								hookEntry: entry
+							});
+						}
 					}
-				}
 
-				// Auto-execute if only "Add new hook" is available (no existing hooks)
-				if (hooksOfType.length === 0) {
-					selectedHook = hookItems[0] as IHookQuickPickItem;
-				} else {
-					picker.items = hookItems;
-					picker.value = '';
-					picker.placeholder = localize('commands.hooks.selectHook.placeholder', 'Select a hook to open or add a new one');
-					picker.title = selectedHookType!.hookType.label;
-					picker.buttons = [backButton];
+					// Add agent-defined hooks grouped by agent name
+					if (agentHooks.length > 0) {
+						const agentNames = [...new Set(agentHooks.map(h => h.agentName!))];
+						for (const agentName of agentNames) {
+							hookItems.push({
+								type: 'separator',
+								label: localize('agentHooks', "Agent: {0}", agentName)
+							});
+
+							for (const entry of agentHooks.filter(h => h.agentName === agentName)) {
+								const description = labelService.getUriLabel(entry.fileUri, { relative: true });
+								hookItems.push({
+									label: entry.commandLabel,
+									description,
+									hookEntry: entry
+								});
+							}
+						}
+					}
 
-					const result = await awaitPick<IHookQuickPickItem>(picker, backButton);
+					// Auto-execute if only "Add new hook" is available (no existing hooks)
+					if (hooksOfType.length === 0) {
+						selectedHook = hookItems[0] as IHookQuickPickItem;
+					} else {
+						picker.items = hookItems;
+						picker.value = '';
+						picker.placeholder = localize('commands.hooks.selectHook.placeholder', 'Select a hook to open or add a new one');
+						picker.title = selectedHookType!.hookTypeMeta.label;
+						picker.buttons = [backButton];
 
-					if (result === 'back') {
-						step = goBack() ?? Step.SelectHookType;
-						break;
-					}
-					if (!result) {
-						picker.hide();
-						return;
-					}
-					selectedHook = result;
-					stepHistory.push(Step.SelectHook);
-				}
+						const result = await awaitPick<IHookQuickPickItem>(picker, backButton);
 
-				// Handle clicking on existing hook (focus into command)
-				if (selectedHook.hookEntry) {
-					const entry = selectedHook.hookEntry;
-					let selection: ITextEditorSelection | undefined;
-
-					// Determine the command field name to highlight based on target platform
-					const commandFieldName = getEffectiveCommandFieldKey(entry.command, targetOS);
-
-					// Try to find the command field to highlight
-					if (commandFieldName) {
-						try {
-							const content = await fileService.readFile(entry.fileUri);
-							selection = findHookCommandSelection(
-								content.value.toString(),
-								entry.originalHookTypeId,
-								entry.index,
-								commandFieldName
-							);
-						} catch {
-							// Ignore errors and just open without selection
+						if (result === 'back') {
+							step = goBack() ?? Step.SelectHookType;
+							break;
 						}
+						if (!result) {
+							return;
+						}
+						selectedHook = result;
+						stepHistory.push(Step.SelectHook);
 					}
 
-					picker.hide();
-					if (callbacks?.openEditor) {
-						await callbacks.openEditor(entry.fileUri, { selection });
-					} else {
-						await editorService.openEditor({
-							resource: entry.fileUri,
-							options: {
-								selection,
-								pinned: false
+					// Handle clicking on existing hook (focus into command)
+					if (selectedHook.hookEntry) {
+						const entry = selectedHook.hookEntry;
+						let selection: ITextEditorSelection | undefined;
+
+						if (entry.agentName) {
+							// Agent hook: search the YAML frontmatter for the command
+							try {
+								const content = await fileService.readFile(entry.fileUri);
+								const commandText = formatHookCommandLabel(entry.command, targetOS);
+								if (commandText) {
+									selection = findHookCommandInYaml(content.value.toString(), commandText);
+								}
+							} catch {
+								// Ignore errors and just open without selection
 							}
-						});
-					}
-					return;
-				}
+						} else {
+							// File hook: use JSON-based selection finder
+							const commandFieldName = getEffectiveCommandFieldKey(entry.command, targetOS);
+
+							if (commandFieldName) {
+								try {
+									const content = await fileService.readFile(entry.fileUri);
+									selection = findHookCommandSelection(
+										content.value.toString(),
+										entry.originalHookTypeId,
+										entry.index,
+										commandFieldName
+									);
+								} catch {
+									// Ignore errors and just open without selection
+								}
+							}
+						}
 
-				// "Add new hook" was selected
-				step = Step.SelectFile;
-				break;
-			}
+						if (options?.openEditor) {
+							await options.openEditor(entry.fileUri, { selection });
+						} else {
+							await editorService.openEditor({
+								resource: entry.fileUri,
+								options: {
+									selection,
+									pinned: false
+								}
+							});
+						}
+						return;
+					}
 
-			case Step.SelectFile: {
-				// Step 3: Handle "Add new hook" - show create new file + existing hook files
-				// Get existing hook files (local storage only, not User Data)
-				const hookFiles = await promptsService.listPromptFilesForStorage(PromptsType.hook, PromptsStorage.local, CancellationToken.None);
+					// "Add new hook" was selected
+					step = Step.SelectFile;
+					break;
+				}
 
-				const fileItems: (IHookFileQuickPickItem | IQuickPickSeparator)[] = [];
+				case Step.SelectFile: {
+					// Step 3: Handle "Add new hook" - show create new file + existing hook files
+					// Get existing hook files (local storage only, not User Data)
+					const hookFiles = await promptsService.listPromptFilesForStorage(PromptsType.hook, PromptsStorage.local, CancellationToken.None);
 
-				// Add "Create new hook config file" option at the top
-				fileItems.push({
-					label: `$(new-file) ${localize('commands.createNewHookFile.label', 'Create new hook config file...')}`,
-					isCreateNewFile: true,
-					alwaysShow: true
-				});
+					const fileItems: (IHookFileQuickPickItem | IQuickPickSeparator)[] = [];
 
-				// Add existing hook files
-				if (hookFiles.length > 0) {
+					// Add "Create new hook config file" option at the top
 					fileItems.push({
-						type: 'separator',
-						label: localize('existingHookFiles', "Existing Hook Files")
+						label: `$(new-file) ${localize('commands.createNewHookFile.label', 'Create new hook config file...')}`,
+						isCreateNewFile: true,
+						alwaysShow: true
 					});
 
-					for (const hookFile of hookFiles) {
-						const relativePath = labelService.getUriLabel(hookFile.uri, { relative: true });
+					// Add existing hook files
+					if (hookFiles.length > 0) {
 						fileItems.push({
-							label: relativePath,
-							fileUri: hookFile.uri
+							type: 'separator',
+							label: localize('existingHookFiles', "Existing Hook Files")
 						});
+
+						for (const hookFile of hookFiles) {
+							const relativePath = labelService.getUriLabel(hookFile.uri, { relative: true });
+							fileItems.push({
+								label: relativePath,
+								fileUri: hookFile.uri
+							});
+						}
 					}
-				}
 
-				// Auto-execute if no existing hook files
-				if (hookFiles.length === 0) {
-					selectedFile = fileItems[0] as IHookFileQuickPickItem;
-				} else {
-					picker.items = fileItems;
-					picker.value = '';
-					picker.placeholder = localize('commands.hooks.selectFile.placeholder', 'Select a hook file or create a new one');
-					picker.title = localize('commands.hooks.addHook.title', 'Add Hook');
-					picker.buttons = [backButton];
+					// Auto-execute if no existing hook files
+					if (hookFiles.length === 0) {
+						selectedFile = fileItems[0] as IHookFileQuickPickItem;
+					} else {
+						picker.items = fileItems;
+						picker.value = '';
+						picker.placeholder = localize('commands.hooks.selectFile.placeholder', 'Select a hook file or create a new one');
+						picker.title = localize('commands.hooks.addHook.title', 'Add Hook');
+						picker.buttons = [backButton];
 
-					const result = await awaitPick<IHookFileQuickPickItem>(picker, backButton);
+						const result = await awaitPick<IHookFileQuickPickItem>(picker, backButton);
 
-					if (result === 'back') {
-						step = goBack() ?? Step.SelectHook;
-						break;
+						if (result === 'back') {
+							step = goBack() ?? Step.SelectHook;
+							break;
+						}
+						if (!result) {
+							return;
+						}
+						selectedFile = result;
+						stepHistory.push(Step.SelectFile);
 					}
-					if (!result) {
-						picker.hide();
+
+					// Handle adding hook to existing file
+					if (selectedFile.fileUri) {
+						await addHookToFile(
+							selectedFile.fileUri,
+							selectedHookType!.hookType,
+							fileService,
+							editorService,
+							notificationService,
+							bulkEditService,
+							options?.openEditor,
+						);
 						return;
 					}
-					selectedFile = result;
-					stepHistory.push(Step.SelectFile);
-				}
 
-				// Handle adding hook to existing file
-				if (selectedFile.fileUri) {
-					picker.hide();
-					await addHookToFile(
-						selectedFile.fileUri,
-						selectedHookType!.hookType.id as HookType,
-						fileService,
-						editorService,
-						notificationService,
-						bulkEditService,
-						callbacks?.openEditor,
-					);
-					return;
+					// "Create new hook config file" was selected
+					step = Step.SelectFolder;
+					break;
 				}
 
-				// "Create new hook config file" was selected
-				step = Step.SelectFolder;
-				break;
-			}
+				case Step.SelectFolder: {
+					// Get source folders for hooks
+					const allFolders = await promptsService.getSourceFolders(PromptsType.hook);
+					const localFolders = allFolders.filter(f => f.storage === PromptsStorage.local);
 
-			case Step.SelectFolder: {
-				// Get source folders for hooks
-				const allFolders = await promptsService.getSourceFolders(PromptsType.hook);
-				const localFolders = allFolders.filter(f => f.storage === PromptsStorage.local);
+					if (localFolders.length === 0) {
+						notificationService.error(localize('commands.hook.noLocalFolders', "Please open a workspace folder to configure hooks."));
+						return;
+					}
 
-				if (localFolders.length === 0) {
-					picker.hide();
-					notificationService.error(localize('commands.hook.noLocalFolders', "Please open a workspace folder to configure hooks."));
-					return;
-				}
+					// Auto-select if only one folder, otherwise show picker
+					selectedFolder = localFolders[0];
+					if (localFolders.length > 1) {
+						const folderItems = localFolders.map(folder => ({
+							label: labelService.getUriLabel(folder.uri, { relative: true }),
+							folder
+						}));
+
+						picker.items = folderItems;
+						picker.value = '';
+						picker.placeholder = localize('commands.hook.selectFolder.placeholder', 'Select a location for the hook file');
+						picker.title = localize('commands.hook.selectFolder.title', 'Hook File Location');
+						picker.buttons = [backButton];
+
+						const result = await awaitPick<typeof folderItems[0]>(picker, backButton);
+
+						if (result === 'back') {
+							step = goBack() ?? Step.SelectFile;
+							break;
+						}
+						if (!result) {
+							return;
+						}
+						selectedFolder = result.folder;
+						stepHistory.push(Step.SelectFolder);
+					}
 
-				// Auto-select if only one folder, otherwise show picker
-				selectedFolder = localFolders[0];
-				if (localFolders.length > 1) {
-					const folderItems = localFolders.map(folder => ({
-						label: labelService.getUriLabel(folder.uri, { relative: true }),
-						folder
-					}));
+					step = Step.EnterFilename;
+					break;
+				}
 
-					picker.items = folderItems;
-					picker.value = '';
-					picker.placeholder = localize('commands.hook.selectFolder.placeholder', 'Select a location for the hook file');
-					picker.title = localize('commands.hook.selectFolder.title', 'Hook File Location');
-					picker.buttons = [backButton];
+				case Step.EnterFilename: {
+					// Hide the picker and show an input box for the filename
+					picker.hide();
 
-					const result = await awaitPick<typeof folderItems[0]>(picker, backButton);
+					const fileNameResult = await new Promise<string | 'back' | undefined>(resolve => {
+						let resolved = false;
+						const done = (value: string | 'back' | undefined) => {
+							if (!resolved) {
+								resolved = true;
+								inputDisposables.dispose();
+								resolve(value);
+							}
+						};
+						const inputDisposables = new DisposableStore();
+						const inputBox = inputDisposables.add(quickInputService.createInputBox());
+						inputBox.prompt = localize('commands.hook.filename.prompt', "Enter hook file name");
+						inputBox.placeholder = localize('commands.hook.filename.placeholder', "e.g., hooks, diagnostics, security");
+						inputBox.title = localize('commands.hook.filename.title', "Hook File Name");
+						inputBox.buttons = [backButton];
+						inputBox.ignoreFocusOut = true;
+
+						inputDisposables.add(inputBox.onDidAccept(async () => {
+							const value = inputBox.value;
+							if (!value || !value.trim()) {
+								inputBox.validationMessage = localize('commands.hook.filename.required', "File name is required");
+								return;
+							}
+							const name = value.trim();
+							if (/[/\\:*?"<>|]/.test(name)) {
+								inputBox.validationMessage = localize('commands.hook.filename.invalidChars', "File name contains invalid characters");
+								return;
+							}
+							done(name);
+						}));
+						inputDisposables.add(inputBox.onDidChangeValue(() => {
+							inputBox.validationMessage = undefined;
+						}));
+						inputDisposables.add(inputBox.onDidTriggerButton(button => {
+							if (button === backButton) {
+								done('back');
+							}
+						}));
+						inputDisposables.add(inputBox.onDidHide(() => {
+							done(undefined);
+						}));
+						inputBox.show();
+					});
 
-					if (result === 'back') {
-						step = goBack() ?? Step.SelectFile;
+					if (fileNameResult === 'back') {
+						// Re-show the picker for the previous step
+						picker.show();
+						step = goBack() ?? Step.SelectFolder;
 						break;
 					}
-					if (!result) {
-						picker.hide();
+					if (!fileNameResult) {
 						return;
 					}
-					selectedFolder = result.folder;
-					stepHistory.push(Step.SelectFolder);
-				}
 
-				step = Step.EnterFilename;
-				break;
-			}
+					// Create the hooks folder if it doesn't exist
+					await fileService.createFolder(selectedFolder!.uri);
+
+					// Use user-provided filename with .json extension
+					const hookFileName = fileNameResult.endsWith('.json') ? fileNameResult : `${fileNameResult}.json`;
+					const hookFileUri = URI.joinPath(selectedFolder!.uri, hookFileName);
+
+					// Check if file already exists
+					if (await fileService.exists(hookFileUri)) {
+						// File exists - add hook to it instead of creating new
+						await addHookToFile(
+							hookFileUri,
+							selectedHookType!.hookType,
+							fileService,
+							editorService,
+							notificationService,
+							bulkEditService,
+							options?.openEditor,
+						);
+						return;
+					}
 
-			case Step.EnterFilename: {
-				// Hide the picker and show an input box for the filename
-				suppressHideDispose = true;
-				picker.hide();
-				suppressHideDispose = false;
-
-				const fileNameResult = await new Promise<string | 'back' | undefined>(resolve => {
-					let resolved = false;
-					const done = (value: string | 'back' | undefined) => {
-						if (!resolved) {
-							resolved = true;
-							inputDisposables.dispose();
-							resolve(value);
+					// Detect if new file is a Claude hooks file based on its path
+					const newFileFormat = getHookSourceFormat(hookFileUri);
+					const isClaudeNewFile = newFileFormat === HookSourceFormat.Claude;
+					const isCopilotCliOnly = !isClaudeNewFile
+						&& !new Set(Object.values(HOOKS_BY_TARGET[Target.VSCode])).has(selectedHookType!.hookType)
+						&& new Set(Object.values(HOOKS_BY_TARGET[Target.GitHubCopilot])).has(selectedHookType!.hookType);
+					const hookTypeKey = isClaudeNewFile
+						? (getClaudeHookTypeName(selectedHookType!.hookType) ?? selectedHookType!.hookType)
+						: isCopilotCliOnly
+							? (getCopilotCliHookTypeName(selectedHookType!.hookType) ?? selectedHookType!.hookType)
+							: selectedHookType!.hookType;
+					const newFileHookEntry = isCopilotCliOnly
+						? { type: 'command', [targetOS === OperatingSystem.Windows ? 'powershell' : 'bash']: '' }
+						: buildNewHookEntry(newFileFormat);
+					const commandFieldKey = isCopilotCliOnly
+						? (targetOS === OperatingSystem.Windows ? 'powershell' : 'bash')
+						: 'command';
+
+					// Create new hook file with the selected hook type
+					const hooksContent: Record<string, unknown> = {
+						...(isCopilotCliOnly ? { version: 1 } : {}),
+						hooks: {
+							[hookTypeKey]: [
+								newFileHookEntry
+							]
 						}
 					};
-					const inputDisposables = new DisposableStore();
-					const inputBox = inputDisposables.add(quickInputService.createInputBox());
-					inputBox.prompt = localize('commands.hook.filename.prompt', "Enter hook file name");
-					inputBox.placeholder = localize('commands.hook.filename.placeholder', "e.g., hooks, diagnostics, security");
-					inputBox.title = localize('commands.hook.filename.title', "Hook File Name");
-					inputBox.buttons = [backButton];
-					inputBox.ignoreFocusOut = true;
-
-					inputDisposables.add(inputBox.onDidAccept(async () => {
-						const value = inputBox.value;
-						if (!value || !value.trim()) {
-							inputBox.validationMessage = localize('commands.hook.filename.required', "File name is required");
-							return;
-						}
-						const name = value.trim();
-						if (/[/\\:*?"<>|]/.test(name)) {
-							inputBox.validationMessage = localize('commands.hook.filename.invalidChars', "File name contains invalid characters");
-							return;
-						}
-						done(name);
-					}));
-					inputDisposables.add(inputBox.onDidChangeValue(() => {
-						inputBox.validationMessage = undefined;
-					}));
-					inputDisposables.add(inputBox.onDidTriggerButton(button => {
-						if (button === backButton) {
-							done('back');
-						}
-					}));
-					inputDisposables.add(inputBox.onDidHide(() => {
-						done(undefined);
-					}));
-					inputBox.show();
-				});
 
-				if (fileNameResult === 'back') {
-					// Re-show the picker for the previous step
-					picker.show();
-					step = goBack() ?? Step.SelectFolder;
-					break;
-				}
-				if (!fileNameResult) {
-					store.dispose();
-					return;
-				}
+					const jsonContent = JSON.stringify(hooksContent, null, '\t');
+					await fileService.writeFile(hookFileUri, VSBuffer.fromString(jsonContent));
 
-				// Create the hooks folder if it doesn't exist
-				await fileService.createFolder(selectedFolder!.uri);
-
-				// Use user-provided filename with .json extension
-				const hookFileName = fileNameResult.endsWith('.json') ? fileNameResult : `${fileNameResult}.json`;
-				const hookFileUri = URI.joinPath(selectedFolder!.uri, hookFileName);
-
-				// Check if file already exists
-				if (await fileService.exists(hookFileUri)) {
-					// File exists - add hook to it instead of creating new
-					store.dispose();
-					await addHookToFile(
-						hookFileUri,
-						selectedHookType!.hookType.id as HookType,
-						fileService,
-						editorService,
-						notificationService,
-						bulkEditService,
-						callbacks?.openEditor,
-					);
-					return;
-				}
+					options?.onHookFileCreated?.(hookFileUri);
+
+					// Find the selection for the new hook's command field
+					const selection = findHookCommandSelection(jsonContent, hookTypeKey, 0, commandFieldKey);
 
-				// Detect if new file is a Claude hooks file based on its path
-				const newFileFormat = getHookSourceFormat(hookFileUri);
-				const isClaudeNewFile = newFileFormat === HookSourceFormat.Claude;
-				const hookTypeKey = isClaudeNewFile
-					? (getClaudeHookTypeName(selectedHookType!.hookType.id as HookType) ?? selectedHookType!.hookType.id)
-					: selectedHookType!.hookType.id;
-				const newFileHookEntry = buildNewHookEntry(newFileFormat);
-
-				// Create new hook file with the selected hook type
-				const hooksContent = {
-					hooks: {
-						[hookTypeKey]: [
-							newFileHookEntry
-						]
+					// Open editor with selection
+					if (options?.openEditor) {
+						await options.openEditor(hookFileUri, { selection });
+					} else {
+						await editorService.openEditor({
+							resource: hookFileUri,
+							options: {
+								selection,
+								pinned: false
+							}
+						});
 					}
-				};
-
-				const jsonContent = JSON.stringify(hooksContent, null, '\t');
-				await fileService.writeFile(hookFileUri, VSBuffer.fromString(jsonContent));
-
-				callbacks?.onHookFileCreated?.(hookFileUri);
-
-				// Find the selection for the new hook's command field
-				const selection = findHookCommandSelection(jsonContent, hookTypeKey, 0, 'command');
-
-				// Open editor with selection
-				store.dispose();
-				if (callbacks?.openEditor) {
-					await callbacks.openEditor(hookFileUri, { selection });
-				} else {
-					await editorService.openEditor({
-						resource: hookFileUri,
-						options: {
-							selection,
-							pinned: false
-						}
-					});
+					return;
 				}
-				return;
 			}
 		}
+	} finally {
+		store.dispose();
 	}
 }
 
diff --git a/src/vs/workbench/contrib/chat/browser/promptSyntax/hookUtils.ts b/src/vs/workbench/contrib/chat/browser/promptSyntax/hookUtils.ts
index e6dd6668f35ef..e019aecb93f25 100644
--- a/src/vs/workbench/contrib/chat/browser/promptSyntax/hookUtils.ts
+++ b/src/vs/workbench/contrib/chat/browser/promptSyntax/hookUtils.ts
@@ -10,7 +10,8 @@ import { IPromptsService } from '../../common/promptSyntax/service/promptsServic
 import { PromptsType } from '../../common/promptSyntax/promptTypes.js';
 import { IFileService } from '../../../../../platform/files/common/files.js';
 import { CancellationToken } from '../../../../../base/common/cancellation.js';
-import { formatHookCommandLabel, HOOK_TYPES, HookType, IHookCommand } from '../../common/promptSyntax/hookSchema.js';
+import { formatHookCommandLabel, IHookCommand } from '../../common/promptSyntax/hookSchema.js';
+import { HOOK_METADATA, HookType } from '../../common/promptSyntax/hookTypes.js';
 import { parseHooksFromFile, parseHooksIgnoringDisableAll } from '../../common/promptSyntax/hookCompatibility.js';
 import * as nls from '../../../../../nls.js';
 import { ILabelService } from '../../../../../platform/label/common/label.js';
@@ -113,6 +114,54 @@ export function findHookCommandSelection(content: string, hookType: string, inde
 	};
 }
 
+/**
+ * Finds the selection range for a hook command string in a YAML/Markdown file
+ * (e.g., an agent `.md` file with YAML frontmatter).
+ *
+ * Searches for the command text within command field lines and selects the value.
+ * Supports all hook command field keys: command, windows, linux, osx, bash, powershell.
+ *
+ * @param content The full file content
+ * @param commandText The command string to locate
+ * @returns The selection range, or undefined if not found
+ */
+export function findHookCommandInYaml(content: string, commandText: string): ITextEditorSelection | undefined {
+	const commandFieldKeys = ['command', 'windows', 'linux', 'osx', 'bash', 'powershell'];
+	const lines = content.split('\n');
+	for (let i = 0; i < lines.length; i++) {
+		const line = lines[i];
+		const trimmed = line.trimStart();
+
+		// Only match lines whose YAML key is a known command field
+		const matchedKey = commandFieldKeys.find(key =>
+			trimmed.startsWith(`${key}:`) || trimmed.startsWith(`- ${key}:`)
+		);
+		if (!matchedKey) {
+			continue;
+		}
+
+		// Search after the colon to avoid matching within the key name itself
+		const colonIdx = line.indexOf(':');
+		const idx = line.indexOf(commandText, colonIdx + 1);
+		if (idx !== -1) {
+			// Verify this is a full match (not a substring of a longer command)
+			const afterIdx = idx + commandText.length;
+			const charAfter = afterIdx < line.length ? line.charCodeAt(afterIdx) : -1;
+			// Accept if what follows is end of line, a quote, or whitespace
+			if (charAfter === -1 || charAfter === 34 /* " */ || charAfter === 39 /* ' */ || charAfter === 32 /* space */ || charAfter === 9 /* tab */) {
+				return {
+					startLineNumber: i + 1,
+					startColumn: idx + 1,
+					endLineNumber: i + 1,
+					endColumn: idx + 1 + commandText.length
+				};
+			}
+		}
+	}
+
+	return undefined;
+}
+
 /**
  * Parsed hook information.
  */
@@ -128,11 +177,15 @@ export interface IParsedHook {
 	originalHookTypeId: string;
 	/** If true, this hook is disabled via `disableAllHooks: true` in its file */
 	disabled?: boolean;
+	/** If set, this hook came from a custom agent's frontmatter */
+	agentName?: string;
 }
 
 export interface IParseAllHookFilesOptions {
 	/** Additional file URIs to parse (e.g., files skipped due to disableAllHooks) */
 	additionalDisabledFileUris?: readonly URI[];
+	/** If true, also collect hooks from custom agent frontmatter */
+	includeAgentHooks?: boolean;
 }
 
 /**
@@ -161,7 +214,7 @@ export async function parseAllHookFiles(
 			const { hooks } = parseHooksFromFile(hookFile.uri, json, workspaceRootUri, userHome);
 
 			for (const [hookType, { hooks: commands, originalId }] of hooks) {
-				const hookTypeMeta = HOOK_TYPES.find(h => h.id === hookType);
+				const hookTypeMeta = HOOK_METADATA[hookType];
 				if (!hookTypeMeta) {
 					continue;
 				}
@@ -199,7 +252,7 @@ export async function parseAllHookFiles(
 				const { hooks } = parseHooksIgnoringDisableAll(uri, json, workspaceRootUri, userHome);
 
 				for (const [hookType, { hooks: commands, originalId }] of hooks) {
-					const hookTypeMeta = HOOK_TYPES.find(h => h.id === hookType);
+					const hookTypeMeta = HOOK_METADATA[hookType];
 					if (!hookTypeMeta) {
 						continue;
 					}
@@ -226,5 +279,40 @@ export async function parseAllHookFiles(
 		}
 	}
 
+	// Collect hooks from custom agents' frontmatter
+	if (options?.includeAgentHooks) {
+		const agents = await promptsService.getCustomAgents(token);
+		for (const agent of agents) {
+			if (!agent.hooks) {
+				continue;
+			}
+			for (const hookTypeValue of Object.values(HookType)) {
+				const commands = agent.hooks[hookTypeValue];
+				if (!commands || commands.length === 0) {
+					continue;
+				}
+				const hookTypeMeta = HOOK_METADATA[hookTypeValue];
+				if (!hookTypeMeta) {
+					continue;
+				}
+				for (let i = 0; i < commands.length; i++) {
+					const command = commands[i];
+					const commandLabel = formatHookCommandLabel(command, os) || nls.localize('commands.hook.emptyCommand', '(empty command)');
+					parsedHooks.push({
+						hookType: hookTypeValue,
+						hookTypeLabel: hookTypeMeta.label,
+						command,
+						commandLabel,
+						fileUri: agent.uri,
+						filePath: labelService.getUriLabel(agent.uri, { relative: true }),
+						index: i,
+						originalHookTypeId: hookTypeValue,
+						agentName: agent.name,
+					});
+				}
+			}
+		}
+	}
+
 	return parsedHooks;
 }
diff --git a/src/vs/workbench/contrib/chat/browser/promptSyntax/newPromptFileActions.ts b/src/vs/workbench/contrib/chat/browser/promptSyntax/newPromptFileActions.ts
index 15f6f5b34f604..a5c04f02c1eef 100644
--- a/src/vs/workbench/contrib/chat/browser/promptSyntax/newPromptFileActions.ts
+++ b/src/vs/workbench/contrib/chat/browser/promptSyntax/newPromptFileActions.ts
@@ -16,7 +16,7 @@ import { KeybindingWeight } from '../../../../../platform/keybinding/common/keyb
 import { ILogService } from '../../../../../platform/log/common/log.js';
 import { INotificationService, NeverShowAgainScope, Severity } from '../../../../../platform/notification/common/notification.js';
 import { IOpenerService } from '../../../../../platform/opener/common/opener.js';
-import { getLanguageIdForPromptsType, PromptsType } from '../../common/promptSyntax/promptTypes.js';
+import { getLanguageIdForPromptsType, PromptsType, Target } from '../../common/promptSyntax/promptTypes.js';
 import { IUserDataSyncEnablementService, SyncResource } from '../../../../../platform/userDataSync/common/userDataSync.js';
 import { IEditorService } from '../../../../services/editor/common/editorService.js';
 import { CONFIGURE_SYNC_COMMAND_ID } from '../../../../services/userDataSync/common/userDataSync.js';
@@ -26,8 +26,8 @@ import { askForPromptFileName } from './pickers/askForPromptName.js';
 import { askForPromptSourceFolder } from './pickers/askForPromptSourceFolder.js';
 import { IQuickInputService } from '../../../../../platform/quickinput/common/quickInput.js';
 import { getCleanPromptName, SKILL_FILENAME } from '../../common/promptSyntax/config/promptFileLocations.js';
-import { Target, PromptsStorage } from '../../common/promptSyntax/service/promptsService.js';
-import { getTarget } from '../../common/promptSyntax/languageProviders/promptValidator.js';
+import { PromptsStorage } from '../../common/promptSyntax/service/promptsService.js';
+import { getTarget } from '../../common/promptSyntax/languageProviders/promptFileAttributes.js';
 
 /**
  * Options to override the default folder-picker and editor-open behaviour
@@ -186,7 +186,7 @@ function getDefaultContentSnippet(promptType: PromptsType, name: string | undefi
 					`. - "src/**/*.ts"`,
 					`---`,
 					``,
-					`<!-- Tip: Use /create-instruction in chat to generate content with agent assistance -->`,
+					`<!-- Tip: Use /create-instructions in chat to generate content with agent assistance -->`,
 					``,
 					`\${2:Provide coding guidelines that AI should follow when generating code, answering questions, or reviewing changes.}`,
 				].join('\n');
@@ -197,7 +197,7 @@ function getDefaultContentSnippet(promptType: PromptsType, name: string | undefi
 					`# applyTo: '\${1|**,**/*.ts|}' # when provided, instructions will automatically be added to the request context when the pattern matches an attached file`,
 					`---`,
 					``,
-					`<!-- Tip: Use /create-instruction in chat to generate content with agent assistance -->`,
+					`<!-- Tip: Use /create-instructions in chat to generate content with agent assistance -->`,
 					``,
 					`\${2:Provide project context and coding guidelines that AI should follow when generating code, answering questions, or reviewing changes.}`,
 				].join('\n');
diff --git a/src/vs/workbench/contrib/chat/browser/promptSyntax/pickers/promptFilePickers.ts b/src/vs/workbench/contrib/chat/browser/promptSyntax/pickers/promptFilePickers.ts
index 5113db79b5cfe..a2cfc90f7cd4b 100644
--- a/src/vs/workbench/contrib/chat/browser/promptSyntax/pickers/promptFilePickers.ts
+++ b/src/vs/workbench/contrib/chat/browser/promptSyntax/pickers/promptFilePickers.ts
@@ -8,7 +8,7 @@ import { URI } from '../../../../../../base/common/uri.js';
 import { Codicon } from '../../../../../../base/common/codicons.js';
 import { ThemeIcon } from '../../../../../../base/common/themables.js';
 import { AgentFileType, IExtensionPromptPath, IPromptPath, IPromptsService, PromptsStorage } from '../../../common/promptSyntax/service/promptsService.js';
-import { dirname, extUri, joinPath } from '../../../../../../base/common/resources.js';
+import { basename, dirname, extUri, joinPath } from '../../../../../../base/common/resources.js';
 import { DisposableStore } from '../../../../../../base/common/lifecycle.js';
 import { IFileService } from '../../../../../../platform/files/common/files.js';
 import { IOpenerService } from '../../../../../../platform/opener/common/opener.js';
@@ -17,7 +17,7 @@ import { ICommandService } from '../../../../../../platform/commands/common/comm
 import { getCleanPromptName } from '../../../common/promptSyntax/config/promptFileLocations.js';
 import { PromptsType, INSTRUCTIONS_DOCUMENTATION_URL, AGENT_DOCUMENTATION_URL, PROMPT_DOCUMENTATION_URL, SKILL_DOCUMENTATION_URL, HOOK_DOCUMENTATION_URL } from '../../../common/promptSyntax/promptTypes.js';
 import { NEW_PROMPT_COMMAND_ID, NEW_INSTRUCTIONS_COMMAND_ID, NEW_AGENT_COMMAND_ID, NEW_SKILL_COMMAND_ID } from '../newPromptFileActions.js';
-import { GENERATE_INSTRUCTIONS_COMMAND_ID, GENERATE_INSTRUCTION_COMMAND_ID, GENERATE_PROMPT_COMMAND_ID, GENERATE_SKILL_COMMAND_ID, GENERATE_AGENT_COMMAND_ID } from '../../actions/chatActions.js';
+import { GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID, GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID, GENERATE_PROMPT_COMMAND_ID, GENERATE_SKILL_COMMAND_ID, GENERATE_AGENT_COMMAND_ID } from '../../actions/chatActions.js';
 import { IKeyMods, IQuickInputButton, IQuickInputService, IQuickPick, IQuickPickItem, IQuickPickItemButtonEvent, IQuickPickSeparator } from '../../../../../../platform/quickinput/common/quickInput.js';
 import { askForPromptFileName } from './askForPromptName.js';
 import { IInstantiationService } from '../../../../../../platform/instantiation/common/instantiation.js';
@@ -27,6 +27,7 @@ import { ILabelService } from '../../../../../../platform/label/common/label.js'
 import { IProductService } from '../../../../../../platform/product/common/productService.js';
 import { PromptFileRewriter } from '../promptFileRewriter.js';
 import { isOrganizationPromptFile } from '../../../common/promptSyntax/utils/promptsServiceUtils.js';
+import { assertNever } from '../../../../../../base/common/assert.js';
 
 /**
  * Options for the {@link askToSelectInstructions} function.
@@ -53,6 +54,7 @@ export interface ISelectOptions {
 	readonly optionRename?: boolean;
 	readonly optionCopy?: boolean;
 	readonly optionVisibility?: boolean;
+	readonly optionRun?: boolean;
 }
 
 export interface ISelectPromptResult {
@@ -169,33 +171,33 @@ const NEW_INSTRUCTIONS_FILE_OPTION: IPromptPickerQuickPickItem = {
 };
 
 /**
- * A quick pick item that starts the 'Generate Workspace Instructions' command.
+ * A quick pick item that starts the 'Generate Agent Instructions' command.
  */
-const GENERATE_WORKSPACE_INSTRUCTIONS_OPTION: IPromptPickerQuickPickItem = {
+const GENERATE_AGENT_INSTRUCTIONS_OPTION: IPromptPickerQuickPickItem = {
 	type: 'item',
 	label: `$(sparkle) ${localize(
-		'commands.generate-workspace-instructions.select-dialog.label',
-		'Generate workspace instructions with agent...',
+		'commands.generate-agent-instructions.select-dialog.label',
+		'Generate agent instructions...',
 	)}`,
 	pickable: false,
 	alwaysShow: true,
 	buttons: [newHelpButton(PromptsType.instructions)],
-	commandId: GENERATE_INSTRUCTIONS_COMMAND_ID,
+	commandId: GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID,
 };
 
 /**
- * A quick pick item that starts the 'Generate On-demand Instruction' command.
+ * A quick pick item that starts the 'Generate On-demand Instructions' command.
  */
-const GENERATE_INSTRUCTION_OPTION: IPromptPickerQuickPickItem = {
+const GENERATE_ON_DEMAND_INSTRUCTIONS_OPTION: IPromptPickerQuickPickItem = {
 	type: 'item',
 	label: `$(sparkle) ${localize(
-		'commands.generate-instruction.select-dialog.label',
-		'Generate on-demand instruction with agent...',
+		'commands.generate-on-demand-instructions.select-dialog.label',
+		'Generate on-demand instructions...',
 	)}`,
 	pickable: false,
 	alwaysShow: true,
 	buttons: [newHelpButton(PromptsType.instructions)],
-	commandId: GENERATE_INSTRUCTION_COMMAND_ID,
+	commandId: GENERATE_ON_DEMAND_INSTRUCTIONS_COMMAND_ID,
 };
 
 /**
@@ -235,7 +237,7 @@ const GENERATE_PROMPT_OPTION: IPromptPickerQuickPickItem = {
 	type: 'item',
 	label: `$(sparkle) ${localize(
 		'commands.generate-prompt.select-dialog.label',
-		'Generate prompt with agent...',
+		'Generate prompt...',
 	)}`,
 	pickable: false,
 	alwaysShow: true,
@@ -250,7 +252,7 @@ const GENERATE_SKILL_OPTION: IPromptPickerQuickPickItem = {
 	type: 'item',
 	label: `$(sparkle) ${localize(
 		'commands.generate-skill.select-dialog.label',
-		'Generate skill with agent...',
+		'Generate skill...',
 	)}`,
 	pickable: false,
 	alwaysShow: true,
@@ -265,7 +267,7 @@ const GENERATE_AGENT_OPTION: IPromptPickerQuickPickItem = {
 	type: 'item',
 	label: `$(sparkle) ${localize(
 		'commands.generate-agent.select-dialog.label',
-		'Generate agent with agent...',
+		'Generate agent...',
 	)}`,
 	pickable: false,
 	alwaysShow: true,
@@ -322,6 +324,11 @@ const MAKE_INVISIBLE_BUTTON: IQuickInputButton = {
 	iconClass: ThemeIcon.asClassName(Codicon.eye),
 };
 
+const RUN_IN_CHAT_BUTTON: IQuickInputButton = {
+	tooltip: localize('runInChat', "Run in Chat View"),
+	iconClass: ThemeIcon.asClassName(Codicon.play),
+};
+
 export class PromptFilePickers {
 	constructor(
 		@IQuickInputService private readonly _quickInputService: IQuickInputService,
@@ -424,6 +431,9 @@ export class PromptFilePickers {
 
 	private async _createPromptPickItems(options: ISelectOptions, token: CancellationToken): Promise<(IPromptPickerQuickPickItem | IQuickPickSeparator)[]> {
 		const buttons: IQuickInputButton[] = [];
+		if (options.type === PromptsType.prompt && options.optionRun !== false) {
+			buttons.push(RUN_IN_CHAT_BUTTON);
+		}
 		if (options.optionEdit !== false) {
 			buttons.push(EDIT_BUTTON);
 		}
@@ -480,6 +490,9 @@ export class PromptFilePickers {
 		const exts = (await this._promptsService.listPromptFilesForStorage(options.type, PromptsStorage.extension, token)).filter(isExtensionPromptPath);
 		if (exts.length) {
 			const extButtons: IQuickInputButton[] = [];
+			if (options.type === PromptsType.prompt && options.optionRun !== false) {
+				extButtons.push(RUN_IN_CHAT_BUTTON);
+			}
 			if (options.optionEdit !== false) {
 				extButtons.push(EDIT_BUTTON);
 			}
@@ -507,6 +520,25 @@ export class PromptFilePickers {
 			result.push({ type: 'separator', label: localize('separator.user', "User Data") });
 			result.push(...sortByLabel(await Promise.all(users.map(u => this._createPromptPickItem(u, buttons, getVisibility(u), token)))));
 		}
+
+		// Plugin files are read-only so only copy button is available
+		const plugins = await this._promptsService.listPromptFilesForStorage(options.type, PromptsStorage.plugin, token);
+		if (plugins.length) {
+			const pluginButtons: IQuickInputButton[] = [];
+			if (options.optionCopy !== false) {
+				pluginButtons.push(COPY_BUTTON);
+			}
+			result.push({ type: 'separator', label: localize('separator.plugins', "Plugins") });
+			result.push(...sortByLabel(await Promise.all(plugins.map(p => this._createPromptPickItem(p, pluginButtons, getVisibility(p), token)))));
+		}
+
+		// Internal built-in files are read-only
+		const internals = await this._promptsService.listPromptFilesForStorage(options.type, PromptsStorage.internal, token);
+		if (internals.length) {
+			const internalButtons: IQuickInputButton[] = [];
+			result.push({ type: 'separator', label: localize('separator.builtin', "Built-in") });
+			result.push(...sortByLabel(await Promise.all(internals.map(p => this._createPromptPickItem(p, internalButtons, getVisibility(p), token)))));
+		}
 		return result;
 	}
 
@@ -525,7 +557,7 @@ export class PromptFilePickers {
 			case PromptsType.prompt:
 				return [NEW_PROMPT_FILE_OPTION, GENERATE_PROMPT_OPTION];
 			case PromptsType.instructions:
-				return [NEW_INSTRUCTIONS_FILE_OPTION, GENERATE_INSTRUCTION_OPTION, GENERATE_WORKSPACE_INSTRUCTIONS_OPTION];
+				return [NEW_INSTRUCTIONS_FILE_OPTION, GENERATE_ON_DEMAND_INSTRUCTIONS_OPTION, GENERATE_AGENT_INSTRUCTIONS_OPTION];
 			case PromptsType.agent:
 				return [NEW_AGENT_FILE_OPTION, GENERATE_AGENT_OPTION];
 			case PromptsType.skill:
@@ -552,6 +584,14 @@ export class PromptFilePickers {
 			case PromptsStorage.user:
 				tooltip = undefined;
 				break;
+			case PromptsStorage.plugin:
+				tooltip = promptFile.name;
+				break;
+			case PromptsStorage.internal:
+				tooltip = undefined;
+				break;
+			default:
+				assertNever(promptFile);
 		}
 		let iconClass: string | undefined;
 		if (visibility === false) {
@@ -596,6 +636,15 @@ export class PromptFilePickers {
 		}
 		const value = item.promptFileUri;
 
+		if (button === RUN_IN_CHAT_BUTTON) {
+			const commandId = quickPick.keyMods.ctrlCmd === true
+				? 'workbench.action.chat.run-in-new-chat.prompt.current'
+				: 'workbench.action.chat.run.prompt.current';
+			await this._commandService.executeCommand(commandId, value);
+			quickPick.hide();
+			return false;
+		}
+
 		// `edit` button was pressed, open the prompt file in editor
 		if (button === EDIT_BUTTON) {
 			await this._openerService.open(value);
@@ -634,16 +683,23 @@ export class PromptFilePickers {
 			// don't close the main prompt selection dialog by the confirmation dialog
 			return await this.keepQuickPickOpen(quickPick, async () => {
 
-				const filename = getCleanPromptName(value);
-				const message = localize('commands.prompts.use.select-dialog.delete-prompt.confirm.message', "Are you sure you want to delete '{0}'?", filename);
+				const isSkill = options.type === PromptsType.skill;
+				// For skills, use the parent folder name as the display name
+				// since skills are structured as <skillname>/SKILL.md.
+				const filename = isSkill ? basename(dirname(value)) : item.label;
+				const message = isSkill
+					? localize('commands.prompts.use.select-dialog.delete-skill.confirm.message', "Are you sure you want to delete skill '{0}' and its folder?", filename)
+					: localize('commands.prompts.use.select-dialog.delete-prompt.confirm.message', "Are you sure you want to delete '{0}'?", filename);
 				const { confirmed } = await this._dialogService.confirm({ message });
 				// if prompt deletion was not confirmed, nothing to do
 				if (!confirmed) {
 					return false;
 				}
 
-				// prompt deletion was confirmed so delete the prompt file
-				await this._fileService.del(value);
+				// For skills, delete the parent folder (e.g. .github/skills/my-skill/)
+				// since each skill is a folder containing SKILL.md.
+				const deleteTarget = isSkill ? dirname(value) : value;
+				await this._fileService.del(deleteTarget, { recursive: isSkill, useTrash: true });
 				return true;
 			});
 
@@ -686,7 +742,8 @@ export class PromptFilePickers {
 			optionDelete: true,
 			optionRename: true,
 			optionCopy: true,
-			optionVisibility: false
+			optionVisibility: false,
+			optionRun: false
 		};
 
 		try {
diff --git a/src/vs/workbench/contrib/chat/browser/promptSyntax/promptToolsCodeLensProvider.ts b/src/vs/workbench/contrib/chat/browser/promptSyntax/promptToolsCodeLensProvider.ts
index ac323f512e4e3..599946c97bf45 100644
--- a/src/vs/workbench/contrib/chat/browser/promptSyntax/promptToolsCodeLensProvider.ts
+++ b/src/vs/workbench/contrib/chat/browser/promptSyntax/promptToolsCodeLensProvider.ts
@@ -14,15 +14,15 @@ import { CommandsRegistry } from '../../../../../platform/commands/common/comman
 import { IInstantiationService } from '../../../../../platform/instantiation/common/instantiation.js';
 import { showToolsPicker } from '../actions/chatToolPicker.js';
 import { ILanguageModelToolsService } from '../../common/tools/languageModelToolsService.js';
-import { ALL_PROMPTS_LANGUAGE_SELECTOR, getPromptsTypeForLanguageId, PromptsType } from '../../common/promptSyntax/promptTypes.js';
-import { IPromptsService, Target } from '../../common/promptSyntax/service/promptsService.js';
+import { ALL_PROMPTS_LANGUAGE_SELECTOR, getPromptsTypeForLanguageId, PromptsType, Target } from '../../common/promptSyntax/promptTypes.js';
+import { IPromptsService } from '../../common/promptSyntax/service/promptsService.js';
 import { registerEditorFeature } from '../../../../../editor/common/editorFeatures.js';
 import { PromptFileRewriter } from './promptFileRewriter.js';
 import { Range } from '../../../../../editor/common/core/range.js';
 import { IEditorModel } from '../../../../../editor/common/editorCommon.js';
-import { isTarget, parseCommaSeparatedList, PromptHeaderAttributes } from '../../common/promptSyntax/promptFileParser.js';
-import { getTarget, isVSCodeOrDefaultTarget } from '../../common/promptSyntax/languageProviders/promptValidator.js';
+import { parseCommaSeparatedList, PromptHeaderAttributes } from '../../common/promptSyntax/promptFileParser.js';
 import { isBoolean } from '../../../../../base/common/types.js';
+import { getTarget, isTarget, isVSCodeOrDefaultTarget } from '../../common/promptSyntax/languageProviders/promptFileAttributes.js';
 
 class PromptToolsCodeLensProvider extends Disposable implements CodeLensProvider {
 
diff --git a/src/vs/workbench/contrib/chat/browser/promptSyntax/promptUrlHandler.ts b/src/vs/workbench/contrib/chat/browser/promptSyntax/promptUrlHandler.ts
index b77665f235153..5e8f2943516be 100644
--- a/src/vs/workbench/contrib/chat/browser/promptSyntax/promptUrlHandler.ts
+++ b/src/vs/workbench/contrib/chat/browser/promptSyntax/promptUrlHandler.ts
@@ -84,7 +84,7 @@ export class PromptUrlHandler extends Disposable implements IWorkbenchContributi
 				return true;
 			}
 
-			const result = await this.requestService.request({ type: 'GET', url: urlString }, CancellationToken.None);
+			const result = await this.requestService.request({ type: 'GET', url: urlString, callSite: 'promptUrlHandler.resolveUrl' }, CancellationToken.None);
 			if (result.res.statusCode !== 200) {
 				this.logService.error(`[PromptUrlHandler] Failed to fetch URL: ${urlString}`);
 				this.notificationService.error(localize('failed', 'Failed to fetch URL: {0}', urlString));
diff --git a/src/vs/workbench/contrib/chat/browser/promptsDebugContribution.ts b/src/vs/workbench/contrib/chat/browser/promptsDebugContribution.ts
index 9620797fe5efe..85c07a6c599e8 100644
--- a/src/vs/workbench/contrib/chat/browser/promptsDebugContribution.ts
+++ b/src/vs/workbench/contrib/chat/browser/promptsDebugContribution.ts
@@ -7,7 +7,6 @@ import { Disposable } from '../../../../base/common/lifecycle.js';
 import { generateUuid } from '../../../../base/common/uuid.js';
 import { IWorkbenchContribution } from '../../../common/contributions.js';
 import { IChatDebugResolvedEventContent, IChatDebugService } from '../common/chatDebugService.js';
-import { LocalChatSessionUri } from '../common/model/chatUri.js';
 import { IPromptDiscoveryInfo, IPromptsService } from '../common/promptSyntax/service/promptsService.js';
 
 /**
@@ -15,7 +14,7 @@ import { IPromptDiscoveryInfo, IPromptsService } from '../common/promptSyntax/se
  *
  * This contribution listens for discovery events emitted by the prompts service
  * and forwards them as debug log entries. It also registers a resolve provider
- * so expanding a discovery event in the debug panel shows the full file list.
+ * so expanding a discovery event in the Agent Debug Logs shows the full file list.
  */
 export class PromptsDebugContribution extends Disposable implements IWorkbenchContribution {
 
@@ -52,17 +51,37 @@ export class PromptsDebugContribution extends Disposable implements IWorkbenchCo
 				}
 			}
 
+			// Enrich details with file paths so they appear in the event
+			// payload (e.g. forwarded via onDidReceiveChatDebugEvent to the
+			// extension's JSONL file logger).
+			let details = entry.details;
+			if (entry.discoveryInfo) {
+				const info = entry.discoveryInfo;
+				const loaded = info.files.filter(f => f.status === 'loaded').map(f => f.name ?? f.uri.path.split('/').pop() ?? f.uri.toString());
+				const skipped = info.files.filter(f => f.status === 'skipped').map(f => {
+					const label = f.uri.toString();
+					return f.skipReason ? `${label} (${f.skipReason})` : label;
+				});
+				const folders = info.sourceFolders?.map(sf => sf.uri.path) ?? [];
+				const parts: string[] = [];
+				if (details) { parts.push(details); }
+				if (loaded.length > 0) { parts.push(`loaded: [${truncateList(loaded)}]`); }
+				if (skipped.length > 0) { parts.push(`skipped: [${truncateList(skipped)}]`); }
+				if (folders.length > 0) { parts.push(`folders: [${truncateList(folders)}]`); }
+				details = parts.join(' | ') || undefined;
+			}
+
 			chatDebugService.log(
-				LocalChatSessionUri.forSession(entry.sessionId),
+				entry.sessionResource,
 				entry.name,
-				entry.details,
+				details,
 				undefined,
 				{ id: eventId, category: entry.category },
 			);
 		}));
 
 		// Register a resolve provider so expanding a discovery event
-		// in the debug panel shows the full file list.
+		// in the Agent Debug Logs shows the full file list.
 		this._register(chatDebugService.registerProvider({
 			provideChatDebugLog: async () => undefined,
 			resolveChatDebugLogEvent: async (eventId) => {
@@ -93,10 +112,20 @@ export class PromptsDebugContribution extends Disposable implements IWorkbenchCo
 			sourceFolders: info.sourceFolders?.map(sf => ({
 				uri: sf.uri,
 				storage: sf.storage,
-				exists: sf.exists,
-				fileCount: sf.fileCount,
-				errorMessage: sf.errorMessage,
 			})),
 		};
 	}
 }
+
+const MAX_LIST_ITEMS = 100;
+
+/**
+ * Join a list of strings, truncating after {@link MAX_LIST_ITEMS} entries.
+ * Full details are available via {@link IChatDebugService.resolveEvent}.
+ */
+function truncateList(items: string[]): string {
+	if (items.length <= MAX_LIST_ITEMS) {
+		return items.join(', ');
+	}
+	return items.slice(0, MAX_LIST_ITEMS).join(', ') + ` (+${items.length - MAX_LIST_ITEMS} more)`;
+}
diff --git a/src/vs/workbench/contrib/chat/browser/tools/languageModelToolsConfirmationService.ts b/src/vs/workbench/contrib/chat/browser/tools/languageModelToolsConfirmationService.ts
index 50a3495c4f845..3661f5a27c379 100644
--- a/src/vs/workbench/contrib/chat/browser/tools/languageModelToolsConfirmationService.ts
+++ b/src/vs/workbench/contrib/chat/browser/tools/languageModelToolsConfirmationService.ts
@@ -424,7 +424,15 @@ export class LanguageModelToolsConfirmationService extends Disposable implements
 		};
 	}
 
-	manageConfirmationPreferences(tools: readonly IToolData[], options?: { defaultScope?: 'workspace' | 'profile' | 'session' }): void {
+	toolCanManageConfirmation(tool: IToolData): boolean {
+		return !!tool.canRequestPreApproval
+			|| !!tool.canRequestPostApproval
+			|| this._contributions.has(tool.id)
+			|| !!this._preExecutionToolConfirmStore.checkAutoConfirmation(tool.id)
+			|| !!this._postExecutionToolConfirmStore.checkAutoConfirmation(tool.id);
+	}
+
+	manageConfirmationPreferences(tools: readonly IToolData[], options?: { defaultScope?: 'workspace' | 'profile' | 'session'; focusToolId?: string }): void {
 		interface IToolTreeItem extends IQuickTreeItem {
 			type: 'tool' | 'server' | 'tool-pre' | 'tool-post' | 'server-pre' | 'server-post' | 'manage';
 			toolId?: string;
@@ -690,7 +698,7 @@ export class LanguageModelToolsConfirmationService extends Disposable implements
 					description,
 					checked,
 					pickable,
-					collapsed: true,
+					collapsed: tools.length > 1,
 					children: toolChildren.length > 0 ? toolChildren : undefined
 				});
 			}
@@ -773,12 +781,12 @@ export class LanguageModelToolsConfirmationService extends Disposable implements
 			}
 		}));
 
-		disposables.add(quickTree.onDidAccept(() => {
-			for (const item of quickTree.activeItems) {
-				if (item.type === 'manage') {
-					(item as ILanguageModelToolConfirmationContributionQuickTreeItem).onDidOpen?.();
-					quickTree.hide();
-				}
+		disposables.add(quickTree.onDidAccept(async () => {
+			const manageItem = quickTree.activeItems.find(i => i.type === 'manage');
+			if (manageItem) {
+				quickTree.hide();
+				await (manageItem as ILanguageModelToolConfirmationContributionQuickTreeItem).onDidOpen?.();
+				this.manageConfirmationPreferences(tools, options);
 			}
 		}));
 
@@ -787,6 +795,23 @@ export class LanguageModelToolsConfirmationService extends Disposable implements
 		}));
 
 		quickTree.show();
+
+		// If a focus tool was specified, expand its parent and set it as active.
+		// Must happen after show() since the tree data is applied via autorun on visibility.
+		if (options?.focusToolId) {
+			const focusToolId = options.focusToolId;
+			for (const serverItem of quickTree.itemTree) {
+				const serverItemTyped = serverItem as IToolTreeItem;
+				if (serverItemTyped.children) {
+					const toolItem = (serverItemTyped.children as IToolTreeItem[]).find(c => c.type === 'tool' && c.toolId === focusToolId);
+					if (toolItem) {
+						quickTree.expand(serverItem);
+						quickTree.reveal(toolItem);
+						break;
+					}
+				}
+			}
+		}
 	}
 
 	public resetToolAutoConfirmation(): void {
diff --git a/src/vs/workbench/contrib/chat/browser/tools/languageModelToolsService.ts b/src/vs/workbench/contrib/chat/browser/tools/languageModelToolsService.ts
index a367b84a045b7..f41293507bed6 100644
--- a/src/vs/workbench/contrib/chat/browser/tools/languageModelToolsService.ts
+++ b/src/vs/workbench/contrib/chat/browser/tools/languageModelToolsService.ts
@@ -16,6 +16,7 @@ import { Emitter, Event } from '../../../../../base/common/event.js';
 import { createMarkdownCommandLink, MarkdownString } from '../../../../../base/common/htmlContent.js';
 import { Iterable } from '../../../../../base/common/iterator.js';
 import { combinedDisposable, Disposable, DisposableStore, IDisposable, toDisposable } from '../../../../../base/common/lifecycle.js';
+import { getMediaMime } from '../../../../../base/common/mime.js';
 import { derived, derivedOpts, IObservable, IReader, observableFromEventOpts, ObservableSet, observableSignal, transaction } from '../../../../../base/common/observable.js';
 import Severity from '../../../../../base/common/severity.js';
 import { StopWatch } from '../../../../../base/common/stopwatch.js';
@@ -40,15 +41,16 @@ import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
 import { ChatRequestToolReferenceEntry, toToolSetVariableEntry, toToolVariableEntry } from '../../common/attachments/chatVariableEntries.js';
 import { IVariableReference } from '../../common/chatModes.js';
 import { ConfirmedReason, IChatService, IChatToolInvocation, ToolConfirmKind } from '../../common/chatService/chatService.js';
-import { ChatConfiguration } from '../../common/constants.js';
+import { ChatConfiguration, isAutoApproveLevel } from '../../common/constants.js';
 import { ILanguageModelChatMetadata } from '../../common/languageModels.js';
 import { IChatModel, IChatRequestModel } from '../../common/model/chatModel.js';
 import { ChatToolInvocation } from '../../common/model/chatProgressTypes/chatToolInvocation.js';
 import { chatSessionResourceToId } from '../../common/model/chatUri.js';
-import { HookType } from '../../common/promptSyntax/hookSchema.js';
+import { HookType } from '../../common/promptSyntax/hookTypes.js';
 import { ILanguageModelToolsConfirmationService } from '../../common/tools/languageModelToolsConfirmationService.js';
 import { CountTokensCallback, createToolSchemaUri, IBeginToolCallOptions, IExternalPreToolUseHookResult, ILanguageModelToolsService, IPreparedToolInvocation, isToolSet, IToolAndToolSetEnablementMap, IToolData, IToolImpl, IToolInvocation, IToolInvokedEvent, IToolResult, IToolResultInputOutputDetails, IToolSet, SpecedToolAliases, stringifyPromptTsxPart, ToolDataSource, ToolInvocationPresentation, toolMatchesModel, ToolSet, ToolSetForModel, VSCodeToolReference } from '../../common/tools/languageModelToolsService.js';
 import { getToolConfirmationAlert } from '../accessibility/chatAccessibilityProvider.js';
+import { IChatWidgetService } from '../chat.js';
 
 const jsonSchemaRegistry = Registry.as<JSONContributionRegistry.IJSONContributionRegistry>(JSONContributionRegistry.Extensions.JSONContribution);
 
@@ -61,7 +63,7 @@ interface ITrackedCall {
 	store: IDisposable;
 }
 
-const enum AutoApproveStorageKeys {
+export const enum AutoApproveStorageKeys {
 	GlobalAutoApproveOptIn = 'chat.tools.global.autoApprove.optIn'
 }
 
@@ -69,7 +71,10 @@ const SkipAutoApproveConfirmationKey = 'vscode.chat.tools.global.autoApprove.tes
 
 // This tool will always require user confirmation even in auto approval mode.
 // Users cannot auto approve this tool via settings either, as this is a tool used before the agentic loop.
-const toolIdThatCannotBeAutoApproved = 'vscode_get_confirmation_with_options';
+const toolIdsThatCannotBeAutoApproved = new Set([
+	'vscode_get_confirmation_with_options',
+	'vscode_get_modified_files_confirmation',
+]);
 
 export const globalAutoApproveDescription = localize2(
 	{
@@ -79,10 +84,10 @@ export const globalAutoApproveDescription = localize2(
 			'{Locked=\'](https://marketplace.visualstudio.com/items?itemName=ms-vscode-remote.remote-containers)\'}',
 			'{Locked=\'](https://code.visualstudio.com/docs/copilot/security)\'}',
 			'{Locked=\'**\'}',
-			'{Locked=\'`#chat.autoReply#`\'}',
+			'{Locked=\'[`chat.autoReply`](command:workbench.action.openSettings?%5B%22chat.autoReply%22%5D)\'}',
 		]
 	},
-	'Global auto approve also known as "YOLO mode" disables manual approval completely for _all tools in all workspaces_, allowing the agent to act fully autonomously. This is extremely dangerous and is *never* recommended, even containerized environments like [Codespaces](https://github.com/features/codespaces) and [Dev Containers](https://marketplace.visualstudio.com/items?itemName=ms-vscode-remote.remote-containers) have user keys forwarded into the container that could be compromised.\n\n**This feature disables [critical security protections](https://code.visualstudio.com/docs/copilot/security) and makes it much easier for an attacker to compromise the machine.**\n\nNote: This setting only controls tool approval and does not prevent the agent from asking questions. To automatically answer agent questions, use `#chat.autoReply#`.'
+	'Global auto approve also known as "YOLO mode" disables manual approval completely for _all tools in all workspaces_, allowing the agent to act fully autonomously. This is extremely dangerous and is *never* recommended, even containerized environments like [Codespaces](https://github.com/features/codespaces) and [Dev Containers](https://marketplace.visualstudio.com/items?itemName=ms-vscode-remote.remote-containers) have user keys forwarded into the container that could be compromised.\n\n**This feature disables [critical security protections](https://code.visualstudio.com/docs/copilot/security) and makes it much easier for an attacker to compromise the machine.**\n\nNote: This setting only controls tool approval and does not prevent the agent from asking questions. To automatically answer agent questions, use the [`chat.autoReply`](command:workbench.action.openSettings?%5B%22chat.autoReply%22%5D) setting.'
 );
 
 export class LanguageModelToolsService extends Disposable implements ILanguageModelToolsService {
@@ -110,6 +115,9 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 	/** Pending tool calls in the streaming phase, keyed by toolCallId */
 	private readonly _pendingToolCalls = new Map<string, ChatToolInvocation>();
 
+	/** Deduplicates _checkGlobalAutoApprove calls within this window */
+	private _pendingGlobalAutoApproveCheck: Promise<boolean> | undefined;
+
 	private readonly _isAgentModeEnabled: IObservable<boolean>;
 
 	constructor(
@@ -126,6 +134,7 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 		@IStorageService private readonly _storageService: IStorageService,
 		@ILanguageModelToolsConfirmationService private readonly _confirmationService: ILanguageModelToolsConfirmationService,
 		@ICommandService private readonly _commandService: ICommandService,
+		@IChatWidgetService private readonly _chatWidgetService: IChatWidgetService,
 	) {
 		super();
 
@@ -583,7 +592,7 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 				dto.toolSpecificData = toolInvocation?.toolSpecificData;
 				if (preparedInvocation?.confirmationMessages?.title) {
 					if (!IChatToolInvocation.executionConfirmedOrDenied(toolInvocation) && !autoConfirmed) {
-						this.playAccessibilitySignal([toolInvocation]);
+						this.playAccessibilitySignal([toolInvocation], dto.context?.sessionResource);
 					}
 					const userConfirmed = await IChatToolInvocation.awaitConfirmation(toolInvocation, token);
 					if (userConfirmed.type === ToolConfirmKind.Denied) {
@@ -635,10 +644,10 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 				}
 			}, token);
 			invocationTimeWatch.stop();
-			this.ensureToolDetails(dto, toolResult, tool.data);
+			this.ensureToolDetails(dto, toolResult, tool.data, toolInvocation);
 
 			const afterExecuteState = await toolInvocation?.didExecuteTool(toolResult, undefined, () =>
-				this.shouldAutoConfirmPostExecution(tool.data.id, tool.data.runsInWorkspace, tool.data.source, dto.parameters, dto.context?.sessionResource));
+				this.shouldAutoConfirmPostExecution(tool.data.id, tool.data.runsInWorkspace, tool.data.source, dto.parameters, dto.context?.sessionResource, dto.chatRequestId));
 
 			if (toolInvocation && afterExecuteState?.type === IChatToolInvocation.StateKind.WaitingForPostApproval) {
 				const postConfirm = await IChatToolInvocation.awaitPostConfirmation(toolInvocation, token);
@@ -788,7 +797,7 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 		}
 
 		// No hook decision - use normal auto-confirm logic
-		const autoConfirmed = await this.shouldAutoConfirm(tool.data.id, tool.data.runsInWorkspace, tool.data.source, dto.parameters, sessionResource);
+		const autoConfirmed = await this.shouldAutoConfirm(tool.data.id, tool.data.runsInWorkspace, tool.data.source, dto.parameters, sessionResource, dto.chatRequestId);
 		return { autoConfirmed, preparedInvocation };
 	}
 
@@ -833,14 +842,14 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 				...prepared.confirmationMessages,
 				title: localize('defaultToolConfirmation.title', 'Confirm tool execution'),
 				message: localize('defaultToolConfirmation.message', 'Run the \'{0}\' tool?', fullReferenceName),
-				disclaimer: tool.data.id === toolIdThatCannotBeAutoApproved ? undefined : new MarkdownString(localize('defaultToolConfirmation.disclaimer', 'Auto approval for \'{0}\' is restricted via {1}.', getToolFullReferenceName(tool.data), createMarkdownCommandLink({ title: '`' + ChatConfiguration.EligibleForAutoApproval + '`', id: 'workbench.action.openSettings', arguments: [ChatConfiguration.EligibleForAutoApproval] }, false)), { isTrusted: true }),
+				disclaimer: toolIdsThatCannotBeAutoApproved.has(tool.data.id) ? undefined : new MarkdownString(localize('defaultToolConfirmation.disclaimer', 'Auto approval for \'{0}\' is restricted via {1}.', getToolFullReferenceName(tool.data), createMarkdownCommandLink({ text: '`' + ChatConfiguration.EligibleForAutoApproval + '`', id: 'workbench.action.openSettings', arguments: [ChatConfiguration.EligibleForAutoApproval], tooltip: localize('openSettings.autoApproval.tooltip', 'Open settings to configure auto-approval') }, false)), { isTrusted: true }),
 				allowAutoConfirm: false,
 			};
 		}
 
 		if (!isEligibleForAutoApproval && prepared?.confirmationMessages?.title) {
 			// Always overwrite the disclaimer if not eligible for auto-approval
-			prepared.confirmationMessages.disclaimer = tool.data.id === toolIdThatCannotBeAutoApproved ? undefined : new MarkdownString(localize('defaultToolConfirmation.disclaimer', 'Auto approval for \'{0}\' is restricted via {1}.', getToolFullReferenceName(tool.data), createMarkdownCommandLink({ title: '`' + ChatConfiguration.EligibleForAutoApproval + '`', id: 'workbench.action.openSettings', arguments: [ChatConfiguration.EligibleForAutoApproval] }, false)), { isTrusted: true });
+			prepared.confirmationMessages.disclaimer = toolIdsThatCannotBeAutoApproved.has(tool.data.id) ? undefined : new MarkdownString(localize('defaultToolConfirmation.disclaimer', 'Auto approval for \'{0}\' is restricted via {1}.', getToolFullReferenceName(tool.data), createMarkdownCommandLink({ text: '`' + ChatConfiguration.EligibleForAutoApproval + '`', id: 'workbench.action.openSettings', arguments: [ChatConfiguration.EligibleForAutoApproval], tooltip: localize('openSettings.autoApproval.tooltip', 'Open settings to configure auto-approval') }, false)), { isTrusted: true });
 		}
 
 		if (prepared?.confirmationMessages?.title) {
@@ -940,12 +949,21 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 		}
 	}
 
-	private playAccessibilitySignal(toolInvocations: ChatToolInvocation[]): void {
+	private playAccessibilitySignal(toolInvocations: ChatToolInvocation[], chatSessionResource: URI | undefined): void {
 		const autoApproved = this._configurationService.getValue(ChatConfiguration.GlobalAutoApprove);
 		if (autoApproved) {
 			return;
 		}
 
+		// Autopilot/auto-approve permission levels auto-approve all tools, skip signal
+		if (chatSessionResource) {
+			const model = this._chatService.getSession(chatSessionResource);
+			const request = model?.getRequests().at(-1);
+			if (isAutoApproveLevel(request?.modeInfo?.permissionLevel) || this._isSessionLiveAutoApproveLevel(chatSessionResource)) {
+				return;
+			}
+		}
+
 		// Filter out any tool invocations that have already been confirmed/denied.
 		// This is a defensive check - normally the call site should prevent this,
 		// but tools may be auto-approved through various mechanisms (per-session rules,
@@ -966,8 +984,8 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 		}
 	}
 
-	private ensureToolDetails(dto: IToolInvocation, toolResult: IToolResult, toolData: IToolData): void {
-		if (!toolResult.toolResultDetails && toolData.alwaysDisplayInputOutput) {
+	private ensureToolDetails(dto: IToolInvocation, toolResult: IToolResult, toolData: IToolData, toolInvocation: ChatToolInvocation | undefined): void {
+		if (!toolResult.toolResultDetails && (toolData.alwaysDisplayInputOutput || (this.toolResultHasImages(toolResult) && !this.toolResultMessageHasImageFileWidgets(toolResult, toolInvocation)))) {
 			toolResult.toolResultDetails = {
 				input: this.formatToolInput(dto),
 				output: this.toolResultToIO(toolResult),
@@ -975,6 +993,41 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 		}
 	}
 
+	private toolResultHasImages(toolResult: IToolResult): boolean {
+		return toolResult.content.some(part => part.kind === 'data' && part.value.mimeType?.startsWith('image/'));
+	}
+
+	/**
+	 * Returns true if the tool result message (or falling back to the tool invocation's
+	 * pastTenseMessage from streaming) contains empty markdown links pointing to image
+	 * files (the `[](imageUri)` pattern) that will be rendered as file pills by renderFileWidgets.
+	 */
+	private toolResultMessageHasImageFileWidgets(toolResult: IToolResult, toolInvocation: ChatToolInvocation | undefined): boolean {
+		// Check toolResult.toolResultMessage first — this is what didExecuteTool will
+		// copy into pastTenseMessage, and it's already available at this point.
+		// Fall back to pastTenseMessage which may have been set during the streaming phase.
+		const message = toolResult.toolResultMessage ?? toolInvocation?.pastTenseMessage;
+		if (!message) {
+			return false;
+		}
+		const value = typeof message === 'string' ? message : message.value;
+		// Match empty-text markdown links: [](uri) or [ ](uri), capturing the uri
+		const linkPattern = /\[\s*\]\((?<uri>[^)]+)\)/g;
+		let match: RegExpExecArray | null;
+		while ((match = linkPattern.exec(value)) !== null) {
+			try {
+				const parsed = URI.parse(match.groups!.uri);
+				const mime = getMediaMime(parsed.path);
+				if (mime?.startsWith('image/')) {
+					return true;
+				}
+			} catch {
+				// Invalid URI, skip
+			}
+		}
+		return false;
+	}
+
 	private formatToolInput(dto: IToolInvocation): string {
 		return JSON.stringify(dto.parameters, undefined, 2);
 	}
@@ -993,6 +1046,26 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 		});
 	}
 
+	/**
+	 * Returns true if enterprise policy has explicitly disabled the global auto-approve setting.
+	 * When this is the case, Bypass Approvals and Autopilot permission levels should not auto-approve tools.
+	 */
+	private _isAutoApprovePolicyRestricted(): boolean {
+		const inspected = this._configurationService.inspect<boolean>(ChatConfiguration.GlobalAutoApprove);
+		return inspected.policyValue === false;
+	}
+
+	/**
+	 * Returns true if the session's current (live) permission picker level is auto-approve.
+	 * This checks the widget's current state, not what was stamped on the request,
+	 * so switching to Autopilot mid-session takes effect immediately.
+	 */
+	private _isSessionLiveAutoApproveLevel(chatSessionResource: URI): boolean {
+		const widget = this._chatWidgetService.getWidgetBySessionResource(chatSessionResource)
+			?? this._chatWidgetService.lastFocusedWidget;
+		return !!widget && isAutoApproveLevel(widget.input.currentModeInfo.permissionLevel);
+	}
+
 	private getEligibleForAutoApprovalSpecialCase(toolData: IToolData): string | undefined {
 		if (toolData.id === 'vscode_fetchWebPage_internal') {
 			return 'fetch';
@@ -1006,7 +1079,7 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 			// Special case, this fetch will call an internal tool 'vscode_fetchWebPage_internal'
 			return true;
 		}
-		if (toolData.id === toolIdThatCannotBeAutoApproved) {
+		if (toolIdsThatCannotBeAutoApproved.has(toolData.id)) {
 			// Special case, this tool will always require user confirmation as there are multiple options,
 			// These aren't LM generated instead are generated by extension before agentic loop starts.
 			return false;
@@ -1037,12 +1110,24 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 		return true;
 	}
 
-	private async shouldAutoConfirm(toolId: string, runsInWorkspace: boolean | undefined, source: ToolDataSource, parameters: unknown, chatSessionResource: URI | undefined): Promise<ConfirmedReason | undefined> {
+	private async shouldAutoConfirm(toolId: string, runsInWorkspace: boolean | undefined, source: ToolDataSource, parameters: unknown, chatSessionResource: URI | undefined, chatRequestId: string | undefined): Promise<ConfirmedReason | undefined> {
 		const tool = this._tools.get(toolId);
 		if (!tool) {
 			return undefined;
 		}
 
+		// Auto-Approve All permission level bypasses all tool confirmations,
+		// unless enterprise policy has explicitly disabled global auto-approve.
+		// Check both the request-stamped level AND the live picker level so that
+		// switching to Autopilot mid-session takes effect immediately.
+		if (chatSessionResource && !this._isAutoApprovePolicyRestricted()) {
+			const model = this._chatService.getSession(chatSessionResource);
+			const request = model?.getRequests().at(-1);
+			if (isAutoApproveLevel(request?.modeInfo?.permissionLevel) || this._isSessionLiveAutoApproveLevel(chatSessionResource)) {
+				return { type: ToolConfirmKind.ConfirmationNotNeeded, reason: 'auto-approve-all' };
+			}
+		}
+
 		if (!this.isToolEligibleForAutoApproval(tool.data)) {
 			return undefined;
 		}
@@ -1074,7 +1159,18 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 		return undefined;
 	}
 
-	private async shouldAutoConfirmPostExecution(toolId: string, runsInWorkspace: boolean | undefined, source: ToolDataSource, parameters: unknown, chatSessionResource: URI | undefined): Promise<ConfirmedReason | undefined> {
+	private async shouldAutoConfirmPostExecution(toolId: string, runsInWorkspace: boolean | undefined, source: ToolDataSource, parameters: unknown, chatSessionResource: URI | undefined, chatRequestId: string | undefined): Promise<ConfirmedReason | undefined> {
+		// Auto-Approve All permission level bypasses all post-execution confirmations,
+		// unless enterprise policy has explicitly disabled global auto-approve.
+		// Check both the request-stamped level AND the live picker level.
+		if (chatSessionResource && !this._isAutoApprovePolicyRestricted()) {
+			const model = this._chatService.getSession(chatSessionResource);
+			const request = model?.getRequests().at(-1);
+			if (isAutoApproveLevel(request?.modeInfo?.permissionLevel) || this._isSessionLiveAutoApproveLevel(chatSessionResource)) {
+				return { type: ToolConfirmKind.ConfirmationNotNeeded, reason: 'auto-approve-all' };
+			}
+		}
+
 		if (this._configurationService.getValue<boolean>(ChatConfiguration.GlobalAutoApprove) && await this._checkGlobalAutoApprove()) {
 			return { type: ToolConfirmKind.Setting, id: ChatConfiguration.GlobalAutoApprove };
 		}
@@ -1092,35 +1188,68 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 			return true;
 		}
 
-		const promptResult = await this._dialogService.prompt({
-			type: Severity.Warning,
-			message: localize('autoApprove2.title', 'Enable global auto approve?'),
-			buttons: [
-				{
-					label: localize('autoApprove2.button.enable', 'Enable'),
-					run: () => true
-				},
-				{
-					label: localize('autoApprove2.button.disable', 'Disable'),
-					run: () => false
+		if (this._pendingGlobalAutoApproveCheck) {
+			return this._pendingGlobalAutoApproveCheck;
+		}
+
+		this._pendingGlobalAutoApproveCheck = this._doCheckGlobalAutoApprove();
+		try {
+			return await this._pendingGlobalAutoApproveCheck;
+		} finally {
+			this._pendingGlobalAutoApproveCheck = undefined;
+		}
+	}
+
+	private async _doCheckGlobalAutoApprove(): Promise<boolean> {
+		const store = new DisposableStore();
+		try {
+			// Dismiss the dialog automatically if another window stores the
+			// opt-in flag, avoiding duplicate approval prompts.
+			const cts = new CancellationTokenSource();
+			store.add(cts);
+			store.add(this._storageService.onDidChangeValue(StorageScope.APPLICATION, AutoApproveStorageKeys.GlobalAutoApproveOptIn, store)(() => {
+				if (this._storageService.getBoolean(AutoApproveStorageKeys.GlobalAutoApproveOptIn, StorageScope.APPLICATION, false)) {
+					cts.cancel();
+				}
+			}));
+
+			const promptResult = await this._dialogService.prompt({
+				type: Severity.Warning,
+				message: localize('autoApprove2.title', 'Enable global auto approve?'),
+				buttons: [
+					{
+						label: localize('autoApprove2.button.enable', 'Enable'),
+						run: () => true
+					},
+					{
+						label: localize('autoApprove2.button.disable', 'Disable'),
+						run: () => false
+					},
+				],
+				custom: {
+					icon: Codicon.warning,
+					markdownDetails: [{
+						markdown: new MarkdownString(globalAutoApproveDescription.value, { isTrusted: { enabledCommands: ['workbench.action.openSettings'] } }),
+					}],
 				},
-			],
-			custom: {
-				icon: Codicon.warning,
-				disableCloseAction: true,
-				markdownDetails: [{
-					markdown: new MarkdownString(globalAutoApproveDescription.value),
-				}],
+				token: cts.token,
+			});
+
+			// If cancelled by cross-window approval, treat as approved
+			if (cts.token.isCancellationRequested) {
+				return true;
 			}
-		});
 
-		if (promptResult.result !== true) {
-			await this._configurationService.updateValue(ChatConfiguration.GlobalAutoApprove, false);
-			return false;
-		}
+			if (promptResult.result !== true) {
+				await this._configurationService.updateValue(ChatConfiguration.GlobalAutoApprove, false);
+				return false;
+			}
 
-		this._storageService.store(AutoApproveStorageKeys.GlobalAutoApproveOptIn, true, StorageScope.APPLICATION, StorageTarget.USER);
-		return true;
+			this._storageService.store(AutoApproveStorageKeys.GlobalAutoApproveOptIn, true, StorageScope.APPLICATION, StorageTarget.USER);
+			return true;
+		} finally {
+			store.dispose();
+		}
 	}
 
 	private cleanupCallDisposables(requestId: string | undefined, store: DisposableStore): void {
@@ -1150,7 +1279,6 @@ export class LanguageModelToolsService extends Disposable implements ILanguageMo
 		// Clean up any pending tool calls that belong to this request
 		for (const [toolCallId, invocation] of this._pendingToolCalls) {
 			if (invocation.chatRequestId === requestId) {
-				invocation.cancelFromStreaming(ToolConfirmKind.Skipped);
 				this._pendingToolCalls.delete(toolCallId);
 			}
 		}
diff --git a/src/vs/workbench/contrib/chat/browser/tools/usagesTool.ts b/src/vs/workbench/contrib/chat/browser/tools/usagesTool.ts
index 075977bc799a1..153763ce7b059 100644
--- a/src/vs/workbench/contrib/chat/browser/tools/usagesTool.ts
+++ b/src/vs/workbench/contrib/chat/browser/tools/usagesTool.ts
@@ -11,7 +11,7 @@ import { escapeRegExpCharacters } from '../../../../../base/common/strings.js';
 import { Disposable, IDisposable } from '../../../../../base/common/lifecycle.js';
 import { ResourceSet } from '../../../../../base/common/map.js';
 import { ThemeIcon } from '../../../../../base/common/themables.js';
-import { relativePath } from '../../../../../base/common/resources.js';
+import { isEqual, relativePath } from '../../../../../base/common/resources.js';
 import { Position } from '../../../../../editor/common/core/position.js';
 import { Range } from '../../../../../editor/common/core/range.js';
 import { Location, LocationLink } from '../../../../../editor/common/languages.js';
@@ -297,7 +297,7 @@ export class UsagesTool extends Disposable implements IToolImpl {
 	}
 
 	private _overlaps(a: LocationLink, b: LocationLink): boolean {
-		if (a.uri.toString() !== b.uri.toString()) {
+		if (!isEqual(a.uri, b.uri)) {
 			return false;
 		}
 		return Range.areIntersectingOrTouching(a.range, b.range);
diff --git a/src/vs/workbench/contrib/chat/browser/viewsWelcome/chatViewWelcomeController.ts b/src/vs/workbench/contrib/chat/browser/viewsWelcome/chatViewWelcomeController.ts
index 15899bc63071e..7cc5960a26f4d 100644
--- a/src/vs/workbench/contrib/chat/browser/viewsWelcome/chatViewWelcomeController.ts
+++ b/src/vs/workbench/contrib/chat/browser/viewsWelcome/chatViewWelcomeController.ts
@@ -6,31 +6,23 @@
 import { asCSSUrl } from '../../../../../base/browser/cssValue.js';
 import * as dom from '../../../../../base/browser/dom.js';
 import { createCSSRule } from '../../../../../base/browser/domStylesheets.js';
-import { StandardKeyboardEvent } from '../../../../../base/browser/keyboardEvent.js';
 import { IRenderedMarkdown } from '../../../../../base/browser/markdownRenderer.js';
 import { Button } from '../../../../../base/browser/ui/button/button.js';
 import { renderIcon } from '../../../../../base/browser/ui/iconLabel/iconLabels.js';
-import { Action, IAction } from '../../../../../base/common/actions.js';
-import { Codicon } from '../../../../../base/common/codicons.js';
 import { Event } from '../../../../../base/common/event.js';
 import { StringSHA1 } from '../../../../../base/common/hash.js';
 import { IMarkdownString } from '../../../../../base/common/htmlContent.js';
-import { KeyCode } from '../../../../../base/common/keyCodes.js';
 import { Disposable, DisposableStore } from '../../../../../base/common/lifecycle.js';
 import { IObservable, ISettableObservable, observableValue } from '../../../../../base/common/observable.js';
 import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { URI } from '../../../../../base/common/uri.js';
-import { localize } from '../../../../../nls.js';
 import { IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
-import { IContextMenuService } from '../../../../../platform/contextview/browser/contextView.js';
 import { IInstantiationService } from '../../../../../platform/instantiation/common/instantiation.js';
 import { ILogService } from '../../../../../platform/log/common/log.js';
 import { IMarkdownRendererService } from '../../../../../platform/markdown/browser/markdownRenderer.js';
 import { IOpenerService } from '../../../../../platform/opener/common/opener.js';
-import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
 import { defaultButtonStyles } from '../../../../../platform/theme/browser/defaultStyles.js';
 import { ChatAgentLocation } from '../../common/constants.js';
-import { IChatWidgetService } from '../chat.js';
 import { chatViewsWelcomeRegistry, IChatViewsWelcomeDescriptor } from './chatViewsWelcome.js';
 
 const $ = dom.$;
@@ -133,18 +125,9 @@ export interface IChatViewWelcomeContent {
 	readonly additionalMessage?: string | IMarkdownString;
 	tips?: IMarkdownString;
 	readonly inputPart?: HTMLElement;
-	readonly suggestedPrompts?: readonly IChatSuggestedPrompts[];
 	readonly useLargeIcon?: boolean;
 }
 
-export interface IChatSuggestedPrompts {
-	readonly icon?: ThemeIcon;
-	readonly label: string;
-	readonly description?: string;
-	readonly prompt: string;
-	readonly uri?: URI;
-}
-
 export interface IChatViewWelcomeRenderOptions {
 	readonly firstLinkToButton?: boolean;
 	readonly location: ChatAgentLocation;
@@ -159,10 +142,7 @@ export class ChatViewWelcomePart extends Disposable {
 		options: IChatViewWelcomeRenderOptions | undefined,
 		@IOpenerService private openerService: IOpenerService,
 		@ILogService private logService: ILogService,
-		@IChatWidgetService private chatWidgetService: IChatWidgetService,
-		@ITelemetryService private telemetryService: ITelemetryService,
 		@IMarkdownRendererService private readonly markdownRendererService: IMarkdownRendererService,
-		@IContextMenuService private readonly contextMenuService: IContextMenuService,
 	) {
 		super();
 
@@ -213,88 +193,6 @@ export class ChatViewWelcomePart extends Disposable {
 				}
 			}
 
-			// Render suggested prompts for both new user and regular modes
-			if (content.suggestedPrompts && content.suggestedPrompts.length) {
-				const suggestedPromptsContainer = dom.append(this.element, $('.chat-welcome-view-suggested-prompts'));
-				const titleElement = dom.append(suggestedPromptsContainer, $('.chat-welcome-view-suggested-prompts-title'));
-				titleElement.textContent = localize('chatWidget.suggestedActions', 'Suggested Actions');
-
-				for (const prompt of content.suggestedPrompts) {
-					const promptElement = dom.append(suggestedPromptsContainer, $('.chat-welcome-view-suggested-prompt'));
-					// Make the prompt element keyboard accessible
-					promptElement.setAttribute('role', 'button');
-					promptElement.setAttribute('tabindex', '0');
-					const promptAriaLabel = prompt.description
-						? localize('suggestedPromptAriaLabelWithDescription', 'Suggested prompt: {0}, {1}', prompt.label, prompt.description)
-						: localize('suggestedPromptAriaLabel', 'Suggested prompt: {0}', prompt.label);
-					promptElement.setAttribute('aria-label', promptAriaLabel);
-					const titleElement = dom.append(promptElement, $('.chat-welcome-view-suggested-prompt-title'));
-					titleElement.textContent = prompt.label;
-					const tooltip = localize('runPromptTitle', "Suggested prompt: {0}", prompt.prompt);
-					promptElement.title = tooltip;
-					titleElement.title = tooltip;
-					if (prompt.description) {
-						const descriptionElement = dom.append(promptElement, $('.chat-welcome-view-suggested-prompt-description'));
-						descriptionElement.textContent = prompt.description;
-						descriptionElement.title = prompt.description;
-					}
-					const executePrompt = () => {
-						type SuggestedPromptClickEvent = { suggestedPrompt: string };
-
-						type SuggestedPromptClickData = {
-							owner: 'bhavyaus';
-							comment: 'Event used to gain insights into when suggested prompts are clicked.';
-							suggestedPrompt: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The suggested prompt clicked.' };
-						};
-
-						this.telemetryService.publicLog2<SuggestedPromptClickEvent, SuggestedPromptClickData>('chat.clickedSuggestedPrompt', {
-							suggestedPrompt: prompt.prompt,
-						});
-
-						if (!this.chatWidgetService.lastFocusedWidget) {
-							const widgets = this.chatWidgetService.getWidgetsByLocations(ChatAgentLocation.Chat);
-							if (widgets.length) {
-								widgets[0].setInput(prompt.prompt);
-							}
-						} else {
-							this.chatWidgetService.lastFocusedWidget.setInput(prompt.prompt);
-						}
-					};
-					// Add context menu handler
-					this._register(dom.addDisposableListener(promptElement, dom.EventType.CONTEXT_MENU, (e: MouseEvent) => {
-						e.preventDefault();
-						e.stopImmediatePropagation();
-
-						const actions = this.getPromptContextMenuActions(prompt);
-
-						this.contextMenuService.showContextMenu({
-							getAnchor: () => ({ x: e.clientX, y: e.clientY }),
-							getActions: () => actions,
-						});
-					}));
-					// Add click handler
-					this._register(dom.addDisposableListener(promptElement, dom.EventType.CLICK, executePrompt));
-					// Add keyboard handler
-					this._register(dom.addDisposableListener(promptElement, dom.EventType.KEY_DOWN, (e) => {
-						const event = new StandardKeyboardEvent(e);
-						if (event.equals(KeyCode.Enter) || event.equals(KeyCode.Space)) {
-							e.preventDefault();
-							e.stopPropagation();
-							executePrompt();
-						}
-						else if (event.equals(KeyCode.F10) && event.shiftKey) {
-							e.preventDefault();
-							e.stopPropagation();
-							const actions = this.getPromptContextMenuActions(prompt);
-							this.contextMenuService.showContextMenu({
-								getAnchor: () => promptElement,
-								getActions: () => actions,
-							});
-						}
-					}));
-				}
-			}
-
 			// Tips
 			if (content.tips) {
 				const tips = dom.append(this.element, $('.chat-welcome-view-tips'));
@@ -306,39 +204,13 @@ export class ChatViewWelcomePart extends Disposable {
 		}
 	}
 
-	private getPromptContextMenuActions(prompt: IChatSuggestedPrompts): IAction[] {
-		const actions: IAction[] = [];
-		if (prompt.uri) {
-			const uri = prompt.uri;
-			actions.push(new Action(
-				'chat.editPromptFile',
-				localize('editPromptFile', "Edit Prompt File"),
-				ThemeIcon.asClassName(Codicon.goToFile),
-				true,
-				async () => {
-					try {
-						await this.openerService.open(uri);
-					} catch (error) {
-						this.logService.error('Failed to open prompt file:', error);
-					}
-				}
-			));
-		}
-		return actions;
-	}
-
 	public needsRerender(content: IChatViewWelcomeContent): boolean {
 		// Heuristic based on content that changes between states
 		return !!(
 			this.content.title !== content.title ||
 			this.content.message.value !== content.message.value ||
 			this.content.additionalMessage !== content.additionalMessage ||
-			this.content.tips?.value !== content.tips?.value ||
-			this.content.suggestedPrompts?.length !== content.suggestedPrompts?.length ||
-			this.content.suggestedPrompts?.some((prompt, index) => {
-				const incoming = content.suggestedPrompts?.[index];
-				return incoming?.label !== prompt.label || incoming?.description !== prompt.description;
-			}));
+			this.content.tips?.value !== content.tips?.value);
 	}
 
 	private renderMarkdownMessageContent(content: IMarkdownString, options: IChatViewWelcomeRenderOptions | undefined): IRenderedMarkdown {
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentMarkdownRenderer.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentMarkdownRenderer.ts
index 5a7f98614d689..adeb31756e933 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentMarkdownRenderer.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentMarkdownRenderer.ts
@@ -14,6 +14,9 @@ import { IConfigurationService } from '../../../../../platform/configuration/com
 import { IHoverService } from '../../../../../platform/hover/browser/hover.js';
 import { IOpenerService } from '../../../../../platform/opener/common/opener.js';
 import product from '../../../../../platform/product/common/product.js';
+import { CHAT_INTERNAL_SCHEME } from '../../common/promptSyntax/internalCustomizations/internalPromptFileSystem.js';
+
+const _remoteImageDisallowed = () => false;
 
 export const allowedChatMarkdownHtmlTags = Object.freeze([
 	'b',
@@ -78,8 +81,8 @@ export class ChatContentMarkdownRenderer implements IMarkdownRenderer {
 					override: allowedChatMarkdownHtmlTags,
 				},
 				...options?.sanitizerConfig,
-				allowedLinkSchemes: { augment: [product.urlProtocol] },
-				remoteImageIsAllowed: (_uri) => false,
+				allowedLinkSchemes: { augment: [product.urlProtocol, CHAT_INTERNAL_SCHEME, 'copilot-skill'] },
+				remoteImageIsAllowed: _remoteImageDisallowed,
 			}
 		};
 
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatAttachmentsContentPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatAttachmentsContentPart.ts
index 92a5a84d9af2a..6cff3c02973ae 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatAttachmentsContentPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatAttachmentsContentPart.ts
@@ -14,6 +14,7 @@ import { ResourceLabels } from '../../../../../browser/labels.js';
 import { IChatRequestVariableEntry, isElementVariableEntry, isImageVariableEntry, isNotebookOutputVariableEntry, isPasteVariableEntry, isPromptFileVariableEntry, isPromptTextVariableEntry, isSCMHistoryItemChangeRangeVariableEntry, isSCMHistoryItemChangeVariableEntry, isSCMHistoryItemVariableEntry, isTerminalVariableEntry, isWorkspaceVariableEntry, OmittedState } from '../../../common/attachments/chatVariableEntries.js';
 import { ChatResponseReferencePartStatusKind, IChatContentReference } from '../../../common/chatService/chatService.js';
 import { DefaultChatAttachmentWidget, ElementChatAttachmentWidget, FileAttachmentWidget, ImageAttachmentWidget, NotebookCellOutputChatAttachmentWidget, PasteAttachmentWidget, PromptFileAttachmentWidget, PromptTextAttachmentWidget, SCMHistoryItemAttachmentWidget, SCMHistoryItemChangeAttachmentWidget, SCMHistoryItemChangeRangeAttachmentWidget, TerminalCommandAttachmentWidget, ToolSetOrToolItemAttachmentWidget } from '../../attachments/chatAttachmentWidgets.js';
+import { IChatAttachmentWidgetRegistry } from '../../attachments/chatAttachmentWidgetRegistry.js';
 
 export interface IChatAttachmentsContentPartOptions {
 	readonly variables: readonly IChatRequestVariableEntry[];
@@ -39,6 +40,7 @@ export class ChatAttachmentsContentPart extends Disposable {
 	constructor(
 		options: IChatAttachmentsContentPartOptions,
 		@IInstantiationService private readonly instantiationService: IInstantiationService,
+		@IChatAttachmentWidgetRegistry private readonly chatAttachmentWidgetRegistry: IChatAttachmentWidgetRegistry,
 	) {
 		super();
 		this._variables = options.variables;
@@ -167,7 +169,8 @@ export class ChatAttachmentsContentPart extends Disposable {
 			// skip workspace attachments
 			return;
 		} else {
-			widget = this.instantiationService.createInstance(DefaultChatAttachmentWidget, resource, range, attachment, correspondingContentReference, undefined, { shouldFocusClearButton: false, supportsDeletion: false }, container, this._contextResourceLabels);
+			widget = this.chatAttachmentWidgetRegistry.createWidget(attachment, { shouldFocusClearButton: false, supportsDeletion: false }, container)
+				?? this.instantiationService.createInstance(DefaultChatAttachmentWidget, resource, range, attachment, correspondingContentReference, undefined, { shouldFocusClearButton: false, supportsDeletion: false }, container, this._contextResourceLabels);
 		}
 
 		let ariaLabel: string | null = null;
@@ -180,7 +183,7 @@ export class ChatAttachmentsContentPart extends Disposable {
 			ariaLabel = `${ariaLabel}${description ? ` ${description}` : ''}`;
 			for (const selector of ['.monaco-icon-suffix-container', '.monaco-icon-name-container']) {
 				// eslint-disable-next-line no-restricted-syntax
-				const element = widget.label.element.querySelector(selector);
+				const element = widget.label?.element.querySelector(selector);
 				if (element) {
 					element.classList.add('warning');
 				}
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatContentParts.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatContentParts.ts
index e15b3d1fafd03..e0d39e078e583 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatContentParts.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatContentParts.ts
@@ -3,13 +3,17 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { IDisposable } from '../../../../../../base/common/lifecycle.js';
+import { Disposable, IDisposable, ReferenceCollection } from '../../../../../../base/common/lifecycle.js';
 import { ChatTreeItem, IChatCodeBlockInfo } from '../../chat.js';
 import { IChatRendererContent, IChatRequestViewModel, IChatResponseViewModel } from '../../../common/model/chatViewModel.js';
 import { CodeBlockModelCollection } from '../../../common/widget/codeBlockModelCollection.js';
 import { DiffEditorPool, EditorPool } from './chatContentCodePools.js';
 import { IObservable } from '../../../../../../base/common/observable.js';
 import { Event } from '../../../../../../base/common/event.js';
+import { ITextModel } from '../../../../../../editor/common/model.js';
+import { ILanguageSelection } from '../../../../../../editor/common/languages/language.js';
+import { IModelService } from '../../../../../../editor/common/services/model.js';
+import { URI } from '../../../../../../base/common/uri.js';
 
 export interface IChatContentPart extends IDisposable {
 	domNode: HTMLElement | undefined;
@@ -53,4 +57,37 @@ export interface IChatContentPartRenderContext {
 	readonly codeBlockModelCollection: CodeBlockModelCollection;
 	readonly currentWidth: IObservable<number>;
 	readonly onDidChangeVisibility: Event<boolean>;
+	readonly inlineTextModels: InlineTextModelCollection;
+}
+
+/**
+ * Ref-counted collection of inline text models keyed by URI. Models are
+ * created on first acquire and disposed only when the last reference is
+ * released, preventing duplicate-model errors during re-renders.
+ */
+export class InlineTextModelCollection extends Disposable {
+	private readonly _collection: InlineTextModelReferenceCollection;
+
+	constructor(@IModelService modelService: IModelService) {
+		super();
+		this._collection = new InlineTextModelReferenceCollection(modelService);
+	}
+
+	acquire(uri: URI, value: string, languageSelection: ILanguageSelection | null, isForSimpleWidget: boolean) {
+		return this._collection.acquire(uri.toString(), uri, value, languageSelection, isForSimpleWidget);
+	}
+}
+
+class InlineTextModelReferenceCollection extends ReferenceCollection<ITextModel> {
+	constructor(private readonly modelService: IModelService) {
+		super();
+	}
+
+	protected override createReferencedObject(key: string, uri: URI, value: string, languageSelection: ILanguageSelection | null, isForSimpleWidget: boolean): ITextModel {
+		return this.modelService.createModel(value, languageSelection, uri, isForSimpleWidget);
+	}
+
+	protected override destroyReferencedObject(_key: string, model: ITextModel): void {
+		model.dispose();
+	}
 }
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatDisabledClaudeHooksContentPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatDisabledClaudeHooksContentPart.ts
index 7939aaa309915..67b9be3d84d1c 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatDisabledClaudeHooksContentPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatDisabledClaudeHooksContentPart.ts
@@ -33,9 +33,10 @@ export class ChatDisabledClaudeHooksContentPart extends Disposable implements IC
 		icon.classList.add(...ThemeIcon.asClassNameArray(Codicon.info));
 
 		const enableLink = createMarkdownCommandLink({
-			title: localize('chat.disabledClaudeHooks.enableLink', "Enable"),
+			text: localize('chat.disabledClaudeHooks.enableLink', "Enable"),
 			id: 'workbench.action.openSettings',
 			arguments: [PromptsConfig.USE_CLAUDE_HOOKS],
+			tooltip: localize('chat.disabledClaudeHooks.enableLink.tooltip', "Open settings to enable Claude Code hooks"),
 		});
 		const message = localize('chat.disabledClaudeHooks.message', "Claude Code hooks are available for this workspace. {0}", enableLink);
 		const content = new MarkdownString(message, { isTrusted: true });
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatHookContentPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatHookContentPart.ts
index 2ed104c1de8be..e7f8800ecee97 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatHookContentPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatHookContentPart.ts
@@ -10,14 +10,14 @@ import { IHoverService } from '../../../../../../platform/hover/browser/hover.js
 import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
 import { IChatHookPart } from '../../../common/chatService/chatService.js';
 import { IChatRendererContent } from '../../../common/model/chatViewModel.js';
-import { HookType, HOOK_TYPES, HookTypeValue } from '../../../common/promptSyntax/hookSchema.js';
+import { HookType, HOOK_METADATA, HookTypeValue } from '../../../common/promptSyntax/hookTypes.js';
 import { ChatTreeItem } from '../../chat.js';
 import { ChatCollapsibleContentPart } from './chatCollapsibleContentPart.js';
 import { IChatContentPart, IChatContentPartRenderContext } from './chatContentParts.js';
 import './media/chatHookContentPart.css';
 
 function getHookTypeLabel(hookType: HookTypeValue): string {
-	return HOOK_TYPES.find(hook => hook.id === hookType)?.label ?? hookType;
+	return HOOK_METADATA[hookType as HookType]?.label ?? hookType;
 }
 
 export class ChatHookContentPart extends ChatCollapsibleContentPart implements IChatContentPart {
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatInlineAnchorWidget.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatInlineAnchorWidget.ts
index d499fda339e62..d4aaa78836493 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatInlineAnchorWidget.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatInlineAnchorWidget.ts
@@ -23,7 +23,7 @@ import { getFlatContextMenuActions } from '../../../../../../platform/actions/br
 import { Action2, IMenuService, MenuId, registerAction2 } from '../../../../../../platform/actions/common/actions.js';
 import { IClipboardService } from '../../../../../../platform/clipboard/common/clipboardService.js';
 import { ICommandService } from '../../../../../../platform/commands/common/commands.js';
-import { IContextKeyService } from '../../../../../../platform/contextkey/common/contextkey.js';
+import { IContextKey, IContextKeyService } from '../../../../../../platform/contextkey/common/contextkey.js';
 import { IContextMenuService } from '../../../../../../platform/contextview/browser/contextView.js';
 import { IResourceStat } from '../../../../../../platform/dnd/browser/dnd.js';
 import { ITextResourceEditorInput } from '../../../../../../platform/editor/common/editor.js';
@@ -44,10 +44,12 @@ import { ExplorerFolderContext } from '../../../../files/common/files.js';
 import { IWorkspaceSymbol } from '../../../../search/common/search.js';
 import { IChatContentInlineReference } from '../../../common/chatService/chatService.js';
 import { IChatWidgetService } from '../../chat.js';
+import { IChatImageCarouselService } from '../../chatImageCarouselService.js';
 import { chatAttachmentResourceContextKey, hookUpSymbolAttachmentDragAndContextMenu } from '../../attachments/chatAttachmentWidgets.js';
 import { IChatMarkdownAnchorService } from './chatMarkdownAnchorService.js';
 import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
 import { ChatConfiguration } from '../../../common/constants.js';
+import { getMediaMime } from '../../../../../../base/common/mime.js';
 
 /**
  * Returns the editor ID to use when opening a resource from chat pills (inline anchors), based on the
@@ -110,6 +112,11 @@ export function renderFileWidgets(element: HTMLElement, instantiationService: II
 					linkText
 				};
 				shouldRenderWidget = true;
+
+				// Strip vscodeLinkType from the URI once we've extracted the metadata for better compatibility with different FS
+				searchParams.delete('vscodeLinkType');
+				const remainingQuery = searchParams.toString();
+				uri = uri.with({ query: remainingQuery });
 			}
 		}
 
@@ -131,6 +138,7 @@ export class InlineAnchorWidget extends Disposable {
 		private readonly element: HTMLAnchorElement | HTMLElement,
 		public readonly inlineReference: IChatContentInlineReference,
 		private readonly metadata: InlineAnchorWidgetMetadata | undefined,
+		@IChatImageCarouselService private readonly chatImageCarouselService: IChatImageCarouselService,
 		@IConfigurationService private readonly configurationService: IConfigurationService,
 		@IContextKeyService originalContextKeyService: IContextKeyService,
 		@IContextMenuService contextMenuService: IContextMenuService,
@@ -199,10 +207,6 @@ export class InlineAnchorWidget extends Disposable {
 				iconEl.classList.add(...iconClasses);
 			};
 
-			this._register(themeService.onDidFileIconThemeChange(() => {
-				refreshIconClasses();
-			}));
-
 			let isDirectory = false;
 			fileService.stat(location.uri)
 				.then(stat => {
@@ -214,31 +218,42 @@ export class InlineAnchorWidget extends Disposable {
 				})
 				.catch(() => { });
 
-			// Context menu
-			const contextKeyService = this._register(originalContextKeyService.createScoped(element));
-			chatAttachmentResourceContextKey.bindTo(contextKeyService).set(location.uri.toString());
-			const isFolderContext = ExplorerFolderContext.bindTo(contextKeyService);
+			// Context menu (context key service created lazily on first context menu open)
+			let contextKeyService: IContextKeyService | undefined;
+			let isFolderContext: IContextKey<boolean> | undefined;
 			let contextMenuInitialized = false;
+
+			const ensureContextKeyService = () => {
+				if (!contextKeyService) {
+					contextKeyService = this._register(originalContextKeyService.createScoped(element));
+					chatAttachmentResourceContextKey.bindTo(contextKeyService).set(location.uri.toString());
+					isFolderContext = ExplorerFolderContext.bindTo(contextKeyService);
+				}
+				return contextKeyService;
+			};
+
 			this._register(dom.addDisposableListener(element, dom.EventType.CONTEXT_MENU, async domEvent => {
 				const event = new StandardMouseEvent(dom.getWindow(domEvent), domEvent);
 				dom.EventHelper.stop(domEvent, true);
 
+				const cks = ensureContextKeyService();
+
 				if (!contextMenuInitialized) {
 					contextMenuInitialized = true;
-					const resourceContextKey = new StaticResourceContextKey(contextKeyService, fileService, languageService, modelService);
+					const resourceContextKey = new StaticResourceContextKey(cks, fileService, languageService, modelService);
 					resourceContextKey.set(location.uri);
 				}
-				isFolderContext.set(isDirectory);
+				isFolderContext!.set(isDirectory);
 
 				if (this._store.isDisposed) {
 					return;
 				}
 
 				contextMenuService.showContextMenu({
-					contextKeyService,
+					contextKeyService: cks,
 					getAnchor: () => event,
 					getActions: () => {
-						const menu = menuService.getMenuActions(MenuId.ChatInlineResourceAnchorContext, contextKeyService, { arg: location.uri });
+						const menu = menuService.getMenuActions(MenuId.ChatInlineResourceAnchorContext, cks, { arg: location.uri });
 						return getFlatContextMenuActions(menu);
 					},
 				});
@@ -291,6 +306,14 @@ export class InlineAnchorWidget extends Disposable {
 		// Click handler to open with custom editor association from chat.editorAssociations setting
 		this._register(dom.addDisposableListener(element, 'click', async (e) => {
 			dom.EventHelper.stop(e, true);
+
+			// If the reference is an image file and the carousel is enabled, open the carousel
+			const mimeType = getMediaMime(location.uri.path);
+			if (mimeType?.startsWith('image/') && this.configurationService.getValue<boolean>(ChatConfiguration.ImageCarouselEnabled)) {
+				await this.chatImageCarouselService.openCarouselAtResource(location.uri);
+				return;
+			}
+
 			const editorOverride = getEditorOverrideForChatResource(location.uri, this.configurationService);
 			const editorOptions: { override: string | undefined; selection?: IRange } = {
 				override: editorOverride,
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatMarkdownContentPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatMarkdownContentPart.ts
index 44abea609e977..e1cb498c7cd1c 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatMarkdownContentPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatMarkdownContentPart.ts
@@ -10,15 +10,18 @@ import { status } from '../../../../../../base/browser/ui/aria/aria.js';
 import { HoverStyle } from '../../../../../../base/browser/ui/hover/hover.js';
 import { HoverPosition } from '../../../../../../base/browser/ui/hover/hoverWidget.js';
 import { DomScrollableElement } from '../../../../../../base/browser/ui/scrollbar/scrollableElement.js';
+import { wrapTablesWithScrollable } from './chatMarkdownTableScrolling.js';
 import { coalesce } from '../../../../../../base/common/arrays.js';
 import { findLast } from '../../../../../../base/common/arraysFind.js';
 import { Codicon } from '../../../../../../base/common/codicons.js';
 import { Lazy } from '../../../../../../base/common/lazy.js';
 import { Disposable, DisposableStore, IDisposable, MutableDisposable, toDisposable } from '../../../../../../base/common/lifecycle.js';
+import { Emitter, Event } from '../../../../../../base/common/event.js';
 import { autorun, autorunSelfDisposable, derived } from '../../../../../../base/common/observable.js';
 import { ScrollbarVisibility } from '../../../../../../base/common/scrollable.js';
 import { equalsIgnoreCase } from '../../../../../../base/common/strings.js';
 import { ThemeIcon } from '../../../../../../base/common/themables.js';
+import { isEqual } from '../../../../../../base/common/resources.js';
 import { URI } from '../../../../../../base/common/uri.js';
 import { Range } from '../../../../../../editor/common/core/range.js';
 import { ILanguageService } from '../../../../../../editor/common/languages/language.js';
@@ -89,6 +92,10 @@ export class ChatMarkdownContentPart extends Disposable implements IChatContentP
 	readonly codeblocksPartId = String(++ChatMarkdownContentPart.ID_POOL);
 	readonly domNode: HTMLElement;
 
+	// This Event exists for one specific scenario and the pattern shouldn't be copied without a good reason
+	private readonly _onDidChangeHeight = this._register(new Emitter<void>());
+	readonly onDidChangeHeight: Event<void> = this._onDidChangeHeight.event;
+
 	private readonly allRefs: IDisposableReference<CodeBlockPart | CollapsedCodeBlock | MarkdownDiffBlockPart>[] = [];
 
 	private readonly _codeblocks: IMarkdownPartCodeBlockInfo[] = [];
@@ -369,6 +376,8 @@ export class ChatMarkdownContentPart extends Disposable implements IChatContentP
 				scrollable.scanDomNode();
 			}
 
+			orderedDisposablesList.push(wrapTablesWithScrollable(this.domNode, layoutParticipants));
+
 			orderedDisposablesList.reverse().forEach(d => store.add(d));
 		};
 
@@ -407,7 +416,14 @@ export class ChatMarkdownContentPart extends Disposable implements IChatContentP
 			this._codeblocks[data.codeBlockPartIndex].codemapperUri = e.codemapperUri;
 		});
 
-		editorInfo.render(data, currentWidth);
+		editorInfo.render(data, currentWidth).then(() => {
+			// There is a scenario where we set the model on the editor in a request and the ResizeObserver is not triggered.
+			// Work around it with this targeted onDidHeightChange. But this pattern generally shouldn't be necessary and
+			// shouldn't be copied elsewhere.
+			if (!this._store.isDisposed && isRequestVM(data.element)) {
+				this._onDidChangeHeight.fire();
+			}
+		});
 
 		return ref;
 	}
@@ -438,7 +454,7 @@ export class ChatMarkdownContentPart extends Disposable implements IChatContentP
 				ref.object.layout(width);
 			} else if (ref.object instanceof CollapsedCodeBlock) {
 				const codeblockModel = this._codeblocks[index];
-				if (codeblockModel.codemapperUri && ref.object.uri?.toString() !== codeblockModel.codemapperUri.toString()) {
+				if (codeblockModel.codemapperUri && !isEqual(ref.object.uri, codeblockModel.codemapperUri)) {
 					ref.object.render(codeblockModel.codemapperUri);
 				}
 			}
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatMarkdownTableScrolling.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatMarkdownTableScrolling.ts
new file mode 100644
index 0000000000000..517fe538dc693
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatMarkdownTableScrolling.ts
@@ -0,0 +1,82 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../../../base/browser/dom.js';
+import { DomScrollableElement } from '../../../../../../base/browser/ui/scrollbar/scrollableElement.js';
+import { Lazy } from '../../../../../../base/common/lazy.js';
+import { DisposableStore } from '../../../../../../base/common/lifecycle.js';
+
+import { ScrollbarVisibility } from '../../../../../../base/common/scrollable.js';
+
+/**
+ * Finds all tables in `domNode` and wraps each in a {@link DomScrollableElement}
+ * so they scroll horizontally with the custom VS Code scrollbar instead of the
+ * native one. Each wrapped table is pushed onto `orderedDisposablesList` and a
+ * `scanDomNode` callback is registered on `layoutParticipants` so the scrollbar
+ * re-measures whenever the container is resized.
+ *
+ * Each column's `min-width` is also set to the maximum character count across
+ * all cells in that column (in `ch` units), preventing short-content columns
+ * like "001" from being squeezed to one character wide. Single-character columns
+ * are left unchanged. This is layout-free: only `textContent` lengths are read.
+ */
+export function wrapTablesWithScrollable(domNode: HTMLElement, layoutParticipants: Lazy<Set<() => void>>): DisposableStore {
+	const store = new DisposableStore();
+	// eslint-disable-next-line no-restricted-syntax
+	for (const table of domNode.querySelectorAll('table')) {
+		if (!dom.isHTMLElement(table)) {
+			continue;
+		}
+
+		applyTableColumnMinWidths(table);
+
+		// Wrap the table in a div so DomScrollableElement can compare the div's
+		// constrained clientWidth against the table's natural scrollWidth.
+		// Passing the table directly doesn't work because a table always expands
+		// to its content width, so clientWidth == scrollWidth and no scrollbar appears.
+		const parent = table.parentElement;
+		const nextSibling = table.nextSibling;
+		const tableContainer = document.createElement('div');
+		tableContainer.appendChild(table); // moves table out of DOM
+		const scrollable = store.add(new DomScrollableElement(tableContainer, { // moves tableContainer into scrollNode
+			vertical: ScrollbarVisibility.Hidden,
+			horizontal: ScrollbarVisibility.Auto,
+		}));
+		const scrollNode = scrollable.getDomNode();
+		scrollNode.classList.add('rendered-markdown-table-scroll-wrapper');
+		parent?.insertBefore(scrollNode, nextSibling);
+
+		layoutParticipants.value.add(() => { scrollable.scanDomNode(); });
+		scrollable.scanDomNode();
+	}
+	return store;
+}
+
+/** Maximum `min-width` (in `ch`) applied to any table column, regardless of its content length. */
+const TABLE_COLUMN_MIN_WIDTH_CAP_CH = 3;
+
+function applyTableColumnMinWidths(table: HTMLTableElement): void {
+	const rows = table.rows;
+	const colMaxChars: number[] = [];
+	for (const row of rows) {
+		for (let c = 0; c < row.cells.length; c++) {
+			const len = row.cells[c].textContent?.length ?? 0;
+			if (len > (colMaxChars[c] ?? 0)) {
+				colMaxChars[c] = len;
+			}
+		}
+	}
+	// Apply min-width only to the first row's cells so each column width
+	// constraint is set once rather than touching every cell in the table.
+	const firstRow = rows[0];
+	if (firstRow) {
+		for (let c = 0; c < firstRow.cells.length; c++) {
+			const minCh = colMaxChars[c];
+			if (minCh !== undefined && minCh > 1) {
+				firstRow.cells[c].style.minWidth = Math.min(minCh, TABLE_COLUMN_MIN_WIDTH_CAP_CH) + 'ch';
+			}
+		}
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatMcpServersInteractionContentPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatMcpServersInteractionContentPart.ts
index 101b84d981099..0fec722d8a211 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatMcpServersInteractionContentPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatMcpServersInteractionContentPart.ts
@@ -105,16 +105,18 @@ export class ChatMcpServersInteractionContentPart extends Disposable implements
 
 	private createServerCommandLinks(servers: Array<{ id: string; label: string }>): string {
 		return servers.map(s => createMarkdownCommandLink({
-			title: '`' + escapeMarkdownSyntaxTokens(s.label) + '`',
+			text: '`' + escapeMarkdownSyntaxTokens(s.label) + '`',
 			id: McpCommandIds.ServerOptions,
 			arguments: [s.id],
+			tooltip: localize('mcp.server.options.tooltip', 'Show options for {0}', s.label),
 		}, false)).join(', ');
 	}
 
 	private updateDetailedProgress(state: IAutostartResult): void {
 		const skipText = createMarkdownCommandLink({
-			title: localize('mcp.skip.link', 'Skip?'),
+			text: localize('mcp.skip.link', 'Skip?'),
 			id: McpCommandIds.SkipCurrentAutostart,
+			tooltip: localize('mcp.skip.tooltip', 'Skip starting this MCP server'),
 		});
 
 		let content: MarkdownString;
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatProgressContentPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatProgressContentPart.ts
index 03f160cdd7296..4a3ec940760e8 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatProgressContentPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatProgressContentPart.ts
@@ -4,13 +4,14 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { $, append } from '../../../../../../base/browser/dom.js';
+import { IRenderedMarkdown, renderAsPlaintext } from '../../../../../../base/browser/markdownRenderer.js';
 import { alert } from '../../../../../../base/browser/ui/aria/aria.js';
 import { Codicon } from '../../../../../../base/common/codicons.js';
 import { MarkdownString, type IMarkdownString } from '../../../../../../base/common/htmlContent.js';
+import { stripIcons } from '../../../../../../base/common/iconLabels.js';
 import { Disposable, DisposableStore, MutableDisposable } from '../../../../../../base/common/lifecycle.js';
 import { ThemeIcon } from '../../../../../../base/common/themables.js';
 import { IMarkdownRenderer } from '../../../../../../platform/markdown/browser/markdownRenderer.js';
-import { IRenderedMarkdown } from '../../../../../../base/browser/markdownRenderer.js';
 import { IInstantiationService } from '../../../../../../platform/instantiation/common/instantiation.js';
 import { localize } from '../../../../../../nls.js';
 import { IChatProgressMessage, IChatTask, IChatTaskSerialized, IChatToolInvocation, IChatToolInvocationSerialized } from '../../../common/chatService/chatService.js';
@@ -61,13 +62,13 @@ export class ChatProgressContentPart extends Disposable implements IChatContentP
 			return;
 		}
 
-		if (this.showSpinner && !this.configurationService.getValue(AccessibilityWorkbenchSettingId.VerboseChatProgressUpdates)) {
-			// TODO@roblourens is this the right place for this?
+		if (this.showSpinner && this.configurationService.getValue(AccessibilityWorkbenchSettingId.VerboseChatProgressUpdates)) {
 			// this step is in progress, communicate it to SR users
-			alert(progress.content.value);
+			alert(stripIcons(renderAsPlaintext(progress.content)));
 		}
 		const isLoadingIcon = icon && ThemeIcon.isEqual(icon, ThemeIcon.modify(Codicon.loading, 'spin'));
-		const useShimmer = shimmer ?? ((!icon || isLoadingIcon) && this.showSpinner);
+		// Even if callers request shimmer, only the active (spinner-visible) progress row should animate.
+		const useShimmer = (shimmer ?? (!icon || isLoadingIcon)) && this.showSpinner;
 		// if we have shimmer, don't show spinner
 		const codicon = useShimmer ? Codicon.check : (icon ?? (this.showSpinner ? ThemeIcon.modify(Codicon.loading, 'spin') : Codicon.check));
 		const result = this.chatContentMarkdownRenderer.render(progress.content);
@@ -151,6 +152,10 @@ export class ChatProgressSubPart extends Disposable {
 				content: tooltip,
 				style: HoverStyle.Pointer,
 			}));
+			this._register(hoverService.setupDelayedHover(messageElement, {
+				content: tooltip,
+				style: HoverStyle.Pointer,
+			}));
 		}
 		append(this.domNode, iconElement);
 
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatQuestionCarouselPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatQuestionCarouselPart.ts
index 15170e05679de..704052557be9c 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatQuestionCarouselPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatQuestionCarouselPart.ts
@@ -10,6 +10,7 @@ import { Emitter, Event } from '../../../../../../base/common/event.js';
 import { IMarkdownString, MarkdownString, isMarkdownString } from '../../../../../../base/common/htmlContent.js';
 import { KeyCode } from '../../../../../../base/common/keyCodes.js';
 import { Disposable, DisposableStore, MutableDisposable } from '../../../../../../base/common/lifecycle.js';
+import { isMacintosh } from '../../../../../../base/common/platform.js';
 import { hasKey } from '../../../../../../base/common/types.js';
 import { localize } from '../../../../../../nls.js';
 import { IAccessibilityService } from '../../../../../../platform/accessibility/common/accessibility.js';
@@ -17,8 +18,10 @@ import { IMarkdownRendererService } from '../../../../../../platform/markdown/br
 import { defaultButtonStyles, defaultCheckboxStyles, defaultInputBoxStyles } from '../../../../../../platform/theme/browser/defaultStyles.js';
 import { Button } from '../../../../../../base/browser/ui/button/button.js';
 import { InputBox } from '../../../../../../base/browser/ui/inputbox/inputBox.js';
+import { DomScrollableElement } from '../../../../../../base/browser/ui/scrollbar/scrollableElement.js';
 import { Checkbox } from '../../../../../../base/browser/ui/toggle/toggle.js';
-import { IChatQuestion, IChatQuestionCarousel } from '../../../common/chatService/chatService.js';
+import { IChatQuestion, IChatQuestionCarousel, IChatQuestionAnswerValue, IChatQuestionValidation, IChatSingleSelectAnswer, IChatMultiSelectAnswer } from '../../../common/chatService/chatService.js';
+import { ChatQuestionCarouselData } from '../../../common/model/chatProgressTypes/chatQuestionCarouselData.js';
 import { IChatContentPart, IChatContentPartRenderContext } from './chatContentParts.js';
 import { IChatRendererContent, isResponseVM } from '../../../common/model/chatViewModel.js';
 import { ChatTreeItem } from '../../chat.js';
@@ -28,13 +31,13 @@ import { IHoverService } from '../../../../../../platform/hover/browser/hover.js
 import { IContextKey, IContextKeyService } from '../../../../../../platform/contextkey/common/contextkey.js';
 import { IKeybindingService } from '../../../../../../platform/keybinding/common/keybinding.js';
 import { ChatContextKeys } from '../../../common/actions/chatContextKeys.js';
+import { ScrollbarVisibility } from '../../../../../../base/common/scrollable.js';
 import './media/chatQuestionCarousel.css';
 
 const PREVIOUS_QUESTION_ACTION_ID = 'workbench.action.chat.previousQuestion';
 const NEXT_QUESTION_ACTION_ID = 'workbench.action.chat.nextQuestion';
-
 export interface IChatQuestionCarouselOptions {
-	onSubmit: (answers: Map<string, unknown> | undefined) => void;
+	onSubmit: (answers: Map<string, IChatQuestionAnswerValue> | undefined) => void;
 	shouldAutoFocus?: boolean;
 }
 
@@ -45,16 +48,16 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 	public readonly onDidChangeHeight: Event<void> = this._onDidChangeHeight.event;
 
 	private _currentIndex = 0;
-	private readonly _answers = new Map<string, unknown>();
+	private readonly _answers = new Map<string, IChatQuestionAnswerValue>();
 
 	private _questionContainer: HTMLElement | undefined;
 	private _closeButtonContainer: HTMLElement | undefined;
 	private _footerRow: HTMLElement | undefined;
 	private _stepIndicator: HTMLElement | undefined;
-	private _navigationButtons: HTMLElement | undefined;
+	private _submitHint: HTMLElement | undefined;
+	private _submitButton: Button | undefined;
 	private _prevButton: Button | undefined;
 	private _nextButton: Button | undefined;
-	private readonly _nextButtonHover: MutableDisposable<{ dispose(): void }> = this._register(new MutableDisposable());
 	private _skipAllButton: Button | undefined;
 
 	private _isSkipped = false;
@@ -65,6 +68,7 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 	private readonly _freeformTextareas: Map<string, HTMLTextAreaElement> = new Map();
 	private readonly _inputBoxes: DisposableStore = this._register(new DisposableStore());
 	private readonly _questionRenderStore = this._register(new MutableDisposable<DisposableStore>());
+	private _inputScrollable: DomScrollableElement | undefined;
 
 	/**
 	 * Disposable store for interactive UI components (header, nav buttons, etc.)
@@ -72,6 +76,8 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 	 */
 	private readonly _interactiveUIStore: MutableDisposable<DisposableStore> = this._register(new MutableDisposable());
 	private readonly _inChatQuestionCarouselContextKey: IContextKey<boolean>;
+	private _validationMessageElement: HTMLElement | undefined;
+	private _currentValidationError: string | undefined;
 
 	constructor(
 		public readonly carousel: IChatQuestionCarousel,
@@ -98,7 +104,20 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 		this.domNode.setAttribute('aria-roledescription', localize('chat.questionCarousel.roleDescription', 'chat question'));
 		this._updateAriaLabel();
 
-		// Restore answers from carousel data if already submitted (e.g., after re-render due to virtualization)
+		// Restore draft state from transient runtime fields when available.
+		if (carousel instanceof ChatQuestionCarouselData) {
+			if (typeof carousel.draftCurrentIndex === 'number') {
+				this._currentIndex = Math.max(0, Math.min(carousel.draftCurrentIndex, carousel.questions.length - 1));
+			}
+
+			if (carousel.draftAnswers) {
+				for (const [key, value] of Object.entries(carousel.draftAnswers)) {
+					this._answers.set(key, value);
+				}
+			}
+		}
+
+		// Restore submitted answers for summary rendering.
 		if (carousel.data) {
 			for (const [key, value] of Object.entries(carousel.data)) {
 				this._answers.set(key, value);
@@ -129,70 +148,37 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 			const skipAllTitle = localize('chat.questionCarousel.skipAllTitle', 'Skip all questions');
 			const skipAllButton = interactiveStore.add(new Button(this._closeButtonContainer, { ...defaultButtonStyles, secondary: true, supportIcons: true }));
 			skipAllButton.label = `$(${Codicon.close.id})`;
-			skipAllButton.element.classList.add('chat-question-nav-arrow', 'chat-question-close');
+			skipAllButton.element.classList.add('chat-question-close');
 			skipAllButton.element.setAttribute('aria-label', skipAllTitle);
 			interactiveStore.add(this._hoverService.setupDelayedHover(skipAllButton.element, { content: skipAllTitle }));
 			this._skipAllButton = skipAllButton;
 		}
 
-		// Footer row with step indicator and navigation buttons
-		this._footerRow = dom.$('.chat-question-footer-row');
-
-		// Step indicator (e.g., "2/4") on the left
-		this._stepIndicator = dom.$('.chat-question-step-indicator');
-		this._footerRow.appendChild(this._stepIndicator);
-
-		// Navigation controls (< >) - placed in footer row
-		this._navigationButtons = dom.$('.chat-question-carousel-nav');
-		this._navigationButtons.setAttribute('role', 'navigation');
-		this._navigationButtons.setAttribute('aria-label', localize('chat.questionCarousel.navigation', 'Question navigation'));
-
-		// Group prev/next buttons together
-		const arrowsContainer = dom.$('.chat-question-nav-arrows');
-
-		const previousLabel = localize('previous', 'Previous');
-		const previousLabelWithKeybinding = this.getLabelWithKeybinding(previousLabel, PREVIOUS_QUESTION_ACTION_ID);
-		const prevButton = interactiveStore.add(new Button(arrowsContainer, { ...defaultButtonStyles, secondary: true, supportIcons: true }));
-		prevButton.element.classList.add('chat-question-nav-arrow', 'chat-question-nav-prev');
-		prevButton.label = `$(${Codicon.chevronLeft.id})`;
-		prevButton.element.setAttribute('aria-label', previousLabelWithKeybinding);
-		interactiveStore.add(this._hoverService.setupDelayedHover(prevButton.element, { content: previousLabelWithKeybinding }));
-		this._prevButton = prevButton;
-
-		const nextButton = interactiveStore.add(new Button(arrowsContainer, { ...defaultButtonStyles, secondary: true, supportIcons: true }));
-		nextButton.element.classList.add('chat-question-nav-arrow', 'chat-question-nav-next');
-		nextButton.label = `$(${Codicon.chevronRight.id})`;
-		this._nextButton = nextButton;
-
-		this._navigationButtons.appendChild(arrowsContainer);
-		this._footerRow.appendChild(this._navigationButtons);
-		this.domNode.append(this._footerRow);
-
-
 		// Register event listeners
-		interactiveStore.add(prevButton.onDidClick(() => this.navigate(-1)));
-		interactiveStore.add(nextButton.onDidClick(() => this.handleNext()));
 		if (this._skipAllButton) {
 			interactiveStore.add(this._skipAllButton.onDidClick(() => this.ignore()));
 		}
 
-		// Register keyboard navigation - handle Enter on text inputs and freeform textareas
+		// Register keyboard navigation
 		interactiveStore.add(dom.addDisposableListener(this.domNode, dom.EventType.KEY_DOWN, (e: KeyboardEvent) => {
 			const event = new StandardKeyboardEvent(e);
 			if (event.keyCode === KeyCode.Escape && this.carousel.allowSkip) {
 				e.preventDefault();
 				e.stopPropagation();
 				this.ignore();
+			} else if (event.keyCode === KeyCode.Enter && (event.metaKey || event.ctrlKey)) {
+				// Cmd/Ctrl+Enter submits immediately from anywhere
+				e.preventDefault();
+				e.stopPropagation();
+				this.submit();
 			} else if (event.keyCode === KeyCode.Enter && !event.shiftKey) {
-				// Handle Enter key for text inputs and freeform textareas, not radio/checkbox or buttons
-				// Buttons have their own Enter/Space handling via Button class
 				const target = e.target as HTMLElement;
 				const isTextInput = target.tagName === 'INPUT' && (target as HTMLInputElement).type === 'text';
 				const isFreeformTextarea = target.tagName === 'TEXTAREA' && target.classList.contains('chat-question-freeform-textarea');
 				if (isTextInput || isFreeformTextarea) {
 					e.preventDefault();
 					e.stopPropagation();
-					this.handleNext();
+					this.handleNextOrSubmit();
 				}
 			} else if ((event.ctrlKey || event.metaKey) && (event.keyCode === KeyCode.Backspace || event.keyCode === KeyCode.Delete)) {
 				e.stopPropagation();
@@ -211,7 +197,33 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 		const answer = this.getCurrentAnswer();
 		if (answer !== undefined) {
 			this._answers.set(currentQuestion.id, answer);
+		} else {
+			this._answers.delete(currentQuestion.id);
+		}
+
+		// Validate on change to update the Next button state
+		if (currentQuestion?.validation && typeof answer === 'string' && answer !== '') {
+			const error = this.getValidationError(answer, currentQuestion.validation);
+			if (error) {
+				this.showValidationError(error);
+			} else {
+				this.clearValidationError();
+			}
+		} else {
+			this.clearValidationError();
+		}
+
+		this.updateFooterState();
+		this.persistDraftState();
+	}
+
+	private persistDraftState(): void {
+		if (this.carousel.isUsed || !(this.carousel instanceof ChatQuestionCarouselData)) {
+			return;
 		}
+
+		this.carousel.draftAnswers = Object.fromEntries(this._answers.entries());
+		this.carousel.draftCurrentIndex = this._currentIndex;
 	}
 
 	/**
@@ -223,28 +235,53 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 		if (newIndex >= 0 && newIndex < this.carousel.questions.length) {
 			this.saveCurrentAnswer();
 			this._currentIndex = newIndex;
+			this.persistDraftState();
 			this.renderCurrentQuestion(true);
+			this.domNode.focus();
 		}
 	}
 
 	/**
-	 * Handles the next/submit button action.
-	 * Either advances to the next question or submits.
+	 * Handles the next/submit behavior for keyboard and option selection flows.
+	 * Either advances to the next question or submits when on the last question.
 	 */
-	private handleNext(): void {
+	private handleNextOrSubmit(): void {
 		this.saveCurrentAnswer();
 
+		if (!this.validateCurrentQuestion()) {
+			return;
+		}
+
 		if (this._currentIndex < this.carousel.questions.length - 1) {
 			// Move to next question
 			this._currentIndex++;
+			this.persistDraftState();
 			this.renderCurrentQuestion(true);
 		} else {
 			// Submit
+			if (!this.validateRequiredFields()) {
+				return;
+			}
 			this._options.onSubmit(this._answers);
 			this.hideAndShowSummary();
 		}
 	}
 
+	/**
+	 * Handles explicit submit action from the dedicated submit button.
+	 */
+	private submit(): void {
+		this.saveCurrentAnswer();
+		if (!this.validateCurrentQuestion()) {
+			return;
+		}
+		if (!this.validateRequiredFields()) {
+			return;
+		}
+		this._options.onSubmit(this._answers);
+		this.hideAndShowSummary();
+	}
+
 	/**
 	 * Focuses the container element and announces the question for screen reader users.
 	 */
@@ -295,12 +332,70 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 		// Clear references to disposed elements
 		this._prevButton = undefined;
 		this._nextButton = undefined;
+		this._submitButton = undefined;
 		this._skipAllButton = undefined;
 		this._questionContainer = undefined;
-		this._navigationButtons = undefined;
 		this._closeButtonContainer = undefined;
 		this._footerRow = undefined;
 		this._stepIndicator = undefined;
+		this._submitHint = undefined;
+		this._inputScrollable = undefined;
+	}
+
+	private layoutInputScrollable(inputScrollable: DomScrollableElement): void {
+		if (!this._questionContainer) {
+			return;
+		}
+
+		const scrollableNode = inputScrollable.getDomNode();
+		const scrollableContent = scrollableNode.firstElementChild;
+		if (!dom.isHTMLElement(scrollableContent)) {
+			return;
+		}
+
+		// Clear stale size constraints first so this step can shrink after
+		// navigating from a taller question.
+		if (scrollableNode.style.height !== '' || scrollableNode.style.maxHeight !== '') {
+			scrollableNode.style.height = '';
+			scrollableNode.style.maxHeight = '';
+		}
+		if (scrollableContent.style.height !== '' || scrollableContent.style.maxHeight !== '') {
+			scrollableContent.style.height = '';
+			scrollableContent.style.maxHeight = '';
+		}
+
+		// Use the flex-resolved container height (constrained by CSS max-height)
+		// instead of window.innerHeight, so the scroll viewport tracks actual chat space.
+		const maxContainerHeight = this._questionContainer.clientHeight;
+
+		const computedStyle = dom.getWindow(this._questionContainer).getComputedStyle(this._questionContainer);
+		const contentVerticalPadding =
+			Number.parseFloat(computedStyle.paddingTop || '0') +
+			Number.parseFloat(computedStyle.paddingBottom || '0');
+
+		const nonScrollableContentHeight = Array.from(this._questionContainer.children)
+			.filter(child => child !== scrollableNode)
+			.reduce((sum, child) => sum + (child as HTMLElement).offsetHeight, 0);
+
+		const availableScrollableHeight = Math.floor(maxContainerHeight - contentVerticalPadding - nonScrollableContentHeight);
+
+		const contentScrollableHeight = scrollableContent.scrollHeight;
+		const constrainedScrollableHeight = Math.max(0, Math.min(availableScrollableHeight, contentScrollableHeight));
+		const constrainedScrollableHeightPx = `${constrainedScrollableHeight}px`;
+
+		// Constrain wrapper + content so no stale flex sizing survives between steps.
+		if (scrollableNode.style.height !== constrainedScrollableHeightPx || scrollableNode.style.maxHeight !== constrainedScrollableHeightPx) {
+			scrollableNode.style.height = constrainedScrollableHeightPx;
+			scrollableNode.style.maxHeight = constrainedScrollableHeightPx;
+		}
+
+		// Constrain the content element (DomScrollableElement._element) so that
+		// scanDomNode sees clientHeight < scrollHeight and enables scrolling.
+		if (scrollableContent.style.height !== constrainedScrollableHeightPx || scrollableContent.style.maxHeight !== constrainedScrollableHeightPx) {
+			scrollableContent.style.height = constrainedScrollableHeightPx;
+			scrollableContent.style.maxHeight = constrainedScrollableHeightPx;
+		}
+		inputScrollable.scanDomNode();
 	}
 
 	/**
@@ -350,8 +445,8 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 	/**
 	 * Collects default values for all questions in the carousel.
 	 */
-	private getDefaultAnswers(): Map<string, unknown> {
-		const answers = new Map<string, unknown>();
+	private getDefaultAnswers(): Map<string, IChatQuestionAnswerValue> {
+		const answers = new Map<string, IChatQuestionAnswerValue>();
 		for (const question of this.carousel.questions) {
 			const defaultAnswer = this.getDefaultAnswerForQuestion(question);
 			if (defaultAnswer !== undefined) {
@@ -364,10 +459,10 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 	/**
 	 * Gets the default answer for a specific question.
 	 */
-	private getDefaultAnswerForQuestion(question: IChatQuestion): unknown {
+	private getDefaultAnswerForQuestion(question: IChatQuestion): IChatQuestionAnswerValue | undefined {
 		switch (question.type) {
 			case 'text':
-				return question.defaultValue;
+				return typeof question.defaultValue === 'string' ? question.defaultValue : undefined;
 
 			case 'singleSelect': {
 				const defaultOptionId = typeof question.defaultValue === 'string' ? question.defaultValue : undefined;
@@ -376,8 +471,7 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 					: undefined;
 				const selectedValue = defaultOption?.value;
 
-				// Always return structured format for single-select (freeform is always shown)
-				return selectedValue !== undefined ? { selectedValue, freeformValue: undefined } : undefined;
+				return selectedValue !== undefined ? { selectedValue, freeformValue: undefined } satisfies IChatSingleSelectAnswer : undefined;
 			}
 
 			case 'multiSelect': {
@@ -389,12 +483,11 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 					.map(opt => opt.value)
 					.filter(v => v !== undefined) ?? [];
 
-				// Always return structured format for multi-select (freeform is always shown)
-				return selectedValues.length > 0 ? { selectedValues, freeformValue: undefined } : undefined;
+				return selectedValues.length > 0 ? { selectedValues, freeformValue: undefined } satisfies IChatMultiSelectAnswer : undefined;
 			}
 
 			default:
-				return question.defaultValue;
+				return typeof question.defaultValue === 'string' ? question.defaultValue : Array.isArray(question.defaultValue) ? { selectedValues: question.defaultValue } : undefined;
 		}
 	}
 
@@ -464,12 +557,13 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 	}
 
 	private renderCurrentQuestion(focusContainerForScreenReader: boolean = false): void {
-		if (!this._questionContainer || !this._prevButton || !this._nextButton) {
+		if (!this._questionContainer) {
 			return;
 		}
 
 		const questionRenderStore = new DisposableStore();
 		this._questionRenderStore.value = questionRenderStore;
+		this._inputScrollable = undefined;
 
 		// Clear previous input boxes and stale references
 		this._inputBoxes.clear();
@@ -486,83 +580,104 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 			return;
 		}
 
-		// Render question header row with title and close button
+		// Render unified question title (message ?? title)
 		const headerRow = dom.$('.chat-question-header-row');
+		const titleRow = dom.$('.chat-question-title-row');
+
+		// Render carousel-level message if present (e.g. from MCP elicitation)
+		if (this.carousel.message && this._currentIndex === 0) {
+			const messageMd = isMarkdownString(this.carousel.message) ? MarkdownString.lift(this.carousel.message) : new MarkdownString(this.carousel.message);
+			const carouselMessage = dom.$('.chat-question-carousel-message');
+			const renderedMessage = questionRenderStore.add(this._markdownRendererService.render(messageMd));
+			carouselMessage.appendChild(renderedMessage.element);
+			headerRow.appendChild(carouselMessage);
+		}
 
-		// Render question message with title styling (no progress prefix)
-		// Fall back to question.title if message is not provided
 		const questionText = question.message ?? question.title;
 		if (questionText) {
 			const title = dom.$('.chat-question-title');
 			const messageContent = this.getQuestionText(questionText);
-
 			title.setAttribute('aria-label', messageContent);
 
-			if (isMarkdownString(questionText)) {
-				const renderedTitle = questionRenderStore.add(this._markdownRendererService.render(MarkdownString.lift(questionText)));
-				title.appendChild(renderedTitle.element);
-			} else {
-				// Check for subtitle in parentheses at the end
-				const parenMatch = messageContent.match(/^(.+?)\s*(\([^)]+\))\s*$/);
-				if (parenMatch) {
-					// Main title (bold)
-					const mainTitle = dom.$('span.chat-question-title-main');
-					mainTitle.textContent = parenMatch[1];
-					title.appendChild(mainTitle);
-
-					// Subtitle in parentheses (normal weight)
-					const subtitle = dom.$('span.chat-question-title-subtitle');
-					subtitle.textContent = ' ' + parenMatch[2];
-					title.appendChild(subtitle);
-				} else {
-					title.textContent = messageContent;
-				}
-			}
-			headerRow.appendChild(title);
+			const titleText = question.required
+				? new MarkdownString(`${isMarkdownString(questionText) ? questionText.value : questionText} *`)
+				: (isMarkdownString(questionText) ? MarkdownString.lift(questionText) : new MarkdownString(questionText));
+			const renderedTitle = questionRenderStore.add(this._markdownRendererService.render(titleText));
+			title.appendChild(renderedTitle.element);
+			titleRow.appendChild(title);
 		}
 
-		// Add close button to header row (if allowSkip is enabled)
+		headerRow.appendChild(titleRow);
+
+		// Always keep the close button in the title row so it does not overlap content.
 		if (this._closeButtonContainer) {
-			headerRow.appendChild(this._closeButtonContainer);
+			titleRow.appendChild(this._closeButtonContainer);
 		}
 
 		this._questionContainer.appendChild(headerRow);
 
-		const isSingleQuestion = this.carousel.questions.length === 1;
-		// Update step indicator in footer
-		if (this._stepIndicator) {
-			this._stepIndicator.textContent = `${this._currentIndex + 1}/${this.carousel.questions.length}`;
-			this._stepIndicator.style.display = isSingleQuestion ? 'none' : '';
+		// Render description if present
+		if (question.description) {
+			const descriptionEl = dom.$('.chat-question-description');
+			descriptionEl.textContent = question.description;
+			this._questionContainer.appendChild(descriptionEl);
 		}
 
 		// Render input based on question type
 		const inputContainer = dom.$('.chat-question-input-container');
 		this.renderInput(inputContainer, question);
-		this._questionContainer.appendChild(inputContainer);
-
-		// Update navigation button states (prevButton and nextButton are guaranteed non-null from guard above)
-		this._prevButton!.enabled = this._currentIndex > 0;
-		this._prevButton!.element.style.display = isSingleQuestion ? 'none' : '';
-
-		// Update next button icon/label for last question
-		const isLastQuestion = this._currentIndex === this.carousel.questions.length - 1;
-		const submitLabel = localize('submit', 'Submit');
-		const nextLabel = localize('next', 'Next');
-		const nextLabelWithKeybinding = this.getLabelWithKeybinding(nextLabel, NEXT_QUESTION_ACTION_ID);
-		if (isLastQuestion) {
-			this._nextButton!.label = submitLabel;
-			this._nextButton!.element.setAttribute('aria-label', submitLabel);
-			// Switch to primary style for submit
-			this._nextButton!.element.classList.add('chat-question-nav-submit');
-			this._nextButtonHover.value = this._hoverService.setupDelayedHover(this._nextButton!.element, { content: submitLabel });
+
+		const inputScrollable = questionRenderStore.add(new DomScrollableElement(inputContainer, {
+			vertical: ScrollbarVisibility.Visible,
+			horizontal: ScrollbarVisibility.Hidden,
+			consumeMouseWheelIfScrollbarIsNeeded: true,
+		}));
+		this._inputScrollable = inputScrollable;
+		const inputScrollableNode = inputScrollable.getDomNode();
+		inputScrollableNode.classList.add('chat-question-input-scrollable');
+		this._questionContainer.appendChild(inputScrollableNode);
+
+		// Validation message element below the scrollable area (not inside it)
+		this._validationMessageElement = dom.$('.chat-question-validation-message');
+		this._validationMessageElement.style.display = 'none';
+		this._questionContainer.appendChild(this._validationMessageElement);
+
+		const isSingleQuestion = this.carousel.questions.length === 1;
+
+		// Render footer before first layout so the scrollable area is measured against
+		// its final available height and does not visibly resize twice.
+		if (!isSingleQuestion) {
+			this.renderFooter();
 		} else {
-			this._nextButton!.label = `$(${Codicon.chevronRight.id})`;
-			this._nextButton!.element.setAttribute('aria-label', nextLabelWithKeybinding);
-			// Keep secondary style for next
-			this._nextButton!.element.classList.remove('chat-question-nav-submit');
-			this._nextButtonHover.value = this._hoverService.setupDelayedHover(this._nextButton!.element, { content: nextLabelWithKeybinding });
+			this.renderSingleQuestionFooter();
 		}
 
+		let relayoutScheduled = false;
+		const relayoutScheduler = questionRenderStore.add(new MutableDisposable());
+		const scheduleLayoutInputScrollable = () => {
+			if (relayoutScheduled) {
+				return;
+			}
+
+			relayoutScheduled = true;
+			relayoutScheduler.value = dom.runAtThisOrScheduleAtNextAnimationFrame(dom.getWindow(this.domNode), () => {
+				relayoutScheduled = false;
+				this.layoutInputScrollable(inputScrollable);
+			});
+		};
+
+		const inputResizeObserver = questionRenderStore.add(new dom.DisposableResizeObserver(() => scheduleLayoutInputScrollable()));
+		questionRenderStore.add(inputResizeObserver.observe(inputScrollableNode));
+		questionRenderStore.add(inputResizeObserver.observe(inputContainer));
+		questionRenderStore.add(dom.addDisposableListener(dom.getWindow(this.domNode), dom.EventType.RESIZE, () => scheduleLayoutInputScrollable()));
+		scheduleLayoutInputScrollable();
+		questionRenderStore.add(dom.runAtThisOrScheduleAtNextAnimationFrame(dom.getWindow(this.domNode), () => {
+			inputContainer.scrollTop = 0;
+			inputContainer.scrollLeft = 0;
+			inputScrollable.setScrollPosition({ scrollTop: 0, scrollLeft: 0 });
+			inputScrollable.scanDomNode();
+		}));
+
 		// Update aria-label to reflect the current question
 		this._updateAriaLabel();
 
@@ -575,6 +690,143 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 		this._onDidChangeHeight.fire();
 	}
 
+	/**
+	 * Renders or updates the persistent footer with nav arrows, step indicator, and submit button.
+	 */
+	private renderFooter(): void {
+		if (!this._footerRow) {
+			const interactiveStore = this._interactiveUIStore.value;
+			if (!interactiveStore) {
+				return;
+			}
+
+			this._footerRow = dom.$('.chat-question-footer-row');
+
+			// Left side: nav arrows + step indicator
+			const leftControls = dom.$('.chat-question-footer-left.chat-question-carousel-nav');
+			leftControls.setAttribute('role', 'navigation');
+			leftControls.setAttribute('aria-label', localize('chat.questionCarousel.navigation', 'Question navigation'));
+
+			const arrowsContainer = dom.$('.chat-question-nav-arrows');
+
+			const previousLabel = this.getLabelWithKeybinding(localize('previous', 'Previous'), PREVIOUS_QUESTION_ACTION_ID);
+			const prevButton = interactiveStore.add(new Button(arrowsContainer, { ...defaultButtonStyles, secondary: true, supportIcons: true }));
+			prevButton.element.classList.add('chat-question-nav-arrow', 'chat-question-nav-prev');
+			prevButton.label = `$(${Codicon.chevronLeft.id})`;
+			prevButton.element.setAttribute('aria-label', previousLabel);
+			interactiveStore.add(this._hoverService.setupDelayedHover(prevButton.element, { content: previousLabel }));
+			interactiveStore.add(prevButton.onDidClick(() => this.navigate(-1)));
+			this._prevButton = prevButton;
+
+			const nextLabel = this.getLabelWithKeybinding(localize('next', 'Next'), NEXT_QUESTION_ACTION_ID);
+			const nextButton = interactiveStore.add(new Button(arrowsContainer, { ...defaultButtonStyles, secondary: true, supportIcons: true }));
+			nextButton.element.classList.add('chat-question-nav-arrow', 'chat-question-nav-next');
+			nextButton.label = `$(${Codicon.chevronRight.id})`;
+			nextButton.element.setAttribute('aria-label', nextLabel);
+			interactiveStore.add(this._hoverService.setupDelayedHover(nextButton.element, { content: nextLabel }));
+			interactiveStore.add(nextButton.onDidClick(() => this.navigate(1)));
+			this._nextButton = nextButton;
+
+			leftControls.appendChild(arrowsContainer);
+
+			this._stepIndicator = dom.$('.chat-question-step-indicator');
+			leftControls.appendChild(this._stepIndicator);
+
+			this._footerRow.appendChild(leftControls);
+
+			// Right side: hint + submit
+			const rightControls = dom.$('.chat-question-footer-right');
+
+			const hint = dom.$('span.chat-question-submit-hint');
+			hint.textContent = isMacintosh
+				? localize('chat.questionCarousel.submitHintMac', '\u2318\u23CE to submit')
+				: localize('chat.questionCarousel.submitHintOther', 'Ctrl+Enter to submit');
+			rightControls.appendChild(hint);
+			this._submitHint = hint;
+
+			const submitButton = interactiveStore.add(new Button(rightControls, { ...defaultButtonStyles }));
+			submitButton.element.classList.add('chat-question-submit-button');
+			submitButton.label = localize('submit', 'Submit');
+			interactiveStore.add(submitButton.onDidClick(() => this.submit()));
+			this._submitButton = submitButton;
+
+			this._footerRow.appendChild(rightControls);
+			this.domNode.append(this._footerRow);
+		}
+
+		this.updateFooterState();
+	}
+
+	/**
+	 * Updates the footer nav button enabled state and step indicator text.
+	 */
+	private updateFooterState(): void {
+		if (this._prevButton) {
+			this._prevButton.enabled = this._currentIndex > 0;
+		}
+		if (this._nextButton) {
+			const canAdvance = this._currentIndex < this.carousel.questions.length - 1;
+			const question = this.carousel.questions[this._currentIndex];
+			const answer = this._answers.get(question?.id);
+			const hasAnswer = answer !== undefined && answer !== '';
+			const hasValidationError = !!this._currentValidationError;
+			this._nextButton.enabled = canAdvance && (!question?.required || hasAnswer) && !hasValidationError;
+		}
+		if (this._stepIndicator) {
+			this._stepIndicator.textContent = localize(
+				'chat.questionCarousel.stepIndicator',
+				'{0}/{1}',
+				this._currentIndex + 1,
+				this.carousel.questions.length
+			);
+		}
+		if (this._submitButton) {
+			const isLastQuestion = this._currentIndex === this.carousel.questions.length - 1;
+			this._submitButton.element.style.display = isLastQuestion ? '' : 'none';
+			if (this._submitHint) {
+				this._submitHint.style.display = isLastQuestion ? '' : 'none';
+			}
+		}
+	}
+
+	/**
+	 * Renders a simplified footer with just a submit button for single-question multi-select carousels.
+	 */
+	private renderSingleQuestionFooter(): void {
+		if (!this._footerRow) {
+			const interactiveStore = this._interactiveUIStore.value;
+			if (!interactiveStore) {
+				return;
+			}
+
+			this._footerRow = dom.$('.chat-question-footer-row');
+
+			// Spacer to push controls to the right
+			const leftControls = dom.$('.chat-question-footer-left.chat-question-carousel-nav');
+			leftControls.setAttribute('role', 'navigation');
+			leftControls.setAttribute('aria-label', localize('chat.questionCarousel.navigation', 'Question navigation'));
+			this._footerRow.appendChild(leftControls);
+
+			const rightControls = dom.$('.chat-question-footer-right');
+
+			const hint = dom.$('span.chat-question-submit-hint');
+			hint.textContent = isMacintosh
+				? localize('chat.questionCarousel.submitHintMac', '\u2318\u23CE to submit')
+				: localize('chat.questionCarousel.submitHintOther', 'Ctrl+Enter to submit');
+			rightControls.appendChild(hint);
+			this._submitHint = hint;
+
+			const submitButton = interactiveStore.add(new Button(rightControls, { ...defaultButtonStyles }));
+			submitButton.element.classList.add('chat-question-submit-button');
+			submitButton.label = localize('submit', 'Submit');
+			interactiveStore.add(submitButton.onDidClick(() => this.submit()));
+			this._submitButton = submitButton;
+
+			this._footerRow.appendChild(rightControls);
+			this.domNode.append(this._footerRow);
+		}
+	}
+
 	private getLabelWithKeybinding(label: string, actionId: string): string {
 		const keybindingLabel = this._keybindingService.lookupKeybinding(actionId, this._contextKeyService)?.getLabel();
 		return keybindingLabel
@@ -604,6 +856,9 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 		const autoResize = () => {
 			textarea.style.height = 'auto';
 			textarea.style.height = `${Math.min(textarea.scrollHeight, 200)}px`;
+			if (this._inputScrollable) {
+				this.layoutInputScrollable(this._inputScrollable);
+			}
 			this._onDidChangeHeight.fire();
 		};
 		this._inputBoxes.add(dom.addDisposableListener(textarea, dom.EventType.INPUT, autoResize));
@@ -614,6 +869,21 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 		const inputBox = this._inputBoxes.add(new InputBox(container, undefined, {
 			placeholder: localize('chat.questionCarousel.enterText', 'Enter your answer'),
 			inputBoxStyles: defaultInputBoxStyles,
+			validationOptions: question.validation ? {
+				validation: (value: string) => {
+					if (!value && !question.required) {
+						return null;
+					}
+					const error = this.getValidationError(value, question.validation!);
+					if (error) {
+						return { type: 2 /* MessageType.WARNING */, content: error };
+					}
+					return null;
+				}
+			} : undefined,
+		}));
+		this._inputBoxes.add(inputBox.onDidChange(() => {
+			this.saveCurrentAnswer();
 		}));
 
 		// Restore previous answer if exists
@@ -642,12 +912,9 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 
 		// Restore previous answer if exists
 		const previousAnswer = this._answers.get(question.id);
-		const previousFreeform = typeof previousAnswer === 'object' && previousAnswer !== null && hasKey(previousAnswer, { freeformValue: true })
-			? (previousAnswer as { freeformValue?: string }).freeformValue
-			: undefined;
-		const previousSelectedValue = typeof previousAnswer === 'object' && previousAnswer !== null && hasKey(previousAnswer, { selectedValue: true })
-			? (previousAnswer as { selectedValue?: unknown }).selectedValue
-			: previousAnswer;
+		const prevSingle = typeof previousAnswer === 'object' && previousAnswer !== null && hasKey(previousAnswer, { selectedValue: true }) ? previousAnswer as IChatSingleSelectAnswer : undefined;
+		const previousFreeform = prevSingle?.freeformValue;
+		const previousSelectedValue = prevSingle?.selectedValue;
 
 		// Get default option id (for singleSelect, defaultValue is a single string)
 		const defaultOptionId = typeof question.defaultValue === 'string' ? question.defaultValue : undefined;
@@ -683,6 +950,8 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 			if (data) {
 				data.selectedIndex = newIndex;
 			}
+
+			this.saveCurrentAnswer();
 		};
 
 		options.forEach((option, index) => {
@@ -709,12 +978,13 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 			const label = dom.$('.chat-question-list-label');
 			const separatorIndex = option.label.indexOf(' - ');
 			if (separatorIndex !== -1) {
+				listItem.classList.add('has-description');
 				const titleSpan = dom.$('span.chat-question-list-label-title');
 				titleSpan.textContent = option.label.substring(0, separatorIndex);
 				label.appendChild(titleSpan);
 
 				const descSpan = dom.$('span.chat-question-list-label-desc');
-				descSpan.textContent = ': ' + option.label.substring(separatorIndex + 3);
+				descSpan.textContent = option.label.substring(separatorIndex + 3);
 				label.appendChild(descSpan);
 			} else {
 				label.textContent = option.label;
@@ -735,7 +1005,7 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 				if (freeform) {
 					freeform.value = '';
 				}
-				this.handleNext();
+				this.handleNextOrSubmit();
 			}));
 
 			this._inputBoxes.add(this._hoverService.setupDelayedHover(listItem, {
@@ -755,34 +1025,45 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 			selectContainer.setAttribute('aria-activedescendant', listItems[selectedIndex].id);
 		}
 
-		// Always show freeform input for single-select questions
-		const freeformContainer = dom.$('.chat-question-freeform');
+		// Show freeform input only when explicitly allowed
+		let freeformTextarea: HTMLTextAreaElement | undefined;
+		if (question.allowFreeformInput !== false) {
+			const freeformContainer = dom.$('.chat-question-freeform');
 
-		const freeformNumber = dom.$('.chat-question-freeform-number');
-		freeformNumber.textContent = `${options.length + 1}`;
-		freeformContainer.appendChild(freeformNumber);
+			const freeformNumber = dom.$('.chat-question-freeform-number');
+			freeformNumber.textContent = `${options.length + 1}`;
+			freeformContainer.appendChild(freeformNumber);
 
-		const freeformTextarea = dom.$<HTMLTextAreaElement>('textarea.chat-question-freeform-textarea');
-		freeformTextarea.placeholder = localize('chat.questionCarousel.enterCustomAnswer', 'Enter custom answer');
-		freeformTextarea.rows = 1;
+			freeformTextarea = dom.$<HTMLTextAreaElement>('textarea.chat-question-freeform-textarea');
+			freeformTextarea.placeholder = localize('chat.questionCarousel.enterCustomAnswer', 'Enter custom answer');
+			freeformTextarea.rows = 1;
 
-		if (previousFreeform !== undefined) {
-			freeformTextarea.value = previousFreeform;
-		}
+			if (previousFreeform !== undefined) {
+				freeformTextarea.value = previousFreeform;
+			}
 
-		// Setup auto-resize behavior
-		const autoResize = this.setupTextareaAutoResize(freeformTextarea);
+			// Setup auto-resize behavior
+			const autoResize = this.setupTextareaAutoResize(freeformTextarea);
 
-		// clear when we start typing in freeform
-		this._inputBoxes.add(dom.addDisposableListener(freeformTextarea, dom.EventType.INPUT, () => {
-			if (freeformTextarea.value.length > 0) {
-				updateSelection(-1);
-			}
-		}));
+			// clear when we start typing in freeform
+			const capturedFreeform = freeformTextarea;
+			this._inputBoxes.add(dom.addDisposableListener(capturedFreeform, dom.EventType.INPUT, () => {
+				if (capturedFreeform.value.length > 0) {
+					updateSelection(-1);
+				} else {
+					this.saveCurrentAnswer();
+				}
+			}));
 
-		freeformContainer.appendChild(freeformTextarea);
-		container.appendChild(freeformContainer);
-		this._freeformTextareas.set(question.id, freeformTextarea);
+			freeformContainer.appendChild(freeformTextarea);
+			container.appendChild(freeformContainer);
+			this._freeformTextareas.set(question.id, freeformTextarea);
+
+			// Resize textarea if it has restored content
+			if (previousFreeform !== undefined) {
+				this._inputBoxes.add(dom.runAtThisOrScheduleAtNextAnimationFrame(dom.getWindow(capturedFreeform), () => autoResize()));
+			}
+		}
 
 		// Keyboard navigation for the list
 		this._inputBoxes.add(dom.addDisposableListener(selectContainer, dom.EventType.KEY_DOWN, (e: KeyboardEvent) => {
@@ -799,11 +1080,11 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 			} else if (event.keyCode === KeyCode.UpArrow) {
 				e.preventDefault();
 				newIndex = Math.max(data.selectedIndex - 1, 0);
-			} else if (event.keyCode === KeyCode.Enter || event.keyCode === KeyCode.Space) {
+			} else if ((event.keyCode === KeyCode.Enter || event.keyCode === KeyCode.Space) && !event.metaKey && !event.ctrlKey) {
 				// Enter confirms current selection and advances to next question
 				e.preventDefault();
 				e.stopPropagation();
-				this.handleNext();
+				this.handleNextOrSubmit();
 				return;
 			} else if (event.keyCode >= KeyCode.Digit1 && event.keyCode <= KeyCode.Digit9) {
 				// Number keys 1-9 select the corresponding option, or focus freeform for next number
@@ -811,7 +1092,7 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 				if (numberIndex < listItems.length) {
 					e.preventDefault();
 					updateSelection(numberIndex);
-				} else if (numberIndex === listItems.length) {
+				} else if (freeformTextarea && numberIndex === listItems.length) {
 					e.preventDefault();
 					updateSelection(-1);
 					freeformTextarea.focus();
@@ -824,16 +1105,12 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 			}
 		}));
 
-		// Resize textarea if it has restored content
-		if (previousFreeform !== undefined) {
-			this._inputBoxes.add(dom.runAtThisOrScheduleAtNextAnimationFrame(dom.getWindow(freeformTextarea), () => autoResize()));
-		}
-
 		// focus on the row when first rendered or textarea if it has content
 		if (this._shouldAutoFocus()) {
-			if (previousFreeform) {
-				this._inputBoxes.add(dom.runAtThisOrScheduleAtNextAnimationFrame(dom.getWindow(freeformTextarea), () => {
-					freeformTextarea.focus();
+			if (freeformTextarea && previousFreeform) {
+				const capturedFreeform = freeformTextarea;
+				this._inputBoxes.add(dom.runAtThisOrScheduleAtNextAnimationFrame(dom.getWindow(capturedFreeform), () => {
+					capturedFreeform.focus();
 				}));
 			} else if (listItems.length > 0) {
 				const focusIndex = selectedIndex >= 0 ? selectedIndex : 0;
@@ -859,12 +1136,9 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 
 		// Restore previous answer if exists
 		const previousAnswer = this._answers.get(question.id);
-		const previousFreeform = typeof previousAnswer === 'object' && previousAnswer !== null && hasKey(previousAnswer, { freeformValue: true })
-			? (previousAnswer as { freeformValue?: string }).freeformValue
-			: undefined;
-		const previousSelectedValues = typeof previousAnswer === 'object' && previousAnswer !== null && hasKey(previousAnswer, { selectedValues: true })
-			? (previousAnswer as { selectedValues?: unknown[] }).selectedValues
-			: (Array.isArray(previousAnswer) ? previousAnswer : []);
+		const prevMulti = typeof previousAnswer === 'object' && previousAnswer !== null && hasKey(previousAnswer, { selectedValues: true }) ? previousAnswer as IChatMultiSelectAnswer : undefined;
+		const previousFreeform = prevMulti?.freeformValue;
+		const previousSelectedValues = prevMulti?.selectedValues ?? [];
 
 		// Get default option ids (for multiSelect, defaultValue can be string or string[])
 		const defaultOptionIds: string[] = Array.isArray(question.defaultValue)
@@ -907,12 +1181,13 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 			const label = dom.$('.chat-question-list-label');
 			const separatorIndex = option.label.indexOf(' - ');
 			if (separatorIndex !== -1) {
+				listItem.classList.add('has-description');
 				const titleSpan = dom.$('span.chat-question-list-label-title');
 				titleSpan.textContent = option.label.substring(0, separatorIndex);
 				label.appendChild(titleSpan);
 
 				const descSpan = dom.$('span.chat-question-list-label-desc');
-				descSpan.textContent = ': ' + option.label.substring(separatorIndex + 3);
+				descSpan.textContent = option.label.substring(separatorIndex + 3);
 				label.appendChild(descSpan);
 			} else {
 				label.textContent = option.label;
@@ -930,6 +1205,7 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 			this._inputBoxes.add(checkbox.onChange(() => {
 				listItem.classList.toggle('checked', checkbox.checked);
 				listItem.setAttribute('aria-selected', String(checkbox.checked));
+				this.saveCurrentAnswer();
 			}));
 
 			// Click handler for the entire row (toggle checkbox)
@@ -956,28 +1232,37 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 
 		this._multiSelectCheckboxes.set(question.id, checkboxes);
 
-		// Always show freeform input for multi-select questions
-		const freeformContainer = dom.$('.chat-question-freeform');
+		// Show freeform input only when explicitly allowed
+		let freeformTextarea: HTMLTextAreaElement | undefined;
+		if (question.allowFreeformInput !== false) {
+			const freeformContainer = dom.$('.chat-question-freeform');
 
-		// Number indicator for freeform (comes after all options)
-		const freeformNumber = dom.$('.chat-question-freeform-number');
-		freeformNumber.textContent = `${options.length + 1}`;
-		freeformContainer.appendChild(freeformNumber);
+			// Number indicator for freeform (comes after all options)
+			const freeformNumber = dom.$('.chat-question-freeform-number');
+			freeformNumber.textContent = `${options.length + 1}`;
+			freeformContainer.appendChild(freeformNumber);
 
-		const freeformTextarea = dom.$<HTMLTextAreaElement>('textarea.chat-question-freeform-textarea');
-		freeformTextarea.placeholder = localize('chat.questionCarousel.enterCustomAnswer', 'Enter custom answer');
-		freeformTextarea.rows = 1;
+			freeformTextarea = dom.$<HTMLTextAreaElement>('textarea.chat-question-freeform-textarea');
+			freeformTextarea.placeholder = localize('chat.questionCarousel.enterCustomAnswer', 'Enter custom answer');
+			freeformTextarea.rows = 1;
 
-		if (previousFreeform !== undefined) {
-			freeformTextarea.value = previousFreeform;
-		}
+			if (previousFreeform !== undefined) {
+				freeformTextarea.value = previousFreeform;
+			}
+
+			// Setup auto-resize behavior
+			const autoResize = this.setupTextareaAutoResize(freeformTextarea);
+			this._inputBoxes.add(dom.addDisposableListener(freeformTextarea, dom.EventType.INPUT, () => this.saveCurrentAnswer()));
 
-		// Setup auto-resize behavior
-		const autoResize = this.setupTextareaAutoResize(freeformTextarea);
+			freeformContainer.appendChild(freeformTextarea);
+			container.appendChild(freeformContainer);
+			this._freeformTextareas.set(question.id, freeformTextarea);
 
-		freeformContainer.appendChild(freeformTextarea);
-		container.appendChild(freeformContainer);
-		this._freeformTextareas.set(question.id, freeformTextarea);
+			// Resize textarea if it has restored content
+			if (previousFreeform !== undefined) {
+				this._inputBoxes.add(dom.runAtThisOrScheduleAtNextAnimationFrame(dom.getWindow(freeformTextarea), () => autoResize()));
+			}
+		}
 
 		// Keyboard navigation for the list
 		this._inputBoxes.add(dom.addDisposableListener(selectContainer, dom.EventType.KEY_DOWN, (e: KeyboardEvent) => {
@@ -996,10 +1281,10 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 				e.preventDefault();
 				focusedIndex = Math.max(focusedIndex - 1, 0);
 				listItems[focusedIndex].focus();
-			} else if (event.keyCode === KeyCode.Enter) {
+			} else if (event.keyCode === KeyCode.Enter && !event.metaKey && !event.ctrlKey) {
 				e.preventDefault();
 				e.stopPropagation();
-				this.handleNext();
+				this.handleNextOrSubmit();
 			} else if (event.keyCode === KeyCode.Space) {
 				e.preventDefault();
 				// Toggle the currently focused checkbox using click() to trigger onChange
@@ -1012,23 +1297,19 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 				if (numberIndex < checkboxes.length) {
 					e.preventDefault();
 					checkboxes[numberIndex].domNode.click();
-				} else if (numberIndex === checkboxes.length) {
+				} else if (freeformTextarea && numberIndex === checkboxes.length) {
 					e.preventDefault();
 					freeformTextarea.focus();
 				}
 			}
 		}));
 
-		// Resize textarea if it has restored content
-		if (previousFreeform !== undefined) {
-			this._inputBoxes.add(dom.runAtThisOrScheduleAtNextAnimationFrame(dom.getWindow(freeformTextarea), () => autoResize()));
-		}
-
 		// Focus on the appropriate row when rendered or textarea if it has content
 		if (this._shouldAutoFocus()) {
-			if (previousFreeform) {
-				this._inputBoxes.add(dom.runAtThisOrScheduleAtNextAnimationFrame(dom.getWindow(freeformTextarea), () => {
-					freeformTextarea.focus();
+			if (freeformTextarea && previousFreeform) {
+				const capturedFreeform = freeformTextarea;
+				this._inputBoxes.add(dom.runAtThisOrScheduleAtNextAnimationFrame(dom.getWindow(capturedFreeform), () => {
+					capturedFreeform.focus();
 				}));
 			} else if (listItems.length > 0) {
 				const initialFocusIndex = firstCheckedIndex >= 0 ? firstCheckedIndex : 0;
@@ -1040,7 +1321,7 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 		}
 	}
 
-	private getCurrentAnswer(): unknown {
+	private getCurrentAnswer(): IChatQuestionAnswerValue | undefined {
 		const question = this.carousel.questions[this._currentIndex];
 		if (!question) {
 			return undefined;
@@ -1049,12 +1330,12 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 		switch (question.type) {
 			case 'text': {
 				const inputBox = this._textInputBoxes.get(question.id);
-				return inputBox?.value ?? question.defaultValue;
+				return inputBox?.value ?? (typeof question.defaultValue === 'string' ? question.defaultValue : Array.isArray(question.defaultValue) ? { selectedValues: question.defaultValue } : undefined);
 			}
 
 			case 'singleSelect': {
 				const data = this._singleSelectItems.get(question.id);
-				let selectedValue: unknown = undefined;
+				let selectedValue: string | undefined = undefined;
 				if (data && data.selectedIndex >= 0) {
 					selectedValue = question.options?.[data.selectedIndex]?.value;
 				}
@@ -1069,17 +1350,17 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 				const freeformValue = freeformTextarea?.value !== '' ? freeformTextarea?.value : undefined;
 				if (freeformValue) {
 					// Freeform takes priority - ignore selectedValue
-					return { selectedValue: undefined, freeformValue };
+					return { selectedValue: undefined, freeformValue } satisfies IChatSingleSelectAnswer;
 				}
 				if (selectedValue !== undefined) {
-					return { selectedValue, freeformValue: undefined };
+					return { selectedValue, freeformValue: undefined } satisfies IChatSingleSelectAnswer;
 				}
 				return undefined;
 			}
 
 			case 'multiSelect': {
 				const checkboxes = this._multiSelectCheckboxes.get(question.id);
-				const selectedValues: unknown[] = [];
+				const selectedValues: string[] = [];
 				if (checkboxes) {
 					checkboxes.forEach((checkbox, index) => {
 						if (checkbox.checked) {
@@ -1098,13 +1379,13 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 				// Return whatever was selected - defaults are applied at render time when
 				// checkboxes are initially checked, so empty selection means user unchecked all
 				if (freeformValue || selectedValues.length > 0) {
-					return { selectedValues, freeformValue };
+					return { selectedValues, freeformValue } satisfies IChatMultiSelectAnswer;
 				}
 				return undefined;
 			}
 
 			default:
-				return question.defaultValue;
+				return typeof question.defaultValue === 'string' ? question.defaultValue : Array.isArray(question.defaultValue) ? { selectedValues: question.defaultValue } : undefined;
 		}
 	}
 
@@ -1135,40 +1416,25 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 
 		for (const question of this.carousel.questions) {
 			const answer = this._answers.get(question.id);
-			if (answer === undefined) {
-				continue;
-			}
 
 			const summaryItem = dom.$('.chat-question-summary-item');
 
-			// Category label (use same text as shown in question UI: message ?? title)
-			const questionLabel = dom.$('span.chat-question-summary-label');
+			const questionRow = dom.$('div.chat-question-summary-label');
 			const questionText = question.message ?? question.title;
 			let labelText = typeof questionText === 'string' ? questionText : questionText.value;
-			// Remove trailing colons and whitespace to avoid double colons (CSS adds ': ')
 			labelText = labelText.replace(/[:\s]+$/, '');
-			questionLabel.textContent = labelText;
-			summaryItem.appendChild(questionLabel);
-
-			// Format answer with title and description parts
-			const formattedAnswer = this.formatAnswerForSummary(question, answer);
-			const separatorIndex = formattedAnswer.indexOf(' - ');
-
-			if (separatorIndex !== -1) {
-				// Answer title (bold)
-				const answerTitle = dom.$('span.chat-question-summary-answer-title');
-				answerTitle.textContent = formattedAnswer.substring(0, separatorIndex);
-				summaryItem.appendChild(answerTitle);
-
-				// Answer description (normal)
-				const answerDesc = dom.$('span.chat-question-summary-answer-desc');
-				answerDesc.textContent = ' - ' + formattedAnswer.substring(separatorIndex + 3);
-				summaryItem.appendChild(answerDesc);
+			questionRow.textContent = localize('chat.questionCarousel.summaryQuestion', 'Q: {0}', labelText);
+			summaryItem.appendChild(questionRow);
+
+			if (answer !== undefined) {
+				const formattedAnswer = this.formatAnswerForSummary(question, answer);
+				const answerRow = dom.$('div.chat-question-summary-answer-title');
+				answerRow.textContent = localize('chat.questionCarousel.summaryAnswer', 'A: {0}', formattedAnswer);
+				summaryItem.appendChild(answerRow);
 			} else {
-				// Just the answer value (bold)
-				const answerValue = dom.$('span.chat-question-summary-answer-title');
-				answerValue.textContent = formattedAnswer;
-				summaryItem.appendChild(answerValue);
+				const unanswered = dom.$('div.chat-question-summary-unanswered');
+				unanswered.textContent = localize('chat.questionCarousel.notAnsweredYet', 'Not answered yet');
+				summaryItem.appendChild(unanswered);
 			}
 
 			summaryContainer.appendChild(summaryItem);
@@ -1180,15 +1446,15 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 	/**
 	 * Formats an answer for display in the summary.
 	 */
-	private formatAnswerForSummary(question: IChatQuestion, answer: unknown): string {
+	private formatAnswerForSummary(question: IChatQuestion, answer: IChatQuestionAnswerValue): string {
 		switch (question.type) {
 			case 'text':
 				return String(answer);
 
 			case 'singleSelect': {
-				if (typeof answer === 'object' && answer !== null && hasKey(answer, { selectedValue: true })) {
-					const { selectedValue, freeformValue } = answer as { selectedValue?: unknown; freeformValue?: string };
-					const selectedLabel = question.options?.find(opt => opt.value === selectedValue)?.label;
+				if (typeof answer === 'object') {
+					const { selectedValue, freeformValue } = answer as IChatSingleSelectAnswer;
+					const selectedLabel = selectedValue !== undefined ? question.options?.find(opt => opt.value === selectedValue)?.label : undefined;
 					// For singleSelect, freeform takes priority over selection
 					if (freeformValue) {
 						return freeformValue;
@@ -1200,9 +1466,9 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 			}
 
 			case 'multiSelect': {
-				if (typeof answer === 'object' && answer !== null && hasKey(answer, { selectedValues: true })) {
-					const { selectedValues, freeformValue } = answer as { selectedValues?: unknown[]; freeformValue?: string };
-					const labels = (selectedValues ?? [])
+				if (typeof answer === 'object' && hasKey(answer, { selectedValues: true })) {
+					const { selectedValues, freeformValue } = answer;
+					const labels = selectedValues
 						.map(v => question.options?.find(opt => opt.value === v)?.label ?? String(v));
 					// For multiSelect, combine selections and freeform with comma separator
 					if (freeformValue) {
@@ -1210,11 +1476,6 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 					}
 					return labels.join(localize('chat.questionCarousel.listSeparator', ', '));
 				}
-				if (Array.isArray(answer)) {
-					return answer
-						.map(v => question.options?.find(opt => opt.value === v)?.label ?? String(v))
-						.join(localize('chat.questionCarousel.listSeparator', ', '));
-				}
 				return String(answer);
 			}
 
@@ -1224,11 +1485,133 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 	}
 
 	private getQuestionText(questionText: string | IMarkdownString): string {
-		if (typeof questionText === 'string') {
-			return questionText;
+		const md = typeof questionText === 'string' ? new MarkdownString(questionText) : questionText;
+		return renderAsPlaintext(md);
+	}
+
+	/**
+	 * Validates the current question's answer against its validation rules.
+	 * Returns true if valid, false if validation errors were shown.
+	 */
+	private validateCurrentQuestion(): boolean {
+		const question = this.carousel.questions[this._currentIndex];
+		if (!question) {
+			return true;
 		}
 
-		return renderAsPlaintext(questionText);
+		const answer = this._answers.get(question.id);
+
+		// Check required
+		if (question.required && (answer === undefined || answer === '')) {
+			this.showValidationError(localize('chat.questionCarousel.required', 'This field is required'));
+			return false;
+		}
+
+		// Validate text inputs
+		if (question.type === 'text' && question.validation && typeof answer === 'string' && answer !== '') {
+			const error = this.getValidationError(answer, question.validation);
+			if (error) {
+				this.showValidationError(error);
+				return false;
+			}
+		}
+
+		this.clearValidationError();
+		return true;
+	}
+
+	/**
+	 * Validates that all required questions have been answered.
+	 * Returns true if all required fields are satisfied.
+	 */
+	private validateRequiredFields(): boolean {
+		for (let i = 0; i < this.carousel.questions.length; i++) {
+			const question = this.carousel.questions[i];
+			if (!question.required) {
+				continue;
+			}
+			const answer = this._answers.get(question.id);
+			if (answer === undefined || answer === '') {
+				// Navigate to the unanswered required question
+				this.saveCurrentAnswer();
+				this._currentIndex = i;
+				this.persistDraftState();
+				this.renderCurrentQuestion(true);
+				this.showValidationError(localize('chat.questionCarousel.required', 'This field is required'));
+				return false;
+			}
+		}
+		return true;
+	}
+
+	/**
+	 * Returns a validation error message for the given value, or undefined if valid.
+	 */
+	private getValidationError(value: string, validation: IChatQuestionValidation): string | undefined {
+		if (validation.minLength !== undefined && value.length < validation.minLength) {
+			return localize('chat.questionCarousel.validation.minLength', 'Minimum length is {0}', validation.minLength);
+		}
+		if (validation.maxLength !== undefined && value.length > validation.maxLength) {
+			return localize('chat.questionCarousel.validation.maxLength', 'Maximum length is {0}', validation.maxLength);
+		}
+		if (validation.format) {
+			switch (validation.format) {
+				case 'email':
+					if (!value.includes('@')) {
+						return localize('chat.questionCarousel.validation.email', 'Please enter a valid email address');
+					}
+					break;
+				case 'uri':
+					if (!URL.canParse(value)) {
+						return localize('chat.questionCarousel.validation.uri', 'Please enter a valid URI');
+					}
+					break;
+				case 'date': {
+					const dateRegex = /^\d{4}-\d{2}-\d{2}$/;
+					if (!dateRegex.test(value) || isNaN(new Date(value).getTime())) {
+						return localize('chat.questionCarousel.validation.date', 'Please enter a valid date (YYYY-MM-DD)');
+					}
+					break;
+				}
+				case 'date-time':
+					if (isNaN(new Date(value).getTime())) {
+						return localize('chat.questionCarousel.validation.dateTime', 'Please enter a valid date-time');
+					}
+					break;
+			}
+		}
+		if (validation.isInteger !== undefined || validation.minimum !== undefined || validation.maximum !== undefined) {
+			const num = Number(value);
+			if (isNaN(num)) {
+				return localize('chat.questionCarousel.validation.number', 'Please enter a valid number');
+			}
+			if (validation.isInteger && !Number.isInteger(num)) {
+				return localize('chat.questionCarousel.validation.integer', 'Please enter a valid integer');
+			}
+			if (validation.minimum !== undefined && num < validation.minimum) {
+				return localize('chat.questionCarousel.validation.minimum', 'Minimum value is {0}', validation.minimum);
+			}
+			if (validation.maximum !== undefined && num > validation.maximum) {
+				return localize('chat.questionCarousel.validation.maximum', 'Maximum value is {0}', validation.maximum);
+			}
+		}
+		return undefined;
+	}
+
+	private showValidationError(message: string): void {
+		this._currentValidationError = message;
+		if (this._validationMessageElement) {
+			this._validationMessageElement.textContent = message;
+			this._validationMessageElement.style.display = '';
+		}
+	}
+
+	private clearValidationError(): void {
+		this._currentValidationError = undefined;
+		if (this._validationMessageElement) {
+			this._validationMessageElement.textContent = '';
+			this._validationMessageElement.style.display = 'none';
+		}
 	}
 
 	hasSameContent(other: IChatRendererContent, _followingContent: IChatRendererContent[], element: ChatTreeItem): boolean {
@@ -1242,4 +1625,12 @@ export class ChatQuestionCarouselPart extends Disposable implements IChatContent
 	addDisposable(disposable: { dispose(): void }): void {
 		this._register(disposable);
 	}
+
+	override dispose(): void {
+		if (!this._isSkipped && !this.carousel.isUsed) {
+			this.saveCurrentAnswer();
+		}
+
+		super.dispose();
+	}
 }
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatReferencesContentPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatReferencesContentPart.ts
index 6ff863773dbbb..849393873dd5a 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatReferencesContentPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatReferencesContentPart.ts
@@ -56,6 +56,7 @@ export interface IChatReferenceListItem extends IChatContentReference {
 	description?: string;
 	state?: ModifiedFileEntryState;
 	excluded?: boolean;
+	showModifiedState?: boolean;
 }
 
 export type IChatCollapsibleListItem = IChatReferenceListItem | IChatWarningMessage;
@@ -389,8 +390,7 @@ class CollapsibleListRenderer implements IListRenderer<IChatCollapsibleListItem,
 				const label = `Kernel variable`;
 				templateData.label.setLabel(label, asVariableName, { title: data.options?.status?.description });
 			} else {
-				// Nothing else is expected to fall into here
-				templateData.label.setLabel('Unknown variable type: ' + reference.variableName);
+				templateData.label.setLabel(reference.variableName, undefined, { title: data.options?.status?.description ?? data.title });
 			}
 		} else if (typeof reference === 'string') {
 			templateData.label.setLabel(reference, undefined, { iconPath: URI.isUri(icon) ? icon : undefined, title: data.options?.status?.description ?? data.title });
@@ -434,7 +434,7 @@ class CollapsibleListRenderer implements IListRenderer<IChatCollapsibleListItem,
 		}
 
 		if (data.state !== undefined) {
-			if (templateData.actionBarContainer) {
+			if (templateData.actionBarContainer || data.showModifiedState) {
 				const diffMeta = data?.options?.diffMeta;
 				if (diffMeta) {
 					if (!templateData.fileDiffsContainer || !templateData.addedSpan || !templateData.removedSpan) {
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatResourceGroupWidget.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatResourceGroupWidget.ts
new file mode 100644
index 0000000000000..dcd85778a0e6f
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatResourceGroupWidget.ts
@@ -0,0 +1,241 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../../../base/browser/dom.js';
+import { disposableTimeout } from '../../../../../../base/common/async.js';
+import { decodeBase64 } from '../../../../../../base/common/buffer.js';
+import { Codicon } from '../../../../../../base/common/codicons.js';
+import { Disposable } from '../../../../../../base/common/lifecycle.js';
+import { basename, joinPath } from '../../../../../../base/common/resources.js';
+import { URI } from '../../../../../../base/common/uri.js';
+import { generateUuid } from '../../../../../../base/common/uuid.js';
+import { localize, localize2 } from '../../../../../../nls.js';
+import { MenuWorkbenchToolBar } from '../../../../../../platform/actions/browser/toolbar.js';
+import { Action2, MenuId, registerAction2 } from '../../../../../../platform/actions/common/actions.js';
+import { ICommandService } from '../../../../../../platform/commands/common/commands.js';
+import { IContextMenuService } from '../../../../../../platform/contextview/browser/contextView.js';
+import { IFileDialogService } from '../../../../../../platform/dialogs/common/dialogs.js';
+import { IFileService } from '../../../../../../platform/files/common/files.js';
+import { IInstantiationService, ServicesAccessor } from '../../../../../../platform/instantiation/common/instantiation.js';
+import { ILabelService } from '../../../../../../platform/label/common/label.js';
+import { INotificationService } from '../../../../../../platform/notification/common/notification.js';
+import { IProgressService, ProgressLocation } from '../../../../../../platform/progress/common/progress.js';
+import { IWorkspaceContextService } from '../../../../../../platform/workspace/common/workspace.js';
+import { REVEAL_IN_EXPLORER_COMMAND_ID } from '../../../../files/browser/fileConstants.js';
+import { getAttachableImageExtension } from '../../../common/model/chatModel.js';
+import { IChatRequestVariableEntry } from '../../../common/attachments/chatVariableEntries.js';
+import { ChatAttachmentsContentPart } from './chatAttachmentsContentPart.js';
+import { IChatCollapsibleIODataPart } from './chatToolInputOutputContentPart.js';
+
+export interface IChatToolOutputResourceToolbarContext {
+	parts: IChatCollapsibleIODataPart[];
+}
+
+/**
+ * Delay in milliseconds before decoding base64 image data.
+ * This avoids expensive decode operations during scrolling.
+ */
+const IMAGE_DECODE_DELAY_MS = 100;
+
+/**
+ * A reusable widget for rendering a group of resource data parts (files, images)
+ * with attachment pills and a toolbar with save actions.
+ *
+ * Used by ChatToolOutputContentSubPart and ChatMcpAppSubPart (for download resources).
+ */
+export class ChatResourceGroupWidget extends Disposable {
+	public readonly domNode: HTMLElement;
+
+	constructor(
+		parts: IChatCollapsibleIODataPart[],
+		@IInstantiationService private readonly _instantiationService: IInstantiationService,
+		@IContextMenuService private readonly _contextMenuService: IContextMenuService,
+		@IFileService private readonly _fileService: IFileService,
+	) {
+		super();
+
+		const el = dom.h('.chat-collapsible-io-resource-group', [
+			dom.h('.chat-collapsible-io-resource-items@items'),
+			dom.h('.chat-collapsible-io-resource-actions@actions'),
+		]);
+
+		this.domNode = el.root;
+		this._fillInResourceGroup(parts, el.items, el.actions);
+	}
+
+	private async _fillInResourceGroup(parts: IChatCollapsibleIODataPart[], itemsContainer: HTMLElement, actionsContainer: HTMLElement) {
+		// First pass: create entries immediately, using file placeholders for base64 images
+		const entries: IChatRequestVariableEntry[] = [];
+		const deferredImageParts: { index: number; part: IChatCollapsibleIODataPart }[] = [];
+
+		for (let i = 0; i < parts.length; i++) {
+			const part = parts[i];
+			if (part.mimeType && getAttachableImageExtension(part.mimeType)) {
+				if (part.base64Value) {
+					// Defer base64 decode - use file placeholder for now
+					entries.push({ kind: 'file', id: generateUuid(), name: basename(part.uri), fullName: part.uri.path, value: part.uri });
+					deferredImageParts.push({ index: i, part });
+				} else if (part.value) {
+					entries.push({ kind: 'image', id: generateUuid(), name: basename(part.uri), value: part.value, mimeType: part.mimeType, isURL: false, references: [{ kind: 'reference', reference: part.uri }] });
+				} else {
+					const value = await this._fileService.readFile(part.uri).then(f => f.value.buffer, () => undefined);
+					if (!value) {
+						entries.push({ kind: 'file', id: generateUuid(), name: basename(part.uri), fullName: part.uri.path, value: part.uri });
+					} else {
+						entries.push({ kind: 'image', id: generateUuid(), name: basename(part.uri), value, mimeType: part.mimeType, isURL: false, references: [{ kind: 'reference', reference: part.uri }] });
+					}
+				}
+			} else {
+				entries.push({ kind: 'file', id: generateUuid(), name: basename(part.uri), fullName: part.uri.path, value: part.uri });
+			}
+		}
+
+		if (this._store.isDisposed) {
+			return;
+		}
+
+		// Render attachments immediately with placeholders
+		const attachments = this._register(this._instantiationService.createInstance(
+			ChatAttachmentsContentPart,
+			{
+				variables: entries,
+				limit: 5,
+				contentReferences: undefined,
+				domNode: undefined
+			}
+		));
+
+		attachments.contextMenuHandler = (attachment, event) => {
+			const index = entries.indexOf(attachment);
+			const part = parts[index];
+			if (part) {
+				event.preventDefault();
+				event.stopPropagation();
+
+				this._contextMenuService.showContextMenu({
+					menuId: MenuId.ChatToolOutputResourceContext,
+					menuActionOptions: { shouldForwardArgs: true },
+					getAnchor: () => ({ x: event.pageX, y: event.pageY }),
+					getActionsContext: () => ({ parts: [part] } satisfies IChatToolOutputResourceToolbarContext),
+				});
+			}
+		};
+
+		itemsContainer.appendChild(attachments.domNode!);
+
+		const toolbar = this._register(this._instantiationService.createInstance(MenuWorkbenchToolBar, actionsContainer, MenuId.ChatToolOutputResourceToolbar, {
+			menuOptions: {
+				shouldForwardArgs: true,
+			},
+		}));
+		toolbar.context = { parts } satisfies IChatToolOutputResourceToolbarContext;
+
+		// Second pass: decode base64 images asynchronously and update in place
+		if (deferredImageParts.length > 0) {
+			this._register(disposableTimeout(() => {
+				for (const { index, part } of deferredImageParts) {
+					try {
+						const value = decodeBase64(part.base64Value!).buffer;
+						entries[index] = { kind: 'image', id: generateUuid(), name: basename(part.uri), value, mimeType: part.mimeType!, isURL: false, references: [{ kind: 'reference', reference: part.uri }] };
+					} catch {
+						// Keep the file placeholder on decode failure
+					}
+				}
+
+				// Update attachments in place
+				attachments.updateVariables(entries);
+			}, IMAGE_DECODE_DELAY_MS));
+		}
+	}
+}
+
+
+class SaveResourcesAction extends Action2 {
+	public static readonly ID = 'chat.toolOutput.save';
+	constructor() {
+		super({
+			id: SaveResourcesAction.ID,
+			title: localize2('chat.saveResources', "Save..."),
+			icon: Codicon.cloudDownload,
+			menu: [{
+				id: MenuId.ChatToolOutputResourceToolbar,
+				group: 'navigation',
+				order: 1
+			}, {
+				id: MenuId.ChatToolOutputResourceContext,
+			}]
+		});
+	}
+
+	async run(accessor: ServicesAccessor, context: IChatToolOutputResourceToolbarContext) {
+		const fileDialog = accessor.get(IFileDialogService);
+		const fileService = accessor.get(IFileService);
+		const notificationService = accessor.get(INotificationService);
+		const progressService = accessor.get(IProgressService);
+		const workspaceContextService = accessor.get(IWorkspaceContextService);
+		const commandService = accessor.get(ICommandService);
+		const labelService = accessor.get(ILabelService);
+		const defaultFilepath = await fileDialog.defaultFilePath();
+
+		const savePart = async (part: IChatCollapsibleIODataPart, isFolder: boolean, uri: URI) => {
+			const target = isFolder ? joinPath(uri, basename(part.uri)) : uri;
+			try {
+				if (part.kind === 'data') {
+					await fileService.copy(part.uri, target, true);
+				} else {
+					// MCP doesn't support streaming data, so no sense trying
+					const contents = await fileService.readFile(part.uri);
+					await fileService.writeFile(target, contents.value);
+				}
+			} catch (e) {
+				notificationService.error(localize('chat.saveResources.error', "Failed to save {0}: {1}", basename(part.uri), e));
+			}
+		};
+
+		const withProgress = async (thenReveal: URI, todo: (() => Promise<void>)[]) => {
+			await progressService.withProgress({
+				location: ProgressLocation.Notification,
+				delay: 5_000,
+				title: localize('chat.saveResources.progress', "Saving resources..."),
+			}, async report => {
+				for (const task of todo) {
+					await task();
+					report.report({ increment: 1, total: todo.length });
+				}
+			});
+
+			if (workspaceContextService.isInsideWorkspace(thenReveal)) {
+				commandService.executeCommand(REVEAL_IN_EXPLORER_COMMAND_ID, thenReveal);
+			} else {
+				notificationService.info(localize('chat.saveResources.reveal', "Saved resources to {0}", labelService.getUriLabel(thenReveal)));
+			}
+		};
+
+		if (context.parts.length === 1) {
+			const part = context.parts[0];
+			const uri = await fileDialog.pickFileToSave(joinPath(defaultFilepath, basename(part.uri)));
+			if (!uri) {
+				return;
+			}
+			await withProgress(uri, [() => savePart(part, false, uri)]);
+		} else {
+			const uris = await fileDialog.showOpenDialog({
+				title: localize('chat.saveResources.title', "Pick folder to save resources"),
+				canSelectFiles: false,
+				canSelectFolders: true,
+				canSelectMany: false,
+				defaultUri: workspaceContextService.getWorkspace().folders[0]?.uri,
+			});
+
+			if (!uris?.length) {
+				return;
+			}
+
+			await withProgress(uris[0], context.parts.map(part => () => savePart(part, true, uris[0])));
+		}
+	}
+}
+
+registerAction2(SaveResourcesAction);
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatSubagentContentPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatSubagentContentPart.ts
index 969d7b506a0d0..b39a3230afadb 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatSubagentContentPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatSubagentContentPart.ts
@@ -102,7 +102,7 @@ export class ChatSubagentContentPart extends ChatCollapsibleContentPart implemen
 	// Persistent title elements for shimmer
 	private titleShimmerSpan: HTMLElement | undefined;
 	private titleDetailContainer: HTMLElement | undefined;
-	private titleDetailRendered: IRenderedMarkdown | undefined;
+	private readonly _titleDetailRendered = this._register(new MutableDisposable<IRenderedMarkdown>());
 
 	/**
 	 * Check if a tool invocation is the parent subagent tool (the tool that spawns a subagent).
@@ -379,6 +379,26 @@ export class ChatSubagentContentPart extends ChatCollapsibleContentPart implemen
 
 		const labelElement = this._collapseButton.labelElement;
 
+		if (!this.isActive) {
+			labelElement.textContent = '';
+			this.titleShimmerSpan = undefined;
+
+			this._titleDetailRendered.clear();
+			this.titleDetailContainer = undefined;
+
+			const prefixSpan = $('span');
+			prefixSpan.textContent = `${prefix}:`;
+			labelElement.appendChild(prefixSpan);
+
+			const descSpan = $('span.chat-thinking-title-detail-text');
+			descSpan.textContent = ` ${this.description}`;
+			labelElement.appendChild(descSpan);
+
+			this._collapseButton.element.ariaLabel = shimmerText;
+			this._collapseButton.element.ariaExpanded = String(this.isExpanded());
+			return;
+		}
+
 		// Ensure the persistent shimmer span exists
 		if (!this.titleShimmerSpan || !this.titleShimmerSpan.parentElement) {
 			labelElement.textContent = '';
@@ -388,10 +408,7 @@ export class ChatSubagentContentPart extends ChatCollapsibleContentPart implemen
 		this.titleShimmerSpan.textContent = shimmerText;
 
 		// Dispose previous detail rendering
-		if (this.titleDetailRendered) {
-			this.titleDetailRendered.dispose();
-			this.titleDetailRendered = undefined;
-		}
+		this._titleDetailRendered.clear();
 
 		if (!toolCallText) {
 			if (this.titleDetailContainer) {
@@ -402,7 +419,7 @@ export class ChatSubagentContentPart extends ChatCollapsibleContentPart implemen
 			const result = this.chatContentMarkdownRenderer.render(new MarkdownString(toolCallText));
 			result.element.classList.add('collapsible-title-content', 'chat-thinking-title-detail');
 			renderFileWidgets(result.element, this.instantiationService, this.chatMarkdownAnchorService, this._store);
-			this.titleDetailRendered = result;
+			this._titleDetailRendered.value = result;
 
 			if (this.titleDetailContainer) {
 				this.titleDetailContainer.replaceWith(result.element);
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatSuggestNextWidget.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatSuggestNextWidget.ts
index c9e3d0c4a962e..5d1fcbe700410 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatSuggestNextWidget.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatSuggestNextWidget.ts
@@ -9,7 +9,11 @@ import { Emitter, Event } from '../../../../../../base/common/event.js';
 import { Disposable, DisposableStore } from '../../../../../../base/common/lifecycle.js';
 import { ThemeIcon } from '../../../../../../base/common/themables.js';
 import { localize } from '../../../../../../nls.js';
+import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
+import { IContextKeyService } from '../../../../../../platform/contextkey/common/contextkey.js';
 import { IContextMenuService } from '../../../../../../platform/contextview/browser/contextView.js';
+import { ChatContextKeys } from '../../../common/actions/chatContextKeys.js';
+import { ChatConfiguration } from '../../../common/constants.js';
 import { IChatMode } from '../../../common/chatModes.js';
 import { IChatSessionsService } from '../../../common/chatSessionsService.js';
 import { IHandOff } from '../../../common/promptSyntax/promptFileParser.js';
@@ -18,6 +22,7 @@ import { getAgentCanContinueIn, getAgentSessionProvider, getAgentSessionProvider
 export interface INextPromptSelection {
 	readonly handoff: IHandOff;
 	readonly agentId?: string;
+	readonly withAutopilot?: boolean;
 }
 
 export class ChatSuggestNextWidget extends Disposable {
@@ -35,8 +40,10 @@ export class ChatSuggestNextWidget extends Disposable {
 	private buttonDisposables = new Map<HTMLElement, DisposableStore>();
 
 	constructor(
+		@IConfigurationService private readonly configurationService: IConfigurationService,
 		@IContextMenuService private readonly contextMenuService: IContextMenuService,
-		@IChatSessionsService private readonly chatSessionsService: IChatSessionsService
+		@IChatSessionsService private readonly chatSessionsService: IChatSessionsService,
+		@IContextKeyService private readonly contextKeyService: IContextKeyService
 	) {
 		super();
 		this.domNode = this.createSuggestNextWidget();
@@ -92,9 +99,17 @@ export class ChatSuggestNextWidget extends Disposable {
 			this.promptsContainer.removeChild(child);
 		}
 
+		const isAutopilotEnabled = this.configurationService.getValue<boolean>(ChatConfiguration.AutopilotEnabled) !== false;
+		const firstAutoSendHandoff = isAutopilotEnabled ? handoffs.find(h => h.send) : undefined;
+
 		for (const handoff of handoffs) {
 			const promptButton = this.createPromptButton(handoff);
 			this.promptsContainer.appendChild(promptButton);
+
+			if (handoff === firstAutoSendHandoff) {
+				const autopilotButton = this.createAutopilotButton(handoff);
+				this.promptsContainer.appendChild(autopilotButton);
+			}
 		}
 
 		this.domNode.style.display = 'flex';
@@ -126,11 +141,15 @@ export class ChatSuggestNextWidget extends Disposable {
 		// Get chat session contributions to show in chevron dropdown
 		// Filter to only first-party providers that support "continue in".
 		// TODO: Expand later to any agent with `canDelegate` === true.
+		const currentSessionType = this.contextKeyService.getContextKeyValue<string>(ChatContextKeys.chatSessionType.key);
 		const contributions = this.chatSessionsService.getAllChatSessionContributions();
 		const availableContributions = contributions.filter(c => {
 			if (!c.canDelegate) {
 				return false;
 			}
+			if (c.type === currentSessionType) {
+				return false;
+			}
 			const provider = getAgentSessionProvider(c.type);
 			return provider !== undefined && getAgentCanContinueIn(provider);
 		});
@@ -221,6 +240,46 @@ export class ChatSuggestNextWidget extends Disposable {
 		return button;
 	}
 
+	private createAutopilotButton(handoff: IHandOff): HTMLElement {
+		const disposables = new DisposableStore();
+
+		const handoffLabel = handoff.label;
+		const getCurrentHandoff = (): IHandOff | undefined => {
+			const currentHandoffs = this._currentMode?.handOffs?.get();
+			return currentHandoffs?.find(h => h.label === handoffLabel) ?? handoff;
+		};
+
+		const label = localize('chat.suggestNext.startWithAutopilot', "Start with Autopilot");
+		const button = dom.$('.chat-welcome-view-suggested-prompt');
+		button.setAttribute('tabindex', '0');
+		button.setAttribute('role', 'button');
+		button.setAttribute('aria-label', label);
+
+		const titleElement = dom.append(button, dom.$('.chat-welcome-view-suggested-prompt-title'));
+		titleElement.textContent = label;
+
+		disposables.add(dom.addDisposableListener(button, 'click', () => {
+			const currentHandoff = getCurrentHandoff();
+			if (currentHandoff) {
+				this._onDidSelectPrompt.fire({ handoff: currentHandoff, withAutopilot: true });
+			}
+		}));
+
+		disposables.add(dom.addDisposableListener(button, 'keydown', e => {
+			if (e.key === 'Enter' || e.key === ' ') {
+				e.preventDefault();
+				const currentHandoff = getCurrentHandoff();
+				if (currentHandoff) {
+					this._onDidSelectPrompt.fire({ handoff: currentHandoff, withAutopilot: true });
+				}
+			}
+		}));
+
+		this.buttonDisposables.set(button, disposables);
+
+		return button;
+	}
+
 	public hide(): void {
 		if (this.domNode.style.display !== 'none') {
 			this._currentMode = undefined;
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatThinkingContentPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatThinkingContentPart.ts
index f5865ba459266..444016672bc21 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatThinkingContentPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatThinkingContentPart.ts
@@ -14,6 +14,7 @@ import { ChatConfiguration, ThinkingDisplayMode } from '../../../common/constant
 import { ChatTreeItem } from '../../chat.js';
 import { IInstantiationService } from '../../../../../../platform/instantiation/common/instantiation.js';
 import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
+import { AccessibilityWorkbenchSettingId } from '../../../../accessibility/browser/accessibilityConfiguration.js';
 import { MarkdownString } from '../../../../../../base/common/htmlContent.js';
 import { IRenderedMarkdown } from '../../../../../../base/browser/markdownRenderer.js';
 import { IMarkdownRenderer } from '../../../../../../platform/markdown/browser/markdownRenderer.js';
@@ -26,12 +27,11 @@ import { Codicon } from '../../../../../../base/common/codicons.js';
 import { ThemeIcon } from '../../../../../../base/common/themables.js';
 import { Lazy } from '../../../../../../base/common/lazy.js';
 import { Emitter } from '../../../../../../base/common/event.js';
-import { DisposableMap, DisposableStore, IDisposable } from '../../../../../../base/common/lifecycle.js';
+import { DisposableMap, DisposableStore, IDisposable, MutableDisposable } from '../../../../../../base/common/lifecycle.js';
 import { autorun } from '../../../../../../base/common/observable.js';
 import { CancellationTokenSource } from '../../../../../../base/common/cancellation.js';
 import { IChatMarkdownAnchorService } from './chatMarkdownAnchorService.js';
 import { ChatMessageRole, ILanguageModelsService } from '../../../common/languageModels.js';
-import { ExtensionIdentifier } from '../../../../../../platform/extensions/common/extensions.js';
 import './media/chatThinkingContent.css';
 import { IHoverService } from '../../../../../../platform/hover/browser/hover.js';
 
@@ -66,7 +66,8 @@ export function getToolInvocationIcon(toolId: string): ThemeIcon {
 
 	if (
 		lowerToolId.includes('edit') ||
-		lowerToolId.includes('create')
+		lowerToolId.includes('create') ||
+		lowerToolId.includes('replace')
 	) {
 		return Codicon.pencil;
 	}
@@ -139,10 +140,18 @@ const toolMessages = [
 ];
 
 export class ChatThinkingContentPart extends ChatCollapsibleContentPart implements IChatContentPart {
+
+	private static _codeBlockRendererSync(_languageId: string, text: string, _raw?: string): HTMLElement {
+		const codeElement = $('code');
+		codeElement.textContent = text;
+		return codeElement;
+	}
+
 	public readonly codeblocks: undefined;
 	public readonly codeblocksPartId: undefined;
 
 	private readonly _onDidChangeHeight = this._register(new Emitter<void>());
+	private readonly _asyncRenderCallback = () => this._onDidChangeHeight.fire();
 
 	private id: string | undefined;
 	private content: IChatThinkingPart;
@@ -150,7 +159,7 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 	private currentTitle: string;
 	private defaultTitle = localize('chat.thinking.header', 'Working');
 	private textContainer!: HTMLElement;
-	private markdownResult: IRenderedMarkdown | undefined;
+	private readonly _markdownResult = this._register(new MutableDisposable<IRenderedMarkdown>());
 	private wrapper!: HTMLElement;
 	private fixedScrollingMode: boolean = false;
 	private autoScrollEnabled: boolean = true;
@@ -163,7 +172,7 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 	private toolInvocations: (IChatToolInvocation | IChatToolInvocationSerialized)[] = [];
 	private allThinkingParts: IChatThinkingPart[] = [];
 	private hookCount: number = 0;
-	private singleItemInfo: { element: HTMLElement; originalParent: HTMLElement; originalNextSibling: Node | null } | undefined;
+	private singleItemInfo: { element: HTMLElement; originalParent: HTMLElement; originalNextSibling: Node | null; toolInvocation?: IChatToolInvocation | IChatToolInvocationSerialized } | undefined;
 	private lazyItems: ILazyItem[] = [];
 	private hasExpandedOnce: boolean = false;
 	private workingSpinnerElement: HTMLElement | undefined;
@@ -178,7 +187,7 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 	private isUpdatingDimensions: boolean = false;
 	private titleShimmerSpan: HTMLElement | undefined;
 	private titleDetailContainer: HTMLElement | undefined;
-	private titleDetailRendered: IRenderedMarkdown | undefined;
+	private readonly _titleDetailRendered = this._register(new MutableDisposable<IRenderedMarkdown>());
 
 	private getRandomWorkingMessage(category: WorkingMessageCategory = WorkingMessageCategory.Tool): string {
 		let pool = this.availableMessagesByCategory.get(category);
@@ -260,7 +269,9 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 		}
 
 		// Alert screen reader users that thinking has started
-		alert(localize('chat.thinking.started', 'Thinking'));
+		if (this.configurationService.getValue(AccessibilityWorkbenchSettingId.VerboseChatProgressUpdates)) {
+			alert(localize('chat.thinking.started', 'Thinking'));
+		}
 
 		if (configuredMode === ThinkingDisplayMode.Collapsed) {
 			this.setExpanded(false);
@@ -317,6 +328,8 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 			// Materialize lazy items when first expanded
 			if (isExpanded && !this.hasExpandedOnce && this.lazyItems.length > 0) {
 				this.hasExpandedOnce = true;
+				// Flush pending removals so that completed hidden tools are removed from lazyItems before materialization
+				this.processPendingRemovals();
 				for (const item of this.lazyItems) {
 					this.materializeLazyItem(item);
 				}
@@ -447,20 +460,11 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 		}
 	}
 
-	// try to schedule scroll
+	// Schedule a batched scroll dimension update for the next animation frame.
+	// All calls during a single frame (from updateThinking, MutationObserver, etc.)
+	// are coalesced into one layout read, avoiding forced synchronous layouts
+	// during tree splice operations.
 	private syncDimensionsAndScheduleScroll(): void {
-		if (this.autoScrollEnabled && this.scrollableElement) {
-			this.isUpdatingDimensions = true;
-			try {
-				this.updateScrollDimensions();
-				this.scrollToBottom();
-			} finally {
-				this.isUpdatingDimensions = false;
-			}
-			return;
-		}
-
-		// debounce animation
 		if (this.pendingScrollDisposable) {
 			return;
 		}
@@ -471,21 +475,24 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 			}
 			this.isUpdatingDimensions = true;
 			try {
-				this.updateScrollDimensions();
+				const contentHeight = this.updateScrollDimensions();
+				if (this.autoScrollEnabled && contentHeight !== undefined) {
+					this.scrollToBottom(contentHeight);
+				}
 			} finally {
 				this.isUpdatingDimensions = false;
 			}
 		});
 	}
 
-	private updateScrollDimensions(): void {
+	private updateScrollDimensions(): number | undefined {
 		if (!this.scrollableElement) {
-			return;
+			return undefined;
 		}
 
 		const isCollapsed = this.domNode.classList.contains('chat-used-context-collapsed');
 		if (!isCollapsed) {
-			return;
+			return undefined;
 		}
 
 		const contentHeight = this.wrapper.scrollHeight;
@@ -497,14 +504,19 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 			height: viewportHeight,
 			scrollHeight: contentHeight
 		});
+
+		// Re-evaluate hover feedback as content grows past the max height,
+		// reusing the already-measured contentHeight to avoid an extra layout read.
+		this.updateDropdownClickability(contentHeight);
+
+		return contentHeight;
 	}
 
-	private scrollToBottom(): void {
+	private scrollToBottom(contentHeight: number): void {
 		if (!this.scrollableElement) {
 			return;
 		}
 
-		const contentHeight = this.wrapper.scrollHeight;
 		const viewportHeight = Math.min(contentHeight, THINKING_SCROLL_MAX_HEIGHT);
 
 		if (contentHeight > viewportHeight) {
@@ -542,10 +554,7 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 		}
 		const cleanedContent = content.trim();
 		if (!cleanedContent) {
-			if (this.markdownResult) {
-				this.markdownResult.dispose();
-				this.markdownResult = undefined;
-			}
+			this._markdownResult.clear();
 			if (this.textContainer) {
 				clearNode(this.textContainer);
 			}
@@ -558,22 +567,14 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 			contentToRender = cleanedContent.slice(2, -2);
 		}
 
-		const target = reuseExisting ? this.markdownResult?.element : undefined;
-		if (this.markdownResult) {
-			this.markdownResult.dispose();
-			this.markdownResult = undefined;
-		}
+		const target = reuseExisting ? this._markdownResult.value?.element : undefined;
 
-		const rendered = this._register(this.chatContentMarkdownRenderer.render(new MarkdownString(contentToRender), {
+		const rendered = this.chatContentMarkdownRenderer.render(new MarkdownString(contentToRender), {
 			fillInIncompleteTokens: true,
-			asyncRenderCallback: () => this._onDidChangeHeight.fire(),
-			codeBlockRendererSync: (_languageId, text, raw) => {
-				const codeElement = $('code');
-				codeElement.textContent = text;
-				return codeElement;
-			}
-		}, target));
-		this.markdownResult = rendered;
+			asyncRenderCallback: this._asyncRenderCallback,
+			codeBlockRendererSync: ChatThinkingContentPart._codeBlockRendererSync,
+		}, target);
+		this._markdownResult.value = rendered;
 		if (!target) {
 			if (this.textContainer) {
 				clearNode(this.textContainer);
@@ -583,13 +584,41 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 		}
 	}
 
+	private setFinalizedTitle(title: string): void {
+		if (!this._collapseButton) {
+			return;
+		}
+
+		const labelElement = this._collapseButton.labelElement;
+		labelElement.textContent = '';
+
+		const firstSpaceIndex = title.indexOf(' ');
+		if (firstSpaceIndex === -1) {
+			// Single word title, no need to split
+			labelElement.textContent = title;
+		} else {
+			const verb = title.substring(0, firstSpaceIndex);
+			const rest = title.substring(firstSpaceIndex);
+
+			const verbSpan = $('span');
+			verbSpan.textContent = verb;
+			labelElement.appendChild(verbSpan);
+
+			const restSpan = $('span.chat-thinking-title-detail-text');
+			restSpan.textContent = rest;
+			labelElement.appendChild(restSpan);
+		}
+
+		this._collapseButton.element.ariaLabel = title;
+	}
+
 	private setDropdownClickable(clickable: boolean): void {
 		if (this._collapseButton) {
 			this._collapseButton.element.style.pointerEvents = clickable ? 'auto' : 'none';
 		}
 
 		if (!clickable && this.streamingCompleted) {
-			super.setTitle(this.lastExtractedTitle ?? this.currentTitle);
+			this.setFinalizedTitle(this.lastExtractedTitle ?? this.currentTitle);
 		}
 	}
 
@@ -620,8 +649,17 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 		return !(!strippedContent || strippedContent === titleToCompare);
 	}
 
-	private updateDropdownClickability(): void {
-		const allowExpansion = this.shouldAllowExpansion();
+	private updateDropdownClickability(knownContentHeight?: number): void {
+		let allowExpansion = this.shouldAllowExpansion();
+
+		// don't allow feedback on fixed scrolling before reaching max height.
+		if (allowExpansion && this.fixedScrollingMode && !this.streamingCompleted && !this.element.isComplete && this.wrapper) {
+			const contentHeight = knownContentHeight ?? this.wrapper.scrollHeight;
+			if (contentHeight <= THINKING_SCROLL_MAX_HEIGHT) {
+				allowExpansion = false;
+			}
+		}
+
 		if (!allowExpansion && this.isExpanded()) {
 			this.setExpanded(false);
 		}
@@ -669,7 +707,7 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 			return;
 		}
 		const previousValue = this.currentThinkingValue;
-		const reuseExisting = !!(this.markdownResult && next.startsWith(previousValue) && next.length > previousValue.length);
+		const reuseExisting = !!(this._markdownResult.value && next.startsWith(previousValue) && next.length > previousValue.length);
 		this.currentThinkingValue = next;
 		this.renderMarkdown(next, reuseExisting);
 
@@ -710,6 +748,11 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 			this.workingSpinnerElement = undefined;
 			this.workingSpinnerLabel = undefined;
 		}
+
+		// Clear the attached-to-thinking flag on all tool invocations
+		for (const toolInvocation of this.toolInvocations) {
+			toolInvocation.isAttachedToThinking = false;
+		}
 	}
 
 	public finalizeTitleIfDefault(): void {
@@ -745,7 +788,7 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 
 		if (this.content.generatedTitle) {
 			this.currentTitle = this.content.generatedTitle;
-			super.setTitle(this.content.generatedTitle);
+			this.setFinalizedTitle(this.content.generatedTitle);
 			return;
 		}
 
@@ -755,28 +798,32 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 			this.currentTitle = existingTitle;
 			this.content.generatedTitle = existingTitle;
 			this.setGeneratedTitleOnAllParts(existingTitle);
-			super.setTitle(existingTitle);
+			this.setFinalizedTitle(existingTitle);
 			return;
 		}
 
 		// case where we only have one item (tool or edit) in the thinking container and no thinking parts, we want to move it back to its original position
-		if (this.appendedItemCount === 1 && this.currentThinkingValue.trim() === '') {
+		if (this.toolInvocationCount === 1 && this.hookCount === 0 && this.currentThinkingValue.trim() === '') {
 			// If singleItemInfo wasn't set (item was lazy/deferred), materialize it now
 			if (!this.singleItemInfo) {
 				const lazyItem = this.lazyItems.find(item => item.kind === 'tool' && item.originalParent);
 				if (lazyItem && lazyItem.kind === 'tool') {
+					const toolInvocation = lazyItem.toolInvocationOrMarkdown && (lazyItem.toolInvocationOrMarkdown.kind === 'toolInvocation' || lazyItem.toolInvocationOrMarkdown.kind === 'toolInvocationSerialized') ? lazyItem.toolInvocationOrMarkdown : undefined;
 					const result = lazyItem.lazy.value;
 					this.singleItemInfo = {
 						element: result.domNode,
 						originalParent: lazyItem.originalParent!,
-						originalNextSibling: this.domNode
+						originalNextSibling: this.domNode,
+						toolInvocation
 					};
 					if (result.disposable) {
 						this._register(result.disposable);
 					}
 				}
 			}
-			if (this.singleItemInfo && this.restoreSingleItemToOriginalPosition()) {
+			// Only restore if the tool is complete so the progress spinner is resolved
+			const toolIsComplete = !this.singleItemInfo?.toolInvocation || IChatToolInvocation.isComplete(this.singleItemInfo.toolInvocation);
+			if (toolIsComplete && this.singleItemInfo && this.restoreSingleItemToOriginalPosition()) {
 				return;
 			}
 		}
@@ -787,7 +834,7 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 			this.currentTitle = title;
 			this.content.generatedTitle = title;
 			this.setGeneratedTitleOnAllParts(title);
-			super.setTitle(title);
+			this.setFinalizedTitle(title);
 			return;
 		}
 
@@ -837,6 +884,7 @@ export class ChatThinkingContentPart extends ChatCollapsibleContentPart implemen
 			OUTPUT FORMAT:
 			- MUST be a single sentence
 			- MUST be under 10 words
+			- The FIRST word MUST be a past tense verb (e.g. "Updated", "Reviewed", "Created", "Searched", "Analyzed")
 			- No quotes, no trailing punctuation
 
 			GENERAL:
@@ -925,7 +973,7 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 
 			const response = await this.languageModelsService.sendChatRequest(
 				models[0],
-				new ExtensionIdentifier('core'),
+				undefined,
 				[{ role: ChatMessageRole.User, content: [{ type: 'text', value: prompt }] }],
 				{},
 				cts.token
@@ -962,9 +1010,7 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 
 			if (generatedTitle && !this._store.isDisposed) {
 				this.currentTitle = generatedTitle;
-				if (this._collapseButton) {
-					this._collapseButton.label = generatedTitle;
-				}
+				this.setFinalizedTitle(generatedTitle);
 				this.content.generatedTitle = generatedTitle;
 				this.setGeneratedTitleOnAllParts(generatedTitle);
 				return;
@@ -984,7 +1030,7 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 			return false;
 		}
 
-		const { element, originalParent, originalNextSibling } = this.singleItemInfo;
+		const { element, originalParent, originalNextSibling, toolInvocation } = this.singleItemInfo;
 
 		// don't restore it to original position - it contains multiple rendered elements
 		if (element.childElementCount > 1) {
@@ -998,6 +1044,10 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 			originalParent.appendChild(element);
 		}
 
+		if (toolInvocation) {
+			toolInvocation.isAttachedToThinking = false;
+		}
+
 		hide(this.domNode);
 		this.singleItemInfo = undefined;
 		return true;
@@ -1018,7 +1068,7 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 
 		if (this._collapseButton) {
 			this._collapseButton.icon = Codicon.check;
-			this._collapseButton.label = finalLabel;
+			this.setFinalizedTitle(finalLabel);
 		}
 
 		this.updateDropdownClickability();
@@ -1095,6 +1145,11 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 			this.toolInvocationCount--;
 		}
 
+		// Clear the attached-to-thinking flag on the removed tool invocation
+		if (removedItem.kind === 'tool' && removedItem.toolInvocationOrMarkdown && (removedItem.toolInvocationOrMarkdown.kind === 'toolInvocation' || removedItem.toolInvocationOrMarkdown.kind === 'toolInvocationSerialized')) {
+			removedItem.toolInvocationOrMarkdown.isAttachedToThinking = false;
+		}
+
 		const toolInvocationsIndex = this.toolInvocations.findIndex(t =>
 			(t.kind === 'toolInvocation' || t.kind === 'toolInvocationSerialized') && t.toolId === toolInvocationId
 		);
@@ -1155,6 +1210,10 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 			item.toolInvocationOrMarkdown.toolCallId === toolCallId
 		);
 		if (lazyIndex !== -1) {
+			const removedLazyItem = this.lazyItems[lazyIndex];
+			if (removedLazyItem.kind === 'tool' && removedLazyItem.toolInvocationOrMarkdown && (removedLazyItem.toolInvocationOrMarkdown.kind === 'toolInvocation' || removedLazyItem.toolInvocationOrMarkdown.kind === 'toolInvocationSerialized')) {
+				removedLazyItem.toolInvocationOrMarkdown.isAttachedToThinking = false;
+			}
 			this.lazyItems.splice(lazyIndex, 1);
 		}
 
@@ -1171,7 +1230,6 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 		if (titleIndex !== -1) {
 			this.extractedTitles.splice(titleIndex, 1);
 		}
-
 		this.updateDropdownClickability();
 		this._onDidChangeHeight.fire();
 	}
@@ -1255,6 +1313,11 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 
 					if (currentState.type === IChatToolInvocation.StateKind.Completed ||
 						currentState.type === IChatToolInvocation.StateKind.Cancelled) {
+						// Remove tools that should be hidden now or after completion.
+						if (toolInvocationOrMarkdown.presentation === 'hidden' || toolInvocationOrMarkdown.presentation === 'hiddenAfterComplete') {
+							this.pendingRemovals.push({ toolCallId: toolInvocationOrMarkdown.toolCallId, toolLabel: currentToolLabel });
+							this.schedulePendingRemovalsFlush();
+						}
 						isComplete = true;
 						return;
 					}
@@ -1330,11 +1393,13 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 		}
 
 		// Save the first item info for potential restoration later
-		if (this.appendedItemCount === 1 && originalParent) {
+		if (this.toolInvocationCount === 1 && this.hookCount === 0 && originalParent) {
+			const toolInvocation = toolInvocationOrMarkdown && (toolInvocationOrMarkdown.kind === 'toolInvocation' || toolInvocationOrMarkdown.kind === 'toolInvocationSerialized') ? toolInvocationOrMarkdown : undefined;
 			this.singleItemInfo = {
 				element: content,
 				originalParent,
-				originalNextSibling: this.domNode
+				originalNextSibling: this.domNode,
+				toolInvocation
 			};
 		} else {
 			this.singleItemInfo = undefined;
@@ -1464,10 +1529,7 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 			}
 			this.titleShimmerSpan = undefined;
 			this.titleDetailContainer = undefined;
-			if (this.titleDetailRendered) {
-				this.titleDetailRendered.dispose();
-				this.titleDetailRendered = undefined;
-			}
+			this._titleDetailRendered.clear();
 			this.currentTitle = title;
 			return;
 		}
@@ -1491,15 +1553,12 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 		this.titleShimmerSpan.textContent = 'Working: ';
 
 		// Dispose previous detail rendering
-		if (this.titleDetailRendered) {
-			this.titleDetailRendered.dispose();
-			this.titleDetailRendered = undefined;
-		}
+		this._titleDetailRendered.clear();
 
 		const result = this.chatContentMarkdownRenderer.render(new MarkdownString(title));
 		result.element.classList.add('collapsible-title-content', 'chat-thinking-title-detail');
 		renderFileWidgets(result.element, this.instantiationService, this.chatMarkdownAnchorService, this._store);
-		this.titleDetailRendered = result;
+		this._titleDetailRendered.value = result;
 
 		if (this.titleDetailContainer) {
 			// Replace old detail in-place
@@ -1527,14 +1586,6 @@ ${this.hookCount > 0 ? `EXAMPLES WITH BLOCKED CONTENT (from hooks):
 
 	override dispose(): void {
 		this.isActive = false;
-		if (this.markdownResult) {
-			this.markdownResult.dispose();
-			this.markdownResult = undefined;
-		}
-		if (this.titleDetailRendered) {
-			this.titleDetailRendered.dispose();
-			this.titleDetailRendered = undefined;
-		}
 		if (this.workingSpinnerElement) {
 			this.workingSpinnerElement.remove();
 			this.workingSpinnerElement = undefined;
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatTipContentPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatTipContentPart.ts
index f715e54ab038f..3e195b32ada8e 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatTipContentPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatTipContentPart.ts
@@ -6,7 +6,6 @@
 import './media/chatTipContent.css';
 import * as dom from '../../../../../../base/browser/dom.js';
 import { StandardMouseEvent } from '../../../../../../base/browser/mouseEvent.js';
-import { renderIcon } from '../../../../../../base/browser/ui/iconLabel/iconLabels.js';
 import { Codicon } from '../../../../../../base/common/codicons.js';
 import { Emitter } from '../../../../../../base/common/event.js';
 import { onUnexpectedError } from '../../../../../../base/common/errors.js';
@@ -39,6 +38,7 @@ export class ChatTipContentPart extends Disposable {
 	private readonly _toolbar = this._register(new MutableDisposable<MenuWorkbenchToolBar>());
 
 	private readonly _inChatTipContextKey: IContextKey<boolean>;
+	private readonly _multipleChatTipsContextKey: IContextKey<boolean>;
 
 	constructor(
 		tip: IChatTip,
@@ -60,21 +60,21 @@ export class ChatTipContentPart extends Disposable {
 		this.domNode.setAttribute('aria-roledescription', localize('chatTipRoleDescription', "tip"));
 
 		this._inChatTipContextKey = ChatContextKeys.inChatTip.bindTo(this._contextKeyService);
+		this._multipleChatTipsContextKey = ChatContextKeys.multipleChatTips.bindTo(this._contextKeyService);
 		const focusTracker = this._register(dom.trackFocus(this.domNode));
 		this._register(focusTracker.onDidFocus(() => this._inChatTipContextKey.set(true)));
 		this._register(focusTracker.onDidBlur(() => this._inChatTipContextKey.set(false)));
-		this._register({ dispose: () => this._inChatTipContextKey.reset() });
+		this._register({
+			dispose: () => {
+				this._inChatTipContextKey.reset();
+				this._multipleChatTipsContextKey.reset();
+			}
+		});
 
 		this._renderTip(tip);
 
 		this._register(this._chatTipService.onDidDismissTip(() => {
-			const nextTip = this._chatTipService.navigateToNextTip();
-			if (nextTip) {
-				this._renderTip(nextTip);
-				dom.runAtThisOrScheduleAtNextAnimationFrame(dom.getWindow(this.domNode), () => this.focus());
-			} else {
-				this._onDidHide.fire();
-			}
+			this._onDidHide.fire();
 		}));
 
 		this._register(this._chatTipService.onDidNavigateTip(tip => {
@@ -114,8 +114,8 @@ export class ChatTipContentPart extends Disposable {
 	private _renderTip(tip: IChatTip): void {
 		dom.clearNode(this.domNode);
 		this._toolbar.clear();
+		this._multipleChatTipsContextKey.set(this._chatTipService.hasMultipleTips());
 
-		this.domNode.appendChild(renderIcon(Codicon.lightbulb));
 		const markdownContent = this._renderer.render(tip.content, {
 			actionHandler: (link, md) => { this._handleTipAction(link, md).catch(onUnexpectedError); }
 		});
@@ -168,6 +168,7 @@ registerAction2(class PreviousTipAction extends Action2 {
 			id: 'workbench.action.chat.previousTip',
 			title: localize2('chatTip.previous', "Previous tip"),
 			icon: Codicon.chevronLeft,
+			precondition: ChatContextKeys.multipleChatTips,
 			f1: false,
 			menu: [{
 				id: MenuId.ChatTipToolbar,
@@ -189,6 +190,7 @@ registerAction2(class NextTipAction extends Action2 {
 			id: 'workbench.action.chat.nextTip',
 			title: localize2('chatTip.next', "Next tip"),
 			icon: Codicon.chevronRight,
+			precondition: ChatContextKeys.multipleChatTips,
 			f1: false,
 			menu: [{
 				id: MenuId.ChatTipToolbar,
@@ -220,7 +222,7 @@ registerAction2(class DismissTipToolbarAction extends Action2 {
 	}
 
 	override async run(accessor: ServicesAccessor): Promise<void> {
-		accessor.get(IChatTipService).dismissTip();
+		accessor.get(IChatTipService).dismissTipForSession();
 	}
 });
 
@@ -243,7 +245,7 @@ registerAction2(class DismissTipAction extends Action2 {
 	}
 
 	override async run(accessor: ServicesAccessor): Promise<void> {
-		accessor.get(IChatTipService).dismissTip();
+		accessor.get(IChatTipService).dismissTipForSession();
 	}
 });
 
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatToolOutputContentSubPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatToolOutputContentSubPart.ts
index 89cd89aea18c2..46171ef0343fb 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatToolOutputContentSubPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/chatToolOutputContentSubPart.ts
@@ -4,39 +4,19 @@
  *--------------------------------------------------------------------------------------------*/
 
 import * as dom from '../../../../../../base/browser/dom.js';
-import { disposableTimeout } from '../../../../../../base/common/async.js';
-import { decodeBase64 } from '../../../../../../base/common/buffer.js';
-import { Codicon } from '../../../../../../base/common/codicons.js';
 import { Disposable } from '../../../../../../base/common/lifecycle.js';
-import { basename, joinPath } from '../../../../../../base/common/resources.js';
-import { URI } from '../../../../../../base/common/uri.js';
-import { generateUuid } from '../../../../../../base/common/uuid.js';
 import { ILanguageService } from '../../../../../../editor/common/languages/language.js';
 import { IModelService } from '../../../../../../editor/common/services/model.js';
-import { localize, localize2 } from '../../../../../../nls.js';
-import { MenuWorkbenchToolBar } from '../../../../../../platform/actions/browser/toolbar.js';
-import { Action2, MenuId, registerAction2 } from '../../../../../../platform/actions/common/actions.js';
-import { ICommandService } from '../../../../../../platform/commands/common/commands.js';
+import { IInstantiationService } from '../../../../../../platform/instantiation/common/instantiation.js';
 import { IContextKeyService } from '../../../../../../platform/contextkey/common/contextkey.js';
-import { IContextMenuService } from '../../../../../../platform/contextview/browser/contextView.js';
-import { IFileDialogService } from '../../../../../../platform/dialogs/common/dialogs.js';
-import { IFileService } from '../../../../../../platform/files/common/files.js';
-import { IInstantiationService, ServicesAccessor } from '../../../../../../platform/instantiation/common/instantiation.js';
-import { ILabelService } from '../../../../../../platform/label/common/label.js';
-import { INotificationService } from '../../../../../../platform/notification/common/notification.js';
-import { IProgressService, ProgressLocation } from '../../../../../../platform/progress/common/progress.js';
-import { IWorkspaceContextService } from '../../../../../../platform/workspace/common/workspace.js';
-import { REVEAL_IN_EXPLORER_COMMAND_ID } from '../../../../files/browser/fileConstants.js';
-import { getAttachableImageExtension } from '../../../common/model/chatModel.js';
 import { IMarkdownString, MarkdownString } from '../../../../../../base/common/htmlContent.js';
 import { IMarkdownRendererService } from '../../../../../../platform/markdown/browser/markdownRenderer.js';
-import { IChatRequestVariableEntry } from '../../../common/attachments/chatVariableEntries.js';
 import { IChatCodeBlockInfo } from '../../chat.js';
 import { CodeBlockPart, ICodeBlockData } from './codeBlockPart.js';
-import { ChatAttachmentsContentPart } from './chatAttachmentsContentPart.js';
 import { IDisposableReference } from './chatCollections.js';
 import { IChatContentPartRenderContext } from './chatContentParts.js';
 import { ChatCollapsibleIOPart, IChatCollapsibleIOCodePart, IChatCollapsibleIODataPart } from './chatToolInputOutputContentPart.js';
+import { ChatResourceGroupWidget } from './chatResourceGroupWidget.js';
 
 /**
  * A reusable component for rendering tool output consisting of code blocks and/or resources.
@@ -52,8 +32,6 @@ export class ChatToolOutputContentSubPart extends Disposable {
 		private readonly parts: ChatCollapsibleIOPart[],
 		@IInstantiationService private readonly _instantiationService: IInstantiationService,
 		@IContextKeyService private readonly contextKeyService: IContextKeyService,
-		@IContextMenuService private readonly _contextMenuService: IContextMenuService,
-		@IFileService private readonly _fileService: IFileService,
 		@IMarkdownRendererService private readonly _markdownRendererService: IMarkdownRendererService,
 		@IModelService private readonly modelService: IModelService,
 		@ILanguageService private readonly languageService: ILanguageService,
@@ -101,106 +79,8 @@ export class ChatToolOutputContentSubPart extends Disposable {
 	}
 
 	private addResourceGroup(parts: IChatCollapsibleIODataPart[], container: HTMLElement) {
-		const el = dom.h('.chat-collapsible-io-resource-group', [
-			dom.h('.chat-collapsible-io-resource-items@items'),
-			dom.h('.chat-collapsible-io-resource-actions@actions'),
-		]);
-
-		this.fillInResourceGroup(parts, el.items, el.actions);
-
-		container.appendChild(el.root);
-		return el.root;
-	}
-
-	/**
-	 * Delay in milliseconds before decoding base64 image data.
-	 * This avoids expensive decode operations during scrolling.
-	 */
-	private static readonly IMAGE_DECODE_DELAY_MS = 100;
-
-	private async fillInResourceGroup(parts: IChatCollapsibleIODataPart[], itemsContainer: HTMLElement, actionsContainer: HTMLElement) {
-		// First pass: create entries immediately, using file placeholders for base64 images
-		const entries: IChatRequestVariableEntry[] = [];
-		const deferredImageParts: { index: number; part: IChatCollapsibleIODataPart }[] = [];
-
-		for (let i = 0; i < parts.length; i++) {
-			const part = parts[i];
-			if (part.mimeType && getAttachableImageExtension(part.mimeType)) {
-				if (part.base64Value) {
-					// Defer base64 decode - use file placeholder for now
-					entries.push({ kind: 'file', id: generateUuid(), name: basename(part.uri), fullName: part.uri.path, value: part.uri });
-					deferredImageParts.push({ index: i, part });
-				} else if (part.value) {
-					entries.push({ kind: 'image', id: generateUuid(), name: basename(part.uri), value: part.value, mimeType: part.mimeType, isURL: false, references: [{ kind: 'reference', reference: part.uri }] });
-				} else {
-					const value = await this._fileService.readFile(part.uri).then(f => f.value.buffer, () => undefined);
-					if (!value) {
-						entries.push({ kind: 'file', id: generateUuid(), name: basename(part.uri), fullName: part.uri.path, value: part.uri });
-					} else {
-						entries.push({ kind: 'image', id: generateUuid(), name: basename(part.uri), value, mimeType: part.mimeType, isURL: false, references: [{ kind: 'reference', reference: part.uri }] });
-					}
-				}
-			} else {
-				entries.push({ kind: 'file', id: generateUuid(), name: basename(part.uri), fullName: part.uri.path, value: part.uri });
-			}
-		}
-
-		if (this._store.isDisposed) {
-			return;
-		}
-
-		// Render attachments immediately with placeholders
-		const attachments = this._register(this._instantiationService.createInstance(
-			ChatAttachmentsContentPart,
-			{
-				variables: entries,
-				limit: 5,
-				contentReferences: undefined,
-				domNode: undefined
-			}
-		));
-
-		attachments.contextMenuHandler = (attachment, event) => {
-			const index = entries.indexOf(attachment);
-			const part = parts[index];
-			if (part) {
-				event.preventDefault();
-				event.stopPropagation();
-
-				this._contextMenuService.showContextMenu({
-					menuId: MenuId.ChatToolOutputResourceContext,
-					menuActionOptions: { shouldForwardArgs: true },
-					getAnchor: () => ({ x: event.pageX, y: event.pageY }),
-					getActionsContext: () => ({ parts: [part] } satisfies IChatToolOutputResourceToolbarContext),
-				});
-			}
-		};
-
-		itemsContainer.appendChild(attachments.domNode!);
-
-		const toolbar = this._register(this._instantiationService.createInstance(MenuWorkbenchToolBar, actionsContainer, MenuId.ChatToolOutputResourceToolbar, {
-			menuOptions: {
-				shouldForwardArgs: true,
-			},
-		}));
-		toolbar.context = { parts } satisfies IChatToolOutputResourceToolbarContext;
-
-		// Second pass: decode base64 images asynchronously and update in place
-		if (deferredImageParts.length > 0) {
-			this._register(disposableTimeout(() => {
-				for (const { index, part } of deferredImageParts) {
-					try {
-						const value = decodeBase64(part.base64Value!).buffer;
-						entries[index] = { kind: 'image', id: generateUuid(), name: basename(part.uri), value, mimeType: part.mimeType!, isURL: false, references: [{ kind: 'reference', reference: part.uri }] };
-					} catch {
-						// Keep the file placeholder on decode failure
-					}
-				}
-
-				// Update attachments in place
-				attachments.updateVariables(entries);
-			}, ChatToolOutputContentSubPart.IMAGE_DECODE_DELAY_MS));
-		}
+		const widget = this._register(this._instantiationService.createInstance(ChatResourceGroupWidget, parts));
+		container.appendChild(widget.domNode);
 	}
 
 	private addCodeBlock(parts: IChatCollapsibleIOCodePart[], container: HTMLElement): void {
@@ -253,97 +133,3 @@ export class ChatToolOutputContentSubPart extends Disposable {
 		this._editorReferences.forEach(r => r.object.layout(width));
 	}
 }
-
-interface IChatToolOutputResourceToolbarContext {
-	parts: IChatCollapsibleIODataPart[];
-}
-
-
-
-class SaveResourcesAction extends Action2 {
-	public static readonly ID = 'chat.toolOutput.save';
-	constructor() {
-		super({
-			id: SaveResourcesAction.ID,
-			title: localize2('chat.saveResources', "Save As..."),
-			icon: Codicon.cloudDownload,
-			menu: [{
-				id: MenuId.ChatToolOutputResourceToolbar,
-				group: 'navigation',
-				order: 1
-			}, {
-				id: MenuId.ChatToolOutputResourceContext,
-			}]
-		});
-	}
-
-	async run(accessor: ServicesAccessor, context: IChatToolOutputResourceToolbarContext) {
-		const fileDialog = accessor.get(IFileDialogService);
-		const fileService = accessor.get(IFileService);
-		const notificationService = accessor.get(INotificationService);
-		const progressService = accessor.get(IProgressService);
-		const workspaceContextService = accessor.get(IWorkspaceContextService);
-		const commandService = accessor.get(ICommandService);
-		const labelService = accessor.get(ILabelService);
-		const defaultFilepath = await fileDialog.defaultFilePath();
-
-		const savePart = async (part: IChatCollapsibleIODataPart, isFolder: boolean, uri: URI) => {
-			const target = isFolder ? joinPath(uri, basename(part.uri)) : uri;
-			try {
-				if (part.kind === 'data') {
-					await fileService.copy(part.uri, target, true);
-				} else {
-					// MCP doesn't support streaming data, so no sense trying
-					const contents = await fileService.readFile(part.uri);
-					await fileService.writeFile(target, contents.value);
-				}
-			} catch (e) {
-				notificationService.error(localize('chat.saveResources.error', "Failed to save {0}: {1}", basename(part.uri), e));
-			}
-		};
-
-		const withProgress = async (thenReveal: URI, todo: (() => Promise<void>)[]) => {
-			await progressService.withProgress({
-				location: ProgressLocation.Notification,
-				delay: 5_000,
-				title: localize('chat.saveResources.progress', "Saving resources..."),
-			}, async report => {
-				for (const task of todo) {
-					await task();
-					report.report({ increment: 1, total: todo.length });
-				}
-			});
-
-			if (workspaceContextService.isInsideWorkspace(thenReveal)) {
-				commandService.executeCommand(REVEAL_IN_EXPLORER_COMMAND_ID, thenReveal);
-			} else {
-				notificationService.info(localize('chat.saveResources.reveal', "Saved resources to {0}", labelService.getUriLabel(thenReveal)));
-			}
-		};
-
-		if (context.parts.length === 1) {
-			const part = context.parts[0];
-			const uri = await fileDialog.pickFileToSave(joinPath(defaultFilepath, basename(part.uri)));
-			if (!uri) {
-				return;
-			}
-			await withProgress(uri, [() => savePart(part, false, uri)]);
-		} else {
-			const uris = await fileDialog.showOpenDialog({
-				title: localize('chat.saveResources.title', "Pick folder to save resources"),
-				canSelectFiles: false,
-				canSelectFolders: true,
-				canSelectMany: false,
-				defaultUri: workspaceContextService.getWorkspace().folders[0]?.uri,
-			});
-
-			if (!uris?.length) {
-				return;
-			}
-
-			await withProgress(uris[0], context.parts.map(part => () => savePart(part, true, uris[0])));
-		}
-	}
-}
-
-registerAction2(SaveResourcesAction);
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatCodeBlockPill.css b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatCodeBlockPill.css
index c546f8192a2be..d459decaef8a6 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatCodeBlockPill.css
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatCodeBlockPill.css
@@ -4,14 +4,13 @@
  *--------------------------------------------------------------------------------------------*/
 
 .interactive-item-container.interactive-response .value .chat-markdown-part.rendered-markdown .code:has(.chat-codeblock-pill-container) {
-	margin-bottom: 8px;
+	margin-bottom: 16px;
 }
 
 .chat-markdown-part.rendered-markdown .code .chat-codeblock-pill-container {
 	display: flex;
 	align-items: center;
 	gap: 5px;
-	margin: 0 0 6px 0px;
 	font-size: var(--vscode-chat-font-size-body-s);
 	color: var(--vscode-descriptionForeground);
 
@@ -29,7 +28,7 @@
 			color: var(--vscode-icon-foreground) !important;
 
 			&::before {
-				font-size: var(--vscode-chat-font-size-body-s);
+				font-size: 12px;
 			}
 		}
 
@@ -39,6 +38,8 @@
 
 		.show-checkmarks & .codicon.codicon-check {
 			display: inline-flex;
+			padding-left: 2px;
+			margin-left: 0.2em;
 		}
 
 		.status-label {
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatConfirmationWidget.css b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatConfirmationWidget.css
index c96e09ae84995..43efe1b98e0bb 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatConfirmationWidget.css
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatConfirmationWidget.css
@@ -104,6 +104,7 @@
 
 .chat-confirmation-widget-title small {
 	font-size: 1em;
+	opacity: 0.7;
 
 	&::before {
 		content: ' \2013  ';
@@ -192,6 +193,23 @@
 	}
 }
 
+.mcp-app-downloads {
+	margin-top: 8px;
+
+	.chat-collapsible-io-resource-group {
+		animation: mcpDownloadFadeIn 300ms ease-in;
+	}
+}
+
+.mcp-app-downloads:empty {
+	display: none;
+}
+
+@keyframes mcpDownloadFadeIn {
+	from { opacity: 0; }
+	to { opacity: 1; }
+}
+
 .chat-confirmation-widget2 {
 	margin-bottom: 8px;
 	border: 1px solid var(--vscode-chat-requestBorder);
@@ -248,6 +266,138 @@
 	}
 }
 
+.chat-confirmation-widget2 .chat-modified-files-confirmation-list {
+	margin: 8px -9px 0;
+	border-top: 1px solid var(--vscode-chat-requestBorder);
+	border-left: none;
+	border-right: none;
+	border-bottom: none;
+	border-radius: 0;
+	padding: 3px 0 0;
+
+	.chat-editing-session-overview {
+		display: flex;
+		align-items: center;
+		justify-content: space-between;
+		gap: 6px;
+		min-height: 22px;
+		cursor: pointer;
+	}
+
+	.working-set-title {
+		flex: 1;
+		min-width: 0;
+		color: var(--vscode-descriptionForeground);
+		font-size: 12px;
+		white-space: nowrap;
+		overflow: hidden;
+		text-overflow: ellipsis;
+		align-content: center;
+
+		.monaco-button {
+			width: fit-content;
+			max-width: 100%;
+			padding: 4px 6px 4px 0;
+			border: none;
+			border-radius: 2px;
+			background-color: unset;
+			color: var(--vscode-descriptionForeground);
+		}
+
+		.monaco-button:focus {
+			outline: none !important;
+			box-shadow: none !important;
+		}
+
+		.monaco-button:hover {
+			background-color: transparent;
+		}
+
+		.monaco-button:focus-visible {
+			outline: none !important;
+			box-shadow: none !important;
+		}
+
+		.monaco-button-mdlabel {
+			display: flex;
+			align-items: center;
+			width: auto;
+			flex: 0 1 auto;
+			text-align: left;
+		}
+	}
+
+	.working-set-line-counts {
+		display: inline-flex;
+		gap: 4px;
+		margin-left: 6px;
+		font-size: 11px;
+		font-weight: 500;
+		flex-shrink: 0;
+	}
+
+	.working-set-lines-added {
+		color: var(--vscode-chat-linesAddedForeground);
+	}
+
+	.working-set-lines-removed {
+		color: var(--vscode-chat-linesRemovedForeground);
+	}
+
+	.chat-editing-session-actions {
+		display: flex;
+		align-items: center;
+		gap: 6px;
+		flex-shrink: 0;
+		padding-right: 8px;
+	}
+
+	.chat-editing-session-actions .monaco-button.secondary.monaco-text-button.codicon {
+		cursor: pointer;
+		padding: 2px;
+		border-radius: 4px;
+		display: inline-flex;
+	}
+
+	.chat-editing-session-list {
+		margin-top: 4px;
+	}
+
+	.chat-editing-session-list.collapsed {
+		display: none;
+	}
+
+	.chat-editing-session-list .monaco-scrollable-element {
+		border-radius: 0;
+	}
+
+	.chat-editing-session-list .monaco-list-row {
+		border-radius: 4px;
+	}
+
+	.chat-editing-session-list .monaco-list-row:hover {
+		background-color: var(--vscode-list-hoverBackground) !important;
+	}
+
+	.chat-editing-session-list .monaco-icon-label {
+		padding: 0 3px;
+	}
+
+	.chat-editing-session-list .working-set-line-counts {
+		margin: 0 6px;
+	}
+
+	.chat-collapsible-list-action-bar {
+		display: none;
+	}
+
+	.monaco-list-row:hover .chat-collapsible-list-action-bar:not(.has-no-actions),
+	.monaco-list-row.focused .chat-collapsible-list-action-bar:not(.has-no-actions),
+	.monaco-list-row.selected .chat-collapsible-list-action-bar:not(.has-no-actions) {
+		display: inherit;
+	}
+}
+
 .chat-confirmation-widget2 .chat-confirmation-message-terminal .chat-confirmation-message-terminal-editor {
 	border-bottom: 1px solid var(--vscode-chat-requestBorder);
 }
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatHookContentPart.css b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatHookContentPart.css
index 179a2b06dc892..b019d98a50a8c 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatHookContentPart.css
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatHookContentPart.css
@@ -22,12 +22,14 @@
 .chat-hook-reason {
 	font-size: var(--vscode-chat-font-size-body-s);
 	padding: 4px 10px;
+	white-space: pre-wrap;
 }
 
 .chat-hook-message {
 	font-size: var(--vscode-chat-font-size-body-s);
 	padding: 4px 10px;
 	color: var(--vscode-descriptionForeground);
+	white-space: pre-wrap;
 }
 
 /* When both reason and message are shown, add a subtle separator */
@@ -37,6 +39,9 @@
 	padding-top: 6px;
 }
 
-.chat-used-context.chat-hook-outcome-warning .chat-used-context-label .monaco-button {
-	gap: 4px;
+.chat-used-context.chat-hook-outcome-warning,
+.chat-used-context.chat-hook-outcome-blocked {
+	.chat-used-context-label .monaco-button {
+		gap: 4px;
+	}
 }
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatQuestionCarousel.css b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatQuestionCarousel.css
index 8652ea889d7a2..45e5b303c2eaf 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatQuestionCarousel.css
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatQuestionCarousel.css
@@ -4,148 +4,155 @@
  *--------------------------------------------------------------------------------------------*/
 
 /* question carousel - this is above edits and todos */
-.interactive-session .interactive-input-part > .chat-question-carousel-widget-container:empty {
+.interactive-session .interactive-input-part > .chat-question-carousel-widget-container:empty,
+.interactive-session .interactive-input-part .interactive-input-and-edit-session > .chat-question-carousel-widget-container:empty {
 	display: none;
 }
 
 /* input specific styling */
-.interactive-session .interactive-input-part > .chat-question-carousel-widget-container .chat-question-carousel-container {
+.interactive-session .interactive-input-part > .chat-question-carousel-widget-container .chat-question-carousel-container,
+.interactive-session .interactive-input-part .interactive-input-and-edit-session > .chat-question-carousel-widget-container .chat-question-carousel-container {
 	margin: 0;
 	border: 1px solid var(--vscode-input-border, transparent);
-	background-color: var(--vscode-editor-background);
-	border-radius: 4px;
+	background-color: var(--vscode-panel-background);
+	border-radius: var(--vscode-cornerRadius-large);
 }
 
 /* general questions styling */
 .interactive-session .chat-question-carousel-container {
 	margin: 8px 0;
 	border: 1px solid var(--vscode-chat-requestBorder);
-	border-radius: 4px;
+	border-radius: var(--vscode-cornerRadius-large);
 	display: flex;
 	flex-direction: column;
 	overflow: hidden;
 	container-type: inline-size;
+	max-height: min(420px, 45vh);
+	position: relative;
 }
 
-/* container and header */
-.interactive-session .interactive-input-part > .chat-question-carousel-widget-container {
+/* input part wrapper */
+.interactive-session .interactive-input-part > .chat-question-carousel-widget-container,
+.interactive-session .interactive-input-part .interactive-input-and-edit-session > .chat-question-carousel-widget-container {
 	width: 100%;
 	position: relative;
+	display: flex;
+	flex-direction: column;
+	gap: 8px;
+}
+
+.interactive-session .interactive-input-part > .chat-question-carousel-widget-container:not(:empty),
+.interactive-session .interactive-input-part .interactive-input-and-edit-session > .chat-question-carousel-widget-container:not(:empty) {
+	margin-top: 8px;
+}
+
+.interactive-session .interactive-input-part > .chat-question-carousel-widget-container .chat-question-carousel-content,
+.interactive-session .interactive-input-part .interactive-input-and-edit-session > .chat-question-carousel-widget-container .chat-question-carousel-content {
+	min-height: 0;
+}
+
+/* container and header */
+.interactive-session .chat-question-carousel-container .chat-question-carousel-content {
+	display: flex;
+	flex-direction: column;
+	min-height: 0;
+	overflow: hidden;
 
-	.chat-question-carousel-content {
+	.chat-question-header-row {
 		display: flex;
 		flex-direction: column;
-		background: var(--vscode-chat-requestBackground);
-		padding: 8px 16px 10px 16px;
+		flex-shrink: 0;
 		overflow: hidden;
 
-		.chat-question-header-row {
+		.chat-question-title-row {
 			display: flex;
 			justify-content: space-between;
 			align-items: center;
 			gap: 8px;
 			min-width: 0;
-			padding-bottom: 5px;
-			margin-left: -16px;
-			margin-right: -16px;
-			padding-left: 16px;
-			padding-right: 16px;
+			padding: 8px 8px 8px 16px;
 			border-bottom: 1px solid var(--vscode-chat-requestBorder);
+		}
 
-			.chat-question-title {
-				flex: 1;
-				min-width: 0;
-				word-wrap: break-word;
-				overflow-wrap: break-word;
-				font-weight: 500;
-				font-size: var(--vscode-chat-font-size-body-s);
-				margin: 0;
-
-				.rendered-markdown {
-					a {
-						color: var(--vscode-textLink-foreground);
-					}
-
-					a:hover,
-					a:active {
-						color: var(--vscode-textLink-activeForeground);
-					}
+		.chat-question-title {
+			flex: 1;
+			min-width: 0;
+			word-wrap: break-word;
+			overflow-wrap: break-word;
+			font-weight: 500;
+			font-size: var(--vscode-chat-font-size-body-s);
+			margin: 0;
 
-					p {
-						margin: 0;
-					}
+			.rendered-markdown {
+				a {
+					color: var(--vscode-textLink-foreground);
 				}
 
-				.chat-question-title-main {
-					font-weight: 500;
+				a:hover,
+				a:active {
+					color: var(--vscode-textLink-activeForeground);
 				}
 
-				.chat-question-title-subtitle {
-					font-weight: normal;
-					color: var(--vscode-descriptionForeground);
+				p {
+					margin: 0;
 				}
 			}
+		}
 
-			.chat-question-close-container {
-				flex-shrink: 0;
+		.chat-question-close-container {
+			flex-shrink: 0;
 
-				.monaco-button.chat-question-close {
-					min-width: 22px;
-					width: 22px;
-					height: 22px;
-					padding: 0;
-					border: none;
-					background: transparent !important;
-					color: var(--vscode-foreground) !important;
-				}
+			.monaco-button.chat-question-close {
+				min-width: 22px;
+				width: 22px;
+				height: 22px;
+				padding: 0;
+				border: none !important;
+				box-shadow: none !important;
+				background: transparent !important;
+				color: var(--vscode-icon-foreground) !important;
+			}
 
-				.monaco-button.chat-question-close:hover:not(.disabled) {
-					background: var(--vscode-toolbar-hoverBackground) !important;
-				}
+			.monaco-button.chat-question-close:hover:not(.disabled) {
+				background: var(--vscode-toolbar-hoverBackground) !important;
 			}
 		}
 	}
 }
 
 /* questions list and freeform area */
-.interactive-session .interactive-input-part > .chat-question-carousel-widget-container .chat-question-input-container {
+.interactive-session .chat-question-carousel-container .chat-question-input-container {
 	display: flex;
 	flex-direction: column;
-	margin-top: 4px;
+	padding: 8px;
 	min-width: 0;
 
+	&::after {
+		content: '';
+		display: block;
+		height: 8px;
+		flex-shrink: 0;
+	}
+
 	/* some hackiness to get the focus looking right */
-	.chat-question-list-item:focus:not(.selected),
+	.chat-question-list-item:focus,
 	.chat-question-list:focus {
 		outline: none;
 	}
 
-	.chat-question-list:focus-visible {
-		outline: 1px solid var(--vscode-focusBorder);
-		outline-offset: -1px;
-	}
-
-	.chat-question-list:focus-within .chat-question-list-item.selected {
-		outline-width: 1px;
-		outline-style: solid;
-		outline-offset: -1px;
-		outline-color: var(--vscode-focusBorder);
-	}
-
 	.chat-question-list {
 		display: flex;
 		flex-direction: column;
-		gap: 3px;
 		outline: none;
-		padding: 4px 0;
+		padding: 0;
 
 		.chat-question-list-item {
 			display: flex;
 			align-items: center;
-			gap: 8px;
-			padding: 3px 8px;
+			gap: 12px;
+			padding: 6px 8px;
 			cursor: pointer;
-			border-radius: 3px;
+			border-radius: var(--vscode-cornerRadius-medium);
 			user-select: none;
 
 			.chat-question-list-indicator {
@@ -156,6 +163,8 @@
 				justify-content: center;
 				flex-shrink: 0;
 				margin-left: auto;
+				align-self: flex-start;
+				margin-top: 2px;
 			}
 
 			.chat-question-list-indicator.codicon-check {
@@ -166,13 +175,15 @@
 			.chat-question-list-label {
 				font-size: var(--vscode-chat-font-size-body-s);
 				flex: 1;
-				overflow: hidden;
-				text-overflow: ellipsis;
-				white-space: nowrap;
+				word-wrap: break-word;
+				overflow-wrap: break-word;
+				display: flex;
+				flex-direction: column;
 			}
 
 			.chat-question-list-label-title {
-				font-weight: 600;
+				font-weight: 500;
+				line-height: 1.4;
 			}
 
 			.chat-question-list-label-desc {
@@ -181,13 +192,28 @@
 			}
 		}
 
+		.chat-question-list-item.has-description {
+			align-items: flex-start;
+
+			.chat-question-list-number {
+				line-height: 1.4;
+				font-size: var(--vscode-chat-font-size-body-s);
+				font-weight: 500;
+			}
+
+			.chat-question-list-checkbox {
+				/* Title line-height is ~17px (1.4 * body-s), checkbox is 16px: 1px offset */
+				margin-top: 1px;
+			}
+		}
+
 		.chat-question-list-item:hover {
 			background-color: var(--vscode-list-hoverBackground);
 		}
 
 		/* Single-select: highlight entire row when selected */
 		.chat-question-list-item.selected {
-			background-color: var(--vscode-list-activeSelectionBackground);
+			background-color: var(--vscode-list-hoverBackground);
 			color: var(--vscode-list-activeSelectionForeground);
 
 			.chat-question-label {
@@ -204,16 +230,12 @@
 			}
 
 			.chat-question-list-number {
-				background-color: transparent;
 				color: var(--vscode-list-activeSelectionForeground);
-				border-color: var(--vscode-list-activeSelectionForeground);
-				border-bottom-color: var(--vscode-list-activeSelectionForeground);
-				box-shadow: none;
 			}
 		}
 
 		.chat-question-list-item.selected:hover {
-			background-color: var(--vscode-list-activeSelectionBackground);
+			background-color: var(--vscode-list-hoverBackground);
 		}
 
 		/* Checkbox for multi-select */
@@ -227,11 +249,12 @@
 	}
 
 	.chat-question-freeform {
-		margin-left: 8px;
+		margin: 0;
 		display: flex;
 		flex-direction: row;
 		align-items: center;
-		gap: 8px;
+		padding: 4px 8px;
+		gap: 12px;
 
 		.chat-question-freeform-number {
 			height: fit-content;
@@ -274,45 +297,43 @@
 	/* todo: change to use keybinding service so we don't have to recreate this */
 	.chat-question-list-number,
 	.chat-question-freeform-number {
-		display: inline-flex;
-		align-items: center;
-		justify-content: center;
-		min-width: 14px;
-		padding: 0px 4px;
-		border-style: solid;
-		border-width: 1px;
-		border-radius: 3px;
-		font-size: 11px;
-		font-weight: normal;
-		background-color: var(--vscode-keybindingLabel-background);
-		color: var(--vscode-keybindingLabel-foreground);
-		border-color: var(--vscode-keybindingLabel-border);
-		border-bottom-color: var(--vscode-keybindingLabel-bottomBorder);
-		box-shadow: inset 0 -1px 0 var(--vscode-widget-shadow);
+		font-size: var(--vscode-chat-font-size-body-s);
+		color: var(--vscode-descriptionForeground);
 		flex-shrink: 0;
+		min-width: 1ch;
+		text-align: right;
 	}
 }
 
-/* footer with step indicator and nav buttons */
-.interactive-session .interactive-input-part > .chat-question-carousel-widget-container .chat-question-footer-row {
+.interactive-session .chat-question-carousel-container .chat-question-input-container > * {
+	flex-shrink: 0;
+}
+
+.interactive-session .chat-question-carousel-container .chat-question-input-scrollable {
+	flex: 0 1 auto;
+	min-height: 0;
+	overscroll-behavior: contain;
+}
+
+/* footer with nav arrows, step indicator, and submit */
+.interactive-session .chat-question-carousel-container .chat-question-footer-row {
 	display: flex;
 	justify-content: space-between;
 	align-items: center;
-	padding: 4px 16px;
+	padding: 4px 8px;
 	border-top: 1px solid var(--vscode-chat-requestBorder);
-	background: var(--vscode-chat-requestBackground);
+	flex-shrink: 0;
 
-	.chat-question-step-indicator {
-		font-size: var(--vscode-chat-font-size-body-s);
-		color: var(--vscode-descriptionForeground);
+	.chat-question-footer-left {
+		display: flex;
+		align-items: center;
+		gap: 8px;
 	}
 
-	.chat-question-carousel-nav {
+	.chat-question-footer-right {
 		display: flex;
 		align-items: center;
-		gap: 4px;
-		flex-shrink: 0;
-		margin-left: auto;
+		gap: 8px;
 	}
 
 	.chat-question-nav-arrows {
@@ -321,49 +342,77 @@
 		gap: 4px;
 	}
 
-	.chat-question-carousel-nav .monaco-button.chat-question-nav-arrow {
+	.monaco-button.chat-question-nav-arrow {
 		min-width: 22px;
 		width: 22px;
 		height: 22px;
 		padding: 0;
-		border: none;
+		border: none !important;
+		box-shadow: none !important;
+		background: transparent !important;
+		color: var(--vscode-foreground) !important;
 	}
 
-	/* Secondary buttons (prev, next) use gray secondary background */
-	.chat-question-carousel-nav .monaco-button.chat-question-nav-arrow.chat-question-nav-prev,
-	.chat-question-carousel-nav .monaco-button.chat-question-nav-arrow.chat-question-nav-next {
-		background: var(--vscode-button-secondaryBackground) !important;
-		color: var(--vscode-button-secondaryForeground) !important;
+	.monaco-button.chat-question-nav-arrow:hover:not(.disabled) {
+		background: var(--vscode-toolbar-hoverBackground) !important;
 	}
 
-	.chat-question-carousel-nav .monaco-button.chat-question-nav-arrow.chat-question-nav-prev:hover:not(.disabled),
-	.chat-question-carousel-nav .monaco-button.chat-question-nav-arrow.chat-question-nav-next:hover:not(.disabled) {
-		background: var(--vscode-button-secondaryHoverBackground) !important;
+	.monaco-button.chat-question-nav-arrow.disabled {
+		opacity: 0.4;
 	}
 
-	/* Submit button (next on last question) uses primary background */
-	.chat-question-carousel-nav .monaco-button.chat-question-nav-arrow.chat-question-nav-submit {
+	.chat-question-step-indicator {
+		font-size: var(--vscode-chat-font-size-body-s);
+		color: var(--vscode-descriptionForeground);
+	}
+
+	.chat-question-submit-hint {
+		font-size: 11px;
+		color: var(--vscode-descriptionForeground);
+	}
+
+	.monaco-button.chat-question-submit-button {
 		background: var(--vscode-button-background) !important;
 		color: var(--vscode-button-foreground) !important;
+		height: 22px;
 		width: auto;
+		flex: 0 0 auto;
 		min-width: auto;
 		padding: 0 8px;
 	}
 
-	.chat-question-carousel-nav .monaco-button.chat-question-nav-arrow.chat-question-nav-submit:hover:not(.disabled) {
+	.monaco-button.chat-question-submit-button:hover:not(.disabled) {
 		background: var(--vscode-button-hoverBackground) !important;
 	}
+}
 
-	/* Close button uses transparent background */
-	.chat-question-carousel-nav .monaco-button.chat-question-nav-arrow.chat-question-close {
-		background: transparent !important;
-		color: var(--vscode-foreground) !important;
+/* carousel-level message (e.g. from MCP elicitation) */
+.interactive-session .chat-question-carousel-container .chat-question-carousel-message {
+	padding: 8px 16px 0;
+	font-size: var(--vscode-chat-font-size-body-s);
+	color: var(--vscode-descriptionForeground);
+	max-height: min(220px, 25vh);
+	overflow-y: auto;
+	overscroll-behavior: contain;
+
+	.rendered-markdown p {
+		margin: 0;
 	}
+}
 
-	.chat-question-carousel-nav .monaco-button.chat-question-nav-arrow.chat-question-close:hover:not(.disabled) {
-		background: var(--vscode-toolbar-hoverBackground) !important;
-	}
+/* field description below question title */
+.interactive-session .chat-question-carousel-container .chat-question-description {
+	padding: 4px 16px;
+	font-size: var(--vscode-chat-font-size-body-s);
+	color: var(--vscode-descriptionForeground);
+}
 
+/* validation error message below input area */
+.interactive-session .chat-question-carousel-container .chat-question-validation-message {
+	padding: 0 16px 4px;
+	font-size: var(--vscode-chat-font-size-body-s);
+	color: var(--vscode-editorWarning-foreground);
+	flex-shrink: 0;
 }
 
 /* summary (after finished) */
@@ -371,14 +420,11 @@
 	display: flex;
 	flex-direction: column;
 	gap: 8px;
-	padding: 8px 16px;
-	margin-bottom: 4px;
+	padding: 8px;
 
 	.chat-question-summary-item {
 		display: flex;
-		flex-direction: row;
-		flex-wrap: wrap;
-		align-items: baseline;
+		flex-direction: column;
 		gap: 0;
 		font-size: var(--vscode-chat-font-size-body-s);
 	}
@@ -389,11 +435,6 @@
 		overflow-wrap: break-word;
 	}
 
-	.chat-question-summary-label::after {
-		content: ': ';
-		white-space: pre;
-	}
-
 	.chat-question-summary-answer-title {
 		color: var(--vscode-foreground);
 		font-weight: 600;
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatTerminalToolProgressPart.css b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatTerminalToolProgressPart.css
index 4447aa118e69d..198f0f4f3b4f9 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatTerminalToolProgressPart.css
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatTerminalToolProgressPart.css
@@ -132,7 +132,6 @@
 	}
 }
 
-.chat-terminal-output-container.collapsed { display: none; }
 .chat-terminal-output-container {
 	border: 1px solid var(--vscode-chat-requestBorder);
 	border-bottom-left-radius: var(--vscode-cornerRadius-medium);
@@ -145,6 +144,12 @@
 	padding: 0;
 }
 
+/* Keep collapsed output fully hidden so it cannot contribute an extra border line. */
+.chat-terminal-output-container.collapsed,
+.chat-terminal-output-container:not(.expanded) {
+	display: none;
+}
+
 .chat-terminal-content-part .chat-terminal-content-title.chat-terminal-content-title-no-bottom-radius {
 	border-bottom-left-radius: 0px;
 	border-bottom-right-radius: 0px;
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatThinkingContent.css b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatThinkingContent.css
index 1097c935dcb64..df4551eaa3531 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatThinkingContent.css
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatThinkingContent.css
@@ -18,6 +18,8 @@
 	}
 
 	> .chat-used-context-label .monaco-button.monaco-icon-button {
+		display: flex;
+		align-items: center;
 		line-height: 1.5em;
 		font-size: 13px;
 
@@ -35,11 +37,18 @@
 
 		.rendered-markdown.chat-thinking-title-detail {
 			display: inline;
+			font-size: inherit;
+			line-height: inherit;
 
 			> p {
 				display: inline;
+				margin: 0;
 			}
 		}
+
+		.chat-thinking-title-detail-text {
+			opacity: 0.7;
+		}
 	}
 
 	&.chat-thinking-active > .chat-used-context-label .monaco-button.monaco-icon-button {
@@ -102,46 +111,44 @@
 
 		.chat-thinking-tool-wrapper {
 			.chat-used-context {
-					margin-bottom: 0px;
-					margin-left: 4px;
-					padding-left: 2px;
-				}
-
-				.chat-used-context {
-					.monaco-button.monaco-text-button {
-						color: var(--vscode-descriptionForeground);
+				margin-bottom: 0px;
+				margin-left: 4px;
+				padding-left: 2px;
 
-						:hover {
-							color: var(--vscode-foreground);
-						}
+				.monaco-button.monaco-text-button {
+					color: var(--vscode-descriptionForeground);
+					display: flex;
+					align-items: center;
 
-						.monaco-button:hover .chat-collapsible-hover-chevron {
-							opacity: 1;
-						}
+					:hover {
+						color: var(--vscode-foreground);
 					}
-				}
 
-				.chat-used-context:not(.chat-used-context-collapsed) {
-					.monaco-button.monaco-text-button {
-						color: var(--vscode-foreground);
+					.monaco-button:hover .chat-collapsible-hover-chevron {
+						opacity: 1;
 					}
 				}
+			}
 
-				.progress-container,
-				.chat-confirmation-widget-container {
-					margin: 0 0 2px 6px;
+			.chat-used-context:not(.chat-used-context-collapsed) {
+				.monaco-button.monaco-text-button {
+					color: var(--vscode-foreground);
 				}
+			}
 
-				.codicon:not(.chat-thinking-icon) {
-					display: none;
-				}
+			.progress-container,
+			.chat-confirmation-widget-container {
+				margin: 0 0 2px 6px;
+			}
 
-				.chat-collapsible-hover-chevron.codicon {
-					display: inline-flex;
-				}
+			/* todo: ideally not !important, but the competing css has 14 specificity */
+			.codicon.codicon-check,
+			.codicon.codicon-loading {
+				display: none !important;
+			}
 
-			.chat-used-context.show-checkmarks .chat-used-context-label .monaco-icon-button > .codicon:first-child:not(.chat-collapsible-hover-chevron) {
-				display: inline-block;
+			.chat-collapsible-hover-chevron.codicon {
+				display: inline-flex;
 			}
 
 			.show-checkmarks .chat-confirmation-widget-title > .codicon:first-child:not(.chat-collapsible-hover-chevron) {
@@ -163,7 +170,6 @@
 			padding: 6px 12px 6px 24px;
 			position: relative;
 			font-size: var(--vscode-chat-font-size-body-s);
-
 			.progress-container {
 				margin-bottom: 0px;
 				padding-top: 0px;
@@ -179,7 +185,7 @@
 		}
 
 		.chat-thinking-tool-wrapper .chat-markdown-part.rendered-markdown {
-			padding: 5px 12px 4px 20px;
+			padding: 5px 12px 4px 24px;
 
 			.status-icon.codicon-check {
 				display: none;
@@ -292,6 +298,11 @@
 	flex-direction: column;
 	width: 100%;
 
+	.monaco-button.monaco-text-button {
+		display: flex;
+		align-items: center;
+	}
+
 	.chat-used-context-list.chat-terminal-thinking-content {
 		border: none;
 		padding: 0;
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatTipContent.css b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatTipContent.css
index 43a9186f4978c..66dbbe1f82865 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatTipContent.css
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/media/chatTipContent.css
@@ -17,7 +17,6 @@
 	background-color: var(--vscode-editorWidget-background);
 	border: 1px solid var(--vscode-chat-requestBorder);
 	border-radius: var(--vscode-cornerRadius-medium);
-	z-index: 100;
 	transition: opacity 0.1s ease-in-out;
 }
 
@@ -82,11 +81,6 @@
 	color: var(--vscode-textLink-activeForeground);
 }
 
-.chat-getting-started-tip-container .chat-tip-widget .codicon-lightbulb {
-	font-size: 12px;
-	color: var(--vscode-notificationsWarningIcon-foreground);
-}
-
 .chat-getting-started-tip-container .chat-tip-widget .rendered-markdown p {
 	margin: 0;
 }
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatInputOutputMarkdownProgressPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatInputOutputMarkdownProgressPart.ts
index 32dcfbc757ac9..c9327e5097f28 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatInputOutputMarkdownProgressPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatInputOutputMarkdownProgressPart.ts
@@ -42,6 +42,7 @@ export class ChatInputOutputMarkdownProgressPart extends BaseChatToolInvocationS
 		message: string | IMarkdownString,
 		subtitle: string | IMarkdownString | undefined,
 		input: string,
+		inputLanguage: string | undefined,
 		output: IToolResultInputOutputDetails['output'] | undefined,
 		isError: boolean,
 		@IInstantiationService instantiationService: IInstantiationService,
@@ -54,10 +55,10 @@ export class ChatInputOutputMarkdownProgressPart extends BaseChatToolInvocationS
 		let codeBlockIndex = codeBlockStartIndex;
 
 		// Simple factory to create code part data objects
-		const createCodePart = (data: string): IChatCollapsibleIOCodePart => ({
+		const createCodePart = (data: string, languageId = 'json'): IChatCollapsibleIOCodePart => ({
 			kind: 'code',
 			data,
-			languageId: 'json',
+			languageId,
 			codeBlockIndex: codeBlockIndex++,
 			ownerMarkdownPartId: this.codeblocksPartId,
 			options: {
@@ -82,7 +83,7 @@ export class ChatInputOutputMarkdownProgressPart extends BaseChatToolInvocationS
 			subtitle,
 			this.getAutoApproveMessageContent(),
 			context,
-			createCodePart(input),
+			createCodePart(input, inputLanguage),
 			processedOutput && processedOutput.length > 0 ? {
 				parts: processedOutput.map((o, i): ChatCollapsibleIOPart => {
 					const permalinkBasename = o.type === 'ref' || o.uri
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatMcpAppModel.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatMcpAppModel.ts
index 7541799ba2903..4c83b8ac18a2a 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatMcpAppModel.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatMcpAppModel.ts
@@ -17,12 +17,15 @@ import { autorun, autorunSelfDisposable, IObservable, observableValue } from '..
 import { basename } from '../../../../../../../base/common/resources.js';
 import { isFalsyOrWhitespace } from '../../../../../../../base/common/strings.js';
 import { hasKey, isDefined } from '../../../../../../../base/common/types.js';
+import { URI } from '../../../../../../../base/common/uri.js';
 import { localize } from '../../../../../../../nls.js';
+import { IChatResponseResourceFileSystemProvider } from '../../../../common/widget/chatResponseResourceFileSystemProvider.js';
 import { IInstantiationService } from '../../../../../../../platform/instantiation/common/instantiation.js';
 import { ILogService } from '../../../../../../../platform/log/common/log.js';
 import { IOpenerService } from '../../../../../../../platform/opener/common/opener.js';
 import { IProductService } from '../../../../../../../platform/product/common/productService.js';
 import { IStorageService } from '../../../../../../../platform/storage/common/storage.js';
+
 import { IMcpAppResourceContent, McpToolCallUI } from '../../../../../mcp/browser/mcpToolCallUI.js';
 import { McpResourceURI } from '../../../../../mcp/common/mcpTypes.js';
 import { MCP } from '../../../../../mcp/common/modelContextProtocol.js';
@@ -32,6 +35,7 @@ import { IChatRequestVariableEntry } from '../../../../common/attachments/chatVa
 import { IChatToolInvocation, IChatToolInvocationSerialized } from '../../../../common/chatService/chatService.js';
 import { isToolResultInputOutputDetails, IToolResult } from '../../../../common/tools/languageModelToolsService.js';
 import { IChatWidgetService } from '../../../chat.js';
+import { IChatCollapsibleIODataPart } from '../chatToolInputOutputContentPart.js';
 import { IMcpAppRenderData } from './chatMcpAppSubPart.js';
 
 /** Storage key for persistent webview origins */
@@ -84,6 +88,10 @@ export class ChatMcpAppModel extends Disposable {
 	private readonly _onDidChangeHeight = this._register(new Emitter<void>());
 	public readonly onDidChangeHeight: Event<void> = this._onDidChangeHeight.event;
 
+	/** Accumulated download resource parts from ui/download-file calls */
+	private readonly _downloadParts = observableValue<IChatCollapsibleIODataPart[]>(this, []);
+	public readonly downloadParts: IObservable<IChatCollapsibleIODataPart[]> = this._downloadParts;
+
 	/** Full host context for the MCP App */
 	public readonly hostContext: IObservable<McpApps.McpUiHostContext>;
 
@@ -97,6 +105,7 @@ export class ChatMcpAppModel extends Disposable {
 		@IChatWidgetService private readonly _chatWidgetService: IChatWidgetService,
 		@IWebviewService private readonly _webviewService: IWebviewService,
 		@IStorageService storageService: IStorageService,
+		@IChatResponseResourceFileSystemProvider private readonly _chatResponseResourceFsProvider: IChatResponseResourceFileSystemProvider,
 		@ILogService private readonly _logService: ILogService,
 		@IProductService private readonly _productService: IProductService,
 		@IOpenerService private readonly _openerService: IOpenerService,
@@ -437,6 +446,10 @@ export class ChatMcpAppModel extends Disposable {
 					result = await this._handleOpenLink(request.params);
 					break;
 
+				case 'ui/download-file':
+					result = await this._handleDownloadFile(request.params);
+					break;
+
 				case 'ui/request-display-mode':
 					// VS Code only supports inline display mode
 					result = { mode: 'inline' } satisfies McpApps.McpUiRequestDisplayModeResult;
@@ -543,7 +556,8 @@ export class ChatMcpAppModel extends Disposable {
 					resourceLink: {},
 					resource: {},
 					structuredContent: {},
-				}
+				},
+				downloadFile: {},
 			},
 			hostContext: this.hostContext.get(),
 		} satisfies Required<McpApps.McpUiInitializeResult>;
@@ -682,6 +696,45 @@ export class ChatMcpAppModel extends Disposable {
 		widget?.delegateScrollFromMouseWheelEvent(evt as IMouseWheelEvent);
 	}
 
+	private async _handleDownloadFile(params: McpApps.McpUiDownloadFileRequest['params']): Promise<McpApps.McpUiDownloadFileResult> {
+		const newParts: IChatCollapsibleIODataPart[] = [];
+		let hadError = false;
+
+		for (const content of params.contents) {
+			try {
+				if (content.type === 'resource') {
+					// EmbeddedResource — associate inline content with the chat response FS
+					const resource = content.resource;
+					const parsed = URI.parse(resource.uri);
+
+					const data: Uint8Array | { base64: string } = hasKey(resource, { text: true })
+						? new TextEncoder().encode(resource.text)
+						: { base64: resource.blob };
+
+					const uri = this._chatResponseResourceFsProvider.associate(this.renderData.sessionResource, data, basename(parsed));
+					newParts.push({ kind: 'data', mimeType: resource.mimeType, uri });
+				} else if (content.type === 'resource_link') {
+					// ResourceLink — create a part with an MCP resource URI, resolved lazily on save
+					const mcpUri = McpResourceURI.fromServer(
+						{ id: this.renderData.serverDefinitionId, label: '' },
+						content.uri,
+					);
+					newParts.push({ kind: 'data', mimeType: content.mimeType, uri: mcpUri });
+				}
+			} catch (error) {
+				hadError = true;
+				this._logService.warn('[MCP App] Failed to process ui/download-file content', error);
+			}
+		}
+
+		if (newParts.length > 0) {
+			const existing = this._downloadParts.get();
+			this._downloadParts.set([...existing, ...newParts], undefined);
+		}
+
+		return hadError ? { isError: true } : {};
+	}
+
 	private async _handleOpenLink(params: McpApps.McpUiOpenLinkRequest['params']): Promise<McpApps.McpUiOpenLinkResult> {
 		const ok = await this._openerService.open(params.url);
 		return { isError: !ok };
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatMcpAppSubPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatMcpAppSubPart.ts
index cf8f4d62ffa86..db87356f0047a 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatMcpAppSubPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatMcpAppSubPart.ts
@@ -21,6 +21,7 @@ import { IChatCodeBlockInfo } from '../../../chat.js';
 import { IChatContentPartRenderContext } from '../chatContentParts.js';
 import { ChatErrorWidget } from '../chatErrorContentPart.js';
 import { ChatProgressSubPart } from '../chatProgressContentPart.js';
+import { ChatResourceGroupWidget } from '../chatResourceGroupWidget.js';
 import { ChatMcpAppModel, McpAppLoadState } from './chatMcpAppModel.js';
 import { BaseChatToolInvocationSubPart } from './chatToolInvocationSubPart.js';
 
@@ -63,6 +64,12 @@ export class ChatMcpAppSubPart extends BaseChatToolInvocationSubPart {
 	/** Current error node */
 	private _errorNode: HTMLElement | undefined;
 
+	/** Container for download resource pills */
+	private readonly _downloadContainer: HTMLElement;
+
+	/** Current resource group widget for downloads */
+	private readonly _downloadWidget = this._register(new MutableDisposable<ChatResourceGroupWidget>());
+
 	constructor(
 		toolInvocation: IChatToolInvocation | IChatToolInvocationSerialized,
 		onDidRemount: Event<void>,
@@ -81,6 +88,10 @@ export class ChatMcpAppSubPart extends BaseChatToolInvocationSubPart {
 		this._webviewContainer.style.height = '300px'; // Initial height, will be updated by model
 		this.domNode.appendChild(this._webviewContainer);
 
+		// Download container — below webview, for ui/download-file resources
+		this._downloadContainer = dom.$('div.mcp-app-downloads');
+		this.domNode.appendChild(this._downloadContainer);
+
 		const targetWindow = dom.getWindow(this.domNode);
 		const getMaxHeight = () => maxWebviewHeightPct * targetWindow.innerHeight;
 		const maxHeight = observableValue('mcpAppMaxHeight', getMaxHeight());
@@ -110,6 +121,21 @@ export class ChatMcpAppSubPart extends BaseChatToolInvocationSubPart {
 			this._updateContainerHeight();
 		}));
 
+		// Observe download parts and render resource group widget
+		this._register(autorun(reader => {
+			const parts = this._model.downloadParts.read(reader);
+			if (parts.length === 0) {
+				this._downloadWidget.clear();
+				dom.clearNode(this._downloadContainer);
+				return;
+			}
+
+			dom.clearNode(this._downloadContainer);
+			const widget = this._instantiationService.createInstance(ChatResourceGroupWidget, parts);
+			this._downloadWidget.value = widget;
+			this._downloadContainer.appendChild(widget.domNode);
+		}));
+
 		this._register(onDidRemount(() => {
 			this._model.remount();
 		}));
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatModifiedFilesConfirmationSubPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatModifiedFilesConfirmationSubPart.ts
new file mode 100644
index 0000000000000..8bf86a6b9d197
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatModifiedFilesConfirmationSubPart.ts
@@ -0,0 +1,284 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../../../../base/browser/dom.js';
+import { Button, ButtonWithIcon } from '../../../../../../../base/browser/ui/button/button.js';
+import { Codicon } from '../../../../../../../base/common/codicons.js';
+import { IMarkdownString, MarkdownString } from '../../../../../../../base/common/htmlContent.js';
+import { toDisposable } from '../../../../../../../base/common/lifecycle.js';
+import { hasKey } from '../../../../../../../base/common/types.js';
+import { URI } from '../../../../../../../base/common/uri.js';
+import { localize } from '../../../../../../../nls.js';
+import { ICommandService } from '../../../../../../../platform/commands/common/commands.js';
+import { IContextKeyService } from '../../../../../../../platform/contextkey/common/contextkey.js';
+import { IInstantiationService } from '../../../../../../../platform/instantiation/common/instantiation.js';
+import { IKeybindingService } from '../../../../../../../platform/keybinding/common/keybinding.js';
+import { IMarkdownRendererService } from '../../../../../../../platform/markdown/browser/markdownRenderer.js';
+import { defaultButtonStyles } from '../../../../../../../platform/theme/browser/defaultStyles.js';
+import { IChatModifiedFilesConfirmationData, IChatToolInvocation, ToolConfirmKind } from '../../../../common/chatService/chatService.js';
+import { ILanguageModelToolsService } from '../../../../common/tools/languageModelToolsService.js';
+import { ModifiedFileEntryState } from '../../../../common/editing/chatEditingService.js';
+import { ChatContextKeys } from '../../../../common/actions/chatContextKeys.js';
+import { IChatCodeBlockInfo, IChatWidgetService } from '../../../chat.js';
+import { IChatContentPartRenderContext } from '../chatContentParts.js';
+import { ChatCustomConfirmationWidget, IChatConfirmationButton } from '../chatConfirmationWidget.js';
+import { CollapsibleListPool, IChatCollapsibleListItem } from '../chatReferencesContentPart.js';
+import { IEditorService } from '../../../../../../services/editor/common/editorService.js';
+import { AbstractToolConfirmationSubPart } from './abstractToolConfirmationSubPart.js';
+
+export class ChatModifiedFilesConfirmationSubPart extends AbstractToolConfirmationSubPart {
+	public override readonly domNode: HTMLElement;
+	public override readonly codeblocks: IChatCodeBlockInfo[] = [];
+
+	constructor(
+		toolInvocation: IChatToolInvocation,
+		context: IChatContentPartRenderContext,
+		private readonly listPool: CollapsibleListPool,
+		@IInstantiationService instantiationService: IInstantiationService,
+		@IKeybindingService keybindingService: IKeybindingService,
+		@IContextKeyService contextKeyService: IContextKeyService,
+		@IChatWidgetService chatWidgetService: IChatWidgetService,
+		@ILanguageModelToolsService languageModelToolsService: ILanguageModelToolsService,
+		@IMarkdownRendererService private readonly markdownRendererService: IMarkdownRendererService,
+		@IEditorService private readonly editorService: IEditorService,
+		@ICommandService private readonly commandService: ICommandService,
+	) {
+		super(toolInvocation, context, instantiationService, keybindingService, contextKeyService, chatWidgetService, languageModelToolsService);
+
+		const state = toolInvocation.state.get();
+		if (state.type !== IChatToolInvocation.StateKind.WaitingForConfirmation || !state.confirmationMessages?.title) {
+			throw new Error('Modified files confirmation messages are missing');
+		}
+
+		const data = toolInvocation.toolSpecificData;
+		if (!data || data.kind !== 'modifiedFilesConfirmation') {
+			throw new Error('Modified files confirmation data is missing');
+		}
+
+		const tool = languageModelToolsService.getTool(toolInvocation.toolId);
+		const confirmWidget = this._register(this.instantiationService.createInstance(
+			ChatCustomConfirmationWidget<() => void>,
+			this.context,
+			{
+				title: this.getTitle(),
+				icon: tool?.icon && hasKey(tool.icon, { id: true }) ? tool.icon : Codicon.tools,
+				subtitle: typeof toolInvocation.originMessage === 'string' ? toolInvocation.originMessage : toolInvocation.originMessage?.value,
+				buttons: this.createButtons(data.options),
+				message: this.createWidgetContentElement(state.confirmationMessages.message, data),
+			}
+		));
+
+		const hasToolConfirmation = ChatContextKeys.Editing.hasToolConfirmation.bindTo(this.contextKeyService);
+		hasToolConfirmation.set(true);
+
+		this._register(confirmWidget.onDidClick(button => {
+			button.data();
+			this.chatWidgetService.getWidgetBySessionResource(this.context.element.sessionResource)?.focusInput();
+		}));
+
+		this._register(toDisposable(() => hasToolConfirmation.reset()));
+		this.domNode = confirmWidget.domNode;
+	}
+
+	private createButtons(options: readonly string[]): IChatConfirmationButton<() => void>[] {
+		const [primaryOption, ...secondaryOptions] = options;
+		return [
+			{
+				label: primaryOption,
+				data: () => this.confirmWith(this.toolInvocation, { type: ToolConfirmKind.UserAction, selectedButton: primaryOption }),
+				moreActions: secondaryOptions.map(option => ({
+					label: option,
+					data: () => this.confirmWith(this.toolInvocation, { type: ToolConfirmKind.UserAction, selectedButton: option }),
+				}))
+			},
+			{
+				label: localize('cancel', 'Cancel'),
+				data: () => this.confirmWith(this.toolInvocation, { type: ToolConfirmKind.Skipped }),
+				isSecondary: true,
+			}
+		];
+	}
+
+	private createWidgetContentElement(message: string | IMarkdownString | undefined, data: IChatModifiedFilesConfirmationData): HTMLElement {
+		const container = dom.$('.chat-modified-files-confirmation');
+
+		if (message) {
+			const renderedMessage = this._register(this.markdownRendererService.render(typeof message === 'string' ? new MarkdownString(message) : message));
+			container.append(renderedMessage.element);
+		}
+
+		container.append(this.createModifiedFilesElement(data));
+		return container;
+	}
+
+	private createModifiedFilesElement(data: IChatModifiedFilesConfirmationData): HTMLElement {
+		const container = dom.$('.chat-modified-files-confirmation-list.chat-editing-session-container.show-file-icons');
+		const overview = dom.append(container, dom.$('.chat-editing-session-overview'));
+		const title = dom.append(overview, dom.$('.working-set-title'));
+		const titleButton = this._register(new ButtonWithIcon(title, {
+			buttonBackground: undefined,
+			buttonBorder: undefined,
+			buttonForeground: undefined,
+			buttonHoverBackground: undefined,
+			buttonSecondaryBackground: undefined,
+			buttonSecondaryForeground: undefined,
+			buttonSecondaryHoverBackground: undefined,
+			buttonSeparator: undefined,
+			supportIcons: true,
+		}));
+		const actions = dom.append(overview, dom.$('.chat-editing-session-actions'));
+		const countsContainer = dom.$('.working-set-line-counts');
+		const addedSpan = dom.append(countsContainer, dom.$('.working-set-lines-added'));
+		const removedSpan = dom.append(countsContainer, dom.$('.working-set-lines-removed'));
+		titleButton.element.appendChild(countsContainer);
+
+		const filesLabel = data.modifiedFiles.length === 1
+			? localize('oneFileChanged', '1 file changed')
+			: localize('manyFilesChanged', '{0} files changed', data.modifiedFiles.length);
+		titleButton.label = filesLabel;
+
+		let added = 0;
+		let removed = 0;
+		let hasDiffStats = false;
+		for (const file of data.modifiedFiles) {
+			if (typeof file.insertions === 'number' || typeof file.deletions === 'number') {
+				hasDiffStats = true;
+				added += file.insertions ?? 0;
+				removed += file.deletions ?? 0;
+			}
+		}
+
+		if (hasDiffStats) {
+			addedSpan.textContent = `+${added}`;
+			removedSpan.textContent = `-${removed}`;
+			titleButton.element.setAttribute('aria-label', localize('modifiedFilesSummaryWithCounts', '{0}, {1} lines added, {2} lines removed', filesLabel, added, removed));
+			countsContainer.setAttribute('aria-label', localize('modifiedFilesCounts', '{0} lines added, {1} lines removed', added, removed));
+		} else {
+			countsContainer.remove();
+			titleButton.element.setAttribute('aria-label', filesLabel);
+		}
+
+		const viewAllChangesButton = this._register(new Button(actions, {
+			...defaultButtonStyles,
+			secondary: true,
+			small: true,
+			supportIcons: true,
+			ariaLabel: localize('viewAllChanges', 'View All Changes'),
+			title: localize('viewAllChanges', 'View All Changes'),
+		}));
+		viewAllChangesButton.element.classList.add('default-colors');
+		viewAllChangesButton.icon = Codicon.diffMultiple;
+		viewAllChangesButton.label = ' ';
+		this._register(viewAllChangesButton.onDidClick(async () => {
+			await this.openAllChanges(data);
+		}));
+
+		const listReference = this._register(this.listPool.get());
+		const list = listReference.object;
+		const listItems = data.modifiedFiles.map<IChatCollapsibleListItem>(file => {
+			const resource = URI.revive(file.uri);
+			const originalUri = file.originalUri ? URI.revive(file.originalUri) : undefined;
+			return {
+				kind: 'reference',
+				reference: resource,
+				title: file.title,
+				description: file.description,
+				state: ModifiedFileEntryState.Accepted,
+				showModifiedState: true,
+				options: {
+					diffMeta: typeof file.insertions === 'number' || typeof file.deletions === 'number' ? {
+						added: file.insertions ?? 0,
+						removed: file.deletions ?? 0,
+					} : undefined,
+					originalUri,
+					status: undefined,
+				}
+			};
+		});
+
+		this._register(list.onDidOpen(async e => {
+			if (e.element?.kind !== 'reference' || !URI.isUri(e.element.reference)) {
+				return;
+			}
+
+			const modifiedUri = e.element.reference;
+			const originalUri = e.element.options?.originalUri;
+			if (originalUri) {
+				await this.editorService.openEditor({
+					original: { resource: originalUri },
+					modified: { resource: modifiedUri },
+					options: e.editorOptions,
+				});
+				return;
+			}
+
+			await this.editorService.openEditor({
+				resource: modifiedUri,
+				options: e.editorOptions,
+			});
+		}));
+
+		const maxItemsShown = 6;
+		const itemsShown = Math.min(listItems.length, maxItemsShown);
+		const height = itemsShown * 22;
+		const workingSetContainer = dom.append(container, dom.$('.chat-editing-session-list.collapsed'));
+		list.layout(height);
+		list.getHTMLElement().style.height = `${height}px`;
+		list.splice(0, list.length, listItems);
+		workingSetContainer.append(list.getHTMLElement());
+
+		let isCollapsed = true;
+		const setExpansionState = () => {
+			titleButton.icon = isCollapsed ? Codicon.chevronRight : Codicon.chevronDown;
+			workingSetContainer.classList.toggle('collapsed', isCollapsed);
+		};
+		setExpansionState();
+
+		const toggleWorkingSet = () => {
+			isCollapsed = !isCollapsed;
+			setExpansionState();
+		};
+
+		this._register(titleButton.onDidClick(toggleWorkingSet));
+		this._register(dom.addDisposableListener(overview, 'click', e => {
+			if (e.defaultPrevented) {
+				return;
+			}
+
+			const target = e.target as HTMLElement;
+			if (target.closest('.monaco-button')) {
+				return;
+			}
+
+			toggleWorkingSet();
+		}));
+
+		return container;
+	}
+
+	private async openAllChanges(data: IChatModifiedFilesConfirmationData): Promise<void> {
+		await this.commandService.executeCommand('_workbench.openMultiDiffEditor', {
+			title: localize('modifiedFilesAllChangesTitle', 'All Changes'),
+			resources: data.modifiedFiles.map(file => ({
+				originalUri: file.originalUri ? URI.revive(file.originalUri) : undefined,
+				modifiedUri: URI.revive(file.uri),
+			}))
+		});
+	}
+
+	protected createContentElement(): HTMLElement | string {
+		throw new Error('Not used');
+	}
+
+	protected getTitle(): string {
+		const state = this.toolInvocation.state.get();
+		if (state.type !== IChatToolInvocation.StateKind.WaitingForConfirmation) {
+			return '';
+		}
+
+		const title = state.confirmationMessages?.title;
+		return typeof title === 'string' ? title : title?.value ?? '';
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatTerminalToolProgressPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatTerminalToolProgressPart.ts
index 25f8e21898d08..8f70589d4d4b5 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatTerminalToolProgressPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatTerminalToolProgressPart.ts
@@ -17,7 +17,10 @@ import { ChatQueryTitlePart } from '../chatConfirmationWidget.js';
 import { IChatContentPartRenderContext } from '../chatContentParts.js';
 import { ChatMarkdownContentPart, type IChatMarkdownContentPartOptions } from '../chatMarkdownContentPart.js';
 import { ChatProgressSubPart } from '../chatProgressContentPart.js';
+import { ChatResourceGroupWidget } from '../chatResourceGroupWidget.js';
+import { IChatCollapsibleIODataPart } from '../chatToolInputOutputContentPart.js';
 import { BaseChatToolInvocationSubPart } from './chatToolInvocationSubPart.js';
+import { extractImagesFromToolInvocationOutputDetails } from '../../../../common/chatImageExtraction.js';
 import { TerminalToolAutoExpand } from './terminalToolAutoExpand.js';
 import { ChatCollapsibleContentPart } from '../chatCollapsibleContentPart.js';
 import { IChatRendererContent } from '../../../../common/model/chatViewModel.js';
@@ -28,6 +31,7 @@ import { timeout } from '../../../../../../../base/common/async.js';
 import { IChatTerminalToolProgressPart, ITerminalChatService, ITerminalConfigurationService, ITerminalEditorService, ITerminalGroupService, ITerminalInstance, ITerminalService } from '../../../../../terminal/browser/terminal.js';
 import { Disposable, DisposableStore, MutableDisposable, toDisposable, type IDisposable } from '../../../../../../../base/common/lifecycle.js';
 import { Emitter } from '../../../../../../../base/common/event.js';
+import { autorun } from '../../../../../../../base/common/observable.js';
 import { ThemeIcon } from '../../../../../../../base/common/themables.js';
 import { DecorationSelector, getTerminalCommandDecorationState, getTerminalCommandDecorationTooltip } from '../../../../../terminal/browser/xterm/decorationStyles.js';
 import * as dom from '../../../../../../../base/browser/dom.js';
@@ -56,9 +60,36 @@ import { PANEL_BACKGROUND } from '../../../../../../common/theme.js';
 import { editorBackground } from '../../../../../../../platform/theme/common/colorRegistry.js';
 import { IThemeService } from '../../../../../../../platform/theme/common/themeService.js';
 
+/**
+ * Minimum number of rows to display in the terminal output view.
+ */
 const MIN_OUTPUT_ROWS = 1;
+
+/**
+ * Maximum number of rows to display in the terminal output view before scrolling.
+ */
 const MAX_OUTPUT_ROWS = 10;
 
+/**
+ * Maximum number of characters to display in the command title before truncating.
+ */
+const MAX_COMMAND_TITLE_LENGTH = 50;
+
+/**
+ * Maximum number of retries when waiting for terminal output to appear.
+ */
+const MAX_OUTPUT_POLL_RETRIES = 10;
+
+/**
+ * Delay between retries when polling for terminal output (in milliseconds).
+ */
+const OUTPUT_POLL_DELAY_MS = 100;
+
+/**
+ * Minimum number of data events that indicate real output (vs shell integration sequences).
+ */
+const MIN_DATA_EVENTS_FOR_REAL_OUTPUT = 2;
+
 /**
  * Remembers whether a tool invocation was last expanded so state survives virtualization re-renders.
  */
@@ -195,6 +226,25 @@ class TerminalCommandDecoration extends Disposable {
 	}
 }
 
+/**
+ * A chat content part that displays terminal tool invocation progress.
+ *
+ * This component shows:
+ * - The command being executed with syntax highlighting
+ * - A status decoration indicating success/failure/running state
+ * - Expandable terminal output with live streaming support
+ * - Actions to focus the terminal, show/hide output, and continue in background
+ *
+ * The component supports two rendering modes:
+ * - Standard mode: Shows full progress with status indicators
+ * - Collapsible wrapper mode: For thinking containers with simplified UI
+ *
+ * Output auto-expansion behavior:
+ * - Long-running commands with output auto-expand after a short delay
+ * - Fast commands that complete quickly don't auto-expand (prevents flickering)
+ * - Failed commands can be configured to auto-expand via settings
+ * - Successful commands auto-collapse if output was auto-expanded
+ */
 export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart implements IChatTerminalToolProgressPart {
 	public readonly domNode: HTMLElement;
 
@@ -382,6 +432,8 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 			}));
 		}
 
+		this._renderImagePills(toolInvocation, context, elements.container);
+
 		// Only auto-expand in thinking containers if there's actual output to show
 		const hasStoredOutput = !!terminalData.terminalCommandOutput;
 		if (expandedStateByInvocation.get(toolInvocation) || (this._isInThinkingContainer && IChatToolInvocation.isComplete(toolInvocation) && hasStoredOutput)) {
@@ -390,11 +442,61 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 		this._register(this._terminalChatService.registerProgressPart(this));
 	}
 
+	/**
+	 * Renders image attachment pills below the terminal output when the tool
+	 * result contains image data parts. For collapsible wrappers, the single
+	 * widget is reparented between inside/outside based on expanded state.
+	 */
+	private _renderImagePills(toolInvocation: IChatToolInvocation | IChatToolInvocationSerialized, context: IChatContentPartRenderContext, innerContainer: HTMLElement): void {
+		const renderImages = () => {
+			const extracted = extractImagesFromToolInvocationOutputDetails(toolInvocation, context.element.sessionResource);
+			const imageParts: IChatCollapsibleIODataPart[] = extracted.map(img => ({
+				kind: 'data',
+				value: img.data.buffer,
+				mimeType: img.mimeType,
+				uri: img.uri,
+			}));
+			if (imageParts.length === 0) {
+				return;
+			}
+
+			const widget = this._register(this._instantiationService.createInstance(ChatResourceGroupWidget, imageParts));
+
+			if (this._thinkingCollapsibleWrapper) {
+				// Reparent the single widget between inner (expanded) and outer (collapsed)
+				const wrapper = this._thinkingCollapsibleWrapper;
+				const placeWidget = (expanded: boolean) => {
+					if (expanded) {
+						innerContainer.appendChild(widget.domNode);
+					} else {
+						wrapper.domNode.appendChild(widget.domNode);
+					}
+				};
+				placeWidget(wrapper.expanded.get());
+				this._register(autorun(reader => {
+					placeWidget(wrapper.expanded.read(reader));
+				}));
+			} else {
+				innerContainer.appendChild(widget.domNode);
+			}
+		};
+
+		if (toolInvocation.kind === 'toolInvocationSerialized') {
+			renderImages();
+		} else {
+			this._register(autorun(reader => {
+				const state = toolInvocation.state.read(reader);
+				if (state.type === IChatToolInvocation.StateKind.Completed) {
+					renderImages();
+				}
+			}));
+		}
+	}
+
 	private _createCollapsibleWrapper(contentElement: HTMLElement, commandText: string, toolInvocation: IChatToolInvocation | IChatToolInvocationSerialized, context: IChatContentPartRenderContext): HTMLElement {
 		// truncate header when it's too long
-		const maxCommandLength = 50;
-		const truncatedCommand = commandText.length > maxCommandLength
-			? commandText.substring(0, maxCommandLength) + '...'
+		const truncatedCommand = commandText.length > MAX_COMMAND_TITLE_LENGTH
+			? commandText.substring(0, MAX_COMMAND_TITLE_LENGTH) + '...'
 			: commandText;
 
 		const isComplete = IChatToolInvocation.isComplete(toolInvocation);
@@ -412,6 +514,18 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 		));
 		this._thinkingCollapsibleWrapper = wrapper;
 
+		// Sync terminal output expansion with the collapsible wrapper.
+		// Skip the initial run — initial state is handled separately.
+		let isFirstRun = true;
+		this._register(autorun(r => {
+			const expanded = wrapper.expanded.read(r);
+			if (isFirstRun) {
+				isFirstRun = false;
+				return;
+			}
+			this._toggleOutput(expanded);
+		}));
+
 		return wrapper.domNode;
 	}
 
@@ -584,6 +698,27 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 		this._decoration.update();
 	}
 
+	/**
+	 * Determines whether the terminal output should auto-expand.
+	 * Returns false if already expanded, user has manually toggled, component is disposed,
+	 * or if the invocation was previously expanded (to preserve state across re-renders).
+	 */
+	private _shouldAutoExpand(): boolean {
+		return !this._outputView.isExpanded &&
+			!this._userToggledOutput &&
+			!this._store.isDisposed &&
+			!expandedStateByInvocation.get(this.toolInvocation);
+	}
+
+	/**
+	 * Registers event listeners on the terminal instance to track command execution,
+	 * manage auto-expansion of output, and handle command completion.
+	 *
+	 * This method sets up:
+	 * - Command detection listeners for tracking command lifecycle
+	 * - Auto-expand logic based on command output and duration
+	 * - Instance disposal handling to clean up actions and state
+	 */
 	private _registerInstanceListener(terminalInstance: ITerminalInstance): void {
 		const commandDetectionListener = this._register(new MutableDisposable<IDisposable>());
 		const tryResolveCommand = async (): Promise<ITerminalCommand | undefined> => {
@@ -624,14 +759,14 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 				// hasn't moved past the marker (e.g., progress bars updating on same line)
 				// Shell integration sequences fire a couple times per command (PromptStart, CommandStart,
 				// CommandExecuted), so we need a small threshold to filter those out
-				return receivedDataCount > 2;
+				return receivedDataCount > MIN_DATA_EVENTS_FOR_REAL_OUTPUT;
 			};
 
 			// Use the extracted auto-expand logic
 			const autoExpand = store.add(new TerminalToolAutoExpand({
 				commandDetection,
 				onWillData: terminalInstance.onWillData,
-				shouldAutoExpand: () => !this._outputView.isExpanded && !this._userToggledOutput && !this._store.isDisposed && !expandedStateByInvocation.get(this.toolInvocation),
+				shouldAutoExpand: () => this._shouldAutoExpand(),
 				hasRealOutput,
 			}));
 			store.add(autoExpand.onDidRequestExpand(() => {
@@ -654,18 +789,8 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 				this._addActions(terminalInstance, this._terminalData.terminalToolSessionId);
 				const resolvedCommand = this._getResolvedCommand(terminalInstance);
 
-				// update title
-				this.markCollapsibleWrapperComplete();
+				this._handleCommandCompletion(resolvedCommand);
 
-				// Auto-collapse on success
-				if (resolvedCommand?.exitCode === 0 && this._outputView.isExpanded && !this._userToggledOutput) {
-					this._toggleOutput(false);
-				}
-				// keep outer wrapper expanded on error
-				const autoExpandFailures = this._configurationService.getValue<boolean>(ChatConfiguration.AutoExpandToolFailures);
-				if (autoExpandFailures && resolvedCommand?.exitCode !== undefined && resolvedCommand.exitCode !== 0 && this._thinkingCollapsibleWrapper) {
-					this.expandCollapsibleWrapper();
-				}
 				if (resolvedCommand?.endMarker) {
 					commandDetectionListener.clear();
 				}
@@ -675,17 +800,7 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 			const resolvedImmediately = await tryResolveCommand();
 			if (resolvedImmediately?.endMarker) {
 				commandDetectionListener.clear();
-				// update title
-				this.markCollapsibleWrapperComplete();
-				// Auto-collapse on success
-				if (resolvedImmediately.exitCode === 0 && this._outputView.isExpanded && !this._userToggledOutput) {
-					this._toggleOutput(false);
-				}
-				// keep outer wrapper expanded on error
-				const autoExpandFailures = this._configurationService.getValue<boolean>(ChatConfiguration.AutoExpandToolFailures);
-				if (autoExpandFailures && resolvedImmediately.exitCode !== undefined && resolvedImmediately.exitCode !== 0 && this._thinkingCollapsibleWrapper) {
-					this.expandCollapsibleWrapper();
-				}
+				this._handleCommandCompletion(resolvedImmediately);
 				return;
 			}
 		};
@@ -740,6 +855,29 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 		this._continueInBackgroundAction.clear();
 	}
 
+	/**
+	 * Handles the completion of a terminal command by updating the UI state.
+	 * This includes marking the collapsible wrapper as complete, auto-collapsing
+	 * successful commands, and keeping failed commands expanded.
+	 *
+	 * @param resolvedCommand The completed terminal command with exit code information.
+	 */
+	private _handleCommandCompletion(resolvedCommand: ITerminalCommand | undefined): void {
+		// Update title to show completion state
+		this.markCollapsibleWrapperComplete();
+
+		// Auto-collapse on success (exit code 0)
+		if (resolvedCommand?.exitCode === 0 && this._outputView.isExpanded && !this._userToggledOutput) {
+			this._toggleOutput(false);
+		}
+
+		// Keep outer wrapper expanded on error for visibility
+		const autoExpandFailures = this._configurationService.getValue<boolean>(ChatConfiguration.AutoExpandToolFailures);
+		if (autoExpandFailures && resolvedCommand?.exitCode !== undefined && resolvedCommand.exitCode !== 0 && this._thinkingCollapsibleWrapper) {
+			this.expandCollapsibleWrapper();
+		}
+	}
+
 	private async _toggleOutput(expanded: boolean): Promise<boolean> {
 		const didChange = await this._outputView.toggle(expanded);
 		const isExpanded = this._outputView.isExpanded;
@@ -864,6 +1002,21 @@ export class ChatTerminalToolProgressPart extends BaseChatToolInvocationSubPart
 	}
 }
 
+/**
+ * A component that displays terminal command output in an expandable/collapsible section.
+ *
+ * This component supports two modes of displaying output:
+ * - **Live output**: Mirrors the output from a running terminal instance in real-time,
+ *   supporting streaming updates, scroll-lock behavior, and user input forwarding.
+ * - **Snapshot output**: Displays a static snapshot of previously captured terminal output,
+ *   useful for serialized/restored chat sessions.
+ *
+ * Features:
+ * - Automatic height calculation based on line count (min/max row limits)
+ * - Scroll-lock behavior: stays at bottom during streaming, respects user scroll position
+ * - Accessibility: proper ARIA labels and accessible view support
+ * - Theme-aware background color that adapts to panel vs editor context
+ */
 class ChatTerminalToolOutputSection extends Disposable {
 	public readonly domNode: HTMLElement;
 
@@ -1117,9 +1270,8 @@ class ChatTerminalToolOutputSection extends Disposable {
 		// 1. Command is running but executedMarker isn't set yet (renderCommand returns undefined)
 		// 2. Command finished quickly but buffer isn't ready yet
 		if (!hasOutput) {
-			const maxRetries = 10;
-			for (let retry = 0; retry < maxRetries && !hasOutput; retry++) {
-				await timeout(100);
+			for (let retry = 0; retry < MAX_OUTPUT_POLL_RETRIES && !hasOutput; retry++) {
+				await timeout(OUTPUT_POLL_DELAY_MS);
 				if (this._store.isDisposed) {
 					return true;
 				}
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatToolConfirmationSubPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatToolConfirmationSubPart.ts
index 4d4423755620b..93eb27ff036be 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatToolConfirmationSubPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatToolConfirmationSubPart.ts
@@ -13,7 +13,6 @@ import { isEmptyObject } from '../../../../../../../base/common/types.js';
 import { generateUuid } from '../../../../../../../base/common/uuid.js';
 import { ElementSizeObserver } from '../../../../../../../editor/browser/config/elementSizeObserver.js';
 import { ILanguageService } from '../../../../../../../editor/common/languages/language.js';
-import { IModelService } from '../../../../../../../editor/common/services/model.js';
 import { localize } from '../../../../../../../nls.js';
 import { ICommandService } from '../../../../../../../platform/commands/common/commands.js';
 import { IContextKeyService } from '../../../../../../../platform/contextkey/common/contextkey.js';
@@ -53,7 +52,6 @@ export class ToolConfirmationSubPart extends AbstractToolConfirmationSubPart {
 		private readonly codeBlockStartIndex: number,
 		@IInstantiationService instantiationService: IInstantiationService,
 		@IKeybindingService keybindingService: IKeybindingService,
-		@IModelService private readonly modelService: IModelService,
 		@ILanguageService private readonly languageService: ILanguageService,
 		@IContextKeyService contextKeyService: IContextKeyService,
 		@IChatWidgetService chatWidgetService: IChatWidgetService,
@@ -185,13 +183,14 @@ export class ToolConfirmationSubPart extends AbstractToolConfirmationSubPart {
 				const langId = this.languageService.getLanguageIdByLanguageName('json');
 				const rawJsonInput = JSON.stringify(inputData.rawInput ?? {}, null, 1);
 				const canSeeMore = count(rawJsonInput, '\n') > 2; // if more than one key:value
-				const model = this._register(this.modelService.createModel(
+				const modelRef = this._register(this.context.inlineTextModels.acquire(
+					createToolInputUri(toolInvocation.toolCallId),
 					// View a single JSON line by default until they 'see more'
 					rawJsonInput.replace(/\n */g, ' '),
 					this.languageService.createById(langId),
-					createToolInputUri(toolInvocation.toolCallId),
 					true
 				));
+				const model = modelRef.object;
 
 				const markerOwner = generateUuid();
 				const schemaUri = createToolSchemaUri(toolInvocation.toolId);
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatToolInvocationPart.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatToolInvocationPart.ts
index 8b2f2365905c0..eacf8b39b11ec 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatToolInvocationPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatToolInvocationPart.ts
@@ -23,6 +23,7 @@ import { ChatInputOutputMarkdownProgressPart } from './chatInputOutputMarkdownPr
 import { ChatMcpAppSubPart, IMcpAppRenderData } from './chatMcpAppSubPart.js';
 import { ChatResultListSubPart } from './chatResultListSubPart.js';
 import { ChatSimpleToolProgressPart } from './chatSimpleToolProgressPart.js';
+import { ChatModifiedFilesConfirmationSubPart } from './chatModifiedFilesConfirmationSubPart.js';
 import { ChatTerminalToolConfirmationSubPart } from './chatTerminalToolConfirmationSubPart.js';
 import { ChatTerminalToolProgressPart } from './chatTerminalToolProgressPart.js';
 import { ToolConfirmationSubPart } from './chatToolConfirmationSubPart.js';
@@ -120,6 +121,7 @@ export class ChatToolInvocationPart extends Disposable implements IChatContentPa
 			// Add class when displaying a confirmation widget
 			const isConfirmation = this.subPart instanceof ToolConfirmationSubPart ||
 				this.subPart instanceof ChatTerminalToolConfirmationSubPart ||
+				this.subPart instanceof ChatModifiedFilesConfirmationSubPart ||
 				this.subPart instanceof ExtensionsInstallConfirmationWidgetSubPart ||
 				this.subPart instanceof ChatToolPostExecuteConfirmationPart;
 			this.domNode.classList.toggle('has-confirmation', isConfirmation);
@@ -173,6 +175,8 @@ export class ChatToolInvocationPart extends Disposable implements IChatContentPa
 			if (state.type === IChatToolInvocation.StateKind.WaitingForConfirmation) {
 				if (this.toolInvocation.toolSpecificData?.kind === 'terminal') {
 					return this.instantiationService.createInstance(ChatTerminalToolConfirmationSubPart, this.toolInvocation, this.toolInvocation.toolSpecificData, this.context, this.renderer, this.editorPool, this.currentWidthDelegate, this.codeBlockModelCollection, this.codeBlockStartIndex);
+				} else if (this.toolInvocation.toolSpecificData?.kind === 'modifiedFilesConfirmation') {
+					return this.instantiationService.createInstance(ChatModifiedFilesConfirmationSubPart, this.toolInvocation, this.context, this.listPool);
 				} else {
 					return this.instantiationService.createInstance(ToolConfirmationSubPart, this.toolInvocation, this.context, this.renderer, this.editorPool, this.currentWidthDelegate, this.codeBlockModelCollection, this.codeBlockStartIndex);
 				}
@@ -222,6 +226,7 @@ export class ChatToolInvocationPart extends Disposable implements IChatContentPa
 				this.toolInvocation.pastTenseMessage ?? this.toolInvocation.invocationMessage,
 				this.toolInvocation.originMessage,
 				resultDetails.input,
+				resultDetails.inputLanguage,
 				resultDetails.output,
 				!!resultDetails.isError,
 			);
@@ -237,6 +242,7 @@ export class ChatToolInvocationPart extends Disposable implements IChatContentPa
 				this.toolInvocation.originMessage,
 				typeof this.toolInvocation.toolSpecificData.rawInput === 'string' ? this.toolInvocation.toolSpecificData.rawInput : JSON.stringify(this.toolInvocation.toolSpecificData.rawInput, null, 2),
 				undefined,
+				undefined,
 				false,
 			);
 		}
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatToolPartUtilities.ts b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatToolPartUtilities.ts
index aa7a82177c6fc..0aba9ec84a9d7 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatToolPartUtilities.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatContentParts/toolInvocationParts/chatToolPartUtilities.ts
@@ -30,7 +30,7 @@ export function getApprovalMessageFromReason(reason: ConfirmedReason): IMarkdown
 	let md: string;
 	switch (reason.type) {
 		case ToolConfirmKind.Setting:
-			md = localize('chat.autoapprove.setting', 'Auto approved by {0}', createMarkdownCommandLink({ title: '`' + reason.id + '`', id: 'workbench.action.openSettings', arguments: [reason.id] }, false));
+			md = localize('chat.autoapprove.setting', 'Auto approved by {0}', createMarkdownCommandLink({ text: '`' + reason.id + '`', id: 'workbench.action.openSettings', arguments: [reason.id], tooltip: localize('openSettings.tooltip', 'Open settings') }, false));
 			break;
 		case ToolConfirmKind.LmServicePerTool:
 			md = reason.scope === 'session'
@@ -38,7 +38,7 @@ export function getApprovalMessageFromReason(reason: ConfirmedReason): IMarkdown
 				: reason.scope === 'workspace'
 					? localize('chat.autoapprove.lmServicePerTool.workspace', 'Auto approved for this workspace')
 					: localize('chat.autoapprove.lmServicePerTool.profile', 'Auto approved for this profile');
-			md += ' (' + createMarkdownCommandLink({ title: localize('edit', 'Edit'), id: 'workbench.action.chat.editToolApproval', arguments: [reason.scope] }) + ')';
+			md += ' (' + createMarkdownCommandLink({ text: localize('edit', 'Edit'), id: 'workbench.action.chat.editToolApproval', arguments: [reason.scope], tooltip: localize('editToolApproval.tooltip', 'Edit tool approval settings') }) + ')';
 			break;
 		case ToolConfirmKind.ConfirmationNotNeeded:
 			if (reason.reason) {
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatListRenderer.ts b/src/vs/workbench/contrib/chat/browser/widget/chatListRenderer.ts
index ae17dc3f8ba9f..441cdcaaf361a 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatListRenderer.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatListRenderer.ts
@@ -23,7 +23,6 @@ import { FuzzyScore } from '../../../../../base/common/filters.js';
 import { MarkdownString } from '../../../../../base/common/htmlContent.js';
 import { Iterable } from '../../../../../base/common/iterator.js';
 import { KeyCode } from '../../../../../base/common/keyCodes.js';
-import { CancellationTokenSource } from '../../../../../base/common/cancellation.js';
 import { Disposable, DisposableStore, IDisposable, dispose, thenIfNotDisposed, toDisposable } from '../../../../../base/common/lifecycle.js';
 import { ResourceMap } from '../../../../../base/common/map.js';
 import { ScrollEvent } from '../../../../../base/common/scrollable.js';
@@ -50,13 +49,13 @@ import { AccessibilitySignal, IAccessibilitySignalService } from '../../../../..
 import { IChatEntitlementService } from '../../../../services/chat/common/chatEntitlementService.js';
 import { IWorkbenchIssueService } from '../../../issue/common/issue.js';
 import { CodiconActionViewItem } from '../../../notebook/browser/view/cellParts/cellActionView.js';
-import { annotateSpecialMarkdownContent, extractSubAgentInvocationIdFromText, hasCodeblockUriTag } from '../../common/widget/annotations.js';
+import { annotateSpecialMarkdownContent, extractSubAgentInvocationIdFromText, hasCodeblockUriTag, hasEditCodeblockUriTag } from '../../common/widget/annotations.js';
 import { checkModeOption } from '../../common/chat.js';
 import { IChatAgentMetadata } from '../../common/participants/chatAgents.js';
 import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
 import { IChatTextEditGroup } from '../../common/model/chatModel.js';
 import { chatSubcommandLeader } from '../../common/requestParser/chatParserTypes.js';
-import { ChatAgentVoteDirection, ChatAgentVoteDownReason, ChatErrorLevel, ChatRequestQueueKind, IChatConfirmation, IChatContentReference, IChatDisabledClaudeHooksPart, IChatElicitationRequest, IChatElicitationRequestSerialized, IChatExtensionsContent, IChatFollowup, IChatHookPart, IChatMarkdownContent, IChatMcpServersStarting, IChatMcpServersStartingSerialized, IChatMultiDiffData, IChatMultiDiffDataSerialized, IChatPullRequestContent, IChatQuestionCarousel, IChatService, IChatTask, IChatTaskSerialized, IChatThinkingPart, IChatToolInvocation, IChatToolInvocationSerialized, IChatTreeData, IChatUndoStop, isChatFollowup } from '../../common/chatService/chatService.js';
+import { ChatAgentVoteDirection, ChatAgentVoteDownReason, ChatErrorLevel, ChatRequestQueueKind, IChatConfirmation, IChatContentReference, IChatDisabledClaudeHooksPart, IChatElicitationRequest, IChatElicitationRequestSerialized, IChatExtensionsContent, IChatFollowup, IChatHookPart, IChatMarkdownContent, IChatMcpServersStarting, IChatMcpServersStartingSerialized, IChatMultiDiffData, IChatMultiDiffDataSerialized, IChatPullRequestContent, IChatQuestionAnswerValue, IChatQuestionAnswers, IChatQuestionCarousel, IChatService, IChatTask, IChatTaskSerialized, IChatThinkingPart, IChatToolInvocation, IChatToolInvocationSerialized, IChatTreeData, IChatUndoStop, isChatFollowup } from '../../common/chatService/chatService.js';
 import { ChatQuestionCarouselData } from '../../common/model/chatProgressTypes/chatQuestionCarouselData.js';
 import { localChatSessionType } from '../../common/chatSessionsService.js';
 import { getChatSessionType } from '../../common/model/chatUri.js';
@@ -78,7 +77,7 @@ import { ChatCodeCitationContentPart } from './chatContentParts/chatCodeCitation
 import { ChatCommandButtonContentPart } from './chatContentParts/chatCommandContentPart.js';
 import { ChatConfirmationContentPart } from './chatContentParts/chatConfirmationContentPart.js';
 import { DiffEditorPool, EditorPool } from './chatContentParts/chatContentCodePools.js';
-import { IChatContentPart, IChatContentPartRenderContext } from './chatContentParts/chatContentParts.js';
+import { IChatContentPart, IChatContentPartRenderContext, InlineTextModelCollection } from './chatContentParts/chatContentParts.js';
 import { ChatElicitationContentPart } from './chatContentParts/chatElicitationContentPart.js';
 import { ChatErrorConfirmationContentPart } from './chatContentParts/chatErrorConfirmationPart.js';
 import { ChatErrorContentPart } from './chatContentParts/chatErrorContentPart.js';
@@ -107,9 +106,9 @@ import { isEqual } from '../../../../../base/common/resources.js';
 import { IAccessibilityService } from '../../../../../platform/accessibility/common/accessibility.js';
 import { ChatHookContentPart } from './chatContentParts/chatHookContentPart.js';
 import { ChatPendingDragController } from './chatPendingDragAndDrop.js';
-import { HookType } from '../../common/promptSyntax/hookSchema.js';
-import { ChatQuestionCarouselAutoReply } from './chatQuestionCarouselAutoReply.js';
+import { HookType } from '../../common/promptSyntax/hookTypes.js';
 import { IWorkbenchEnvironmentService } from '../../../../services/environment/common/environmentService.js';
+import { AccessibilityWorkbenchSettingId } from '../../../accessibility/browser/accessibilityConfiguration.js';
 
 const $ = dom.$;
 
@@ -195,9 +194,6 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 
 	/** Track pending question carousels by session resource for auto-skip on chat submission */
 	private readonly pendingQuestionCarousels = new ResourceMap<Set<ChatQuestionCarouselPart>>();
-	private readonly _autoRepliedQuestionCarousels = new Set<string>();
-	private readonly _autoReply: ChatQuestionCarouselAutoReply;
-
 	private readonly _notifiedQuestionCarousels = new Set<string>();
 
 	private readonly chatContentMarkdownRenderer: IMarkdownRenderer;
@@ -242,6 +238,7 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 	 * TODO@roblourens shouldn't use the CodeBlockModelCollection at all
 	 */
 	private readonly _toolInvocationCodeBlockCollection: CodeBlockModelCollection;
+	private readonly _inlineTextModels: InlineTextModelCollection;
 
 	/**
 	 * Prevents re-announcement of already rendered chat progress
@@ -281,9 +278,8 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		this._contentReferencesListPool = this._register(this.instantiationService.createInstance(CollapsibleListPool, this._onDidChangeVisibility.event, undefined, undefined));
 
 		this._register(this.instantiationService.createInstance(ChatCodeBlockContentProvider));
+		this._inlineTextModels = this._register(this.instantiationService.createInstance(InlineTextModelCollection));
 		this._toolInvocationCodeBlockCollection = this._register(this.instantiationService.createInstance(CodeBlockModelCollection, 'tools'));
-		this._autoReply = this._register(this.instantiationService.createInstance(ChatQuestionCarouselAutoReply));
-
 		// Auto-skip pending question carousels when user submits a new chat message
 		this._register(this.chatService.onDidSubmitRequest(e => {
 			const carousels = this.pendingQuestionCarousels.get(e.chatSessionResource);
@@ -294,6 +290,18 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 				carousels.clear();
 			}
 		}));
+
+		// Auto-skip all pending question carousels when auto-reply is enabled mid-session
+		this._register(this.configService.onDidChangeConfiguration(e => {
+			if (e.affectsConfiguration(ChatConfiguration.AutoReply) && this.configService.getValue<boolean>(ChatConfiguration.AutoReply)) {
+				for (const [, carousels] of this.pendingQuestionCarousels) {
+					for (const carousel of carousels) {
+						carousel.skip();
+					}
+					carousels.clear();
+				}
+			}
+		}));
 	}
 
 	private _pendingDragController: ChatPendingDragController | undefined;
@@ -324,6 +332,23 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		}
 	}
 
+	private fireItemHeightChange(template: IChatListItemTemplate, measuredHeight?: number): void {
+		if (!template.currentElement || !template.rowContainer.isConnected) {
+			return;
+		}
+
+		const height = measuredHeight ?? template.rowContainer.getBoundingClientRect().height;
+		if (height === 0 || !height) {
+			return;
+		}
+
+		const normalizedHeight = Math.ceil(height);
+		template.currentElement.currentRenderedHeight = normalizedHeight;
+		if (template.currentElement !== this._elementBeingRendered) {
+			this._onDidChangeItemHeight.fire({ element: template.currentElement, height: normalizedHeight });
+		}
+	}
+
 	/**
 	 * Compute a rate to render at in words/s.
 	 */
@@ -359,7 +384,6 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 	updateViewModel(viewModel: IChatViewModel | undefined): void {
 		this.viewModel = viewModel;
 		this._announcedToolProgressKeys.clear();
-		this._autoRepliedQuestionCarousels.clear();
 		this._notifiedQuestionCarousels.clear();
 		this.codeBlocksByEditorUri.clear();
 		this.codeBlocksByResponseId.clear();
@@ -512,7 +536,6 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		}
 
 		const footerToolbar = templateDisposables.add(scopedInstantiationService.createInstance(MenuWorkbenchToolBar, footerToolbarContainer, MenuId.ChatMessageFooter, {
-			eventDebounceDelay: 0,
 			menuOptions: { shouldForwardArgs: true, renderShortTitle: true },
 			toolbarOptions: { shouldInlineSubmenu: submenu => submenu.actions.length <= 1 },
 			actionViewItemProvider: (action: IAction, options: IActionViewItemOptions) => {
@@ -610,23 +633,9 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		}));
 
 		const resizeObserver = templateDisposables.add(new dom.DisposableResizeObserver((entries) => {
-			if (!template.currentElement) {
-				return;
-			}
-
 			const entry = entries[0];
 			if (entry) {
-				const height = entry.borderBoxSize.at(0)?.blockSize;
-				if (height === 0 || !height || !template.rowContainer.isConnected) {
-					// Don't fire for changes that happen from the row being removed from the DOM
-					return;
-				}
-
-				const normalizedHeight = Math.ceil(height);
-				template.currentElement.currentRenderedHeight = normalizedHeight;
-				if (template.currentElement !== this._elementBeingRendered) {
-					this._onDidChangeItemHeight.fire({ element: template.currentElement, height: normalizedHeight });
-				}
+				this.fireItemHeightChange(template, entry.borderBoxSize.at(0)?.blockSize);
 			}
 		}));
 		templateDisposables.add(resizeObserver.observe(rowContainer));
@@ -652,6 +661,8 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 			dispose(coalesce(templateData.renderedParts));
 			templateData.renderedParts = undefined;
 			dom.clearNode(templateData.value);
+		} else if (isPendingDividerVM(templateData.currentElement)) {
+			dom.clearNode(templateData.value);
 		}
 
 		// This template item is no longer in use, or having another element rendered into it,
@@ -678,6 +689,14 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		templateData.currentElement = element;
 		this.templateDataByRequestId.set(element.id, templateData);
 
+		// Clear pending-related classes and drag handle from previous renders
+		// Do this before element-type checks to ensure dividers also get cleaned up
+		templateData.rowContainer.classList.remove('pending-item', 'pending-divider', 'pending-request', 'chat-pending-dragging');
+		templateData.dragHandle?.remove();
+		templateData.dragHandle = undefined;
+		delete templateData.rowContainer.dataset.pendingRequestId;
+		delete templateData.rowContainer.dataset.pendingKind;
+
 		// Handle pending divider with simplified rendering
 		if (isPendingDividerVM(element)) {
 			this.renderPendingDivider(element, templateData);
@@ -723,12 +742,6 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		templateData.rowContainer.classList.toggle('editing-session', location === ChatAgentLocation.Chat);
 		templateData.rowContainer.classList.toggle('interactive-request', isRequestVM(element));
 		templateData.rowContainer.classList.toggle('interactive-response', isResponseVM(element));
-		// Clear pending-related classes and drag handle from previous renders
-		templateData.rowContainer.classList.remove('pending-item', 'pending-divider', 'pending-request');
-		templateData.dragHandle?.remove();
-		templateData.dragHandle = undefined;
-		delete templateData.rowContainer.dataset.pendingRequestId;
-		delete templateData.rowContainer.dataset.pendingKind;
 		const progressMessageAtBottomOfResponse = checkModeOption(this.delegate.currentChatMode(), this.rendererOptions.progressMessageAtBottomOfResponse);
 		templateData.rowContainer.classList.toggle('show-detail-progress', isResponseVM(element) && !element.isComplete && !element.progressMessages.length && !progressMessageAtBottomOfResponse);
 		if (!this.rendererOptions.noHeader) {
@@ -752,6 +765,12 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 
 		templateData.checkpointContainer.classList.toggle('hidden', isResponseVM(element) || isPendingRequest || !(checkpointEnabled));
 
+		// Force toolbars to synchronously re-evaluate after context key changes
+		// to avoid size measurement issues from the debounced menu update.
+		templateData.footerToolbar.refresh();
+		templateData.checkpointToolbar.refresh();
+		templateData.checkpointRestoreToolbar.refresh();
+
 		// Track response template data by request ID for cross-row hover effects
 		if (isResponseVM(element)) {
 			this.responseTemplateDataByRequestId.set(element.requestId, templateData);
@@ -909,6 +928,14 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 			dom.append(templateData.detail, $('span.confirmation-text', undefined, localize('chatConfirmationAction', 'Selected "{0}"', element.confirmation)));
 			templateData.header?.classList.remove('header-disabled');
 			templateData.header?.classList.add('partially-disabled');
+
+			const updateCheckmarks = () => templateData.detail.classList.toggle('show-checkmarks', !!this.configService.getValue<boolean>(AccessibilityWorkbenchSettingId.ShowChatCheckmarks));
+			updateCheckmarks();
+			templateData.elementDisposables.add(this.configService.onDidChangeConfiguration(e => {
+				if (e.affectsConfiguration(AccessibilityWorkbenchSettingId.ShowChatCheckmarks)) {
+					updateCheckmarks();
+				}
+			}));
 		}
 	}
 
@@ -983,7 +1010,7 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		this.renderChatContentDiff(diff, content, element, index, templateData);
 	}
 
-	private shouldShowWorkingProgress(element: IChatResponseViewModel, partsToRender: IChatRendererContent[], templateData: IChatListItemTemplate): boolean {
+	private shouldShowWorkingProgress(element: IChatResponseViewModel, partsToRender: IChatRendererContent[], moreContentAvailable: boolean, templateData: IChatListItemTemplate): boolean {
 		if (element.agentOrSlashCommandDetected || this.rendererOptions.renderStyle === 'minimal' || element.isComplete || !checkModeOption(this.delegate.currentChatMode(), this.rendererOptions.progressMessageAtBottomOfResponse)) {
 			return false;
 		}
@@ -996,10 +1023,6 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		// Show if no content, only "used references", ends with a complete tool call, or ends with complete text edits and there is no incomplete tool call (edits are still being applied some time after they are all generated)
 		const lastPart = findLast(partsToRender, part => part.kind !== 'markdownContent' || part.content.value.trim().length > 0);
 
-		// don't show working progress when there is thinking content in partsToRender (about to be rendered)
-		if (partsToRender.some(part => part.kind === 'thinking')) {
-			return false;
-		}
 
 		// never show working progress when there is an active thinking piece
 		const lastThinking = this.getLastThinkingPart(templateData.renderedParts);
@@ -1007,18 +1030,22 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 			return false;
 		}
 
-		const collapsedToolsMode = this.configService.getValue<CollapsedToolsDisplayMode>('chat.agent.thinking.collapsedTools');
-		if (collapsedToolsMode !== CollapsedToolsDisplayMode.Off &&
-			partsToRender.some(part =>
-				(part.kind === 'toolInvocation' || part.kind === 'toolInvocationSerialized') &&
-				this.shouldPinPart(part, element)
-			)) {
-			return false;
+		// Never show working when the last part is a tool invocation that is attached to thinking,
+		// or *will be* attached to thinking during the upcoming render pass
+		if (lastPart && (lastPart.kind === 'toolInvocation' || lastPart.kind === 'toolInvocationSerialized')) {
+			if (lastPart.isAttachedToThinking) {
+				return false;
+			}
+			const collapsedToolsMode = this.configService.getValue<CollapsedToolsDisplayMode>('chat.agent.thinking.collapsedTools');
+			if (collapsedToolsMode !== CollapsedToolsDisplayMode.Off && this.shouldPinPart(lastPart, isResponseVM(element) ? element : undefined)) {
+				return false;
+			}
 		}
 
 
+
 		const hasRenderedThinkingPart = (templateData.renderedParts ?? []).some(part => part instanceof ChatThinkingContentPart);
-		const hasEditPillMarkdown = partsToRender.some(part => part.kind === 'markdownContent' && this.hasCodeblockUri(part));
+		const hasEditPillMarkdown = partsToRender.some(part => part.kind === 'markdownContent' && this.hasEditCodeblockUri(part));
 		if (hasRenderedThinkingPart && hasEditPillMarkdown) {
 			return false;
 		}
@@ -1031,6 +1058,7 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		if (
 			!lastPart ||
 			lastPart.kind === 'references' ||
+			(lastPart.kind === 'markdownContent' && !moreContentAvailable) ||
 			((lastPart.kind === 'toolInvocation' || lastPart.kind === 'toolInvocationSerialized') && (IChatToolInvocation.isComplete(lastPart) || lastPart.presentation === 'hidden')) ||
 			((lastPart.kind === 'textEditGroup' || lastPart.kind === 'notebookEditGroup') && lastPart.done && !partsToRender.some(part => part.kind === 'toolInvocation' && !IChatToolInvocation.isComplete(part))) ||
 			(lastPart.kind === 'progressTask' && lastPart.deferred.isSettled) ||
@@ -1110,6 +1138,7 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		const parts: IChatContentPart[] = [];
 
 		let inlineSlashCommandRendered = false;
+		let codeBlockStartIndex = 0;
 		content.forEach((data, contentIndex) => {
 			const context: IChatContentPartRenderContext = {
 				element,
@@ -1122,12 +1151,9 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 				codeBlockModelCollection: this.codeBlockModelCollection,
 				currentWidth: this._currentLayoutWidth,
 				onDidChangeVisibility: this._onDidChangeVisibility.event,
-				get codeBlockStartIndex() {
-					return parts.reduce((acc, part) => acc + (part.codeblocks?.length ?? 0), 0);
-				},
-				get treeStartIndex() {
-					return parts.filter(part => part instanceof ChatTreeContentPart).length;
-				}
+				inlineTextModels: this._inlineTextModels,
+				codeBlockStartIndex,
+				treeStartIndex: 0, // no trees in requests
 			};
 			const newPart = this.renderChatContentPart(data, templateData, context);
 			if (newPart) {
@@ -1150,6 +1176,7 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 					templateData.value.appendChild(newPart.domNode);
 				}
 				parts.push(newPart);
+				codeBlockStartIndex += newPart.codeblocks?.length ?? 0;
 			}
 		});
 
@@ -1218,7 +1245,20 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		const renderedParts = templateData.renderedParts ?? [];
 		templateData.renderedParts = renderedParts;
 		const lastMarkdownIndex = partsToRender.findLastIndex(part => part?.kind === 'markdownContent');
+		let codeBlockStartIndex = 0;
+		let treeStartIndex = 0;
 		partsToRender.forEach((partToRender, contentIndex) => {
+			// Accumulate counts from the part that ended up at the previous index
+			if (contentIndex > 0) {
+				const prevPart = renderedParts[contentIndex - 1];
+				if (prevPart) {
+					codeBlockStartIndex += prevPart.codeblocks?.length ?? 0;
+					if (prevPart instanceof ChatTreeContentPart) {
+						treeStartIndex++;
+					}
+				}
+			}
+
 			const alreadyRenderedPart = templateData.renderedParts?.[contentIndex];
 			const isFinalAnswerPart = partToRender?.kind === 'markdownContent' && contentIndex === lastMarkdownIndex && element.isComplete;
 
@@ -1256,7 +1296,6 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 				}
 			}
 
-			const preceedingContentParts = renderedParts.slice(0, contentIndex);
 			const context: IChatContentPartRenderContext = {
 				element,
 				elementIndex: elementIndex,
@@ -1268,12 +1307,9 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 				codeBlockModelCollection: this.codeBlockModelCollection,
 				currentWidth: this._currentLayoutWidth,
 				onDidChangeVisibility: this._onDidChangeVisibility.event,
-				get codeBlockStartIndex() {
-					return preceedingContentParts.reduce((acc, part) => acc + (part.codeblocks?.length ?? 0), 0);
-				},
-				get treeStartIndex() {
-					return preceedingContentParts.filter(part => part instanceof ChatTreeContentPart).length;
-				}
+				inlineTextModels: this._inlineTextModels,
+				codeBlockStartIndex,
+				treeStartIndex,
 			};
 
 			// combine tool invocations into thinking part if needed. render the tool, but do not replace the working spinner with the new part's dom node since it is already inside the thinking part.
@@ -1390,7 +1426,7 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 			element.renderData = { lastRenderTime: Date.now(), renderedWordCount: newRenderedWordCount, renderedParts: partsToRender };
 		}
 
-		if (this.shouldShowWorkingProgress(element, partsToRender, templateData)) {
+		if (this.shouldShowWorkingProgress(element, partsToRender, moreContentAvailable, templateData)) {
 			partsToRender.push({ kind: 'working' });
 		}
 
@@ -1468,11 +1504,11 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		return !!dom.findParentWithClass(renderedPart.domNode, 'chat-thinking-box');
 	}
 
-	private hasCodeblockUri(part: IChatRendererContent): boolean {
+	private hasEditCodeblockUri(part: IChatRendererContent): boolean {
 		if (part.kind !== 'markdownContent') {
 			return false;
 		}
-		return hasCodeblockUriTag(part.content.value);
+		return hasEditCodeblockUriTag(part.content.value);
 	}
 
 	private isCodeblockComplete(part: IChatRendererContent, element: ChatTreeItem): boolean {
@@ -1509,7 +1545,7 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		}
 
 		// is an edit related part
-		if (this.hasCodeblockUri(part) || part.kind === 'textEditGroup') {
+		if (this.hasEditCodeblockUri(part) || part.kind === 'textEditGroup') {
 			return true;
 		}
 
@@ -1756,7 +1792,8 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 			} else if (content.kind === 'markdownContent') {
 				return this.renderMarkdown(content, templateData, context);
 			} else if (content.kind === 'references') {
-				if (isResponseVM(context.element) && context.element.model.request?.modeInfo?.modeId === ChatModeKind.Agent) {
+				// Only show references for chat participants, not agents
+				if (isResponseVM(context.element) && context.element.agent?.isDefault && !context.element.agent.modes.includes(ChatModeKind.Ask)) {
 					return this.renderNoContent(other => other.kind === content.kind);
 				}
 				return this.renderContentReferencesListData(content, undefined, context, templateData);
@@ -1951,6 +1988,7 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 
 				if (thinkingPart instanceof ChatThinkingContentPart) {
 					// Append using factory - thinking part decides whether to render lazily
+					toolInvocation.isAttachedToThinking = true;
 					thinkingPart.appendItem(createToolPart, toolInvocation.toolId, toolInvocation, templateData.value);
 					this.setupConfirmationTransitionWatcher(toolInvocation, thinkingPart, () => lazilyCreatedPart, createToolPart, context, templateData);
 				}
@@ -1961,6 +1999,7 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 			if (this.shouldPinPart(toolInvocation, context.element)) {
 				if (lastThinking && toolInvocation.presentation !== 'hidden') {
 					// Append using factory - thinking part decides whether to render lazily
+					toolInvocation.isAttachedToThinking = true;
 					lastThinking.appendItem(createToolPart, toolInvocation.toolId, toolInvocation, templateData.value);
 					this.setupConfirmationTransitionWatcher(toolInvocation, lastThinking, () => lazilyCreatedPart, createToolPart, context, templateData);
 					return this.renderNoContent((other, followingContent, element) => lazilyCreatedPart ?
@@ -2000,6 +2039,7 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		const removeConfirmationWidget = () => {
 			const createdPart = getCreatedPart();
 			// move the created part out of thinking and into the main template
+			toolInvocation.isAttachedToThinking = false;
 			if (createdPart?.domNode) {
 				const wrapper = createdPart.domNode.parentElement;
 				if (wrapper?.classList.contains('chat-thinking-tool-wrapper')) {
@@ -2134,18 +2174,16 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 
 		const widget = isResponseVM(context.element) ? this.chatWidgetService.getWidgetBySessionResource(context.element.sessionResource) : undefined;
 		const shouldAutoFocus = widget ? widget.getInput() === '' : true;
-		const modelName = widget?.input.currentLanguageModel;
 		const responseId = isResponseVM(context.element) ? context.element.requestId : undefined;
-		const requestMessageText = isResponseVM(context.element) ? this.getRequestMessageText(context.element) : undefined;
 
-		const handleSubmit = async (answers: Map<string, unknown> | undefined, part: ChatQuestionCarouselPart) => {
+		const handleSubmit = async (answers: Map<string, IChatQuestionAnswerValue> | undefined, part: ChatQuestionCarouselPart) => {
 			// Mark the carousel as used and store the answers
-			const answersRecord = answers ? Object.fromEntries(answers) : undefined;
-			if (answersRecord) {
-				carousel.data = answersRecord;
-			}
+			const answersRecord: IChatQuestionAnswers | undefined = answers ? Object.fromEntries(answers) : undefined;
+			carousel.data = answersRecord ?? {};
 			carousel.isUsed = true;
 			if (carousel instanceof ChatQuestionCarouselData) {
+				carousel.draftAnswers = undefined;
+				carousel.draftCurrentIndex = undefined;
 				carousel.completion.complete({ answers: answersRecord });
 			}
 
@@ -2157,8 +2195,9 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 			// Remove from pending carousels
 			this.removeCarouselFromTracking(context, part);
 
-			// Clear from input part (always clear on submit, no response check needed)
-			widget?.input.clearQuestionCarousel();
+			// Clear from input part (clear only the submitted carousel by its key)
+			const carouselKey = carousel.resolveId ?? `${responseId}_${context.contentIndex}`;
+			widget?.input.clearQuestionCarousel(undefined, carouselKey);
 		};
 
 		// If carousel is already used or response is complete/canceled, render summary inline in the list
@@ -2166,10 +2205,12 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		const inputPartHasCarousel = widget?.input.questionCarousel !== undefined;
 
 		if (carousel.isUsed || responseIsComplete) {
-			if (responseIsComplete && !carousel.isUsed && isResponseVM(context.element) && carousel.resolveId && carousel.data === undefined) {
+			if (responseIsComplete && !carousel.isUsed && isResponseVM(context.element) && carousel.resolveId) {
 				carousel.data = {};
 				carousel.isUsed = true;
 				if (carousel instanceof ChatQuestionCarouselData) {
+					carousel.draftAnswers = undefined;
+					carousel.draftCurrentIndex = undefined;
 					carousel.completion.complete({ answers: undefined });
 				}
 				this.chatService.notifyQuestionCarouselAnswer(context.element.requestId, carousel.resolveId, undefined);
@@ -2202,12 +2243,9 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 				shouldAutoFocus,
 				onSubmit: async (answers) => handleSubmit(answers, fallbackPart)
 			});
-			this.maybeAutoReplyToQuestionCarousel(context, carousel, fallbackPart, answers => handleSubmit(answers, fallbackPart), modelName, requestMessageText);
 			return fallbackPart;
 		}
 
-		this.maybeAutoReplyToQuestionCarousel(context, carousel, part, answers => handleSubmit(answers, part), modelName, requestMessageText);
-
 		// Track the carousel for auto-skip when user submits a new message
 		// Only add tracking if not already tracked (prevents duplicate tracking on re-render)
 		if (isResponseVM(context.element) && carousel.allowSkip && !carousel.isUsed) {
@@ -2285,61 +2323,6 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		// OS toast notification is handled by ChatWindowNotifier
 	}
 
-	private maybeAutoReplyToQuestionCarousel(
-		context: IChatContentPartRenderContext,
-		carousel: IChatQuestionCarousel,
-		part: ChatQuestionCarouselPart,
-		submit: (answers: Map<string, unknown> | undefined) => Promise<void>,
-		modelName: string | undefined,
-		requestMessageText: string | undefined,
-	): void {
-		if (carousel.isUsed) {
-			return;
-		}
-
-		// Use a stable key based on requestId + resolveId to prevent duplicate
-		// auto-replies across re-renders of the same logical carousel.
-		const stableKey = this._getCarouselStableKey(context, carousel);
-		if (stableKey) {
-			if (this._autoRepliedQuestionCarousels.has(stableKey)) {
-				return;
-			}
-			// Mark as in-progress before the async opt-in check to prevent
-			// duplicate prompts/requests from concurrent re-renders.
-			this._autoRepliedQuestionCarousels.add(stableKey);
-		}
-
-		void this._autoReply.shouldAutoReply().then(shouldAutoReply => {
-			if (!shouldAutoReply) {
-				// Roll back the in-progress mark if auto-reply is not enabled.
-				if (stableKey) {
-					this._autoRepliedQuestionCarousels.delete(stableKey);
-				}
-				return;
-			}
-
-			const cts = new CancellationTokenSource();
-			part.addDisposable(toDisposable(() => {
-				cts.cancel();
-				cts.dispose();
-			}));
-
-			this._autoReply.autoReply(carousel, submit, modelName, requestMessageText, cts.token).catch(err => {
-				this.logService.debug('#ChatQuestionCarousel: Auto reply failed', toErrorMessage(err));
-			});
-		});
-	}
-
-
-	private getRequestMessageText(response: IChatResponseViewModel): string | undefined {
-		const requestId = response.requestId;
-		const items = response.session.getItems();
-		const request = items.find(item => isRequestVM(item) && item.id === requestId) as IChatRequestViewModel | undefined;
-		return request?.messageText;
-	}
-
-
-
 	private removeCarouselFromTracking(context: IChatContentPartRenderContext, part: ChatQuestionCarouselPart): void {
 		if (isResponseVM(context.element)) {
 			const carousels = this.pendingQuestionCarousels.get(context.element.sessionResource);
@@ -2372,12 +2355,20 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 		const isFinalRenderPass = isResponseVM(element) && element.isComplete && !element.renderData;
 		const lastPinnedPartIndex = isFinalRenderPass ? context.content.findLastIndex(c => c.kind === 'thinking' || c.kind === 'toolInvocation' || c.kind === 'toolInvocationSerialized') : -1;
 		const isFinalAnswerPart = isFinalRenderPass && context.contentIndex > lastPinnedPartIndex;
-		if (!this.hasCodeblockUri(markdown) || isFinalAnswerPart) {
+		const isBlankMarkdown = !markdown.content.value.trim();
+		// Don't finalize thinking if the markdown has an incomplete codeblock with a
+		// vscode_codeblock_uri tag — the isEdit annotation may not have arrived yet.
+		// Only check codeblocks that contain a URI tag to avoid catching regular non-edit codeblocks.
+		const hasPendingEditCodeblock = isResponseVM(element) && !element.isComplete
+			&& hasCodeblockUriTag(markdown.content.value)
+			&& !codeblockHasClosingBackticks(markdown.content.value);
+		if ((!this.hasEditCodeblockUri(markdown) || isFinalAnswerPart) && !isBlankMarkdown && !hasPendingEditCodeblock) {
 			this.finalizeCurrentThinkingPart(context, templateData);
 		}
 		const fillInIncompleteTokens = isResponseVM(element) && (!element.isComplete || element.isCanceled || element.errorDetails?.responseIsFiltered || element.errorDetails?.responseIsIncomplete || !!element.renderData);
 		const codeBlockStartIndex = context.codeBlockStartIndex;
 		const markdownPart = templateData.instantiationService.createInstance(ChatMarkdownContentPart, markdown, context, this._editorPool, fillInIncompleteTokens, codeBlockStartIndex, this.chatContentMarkdownRenderer, undefined, this._currentLayoutWidth.get(), this.codeBlockModelCollection, {});
+		markdownPart.addDisposable(markdownPart.onDidChangeHeight(() => this.fireItemHeightChange(templateData)));
 		if (isRequestVM(element)) {
 			markdownPart.domNode.tabIndex = 0;
 			if (this.configService.getValue<string>('chat.editRequests') === 'inline' && this.rendererOptions.editable) {
@@ -2477,7 +2468,7 @@ export class ChatListItemRenderer extends Disposable implements ITreeRenderer<Ch
 						templateData.value
 					);
 				}
-			} else if (!this.shouldPinPart(markdown, context.element)) {
+			} else if (!this.shouldPinPart(markdown, context.element) && !isBlankMarkdown && !hasPendingEditCodeblock) {
 				this.finalizeCurrentThinkingPart(context, templateData);
 			}
 		}
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatQuestionCarouselAutoReply.ts b/src/vs/workbench/contrib/chat/browser/widget/chatQuestionCarouselAutoReply.ts
deleted file mode 100644
index eca6e1608144a..0000000000000
--- a/src/vs/workbench/contrib/chat/browser/widget/chatQuestionCarouselAutoReply.ts
+++ /dev/null
@@ -1,455 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-
-import { Codicon } from '../../../../../base/common/codicons.js';
-import { toErrorMessage } from '../../../../../base/common/errorMessage.js';
-import { MarkdownString } from '../../../../../base/common/htmlContent.js';
-import { CancellationToken } from '../../../../../base/common/cancellation.js';
-import { Disposable } from '../../../../../base/common/lifecycle.js';
-import Severity from '../../../../../base/common/severity.js';
-import { hasKey } from '../../../../../base/common/types.js';
-import { localize } from '../../../../../nls.js';
-import { IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
-import { IDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
-import { ExtensionIdentifier } from '../../../../../platform/extensions/common/extensions.js';
-import { ILogService } from '../../../../../platform/log/common/log.js';
-import { IStorageService, StorageScope, StorageTarget } from '../../../../../platform/storage/common/storage.js';
-import { IChatQuestion, IChatQuestionCarousel } from '../../common/chatService/chatService.js';
-import { ChatConfiguration } from '../../common/constants.js';
-import { ChatMessageRole, getTextResponseFromStream, ILanguageModelsService } from '../../common/languageModels.js';
-import { Event } from '../../../../../base/common/event.js';
-
-const enum AutoReplyStorageKeys {
-	AutoReplyOptIn = 'chat.autoReply.optIn'
-}
-
-/**
- * Encapsulates the logic for automatically replying to question carousels,
- * including opt-in state management, LLM-based answer resolution, fallback
- * answer generation, and answer parsing/merging.
- */
-export class ChatQuestionCarouselAutoReply extends Disposable {
-
-	constructor(
-		@IConfigurationService private readonly configService: IConfigurationService,
-		@IDialogService private readonly dialogService: IDialogService,
-		@ILogService private readonly logService: ILogService,
-		@IStorageService private readonly storageService: IStorageService,
-		@ILanguageModelsService private readonly languageModelsService: ILanguageModelsService,
-	) {
-		super();
-
-		// Clear out warning accepted state if the setting is disabled
-		this._register(Event.runAndSubscribe(this.configService.onDidChangeConfiguration, e => {
-			if (!e || e.affectsConfiguration(ChatConfiguration.AutoReply)) {
-				if (this.configService.getValue(ChatConfiguration.AutoReply) !== true) {
-					this.storageService.remove(AutoReplyStorageKeys.AutoReplyOptIn, StorageScope.APPLICATION);
-				}
-			}
-		}));
-	}
-
-	async shouldAutoReply(): Promise<boolean> {
-		if (!this.configService.getValue<boolean>(ChatConfiguration.AutoReply)) {
-			return false;
-		}
-		return this.checkOptIn();
-	}
-
-	async autoReply(
-		carousel: IChatQuestionCarousel,
-		submit: (answers: Map<string, unknown> | undefined) => Promise<void>,
-		modelName: string | undefined,
-		requestMessageText: string | undefined,
-		token: CancellationToken,
-	): Promise<void> {
-		if (token.isCancellationRequested || carousel.isUsed || carousel.questions.length === 0) {
-			return;
-		}
-
-		const fallbackAnswers = this.buildFallbackCarouselAnswers(carousel, requestMessageText);
-		let resolvedAnswers = fallbackAnswers;
-
-		const modelId = await this.getModelId(modelName);
-		if (modelId && !token.isCancellationRequested) {
-			try {
-				const parsedAnswers = await this.requestAnswers(modelId, carousel, requestMessageText, token);
-				if (parsedAnswers.size > 0) {
-					resolvedAnswers = this.mergeAnswers(carousel, parsedAnswers, fallbackAnswers);
-				}
-			} catch (err) {
-				this.logService.debug('#ChatQuestionCarousel: Failed to resolve auto reply', toErrorMessage(err));
-			}
-		}
-
-		if (token.isCancellationRequested || carousel.isUsed) {
-			return;
-		}
-
-		await submit(resolvedAnswers);
-	}
-
-	// #region Opt-in
-
-	private async checkOptIn(): Promise<boolean> {
-		const optedIn = this.storageService.getBoolean(AutoReplyStorageKeys.AutoReplyOptIn, StorageScope.APPLICATION, false);
-		if (optedIn) {
-			return true;
-		}
-
-		const promptResult = await this.dialogService.prompt({
-			type: Severity.Warning,
-			message: localize('chat.autoReply.enable.title', 'Enable chat auto reply?'),
-			buttons: [
-				{
-					label: localize('chat.autoReply.enable', 'Enable'),
-					run: () => true
-				},
-				{
-					label: localize('chat.autoReply.disable', 'Disable'),
-					run: () => false
-				},
-			],
-			custom: {
-				icon: Codicon.warning,
-				disableCloseAction: true,
-				markdownDetails: [{
-					markdown: new MarkdownString(localize('chat.autoReply.enable.details', 'Chat auto reply answers question carousels using the current model and may make unintended choices. Review your settings and outputs carefully.')),
-				}],
-			}
-		});
-
-		if (promptResult.result !== true) {
-			await this.configService.updateValue(ChatConfiguration.AutoReply, false);
-			return false;
-		}
-
-		this.storageService.store(AutoReplyStorageKeys.AutoReplyOptIn, true, StorageScope.APPLICATION, StorageTarget.USER);
-		return true;
-	}
-
-	// #endregion
-
-	// #region LLM interaction
-
-	private async getModelId(modelName: string | undefined): Promise<string | undefined> {
-		if (!modelName) {
-			return undefined;
-		}
-
-		let models = await this.languageModelsService.selectLanguageModels({ id: modelName });
-		if (models.length > 0) {
-			return models[0];
-		}
-
-		if (modelName.startsWith('copilot/')) {
-			models = await this.languageModelsService.selectLanguageModels({ vendor: 'copilot', family: modelName.replace(/^copilot\//, '') });
-			return models[0];
-		}
-
-		return undefined;
-	}
-
-	private buildPrompt(carousel: IChatQuestionCarousel, requestMessageText: string | undefined, strict: boolean): string {
-		const questions = carousel.questions.map(question => ({
-			id: question.id,
-			type: question.type,
-			title: question.title,
-			message: typeof question.message === 'string' ? question.message : question.message?.value,
-			options: question.options?.map(option => ({ id: option.id, label: option.label })) ?? [],
-			allowFreeformInput: question.allowFreeformInput ?? false,
-		}));
-
-		const contextLines: string[] = [];
-		if (requestMessageText) {
-			contextLines.push(`Original user request: ${JSON.stringify(requestMessageText)}`);
-		}
-
-		return [
-			'Choose default answers for the following questions.',
-			'Return a JSON object keyed by question id.',
-			'For text questions, the value should be a string.',
-			'For singleSelect questions, the value should be { "selectedId": string } or { "freeform": string }.',
-			'For multiSelect questions, the value should be { "selectedIds": string[] } and may include { "freeform": string }.',
-			'If a question allows freeform input and has no options, return a freeform answer based on the user request when possible.',
-			'Use option ids from the provided options.',
-			...contextLines,
-			'Questions:',
-			JSON.stringify(questions),
-			strict ? 'Return ONLY valid JSON. Do not include markdown or explanations.' : undefined,
-		].filter(Boolean).join('\n');
-	}
-
-	private async requestAnswers(
-		modelId: string,
-		carousel: IChatQuestionCarousel,
-		requestMessageText: string | undefined,
-		token: CancellationToken,
-	): Promise<Map<string, unknown>> {
-		const prompt = this.buildPrompt(carousel, requestMessageText, false);
-		const response = await this.languageModelsService.sendChatRequest(
-			modelId,
-			new ExtensionIdentifier('core'),
-			[{ role: ChatMessageRole.User, content: [{ type: 'text', value: prompt }] }],
-			{},
-			token,
-		);
-		const responseText = await getTextResponseFromStream(response);
-		const parsedAnswers = this.parseAnswers(responseText, carousel);
-		if (parsedAnswers.size > 0 || token.isCancellationRequested) {
-			return parsedAnswers;
-		}
-
-		const retryPrompt = this.buildPrompt(carousel, requestMessageText, true);
-		const retryResponse = await this.languageModelsService.sendChatRequest(
-			modelId,
-			new ExtensionIdentifier('core'),
-			[{ role: ChatMessageRole.User, content: [{ type: 'text', value: retryPrompt }] }],
-			{},
-			token,
-		);
-		const retryText = await getTextResponseFromStream(retryResponse);
-		return this.parseAnswers(retryText, carousel);
-	}
-
-	// #endregion
-
-	// #region Answer parsing and resolution
-
-	private parseAnswers(responseText: string, carousel: IChatQuestionCarousel): Map<string, unknown> {
-		const parsed = this.tryParseJsonObject(responseText);
-		if (!parsed) {
-			return new Map();
-		}
-
-		const answers = new Map<string, unknown>();
-		for (const question of carousel.questions) {
-			const rawAnswer = parsed[question.id];
-			const resolved = this.resolveAnswerFromRaw(question, rawAnswer);
-			if (resolved !== undefined) {
-				answers.set(question.id, resolved);
-			}
-		}
-		return answers;
-	}
-
-	private mergeAnswers(
-		carousel: IChatQuestionCarousel,
-		resolvedAnswers: Map<string, unknown>,
-		fallbackAnswers: Map<string, unknown>,
-	): Map<string, unknown> {
-		const merged = new Map<string, unknown>();
-		for (const question of carousel.questions) {
-			const fallback = fallbackAnswers.get(question.id);
-			if (this.hasDefaultValue(question) && fallback !== undefined) {
-				merged.set(question.id, fallback);
-				continue;
-			}
-			if (resolvedAnswers.has(question.id)) {
-				merged.set(question.id, resolvedAnswers.get(question.id)!);
-				continue;
-			}
-			if (fallback !== undefined) {
-				merged.set(question.id, fallback);
-			}
-		}
-		return merged;
-	}
-
-	private hasDefaultValue(question: IChatQuestion): boolean {
-		switch (question.type) {
-			case 'text':
-				return question.defaultValue !== undefined;
-			case 'singleSelect':
-				return typeof question.defaultValue === 'string';
-			case 'multiSelect':
-				return Array.isArray(question.defaultValue)
-					? question.defaultValue.length > 0
-					: typeof question.defaultValue === 'string';
-		}
-	}
-
-	private resolveAnswerFromRaw(question: IChatQuestion, raw: unknown): unknown | undefined {
-		switch (question.type) {
-			case 'text': {
-				if (typeof raw === 'string') {
-					const value = raw.trim();
-					return value.length > 0 ? value : undefined;
-				}
-				if (raw && typeof raw === 'object' && hasKey(raw, { value: true }) && typeof (raw as { value: unknown }).value === 'string') {
-					const value = (raw as { value: string }).value.trim();
-					return value.length > 0 ? value : undefined;
-				}
-				return undefined;
-			}
-			case 'singleSelect': {
-				let selectedInput: string | undefined;
-				let freeformInput: string | undefined;
-				if (typeof raw === 'string') {
-					selectedInput = raw;
-				} else if (raw && typeof raw === 'object') {
-					if (hasKey(raw, { selectedId: true }) && typeof (raw as { selectedId: unknown }).selectedId === 'string') {
-						selectedInput = (raw as { selectedId: string }).selectedId;
-					} else if (hasKey(raw, { selectedLabel: true }) && typeof (raw as { selectedLabel: unknown }).selectedLabel === 'string') {
-						selectedInput = (raw as { selectedLabel: string }).selectedLabel;
-					}
-					if (hasKey(raw, { freeform: true }) && typeof (raw as { freeform: unknown }).freeform === 'string') {
-						freeformInput = (raw as { freeform: string }).freeform;
-					}
-				}
-
-				if (freeformInput && freeformInput.trim().length > 0) {
-					return { selectedValue: undefined, freeformValue: freeformInput.trim() };
-				}
-
-				const match = selectedInput ? this.matchQuestionOption(question, selectedInput) : undefined;
-				if (match) {
-					return { selectedValue: match.value, freeformValue: undefined };
-				}
-				return undefined;
-			}
-			case 'multiSelect': {
-				let selectedInputs: string[] = [];
-				let freeformInput: string | undefined;
-				if (Array.isArray(raw)) {
-					selectedInputs = raw.filter(item => typeof item === 'string') as string[];
-				} else if (typeof raw === 'string') {
-					selectedInputs = raw.split(',').map(item => item.trim()).filter(item => item.length > 0);
-				} else if (raw && typeof raw === 'object') {
-					if (hasKey(raw, { selectedIds: true })) {
-						const selectedIdsValue = (raw as { selectedIds?: unknown }).selectedIds;
-						if (Array.isArray(selectedIdsValue)) {
-							selectedInputs = selectedIdsValue.filter((item: unknown): item is string => typeof item === 'string');
-						}
-					}
-					if (hasKey(raw, { freeform: true }) && typeof (raw as { freeform?: unknown }).freeform === 'string') {
-						freeformInput = (raw as { freeform: string }).freeform;
-					}
-				}
-
-				const selectedValues = selectedInputs
-					.map(input => this.matchQuestionOption(question, input)?.value)
-					.filter(value => value !== undefined);
-				const freeformValue = freeformInput?.trim();
-
-				if (selectedValues.length > 0 || (freeformValue && freeformValue.length > 0)) {
-					return { selectedValues, freeformValue };
-				}
-				return undefined;
-			}
-		}
-	}
-
-	private matchQuestionOption(question: IChatQuestion, rawInput: string): { id: string; value: unknown } | undefined {
-		const options = question.options ?? [];
-		if (!options.length) {
-			return undefined;
-		}
-
-		const normalized = rawInput.trim().toLowerCase();
-		const numeric = Number.parseInt(normalized, 10);
-		if (!Number.isNaN(numeric) && numeric > 0 && numeric <= options.length) {
-			const option = options[numeric - 1];
-			return { id: option.id, value: option.value };
-		}
-
-		const exactId = options.find(option => option.id.toLowerCase() === normalized);
-		if (exactId) {
-			return { id: exactId.id, value: exactId.value };
-		}
-		const exactLabel = options.find(option => option.label.toLowerCase() === normalized);
-		if (exactLabel) {
-			return { id: exactLabel.id, value: exactLabel.value };
-		}
-		const partialLabel = options.find(option => option.label.toLowerCase().includes(normalized));
-		if (partialLabel) {
-			return { id: partialLabel.id, value: partialLabel.value };
-		}
-
-		return undefined;
-	}
-
-	// #endregion
-
-	// #region Fallback answers
-
-	buildFallbackCarouselAnswers(carousel: IChatQuestionCarousel, requestMessageText: string | undefined): Map<string, unknown> {
-		const answers = new Map<string, unknown>();
-		for (const question of carousel.questions) {
-			const answer = this.getFallbackAnswerForQuestion(question, requestMessageText);
-			if (answer !== undefined) {
-				answers.set(question.id, answer);
-			}
-		}
-		return answers;
-	}
-
-	private getFallbackAnswerForQuestion(question: IChatQuestion, requestMessageText: string | undefined): unknown {
-		const fallbackFreeform = requestMessageText?.trim() || localize('chat.questionCarousel.autoReplyFallback', 'OK');
-
-		switch (question.type) {
-			case 'text':
-				return question.defaultValue ?? fallbackFreeform;
-			case 'singleSelect': {
-				const defaultOptionId = typeof question.defaultValue === 'string' ? question.defaultValue : undefined;
-				const defaultOption = defaultOptionId ? question.options?.find(opt => opt.id === defaultOptionId) : undefined;
-				if (defaultOption) {
-					return { selectedValue: defaultOption.value, freeformValue: undefined };
-				}
-				if (question.options && question.options.length > 0) {
-					return { selectedValue: question.options[0].value, freeformValue: undefined };
-				}
-				if (question.allowFreeformInput) {
-					return { selectedValue: undefined, freeformValue: fallbackFreeform };
-				}
-				return undefined;
-			}
-			case 'multiSelect': {
-				const defaultIds = Array.isArray(question.defaultValue)
-					? question.defaultValue
-					: (typeof question.defaultValue === 'string' ? [question.defaultValue] : []);
-				const selectedValues = question.options
-					?.filter(opt => defaultIds.includes(opt.id))
-					.map(opt => opt.value)
-					.filter(value => value !== undefined) ?? [];
-				if (selectedValues.length > 0) {
-					return { selectedValues, freeformValue: undefined };
-				}
-				if (question.options && question.options.length > 0) {
-					return { selectedValues: [question.options[0].value], freeformValue: undefined };
-				}
-				if (question.allowFreeformInput) {
-					return { selectedValues: [], freeformValue: fallbackFreeform };
-				}
-				return undefined;
-			}
-		}
-	}
-
-	// #endregion
-
-	// #region Utilities
-
-	private tryParseJsonObject(text: string): Record<string, unknown> | undefined {
-		const trimmed = text.trim();
-		if (!trimmed) {
-			return undefined;
-		}
-		const start = trimmed.indexOf('{');
-		const end = trimmed.lastIndexOf('}');
-		const candidate = start >= 0 && end > start ? trimmed.slice(start, end + 1) : trimmed;
-		try {
-			const parsed = JSON.parse(candidate) as unknown;
-			if (parsed && typeof parsed === 'object' && !Array.isArray(parsed)) {
-				return parsed as Record<string, unknown>;
-			}
-		} catch {
-			return undefined;
-		}
-		return undefined;
-	}
-
-	// #endregion
-}
diff --git a/src/vs/workbench/contrib/chat/browser/widget/chatWidget.ts b/src/vs/workbench/contrib/chat/browser/widget/chatWidget.ts
index 9b1dea8a0be3e..ab48ca5e1b8b1 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/chatWidget.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/chatWidget.ts
@@ -20,9 +20,10 @@ import { Iterable } from '../../../../../base/common/iterator.js';
 import { Disposable, DisposableStore, IDisposable, MutableDisposable, thenIfNotDisposed } from '../../../../../base/common/lifecycle.js';
 import { ResourceSet } from '../../../../../base/common/map.js';
 import { Schemas } from '../../../../../base/common/network.js';
+import { IsSessionsWindowContext } from '../../../../common/contextkeys.js';
 import { filter } from '../../../../../base/common/objects.js';
 import { autorun, derived, observableFromEvent, observableValue } from '../../../../../base/common/observable.js';
-import { basename, extUri, isEqual } from '../../../../../base/common/resources.js';
+import { extUri, isEqual } from '../../../../../base/common/resources.js';
 import { MicrotaskDelay } from '../../../../../base/common/symbols.js';
 import { isDefined } from '../../../../../base/common/types.js';
 import { URI } from '../../../../../base/common/uri.js';
@@ -33,7 +34,7 @@ import { Range } from '../../../../../editor/common/core/range.js';
 import { localize } from '../../../../../nls.js';
 import { MenuId } from '../../../../../platform/actions/common/actions.js';
 import { IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
-import { ContextKeyExpr, IContextKey, IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
+import { IContextKey, IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
 import { IDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
 
 import { ITextResourceEditorInput } from '../../../../../platform/editor/common/editor.js';
@@ -44,9 +45,6 @@ import { bindContextKey } from '../../../../../platform/observable/common/platfo
 import product from '../../../../../platform/product/common/product.js';
 import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
 import { IThemeService } from '../../../../../platform/theme/common/themeService.js';
-import { IWorkspaceContextService, WorkbenchState } from '../../../../../platform/workspace/common/workspace.js';
-import { EditorResourceAccessor } from '../../../../common/editor.js';
-import { IEditorService } from '../../../../services/editor/common/editorService.js';
 import { IChatEntitlementService } from '../../../../services/chat/common/chatEntitlementService.js';
 import { ILifecycleService } from '../../../../services/lifecycle/common/lifecycle.js';
 import { checkModeOption } from '../../common/chat.js';
@@ -55,9 +53,10 @@ import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
 import { applyingChatEditsFailedContextKey, decidedChatEditingResourceContextKey, hasAppliedChatEditsContextKey, hasUndecidedChatEditingResourceContextKey, IChatEditingService, IChatEditingSession, inChatEditingSessionContextKey, ModifiedFileEntryState } from '../../common/editing/chatEditingService.js';
 import { IChatLayoutService } from '../../common/widget/chatLayoutService.js';
 import { IChatModel, IChatModelInputState, IChatResponseModel } from '../../common/model/chatModel.js';
-import { ChatMode, getModeNameForTelemetry, IChatModeService } from '../../common/chatModes.js';
+import { ChatMode, getModeNameForTelemetry, IChatMode, IChatModeService } from '../../common/chatModes.js';
 import { chatAgentLeader, ChatRequestAgentPart, ChatRequestDynamicVariablePart, ChatRequestSlashPromptPart, ChatRequestToolPart, ChatRequestToolSetPart, chatSubcommandLeader, formatChatQuestion, IParsedChatRequest } from '../../common/requestParser/chatParserTypes.js';
 import { ChatRequestParser } from '../../common/requestParser/chatRequestParser.js';
+import { getDynamicVariablesForWidget, getSelectedToolAndToolSetsForWidget } from '../attachments/chatVariables.js';
 import { ChatRequestQueueKind, ChatSendResult, IChatLocationData, IChatSendRequestOptions, IChatService } from '../../common/chatService/chatService.js';
 import { IChatSessionsService } from '../../common/chatSessionsService.js';
 import { IChatSlashCommandService } from '../../common/participants/chatSlashCommands.js';
@@ -65,13 +64,12 @@ import { IChatTodoListService } from '../../common/tools/chatTodoListService.js'
 import { ChatRequestVariableSet, IChatRequestVariableEntry, isPromptFileVariableEntry, isPromptTextVariableEntry, isWorkspaceVariableEntry, PromptFileVariableKind, toPromptFileVariableEntry } from '../../common/attachments/chatVariableEntries.js';
 import { ChatViewModel, IChatResponseViewModel, isRequestVM, isResponseVM } from '../../common/model/chatViewModel.js';
 import { CodeBlockModelCollection } from '../../common/widget/codeBlockModelCollection.js';
-import { ChatAgentLocation, ChatConfiguration, ChatModeKind } from '../../common/constants.js';
+import { ChatAgentLocation, ChatConfiguration, ChatModeKind, ChatPermissionLevel } from '../../common/constants.js';
 import { ILanguageModelToolsService, isToolSet } from '../../common/tools/languageModelToolsService.js';
 import { ComputeAutomaticInstructions } from '../../common/promptSyntax/computeAutomaticInstructions.js';
-import { PromptsConfig } from '../../common/promptSyntax/config/config.js';
 import { IHandOff, PromptHeader } from '../../common/promptSyntax/promptFileParser.js';
 import { IPromptsService, PromptsStorage } from '../../common/promptSyntax/service/promptsService.js';
-import { handleModeSwitch } from '../actions/chatActions.js';
+import { GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID, handleModeSwitch } from '../actions/chatActions.js';
 import { ChatTreeItem, IChatAcceptInputOptions, IChatAccessibilityService, IChatCodeBlockInfo, IChatFileTreeInfo, IChatListItemRendererOptions, IChatWidget, IChatWidgetService, IChatWidgetViewContext, IChatWidgetViewModelChangeEvent, IChatWidgetViewOptions, isIChatResourceViewContext, isIChatViewViewContext } from '../chat.js';
 import { ChatAttachmentModel } from '../attachments/chatAttachmentModel.js';
 import { IChatAttachmentResolveService } from '../attachments/chatAttachmentResolveService.js';
@@ -81,7 +79,7 @@ import { ChatInputPart, IChatInputPartOptions, IChatInputStyles } from './input/
 import { IChatListItemTemplate } from './chatListRenderer.js';
 import { ChatListWidget } from './chatListWidget.js';
 import { ChatEditorOptions } from './chatOptions.js';
-import { ChatViewWelcomePart, IChatSuggestedPrompts, IChatViewWelcomeContent } from '../viewsWelcome/chatViewWelcomeController.js';
+import { ChatViewWelcomePart, IChatViewWelcomeContent } from '../viewsWelcome/chatViewWelcomeController.js';
 import { IChatTipService } from '../chatTipService.js';
 import { ChatTipContentPart } from './chatContentParts/chatTipContentPart.js';
 import { ChatContentMarkdownRenderer } from './chatContentMarkdownRenderer.js';
@@ -186,9 +184,10 @@ const supportsAllAttachments: Required<IChatAgentAttachmentCapabilities> = {
 	supportsSymbolAttachments: true,
 	supportsTerminalAttachments: true,
 	supportsPromptAttachments: true,
+	supportsHandOffs: true,
 };
 
-const DISCLAIMER = localize('chatDisclaimer', "AI responses may be inaccurate.");
+const DISCLAIMER = localize('chatDisclaimer', "AI responses may be inaccurate");
 
 export class ChatWidget extends Disposable implements IChatWidget {
 
@@ -287,17 +286,13 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		displayName: string;
 	};
 	private readonly _lockedToCodingAgentContextKey: IContextKey<boolean>;
+	private readonly _lockedCodingAgentIdContextKey: IContextKey<string>;
 	private readonly _agentSupportsAttachmentsContextKey: IContextKey<boolean>;
 	private readonly _sessionIsEmptyContextKey: IContextKey<boolean>;
 	private readonly _hasPendingRequestsContextKey: IContextKey<boolean>;
 	private readonly _sessionHasDebugDataContextKey: IContextKey<boolean>;
 	private _attachmentCapabilities: IChatAgentAttachmentCapabilities = supportsAllAttachments;
 
-	// Cache for prompt file descriptions to avoid async calls during rendering
-	private readonly promptDescriptionsCache = new Map<string, string>();
-	private readonly promptUriCache = new Map<string, URI>();
-	private _isLoadingPromptDescriptions = false;
-
 	private readonly viewModelDisposables = this._register(new DisposableStore());
 	private _viewModel: ChatViewModel | undefined;
 
@@ -340,7 +335,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 			}
 
 			this.parsedChatRequest = this.instantiationService.createInstance(ChatRequestParser)
-				.parseChatRequest(this.viewModel.sessionResource, this.getInput(), this.location, {
+				.parseChatRequestWithReferences(getDynamicVariablesForWidget(this), getSelectedToolAndToolSetsForWidget(this), this.getInput(), this.location, {
 					selectedAgent: this._lastSelectedAgent,
 					mode: this.input.currentModeKind,
 					attachmentCapabilities: this.attachmentCapabilities,
@@ -377,7 +372,6 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		private readonly viewOptions: IChatWidgetViewOptions,
 		private readonly styles: IChatWidgetStyles,
 		@ICodeEditorService private readonly codeEditorService: ICodeEditorService,
-		@IEditorService private readonly editorService: IEditorService,
 		@IConfigurationService private readonly configurationService: IConfigurationService,
 		@IDialogService private readonly dialogService: IDialogService,
 		@IContextKeyService private readonly contextKeyService: IContextKeyService,
@@ -399,7 +393,6 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		@IChatSessionsService private readonly chatSessionsService: IChatSessionsService,
 		@IAgentSessionsService private readonly agentSessionsService: IAgentSessionsService,
 		@IChatTodoListService private readonly chatTodoListService: IChatTodoListService,
-		@IWorkspaceContextService private readonly contextService: IWorkspaceContextService,
 		@ILifecycleService private readonly lifecycleService: ILifecycleService,
 		@IChatAttachmentResolveService private readonly chatAttachmentResolveService: IChatAttachmentResolveService,
 		@IChatTipService private readonly chatTipService: IChatTipService,
@@ -408,6 +401,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		super();
 
 		this._lockedToCodingAgentContextKey = ChatContextKeys.lockedToCodingAgent.bindTo(this.contextKeyService);
+		this._lockedCodingAgentIdContextKey = ChatContextKeys.lockedCodingAgentId.bindTo(this.contextKeyService);
 		this._agentSupportsAttachmentsContextKey = ChatContextKeys.agentSupportsAttachments.bindTo(this.contextKeyService);
 		this._sessionIsEmptyContextKey = ChatContextKeys.chatSessionIsEmpty.bindTo(this.contextKeyService);
 		this._hasPendingRequestsContextKey = ChatContextKeys.hasPendingRequests.bindTo(this.contextKeyService);
@@ -532,7 +526,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 			this.renderChatEditingSessionState();
 		}));
 
-		this._register(codeEditorService.registerCodeEditorOpenHandler(async (input: ITextResourceEditorInput, _source: ICodeEditor | null, _sideBySide?: boolean): Promise<ICodeEditor | null> => {
+		this._register(this.codeEditorService.registerCodeEditorOpenHandler(async (input: ITextResourceEditorInput, _source: ICodeEditor | null, _sideBySide?: boolean): Promise<ICodeEditor | null> => {
 			const resource = input.resource;
 			if (resource.scheme !== Schemas.vscodeChatCodeBlock) {
 				return null;
@@ -681,8 +675,8 @@ export class ChatWidget extends Disposable implements IChatWidget {
 				this.layout(this.bodyDimension.height, this.bodyDimension.width);
 			}
 		}));
-		this._register(this.chatSuggestNextWidget.onDidSelectPrompt(({ handoff, agentId }) => {
-			this.handleNextPromptSelection(handoff, agentId);
+		this._register(this.chatSuggestNextWidget.onDidSelectPrompt(({ handoff, agentId, withAutopilot }) => {
+			this.handleNextPromptSelection(handoff, agentId, withAutopilot);
 		}));
 
 		if (renderInputOnTop) {
@@ -699,6 +693,14 @@ export class ChatWidget extends Disposable implements IChatWidget {
 
 		// Forward scroll events from the parent container margins (outside the max-width area) to the chat list
 		this._register(dom.addDisposableListener(parent, dom.EventType.MOUSE_WHEEL, (e: IMouseWheelEvent) => {
+			if (e.defaultPrevented) {
+				return;
+			}
+
+			if (dom.isAncestor(e.target as Node | null, this.container)) {
+				return;
+			}
+
 			this.listWidget.delegateScrollFromMouseWheelEvent(e);
 		}));
 
@@ -855,7 +857,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		}
 
 		const previous = this.parsedChatRequest;
-		this.parsedChatRequest = this.instantiationService.createInstance(ChatRequestParser).parseChatRequest(this.viewModel.sessionResource, this.getInput(), this.location, { selectedAgent: this._lastSelectedAgent, mode: this.input.currentModeKind, attachmentCapabilities: this.attachmentCapabilities });
+		this.parsedChatRequest = this.instantiationService.createInstance(ChatRequestParser).parseChatRequestWithReferences(getDynamicVariablesForWidget(this), getSelectedToolAndToolSetsForWidget(this), this.getInput(), this.location, { selectedAgent: this._lastSelectedAgent, mode: this.input.currentModeKind, attachmentCapabilities: this.attachmentCapabilities });
 		if (!previous || !IParsedChatRequest.equals(previous, this.parsedChatRequest)) {
 			this._onDidChangeParsedInput.fire();
 		}
@@ -1022,18 +1024,23 @@ export class ChatWidget extends Disposable implements IChatWidget {
 
 		const tipContainer = this.inputPart.gettingStartedTipContainerElement;
 
-		// Already showing a tip
-		if (this._gettingStartedTipPart.value) {
-			dom.setVisibility(true, tipContainer);
-			return;
-		}
-
 		const tip = this.chatTipService.getWelcomeTip(this.contextKeyService);
 		if (!tip) {
+			if (this._gettingStartedTipPart.value) {
+				this._gettingStartedTipPartRef = undefined;
+				this._gettingStartedTipPart.clear();
+				dom.clearNode(tipContainer);
+			}
 			dom.setVisibility(false, tipContainer);
 			return;
 		}
 
+		// Already showing an eligible tip
+		if (this._gettingStartedTipPart.value) {
+			dom.setVisibility(true, tipContainer);
+			return;
+		}
+
 		const store = new DisposableStore();
 		const renderer = this.instantiationService.createInstance(ChatContentMarkdownRenderer);
 		const tipPart = store.add(this.instantiationService.createInstance(ChatTipContentPart,
@@ -1076,12 +1083,11 @@ export class ChatWidget extends Disposable implements IChatWidget {
 			return new MarkdownString('');
 		} else if (this._instructionFilesExist === false) {
 			// Show generate instructions message if no files exist
-			const generateInstructionsCommand = 'workbench.action.chat.generateInstructions';
 			return new MarkdownString(localize(
 				'chatWidget.instructions',
 				"[Generate Agent Instructions]({0}) to onboard AI onto your codebase.",
-				`command:${generateInstructionsCommand}`
-			), { isTrusted: { enabledCommands: [generateInstructionsCommand] } });
+				`command:${GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID}`
+			), { isTrusted: { enabledCommands: [GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID] } });
 		}
 
 		// While checking, don't show the generate instructions message
@@ -1107,9 +1113,10 @@ export class ChatWidget extends Disposable implements IChatWidget {
 	private getWelcomeViewContent(additionalMessage: string | IMarkdownString | undefined): IChatViewWelcomeContent {
 		if (this.isLockedToCodingAgent) {
 			// Check for provider-specific customizations from chat sessions service
-			const providerIcon = this._lockedAgent ? this.chatSessionsService.getIconForSessionType(this._lockedAgent.id) : undefined;
-			const providerTitle = this._lockedAgent ? this.chatSessionsService.getWelcomeTitleForSessionType(this._lockedAgent.id) : undefined;
-			const providerMessage = this._lockedAgent ? this.chatSessionsService.getWelcomeMessageForSessionType(this._lockedAgent.id) : undefined;
+			const contribution = this._lockedAgent ? this.chatSessionsService.getChatSessionContribution(this._lockedAgent.id) : undefined;
+			const providerIcon = contribution?.icon;
+			const providerTitle = contribution?.welcomeTitle;
+			const providerMessage = contribution?.welcomeMessage;
 
 			// Fallback to default messages if provider doesn't specify
 			const message = providerMessage
@@ -1141,183 +1148,9 @@ export class ChatWidget extends Disposable implements IChatWidget {
 			message: new MarkdownString(DISCLAIMER),
 			icon: Codicon.chatSparkle,
 			additionalMessage,
-			suggestedPrompts: this.getPromptFileSuggestions(),
 		};
 	}
 
-	private getPromptFileSuggestions(): IChatSuggestedPrompts[] {
-
-		// Use predefined suggestions for new users
-		if (!this.chatEntitlementService.sentiment.installed) {
-			const isEmpty = this.contextService.getWorkbenchState() === WorkbenchState.EMPTY;
-			if (isEmpty) {
-				return [
-					{
-						icon: Codicon.vscode,
-						label: localize('chatWidget.suggestedPrompts.gettingStarted', "Ask @vscode"),
-						prompt: localize('chatWidget.suggestedPrompts.gettingStartedPrompt', "@vscode How do I change the theme to light mode?"),
-					},
-					{
-						icon: Codicon.newFolder,
-						label: localize('chatWidget.suggestedPrompts.newProject', "Create Project"),
-						prompt: localize('chatWidget.suggestedPrompts.newProjectPrompt', "Create a #new Hello World project in TypeScript"),
-					}
-				];
-			} else {
-				return [
-					{
-						icon: Codicon.debugAlt,
-						label: localize('chatWidget.suggestedPrompts.buildWorkspace', "Build Workspace"),
-						prompt: localize('chatWidget.suggestedPrompts.buildWorkspacePrompt', "How do I build this workspace?"),
-					},
-					{
-						icon: Codicon.gear,
-						label: localize('chatWidget.suggestedPrompts.findConfig', "Show Config"),
-						prompt: localize('chatWidget.suggestedPrompts.findConfigPrompt', "Where is the configuration for this project defined?"),
-					}
-				];
-			}
-		}
-
-		// Get the current workspace folder context if available
-		const activeEditor = this.editorService.activeEditor;
-		const resource = activeEditor ? EditorResourceAccessor.getOriginalUri(activeEditor) : undefined;
-
-		// Get the prompt file suggestions configuration
-		const suggestions = PromptsConfig.getPromptFilesRecommendationsValue(this.configurationService, resource);
-		if (!suggestions) {
-			return [];
-		}
-
-		const result: IChatSuggestedPrompts[] = [];
-		const promptsToLoad: string[] = [];
-
-		// First, collect all prompts that need loading (regardless of shouldInclude)
-		for (const [promptName] of Object.entries(suggestions)) {
-			const description = this.promptDescriptionsCache.get(promptName);
-			if (description === undefined) {
-				promptsToLoad.push(promptName);
-			}
-		}
-
-		// If we have prompts to load, load them asynchronously and don't return anything yet
-		// But only if we're not already loading to prevent infinite loop
-		if (promptsToLoad.length > 0 && !this._isLoadingPromptDescriptions) {
-			this.loadPromptDescriptions(promptsToLoad);
-			return [];
-		}
-
-		// Now process the suggestions with loaded descriptions
-		const promptsWithScores: { promptName: string; condition: boolean | string; score: number }[] = [];
-
-		for (const [promptName, condition] of Object.entries(suggestions)) {
-			let score = 0;
-
-			// Handle boolean conditions
-			if (typeof condition === 'boolean') {
-				score = condition ? 1 : 0;
-			}
-			// Handle when clause conditions
-			else if (typeof condition === 'string') {
-				try {
-					const whenClause = ContextKeyExpr.deserialize(condition);
-					if (whenClause) {
-						// Test against all open code editors
-						const allEditors = this.codeEditorService.listCodeEditors();
-
-						if (allEditors.length > 0) {
-							// Count how many editors match the when clause
-							score = allEditors.reduce((count, editor) => {
-								try {
-									const editorContext = this.contextKeyService.getContext(editor.getDomNode());
-									return count + (whenClause.evaluate(editorContext) ? 1 : 0);
-								} catch (error) {
-									// Log error for this specific editor but continue with others
-									this.logService.warn('Failed to evaluate when clause for editor:', error);
-									return count;
-								}
-							}, 0);
-						} else {
-							// Fallback to global context if no editors are open
-							score = this.contextKeyService.contextMatchesRules(whenClause) ? 1 : 0;
-						}
-					} else {
-						score = 0;
-					}
-				} catch (error) {
-					// Log the error but don't fail completely
-					this.logService.warn('Failed to parse when clause for prompt file suggestion:', condition, error);
-					score = 0;
-				}
-			}
-
-			if (score > 0) {
-				promptsWithScores.push({ promptName, condition, score });
-			}
-		}
-
-		// Sort by score (descending) and take top 5
-		promptsWithScores.sort((a, b) => b.score - a.score);
-		const topPrompts = promptsWithScores.slice(0, 5);
-
-		// Build the final result array
-		for (const { promptName } of topPrompts) {
-			const description = this.promptDescriptionsCache.get(promptName);
-			const commandLabel = localize('chatWidget.promptFile.commandLabel', "{0}", promptName);
-			const uri = this.promptUriCache.get(promptName);
-			const descriptionText = description?.trim() ? description : undefined;
-			result.push({
-				icon: Codicon.run,
-				label: commandLabel,
-				description: descriptionText,
-				prompt: `/${promptName} `,
-				uri: uri
-			});
-		}
-
-		return result;
-	}
-
-	private async loadPromptDescriptions(promptNames: string[]): Promise<void> {
-		// Don't start loading if the widget is being disposed
-		if (this._store.isDisposed) {
-			return;
-		}
-
-		// Set loading guard to prevent infinite loop
-		this._isLoadingPromptDescriptions = true;
-		try {
-			// Get all available prompt files with their metadata
-			const promptCommands = await this.promptsService.getPromptSlashCommands(CancellationToken.None);
-
-			let cacheUpdated = false;
-			// Load descriptions only for the specified prompts
-			for (const promptCommand of promptCommands) {
-				if (promptNames.includes(promptCommand.name)) {
-					const description = promptCommand.description;
-					if (description) {
-						this.promptDescriptionsCache.set(promptCommand.name, description);
-						cacheUpdated = true;
-					} else {
-						// Set empty string to indicate we've checked this prompt
-						this.promptDescriptionsCache.set(promptCommand.name, '');
-						cacheUpdated = true;
-					}
-				}
-			}
-
-			// Fire event to trigger a re-render of the welcome view only if cache was updated
-			if (cacheUpdated) {
-				this.renderWelcomeViewContentIfNeeded();
-			}
-		} catch (error) {
-			this.logService.warn('Failed to load specific prompt descriptions:', error);
-		} finally {
-			// Always clear the loading guard, even on error
-			this._isLoadingPromptDescriptions = false;
-		}
-	}
-
 	private async renderChatEditingSessionState() {
 		if (!this.input) {
 			return;
@@ -1339,8 +1172,8 @@ export class ChatWidget extends Disposable implements IChatWidget {
 			return;
 		}
 
-		// Skip rendering in coding agent sessions
-		if (this.isLockedToCodingAgent) {
+		// Skip rendering in coding agent sessions unless the agent supports hand-offs
+		if (this.isLockedToCodingAgent && !this._attachmentCapabilities.supportsHandOffs) {
 			this.chatSuggestNextWidget.hide();
 			return;
 		}
@@ -1352,27 +1185,45 @@ export class ChatWidget extends Disposable implements IChatWidget {
 
 		const lastItem = items[items.length - 1];
 		const lastResponseComplete = lastItem && isResponseVM(lastItem) && lastItem.isComplete;
-		if (!lastResponseComplete) {
+		if (!lastResponseComplete || lastItem.isCanceled) {
+			this.chatSuggestNextWidget.hide();
 			return;
 		}
-		// Get the currently selected mode directly from the observable
-		// Note: We use currentModeObs instead of currentModeKind because currentModeKind returns
-		// the ChatModeKind enum (e.g., 'agent'), which doesn't distinguish between custom modes.
-		// Custom modes all have kind='agent' but different IDs.
-		const currentMode = this.input.currentModeObs.get();
-		const handoffs = currentMode?.handOffs?.get();
 
-		// Only show if: mode has handoffs AND chat has content AND not quick chat
-		const shouldShow = currentMode && handoffs && handoffs.length > 0;
+		// Derive handoffs from the mode that generated the last response, not the current UI selection.
+		// This ensures handoffs reflect what the response agent offers, regardless of mode picker state.
+		// Fall back to the current mode picker for old sessions where modeInfo was not persisted.
+		const modeInfo = lastItem.model.request?.modeInfo;
+		let responseMode: IChatMode | undefined;
+		if (modeInfo?.modeInstructions?.name) {
+			responseMode = this.chatModeService.findModeByName(modeInfo.modeInstructions.name);
+		} else if (modeInfo?.modeId) {
+			responseMode = this.chatModeService.findModeById(modeInfo.modeId);
+		} else {
+			responseMode = this.input.currentModeObs.get();
+		}
+
+		const handoffs = responseMode?.handOffs?.get();
+
+		if (responseMode && handoffs && handoffs.length > 0) {
+			// In Autopilot mode, automatically trigger the first auto-send handoff
+			// so the plan flows seamlessly into implementation without user interaction.
+			const permissionLevel = this.inputPart.currentModeInfo.permissionLevel;
+			if (permissionLevel === ChatPermissionLevel.Autopilot) {
+				const autoSendHandoff = handoffs.find(h => h.send);
+				if (autoSendHandoff) {
+					this.handleNextPromptSelection(autoSendHandoff);
+					return;
+				}
+			}
 
-		if (shouldShow) {
 			// Log telemetry only when widget transitions from hidden to visible
 			const wasHidden = this.chatSuggestNextWidget.domNode.style.display === 'none';
-			this.chatSuggestNextWidget.render(currentMode);
+			this.chatSuggestNextWidget.render(responseMode);
 
 			if (wasHidden) {
 				this.telemetryService.publicLog2<ChatHandoffWidgetShownEvent, ChatHandoffWidgetShownClassification>('chat.handoffWidgetShown', {
-					agent: getModeNameForTelemetry(currentMode),
+					agent: getModeNameForTelemetry(responseMode),
 					handoffCount: handoffs.length
 				});
 			}
@@ -1386,10 +1237,15 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		}
 	}
 
-	private handleNextPromptSelection(handoff: IHandOff, agentId?: string): void {
+	private handleNextPromptSelection(handoff: IHandOff, agentId?: string, withAutopilot?: boolean): void {
 		// Hide the widget after selection
 		this.chatSuggestNextWidget.hide();
 
+		// If starting with Autopilot, set permission level before submitting
+		if (withAutopilot) {
+			this.inputPart.setPermissionLevel(ChatPermissionLevel.Autopilot);
+		}
+
 		const promptToUse = handoff.prompt;
 
 		// Log telemetry
@@ -1543,8 +1399,9 @@ export class ChatWidget extends Disposable implements IChatWidget {
 	}
 
 	private async archiveLocalParentSession(sessionResource: URI): Promise<void> {
-		if (sessionResource.scheme !== Schemas.vscodeLocalChatSession) {
-			this.logService.debug(`[Delegation] archiveLocalParentSession: skipping, scheme=${sessionResource.scheme} is not vscodeLocalChatSession`);
+		// In the regular workbench, only archive local chat sessions.
+		// In the sessions window, allow archiving any session type after delegation.
+		if (sessionResource.scheme !== Schemas.vscodeLocalChatSession && !IsSessionsWindowContext.getValue(this.contextKeyService)) {
 			return;
 		}
 
@@ -1711,7 +1568,11 @@ export class ChatWidget extends Disposable implements IChatWidget {
 				ChatContextKeys.currentlyEditing.bindTo(item.contextKeyService).set(true);
 			}
 
-			const isEditingSentRequest = currentElement.pendingKind === undefined ? ChatContextKeys.EditingRequestType.Sent : ChatContextKeys.EditingRequestType.QueueOrSteer;
+			const isEditingSentRequest = currentElement.pendingKind === undefined
+				? ChatContextKeys.EditingRequestType.Sent
+				: currentElement.pendingKind === ChatRequestQueueKind.Queued
+					? ChatContextKeys.EditingRequestType.Queue
+					: ChatContextKeys.EditingRequestType.Steer;
 			const isInput = this.configurationService.getValue<string>('chat.editRequests') === 'input';
 			this.inputPart?.setEditing(!!this.viewModel?.editing && isInput, isEditingSentRequest);
 
@@ -1721,6 +1582,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 				rowContainer.appendChild(this.inputContainer);
 				this.createInput(this.inputContainer);
 				this.input.setChatMode(this.inputPart.currentModeObs.get().id);
+				this.input.setPermissionLevel(this.inputPart.currentModeInfo.permissionLevel ?? ChatPermissionLevel.Default);
 				this.input.setEditing(true, isEditingSentRequest);
 				this._onDidChangeActiveInputEditor.fire();
 			} else {
@@ -1821,6 +1683,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 
 		if (!isInput) {
 			this.inputPart.setChatMode(this.input.currentModeObs.get().id);
+			this.inputPart.setPermissionLevel(this.input.currentModeInfo.permissionLevel ?? ChatPermissionLevel.Default);
 			const currentModel = this.input.selectedLanguageModel.get();
 			if (currentModel) {
 				this.inputPart.switchModel(currentModel.metadata);
@@ -1899,10 +1762,12 @@ export class ChatWidget extends Disposable implements IChatWidget {
 			renderWorkingSet: this.viewOptions.enableWorkingSet === 'explicit',
 			supportsChangingModes: this.viewOptions.supportsChangingModes,
 			dndContainer: this.viewOptions.dndContainer,
+			inputEditorMinLines: this.viewOptions.inputEditorMinLines,
 			widgetViewKindTag: this.getWidgetViewKindTag(),
 			defaultMode: this.viewOptions.defaultMode,
 			sessionTypePickerDelegate: this.viewOptions.sessionTypePickerDelegate,
 			workspacePickerDelegate: this.viewOptions.workspacePickerDelegate,
+			isSessionsWindow: this.viewOptions.isSessionsWindow,
 		};
 
 		if (this.viewModel?.editing) {
@@ -2002,6 +1867,12 @@ export class ChatWidget extends Disposable implements IChatWidget {
 			this.renderFollowups();
 			this.renderChatSuggestNextWidget();
 		}));
+		const foregroundSessionCountContextKeys = new Set([ChatContextKeys.foregroundSessionCount.key]);
+		this._register(this.contextKeyService.onDidChangeContext(e => {
+			if (e.affectsSome(foregroundSessionCountContextKeys) && this.isEmpty()) {
+				this.renderGettingStartedTipIfNeeded();
+			}
+		}));
 		let previousModelIdentifier: string | undefined;
 		this._register(autorun(reader => {
 			const modelIdentifier = this.inputPart.selectedLanguageModel.read(reader)?.identifier;
@@ -2076,16 +1947,27 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		this.chatSuggestNextWidget.hide();
 		this.chatTipService.resetSession();
 
-		this._codeBlockModelCollection.clear();
+		// Switching sessions resets tip service state; clear any rendered tip so
+		// empty-state rendering picks a fresh, context-appropriate tip.
+		this._gettingStartedTipPartRef = undefined;
+		this._gettingStartedTipPart.clear();
+		const tipContainer = this.inputPart.gettingStartedTipContainerElement;
+		dom.clearNode(tipContainer);
+		dom.setVisibility(false, tipContainer);
 
-		this.viewModel = this.instantiationService.createInstance(ChatViewModel, model, this._codeBlockModelCollection, undefined);
+		this._codeBlockModelCollection.clear();
 
+		// Set the input model on the inputPart before assigning this.viewModel. Assigning this.viewModel
+		// fires onDidChangeViewModel, which ChatInputPart listens to and expects the input model to be initialized.
 		// Pass input model reference to input part for state syncing
 		this.inputPart.setInputModel(model.inputModel, model.getRequests().length === 0);
+
+		this.viewModel = this.instantiationService.createInstance(ChatViewModel, model, this._codeBlockModelCollection, undefined);
+
 		this.listWidget.setViewModel(this.viewModel);
 
 		if (this._lockedAgent) {
-			let placeholder = this.chatSessionsService.getInputPlaceholderForSessionType(this._lockedAgent.id);
+			let placeholder = this.chatSessionsService.getChatSessionContribution(this._lockedAgent.id)?.inputPlaceholder;
 			if (!placeholder) {
 				placeholder = localize('chat.input.placeholder.lockedToAgent', "Chat with {0}", this._lockedAgent.id);
 			}
@@ -2150,6 +2032,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 			if (e.kind === 'addRequest') {
 				this.inputPart.clearTodoListWidget(this.viewModel?.sessionResource, false);
 				this._sessionIsEmptyContextKey.set(false);
+				this.chatSuggestNextWidget.hide();
 			}
 			// Hide widget on request removal
 			if (e.kind === 'removeRequest') {
@@ -2180,6 +2063,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 			this.listWidget.scrollToEnd();
 		}
 
+		this.renderChatSuggestNextWidget();
 		this.updateChatInputContext();
 		this.input.renderChatTodoListWidget(this.viewModel.sessionResource);
 	}
@@ -2230,6 +2114,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 			displayName
 		};
 		this._lockedToCodingAgentContextKey.set(true);
+		this._lockedCodingAgentIdContextKey.set(agentId);
 		this.renderWelcomeViewContentIfNeeded();
 		// Update capabilities for the locked agent
 		const agent = this.chatAgentService.getAgent(agentId);
@@ -2244,6 +2129,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		// Clear all state related to locking
 		this._lockedAgent = undefined;
 		this._lockedToCodingAgentContextKey.set(false);
+		this._lockedCodingAgentIdContextKey.set('');
 		this._updateAgentCapabilitiesContextKeys(undefined);
 
 		// Explicitly update the DOM to reflect unlocked state
@@ -2290,7 +2176,8 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		const options: IChatSendRequestOptions = {
 			attempt: lastRequest.attempt + 1,
 			location: this.location,
-			userSelectedModelId: this.input.currentLanguageModel
+			userSelectedModelId: this.input.currentLanguageModel,
+			modeInfo: this.input.currentModeInfo,
 		};
 		return await this.chatService.resendRequest(lastRequest, options);
 	}
@@ -2302,6 +2189,10 @@ export class ChatWidget extends Disposable implements IChatWidget {
 			return;
 		}
 
+		// Prompt slash commands are transformed out of the input before sendRequest.
+		// Track them now so tip exclusions still update for commands like /init.
+		this.chatTipService.recordSlashCommandUsage(agentSlashPromptPart.name);
+
 		// need to resolve the slash command to get the prompt file
 		const slashCommand = await this.promptsService.resolvePromptSlashCommand(agentSlashPromptPart.name, CancellationToken.None);
 		if (!slashCommand) {
@@ -2313,9 +2204,6 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		const toolReferences = this.toolsService.toToolReferences(refs);
 		requestInput.attachedContext.insertFirst(toPromptFileVariableEntry(parseResult.uri, PromptFileVariableKind.PromptFile, undefined, true, toolReferences));
 
-		// remove the slash command from the input
-		requestInput.input = this.parsedInput.parts.filter(part => !(part instanceof ChatRequestSlashPromptPart)).map(part => part.text).join('').trim();
-
 		const promptPath = slashCommand.promptPath;
 		const promptRunEvent: ChatPromptRunEvent = {
 			storage: promptPath.storage,
@@ -2328,12 +2216,6 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		}
 		this.telemetryService.publicLog2<ChatPromptRunEvent, ChatPromptRunClassification>('chat.promptRun', promptRunEvent);
 
-		const input = requestInput.input.trim();
-		requestInput.input = `Follow instructions in [${basename(parseResult.uri)}](${parseResult.uri.toString()}).`;
-		if (input) {
-			// if the input is not empty, append it to the prompt
-			requestInput.input += `\n${input}`;
-		}
 		if (parseResult.header) {
 			await this._applyPromptMetadata(parseResult.header, requestInput);
 		}
@@ -2373,7 +2255,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		const editorValue = this.getInput();
 		const requestInputs: IChatRequestInputOptions = {
 			input: !query ? editorValue : query.query,
-			attachedContext: options?.enableImplicitContext === false ? this.input.getAttachedContext(this.viewModel.sessionResource) : this.input.getAttachedAndImplicitContext(this.viewModel.sessionResource),
+			attachedContext: options?.enableImplicitContext === false ? this.input.getAttachedContext() : this.input.getAttachedAndImplicitContext(),
 		};
 
 		const isUserQuery = !query;
@@ -2385,7 +2267,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 				this.chatService.removePendingRequest(this.viewModel.sessionResource, editingRequestId);
 				options.queue ??= editingPendingRequest;
 			} else {
-				this.chatService.cancelCurrentRequestForSession(this.viewModel.sessionResource);
+				await this.chatService.cancelCurrentRequestForSession(this.viewModel.sessionResource, 'acceptInput-editing');
 				options.queue = undefined;
 			}
 
@@ -2405,7 +2287,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 			options.queue ??= ChatRequestQueueKind.Queued;
 		}
 		if (model.requestNeedsInput.get() && !model.getPendingRequests().length) {
-			this.chatService.cancelCurrentRequestForSession(this.viewModel.sessionResource);
+			await this.chatService.cancelCurrentRequestForSession(this.viewModel.sessionResource, 'acceptInput-needsInput');
 			options.queue ??= ChatRequestQueueKind.Queued;
 		}
 		if (requestInProgress) {
@@ -2419,7 +2301,7 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		await this._applyPromptFileIfSet(requestInputs);
 		await this._autoAttachInstructions(requestInputs);
 
-		if (this.viewOptions.enableWorkingSet !== undefined && this.input.currentModeKind === ChatModeKind.Edit && !this.chatService.edits2Enabled) {
+		if (this.viewOptions.enableWorkingSet !== undefined && this.input.currentModeKind === ChatModeKind.Edit) {
 			const uniqueWorkingSetEntries = new ResourceSet(); // NOTE: this is used for bookkeeping so the UI can avoid rendering references in the UI that are already shown in the working set
 			const editingSessionAttachedContext: ChatRequestVariableSet = requestInputs.attachedContext;
 
@@ -2496,6 +2378,15 @@ export class ChatWidget extends Disposable implements IChatWidget {
 
 		this._onDidSubmitAgent.fire({ agent: sent.data.agent, slashCommand: sent.data.slashCommand });
 		this.handleDelegationExitIfNeeded(this._lockedAgent, sent.data.agent);
+
+		// If the session was replaced (untitled -> real contributed session), swap the widget's model
+		if (sent.newSessionResource) {
+			const newModel = this.chatService.getSession(sent.newSessionResource);
+			if (newModel) {
+				this.setModel(newModel);
+			}
+		}
+
 		sent.data.responseCreatedPromise.then(() => {
 			// Only start accessibility progress once a real request/response model exists.
 			this.chatAccessibilityService.acceptRequest(submittedSessionResource);
@@ -2578,15 +2469,17 @@ export class ChatWidget extends Disposable implements IChatWidget {
 
 	getModeRequestOptions(): Partial<IChatSendRequestOptions> {
 		const sessionResource = this.viewModel?.sessionResource;
+		const capturedModeId = this.input.currentModeObs.get().id;
 		const userSelectedTools = this.input.selectedToolsModel.userSelectedTools;
 
 		let lastToolsSnapshot = userSelectedTools.get();
 
 		// When the widget has loaded a new session, return a snapshot of the tools for this session.
-		// Only sync with the tools model when this session is shown.
+		// Only sync with the tools model when this session is shown with the same mode.
 		const scopedTools = derived(reader => {
 			const activeSession = this._viewModelObs.read(reader)?.sessionResource;
-			if (isEqual(activeSession, sessionResource)) {
+			const currentModeId = this.input.currentModeObs.read(reader).id;
+			if (isEqual(activeSession, sessionResource) && currentModeId === capturedModeId) {
 				const tools = userSelectedTools.read(reader);
 				lastToolsSnapshot = tools;
 				return tools;
@@ -2818,8 +2711,8 @@ export class ChatWidget extends Disposable implements IChatWidget {
 		this.logService.debug(`ChatWidget#_autoAttachInstructions: prompt files are always enabled`);
 		const enabledTools = this.input.currentModeKind === ChatModeKind.Agent ? this.input.selectedToolsModel.userSelectedTools.get() : undefined;
 		const enabledSubAgents = this.input.currentModeKind === ChatModeKind.Agent ? this.input.currentModeObs.get().agents?.get() : undefined;
-		const sessionId = this._viewModel?.model.sessionId;
-		const computer = this.instantiationService.createInstance(ComputeAutomaticInstructions, this.input.currentModeKind, enabledTools, enabledSubAgents, sessionId);
+		const sessionResource = this._viewModel?.model.sessionResource;
+		const computer = this.instantiationService.createInstance(ComputeAutomaticInstructions, this.input.currentModeKind, enabledTools, enabledSubAgents, sessionResource);
 		await computer.collect(attachedContext, CancellationToken.None);
 	}
 
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/chatInputPart.ts b/src/vs/workbench/contrib/chat/browser/widget/input/chatInputPart.ts
index 46f466578863d..f61842a8ec6a1 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/chatInputPart.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/chatInputPart.ts
@@ -22,7 +22,7 @@ import { Emitter, Event } from '../../../../../../base/common/event.js';
 import { Iterable } from '../../../../../../base/common/iterator.js';
 import { KeyCode } from '../../../../../../base/common/keyCodes.js';
 import { Lazy } from '../../../../../../base/common/lazy.js';
-import { Disposable, DisposableStore, IDisposable, MutableDisposable, toDisposable } from '../../../../../../base/common/lifecycle.js';
+import { Disposable, DisposableMap, DisposableStore, IDisposable, MutableDisposable, toDisposable } from '../../../../../../base/common/lifecycle.js';
 import { ResourceSet } from '../../../../../../base/common/map.js';
 import { MarshalledId } from '../../../../../../base/common/marshallingIds.js';
 import { Schemas } from '../../../../../../base/common/network.js';
@@ -35,7 +35,7 @@ import { URI } from '../../../../../../base/common/uri.js';
 import { IEditorConstructionOptions } from '../../../../../../editor/browser/config/editorConfiguration.js';
 import { EditorExtensionsRegistry } from '../../../../../../editor/browser/editorExtensions.js';
 import { CodeEditorWidget } from '../../../../../../editor/browser/widget/codeEditor/codeEditorWidget.js';
-import { EditorLayoutInfo, EditorOptions, IEditorOptions } from '../../../../../../editor/common/config/editorOptions.js';
+import { EditorOptions, IEditorOptions, IEditorScrollbarOptions } from '../../../../../../editor/common/config/editorOptions.js';
 import { IDimension } from '../../../../../../editor/common/core/2d/dimension.js';
 import { IPosition } from '../../../../../../editor/common/core/position.js';
 import { IRange, Range } from '../../../../../../editor/common/core/range.js';
@@ -82,20 +82,20 @@ import { InlineChatConfigKeys } from '../../../../inlineChat/common/inlineChat.j
 import { IChatViewTitleActionContext } from '../../../common/actions/chatActions.js';
 import { ChatContextKeys } from '../../../common/actions/chatContextKeys.js';
 import { ChatRequestVariableSet, IChatRequestVariableEntry, isElementVariableEntry, isImageVariableEntry, isNotebookOutputVariableEntry, isPasteVariableEntry, isPromptFileVariableEntry, isPromptTextVariableEntry, isSCMHistoryItemChangeRangeVariableEntry, isSCMHistoryItemChangeVariableEntry, isSCMHistoryItemVariableEntry, isStringVariableEntry } from '../../../common/attachments/chatVariableEntries.js';
-import { ChatMode, IChatMode, IChatModeService } from '../../../common/chatModes.js';
+import { ChatMode, getModeNameForTelemetry, IChatMode, IChatModeService } from '../../../common/chatModes.js';
 import { IChatFollowup, IChatQuestionCarousel, IChatService, IChatSessionContext } from '../../../common/chatService/chatService.js';
 import { agentOptionId, IChatSessionProviderOptionGroup, IChatSessionProviderOptionItem, IChatSessionsService, isIChatSessionFileChange2, localChatSessionType } from '../../../common/chatSessionsService.js';
-import { ChatAgentLocation, ChatConfiguration, ChatModeKind, validateChatMode } from '../../../common/constants.js';
+import { ChatAgentLocation, ChatConfiguration, ChatModeKind, ChatPermissionLevel, isAutoApproveLevel, validateChatMode } from '../../../common/constants.js';
 import { IChatEditingSession, IModifiedFileEntry, ModifiedFileEntryState } from '../../../common/editing/chatEditingService.js';
 import { ILanguageModelChatMetadata, ILanguageModelChatMetadataAndIdentifier, ILanguageModelsService } from '../../../common/languageModels.js';
 import { IChatModelInputState, IChatRequestModeInfo, IInputModel } from '../../../common/model/chatModel.js';
-import { ChatQuestionCarouselData } from '../../../common/model/chatProgressTypes/chatQuestionCarouselData.js';
+import { filterModelsForSession, findDefaultModel, hasModelsTargetingSession, isModelValidForSession, mergeModelsWithCache, resolveModelFromSyncState, shouldResetModelToDefault, shouldResetOnModelListChange, shouldRestoreLateArrivingModel, shouldRestorePersistedModel } from './chatModelSelectionLogic.js';
 import { getChatSessionType } from '../../../common/model/chatUri.js';
 import { IChatResponseViewModel, isResponseVM } from '../../../common/model/chatViewModel.js';
 import { IChatAgentService } from '../../../common/participants/chatAgents.js';
 import { ILanguageModelToolsService } from '../../../common/tools/languageModelToolsService.js';
 import { ChatHistoryNavigator } from '../../../common/widget/chatWidgetHistoryService.js';
-import { ChatSessionPrimaryPickerAction, ChatSubmitAction, IChatExecuteActionContext, OpenDelegationPickerAction, OpenModelPickerAction, OpenModePickerAction, OpenSessionTargetPickerAction, OpenWorkspacePickerAction } from '../../actions/chatExecuteActions.js';
+import { ChatSessionPrimaryPickerAction, ChatSubmitAction, IChatExecuteActionContext, OpenDelegationPickerAction, OpenModelPickerAction, OpenModePickerAction, OpenPermissionPickerAction, OpenSessionTargetPickerAction, OpenWorkspacePickerAction } from '../../actions/chatExecuteActions.js';
 import { AgentSessionProviders, getAgentSessionProvider } from '../../agentSessions/agentSessions.js';
 import { IAgentSessionsService } from '../../agentSessions/agentSessionsService.js';
 import { ChatAttachmentModel } from '../../attachments/chatAttachmentModel.js';
@@ -122,16 +122,20 @@ import { ChatSelectedTools } from './chatSelectedTools.js';
 import { DelegationSessionPickerActionItem } from './delegationSessionPickerActionItem.js';
 import { IModelPickerDelegate } from './modelPickerActionItem.js';
 import { IModePickerDelegate, ModePickerActionItem } from './modePickerActionItem.js';
+import { IPermissionPickerDelegate, PermissionPickerActionItem } from './permissionPickerActionItem.js';
 import { SessionTypePickerActionItem } from './sessionTargetPickerActionItem.js';
 import { WorkspacePickerActionItem } from './workspacePickerActionItem.js';
 import { ChatContextUsageWidget } from '../../widgetHosts/viewPane/chatContextUsageWidget.js';
-import { Target } from '../../../common/promptSyntax/service/promptsService.js';
+import { Target } from '../../../common/promptSyntax/promptTypes.js';
 import { EnhancedModelPickerActionItem } from './modelPickerActionItem2.js';
 
 const $ = dom.$;
 
 const INPUT_EDITOR_MAX_HEIGHT = 250;
+const INPUT_EDITOR_LINE_HEIGHT = 20;
+const INPUT_EDITOR_PADDING = { compact: { top: 2, bottom: 2 }, default: { top: 12, bottom: 12 } };
 const CachedLanguageModelsKey = 'chat.cachedLanguageModels.v2';
+const CHAT_INPUT_PICKER_COLLAPSE_WIDTH = 320;
 
 export interface IChatInputStyles {
 	overlayBackground: string;
@@ -154,6 +158,7 @@ export interface IChatInputPartOptions {
 	enableImplicitContext?: boolean;
 	supportsChangingModes?: boolean;
 	dndContainer?: HTMLElement;
+	inputEditorMinLines?: number;
 	widgetViewKindTag: string;
 	/**
 	 * Optional delegate for the session target picker.
@@ -166,6 +171,11 @@ export interface IChatInputPartOptions {
 	 * for their chat request. This is useful for empty window contexts.
 	 */
 	workspacePickerDelegate?: IWorkspacePickerDelegate;
+	/**
+	 * Whether we are running in the sessions window.
+	 * When true, the secondary toolbar (permissions picker) is hidden.
+	 */
+	isSessionsWindow?: boolean;
 }
 
 export interface IWorkingSetEntry {
@@ -206,17 +216,22 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 	private static _counter = 0;
 
 	private _workingSetCollapsed = observableValue('chatInputPart.workingSetCollapsed', true);
+	private _stableInputPartWidth = observableValue('chatInputPart.stableInputPartWidth', 0);
 	private readonly _chatInputTodoListWidget = this._register(new MutableDisposable<ChatTodoListWidget>());
-	private readonly _chatQuestionCarouselWidget = this._register(new MutableDisposable<ChatQuestionCarouselPart>());
-	private readonly _chatQuestionCarouselDisposables = this._register(new DisposableStore());
-	private _currentQuestionCarouselResponseId: string | undefined;
-	private _currentQuestionCarouselSessionResource: URI | undefined;
+	private readonly _chatQuestionCarouselWidgets = this._register(new DisposableMap<string, ChatQuestionCarouselPart>());
+	private readonly _questionCarouselResponseIds = new Map<string, string>();
+	private readonly _questionCarouselSessionResources = new Map<string, URI>();
 	private _hasQuestionCarouselContextKey: IContextKey<boolean> | undefined;
 	private readonly _chatEditingTodosDisposables = this._register(new DisposableStore());
 	private _lastEditingSessionResource: URI | undefined;
 
 	private _onDidLoadInputState: Emitter<void> = this._register(new Emitter());
 	readonly onDidLoadInputState: Event<void> = this._onDidLoadInputState.event;
+	private readonly _toolbarRelayoutScheduler = this._register(new RunOnceScheduler(() => {
+		if (typeof this.cachedWidth === 'number') {
+			this.layout(this.cachedWidth);
+		}
+	}, 0));
 
 	private _onDidFocus = this._register(new Emitter<void>());
 	readonly onDidFocus: Event<void> = this._onDidFocus.event;
@@ -241,15 +256,15 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 
 	readonly selectedToolsModel: ChatSelectedTools;
 
-	public getAttachedContext(sessionResource: URI) {
+	public getAttachedContext() {
 		const contextArr = new ChatRequestVariableSet();
 		contextArr.add(...this.attachmentModel.attachments, ...this.chatContextService.getWorkspaceContextItems());
 		return contextArr;
 	}
 
-	public getAttachedAndImplicitContext(sessionResource: URI): ChatRequestVariableSet {
+	public getAttachedAndImplicitContext(): ChatRequestVariableSet {
 
-		const contextArr = this.getAttachedContext(sessionResource);
+		const contextArr = this.getAttachedContext();
 
 		if (this.implicitContext) {
 			const implicitChatVariables = this.implicitContext.enabledBaseEntries(this.configurationService.getValue<boolean>('chat.implicitContext.suggestedContext'));
@@ -272,10 +287,13 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 	private readonly _contextResourceLabels: ResourceLabels;
 
 	private readonly inputEditorMaxHeight: number;
+	private readonly inputEditorMinHeight: number | undefined;
 	private inputEditorHeight: number = 0;
 	private container!: HTMLElement;
 
 	private inputSideToolbarContainer?: HTMLElement;
+	private secondaryToolbarContainer!: HTMLElement;
+	private secondaryToolbar!: MenuWorkbenchToolBar;
 
 	private followupsContainer!: HTMLElement;
 	private readonly followupsDisposables: DisposableStore = this._register(new DisposableStore());
@@ -312,6 +330,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 
 	private _inputEditor!: CodeEditorWidget;
 	private _inputEditorElement!: HTMLElement;
+	private _forceVisibleScrollbarUntilAccept = false;
 
 	// Reference to the input model for syncing input state
 	private _inputModel: IInputModel | undefined;
@@ -357,11 +376,13 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 	private chatSessionHasTargetedModels: IContextKey<boolean>;
 	private modelWidget: EnhancedModelPickerActionItem | undefined;
 	private modeWidget: ModePickerActionItem | undefined;
+	private permissionWidget: PermissionPickerActionItem | undefined;
 	private sessionTargetWidget: SessionTypePickerActionItem | undefined;
 	private delegationWidget: DelegationSessionPickerActionItem | undefined;
 	private chatSessionPickerWidgets: Map<string, ChatSessionPickerActionItem | SearchableOptionPickerActionItem> = new Map();
 	private chatSessionPickerContainer: HTMLElement | undefined;
 	private _lastSessionPickerAction: MenuItemAction | undefined;
+	private _lastSessionPickerOptions: IChatInputPickerOptions | undefined;
 	private readonly _waitForPersistedLanguageModel: MutableDisposable<IDisposable> = this._register(new MutableDisposable<IDisposable>());
 	private readonly _chatSessionOptionEmitters: Map<string, Emitter<IChatSessionProviderOptionItem>> = new Map();
 
@@ -391,6 +412,8 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 	readonly onDidChangeCurrentChatMode: Event<void> = this._onDidChangeCurrentChatMode.event;
 
 	private readonly _currentModeObservable: ISettableObservable<IChatMode>;
+	private readonly _currentPermissionLevel: ISettableObservable<ChatPermissionLevel>;
+	private permissionLevelKey: IContextKey<ChatPermissionLevel>;
 
 	public get currentModeKind(): ChatModeKind {
 		const mode = this._currentModeObservable.get();
@@ -403,6 +426,10 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		return this._currentModeObservable;
 	}
 
+	public get currentPermissionLevelObs(): IObservable<ChatPermissionLevel> {
+		return this._currentPermissionLevel;
+	}
+
 	public get currentModeInfo(): IChatRequestModeInfo {
 		const mode = this._currentModeObservable.get();
 		const modeId: 'ask' | 'agent' | 'edit' | 'custom' | undefined = mode.isBuiltin ? this.currentModeKind : 'custom';
@@ -412,13 +439,17 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 			kind: this.currentModeKind,
 			isBuiltin: mode.isBuiltin,
 			modeInstructions: modeInstructions ? {
+				uri: mode.uri?.get(),
 				name: mode.name.get(),
 				content: modeInstructions.content,
 				toolReferences: this.toolService.toToolReferences(modeInstructions.toolReferences),
 				metadata: modeInstructions.metadata,
+				isBuiltin: mode.isBuiltin
 			} : undefined,
 			modeId: modeId,
+			modeName: getModeNameForTelemetry(mode),
 			applyCodeBlockSuggestionId: undefined,
+			permissionLevel: this._currentPermissionLevel.get(),
 		};
 	}
 
@@ -519,6 +550,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 
 		this._contextResourceLabels = this._register(this.instantiationService.createInstance(ResourceLabels, { onDidChangeVisibility: this._onDidChangeVisibility.event }));
 		this._currentModeObservable = observableValue<IChatMode>('currentMode', this.options.defaultMode ?? ChatMode.Agent);
+		this._currentPermissionLevel = observableValue<ChatPermissionLevel>('permissionLevel', ChatPermissionLevel.Default);
 		this._register(this.editorService.onDidActiveEditorChange(() => {
 			this._indexOfLastOpenedContext = -1;
 			this.refreshChatSessionPickers();
@@ -538,7 +570,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 			if (sessionResource) {
 				const ctx = this.chatService.getChatSessionFromInternalUri(sessionResource);
 				const delegateSessionType = this.options.sessionTypePickerDelegate?.getActiveSessionProvider?.();
-				if (ctx?.chatSessionType === chatSessionType || delegateSessionType === chatSessionType) {
+				if (ctx && (getChatSessionType(ctx.chatSessionResource) === chatSessionType) || delegateSessionType === chatSessionType) {
 					this.refreshChatSessionPickers();
 				}
 			}
@@ -560,6 +592,8 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		this.dnd = this._register(this.instantiationService.createInstance(ChatDragAndDrop, () => this._widget, this._attachmentModel, styles));
 
 		this.inputEditorMaxHeight = this.options.renderStyle === 'compact' ? INPUT_EDITOR_MAX_HEIGHT / 3 : INPUT_EDITOR_MAX_HEIGHT;
+		const padding = this.options.renderStyle === 'compact' ? INPUT_EDITOR_PADDING.compact : INPUT_EDITOR_PADDING.default;
+		this.inputEditorMinHeight = this.options.inputEditorMinLines ? this.options.inputEditorMinLines * INPUT_EDITOR_LINE_HEIGHT + padding.top + padding.bottom : undefined;
 
 		this.inputEditorHasText = ChatContextKeys.inputHasText.bindTo(contextKeyService);
 		this.chatCursorAtTop = ChatContextKeys.inputCursorAtTop.bindTo(contextKeyService);
@@ -568,6 +602,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		this.chatModeKindKey = ChatContextKeys.chatModeKind.bindTo(contextKeyService);
 		this.chatModeNameKey = ChatContextKeys.chatModeName.bindTo(contextKeyService);
 		this.chatModelIdKey = ChatContextKeys.chatModelId.bindTo(contextKeyService);
+		this.permissionLevelKey = ChatContextKeys.chatPermissionLevel.bindTo(contextKeyService);
 		this.withinEditSessionKey = ChatContextKeys.withinEditSessionDiff.bindTo(contextKeyService);
 		this.filePartOfEditSessionKey = ChatContextKeys.filePartOfEditSession.bindTo(contextKeyService);
 		this.chatSessionHasOptions = ChatContextKeys.chatSessionHasModels.bindTo(contextKeyService);
@@ -613,19 +648,8 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 
 		this.initSelectedModel();
 
-		this._register(this.languageModelsService.onDidChangeLanguageModels((vendor) => {
-			// Remove vendor from cache since the models changed and what is stored is no longer valid
-			// TODO @lramos15 - The cache should be less confusing since we have the LM Service cache + the view cache interacting weirdly
-			this.storageService.store(
-				CachedLanguageModelsKey,
-				this.storageService.getObject<ILanguageModelChatMetadataAndIdentifier[]>(CachedLanguageModelsKey, StorageScope.APPLICATION, []).filter(m => !m.identifier.startsWith(vendor)),
-				StorageScope.APPLICATION,
-				StorageTarget.MACHINE
-			);
-
-			// We've changed models and the current one is no longer available. Select a new one
-			const selectedModel = this._currentLanguageModel ? this.getModels().find(m => m.identifier === this._currentLanguageModel.get()?.identifier) : undefined;
-			if (!this.currentLanguageModel || !selectedModel) {
+		this._register(this.languageModelsService.onDidChangeLanguageModels(() => {
+			if (shouldResetOnModelListChange(this._currentLanguageModel.get()?.identifier, this.getModels())) {
 				this.setCurrentLanguageModelToDefault();
 			}
 		}));
@@ -663,10 +687,21 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 			if (sessionResource) {
 				const ctx = this.chatService.getChatSessionFromInternalUri(sessionResource);
 				if (ctx) {
-					this.chatSessionsService.notifySessionOptionsChange(
-						ctx.chatSessionResource,
-						[{ optionId: agentOptionId, value: mode.isBuiltin ? '' : modeName }]
-					).catch(err => this.logService.error('Failed to notify extension of agent change:', err));
+					let needsUpdate = true;
+					const agentOption = this.chatSessionsService.getSessionOption(ctx.chatSessionResource, agentOptionId);
+					if (typeof agentOption !== 'undefined') {
+						const agentId = (typeof agentOption === 'string' ? agentOption : agentOption.id) || ChatMode.Agent.id;
+						const isDefaultAgent = agentId === ChatMode.Agent.id;
+						needsUpdate = isDefaultAgent
+							? mode.id !== ChatMode.Agent.id
+							: mode.label.read(undefined) !== agentId; // Extensions use Label (name) as identifier for custom agents.
+					}
+					if (needsUpdate) {
+						this.chatSessionsService.notifySessionOptionsChange(
+							ctx.chatSessionResource,
+							[{ optionId: agentOptionId, value: mode.isBuiltin ? '' : modeName }]
+						).catch(err => this.logService.error('Failed to notify extension of agent change:', err));
+					}
 				}
 			}
 		}));
@@ -707,25 +742,20 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		const persistedAsDefault = this.storageService.getBoolean(this.getSelectedModelIsDefaultStorageKey(), StorageScope.APPLICATION, true);
 
 		if (persistedSelection) {
-			const model = this.getModels().find(m => m.identifier === persistedSelection);
-			if (model) {
-				// Only restore the model if it wasn't the default at the time of storing or it is now the default
-				if (!persistedAsDefault || model.metadata.isDefaultForLocation[this.location]) {
-					this.setCurrentLanguageModel(model);
-					this.checkModelSupported();
-				}
-			} else {
+			const result = shouldRestorePersistedModel(persistedSelection, persistedAsDefault, this.getModels(), this.location);
+			if (result.shouldRestore && result.model) {
+				this.setCurrentLanguageModel(result.model);
+				this.checkModelSupported();
+			} else if (!result.model) {
 				this._waitForPersistedLanguageModel.value = this.languageModelsService.onDidChangeLanguageModels(e => {
 					const persistedModel = this.languageModelsService.lookupLanguageModel(persistedSelection);
 					if (persistedModel) {
 						this._waitForPersistedLanguageModel.clear();
 
-						// Only restore the model if it wasn't the default at the time of storing or it is now the default
-						if (!persistedAsDefault || persistedModel.isDefaultForLocation[this.location]) {
-							if (persistedModel.isUserSelectable) {
-								this.setCurrentLanguageModel({ metadata: persistedModel, identifier: persistedSelection });
-								this.checkModelSupported();
-							}
+						const lateModel = { metadata: persistedModel, identifier: persistedSelection };
+						if (shouldRestoreLateArrivingModel(persistedSelection, persistedAsDefault, lateModel, this.location)) {
+							this.setCurrentLanguageModel(lateModel);
+							this.checkModelSupported();
 						}
 					} else {
 						this.setCurrentLanguageModelToDefault();
@@ -737,11 +767,6 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		this._register(this._onDidChangeCurrentChatMode.event(() => {
 			this.checkModelSupported();
 		}));
-		this._register(this.configurationService.onDidChangeConfiguration(e => {
-			if (e.affectsConfiguration(ChatConfiguration.Edits2Enabled)) {
-				this.checkModelSupported();
-			}
-		}));
 	}
 
 	public setEditing(enabled: boolean, editingSentRequest: ChatContextKeys.EditingRequestType | undefined) {
@@ -788,6 +813,16 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		this.modeWidget?.show();
 	}
 
+	public openPermissionPicker(): void {
+		this.permissionWidget?.show();
+	}
+
+	public setPermissionLevel(level: ChatPermissionLevel): void {
+		this._currentPermissionLevel.set(level, undefined);
+		this.permissionLevelKey.set(level);
+		this.permissionWidget?.refresh();
+	}
+
 	public openSessionTargetPicker(): void {
 		this.sessionTargetWidget?.show();
 	}
@@ -805,8 +840,9 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 	/**
 	 * Create picker widgets for all option groups available for the current session type.
 	 */
-	private createChatSessionPickerWidgets(action: MenuItemAction): (ChatSessionPickerActionItem | SearchableOptionPickerActionItem)[] {
+	private createChatSessionPickerWidgets(action: MenuItemAction, pickerOptions?: IChatInputPickerOptions): (ChatSessionPickerActionItem | SearchableOptionPickerActionItem)[] {
 		this._lastSessionPickerAction = action;
+		this._lastSessionPickerOptions = pickerOptions;
 
 		const result = this.computeVisibleOptionGroups();
 		if (!result) {
@@ -857,7 +893,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 				}
 			};
 
-			const widget = this.instantiationService.createInstance(optionGroup.searchable ? SearchableOptionPickerActionItem : ChatSessionPickerActionItem, action, initialState, itemDelegate);
+			const widget = this.instantiationService.createInstance(optionGroup.searchable ? SearchableOptionPickerActionItem : ChatSessionPickerActionItem, action, initialState, itemDelegate, pickerOptions);
 			this.chatSessionPickerWidgets.set(optionGroup.id, widget);
 			widgets.push(widget);
 		}
@@ -874,6 +910,14 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		this.selectedToolsModel.resetSessionEnablementState();
 		this._chatSessionIsEmpty = chatSessionIsEmpty;
 
+		// Reset permission level on new sessions, unless global auto-approve is on
+		// or the current permission level is already auto-approve/autopilot
+		if (chatSessionIsEmpty && !this.configurationService.getValue<boolean>(ChatConfiguration.GlobalAutoApprove) && !isAutoApproveLevel(this._currentPermissionLevel.get())) {
+			this._currentPermissionLevel.set(ChatPermissionLevel.Default, undefined);
+			this.permissionLevelKey.set(ChatPermissionLevel.Default);
+			this.permissionWidget?.refresh();
+		}
+
 		// TODO@roblourens This is for an experiment which will be obsolete in a month or two and can then be removed.
 		if (chatSessionIsEmpty) {
 			this._setEmptyModelState();
@@ -939,14 +983,18 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 
 			// Sync selected model - validate it belongs to the current session's model pool
 			if (state?.selectedModel) {
-				const lm = this._currentLanguageModel.get();
-				if (!lm || lm.identifier !== state.selectedModel.identifier) {
-					if (this.isModelValidForCurrentSession(state.selectedModel)) {
-						this.setCurrentLanguageModel(state.selectedModel);
-					} else {
-						// Model from state doesn't belong to this session's pool - use default
-						this.setCurrentLanguageModelToDefault();
-					}
+				const allModels = this.getAllMergedModels();
+				const sessionType = this.getCurrentSessionType();
+				const syncResult = resolveModelFromSyncState(state.selectedModel, this._currentLanguageModel.get(), allModels, sessionType, {
+					location: this.location,
+					currentModeKind: this.currentModeKind,
+					isInlineChatV2Enabled: !!this.configurationService.getValue(InlineChatConfigKeys.EnableV2),
+					sessionType,
+				});
+				if (syncResult.action === 'apply') {
+					this.setCurrentLanguageModel(state.selectedModel);
+				} else if (syncResult.action === 'default') {
+					this.setCurrentLanguageModelToDefault();
 				}
 			}
 
@@ -1012,7 +1060,13 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 
 	private checkModelSupported(): void {
 		const lm = this._currentLanguageModel.get();
-		if (lm && (!this.modelSupportedForDefaultAgent(lm) || !this.modelSupportedForInlineChat(lm) || !this.isModelValidForCurrentSession(lm))) {
+		const allModels = this.getAllMergedModels();
+		if (shouldResetModelToDefault(lm, this.getModels(), {
+			location: this.location,
+			currentModeKind: this.currentModeKind,
+			isInlineChatV2Enabled: !!this.configurationService.getValue(InlineChatConfigKeys.EnableV2),
+			sessionType: this.getCurrentSessionType(),
+		}, allModels)) {
 			this.setCurrentLanguageModelToDefault();
 		}
 	}
@@ -1026,6 +1080,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		}
 
 		const mode2 = this.chatModeService.findModeById(mode) ??
+			this.chatModeService.findModeByName(mode) ??
 			this.chatModeService.findModeById(ChatModeKind.Agent) ??
 			ChatMode.Ask;
 		this.setChatMode2(mode2, storeSelection);
@@ -1043,43 +1098,29 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		this._syncInputStateToModel();
 	}
 
-	private modelSupportedForDefaultAgent(model: ILanguageModelChatMetadataAndIdentifier): boolean {
-		// Probably this logic could live in configuration on the agent, or somewhere else, if it gets more complex
-		if (this.currentModeKind === ChatModeKind.Agent || (this.currentModeKind === ChatModeKind.Edit && this.configurationService.getValue(ChatConfiguration.Edits2Enabled))) {
-			return ILanguageModelChatMetadata.suitableForAgentMode(model.metadata);
-		}
-
-		return true;
-	}
+	/**
+	 * Get all models merged from live and cache, without session/mode filtering.
+	 * This is the canonical source for the full model pool, including cached models
+	 * that bridge startup races when live models haven't loaded yet.
+	 */
+	private getAllMergedModels(): ILanguageModelChatMetadataAndIdentifier[] {
+		const cachedModels = this.storageService.getObject<ILanguageModelChatMetadataAndIdentifier[]>(CachedLanguageModelsKey, StorageScope.APPLICATION, []);
+		const liveModels = this.languageModelsService.getLanguageModelIds()
+			.map(modelId => ({ identifier: modelId, metadata: this.languageModelsService.lookupLanguageModel(modelId)! }));
 
-	private modelSupportedForInlineChat(model: ILanguageModelChatMetadataAndIdentifier): boolean {
-		if (this.location !== ChatAgentLocation.EditorInline || !this.configurationService.getValue(InlineChatConfigKeys.EnableV2)) {
-			return true;
+		const contributedVendors = new Set(this.languageModelsService.getVendors().map(v => v.vendor));
+		const models = mergeModelsWithCache(liveModels, cachedModels, contributedVendors);
+		if (liveModels.length > 0) {
+			this.storageService.store(CachedLanguageModelsKey, models, StorageScope.APPLICATION, StorageTarget.MACHINE);
 		}
-		return !!model.metadata.capabilities?.toolCalling;
+		return models;
 	}
 
 	private getModels(): ILanguageModelChatMetadataAndIdentifier[] {
-		const cachedModels = this.storageService.getObject<ILanguageModelChatMetadataAndIdentifier[]>(CachedLanguageModelsKey, StorageScope.APPLICATION, []);
-		let models = this.languageModelsService.getLanguageModelIds()
-			.map(modelId => ({ identifier: modelId, metadata: this.languageModelsService.lookupLanguageModel(modelId)! }));
-		if (models.length === 0 || models.some(m => m.metadata.isDefaultForLocation[this.location]) === false) {
-			models = cachedModels;
-		} else {
-			this.storageService.store(CachedLanguageModelsKey, models, StorageScope.APPLICATION, StorageTarget.MACHINE);
-		}
+		const models = this.getAllMergedModels();
 		models.sort((a, b) => a.metadata.name.localeCompare(b.metadata.name));
 
-		const sessionType = this.getCurrentSessionType();
-		if (sessionType && sessionType !== AgentSessionProviders.Local) {
-			// Session has a specific chat session type - show only models that target
-			// this session type, if any such models exist.
-			return models.filter(entry => entry.metadata?.targetChatSessionType === sessionType && entry.metadata?.isUserSelectable);
-		}
-
-		// No session type or no targeted models - show general models (those without
-		// a targetChatSessionType) filtered by the standard criteria.
-		return models.filter(entry => !entry.metadata?.targetChatSessionType && entry.metadata?.isUserSelectable && this.modelSupportedForDefaultAgent(entry) && this.modelSupportedForInlineChat(entry));
+		return filterModelsForSession(models, this.getCurrentSessionType(), this.currentModeKind, this.location, !!this.configurationService.getValue(InlineChatConfigKeys.EnableV2));
 	}
 
 	/**
@@ -1093,7 +1134,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		}
 		const sessionResource = this._widget?.viewModel?.model.sessionResource;
 		const ctx = sessionResource ? this.chatService.getChatSessionFromInternalUri(sessionResource) : undefined;
-		return ctx?.chatSessionType;
+		return ctx ? getChatSessionType(ctx.chatSessionResource) : undefined;
 	}
 
 	/**
@@ -1101,28 +1142,11 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 	 * This is used to set the context key that controls model picker visibility.
 	 */
 	private hasModelsTargetingSessionType(): boolean {
-		const sessionType = this.getCurrentSessionType();
-		if (!sessionType) {
-			return false;
-		}
-		return this.languageModelsService.getLanguageModelIds().some(modelId => {
-			const metadata = this.languageModelsService.lookupLanguageModel(modelId);
-			return metadata?.targetChatSessionType === sessionType;
-		});
+		return hasModelsTargetingSession(this.getAllMergedModels(), this.getCurrentSessionType());
 	}
 
-	/**
-	 * Check if a model is valid for the current session's model pool.
-	 * If the session has targeted models, the model must target this session type.
-	 * If no models target this session, the model must not have a targetChatSessionType.
-	 */
 	private isModelValidForCurrentSession(model: ILanguageModelChatMetadataAndIdentifier): boolean {
-		if (this.hasModelsTargetingSessionType()) {
-			// Session has targeted models - model must match
-			return model.metadata.targetChatSessionType === this.getCurrentSessionType();
-		}
-		// No targeted models - model must not be session-specific
-		return !model.metadata.targetChatSessionType;
+		return isModelValidForSession(model, this.getAllMergedModels(), this.getCurrentSessionType());
 	}
 
 	/**
@@ -1145,7 +1169,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 	private preselectModelFromSessionHistory(): void {
 		const sessionResource = this._widget?.viewModel?.model.sessionResource;
 		const ctx = sessionResource ? this.chatService.getChatSessionFromInternalUri(sessionResource) : undefined;
-		const requiresCustomModels = ctx && this.chatSessionsService.requiresCustomModelsForSessionType(ctx.chatSessionType);
+		const requiresCustomModels = ctx && this.chatSessionsService.requiresCustomModelsForSessionType(getChatSessionType(ctx.chatSessionResource));
 		if (!requiresCustomModels) {
 			return;
 		}
@@ -1197,7 +1221,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 
 	private setCurrentLanguageModelToDefault() {
 		const allModels = this.getModels();
-		const defaultModel = allModels.find(m => m.metadata.isDefaultForLocation[this.location]) || allModels[0];
+		const defaultModel = findDefaultModel(allModels, this.location);
 		if (defaultModel) {
 			this.setCurrentLanguageModel(defaultModel);
 		}
@@ -1437,6 +1461,8 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 			this.history.append(this._getFilteredEntry(userQuery));
 		}
 
+		this.resetScrollbarVisibilityAfterAccept();
+
 		if (this._chatSessionIsEmpty) {
 			this._chatSessionIsEmpty = false;
 			this._emptyInputState.set(undefined, undefined);
@@ -1579,11 +1605,11 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		const ctx = sessionResource ? this.chatService.getChatSessionFromInternalUri(sessionResource) : undefined;
 
 		// Check if this session type has a customAgentTarget
-		const customAgentTarget = ctx && this.chatSessionsService.getCustomAgentTargetForSessionType(ctx.chatSessionType);
+		const customAgentTarget = ctx && this.chatSessionsService.getCustomAgentTargetForSessionType(getChatSessionType(ctx.chatSessionResource));
 		this.chatSessionHasCustomAgentTarget.set(customAgentTarget !== Target.Undefined);
 
 		// Check if this session type requires custom models
-		const requiresCustomModels = ctx && this.chatSessionsService.requiresCustomModelsForSessionType(ctx.chatSessionType);
+		const requiresCustomModels = ctx && this.chatSessionsService.requiresCustomModelsForSessionType(getChatSessionType(ctx.chatSessionResource));
 		this.chatSessionHasTargetedModels.set(!!requiresCustomModels);
 
 		// Handle agent option from session - set initial mode
@@ -1607,7 +1633,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		// - Panel/Editor: Use actual session's type (ctx available)
 		// - Welcome view: Use delegate's type (ctx may not exist yet)
 		const delegateSessionType = this.options.sessionTypePickerDelegate?.getActiveSessionProvider?.();
-		const effectiveSessionType = delegateSessionType ?? ctx?.chatSessionType;
+		const effectiveSessionType = delegateSessionType ?? (ctx ? getChatSessionType(ctx.chatSessionResource) : undefined);
 
 		if (!effectiveSessionType) {
 			setNoOptions();
@@ -1699,7 +1725,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 			!Array.from(visibleGroupIds).every(id => currentWidgetGroupIds.has(id));
 
 		if (needsRecreation && this._lastSessionPickerAction && this.chatSessionPickerContainer) {
-			const widgets = this.createChatSessionPickerWidgets(this._lastSessionPickerAction);
+			const widgets = this.createChatSessionPickerWidgets(this._lastSessionPickerAction, this._lastSessionPickerOptions);
 			dom.clearNode(this.chatSessionPickerContainer);
 			for (const widget of widgets) {
 				const container = dom.$('.action-item.chat-sessionPicker-item');
@@ -1791,7 +1817,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 	}
 
 	private getEffectiveSessionType(ctx: IChatSessionContext | undefined, delegate: ISessionTypePickerDelegate | undefined): string {
-		return this.options.sessionTypePickerDelegate?.getActiveSessionProvider?.() || ctx?.chatSessionType || '';
+		return this.options.sessionTypePickerDelegate?.getActiveSessionProvider?.() || (ctx && getChatSessionType(ctx.chatSessionResource)) || '';
 	}
 
 	/**
@@ -1907,7 +1933,16 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 			this.refreshChatSessionPickers();
 			this.tryUpdateWidgetController();
 			this.updateContextUsageWidget();
-			if (this._currentQuestionCarouselSessionResource && (!e.currentSessionResource || !isEqual(this._currentQuestionCarouselSessionResource, e.currentSessionResource))) {
+			let hasMatchingResource = false;
+			if (e.currentSessionResource) {
+				for (const r of this._questionCarouselSessionResources.values()) {
+					if (isEqual(r, e.currentSessionResource)) {
+						hasMatchingResource = true;
+						break;
+					}
+				}
+			}
+			if (this._questionCarouselSessionResources.size > 0 && (!e.currentSessionResource || !hasMatchingResource)) {
 				this.clearQuestionCarousel();
 			}
 
@@ -1915,14 +1950,12 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 			// when the session type changes (different session types may have
 			// different model pools via targetChatSessionType).
 			const newSessionType = this.getCurrentSessionType();
-			if (newSessionType !== this._currentSessionType) {
+			if (e.currentSessionResource && newSessionType !== this._currentSessionType) {
 				this._currentSessionType = newSessionType;
 				this.initSelectedModel();
+				this.checkModelInSessionPool();
 			}
 
-			// Validate that the current model belongs to the new session's pool
-			this.checkModelInSessionPool();
-
 			// For contributed sessions with history, pre-select the model
 			// from the last request so the user resumes with the same model.
 			this.preselectModelFromSessionHistory();
@@ -1940,11 +1973,12 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 					dom.h('.interactive-input-and-side-toolbar@inputAndSideToolbar', [
 						dom.h('.chat-input-container@inputContainer', [
 							dom.h('.chat-editor-container@editorContainer'),
-							dom.h('.chat-input-toolbars@inputToolbars', [
-								dom.h('.chat-context-usage-container@contextUsageWidgetContainer'),
-							]),
+							dom.h('.chat-input-toolbars@inputToolbars'),
 						]),
 					]),
+					dom.h('.chat-secondary-toolbar@secondaryToolbar', [
+						dom.h('.chat-context-usage-container@contextUsageWidgetContainer'),
+					]),
 					dom.h('.chat-attachments-container@attachmentsContainer', [
 						dom.h('.chat-attached-context@attachedContextContainer'),
 					]),
@@ -1965,11 +1999,12 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 							dom.h('.chat-attached-context@attachedContextContainer'),
 						]),
 						dom.h('.chat-editor-container@editorContainer'),
-						dom.h('.chat-input-toolbars@inputToolbars', [
-							dom.h('.chat-context-usage-container@contextUsageWidgetContainer'),
-						]),
+						dom.h('.chat-input-toolbars@inputToolbars'),
 					]),
 				]),
+				dom.h('.chat-secondary-toolbar@secondaryToolbar', [
+					dom.h('.chat-context-usage-container@contextUsageWidgetContainer'),
+				]),
 			]);
 		}
 		this.container = elements.root;
@@ -1990,6 +2025,10 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		this.attachmentsContainer = elements.attachmentsContainer;
 		this.attachedContextContainer = elements.attachedContextContainer;
 		const toolbarsContainer = elements.inputToolbars;
+		this.secondaryToolbarContainer = elements.secondaryToolbar;
+		if (this.options.renderStyle === 'compact') {
+			this.secondaryToolbarContainer.style.display = 'none';
+		}
 		this.chatEditingSessionWidgetContainer = elements.chatEditingSessionWidgetContainer;
 		this.chatInputTodoListWidgetContainer = elements.chatInputTodoListWidgetContainer;
 		this.chatGettingStartedTipContainer = elements.chatGettingStartedTipContainer;
@@ -1998,6 +2037,10 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		this.chatInputWidgetsContainer = elements.chatInputWidgetsContainer;
 		this.contextUsageWidgetContainer = elements.contextUsageWidgetContainer;
 
+		if (this.options.isSessionsWindow || this.options.renderStyle === 'compact') {
+			toolbarsContainer.prepend(this.contextUsageWidgetContainer);
+		}
+
 		// Context usage widget — will be positioned in the toolbar after toolbars are created
 		this.contextUsageWidget = this._register(this.instantiationService.createInstance(ChatContextUsageWidget));
 		this.contextUsageWidgetContainer.appendChild(this.contextUsageWidget.domNode);
@@ -2047,8 +2090,8 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		options.ariaLabel = this._getAriaLabel();
 		options.fontFamily = DEFAULT_FONT_FAMILY;
 		options.fontSize = 13;
-		options.lineHeight = 20;
-		options.padding = this.options.renderStyle === 'compact' ? { top: 2, bottom: 2 } : { top: 8, bottom: 8 };
+		options.lineHeight = INPUT_EDITOR_LINE_HEIGHT;
+		options.padding = this.options.renderStyle === 'compact' ? INPUT_EDITOR_PADDING.compact : INPUT_EDITOR_PADDING.default;
 		options.cursorWidth = 1;
 		options.wrappingStrategy = 'advanced';
 		options.bracketPairColorization = { enabled: false };
@@ -2063,7 +2106,13 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 			showStatusBar: false,
 			insertMode: 'insert',
 		};
-		options.scrollbar = { ...(options.scrollbar ?? {}), vertical: 'hidden' };
+		options.scrollbar = this.options.renderStyle === 'compact'
+			? { ...(options.scrollbar ?? {}), vertical: 'hidden' }
+			: {
+				...(options.scrollbar ?? {}),
+				vertical: 'auto',
+				verticalScrollbarSize: 7,
+			};
 		options.stickyScroll = { enabled: false };
 
 		this._inputEditorElement = dom.append(editorContainer, $(chatInputEditorContainerSelector));
@@ -2142,10 +2191,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		const pickerOptions: IChatInputPickerOptions = {
 			getOverflowAnchor: () => this.inputActionsToolbar.getElement(),
 			actionContext: { widget },
-			onlyShowIconsForDefaultActions: observableFromEvent(
-				this._inputEditor.onDidLayoutChange,
-				(l?: EditorLayoutInfo) => (l?.width ?? this._inputEditor.getLayoutInfo().width) < 650 /* This is a magical number based on testing*/
-			).recomputeInitiallyAndOnChange(this._store),
+			hideChevrons: derived(reader => this._stableInputPartWidth.read(reader) < CHAT_INPUT_PICKER_COLLAPSE_WIDTH),
 			hoverPosition: {
 				forcePosition: true,
 				hoverPosition: location === ChatWidgetLocation.SidebarRight && !isMaximized ? HoverPosition.LEFT : HoverPosition.RIGHT
@@ -2163,7 +2209,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 				enabled: true,
 				kind: 'last',
 				minItems: 1,
-				actionMinWidth: 40
+				actionMinWidth: 22
 			},
 			actionViewItemProvider: (action, options) => {
 				if (action.id === OpenModelPickerAction.ID && action instanceof MenuItemAction) {
@@ -2179,10 +2225,22 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 							this.renderAttachedContext();
 						},
 						getModels: () => this.getModels(),
-						canManageModels: () => {
+						useGroupedModelPicker: () => {
 							const sessionType = this.getCurrentSessionType();
 							return !sessionType || sessionType === localChatSessionType;
-						}
+						},
+						showManageModelsAction: () => {
+							const sessionType = this.getCurrentSessionType();
+							return !sessionType || sessionType === localChatSessionType;
+						},
+						showUnavailableFeatured: () => {
+							const sessionType = this.getCurrentSessionType();
+							return !sessionType || sessionType === localChatSessionType;
+						},
+						showFeatured: () => {
+							const sessionType = this.getCurrentSessionType();
+							return !sessionType || sessionType === localChatSessionType;
+						},
 					};
 					return this.modelWidget = this.instantiationService.createInstance(EnhancedModelPickerActionItem, action, itemDelegate, pickerOptions);
 				} else if (action.id === OpenModePickerAction.ID && action instanceof MenuItemAction) {
@@ -2192,7 +2250,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 						customAgentTarget: () => {
 							const sessionResource = this._widget?.viewModel?.model.sessionResource;
 							const ctx = sessionResource && this.chatService.getChatSessionFromInternalUri(sessionResource);
-							return (ctx && this.chatSessionsService.getCustomAgentTargetForSessionType(ctx.chatSessionType)) ?? Target.Undefined;
+							return (ctx && this.chatSessionsService.getCustomAgentTargetForSessionType(getChatSessionType(ctx.chatSessionResource))) ?? Target.Undefined;
 						},
 					};
 					return this.modeWidget = this.instantiationService.createInstance(ModePickerActionItem, action, delegate, pickerOptions);
@@ -2224,17 +2282,13 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 					if (this.workspaceContextService.getWorkbenchState() === WorkbenchState.EMPTY && this.options.workspacePickerDelegate) {
 						return this.instantiationService.createInstance(WorkspacePickerActionItem, action, this.options.workspacePickerDelegate, pickerOptions);
 					} else {
-						const empty = new BaseActionViewItem(undefined, action);
-						if (empty.element) {
-							empty.element.style.display = 'none';
-						}
-						return empty;
+						return new HiddenActionViewItem(action);
 					}
 				} else if (action.id === ChatSessionPrimaryPickerAction.ID && action instanceof MenuItemAction) {
 					// Create all pickers and return a container action view item
-					const widgets = this.createChatSessionPickerWidgets(action);
+					const widgets = this.createChatSessionPickerWidgets(action, pickerOptions);
 					if (widgets.length === 0) {
-						return undefined;
+						return new HiddenActionViewItem(action);
 					}
 					// Create a container to hold all picker widgets
 					return this.instantiationService.createInstance(ChatSessionPickersContainerActionItem, action, widgets);
@@ -2250,9 +2304,8 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 			// eslint-disable-next-line no-restricted-syntax
 			const container = toolbarElement.querySelector('.chat-sessionPicker-container');
 			this.chatSessionPickerContainer = container as HTMLElement | undefined;
-
 			if (this.cachedWidth && typeof this.cachedInputToolbarWidth === 'number' && this.cachedInputToolbarWidth !== this.inputActionsToolbar.getItemsWidth()) {
-				this.layout(this.cachedWidth);
+				this._toolbarRelayoutScheduler.schedule();
 			}
 		}));
 		this.executeToolbar = this._register(this.instantiationService.createInstance(MenuWorkbenchToolBar, toolbarsContainer, this.options.menus.executeToolbar, {
@@ -2267,7 +2320,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		this.executeToolbar.context = { widget } satisfies IChatExecuteActionContext;
 		this._register(this.executeToolbar.onDidChangeMenuItems(() => {
 			if (this.cachedWidth && typeof this.cachedExecuteToolbarWidth === 'number' && this.cachedExecuteToolbarWidth !== this.executeToolbar.getItemsWidth()) {
-				this.layout(this.cachedWidth);
+				this._toolbarRelayoutScheduler.schedule();
 			}
 		}));
 		if (this.options.menus.inputSideToolbar) {
@@ -2283,6 +2336,62 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 			toolbarSide.context = { widget } satisfies IChatExecuteActionContext;
 		}
 
+		// Secondary toolbar (permissions) — below the input box
+		this.secondaryToolbar = this._register(this.instantiationService.createInstance(MenuWorkbenchToolBar, this.secondaryToolbarContainer, MenuId.ChatInputSecondary, {
+			telemetrySource: this.options.menus.telemetrySource,
+			menuOptions: { shouldForwardArgs: true },
+			hiddenItemStrategy: HiddenItemStrategy.NoHide,
+			hoverDelegate,
+			actionViewItemProvider: (action, options) => {
+				if ((action.id === OpenSessionTargetPickerAction.ID || action.id === OpenDelegationPickerAction.ID) && action instanceof MenuItemAction) {
+					const getActiveSessionType = () => {
+						const sessionResource = this._widget?.viewModel?.sessionResource;
+						return sessionResource ? getAgentSessionProvider(sessionResource) : undefined;
+					};
+					const delegate: ISessionTypePickerDelegate = this.options.sessionTypePickerDelegate ?? {
+						getActiveSessionProvider: () => {
+							return getActiveSessionType();
+						},
+						getPendingDelegationTarget: () => {
+							return this._pendingDelegationTarget;
+						},
+						setPendingDelegationTarget: (provider: AgentSessionProviders) => {
+							const isActive = getActiveSessionType() === provider;
+							this._pendingDelegationTarget = isActive ? undefined : provider;
+							this.updateWidgetLockStateFromSessionType(provider);
+							this.updateAgentSessionTypeContextKey();
+							this.refreshChatSessionPickers();
+						},
+					};
+					const isWelcomeViewMode = !!this.options.sessionTypePickerDelegate?.setActiveSessionProvider;
+					const Picker = (action.id === OpenSessionTargetPickerAction.ID || isWelcomeViewMode) ? SessionTypePickerActionItem : DelegationSessionPickerActionItem;
+					return this.sessionTargetWidget = this.instantiationService.createInstance(Picker, action, location === ChatWidgetLocation.Editor ? 'editor' : 'sidebar', delegate, pickerOptions);
+				} else if (action.id === OpenWorkspacePickerAction.ID && action instanceof MenuItemAction) {
+					if (this.workspaceContextService.getWorkbenchState() === WorkbenchState.EMPTY && this.options.workspacePickerDelegate) {
+						return this.instantiationService.createInstance(WorkspacePickerActionItem, action, this.options.workspacePickerDelegate, pickerOptions);
+					} else {
+						const empty = new BaseActionViewItem(undefined, action);
+						if (empty.element) {
+							empty.element.style.display = 'none';
+						}
+						return empty;
+					}
+				} else if (action.id === OpenPermissionPickerAction.ID && action instanceof MenuItemAction) {
+					const delegate: IPermissionPickerDelegate = {
+						currentPermissionLevel: this._currentPermissionLevel,
+						setPermissionLevel: (level: ChatPermissionLevel) => {
+							this._currentPermissionLevel.set(level, undefined);
+							this.permissionLevelKey.set(level);
+						},
+					};
+					return this.permissionWidget = this.instantiationService.createInstance(PermissionPickerActionItem, action, delegate, pickerOptions);
+				}
+				return undefined;
+			}
+		}));
+		this.secondaryToolbar.getElement().classList.add('chat-secondary-input-toolbar');
+		this.secondaryToolbar.context = { widget } satisfies IChatExecuteActionContext;
+
 		let inputModel = this.modelService.getModel(this.inputUri);
 		if (!inputModel) {
 			inputModel = this.modelService.createModel('', null, this.inputUri, true);
@@ -2574,60 +2683,74 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 
 	renderQuestionCarousel(carousel: IChatQuestionCarousel, context: IChatContentPartRenderContext, options: IChatQuestionCarouselOptions): ChatQuestionCarouselPart {
 
-		if (this._chatQuestionCarouselWidget.value) {
-			const existingCarousel = this._chatQuestionCarouselWidget.value;
-			const existingResolveId = existingCarousel.carousel.resolveId;
-			if (existingResolveId && carousel.resolveId && existingResolveId === carousel.resolveId) {
-				return existingCarousel;
-			}
+		const carouselKey = carousel.resolveId ?? `${isResponseVM(context.element) ? context.element.requestId : ''}_${context.contentIndex}`;
 
-			// Complete the old carousel's completion promise as skipped before clearing
-			// This prevents the askQuestions tool from hanging when parallel subagents invoke it
-			const oldCarousel = existingCarousel.carousel;
-			if (oldCarousel instanceof ChatQuestionCarouselData && !oldCarousel.completion.isSettled) {
-				oldCarousel.completion.complete({ answers: undefined });
-			}
-
-			this.clearQuestionCarousel();
+		// If a carousel with the same key already exists, return it
+		const existing = this._chatQuestionCarouselWidgets.get(carouselKey);
+		if (existing) {
+			return existing;
 		}
 
-		// track the response id and session
-		this._currentQuestionCarouselResponseId = isResponseVM(context.element) ? context.element.requestId : undefined;
-		this._currentQuestionCarouselSessionResource = isResponseVM(context.element) ? context.element.sessionResource : undefined;
+		// Track the response id and session for this carousel
+		if (isResponseVM(context.element)) {
+			this._questionCarouselResponseIds.set(carouselKey, context.element.requestId);
+			this._questionCarouselSessionResources.set(carouselKey, context.element.sessionResource);
+		}
 
-		const part = this._chatQuestionCarouselDisposables.add(
-			this.instantiationService.createInstance(ChatQuestionCarouselPart, carousel, context, options)
-		);
-		this._chatQuestionCarouselWidget.value = part;
+		const part = this.instantiationService.createInstance(ChatQuestionCarouselPart, carousel, context, options);
+		this._chatQuestionCarouselWidgets.set(carouselKey, part);
 		this._hasQuestionCarouselContextKey?.set(true);
 
-		dom.clearNode(this.chatQuestionCarouselContainer);
 		dom.append(this.chatQuestionCarouselContainer, part.domNode);
 
 		return part;
 	}
 
-	clearQuestionCarousel(responseId?: string): void {
-		if (responseId && this._currentQuestionCarouselResponseId !== responseId) {
-			return;
+	clearQuestionCarousel(responseId?: string, resolveId?: string): void {
+		if (resolveId !== undefined) {
+			// Remove a specific carousel by resolveId
+			const part = this._chatQuestionCarouselWidgets.get(resolveId);
+			if (part) {
+				part.domNode.remove();
+				this._chatQuestionCarouselWidgets.deleteAndDispose(resolveId);
+			}
+			this._questionCarouselResponseIds.delete(resolveId);
+			this._questionCarouselSessionResources.delete(resolveId);
+		} else if (responseId !== undefined) {
+			// Remove all carousels associated with a given responseId
+			for (const [key, rid] of this._questionCarouselResponseIds) {
+				if (rid === responseId) {
+					const part = this._chatQuestionCarouselWidgets.get(key);
+					if (part) {
+						part.domNode.remove();
+						this._chatQuestionCarouselWidgets.deleteAndDispose(key);
+					}
+					this._questionCarouselResponseIds.delete(key);
+					this._questionCarouselSessionResources.delete(key);
+				}
+			}
+		} else {
+			// Clear all carousels
+			this._chatQuestionCarouselWidgets.clearAndDisposeAll();
+			this._questionCarouselResponseIds.clear();
+			this._questionCarouselSessionResources.clear();
+			dom.clearNode(this.chatQuestionCarouselContainer);
 		}
-		this._chatQuestionCarouselDisposables.clear();
-		this._chatQuestionCarouselWidget.clear();
-		this._currentQuestionCarouselResponseId = undefined;
-		this._currentQuestionCarouselSessionResource = undefined;
-		this._hasQuestionCarouselContextKey?.set(false);
-		dom.clearNode(this.chatQuestionCarouselContainer);
-	}
-	get questionCarouselResponseId(): string | undefined {
-		return this._currentQuestionCarouselResponseId;
+		this._hasQuestionCarouselContextKey?.set(this._chatQuestionCarouselWidgets.size > 0);
 	}
 
 	get questionCarousel(): ChatQuestionCarouselPart | undefined {
-		return this._chatQuestionCarouselWidget.value;
+		// Return the focused carousel, or the first one
+		for (const part of this._chatQuestionCarouselWidgets.values()) {
+			if (part.hasFocus()) {
+				return part;
+			}
+		}
+		return this._chatQuestionCarouselWidgets.size > 0 ? this._chatQuestionCarouselWidgets.values().next().value : undefined;
 	}
 
 	focusQuestionCarousel(): boolean {
-		const carousel = this._chatQuestionCarouselWidget.value;
+		const carousel = this.questionCarousel;
 		if (carousel) {
 			carousel.focus();
 			return true;
@@ -2636,17 +2759,21 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 	}
 
 	isQuestionCarouselFocused(): boolean {
-		const carousel = this._chatQuestionCarouselWidget.value;
-		return carousel?.hasFocus() ?? false;
+		for (const part of this._chatQuestionCarouselWidgets.values()) {
+			if (part.hasFocus()) {
+				return true;
+			}
+		}
+		return false;
 	}
 
 	navigateToPreviousQuestion(): boolean {
-		const carousel = this._chatQuestionCarouselWidget.value;
+		const carousel = this.questionCarousel;
 		return carousel?.navigateToPreviousQuestion() ?? false;
 	}
 
 	navigateToNextQuestion(): boolean {
-		const carousel = this._chatQuestionCarouselWidget.value;
+		const carousel = this.questionCarousel;
 		return carousel?.navigateToNextQuestion() ?? false;
 	}
 
@@ -2988,6 +3115,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 	 */
 	layout(width: number) {
 		this.cachedWidth = width;
+		this._stableInputPartWidth.set(width, undefined);
 
 		return this._layout(width);
 	}
@@ -3001,7 +3129,7 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 
 		const initialEditorScrollWidth = this._inputEditor.getScrollWidth();
 		const newEditorWidth = width - data.inputPartHorizontalPadding - data.editorBorder - data.inputPartHorizontalPaddingInside - data.toolbarsWidth - data.sideToolbarWidth;
-		const inputEditorHeight = Math.min(this._inputEditor.getContentHeight(), this.inputEditorMaxHeight);
+		const inputEditorHeight = this.inputEditorMinHeight ? Math.max(this.inputEditorMinHeight, Math.min(this._inputEditor.getContentHeight(), this.inputEditorMaxHeight)) : Math.min(this._inputEditor.getContentHeight(), this.inputEditorMaxHeight);
 		const newDimension = { width: newEditorWidth, height: inputEditorHeight };
 		if (!this.previousInputEditorDimension || (this.previousInputEditorDimension.width !== newDimension.width || this.previousInputEditorDimension.height !== newDimension.height)) {
 			// This layout call has side-effects that are hard to understand. eg if we are calling this inside a onDidChangeContent handler, this can trigger the next onDidChangeContent handler
@@ -3031,18 +3159,20 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		const inputSideToolbarWidth = this.inputSideToolbarContainer ? dom.getTotalWidth(this.inputSideToolbarContainer) : 0;
 
 		const getToolbarsWidthCompact = () => {
+			const toolbarItemGap = 4;
 			const executeToolbarWidth = this.cachedExecuteToolbarWidth = this.executeToolbar.getItemsWidth();
 			const inputToolbarWidth = this.cachedInputToolbarWidth = this.inputActionsToolbar.getItemsWidth();
-			const executeToolbarPadding = (this.executeToolbar.getItemsLength() - 1) * 4;
-			const inputToolbarPadding = this.inputActionsToolbar.getItemsLength() ? (this.inputActionsToolbar.getItemsLength() - 1) * 4 : 0;
+			const executeToolbarPadding = (this.executeToolbar.getItemsLength() - 1) * toolbarItemGap;
+			const inputToolbarPadding = this.inputActionsToolbar.getItemsLength() ? (this.inputActionsToolbar.getItemsLength() - 1) * toolbarItemGap : 0;
 			const contextUsageWidth = dom.getTotalWidth(this.contextUsageWidgetContainer);
-			return executeToolbarWidth + executeToolbarPadding + contextUsageWidth + (this.options.renderInputToolbarBelowInput ? 0 : inputToolbarWidth + inputToolbarPadding);
+			const inputToolbarsPadding = 12; // pdading between input toolbar/execute toolbar/contextUsage.
+			return executeToolbarWidth + executeToolbarPadding + contextUsageWidth + (this.options.renderInputToolbarBelowInput ? 0 : inputToolbarWidth + inputToolbarPadding + inputToolbarsPadding);
 		};
 
 		return {
 			editorBorder: 2,
-			inputPartHorizontalPadding: this.options.renderStyle === 'compact' ? 16 : 32,
-			inputPartHorizontalPaddingInside: 12,
+			inputPartHorizontalPadding: this.options.renderStyle === 'compact' ? 16 : 24,
+			inputPartHorizontalPaddingInside: this.options.renderStyle === 'compact' ? 12 : 10,
 			toolbarsWidth: this.options.renderStyle === 'compact' ? getToolbarsWidthCompact() : 0,
 			sideToolbarWidth: inputSideToolbarWidth > 0 ? inputSideToolbarWidth + 4 /*gap*/ : 0,
 		};
@@ -3088,6 +3218,42 @@ export class ChatInputPart extends Disposable implements IHistoryNavigationWidge
 		// Fallback for unknown contexts
 		return { location: ChatWidgetLocation.Editor, isMaximized: false };
 	}
+
+	private getDefaultScrollbarOptions(): IEditorScrollbarOptions {
+		const scrollbar = this._inputEditor.getRawOptions().scrollbar ?? {};
+		return this.options.renderStyle === 'compact'
+			? { ...scrollbar, vertical: 'hidden' }
+			: { ...scrollbar, vertical: 'auto', verticalScrollbarSize: 7 };
+	}
+
+	private getVisibleScrollbarOptions(): IEditorScrollbarOptions {
+		const scrollbar = this._inputEditor.getRawOptions().scrollbar ?? {};
+		return this.options.renderStyle === 'compact'
+			? { ...scrollbar, vertical: 'hidden' }
+			: { ...scrollbar, vertical: 'visible', verticalScrollbarSize: 7 };
+	}
+
+	private updateInputEditorScrollbarOptions(): void {
+		this._inputEditor.updateOptions({
+			scrollbar: this._forceVisibleScrollbarUntilAccept
+				? this.getVisibleScrollbarOptions()
+				: this.getDefaultScrollbarOptions()
+		});
+	}
+
+	showScrollbarUntilAccept(): void {
+		this._forceVisibleScrollbarUntilAccept = true;
+		this.updateInputEditorScrollbarOptions();
+	}
+
+	private resetScrollbarVisibilityAfterAccept(): void {
+		if (!this._forceVisibleScrollbarUntilAccept) {
+			return;
+		}
+
+		this._forceVisibleScrollbarUntilAccept = false;
+		this.updateInputEditorScrollbarOptions();
+	}
 }
 
 
@@ -3125,3 +3291,14 @@ class ChatSessionPickersContainerActionItem extends ActionViewItem {
 		super.dispose();
 	}
 }
+
+class HiddenActionViewItem extends BaseActionViewItem {
+	constructor(action: IAction) {
+		super(undefined, action);
+	}
+
+	override render(container: HTMLElement): void {
+		super.render(container);
+		container.style.display = 'none';
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/chatInputPickerActionItem.ts b/src/vs/workbench/contrib/chat/browser/widget/input/chatInputPickerActionItem.ts
index 1377aa5260793..13682b907d93c 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/chatInputPickerActionItem.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/chatInputPickerActionItem.ts
@@ -24,7 +24,7 @@ export interface IChatInputPickerOptions {
 
 	readonly actionContext?: IChatExecuteActionContext;
 
-	readonly onlyShowIconsForDefaultActions: IObservable<boolean>;
+	readonly hideChevrons: IObservable<boolean>;
 
 	readonly hoverPosition?: IHoverPositionOptions;
 }
@@ -53,8 +53,9 @@ export abstract class ChatInputPickerActionViewItem extends ActionWidgetDropdown
 		super(action, optionsWithAnchor, actionWidgetService, keybindingService, contextKeyService, telemetryService);
 
 		this._register(autorun(reader => {
-			this.pickerOptions.onlyShowIconsForDefaultActions.read(reader);
+			const hideChevrons = this.pickerOptions.hideChevrons.read(reader);
 			if (this.element) {
+				this.element.classList.toggle('hide-chevrons', hideChevrons);
 				this.renderLabel(this.element);
 			}
 		}));
@@ -74,5 +75,12 @@ export abstract class ChatInputPickerActionViewItem extends ActionWidgetDropdown
 	override render(container: HTMLElement): void {
 		super.render(container);
 		container.classList.add('chat-input-picker-item');
+
+		// Apply initial collapsed state now that this.element exists
+		const hideChevrons = this.pickerOptions.hideChevrons.get();
+		if (this.element) {
+			this.element.classList.toggle('hide-chevrons', hideChevrons);
+			this.renderLabel(this.element);
+		}
 	}
 }
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/chatModelPicker.ts b/src/vs/workbench/contrib/chat/browser/widget/input/chatModelPicker.ts
index ce813638d782f..f22b8bd88340d 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/chatModelPicker.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/chatModelPicker.ts
@@ -12,9 +12,11 @@ import { Emitter, Event } from '../../../../../../base/common/event.js';
 import { MarkdownString } from '../../../../../../base/common/htmlContent.js';
 import { KeyCode } from '../../../../../../base/common/keyCodes.js';
 import { Disposable } from '../../../../../../base/common/lifecycle.js';
+import { autorun, IObservable } from '../../../../../../base/common/observable.js';
 import { ThemeIcon } from '../../../../../../base/common/themables.js';
 import { localize } from '../../../../../../nls.js';
 import { ActionListItemKind, IActionListItem } from '../../../../../../platform/actionWidget/browser/actionList.js';
+import { IHoverPositionOptions } from '../../../../../../base/browser/ui/hover/hover.js';
 import { IActionWidgetService } from '../../../../../../platform/actionWidget/browser/actionWidget.js';
 import { IActionWidgetDropdownAction } from '../../../../../../platform/actionWidget/browser/actionWidgetDropdown.js';
 import { ICommandService } from '../../../../../../platform/commands/common/commands.js';
@@ -75,6 +77,7 @@ type ChatModelChangeEvent = {
 function createModelItem(
 	action: IActionWidgetDropdownAction & { section?: string },
 	model?: ILanguageModelChatMetadataAndIdentifier,
+	hoverPosition?: IHoverPositionOptions,
 ): IActionListItem<IActionWidgetDropdownAction> {
 	return {
 		item: action,
@@ -84,7 +87,7 @@ function createModelItem(
 		group: { title: '', icon: action.icon ?? ThemeIcon.fromId(action.checked ? Codicon.check.id : Codicon.blank.id) },
 		hideIcon: false,
 		section: action.section,
-		hover: model ? { content: getModelHoverContent(model) } : undefined,
+		hover: model ? { content: getModelHoverContent(model), position: hoverPosition } : undefined,
 	};
 }
 
@@ -108,6 +111,27 @@ function createModelAction(
 	};
 }
 
+function shouldShowManageModelsAction(chatEntitlementService: IChatEntitlementService): boolean {
+	return chatEntitlementService.entitlement === ChatEntitlement.Free ||
+		chatEntitlementService.entitlement === ChatEntitlement.Pro ||
+		chatEntitlementService.entitlement === ChatEntitlement.ProPlus ||
+		chatEntitlementService.entitlement === ChatEntitlement.Business ||
+		chatEntitlementService.entitlement === ChatEntitlement.Enterprise ||
+		chatEntitlementService.isInternal;
+}
+
+function createManageModelsAction(commandService: ICommandService): IActionWidgetDropdownAction {
+	return {
+		id: 'manageModels',
+		enabled: true,
+		checked: false,
+		class: ThemeIcon.asClassName(Codicon.gear),
+		tooltip: localize('chat.manageModels.tooltip', "Manage Language Models"),
+		label: localize('chat.manageModels', "Manage Models..."),
+		run: () => { commandService.executeCommand(MANAGE_CHAT_COMMAND_ID); }
+	};
+}
+
 /**
  * Builds the grouped items for the model picker dropdown.
  *
@@ -116,8 +140,8 @@ function createModelAction(
  * 2. Promoted section (selected + recently used + featured models from control manifest)
  *    - Available models sorted alphabetically, followed by unavailable models
  *    - Unavailable models show upgrade/update/admin status
- * 3. Other Models (collapsible toggle, sorted by vendor then name)
- *    - Last item is "Manage Models..." (always visible during filtering)
+ * 3. Other Models (collapsible toggle, available first, then sorted by vendor then name)
+ * 4. Optional "Manage Models..." action shown in Other Models after a separator
  */
 export function buildModelPickerItems(
 	models: ILanguageModelChatMetadataAndIdentifier[],
@@ -128,9 +152,12 @@ export function buildModelPickerItems(
 	updateStateType: StateType,
 	onSelect: (model: ILanguageModelChatMetadataAndIdentifier) => void,
 	manageSettingsUrl: string | undefined,
-	canManageModels: boolean,
-	commandService: ICommandService,
+	useGroupedModelPicker: boolean,
+	manageModelsAction: IActionWidgetDropdownAction | undefined,
 	chatEntitlementService: IChatEntitlementService,
+	showUnavailableFeatured: boolean,
+	showFeatured: boolean,
+	hoverPosition?: IHoverPositionOptions,
 ): IActionListItem<IActionWidgetDropdownAction>[] {
 	const items: IActionListItem<IActionWidgetDropdownAction>[] = [];
 	if (models.length === 0) {
@@ -145,224 +172,238 @@ export function buildModelPickerItems(
 		}));
 	}
 
-	if (!canManageModels) {
-		// Flat list: auto first, then all models sorted alphabetically
-		const autoModel = models.find(m => m.metadata.id === 'auto' && m.metadata.vendor === 'copilot');
-		if (autoModel) {
-			items.push(createModelItem(createModelAction(autoModel, selectedModelId, onSelect), autoModel));
-		}
-		const sortedModels = models
-			.filter(m => m !== autoModel)
-			.sort((a, b) => {
-				const vendorCmp = a.metadata.vendor.localeCompare(b.metadata.vendor);
-				return vendorCmp !== 0 ? vendorCmp : a.metadata.name.localeCompare(b.metadata.name);
-			});
-		for (const model of sortedModels) {
-			items.push(createModelItem(createModelAction(model, selectedModelId, onSelect), model));
-		}
-		return items;
-	}
-
-	const isPro = isProUser(chatEntitlementService.entitlement);
-	let otherModels: ILanguageModelChatMetadataAndIdentifier[] = [];
-	if (models.length) {
-		// Collect all available models into lookup maps
-		const allModelsMap = new Map<string, ILanguageModelChatMetadataAndIdentifier>();
-		const modelsByMetadataId = new Map<string, ILanguageModelChatMetadataAndIdentifier>();
-		for (const model of models) {
-			allModelsMap.set(model.identifier, model);
-			modelsByMetadataId.set(model.metadata.id, model);
-		}
+	if (useGroupedModelPicker) {
+		const isPro = isProUser(chatEntitlementService.entitlement);
+		let otherModels: ILanguageModelChatMetadataAndIdentifier[] = [];
+		if (models.length) {
+			// Collect all available models into lookup maps
+			const allModelsMap = new Map<string, ILanguageModelChatMetadataAndIdentifier>();
+			const modelsByMetadataId = new Map<string, ILanguageModelChatMetadataAndIdentifier>();
+			for (const model of models) {
+				allModelsMap.set(model.identifier, model);
+				modelsByMetadataId.set(model.metadata.id, model);
+			}
 
-		const placed = new Set<string>();
+			const placed = new Set<string>();
 
-		const markPlaced = (identifierOrId: string, metadataId?: string) => {
-			placed.add(identifierOrId);
-			if (metadataId) {
-				placed.add(metadataId);
-			}
-		};
+			const markPlaced = (identifierOrId: string, metadataId?: string) => {
+				placed.add(identifierOrId);
+				if (metadataId) {
+					placed.add(metadataId);
+				}
+			};
 
-		const resolveModel = (id: string) => allModelsMap.get(id) ?? modelsByMetadataId.get(id);
+			const resolveModel = (id: string) => allModelsMap.get(id) ?? modelsByMetadataId.get(id);
 
-		const getUnavailableReason = (entry: IModelControlEntry): 'upgrade' | 'update' | 'admin' => {
-			if (!isPro) {
-				return 'upgrade';
-			}
-			if (entry.minVSCodeVersion && !isVersionAtLeast(currentVSCodeVersion, entry.minVSCodeVersion)) {
-				return 'update';
+			const getUnavailableReason = (entry: IModelControlEntry): 'upgrade' | 'update' | 'admin' => {
+				if (!isPro) {
+					return 'upgrade';
+				}
+				if (entry.minVSCodeVersion && !isVersionAtLeast(currentVSCodeVersion, entry.minVSCodeVersion)) {
+					return 'update';
+				}
+				return 'admin';
+			};
+
+			// --- 1. Auto ---
+			const autoModel = models.find(m => m.metadata.id === 'auto' && m.metadata.vendor === 'copilot');
+			if (autoModel) {
+				markPlaced(autoModel.identifier, autoModel.metadata.id);
+				items.push(createModelItem(createModelAction(autoModel, selectedModelId, onSelect), autoModel, hoverPosition));
 			}
-			return 'admin';
-		};
-
-		// --- 1. Auto ---
-		const autoModel = models.find(m => m.metadata.id === 'auto' && m.metadata.vendor === 'copilot');
-		if (autoModel) {
-			markPlaced(autoModel.identifier, autoModel.metadata.id);
-			items.push(createModelItem(createModelAction(autoModel, selectedModelId, onSelect), autoModel));
-		}
 
-		// --- 2. Promoted section (selected + recently used + featured) ---
-		type PromotedItem =
-			| { kind: 'available'; model: ILanguageModelChatMetadataAndIdentifier }
-			| { kind: 'unavailable'; id: string; entry: IModelControlEntry; reason: 'upgrade' | 'update' | 'admin' };
+			// --- 2. Promoted section (selected + recently used + featured) ---
+			type PromotedItem =
+				| { kind: 'available'; model: ILanguageModelChatMetadataAndIdentifier }
+				| { kind: 'unavailable'; id: string; entry: IModelControlEntry; reason: 'upgrade' | 'update' | 'admin' };
 
-		const promotedItems: PromotedItem[] = [];
+			const promotedItems: PromotedItem[] = [];
 
-		// Try to place a model by id. Returns true if handled.
-		const tryPlaceModel = (id: string): boolean => {
-			if (placed.has(id)) {
-				return false;
-			}
-			const model = resolveModel(id);
-			if (model && !placed.has(model.identifier)) {
-				markPlaced(model.identifier, model.metadata.id);
-				const entry = controlModels[model.metadata.id];
-				if (entry?.minVSCodeVersion && !isVersionAtLeast(currentVSCodeVersion, entry.minVSCodeVersion)) {
-					promotedItems.push({ kind: 'unavailable', id: model.metadata.id, entry, reason: 'update' });
-				} else {
-					promotedItems.push({ kind: 'available', model });
+			// Try to place a model by id. Returns true if handled.
+			const tryPlaceModel = (id: string): boolean => {
+				if (placed.has(id)) {
+					return false;
 				}
-				return true;
-			}
-			if (!model) {
-				const entry = controlModels[id];
-				if (entry && !entry.exists) {
-					markPlaced(id);
-					promotedItems.push({ kind: 'unavailable', id, entry, reason: getUnavailableReason(entry) });
+				const model = resolveModel(id);
+				if (model && !placed.has(model.identifier)) {
+					markPlaced(model.identifier, model.metadata.id);
+					const entry = controlModels[model.metadata.id];
+					if (entry?.minVSCodeVersion && !isVersionAtLeast(currentVSCodeVersion, entry.minVSCodeVersion)) {
+						promotedItems.push({ kind: 'unavailable', id: model.metadata.id, entry, reason: 'update' });
+					} else {
+						promotedItems.push({ kind: 'available', model });
+					}
 					return true;
 				}
-			}
-			return false;
-		};
+				if (!model) {
+					const entry = controlModels[id];
+					if (entry && !entry.exists) {
+						markPlaced(id);
+						promotedItems.push({ kind: 'unavailable', id, entry, reason: getUnavailableReason(entry) });
+						return true;
+					}
+				}
+				return false;
+			};
 
-		// Selected model
-		if (selectedModelId && selectedModelId !== autoModel?.identifier) {
-			tryPlaceModel(selectedModelId);
-		}
+			// Selected model
+			if (selectedModelId && selectedModelId !== autoModel?.identifier) {
+				tryPlaceModel(selectedModelId);
+			}
 
-		// Recently used models
-		for (const id of recentModelIds) {
-			tryPlaceModel(id);
-		}
+			// Recently used models
+			for (const id of recentModelIds) {
+				tryPlaceModel(id);
+			}
 
-		// Featured models from control manifest
-		for (const [entryId, entry] of Object.entries(controlModels)) {
-			if (!entry.featured || placed.has(entryId)) {
-				continue;
+			// Featured models from control manifest
+			if (showFeatured) {
+				for (const [entryId, entry] of Object.entries(controlModels)) {
+					if (!entry.featured || placed.has(entryId)) {
+						continue;
+					}
+					const model = resolveModel(entryId);
+					if (model && !placed.has(model.identifier)) {
+						if (entry.minVSCodeVersion && !isVersionAtLeast(currentVSCodeVersion, entry.minVSCodeVersion)) {
+							if (showUnavailableFeatured) {
+								markPlaced(model.identifier, model.metadata.id);
+								promotedItems.push({ kind: 'unavailable', id: entryId, entry, reason: 'update' });
+							}
+						} else {
+							markPlaced(model.identifier, model.metadata.id);
+							promotedItems.push({ kind: 'available', model });
+						}
+					} else if (!model && !entry.exists) {
+						if (showUnavailableFeatured) {
+							markPlaced(entryId);
+							promotedItems.push({ kind: 'unavailable', id: entryId, entry, reason: getUnavailableReason(entry) });
+						}
+					}
+				}
 			}
-			const model = resolveModel(entryId);
-			if (model && !placed.has(model.identifier)) {
-				markPlaced(model.identifier, model.metadata.id);
-				if (entry.minVSCodeVersion && !isVersionAtLeast(currentVSCodeVersion, entry.minVSCodeVersion)) {
-					promotedItems.push({ kind: 'unavailable', id: entryId, entry, reason: 'update' });
-				} else {
-					promotedItems.push({ kind: 'available', model });
+
+			// Render promoted section: available first, then sorted alphabetically by name
+			if (promotedItems.length > 0) {
+				promotedItems.sort((a, b) => {
+					const aAvail = a.kind === 'available' ? 0 : 1;
+					const bAvail = b.kind === 'available' ? 0 : 1;
+					if (aAvail !== bAvail) {
+						return aAvail - bAvail;
+					}
+					const aName = a.kind === 'available' ? a.model.metadata.name : a.entry.label;
+					const bName = b.kind === 'available' ? b.model.metadata.name : b.entry.label;
+					return aName.localeCompare(bName);
+				});
+
+				for (const item of promotedItems) {
+					if (item.kind === 'available') {
+						items.push(createModelItem(createModelAction(item.model, selectedModelId, onSelect), item.model, hoverPosition));
+					} else {
+						items.push(createUnavailableModelItem(item.id, item.entry, item.reason, manageSettingsUrl, updateStateType, undefined, hoverPosition));
+					}
 				}
-			} else if (!model && !entry.exists) {
-				markPlaced(entryId);
-				promotedItems.push({ kind: 'unavailable', id: entryId, entry, reason: getUnavailableReason(entry) });
 			}
-		}
 
-		// Render promoted section: sorted alphabetically by name
-		let hasShownActionLink = false;
-		if (promotedItems.length > 0) {
-			promotedItems.sort((a, b) => {
-				const aName = a.kind === 'available' ? a.model.metadata.name : a.entry.label;
-				const bName = b.kind === 'available' ? b.model.metadata.name : b.entry.label;
-				return aName.localeCompare(bName);
-			});
+			// --- 3. Other Models (collapsible) ---
+			otherModels = models
+				.filter(m => !placed.has(m.identifier) && !placed.has(m.metadata.id))
+				.sort((a, b) => {
+					const aEntry = controlModels[a.metadata.id] ?? controlModels[a.identifier];
+					const bEntry = controlModels[b.metadata.id] ?? controlModels[b.identifier];
+					const aAvail = aEntry?.minVSCodeVersion && !isVersionAtLeast(currentVSCodeVersion, aEntry.minVSCodeVersion) ? 1 : 0;
+					const bAvail = bEntry?.minVSCodeVersion && !isVersionAtLeast(currentVSCodeVersion, bEntry.minVSCodeVersion) ? 1 : 0;
+					if (aAvail !== bAvail) {
+						return aAvail - bAvail;
+					}
+					const aCopilot = a.metadata.vendor === 'copilot' ? 0 : 1;
+					const bCopilot = b.metadata.vendor === 'copilot' ? 0 : 1;
+					if (aCopilot !== bCopilot) {
+						return aCopilot - bCopilot;
+					}
+					const vendorCmp = a.metadata.vendor.localeCompare(b.metadata.vendor);
+					return vendorCmp !== 0 ? vendorCmp : a.metadata.name.localeCompare(b.metadata.name);
+				});
 
-			for (const item of promotedItems) {
-				if (item.kind === 'available') {
-					items.push(createModelItem(createModelAction(item.model, selectedModelId, onSelect), item.model));
-				} else {
-					const showActionLink = item.reason === 'upgrade' ? !hasShownActionLink : true;
-					if (showActionLink && item.reason === 'upgrade') {
-						hasShownActionLink = true;
+			if (otherModels.length > 0) {
+				if (items.length > 0) {
+					items.push({ kind: ActionListItemKind.Separator });
+				}
+				items.push({
+					item: {
+						id: 'otherModels',
+						enabled: true,
+						checked: false,
+						class: undefined,
+						tooltip: localize('chat.modelPicker.otherModels', "Other Models"),
+						label: localize('chat.modelPicker.otherModels', "Other Models"),
+						run: () => { /* toggle handled by isSectionToggle */ }
+					},
+					kind: ActionListItemKind.Action,
+					label: localize('chat.modelPicker.otherModels', "Other Models"),
+					group: { title: '', icon: Codicon.chevronDown },
+					hideIcon: false,
+					section: ModelPickerSection.Other,
+					isSectionToggle: true,
+				});
+				for (const model of otherModels) {
+					const entry = controlModels[model.metadata.id] ?? controlModels[model.identifier];
+					if (entry?.minVSCodeVersion && !isVersionAtLeast(currentVSCodeVersion, entry.minVSCodeVersion)) {
+						items.push(createUnavailableModelItem(model.metadata.id, entry, 'update', manageSettingsUrl, updateStateType, ModelPickerSection.Other, hoverPosition));
+					} else {
+						items.push(createModelItem(createModelAction(model, selectedModelId, onSelect, ModelPickerSection.Other), model, hoverPosition));
 					}
-					items.push(createUnavailableModelItem(item.id, item.entry, item.reason, manageSettingsUrl, updateStateType, undefined, showActionLink));
 				}
 			}
 		}
 
-		// --- 3. Other Models (collapsible) ---
-		otherModels = models
-			.filter(m => !placed.has(m.identifier) && !placed.has(m.metadata.id))
-			.sort((a, b) => {
-				const aCopilot = a.metadata.vendor === 'copilot' ? 0 : 1;
-				const bCopilot = b.metadata.vendor === 'copilot' ? 0 : 1;
-				if (aCopilot !== bCopilot) {
-					return aCopilot - bCopilot;
-				}
-				const vendorCmp = a.metadata.vendor.localeCompare(b.metadata.vendor);
-				return vendorCmp !== 0 ? vendorCmp : a.metadata.name.localeCompare(b.metadata.name);
-			});
-
-		if (otherModels.length > 0) {
-			if (items.length > 0) {
-				items.push({ kind: ActionListItemKind.Separator });
-			}
+		if (manageModelsAction) {
+			items.push({ kind: ActionListItemKind.Separator, section: otherModels.length ? ModelPickerSection.Other : undefined });
 			items.push({
-				item: {
-					id: 'otherModels',
-					enabled: true,
-					checked: false,
-					class: undefined,
-					tooltip: localize('chat.modelPicker.otherModels', "Other Models"),
-					label: localize('chat.modelPicker.otherModels', "Other Models"),
-					run: () => { /* toggle handled by isSectionToggle */ }
-				},
+				item: manageModelsAction,
 				kind: ActionListItemKind.Action,
-				label: localize('chat.modelPicker.otherModels', "Other Models"),
-				group: { title: '', icon: Codicon.chevronDown },
+				label: manageModelsAction.label,
+				group: { title: '', icon: Codicon.blank },
 				hideIcon: false,
-				section: ModelPickerSection.Other,
-				isSectionToggle: true,
+				section: otherModels.length ? ModelPickerSection.Other : undefined,
+				showAlways: true,
 			});
-			for (const model of otherModels) {
-				const entry = controlModels[model.metadata.id] ?? controlModels[model.identifier];
-				if (entry?.minVSCodeVersion && !isVersionAtLeast(currentVSCodeVersion, entry.minVSCodeVersion)) {
-					items.push(createUnavailableModelItem(model.metadata.id, entry, 'update', manageSettingsUrl, updateStateType, ModelPickerSection.Other, true));
-				} else {
-					items.push(createModelItem(createModelAction(model, selectedModelId, onSelect, ModelPickerSection.Other), model));
-				}
-			}
 		}
-	}
-
-	if (
-		chatEntitlementService.entitlement === ChatEntitlement.Free ||
-		chatEntitlementService.entitlement === ChatEntitlement.Pro ||
-		chatEntitlementService.entitlement === ChatEntitlement.ProPlus ||
-		chatEntitlementService.entitlement === ChatEntitlement.Business ||
-		chatEntitlementService.entitlement === ChatEntitlement.Enterprise ||
-		chatEntitlementService.isInternal
-	) {
-		items.push({ kind: ActionListItemKind.Separator, section: otherModels.length ? ModelPickerSection.Other : undefined });
-		items.push({
-			item: {
-				id: 'manageModels',
-				enabled: true,
-				checked: false,
-				class: undefined,
-				tooltip: localize('chat.manageModels.tooltip', "Manage Language Models"),
-				label: localize('chat.manageModels', "Manage Models..."),
-				run: () => { commandService.executeCommand(MANAGE_CHAT_COMMAND_ID); }
-			},
-			kind: ActionListItemKind.Action,
-			label: localize('chat.manageModels', "Manage Models..."),
-			group: { title: '', icon: Codicon.blank },
-			hideIcon: false,
-			section: otherModels.length ? ModelPickerSection.Other : undefined,
-			showAlways: true,
-		});
+	} else {
+		// Flat list: auto first, then all models sorted alphabetically
+		const autoModel = models.find(m => m.metadata.id === 'auto' && m.metadata.vendor === 'copilot');
+		if (autoModel) {
+			items.push(createModelItem(createModelAction(autoModel, selectedModelId, onSelect), autoModel, hoverPosition));
+		}
+		const sortedModels = models
+			.filter(m => m !== autoModel)
+			.sort((a, b) => {
+				const vendorCmp = a.metadata.vendor.localeCompare(b.metadata.vendor);
+				return vendorCmp !== 0 ? vendorCmp : a.metadata.name.localeCompare(b.metadata.name);
+			});
+		for (const model of sortedModels) {
+			items.push(createModelItem(createModelAction(model, selectedModelId, onSelect), model, hoverPosition));
+		}
 	}
 
 	return items;
 }
 
+export function getModelPickerAccessibilityProvider() {
+	return {
+		isChecked(element: IActionListItem<IActionWidgetDropdownAction>) {
+			return element.kind === ActionListItemKind.Action ? !!element?.item?.checked : undefined;
+		},
+		getRole: (element: IActionListItem<IActionWidgetDropdownAction>) => {
+			switch (element.kind) {
+				case ActionListItemKind.Action: return 'menuitemradio';
+				case ActionListItemKind.Separator: return 'separator';
+				default: return 'separator';
+			}
+		},
+		getWidgetRole: () => 'menu',
+	} as const;
+}
+
 function createUnavailableModelItem(
 	id: string,
 	entry: IModelControlEntry,
@@ -370,14 +411,12 @@ function createUnavailableModelItem(
 	manageSettingsUrl: string | undefined,
 	updateStateType: StateType,
 	section?: string,
-	showActionLink: boolean = true,
+	hoverPosition?: IHoverPositionOptions,
 ): IActionListItem<IActionWidgetDropdownAction> {
 	let description: string | MarkdownString | undefined;
 
 	if (reason === 'upgrade') {
-		description = showActionLink
-			? new MarkdownString(localize('chat.modelPicker.upgradeLink', "[Upgrade your plan](command:workbench.action.chat.upgradePlan \" \")"), { isTrusted: true })
-			: undefined;
+		description = new MarkdownString(localize('chat.modelPicker.upgradeLink', "[Upgrade](command:workbench.action.chat.upgradePlan \" \")"), { isTrusted: true });
 	} else if (reason === 'update') {
 		description = localize('chat.modelPicker.updateDescription', "Update VS Code");
 	} else {
@@ -389,7 +428,7 @@ function createUnavailableModelItem(
 	let hoverContent: MarkdownString;
 	if (reason === 'upgrade') {
 		hoverContent = new MarkdownString('', { isTrusted: true, supportThemeIcons: true });
-		hoverContent.appendMarkdown(localize('chat.modelPicker.upgradeHover', "[Upgrade your plan](command:workbench.action.chat.upgradePlan \" \") to use this model."));
+		hoverContent.appendMarkdown(localize('chat.modelPicker.upgradeHover', "[Upgrade to GitHub Copilot Pro](command:workbench.action.chat.upgradePlan \" \") with a free 30-day trial to use the best models."));
 	} else if (reason === 'update') {
 		hoverContent = getUpdateHoverContent(updateStateType);
 	} else {
@@ -416,7 +455,7 @@ function createUnavailableModelItem(
 		hideIcon: false,
 		className: 'chat-model-picker-unavailable',
 		section,
-		hover: { content: hoverContent },
+		hover: { content: hoverContent, position: hoverPosition },
 	};
 }
 
@@ -439,6 +478,7 @@ export class ModelPickerWidget extends Disposable {
 
 	private _selectedModel: ILanguageModelChatMetadataAndIdentifier | undefined;
 	private _badge: ModelPickerBadge | undefined;
+	private _hideChevrons: IObservable<boolean> | undefined;
 
 	private _domNode: HTMLElement | undefined;
 	private _badgeIcon: HTMLElement | undefined;
@@ -453,6 +493,7 @@ export class ModelPickerWidget extends Disposable {
 
 	constructor(
 		private readonly _delegate: IModelPickerDelegate,
+		private readonly _hoverPosition: IHoverPositionOptions | undefined,
 		@IActionWidgetService private readonly _actionWidgetService: IActionWidgetService,
 		@ICommandService private readonly _commandService: ICommandService,
 		@ITelemetryService private readonly _telemetryService: ITelemetryService,
@@ -464,6 +505,17 @@ export class ModelPickerWidget extends Disposable {
 		super();
 	}
 
+	setHideChevrons(hideChevrons: IObservable<boolean>): void {
+		this._hideChevrons = hideChevrons;
+		this._register(autorun(reader => {
+			const hide = hideChevrons.read(reader);
+			if (this._domNode) {
+				this._domNode.classList.toggle('hide-chevrons', hide);
+			}
+			this._renderLabel();
+		}));
+	}
+
 	setSelectedModel(model: ILanguageModelChatMetadataAndIdentifier | undefined): void {
 		this._selectedModel = model;
 		this._renderLabel();
@@ -481,6 +533,11 @@ export class ModelPickerWidget extends Disposable {
 		this._domNode.setAttribute('aria-haspopup', 'true');
 		this._domNode.setAttribute('aria-expanded', 'false');
 
+		// Apply initial collapsed state now that _domNode exists
+		if (this._hideChevrons?.get()) {
+			this._domNode.classList.toggle('hide-chevrons', true);
+		}
+
 		this._badgeIcon = dom.append(this._domNode, dom.$('span.model-picker-badge'));
 		this._updateBadge();
 
@@ -524,9 +581,12 @@ export class ModelPickerWidget extends Disposable {
 		};
 
 		const models = this._delegate.getModels();
+		const showFilter = models.length >= 10;
 		const isPro = isProUser(this._entitlementService.entitlement);
 		const manifest = this._languageModelsService.getModelsControlManifest();
 		const controlModelsForTier = isPro ? manifest.paid : manifest.free;
+		const canShowManageModelsAction = this._delegate.showManageModelsAction() && shouldShowManageModelsAction(this._entitlementService);
+		const manageModelsAction = canShowManageModelsAction ? createManageModelsAction(this._commandService) : undefined;
 		const items = buildModelPickerItems(
 			models,
 			this._selectedModel?.identifier,
@@ -536,17 +596,21 @@ export class ModelPickerWidget extends Disposable {
 			this._updateService.state.type,
 			onSelect,
 			this._productService.defaultChatAgent?.manageSettingsUrl,
-			this._delegate.canManageModels(),
-			this._commandService,
+			this._delegate.useGroupedModelPicker(),
+			!showFilter ? manageModelsAction : undefined,
 			this._entitlementService,
+			this._delegate.showUnavailableFeatured(),
+			this._delegate.showFeatured(),
+			this._hoverPosition,
 		);
 
 		const listOptions = {
-			showFilter: models.length >= 10,
+			showFilter,
 			filterPlaceholder: localize('chat.modelPicker.search', "Search models"),
+			filterActions: showFilter && manageModelsAction ? [manageModelsAction] : undefined,
 			focusFilterOnOpen: true,
 			collapsedByDefault: new Set([ModelPickerSection.Other]),
-			minWidth: 300,
+			minWidth: 200,
 		};
 		const previouslyFocusedElement = dom.getActiveElement();
 
@@ -573,21 +637,14 @@ export class ModelPickerWidget extends Disposable {
 			anchorElement,
 			undefined,
 			[],
-			{
-				isChecked(element) {
-					return element.kind === 'action' && !!element?.item?.checked;
-				},
-				getRole: (e) => {
-					switch (e.kind) {
-						case 'action': return 'menuitemcheckbox';
-						case 'separator': return 'separator';
-						default: return 'separator';
-					}
-				},
-				getWidgetRole: () => 'menu',
-			},
+			getModelPickerAccessibilityProvider(),
 			listOptions
 		);
+
+		const activeElement = dom.getActiveElement();
+		if (dom.isHTMLInputElement(activeElement) && activeElement.classList.contains('action-list-filter-input')) {
+			activeElement.classList.add('chat-model-picker-filter-input');
+		}
 	}
 
 	private _updateBadge(): void {
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/chatModelSelectionLogic.ts b/src/vs/workbench/contrib/chat/browser/widget/input/chatModelSelectionLogic.ts
new file mode 100644
index 0000000000000..206a3d5476563
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/chatModelSelectionLogic.ts
@@ -0,0 +1,288 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { ChatAgentLocation, ChatModeKind } from '../../../common/constants.js';
+import { ILanguageModelChatMetadata, ILanguageModelChatMetadataAndIdentifier } from '../../../common/languageModels.js';
+
+/**
+ * Describes the context needed for model selection decisions.
+ */
+export interface IModelSelectionContext {
+	readonly location: ChatAgentLocation;
+	readonly currentModeKind: ChatModeKind;
+	readonly isInlineChatV2Enabled: boolean;
+	readonly sessionType: string | undefined;
+}
+
+/**
+ * Filter models based on session type.
+ * When a session has a specific type (and it's not 'local'), only models targeting that
+ * session type are returned. Otherwise, general-purpose models are returned.
+ */
+export function filterModelsForSession(
+	models: ILanguageModelChatMetadataAndIdentifier[],
+	sessionType: string | undefined,
+	currentModeKind: ChatModeKind,
+	location: ChatAgentLocation,
+	isInlineChatV2Enabled: boolean,
+): ILanguageModelChatMetadataAndIdentifier[] {
+	if (sessionType && sessionType !== 'local' && hasModelsTargetingSession(models, sessionType)) {
+		return models.filter(entry =>
+			entry.metadata?.targetChatSessionType === sessionType &&
+			entry.metadata?.isUserSelectable
+		);
+	}
+
+	return models.filter(entry =>
+		!entry.metadata?.targetChatSessionType &&
+		entry.metadata?.isUserSelectable &&
+		isModelSupportedForMode(entry, currentModeKind) &&
+		isModelSupportedForInlineChat(entry, location, isInlineChatV2Enabled)
+	);
+}
+
+/**
+ * Check if a model is suitable for the current chat mode (e.g., agent mode requires tool calling).
+ */
+export function isModelSupportedForMode(
+	model: ILanguageModelChatMetadataAndIdentifier,
+	currentModeKind: ChatModeKind,
+): boolean {
+	if (currentModeKind === ChatModeKind.Agent) {
+		return ILanguageModelChatMetadata.suitableForAgentMode(model.metadata);
+	}
+	return true;
+}
+
+/**
+ * Check if a model is suitable for inline chat (editor inline) usage.
+ */
+export function isModelSupportedForInlineChat(
+	model: ILanguageModelChatMetadataAndIdentifier,
+	location: ChatAgentLocation,
+	isInlineChatV2Enabled: boolean,
+): boolean {
+	if (location !== ChatAgentLocation.EditorInline || !isInlineChatV2Enabled) {
+		return true;
+	}
+	return !!model.metadata.capabilities?.toolCalling;
+}
+
+/**
+ * Check if any models in the pool target a specific session type.
+ */
+export function hasModelsTargetingSession(
+	allModels: ILanguageModelChatMetadataAndIdentifier[],
+	sessionType: string | undefined,
+): boolean {
+	if (!sessionType) {
+		return false;
+	}
+	return allModels.some(m => m.metadata.targetChatSessionType === sessionType);
+}
+
+/**
+ * Check if a model is valid for the current session's model pool.
+ * If the session has targeted models, the model must target that session type.
+ * If no models target this session, the model must not be session-specific.
+ */
+export function isModelValidForSession(
+	model: ILanguageModelChatMetadataAndIdentifier,
+	allModels: ILanguageModelChatMetadataAndIdentifier[],
+	sessionType: string | undefined,
+): boolean {
+	if (hasModelsTargetingSession(allModels, sessionType)) {
+		return model.metadata.targetChatSessionType === sessionType;
+	}
+	return !model.metadata.targetChatSessionType;
+}
+
+/**
+ * Find the default model for a given location from a list of models.
+ * Prefers the model marked as default for the location, falls back to the first model.
+ */
+export function findDefaultModel(
+	models: ILanguageModelChatMetadataAndIdentifier[],
+	location: ChatAgentLocation,
+): ILanguageModelChatMetadataAndIdentifier | undefined {
+	return models.find(m => m.metadata.isDefaultForLocation[location]) || models[0];
+}
+
+/**
+ * Determine whether a persisted model selection should be restored.
+ *
+ * A persisted model should be restored if:
+ * 1. The model still exists in the available models list
+ * 2. Either the model wasn't the default at the time it was persisted,
+ *    OR it is currently the default for the location
+ *
+ * This prevents scenarios where a user's explicit model choice gets overridden
+ * when the default model changes, while still tracking default model changes
+ * for users who never explicitly chose a model.
+ */
+export function shouldRestorePersistedModel(
+	persistedModelId: string,
+	persistedAsDefault: boolean,
+	availableModels: ILanguageModelChatMetadataAndIdentifier[],
+	location: ChatAgentLocation,
+): { shouldRestore: boolean; model: ILanguageModelChatMetadataAndIdentifier | undefined } {
+	const model = availableModels.find(m => m.identifier === persistedModelId);
+	if (!model) {
+		return { shouldRestore: false, model: undefined };
+	}
+
+	if (!persistedAsDefault || model.metadata.isDefaultForLocation[location]) {
+		return { shouldRestore: true, model };
+	}
+
+	return { shouldRestore: false, model };
+}
+
+/**
+ * Determines whether the current model should be reset because it is no longer
+ * compatible with the current mode, session, or availability.
+ *
+ * Returns true if the model should be reset to default.
+ */
+export function shouldResetModelToDefault(
+	currentModel: ILanguageModelChatMetadataAndIdentifier | undefined,
+	availableModels: ILanguageModelChatMetadataAndIdentifier[],
+	context: IModelSelectionContext,
+	allModels: ILanguageModelChatMetadataAndIdentifier[],
+): boolean {
+	if (!currentModel) {
+		return true;
+	}
+
+	// Model is no longer in the available list
+	if (!availableModels.some(m => m.identifier === currentModel.identifier)) {
+		return true;
+	}
+
+	// Model not supported for current mode
+	if (!isModelSupportedForMode(currentModel, context.currentModeKind)) {
+		return true;
+	}
+
+	// Model not supported for inline chat
+	if (!isModelSupportedForInlineChat(currentModel, context.location, context.isInlineChatV2Enabled)) {
+		return true;
+	}
+
+	// Model not valid for current session
+	if (!isModelValidForSession(currentModel, allModels, context.sessionType)) {
+		return true;
+	}
+
+	return false;
+}
+
+/**
+ * Determines whether a model from a sync state should be applied to the current view.
+ *
+ * Returns an action:
+ * - `'keep'`    - the view already has the same model; no change needed.
+ * - `'apply'`   - the state model is valid; the caller should switch to it.
+ * - `'default'` - the state model is incompatible (wrong session pool, unsupported
+ *                 mode, or missing inline-chat capability); the caller should fall
+ *                 back to the default model for the current location.
+ *
+ * @param context Optional because some callers (e.g. unit tests, or code paths
+ *   that only care about session-pool validation) don't have a full UI context
+ *   available. When omitted, mode and inline-chat checks are skipped and only
+ *   session-pool membership is validated.
+ */
+export function resolveModelFromSyncState(
+	stateModel: ILanguageModelChatMetadataAndIdentifier,
+	currentModel: ILanguageModelChatMetadataAndIdentifier | undefined,
+	allModels: ILanguageModelChatMetadataAndIdentifier[],
+	sessionType: string | undefined,
+	context?: IModelSelectionContext,
+): { action: 'keep' | 'apply' | 'default' } {
+	// Already the same model — nothing to do
+	if (currentModel && currentModel.identifier === stateModel.identifier) {
+		return { action: 'keep' };
+	}
+
+	// Validate the state model belongs to this session's model pool
+	if (!isModelValidForSession(stateModel, allModels, sessionType)) {
+		return { action: 'default' };
+	}
+
+	// When a UI context is available, also validate mode and inline-chat compatibility
+	if (context) {
+		if (!isModelSupportedForMode(stateModel, context.currentModeKind)) {
+			return { action: 'default' };
+		}
+		if (!isModelSupportedForInlineChat(stateModel, context.location, context.isInlineChatV2Enabled)) {
+			return { action: 'default' };
+		}
+	}
+
+	return { action: 'apply' };
+}
+
+/**
+ * Merges live models with cached models per-vendor.
+ * For vendors whose models have resolved, uses live data.
+ * For vendors that are contributed but haven't resolved yet (startup race), keeps cached models.
+ * Vendors no longer contributed are evicted from cache.
+ */
+export function mergeModelsWithCache(
+	liveModels: ILanguageModelChatMetadataAndIdentifier[],
+	cachedModels: ILanguageModelChatMetadataAndIdentifier[],
+	contributedVendors: Set<string>,
+): ILanguageModelChatMetadataAndIdentifier[] {
+	if (liveModels.length > 0) {
+		const liveVendors = new Set(liveModels.map(m => m.metadata.vendor));
+		return [
+			...liveModels,
+			...cachedModels.filter(m => !liveVendors.has(m.metadata.vendor) && contributedVendors.has(m.metadata.vendor)),
+		];
+	}
+	return cachedModels;
+}
+
+/**
+ * Determines whether the currently selected model should be reset to default
+ * when the language model list changes.
+ *
+ * Returns true if the model should be reset to default (i.e., the selected model
+ * is no longer in the available models list).
+ */
+export function shouldResetOnModelListChange(
+	currentModelId: string | undefined,
+	availableModels: ILanguageModelChatMetadataAndIdentifier[],
+): boolean {
+	if (!currentModelId) {
+		return true;
+	}
+	return !availableModels.some(m => m.identifier === currentModelId);
+}
+
+/**
+ * Determines whether a late-arriving persisted model should be restored.
+ * This handles the startup race where the model wasn't available during
+ * `initSelectedModel` but arrives later via `onDidChangeLanguageModels`.
+ *
+ * The model must pass both the persisted-default check and the `isUserSelectable` check.
+ */
+export function shouldRestoreLateArrivingModel(
+	persistedModelId: string,
+	persistedAsDefault: boolean,
+	model: ILanguageModelChatMetadataAndIdentifier,
+	location: ChatAgentLocation,
+): boolean {
+	if (!model.metadata.isUserSelectable) {
+		return false;
+	}
+	const result = shouldRestorePersistedModel(
+		persistedModelId,
+		persistedAsDefault,
+		[model],
+		location,
+	);
+	return result.shouldRestore;
+}
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/chatQueuePickerActionItem.ts b/src/vs/workbench/contrib/chat/browser/widget/input/chatQueuePickerActionItem.ts
index fac726fe312a2..d9beb3af8bb52 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/chatQueuePickerActionItem.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/chatQueuePickerActionItem.ts
@@ -3,7 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { $, addDisposableListener, append, EventType } from '../../../../../../base/browser/dom.js';
+import { $, addDisposableListener, append, EventType, ModifierKeyEmitter } from '../../../../../../base/browser/dom.js';
 import { StandardKeyboardEvent } from '../../../../../../base/browser/keyboardEvent.js';
 import { ActionViewItem, BaseActionViewItem, IActionViewItemOptions } from '../../../../../../base/browser/ui/actionbar/actionViewItems.js';
 import { Action, IAction } from '../../../../../../base/common/actions.js';
@@ -42,6 +42,7 @@ export class ChatQueuePickerActionItem extends BaseActionViewItem {
 	private readonly _primaryActionAction: Action;
 	private readonly _primaryAction: ActionViewItem;
 	private readonly _dropdown: ActionWidgetDropdownActionViewItem;
+	private _altKeyPressed = false;
 
 	constructor(
 		action: IAction,
@@ -61,7 +62,7 @@ export class ChatQueuePickerActionItem extends BaseActionViewItem {
 		this._primaryActionAction = this._register(new Action(
 			'chat.queuePickerPrimary',
 			isSteerDefault ? localize('chat.steerWithMessage', "Steer with Message") : localize('chat.queueMessage', "Add to Queue"),
-			ThemeIcon.asClassName(Codicon.arrowUp),
+			ThemeIcon.asClassName(isSteerDefault ? Codicon.arrowUp : Codicon.add),
 			!!contextKeyService.getContextKeyValue(ChatContextKeys.inputHasText.key),
 			() => this._runDefaultAction()
 		));
@@ -91,21 +92,35 @@ export class ChatQueuePickerActionItem extends BaseActionViewItem {
 				this._updatePrimaryAction();
 			}
 		}));
+
+		// Toggle icon when Alt key is pressed/released
+		this._register(ModifierKeyEmitter.getInstance().event(status => {
+			if (this._altKeyPressed !== status.altKey) {
+				this._altKeyPressed = status.altKey;
+				this._updatePrimaryAction();
+			}
+		}));
 	}
 
 	private _isSteerDefault(): boolean {
 		return this.configurationService.getValue<string>(ChatConfiguration.RequestQueueingDefaultAction) === 'steer';
 	}
 
-	private _updatePrimaryAction(): void {
+	private _isEffectiveSteer(): boolean {
 		const isSteerDefault = this._isSteerDefault();
-		this._primaryActionAction.label = isSteerDefault
+		return this._altKeyPressed ? !isSteerDefault : isSteerDefault;
+	}
+
+	private _updatePrimaryAction(): void {
+		const isSteer = this._isEffectiveSteer();
+		this._primaryActionAction.label = isSteer
 			? localize('chat.steerWithMessage', "Steer with Message")
 			: localize('chat.queueMessage', "Add to Queue");
+		this._primaryActionAction.class = ThemeIcon.asClassName(isSteer ? Codicon.arrowUp : Codicon.add);
 	}
 
 	private _runDefaultAction(): void {
-		const actionId = this._isSteerDefault()
+		const actionId = this._isEffectiveSteer()
 			? ChatSteerWithMessageAction.ID
 			: ChatQueueMessageAction.ID;
 		this.commandService.executeCommand(actionId);
@@ -159,11 +174,14 @@ export class ChatQueuePickerActionItem extends BaseActionViewItem {
 	}
 
 	private _getDropdownActions(): IActionWidgetDropdownAction[] {
+		const isSteerDefault = this._isSteerDefault();
+
 		const queueAction: IActionWidgetDropdownAction = {
 			id: ChatQueueMessageAction.ID,
 			label: localize('chat.queueMessage', "Add to Queue"),
 			tooltip: '',
 			enabled: true,
+			checked: !isSteerDefault,
 			icon: Codicon.add,
 			class: undefined,
 			hover: {
@@ -179,7 +197,8 @@ export class ChatQueuePickerActionItem extends BaseActionViewItem {
 			label: localize('chat.steerWithMessage', "Steer with Message"),
 			tooltip: '',
 			enabled: true,
-			icon: Codicon.arrowRight,
+			checked: isSteerDefault,
+			icon: Codicon.arrowUp,
 			class: undefined,
 			hover: {
 				content: localize('chat.steerWithMessage.hover', "Send this message at the next opportunity, signaling the current request to yield. The current response will stop and the new message will be sent immediately."),
@@ -194,7 +213,7 @@ export class ChatQueuePickerActionItem extends BaseActionViewItem {
 			label: localize('chat.sendImmediately', "Stop and Send"),
 			tooltip: '',
 			enabled: true,
-			icon: Codicon.arrowUp,
+			icon: Codicon.arrowRight,
 			class: undefined,
 			hover: {
 				content: localize('chat.sendImmediately.hover', "Cancel the current request and send this message immediately."),
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/delegationSessionPickerActionItem.ts b/src/vs/workbench/contrib/chat/browser/widget/input/delegationSessionPickerActionItem.ts
index 9e5218f2afbf1..f7d921a424561 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/delegationSessionPickerActionItem.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/delegationSessionPickerActionItem.ts
@@ -7,9 +7,20 @@ import { IAction } from '../../../../../../base/common/actions.js';
 import { Codicon } from '../../../../../../base/common/codicons.js';
 import { URI } from '../../../../../../base/common/uri.js';
 import { localize } from '../../../../../../nls.js';
+import { IActionWidgetService } from '../../../../../../platform/actionWidget/browser/actionWidget.js';
 import { IActionWidgetDropdownAction } from '../../../../../../platform/actionWidget/browser/actionWidgetDropdown.js';
+import { MenuItemAction } from '../../../../../../platform/actions/common/actions.js';
+import { ICommandService } from '../../../../../../platform/commands/common/commands.js';
+import { IContextKeyService } from '../../../../../../platform/contextkey/common/contextkey.js';
+import { IKeybindingService } from '../../../../../../platform/keybinding/common/keybinding.js';
+import { IOpenerService } from '../../../../../../platform/opener/common/opener.js';
+import { ITelemetryService } from '../../../../../../platform/telemetry/common/telemetry.js';
+import { IsSessionsWindowContext } from '../../../../../common/contextkeys.js';
+import { IChatSessionsService } from '../../../common/chatSessionsService.js';
 import { ACTION_ID_NEW_CHAT } from '../../actions/chatActions.js';
 import { AgentSessionProviders, getAgentCanContinueIn, getAgentSessionProvider, isFirstPartyAgentSessionProvider } from '../../agentSessions/agentSessions.js';
+import { ISessionTypePickerDelegate } from '../../chat.js';
+import { IChatInputPickerOptions } from './chatInputPickerActionItem.js';
 import { ISessionTypeItem, SessionTypePickerActionItem } from './sessionTargetPickerActionItem.js';
 
 /**
@@ -17,6 +28,26 @@ import { ISessionTypeItem, SessionTypePickerActionItem } from './sessionTargetPi
  * This picker allows switching to remote execution providers when the session is not empty.
  */
 export class DelegationSessionPickerActionItem extends SessionTypePickerActionItem {
+
+	private readonly _isSessionsWindow: boolean;
+
+	constructor(
+		action: MenuItemAction,
+		chatSessionPosition: 'sidebar' | 'editor',
+		delegate: ISessionTypePickerDelegate,
+		pickerOptions: IChatInputPickerOptions,
+		@IActionWidgetService actionWidgetService: IActionWidgetService,
+		@IKeybindingService keybindingService: IKeybindingService,
+		@IContextKeyService contextKeyService: IContextKeyService,
+		@IChatSessionsService chatSessionsService: IChatSessionsService,
+		@ICommandService commandService: ICommandService,
+		@IOpenerService openerService: IOpenerService,
+		@ITelemetryService telemetryService: ITelemetryService,
+	) {
+		super(action, chatSessionPosition, delegate, pickerOptions, actionWidgetService, keybindingService, contextKeyService, chatSessionsService, commandService, openerService, telemetryService);
+		this._isSessionsWindow = IsSessionsWindowContext.getValue(contextKeyService) === true;
+	}
+
 	protected override _run(sessionTypeItem: ISessionTypeItem): void {
 		if (this.delegate.setPendingDelegationTarget) {
 			this.delegate.setPendingDelegationTarget(sessionTypeItem.type);
@@ -38,11 +69,17 @@ export class DelegationSessionPickerActionItem extends SessionTypePickerActionIt
 		const allContributions = this.chatSessionsService.getAllChatSessionContributions();
 		const contribution = allContributions.find(contribution => getAgentSessionProvider(contribution.type) === type);
 
-		if (this.delegate.getActiveSessionProvider() !== AgentSessionProviders.Local) {
-			return false; // Can only delegate when active session is local
+		// In core VS Code, only allow delegation from local sessions.
+		// In the sessions window, only allow delegation from background sessions (not cloud).
+		const activeProvider = this.delegate.getActiveSessionProvider();
+		if (!this._isSessionsWindow && activeProvider !== AgentSessionProviders.Local) {
+			return false;
+		}
+		if (this._isSessionsWindow && activeProvider !== AgentSessionProviders.Background) {
+			return false;
 		}
 
-		if (contribution && !contribution.canDelegate && this.delegate.getActiveSessionProvider() !== type /* Allow switching back to active type */) {
+		if (contribution && !contribution.canDelegate && activeProvider !== type /* Allow switching back to active type */) {
 			return false;
 		}
 
@@ -50,6 +87,11 @@ export class DelegationSessionPickerActionItem extends SessionTypePickerActionIt
 	}
 
 	protected override _isVisible(type: AgentSessionProviders): boolean {
+		// In the sessions window, only show Background and Cloud targets
+		if (this._isSessionsWindow && type === AgentSessionProviders.Local) {
+			return false;
+		}
+
 		if (this.delegate.getActiveSessionProvider() === type) {
 			return true; // Always show active session type
 		}
@@ -79,6 +121,9 @@ export class DelegationSessionPickerActionItem extends SessionTypePickerActionIt
 	}
 
 	protected override _getAdditionalActions(): IActionWidgetDropdownAction[] {
+		if (this._isSessionsWindow) {
+			return [];
+		}
 		return [{
 			id: 'newChatSession',
 			class: undefined,
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/editor/chatInputCompletions.ts b/src/vs/workbench/contrib/chat/browser/widget/input/editor/chatInputCompletions.ts
index e86cda4d36cda..7d959ef24f728 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/editor/chatInputCompletions.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/editor/chatInputCompletions.ts
@@ -55,10 +55,19 @@ import { ChatAgentLocation, ChatModeKind, isSupportedChatFileScheme } from '../.
 import { isToolSet } from '../../../../common/tools/languageModelToolsService.js';
 import { IChatSessionsService } from '../../../../common/chatSessionsService.js';
 import { IPromptsService } from '../../../../common/promptSyntax/service/promptsService.js';
+import {
+	PromptsType,
+	Target
+} from '../../../../common/promptSyntax/promptTypes.js';
 import { ChatSubmitAction, IChatExecuteActionContext } from '../../../actions/chatExecuteActions.js';
 import { IChatWidget, IChatWidgetService } from '../../../chat.js';
 import { resizeImage } from '../../../chatImageUtils.js';
 import { ChatDynamicVariableModel } from '../../../attachments/chatDynamicVariables.js';
+import { IChatService } from '../../../../common/chatService/chatService.js';
+import { IChatDebugService } from '../../../../common/chatDebugService.js';
+import { createDebugEventsAttachment } from '../../../chatDebug/chatDebugAttachment.js';
+import { getPromptFileType } from '../../../../common/promptSyntax/config/promptFileLocations.js';
+import { getChatSessionType } from '../../../../common/model/chatUri.js';
 
 /**
  * Regex matching a slash command word (e.g. `/foo`). Uses `\p{L}` for Unicode
@@ -77,6 +86,8 @@ class SlashCommandCompletions extends Disposable {
 		@IChatWidgetService private readonly chatWidgetService: IChatWidgetService,
 		@IChatSlashCommandService private readonly chatSlashCommandService: IChatSlashCommandService,
 		@IPromptsService private readonly promptsService: IPromptsService,
+		@IChatService chatService: IChatService,
+		@IChatSessionsService chatSessionsService: IChatSessionsService,
 		@IMcpService mcpService: IMcpService,
 	) {
 		super();
@@ -90,8 +101,15 @@ class SlashCommandCompletions extends Disposable {
 					return null;
 				}
 
-				if (widget.lockedAgentId && !widget.attachmentCapabilities.supportsPromptAttachments) {
-					return null;
+
+				let customAgentTarget: Target | undefined = undefined;
+				if (widget.lockedAgentId) {
+					if (!widget.attachmentCapabilities.supportsPromptAttachments) {
+						return null;
+					}
+					const sessionResource = widget.viewModel.model.sessionResource;
+					const ctx = sessionResource && chatService.getChatSessionFromInternalUri(sessionResource);
+					customAgentTarget = (ctx ? chatSessionsService.getCustomAgentTargetForSessionType(getChatSessionType(sessionResource)) : undefined) ?? Target.Undefined;
 				}
 
 				const range = computeCompletionRanges(model, position, SlashCommandWord);
@@ -117,18 +135,31 @@ class SlashCommandCompletions extends Disposable {
 				}
 
 				return {
-					suggestions: slashCommands.map((c, i): CompletionItem => {
-						const withSlash = `/${c.command}`;
-						return {
-							label: withSlash,
-							insertText: c.executeImmediately ? '' : `${withSlash} `,
-							documentation: c.detail,
-							range,
-							sortText: c.sortText ?? 'a'.repeat(i + 1),
-							kind: CompletionItemKind.Text, // The icons are disabled here anyway,
-							command: c.executeImmediately ? { id: ChatSubmitAction.ID, title: withSlash, arguments: [{ widget, inputValue: `${withSlash} ` } satisfies IChatExecuteActionContext] } : undefined,
-						};
-					})
+					suggestions: slashCommands
+						.filter(c => {
+							if (!widget.lockedAgentId) {
+								return true;
+							}
+							if (c.modes && c.modes.length && !c.modes.includes(ChatModeKind.Agent)) {
+								return false;
+							}
+							if (c.target && customAgentTarget && c.target !== customAgentTarget) {
+								return false;
+							}
+							return true;
+						})
+						.map((c, i): CompletionItem => {
+							const withSlash = `/${c.command}`;
+							return {
+								label: { label: withSlash, description: c.detail },
+								insertText: c.executeImmediately ? '' : `${withSlash} `,
+								documentation: c.detail,
+								range,
+								sortText: c.sortText ?? 'a'.repeat(i + 1),
+								kind: CompletionItemKind.Text, // The icons are disabled here anyway,
+								command: c.executeImmediately ? { id: ChatSubmitAction.ID, title: withSlash, arguments: [{ widget, inputValue: `${withSlash} ` } satisfies IChatExecuteActionContext] } : undefined,
+							};
+						})
 				};
 			}
 		}));
@@ -164,7 +195,7 @@ class SlashCommandCompletions extends Disposable {
 					suggestions: slashCommands.map((c, i): CompletionItem => {
 						const withSlash = `${chatSubcommandLeader}${c.command}`;
 						return {
-							label: withSlash,
+							label: { label: withSlash, description: c.detail },
 							insertText: c.executeImmediately ? '' : `${withSlash} `,
 							documentation: c.detail,
 							range,
@@ -213,7 +244,27 @@ class SlashCommandCompletions extends Disposable {
 				}
 
 				// Filter out commands that are not user-invocable (hidden from / menu)
-				const userInvocableCommands = promptCommands.filter(c => c.parsedPromptFile?.header?.userInvocable !== false);
+				const userInvocableCommands = promptCommands
+					.filter(c => {
+						if (widget.lockedAgentId) {
+							// Exclude extension-provided prompt files for locked agents.
+							if (c.promptPath.extension) {
+								return false;
+							}
+							// Exclude hooks as those don't work in locked agent scenarios.
+							try {
+								const promptType = getPromptFileType(c.promptPath.uri);
+								if (promptType && promptType === PromptsType.hook) {
+									return false;
+								}
+							} catch {
+
+							}
+						}
+						return true;
+					})
+					.filter(c => c.parsedPromptFile?.header?.userInvocable !== false)
+					.filter(c => !c.when || widget.scopedContextKeyService.contextMatchesRules(c.when));
 				if (userInvocableCommands.length === 0) {
 					return null;
 				}
@@ -801,6 +852,7 @@ interface IVariableCompletionsDetails {
 
 class BuiltinDynamicCompletions extends Disposable {
 	private static readonly addReferenceCommand = '_addReferenceCmd';
+	private static readonly addDebugEventsSnapshotCommand = '_addDebugEventsSnapshotCmd';
 	private static readonly VariableNameDef = new RegExp(`${chatVariableLeader}[\\w:-]*`, 'g'); // MUST be using `g`-flag
 
 
@@ -817,6 +869,7 @@ class BuiltinDynamicCompletions extends Disposable {
 		@ICodeEditorService private readonly codeEditorService: ICodeEditorService,
 		@IChatAgentService private readonly chatAgentService: IChatAgentService,
 		@IInstantiationService private readonly instantiationService: IInstantiationService,
+		@IChatDebugService private readonly chatDebugService: IChatDebugService,
 	) {
 		super();
 
@@ -902,10 +955,46 @@ class BuiltinDynamicCompletions extends Disposable {
 			return result;
 		});
 
+		// Debug Events Snapshot completion
+		this.registerVariableCompletions('debugEventsSnapshot', ({ widget, range }) => {
+			if (widget.location !== ChatAgentLocation.Chat) {
+				return;
+			}
+
+			const sessionResource = widget.viewModel?.sessionResource;
+			if (!sessionResource || this.chatDebugService.getEvents(sessionResource).length === 0) {
+				return;
+			}
+
+			const text = `${chatVariableLeader}debugEventsSnapshot`;
+			const result: CompletionList = { suggestions: [] };
+			result.suggestions.push({
+				label: { label: text, description: localize('debugEventsSnapshot.description', 'Attach debug events snapshot') },
+				filterText: text,
+				insertText: '',
+				range,
+				kind: CompletionItemKind.Text,
+				sortText: 'z',
+				command: {
+					id: BuiltinDynamicCompletions.addDebugEventsSnapshotCommand, title: '', arguments: [widget]
+				}
+			});
+			return result;
+		});
+
 		this._register(CommandsRegistry.registerCommand(BuiltinDynamicCompletions.addReferenceCommand, (_services, arg) => {
 			assertType(arg instanceof ReferenceArgument);
 			return this.cmdAddReference(arg);
 		}));
+
+		this._register(CommandsRegistry.registerCommand(BuiltinDynamicCompletions.addDebugEventsSnapshotCommand, async (_services, widget: IChatWidget) => {
+			const sessionResource = widget.viewModel?.sessionResource;
+			if (!sessionResource) {
+				return;
+			}
+			const attachment = await createDebugEventsAttachment(sessionResource, this.chatDebugService);
+			widget.attachmentModel.addContext(attachment);
+		}));
 	}
 
 	private findActiveCodeEditor(): ICodeEditor | undefined {
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/editor/chatInputEditorContrib.ts b/src/vs/workbench/contrib/chat/browser/widget/input/editor/chatInputEditorContrib.ts
index ce838a3e0a146..0bf73505e4e6f 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/editor/chatInputEditorContrib.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/editor/chatInputEditorContrib.ts
@@ -20,6 +20,7 @@ import { IChatAgentCommand, IChatAgentData, IChatAgentService } from '../../../.
 import { chatSlashCommandBackground, chatSlashCommandForeground } from '../../../../common/widget/chatColors.js';
 import { ChatRequestAgentPart, ChatRequestAgentSubcommandPart, ChatRequestDynamicVariablePart, ChatRequestSlashCommandPart, ChatRequestSlashPromptPart, ChatRequestTextPart, ChatRequestToolPart, ChatRequestToolSetPart, IParsedChatRequestPart, chatAgentLeader, chatSubcommandLeader } from '../../../../common/requestParser/chatParserTypes.js';
 import { ChatRequestParser } from '../../../../common/requestParser/chatRequestParser.js';
+import { getDynamicVariablesForWidget, getSelectedToolAndToolSetsForWidget } from '../../../attachments/chatVariables.js';
 import { IPromptsService } from '../../../../common/promptSyntax/service/promptsService.js';
 import { IChatWidget } from '../../../chat.js';
 import { ChatWidget } from '../../chatWidget.js';
@@ -411,7 +412,7 @@ class ChatTokenDeleter extends Disposable {
 			// If this was a simple delete, try to find out whether it was inside a token
 			if (!change.text && this.widget.viewModel) {
 				const attachmentCapabilities = previousSelectedAgent?.capabilities ?? this.widget.attachmentCapabilities;
-				const previousParsedValue = parser.parseChatRequest(this.widget.viewModel.sessionResource, previousInputValue, widget.location, { selectedAgent: previousSelectedAgent, mode: this.widget.input.currentModeKind, attachmentCapabilities });
+				const previousParsedValue = parser.parseChatRequestWithReferences(getDynamicVariablesForWidget(this.widget), getSelectedToolAndToolSetsForWidget(this.widget), previousInputValue, this.widget.location, { selectedAgent: previousSelectedAgent, mode: this.widget.input.currentModeKind, attachmentCapabilities });
 
 				// For dynamic variables, this has to happen in ChatDynamicVariableModel with the other bookkeeping
 				const deletableTokens = previousParsedValue.parts.filter(p => p instanceof ChatRequestAgentPart || p instanceof ChatRequestAgentSubcommandPart || p instanceof ChatRequestSlashCommandPart || p instanceof ChatRequestSlashPromptPart || p instanceof ChatRequestToolPart);
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/editor/chatPasteProviders.ts b/src/vs/workbench/contrib/chat/browser/widget/input/editor/chatPasteProviders.ts
index 65089b2020086..be28fc3feedb6 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/editor/chatPasteProviders.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/editor/chatPasteProviders.ts
@@ -5,6 +5,7 @@
 import { CancellationToken } from '../../../../../../../base/common/cancellation.js';
 import { Codicon } from '../../../../../../../base/common/codicons.js';
 import { createStringDataTransferItem, IDataTransferItem, IReadonlyVSDataTransfer, VSDataTransfer } from '../../../../../../../base/common/dataTransfer.js';
+import { alert } from '../../../../../../../base/browser/ui/aria/aria.js';
 import { HierarchicalKind } from '../../../../../../../base/common/hierarchicalKind.js';
 import { Disposable } from '../../../../../../../base/common/lifecycle.js';
 import { revive } from '../../../../../../../base/common/marshalling.js';
@@ -12,20 +13,25 @@ import { Mimes } from '../../../../../../../base/common/mime.js';
 import { Schemas } from '../../../../../../../base/common/network.js';
 import { basename, joinPath } from '../../../../../../../base/common/resources.js';
 import { URI, UriComponents } from '../../../../../../../base/common/uri.js';
+import { Position } from '../../../../../../../editor/common/core/position.js';
 import { IRange } from '../../../../../../../editor/common/core/range.js';
-import { DocumentPasteContext, DocumentPasteEdit, DocumentPasteEditProvider, DocumentPasteEditsSession } from '../../../../../../../editor/common/languages.js';
+import { DocumentPasteContext, DocumentPasteEdit, DocumentPasteEditProvider, DocumentPasteEditsSession, SymbolKinds } from '../../../../../../../editor/common/languages.js';
 import { ITextModel } from '../../../../../../../editor/common/model.js';
 import { ILanguageFeaturesService } from '../../../../../../../editor/common/services/languageFeatures.js';
 import { IModelService } from '../../../../../../../editor/common/services/model.js';
+import { IOutlineModelService } from '../../../../../../../editor/contrib/documentSymbols/browser/outlineModel.js';
+import { getDefinitionsAtPosition } from '../../../../../../../editor/contrib/gotoSymbol/browser/goToSymbol.js';
 import { localize } from '../../../../../../../nls.js';
 import { IEnvironmentService } from '../../../../../../../platform/environment/common/environment.js';
 import { IFileService } from '../../../../../../../platform/files/common/files.js';
 import { IInstantiationService } from '../../../../../../../platform/instantiation/common/instantiation.js';
 import { ILogService } from '../../../../../../../platform/log/common/log.js';
 import { IExtensionService, isProposedApiEnabled } from '../../../../../../services/extensions/common/extensions.js';
-import { IChatRequestPasteVariableEntry, IChatRequestVariableEntry } from '../../../../common/attachments/chatVariableEntries.js';
-import { IChatVariablesService, IDynamicVariable } from '../../../../common/attachments/chatVariables.js';
+import { IChatRequestPasteVariableEntry, IChatRequestVariableEntry, isImageVariableEntry } from '../../../../common/attachments/chatVariableEntries.js';
+import { chatVariableLeader } from '../../../../common/requestParser/chatParserTypes.js';
+import { IDynamicVariable } from '../../../../common/attachments/chatVariables.js';
 import { IChatWidgetService } from '../../../chat.js';
+import { getDynamicVariablesForWidget } from '../../../attachments/chatVariables.js';
 import { ChatDynamicVariableModel } from '../../../attachments/chatDynamicVariables.js';
 import { cleanupOldImages, createFileForMedia, resizeImage } from '../../../chatImageUtils.js';
 
@@ -36,6 +42,16 @@ interface SerializedCopyData {
 	readonly range: IRange;
 }
 
+interface ResolvedSymbolReference {
+	id: string;
+	fullName: string;
+	data: {
+		uri: URI;
+		range: IRange;
+	};
+	icon: IDynamicVariable['icon'];
+}
+
 export class PasteImageProvider implements DocumentPasteEditProvider {
 	private readonly imagesFolder: URI;
 
@@ -177,6 +193,12 @@ export class CopyTextProvider implements DocumentPasteEditProvider {
 	public readonly copyMimeTypes = [COPY_MIME_TYPES];
 	public readonly pasteMimeTypes = [];
 
+	constructor(
+		@IModelService private readonly modelService: IModelService,
+		@ILanguageFeaturesService private readonly languageFeaturesService: ILanguageFeaturesService,
+		@IOutlineModelService private readonly outlineModelService: IOutlineModelService,
+	) { }
+
 	async prepareDocumentPaste(model: ITextModel, ranges: readonly IRange[], dataTransfer: IReadonlyVSDataTransfer, token: CancellationToken): Promise<undefined | IReadonlyVSDataTransfer> {
 		if (model.uri.scheme === Schemas.vscodeChatInput) {
 			return;
@@ -185,8 +207,35 @@ export class CopyTextProvider implements DocumentPasteEditProvider {
 		const customDataTransfer = new VSDataTransfer();
 		const data: SerializedCopyData = { range: ranges[0], uri: model.uri.toJSON() };
 		customDataTransfer.append(COPY_MIME_TYPES, createStringDataTransferItem(JSON.stringify(data)));
+
+		const text = dataTransfer.get(Mimes.text);
+		if (text && ranges.length) {
+			void this.primeSymbolReferenceCache(model, ranges[0], text, token);
+		}
+
 		return customDataTransfer;
 	}
+
+	private async primeSymbolReferenceCache(model: ITextModel, range: IRange, textItem: IDataTransferItem, token: CancellationToken): Promise<void> {
+		const copiedText = model.getValueInRange(range);
+		if (range.startLineNumber !== range.endLineNumber) {
+			return;
+		}
+
+		if (token.isCancellationRequested || !identifierPattern.test(copiedText)) {
+			return;
+		}
+
+		cacheSymbolReference(model.uri, range, copiedText, resolveSymbolReference(
+			this.modelService,
+			this.languageFeaturesService,
+			this.outlineModelService,
+			model.uri,
+			range,
+			copiedText,
+			token,
+		));
+	}
 }
 
 class CopyAttachmentsProvider implements DocumentPasteEditProvider {
@@ -201,7 +250,6 @@ class CopyAttachmentsProvider implements DocumentPasteEditProvider {
 
 	constructor(
 		@IChatWidgetService private readonly chatWidgetService: IChatWidgetService,
-		@IChatVariablesService private readonly chatVariableService: IChatVariablesService
 	) { }
 
 	async prepareDocumentPaste(model: ITextModel, _ranges: readonly IRange[], _dataTransfer: IReadonlyVSDataTransfer, _token: CancellationToken): Promise<undefined | IReadonlyVSDataTransfer> {
@@ -212,7 +260,7 @@ class CopyAttachmentsProvider implements DocumentPasteEditProvider {
 		}
 
 		const attachments = widget.attachmentModel.attachments;
-		const dynamicVariables = this.chatVariableService.getDynamicVariables(widget.viewModel.sessionResource);
+		const dynamicVariables = getDynamicVariablesForWidget(widget);
 
 		if (attachments.length === 0 && dynamicVariables.length === 0) {
 			return undefined;
@@ -386,6 +434,7 @@ function createCustomPasteEdit(model: ITextModel, context: IChatRequestVariableE
 	const label = context.length === 1
 		? context[0].name
 		: localize('pastedAttachment.multiple', '{0} and {1} more', context[0].name, context.length - 1);
+	const announceImageAttachment = context.length === 1 && isImageVariableEntry(context[0]);
 
 	const customEdit = {
 		resource: model.uri,
@@ -403,6 +452,9 @@ function createCustomPasteEdit(model: ITextModel, context: IChatRequestVariableE
 				throw new Error('No widget found for redo');
 			}
 			widget.attachmentModel.addContext(...context);
+			if (announceImageAttachment) {
+				alert(localize('chat.pastedImageAttached', 'Attached image'));
+			}
 		},
 		metadata: {
 			needsConfirmation: false,
@@ -428,6 +480,205 @@ function createEditSession(edit: DocumentPasteEdit): DocumentPasteEditsSession {
 	};
 }
 
+const identifierPattern = /^[a-zA-Z_$][a-zA-Z0-9_$]*$/;
+const symbolCacheMaxSize = 3;
+type SymbolReferenceCacheEntry = {
+	key: string;
+	promise?: Promise<ResolvedSymbolReference | undefined>;
+};
+
+const symbolReferenceCache: SymbolReferenceCacheEntry[] = [];
+
+function getSymbolReferenceCacheKey(uri: URI, range: IRange, text: string): string {
+	return `${uri.toString()}|${range.startLineNumber}:${range.startColumn}-${range.endLineNumber}:${range.endColumn}|${text}`;
+}
+
+async function getCachedSymbolReference(uri: URI, range: IRange, text: string): Promise<ResolvedSymbolReference | undefined> {
+	const key = getSymbolReferenceCacheKey(uri, range, text);
+	return symbolReferenceCache.find(e => e.key === key)?.promise;
+}
+
+function cacheSymbolReference(uri: URI, range: IRange, text: string, valuePromise: Promise<ResolvedSymbolReference | undefined>): void {
+	const entry: SymbolReferenceCacheEntry = {
+		key: getSymbolReferenceCacheKey(uri, range, text),
+		promise: valuePromise,
+	};
+	symbolReferenceCache.unshift(entry);
+	while (symbolReferenceCache.length > symbolCacheMaxSize) {
+		symbolReferenceCache.pop();
+	}
+
+	valuePromise.catch(() => {
+		const i = symbolReferenceCache.indexOf(entry);
+		if (i !== -1) {
+			symbolReferenceCache.splice(i, 1);
+		}
+	});
+}
+
+async function resolveSymbolReference(
+	modelService: IModelService,
+	languageFeaturesService: ILanguageFeaturesService,
+	outlineModelService: IOutlineModelService,
+	sourceUri: URI,
+	sourceRange: IRange,
+	pastedText: string,
+	token: CancellationToken,
+): Promise<ResolvedSymbolReference | undefined> {
+	const sourceModel = modelService.getModel(sourceUri);
+	if (!sourceModel) {
+		return;
+	}
+
+	const sourcePosition = new Position(sourceRange.startLineNumber, sourceRange.startColumn);
+	const definitions = await getDefinitionsAtPosition(languageFeaturesService.definitionProvider, sourceModel, sourcePosition, false, token);
+	if (token.isCancellationRequested || !definitions.length) {
+		return;
+	}
+
+	const def = definitions[0];
+	const defRange = def.targetSelectionRange ?? def.range;
+	const defLocation = { uri: def.uri, range: defRange };
+
+	let icon = Codicon.symbolProperty;
+	const defModel = modelService.getModel(def.uri);
+	if (defModel) {
+		try {
+			const outline = await outlineModelService.getOrCreate(defModel, token);
+			if (!token.isCancellationRequested) {
+				const element = outline.getItemEnclosingPosition({ lineNumber: defRange.startLineNumber, column: defRange.startColumn });
+				if (element) {
+					icon = SymbolKinds.toIcon(element.symbol.kind);
+				}
+			}
+		} catch {
+			// Use default icon.
+		}
+	}
+
+	if (token.isCancellationRequested) {
+		return;
+	}
+
+	return {
+		id: `vscode.symbol/${JSON.stringify(defLocation)}`,
+		fullName: pastedText,
+		data: defLocation,
+		icon
+	};
+}
+
+class PasteSymbolProvider implements DocumentPasteEditProvider {
+
+	public readonly kind = new HierarchicalKind('chat.attach.symbol');
+	public readonly providedPasteEditKinds = [this.kind];
+
+	public readonly copyMimeTypes = [];
+	public readonly pasteMimeTypes = [COPY_MIME_TYPES];
+
+	constructor(
+		@IChatWidgetService private readonly chatWidgetService: IChatWidgetService,
+		@IModelService private readonly modelService: IModelService,
+		@ILanguageFeaturesService private readonly languageFeaturesService: ILanguageFeaturesService,
+		@IOutlineModelService private readonly outlineModelService: IOutlineModelService,
+	) { }
+
+	async provideDocumentPasteEdits(model: ITextModel, ranges: readonly IRange[], dataTransfer: IReadonlyVSDataTransfer, _context: DocumentPasteContext, token: CancellationToken): Promise<DocumentPasteEditsSession | undefined> {
+		if (model.uri.scheme !== Schemas.vscodeChatInput) {
+			return;
+		}
+
+		const text = dataTransfer.get(Mimes.text);
+		const additionalEditorData = dataTransfer.get(COPY_MIME_TYPES);
+		if (!text || !additionalEditorData) {
+			return;
+		}
+
+		const pastedText = await text.asString();
+		if (!identifierPattern.test(pastedText)) {
+			return;
+		}
+
+		let additionalData: SerializedCopyData;
+		try {
+			additionalData = JSON.parse(await additionalEditorData.asString());
+		} catch {
+			return;
+		}
+
+		const sourceUri = URI.revive(additionalData.uri);
+		const sourceRange = additionalData.range;
+
+		const widget = this.chatWidgetService.getWidgetByInputUri(model.uri);
+		if (!widget) {
+			return;
+		}
+
+		const cached = await getCachedSymbolReference(sourceUri, sourceRange, pastedText);
+		let resolved = cached;
+		if (!resolved) {
+			resolved = await resolveSymbolReference(
+				this.modelService,
+				this.languageFeaturesService,
+				this.outlineModelService,
+				sourceUri,
+				sourceRange,
+				pastedText,
+				token,
+			);
+		}
+		if (!resolved) {
+			return;
+		}
+
+		if (token.isCancellationRequested) {
+			return;
+		}
+
+		const symText = `${chatVariableLeader}sym:${pastedText}`;
+		const pasteRange = ranges[0];
+		const insertText = `${symText} `;
+
+		const refRange = {
+			startLineNumber: pasteRange.startLineNumber,
+			startColumn: pasteRange.startColumn,
+			endLineNumber: pasteRange.startLineNumber,
+			endColumn: pasteRange.startColumn + symText.length
+		};
+
+		const dynamicRef = {
+			id: resolved.id,
+			fullName: resolved.fullName,
+			range: refRange,
+			data: resolved.data,
+			icon: resolved.icon
+		};
+
+		const edit: DocumentPasteEdit = {
+			insertText,
+			title: localize('pastedSymbolReference', 'Pasted Symbol Reference'),
+			kind: this.kind,
+			handledMimeType: COPY_MIME_TYPES,
+			additionalEdit: {
+				edits: [{
+					resource: model.uri,
+					redo: () => {
+						const w = this.chatWidgetService.getWidgetByInputUri(model.uri);
+						w?.getContrib<ChatDynamicVariableModel>(ChatDynamicVariableModel.ID)?.addReference(dynamicRef);
+					},
+					undo: () => {
+						// The text removal by undo is sufficient; the dynamic variable
+						// model auto-cleans when the decoration text changes.
+					}
+				}]
+			}
+		};
+
+		edit.yieldTo = [{ kind: new HierarchicalKind('chat.attach.text') }];
+		return createEditSession(edit);
+	}
+}
+
 export class ChatPasteProvidersFeature extends Disposable {
 	constructor(
 		@IInstantiationService instaService: IInstantiationService,
@@ -443,7 +694,7 @@ export class ChatPasteProvidersFeature extends Disposable {
 		this._register(languageFeaturesService.documentPasteEditProvider.register({ scheme: Schemas.vscodeChatInput, pattern: '*', hasAccessToAllModels: true }, instaService.createInstance(CopyAttachmentsProvider)));
 		this._register(languageFeaturesService.documentPasteEditProvider.register({ scheme: Schemas.vscodeChatInput, pattern: '*', hasAccessToAllModels: true }, new PasteImageProvider(chatWidgetService, extensionService, fileService, environmentService, logService)));
 		this._register(languageFeaturesService.documentPasteEditProvider.register({ scheme: Schemas.vscodeChatInput, pattern: '*', hasAccessToAllModels: true }, new PasteTextProvider(chatWidgetService, modelService)));
-		this._register(languageFeaturesService.documentPasteEditProvider.register('*', new CopyTextProvider()));
-		this._register(languageFeaturesService.documentPasteEditProvider.register('*', new CopyTextProvider()));
+		this._register(languageFeaturesService.documentPasteEditProvider.register({ scheme: Schemas.vscodeChatInput, pattern: '*', hasAccessToAllModels: true }, instaService.createInstance(PasteSymbolProvider)));
+		this._register(languageFeaturesService.documentPasteEditProvider.register('*', instaService.createInstance(CopyTextProvider)));
 	}
 }
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/modePickerActionItem.ts b/src/vs/workbench/contrib/chat/browser/widget/input/modePickerActionItem.ts
index 3b552379ad1e8..fbd4a16a5794a 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/modePickerActionItem.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/modePickerActionItem.ts
@@ -28,7 +28,8 @@ import { IChatAgentService } from '../../../common/participants/chatAgents.js';
 import { ChatMode, IChatMode, IChatModeService } from '../../../common/chatModes.js';
 import { isOrganizationPromptFile } from '../../../common/promptSyntax/utils/promptsServiceUtils.js';
 import { ChatAgentLocation, ChatConfiguration, ChatModeKind } from '../../../common/constants.js';
-import { PromptsStorage, Target } from '../../../common/promptSyntax/service/promptsService.js';
+import { PromptsStorage } from '../../../common/promptSyntax/service/promptsService.js';
+import { Target } from '../../../common/promptSyntax/promptTypes.js';
 import { getOpenChatActionIdForMode } from '../../actions/chatActions.js';
 import { IToggleChatModeArgs, ToggleAgentModeActionId } from '../../actions/chatExecuteActions.js';
 import { ChatInputPickerActionViewItem, IChatInputPickerOptions } from './chatInputPickerActionItem.js';
@@ -260,11 +261,15 @@ export class ModePickerActionItem extends ChatInputPickerActionViewItem {
 		return menuContributions;
 	}
 
+	override render(container: HTMLElement): void {
+		super.render(container);
+		container.classList.add('chat-mode-picker-item');
+	}
+
 	protected override renderLabel(element: HTMLElement): IDisposable | null {
 		this.setAriaLabelAttributes(element);
 
 		const currentMode = this.delegate.currentMode.get();
-		const isDefault = currentMode.id === ChatMode.Agent.id;
 		const state = currentMode.label.get();
 		let icon = currentMode.icon.get();
 
@@ -274,13 +279,16 @@ export class ModePickerActionItem extends ChatInputPickerActionViewItem {
 		}
 
 		const labelElements = [];
+		const collapsed = this.pickerOptions.hideChevrons.get();
 		if (icon) {
 			labelElements.push(...renderLabelWithIcons(`$(${icon.id})`));
 		}
-		if (!isDefault || !icon || !this.pickerOptions.onlyShowIconsForDefaultActions.get()) {
+		if (!collapsed || !icon) {
 			labelElements.push(dom.$('span.chat-input-picker-label', undefined, state));
 		}
-		labelElements.push(...renderLabelWithIcons(`$(chevron-down)`));
+		if (!collapsed) {
+			labelElements.push(...renderLabelWithIcons(`$(chevron-down)`));
+		}
 
 		dom.reset(element, ...labelElements);
 		return null;
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/modelPickerActionItem.ts b/src/vs/workbench/contrib/chat/browser/widget/input/modelPickerActionItem.ts
index af61812b3a91f..adeaa775f4981 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/modelPickerActionItem.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/modelPickerActionItem.ts
@@ -29,7 +29,10 @@ export interface IModelPickerDelegate {
 	readonly currentModel: IObservable<ILanguageModelChatMetadataAndIdentifier | undefined>;
 	setModel(model: ILanguageModelChatMetadataAndIdentifier): void;
 	getModels(): ILanguageModelChatMetadataAndIdentifier[];
-	canManageModels(): boolean;
+	useGroupedModelPicker(): boolean;
+	showManageModelsAction(): boolean;
+	showUnavailableFeatured(): boolean;
+	showFeatured(): boolean;
 }
 
 type ChatModelChangeClassification = {
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/modelPickerActionItem2.ts b/src/vs/workbench/contrib/chat/browser/widget/input/modelPickerActionItem2.ts
index 6d302d2e00366..dfc1510a2c81a 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/modelPickerActionItem2.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/modelPickerActionItem2.ts
@@ -39,8 +39,9 @@ export class EnhancedModelPickerActionItem extends BaseActionViewItem {
 	) {
 		super(undefined, action);
 
-		this._pickerWidget = this._register(instantiationService.createInstance(ModelPickerWidget, delegate));
+		this._pickerWidget = this._register(instantiationService.createInstance(ModelPickerWidget, delegate, pickerOptions.hoverPosition));
 		this._pickerWidget.setSelectedModel(delegate.currentModel.get());
+		this._pickerWidget.setHideChevrons(pickerOptions.hideChevrons);
 
 		// Sync delegate → widget when model list or selection changes externally
 		this._register(autorun(t => {
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/permissionPickerActionItem.ts b/src/vs/workbench/contrib/chat/browser/widget/input/permissionPickerActionItem.ts
new file mode 100644
index 0000000000000..461611150227e
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/permissionPickerActionItem.ts
@@ -0,0 +1,231 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../../../base/browser/dom.js';
+import { renderLabelWithIcons } from '../../../../../../base/browser/ui/iconLabel/iconLabels.js';
+import { Codicon } from '../../../../../../base/common/codicons.js';
+import { IDisposable } from '../../../../../../base/common/lifecycle.js';
+import { IObservable } from '../../../../../../base/common/observable.js';
+import { ThemeIcon } from '../../../../../../base/common/themables.js';
+import { localize } from '../../../../../../nls.js';
+import { IActionWidgetService } from '../../../../../../platform/actionWidget/browser/actionWidget.js';
+import { IActionWidgetDropdownAction, IActionWidgetDropdownActionProvider } from '../../../../../../platform/actionWidget/browser/actionWidgetDropdown.js';
+import { IContextKeyService } from '../../../../../../platform/contextkey/common/contextkey.js';
+import { IKeybindingService } from '../../../../../../platform/keybinding/common/keybinding.js';
+import { ITelemetryService } from '../../../../../../platform/telemetry/common/telemetry.js';
+import { ChatConfiguration, ChatPermissionLevel } from '../../../common/constants.js';
+import { MenuItemAction } from '../../../../../../platform/actions/common/actions.js';
+import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
+import { IDialogService } from '../../../../../../platform/dialogs/common/dialogs.js';
+import Severity from '../../../../../../base/common/severity.js';
+import { MarkdownString } from '../../../../../../base/common/htmlContent.js';
+import { ChatInputPickerActionViewItem, IChatInputPickerOptions } from './chatInputPickerActionItem.js';
+
+// Track whether warnings have been shown this VS Code session
+const shownWarnings = new Set<ChatPermissionLevel>();
+
+function hasShownElevatedWarning(level: ChatPermissionLevel): boolean {
+	if (shownWarnings.has(level)) {
+		return true;
+	}
+	// Autopilot is stricter than AutoApprove, so confirming Autopilot
+	// implies the user already accepted the AutoApprove risks.
+	if (level === ChatPermissionLevel.AutoApprove && shownWarnings.has(ChatPermissionLevel.Autopilot)) {
+		return true;
+	}
+	return false;
+}
+
+export interface IPermissionPickerDelegate {
+	readonly currentPermissionLevel: IObservable<ChatPermissionLevel>;
+	readonly setPermissionLevel: (level: ChatPermissionLevel) => void;
+}
+
+export class PermissionPickerActionItem extends ChatInputPickerActionViewItem {
+	constructor(
+		action: MenuItemAction,
+		private readonly delegate: IPermissionPickerDelegate,
+		pickerOptions: IChatInputPickerOptions,
+		@IActionWidgetService actionWidgetService: IActionWidgetService,
+		@IKeybindingService keybindingService: IKeybindingService,
+		@IContextKeyService contextKeyService: IContextKeyService,
+		@ITelemetryService telemetryService: ITelemetryService,
+		@IConfigurationService configurationService: IConfigurationService,
+		@IDialogService private readonly dialogService: IDialogService,
+	) {
+		const isAutoApprovePolicyRestricted = () => configurationService.inspect<boolean>(ChatConfiguration.GlobalAutoApprove).policyValue === false;
+		const isAutopilotEnabled = () => configurationService.getValue<boolean>(ChatConfiguration.AutopilotEnabled) !== false;
+		const actionProvider: IActionWidgetDropdownActionProvider = {
+			getActions: () => {
+				const currentLevel = delegate.currentPermissionLevel.get();
+				const policyRestricted = isAutoApprovePolicyRestricted();
+				const actions: IActionWidgetDropdownAction[] = [
+					{
+						...action,
+						id: 'chat.permissions.default',
+						label: localize('permissions.default', "Default Approvals"),
+						description: localize('permissions.default.subtext', "Copilot uses your configured settings"),
+						icon: ThemeIcon.fromId(Codicon.shield.id),
+						checked: currentLevel === ChatPermissionLevel.Default,
+						tooltip: '',
+						hover: {
+							content: localize('permissions.default.description', "Use configured approval settings"),
+							position: pickerOptions.hoverPosition
+						},
+						run: async () => {
+							delegate.setPermissionLevel(ChatPermissionLevel.Default);
+							if (this.element) {
+								this.renderLabel(this.element);
+							}
+						},
+					} satisfies IActionWidgetDropdownAction,
+					{
+						...action,
+						id: 'chat.permissions.autoApprove',
+						label: localize('permissions.autoApprove', "Bypass Approvals"),
+						description: localize('permissions.autoApprove.subtext', "All tool calls are auto-approved"),
+						icon: ThemeIcon.fromId(Codicon.warning.id),
+						checked: currentLevel === ChatPermissionLevel.AutoApprove,
+						enabled: !policyRestricted,
+						tooltip: policyRestricted ? localize('permissions.autoApprove.policyDisabled', "Disabled by enterprise policy") : '',
+						hover: {
+							content: policyRestricted
+								? localize('permissions.autoApprove.policyDescription', "Disabled by enterprise policy")
+								: localize('permissions.autoApprove.description', "Auto-approve all tool calls and retry on errors"),
+							position: pickerOptions.hoverPosition
+						},
+						run: async () => {
+							if (!hasShownElevatedWarning(ChatPermissionLevel.AutoApprove)) {
+								const result = await this.dialogService.prompt({
+									type: Severity.Warning,
+									message: localize('permissions.autoApprove.warning.title', "Enable Bypass Approvals?"),
+									buttons: [
+										{
+											label: localize('permissions.autoApprove.warning.confirm', "Enable"),
+											run: () => true
+										},
+										{
+											label: localize('permissions.autoApprove.warning.cancel', "Cancel"),
+											run: () => false
+										},
+									],
+									custom: {
+										icon: Codicon.warning,
+										markdownDetails: [{
+											markdown: new MarkdownString(localize('permissions.autoApprove.warning.detail', "Bypass Approvals will auto-approve all tool calls without asking for confirmation. This includes file edits, terminal commands, and external tool calls.")),
+										}],
+									},
+								});
+								if (result.result !== true) {
+									return;
+								}
+								shownWarnings.add(ChatPermissionLevel.AutoApprove);
+							}
+							delegate.setPermissionLevel(ChatPermissionLevel.AutoApprove);
+							if (this.element) {
+								this.renderLabel(this.element);
+							}
+						},
+					} satisfies IActionWidgetDropdownAction,
+				];
+				if (isAutopilotEnabled()) {
+					actions.push({
+						...action,
+						id: 'chat.permissions.autopilot',
+						label: localize('permissions.autopilot', "Autopilot (Preview)"),
+						description: localize('permissions.autopilot.subtext', "Autonomously iterates from start to finish"),
+						icon: ThemeIcon.fromId(Codicon.rocket.id),
+						checked: currentLevel === ChatPermissionLevel.Autopilot,
+						enabled: !policyRestricted,
+						tooltip: policyRestricted ? localize('permissions.autopilot.policyDisabled', "Disabled by enterprise policy") : '',
+						hover: {
+							content: policyRestricted
+								? localize('permissions.autopilot.policyDescription', "Disabled by enterprise policy")
+								: localize('permissions.autopilot.description', "Auto-approve all tool calls and continue until the task is done"),
+							position: pickerOptions.hoverPosition
+						},
+						run: async () => {
+							if (!hasShownElevatedWarning(ChatPermissionLevel.Autopilot)) {
+								const result = await this.dialogService.prompt({
+									type: Severity.Warning,
+									message: localize('permissions.autopilot.warning.title', "Enable Autopilot?"),
+									buttons: [
+										{
+											label: localize('permissions.autopilot.warning.confirm', "Enable"),
+											run: () => true
+										},
+										{
+											label: localize('permissions.autopilot.warning.cancel', "Cancel"),
+											run: () => false
+										},
+									],
+									custom: {
+										icon: Codicon.rocket,
+										markdownDetails: [{
+											markdown: new MarkdownString(localize('permissions.autopilot.warning.detail', "Autopilot will auto-approve all tool calls and continue working autonomously until the task is complete. The agent will make decisions on your behalf without asking for confirmation.\n\nYou can stop the agent at any time by clicking the stop button. This applies to the current session only.")),
+										}],
+									},
+								});
+								if (result.result !== true) {
+									return;
+								}
+								shownWarnings.add(ChatPermissionLevel.Autopilot);
+							}
+							delegate.setPermissionLevel(ChatPermissionLevel.Autopilot);
+							if (this.element) {
+								this.renderLabel(this.element);
+							}
+						},
+					} satisfies IActionWidgetDropdownAction);
+				}
+				return actions;
+			}
+		};
+
+		super(action, {
+			actionProvider,
+			reporter: { id: 'ChatPermissionPicker', name: 'ChatPermissionPicker', includeOptions: true },
+			listOptions: { descriptionBelow: true, minWidth: 255 },
+		}, pickerOptions, actionWidgetService, keybindingService, contextKeyService, telemetryService);
+	}
+
+	protected override renderLabel(element: HTMLElement): IDisposable | null {
+		this.setAriaLabelAttributes(element);
+
+		const level = this.delegate.currentPermissionLevel.get();
+		let icon: ThemeIcon;
+		let label: string;
+		switch (level) {
+			case ChatPermissionLevel.Autopilot:
+				icon = Codicon.rocket;
+				label = localize('permissions.autopilot.label', "Autopilot (Preview)");
+				break;
+			case ChatPermissionLevel.AutoApprove:
+				icon = Codicon.warning;
+				label = localize('permissions.autoApprove.label', "Bypass Approvals");
+				break;
+			default:
+				icon = Codicon.shield;
+				label = localize('permissions.default.label', "Default Approvals");
+				break;
+		}
+
+		const labelElements = [];
+		labelElements.push(...renderLabelWithIcons(`$(${icon.id})`));
+		labelElements.push(dom.$('span.chat-input-picker-label', undefined, label));
+		labelElements.push(...renderLabelWithIcons(`$(chevron-down)`));
+
+		dom.reset(element, ...labelElements);
+		element.classList.toggle('warning', level === ChatPermissionLevel.Autopilot);
+		element.classList.toggle('info', level === ChatPermissionLevel.AutoApprove);
+		return null;
+	}
+
+	public refresh(): void {
+		if (this.element) {
+			this.renderLabel(this.element);
+		}
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/sessionTargetPickerActionItem.ts b/src/vs/workbench/contrib/chat/browser/widget/input/sessionTargetPickerActionItem.ts
index 5a31e7f187cb8..d70bfd5969581 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/sessionTargetPickerActionItem.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/sessionTargetPickerActionItem.ts
@@ -18,11 +18,11 @@ import { IKeybindingService } from '../../../../../../platform/keybinding/common
 import { IOpenerService } from '../../../../../../platform/opener/common/opener.js';
 import { ITelemetryService } from '../../../../../../platform/telemetry/common/telemetry.js';
 import { IChatSessionsService } from '../../../common/chatSessionsService.js';
-import { AgentSessionProviders, backgroundAgentDisplayName, getAgentSessionProvider, getAgentSessionProviderDescription, getAgentSessionProviderIcon, getAgentSessionProviderName, isFirstPartyAgentSessionProvider } from '../../agentSessions/agentSessions.js';
+import { AgentSessionProviders, getAgentSessionProvider, getAgentSessionProviderDescription, getAgentSessionProviderIcon, getAgentSessionProviderName, isFirstPartyAgentSessionProvider } from '../../agentSessions/agentSessions.js';
 import { ChatInputPickerActionViewItem, IChatInputPickerOptions } from './chatInputPickerActionItem.js';
 import { ISessionTypePickerDelegate } from '../../chat.js';
 import { IActionProvider } from '../../../../../../base/browser/ui/dropdown/dropdown.js';
-import { autorun } from '../../../../../../base/common/observable.js';
+
 
 export interface ISessionTypeItem {
 	type: AgentSessionProviders;
@@ -105,15 +105,7 @@ export class SessionTypePickerActionItem extends ChatInputPickerActionViewItem {
 			this._updateAgentSessionItems();
 		}));
 
-		// Re-render when the background agent display name changes via experiment
-		// Note: autorun runs immediately, so this also handles initial population
-		this._register(autorun(reader => {
-			backgroundAgentDisplayName.read(reader);
-			this._updateAgentSessionItems();
-			if (this.element) {
-				this.renderLabel(this.element);
-			}
-		}));
+		this._updateAgentSessionItems();
 	}
 
 	protected _run(sessionTypeItem: ISessionTypeItem): void {
@@ -200,6 +192,11 @@ export class SessionTypePickerActionItem extends ChatInputPickerActionViewItem {
 		return undefined;
 	}
 
+	override render(container: HTMLElement): void {
+		super.render(container);
+		container.classList.add('chat-session-target-picker-item');
+	}
+
 	protected override renderLabel(element: HTMLElement): IDisposable | null {
 		this.setAriaLabelAttributes(element);
 		const currentType = this._getSelectedSessionType();
@@ -209,9 +206,7 @@ export class SessionTypePickerActionItem extends ChatInputPickerActionViewItem {
 
 		const labelElements = [];
 		labelElements.push(...renderLabelWithIcons(`$(${icon.id})`));
-		if (!this.pickerOptions.onlyShowIconsForDefaultActions.get()) {
-			labelElements.push(dom.$('span.chat-input-picker-label', undefined, label));
-		}
+		labelElements.push(dom.$('span.chat-input-picker-label', undefined, label));
 		labelElements.push(...renderLabelWithIcons(`$(chevron-down)`));
 
 		dom.reset(element, ...labelElements);
diff --git a/src/vs/workbench/contrib/chat/browser/widget/input/workspacePickerActionItem.ts b/src/vs/workbench/contrib/chat/browser/widget/input/workspacePickerActionItem.ts
index 989c3bc64e8ed..828664f9a8853 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/input/workspacePickerActionItem.ts
+++ b/src/vs/workbench/contrib/chat/browser/widget/input/workspacePickerActionItem.ts
@@ -118,7 +118,9 @@ export class WorkspacePickerActionItem extends ChatInputPickerActionViewItem {
 			labelElements.push(dom.$('span.chat-input-picker-label', undefined, localize('selectWorkspace', "Workspace")));
 		}
 
-		labelElements.push(...renderLabelWithIcons(`$(chevron-down)`));
+		if (!this.pickerOptions.hideChevrons.get()) {
+			labelElements.push(...renderLabelWithIcons(`$(chevron-down)`));
+		}
 
 		dom.reset(element, ...labelElements);
 
diff --git a/src/vs/workbench/contrib/chat/browser/widget/media/chat.css b/src/vs/workbench/contrib/chat/browser/widget/media/chat.css
index 35e910c2c37a7..1278d6c1e7982 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/media/chat.css
+++ b/src/vs/workbench/contrib/chat/browser/widget/media/chat.css
@@ -282,7 +282,11 @@
 }
 
 .interactive-item-container > .value .chat-used-context {
-	margin-bottom: 10px;
+	margin-bottom: 16px;
+}
+
+.interactive-item-container > .value .chat-used-context .chat-used-context-list {
+	margin-bottom: 0;
 }
 
 .interactive-item-container .value .rendered-markdown:not(:has(.chat-extensions-content-part)) {
@@ -309,10 +313,13 @@
 	font-weight: 600;
 }
 
-.interactive-item-container .value .rendered-markdown table {
+.interactive-item-container .value .rendered-markdown .rendered-markdown-table-scroll-wrapper {
 	width: 100%;
-	text-align: left;
 	margin-bottom: 16px;
+}
+
+.interactive-item-container .value .rendered-markdown table {
+	text-align: left;
 	border-radius: var(--vscode-cornerRadius-medium);
 	overflow: hidden;
 	border-collapse: separate;
@@ -328,6 +335,11 @@
 	padding: 4px 6px;
 }
 
+.interactive-item-container .value .rendered-markdown table th {
+	white-space: normal;
+	overflow-wrap: break-word;
+}
+
 .interactive-item-container .value .rendered-markdown table td:last-child,
 .interactive-item-container .value .rendered-markdown table th:last-child {
 	border-right: none;
@@ -612,7 +624,7 @@
 	}
 
 	&:not(:last-child) {
-		margin-bottom: 12px;
+		margin-bottom: 16px;
 	}
 }
 
@@ -808,11 +820,26 @@ have to be updated for changes to the rules above, or to support more deeply nes
 	position: relative;
 }
 
-/* Context usage widget container - positioned in the bottom toolbar */
-.interactive-session .chat-input-toolbars .chat-context-usage-container {
+/* Prevent contents from covering border corners. Not applied in compact mode
+	because overflow:hidden creates a BFC that causes a ResizeObserver ↔ layout
+	feedback loop when toolbars share width with the editor. */
+.interactive-session .interactive-input-part:not(.compact) .chat-input-container {
+	/* Prevent contents from covering border corner */
+	overflow: hidden;
+}
+
+/* Context usage widget container - positioned in the secondary toolbar below input */
+.interactive-session .chat-input-toolbars .chat-context-usage-container,
+.interactive-session .chat-secondary-toolbar .chat-context-usage-container {
 	display: flex;
 	align-items: center;
 	flex-shrink: 0;
+	margin-left: auto;
+	order: 1;
+}
+
+/* When context usage is inside the toolbars (compact mode), keep the ordering */
+.interactive-session .chat-input-toolbars .chat-context-usage-container {
 	order: 1;
 }
 
@@ -1253,6 +1280,8 @@ have to be updated for changes to the rules above, or to support more deeply nes
 	display: flex;
 	justify-content: space-between;
 	padding-bottom: 0;
+	/* no scrollbar */
+	padding-right: 6px;
 	border-radius: var(--vscode-cornerRadius-small);
 }
 
@@ -1268,7 +1297,12 @@ have to be updated for changes to the rules above, or to support more deeply nes
 }
 
 .chat-editor-container {
-	padding: 0 4px;
+	padding: 0 0 0 4px;
+}
+
+.interactive-session .interactive-input-part.compact .chat-editor-container {
+	/* No scrollbar */
+	padding-right: 4px;
 }
 
 .chat-editor-container .monaco-editor .mtk1 {
@@ -1309,10 +1343,94 @@ have to be updated for changes to the rules above, or to support more deeply nes
 	margin-top: 4px;
 }
 
+/* Secondary toolbar below the input box */
+.interactive-session .chat-secondary-toolbar {
+	display: flex;
+	align-items: center;
+	gap: 6px;
+	padding: 0 4px 0 5px;
+}
+
+.interactive-session .chat-secondary-toolbar:empty {
+	display: none;
+}
+
+.interactive-session .chat-secondary-toolbar > .chat-secondary-input-toolbar {
+	overflow: hidden;
+	min-width: 0px;
+	color: var(--vscode-icon-foreground);
+
+	.monaco-action-bar .action-item .codicon {
+		color: var(--vscode-icon-foreground);
+	}
+
+	.chat-input-picker-item {
+		min-width: 0px;
+		overflow: hidden;
+
+		.action-label {
+			min-width: 0px;
+			overflow: hidden;
+			position: relative;
+
+			.chat-input-picker-label {
+				overflow: hidden;
+				text-overflow: ellipsis;
+			}
+
+			span + .chat-input-picker-label {
+				margin-left: 2px;
+			}
+
+			.codicon {
+				font-size: 12px;
+			}
+		}
+
+		.codicon {
+			flex-shrink: 0;
+		}
+	}
+}
+
+.interactive-session .chat-secondary-toolbar .chat-input-picker-item .action-label {
+	height: 16px;
+	padding: 3px 0px 3px 6px;
+	display: flex;
+	align-items: center;
+	color: var(--vscode-icon-foreground);
+}
+
+.interactive-session .chat-secondary-toolbar .chat-input-picker-item .action-label.warning {
+	color: var(--vscode-problemsWarningIcon-foreground);
+}
+
+.interactive-session .chat-secondary-toolbar .chat-input-picker-item .action-label.warning .codicon {
+	color: var(--vscode-problemsWarningIcon-foreground) !important;
+}
+
+.interactive-session .chat-secondary-toolbar .chat-input-picker-item .action-label.info {
+	color: var(--vscode-problemsInfoIcon-foreground);
+}
+
+.interactive-session .chat-secondary-toolbar .chat-input-picker-item .action-label.info .codicon {
+	color: var(--vscode-problemsInfoIcon-foreground) !important;
+}
+
+.monaco-workbench .interactive-session .chat-secondary-toolbar .chat-input-picker-item .action-label .codicon-chevron-down {
+	font-size: 10px;
+	margin-left: 4px;
+	opacity: 0.75;
+}
+
 .interactive-session .chat-input-toolbars :not(.responsive.chat-input-toolbar) .actions-container:first-child {
 	margin-right: auto;
 }
 
+.interactive-session .chat-input-toolbars > .chat-input-toolbar .actions-container:first-child {
+	margin-right: 0;
+}
+
 .interactive-session .chat-input-toolbars .tool-warning-indicator {
 	position: absolute;
 	bottom: 0;
@@ -1390,19 +1508,57 @@ have to be updated for changes to the rules above, or to support more deeply nes
 .interactive-session .chat-input-toolbar .chat-input-picker-item .action-label,
 .interactive-session .chat-input-toolbar .chat-sessionPicker-item .action-label {
 	height: 16px;
-	padding: 3px 0px 3px 6px;
+	padding: 3px 1px 3px 7px;
 	display: flex;
 	align-items: center;
 	color: var(--vscode-icon-foreground);
 }
 
+/* Keep hover background while picker dropdown is open */
+.interactive-session .chat-input-toolbar .action-label[aria-expanded="true"],
+.interactive-session .chat-secondary-toolbar .action-label[aria-expanded="true"] {
+	background-color: var(--vscode-toolbar-hoverBackground);
+}
+
+/* When chevrons are hidden and only showing an icon (no label), size to 22x22 with centered icon */
+.interactive-session .chat-input-toolbar .chat-input-picker-item .action-label.hide-chevrons:not(:has(.chat-input-picker-label)),
+.interactive-session .chat-input-toolbar .chat-input-picker-item.hide-chevrons .action-label:not(:has(.chat-input-picker-label)),
+.interactive-session .chat-input-toolbar .chat-sessionPicker-item .action-label.hide-chevrons:not(:has(.chat-input-picker-label)) {
+	width: 22px;
+	min-width: 22px;
+	height: 22px;
+	padding: 0;
+	box-sizing: border-box;
+	display: flex;
+	align-items: center;
+	justify-content: center;
+
+	.codicon {
+		justify-content: center;
+	}
+}
+
+
+/* Add context button icon sizing */
+.interactive-session .chat-input-toolbar .action-item:has(.codicon-add) .action-label {
+	display: flex;
+	align-items: center;
+	justify-content: center;
+}
+
+.interactive-session .chat-input-toolbar .action-item:has(.codicon-add) .codicon-add {
+	font-size: 14px;
+}
+
 .monaco-workbench .interactive-session .chat-input-toolbar .chat-input-picker-item .action-label .codicon-chevron-down,
 .monaco-workbench .interactive-session .chat-input-toolbar .chat-sessionPicker-item .action-label .codicon-chevron-down {
-	font-size: 12px;
-	margin-left: 2px;
+	font-size: 10px;
+	margin-left: 4px;
+	opacity: 0.75;
 }
 
-.interactive-session .chat-input-toolbars .monaco-action-bar .actions-container {
+.interactive-session .chat-input-toolbars .monaco-action-bar .actions-container,
+.interactive-session .chat-secondary-toolbar .monaco-action-bar .actions-container {
 	display: flex;
 	gap: 4px;
 }
@@ -1432,6 +1588,18 @@ have to be updated for changes to the rules above, or to support more deeply nes
 	color: var(--vscode-textLink-activeForeground);
 }
 
+.action-widget .action-list-filter-input.chat-model-picker-filter-input,
+.action-widget .action-list-filter-input.chat-model-picker-filter-input:focus {
+	outline: none;
+	box-shadow: none;
+	border-color: transparent;
+	background-color: transparent;
+}
+
+.action-widget .action-list-filter:has(.chat-model-picker-filter-input) {
+	margin-bottom: 4px;
+}
+
 .interactive-session .chat-input-toolbars .codicon-debug-stop {
 	color: var(--vscode-icon-foreground) !important;
 }
@@ -1602,7 +1770,7 @@ have to be updated for changes to the rules above, or to support more deeply nes
 
 .interactive-session .interactive-input-part {
 	margin: 0px 12px;
-	padding: 4px 0 12px 0px;
+	padding: 4px 0 4px 0px;
 	display: flex;
 	flex-direction: column;
 	gap: 4px;
@@ -2239,7 +2407,7 @@ have to be updated for changes to the rules above, or to support more deeply nes
 	display: flex;
 	align-items: center;
 	gap: 4px;
-	margin: 0 0 6px 0;
+	margin: 0 0 14px 0;
 	font-size: 13px;
 
 	/* Tool calls transition from a progress to a collapsible list part, which needs to have this top padding.
@@ -2313,6 +2481,7 @@ have to be updated for changes to the rules above, or to support more deeply nes
 .show-checkmarks .progress-container > .codicon.codicon-check,
 .progress-container.show-checkmarks > .codicon.codicon-check {
 	display: inline-flex;
+	margin-left: 4px;
 }
 
 .interactive-item-container .chat-command-button {
@@ -2721,15 +2890,25 @@ have to be updated for changes to the rules above, or to support more deeply nes
 	}
 
 	.interactive-request .header.partially-disabled .detail-container {
-		margin-left: 4px;
+		margin-left: 0px;
 	}
 
 	.interactive-item-container .header .detail .codicon-check {
 		margin-right: 7px;
 		vertical-align: middle;
 		font-size: 11px;
+		display: none;
+	}
+
+	.interactive-item-container .header.partially-disabled .detail.show-checkmarks {
+		margin-left: 4px;
+
+		.codicon-check {
+			display: inline;
+		}
 	}
 
+
 	.request-hover {
 		position: absolute;
 		overflow: hidden;
diff --git a/src/vs/workbench/contrib/chat/browser/widget/media/chatViewWelcome.css b/src/vs/workbench/contrib/chat/browser/widget/media/chatViewWelcome.css
index 17c3b7dd1c2de..8a6e91f1861b9 100644
--- a/src/vs/workbench/contrib/chat/browser/widget/media/chatViewWelcome.css
+++ b/src/vs/workbench/contrib/chat/browser/widget/media/chatViewWelcome.css
@@ -16,13 +16,13 @@
 
 .interactive-session.chat-view-getting-started-disabled {
 
-	/* hide most welcome pieces (except suggested actions) when we show recent sessions to make some space */
+	/* hide most welcome pieces when we show recent sessions to make some space */
 	.chat-welcome-view .chat-welcome-view-icon,
 	.chat-welcome-view .chat-welcome-view-title,
 	.chat-welcome-view .chat-welcome-view-message,
 	.chat-welcome-view .chat-welcome-view-disclaimer,
 	.chat-welcome-view .chat-welcome-view-tips {
-		visibility: hidden;
+		display: none;
 	}
 }
 
@@ -53,11 +53,13 @@ div.chat-welcome-view {
 	padding: 12px;
 
 	& > .chat-welcome-view-icon {
-		min-height: 48px;
+		min-height: 40px;
 	}
 
 	& > .chat-welcome-view-icon .codicon {
+		color: var(--vscode-descriptionForeground);
 		font-size: 40px;
+		margin-bottom: 24px;
 	}
 
 	& > .chat-welcome-view-icon.custom-icon {
@@ -84,7 +86,9 @@ div.chat-welcome-view {
 	}
 
 	& > .chat-welcome-view-title {
-		font-size: 24px;
+		font-size: 13px;
+		font-weight: 600;
+		color: var(--vscode-foreground);
 		margin-top: 5px;
 		text-align: center;
 		line-height: normal;
@@ -94,10 +98,11 @@ div.chat-welcome-view {
 	& > .chat-welcome-view-message {
 		position: relative;
 		text-align: center;
-		max-width: 100%;
+		max-width: 280px;
 		padding: 0 20px;
-		margin: 0 auto;
-		color: var(--vscode-foreground);
+		margin: 8px auto 0;
+		color: var(--vscode-descriptionForeground);
+		font-size: 12px;
 
 		a {
 			color: var(--vscode-textLink-foreground);
@@ -110,8 +115,7 @@ div.chat-welcome-view {
 		}
 
 		p {
-			margin-top: 8px;
-			margin-bottom: 8px;
+			margin: 0;
 		}
 	}
 
@@ -153,11 +157,16 @@ div.chat-welcome-view {
 	}
 
 	& > .chat-welcome-view-disclaimer {
-		color: var(--vscode-foreground);
+		color: var(--vscode-descriptionForeground);
 		text-align: center;
-		margin: -16px auto;
-		max-width: 400px;
+		margin: 0;
+		max-width: 256px;
 		padding: 0 12px;
+		font-size: 12px;
+
+		p {
+			margin: 0;
+		}
 
 		a {
 			color: var(--vscode-textLink-foreground);
@@ -190,9 +199,7 @@ div.chat-welcome-view {
 		position: absolute;
 		top: 8px;
 		left: 16px;
-		font-size: 11px;
-		text-transform: uppercase;
-		letter-spacing: 0.5px;
+		font-size: 12px;
 		color: var(--vscode-descriptionForeground);
 		margin: 0;
 		text-align: left;
@@ -202,8 +209,8 @@ div.chat-welcome-view {
 		display: flex;
 		align-items: center;
 		gap: 6px;
-		height: 24px;
-		padding: 0 8px;
+		height: 20px;
+		padding: 0 6px;
 		border-radius: 4px;
 		background-color: var(--vscode-editorWidget-background);
 		cursor: pointer;
@@ -214,20 +221,10 @@ div.chat-welcome-view {
 		flex: 0 0 auto;
 
 		& > .chat-welcome-view-suggested-prompt-title {
-			font-size: 13px;
+			font-size: 12px;
 			color: var(--vscode-editorWidget-foreground);
 			white-space: nowrap;
 		}
-
-		& > .chat-welcome-view-suggested-prompt-description {
-			font-size: 13px;
-			color: var(--vscode-descriptionForeground);
-			overflow: hidden;
-			text-overflow: ellipsis;
-			white-space: nowrap;
-			flex: 0 1 auto;
-			min-width: 0;
-		}
 	}
 
 	> .chat-welcome-view-suggested-prompt:hover {
diff --git a/src/vs/workbench/contrib/chat/browser/widgetHosts/editor/chatEditor.ts b/src/vs/workbench/contrib/chat/browser/widgetHosts/editor/chatEditor.ts
index 8a1c71fb6156b..0a3344392bc4f 100644
--- a/src/vs/workbench/contrib/chat/browser/widgetHosts/editor/chatEditor.ts
+++ b/src/vs/workbench/contrib/chat/browser/widgetHosts/editor/chatEditor.ts
@@ -219,7 +219,7 @@ export class ChatEditor extends AbstractEditorWithViewState<IChatEditorViewState
 
 		if (chatSessionType !== localChatSessionType) {
 			try {
-				await raceCancellationError(this.chatSessionsService.canResolveChatSession(input.resource), token);
+				await raceCancellationError(this.chatSessionsService.canResolveChatSession(input.resource.scheme), token);
 				const contributions = this.chatSessionsService.getAllChatSessionContributions();
 				const contribution = contributions.find(c => c.type === chatSessionType);
 				if (contribution) {
diff --git a/src/vs/workbench/contrib/chat/browser/widgetHosts/editor/chatEditorInput.ts b/src/vs/workbench/contrib/chat/browser/widgetHosts/editor/chatEditorInput.ts
index 47214b2d68d4e..7a5b0d5d880cb 100644
--- a/src/vs/workbench/contrib/chat/browser/widgetHosts/editor/chatEditorInput.ts
+++ b/src/vs/workbench/contrib/chat/browser/widgetHosts/editor/chatEditorInput.ts
@@ -61,6 +61,7 @@ export class ChatEditorInput extends EditorInput implements IEditorCloseHandler
 		@IChatService private readonly chatService: IChatService,
 		@IDialogService private readonly dialogService: IDialogService,
 		@IChatSessionsService private readonly chatSessionsService: IChatSessionsService,
+		@IInstantiationService private readonly instantiationService: IInstantiationService,
 	) {
 		super();
 
@@ -107,7 +108,11 @@ export class ChatEditorInput extends EditorInput implements IEditorCloseHandler
 	}
 
 	override get capabilities(): EditorInputCapabilities {
-		return super.capabilities | EditorInputCapabilities.Singleton | EditorInputCapabilities.CanDropIntoEditor;
+		return super.capabilities | EditorInputCapabilities.ForceReveal | EditorInputCapabilities.CanDropIntoEditor;
+	}
+
+	override copy(): EditorInput {
+		return this.instantiationService.createInstance(ChatEditorInput, ChatEditorInput.getNewEditorUri(), {});
 	}
 
 	override matches(otherInput: EditorInput | IUntypedEditorInput): boolean {
@@ -189,10 +194,7 @@ export class ChatEditorInput extends EditorInput implements IEditorCloseHandler
 		// TODO@osortega,@rebornix double check: Chat Session Item icon is reserved for chat session list and deprecated for chat session status. thus here we use session type icon. We may want to show status for the Editor Title.
 		const sessionType = this.getSessionType();
 		if (sessionType !== localChatSessionType) {
-			const typeIcon = this.chatSessionsService.getIconForSessionType(sessionType);
-			if (typeIcon) {
-				return typeIcon;
-			}
+			return this.chatSessionsService.getChatSessionContribution(sessionType)?.icon;
 		}
 
 		return undefined;
diff --git a/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/chatContextUsageDetails.ts b/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/chatContextUsageDetails.ts
index 43fc982f081a2..15127efd3ad9d 100644
--- a/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/chatContextUsageDetails.ts
+++ b/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/chatContextUsageDetails.ts
@@ -22,8 +22,10 @@ export interface IChatContextUsagePromptTokenDetail {
 
 export interface IChatContextUsageData {
 	usedTokens: number;
+	completionTokens: number;
 	totalContextWindow: number;
 	percentage: number;
+	outputBufferPercentage?: number;
 	promptTokenDetails?: readonly IChatContextUsagePromptTokenDetail[];
 }
 
@@ -39,6 +41,8 @@ export class ChatContextUsageDetails extends Disposable {
 	private readonly percentageLabel: HTMLElement;
 	private readonly tokenCountLabel: HTMLElement;
 	private readonly progressFill: HTMLElement;
+	private readonly outputBufferFill: HTMLElement;
+	private readonly outputBufferLegend: HTMLElement;
 	private readonly tokenDetailsContainer: HTMLElement;
 	private readonly warningMessage: HTMLElement;
 	private readonly actionsSection: HTMLElement;
@@ -52,36 +56,40 @@ export class ChatContextUsageDetails extends Disposable {
 
 		this.domNode = $('.chat-context-usage-details');
 
-		// Using same structure as ChatUsageWidget quota items
-		this.quotaItem = this.domNode.appendChild($('.quota-item'));
+		// Quota indicator — using same structure as ChatStatusDashboard
+		this.quotaItem = this.domNode.appendChild($('.quota-indicator'));
 
-		// Header row with label
-		const quotaItemHeader = this.quotaItem.appendChild($('.quota-item-header'));
-		const quotaItemLabel = quotaItemHeader.appendChild($('.quota-item-label'));
-		quotaItemLabel.textContent = localize('contextWindow', "Context Window");
+		// Header row
+		const header = this.domNode.insertBefore($('div.header'), this.quotaItem);
+		header.textContent = localize('contextWindow', "Context Window");
 
-		// Token count and percentage row (on same line)
-		const tokenRow = this.quotaItem.appendChild($('.token-row'));
-		this.tokenCountLabel = tokenRow.appendChild($('.token-count-label'));
-		this.percentageLabel = tokenRow.appendChild($('.quota-item-value'));
+		// Quota label row with token count + percentage
+		const quotaLabel = this.quotaItem.appendChild($('.quota-label'));
+		this.tokenCountLabel = quotaLabel.appendChild($('span'));
+		this.percentageLabel = quotaLabel.appendChild($('span.quota-value'));
 
-		// Progress bar - using same structure as chat usage widget
+		// Progress bar
 		const progressBar = this.quotaItem.appendChild($('.quota-bar'));
 		this.progressFill = progressBar.appendChild($('.quota-bit'));
+		this.outputBufferFill = progressBar.appendChild($('.quota-bit.output-buffer'));
+
+		// Output buffer legend (shown only when outputBuffer is provided)
+		this.outputBufferLegend = this.quotaItem.appendChild($('.output-buffer-legend'));
+		this.outputBufferLegend.appendChild($('.output-buffer-swatch'));
+		const legendLabel = this.outputBufferLegend.appendChild($('span'));
+		legendLabel.textContent = localize('outputReserved', "Reserved for response");
+		this.outputBufferLegend.style.display = 'none';
 
 		// Token details container (for category breakdown)
 		this.tokenDetailsContainer = this.domNode.appendChild($('.token-details-container'));
 
 		// Warning message (shown when usage is high)
-		this.warningMessage = this.domNode.appendChild($('.warning-message'));
+		this.warningMessage = this.domNode.appendChild($('div.description'));
 		this.warningMessage.textContent = localize('qualityWarning', "Quality may decline as limit nears.");
 		this.warningMessage.style.display = 'none';
 
-		// Actions section with header, separator, and button bar
+		// Actions section with button bar
 		this.actionsSection = this.domNode.appendChild($('.actions-section'));
-		this.actionsSection.appendChild($('.separator'));
-		const actionsHeader = this.actionsSection.appendChild($('.actions-header'));
-		actionsHeader.textContent = localize('actions', "Actions");
 		const buttonBarContainer = this.actionsSection.appendChild($('.button-bar-container'));
 		this._register(this.instantiationService.createInstance(MenuWorkbenchButtonBar, buttonBarContainer, MenuId.ChatContextUsageActions, {
 			toolbarOptions: {
@@ -102,21 +110,33 @@ export class ChatContextUsageDetails extends Disposable {
 	}
 
 	update(data: IChatContextUsageData): void {
-		const { percentage, usedTokens, totalContextWindow, promptTokenDetails } = data;
+		const { percentage, usedTokens, totalContextWindow, outputBufferPercentage, promptTokenDetails } = data;
 
-		// Update token count and percentage on same line
+		// Update token count and percentage — reflects actual usage only
 		this.tokenCountLabel.textContent = localize(
 			'tokenCount',
 			"{0} / {1} tokens",
 			this.formatTokenCount(usedTokens, 1),
 			this.formatTokenCount(totalContextWindow, 0)
 		);
-		this.percentageLabel.textContent = `• ${percentage.toFixed(0)}%`;
-
-		// Update progress bar
-		this.progressFill.style.width = `${Math.min(100, percentage)}%`;
+		this.percentageLabel.textContent = localize('quotaDisplay', "{0}%", Math.min(100, percentage).toFixed(0));
+
+		// Progress bar: actual usage fill + remaining reserved output fill
+		const usageBarWidth = Math.max(0, Math.min(100, percentage));
+		this.progressFill.style.width = `${usageBarWidth}%`;
+
+		if (outputBufferPercentage !== undefined && outputBufferPercentage > 0) {
+			// Clamp so the reserve never overflows the bar
+			this.outputBufferFill.style.width = `${Math.max(0, Math.min(100 - usageBarWidth, outputBufferPercentage))}%`;
+			this.outputBufferFill.style.display = '';
+			this.outputBufferLegend.style.display = '';
+		} else {
+			this.outputBufferFill.style.width = '0';
+			this.outputBufferFill.style.display = 'none';
+			this.outputBufferLegend.style.display = 'none';
+		}
 
-		// Update color classes based on usage level on the quota item
+		// Color classes based on actual usage percentage
 		this.quotaItem.classList.remove('warning', 'error');
 		if (percentage >= 90) {
 			this.quotaItem.classList.add('error');
diff --git a/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/chatContextUsageWidget.ts b/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/chatContextUsageWidget.ts
index b20f39c7cf678..f81c8d79f907d 100644
--- a/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/chatContextUsageWidget.ts
+++ b/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/chatContextUsageWidget.ts
@@ -92,6 +92,7 @@ export class ChatContextUsageWidget extends Disposable {
 	readonly domNode: HTMLElement;
 
 	private readonly progressIndicator: CircularProgressIndicator;
+	private readonly percentageLabel: HTMLElement;
 
 	private readonly _isVisible = observableValue<boolean>(this, false);
 	get isVisible(): IObservable<boolean> { return this._isVisible; }
@@ -130,6 +131,9 @@ export class ChatContextUsageWidget extends Disposable {
 		this.progressIndicator = new CircularProgressIndicator();
 		iconContainer.appendChild(this.progressIndicator.domNode);
 
+		// Percentage label (visible on hover/focus)
+		this.percentageLabel = this.domNode.appendChild($('.percentage-label'));
+
 		// Track context usage opened state
 		this._contextUsageOpenedKey = ChatContextKeys.contextUsageHasBeenOpened.bindTo(this.contextKeyService);
 
@@ -270,23 +274,36 @@ export class ChatContextUsageWidget extends Disposable {
 		}
 
 		const promptTokens = usage.promptTokens;
+		const completionTokens = usage.completionTokens;
 		const promptTokenDetails = usage.promptTokenDetails;
+		const outputBuffer = usage.outputBuffer;
 		const totalContextWindow = maxInputTokens + maxOutputTokens;
-		const usedTokens = promptTokens + maxOutputTokens;
-		const percentage = Math.min(100, (usedTokens / totalContextWindow) * 100);
+		const usedTokens = promptTokens + completionTokens;
+		const percentage = (usedTokens / totalContextWindow) * 100;
+
+		// Remaining reserve = whatever the model reserved minus what completions
+		// have already consumed. Once completions exceed the reserve, it drops to 0.
+		const outputBufferPercentage = outputBuffer !== undefined
+			? (Math.max(0, outputBuffer - completionTokens) / totalContextWindow) * 100
+			: undefined;
 
-		this.render(percentage, usedTokens, totalContextWindow, promptTokenDetails);
+		this.render(percentage, completionTokens, usedTokens, totalContextWindow, outputBufferPercentage, promptTokenDetails);
 		this.show();
 	}
 
-	private render(percentage: number, usedTokens: number, totalContextWindow: number, promptTokenDetails?: readonly { category: string; label: string; percentageOfPrompt: number }[]): void {
+	private render(percentage: number, completionTokens: number, usedTokens: number, totalContextWindow: number, outputBufferPercentage: number | undefined, promptTokenDetails?: readonly { category: string; label: string; percentageOfPrompt: number }[]): void {
 		// Store current data for use in details popup
-		this.currentData = { usedTokens, totalContextWindow, percentage, promptTokenDetails };
+		this.currentData = { usedTokens, completionTokens, totalContextWindow, percentage, outputBufferPercentage, promptTokenDetails };
 
-		// Update pie chart progress
+		// Pie chart shows actual usage percentage only
 		this.progressIndicator.setProgress(percentage);
 
-		// Update color based on usage level
+		// Update percentage label and aria-label (clamp display to 100)
+		const roundedPercentage = Math.min(100, Math.round(percentage));
+		this.percentageLabel.textContent = `${roundedPercentage}%`;
+		this.domNode.setAttribute('aria-label', localize('contextUsagePercentageLabel', "Context window usage: {0}%", roundedPercentage));
+
+		// Color based on actual usage percentage
 		this.domNode.classList.remove('warning', 'error');
 		if (percentage >= 90) {
 			this.domNode.classList.add('error');
diff --git a/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/chatViewPane.ts b/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/chatViewPane.ts
index 8db0ce90838c9..e1184c2f82b33 100644
--- a/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/chatViewPane.ts
+++ b/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/chatViewPane.ts
@@ -66,6 +66,7 @@ import { IAgentSession } from '../../agentSessions/agentSessionsModel.js';
 import { IChatEntitlementService } from '../../../../../services/chat/common/chatEntitlementService.js';
 import { toErrorMessage } from '../../../../../../base/common/errorMessage.js';
 import { IWorkbenchEnvironmentService } from '../../../../../services/environment/common/environmentService.js';
+import { IHostService } from '../../../../../services/host/browser/host.js';
 
 interface IChatViewPaneState extends Partial<IChatModelInputState> {
 	/**
@@ -126,6 +127,7 @@ export class ChatViewPane extends ViewPane implements IViewWelcomeDelegate {
 		@ICommandService private readonly commandService: ICommandService,
 		@IActivityService private readonly activityService: IActivityService,
 		@IWorkbenchEnvironmentService private readonly workbenchEnvironmentService: IWorkbenchEnvironmentService,
+		@IHostService private readonly hostService: IHostService,
 	) {
 		super(options, keybindingService, contextMenuService, configurationService, contextKeyService, viewDescriptorService, instantiationService, openerService, themeService, hoverService);
 
@@ -397,6 +399,13 @@ export class ChatViewPane extends ViewPane implements IViewWelcomeDelegate {
 
 		sessionsToolbar.context = sessionsControl;
 
+		// Refresh sessions when window gets focus to compensate for missing events
+		this._register(this.hostService.onDidChangeFocus(hasFocus => {
+			if (hasFocus) {
+				sessionsControl.refresh();
+			}
+		}));
+
 		// Deal with orientation configuration
 		this._register(Event.runAndSubscribe(Event.filter(this.configurationService.onDidChangeConfiguration, e => e.affectsConfiguration(ChatConfiguration.ChatViewSessionsOrientation)), e => {
 			const newSessionsViewerOrientationConfiguration = this.configurationService.getValue<'stacked' | 'sideBySide' | unknown>(ChatConfiguration.ChatViewSessionsOrientation);
@@ -530,6 +539,8 @@ export class ChatViewPane extends ViewPane implements IViewWelcomeDelegate {
 					: 'explicit',
 				supportsChangingModes: true,
 				dndContainer: parent,
+				inputEditorMinLines: this.workbenchEnvironmentService.isSessionsWindow ? 2 : undefined,
+				isSessionsWindow: this.workbenchEnvironmentService.isSessionsWindow,
 			},
 			{
 				listForeground: SIDE_BAR_FOREGROUND,
@@ -697,7 +708,7 @@ export class ChatViewPane extends ViewPane implements IViewWelcomeDelegate {
 		const model = ref?.object;
 
 		if (model) {
-			await this.updateWidgetLockState(model.sessionResource); // Update widget lock state based on session type
+			await this.updateWidgetLockState(getChatSessionType(model.sessionResource)); // Update widget lock state based on session type
 
 			// remember as model to restore in view state
 			this.viewState.sessionResource = model.sessionResource;
@@ -719,8 +730,7 @@ export class ChatViewPane extends ViewPane implements IViewWelcomeDelegate {
 		return model;
 	}
 
-	private async updateWidgetLockState(sessionResource: URI): Promise<void> {
-		const sessionType = getChatSessionType(sessionResource);
+	private async updateWidgetLockState(sessionType: string): Promise<void> {
 		if (sessionType === localChatSessionType) {
 			this._widget.unlockFromCodingAgent();
 			return;
@@ -728,9 +738,9 @@ export class ChatViewPane extends ViewPane implements IViewWelcomeDelegate {
 
 		let canResolve = false;
 		try {
-			canResolve = await this.chatSessionsService.canResolveChatSession(sessionResource);
+			canResolve = await this.chatSessionsService.canResolveChatSession(sessionType);
 		} catch (error) {
-			this.logService.warn(`Failed to resolve chat session '${sessionResource.toString()}' for locking`, error);
+			this.logService.warn(`Failed to resolve chat session type '${sessionType}' for locking`, error);
 		}
 
 		if (!canResolve) {
@@ -740,7 +750,7 @@ export class ChatViewPane extends ViewPane implements IViewWelcomeDelegate {
 
 		const contribution = this.chatSessionsService.getChatSessionContribution(sessionType);
 		if (contribution) {
-			this._widget.lockToCodingAgent(contribution.name, contribution.displayName, contribution.type);
+			this._widget.lockToCodingAgent(contribution.name, contribution.displayName, sessionType);
 		} else {
 			this._widget.unlockFromCodingAgent();
 		}
diff --git a/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/media/chatContextUsageDetails.css b/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/media/chatContextUsageDetails.css
index 41b7a7ad9d1d1..9eecdcc1c5f72 100644
--- a/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/media/chatContextUsageDetails.css
+++ b/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/media/chatContextUsageDetails.css
@@ -15,7 +15,8 @@
 .chat-context-usage-details {
 	display: flex;
 	flex-direction: column;
-	padding: 4px 0;
+	margin-top: 4px;
+	margin-bottom: 4px;
 	min-width: 200px;
 }
 
@@ -23,97 +24,172 @@
 	outline: none;
 }
 
-/* Using same structure as ChatUsageWidget quota items */
-.chat-context-usage-details .quota-item {
-	margin-bottom: 4px;
-}
-
-.chat-context-usage-details .quota-item-header {
+/* Section headers — matching ChatStatusDashboard */
+.chat-context-usage-details div.header {
 	display: flex;
 	align-items: center;
-	justify-content: space-between;
-	margin-bottom: 2px;
-}
-
-.chat-context-usage-details .quota-item-label {
-	color: var(--vscode-foreground);
-}
-
-.chat-context-usage-details .quota-item-value {
 	color: var(--vscode-descriptionForeground);
+	margin-bottom: 4px;
+	font-weight: 600;
 }
 
-.chat-context-usage-details .token-row {
+/* Quota indicator — matching ChatStatusDashboard */
+.chat-context-usage-details .quota-indicator .quota-label {
 	display: flex;
-	align-items: center;
-	gap: 4px;
-	margin-bottom: 2px;
+	justify-content: space-between;
+	gap: 20px;
+	margin-bottom: 3px;
 }
 
-.chat-context-usage-details .token-count-label {
-	font-size: 12px;
+.chat-context-usage-details .quota-indicator .quota-label .quota-value {
 	color: var(--vscode-descriptionForeground);
 }
 
-/* Progress bar - matching chat usage implementation */
-.chat-context-usage-details .quota-item .quota-bar {
+.chat-context-usage-details .quota-indicator .quota-bar {
 	width: 100%;
 	height: 4px;
 	background-color: var(--vscode-gauge-background);
 	border-radius: 4px;
 	border: 1px solid var(--vscode-gauge-border);
-	margin: 2px 0;
+	margin: 4px 0;
+	display: flex;
 }
 
-.chat-context-usage-details .quota-item .quota-bar .quota-bit {
+.chat-context-usage-details .quota-indicator .quota-bar .quota-bit {
 	height: 100%;
 	background-color: var(--vscode-gauge-foreground);
 	border-radius: 4px;
 	transition: width 0.3s ease;
 }
 
-.chat-context-usage-details .quota-item.warning .quota-bar {
+.chat-context-usage-details .quota-indicator .quota-bar .quota-bit.output-buffer {
+	background: repeating-linear-gradient(
+		-45deg,
+		var(--vscode-gauge-foreground),
+		var(--vscode-gauge-foreground) 2px,
+		transparent 2px,
+		transparent 4px
+	);
+	border-radius: 0 4px 4px 0;
+}
+
+.chat-context-usage-details .quota-indicator .quota-bar .quota-bit:not(.output-buffer):has(+ .quota-bit.output-buffer:not([style*="display: none"])) {
+	border-radius: 4px 0 0 4px;
+}
+
+/* Output buffer legend */
+.chat-context-usage-details .quota-indicator .output-buffer-legend {
+	display: flex;
+	align-items: center;
+	gap: 6px;
+	margin-top: 4px;
+	font-size: 11px;
+	color: var(--vscode-descriptionForeground);
+}
+
+.chat-context-usage-details .quota-indicator .output-buffer-legend .output-buffer-swatch {
+	width: 12px;
+	height: 8px;
+	border-radius: 2px;
+	background: repeating-linear-gradient(
+		-45deg,
+		var(--vscode-gauge-foreground),
+		var(--vscode-gauge-foreground) 2px,
+		transparent 2px,
+		transparent 4px
+	);
+	flex-shrink: 0;
+}
+
+.chat-context-usage-details .quota-indicator.warning .output-buffer-swatch {
+	background: repeating-linear-gradient(
+		-45deg,
+		var(--vscode-gauge-warningForeground),
+		var(--vscode-gauge-warningForeground) 2px,
+		transparent 2px,
+		transparent 4px
+	);
+}
+
+.chat-context-usage-details .quota-indicator.warning .quota-bar {
 	background-color: var(--vscode-gauge-warningBackground);
 }
 
-.chat-context-usage-details .quota-item.warning .quota-bar .quota-bit {
+.chat-context-usage-details .quota-indicator.warning .quota-bar .quota-bit {
 	background-color: var(--vscode-gauge-warningForeground);
 }
 
-.chat-context-usage-details .quota-item.error .quota-bar {
+.chat-context-usage-details .quota-indicator.warning .quota-bar .quota-bit.output-buffer {
+	background: repeating-linear-gradient(
+		-45deg,
+		var(--vscode-gauge-warningForeground),
+		var(--vscode-gauge-warningForeground) 2px,
+		transparent 2px,
+		transparent 4px
+	);
+}
+
+.chat-context-usage-details .quota-indicator.error .output-buffer-swatch {
+	background: repeating-linear-gradient(
+		-45deg,
+		var(--vscode-gauge-errorForeground),
+		var(--vscode-gauge-errorForeground) 2px,
+		transparent 2px,
+		transparent 4px
+	);
+}
+
+.chat-context-usage-details .quota-indicator.error .quota-bar {
 	background-color: var(--vscode-gauge-errorBackground);
 }
 
-.chat-context-usage-details .quota-item.error .quota-bar .quota-bit {
+.chat-context-usage-details .quota-indicator.error .quota-bar .quota-bit {
 	background-color: var(--vscode-gauge-errorForeground);
 }
 
-.chat-context-usage-details .warning-message {
-	font-size: 12px;
-	color: var(--vscode-descriptionForeground);
-	margin-bottom: 4px;
+.chat-context-usage-details .quota-indicator.error .quota-bar .quota-bit.output-buffer {
+	background: repeating-linear-gradient(
+		-45deg,
+		var(--vscode-gauge-errorForeground),
+		var(--vscode-gauge-errorForeground) 2px,
+		transparent 2px,
+		transparent 4px
+	);
 }
 
-/* Token details breakdown */
-.chat-context-usage-details .token-details-container {
-	margin-top: 4px;
+/* Description / warning text — matching ChatStatusDashboard */
+.chat-context-usage-details div.description {
+	font-size: 11px;
+	color: var(--vscode-descriptionForeground);
+	display: flex;
+	align-items: center;
+	gap: 3px;
 }
 
+/* Token details breakdown */
 .chat-context-usage-details .token-category {
-	margin-bottom: 4px;
+	margin-bottom: 6px;
 }
 
 .chat-context-usage-details .token-category-header {
+	display: flex;
+	align-items: center;
+	color: var(--vscode-descriptionForeground);
+	margin-top: 16px;
+	margin-bottom: 4px;
 	font-weight: 600;
-	color: var(--vscode-foreground);
-	margin-bottom: 2px;
+}
+
+.chat-context-usage-details .token-category:first-child .token-category-header {
+	margin-top: 8px;
 }
 
 .chat-context-usage-details .token-detail-item {
 	display: flex;
 	justify-content: space-between;
 	align-items: center;
-	padding-left: 8px;
+	gap: 20px;
+	margin-bottom: 2px;
 }
 
 .chat-context-usage-details .token-detail-label {
@@ -124,15 +200,9 @@
 	color: var(--vscode-descriptionForeground);
 }
 
-.chat-context-usage-details .actions-section .separator {
-	border-top: 1px solid var(--vscode-editorHoverWidget-border);
-	margin: 4px 0;
-}
-
-.chat-context-usage-details .actions-section .actions-header {
-	font-weight: 600;
-	color: var(--vscode-foreground);
-	margin-bottom: 4px;
+/* Actions section */
+.chat-context-usage-details .actions-section {
+	margin-top: 8px;
 }
 
 .chat-context-usage-details .actions-section .button-bar-container {
diff --git a/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/media/chatContextUsageWidget.css b/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/media/chatContextUsageWidget.css
index c3abb1332f0de..e09c5e1aa2321 100644
--- a/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/media/chatContextUsageWidget.css
+++ b/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/media/chatContextUsageWidget.css
@@ -6,9 +6,7 @@
 .chat-context-usage-widget {
 	display: flex;
 	align-items: center;
-	justify-content: center;
-	height: 22px;
-	width: 22px;
+	gap: 4px;
 	flex-shrink: 0;
 	cursor: pointer;
 	padding: 3px;
@@ -55,7 +53,7 @@
 
 .chat-context-usage-widget .progress-arc {
 	fill: none;
-	stroke: var(--vscode-descriptionForeground);
+	stroke: var(--vscode-icon-foreground);
 	stroke-width: 4;
 	stroke-linecap: round;
 	transform: rotate(-90deg);
@@ -70,3 +68,20 @@
 .chat-context-usage-widget.error .progress-arc {
 	stroke: var(--vscode-editorError-foreground);
 }
+
+.chat-context-usage-widget .percentage-label {
+	font-size: 11px;
+	line-height: 1;
+	color: var(--vscode-descriptionForeground);
+	white-space: nowrap;
+	max-width: 0;
+	opacity: 0;
+	overflow: hidden;
+	transition: max-width 0.1s ease-out, opacity 0.1s ease-out;
+}
+
+.chat-context-usage-widget:hover .percentage-label,
+.chat-context-usage-widget:focus .percentage-label {
+	max-width: 4em;
+	opacity: 1;
+}
diff --git a/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/media/chatViewPane.css b/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/media/chatViewPane.css
index f57aca1530064..83799c15a7bc8 100644
--- a/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/media/chatViewPane.css
+++ b/src/vs/workbench/contrib/chat/browser/widgetHosts/viewPane/media/chatViewPane.css
@@ -130,6 +130,14 @@
 		padding: 0 6px 0 14px;
 	}
 
+	/* Stacked: symmetric padding */
+	&.sessions-control-orientation-stacked {
+
+		.agent-sessions-empty-filter-message {
+			padding-left: 20px;
+		}
+	}
+
 	/* Right position: symmetric padding */
 	&.sessions-control-orientation-sidebyside.chat-view-position-right {
 
diff --git a/src/vs/workbench/contrib/chat/common/actions/chatContextKeys.ts b/src/vs/workbench/contrib/chat/common/actions/chatContextKeys.ts
index 118eff3f41d14..c8fc17b308408 100644
--- a/src/vs/workbench/contrib/chat/common/actions/chatContextKeys.ts
+++ b/src/vs/workbench/contrib/chat/common/actions/chatContextKeys.ts
@@ -9,7 +9,7 @@ import { IsWebContext } from '../../../../../platform/contextkey/common/contextk
 import { RemoteNameContext } from '../../../../common/contextkeys.js';
 import { ViewContainerLocation } from '../../../../common/views.js';
 import { ChatEntitlementContextKeys } from '../../../../services/chat/common/chatEntitlementService.js';
-import { ChatAgentLocation, ChatModeKind } from '../constants.js';
+import { ChatAgentLocation, ChatModeKind, ChatPermissionLevel } from '../constants.js';
 
 export namespace ChatContextKeys {
 	export const responseVote = new RawContextKey<string>('chatSessionResponseVote', '', { type: 'string', description: localize('interactiveSessionResponseVote', "When the response has been voted up, is set to 'up'. When voted down, is set to 'down'. Otherwise an empty string.") });
@@ -23,7 +23,8 @@ export namespace ChatContextKeys {
 
 	export const enum EditingRequestType {
 		Sent = 's',
-		QueueOrSteer = 'qs',
+		Queue = 'q',
+		Steer = 'st',
 	}
 	export const editingRequestType = new RawContextKey<EditingRequestType | undefined>('chatEditingSentRequest', undefined, { type: 'string', description: localize('chatEditingSentRequest', "The type of the current editing request.") });
 
@@ -43,8 +44,10 @@ export namespace ChatContextKeys {
 	export const inChatEditor = new RawContextKey<boolean>('inChatEditor', false, { type: 'boolean', description: localize('inChatEditor', "Whether focus is in a chat editor.") });
 	export const inChatTodoList = new RawContextKey<boolean>('inChatTodoList', false, { type: 'boolean', description: localize('inChatTodoList', "True when focus is in the chat todo list.") });
 	export const inChatTip = new RawContextKey<boolean>('inChatTip', false, { type: 'boolean', description: localize('inChatTip', "True when focus is in a chat tip.") });
+	export const multipleChatTips = new RawContextKey<boolean>('multipleChatTips', false, { type: 'boolean', description: localize('multipleChatTips', "True when there are multiple chat tips available.") });
 	export const inChatTerminalToolOutput = new RawContextKey<boolean>('inChatTerminalToolOutput', false, { type: 'boolean', description: localize('inChatTerminalToolOutput', "True when focus is in the chat terminal output region.") });
 	export const chatModeKind = new RawContextKey<ChatModeKind>('chatAgentKind', ChatModeKind.Ask, { type: 'string', description: localize('agentKind', "The 'kind' of the current agent.") });
+	export const chatPermissionLevel = new RawContextKey<ChatPermissionLevel>('chatPermissionLevel', ChatPermissionLevel.Default, { type: 'string', description: localize('chatPermissionLevel', "The current permission level for tool auto-approval.") });
 	export const chatModeName = new RawContextKey<string>('chatModeName', '', { type: 'string', description: localize('chatModeName', "The name of the current chat mode (e.g. 'Plan' for custom modes).") });
 	export const chatModelId = new RawContextKey<string>('chatModelId', '', { type: 'string', description: localize('chatModelId', "The short id of the currently selected chat model (for example 'gpt-4.1').") });
 
@@ -55,6 +58,7 @@ export namespace ChatContextKeys {
 	 * True when the chat widget is locked to the coding agent session.
 	 */
 	export const lockedToCodingAgent = new RawContextKey<boolean>('lockedToCodingAgent', false, { type: 'boolean', description: localize('lockedToCodingAgent', "True when the chat widget is locked to the coding agent session.") });
+	export const lockedCodingAgentId = new RawContextKey<string>('lockedCodingAgentId', '', { type: 'string', description: localize('lockedCodingAgentId', "The agent ID when the chat widget is locked to a coding agent session.") });
 	/**
 	 * True when the chat session has a customAgentTarget defined in its contribution,
 	 * which means the mode picker should be shown with filtered custom agents.
@@ -88,6 +92,7 @@ export namespace ChatContextKeys {
 	export const chatSessionIsEmpty = new RawContextKey<boolean>('chatSessionIsEmpty', true, { type: 'boolean', description: localize('chatSessionIsEmpty', "True when the current chat session has no requests.") });
 	export const hasPendingRequests = new RawContextKey<boolean>('chatHasPendingRequests', false, { type: 'boolean', description: localize('chatHasPendingRequests', "True when there are pending requests in the queue.") });
 	export const chatSessionHasDebugData = new RawContextKey<boolean>('chatSessionHasDebugData', false, { type: 'boolean', description: localize('chatSessionHasDebugData', "True when the current chat session has debug log data.") });
+	export const chatSessionHasDebugTools = new RawContextKey<boolean>('chatSessionHasDebugTools', false, { type: 'boolean', description: localize('chatSessionHasDebugTools', "True when debug tools are enabled in the current chat session.") });
 
 	export const remoteJobCreating = new RawContextKey<boolean>('chatRemoteJobCreating', false, { type: 'boolean', description: localize('chatRemoteJobCreating', "True when a remote coding agent job is being created.") });
 	export const hasRemoteCodingAgent = new RawContextKey<boolean>('hasRemoteCodingAgent', false, localize('hasRemoteCodingAgent', "Whether any remote coding agent is available"));
@@ -112,6 +117,8 @@ export namespace ChatContextKeys {
 		toolsCount: new RawContextKey<number>('toolsCount', 0, { type: 'number', description: localize('toolsCount', "The count of tools available in the chat.") })
 	};
 
+	export const foregroundSessionCount = new RawContextKey<number>('chatForegroundSessionCount', 0, { type: 'number', description: localize('chatForegroundSessionCount', "The number of foreground chat sessions visible across chat surfaces.") });
+
 	export const Modes = {
 		hasCustomChatModes: new RawContextKey<boolean>('chatHasCustomAgents', false, { type: 'boolean', description: localize('chatHasAgents', "True when the chat has custom agents available.") }),
 		agentModeDisabledByPolicy: new RawContextKey<boolean>('chatAgentModeDisabledByPolicy', false, { type: 'boolean', description: localize('chatAgentModeDisabledByPolicy', "True when agent mode is disabled by organization policy.") }),
@@ -139,6 +146,8 @@ export namespace ChatContextKeys {
 	export const hasUsedCreateSlashCommands = new RawContextKey<boolean>('chatHasUsedCreateSlashCommands', false, { type: 'boolean', description: localize('chatHasUsedCreateSlashCommands', "True when the user has used any of the /create-* slash commands.") });
 
 	export const contextUsageHasBeenOpened = new RawContextKey<boolean>('chatContextUsageHasBeenOpened', false, { type: 'boolean', description: localize('chatContextUsageHasBeenOpened', "True when the user has opened the context window usage details.") });
+
+	export const newChatButtonExperimentIcon = new RawContextKey<string>('chatNewChatButtonExperimentIcon', '', { type: 'string', description: localize('chatNewChatButtonExperimentIcon', "The icon variant for the new chat button, controlled by experiment. Values: 'copilot', 'new-session', 'comment', or empty for default.") });
 }
 
 export namespace ChatContextKeyExprs {
diff --git a/src/vs/workbench/contrib/chat/common/aiCustomizationWorkspaceService.ts b/src/vs/workbench/contrib/chat/common/aiCustomizationWorkspaceService.ts
index b64f5ca45f656..2b6c01066fe4f 100644
--- a/src/vs/workbench/contrib/chat/common/aiCustomizationWorkspaceService.ts
+++ b/src/vs/workbench/contrib/chat/common/aiCustomizationWorkspaceService.ts
@@ -3,10 +3,13 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { CancellationToken } from '../../../../base/common/cancellation.js';
 import { IObservable } from '../../../../base/common/observable.js';
 import { URI } from '../../../../base/common/uri.js';
+import { isEqualOrParent } from '../../../../base/common/resources.js';
 import { createDecorator } from '../../../../platform/instantiation/common/instantiation.js';
 import { PromptsType } from './promptSyntax/promptTypes.js';
+import { IChatPromptSlashCommand, PromptsStorage } from './promptSyntax/service/promptsService.js';
 
 export const IAICustomizationWorkspaceService = createDecorator<IAICustomizationWorkspaceService>('aiCustomizationWorkspaceService');
 
@@ -20,11 +23,47 @@ export const AICustomizationManagementSection = {
 	Prompts: 'prompts',
 	Hooks: 'hooks',
 	McpServers: 'mcpServers',
+	Plugins: 'plugins',
 	Models: 'models',
 } as const;
 
 export type AICustomizationManagementSection = typeof AICustomizationManagementSection[keyof typeof AICustomizationManagementSection];
 
+/**
+ * Per-type filter policy controlling which storage sources and user file
+ * roots are visible for a given customization type.
+ */
+export interface IStorageSourceFilter {
+	/**
+	 * Which storage groups to display (e.g. workspace, user, extension, builtin).
+	 */
+	readonly sources: readonly string[];
+
+	/**
+	 * If set, only user files under these roots are shown (allowlist).
+	 * If `undefined`, all user file roots are included.
+	 */
+	readonly includedUserFileRoots?: readonly URI[];
+}
+
+/**
+ * Applies a storage source filter to an array of items that have uri and storage.
+ * Removes items whose storage is not in the filter's source list,
+ * and for user-storage items, removes those not under an allowed root.
+ */
+export function applyStorageSourceFilter<T extends { readonly uri: URI; readonly storage: string }>(items: readonly T[], filter: IStorageSourceFilter): readonly T[] {
+	const sourceSet = new Set(filter.sources);
+	return items.filter(item => {
+		if (!sourceSet.has(item.storage)) {
+			return false;
+		}
+		if (item.storage === PromptsStorage.user && filter.includedUserFileRoots) {
+			return filter.includedUserFileRoots.some(root => isEqualOrParent(item.uri, root));
+		}
+		return true;
+	});
+}
+
 /**
  * Provides workspace context for AI Customization views.
  */
@@ -47,17 +86,57 @@ export interface IAICustomizationWorkspaceService {
 	readonly managementSections: readonly AICustomizationManagementSection[];
 
 	/**
-	 * Whether the primary creation action should create a file directly
+	 * Returns the storage source filter for a given customization type.
+	 * Controls which storage groups and user file roots are visible.
+	 */
+	getStorageSourceFilter(type: PromptsType): IStorageSourceFilter;
+
+	/**
+	 * Whether this is a sessions window (vs core VS Code).
 	 */
-	readonly preferManualCreation: boolean;
+	readonly isSessionsWindow: boolean;
 
 	/**
 	 * Commits files in the active project.
 	 */
 	commitFiles(projectRoot: URI, fileUris: URI[]): Promise<void>;
 
+	/**
+	 * Commits the deletion of resources that have already been removed from disk.
+	 * The URIs may point to individual files or to directories (for example, when
+	 * deleting a skill, the entire customization folder is removed). Implementations
+	 * should ensure that directory deletions are handled recursively as needed.
+	 * In sessions this stages and commits the removal in the relevant repositories.
+	 */
+	deleteFiles(projectRoot: URI, fileUris: URI[]): Promise<void>;
+
 	/**
 	 * Launches the AI-guided creation flow for the given customization type.
 	 */
 	generateCustomization(type: PromptsType): Promise<void>;
+
+	/**
+	 * Whether a transient project root override is currently active.
+	 */
+	readonly hasOverrideProjectRoot: IObservable<boolean>;
+
+	/**
+	 * Sets a transient override for the active project root.
+	 * While set, `activeProjectRoot` returns this value instead of the
+	 * session- or workspace-derived root. Call `clearOverrideProjectRoot()` to revert.
+	 */
+	setOverrideProjectRoot(root: URI): void;
+
+	/**
+	 * Clears the transient project root override, reverting to the
+	 * session-derived (or workspace-derived) root.
+	 */
+	clearOverrideProjectRoot(): void;
+
+	/**
+	 * Returns prompt/skill slash commands filtered through the workspace
+	 * service's storage source policy, ensuring the results match the
+	 * customizations visible in the AI Customization views.
+	 */
+	getFilteredPromptSlashCommands(token: CancellationToken): Promise<readonly IChatPromptSlashCommand[]>;
 }
diff --git a/src/vs/workbench/contrib/chat/common/attachments/chatVariableEntries.ts b/src/vs/workbench/contrib/chat/common/attachments/chatVariableEntries.ts
index 5655cc695fd95..f03eea0f2a1fe 100644
--- a/src/vs/workbench/contrib/chat/common/attachments/chatVariableEntries.ts
+++ b/src/vs/workbench/contrib/chat/common/attachments/chatVariableEntries.ts
@@ -305,16 +305,26 @@ export interface IAgentFeedbackVariableEntry extends IBaseChatRequestVariableEnt
 		readonly text: string;
 		readonly resourceUri: URI;
 		readonly range: IRange;
+		readonly codeSelection?: string;
 	}>;
 }
 
+export interface IChatRequestDebugEventsVariableEntry extends IBaseChatRequestVariableEntry {
+	readonly kind: 'debugEvents';
+	/** Timestamp when the debug events were snapshotted. */
+	readonly snapshotTime: number;
+	/** The session resource these debug events belong to. */
+	readonly sessionResource: URI;
+}
+
 export type IChatRequestVariableEntry = IGenericChatRequestVariableEntry | IChatRequestImplicitVariableEntry | IChatRequestPasteVariableEntry
 	| ISymbolVariableEntry | ICommandResultVariableEntry | IDiagnosticVariableEntry | IImageVariableEntry
 	| IChatRequestToolEntry | IChatRequestToolSetEntry
 	| IChatRequestDirectoryEntry | IChatRequestFileEntry | INotebookOutputVariableEntry | IElementVariableEntry
 	| IPromptFileVariableEntry | IPromptTextVariableEntry
 	| ISCMHistoryItemVariableEntry | ISCMHistoryItemChangeVariableEntry | ISCMHistoryItemChangeRangeVariableEntry | ITerminalVariableEntry
-	| IChatRequestStringVariableEntry | IChatRequestWorkspaceVariableEntry | IDebugVariableEntry | IAgentFeedbackVariableEntry;
+	| IChatRequestStringVariableEntry | IChatRequestWorkspaceVariableEntry | IDebugVariableEntry | IAgentFeedbackVariableEntry
+	| IChatRequestDebugEventsVariableEntry;
 
 export namespace IChatRequestVariableEntry {
 
@@ -459,17 +469,17 @@ export function isStringImplicitContextValue(value: unknown): value is StringCha
 }
 
 export enum PromptFileVariableKind {
-	Instruction = 'vscode.prompt.instructions.root',
-	InstructionReference = `vscode.prompt.instructions`,
-	PromptFile = 'vscode.prompt.file'
+	Instruction = 'vscode.instructions.file.root',
+	InstructionReference = `vscode.instructions.file.reference`,
+	PromptFile = 'vscode.prompt.file',
 }
 
 /**
  * Utility to convert a {@link uri} to a chat variable entry.
  * The `id` of the chat variable can be one of the following:
  *
- * - `vscode.prompt.instructions__<URI>`: for all non-root prompt instructions references
- * - `vscode.prompt.instructions.root__<URI>`: for *root* prompt instructions references
+ * - `vscode.instructions.file.reference__<URI>`: for all non-root prompt instructions references
+ * - `vscode.instructions.file.root__<URI>`: for *root* prompt instructions references
  * - `vscode.prompt.file__<URI>`: for prompt file references
  *
  * @param uri A resource URI that points to a prompt instructions file.
@@ -490,13 +500,17 @@ export function toPromptFileVariableEntry(uri: URI, kind: PromptFileVariableKind
 	};
 }
 
+enum PromptTextVariableKind {
+	CustomizationsIndex = 'vscode.customizations.index',
+}
+
 export function toPromptTextVariableEntry(content: string, automaticallyAdded = false, toolReferences?: ChatRequestToolReferenceEntry[]): IPromptTextVariableEntry {
 	return {
-		id: `vscode.prompt.instructions.text`,
-		name: `prompt:instructionsList`,
+		id: PromptTextVariableKind.CustomizationsIndex,
+		name: `prompt:customizationsIndex`,
 		value: content,
 		kind: 'promptText',
-		modelDescription: 'Prompt instructions list',
+		modelDescription: 'Chat customizations index',
 		automaticallyAdded,
 		toolReferences
 	};
diff --git a/src/vs/workbench/contrib/chat/common/chatDebugEvents.ts b/src/vs/workbench/contrib/chat/common/chatDebugEvents.ts
new file mode 100644
index 0000000000000..cd7cdee3a5503
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/chatDebugEvents.ts
@@ -0,0 +1,238 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { IChatDebugEvent } from './chatDebugService.js';
+
+/**
+ * Descriptions of each debug event kind for the model. Adding a new event kind
+ * to {@link IChatDebugEvent} without adding an entry here will cause a compile error.
+ */
+export const debugEventKindDescriptions: Record<IChatDebugEvent['kind'], string> = {
+	generic: '- generic (category: "discovery"): File discovery for instructions, skills, agents, hooks. Resolving returns a fileList with full file paths, load status, skip reasons, and source folders. Always resolve these for questions about customization files.\n'
+		+ '- generic (other): Miscellaneous logs. Resolving returns additional text details.',
+	toolCall: '- toolCall: A tool invocation. Resolving returns tool name, input, output, status, and duration.',
+	modelTurn: '- modelTurn: An LLM round-trip. Resolving returns model name, token usage, timing, errors, and prompt sections.',
+	subagentInvocation: '- subagentInvocation: A sub-agent spawn. Resolving returns agent name, status, duration, and counts.',
+	userMessage: '- userMessage: The full prompt sent to the model. Resolving returns the complete message and all prompt sections (system prompt, instructions, context). Essential for understanding what the model received.',
+	agentResponse: '- agentResponse: The model\'s response. Resolving returns the full response text and sections.',
+};
+
+/**
+ * Formats debug events into a compact log-style summary for context attachment.
+ */
+export function formatDebugEventsForContext(events: readonly IChatDebugEvent[]): string {
+	const lines: string[] = [];
+	for (const event of events) {
+		const ts = event.created.toISOString();
+		const id = event.id ? ` [id=${event.id}]` : '';
+		switch (event.kind) {
+			case 'generic':
+				lines.push(`[${ts}]${id} ${event.level >= 3 ? 'ERROR' : event.level >= 2 ? 'WARN' : 'INFO'}: ${event.name}${event.details ? ' - ' + event.details : ''}${event.category ? ' (category: ' + event.category + ')' : ''}`);
+				break;
+			case 'toolCall':
+				lines.push(`[${ts}]${id} TOOL_CALL: ${event.toolName}${event.result ? ' result=' + event.result : ''}${event.durationInMillis !== undefined ? ' duration=' + event.durationInMillis + 'ms' : ''}`);
+				break;
+			case 'modelTurn':
+				lines.push(`[${ts}]${id} MODEL_TURN: ${event.requestName ?? 'unknown'}${event.model ? ' model=' + event.model : ''}${event.inputTokens !== undefined ? ' tokens(in=' + event.inputTokens + ',out=' + (event.outputTokens ?? '?') + ')' : ''}${event.durationInMillis !== undefined ? ' duration=' + event.durationInMillis + 'ms' : ''}`);
+				break;
+			case 'subagentInvocation':
+				lines.push(`[${ts}]${id} SUBAGENT: ${event.agentName}${event.status ? ' status=' + event.status : ''}${event.durationInMillis !== undefined ? ' duration=' + event.durationInMillis + 'ms' : ''}`);
+				break;
+			case 'userMessage':
+				lines.push(`[${ts}]${id} USER_MESSAGE: ${event.message.substring(0, 200)}${event.message.length > 200 ? '...' : ''} (${event.sections.length} sections)`);
+				break;
+			case 'agentResponse':
+				lines.push(`[${ts}]${id} AGENT_RESPONSE: ${event.message.substring(0, 200)}${event.message.length > 200 ? '...' : ''} (${event.sections.length} sections)`);
+				break;
+			default: {
+				const _: never = event;
+				void _;
+				break;
+			}
+		}
+	}
+	return lines.join('\n');
+}
+
+/**
+ * Constructs the model description for the debug events attachment,
+ * explaining to the model how to use the resolveDebugEventDetails tool.
+ */
+export function getDebugEventsModelDescription(): string {
+	return 'These are the debug event logs from the current chat conversation. Analyze them to help answer the user\'s troubleshooting question.\n'
+		+ '\n'
+		+ 'CRITICAL INSTRUCTION: You MUST call the resolveDebugEventDetails tool on relevant events BEFORE answering. The log lines below are only summaries — they do NOT contain the actual data (file paths, prompt content, tool I/O, etc.). The real information is only available by resolving events. Never answer based solely on the summary lines. Always resolve first, then answer.\n'
+		+ '\n'
+		+ 'Call resolveDebugEventDetails in parallel on all events that could be relevant to the user\'s question. When in doubt, resolve more events rather than fewer.\n'
+		+ '\n'
+		+ 'IMPORTANT: Do NOT mention event IDs, tool resolution steps, or internal debug mechanics in your response. The user does not know about debug events or event IDs. Present your findings directly and naturally, as if you simply know the answer. Never say things like "I need to resolve events" or show event IDs.\n'
+		+ '\n'
+		+ 'Event types and what resolving them returns:\n'
+		+ Object.values(debugEventKindDescriptions).join('\n');
+}
+
+/**
+ * Checks whether a debug event matches a single text search term.
+ * Used by both the debug panel filter and the listDebugEvents tool.
+ */
+export function debugEventMatchesText(event: IChatDebugEvent, term: string): boolean {
+	if (event.kind.toLowerCase().includes(term)) {
+		return true;
+	}
+	switch (event.kind) {
+		case 'toolCall':
+			return event.toolName.toLowerCase().includes(term)
+				|| (event.input?.toLowerCase().includes(term) ?? false)
+				|| (event.output?.toLowerCase().includes(term) ?? false);
+		case 'modelTurn':
+			return (event.model?.toLowerCase().includes(term) ?? false)
+				|| (event.requestName?.toLowerCase().includes(term) ?? false);
+		case 'generic':
+			return event.name.toLowerCase().includes(term)
+				|| (event.details?.toLowerCase().includes(term) ?? false)
+				|| (event.category?.toLowerCase().includes(term) ?? false);
+		case 'subagentInvocation':
+			return event.agentName.toLowerCase().includes(term)
+				|| (event.description?.toLowerCase().includes(term) ?? false);
+		case 'userMessage':
+		case 'agentResponse':
+			return event.message.toLowerCase().includes(term)
+				|| event.sections.some(s => s.name.toLowerCase().includes(term) || s.content.toLowerCase().includes(term));
+	}
+}
+
+/**
+ * Regex used to match `before:` and `after:` timestamp tokens inside filter text.
+ */
+const timestampTokenPattern = /\b(?:before|after):\d{4}(?:-\d{2}(?:-\d{2}(?:t\d{1,2}(?::\d{2}(?::\d{2})?)?)?)?)?(\b|$)/g;
+
+/**
+ * Parse a `before:YYYY[-MM[-DD[THH[:MM[:SS]]]]]` or `after:…` token from
+ * free-form filter text. Each component after the year is optional.
+ *
+ * For `before:`, the timestamp is rounded **up** to the end of the most
+ * specific unit given (e.g. `before:2026-03` → end-of-March).
+ * For `after:`, the timestamp is the **start** of the most specific unit.
+ */
+export function parseTimeToken(text: string, prefix: string): number | undefined {
+	const regex = new RegExp(`${prefix}:(\\d{4})(?:-(\\d{2})(?:-(\\d{2})(?:t(\\d{1,2})(?::(\\d{2})(?::(\\d{2}))?)?)?)?)?(?!\\w)`);
+	const m = regex.exec(text);
+	if (!m) {
+		return undefined;
+	}
+
+	const year = parseInt(m[1], 10);
+	const month = m[2] !== undefined ? parseInt(m[2], 10) - 1 : undefined;
+	const day = m[3] !== undefined ? parseInt(m[3], 10) : undefined;
+	const hour = m[4] !== undefined ? parseInt(m[4], 10) : undefined;
+	const minute = m[5] !== undefined ? parseInt(m[5], 10) : undefined;
+	const second = m[6] !== undefined ? parseInt(m[6], 10) : undefined;
+
+	if (prefix === 'before') {
+		if (second !== undefined) {
+			return new Date(year, month!, day!, hour!, minute!, second, 999).getTime();
+		} else if (minute !== undefined) {
+			return new Date(year, month!, day!, hour!, minute, 59, 999).getTime();
+		} else if (hour !== undefined) {
+			return new Date(year, month!, day!, hour, 59, 59, 999).getTime();
+		} else if (day !== undefined) {
+			return new Date(year, month!, day, 23, 59, 59, 999).getTime();
+		} else if (month !== undefined) {
+			return new Date(year, month + 1, 0, 23, 59, 59, 999).getTime();
+		} else {
+			return new Date(year, 11, 31, 23, 59, 59, 999).getTime();
+		}
+	} else {
+		return new Date(
+			year,
+			month ?? 0,
+			day ?? 1,
+			hour ?? 0,
+			minute ?? 0,
+			second ?? 0,
+			0,
+		).getTime();
+	}
+}
+
+/**
+ * Strips `before:…` and `after:…` timestamp tokens from filter text,
+ * returning only the plain text search portion.
+ */
+export function stripTimestampTokens(text: string): string {
+	return text.replace(timestampTokenPattern, '').trim();
+}
+
+/**
+ * Filters debug events by comma-separated text terms and optional
+ * `before:`/`after:` timestamp tokens.
+ *
+ * Terms prefixed with `!` are exclusions; all others are inclusions.
+ * At least one inclusion term must match (if any are present).
+ * Timestamp tokens are parsed and applied as date-range bounds, then
+ * stripped before text matching.
+ */
+export function filterDebugEventsByText(events: readonly IChatDebugEvent[], filterText: string): readonly IChatDebugEvent[] {
+	const beforeTimestamp = parseTimeToken(filterText, 'before');
+	const afterTimestamp = parseTimeToken(filterText, 'after');
+
+	// Strip timestamp tokens before splitting into text search terms
+	const textOnly = stripTimestampTokens(filterText);
+	const terms = textOnly.split(/\s*,\s*/).filter(t => t.length > 0);
+	const includeTerms = terms.filter(t => !t.startsWith('!')).map(t => t.trim());
+	const excludeTerms = terms.filter(t => t.startsWith('!')).map(t => t.slice(1).trim()).filter(t => t.length > 0);
+
+	return events.filter(e => {
+		// Timestamp bounds
+		const time = e.created.getTime();
+		if (beforeTimestamp !== undefined && time > beforeTimestamp) {
+			return false;
+		}
+		if (afterTimestamp !== undefined && time < afterTimestamp) {
+			return false;
+		}
+		// Text matching
+		if (excludeTerms.some(term => debugEventMatchesText(e, term))) {
+			return false;
+		}
+		if (includeTerms.length > 0) {
+			return includeTerms.some(term => debugEventMatchesText(e, term));
+		}
+		return true;
+	});
+}
+
+/**
+ * Description of the text filter syntax for tool schemas and documentation.
+ */
+export const debugEventFilterDescription = 'Comma-separated text search terms. Prefix a term with ! to exclude it. Matches against event kind, tool names, model names, agent names, categories, event names, and message content. Also supports before:YYYY[-MM[-DD[THH[:MM[:SS]]]]] and after:YYYY[-MM[-DD[THH[:MM[:SS]]]]] to filter by timestamp.';
+
+export interface DebugEventFilterOptions {
+	readonly kind?: string;
+	readonly filter?: string;
+	readonly limit?: number;
+}
+
+/**
+ * Applies kind, text, and limit filters to debug events.
+ * Used by the listDebugEvents tool to consolidate all filtering in one place.
+ */
+export function filterDebugEvents(events: readonly IChatDebugEvent[], options: DebugEventFilterOptions): readonly IChatDebugEvent[] {
+	let result = events;
+
+	if (options.kind) {
+		result = result.filter(e => e.kind === options.kind);
+	}
+
+	if (options.filter) {
+		result = filterDebugEventsByText(result, options.filter);
+	}
+
+	if (options.limit !== undefined && options.limit > 0 && result.length > options.limit) {
+		result = result.slice(result.length - options.limit);
+	}
+
+	return result;
+}
diff --git a/src/vs/workbench/contrib/chat/common/chatDebugService.ts b/src/vs/workbench/contrib/chat/common/chatDebugService.ts
index 4e83565a941a1..d97213d3f3e12 100644
--- a/src/vs/workbench/contrib/chat/common/chatDebugService.ts
+++ b/src/vs/workbench/contrib/chat/common/chatDebugService.ts
@@ -48,6 +48,7 @@ export interface IChatDebugToolCallEvent extends IChatDebugEventCommon {
 export interface IChatDebugModelTurnEvent extends IChatDebugEventCommon {
 	readonly kind: 'modelTurn';
 	readonly model?: string;
+	readonly requestName?: string;
 	readonly inputTokens?: number;
 	readonly outputTokens?: number;
 	readonly totalTokens?: number;
@@ -124,6 +125,11 @@ export interface IChatDebugService extends IDisposable {
 	 */
 	readonly onDidAddEvent: Event<IChatDebugEvent>;
 
+	/**
+	 * Fired when provider events are cleared for a session (before re-invoking providers).
+	 */
+	readonly onDidClearProviderEvents: Event<URI>;
+
 	/**
 	 * Log a generic event to the debug service.
 	 */
@@ -166,6 +172,11 @@ export interface IChatDebugService extends IDisposable {
 	 */
 	registerProvider(provider: IChatDebugLogProvider): IDisposable;
 
+	/**
+	 * Check whether providers have already been invoked for a given session.
+	 */
+	hasInvokedProviders(sessionResource: URI): boolean;
+
 	/**
 	 * Invoke all registered providers for a given session resource.
 	 * Called when the Debug View is opened to fetch events from extensions.
@@ -184,6 +195,49 @@ export interface IChatDebugService extends IDisposable {
 	 * Delegates to the registered provider's resolveChatDebugLogEvent.
 	 */
 	resolveEvent(eventId: string): Promise<IChatDebugResolvedEventContent | undefined>;
+
+	/**
+	/**
+	 * Export the debug log for a session via the registered provider.
+	 */
+	exportLog(sessionResource: URI): Promise<Uint8Array | undefined>;
+
+	/**
+	 * Import a previously exported debug log via the registered provider.
+	 * Returns the session URI for the imported data.
+	 */
+	importLog(data: Uint8Array): Promise<URI | undefined>;
+
+	/**
+	 * Returns true if the event was logged by VS Code core
+	 * (not sourced from an external provider).
+	 */
+	isCoreEvent(event: IChatDebugEvent): boolean;
+
+	/**
+	 * Store a human-readable title for an imported session.
+	 */
+	setImportedSessionTitle(sessionResource: URI, title: string): void;
+
+	/**
+	 * Get the stored title for an imported session, if available.
+	 */
+	getImportedSessionTitle(sessionResource: URI): string | undefined;
+
+	/**
+	 * Fired when debug data is attached to a session.
+	 */
+	readonly onDidAttachDebugData: Event<URI>;
+
+	/**
+	 * Mark a session as having debug data attached.
+	 */
+	markDebugDataAttached(sessionResource: URI): void;
+
+	/**
+	 * Check whether a session has had debug data attached.
+	 */
+	hasAttachedDebugData(sessionResource: URI): boolean;
 }
 
 /**
@@ -219,9 +273,6 @@ export interface IChatDebugFileEntry {
 export interface IChatDebugSourceFolderEntry {
 	readonly uri: URI;
 	readonly storage: string;
-	readonly exists: boolean;
-	readonly fileCount: number;
-	readonly errorMessage?: string;
 }
 
 /**
@@ -246,10 +297,44 @@ export interface IChatDebugEventMessageContent {
 	readonly sections: readonly IChatDebugMessageSection[];
 }
 
+/**
+ * Structured tool call content for a resolved debug event.
+ * Contains the tool name, status, arguments, and output for rich rendering.
+ */
+export interface IChatDebugEventToolCallContent {
+	readonly kind: 'toolCall';
+	readonly toolName: string;
+	readonly result?: 'success' | 'error';
+	readonly durationInMillis?: number;
+	readonly input?: string;
+	readonly output?: string;
+}
+
+/**
+ * Structured model turn content for a resolved debug event.
+ * Contains request metadata, token usage, and timing for rich rendering.
+ */
+export interface IChatDebugEventModelTurnContent {
+	readonly kind: 'modelTurn';
+	readonly requestName: string;
+	readonly model?: string;
+	readonly status?: string;
+	readonly durationInMillis?: number;
+	readonly timeToFirstTokenInMillis?: number;
+	readonly maxInputTokens?: number;
+	readonly maxOutputTokens?: number;
+	readonly inputTokens?: number;
+	readonly outputTokens?: number;
+	readonly cachedTokens?: number;
+	readonly totalTokens?: number;
+	readonly errorMessage?: string;
+	readonly sections?: readonly IChatDebugMessageSection[];
+}
+
 /**
  * Union of all resolved event content types.
  */
-export type IChatDebugResolvedEventContent = IChatDebugEventTextContent | IChatDebugEventFileListContent | IChatDebugEventMessageContent;
+export type IChatDebugResolvedEventContent = IChatDebugEventTextContent | IChatDebugEventFileListContent | IChatDebugEventMessageContent | IChatDebugEventToolCallContent | IChatDebugEventModelTurnContent;
 
 /**
  * Provider interface for debug events.
@@ -257,4 +342,6 @@ export type IChatDebugResolvedEventContent = IChatDebugEventTextContent | IChatD
 export interface IChatDebugLogProvider {
 	provideChatDebugLog(sessionResource: URI, token: CancellationToken): Promise<IChatDebugEvent[] | undefined>;
 	resolveChatDebugLogEvent?(eventId: string, token: CancellationToken): Promise<IChatDebugResolvedEventContent | undefined>;
+	provideChatDebugLogExport?(sessionResource: URI, token: CancellationToken): Promise<Uint8Array | undefined>;
+	resolveChatDebugLogImport?(data: Uint8Array, token: CancellationToken): Promise<URI | undefined>;
 }
diff --git a/src/vs/workbench/contrib/chat/common/chatDebugServiceImpl.ts b/src/vs/workbench/contrib/chat/common/chatDebugServiceImpl.ts
index f9787ed7978c7..4279479c1301d 100644
--- a/src/vs/workbench/contrib/chat/common/chatDebugServiceImpl.ts
+++ b/src/vs/workbench/contrib/chat/common/chatDebugServiceImpl.ts
@@ -3,36 +3,124 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { timeout } from '../../../../base/common/async.js';
 import { CancellationToken, CancellationTokenSource } from '../../../../base/common/cancellation.js';
 import { Emitter, Event } from '../../../../base/common/event.js';
 import { onUnexpectedError } from '../../../../base/common/errors.js';
 import { Disposable, IDisposable, toDisposable } from '../../../../base/common/lifecycle.js';
 import { ResourceMap } from '../../../../base/common/map.js';
+import { extUri } from '../../../../base/common/resources.js';
 import { URI } from '../../../../base/common/uri.js';
 import { ChatDebugLogLevel, IChatDebugEvent, IChatDebugLogProvider, IChatDebugResolvedEventContent, IChatDebugService } from './chatDebugService.js';
+import { LocalChatSessionUri } from './model/chatUri.js';
+
+/**
+ * Per-session circular buffer for debug events.
+ * Stores up to `capacity` events using a ring buffer.
+ */
+class SessionEventBuffer {
+	private readonly _buffer: (IChatDebugEvent | undefined)[];
+	private _head = 0;
+	private _size = 0;
+
+	constructor(readonly capacity: number) {
+		this._buffer = new Array(capacity);
+	}
+
+	get size(): number {
+		return this._size;
+	}
+
+	push(event: IChatDebugEvent): void {
+		const idx = (this._head + this._size) % this.capacity;
+		this._buffer[idx] = event;
+		if (this._size < this.capacity) {
+			this._size++;
+		} else {
+			this._head = (this._head + 1) % this.capacity;
+		}
+	}
+
+	/** Return events in insertion order. */
+	toArray(): IChatDebugEvent[] {
+		const result: IChatDebugEvent[] = [];
+		for (let i = 0; i < this._size; i++) {
+			const event = this._buffer[(this._head + i) % this.capacity];
+			if (event) {
+				result.push(event);
+			}
+		}
+		return result;
+	}
+
+	/** Remove events matching the predicate and compact in-place. */
+	removeWhere(predicate: (event: IChatDebugEvent) => boolean): void {
+		let write = 0;
+		for (let i = 0; i < this._size; i++) {
+			const idx = (this._head + i) % this.capacity;
+			const event = this._buffer[idx];
+			if (event && predicate(event)) {
+				continue;
+			}
+			if (write !== i) {
+				const writeIdx = (this._head + write) % this.capacity;
+				this._buffer[writeIdx] = event;
+			}
+			write++;
+		}
+		for (let i = write; i < this._size; i++) {
+			this._buffer[(this._head + i) % this.capacity] = undefined;
+		}
+		this._size = write;
+	}
+
+	clear(): void {
+		this._buffer.fill(undefined);
+		this._head = 0;
+		this._size = 0;
+	}
+}
 
 export class ChatDebugServiceImpl extends Disposable implements IChatDebugService {
 	declare readonly _serviceBrand: undefined;
 
-	private static readonly MAX_EVENTS = 10_000;
+	static readonly MAX_EVENTS_PER_SESSION = 10_000;
+	static readonly MAX_SESSIONS = 5;
 
-	// Circular buffer: fixed-size array with head/size tracking for O(1) append.
-	private readonly _buffer: (IChatDebugEvent | undefined)[] = new Array(ChatDebugServiceImpl.MAX_EVENTS);
-	private _head = 0;  // index of the oldest element
-	private _size = 0;  // number of elements currently stored
+	/** Per-session event buffers. Ordered from oldest to newest session (LRU). */
+	private readonly _sessionBuffers = new ResourceMap<SessionEventBuffer>();
+	/** Ordered list of session URIs for LRU eviction. */
+	private readonly _sessionOrder: URI[] = [];
 
 	private readonly _onDidAddEvent = this._register(new Emitter<IChatDebugEvent>());
 	readonly onDidAddEvent: Event<IChatDebugEvent> = this._onDidAddEvent.event;
 
+	private readonly _onDidClearProviderEvents = this._register(new Emitter<URI>());
+	readonly onDidClearProviderEvents: Event<URI> = this._onDidClearProviderEvents.event;
+
+	private readonly _onDidAttachDebugData = this._register(new Emitter<URI>());
+	readonly onDidAttachDebugData: Event<URI> = this._onDidAttachDebugData.event;
+
+	private readonly _debugDataAttachedSessions = new ResourceMap<boolean>();
+
 	private readonly _providers = new Set<IChatDebugLogProvider>();
 	private readonly _invocationCts = new ResourceMap<CancellationTokenSource>();
 
 	/** Events that were returned by providers (not internally logged). */
 	private readonly _providerEvents = new WeakSet<IChatDebugEvent>();
 
+	/** Session URIs created via import, allowed through the invokeProviders guard. */
+	private readonly _importedSessions = new ResourceMap<boolean>();
+
+	/** Human-readable titles for imported sessions. */
+	private readonly _importedSessionTitles = new ResourceMap<string>();
+
 	activeSessionResource: URI | undefined;
 
 	log(sessionResource: URI, name: string, details?: string, level: ChatDebugLogLevel = ChatDebugLogLevel.Info, options?: { id?: string; category?: string; parentEventId?: string }): void {
+		if (!LocalChatSessionUri.isLocalSession(sessionResource)) {
+			return;
+		}
 		this.addEvent({
 			kind: 'generic',
 			id: options?.id,
@@ -47,13 +135,25 @@ export class ChatDebugServiceImpl extends Disposable implements IChatDebugServic
 	}
 
 	addEvent(event: IChatDebugEvent): void {
-		const idx = (this._head + this._size) % ChatDebugServiceImpl.MAX_EVENTS;
-		this._buffer[idx] = event;
-		if (this._size < ChatDebugServiceImpl.MAX_EVENTS) {
-			this._size++;
+		let buffer = this._sessionBuffers.get(event.sessionResource);
+		if (!buffer) {
+			// Evict least-recently-used session if we are at the session cap.
+			if (this._sessionOrder.length >= ChatDebugServiceImpl.MAX_SESSIONS) {
+				const evicted = this._sessionOrder.shift()!;
+				this._evictSession(evicted);
+			}
+			buffer = new SessionEventBuffer(ChatDebugServiceImpl.MAX_EVENTS_PER_SESSION);
+			this._sessionBuffers.set(event.sessionResource, buffer);
+			this._sessionOrder.push(event.sessionResource);
 		} else {
-			this._head = (this._head + 1) % ChatDebugServiceImpl.MAX_EVENTS;
+			// Move to end of LRU order so actively-used sessions are not evicted.
+			const idx = this._sessionOrder.findIndex(u => extUri.isEqual(u, event.sessionResource));
+			if (idx !== -1 && idx !== this._sessionOrder.length - 1) {
+				this._sessionOrder.splice(idx, 1);
+				this._sessionOrder.push(event.sessionResource);
+			}
 		}
+		buffer.push(event);
 		this._onDidAddEvent.fire(event);
 	}
 
@@ -63,15 +163,14 @@ export class ChatDebugServiceImpl extends Disposable implements IChatDebugServic
 	}
 
 	getEvents(sessionResource?: URI): readonly IChatDebugEvent[] {
-		const result: IChatDebugEvent[] = [];
-		const key = sessionResource?.toString();
-		for (let i = 0; i < this._size; i++) {
-			const event = this._buffer[(this._head + i) % ChatDebugServiceImpl.MAX_EVENTS];
-			if (!event) {
-				continue;
-			}
-			if (!key || event.sessionResource.toString() === key) {
-				result.push(event);
+		let result: IChatDebugEvent[];
+		if (sessionResource) {
+			const buffer = this._sessionBuffers.get(sessionResource);
+			result = buffer ? buffer.toArray() : [];
+		} else {
+			result = [];
+			for (const buffer of this._sessionBuffers.values()) {
+				result.push(...buffer.toArray());
 			}
 		}
 		result.sort((a, b) => a.created.getTime() - b.created.getTime());
@@ -79,25 +178,29 @@ export class ChatDebugServiceImpl extends Disposable implements IChatDebugServic
 	}
 
 	getSessionResources(): readonly URI[] {
-		const seen = new ResourceMap<boolean>();
-		const result: URI[] = [];
-		for (let i = 0; i < this._size; i++) {
-			const event = this._buffer[(this._head + i) % ChatDebugServiceImpl.MAX_EVENTS];
-			if (!event) {
-				continue;
-			}
-			if (!seen.has(event.sessionResource)) {
-				seen.set(event.sessionResource, true);
-				result.push(event.sessionResource);
-			}
-		}
-		return result;
+		return [...this._sessionOrder];
 	}
 
 	clear(): void {
-		this._buffer.fill(undefined);
-		this._head = 0;
-		this._size = 0;
+		this._sessionBuffers.clear();
+		this._sessionOrder.length = 0;
+		this._debugDataAttachedSessions.clear();
+		this._importedSessions.clear();
+		this._importedSessionTitles.clear();
+	}
+
+	/** Remove all ancillary state for an evicted session. */
+	private _evictSession(sessionResource: URI): void {
+		this._sessionBuffers.delete(sessionResource);
+		this._importedSessions.delete(sessionResource);
+		this._importedSessionTitles.delete(sessionResource);
+		this._debugDataAttachedSessions.delete(sessionResource);
+		const cts = this._invocationCts.get(sessionResource);
+		if (cts) {
+			cts.cancel();
+			cts.dispose();
+			this._invocationCts.delete(sessionResource);
+		}
 	}
 
 	registerProvider(provider: IChatDebugLogProvider): IDisposable {
@@ -117,7 +220,15 @@ export class ChatDebugServiceImpl extends Disposable implements IChatDebugServic
 		});
 	}
 
+	hasInvokedProviders(sessionResource: URI): boolean {
+		return this._invocationCts.has(sessionResource);
+	}
+
 	async invokeProviders(sessionResource: URI): Promise<void> {
+
+		if (!LocalChatSessionUri.isLocalSession(sessionResource) && !this._importedSessions.has(sessionResource)) {
+			return;
+		}
 		// Cancel only the previous invocation for THIS session, not others.
 		// Each session has its own pipeline so events from multiple sessions
 		// can be streamed concurrently.
@@ -153,11 +264,21 @@ export class ChatDebugServiceImpl extends Disposable implements IChatDebugServic
 		try {
 			const events = await provider.provideChatDebugLog(sessionResource, token);
 			if (events) {
-				for (const event of events) {
+				// Yield to the event loop periodically so the UI stays
+				// responsive when a provider returns a large batch of events
+				// (e.g. importing a multi-MB log file).
+				const BATCH_SIZE = 500;
+				for (let i = 0; i < events.length; i++) {
+					if (token.isCancellationRequested) {
+						break;
+					}
 					this.addProviderEvent({
-						...event,
-						sessionResource: event.sessionResource ?? sessionResource,
+						...events[i],
+						sessionResource: events[i].sessionResource ?? sessionResource,
 					});
+					if (i > 0 && i % BATCH_SIZE === 0) {
+						await timeout(0);
+					}
 				}
 			}
 		} catch (err) {
@@ -172,29 +293,26 @@ export class ChatDebugServiceImpl extends Disposable implements IChatDebugServic
 			cts.dispose();
 			this._invocationCts.delete(sessionResource);
 		}
+		this._debugDataAttachedSessions.delete(sessionResource);
 	}
 
 	private _clearProviderEvents(sessionResource: URI): void {
-		const key = sessionResource.toString();
-		// Compact the ring buffer in-place, removing matching provider events.
-		let write = 0;
-		for (let i = 0; i < this._size; i++) {
-			const idx = (this._head + i) % ChatDebugServiceImpl.MAX_EVENTS;
-			const event = this._buffer[idx];
-			if (event && this._providerEvents.has(event) && event.sessionResource.toString() === key) {
-				continue; // skip — this event is removed
-			}
-			if (write !== i) {
-				const writeIdx = (this._head + write) % ChatDebugServiceImpl.MAX_EVENTS;
-				this._buffer[writeIdx] = event;
-			}
-			write++;
+		const buffer = this._sessionBuffers.get(sessionResource);
+		if (buffer) {
+			buffer.removeWhere(event => this._providerEvents.has(event));
 		}
-		// Clear trailing slots and update size
-		for (let i = write; i < this._size; i++) {
-			this._buffer[(this._head + i) % ChatDebugServiceImpl.MAX_EVENTS] = undefined;
+		this._onDidClearProviderEvents.fire(sessionResource);
+	}
+
+	markDebugDataAttached(sessionResource: URI): void {
+		if (!this._debugDataAttachedSessions.has(sessionResource)) {
+			this._debugDataAttachedSessions.set(sessionResource, true);
+			this._onDidAttachDebugData.fire(sessionResource);
 		}
-		this._size = write;
+	}
+
+	hasAttachedDebugData(sessionResource: URI): boolean {
+		return this._debugDataAttachedSessions.has(sessionResource);
 	}
 
 	async resolveEvent(eventId: string): Promise<IChatDebugResolvedEventContent | undefined> {
@@ -213,12 +331,59 @@ export class ChatDebugServiceImpl extends Disposable implements IChatDebugServic
 		return undefined;
 	}
 
+	isCoreEvent(event: IChatDebugEvent): boolean {
+		return !this._providerEvents.has(event);
+	}
+
+	setImportedSessionTitle(sessionResource: URI, title: string): void {
+		this._importedSessionTitles.set(sessionResource, title);
+	}
+
+	getImportedSessionTitle(sessionResource: URI): string | undefined {
+		return this._importedSessionTitles.get(sessionResource);
+	}
+
+	async exportLog(sessionResource: URI): Promise<Uint8Array | undefined> {
+		for (const provider of this._providers) {
+			if (provider.provideChatDebugLogExport) {
+				try {
+					const data = await provider.provideChatDebugLogExport(sessionResource, CancellationToken.None);
+					if (data !== undefined) {
+						return data;
+					}
+				} catch (err) {
+					onUnexpectedError(err);
+				}
+			}
+		}
+		return undefined;
+	}
+
+	async importLog(data: Uint8Array): Promise<URI | undefined> {
+		for (const provider of this._providers) {
+			if (provider.resolveChatDebugLogImport) {
+				try {
+					const sessionUri = await provider.resolveChatDebugLogImport(data, CancellationToken.None);
+					if (sessionUri !== undefined) {
+						this._importedSessions.set(sessionUri, true);
+						return sessionUri;
+					}
+				} catch (err) {
+					onUnexpectedError(err);
+				}
+			}
+		}
+		return undefined;
+	}
+
 	override dispose(): void {
 		for (const cts of this._invocationCts.values()) {
 			cts.cancel();
 			cts.dispose();
 		}
 		this._invocationCts.clear();
+		this.clear();
+		this._providers.clear();
 		super.dispose();
 	}
 }
diff --git a/src/vs/workbench/contrib/chat/common/chatImageExtraction.ts b/src/vs/workbench/contrib/chat/common/chatImageExtraction.ts
new file mode 100644
index 0000000000000..08af9fbd6d2b4
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/chatImageExtraction.ts
@@ -0,0 +1,234 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { decodeBase64, VSBuffer } from '../../../../base/common/buffer.js';
+import { getExtensionForMimeType, getMediaMime } from '../../../../base/common/mime.js';
+import { URI } from '../../../../base/common/uri.js';
+import { localize } from '../../../../nls.js';
+import { isLocation } from '../../../../editor/common/languages.js';
+import { IChatResponseViewModel, IChatRequestViewModel, isRequestVM } from './model/chatViewModel.js';
+import { ChatResponseResource } from './model/chatModel.js';
+import { IChatContentInlineReference, IChatToolInvocation, IChatToolInvocationSerialized, IToolResultOutputDetailsSerialized } from './chatService/chatService.js';
+import { isToolResultInputOutputDetails, isToolResultOutputDetails, IToolResultOutputDetails } from './tools/languageModelToolsService.js';
+import { isImageVariableEntry } from './attachments/chatVariableEntries.js';
+
+export interface IChatExtractedImage {
+	readonly id: string;
+	readonly uri: URI;
+	readonly name: string;
+	readonly mimeType: string;
+	readonly data: VSBuffer;
+	readonly source: string;
+	readonly caption: string | undefined;
+}
+
+export interface IChatExtractedImageCollection {
+	readonly id: string;
+	readonly title: string;
+	readonly images: IChatExtractedImage[];
+}
+
+/**
+ * Extract all images from a chat response's tool invocations and inline references.
+ * Tool invocation images are extracted from output details and message URIs.
+ * Inline reference images (file URIs) are read via the provided {@link readFile} callback.
+ */
+export async function extractImagesFromChatResponse(
+	response: IChatResponseViewModel,
+	readFile: (uri: URI) => Promise<VSBuffer>,
+): Promise<IChatExtractedImageCollection> {
+	const allImages: IChatExtractedImage[] = [];
+
+	for (const item of response.response.value) {
+		if (item.kind === 'toolInvocation' || item.kind === 'toolInvocationSerialized') {
+			const images = extractImagesFromToolInvocationOutputDetails(item, response.sessionResource);
+			allImages.push(...images);
+			const messageImages = await extractImagesFromToolInvocationMessages(item, readFile);
+			allImages.push(...messageImages);
+		} else if (item.kind === 'inlineReference') {
+			const image = await extractImageFromInlineReference(item, readFile);
+			if (image) {
+				allImages.push(image);
+			}
+		}
+	}
+
+	// Use the corresponding user request as the carousel title
+	const request = response.session.getItems().find((item): item is IChatRequestViewModel => isRequestVM(item) && item.id === response.requestId);
+	const title = request ? request.messageText : localize('chatImageExtraction.defaultTitle', "Images");
+
+	return {
+		id: response.sessionResource.toString() + '_' + response.id,
+		title,
+		images: allImages,
+	};
+}
+
+export function extractImagesFromToolInvocationOutputDetails(toolInvocation: IChatToolInvocation | IChatToolInvocationSerialized, sessionResource: URI): IChatExtractedImage[] {
+	const images: IChatExtractedImage[] = [];
+
+	const resultDetails = IChatToolInvocation.resultDetails(toolInvocation);
+
+	const msg = toolInvocation.pastTenseMessage ?? toolInvocation.invocationMessage;
+	const caption = msg ? (typeof msg === 'string' ? msg : msg.value) : undefined;
+	const pushImage = (mimeType: string, data: VSBuffer, outputIndex: number) => {
+		const ext = getExtensionForMimeType(mimeType);
+		const permalinkBasename = ext ? `file${ext}` : 'file.bin';
+		const uri = ChatResponseResource.createUri(sessionResource, toolInvocation.toolCallId, outputIndex, permalinkBasename);
+		images.push({
+			id: `${toolInvocation.toolCallId}_${outputIndex}`,
+			uri,
+			name: localize('chatImageExtraction.imageName', "Image {0}", images.length + 1),
+			mimeType,
+			data,
+			source: localize('chatImageExtraction.toolSource', "Tool: {0}", toolInvocation.toolId),
+			caption,
+		});
+	};
+
+	if (isToolResultInputOutputDetails(resultDetails)) {
+		for (let i = 0; i < resultDetails.output.length; i++) {
+			const outputItem = resultDetails.output[i];
+			if (outputItem.type === 'embed' && outputItem.mimeType?.startsWith('image/') && !outputItem.isText) {
+				pushImage(outputItem.mimeType, decodeBase64(outputItem.value), i);
+			}
+		}
+	}
+	else if (isToolResultOutputDetails(resultDetails)) {
+		const output = resultDetails.output;
+		if (output.mimeType?.startsWith('image/')) {
+			const data = getImageDataFromOutputDetails(resultDetails, toolInvocation);
+			if (data) {
+				pushImage(output.mimeType, data, 0);
+			}
+		}
+	}
+
+	return images;
+}
+
+export async function extractImagesFromToolInvocationMessages(
+	toolInvocation: IChatToolInvocation | IChatToolInvocationSerialized,
+	readFile: (uri: URI) => Promise<VSBuffer>
+): Promise<IChatExtractedImage[]> {
+	// Use pastTenseMessage if available, otherwise fall back to invocationMessage.
+	// When pastTenseMessage exists it visually replaces invocationMessage in the UI,
+	// so we only look at its URIs — we don't fall back to invocationMessage URIs.
+	const message = toolInvocation.pastTenseMessage ?? toolInvocation.invocationMessage;
+	if (!message || typeof message === 'string' || !message.uris || Object.keys(message.uris).length === 0) {
+		return [];
+	}
+
+	const images: IChatExtractedImage[] = [];
+	for (const uriComponents of Object.values(message.uris)) {
+		const uri = URI.revive(uriComponents);
+		const mimeType = getMediaMime(uri.path);
+		if (mimeType?.startsWith('image/')) {
+			let data: VSBuffer;
+			try {
+				data = await readFile(uri);
+			} catch {
+				continue;
+			}
+			const name = uri.path.split('/').pop() ?? 'image';
+			images.push({
+				id: uri.toString(),
+				uri,
+				name,
+				mimeType,
+				data,
+				source: localize('chatImageExtraction.toolSource', "Tool: {0}", toolInvocation.toolId),
+				caption: message.value,
+			});
+		}
+	}
+	return images;
+}
+
+function getImageDataFromOutputDetails(resultDetails: IToolResultOutputDetails, toolInvocation: IChatToolInvocation | IChatToolInvocationSerialized): VSBuffer | undefined {
+	if (toolInvocation.kind === 'toolInvocationSerialized') {
+		const serializedDetails = resultDetails as unknown as IToolResultOutputDetailsSerialized;
+		if (serializedDetails.output.base64Data) {
+			return decodeBase64(serializedDetails.output.base64Data);
+		}
+		return undefined;
+	} else {
+		return resultDetails.output.value;
+	}
+}
+
+async function extractImageFromInlineReference(
+	part: IChatContentInlineReference,
+	readFile: (uri: URI) => Promise<VSBuffer>,
+): Promise<IChatExtractedImage | undefined> {
+	const ref = part.inlineReference;
+	const refUri = URI.isUri(ref) ? ref : isLocation(ref) ? ref.uri : ref.location.uri;
+	const mime = getMediaMime(refUri.path);
+	if (!mime?.startsWith('image/')) {
+		return undefined;
+	}
+
+	let data: VSBuffer;
+	try {
+		data = await readFile(refUri);
+	} catch {
+		return undefined;
+	}
+	const name = part.name ?? refUri.path.split('/').pop() ?? 'image';
+	return {
+		id: refUri.toString(),
+		uri: refUri,
+		name,
+		mimeType: mime,
+		data,
+		source: localize('chatImageExtraction.inlineReference', "File"),
+		caption: undefined,
+	};
+}
+
+export function coerceImageBuffer(value: unknown): Uint8Array | undefined {
+	return value instanceof Uint8Array
+		? value
+		: value instanceof ArrayBuffer
+			? new Uint8Array(value)
+			: (value && typeof value === 'object' && !Array.isArray(value))
+				? new Uint8Array(
+					Object.keys(value as Record<string, number>)
+						.sort((a, b) => Number(a) - Number(b))
+						.map(key => (value as Record<string, number>)[key])
+				)
+				: undefined;
+}
+
+/**
+ * Extract images from a chat request's variable attachments (user-attached images).
+ */
+export function extractImagesFromChatRequest(
+	request: IChatRequestViewModel,
+): IChatExtractedImage[] {
+	const images: IChatExtractedImage[] = [];
+	for (const variable of request.variables) {
+		if (!isImageVariableEntry(variable)) {
+			continue;
+		}
+		const buffer = coerceImageBuffer(variable.value);
+		if (!buffer) {
+			continue;
+		}
+		const mimeType = variable.mimeType ?? getMediaMime(variable.name) ?? 'image/png';
+		const uri = variable.references?.[0]?.reference;
+		const imageUri = URI.isUri(uri) ? uri : URI.from({ scheme: 'data', path: variable.name });
+		images.push({
+			id: imageUri.toString(),
+			uri: imageUri,
+			name: variable.name,
+			mimeType,
+			data: VSBuffer.wrap(buffer),
+			source: localize('chatImageExtraction.userAttachment', "Attachment"),
+			caption: undefined,
+		});
+	}
+	return images;
+}
diff --git a/src/vs/workbench/contrib/chat/common/chatModes.ts b/src/vs/workbench/contrib/chat/common/chatModes.ts
index ca181bd19d223..043cc51bf34a9 100644
--- a/src/vs/workbench/contrib/chat/common/chatModes.ts
+++ b/src/vs/workbench/contrib/chat/common/chatModes.ts
@@ -7,7 +7,7 @@ import { CancellationToken } from '../../../../base/common/cancellation.js';
 import { Emitter, Event } from '../../../../base/common/event.js';
 import { Disposable } from '../../../../base/common/lifecycle.js';
 import { constObservable, IObservable, ISettableObservable, observableValue, transaction } from '../../../../base/common/observable.js';
-import { URI } from '../../../../base/common/uri.js';
+import { isUriComponents, URI } from '../../../../base/common/uri.js';
 import { IOffsetRange } from '../../../../editor/common/core/ranges/offsetRange.js';
 import { localize } from '../../../../nls.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
@@ -19,12 +19,14 @@ import { IStorageService, StorageScope, StorageTarget } from '../../../../platfo
 import { IChatAgentService } from './participants/chatAgents.js';
 import { ChatContextKeys } from './actions/chatContextKeys.js';
 import { ChatConfiguration, ChatModeKind } from './constants.js';
-import { IHandOff, isTarget } from './promptSyntax/promptFileParser.js';
-import { ExtensionAgentSourceType, IAgentSource, ICustomAgent, ICustomAgentVisibility, IPromptsService, isCustomAgentVisibility, PromptsStorage, Target } from './promptSyntax/service/promptsService.js';
+import { IHandOff } from './promptSyntax/promptFileParser.js';
+import { ExtensionAgentSourceType, IAgentSource, ICustomAgent, ICustomAgentVisibility, IPromptsService, isCustomAgentVisibility, PromptsStorage } from './promptSyntax/service/promptsService.js';
+import { Target } from './promptSyntax/promptTypes.js';
 import { ThemeIcon } from '../../../../base/common/themables.js';
 import { Codicon } from '../../../../base/common/codicons.js';
 import { hash } from '../../../../base/common/hash.js';
 import { isString } from '../../../../base/common/types.js';
+import { isTarget } from './promptSyntax/languageProviders/promptFileAttributes.js';
 
 export const IChatModeService = createDecorator<IChatModeService>('chatModeService');
 export interface IChatModeService {
@@ -450,17 +452,21 @@ export class CustomChatMode implements IChatMode {
 
 type IChatModeSourceData =
 	| { readonly storage: PromptsStorage.extension; readonly extensionId: string; type?: ExtensionAgentSourceType }
-	| { readonly storage: PromptsStorage.local | PromptsStorage.user };
+	| { readonly storage: PromptsStorage.local | PromptsStorage.user | PromptsStorage.internal }
+	| { readonly storage: PromptsStorage.plugin; readonly pluginUri: URI };
 
 function isChatModeSourceData(value: unknown): value is IChatModeSourceData {
 	if (typeof value !== 'object' || value === null) {
 		return false;
 	}
-	const data = value as { storage?: unknown; extensionId?: unknown };
+	const data = value as { storage?: unknown; extensionId?: unknown; pluginUri?: unknown };
 	if (data.storage === PromptsStorage.extension) {
 		return typeof data.extensionId === 'string';
 	}
-	return data.storage === PromptsStorage.local || data.storage === PromptsStorage.user;
+	if (data.storage === PromptsStorage.plugin) {
+		return isUriComponents(data.pluginUri);
+	}
+	return data.storage === PromptsStorage.local || data.storage === PromptsStorage.user || data.storage === PromptsStorage.internal;
 }
 
 function serializeChatModeSource(source: IAgentSource | undefined): IChatModeSourceData | undefined {
@@ -470,6 +476,9 @@ function serializeChatModeSource(source: IAgentSource | undefined): IChatModeSou
 	if (source.storage === PromptsStorage.extension) {
 		return { storage: PromptsStorage.extension, extensionId: source.extensionId.value, type: source.type };
 	}
+	if (source.storage === PromptsStorage.plugin) {
+		return { storage: PromptsStorage.plugin, pluginUri: source.pluginUri };
+	}
 	return { storage: source.storage };
 }
 
@@ -480,6 +489,12 @@ function reviveChatModeSource(data: IChatModeSourceData | undefined): IAgentSour
 	if (data.storage === PromptsStorage.extension) {
 		return { storage: PromptsStorage.extension, extensionId: new ExtensionIdentifier(data.extensionId), type: data.type ?? ExtensionAgentSourceType.contribution };
 	}
+	if (data.storage === PromptsStorage.plugin) {
+		return { storage: PromptsStorage.plugin, pluginUri: URI.revive(data.pluginUri) };
+	}
+	if (data.storage === PromptsStorage.internal) {
+		return { storage: PromptsStorage.internal };
+	}
 	return { storage: data.storage };
 }
 
@@ -528,7 +543,7 @@ export class BuiltinChatMode implements IChatMode {
 export namespace ChatMode {
 	export const Ask = new BuiltinChatMode(ChatModeKind.Ask, 'Ask', localize('chatDescription', "Explore and understand your code"), Codicon.question);
 	export const Edit = new BuiltinChatMode(ChatModeKind.Edit, 'Edit', localize('editsDescription', "Edit or refactor selected code"), Codicon.edit);
-	export const Agent = new BuiltinChatMode(ChatModeKind.Agent, 'Agent', localize('agentDescription', "Describe what to build next"), Codicon.agent);
+	export const Agent = new BuiltinChatMode(ChatModeKind.Agent, 'Agent', localize('agentDescription', "Describe what to build"), Codicon.agent);
 }
 
 export function isBuiltinChatMode(mode: IChatMode): boolean {
diff --git a/src/vs/workbench/contrib/chat/common/chatService/chatService.ts b/src/vs/workbench/contrib/chat/common/chatService/chatService.ts
index ecf9c393b6b5c..61bd25515b682 100644
--- a/src/vs/workbench/contrib/chat/common/chatService/chatService.ts
+++ b/src/vs/workbench/contrib/chat/common/chatService/chatService.ts
@@ -8,13 +8,13 @@ import { DeferredPromise } from '../../../../../base/common/async.js';
 import { CancellationToken } from '../../../../../base/common/cancellation.js';
 import { Event } from '../../../../../base/common/event.js';
 import { IMarkdownString } from '../../../../../base/common/htmlContent.js';
-import { DisposableStore, IReference } from '../../../../../base/common/lifecycle.js';
+import { DisposableStore, IDisposable, IReference } from '../../../../../base/common/lifecycle.js';
 import { autorun, autorunSelfDisposable, IObservable, IReader } from '../../../../../base/common/observable.js';
 import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { hasKey } from '../../../../../base/common/types.js';
 import { URI, UriComponents } from '../../../../../base/common/uri.js';
 import { IRange, Range } from '../../../../../editor/common/core/range.js';
-import { HookTypeValue } from '../promptSyntax/hookSchema.js';
+import { HookTypeValue } from '../promptSyntax/hookTypes.js';
 import { ISelection } from '../../../../../editor/common/core/selection.js';
 import { Command, Location, TextEdit } from '../../../../../editor/common/languages.js';
 import { FileType } from '../../../../../platform/files/common/files.js';
@@ -151,6 +151,7 @@ export interface IChatUsagePromptTokenDetail {
 export interface IChatUsage {
 	promptTokens: number;
 	completionTokens: number;
+	outputBuffer?: number;
 	promptTokenDetails?: readonly IChatUsagePromptTokenDetail[];
 	kind: 'usage';
 }
@@ -349,6 +350,18 @@ export interface IChatConfirmation {
 	kind: 'confirmation';
 }
 
+/**
+ * Validation rules for a question in a question carousel.
+ */
+export interface IChatQuestionValidation {
+	minLength?: number;
+	maxLength?: number;
+	format?: 'email' | 'uri' | 'date' | 'date-time';
+	minimum?: number;
+	maximum?: number;
+	isInteger?: boolean;
+}
+
 /**
  * Represents an individual question in a question carousel.
  */
@@ -357,11 +370,32 @@ export interface IChatQuestion {
 	type: 'text' | 'singleSelect' | 'multiSelect';
 	title: string;
 	message?: string | IMarkdownString;
-	options?: { id: string; label: string; value: unknown }[];
+	description?: string;
+	options?: { id: string; label: string; value: string }[];
 	defaultValue?: string | string[];
 	allowFreeformInput?: boolean;
+	required?: boolean;
+	validation?: IChatQuestionValidation;
 }
 
+/** Answer shape for a single-select question. */
+export interface IChatSingleSelectAnswer {
+	selectedValue?: string;
+	freeformValue?: string;
+}
+
+/** Answer shape for a multi-select question. */
+export interface IChatMultiSelectAnswer {
+	selectedValues: string[];
+	freeformValue?: string;
+}
+
+/** Union of all possible answer values in a question carousel. */
+export type IChatQuestionAnswerValue = string | IChatSingleSelectAnswer | IChatMultiSelectAnswer;
+
+/** Record mapping question IDs to their typed answer values. */
+export type IChatQuestionAnswers = Record<string, IChatQuestionAnswerValue>;
+
 /**
  * A carousel for presenting multiple questions inline in the chat response.
  * Users can navigate between questions and submit their answers.
@@ -372,9 +406,13 @@ export interface IChatQuestionCarousel {
 	/** Unique identifier for resolving the carousel answers back to the extension */
 	resolveId?: string;
 	/** Storage for collected answers when user submits */
-	data?: Record<string, unknown>;
+	data?: IChatQuestionAnswers;
 	/** Whether the carousel has been submitted/skipped */
 	isUsed?: boolean;
+	/** Top-level message shown above the questions (e.g. from MCP elicitation message) */
+	message?: string | IMarkdownString;
+	/** Source attribution (e.g. MCP server) */
+	source?: ToolDataSource;
 	kind: 'questionCarousel';
 }
 
@@ -557,7 +595,7 @@ export type ConfirmedReason =
 
 export interface IChatToolInvocation {
 	readonly presentation: IPreparedToolInvocation['presentation'];
-	readonly toolSpecificData?: IChatTerminalToolInvocationData | ILegacyChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatPullRequestContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatSimpleToolInvocationData | IChatToolResourcesInvocationData;
+	readonly toolSpecificData?: IChatTerminalToolInvocationData | ILegacyChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatPullRequestContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatSimpleToolInvocationData | IChatToolResourcesInvocationData | IChatModifiedFilesConfirmationData;
 	readonly originMessage: string | IMarkdownString | undefined;
 	readonly invocationMessage: string | IMarkdownString;
 	readonly pastTenseMessage: string | IMarkdownString | undefined;
@@ -567,6 +605,7 @@ export interface IChatToolInvocation {
 	readonly subAgentInvocationId?: string;
 	readonly state: IObservable<IChatToolInvocation.State>;
 	generatedTitle?: string;
+	isAttachedToThinking: boolean;
 
 	kind: 'toolInvocation';
 
@@ -817,7 +856,7 @@ export interface IToolResultOutputDetailsSerialized {
  */
 export interface IChatToolInvocationSerialized {
 	presentation: IPreparedToolInvocation['presentation'];
-	toolSpecificData?: IChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatPullRequestContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatSimpleToolInvocationData | IChatToolResourcesInvocationData;
+	toolSpecificData?: IChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatPullRequestContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatSimpleToolInvocationData | IChatToolResourcesInvocationData | IChatModifiedFilesConfirmationData;
 	invocationMessage: string | IMarkdownString;
 	originMessage: string | IMarkdownString | undefined;
 	pastTenseMessage: string | IMarkdownString | undefined;
@@ -830,6 +869,7 @@ export interface IChatToolInvocationSerialized {
 	source: ToolDataSource | undefined; // undefined on pre-1.104 versions
 	readonly subAgentInvocationId?: string;
 	generatedTitle?: string;
+	isAttachedToThinking?: boolean;
 	kind: 'toolInvocationSerialized';
 }
 
@@ -873,8 +913,9 @@ export interface IChatExternalToolInvocationUpdate {
 	errorMessage?: string;
 	invocationMessage?: string | IMarkdownString;
 	pastTenseMessage?: string | IMarkdownString;
-	toolSpecificData?: IChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatTodoListContent | IChatSubagentToolInvocationData;
+	toolSpecificData?: IChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatModifiedFilesConfirmationData;
 	subagentInvocationId?: string;
+	resultDetails?: IToolResultInputOutputDetails;
 }
 
 export interface IChatTodoListContent {
@@ -897,6 +938,19 @@ export interface IChatToolResourcesInvocationData {
 	readonly values: Array<URI | Location>;
 }
 
+export interface IChatModifiedFilesConfirmationData {
+	readonly kind: 'modifiedFilesConfirmation';
+	readonly options: readonly string[];
+	readonly modifiedFiles: readonly {
+		readonly uri: UriComponents;
+		readonly originalUri?: UriComponents;
+		readonly insertions?: number;
+		readonly deletions?: number;
+		readonly title?: string;
+		readonly description?: string;
+	}[];
+}
+
 export interface IChatMcpServersStarting {
 	readonly kind: 'mcpServersStarting';
 	readonly state?: IObservable<IAutostartResult>; // not hydrated when serialized
@@ -1234,6 +1288,8 @@ export interface ChatSendResultRejected {
 export interface ChatSendResultSent {
 	readonly kind: 'sent';
 	readonly data: IChatSendRequestData;
+	/** Set when the session was replaced by a new one (e.g. untitled -> real contributed session). */
+	readonly newSessionResource?: URI;
 }
 
 export interface ChatSendResultQueued {
@@ -1345,7 +1401,7 @@ export interface IChatService {
 	_serviceBrand: undefined;
 	transferredSessionResource: URI | undefined;
 
-	readonly onDidSubmitRequest: Event<{ readonly chatSessionResource: URI }>;
+	readonly onDidSubmitRequest: Event<{ readonly chatSessionResource: URI; readonly message?: IParsedChatRequest }>;
 
 	readonly onDidCreateModel: Event<IChatModel>;
 
@@ -1409,7 +1465,13 @@ export interface IChatService {
 	resendRequest(request: IChatRequestModel, options?: IChatSendRequestOptions): Promise<void>;
 	adoptRequest(sessionResource: URI, request: IChatRequestModel): Promise<void>;
 	removeRequest(sessionResource: URI, requestId: string): Promise<void>;
-	cancelCurrentRequestForSession(sessionResource: URI): void;
+	cancelCurrentRequestForSession(sessionResource: URI, source?: string): Promise<void>;
+	/**
+	 * Migrates all in-flight and queued pending requests from one session to another.
+	 * Cancels the in-flight request on the original session, removes queued requests,
+	 * and re-sends them all on the target session preserving their original send options.
+	 */
+	migrateRequests(originalResource: URI, targetResource: URI): void;
 	/**
 	 * Sets yieldRequested on the active request for the given session.
 	 */
@@ -1444,19 +1506,22 @@ export interface IChatService {
 	readonly onDidPerformUserAction: Event<IChatUserActionEvent>;
 	notifyUserAction(event: IChatUserActionEvent): void;
 
-	readonly onDidReceiveQuestionCarouselAnswer: Event<{ requestId: string; resolveId: string; answers: Record<string, unknown> | undefined }>;
-	notifyQuestionCarouselAnswer(requestId: string, resolveId: string, answers: Record<string, unknown> | undefined): void;
+	readonly onDidReceiveQuestionCarouselAnswer: Event<{ requestId: string; resolveId: string; answers: IChatQuestionAnswers | undefined }>;
+	notifyQuestionCarouselAnswer(requestId: string, resolveId: string, answers: IChatQuestionAnswers | undefined): void;
 
-	readonly onDidDisposeSession: Event<{ readonly sessionResource: URI[]; readonly reason: 'cleared' }>;
+	readonly onDidDisposeSession: Event<{ readonly sessionResource: readonly URI[]; readonly reason: 'cleared' }>;
 
 	transferChatSession(transferredSessionResource: URI, toWorkspace: URI): Promise<void>;
 
 	activateDefaultAgent(location: ChatAgentLocation): Promise<void>;
 
-	readonly edits2Enabled: boolean;
-
 	readonly requestInProgressObs: IObservable<boolean>;
 
+	/**
+	 * @deprecated
+	 */
+	registerChatModelChangeListeners(chatSessionType: string, onChange: (chatSessionResource: URI) => void): IDisposable;
+
 	/**
 	 * For tests only!
 	 */
@@ -1469,9 +1534,7 @@ export interface IChatService {
 }
 
 export interface IChatSessionContext {
-	readonly chatSessionType: string;
 	readonly chatSessionResource: URI;
-	readonly isUntitled: boolean;
 	readonly initialSessionOptions?: ReadonlyArray<{ optionId: string; value: string | { id: string; name: string } }>;
 }
 
@@ -1485,10 +1548,13 @@ export interface IChatSessionStartOptions {
 export const ChatStopCancellationNoopEventName = 'chat.stopCancellationNoop';
 
 export type ChatStopCancellationNoopEvent = {
-	source: 'cancelAction' | 'chatService';
+	source: string;
 	reason: 'noWidget' | 'noViewModel' | 'noPendingRequest' | 'requestAlreadyCanceled' | 'requestIdUnavailable';
 	requestInProgress: 'true' | 'false' | 'unknown';
 	pendingRequests: number;
+	sessionScheme?: string;
+	lastRequestId?: string;
+	chatSessionId?: string;
 };
 
 export type ChatStopCancellationNoopClassification = {
@@ -1496,6 +1562,9 @@ export type ChatStopCancellationNoopClassification = {
 	reason: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The no-op reason when stop cancellation did not dispatch fully.' };
 	requestInProgress: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Whether request-in-progress was true, false, or unknown at no-op time.' };
 	pendingRequests: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The number of queued pending requests at no-op time when known.'; isMeasurement: true };
+	sessionScheme?: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The URI scheme of the session resource (e.g. vscodeLocalChatSession vs remote).' };
+	lastRequestId?: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The ID of the last request in the session, for correlating with tool invocations.' };
+	chatSessionId?: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The chat session ID.' };
 	owner: 'roblourens';
 	comment: 'Tracks possible no-op stop cancellation paths.';
 };
@@ -1504,12 +1573,16 @@ export const ChatPendingRequestChangeEventName = 'chat.pendingRequestChange';
 
 export type ChatPendingRequestChangeEvent = {
 	action: 'add' | 'remove' | 'notCancelable';
-	source: 'sendRequest' | 'sendRequestComplete' | 'removeRequest' | 'cancelRequest' | 'adoptRequest' | 'remoteSession';
+	source: string;
+	requestId?: string;
+	chatSessionId?: string;
 };
 
 export type ChatPendingRequestChangeClassification = {
 	action: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Whether a pending request was added or removed.' };
 	source: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The method that triggered the pending request change.' };
+	requestId?: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The request ID associated with the pending request change.' };
+	chatSessionId?: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The chat session ID.' };
 	owner: 'roblourens';
 	comment: 'Tracks pending request lifecycle changes in the chat service.';
 };
diff --git a/src/vs/workbench/contrib/chat/common/chatService/chatServiceImpl.ts b/src/vs/workbench/contrib/chat/common/chatService/chatServiceImpl.ts
index 0743b82d5f28c..d16da79960f4e 100644
--- a/src/vs/workbench/contrib/chat/common/chatService/chatServiceImpl.ts
+++ b/src/vs/workbench/contrib/chat/common/chatService/chatServiceImpl.ts
@@ -3,17 +3,17 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { DeferredPromise } from '../../../../../base/common/async.js';
+import { DeferredPromise, raceTimeout } from '../../../../../base/common/async.js';
 import { CancellationToken, CancellationTokenSource } from '../../../../../base/common/cancellation.js';
 import { toErrorMessage } from '../../../../../base/common/errorMessage.js';
 import { BugIndicatingError, ErrorNoTelemetry } from '../../../../../base/common/errors.js';
 import { Emitter, Event } from '../../../../../base/common/event.js';
 import { MarkdownString } from '../../../../../base/common/htmlContent.js';
 import { Iterable } from '../../../../../base/common/iterator.js';
-import { Disposable, DisposableResourceMap, DisposableStore, IDisposable, MutableDisposable } from '../../../../../base/common/lifecycle.js';
+import { Disposable, DisposableResourceMap, DisposableStore, IDisposable, MutableDisposable, toDisposable } from '../../../../../base/common/lifecycle.js';
 import { revive } from '../../../../../base/common/marshalling.js';
 import { Schemas } from '../../../../../base/common/network.js';
-import { autorun, derived, IObservable, ISettableObservable, observableValue } from '../../../../../base/common/observable.js';
+import { autorun, autorunIterableDelta, derived, IObservable, ISettableObservable, observableSignalFromEvent, observableValue } from '../../../../../base/common/observable.js';
 import { isEqual } from '../../../../../base/common/resources.js';
 import { StopWatch } from '../../../../../base/common/stopwatch.js';
 import { isDefined } from '../../../../../base/common/types.js';
@@ -40,20 +40,22 @@ import { ChatModel, ChatRequestModel, ChatRequestRemovalReason, IChatModel, ICha
 import { ChatModelStore, IStartSessionProps } from '../model/chatModelStore.js';
 import { chatAgentLeader, ChatRequestAgentPart, ChatRequestAgentSubcommandPart, ChatRequestSlashCommandPart, ChatRequestTextPart, chatSubcommandLeader, getPromptText, IParsedChatRequest } from '../requestParser/chatParserTypes.js';
 import { ChatRequestParser } from '../requestParser/chatRequestParser.js';
-import { ChatMcpServersStarting, ChatPendingRequestChangeClassification, ChatPendingRequestChangeEvent, ChatPendingRequestChangeEventName, ChatRequestQueueKind, ChatSendResult, ChatSendResultQueued, ChatStopCancellationNoopClassification, ChatStopCancellationNoopEvent, ChatStopCancellationNoopEventName, IChatCompleteResponse, IChatDetail, IChatFollowup, IChatModelReference, IChatProgress, IChatSendRequestOptions, IChatSendRequestResponseState, IChatService, IChatSessionContext, IChatSessionStartOptions, IChatUserActionEvent, ResponseModelState } from './chatService.js';
+import { ChatMcpServersStarting, ChatPendingRequestChangeClassification, ChatPendingRequestChangeEvent, ChatPendingRequestChangeEventName, ChatRequestQueueKind, ChatSendResult, ChatSendResultQueued, ChatSendResultSent, ChatStopCancellationNoopClassification, ChatStopCancellationNoopEvent, ChatStopCancellationNoopEventName, IChatCompleteResponse, IChatDetail, IChatFollowup, IChatModelReference, IChatProgress, IChatQuestionAnswers, IChatSendRequestOptions, IChatSendRequestResponseState, IChatService, IChatSessionContext, IChatSessionStartOptions, IChatUserActionEvent, ResponseModelState } from './chatService.js';
 import { ChatRequestTelemetry, ChatServiceTelemetry } from './chatServiceTelemetry.js';
-import { IChatSessionsService } from '../chatSessionsService.js';
+import { IChatSessionsService, localChatSessionType } from '../chatSessionsService.js';
 import { ChatSessionStore, IChatSessionEntryMetadata } from '../model/chatSessionStore.js';
 import { IChatSlashCommandService } from '../participants/chatSlashCommands.js';
 import { IChatTransferService } from '../model/chatTransferService.js';
-import { LocalChatSessionUri } from '../model/chatUri.js';
+import { chatSessionResourceToId, getChatSessionType, isUntitledChatSession, LocalChatSessionUri } from '../model/chatUri.js';
 import { IChatRequestVariableEntry } from '../attachments/chatVariableEntries.js';
-import { ChatAgentLocation, ChatConfiguration, ChatModeKind } from '../constants.js';
+import { ChatAgentLocation, ChatModeKind } from '../constants.js';
 import { ChatMessageRole, IChatMessage, ILanguageModelsService } from '../languageModels.js';
 import { ILanguageModelToolsService } from '../tools/languageModelToolsService.js';
 import { ChatSessionOperationLog } from '../model/chatSessionOperationLog.js';
 import { IPromptsService } from '../promptSyntax/service/promptsService.js';
-import { IChatRequestHooks } from '../promptSyntax/hookSchema.js';
+import { AGENT_DEBUG_LOG_ENABLED_SETTING, AGENT_DEBUG_LOG_FILE_LOGGING_ENABLED_SETTING, TROUBLESHOOT_COMMAND_NAME, TROUBLESHOOT_SKILL_PATH, COPILOT_SKILL_URI_SCHEME } from '../promptSyntax/promptTypes.js';
+import { ChatRequestHooks, mergeHooks } from '../promptSyntax/hookSchema.js';
+import { ResourceMap } from '../../../../../base/common/map.js';
 
 const serializedChatKey = 'interactive.sessions';
 
@@ -64,9 +66,12 @@ class CancellableRequest implements IDisposable {
 		return this._yieldRequested;
 	}
 
+
 	constructor(
 		public readonly cancellationTokenSource: CancellationTokenSource,
 		public requestId: string | undefined,
+		public readonly responseCompletePromise: Promise<void> | undefined,
+		public sendOptions: IChatSendRequestOptions | undefined,
 		@ILanguageModelToolsService private readonly toolsService: ILanguageModelToolsService
 	) { }
 
@@ -107,7 +112,7 @@ export class ChatService extends Disposable implements IChatService {
 		return this._transferredSessionResource;
 	}
 
-	private readonly _onDidSubmitRequest = this._register(new Emitter<{ readonly chatSessionResource: URI }>());
+	private readonly _onDidSubmitRequest = this._register(new Emitter<{ readonly chatSessionResource: URI; readonly message?: IParsedChatRequest }>());
 	public readonly onDidSubmitRequest = this._onDidSubmitRequest.event;
 
 	public get onDidCreateModel() { return this._sessionModels.onDidCreateModel; }
@@ -115,7 +120,7 @@ export class ChatService extends Disposable implements IChatService {
 	private readonly _onDidPerformUserAction = this._register(new Emitter<IChatUserActionEvent>());
 	public readonly onDidPerformUserAction: Event<IChatUserActionEvent> = this._onDidPerformUserAction.event;
 
-	private readonly _onDidReceiveQuestionCarouselAnswer = this._register(new Emitter<{ requestId: string; resolveId: string; answers: Record<string, unknown> | undefined }>());
+	private readonly _onDidReceiveQuestionCarouselAnswer = this._register(new Emitter<{ requestId: string; resolveId: string; answers: IChatQuestionAnswers | undefined }>());
 	public readonly onDidReceiveQuestionCarouselAnswer = this._onDidReceiveQuestionCarouselAnswer.event;
 
 	private readonly _onDidDisposeSession = this._register(new Emitter<{ readonly sessionResource: URI[]; reason: 'cleared' }>());
@@ -143,10 +148,6 @@ export class ChatService extends Disposable implements IChatService {
 		return this._sessionModels.waitForModelDisposals();
 	}
 
-	public get edits2Enabled(): boolean {
-		return this.configurationService.getValue(ChatConfiguration.Edits2Enabled);
-	}
-
 	private get isEmptyWindow(): boolean {
 		const workspace = this.workspaceContextService.getWorkspace();
 		return !workspace.configuration && workspace.folders.length === 0;
@@ -274,7 +275,7 @@ export class ChatService extends Disposable implements IChatService {
 		}
 	}
 
-	notifyQuestionCarouselAnswer(requestId: string, resolveId: string, answers: Record<string, unknown> | undefined): void {
+	notifyQuestionCarouselAnswer(requestId: string, resolveId: string, answers: IChatQuestionAnswers | undefined): void {
 		this._onDidReceiveQuestionCarouselAnswer.fire({ requestId, resolveId, answers });
 	}
 
@@ -583,7 +584,7 @@ export class ChatService extends Disposable implements IChatService {
 	}
 
 	private async loadRemoteSession(sessionResource: URI, location: ChatAgentLocation, token: CancellationToken): Promise<IChatModelReference | undefined> {
-		await this.chatSessionService.canResolveChatSession(sessionResource);
+		await this.chatSessionService.canResolveChatSession(sessionResource.scheme);
 
 		// Check if session already exists
 		{
@@ -604,7 +605,7 @@ export class ChatService extends Disposable implements IChatService {
 			}
 		}
 
-		const chatSessionType = sessionResource.scheme;
+		const chatSessionType = getChatSessionType(sessionResource);
 
 		// Contributed sessions do not use UI tools
 		const modelRef = this._sessionModels.acquireOrCreate({
@@ -618,8 +619,6 @@ export class ChatService extends Disposable implements IChatService {
 
 		modelRef.object.setContributedChatSession({
 			chatSessionResource: sessionResource,
-			chatSessionType,
-			isUntitled: sessionResource.path.startsWith('/untitled-')  //TODO(jospicer)
 		});
 
 		if (providedSession.title) {
@@ -683,9 +682,9 @@ export class ChatService extends Disposable implements IChatService {
 		}
 
 		if (providedSession.progressObs && lastRequest && providedSession.interruptActiveResponseCallback) {
-			const initialCancellationRequest = this.instantiationService.createInstance(CancellableRequest, new CancellationTokenSource(), undefined);
+			const initialCancellationRequest = this.instantiationService.createInstance(CancellableRequest, new CancellationTokenSource(), undefined, undefined, undefined);
 			this._pendingRequests.set(model.sessionResource, initialCancellationRequest);
-			this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'add', source: 'remoteSession' });
+			this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'add', source: 'remoteSession', chatSessionId: chatSessionResourceToId(model.sessionResource) });
 			const cancellationListener = disposables.add(new MutableDisposable());
 
 			const createCancellationListener = (token: CancellationToken) => {
@@ -693,9 +692,9 @@ export class ChatService extends Disposable implements IChatService {
 					providedSession.interruptActiveResponseCallback?.().then(userConfirmedInterruption => {
 						if (!userConfirmedInterruption) {
 							// User cancelled the interruption
-							const newCancellationRequest = this.instantiationService.createInstance(CancellableRequest, new CancellationTokenSource(), undefined);
+							const newCancellationRequest = this.instantiationService.createInstance(CancellableRequest, new CancellationTokenSource(), undefined, undefined, undefined);
 							this._pendingRequests.set(model.sessionResource, newCancellationRequest);
-							this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'add', source: 'remoteSession' });
+							this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'add', source: 'remoteSession', chatSessionId: chatSessionResourceToId(model.sessionResource) });
 							cancellationListener.value = createCancellationListener(newCancellationRequest.cancellationTokenSource.token);
 						}
 					});
@@ -725,7 +724,7 @@ export class ChatService extends Disposable implements IChatService {
 				}
 			}));
 		} else {
-			this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'notCancelable', source: 'remoteSession' });
+			this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'notCancelable', source: 'remoteSession', chatSessionId: chatSessionResourceToId(model.sessionResource) });
 			if (lastRequest && model.editingSession) {
 				// wait for timeline to load so that a 'changes' part is added when the response completes
 				await chatEditingSessionIsReady(model.editingSession);
@@ -809,11 +808,50 @@ export class ChatService extends Disposable implements IChatService {
 			return { kind: 'rejected', reason: 'Empty message' };
 		}
 
-		const model = this._sessionModels.get(sessionResource);
+		let model = this._sessionModels.get(sessionResource);
 		if (!model) {
 			throw new Error(`Unknown session: ${sessionResource}`);
 		}
 
+		let newSessionResource: URI | undefined;
+
+		// Workaround for the contributed chat sessions
+		//
+		// Internally blank widgets uses special sessions with an untitled- path. We do not want these leaking out
+		// to the rest of code. Instead use `createNewChatSessionItem` to make sure the session gets properly initialized with a real resource before processing the first request.
+		if (!model.hasRequests && isUntitledChatSession(sessionResource) && getChatSessionType(sessionResource) !== localChatSessionType) {
+
+			const parsedRequest = this.parseChatRequest(sessionResource, request, options?.location ?? model.initialLocation, options);
+			const commandPart = parsedRequest.parts.find((r): r is ChatRequestSlashCommandPart => r instanceof ChatRequestSlashCommandPart);
+			const requestText = getPromptText(parsedRequest).message;
+
+			// Capture session options before loading the remote session,
+			// since the alias registration below may change the lookup.
+			const sessionOptions = this.chatSessionService.getSessionOptions(sessionResource);
+			const initialSessionOptions = sessionOptions ? [...sessionOptions].map(([optionId, value]) => ({ optionId, value })) : undefined;
+
+			const newItem = await this.chatSessionService.createNewChatSessionItem(getChatSessionType(sessionResource), { prompt: requestText, command: commandPart?.text, initialSessionOptions }, CancellationToken.None);
+			if (newItem) {
+				model = (await this.loadRemoteSession(newItem.resource, model.initialLocation, CancellationToken.None))?.object as ChatModel | undefined;
+				if (!model) {
+					throw new Error(`Failed to load session for resource: ${newItem.resource}`);
+				}
+
+				// Register alias so session-option lookups work with the new resource
+				this.chatSessionService.registerSessionResourceAlias(sessionResource, newItem.resource);
+
+				// Update the new model's contributed session with initialSessionOptions
+				// so that the agent receives them when invoked.
+				model.setContributedChatSession({
+					chatSessionResource: newItem.resource,
+					initialSessionOptions: sessionOptions ? [...sessionOptions].map(([optionId, value]) => ({ optionId, value })) : undefined,
+				});
+
+				sessionResource = newItem.resource;
+				newSessionResource = newItem.resource;
+			}
+		}
+
 		const hasPendingRequest = this._pendingRequests.has(sessionResource);
 
 		if (options?.queue) {
@@ -851,6 +889,7 @@ export class ChatService extends Disposable implements IChatService {
 		// This method is only returning whether the request was accepted - don't block on the actual request
 		return {
 			kind: 'sent',
+			newSessionResource,
 			data: {
 				...this._sendRequestAsync(model, sessionResource, parsedRequest, attempt, !options?.noCommandDetection, silentAgent ?? defaultAgent, location, options),
 				agent,
@@ -950,11 +989,54 @@ export class ChatService extends Disposable implements IChatService {
 			let detectedAgent: IChatAgentData | undefined;
 			let detectedCommand: IChatAgentCommand | undefined;
 
+			// Gate /troubleshoot and the troubleshoot skill behind the feature flags
+			{
+				const debugLogEnabled = this.configurationService.getValue<boolean>(AGENT_DEBUG_LOG_ENABLED_SETTING);
+				const fileLoggingEnabled = this.configurationService.getValue<boolean>(AGENT_DEBUG_LOG_FILE_LOGGING_ENABLED_SETTING);
+				if (!debugLogEnabled || !fileLoggingEnabled) {
+					const isTroubleshootCommand = agentSlashCommandPart?.command.name === TROUBLESHOOT_COMMAND_NAME;
+					const hasTroubleshootSkill = options?.attachedContext?.some(v => {
+						const uri = IChatRequestVariableEntry.toUri(v);
+						return uri && (uri.scheme === COPILOT_SKILL_URI_SCHEME || uri.path.includes(TROUBLESHOOT_SKILL_PATH));
+					});
+					if (isTroubleshootCommand || hasTroubleshootSkill) {
+						request = model.addRequest(parsedRequest, { variables: [] }, attempt, options?.modeInfo);
+						completeResponseCreated();
+
+						const missingSettings: string[] = [];
+						if (!debugLogEnabled) {
+							missingSettings.push('`' + AGENT_DEBUG_LOG_ENABLED_SETTING + '`');
+						}
+						if (!fileLoggingEnabled) {
+							missingSettings.push('`' + AGENT_DEBUG_LOG_FILE_LOGGING_ENABLED_SETTING + '`');
+						}
+
+						const settingsQuery = !debugLogEnabled && !fileLoggingEnabled
+							? AGENT_DEBUG_LOG_ENABLED_SETTING
+							: !debugLogEnabled ? '@id:' + AGENT_DEBUG_LOG_ENABLED_SETTING : '@id:' + AGENT_DEBUG_LOG_FILE_LOGGING_ENABLED_SETTING;
+						const settingsArg = encodeURIComponent(JSON.stringify(settingsQuery));
+						model.acceptResponseProgress(request, {
+							kind: 'markdownContent',
+							content: new MarkdownString(localize(
+								'agentDebugLog.troubleshootDisabled',
+								"The `{0}` skill requires the following settings to be enabled: {1}. After enabling, reload the window to apply. [Enable in Settings](command:workbench.action.openSettings?{2})",
+								TROUBLESHOOT_COMMAND_NAME,
+								missingSettings.join(', '),
+								settingsArg
+							), { isTrusted: { enabledCommands: ['workbench.action.openSettings'] } }),
+						});
+						model.setResponse(request, {});
+						request.response?.complete();
+						return;
+					}
+				}
+			}
+
 			// Collect hooks from hook .json files
-			let collectedHooks: IChatRequestHooks | undefined;
+			let collectedHooks: ChatRequestHooks | undefined;
 			let hasDisabledClaudeHooks = false;
 			try {
-				const hooksInfo = await this.promptsService.getHooks(token, model.sessionId);
+				const hooksInfo = await this.promptsService.getHooks(token, model.sessionResource);
 				if (hooksInfo) {
 					collectedHooks = hooksInfo.hooks;
 					hasDisabledClaudeHooks = hooksInfo.hasDisabledClaudeHooks;
@@ -963,6 +1045,20 @@ export class ChatService extends Disposable implements IChatService {
 				this.logService.warn('[ChatService] Failed to collect hooks:', error);
 			}
 
+			// Merge hooks from the selected custom agent's frontmatter (if any)
+			const agentName = options?.modeInfo?.modeInstructions?.name;
+			if (agentName) {
+				try {
+					const agents = await this.promptsService.getCustomAgents(token, model.sessionResource);
+					const customAgent = agents.find(a => a.name === agentName);
+					if (customAgent?.hooks) {
+						collectedHooks = mergeHooks(collectedHooks, customAgent.hooks);
+					}
+				} catch (error) {
+					this.logService.warn('[ChatService] Failed to collect agent hooks:', error);
+				}
+			}
+
 			const stopWatch = new StopWatch(false);
 			store.add(token.onCancellationRequested(() => {
 				this.trace('sendRequest', `Request for session ${model.sessionResource} was cancelled`);
@@ -1028,6 +1124,7 @@ export class ChatService extends Disposable implements IChatService {
 							userSelectedModelId: options?.userSelectedModelId,
 							userSelectedTools: options?.userSelectedTools?.get(),
 							modeInstructions: options?.modeInfo?.modeInstructions,
+							permissionLevel: options?.modeInfo?.permissionLevel,
 							editedFileEvents: request.editedFileEvents,
 							hooks: collectedHooks,
 							hasHooksEnabled: !!collectedHooks && Object.values(collectedHooks).some(arr => arr.length > 0),
@@ -1097,16 +1194,19 @@ export class ChatService extends Disposable implements IChatService {
 							}
 						}));
 						pendingRequest.requestId ??= requestProps.requestId;
+						if (pendingRequest.requestId) {
+							this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'add', source: 'sendRequestId', requestId: pendingRequest.requestId, chatSessionId: chatSessionResourceToId(sessionResource) });
+						}
 					}
 					completeResponseCreated();
 
-					// Check for disabled Claude Code hooks and notify the user once per workspace
+					// Check for disabled Claude Code hooks and notify the user once per workspace.
+					// Only set the flag when actually showing the hint, so the setup agent flow
+					// (which may resend requests) doesn't consume the flag before the real request runs.
 					const disabledClaudeHooksDismissedKey = 'chat.disabledClaudeHooks.notification';
-					if (!this.storageService.getBoolean(disabledClaudeHooksDismissedKey, StorageScope.WORKSPACE)) {
+					if (hasDisabledClaudeHooks && !this.storageService.getBoolean(disabledClaudeHooksDismissedKey, StorageScope.WORKSPACE)) {
 						this.storageService.store(disabledClaudeHooksDismissedKey, true, StorageScope.WORKSPACE, StorageTarget.USER);
-						if (hasDisabledClaudeHooks) {
-							progressCallback([{ kind: 'disabledClaudeHooks' }]);
-						}
+						progressCallback([{ kind: 'disabledClaudeHooks' }]);
 					}
 
 					// MCP autostart: only run for native VS Code sessions (sidebar, new editors) but not for extension contributed sessions that have inputType set.
@@ -1139,7 +1239,7 @@ export class ChatService extends Disposable implements IChatService {
 					const message = parsedRequest.text;
 					const commandResult = await this.chatSlashCommandService.executeCommand(commandPart.slashCommand.command, message.substring(commandPart.slashCommand.command.length + 1).trimStart(), new Progress<IChatProgress>(p => {
 						progressCallback([p]);
-					}), history, location, model.sessionResource, token);
+					}), history, location, model.sessionResource, token, options);
 					agentOrCommandFollowups = Promise.resolve(commandResult?.followUp);
 					rawResult = {};
 
@@ -1150,6 +1250,9 @@ export class ChatService extends Disposable implements IChatService {
 				if ((token.isCancellationRequested && !rawResult)) {
 					return;
 				} else if (!request) {
+					// Silent slash command completed successfully — allow queued
+					// requests to proceed.
+					shouldProcessPending = !token.isCancellationRequested;
 					return;
 				} else {
 					if (!rawResult) {
@@ -1181,6 +1284,7 @@ export class ChatService extends Disposable implements IChatService {
 
 					shouldProcessPending = !rawResult.errorDetails && !token.isCancellationRequested;
 					request.response?.complete();
+
 					if (agentOrCommandFollowups) {
 						agentOrCommandFollowups.then(followups => {
 							model.setFollowups(request!, followups);
@@ -1212,13 +1316,13 @@ export class ChatService extends Disposable implements IChatService {
 		let shouldProcessPending = false;
 		const rawResponsePromise = sendRequestInternal();
 		// Note- requestId is not known at this point, assigned later
-		const cancellableRequest = this.instantiationService.createInstance(CancellableRequest, source, undefined);
+		const cancellableRequest = this.instantiationService.createInstance(CancellableRequest, source, undefined, rawResponsePromise, options);
 		this._pendingRequests.set(model.sessionResource, cancellableRequest);
-		this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'add', source: 'sendRequest' });
+		this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'add', source: 'sendRequest', chatSessionId: chatSessionResourceToId(model.sessionResource) });
 		rawResponsePromise.finally(() => {
 			if (this._pendingRequests.get(model.sessionResource) === cancellableRequest) {
 				this._pendingRequests.deleteAndDispose(model.sessionResource);
-				this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'remove', source: 'sendRequestComplete' });
+				this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'remove', source: 'sendRequestComplete', requestId: cancellableRequest.requestId, chatSessionId: chatSessionResourceToId(model.sessionResource) });
 			}
 			// Process the next pending request from the queue if any
 			if (shouldProcessPending) {
@@ -1228,7 +1332,7 @@ export class ChatService extends Disposable implements IChatService {
 		if (options?.userSelectedModelId) {
 			this.languageModelsService.addToRecentlyUsedList(options.userSelectedModelId);
 		}
-		this._onDidSubmitRequest.fire({ chatSessionResource: model.sessionResource });
+		this._onDidSubmitRequest.fire({ chatSessionResource: model.sessionResource, message: parsedRequest });
 		return {
 			responseCreatedPromise: responseCreated.p,
 			responseCompletePromise: rawResponsePromise,
@@ -1245,49 +1349,90 @@ export class ChatService extends Disposable implements IChatService {
 	/**
 	 * Process the next pending request from the model's queue, if any.
 	 * Called after a request completes to continue processing queued requests.
+	 * Multiple consecutive steering requests are combined into a single request.
 	 */
 	private processNextPendingRequest(model: ChatModel): void {
-		const pendingRequest = model.dequeuePendingRequest();
-		if (!pendingRequest) {
+		// Dequeue all consecutive steering requests and combine them into one
+		const steeringRequests = model.dequeueAllSteeringRequests();
+
+		// Then dequeue a single non-steering request if no steering was found
+		const nextQueued = steeringRequests.length === 0 ? model.dequeuePendingRequest() : undefined;
+
+		const allRequests = steeringRequests.length > 0 ? steeringRequests : (nextQueued ? [nextQueued] : []);
+		if (allRequests.length === 0) {
 			return;
 		}
 
-		this.trace('processNextPendingRequest', `Processing queued request for session ${model.sessionResource}`);
+		this.trace('processNextPendingRequest', `Processing ${allRequests.length} queued request(s) for session ${model.sessionResource}`);
 
-		const deferred = this._queuedRequestDeferreds.get(pendingRequest.request.id);
-		this._queuedRequestDeferreds.delete(pendingRequest.request.id);
+		// Collect and remove all deferreds
+		const deferreds: DeferredPromise<ChatSendResult>[] = [];
+		for (const req of allRequests) {
+			const deferred = this._queuedRequestDeferreds.get(req.request.id);
+			this._queuedRequestDeferreds.delete(req.request.id);
+			if (deferred) {
+				deferreds.push(deferred);
+			}
+		}
 
+		// Build send options from the first request, combining attachments from all
+		const firstRequest = allRequests[0];
 		const sendOptions: IChatSendRequestOptions = {
-			...pendingRequest.sendOptions,
-			// Ensure attachedContext is preserved after deserialization, where sendOptions
-			// loses attachedContext but the request model retains it in variableData.
-			attachedContext: pendingRequest.request.variableData.variables.slice(),
+			...firstRequest.sendOptions,
+			attachedContext: allRequests.flatMap(req => req.request.variableData.variables.slice()),
 		};
+
 		const location = sendOptions.location ?? sendOptions.locationData?.type ?? model.initialLocation;
 		const defaultAgent = this.chatAgentService.getDefaultAgent(location, sendOptions.modeInfo?.kind);
 		if (!defaultAgent) {
 			this.logService.warn('processNextPendingRequest', `No default agent for location ${location}`);
-			deferred?.complete({ kind: 'rejected', reason: 'No default agent available' });
+			for (const deferred of deferreds) {
+				deferred.complete({ kind: 'rejected', reason: 'No default agent available' });
+			}
+			return;
+		}
+
+		// For multiple steering requests, combine texts and re-parse; otherwise use as-is
+		let parsedRequest: IParsedChatRequest;
+		try {
+			if (allRequests.length > 1) {
+				const combinedText = allRequests.map(req => req.request.message.text).join('\n\n');
+				// message.text already includes agent/slash-command prefixes from the
+				// original parse, so clear them to avoid double-prefixing.
+				parsedRequest = this.parseChatRequest(model.sessionResource, combinedText, location, {
+					...sendOptions,
+					agentId: undefined,
+					slashCommand: undefined,
+				});
+			} else {
+				parsedRequest = firstRequest.request.message;
+			}
+		} catch (err) {
+			this.logService.error('processNextPendingRequest: failed to parse combined chat request', err);
+			const reason = toErrorMessage(err);
+			for (const deferred of deferreds) {
+				deferred.complete({ kind: 'rejected', reason });
+			}
 			return;
 		}
 
-		const parsedRequest = pendingRequest.request.message;
 		const silentAgent = sendOptions.agentIdSilent ? this.chatAgentService.getAgent(sendOptions.agentIdSilent) : undefined;
 		const agent = silentAgent ?? parsedRequest.parts.find((r): r is ChatRequestAgentPart => r instanceof ChatRequestAgentPart)?.agent ?? defaultAgent;
 		const agentSlashCommandPart = parsedRequest.parts.find((r): r is ChatRequestAgentSubcommandPart => r instanceof ChatRequestAgentSubcommandPart);
 
-		// Send the queued request - this will add it to _pendingRequests and handle it normally
-		const responseState = this._sendRequestAsync(model, model.sessionResource, parsedRequest, pendingRequest.request.attempt, !sendOptions.noCommandDetection, silentAgent ?? defaultAgent, location, sendOptions);
+		const responseState = this._sendRequestAsync(model, model.sessionResource, parsedRequest, firstRequest.request.attempt, !sendOptions.noCommandDetection, silentAgent ?? defaultAgent, location, sendOptions);
 
-		// Resolve the deferred with the sent result
-		deferred?.complete({
+		const result: ChatSendResultSent = {
 			kind: 'sent',
 			data: {
 				...responseState,
 				agent,
 				slashCommand: agentSlashCommandPart?.command,
 			},
-		});
+		};
+		for (const deferred of deferreds) {
+			deferred.complete(result);
+		}
 	}
 
 	private generateInitialChatTitleIfNeeded(model: ChatModel, request: IChatAgentRequest, defaultAgent: IChatAgentData, token: CancellationToken): void {
@@ -1378,7 +1523,7 @@ export class ChatService extends Disposable implements IChatService {
 		if (pendingRequest?.requestId === requestId) {
 			pendingRequest.cancel();
 			this._pendingRequests.deleteAndDispose(sessionResource);
-			this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'remove', source: 'removeRequest' });
+			this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'remove', source: 'removeRequest', requestId, chatSessionId: chatSessionResourceToId(model.sessionResource) });
 		}
 
 		model.removeRequest(requestId);
@@ -1401,8 +1546,8 @@ export class ChatService extends Disposable implements IChatService {
 			if (cts) {
 				cts.requestId = request.id;
 				this._pendingRequests.set(target.sessionResource, cts);
-				this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'remove', source: 'adoptRequest' });
-				this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'add', source: 'adoptRequest' });
+				this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'remove', source: 'adoptRequest', requestId: request.id, chatSessionId: chatSessionResourceToId(oldOwner.sessionResource) });
+				this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'add', source: 'adoptRequest', requestId: request.id, chatSessionId: chatSessionResourceToId(target.sessionResource) });
 			}
 		}
 	}
@@ -1434,26 +1579,35 @@ export class ChatService extends Disposable implements IChatService {
 		request.response?.complete();
 	}
 
-	cancelCurrentRequestForSession(sessionResource: URI): void {
+	async cancelCurrentRequestForSession(sessionResource: URI, source?: string): Promise<void> {
 		this.trace('cancelCurrentRequestForSession', `session: ${sessionResource}`);
 		const pendingRequest = this._pendingRequests.get(sessionResource);
 		if (!pendingRequest) {
 			const model = this._sessionModels.get(sessionResource);
 			const requestInProgress = model?.requestInProgress.get();
 			const pendingRequestsCount = model?.getPendingRequests().length ?? 0;
+			const lastRequest = model?.lastRequest;
 			this.telemetryService.publicLog2<ChatStopCancellationNoopEvent, ChatStopCancellationNoopClassification>(ChatStopCancellationNoopEventName, {
-				source: 'chatService',
+				source: source ?? 'chatService',
 				reason: 'noPendingRequest',
 				requestInProgress: requestInProgress === undefined ? 'unknown' : requestInProgress ? 'true' : 'false',
 				pendingRequests: pendingRequestsCount,
+				sessionScheme: sessionResource.scheme,
+				lastRequestId: lastRequest?.id,
+				chatSessionId: chatSessionResourceToId(sessionResource),
 			});
 			this.info('cancelCurrentRequestForSession', `No pending request was found for session ${sessionResource}. requestInProgress=${requestInProgress ?? 'unknown'}, pendingRequests=${pendingRequestsCount}`);
 			return;
 		}
 
+		const responseCompletePromise = pendingRequest.responseCompletePromise;
 		pendingRequest.cancel();
 		this._pendingRequests.deleteAndDispose(sessionResource);
-		this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'remove', source: 'cancelRequest' });
+		this.telemetryService.publicLog2<ChatPendingRequestChangeEvent, ChatPendingRequestChangeClassification>(ChatPendingRequestChangeEventName, { action: 'remove', source: source ?? 'cancelRequest', requestId: pendingRequest.requestId, chatSessionId: chatSessionResourceToId(sessionResource) });
+
+		if (responseCompletePromise) {
+			await raceTimeout(responseCompletePromise, 1000);
+		}
 	}
 
 	setYieldRequested(sessionResource: URI): void {
@@ -1463,6 +1617,51 @@ export class ChatService extends Disposable implements IChatService {
 		}
 	}
 
+	migrateRequests(originalResource: URI, targetResource: URI): void {
+		const model = this._sessionModels.get(originalResource);
+		if (!model) {
+			return;
+		}
+
+		// Detect an in-flight request that was dequeued and started on the old session
+		const lastRequest = model.lastRequest;
+		const inFlightRequest = lastRequest?.response && !lastRequest.response.isComplete ? lastRequest : undefined;
+		// Capture send options before cancelling, since cancellation disposes the tracking
+		const inFlightSendOptions = inFlightRequest ? this._pendingRequests.get(originalResource)?.sendOptions : undefined;
+
+		const pendingRequests = [...model.getPendingRequests()];
+
+		if (!inFlightRequest && pendingRequests.length === 0) {
+			return;
+		}
+
+		// Cancel the in-flight request on the old session
+		if (inFlightRequest) {
+			void this.cancelCurrentRequestForSession(originalResource);
+		}
+
+		// Remove each remaining pending request from the original session
+		for (const pending of pendingRequests) {
+			this.removePendingRequest(originalResource, pending.request.id);
+		}
+
+		// Re-send the cancelled in-flight request first (it was ahead of the queued ones)
+		if (inFlightRequest) {
+			void this.sendRequest(targetResource, inFlightRequest.message.text, {
+				...inFlightSendOptions,
+				queue: ChatRequestQueueKind.Queued,
+			});
+		}
+
+		// Re-send remaining queued requests
+		for (const pending of pendingRequests) {
+			void this.sendRequest(targetResource, pending.request.message.text, {
+				...pending.sendOptions,
+				queue: pending.kind,
+			});
+		}
+	}
+
 	removePendingRequest(sessionResource: URI, requestId: string): void {
 		const model = this._sessionModels.get(sessionResource) as ChatModel | undefined;
 		if (model) {
@@ -1546,4 +1745,39 @@ export class ChatService extends Disposable implements IChatService {
 		}
 		return localSessionId;
 	}
+
+	public registerChatModelChangeListeners(chatSessionType: string, onChange: (chatSessionResource: URI) => void): IDisposable {
+		const disposableStore = new DisposableStore();
+		const chatModelsICareAbout = this.chatModels.map(models =>
+			Array.from(models).filter((model: IChatModel) => model.sessionResource.scheme === chatSessionType)
+		);
+
+		const listeners = new ResourceMap<IDisposable>();
+		const autoRunDisposable = autorunIterableDelta(
+			reader => chatModelsICareAbout.read(reader),
+			({ addedValues, removedValues }) => {
+				removedValues.forEach((removed) => {
+					const listener = listeners.get(removed.sessionResource);
+					if (listener) {
+						listeners.delete(removed.sessionResource);
+						listener.dispose();
+					}
+				});
+				addedValues.forEach((added) => {
+					const requestChangeListener = added.lastRequestObs.map(last => last?.response && observableSignalFromEvent('chatSessions.modelRequestChangeListener', last.response.onDidChange));
+					const modelChangeListener = observableSignalFromEvent('chatSessions.modelChangeListener', added.onDidChange);
+					listeners.set(added.sessionResource, autorun(reader => {
+						requestChangeListener.read(reader)?.read(reader);
+						modelChangeListener.read(reader);
+						onChange(added.sessionResource);
+					}));
+				});
+			}
+		);
+		disposableStore.add(toDisposable(() => {
+			for (const listener of listeners.values()) { listener.dispose(); }
+		}));
+		disposableStore.add(autoRunDisposable);
+		return disposableStore;
+	}
 }
diff --git a/src/vs/workbench/contrib/chat/common/chatService/chatServiceTelemetry.ts b/src/vs/workbench/contrib/chat/common/chatService/chatServiceTelemetry.ts
index 2a0f2cf7cc8af..d524128a23803 100644
--- a/src/vs/workbench/contrib/chat/common/chatService/chatServiceTelemetry.ts
+++ b/src/vs/workbench/contrib/chat/common/chatService/chatServiceTelemetry.ts
@@ -11,7 +11,7 @@ import { ChatRequestModel, IChatRequestVariableData } from '../model/chatModel.j
 import { ChatRequestAgentSubcommandPart, ChatRequestSlashCommandPart } from '../requestParser/chatParserTypes.js';
 import { ChatAgentVoteDirection, ChatCopyKind, IChatSendRequestOptions, IChatUserActionEvent } from './chatService.js';
 import { isImageVariableEntry } from '../attachments/chatVariableEntries.js';
-import { ChatAgentLocation } from '../constants.js';
+import { ChatAgentLocation, ChatModeKind, ChatPermissionLevel } from '../constants.js';
 import { ILanguageModelsService } from '../languageModels.js';
 import { chatSessionResourceToId } from '../model/chatUri.js';
 
@@ -149,6 +149,9 @@ export type ChatProviderInvokedEvent = {
 	enableCommandDetection: boolean;
 	attachmentKinds: string[];
 	model: string | undefined;
+	permissionLevel: ChatPermissionLevel | undefined;
+	chatMode: string | undefined;
+	sessionType: string | undefined;
 };
 
 export type ChatProviderInvokedClassification = {
@@ -167,6 +170,9 @@ export type ChatProviderInvokedClassification = {
 	enableCommandDetection: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Whether participation detection was disabled for this invocation.' };
 	attachmentKinds: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The types of variables/attachments that the user included with their query.' };
 	model: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The model used to generate the response.' };
+	permissionLevel: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The tool auto-approval permission level selected in the permission picker (default, autoApprove, or autopilot). Undefined when the picker is not applicable (e.g. ask mode or API-driven requests).' };
+	chatMode: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The chat mode used for the request. Built-in modes (ask, agent, edit), extension-contributed names (e.g. Plan), or a hashed identifier for user-created custom agents.' };
+	sessionType: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The session type scheme (e.g. vscodeLocalChatSession for local, or remote session scheme).' };
 	owner: 'roblourens';
 	comment: 'Provides insight into the performance of Chat agents.';
 };
@@ -303,6 +309,9 @@ export class ChatRequestTelemetry {
 			numCodeBlocks: getCodeBlocks(request.response?.response.toString() ?? '').length,
 			attachmentKinds: this.attachmentKindsForTelemetry(request.variableData),
 			model: this.resolveModelId(this.opts.options?.userSelectedModelId),
+			permissionLevel: this.opts.options?.modeInfo?.kind === ChatModeKind.Ask ? undefined : this.opts.options?.modeInfo?.permissionLevel,
+			chatMode: this.opts.options?.modeInfo?.modeName ?? this.opts.options?.modeInfo?.modeId,
+			sessionType: this.opts.sessionResource.scheme,
 		});
 	}
 
diff --git a/src/vs/workbench/contrib/chat/common/chatSessionsService.ts b/src/vs/workbench/contrib/chat/common/chatSessionsService.ts
index ec178df2ab9c1..7f2b2a277aa8f 100644
--- a/src/vs/workbench/contrib/chat/common/chatSessionsService.ts
+++ b/src/vs/workbench/contrib/chat/common/chatSessionsService.ts
@@ -14,8 +14,8 @@ import { createDecorator } from '../../../../platform/instantiation/common/insta
 import { IChatAgentAttachmentCapabilities, IChatAgentRequest } from './participants/chatAgents.js';
 import { IChatEditingSession } from './editing/chatEditingService.js';
 import { IChatModel, IChatRequestVariableData, ISerializableChatModelInputState } from './model/chatModel.js';
-import { IChatProgress, IChatService, IChatSessionTiming } from './chatService/chatService.js';
-import { Target } from './promptSyntax/service/promptsService.js';
+import { IChatProgress, IChatSessionTiming } from './chatService/chatService.js';
+import { Target } from './promptSyntax/promptTypes.js';
 
 export const enum ChatSessionStatus {
 	Failed = 0,
@@ -193,15 +193,27 @@ export interface IChatSessionContentProvider {
 	provideChatSessionContent(sessionResource: URI, token: CancellationToken): Promise<IChatSession>;
 }
 
+export interface IChatNewSessionRequest {
+	readonly prompt: string;
+	readonly command?: string;
+
+	readonly initialSessionOptions?: ReadonlyArray<{ optionId: string; value: string | IChatSessionProviderOptionItem }>;
+}
+
+export interface IChatSessionItemsDelta {
+	readonly addedOrUpdated?: readonly IChatSessionItem[];
+	readonly removed?: readonly URI[];
+}
+
 export interface IChatSessionItemController {
 
-	readonly onDidChangeChatSessionItems: Event<void>;
+	readonly onDidChangeChatSessionItems: Event<IChatSessionItemsDelta>;
 
 	get items(): readonly IChatSessionItem[];
 
 	refresh(token: CancellationToken): Promise<void>;
 
-	newChatSessionItem?(request: IChatAgentRequest, token: CancellationToken): Promise<IChatSessionItem | undefined>;
+	newChatSessionItem?(request: IChatNewSessionRequest, token: CancellationToken): Promise<IChatSessionItem | undefined>;
 }
 
 /**
@@ -213,32 +225,36 @@ export interface IChatSessionOptionsWillNotifyExtensionEvent extends IWaitUntil
 	readonly updates: ReadonlyArray<{ optionId: string; value: string | IChatSessionProviderOptionItem }>;
 }
 
+export type ResolvedChatSessionsExtensionPoint = Omit<IChatSessionsExtensionPoint, 'icon'> & {
+	readonly icon: ThemeIcon | URI | undefined;
+};
+
+export const IChatSessionsService = createDecorator<IChatSessionsService>('chatSessionsService');
+
 export interface IChatSessionsService {
 	readonly _serviceBrand: undefined;
 
 	// #region Chat session item provider support
 	readonly onDidChangeItemsProviders: Event<{ readonly chatSessionType: string }>;
-	readonly onDidChangeSessionItems: Event<{ readonly chatSessionType: string }>;
+	readonly onDidChangeSessionItems: Event<IChatSessionItemsDelta>;
 
 	readonly onDidChangeAvailability: Event<void>;
 	readonly onDidChangeInProgress: Event<void>;
 
-	getChatSessionContribution(chatSessionType: string): IChatSessionsExtensionPoint | undefined;
+	getChatSessionContribution(chatSessionType: string): ResolvedChatSessionsExtensionPoint | undefined;
+	getAllChatSessionContributions(): ResolvedChatSessionsExtensionPoint[];
 
 	registerChatSessionItemController(chatSessionType: string, controller: IChatSessionItemController): IDisposable;
 	activateChatSessionItemProvider(chatSessionType: string): Promise<void>;
 
-	getAllChatSessionContributions(): IChatSessionsExtensionPoint[];
-	getIconForSessionType(chatSessionType: string): ThemeIcon | URI | undefined;
-	getWelcomeTitleForSessionType(chatSessionType: string): string | undefined;
-	getWelcomeMessageForSessionType(chatSessionType: string): string | undefined;
-	getInputPlaceholderForSessionType(chatSessionType: string): string | undefined;
-
 	/**
 	 * Get the list of current chat session items grouped by session type.
+	 *
 	 * @param providerTypeFilter If specified, only returns items from the given providers. If undefined, returns items from all providers.
+	 *
+	 * @returns An async iterable that produces the list of session items for each provider. The order is not guaranteed. Some provider may take a long time to resolve.
 	 */
-	getChatSessionItems(providerTypeFilter: readonly string[] | undefined, token: CancellationToken): Promise<Array<{ readonly chatSessionType: string; readonly items: readonly IChatSessionItem[] }>>;
+	getChatSessionItems(providerTypeFilter: readonly string[] | undefined, token: CancellationToken): AsyncIterable<{ readonly chatSessionType: string; readonly items: readonly IChatSessionItem[] }>;
 
 	/**
 	 * Forces the controllers to refresh their session items, optionally filtered by provider type.
@@ -256,10 +272,11 @@ export interface IChatSessionsService {
 	getContentProviderSchemes(): string[];
 
 	registerChatSessionContentProvider(scheme: string, provider: IChatSessionContentProvider): IDisposable;
-	canResolveChatSession(sessionResource: URI): Promise<boolean>;
+	canResolveChatSession(sessionType: string): Promise<boolean>;
 	getOrCreateChatSession(sessionResource: URI, token: CancellationToken): Promise<IChatSession>;
 
 	hasAnySessionOptions(sessionResource: URI): boolean;
+	getSessionOptions(sessionResource: URI): Map<string, string> | undefined;
 	getSessionOption(sessionResource: URI, optionId: string): string | IChatSessionProviderOptionItem | undefined;
 	setSessionOption(sessionResource: URI, optionId: string, value: string | IChatSessionProviderOptionItem): boolean;
 
@@ -287,6 +304,9 @@ export interface IChatSessionsService {
 
 	getOptionGroupsForSessionType(chatSessionType: string): IChatSessionProviderOptionGroup[] | undefined;
 	setOptionGroupsForSessionType(chatSessionType: string, handle: number, optionGroups?: IChatSessionProviderOptionGroup[]): void;
+
+	getNewSessionOptionsForSessionType(chatSessionType: string): Record<string, string | IChatSessionProviderOptionItem> | undefined;
+	setNewSessionOptionsForSessionType(chatSessionType: string, options: Record<string, string | IChatSessionProviderOptionItem>): void;
 	/**
 	 * Event fired when session options change and need to be sent to the extension.
 	 * MainThreadChatSessions subscribes to this to forward changes to the extension host.
@@ -295,14 +315,19 @@ export interface IChatSessionsService {
 	readonly onRequestNotifyExtension: Event<IChatSessionOptionsWillNotifyExtensionEvent>;
 	notifySessionOptionsChange(sessionResource: URI, updates: ReadonlyArray<{ optionId: string; value: string | IChatSessionProviderOptionItem }>): Promise<void>;
 
-	registerChatModelChangeListeners(chatService: IChatService, chatSessionType: string, onChange: () => void): IDisposable;
 	getInProgressSessionDescription(chatModel: IChatModel): string | undefined;
 
 	/**
 	 * Creates a new chat session item using the controller's newChatSessionItemHandler.
 	 * Returns undefined if the controller doesn't have a handler or if no controller is registered.
 	 */
-	createNewChatSessionItem(chatSessionType: string, request: IChatAgentRequest, token: CancellationToken): Promise<IChatSessionItem | undefined>;
+	createNewChatSessionItem(chatSessionType: string, request: IChatNewSessionRequest, token: CancellationToken): Promise<IChatSessionItem | undefined>;
+
+	/**
+	 * Registers an alias so that session-option lookups by the real resource
+	 * are redirected to the canonical (untitled) resource in the internal session map.
+	 */
+	registerSessionResourceAlias(untitledResource: URI, realResource: URI): void;
 }
 
 export function isSessionInProgressStatus(state: ChatSessionStatus): boolean {
@@ -314,4 +339,3 @@ export function isIChatSessionFileChange2(obj: unknown): obj is IChatSessionFile
 	return candidate && candidate.uri instanceof URI && typeof candidate.insertions === 'number' && typeof candidate.deletions === 'number';
 }
 
-export const IChatSessionsService = createDecorator<IChatSessionsService>('chatSessionsService');
diff --git a/src/vs/workbench/contrib/chat/common/constants.ts b/src/vs/workbench/contrib/chat/common/constants.ts
index d9c776a3618ec..5d51053f843af 100644
--- a/src/vs/workbench/contrib/chat/common/constants.ts
+++ b/src/vs/workbench/contrib/chat/common/constants.ts
@@ -10,7 +10,8 @@ import { RawContextKey } from '../../../../platform/contextkey/common/contextkey
 
 export enum ChatConfiguration {
 	AIDisabled = 'chat.disableAIFeatures',
-	PluginPaths = 'chat.plugins.paths',
+	PluginsEnabled = 'chat.plugins.enabled',
+	PluginLocations = 'chat.pluginLocations',
 	PluginMarketplaces = 'chat.plugins.marketplaces',
 	AgentEnabled = 'chat.agent.enabled',
 	PlanAgentDefaultModel = 'chat.planAgent.defaultModel',
@@ -21,7 +22,6 @@ export enum ChatConfiguration {
 	UnifiedAgentsBar = 'chat.unifiedAgentsBar.enabled',
 	AgentSessionProjectionEnabled = 'chat.agentSessionProjection.enabled',
 	EditModeHidden = 'chat.editMode.hidden',
-	Edits2Enabled = 'chat.edits2.enabled',
 	ExtensionToolsEnabled = 'chat.extensionTools.enabled',
 	RepoInfoEnabled = 'chat.repoInfo.enabled',
 	EditRequests = 'chat.editRequests',
@@ -51,10 +51,11 @@ export enum ChatConfiguration {
 	ShowCodeBlockProgressAnimation = 'chat.agent.codeBlockProgress',
 	RestoreLastPanelSession = 'chat.restoreLastPanelSession',
 	ExitAfterDelegation = 'chat.exitAfterDelegation',
-	AgentsControlClickBehavior = 'chat.agentsControl.clickBehavior',
 	ExplainChangesEnabled = 'chat.editing.explainChanges.enabled',
 	GrowthNotificationEnabled = 'chat.growthNotification.enabled',
 	ChatCustomizationMenuEnabled = 'chat.customizationsMenu.enabled',
+	AutopilotEnabled = 'chat.autopilot.enabled',
+	ImageCarouselEnabled = 'chat.imageCarousel.enabled',
 }
 
 /**
@@ -77,6 +78,26 @@ export function validateChatMode(mode: unknown): ChatModeKind | undefined {
 	}
 }
 
+/**
+ * The permission level controlling tool auto-approval behavior.
+ */
+export enum ChatPermissionLevel {
+	/** Use existing auto-approve settings */
+	Default = 'default',
+	/** Auto-approve all tool calls, auto-retry on error */
+	AutoApprove = 'autoApprove',
+	/** Everything AutoApprove does plus an internal stop hook that continues until the task is done */
+	Autopilot = 'autopilot'
+}
+
+/**
+ * Returns true if the permission level enables auto-approval of all tool calls.
+ * Both {@link ChatPermissionLevel.AutoApprove} and {@link ChatPermissionLevel.Autopilot} enable auto-approval.
+ */
+export function isAutoApproveLevel(level: ChatPermissionLevel | undefined): boolean {
+	return level === ChatPermissionLevel.AutoApprove || level === ChatPermissionLevel.Autopilot;
+}
+
 export function isChatMode(mode: unknown): mode is ChatModeKind {
 	return !!validateChatMode(mode);
 }
@@ -100,11 +121,6 @@ export enum ChatNotificationMode {
 	Always = 'always',
 }
 
-export enum AgentsControlClickBehavior {
-	Default = 'default',
-	Cycle = 'cycle',
-}
-
 export type RawChatParticipantLocation = 'panel' | 'terminal' | 'notebook' | 'editing-session';
 
 export enum ChatAgentLocation {
diff --git a/src/vs/workbench/contrib/chat/common/enablement.ts b/src/vs/workbench/contrib/chat/common/enablement.ts
new file mode 100644
index 0000000000000..e8cb2d26c7b75
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/enablement.ts
@@ -0,0 +1,142 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { IReader } from '../../../../base/common/observable.js';
+import { ObservableMemento, observableMemento } from '../../../../platform/observable/common/observableMemento.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
+
+export const enum ContributionEnablementState {
+	DisabledProfile,
+	DisabledWorkspace,
+	EnabledProfile,
+	EnabledWorkspace,
+}
+
+export function isContributionEnabled(state: ContributionEnablementState): boolean {
+	return state === ContributionEnablementState.EnabledProfile || state === ContributionEnablementState.EnabledWorkspace;
+}
+
+export function isContributionDisabled(state: ContributionEnablementState): boolean {
+	return !isContributionEnabled(state);
+}
+
+export interface IEnablementModel {
+	readEnabled(key: string, reader?: IReader): ContributionEnablementState;
+	setEnabled(key: string, state: ContributionEnablementState): void;
+}
+
+type EnablementMap = ReadonlyMap<string, boolean>;
+
+function mapToStorage(value: EnablementMap): string {
+	return JSON.stringify([...value]);
+}
+
+function mapFromStorage(value: string): EnablementMap {
+	const parsed = JSON.parse(value);
+	return new Map(Array.isArray(parsed) ? parsed : []);
+}
+
+/**
+ * A reusable enablement model for string-keyed contributions. Uses
+ * `observableMemento` to persist enable/disable state in both profile-scoped
+ * and workspace-scoped storage.
+ *
+ * Resolution order: if a workspace-scoped entry exists for a key, it wins.
+ * Otherwise, the profile-scoped entry is used. The default (absence of any
+ * entry) is {@link ContributionEnablementState.EnabledProfile}.
+ */
+export class EnablementModel extends Disposable implements IEnablementModel {
+	private readonly _profileState: ObservableMemento<EnablementMap>;
+	private readonly _workspaceState: ObservableMemento<EnablementMap>;
+
+	constructor(
+		storageKey: string,
+		@IStorageService storageService: IStorageService,
+	) {
+		super();
+
+		const mapMemento = observableMemento<EnablementMap>({
+			key: storageKey,
+			defaultValue: new Map(),
+			toStorage: mapToStorage,
+			fromStorage: mapFromStorage,
+		});
+
+		this._profileState = this._register(
+			mapMemento(StorageScope.PROFILE, StorageTarget.MACHINE, storageService)
+		);
+
+		this._workspaceState = this._register(
+			mapMemento(StorageScope.WORKSPACE, StorageTarget.MACHINE, storageService)
+		);
+	}
+
+	readEnabled(key: string, reader?: IReader): ContributionEnablementState {
+		const wsMap = this._workspaceState.read(reader);
+		if (wsMap.has(key)) {
+			return wsMap.get(key)!
+				? ContributionEnablementState.EnabledWorkspace
+				: ContributionEnablementState.DisabledWorkspace;
+		}
+
+		const profileMap = this._profileState.read(reader);
+		if (profileMap.has(key)) {
+			return profileMap.get(key)!
+				? ContributionEnablementState.EnabledProfile
+				: ContributionEnablementState.DisabledProfile;
+		}
+
+		return ContributionEnablementState.EnabledProfile;
+	}
+
+	setEnabled(key: string, state: ContributionEnablementState): void {
+		switch (state) {
+			case ContributionEnablementState.EnabledProfile: {
+				// Enabled-profile is the default: remove key from profile state,
+				// and also remove any workspace override.
+				this._deleteFromMap(this._profileState, key);
+				this._deleteFromMap(this._workspaceState, key);
+				break;
+			}
+			case ContributionEnablementState.DisabledProfile: {
+				// Store disabled in profile, remove workspace override.
+				this._setInMap(this._profileState, key, false);
+				this._deleteFromMap(this._workspaceState, key);
+				break;
+			}
+			case ContributionEnablementState.EnabledWorkspace: {
+				// Workspace override: always store explicitly.
+				this._setInMap(this._workspaceState, key, true);
+				break;
+			}
+			case ContributionEnablementState.DisabledWorkspace: {
+				// Workspace override: always store explicitly.
+				this._setInMap(this._workspaceState, key, false);
+				break;
+			}
+		}
+	}
+
+	private _setInMap(memento: ObservableMemento<EnablementMap>, key: string, value: boolean): void {
+		const current = memento.get();
+		if (current.get(key) === value) {
+			return;
+		}
+		const next = new Map(current);
+		next.set(key, value);
+		memento.set(next, undefined);
+	}
+
+	private _deleteFromMap(memento: ObservableMemento<EnablementMap>, key: string): void {
+		const current = memento.get();
+		if (!current.has(key)) {
+			return;
+		}
+		const next = new Map(current);
+		next.delete(key);
+		memento.set(next, undefined);
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/common/languageModels.ts b/src/vs/workbench/contrib/chat/common/languageModels.ts
index 803c331fb67ec..d88d5a917f2c6 100644
--- a/src/vs/workbench/contrib/chat/common/languageModels.ts
+++ b/src/vs/workbench/contrib/chat/common/languageModels.ts
@@ -263,13 +263,13 @@ export async function getTextResponseFromStream(response: ILanguageModelChatResp
 export interface ILanguageModelChatProvider {
 	readonly onDidChange: Event<void>;
 	provideLanguageModelChatInfo(options: ILanguageModelChatInfoOptions, token: CancellationToken): Promise<ILanguageModelChatMetadataAndIdentifier[]>;
-	sendChatRequest(modelId: string, messages: IChatMessage[], from: ExtensionIdentifier, options: { [name: string]: unknown }, token: CancellationToken): Promise<ILanguageModelChatResponse>;
+	sendChatRequest(modelId: string, messages: IChatMessage[], from: ExtensionIdentifier | undefined, options: { [name: string]: unknown }, token: CancellationToken): Promise<ILanguageModelChatResponse>;
 	provideTokenCount(modelId: string, message: string | IChatMessage, token: CancellationToken): Promise<number>;
 }
 
 export interface ILanguageModelChat {
 	metadata: ILanguageModelChatMetadata;
-	sendChatRequest(messages: IChatMessage[], from: ExtensionIdentifier, options: { [name: string]: unknown }, token: CancellationToken): Promise<ILanguageModelChatResponse>;
+	sendChatRequest(messages: IChatMessage[], from: ExtensionIdentifier | undefined, options: { [name: string]: unknown }, token: CancellationToken): Promise<ILanguageModelChatResponse>;
 	provideTokenCount(message: string | IChatMessage, token: CancellationToken): Promise<number>;
 }
 
@@ -355,7 +355,7 @@ export interface ILanguageModelsService {
 	deltaLanguageModelChatProviderDescriptors(added: IUserFriendlyLanguageModel[], removed: IUserFriendlyLanguageModel[]): void;
 
 	// eslint-disable-next-line @typescript-eslint/no-explicit-any
-	sendChatRequest(modelId: string, from: ExtensionIdentifier, messages: IChatMessage[], options: { [name: string]: any }, token: CancellationToken): Promise<ILanguageModelChatResponse>;
+	sendChatRequest(modelId: string, from: ExtensionIdentifier | undefined, messages: IChatMessage[], options: { [name: string]: any }, token: CancellationToken): Promise<ILanguageModelChatResponse>;
 
 	computeTokenLength(modelId: string, message: string | IChatMessage, token: CancellationToken): Promise<number>;
 
@@ -927,7 +927,7 @@ export class LanguageModelsService implements ILanguageModelsService {
 	}
 
 	// eslint-disable-next-line @typescript-eslint/no-explicit-any
-	async sendChatRequest(modelId: string, from: ExtensionIdentifier, messages: IChatMessage[], options: { [name: string]: any }, token: CancellationToken): Promise<ILanguageModelChatResponse> {
+	async sendChatRequest(modelId: string, from: ExtensionIdentifier | undefined, messages: IChatMessage[], options: { [name: string]: any }, token: CancellationToken): Promise<ILanguageModelChatResponse> {
 		const provider = this._providers.get(this._modelCache.get(modelId)?.vendor || '');
 		if (!provider) {
 			throw new Error(`Chat provider for model ${modelId} is not registered.`);
@@ -1512,7 +1512,7 @@ export class LanguageModelsService implements ILanguageModelsService {
 
 		let context;
 		try {
-			context = await this._requestService.request({ type: 'GET', url: this._chatControlUrl! }, CancellationToken.None);
+			context = await this._requestService.request({ type: 'GET', url: this._chatControlUrl!, callSite: 'languageModels.fetchChatControlData' }, CancellationToken.None);
 		} catch (err) {
 			this._logService.warn('[LM] Failed to request chat control data', getErrorMessage(err));
 			return;
diff --git a/src/vs/workbench/contrib/chat/common/model/chatModel.ts b/src/vs/workbench/contrib/chat/common/model/chatModel.ts
index a85a969c0b2f0..6bff6a8654455 100644
--- a/src/vs/workbench/contrib/chat/common/model/chatModel.ts
+++ b/src/vs/workbench/contrib/chat/common/model/chatModel.ts
@@ -30,7 +30,7 @@ import { CellUri, ICellEditOperation } from '../../../notebook/common/notebookCo
 import { ChatRequestToolReferenceEntry, IChatRequestVariableEntry, isImplicitVariableEntry, isStringImplicitContextValue, isStringVariableEntry } from '../attachments/chatVariableEntries.js';
 import { migrateLegacyTerminalToolSpecificData } from '../chat.js';
 import { ChatAgentVoteDirection, ChatAgentVoteDownReason, ChatRequestQueueKind, ChatResponseClearToPreviousToolInvocationReason, ElicitationState, IChatAgentMarkdownContentWithVulnerability, IChatClearToPreviousToolInvocation, IChatCodeCitation, IChatCommandButton, IChatConfirmation, IChatContentInlineReference, IChatContentReference, IChatDisabledClaudeHooksPart, IChatEditingSessionAction, IChatElicitationRequest, IChatElicitationRequestSerialized, IChatExternalToolInvocationUpdate, IChatExtensionsContent, IChatFollowup, IChatHookPart, IChatLocationData, IChatMarkdownContent, IChatMcpServersStarting, IChatMcpServersStartingSerialized, IChatModelReference, IChatMultiDiffData, IChatMultiDiffDataSerialized, IChatNotebookEdit, IChatProgress, IChatProgressMessage, IChatPullRequestContent, IChatQuestionCarousel, IChatResponseCodeblockUriPart, IChatResponseProgressFileTreeData, IChatSendRequestOptions, IChatService, IChatSessionContext, IChatSessionTiming, IChatTask, IChatTaskSerialized, IChatTextEdit, IChatThinkingPart, IChatToolInvocation, IChatToolInvocationSerialized, IChatTreeData, IChatUndoStop, IChatUsage, IChatUsedContext, IChatWarningMessage, IChatWorkspaceEdit, ResponseModelState, isIUsedContext } from '../chatService/chatService.js';
-import { ChatAgentLocation, ChatModeKind } from '../constants.js';
+import { ChatAgentLocation, ChatModeKind, ChatPermissionLevel } from '../constants.js';
 import { ChatToolInvocation } from './chatProgressTypes/chatToolInvocation.js';
 import { ToolDataSource, IToolData } from '../tools/languageModelToolsService.js';
 import { IChatEditingService, IChatEditingSession, ModifiedFileEntryState } from '../editing/chatEditingService.js';
@@ -313,14 +313,18 @@ export interface IChatRequestModeInfo {
 	isBuiltin: boolean;
 	modeInstructions: IChatRequestModeInstructions | undefined;
 	modeId: 'ask' | 'agent' | 'edit' | 'custom' | 'applyCodeBlock' | undefined;
+	modeName?: string;
 	applyCodeBlockSuggestionId: EditSuggestionId | undefined;
+	permissionLevel?: ChatPermissionLevel;
 }
 
 export interface IChatRequestModeInstructions {
+	readonly uri?: URI;
 	readonly name: string;
 	readonly content: string;
 	readonly toolReferences: readonly ChatRequestToolReferenceEntry[];
 	readonly metadata?: Record<string, boolean | string | number>;
+	readonly isBuiltin?: boolean;
 }
 
 export interface IChatRequestModelParameters {
@@ -433,13 +437,15 @@ class AbstractResponse implements IResponse {
 
 	/**
 	 * A stringified representation of response data which might be presented to a screenreader or used when copying a response.
+	 * Computed lazily on demand to avoid expensive string rebuilding during streaming.
 	 */
-	protected _responseRepr = '';
+	private _responseRepr: string | undefined;
 
 	/**
-	 * Just the markdown content of the response, used for determining the rendering rate of markdown
+	 * Just the markdown content of the response, used for determining the rendering rate of markdown.
+	 * Computed lazily on demand to avoid expensive string rebuilding during streaming.
 	 */
-	protected _markdownContent = '';
+	private _markdownContent: string | undefined;
 
 	get value(): IChatProgressResponseContent[] {
 		return this._responseParts;
@@ -447,10 +453,12 @@ class AbstractResponse implements IResponse {
 
 	constructor(value: IChatProgressResponseContent[]) {
 		this._responseParts = value;
-		this._updateRepr();
 	}
 
 	toString(): string {
+		if (this._responseRepr === undefined) {
+			this._responseRepr = this.computeRepr();
+		}
 		return this._responseRepr;
 	}
 
@@ -458,23 +466,36 @@ class AbstractResponse implements IResponse {
 	 * _Just_ the content of markdown parts in the response
 	 */
 	getMarkdown(): string {
+		if (this._markdownContent === undefined) {
+			this._markdownContent = this.computeMarkdownContent();
+		}
 		return this._markdownContent;
 	}
 
-	protected _updateRepr() {
-		this._responseRepr = this.partsToRepr(this._responseParts);
+	/**
+	 * Invalidate cached representations so they are recomputed on next access.
+	 */
+	protected _invalidateRepr() {
+		this._responseRepr = undefined;
+		this._markdownContent = undefined;
+	}
 
-		this._markdownContent = this._responseParts.map(part => {
+	private computeMarkdownContent(): string {
+		const segments: string[] = [];
+		for (const part of this._responseParts) {
 			if (part.kind === 'inlineReference') {
-				return this.inlineRefToRepr(part);
+				segments.push(this.inlineRefToRepr(part));
 			} else if (part.kind === 'markdownContent' || part.kind === 'markdownVuln') {
-				return part.content.value;
-			} else {
-				return '';
+				if (part.content.value.length > 0) {
+					segments.push(part.content.value);
+				}
 			}
-		})
-			.filter(s => s.length > 0)
-			.join('');
+		}
+		return segments.join('');
+	}
+
+	protected computeRepr(): string {
+		return this.partsToRepr(this._responseParts);
 	}
 
 	private partsToRepr(parts: readonly IChatProgressResponseContent[]): string {
@@ -670,7 +691,7 @@ export class Response extends AbstractResponse implements IDisposable {
 
 	clear(): void {
 		this._responseParts = [];
-		this._updateRepr(true);
+		this._contentChanged(true);
 	}
 
 	clearToPreviousToolInvocation(message?: string): void {
@@ -691,7 +712,7 @@ export class Response extends AbstractResponse implements IDisposable {
 		if (message) {
 			this._responseParts.push({ kind: 'warning', content: new MarkdownString(message) });
 		}
-		this._updateRepr(true);
+		this._contentChanged(true);
 	}
 
 	updateContent(progress: IChatProgressResponseContent | IChatTextEdit | IChatNotebookEdit | IChatTask | IChatExternalToolInvocationUpdate, quiet?: boolean): void {
@@ -720,7 +741,7 @@ export class Response extends AbstractResponse implements IDisposable {
 				const idx = this._responseParts.indexOf(lastResponsePart);
 				this._responseParts[idx] = { ...lastResponsePart, content: appendMarkdownString(lastResponsePart.content, progress.content) };
 			}
-			this._updateRepr(quiet);
+			this._contentChanged(quiet);
 		} else if (progress.kind === 'thinking') {
 
 			// tries to split thinking chunks if it is an array. only while certain models give us array chunks.
@@ -748,7 +769,7 @@ export class Response extends AbstractResponse implements IDisposable {
 					value: appendMarkdownString(new MarkdownString(lastText), new MarkdownString(currText)).value
 				};
 			}
-			this._updateRepr(quiet);
+			this._contentChanged(quiet);
 		} else if (progress.kind === 'textEdit' || progress.kind === 'notebookEdit') {
 			// merge edits for the same file no matter when they come in
 			const notebookUri = CellUri.parse(progress.uri)?.notebook;
@@ -766,14 +787,14 @@ export class Response extends AbstractResponse implements IDisposable {
 				// Notebook cell edits (ICellEditOperation)
 				this._mergeOrPushNotebookEditGroup(uri, progress.edits, progress.done, isExternalEdit);
 			}
-			this._updateRepr(quiet);
+			this._contentChanged(quiet);
 		} else if (progress.kind === 'progressTask') {
 			// Add a new resolving part
 			const responsePosition = this._responseParts.push(progress) - 1;
-			this._updateRepr(quiet);
+			this._contentChanged(quiet);
 
 			const disp = progress.onDidAddProgress(() => {
-				this._updateRepr(false);
+				this._contentChanged(false);
 			});
 
 			progress.task?.().then((content) => {
@@ -784,32 +805,32 @@ export class Response extends AbstractResponse implements IDisposable {
 				if (typeof content === 'string') {
 					(this._responseParts[responsePosition] as IChatTask).content = new MarkdownString(content);
 				}
-				this._updateRepr(false);
+				this._contentChanged(false);
 			});
 
 		} else if (progress.kind === 'toolInvocation') {
 			autorunSelfDisposable(reader => {
 				progress.state.read(reader); // update repr when state changes
-				this._updateRepr(false);
+				this._contentChanged(false);
 
 				if (IChatToolInvocation.isComplete(progress, reader)) {
 					reader.dispose();
 				}
 			});
 			this._responseParts.push(progress);
-			this._updateRepr(quiet);
+			this._contentChanged(quiet);
 		} else if (progress.kind === 'externalToolInvocationUpdate') {
 			this._handleExternalToolInvocationUpdate(progress);
-			this._updateRepr(quiet);
+			this._contentChanged(quiet);
 		} else {
 			this._responseParts.push(progress);
-			this._updateRepr(quiet);
+			this._contentChanged(quiet);
 		}
 	}
 
 	public addCitation(citation: IChatCodeCitation) {
 		this._citations.push(citation);
-		this._updateRepr();
+		this._contentChanged();
 	}
 
 	private _mergeOrPushTextEditGroup(uri: URI, edits: TextEdit[], done: boolean | undefined, isExternalEdit: boolean | undefined): void {
@@ -846,6 +867,7 @@ export class Response extends AbstractResponse implements IDisposable {
 					content: [],
 					toolResultMessage: progress.pastTenseMessage,
 					toolResultError: progress.errorMessage,
+					toolResultDetails: progress.resultDetails
 				});
 			}
 			if (progress.toolSpecificData !== undefined) {
@@ -882,6 +904,7 @@ export class Response extends AbstractResponse implements IDisposable {
 				content: [],
 				toolResultMessage: progress.pastTenseMessage,
 				toolResultError: progress.errorMessage,
+				toolResultDetails: progress.resultDetails
 			});
 			if (progress.toolSpecificData !== undefined) {
 				invocation.toolSpecificData = progress.toolSpecificData;
@@ -891,14 +914,16 @@ export class Response extends AbstractResponse implements IDisposable {
 		this._responseParts.push(invocation);
 	}
 
-	protected override _updateRepr(quiet?: boolean) {
-		super._updateRepr();
-		if (!this._onDidChangeValue) {
-			return; // called from parent constructor
+	protected override computeRepr(): string {
+		let repr = super.computeRepr();
+		if (this._citations.length) {
+			repr += '\n\n' + getCodeCitationsMessage(this._citations);
 		}
+		return repr;
+	}
 
-		this._responseRepr += this._citations.length ? '\n\n' + getCodeCitationsMessage(this._citations) : '';
-
+	private _contentChanged(quiet?: boolean) {
+		this._invalidateRepr();
 		if (!quiet) {
 			this._onDidChangeValue.fire();
 		}
@@ -1445,6 +1470,7 @@ export interface ISerializableChatRequestData extends ISerializableChatResponseD
 	confirmation?: string;
 	editedFileEvents?: IChatAgentEditedFileEvent[];
 	modelId?: string;
+	modeInfo?: IChatRequestModeInfo;
 }
 
 export interface ISerializableMarkdownInfo {
@@ -1993,6 +2019,21 @@ export class ChatModel extends Disposable implements IChatModel {
 		return request;
 	}
 
+	/**
+	 * @internal Used by ChatService to dequeue all consecutive steering requests at the front of the queue.
+	 * Returns an empty array if the first pending request is not a steering request.
+	 */
+	dequeueAllSteeringRequests(): IChatPendingRequest[] {
+		const steeringRequests: IChatPendingRequest[] = [];
+		while (this._pendingRequests.at(0)?.kind === ChatRequestQueueKind.Steering) {
+			steeringRequests.push(this._pendingRequests.shift()!);
+		}
+		if (steeringRequests.length > 0) {
+			this._onDidChangePendingRequests.fire();
+		}
+		return steeringRequests;
+	}
+
 	/**
 	 * @internal Used by ChatService to clear all pending requests
 	 */
@@ -2296,6 +2337,7 @@ export class ChatModel extends Disposable implements IChatModel {
 			confirmation: raw.confirmation,
 			editedFileEvents: raw.editedFileEvents,
 			modelId: raw.modelId,
+			modeInfo: raw.modeInfo,
 		});
 		request.shouldBeRemovedOnSend = raw.isHidden ? { requestId: raw.requestId } : raw.shouldBeRemovedOnSend;
 		// eslint-disable-next-line @typescript-eslint/no-explicit-any, local/code-no-any-casts
@@ -2638,6 +2680,7 @@ export class ChatModel extends Disposable implements IChatModel {
 					confirmation: r.confirmation,
 					editedFileEvents: r.editedFileEvents,
 					modelId: r.modelId,
+					modeInfo: r.modeInfo,
 					...r.response?.toJSON(),
 				};
 			}),
diff --git a/src/vs/workbench/contrib/chat/common/model/chatProgressTypes/chatQuestionCarouselData.ts b/src/vs/workbench/contrib/chat/common/model/chatProgressTypes/chatQuestionCarouselData.ts
index f0d598be6dbbc..5feb507b75545 100644
--- a/src/vs/workbench/contrib/chat/common/model/chatProgressTypes/chatQuestionCarouselData.ts
+++ b/src/vs/workbench/contrib/chat/common/model/chatProgressTypes/chatQuestionCarouselData.ts
@@ -4,7 +4,9 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { DeferredPromise } from '../../../../../../base/common/async.js';
-import { IChatQuestion, IChatQuestionCarousel } from '../../chatService/chatService.js';
+import { IMarkdownString } from '../../../../../../base/common/htmlContent.js';
+import { IChatQuestion, IChatQuestionAnswers, IChatQuestionCarousel } from '../../chatService/chatService.js';
+import { ToolDataSource } from '../../tools/languageModelToolsService.js';
 
 /**
  * Runtime representation of a question carousel with a {@link DeferredPromise}
@@ -13,14 +15,18 @@ import { IChatQuestion, IChatQuestionCarousel } from '../../chatService/chatServ
  */
 export class ChatQuestionCarouselData implements IChatQuestionCarousel {
 	public readonly kind = 'questionCarousel' as const;
-	public readonly completion = new DeferredPromise<{ answers: Record<string, unknown> | undefined }>();
+	public readonly completion = new DeferredPromise<{ answers: IChatQuestionAnswers | undefined }>();
+	public draftAnswers: IChatQuestionAnswers | undefined;
+	public draftCurrentIndex: number | undefined;
 
 	constructor(
 		public questions: IChatQuestion[],
 		public allowSkip: boolean,
 		public resolveId?: string,
-		public data?: Record<string, unknown>,
+		public data?: IChatQuestionAnswers,
 		public isUsed?: boolean,
+		public message?: string | IMarkdownString,
+		public source?: ToolDataSource,
 	) { }
 
 	toJSON(): IChatQuestionCarousel {
@@ -31,6 +37,8 @@ export class ChatQuestionCarouselData implements IChatQuestionCarousel {
 			resolveId: this.resolveId,
 			data: this.data,
 			isUsed: this.isUsed,
+			message: this.message,
+			source: this.source,
 		};
 	}
 }
diff --git a/src/vs/workbench/contrib/chat/common/model/chatProgressTypes/chatToolInvocation.ts b/src/vs/workbench/contrib/chat/common/model/chatProgressTypes/chatToolInvocation.ts
index da6353f3cd5da..f128efd7e89fe 100644
--- a/src/vs/workbench/contrib/chat/common/model/chatProgressTypes/chatToolInvocation.ts
+++ b/src/vs/workbench/contrib/chat/common/model/chatProgressTypes/chatToolInvocation.ts
@@ -7,7 +7,7 @@ import { encodeBase64 } from '../../../../../../base/common/buffer.js';
 import { IMarkdownString } from '../../../../../../base/common/htmlContent.js';
 import { IObservable, ISettableObservable, observableValue } from '../../../../../../base/common/observable.js';
 import { localize } from '../../../../../../nls.js';
-import { ConfirmedReason, IChatExtensionsContent, IChatSimpleToolInvocationData, IChatSubagentToolInvocationData, IChatTodoListContent, IChatToolInputInvocationData, IChatToolInvocation, IChatToolInvocationSerialized, ToolConfirmKind, type IChatTerminalToolInvocationData } from '../../chatService/chatService.js';
+import { ConfirmedReason, IChatExtensionsContent, IChatModifiedFilesConfirmationData, IChatSimpleToolInvocationData, IChatSubagentToolInvocationData, IChatTodoListContent, IChatToolInputInvocationData, IChatToolInvocation, IChatToolInvocationSerialized, ToolConfirmKind, type IChatTerminalToolInvocationData } from '../../chatService/chatService.js';
 import { IPreparedToolInvocation, isToolResultOutputDetails, IToolConfirmationMessages, IToolData, IToolProgressStep, IToolResult, ToolDataSource } from '../../tools/languageModelToolsService.js';
 
 export interface IStreamingToolCallOptions {
@@ -32,8 +32,9 @@ export class ChatToolInvocation implements IChatToolInvocation {
 	public parameters: unknown;
 	public generatedTitle?: string;
 	public readonly chatRequestId?: string;
+	public isAttachedToThinking: boolean = false;
 
-	public toolSpecificData?: IChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatSimpleToolInvocationData;
+	public toolSpecificData?: IChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatSimpleToolInvocationData | IChatModifiedFilesConfirmationData;
 
 	private readonly _progress = observableValue<{ message?: string | IMarkdownString; progress: number | undefined }>(this, { progress: 0 });
 	private readonly _state: ISettableObservable<IChatToolInvocation.State>;
@@ -74,7 +75,7 @@ export class ChatToolInvocation implements IChatToolInvocation {
 		// For streaming invocations, use a default message until handleToolStream provides one
 		let defaultMessage: string | IMarkdownString = '';
 		if (startOptions.startInStreaming) {
-			defaultMessage = localize('toolInvocationMessage', "Using \"{0}\"", toolData.displayName);
+			defaultMessage = toolData.displayName;
 		} else if (startOptions.startInCancelled) {
 			defaultMessage = startOptions.cancelReasonMessage ?? localize('toolDeniedMessage', "Tool \"{0}\" was denied", toolData.displayName);
 		}
diff --git a/src/vs/workbench/contrib/chat/common/model/chatSessionOperationLog.ts b/src/vs/workbench/contrib/chat/common/model/chatSessionOperationLog.ts
index 767cb087be6a4..9c69890c9a78c 100644
--- a/src/vs/workbench/contrib/chat/common/model/chatSessionOperationLog.ts
+++ b/src/vs/workbench/contrib/chat/common/model/chatSessionOperationLog.ts
@@ -3,7 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { assertNever } from '../../../../../base/common/assert.js';
+import { softAssertNever } from '../../../../../base/common/assert.js';
 import { isMarkdownString } from '../../../../../base/common/htmlContent.js';
 import { equals as objectsEqual } from '../../../../../base/common/objects.js';
 import { isEqual as _urisEqual } from '../../../../../base/common/resources.js';
@@ -90,7 +90,9 @@ const responsePartSchema = Adapt.v<IChatProgressResponseContent, SerializedChatR
 					// If it's a 'static' type that is not expected to change, add it to the 'return true'
 					// block above. However it's a type that is going to change, add it to the 'objectsEqual'
 					// block or make something more tailored.
-					assertNever(a);
+					softAssertNever(a);
+
+					return objectsEqual(a, b);
 				}
 			}
 		}
@@ -148,6 +150,7 @@ const requestSchema = Adapt.object<IChatRequestModel, ISerializableChatRequestDa
 	contentReferences: Adapt.v(m => m.response?.contentReferences, objectsEqual),
 	codeCitations: Adapt.v(m => m.response?.codeCitations, objectsEqual),
 	timeSpentWaiting: Adapt.v(m => m.response?.timestamp), // based on response timestamp
+	modeInfo: Adapt.v(m => m.modeInfo, objectsEqual),
 }, {
 	sealed: (o) => o.modelState?.value === ResponseModelState.Cancelled || o.modelState?.value === ResponseModelState.Failed || o.modelState?.value === ResponseModelState.Complete,
 });
diff --git a/src/vs/workbench/contrib/chat/common/model/chatSessionStore.ts b/src/vs/workbench/contrib/chat/common/model/chatSessionStore.ts
index cecb075bd83f8..3406db66f8477 100644
--- a/src/vs/workbench/contrib/chat/common/model/chatSessionStore.ts
+++ b/src/vs/workbench/contrib/chat/common/model/chatSessionStore.ts
@@ -9,13 +9,15 @@ import { toErrorMessage } from '../../../../../base/common/errorMessage.js';
 import { MarkdownString } from '../../../../../base/common/htmlContent.js';
 import { Disposable } from '../../../../../base/common/lifecycle.js';
 import { revive } from '../../../../../base/common/marshalling.js';
-import { joinPath } from '../../../../../base/common/resources.js';
+import { isEqual, joinPath } from '../../../../../base/common/resources.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { localize } from '../../../../../nls.js';
 import { IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
+import { IDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
 import { IEnvironmentService } from '../../../../../platform/environment/common/environment.js';
 import { FileOperationResult, IFileService, toFileOperationResult } from '../../../../../platform/files/common/files.js';
 import { ILogService } from '../../../../../platform/log/common/log.js';
+import { IOpenerService } from '../../../../../platform/opener/common/opener.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../../platform/storage/common/storage.js';
 import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
 import { IUserDataProfilesService } from '../../../../../platform/userDataProfile/common/userDataProfile.js';
@@ -57,6 +59,8 @@ export class ChatSessionStore extends Disposable {
 		@IUserDataProfilesService private readonly userDataProfilesService: IUserDataProfilesService,
 		@IConfigurationService private readonly configurationService: IConfigurationService,
 		@IWorkspaceEditingService private readonly workspaceEditingService: IWorkspaceEditingService,
+		@IDialogService private readonly dialogService: IDialogService,
+		@IOpenerService private readonly openerService: IOpenerService,
 	) {
 		super();
 
@@ -111,7 +115,7 @@ export class ChatSessionStore extends Disposable {
 			joinPath(this.environmentService.workspaceStorageHome, newWorkspaceId, 'chatSessions');
 
 		// If the storage roots are identical, there is nothing to migrate
-		if (oldStorageRoot.toString() === newStorageRoot.toString()) {
+		if (isEqual(oldStorageRoot, newStorageRoot)) {
 			this.storageRoot = newStorageRoot;
 			return;
 		}
@@ -339,6 +343,8 @@ export class ChatSessionStore extends Disposable {
 		}
 	}
 
+	private _didReportIssue = false;
+
 	private async writeSession(session: ChatModel | ISerializableChatData): Promise<void> {
 		try {
 			const index = this.internalGetIndex();
@@ -349,7 +355,32 @@ export class ChatSessionStore extends Disposable {
 						session.dataSerializer = new ChatSessionOperationLog();
 					}
 
-					const { op, data } = session.dataSerializer.write(session);
+					let op: 'append' | 'replace';
+					let data: VSBuffer;
+					try {
+						({ op, data } = session.dataSerializer.write(session));
+					} catch (e) {
+						// This is a big of an ugly prompt, but there is _something_ going on with
+						// missing sessions. Unfortunately it's hard to root cause because users would
+						// not notice an error until they reload the window, at which point any error
+						// is gone. Throw a very verbose dialog here so we can get some quality
+						// bug reports, if the issue is indeed in the serialized.
+						// todo@connor4312: remove after a little bit
+						if (!this._didReportIssue) {
+							this._didReportIssue = true;
+							this.dialogService.prompt({
+								custom: true, // so text is copyable
+								title: localize('chatSessionStore.serializationError', 'Error saving chat session'),
+								message: localize('chatSessionStore.writeError', 'Error serializing chat session for storage. The session will be lost if the window is closed. Please report this issue to the VS Code team:\n\n{0}', e.stack || toErrorMessage(e)),
+								buttons: [
+									{ label: localize('reportIssue', 'Report Issue'), run: () => this.openerService.open('https://github.com/microsoft/vscode/issues/new?template=bug_report.md') }
+								]
+							});
+						}
+
+						throw e;
+					}
+
 					if (data.byteLength > 0) {
 						await this.fileService.writeFile(storageLocation.log, data, { append: op === 'append' });
 					}
diff --git a/src/vs/workbench/contrib/chat/common/model/chatUri.ts b/src/vs/workbench/contrib/chat/common/model/chatUri.ts
index 911494c6e8057..0a0830b79503f 100644
--- a/src/vs/workbench/contrib/chat/common/model/chatUri.ts
+++ b/src/vs/workbench/contrib/chat/common/model/chatUri.ts
@@ -91,3 +91,7 @@ export function getChatSessionType(resource: URI): string {
 
 	return resource.scheme;
 }
+
+export function isUntitledChatSession(resource: URI): boolean {
+	return resource.path.startsWith('/untitled-');
+}
diff --git a/src/vs/workbench/contrib/chat/common/model/chatViewModel.ts b/src/vs/workbench/contrib/chat/common/model/chatViewModel.ts
index 5c53cac197fd1..0c799d61f2001 100644
--- a/src/vs/workbench/contrib/chat/common/model/chatViewModel.ts
+++ b/src/vs/workbench/contrib/chat/common/model/chatViewModel.ts
@@ -7,6 +7,7 @@ import { Codicon } from '../../../../../base/common/codicons.js';
 import { Emitter, Event } from '../../../../../base/common/event.js';
 import { IMarkdownString } from '../../../../../base/common/htmlContent.js';
 import { Disposable, dispose } from '../../../../../base/common/lifecycle.js';
+import { RunOnceScheduler } from '../../../../../base/common/async.js';
 import { IObservable } from '../../../../../base/common/observable.js';
 import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { URI } from '../../../../../base/common/uri.js';
@@ -645,11 +646,13 @@ export class ChatResponseViewModel extends Disposable implements IChatResponseVi
 			this.liveUpdateTracker = this.instantiationService.createInstance(ChatStreamStatsTracker);
 		}
 
+		const wordCountScheduler = this.liveUpdateTracker ? this._register(new RunOnceScheduler(() => {
+			const wordCount = countWords(_model.entireResponse.getMarkdown());
+			this.liveUpdateTracker!.update({ totalWordCount: wordCount });
+		}, 0)) : undefined;
+
 		this._register(_model.onDidChange(() => {
-			if (this.liveUpdateTracker) {
-				const wordCount = countWords(_model.entireResponse.getMarkdown());
-				this.liveUpdateTracker.update({ totalWordCount: wordCount });
-			}
+			wordCountScheduler?.schedule();
 
 			// new data -> new id, new content to render
 			this._modelChangeCount++;
diff --git a/src/vs/workbench/contrib/chat/common/model/objectMutationLog.ts b/src/vs/workbench/contrib/chat/common/model/objectMutationLog.ts
index 01ce16ae67a9b..1e134a69a6d54 100644
--- a/src/vs/workbench/contrib/chat/common/model/objectMutationLog.ts
+++ b/src/vs/workbench/contrib/chat/common/model/objectMutationLog.ts
@@ -7,6 +7,34 @@ import { assertNever } from '../../../../../base/common/assert.js';
 import { VSBuffer } from '../../../../../base/common/buffer.js';
 import { isUndefinedOrNull } from '../../../../../base/common/types.js';
 
+/**
+ * Updates an error's message and stack trace with a prefix. In V8 the stack
+ * string starts with "ErrorName: message\n  at …", so we rebuild the header
+ * after mutating the message.
+ */
+function prefixError(e: Error, prefix: string): void {
+	e.message = prefix + e.message;
+	if (e.stack) {
+		const nlIdx = e.stack.indexOf('\n');
+		e.stack = nlIdx !== -1
+			? `${e.name}: ${e.message}${e.stack.slice(nlIdx)}`
+			: `${e.name}: ${e.message}`;
+	}
+}
+
+/**
+ * Prepends a path segment to an error as it unwinds through nested extract
+ * calls. Each level adds its segment so the final message reads e.g.
+ * `.responses[2].content: Cannot read property 'x' of undefined`.
+ */
+function rethrowWithPathSegment(e: unknown, segment: string | number): never {
+	if (e instanceof Error) {
+		const part = typeof segment === 'number' ? `[${segment}]` : `.${segment}`;
+		const needsSep = !e.message.startsWith('[') && !e.message.startsWith('.');
+		prefixError(e, part + (needsSep ? ': ' : ''));
+	}
+	throw e;
+}
 
 /** IMPORTANT: `Key` comes first. Then we should sort in order of least->most expensive to diff */
 const enum TransformKind {
@@ -96,7 +124,13 @@ export function array<T, R>(schema: TransformObject<T, R> | TransformValue<T, R>
 	return {
 		kind: TransformKind.Array,
 		itemSchema: schema,
-		extract: from => from?.map(item => schema.extract(item)),
+		extract: from => from?.map((item, i) => {
+			try {
+				return schema.extract(item);
+			} catch (e) {
+				rethrowWithPathSegment(e, i);
+			}
+		}),
 	};
 }
 
@@ -124,7 +158,11 @@ export function object<T, R extends object>(schema: Schema<T, R>, options?: Obje
 
 			const result: Record<string, unknown> = Object.create(null);
 			for (const [key, transform] of entries) {
-				result[key] = transform.extract(from);
+				try {
+					result[key] = transform.extract(from);
+				} catch (e) {
+					rethrowWithPathSegment(e, key);
+				}
 			}
 			return result as R;
 		},
@@ -278,7 +316,15 @@ export class ObjectMutationLog<TFrom, TTo> {
 		// Generate diff entries
 		const entries: Entry[] = [];
 		const path: ObjectPath = [];
-		this._diff(this._transform, path, this._previous, currentValue, entries);
+		try {
+			this._diff(this._transform, path, this._previous, currentValue, entries);
+		} catch (e) {
+			if (e instanceof Error) {
+				const pathStr = path.map(s => typeof s === 'number' ? `[${s}]` : `.${s}`).join('') || '<root>';
+				prefixError(e, `error diffing at ${pathStr}: `);
+			}
+			throw e;
+		}
 
 		if (entries.length === 0) {
 			// No changes
diff --git a/src/vs/workbench/contrib/chat/common/participants/chatAgents.ts b/src/vs/workbench/contrib/chat/common/participants/chatAgents.ts
index a5dbf7f25c50e..e8f4fbe4a03bc 100644
--- a/src/vs/workbench/contrib/chat/common/participants/chatAgents.ts
+++ b/src/vs/workbench/contrib/chat/common/participants/chatAgents.ts
@@ -21,10 +21,10 @@ import { ExtensionIdentifier } from '../../../../../platform/extensions/common/e
 import { createDecorator } from '../../../../../platform/instantiation/common/instantiation.js';
 import { ChatContextKeys } from '../actions/chatContextKeys.js';
 import { IChatAgentEditedFileEvent, IChatProgressHistoryResponseContent, IChatRequestModeInstructions, IChatRequestVariableData, ISerializableChatAgentData } from '../model/chatModel.js';
-import { IChatRequestHooks } from '../promptSyntax/hookSchema.js';
+import { ChatRequestHooks } from '../promptSyntax/hookSchema.js';
 import { IRawChatCommandContribution } from './chatParticipantContribTypes.js';
 import { IChatFollowup, IChatLocationData, IChatProgress, IChatResponseErrorDetails, IChatTaskDto } from '../chatService/chatService.js';
-import { ChatAgentLocation, ChatConfiguration, ChatModeKind } from '../constants.js';
+import { ChatAgentLocation, ChatConfiguration, ChatModeKind, ChatPermissionLevel } from '../constants.js';
 import { ILanguageModelsService } from '../languageModels.js';
 
 //#region agent service, commands etc
@@ -47,6 +47,7 @@ export interface IChatAgentAttachmentCapabilities {
 	supportsSymbolAttachments?: boolean;
 	supportsTerminalAttachments?: boolean;
 	supportsPromptAttachments?: boolean;
+	supportsHandOffs?: boolean;
 }
 
 export interface IChatAgentData {
@@ -152,11 +153,17 @@ export interface IChatAgentRequest {
 	 * Collected hooks configuration for this request.
 	 * Contains all hooks defined in hooks .json files, organized by hook type.
 	 */
-	hooks?: IChatRequestHooks;
+	hooks?: ChatRequestHooks;
 	/**
 	 * Whether any hooks are enabled for this request.
 	 */
 	hasHooksEnabled?: boolean;
+	/**
+	 * The permission level for tool auto-approval in this request.
+	 * - `'autoApprove'`: Auto-approve all tool calls and retry on errors.
+	 * - `'autopilot'`: Everything autoApprove does plus continues until the task is done.
+	 */
+	permissionLevel?: ChatPermissionLevel;
 	/**
 	 * Unique ID for the subagent invocation, used to group tool calls from the same subagent run together.
 	 */
diff --git a/src/vs/workbench/contrib/chat/common/participants/chatSlashCommands.ts b/src/vs/workbench/contrib/chat/common/participants/chatSlashCommands.ts
index 9964cfaa4d27e..35c609e3c7d23 100644
--- a/src/vs/workbench/contrib/chat/common/participants/chatSlashCommands.ts
+++ b/src/vs/workbench/contrib/chat/common/participants/chatSlashCommands.ts
@@ -9,10 +9,11 @@ import { Disposable, IDisposable, toDisposable } from '../../../../../base/commo
 import { createDecorator } from '../../../../../platform/instantiation/common/instantiation.js';
 import { IProgress } from '../../../../../platform/progress/common/progress.js';
 import { IChatMessage } from '../languageModels.js';
-import { IChatFollowup, IChatProgress, IChatResponseProgressFileTreeData } from '../chatService/chatService.js';
+import { IChatFollowup, IChatProgress, IChatResponseProgressFileTreeData, IChatSendRequestOptions } from '../chatService/chatService.js';
 import { IExtensionService } from '../../../../services/extensions/common/extensions.js';
 import { ChatAgentLocation, ChatModeKind } from '../constants.js';
 import { URI } from '../../../../../base/common/uri.js';
+import { Target } from '../promptSyntax/promptTypes.js';
 
 //#region slash service, commands etc
 
@@ -37,12 +38,13 @@ export interface IChatSlashData {
 
 	locations: ChatAgentLocation[];
 	modes?: ChatModeKind[];
+	target?: Target;
 }
 
 export interface IChatSlashFragment {
 	content: string | { treeData: IChatResponseProgressFileTreeData };
 }
-export type IChatSlashCallback = { (prompt: string, progress: IProgress<IChatProgress>, history: IChatMessage[], location: ChatAgentLocation, sessionResource: URI, token: CancellationToken): Promise<{ followUp: IChatFollowup[] } | void> };
+export type IChatSlashCallback = { (prompt: string, progress: IProgress<IChatProgress>, history: IChatMessage[], location: ChatAgentLocation, sessionResource: URI, token: CancellationToken, options?: IChatSendRequestOptions): Promise<{ followUp: IChatFollowup[] } | void> };
 
 export const IChatSlashCommandService = createDecorator<IChatSlashCommandService>('chatSlashCommandService');
 
@@ -53,7 +55,7 @@ export interface IChatSlashCommandService {
 	_serviceBrand: undefined;
 	readonly onDidChangeCommands: Event<void>;
 	registerSlashCommand(data: IChatSlashData, command: IChatSlashCallback): IDisposable;
-	executeCommand(id: string, prompt: string, progress: IProgress<IChatProgress>, history: IChatMessage[], location: ChatAgentLocation, sessionResource: URI, token: CancellationToken): Promise<{ followUp: IChatFollowup[] } | void>;
+	executeCommand(id: string, prompt: string, progress: IProgress<IChatProgress>, history: IChatMessage[], location: ChatAgentLocation, sessionResource: URI, token: CancellationToken, options?: IChatSendRequestOptions): Promise<{ followUp: IChatFollowup[] } | void>;
 	getCommands(location: ChatAgentLocation, mode: ChatModeKind): Array<IChatSlashData>;
 	hasCommand(id: string): boolean;
 }
@@ -103,7 +105,7 @@ export class ChatSlashCommandService extends Disposable implements IChatSlashCom
 		return this._commands.has(id);
 	}
 
-	async executeCommand(id: string, prompt: string, progress: IProgress<IChatProgress>, history: IChatMessage[], location: ChatAgentLocation, sessionResource: URI, token: CancellationToken): Promise<{ followUp: IChatFollowup[] } | void> {
+	async executeCommand(id: string, prompt: string, progress: IProgress<IChatProgress>, history: IChatMessage[], location: ChatAgentLocation, sessionResource: URI, token: CancellationToken, options?: IChatSendRequestOptions): Promise<{ followUp: IChatFollowup[] } | void> {
 		const data = this._commands.get(id);
 		if (!data) {
 			throw new Error('No command with id ${id} NOT registered');
@@ -115,6 +117,6 @@ export class ChatSlashCommandService extends Disposable implements IChatSlashCom
 			throw new Error(`No command with id ${id} NOT resolved`);
 		}
 
-		return await data.command(prompt, progress, history, location, sessionResource, token);
+		return await data.command(prompt, progress, history, location, sessionResource, token, options);
 	}
 }
diff --git a/src/vs/workbench/contrib/chat/common/plugins/AGENTS_PLUGINS.md b/src/vs/workbench/contrib/chat/common/plugins/AGENTS_PLUGINS.md
new file mode 100644
index 0000000000000..74bd0ab92f62b
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/plugins/AGENTS_PLUGINS.md
@@ -0,0 +1,205 @@
+# Agent Plugins Architecture
+
+Agent plugins are a modular extension system that allows external packages of prompts, hooks, skills, agents, and MCP server definitions to be discovered, installed, and contributed into the chat experience. This document describes the architecture of the `src/vs/workbench/contrib/chat/common/plugins/` layer and its browser-side implementations.
+
+## Directory Structure
+
+### Common layer (`common/plugins/`)
+| File | Role |
+|------|------|
+| `agentPluginService.ts` | Core interfaces (`IAgentPlugin`, `IAgentPluginService`, `IAgentPluginDiscovery`) and the discovery registry singleton |
+| `agentPluginServiceImpl.ts` | `AgentPluginService` implementation, `AbstractAgentPluginDiscovery` base class, format adapters (Copilot / Claude / Open Plugin) |
+| `agentPluginRepositoryService.ts` | `IAgentPluginRepositoryService` — abstract repository clone/pull/cache operations |
+| `pluginMarketplaceService.ts` | `IPluginMarketplaceService` — marketplace metadata, installed-plugin storage, trusted-marketplace tracking, periodic update checks |
+| `pluginInstallService.ts` | `IPluginInstallService` — install/update orchestration interface |
+| `pluginSource.ts` | `IPluginSource` — per-source-kind strategy interface (install path, ensure, update, cleanup) |
+
+### Browser layer (`browser/`)
+| File | Role |
+|------|------|
+| `agentPluginRepositoryService.ts` | Browser implementation of `IAgentPluginRepositoryService` (git clone/pull via Git service) |
+| `pluginSources.ts` | Concrete `IPluginSource` implementations: `GitHubPluginSource`, `GitUrlPluginSource`, `NpmPluginSource`, `PipPluginSource`, `RelativePathPluginSource` |
+| `pluginInstallService.ts` | Browser implementation of `IPluginInstallService` |
+| `agentPluginsView.ts` | Installed-plugins tree view UI |
+| `agentPluginActions.ts` | Context-menu actions for plugins |
+| `agentPluginEditor/` | Rich editor for browsing a single plugin's contents |
+
+## Core Interfaces
+
+### IAgentPlugin
+
+Represents a single discovered plugin:
+
+```
+uri              – Unique filesystem URI for the plugin root
+label            – Human-readable display name
+enablement       – Observable enable/disable state (ContributionEnablementState)
+hooks            – Observable list of IAgentPluginHook
+commands         – Observable list of IAgentPluginCommand  (*.md files in commands/)
+skills           – Observable list of IAgentPluginSkill    (dirs with SKILL.md in skills/)
+agents           – Observable list of IAgentPluginAgent    (*.md files in agents/)
+mcpServerDefinitions – Observable list of IAgentPluginMcpServerDefinition
+fromMarketplace  – Set when the plugin was installed from a marketplace
+remove()         – Removes this plugin from its discovery source
+```
+
+### IAgentPluginService
+
+Main entry point consumed by the rest of the workbench:
+
+```
+plugins          – IObservable<readonly IAgentPlugin[]>  (aggregate of all discoveries, deduped by URI)
+enablementModel  – Shared IEnablementModel for plugin enable/disable state
+```
+
+Registered as `InstantiationType.Delayed` — only instantiated when first injected.
+
+### IAgentPluginDiscovery
+
+Strategy for finding plugins from a particular source:
+
+```
+plugins  – IObservable<readonly IAgentPlugin[]>
+start(enablementModel) – Begin watching the source
+```
+
+Discoveries are registered into the global `agentPluginDiscoveryRegistry` singleton and instantiated by `AgentPluginService` on startup.
+
+## Discovery & Plugin Reading
+
+### AbstractAgentPluginDiscovery
+
+Shared base class that handles:
+
+1. **Format detection** — auto-detects whether a plugin uses the Copilot, Claude, or Open Plugin format based on path conventions and manifest existence.
+2. **Content reading** — reads commands, skills, agents, hooks, and MCP server definitions from the filesystem.
+3. **File watching** — watches plugin directories for changes and re-reads contents on a 200 ms debounced scheduler.
+4. **Observable propagation** — sets the `plugins` observable on each refresh cycle.
+
+Subclasses implement `_discoverPluginSources()` to determine *which* plugin URIs exist.
+
+### Discovery Implementations
+
+**ConfiguredAgentPluginDiscovery** — resolves `chat.pluginLocations` configuration entries (absolute, tilde-expanded, or workspace-relative paths) and watches for config changes.
+
+**MarketplaceAgentPluginDiscovery** — discovers plugins from `IPluginMarketplaceService.installedPlugins` and delegates to the install/repository services for on-disk availability.
+
+### Plugin Formats
+
+Three format adapters implement `IAgentPluginFormatAdapter`:
+
+| | Copilot | Claude | Open Plugin |
+|-|---------|--------|-------------|
+| Manifest | `plugin.json` | `.claude-plugin/plugin.json` | `.plugin/plugin.json` |
+| Hooks config | `hooks.json` | `hooks/hooks.json` | `hooks/hooks.json` |
+| Hook parser | `parseCopilotHooks()` | `parseClaudeHooks()` | `parseClaudeHooks()` |
+| Special handling | — | `${CLAUDE_PLUGIN_ROOT}` token replacement, `CLAUDE_PLUGIN_ROOT` env var injection | `${PLUGIN_ROOT}` token replacement, `PLUGIN_ROOT` env var injection |
+
+Auto-detection logic: if a `.plugin/plugin.json` manifest exists, the Open Plugin adapter is used; if the plugin URI path contains `.claude` or a `.claude-plugin/plugin.json` manifest exists, the Claude adapter is used; otherwise, the Copilot adapter is used.
+
+### Plugin Contents (Filesystem Layout)
+
+```
+<plugin-root>/
+├── plugin.json                                    # Copilot manifest
+├── .claude-plugin/plugin.json                     # Claude manifest
+├── .plugin/plugin.json                            # Open Plugin manifest
+├── hooks.json   OR  hooks/hooks.json              # hook definitions
+├── .mcp.json                                      # MCP server definitions (optional)
+├── commands/
+│   ├── do-thing.md                                # → IAgentPluginCommand
+│   └── other.md
+├── skills/
+│   └── my-skill/
+│       └── SKILL.md                               # → IAgentPluginSkill
+└── agents/
+    └── helper.md                                  # → IAgentPluginAgent
+```
+
+## Marketplace & Installation
+
+### IPluginMarketplaceService
+
+Manages the catalog of available and installed plugins:
+
+- **Fetch** — reads `chat.pluginMarketplaces` config (GitHub shorthand, Git URLs, or file URIs), fetches `marketplace.json` from each, and returns parsed `IMarketplacePlugin` entries.
+- **Installed storage** — persists installed plugins in application-scoped storage (`chat.plugins.installed.v1`). Each entry tracks `{ pluginUri, plugin, enabled }`.
+- **Trust** — marketplace canonical IDs must be explicitly trusted before install proceeds (`chat.plugins.trustedMarketplaces.v1`).
+- **Auto-update** — checks for upstream changes approximately every 24 hours when `extensions.autoUpdate` is enabled; sets `hasUpdatesAvailable` observable.
+- **GitHub caching** — caches raw GitHub API responses with an 8-hour TTL to avoid repeated fetches.
+
+### Marketplace Definition Files
+
+Checked in order per repository:
+1. `marketplace.json` → `MarketplaceType.OpenPlugin`
+2. `.plugin/marketplace.json` → `MarketplaceType.OpenPlugin`
+3. `.github/plugin/marketplace.json` → `MarketplaceType.Copilot`
+4. `.claude-plugin/marketplace.json` → `MarketplaceType.Claude`
+
+### IPluginInstallService
+
+Orchestrates install and update workflows:
+
+- `installPlugin()` — checks marketplace trust, delegates to the appropriate source strategy to ensure files are locally available, and registers the plugin in installed storage.
+- `updatePlugin()` / `updateAllPlugins()` — pulls latest changes for cloned repositories and re-runs package-manager installs where applicable.
+
+### Plugin Source Strategies (IPluginSource)
+
+Each `PluginSourceKind` has a strategy that knows how to compute cache paths, provision files, update, and clean up:
+
+| Kind | Provisioning | Cache path |
+|------|-------------|------------|
+| `RelativePath` | No-op (lives inside marketplace repo) | `<cacheRoot>/github.com/<owner>/<repo>/<path>` |
+| `GitHub` | `git clone` / `git pull` | `<cacheRoot>/github.com/<owner>/<repo>[/ref_<ref>]` |
+| `GitUrl` | `git clone` / `git pull` | `<cacheRoot>/<host>/<path>[/ref_<ref>]` |
+| `Npm` | `npm install` in terminal | `<cacheRoot>/npm/<sanitized-package>/` |
+| `Pip` | `pip install` in terminal | `<cacheRoot>/pip/<package>/` |
+
+## Configuration & Storage Keys
+
+### Configuration
+| Key | Type | Default | Description |
+|-----|------|---------|-------------|
+| `chat.pluginsEnabled` | boolean | `true` | Master switch for the plugin system |
+| `chat.pluginLocations` | `Record<string, boolean>` | `{}` | Local plugin directories to discover |
+| `chat.pluginMarketplaces` | `string[]` | `[]` | Marketplace references to fetch from |
+
+### Storage (ApplicationScope, MachineTarget)
+| Key | Description |
+|-----|-------------|
+| `chat.plugins.installed.v1` | Installed marketplace plugins |
+| `chat.plugins.trustedMarketplaces.v1` | User-trusted marketplace canonical IDs |
+| `chat.plugins.lastFetchedPlugins.v2` | Last marketplace fetch results (persisted until next fetch) |
+| `chat.plugins.marketplaces.githubCache.v1` | GitHub API response cache (8 hour TTL) |
+| `chat.plugins.lastUpdateCheck.v1` | Timestamp of last periodic update check |
+
+### Enablement Storage
+| Key | Description |
+|-----|-------------|
+| `agentPlugins.enablement` | Per-plugin enable/disable state (shared `EnablementModel`) |
+
+## Reactivity Model
+
+The entire system is built on `IObservable`:
+
+1. **Configuration observables** (`observableConfigValue`) — push changes when settings are modified.
+2. **Discovery observables** — each `IAgentPluginDiscovery` exposes an `IObservable<readonly IAgentPlugin[]>` updated on filesystem changes.
+3. **Service-level derived** — `AgentPluginService.plugins` is a `derived()` that aggregates all discovery observables, dedupes by URI, and sorts.
+4. **Per-plugin observables** — each `IAgentPlugin` has observable properties for hooks, commands, skills, agents, and MCP definitions that update independently on file changes.
+5. **UI bindings** — views and editors use `autorun()` / `derived()` to reactively render plugin state.
+
+## Integration Points
+
+- **Chat prompts** — plugin hooks are contributed to the prompt system via the hook infrastructure.
+- **MCP servers** — plugins can define MCP server configurations (stdio or SSE) that are registered with the MCP platform.
+- **AI Customization UI** — the AI customization views aggregate plugin stats alongside MCP servers, prompts, and other customization surfaces.
+- **Extension API** — the plugin system is internal; there is no public `vscode` API surface for third-party access.
+
+## Key Design Patterns
+
+- **Strategy pattern** — format adapters (`IAgentPluginFormatAdapter`) and source strategies (`IPluginSource`) allow the system to support multiple plugin formats and installation mechanisms without coupling.
+- **Discovery registry** — `agentPluginDiscoveryRegistry` decouples discovery implementations from the core service via `SyncDescriptor0<IAgentPluginDiscovery>` registration.
+- **Disposable management** — plugin entries are tracked in a `Map` keyed by URI string, each with its own `DisposableStore` for file watchers. Removal or format changes dispose the store.
+- **Debounced refresh** — filesystem changes trigger a 200 ms `RunOnceScheduler` to batch rapid edits into a single re-read.
+- **Deduplication** — multiple discoveries may produce the same plugin URI; the service dedupes via `ResourceSet` and sorts by URI for stable ordering.
+- **Lazy instantiation** — the service is registered as `InstantiationType.Delayed` and only created on first injection.
diff --git a/src/vs/workbench/contrib/chat/common/plugins/agentPluginRepositoryService.ts b/src/vs/workbench/contrib/chat/common/plugins/agentPluginRepositoryService.ts
new file mode 100644
index 0000000000000..ea90fb6f832cb
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/plugins/agentPluginRepositoryService.ts
@@ -0,0 +1,116 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { URI } from '../../../../../base/common/uri.js';
+import { createDecorator } from '../../../../../platform/instantiation/common/instantiation.js';
+import { IMarketplacePlugin, IMarketplaceReference, IPluginSourceDescriptor, MarketplaceType, PluginSourceKind } from './pluginMarketplaceService.js';
+import { IPluginSource } from './pluginSource.js';
+
+export const IAgentPluginRepositoryService = createDecorator<IAgentPluginRepositoryService>('agentPluginRepositoryService');
+
+/**
+ * Options for ensuring a marketplace repository is available locally.
+ */
+export interface IEnsureRepositoryOptions {
+	/** Optional progress notification title shown during clone. */
+	readonly progressTitle?: string;
+	/** Label used in clone failure messaging. */
+	readonly failureLabel?: string;
+	/** Marketplace type metadata to persist in the marketplace index. */
+	readonly marketplaceType?: MarketplaceType;
+}
+
+/**
+ * Options for pulling the latest changes from a cloned marketplace repository.
+ */
+export interface IPullRepositoryOptions {
+	/** Optional plugin name used in progress messaging. */
+	readonly pluginName?: string;
+	/** Label used in pull failure messaging. */
+	readonly failureLabel?: string;
+	/** Marketplace type metadata for repository index updates. */
+	readonly marketplaceType?: MarketplaceType;
+	/** When `true`, suppresses progress notifications. */
+	readonly silent?: boolean;
+}
+
+/**
+ * Manages cloning, cache location resolution, and update operations for
+ * agent plugin marketplace repositories.
+ */
+export interface IAgentPluginRepositoryService {
+	readonly _serviceBrand: undefined;
+
+	/**
+	 * Returns the local cache URI for a marketplace repository reference.
+	 * Uses a storage-backed marketplace index when available.
+	 */
+	getRepositoryUri(marketplace: IMarketplaceReference, marketplaceType?: MarketplaceType): URI;
+
+	/**
+	 * Returns the local install URI for a plugin source directory inside its
+	 * marketplace repository cache.
+	 */
+	getPluginInstallUri(plugin: IMarketplacePlugin): URI;
+
+	/**
+	 * Ensures a marketplace repository is cloned locally and returns its cache URI.
+	 */
+	ensureRepository(marketplace: IMarketplaceReference, options?: IEnsureRepositoryOptions): Promise<URI>;
+
+	/**
+	 * Pulls latest changes for a cloned marketplace repository.
+	 * Returns `true` if the pull brought in new changes.
+	 */
+	pullRepository(marketplace: IMarketplaceReference, options?: IPullRepositoryOptions): Promise<boolean>;
+
+	/**
+	 * Returns the local install URI for a plugin based on its
+	 * {@link IPluginSourceDescriptor}. For non-relative-path sources
+	 * (github, url, npm, pip), this computes a cache location independent
+	 * of the marketplace repository.
+	 */
+	getPluginSourceInstallUri(sourceDescriptor: IPluginSourceDescriptor): URI;
+
+	/**
+	 * Ensures the plugin source is available locally. For github/url sources
+	 * this clones the repository into the cache. For npm/pip sources this is
+	 * a no-op (installation via terminal is handled by the install service).
+	 */
+	ensurePluginSource(plugin: IMarketplacePlugin, options?: IEnsureRepositoryOptions): Promise<URI>;
+
+	/**
+	 * Updates a plugin source that is stored outside the marketplace repository.
+	 * For github/url sources this pulls latest changes and reapplies pinned
+	 * ref/sha checkout. For npm/pip sources this is a no-op.
+	 * Returns `true` if the update brought in new changes.
+	 */
+	updatePluginSource(plugin: IMarketplacePlugin, options?: IPullRepositoryOptions): Promise<boolean>;
+
+	/**
+	 * Returns the {@link IPluginSource} strategy for the given
+	 * source kind, allowing callers to invoke kind-specific operations
+	 * (install, update, label, etc.) directly.
+	 */
+	getPluginSource(kind: PluginSourceKind): IPluginSource;
+
+	/**
+	 * Cleans up on-disk cache for a plugin source that owns its own install
+	 * directory. For marketplace-relative sources this is a no-op (they share
+	 * the marketplace repository cache). For direct sources (github, url, npm,
+	 * pip) the cache directory is deleted.
+	 *
+	 * This is best-effort: failures are logged but do not throw.
+	 */
+	cleanupPluginSource(plugin: IMarketplacePlugin): Promise<void>;
+
+	/**
+	 * Silently fetches remote refs for a cloned marketplace repository and
+	 * returns whether the local branch is behind the remote (i.e. updates
+	 * are available). Returns `false` if the repo is not cloned or on
+	 * network failure.
+	 */
+	fetchRepository(marketplace: IMarketplaceReference): Promise<boolean>;
+}
diff --git a/src/vs/workbench/contrib/chat/common/plugins/agentPluginService.ts b/src/vs/workbench/contrib/chat/common/plugins/agentPluginService.ts
index 1b413761b4b09..392d86f61399d 100644
--- a/src/vs/workbench/contrib/chat/common/plugins/agentPluginService.ts
+++ b/src/vs/workbench/contrib/chat/common/plugins/agentPluginService.ts
@@ -10,7 +10,9 @@ import { URI } from '../../../../../base/common/uri.js';
 import { SyncDescriptor0 } from '../../../../../platform/instantiation/common/descriptors.js';
 import { createDecorator } from '../../../../../platform/instantiation/common/instantiation.js';
 import { IMcpServerConfiguration } from '../../../../../platform/mcp/common/mcpPlatformTypes.js';
-import { HookType, IHookCommand } from '../promptSyntax/hookSchema.js';
+import { ContributionEnablementState, IEnablementModel } from '../enablement.js';
+import { IHookCommand } from '../promptSyntax/hookSchema.js';
+import { HookType } from '../promptSyntax/hookTypes.js';
 import { IMarketplacePlugin } from './pluginMarketplaceService.js';
 
 export const IAgentPluginService = createDecorator<IAgentPluginService>('agentPluginService');
@@ -31,6 +33,16 @@ export interface IAgentPluginSkill {
 	readonly name: string;
 }
 
+export interface IAgentPluginAgent {
+	readonly uri: URI;
+	readonly name: string;
+}
+
+export interface IAgentPluginInstruction {
+	readonly uri: URI;
+	readonly name: string;
+}
+
 export interface IAgentPluginMcpServerDefinition {
 	readonly name: string;
 	readonly configuration: IMcpServerConfiguration;
@@ -38,11 +50,16 @@ export interface IAgentPluginMcpServerDefinition {
 
 export interface IAgentPlugin {
 	readonly uri: URI;
-	readonly enabled: IObservable<boolean>;
-	setEnabled(enabled: boolean): void;
+	/** Human-readable display name for the plugin. */
+	readonly label: string;
+	readonly enablement: IObservable<ContributionEnablementState>;
+	/** Removes this plugin from its discovery source (config or installed storage). */
+	remove(): void;
 	readonly hooks: IObservable<readonly IAgentPluginHook[]>;
 	readonly commands: IObservable<readonly IAgentPluginCommand[]>;
 	readonly skills: IObservable<readonly IAgentPluginSkill[]>;
+	readonly agents: IObservable<readonly IAgentPluginAgent[]>;
+	readonly instructions: IObservable<readonly IAgentPluginInstruction[]>;
 	readonly mcpServerDefinitions: IObservable<readonly IAgentPluginMcpServerDefinition[]>;
 	/** Set when the plugin was installed from a marketplace repository. */
 	readonly fromMarketplace?: IMarketplacePlugin;
@@ -51,13 +68,12 @@ export interface IAgentPlugin {
 export interface IAgentPluginService {
 	readonly _serviceBrand: undefined;
 	readonly plugins: IObservable<readonly IAgentPlugin[]>;
-	readonly allPlugins: IObservable<readonly IAgentPlugin[]>;
-	setPluginEnabled(pluginUri: URI, enabled: boolean): void;
+	readonly enablementModel: IEnablementModel;
 }
 
 export interface IAgentPluginDiscovery extends IDisposable {
 	readonly plugins: IObservable<readonly IAgentPlugin[]>;
-	start(): void;
+	start(enablementModel: IEnablementModel): void;
 }
 
 export function getCanonicalPluginCommandId(plugin: IAgentPlugin, commandName: string): string {
diff --git a/src/vs/workbench/contrib/chat/common/plugins/agentPluginServiceImpl.ts b/src/vs/workbench/contrib/chat/common/plugins/agentPluginServiceImpl.ts
index 5385d796b40d0..8071a8fe44298 100644
--- a/src/vs/workbench/contrib/chat/common/plugins/agentPluginServiceImpl.ts
+++ b/src/vs/workbench/contrib/chat/common/plugins/agentPluginServiceImpl.ts
@@ -4,48 +4,59 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { RunOnceScheduler } from '../../../../../base/common/async.js';
-import { CancellationToken } from '../../../../../base/common/cancellation.js';
+import { Iterable } from '../../../../../base/common/iterator.js';
 import { parse as parseJSONC } from '../../../../../base/common/json.js';
+import { untildify } from '../../../../../base/common/labels.js';
 import { Disposable, DisposableStore } from '../../../../../base/common/lifecycle.js';
 import { ResourceSet } from '../../../../../base/common/map.js';
-import { autorun, derived, IObservable, ISettableObservable, observableValue } from '../../../../../base/common/observable.js';
+import { cloneAndChange, equals } from '../../../../../base/common/objects.js';
+import { autorun, derived, derivedOpts, IObservable, ObservablePromise, observableSignal, observableValue } from '../../../../../base/common/observable.js';
 import {
 	posix,
 	win32
 } from '../../../../../base/common/path.js';
 import {
 	basename,
-	extname, joinPath
+	extname, isEqualOrParent, joinPath, normalizePath
 } from '../../../../../base/common/resources.js';
+import { escapeRegExpCharacters } from '../../../../../base/common/strings.js';
+import { hasKey, Mutable } from '../../../../../base/common/types.js';
 import { URI } from '../../../../../base/common/uri.js';
-import { IConfigurationService, ConfigurationTarget, getConfigValueInTarget } from '../../../../../platform/configuration/common/configuration.js';
+import { ConfigurationTarget, getConfigValueInTarget, IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
 import { IFileService } from '../../../../../platform/files/common/files.js';
 import { IInstantiationService } from '../../../../../platform/instantiation/common/instantiation.js';
 import { ILogService } from '../../../../../platform/log/common/log.js';
-import { IMcpServerConfiguration, IMcpStdioServerConfiguration, McpServerType } from '../../../../../platform/mcp/common/mcpPlatformTypes.js';
+import { IMcpRemoteServerConfiguration, IMcpServerConfiguration, IMcpStdioServerConfiguration, McpServerType } from '../../../../../platform/mcp/common/mcpPlatformTypes.js';
 import { observableConfigValue } from '../../../../../platform/observable/common/platformObservableUtils.js';
+import { IStorageService } from '../../../../../platform/storage/common/storage.js';
 import { IWorkspaceContextService } from '../../../../../platform/workspace/common/workspace.js';
 import { IPathService } from '../../../../services/path/common/pathService.js';
 import { ChatConfiguration } from '../constants.js';
-import { parseCopilotHooks } from '../promptSyntax/hookCompatibility.js';
+import { EnablementModel, IEnablementModel } from '../enablement.js';
 import { parseClaudeHooks } from '../promptSyntax/hookClaudeCompat.js';
-import { agentPluginDiscoveryRegistry, IAgentPlugin, IAgentPluginCommand, IAgentPluginDiscovery, IAgentPluginHook, IAgentPluginMcpServerDefinition, IAgentPluginService, IAgentPluginSkill } from './agentPluginService.js';
-import { cloneAndChange } from '../../../../../base/common/objects.js';
-import { IPluginInstallService } from './pluginInstallService.js';
+import { parseCopilotHooks } from '../promptSyntax/hookCompatibility.js';
+import { IHookCommand } from '../promptSyntax/hookSchema.js';
+import { IAgentPluginRepositoryService } from './agentPluginRepositoryService.js';
+import { agentPluginDiscoveryRegistry, IAgentPlugin, IAgentPluginDiscovery, IAgentPluginHook, IAgentPluginInstruction, IAgentPluginMcpServerDefinition, IAgentPluginService, IAgentPluginSkill } from './agentPluginService.js';
 import { IMarketplacePlugin, IPluginMarketplaceService } from './pluginMarketplaceService.js';
 
 const COMMAND_FILE_SUFFIX = '.md';
 
+/** File suffixes accepted for rule/instruction files (longest first for correct name stripping). */
+const RULE_FILE_SUFFIXES = ['.instructions.md', '.mdc', '.md'];
+
 const enum AgentPluginFormat {
 	Copilot,
 	Claude,
+	OpenPlugin,
 }
 
 interface IAgentPluginFormatAdapter {
 	readonly format: AgentPluginFormat;
-	readonly manifestPaths: readonly string[];
-	readonly hookConfigPaths: readonly string[];
-	readonly hookWatchPaths: readonly string[];
+	readonly manifestPath: string;
+	readonly hookConfigPath: string;
+	readonly pluginRootToken: string | undefined;
+	readonly pluginRootEnvVar: string | undefined;
 	parseHooks(json: unknown, pluginUri: URI, userHome: string): IAgentPluginHook[];
 }
 
@@ -53,71 +64,331 @@ function mapParsedHooks(parsed: Map<IAgentPluginHook['type'], { hooks: IAgentPlu
 	return [...parsed.entries()].map(([type, { hooks, originalId }]) => ({ type, hooks, originalId }));
 }
 
-const copilotPluginFormatAdapter: IAgentPluginFormatAdapter = {
-	format: AgentPluginFormat.Copilot,
-	manifestPaths: ['plugin.json'],
-	hookConfigPaths: ['hooks.json'],
-	hookWatchPaths: ['hooks.json'],
-	parseHooks: (json, pluginUri, userHome) => mapParsedHooks(parseCopilotHooks(json, pluginUri, userHome)),
-};
-
-const claudePluginFormatAdapter: IAgentPluginFormatAdapter = {
-	format: AgentPluginFormat.Claude,
-	manifestPaths: ['.claude-plugin/plugin.json'],
-	hookConfigPaths: ['hooks/hooks.json'],
-	hookWatchPaths: ['hooks'],
-	parseHooks: (json, pluginUri, userHome) => {
-		const replacer = (v: unknown): unknown => {
-			return typeof v === 'string'
-				? v.replaceAll('${CLAUDE_PLUGIN_ROOT}', pluginUri.fsPath)
-				: undefined;
-		};
+/**
+ * Resolves the workspace folder that contains the plugin URI for cwd resolution,
+ * falling back to the first workspace folder for plugins outside the workspace.
+ */
+function resolveWorkspaceRoot(pluginUri: URI, workspaceContextService: IWorkspaceContextService): URI | undefined {
+	const defaultFolder = workspaceContextService.getWorkspace().folders[0];
+	const folder = workspaceContextService.getWorkspaceFolder(pluginUri) ?? defaultFolder;
+	return folder?.uri;
+}
 
-		const { hooks, disabledAllHooks } = parseClaudeHooks(cloneAndChange(json, replacer), pluginUri, userHome);
-		if (disabledAllHooks) {
-			return [];
+class CopilotPluginFormatAdapter implements IAgentPluginFormatAdapter {
+	readonly format = AgentPluginFormat.Copilot;
+	readonly manifestPath = 'plugin.json';
+	readonly hookConfigPath = 'hooks.json';
+	readonly pluginRootToken = undefined;
+	readonly pluginRootEnvVar = undefined;
+
+	constructor(
+		@IWorkspaceContextService private readonly _workspaceContextService: IWorkspaceContextService,
+	) { }
+
+	parseHooks(json: unknown, pluginUri: URI, userHome: string): IAgentPluginHook[] {
+		const workspaceRoot = resolveWorkspaceRoot(pluginUri, this._workspaceContextService);
+		return mapParsedHooks(parseCopilotHooks(json, workspaceRoot, userHome));
+	}
+}
+
+/**
+ * Characters in a file path that require shell quoting to prevent
+ * word splitting or interpretation by common shells (bash, zsh, cmd, PowerShell).
+ */
+const shellUnsafeChars = /[\s&|<>()^;!`"']/;
+
+/**
+ * Replaces `${CLAUDE_PLUGIN_ROOT}` in a shell command string with the
+ * given fsPath. If the path contains characters that would break shell
+ * parsing (e.g. spaces), occurrences are wrapped in double-quotes.
+ *
+ * The token may be followed by additional path segments like
+ * `${CLAUDE_PLUGIN_ROOT}/scripts/run.sh`; the entire resulting path
+ * (including suffix) is quoted as one unit.
+ *
+ */
+export function shellQuotePluginRootInCommand(command: string, fsPath: string, token: string) {
+	if (!command.includes(token)) {
+		return command;
+	}
+
+	if (!shellUnsafeChars.test(fsPath)) {
+		// Path is shell-safe; plain replacement is fine.
+		return command.replaceAll(token, fsPath);
+	}
+
+	// Replace each token occurrence (plus any trailing path chars that form
+	// a single filesystem argument) with a properly double-quoted expansion.
+	const escapedToken = escapeRegExpCharacters(token);
+	const pattern = new RegExp(
+		// Capture an optional leading quote so we know if it's already quoted
+		`(["']?)` + escapedToken + `([\\w./\\\\~:-]*)`,
+		'g',
+	);
+
+	return command.replace(pattern, (_match, leadingQuote: string, suffix: string) => {
+		const fullPath = fsPath + suffix;
+		if (leadingQuote) {
+			// Already inside quotes — don't add more, just expand.
+			return leadingQuote + fullPath;
+		}
+		// Wrap in double quotes, escaping any embedded double-quote chars.
+		return '"' + fullPath.replace(/"/g, '\\"') + '"';
+	});
+}
+
+/**
+ * Replaces `${token}` references in MCP server definition string fields
+ * (command, args, cwd, env values, url, envFile, headers) with the plugin
+ * root filesystem path. No shell quoting is needed because args are already
+ * a string array.
+ */
+function interpolateMcpPluginRoot(
+	def: IAgentPluginMcpServerDefinition,
+	fsPath: string,
+	token: string,
+	envVar: string,
+): IAgentPluginMcpServerDefinition {
+	const replace = (s: string) => s.replaceAll(token, fsPath);
+
+	const config = def.configuration;
+	let interpolated: IMcpServerConfiguration;
+
+	if (config.type === McpServerType.LOCAL) {
+		const local: Mutable<IMcpStdioServerConfiguration> = { ...config };
+		local.command = replace(local.command);
+		if (local.args) {
+			local.args = local.args.map(replace);
+		}
+		if (local.cwd) {
+			local.cwd = replace(local.cwd);
+		}
+		local.env = { ...local.env };
+		for (const [k, v] of Object.entries(local.env)) {
+			if (typeof v === 'string') {
+				local.env[k] = replace(v);
+			}
+		}
+		local.env[envVar] = fsPath;
+		if (local.envFile) {
+			local.envFile = replace(local.envFile);
+		}
+		interpolated = local;
+	} else {
+		const remote: Mutable<IMcpRemoteServerConfiguration> = { ...config };
+		remote.url = replace(remote.url);
+		if (remote.headers) {
+			remote.headers = Object.fromEntries(
+				Object.entries(remote.headers).map(([k, v]) => [k, replace(v)])
+			);
+		}
+		interpolated = remote;
+	}
+
+	return { name: def.name, configuration: interpolated };
+}
+
+/**
+ * Shared hook-parsing logic for plugin formats that use the Claude/open-plugin
+ * hook schema. Replaces `${token}` references in hook commands with the plugin
+ * root path (shell-quoted when necessary), injects an environment variable, and
+ * delegates to {@link parseClaudeHooks} for the actual hook resolution.
+ */
+function parsePluginRootHooks(
+	json: unknown,
+	pluginUri: URI,
+	userHome: string,
+	workspaceContextService: IWorkspaceContextService,
+	token: string,
+	envVar: string,
+): IAgentPluginHook[] {
+	const fsPath = pluginUri.fsPath;
+	const typedJson = json as { hooks?: Record<string, unknown[]> };
+
+	const mutateHookCommand = (hook: Mutable<IHookCommand>): void => {
+		for (const field of ['command', 'windows', 'linux', 'osx'] as const) {
+			if (typeof hook[field] === 'string') {
+				hook[field] = shellQuotePluginRootInCommand(hook[field], fsPath, token);
+			}
+		}
+
+		hook.env ??= {};
+		hook.env[envVar] = fsPath;
+	};
+
+	for (const lifecycle of Object.values(typedJson.hooks ?? {})) {
+		if (!Array.isArray(lifecycle)) {
+			continue;
+		}
+
+		for (const lifecycleEntry of lifecycle) {
+			if (!lifecycleEntry || typeof lifecycleEntry !== 'object') {
+				continue;
+			}
+
+			const entry = lifecycleEntry as { hooks?: Mutable<IHookCommand>[] } & Mutable<IHookCommand>;
+			if (Array.isArray(entry.hooks)) {
+				for (const hook of entry.hooks) {
+					mutateHookCommand(hook);
+				}
+			} else {
+				mutateHookCommand(entry);
+			}
+		}
+	}
+
+	const replacer = (v: unknown): unknown => {
+		return typeof v === 'string'
+			? v.replaceAll(token, pluginUri.fsPath)
+			: undefined;
+	};
+
+	const workspaceRoot = resolveWorkspaceRoot(pluginUri, workspaceContextService);
+	const { hooks, disabledAllHooks } = parseClaudeHooks(cloneAndChange(json, replacer), workspaceRoot, userHome);
+	if (disabledAllHooks) {
+		return [];
+	}
+
+	return mapParsedHooks(hooks);
+}
+
+class ClaudePluginFormatAdapter implements IAgentPluginFormatAdapter {
+	readonly format = AgentPluginFormat.Claude;
+	readonly manifestPath = '.claude-plugin/plugin.json';
+	readonly hookConfigPath = 'hooks/hooks.json';
+	readonly pluginRootToken = '${CLAUDE_PLUGIN_ROOT}';
+	readonly pluginRootEnvVar = 'CLAUDE_PLUGIN_ROOT';
+
+	constructor(
+		@IWorkspaceContextService private readonly _workspaceContextService: IWorkspaceContextService,
+	) { }
+
+	parseHooks(json: unknown, pluginUri: URI, userHome: string): IAgentPluginHook[] {
+		return parsePluginRootHooks(json, pluginUri, userHome, this._workspaceContextService, '${CLAUDE_PLUGIN_ROOT}', 'CLAUDE_PLUGIN_ROOT');
+	}
+}
+
+class OpenPluginFormatAdapter implements IAgentPluginFormatAdapter {
+	readonly format = AgentPluginFormat.OpenPlugin;
+	readonly manifestPath = '.plugin/plugin.json';
+	readonly hookConfigPath = 'hooks/hooks.json';
+	readonly pluginRootToken = '${PLUGIN_ROOT}';
+	readonly pluginRootEnvVar = 'PLUGIN_ROOT';
+
+	constructor(
+		@IWorkspaceContextService private readonly _workspaceContextService: IWorkspaceContextService,
+	) { }
+
+	parseHooks(json: unknown, pluginUri: URI, userHome: string): IAgentPluginHook[] {
+		return parsePluginRootHooks(json, pluginUri, userHome, this._workspaceContextService, '${PLUGIN_ROOT}', 'PLUGIN_ROOT');
+	}
+}
+
+interface IComponentPathConfig {
+	readonly paths: readonly string[];
+	readonly exclusive: boolean;
+}
+
+const emptyComponentPathConfig: IComponentPathConfig = { paths: [], exclusive: false };
+
+/**
+ * Parses a manifest component path field (e.g. `commands`, `skills`, `agents`)
+ * into a normalized config. Supports:
+ * - `undefined` → empty supplemental config
+ * - `string` → single supplemental path
+ * - `string[]` → multiple supplemental paths
+ * - `{ paths: string[], exclusive?: boolean }` → as-is
+ *
+ * Paths that resolve outside the plugin root are silently dropped
+ * in {@link resolveComponentDirs}.
+ */
+function parseComponentPathConfig(raw: unknown): IComponentPathConfig {
+	if (raw === undefined || raw === null) {
+		return emptyComponentPathConfig;
+	}
+
+	if (typeof raw === 'string') {
+		const trimmed = raw.trim();
+		return trimmed ? { paths: [trimmed], exclusive: false } : emptyComponentPathConfig;
+	}
+
+	if (Array.isArray(raw)) {
+		const paths = raw
+			.filter(v => typeof v === 'string')
+			.map(v => v.trim())
+			.filter(v => v.length > 0);
+		return { paths, exclusive: false };
+	}
+
+	if (typeof raw === 'object') {
+		const obj = raw as Record<string, unknown>;
+		if (Array.isArray(obj['paths'])) {
+			const paths = (obj['paths'] as unknown[])
+				.filter(v => typeof v === 'string')
+				.map(v => v.trim())
+				.filter(v => v.length > 0);
+			const exclusive = obj['exclusive'] === true;
+			return { paths, exclusive };
 		}
+	}
 
-		return mapParsedHooks(hooks);
-	},
-};
+	return emptyComponentPathConfig;
+}
+
+/**
+ * Resolves the directories to scan for a given component type, combining
+ * the default directory with any custom paths from the manifest config.
+ * Paths that resolve outside the plugin root are silently ignored.
+ */
+function resolveComponentDirs(pluginUri: URI, defaultDir: string, config: IComponentPathConfig): readonly URI[] {
+	const dirs: URI[] = [];
+	if (!config.exclusive) {
+		dirs.push(joinPath(pluginUri, defaultDir));
+	}
+	for (const p of config.paths) {
+		const resolved = normalizePath(joinPath(pluginUri, p));
+		if (isEqualOrParent(resolved, pluginUri)) {
+			dirs.push(resolved);
+		}
+	}
+	return dirs;
+}
 
 export class AgentPluginService extends Disposable implements IAgentPluginService {
 
 	declare readonly _serviceBrand: undefined;
 
-	public readonly allPlugins: IObservable<readonly IAgentPlugin[]>;
 	public readonly plugins: IObservable<readonly IAgentPlugin[]>;
+	public readonly enablementModel: IEnablementModel;
 
 	constructor(
 		@IInstantiationService instantiationService: IInstantiationService,
+		@IConfigurationService configurationService: IConfigurationService,
+		@IStorageService storageService: IStorageService,
 	) {
 		super();
 
+		this.enablementModel = this._register(new EnablementModel('agentPlugins.enablement', storageService));
+
+		const pluginsEnabled = observableConfigValue(ChatConfiguration.PluginsEnabled, true, configurationService);
+
 		const discoveries: IAgentPluginDiscovery[] = [];
 		for (const descriptor of agentPluginDiscoveryRegistry.getAll()) {
 			const discovery = instantiationService.createInstance(descriptor);
 			this._register(discovery);
 			discoveries.push(discovery);
-			discovery.start();
+			discovery.start(this.enablementModel);
 		}
 
 
-		this.allPlugins = derived(read => this._dedupeAndSort(discoveries.flatMap(d => d.plugins.read(read))));
-
-		this.plugins = derived(reader => {
-			const all = this.allPlugins.read(reader);
-			return all.filter(p => p.enabled.read(reader));
+		this.plugins = derived(read => {
+			if (!pluginsEnabled.read(read)) {
+				return [];
+			}
+			return this._dedupeAndSort(discoveries.flatMap(d => d.plugins.read(read)));
 		});
 	}
 
-	public setPluginEnabled(pluginUri: URI, enabled: boolean): void {
-		const plugin = this.allPlugins.get().find(p => p.uri.toString() === pluginUri.toString());
-		if (plugin) {
-			plugin.setEnabled(enabled);
-		}
-	}
-
 	private _dedupeAndSort(plugins: readonly IAgentPlugin[]): readonly IAgentPlugin[] {
 		const unique: IAgentPlugin[] = [];
 		const seen = new ResourceSet();
@@ -136,43 +407,51 @@ export class AgentPluginService extends Disposable implements IAgentPluginServic
 	}
 }
 
-type PluginEntry = IAgentPlugin & { enabled: ISettableObservable<boolean> };
+type PluginEntry = IAgentPlugin;
+
+/**
+ * Describes a single discovered plugin source, before the shared
+ * infrastructure builds the full {@link IAgentPlugin} from it.
+ */
+interface IPluginSource {
+	readonly uri: URI;
+	readonly fromMarketplace: IMarketplacePlugin | undefined;
+	/** Called when remove is invoked on the plugin */
+	remove(): void;
+}
 
-export class ConfiguredAgentPluginDiscovery extends Disposable implements IAgentPluginDiscovery {
+/**
+ * Shared base class for plugin discovery implementations. Contains the common
+ * logic for reading plugin contents (commands, skills, agents, hooks, MCP server
+ * definitions) from the filesystem and watching for live updates.
+ *
+ * Subclasses implement {@link _discoverPluginSources} to determine *which*
+ * plugins exist, while this class handles the rest.
+ */
+export abstract class AbstractAgentPluginDiscovery extends Disposable implements IAgentPluginDiscovery {
 
-	private readonly _pluginPathsConfig: IObservable<Record<string, boolean>>;
 	private readonly _pluginEntries = new Map<string, { plugin: PluginEntry; store: DisposableStore; adapter: IAgentPluginFormatAdapter }>();
 
 	private readonly _plugins = observableValue<readonly IAgentPlugin[]>('discoveredAgentPlugins', []);
 	public readonly plugins: IObservable<readonly IAgentPlugin[]> = this._plugins;
 
 	private _discoverVersion = 0;
+	protected _enablementModel!: IEnablementModel;
 
 	constructor(
-		@IConfigurationService private readonly _configurationService: IConfigurationService,
-		@IFileService private readonly _fileService: IFileService,
-		@IPluginInstallService private readonly _pluginInstallService: IPluginInstallService,
-		@IPluginMarketplaceService private readonly _pluginMarketplaceService: IPluginMarketplaceService,
-		@IWorkspaceContextService private readonly _workspaceContextService: IWorkspaceContextService,
-		@IPathService private readonly _pathService: IPathService,
-		@ILogService private readonly _logService: ILogService,
+		protected readonly _fileService: IFileService,
+		protected readonly _pathService: IPathService,
+		protected readonly _logService: ILogService,
+		protected readonly _instantiationService: IInstantiationService,
 	) {
 		super();
-		this._pluginPathsConfig = observableConfigValue<Record<string, boolean>>(ChatConfiguration.PluginPaths, {}, _configurationService);
 	}
 
-	public start(): void {
-		const scheduler = this._register(new RunOnceScheduler(() => this._refreshPlugins(), 0));
-		this._register(autorun(reader => {
-			this._pluginPathsConfig.read(reader);
-			scheduler.schedule();
-		}));
-		scheduler.schedule();
-	}
+	public abstract start(enablementModel: IEnablementModel): void;
 
-	private async _refreshPlugins(): Promise<void> {
+	protected async _refreshPlugins(): Promise<void> {
 		const version = ++this._discoverVersion;
-		const plugins = await this._discoverPlugins();
+		const plugins = await this._discoverAndBuildPlugins();
 		if (version !== this._discoverVersion || this._store.isDisposed) {
 			return;
 		}
@@ -180,39 +459,20 @@ export class ConfiguredAgentPluginDiscovery extends Disposable implements IAgent
 		this._plugins.set(plugins, undefined);
 	}
 
-	private async _discoverPlugins(): Promise<readonly IAgentPlugin[]> {
+	/** Subclasses return plugin sources to discover. */
+	protected abstract _discoverPluginSources(): Promise<readonly IPluginSource[]>;
+
+	private async _discoverAndBuildPlugins(): Promise<readonly IAgentPlugin[]> {
+		const sources = await this._discoverPluginSources();
 		const plugins: IAgentPlugin[] = [];
 		const seenPluginUris = new Set<string>();
-		const config = this._pluginPathsConfig.get();
-		// todo: temporary, we should have a dedicated discovery from the marketplace
-		const marketplacePluginsByInstallUri = await this._getMarketplacePluginsByInstallUri();
-
-		for (const [path, enabled] of Object.entries(config)) {
-			if (!path.trim()) {
-				continue;
-			}
 
-			const resources = this._resolvePluginPath(path.trim());
-			for (const resource of resources) {
-				let stat;
-				try {
-					stat = await this._fileService.resolve(resource);
-				} catch {
-					this._logService.debug(`[ConfiguredAgentPluginDiscovery] Could not resolve plugin path: ${resource.toString()}`);
-					continue;
-				}
-
-				if (!stat.isDirectory) {
-					this._logService.debug(`[ConfiguredAgentPluginDiscovery] Plugin path is not a directory: ${resource.toString()}`);
-					continue;
-				}
-
-				const key = stat.resource.toString();
-				if (!seenPluginUris.has(key)) {
-					const adapter = await this._detectPluginFormatAdapter(stat.resource);
-					seenPluginUris.add(key);
-					plugins.push(this._toPlugin(stat.resource, path, enabled, adapter, marketplacePluginsByInstallUri.get(key)));
-				}
+		for (const source of sources) {
+			const key = source.uri.toString();
+			if (!seenPluginUris.has(key)) {
+				seenPluginUris.add(key);
+				const adapter = await this._detectPluginFormatAdapter(source.uri);
+				plugins.push(this._toPlugin(source.uri, adapter, source.fromMarketplace, () => source.remove()));
 			}
 		}
 
@@ -222,86 +482,20 @@ export class ConfiguredAgentPluginDiscovery extends Disposable implements IAgent
 		return plugins;
 	}
 
-	private async _getMarketplacePluginsByInstallUri(): Promise<Map<string, IMarketplacePlugin>> {
-		const result = new Map<string, IMarketplacePlugin>();
-		let marketplacePlugins: readonly IMarketplacePlugin[];
-		try {
-			marketplacePlugins = await this._pluginMarketplaceService.fetchMarketplacePlugins(CancellationToken.None);
-		} catch (err) {
-			this._logService.debug('[ConfiguredAgentPluginDiscovery] Failed to fetch marketplace plugins for provenance mapping:', err);
-			return result;
-		}
-
-		for (const marketplacePlugin of marketplacePlugins) {
-			const installUri = this._pluginInstallService.getPluginInstallUri(marketplacePlugin);
-			result.set(installUri.toString(), marketplacePlugin);
-		}
-
-		return result;
-	}
-
-	/**
-	 * Resolves a plugin path to one or more resource URIs. Absolute paths are
-	 * used directly; relative paths are resolved against each workspace folder.
-	 */
-	private _resolvePluginPath(path: string): URI[] {
-		if (win32.isAbsolute(path) || posix.isAbsolute(path)) {
-			return [URI.file(path)];
-		}
-
-		return this._workspaceContextService.getWorkspace().folders.map(
-			folder => joinPath(folder.uri, path)
-		);
-	}
-
-	/**
-	 * Updates the enabled state of a plugin path in the configuration,
-	 * writing to the most specific config target where the key is defined.
-	 */
-	private _updatePluginPathEnabled(configKey: string, value: boolean): void {
-		const inspected = this._configurationService.inspect<Record<string, boolean>>(ChatConfiguration.PluginPaths);
-
-		// Walk from most specific to least specific to find where this key is defined
-		const targets = [
-			ConfigurationTarget.WORKSPACE_FOLDER,
-			ConfigurationTarget.WORKSPACE,
-			ConfigurationTarget.USER_LOCAL,
-			ConfigurationTarget.USER_REMOTE,
-			ConfigurationTarget.USER,
-			ConfigurationTarget.APPLICATION,
-		];
-
-		for (const target of targets) {
-			const mapping = getConfigValueInTarget(inspected, target);
-			if (mapping && Object.prototype.hasOwnProperty.call(mapping, configKey)) {
-				this._configurationService.updateValue(
-					ChatConfiguration.PluginPaths,
-					{ ...mapping, [configKey]: value },
-					target,
-				);
-				return;
-			}
+	private async _detectPluginFormatAdapter(pluginUri: URI): Promise<IAgentPluginFormatAdapter> {
+		if (await this._pathExists(joinPath(pluginUri, '.plugin', 'plugin.json'))) {
+			return this._instantiationService.createInstance(OpenPluginFormatAdapter);
 		}
 
-		// Key not found in any target; write to USER_LOCAL as default
-		const current = getConfigValueInTarget(inspected, ConfigurationTarget.USER_LOCAL) ?? {};
-		this._configurationService.updateValue(
-			ChatConfiguration.PluginPaths,
-			{ ...current, [configKey]: value },
-			ConfigurationTarget.USER_LOCAL,
-		);
-	}
-
-	private async _detectPluginFormatAdapter(pluginUri: URI): Promise<IAgentPluginFormatAdapter> {
 		const isInClaudeDirectory = pluginUri.path.split('/').includes('.claude');
 		if (isInClaudeDirectory || await this._pathExists(joinPath(pluginUri, '.claude-plugin', 'plugin.json'))) {
-			return claudePluginFormatAdapter;
+			return this._instantiationService.createInstance(ClaudePluginFormatAdapter);
 		}
 
-		return copilotPluginFormatAdapter;
+		return this._instantiationService.createInstance(CopilotPluginFormatAdapter);
 	}
 
-	private async _pathExists(resource: URI): Promise<boolean> {
+	protected async _pathExists(resource: URI): Promise<boolean> {
 		try {
 			await this._fileService.resolve(resource);
 			return true;
@@ -310,7 +504,7 @@ export class ConfiguredAgentPluginDiscovery extends Disposable implements IAgent
 		}
 	}
 
-	private _toPlugin(uri: URI, configKey: string, initialEnabled: boolean, adapter: IAgentPluginFormatAdapter, fromMarketplace: IMarketplacePlugin | undefined): IAgentPlugin {
+	private _toPlugin(uri: URI, adapter: IAgentPluginFormatAdapter, fromMarketplace: IMarketplacePlugin | undefined, removeCallback: () => void): IAgentPlugin {
 		const key = uri.toString();
 		const existing = this._pluginEntries.get(key);
 		if (existing) {
@@ -318,65 +512,107 @@ export class ConfiguredAgentPluginDiscovery extends Disposable implements IAgent
 				existing.store.dispose();
 				this._pluginEntries.delete(key);
 			} else {
-				existing.plugin.enabled.set(initialEnabled, undefined);
 				return existing.plugin;
 			}
 		}
 
 		const store = new DisposableStore();
-		const commands = observableValue<readonly IAgentPluginCommand[]>('agentPluginCommands', []);
-		const skills = observableValue<readonly IAgentPluginSkill[]>('agentPluginSkills', []);
-		const hooks = observableValue<readonly IAgentPluginHook[]>('agentPluginHooks', []);
-		const mcpServerDefinitions = observableValue<readonly IAgentPluginMcpServerDefinition[]>('agentPluginMcpServerDefinitions', []);
-		const enabled = observableValue<boolean>('agentPluginEnabled', initialEnabled);
-
-		const commandsDir = joinPath(uri, 'commands');
-		const skillsDir = joinPath(uri, 'skills');
-
-		const commandsScheduler = store.add(new RunOnceScheduler(async () => {
-			commands.set(await this._readCommands(uri), undefined);
-		}, 200));
-		const skillsScheduler = store.add(new RunOnceScheduler(async () => {
-			skills.set(await this._readSkills(uri), undefined);
-		}, 200));
-		const hooksScheduler = store.add(new RunOnceScheduler(async () => {
-			hooks.set(await this._readHooks(uri, adapter), undefined);
-		}, 200));
-		const mcpScheduler = store.add(new RunOnceScheduler(async () => {
-			mcpServerDefinitions.set(await this._readMcpDefinitions(uri, adapter), undefined);
-		}, 200));
-
-		store.add(this._fileService.watch(uri, { recursive: true, excludes: [] }));
-		store.add(this._fileService.onDidFilesChange(e => {
-			if (e.affects(commandsDir)) {
-				commandsScheduler.schedule();
-			}
-			if (e.affects(skillsDir)) {
-				skillsScheduler.schedule();
-			}
-			if (adapter.hookWatchPaths.some(path => e.affects(joinPath(uri, path)))) {
-				hooksScheduler.schedule();
-			}
-			if (e.affects(joinPath(uri, '.mcp.json')) || adapter.manifestPaths.some(path => e.affects(joinPath(uri, path)))) {
-				mcpScheduler.schedule();
-				hooksScheduler.schedule();
-			}
-		}));
+		const enablement = derived(r => this._enablementModel.readEnabled(key, r));
+
+		// Track current component directories for the file watcher. These are
+		// updated whenever the manifest is read (inside each component reader).
+		const manifest = observableValue<Record<string, unknown> | undefined>('agentPluginManifest', undefined);
+
+		const observeComponent = <T>(
+			prop: string,
+			doRead: (uris: readonly URI[]) => Promise<readonly T[]>,
+			tryReadEmbedded?: (section: unknown) => Promise<T[] | undefined>,
+			defaultPath = prop,
+		): IObservable<readonly T[]> => {
+			const secondObs = derivedOpts({ equalsFn: equals }, reader => manifest.read(reader)?.[prop]);
+
+			const wrapped = derived(reader => {
+				const section = secondObs.read(reader);
+				if (tryReadEmbedded) {
+					if (section && typeof section === 'object' && !Array.isArray(section) && !(hasKey(section, { paths: true }))) {
+						return { kind: 'const', data: new ObservablePromise(tryReadEmbedded(section)) } as const;
+					}
+				}
+
+				const paths = parseComponentPathConfig(section);
+				const dirs = resolveComponentDirs(uri, defaultPath, paths);
+				for (const d of dirs) {
+					const watcher = this._fileService.createWatcher(d, { recursive: false, excludes: [] });
+					reader.store.add(watcher);
+					reader.store.add(watcher.onDidChange(() => changeTrigger.trigger(undefined)));
+				}
+
+				return { kind: 'dirs', dirs: dirs } as const;
+			});
+
+			const changeTrigger = observableSignal('fileChange');
+
+			const promised = derived(reader => {
+				const w = wrapped.read(reader);
+				if (w.kind === 'const') {
+					return w.data.promiseResult;
+				} else {
+					changeTrigger.read(reader); // re-run when a relevant file change occurs
+					const promise = new ObservablePromise(doRead(w.dirs));
+					return promise.promiseResult;
+				}
+			});
+
+			const result = promised.map((w, r) => w.read(r)?.data ?? Iterable.empty());
+
+			return result.recomputeInitiallyAndOnChange(store);
+		};
+
+		const commands = observeComponent('commands', d => this._readMarkdownComponents(d));
+		const skills = observeComponent('skills', d => this._readSkills(uri, d));
+		const agents = observeComponent('agents', d => this._readMarkdownComponents(d));
+		const instructions = observeComponent('rules', d => this._readRules(d));
+		const hooks = observeComponent(
+			'hooks',
+			paths => this._readHooksFromPaths(uri, paths, adapter),
+			async section => {
+				const userHome = (await this._pathService.userHome()).fsPath;
+				return adapter.parseHooks(section, uri, userHome);
+			},
+			adapter.hookConfigPath,
+		);
 
-		commandsScheduler.schedule();
-		skillsScheduler.schedule();
-		hooksScheduler.schedule();
-		mcpScheduler.schedule();
+		const mcpServerDefinitions = observeComponent(
+			'mcpServers',
+			paths => this._readMcpDefinitionsFromPaths(paths, uri.fsPath, adapter),
+			async section => this._parseMcpServerDefinitionMap({ mcpServers: section }, uri.fsPath, adapter),
+			'.mcp.json',
+		);
+
+		// Read the manifest initially and re-read whenever manifest files change.
+		const readManifest = async () => {
+			manifest.set(await this._readManifest(uri, adapter), undefined);
+		};
+
+		const manifestWatcher = this._fileService.createWatcher(
+			joinPath(uri, adapter.manifestPath),
+			{ recursive: false, excludes: [] },
+		);
+		store.add(manifestWatcher);
+		store.add(manifestWatcher.onDidChange(() => readManifest()));
+
+		readManifest();
 
 		const plugin: PluginEntry = {
 			uri,
-			enabled,
-			setEnabled: (value: boolean) => {
-				this._updatePluginPathEnabled(configKey, value);
-			},
+			label: fromMarketplace?.name ?? basename(uri),
+			enablement,
+			remove: removeCallback,
 			hooks,
 			commands,
 			skills,
+			agents,
+			instructions,
 			mcpServerDefinitions,
 			fromMarketplace,
 		};
@@ -386,62 +622,71 @@ export class ConfiguredAgentPluginDiscovery extends Disposable implements IAgent
 		return plugin;
 	}
 
-	private async _readMcpDefinitions(pluginUri: URI, adapter: IAgentPluginFormatAdapter): Promise<readonly IAgentPluginMcpServerDefinition[]> {
-		const mcpUri = joinPath(pluginUri, '.mcp.json');
-
-		const mcpFileConfig = await this._readJsonFile(mcpUri);
-		const fileDefinitions = this._parseMcpServerDefinitionMap(mcpFileConfig);
-
-		const pluginJsonDefinitions = await this._readInlinePluginJsonMcpDefinitions(pluginUri, adapter);
-
-		const merged = new Map<string, IMcpServerConfiguration>();
-		for (const definition of fileDefinitions) {
-			merged.set(definition.name, definition.configuration);
-		}
-		for (const definition of pluginJsonDefinitions) {
-			if (!merged.has(definition.name)) {
-				merged.set(definition.name, definition.configuration);
-			}
+	private async _readManifest(pluginUri: URI, adapter: IAgentPluginFormatAdapter): Promise<Record<string, unknown> | undefined> {
+		const json = await this._readJsonFile(joinPath(pluginUri, adapter.manifestPath));
+		if (json && typeof json === 'object') {
+			return json as Record<string, unknown>;
 		}
-
-		const definitions = [...merged.entries()]
-			.map(([name, configuration]) => ({ name, configuration } satisfies IAgentPluginMcpServerDefinition))
-			.sort((a, b) => a.name.localeCompare(b.name));
-
-		return definitions;
+		return undefined;
 	}
 
-	private async _readInlinePluginJsonMcpDefinitions(pluginUri: URI, adapter: IAgentPluginFormatAdapter): Promise<readonly IAgentPluginMcpServerDefinition[]> {
-		for (const manifestPath of adapter.manifestPaths.map(path => joinPath(pluginUri, path))) {
-			const manifest = await this._readJsonFile(manifestPath);
-			if (!manifest || typeof manifest !== 'object') {
-				continue;
+	/**
+	 * Reads hook definitions from a list of resolved paths (JSON files).
+	 * Each path is tried in order; the first one that contains valid hook
+	 * JSON is used.
+	 */
+	private async _readHooksFromPaths(pluginUri: URI, paths: readonly URI[], adapter: IAgentPluginFormatAdapter): Promise<readonly IAgentPluginHook[]> {
+		const userHome = (await this._pathService.userHome()).fsPath;
+		for (const hookPath of paths) {
+			const json = await this._readJsonFile(hookPath);
+			if (json) {
+				try {
+					return adapter.parseHooks(json, pluginUri, userHome);
+				} catch (e) {
+					this._logService.info(`[AgentPluginDiscovery] Failed to parse hooks from ${hookPath.toString()}:`, e);
+				}
 			}
+		}
+		return [];
+	}
 
-			const manifestRecord = manifest as Record<string, unknown>;
-			const mcpServers = manifestRecord['mcpServers'];
-			const definitions = this._parseMcpServerDefinitionMap(mcpServers);
-			if (definitions.length > 0) {
-				return definitions;
+	/**
+	 * Reads MCP server definitions from a list of resolved paths (JSON files).
+	 * Definitions from all files are merged; the first definition for a given
+	 * server name wins.
+	 */
+	private async _readMcpDefinitionsFromPaths(paths: readonly URI[], pluginFsPath: string, adapter: IAgentPluginFormatAdapter): Promise<readonly IAgentPluginMcpServerDefinition[]> {
+		const merged = new Map<string, IMcpServerConfiguration>();
+		for (const mcpPath of paths) {
+			const json = await this._readJsonFile(mcpPath);
+			for (const def of this._parseMcpServerDefinitionMap(json, pluginFsPath, adapter)) {
+				if (!merged.has(def.name)) {
+					merged.set(def.name, def.configuration);
+				}
 			}
 		}
-
-		return [];
+		return [...merged.entries()]
+			.map(([name, configuration]) => ({ name, configuration } satisfies IAgentPluginMcpServerDefinition))
+			.sort((a, b) => a.name.localeCompare(b.name));
 	}
 
-	private _parseMcpServerDefinitionMap(raw: unknown): IAgentPluginMcpServerDefinition[] {
-		if (!raw || typeof raw !== 'object') {
+	private _parseMcpServerDefinitionMap(raw: unknown, pluginFsPath: string, adapter: IAgentPluginFormatAdapter): IAgentPluginMcpServerDefinition[] {
+		if (!raw || typeof raw !== 'object' || !raw.hasOwnProperty('mcpServers')) {
 			return [];
 		}
 
 		const definitions: IAgentPluginMcpServerDefinition[] = [];
-		for (const [name, configValue] of Object.entries(raw as Record<string, unknown>)) {
+		for (const [name, configValue] of Object.entries((raw as { mcpServers: Record<string, unknown> }).mcpServers)) {
 			const configuration = this._normalizeMcpServerConfiguration(configValue);
 			if (!configuration) {
 				continue;
 			}
 
-			definitions.push({ name, configuration });
+			let def: IAgentPluginMcpServerDefinition = { name, configuration };
+			if (adapter.pluginRootToken && adapter.pluginRootEnvVar) {
+				def = interpolateMcpPluginRoot(def, pluginFsPath, adapter.pluginRootToken, adapter.pluginRootEnvVar);
+			}
+			definitions.push(def);
 		}
 
 		return definitions;
@@ -508,28 +753,6 @@ export class ConfiguredAgentPluginDiscovery extends Disposable implements IAgent
 		return undefined;
 	}
 
-	private async _readHooks(pluginUri: URI, adapter: IAgentPluginFormatAdapter): Promise<readonly IAgentPluginHook[]> {
-		const userHome = (await this._pathService.userHome()).fsPath;
-		for (const hooksUri of adapter.hookConfigPaths.map(path => joinPath(pluginUri, path))) {
-			const json = await this._readJsonFile(hooksUri);
-			if (json) {
-				return adapter.parseHooks(json, pluginUri, userHome);
-			}
-		}
-
-		for (const manifestPath of adapter.manifestPaths.map(path => joinPath(pluginUri, path))) {
-			const manifest = await this._readJsonFile(manifestPath);
-			if (manifest && typeof manifest === 'object') {
-				const hooks = (manifest as Record<string, unknown>)['hooks'];
-				if (hooks && typeof hooks === 'object') {
-					return adapter.parseHooks({ hooks }, pluginUri, userHome);
-				}
-			}
-		}
-
-		return [];
-	}
-
 	private async _readJsonFile(uri: URI): Promise<unknown | undefined> {
 		try {
 			const fileContents = await this._fileService.readFile(uri);
@@ -539,66 +762,160 @@ export class ConfiguredAgentPluginDiscovery extends Disposable implements IAgent
 		}
 	}
 
-	private async _readSkills(uri: URI): Promise<readonly IAgentPluginSkill[]> {
-		const skillsDir = joinPath(uri, 'skills');
-		let stat;
-		try {
-			stat = await this._fileService.resolve(skillsDir);
-		} catch {
-			return [];
-		}
+	private async _readSkills(pluginRoot: URI, dirs: readonly URI[]): Promise<readonly IAgentPluginSkill[]> {
+		const seen = new Set<string>();
+		const skills: IAgentPluginSkill[] = [];
 
-		if (!stat.isDirectory || !stat.children) {
-			return [];
-		}
+		const addSkill = (name: string, skillMd: URI) => {
+			if (!seen.has(name)) {
+				seen.add(name);
+				skills.push({ uri: skillMd, name });
+			}
+		};
 
-		const skills: IAgentPluginSkill[] = [];
-		for (const child of stat.children) {
-			if (!child.isFile || extname(child.resource).toLowerCase() !== COMMAND_FILE_SUFFIX) {
+		for (const dir of dirs) {
+			// If the path points directly to a skill directory (contains SKILL.md),
+			// add it as a single skill instead of scanning its children.
+			const skillMd = URI.joinPath(dir, 'SKILL.md');
+			if (await this._pathExists(skillMd)) {
+				addSkill(basename(dir), skillMd);
 				continue;
 			}
 
-			const name = basename(child.resource).slice(0, -COMMAND_FILE_SUFFIX.length);
+			let stat;
+			try {
+				stat = await this._fileService.resolve(dir);
+			} catch {
+				continue;
+			}
 
-			skills.push({
-				uri: child.resource,
-				name,
-			});
+			if (!stat.isDirectory || !stat.children) {
+				continue;
+			}
+
+			for (const child of stat.children) {
+				const childSkillMd = URI.joinPath(child.resource, 'SKILL.md');
+				if (await this._pathExists(childSkillMd)) {
+					addSkill(basename(child.resource), childSkillMd);
+				}
+			}
+		}
+
+		// Fallback: support single-skill plugins with SKILL.md at the plugin root
+		if (skills.length === 0) {
+			const rootSkillMd = URI.joinPath(pluginRoot, 'SKILL.md');
+			if (await this._pathExists(rootSkillMd)) {
+				addSkill(basename(pluginRoot), rootSkillMd);
+			}
 		}
 
 		skills.sort((a, b) => a.name.localeCompare(b.name));
 		return skills;
 	}
 
-	private async _readCommands(uri: URI): Promise<readonly IAgentPluginCommand[]> {
-		const commandsDir = joinPath(uri, 'commands');
-		let stat;
-		try {
-			stat = await this._fileService.resolve(commandsDir);
-		} catch {
-			return [];
-		}
+	/**
+	 * Scans directories for rule/instruction files (`.mdc`, `.md`,
+	 * `.instructions.md`), returning `{ uri, name }` entries where name is
+	 * derived from the filename minus the matched suffix.
+	 */
+	private async _readRules(dirs: readonly URI[]): Promise<readonly IAgentPluginInstruction[]> {
+		const seen = new Set<string>();
+		const items: IAgentPluginInstruction[] = [];
 
-		if (!stat.isDirectory || !stat.children) {
-			return [];
+		const matchSuffix = (filename: string): string | undefined => {
+			const lower = filename.toLowerCase();
+			return RULE_FILE_SUFFIXES.find(s => lower.endsWith(s));
+		};
+
+		const addItem = (name: string, uri: URI) => {
+			if (!seen.has(name)) {
+				seen.add(name);
+				items.push({ uri, name });
+			}
+		};
+
+		for (const dir of dirs) {
+			let stat;
+			try {
+				stat = await this._fileService.resolve(dir);
+			} catch {
+				continue;
+			}
+
+			if (stat.isFile) {
+				const suffix = matchSuffix(basename(dir));
+				if (suffix) {
+					addItem(basename(dir).slice(0, -suffix.length), dir);
+				}
+				continue;
+			}
+
+			if (!stat.isDirectory || !stat.children) {
+				continue;
+			}
+
+			for (const child of stat.children) {
+				if (!child.isFile) {
+					continue;
+				}
+				const suffix = matchSuffix(child.name);
+				if (suffix) {
+					addItem(child.name.slice(0, -suffix.length), child.resource);
+				}
+			}
 		}
 
-		const commands: IAgentPluginCommand[] = [];
-		for (const child of stat.children) {
-			if (!child.isFile || extname(child.resource).toLowerCase() !== COMMAND_FILE_SUFFIX) {
+		items.sort((a, b) => a.name.localeCompare(b.name));
+		return items;
+	}
+
+	/**
+	 * Scans directories for `.md` files, returning `{ uri, name }` entries
+	 * where name is derived from the filename (minus the `.md` extension).
+	 * If a path points to a specific `.md` file, it is included directly.
+	 * Used for both commands and agents.
+	 */
+	private async _readMarkdownComponents(dirs: readonly URI[]): Promise<readonly { uri: URI; name: string }[]> {
+		const seen = new Set<string>();
+		const items: { uri: URI; name: string }[] = [];
+
+		const addItem = (name: string, uri: URI) => {
+			if (!seen.has(name)) {
+				seen.add(name);
+				items.push({ uri, name });
+			}
+		};
+
+		for (const dir of dirs) {
+			let stat;
+			try {
+				stat = await this._fileService.resolve(dir);
+			} catch {
 				continue;
 			}
 
-			const name = basename(child.resource).slice(0, -COMMAND_FILE_SUFFIX.length);
 
-			commands.push({
-				uri: child.resource,
-				name,
-			});
+			// If the path points to a specific .md file, include it directly.
+			if (stat.isFile && extname(dir).toLowerCase() === COMMAND_FILE_SUFFIX) {
+				addItem(basename(dir).slice(0, -COMMAND_FILE_SUFFIX.length), dir);
+				continue;
+			}
+
+
+			if (!stat.isDirectory || !stat.children) {
+				continue;
+			}
+
+			for (const child of stat.children) {
+				if (!child.isFile || extname(child.resource).toLowerCase() !== COMMAND_FILE_SUFFIX) {
+					continue;
+				}
+				addItem(basename(child.resource).slice(0, -COMMAND_FILE_SUFFIX.length), child.resource);
+			}
 		}
 
-		commands.sort((a, b) => a.name.localeCompare(b.name));
-		return commands;
+		items.sort((a, b) => a.name.localeCompare(b.name));
+		return items;
 	}
 
 	private _disposePluginEntriesExcept(keep: Set<string>): void {
@@ -616,3 +933,182 @@ export class ConfiguredAgentPluginDiscovery extends Disposable implements IAgent
 	}
 }
 
+export class ConfiguredAgentPluginDiscovery extends AbstractAgentPluginDiscovery {
+
+	private readonly _pluginLocationsConfig: IObservable<Record<string, boolean>>;
+
+	constructor(
+		@IConfigurationService private readonly _configurationService: IConfigurationService,
+		@IFileService fileService: IFileService,
+		@IPluginMarketplaceService private readonly _pluginMarketplaceService: IPluginMarketplaceService,
+		@IWorkspaceContextService private readonly _workspaceContextService: IWorkspaceContextService,
+		@IPathService pathService: IPathService,
+		@ILogService logService: ILogService,
+		@IInstantiationService instantiationService: IInstantiationService,
+	) {
+		super(fileService, pathService, logService, instantiationService);
+		this._pluginLocationsConfig = observableConfigValue<Record<string, boolean>>(ChatConfiguration.PluginLocations, {}, _configurationService);
+	}
+
+	public override start(enablementModel: IEnablementModel): void {
+		this._enablementModel = enablementModel;
+		const scheduler = this._register(new RunOnceScheduler(() => this._refreshPlugins(), 0));
+		this._register(autorun(reader => {
+			this._pluginLocationsConfig.read(reader);
+			scheduler.schedule();
+		}));
+		scheduler.schedule();
+	}
+
+	protected override async _discoverPluginSources(): Promise<readonly IPluginSource[]> {
+		const sources: IPluginSource[] = [];
+		const config = this._pluginLocationsConfig.get();
+		const userHome = await this._getUserHome();
+
+		for (const [path, enabled] of Object.entries(config)) {
+			if (!path.trim() || enabled === false) {
+				continue;
+			}
+
+			const resources = this._resolvePluginPath(path.trim(), userHome);
+			for (const resource of resources) {
+				let stat;
+				try {
+					stat = await this._fileService.resolve(resource);
+				} catch {
+					this._logService.debug(`[ConfiguredAgentPluginDiscovery] Could not resolve plugin path: ${resource.toString()}`);
+					continue;
+				}
+
+				if (!stat.isDirectory) {
+					this._logService.debug(`[ConfiguredAgentPluginDiscovery] Plugin path is not a directory: ${resource.toString()}`);
+					continue;
+				}
+
+				const fromMarketplace = this._pluginMarketplaceService.getMarketplacePluginMetadata(stat.resource);
+				const configKey = path;
+				sources.push({
+					uri: stat.resource,
+					fromMarketplace,
+					remove: () => this._removePluginPath(configKey),
+				});
+			}
+		}
+
+		return sources;
+	}
+
+	private async _getUserHome(): Promise<string> {
+		const userHome = await this._pathService.userHome();
+		return userHome.scheme === 'file' ? userHome.fsPath : userHome.path;
+	}
+
+	/**
+	 * Resolves a plugin path to one or more resource URIs. Supports:
+	 * - Absolute paths (used directly)
+	 * - Tilde paths (expanded to user home directory)
+	 * - Relative paths (resolved against each workspace folder)
+	 */
+	private _resolvePluginPath(path: string, userHome: string): URI[] {
+		if (path.startsWith('~')) {
+			path = untildify(path, userHome);
+		}
+
+		// Handle absolute paths
+		if (win32.isAbsolute(path) || posix.isAbsolute(path)) {
+			return [URI.file(path)];
+		}
+
+		return this._workspaceContextService.getWorkspace().folders.map(
+			folder => joinPath(folder.uri, path)
+		);
+	}
+
+	/**
+	 * Removes a plugin path from `chat.pluginLocations` in the most specific
+	 * config target where the key is defined.
+	 */
+	private _removePluginPath(configKey: string): void {
+		const inspected = this._configurationService.inspect<Record<string, boolean>>(ChatConfiguration.PluginLocations);
+
+		const targets = [
+			ConfigurationTarget.WORKSPACE_FOLDER,
+			ConfigurationTarget.WORKSPACE,
+			ConfigurationTarget.USER_LOCAL,
+			ConfigurationTarget.USER_REMOTE,
+			ConfigurationTarget.USER,
+			ConfigurationTarget.APPLICATION,
+		];
+
+		for (const target of targets) {
+			const mapping = getConfigValueInTarget(inspected, target);
+			if (mapping && Object.prototype.hasOwnProperty.call(mapping, configKey)) {
+				const updated = { ...mapping };
+				delete updated[configKey];
+				this._configurationService.updateValue(
+					ChatConfiguration.PluginLocations,
+					updated,
+					target,
+				);
+				return;
+			}
+		}
+	}
+}
+
+export class MarketplaceAgentPluginDiscovery extends AbstractAgentPluginDiscovery {
+
+	constructor(
+		@IPluginMarketplaceService private readonly _pluginMarketplaceService: IPluginMarketplaceService,
+		@IAgentPluginRepositoryService private readonly _pluginRepositoryService: IAgentPluginRepositoryService,
+		@IFileService fileService: IFileService,
+		@IPathService pathService: IPathService,
+		@ILogService logService: ILogService,
+		@IInstantiationService instantiationService: IInstantiationService,
+	) {
+		super(fileService, pathService, logService, instantiationService);
+	}
+
+	public override start(enablementModel: IEnablementModel): void {
+		this._enablementModel = enablementModel;
+		const scheduler = this._register(new RunOnceScheduler(() => this._refreshPlugins(), 0));
+		this._register(autorun(reader => {
+			this._pluginMarketplaceService.installedPlugins.read(reader);
+			scheduler.schedule();
+		}));
+		scheduler.schedule();
+	}
+
+	protected override async _discoverPluginSources(): Promise<readonly IPluginSource[]> {
+		const installed = this._pluginMarketplaceService.installedPlugins.get();
+		const sources: IPluginSource[] = [];
+
+		for (const entry of installed) {
+			let stat;
+			try {
+				stat = await this._fileService.resolve(entry.pluginUri);
+			} catch {
+				this._logService.debug(`[MarketplaceAgentPluginDiscovery] Could not resolve installed plugin: ${entry.pluginUri.toString()}`);
+				continue;
+			}
+
+			if (!stat.isDirectory) {
+				this._logService.debug(`[MarketplaceAgentPluginDiscovery] Installed plugin path is not a directory: ${entry.pluginUri.toString()}`);
+				continue;
+			}
+
+			sources.push({
+				uri: stat.resource,
+				fromMarketplace: entry.plugin,
+				remove: () => {
+					this._pluginMarketplaceService.removeInstalledPlugin(entry.pluginUri);
+					this._pluginRepositoryService.cleanupPluginSource(entry.plugin).catch(error => {
+						this._logService.error('[MarketplaceAgentPluginDiscovery] Failed to clean up plugin source', error);
+					});
+				},
+			});
+		}
+
+		return sources;
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/common/plugins/marketplaceReference.ts b/src/vs/workbench/contrib/chat/common/plugins/marketplaceReference.ts
new file mode 100644
index 0000000000000..a2eabed796fee
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/plugins/marketplaceReference.ts
@@ -0,0 +1,200 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { URI } from '../../../../../base/common/uri.js';
+
+export const enum MarketplaceReferenceKind {
+	GitHubShorthand = 'githubShorthand',
+	GitUri = 'gitUri',
+	LocalFileUri = 'localFileUri',
+}
+
+export interface IMarketplaceReference {
+	readonly rawValue: string;
+	readonly displayLabel: string;
+	readonly cloneUrl: string;
+	readonly canonicalId: string;
+	readonly cacheSegments: readonly string[];
+	readonly kind: MarketplaceReferenceKind;
+	readonly githubRepo?: string;
+	readonly localRepositoryUri?: URI;
+}
+
+export function parseMarketplaceReferences(values: readonly unknown[]): IMarketplaceReference[] {
+	const byCanonicalId = new Map<string, IMarketplaceReference>();
+
+	for (const value of values) {
+		if (typeof value !== 'string') {
+			continue;
+		}
+
+		const parsed = parseMarketplaceReference(value);
+		if (!parsed) {
+			continue;
+		}
+
+		if (!byCanonicalId.has(parsed.canonicalId)) {
+			byCanonicalId.set(parsed.canonicalId, parsed);
+		}
+	}
+
+	return [...byCanonicalId.values()];
+}
+
+/**
+ * Merges two sets of marketplace references, deduplicating by canonical ID.
+ * The first set takes precedence when IDs collide.
+ */
+export function deduplicateMarketplaceReferences(primary: readonly IMarketplaceReference[], secondary: readonly IMarketplaceReference[]): IMarketplaceReference[] {
+	const byCanonicalId = new Map<string, IMarketplaceReference>();
+	for (const ref of primary) {
+		byCanonicalId.set(ref.canonicalId, ref);
+	}
+	for (const ref of secondary) {
+		if (!byCanonicalId.has(ref.canonicalId)) {
+			byCanonicalId.set(ref.canonicalId, ref);
+		}
+	}
+	return [...byCanonicalId.values()];
+}
+
+export function parseMarketplaceReference(value: string): IMarketplaceReference | undefined {
+	const rawValue = value.trim();
+	if (!rawValue) {
+		return undefined;
+	}
+
+	const uriReference = parseUriMarketplaceReference(rawValue);
+	if (uriReference) {
+		return uriReference;
+	}
+
+	const scpReference = parseScpMarketplaceReference(rawValue);
+	if (scpReference) {
+		return scpReference;
+	}
+
+	const shorthandMatch = /^([A-Za-z0-9_.-]+)\/([A-Za-z0-9_.-]+)$/.exec(rawValue);
+	if (shorthandMatch) {
+		const owner = shorthandMatch[1];
+		const repo = shorthandMatch[2];
+		return {
+			rawValue,
+			displayLabel: `${owner}/${repo}`,
+			cloneUrl: `https://github.com/${owner}/${repo}.git`,
+			canonicalId: getGitHubCanonicalId(owner, repo),
+			cacheSegments: ['github.com', owner, repo],
+			kind: MarketplaceReferenceKind.GitHubShorthand,
+			githubRepo: `${owner}/${repo}`,
+		};
+	}
+
+	return undefined;
+}
+
+function parseUriMarketplaceReference(rawValue: string): IMarketplaceReference | undefined {
+	let uri: URI;
+	try {
+		uri = URI.parse(rawValue);
+	} catch {
+		return undefined;
+	}
+
+	const scheme = uri.scheme.toLowerCase();
+	if (scheme === 'file' && /^file:\/\//i.test(rawValue)) {
+		const localRepositoryUri = URI.file(uri.fsPath);
+		return {
+			rawValue,
+			displayLabel: localRepositoryUri.fsPath,
+			cloneUrl: rawValue,
+			canonicalId: `file:${localRepositoryUri.toString().toLowerCase()}`,
+			cacheSegments: [],
+			kind: MarketplaceReferenceKind.LocalFileUri,
+			localRepositoryUri,
+		};
+	}
+
+	if (scheme !== 'http' && scheme !== 'https' && scheme !== 'ssh') {
+		return undefined;
+	}
+
+	if (!uri.authority) {
+		return undefined;
+	}
+
+	const normalizedPath = normalizeGitRepoPath(uri.path);
+	if (!normalizedPath) {
+		return undefined;
+	}
+
+	const gitSuffix = '.git';
+	const sanitizedAuthority = sanitizePathSegment(uri.authority.toLowerCase());
+	const pathHasGitSuffix = normalizedPath.toLowerCase().endsWith(gitSuffix);
+	const pathWithoutGit = pathHasGitSuffix ? normalizedPath.slice(1, normalizedPath.length - gitSuffix.length) : normalizedPath.slice(1);
+	const pathSegments = pathWithoutGit.split('/').map(sanitizePathSegment);
+	// Always normalize the canonical path to include .git so that URLs with and without the suffix deduplicate.
+	const canonicalPath = pathHasGitSuffix ? normalizedPath.slice(1).toLowerCase() : `${normalizedPath.slice(1).toLowerCase()}${gitSuffix}`;
+	return {
+		rawValue,
+		displayLabel: rawValue,
+		cloneUrl: rawValue,
+		canonicalId: `git:${uri.authority.toLowerCase()}/${canonicalPath}`,
+		cacheSegments: [sanitizedAuthority, ...pathSegments],
+		kind: MarketplaceReferenceKind.GitUri,
+	};
+}
+
+function parseScpMarketplaceReference(rawValue: string): IMarketplaceReference | undefined {
+	const match = /^([^@\s]+)@([^:\s]+):(.+\.git)$/i.exec(rawValue);
+	if (!match) {
+		return undefined;
+	}
+
+	const authority = match[2];
+	const pathWithGit = match[3].replace(/^\/+/, '');
+	if (!pathWithGit.toLowerCase().endsWith('.git')) {
+		return undefined;
+	}
+
+	const pathSegments = pathWithGit.slice(0, -4).split('/').map(sanitizePathSegment);
+	return {
+		rawValue,
+		displayLabel: rawValue,
+		cloneUrl: rawValue,
+		canonicalId: `git:${authority.toLowerCase()}/${pathWithGit.toLowerCase()}`,
+		cacheSegments: [sanitizePathSegment(authority.toLowerCase()), ...pathSegments],
+		kind: MarketplaceReferenceKind.GitUri,
+	};
+}
+
+/**
+ * Normalizes a Git repository path and validates that it has at least two segments
+ * (i.e., at least one owner/repo pair below the root). Accepts paths with or without
+ * a `.git` suffix — the suffix is preserved in the returned value so callers can decide
+ * how to treat it.
+ */
+function normalizeGitRepoPath(path: string): string | undefined {
+	const gitSuffix = '.git';
+	const trimmed = path.replace(/\/+/g, '/').replace(/\/+$/g, '');
+
+	const withLeadingSlash = trimmed.startsWith('/') ? trimmed : `/${trimmed}`;
+	// Strip .git suffix (if present) only for the purposes of validating path depth.
+	const pathWithoutGit = withLeadingSlash.toLowerCase().endsWith(gitSuffix)
+		? withLeadingSlash.slice(1, withLeadingSlash.length - gitSuffix.length)
+		: withLeadingSlash.slice(1);
+	if (!pathWithoutGit || !pathWithoutGit.includes('/')) {
+		return undefined;
+	}
+
+	return withLeadingSlash;
+}
+
+function getGitHubCanonicalId(owner: string, repo: string): string {
+	return `github:${owner.toLowerCase()}/${repo.toLowerCase()}`;
+}
+
+function sanitizePathSegment(value: string): string {
+	return value.replace(/[\\/:*?"<>|]/g, '_');
+}
diff --git a/src/vs/workbench/contrib/chat/common/plugins/pluginInstallService.ts b/src/vs/workbench/contrib/chat/common/plugins/pluginInstallService.ts
index abdf81f730311..22bddcd54a56d 100644
--- a/src/vs/workbench/contrib/chat/common/plugins/pluginInstallService.ts
+++ b/src/vs/workbench/contrib/chat/common/plugins/pluginInstallService.ts
@@ -3,30 +3,64 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { CancellationToken } from '../../../../../base/common/cancellation.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { createDecorator } from '../../../../../platform/instantiation/common/instantiation.js';
 import { IMarketplacePlugin } from './pluginMarketplaceService.js';
 
 export const IPluginInstallService = createDecorator<IPluginInstallService>('pluginInstallService');
 
+export interface IUpdateAllPluginsOptions {
+	/**
+	 * When `true`, also re-installs npm/pip packages that have no pinned
+	 * version. Defaults to `false` to avoid interactive terminal prompts
+	 * during background updates.
+	 */
+	readonly force?: boolean;
+
+	/**
+	 * When `true`, suppresses the progress notification. An info
+	 * notification is still shown listing any plugins that were
+	 * updated, and error notifications are shown on failure.
+	 */
+	readonly silent?: boolean;
+}
+
+export interface IUpdateAllPluginsResult {
+	/** Names of plugins/marketplaces that were updated successfully. */
+	readonly updatedNames: readonly string[];
+	/** Names of plugins/marketplaces that failed to update. */
+	readonly failedNames: readonly string[];
+}
+
 export interface IPluginInstallService {
 	readonly _serviceBrand: undefined;
 
 	/**
 	 * Clones the marketplace repository (if not already cached) and registers
-	 * the plugin's source directory in the user's `chat.plugins.paths` config.
+	 * the plugin in the marketplace service's installed plugins storage.
 	 */
 	installPlugin(plugin: IMarketplacePlugin): Promise<void>;
 
 	/**
-	 * Removes the plugin from `chat.plugins.paths` config.
+	 * Installs a plugin directly from a source location string. Accepts
+	 * GitHub shorthand (`owner/repo`) or a full git clone URL. Clones the
+	 * repository, reads marketplace metadata to discover plugins, and
+	 * registers the selected plugin.
 	 */
-	uninstallPlugin(pluginUri: URI): Promise<void>;
+	installPluginFromSource(source: string): Promise<void>;
 
 	/**
 	 * Pulls the latest changes for an already-cloned marketplace repository.
 	 */
-	updatePlugin(plugin: IMarketplacePlugin): Promise<void>;
+	updatePlugin(plugin: IMarketplacePlugin): Promise<boolean>;
+
+	/**
+	 * Updates all installed plugins. First pulls each unique marketplace
+	 * repository, then updates non-relative-path plugins individually
+	 * (git pull, npm install, pip install, etc.).
+	 */
+	updateAllPlugins(options: IUpdateAllPluginsOptions, token: CancellationToken): Promise<IUpdateAllPluginsResult>;
 
 	/**
 	 * Returns the URI where a marketplace plugin would be installed on disk.
diff --git a/src/vs/workbench/contrib/chat/common/plugins/pluginMarketplaceService.ts b/src/vs/workbench/contrib/chat/common/plugins/pluginMarketplaceService.ts
index 32f158121bced..49a873828a952 100644
--- a/src/vs/workbench/contrib/chat/common/plugins/pluginMarketplaceService.ts
+++ b/src/vs/workbench/contrib/chat/common/plugins/pluginMarketplaceService.ts
@@ -3,33 +3,120 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { runWhenGlobalIdle } from '../../../../../base/common/async.js';
 import { CancellationToken } from '../../../../../base/common/cancellation.js';
-import { joinPath, normalizePath, relativePath } from '../../../../../base/common/resources.js';
-import { URI } from '../../../../../base/common/uri.js';
-import { createDecorator } from '../../../../../platform/instantiation/common/instantiation.js';
+import { Event } from '../../../../../base/common/event.js';
+import { parse as parseJSONC } from '../../../../../base/common/json.js';
+import { Lazy } from '../../../../../base/common/lazy.js';
+import { Disposable } from '../../../../../base/common/lifecycle.js';
+import { revive } from '../../../../../base/common/marshalling.js';
+import { derived, IObservable, observableFromEvent, observableValue } from '../../../../../base/common/observable.js';
+import { isEqual, isEqualOrParent, joinPath, normalizePath, relativePath } from '../../../../../base/common/resources.js';
+import { URI, UriComponents } from '../../../../../base/common/uri.js';
 import { IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
-import { asJson, IRequestService } from '../../../../../platform/request/common/request.js';
+import { IFileService } from '../../../../../platform/files/common/files.js';
+import { createDecorator } from '../../../../../platform/instantiation/common/instantiation.js';
 import { ILogService } from '../../../../../platform/log/common/log.js';
+import { ObservableMemento, observableMemento } from '../../../../../platform/observable/common/observableMemento.js';
+import { asJson, IRequestService } from '../../../../../platform/request/common/request.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../../platform/storage/common/storage.js';
+import type { Dto } from '../../../../services/extensions/common/proxyIdentifier.js';
+import { AutoUpdateConfigurationKey, AutoUpdateConfigurationValue } from '../../../extensions/common/extensions.js';
 import { ChatConfiguration } from '../constants.js';
+import { IAgentPluginRepositoryService } from './agentPluginRepositoryService.js';
+import { IWorkspacePluginSettingsService } from './workspacePluginSettingsService.js';
+import { IWorkspaceTrustManagementService } from '../../../../../platform/workspace/common/workspaceTrust.js';
+import { type IMarketplaceReference, deduplicateMarketplaceReferences, MarketplaceReferenceKind, parseMarketplaceReference, parseMarketplaceReferences } from './marketplaceReference.js';
+
+// Re-export marketplace reference types for downstream consumers.
+export { deduplicateMarketplaceReferences, MarketplaceReferenceKind, parseMarketplaceReference, parseMarketplaceReferences } from './marketplaceReference.js';
+export type { IMarketplaceReference } from './marketplaceReference.js';
 
 export const enum MarketplaceType {
 	Copilot = 'copilot',
 	Claude = 'claude',
+	OpenPlugin = 'openPlugin',
+}
+
+export const enum PluginSourceKind {
+	RelativePath = 'relativePath',
+	GitHub = 'github',
+	GitUrl = 'url',
+	Npm = 'npm',
+	Pip = 'pip',
+}
+
+export interface IRelativePathPluginSource {
+	readonly kind: PluginSourceKind.RelativePath;
+	/** Resolved relative path within the marketplace repository. */
+	readonly path: string;
+}
+
+export interface IGitHubPluginSource {
+	readonly kind: PluginSourceKind.GitHub;
+	readonly repo: string;
+	readonly ref?: string;
+	readonly sha?: string;
+}
+
+export interface IGitUrlPluginSource {
+	readonly kind: PluginSourceKind.GitUrl;
+	/** Full git repository URL (must end with .git). */
+	readonly url: string;
+	readonly ref?: string;
+	readonly sha?: string;
+}
+
+export interface INpmPluginSource {
+	readonly kind: PluginSourceKind.Npm;
+	readonly package: string;
+	readonly version?: string;
+	readonly registry?: string;
 }
 
+export interface IPipPluginSource {
+	readonly kind: PluginSourceKind.Pip;
+	readonly package: string;
+	readonly version?: string;
+	readonly registry?: string;
+}
+
+export type IPluginSourceDescriptor =
+	| IRelativePathPluginSource
+	| IGitHubPluginSource
+	| IGitUrlPluginSource
+	| INpmPluginSource
+	| IPipPluginSource;
+
 export interface IMarketplacePlugin {
 	readonly name: string;
 	readonly description: string;
 	readonly version: string;
-	/** Subdirectory within the repository where the plugin lives. */
+	/** Subdirectory within the repository where the plugin lives (for relative-path sources). */
 	readonly source: string;
-	/** The `owner/repo` identifier of the marketplace repository. */
+	/** Structured source descriptor indicating how the plugin should be fetched/installed. */
+	readonly sourceDescriptor: IPluginSourceDescriptor;
+	/** Marketplace label shown in UI and plugin provenance. */
 	readonly marketplace: string;
+	/** Canonical reference for clone/update/install location resolution. */
+	readonly marketplaceReference: IMarketplaceReference;
 	/** The type of marketplace this plugin comes from. */
 	readonly marketplaceType: MarketplaceType;
 	readonly readmeUri?: URI;
 }
 
+/** Raw JSON shape of a remote plugin source object in marketplace.json. */
+interface IJsonPluginSource {
+	readonly source: string;
+	readonly repo?: string;
+	readonly url?: string;
+	readonly package?: string;
+	readonly ref?: string;
+	readonly sha?: string;
+	readonly version?: string;
+	readonly registry?: string;
+}
+
 interface IMarketplaceJson {
 	readonly metadata?: {
 		readonly pluginRoot?: string;
@@ -38,15 +125,58 @@ interface IMarketplaceJson {
 		readonly name?: string;
 		readonly description?: string;
 		readonly version?: string;
-		readonly source?: string;
+		readonly source?: string | IJsonPluginSource;
 	}[];
 }
 
+export interface IMarketplaceInstalledPlugin {
+	readonly pluginUri: URI;
+	readonly plugin: IMarketplacePlugin;
+	readonly enabled: boolean;
+}
+
 export const IPluginMarketplaceService = createDecorator<IPluginMarketplaceService>('pluginMarketplaceService');
 
 export interface IPluginMarketplaceService {
 	readonly _serviceBrand: undefined;
+	readonly onDidChangeMarketplaces: Event<void>;
+	/** Installed marketplace plugins, backed by storage. */
+	readonly installedPlugins: IObservable<readonly IMarketplaceInstalledPlugin[]>;
+	/**
+	 * Observable that is `true` when at least one cloned marketplace
+	 * repository has upstream changes available. Checked periodically
+	 * (approximately once per day) when `extensions.autoUpdate` is enabled.
+	 */
+	readonly hasUpdatesAvailable: IObservable<boolean>;
+	/**
+	 * Observable snapshot of the last {@link fetchMarketplacePlugins} result.
+	 * Empty until the first fetch completes. Views should use this for
+	 * synchronous outdated-detection instead of calling fetchMarketplacePlugins.
+	 */
+	readonly lastFetchedPlugins: IObservable<readonly IMarketplacePlugin[]>;
+	/**
+	 * Set of recommended plugin keys (`"pluginName@marketplaceName"`) aggregated
+	 * from workspace-defined settings (e.g. `.claude/settings.json`). Providers
+	 * may be added over time; consumers should not assume a specific source.
+	 */
+	readonly recommendedPlugins: IObservable<ReadonlySet<string>>;
+	/** Resets {@link hasUpdatesAvailable} to `false`. */
+	clearUpdatesAvailable(): void;
 	fetchMarketplacePlugins(token: CancellationToken): Promise<IMarketplacePlugin[]>;
+	getMarketplacePluginMetadata(pluginUri: URI): IMarketplacePlugin | undefined;
+	addInstalledPlugin(pluginUri: URI, plugin: IMarketplacePlugin): void;
+	removeInstalledPlugin(pluginUri: URI): void;
+	setInstalledPluginEnabled(pluginUri: URI, enabled: boolean): void;
+	/** Returns whether the given marketplace has been explicitly trusted by the user. */
+	isMarketplaceTrusted(ref: IMarketplaceReference): boolean;
+	/** Records that the user trusts the given marketplace, persisted permanently. */
+	trustMarketplace(ref: IMarketplaceReference): void;
+	/**
+	 * Reads marketplace definition files from an already-cloned repository
+	 * directory and returns the declared plugins. Used by direct-install flows
+	 * that clone a repo first, then need to discover its plugins.
+	 */
+	readPluginsFromDirectory(repoDir: URI, reference: IMarketplaceReference): Promise<IMarketplacePlugin[]>;
 }
 
 /**
@@ -54,39 +184,254 @@ export interface IPluginMarketplaceService {
  * The first match determines the marketplace type.
  */
 const MARKETPLACE_DEFINITIONS: { type: MarketplaceType; path: string }[] = [
+	{ type: MarketplaceType.OpenPlugin, path: 'marketplace.json' },
+	{ type: MarketplaceType.OpenPlugin, path: '.plugin/marketplace.json' },
 	{ type: MarketplaceType.Copilot, path: '.github/plugin/marketplace.json' },
 	{ type: MarketplaceType.Claude, path: '.claude-plugin/marketplace.json' },
 ];
 
-export class PluginMarketplaceService implements IPluginMarketplaceService {
+const GITHUB_MARKETPLACE_CACHE_TTL_MS = 8 * 60 * 60 * 1000;
+const GITHUB_MARKETPLACE_CACHE_STORAGE_KEY = 'chat.plugins.marketplaces.githubCache.v1';
+
+/** Interval between periodic plugin update checks (24 hours). */
+const PLUGIN_UPDATE_CHECK_INTERVAL_MS = 24 * 60 * 60 * 1000;
+const PLUGIN_UPDATE_LAST_CHECK_STORAGE_KEY = 'chat.plugins.lastUpdateCheck.v1';
+
+interface IGitHubMarketplaceCacheEntry {
+	readonly plugins: readonly IMarketplacePlugin[];
+	readonly expiresAt: number;
+	readonly referenceRawValue: string;
+}
+
+type IStoredGitHubMarketplaceCache = Dto<Record<string, IGitHubMarketplaceCacheEntry>>;
+
+interface IStoredInstalledPlugin {
+	readonly pluginUri: UriComponents;
+	readonly plugin: IMarketplacePlugin;
+	readonly enabled: boolean;
+}
+
+/**
+ * Ensures that an {@link IMarketplacePlugin} loaded from storage has a
+ * {@link IMarketplacePlugin.sourceDescriptor sourceDescriptor}. Plugins
+ * persisted before the sourceDescriptor field was introduced will only
+ * have the legacy `source` string — this function synthesises a
+ * {@link PluginSourceKind.RelativePath} descriptor from it.
+ */
+function ensureSourceDescriptor(plugin: IMarketplacePlugin): IMarketplacePlugin {
+	if (plugin.sourceDescriptor) {
+		return plugin;
+	}
+	return {
+		...plugin,
+		sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: plugin.source },
+	};
+}
+
+const installedPluginsMemento = observableMemento<readonly IStoredInstalledPlugin[]>({
+	defaultValue: [],
+	key: 'chat.plugins.installed.v1',
+	toStorage: value => JSON.stringify(value),
+	fromStorage: value => {
+		const parsed = JSON.parse(value);
+		return Array.isArray(parsed) ? parsed : [];
+	},
+});
+
+const trustedMarketplacesMemento = observableMemento<readonly string[]>({
+	defaultValue: [],
+	key: 'chat.plugins.trustedMarketplaces.v1',
+	toStorage: value => JSON.stringify(value),
+	fromStorage: value => {
+		const parsed = JSON.parse(value);
+		return Array.isArray(parsed) ? parsed : [];
+	},
+});
+
+interface IStoredLastFetchedPlugins {
+	readonly plugins: readonly IMarketplacePlugin[];
+	readonly fetchedAt: number;
+}
+
+const lastFetchedPluginsMemento = observableMemento<IStoredLastFetchedPlugins>({
+	defaultValue: { plugins: [], fetchedAt: 0 },
+	key: 'chat.plugins.lastFetchedPlugins.v2',
+	toStorage: value => JSON.stringify(value),
+	fromStorage: value => {
+		const parsed = JSON.parse(value);
+		if (parsed && Array.isArray(parsed.plugins)) {
+			return parsed;
+		}
+		return { plugins: [], fetchedAt: 0 };
+	},
+});
+
+export class PluginMarketplaceService extends Disposable implements IPluginMarketplaceService {
 	declare readonly _serviceBrand: undefined;
+	private readonly _gitHubMarketplaceCache = new Lazy<Map<string, IGitHubMarketplaceCacheEntry>>(() => this._loadPersistedGitHubMarketplaceCache());
+	private readonly _installedPluginsStore: ObservableMemento<readonly IStoredInstalledPlugin[]>;
+	private readonly _trustedMarketplacesStore: ObservableMemento<readonly string[]>;
+	private readonly _lastFetchedPluginsStore: ObservableMemento<IStoredLastFetchedPlugins>;
+	private readonly _hasUpdatesAvailable = observableValue<boolean>('hasUpdatesAvailable', false);
+	private _updateCheckTimer: ReturnType<typeof setTimeout> | undefined;
+
+	readonly onDidChangeMarketplaces: Event<void>;
+
+	readonly installedPlugins: IObservable<readonly IMarketplaceInstalledPlugin[]>;
+	readonly hasUpdatesAvailable: IObservable<boolean> = this._hasUpdatesAvailable;
+	readonly lastFetchedPlugins: IObservable<readonly IMarketplacePlugin[]>;
+	readonly recommendedPlugins: IObservable<ReadonlySet<string>>;
 
 	constructor(
 		@IConfigurationService private readonly _configurationService: IConfigurationService,
 		@IRequestService private readonly _requestService: IRequestService,
+		@IFileService private readonly _fileService: IFileService,
+		@IAgentPluginRepositoryService private readonly _pluginRepositoryService: IAgentPluginRepositoryService,
 		@ILogService private readonly _logService: ILogService,
-	) { }
+		@IStorageService private readonly _storageService: IStorageService,
+		@IWorkspacePluginSettingsService private readonly _workspacePluginSettingsService: IWorkspacePluginSettingsService,
+		@IWorkspaceTrustManagementService private readonly _workspaceTrustService: IWorkspaceTrustManagementService,
+	) {
+		super();
+
+		this._installedPluginsStore = this._register(
+			installedPluginsMemento(StorageScope.APPLICATION, StorageTarget.MACHINE, _storageService)
+		);
+
+		this._trustedMarketplacesStore = this._register(
+			trustedMarketplacesMemento(StorageScope.APPLICATION, StorageTarget.MACHINE, _storageService)
+		);
+
+		this._lastFetchedPluginsStore = this._register(
+			lastFetchedPluginsMemento(StorageScope.APPLICATION, StorageTarget.MACHINE, _storageService)
+		);
+
+		this.lastFetchedPlugins = this._lastFetchedPluginsStore.map(s => {
+			const revived = revive(s) as IStoredLastFetchedPlugins;
+			return revived.plugins.map(ensureSourceDescriptor);
+		});
+
+		this.installedPlugins = this._installedPluginsStore.map(s =>
+			(revive(s) as readonly IMarketplaceInstalledPlugin[]).map(e => ({
+				...e,
+				plugin: ensureSourceDescriptor(e.plugin),
+			}))
+		);
+
+		// Aggregate recommended plugin keys from all providers.
+		// Currently sourced from Claude workspace settings; more providers can be
+		// added here via additional observables in the derived computation.
+		// Only expose recommendations when the workspace is trusted.
+		const workspaceTrusted = observableFromEvent(this, this._workspaceTrustService.onDidChangeTrust, () => this._workspaceTrustService.isWorkspaceTrusted());
+		this.recommendedPlugins = derived(reader => {
+			if (!workspaceTrusted.read(reader)) {
+				return new Set<string>();
+			}
+			const enabledMap = this._workspacePluginSettingsService.enabledPlugins.read(reader);
+			const keys = new Set<string>();
+			for (const [key, value] of enabledMap) {
+				if (value) {
+					keys.add(key);
+				}
+			}
+			return keys;
+		});
+
+		this.onDidChangeMarketplaces = Event.any(
+			Event.filter(
+				_configurationService.onDidChangeConfiguration,
+				e => e.affectsConfiguration(ChatConfiguration.PluginsEnabled) || e.affectsConfiguration(ChatConfiguration.PluginMarketplaces),
+			) as Event<unknown> as Event<void>,
+			Event.fromObservableLight(this._workspacePluginSettingsService.extraMarketplaces),
+			Event.map(this._workspaceTrustService.onDidChangeTrust, () => { }),
+		);
+
+		this._register(runWhenGlobalIdle(() => {
+			// Schedule periodic update checks when auto-update is enabled.
+			this._scheduleUpdateCheck();
+			this._register(Event.filter(
+				_configurationService.onDidChangeConfiguration,
+				e => e.affectsConfiguration(AutoUpdateConfigurationKey),
+			)(() => this._scheduleUpdateCheck()));
+		}));
+	}
+
+	override dispose(): void {
+		if (this._updateCheckTimer !== undefined) {
+			clearTimeout(this._updateCheckTimer);
+			this._updateCheckTimer = undefined;
+		}
+		super.dispose();
+	}
+
+	clearUpdatesAvailable(): void {
+		this._hasUpdatesAvailable.set(false, undefined);
+	}
 
 	async fetchMarketplacePlugins(token: CancellationToken): Promise<IMarketplacePlugin[]> {
-		const repos: string[] = this._configurationService.getValue(ChatConfiguration.PluginMarketplaces) ?? [];
+		if (!this._configurationService.getValue<boolean>(ChatConfiguration.PluginsEnabled)) {
+			return [];
+		}
+
+		const configuredRefs = this._configurationService.getValue<unknown[]>(ChatConfiguration.PluginMarketplaces) ?? [];
+		const configRefs = parseMarketplaceReferences(configuredRefs);
+
+		// Merge marketplace references from Claude workspace settings.
+		// Workspace-defined refs take precedence (are primary) so that their
+		// displayLabel overrides any matching global marketplace entry.
+		// Only include workspace-sourced refs when the workspace is trusted.
+		let allRefs: IMarketplaceReference[];
+		if (this._workspaceTrustService.isWorkspaceTrusted()) {
+			const workspaceEntries = this._workspacePluginSettingsService.extraMarketplaces.get();
+			allRefs = deduplicateMarketplaceReferences(workspaceEntries.map(e => e.reference), configRefs);
+		} else {
+			allRefs = configRefs;
+		}
+
+		for (const value of configuredRefs) {
+			if (typeof value !== 'string' || !parseMarketplaceReference(value)) {
+				this._logService.debug(`[PluginMarketplaceService] Ignoring invalid marketplace entry: ${String(value)}`);
+			}
+		}
+
 		const results = await Promise.all(
-			repos
-				.filter(repo => typeof repo === 'string' && /^[^/]+\/[^/]+$/.test(repo.trim()))
-				.map(repo => this._fetchFromRepo(repo.trim(), token))
+			allRefs.map(ref => {
+				if (ref.kind === MarketplaceReferenceKind.GitHubShorthand && ref.githubRepo) {
+					return this._fetchFromGitHubRepo(ref, ref.githubRepo, token);
+				}
+				return this._fetchFromClonedRepo(ref, token);
+			})
 		);
-		return results.flat();
+		const plugins = results.flat();
+		this._lastFetchedPluginsStore.set({ plugins, fetchedAt: Date.now() }, undefined);
+		return plugins;
 	}
 
-	private async _fetchFromRepo(repo: string, token: CancellationToken): Promise<IMarketplacePlugin[]> {
+	private async _fetchFromGitHubRepo(reference: IMarketplaceReference, repo: string, token: CancellationToken): Promise<IMarketplacePlugin[]> {
+		const cache = this._gitHubMarketplaceCache.value;
+
+		const cached = this._getCachedGitHubMarketplacePlugins(cache, reference.canonicalId);
+		if (cached) {
+			return cached.map(c => ({
+				...c,
+				marketplace: reference.displayLabel,
+				marketplaceReference: reference,
+			}));
+		}
+
+		let repoMayBePrivate = true;
+
 		for (const def of MARKETPLACE_DEFINITIONS) {
 			if (token.isCancellationRequested) {
 				return [];
 			}
 			const url = `https://raw.githubusercontent.com/${repo}/main/${def.path}`;
 			try {
-				const context = await this._requestService.request({ type: 'GET', url }, token);
-				if (context.res.statusCode !== 200) {
-					this._logService.debug(`[PluginMarketplaceService] ${url} returned status ${context.res.statusCode}, skipping`);
+				const context = await this._requestService.request({ type: 'GET', url, callSite: 'pluginMarketplaceService.fetchPluginList' }, token);
+				const statusCode = context.res.statusCode;
+				if (statusCode !== 200) {
+					repoMayBePrivate &&= statusCode !== undefined && statusCode >= 400 && statusCode < 500;
+					this._logService.debug(`[PluginMarketplaceService] ${url} returned status ${statusCode}, skipping`);
 					continue;
 				}
 				const json = await asJson<IMarketplaceJson>(context);
@@ -94,35 +439,323 @@ export class PluginMarketplaceService implements IPluginMarketplaceService {
 					this._logService.debug(`[PluginMarketplaceService] ${url} did not contain a valid plugins array, skipping`);
 					continue;
 				}
-				return json.plugins
-					.filter((p): p is { name: string; description?: string; version?: string; source?: string } =>
+				const plugins = json.plugins
+					.filter((p): p is { name: string; description?: string; version?: string; source?: string | IJsonPluginSource } =>
 						typeof p.name === 'string' && !!p.name
 					)
 					.flatMap(p => {
-						const source = resolvePluginSource(json.metadata?.pluginRoot, p.source ?? '');
-						if (source === undefined) {
-							this._logService.warn(`[PluginMarketplaceService] Skipping plugin '${p.name}' in ${repo}: invalid source path '${p.source ?? ''}' with pluginRoot '${json.metadata?.pluginRoot ?? ''}'`);
+						const sourceDescriptor = parsePluginSource(p.source, json.metadata?.pluginRoot, {
+							pluginName: p.name,
+							logService: this._logService,
+							logPrefix: `[PluginMarketplaceService]`,
+						});
+						if (!sourceDescriptor) {
 							return [];
 						}
 
+						const source = sourceDescriptor.kind === PluginSourceKind.RelativePath ? sourceDescriptor.path : '';
+
 						return [{
 							name: p.name,
 							description: p.description ?? '',
 							version: p.version ?? '',
 							source,
-							marketplace: repo,
+							sourceDescriptor,
+							marketplace: reference.displayLabel,
+							marketplaceReference: reference,
 							marketplaceType: def.type,
 							readmeUri: getMarketplaceReadmeUri(repo, source),
 						}];
 					});
+
+				cache.set(reference.canonicalId, {
+					plugins,
+					expiresAt: Date.now() + GITHUB_MARKETPLACE_CACHE_TTL_MS,
+					referenceRawValue: reference.rawValue,
+				});
+				this._savePersistedGitHubMarketplaceCache(cache);
+
+				return plugins;
 			} catch (err) {
 				this._logService.debug(`[PluginMarketplaceService] Failed to fetch marketplace.json from ${url}:`, err);
 				continue;
 			}
 		}
+
+		if (repoMayBePrivate) {
+			this._logService.debug(`[PluginMarketplaceService] ${repo} may be private, attempting clone-based marketplace discovery`);
+			return this._fetchFromClonedRepo(reference, token);
+		}
+
 		this._logService.debug(`[PluginMarketplaceService] No marketplace.json found in ${repo}`);
 		return [];
 	}
+
+	private _getCachedGitHubMarketplacePlugins(cache: Map<string, IGitHubMarketplaceCacheEntry>, cacheKey: string): IMarketplacePlugin[] | undefined {
+		const cached = cache.get(cacheKey);
+		if (!cached) {
+			return undefined;
+		}
+
+		if (cached.expiresAt <= Date.now()) {
+			cache.delete(cacheKey);
+			this._savePersistedGitHubMarketplaceCache(cache);
+			return undefined;
+		}
+
+		return [...cached.plugins];
+	}
+
+	private _loadPersistedGitHubMarketplaceCache(): Map<string, IGitHubMarketplaceCacheEntry> {
+		const cache = new Map<string, IGitHubMarketplaceCacheEntry>();
+		const now = Date.now();
+		const stored = this._storageService.getObject<IStoredGitHubMarketplaceCache>(GITHUB_MARKETPLACE_CACHE_STORAGE_KEY, StorageScope.APPLICATION);
+		if (!stored) {
+			return cache;
+		}
+
+		const revived = revive<IStoredGitHubMarketplaceCache>(stored);
+
+		for (const [cacheKey, entry] of Object.entries(revived)) {
+			if (!entry || !Array.isArray(entry.plugins) || typeof entry.expiresAt !== 'number' || entry.expiresAt <= now || typeof entry.referenceRawValue !== 'string') {
+				continue;
+			}
+
+			const reference = parseMarketplaceReference(entry.referenceRawValue);
+			if (!reference) {
+				continue;
+			}
+
+			const plugins = entry.plugins.map(plugin => ensureSourceDescriptor({
+				...plugin,
+				marketplace: reference.displayLabel,
+				marketplaceReference: reference,
+			}));
+
+			cache.set(cacheKey, {
+				plugins,
+				expiresAt: entry.expiresAt,
+				referenceRawValue: entry.referenceRawValue,
+			});
+		}
+
+		return cache;
+	}
+
+	private _savePersistedGitHubMarketplaceCache(cache: Map<string, IGitHubMarketplaceCacheEntry>): void {
+		const serialized: IStoredGitHubMarketplaceCache = {};
+		for (const [cacheKey, entry] of cache) {
+			if (!entry.plugins.length || entry.expiresAt <= Date.now()) {
+				continue;
+			}
+
+			serialized[cacheKey] = {
+				expiresAt: entry.expiresAt,
+				referenceRawValue: entry.referenceRawValue,
+				plugins: entry.plugins,
+			};
+		}
+
+		if (Object.keys(serialized).length === 0) {
+			this._storageService.remove(GITHUB_MARKETPLACE_CACHE_STORAGE_KEY, StorageScope.APPLICATION);
+			return;
+		}
+
+		this._storageService.store(
+			GITHUB_MARKETPLACE_CACHE_STORAGE_KEY,
+			JSON.stringify(serialized),
+			StorageScope.APPLICATION,
+			StorageTarget.MACHINE,
+		);
+	}
+
+	getMarketplacePluginMetadata(pluginUri: URI): IMarketplacePlugin | undefined {
+		const installed = this.installedPlugins.get();
+		return installed.find(e => isEqualOrParent(pluginUri, e.pluginUri))?.plugin;
+	}
+
+	addInstalledPlugin(pluginUri: URI, plugin: IMarketplacePlugin): void {
+		const current = this.installedPlugins.get();
+		const existing = current.find(e => isEqual(e.pluginUri, pluginUri));
+		if (existing) {
+			// Still update to trigger watchers to re-check, something might have happened that we want to know about
+			this._installedPluginsStore.set(current.map(c => c === existing ? { pluginUri, plugin, enabled: existing.enabled } : c), undefined);
+		} else {
+			this._installedPluginsStore.set([...current, { pluginUri, plugin, enabled: true }], undefined);
+		}
+	}
+
+	removeInstalledPlugin(pluginUri: URI): void {
+		const current = this.installedPlugins.get();
+		this._installedPluginsStore.set(current.filter(e => !isEqual(e.pluginUri, pluginUri)), undefined);
+	}
+
+	setInstalledPluginEnabled(pluginUri: URI, enabled: boolean): void {
+		const current = this.installedPlugins.get();
+		this._installedPluginsStore.set(
+			current.map(e => isEqual(e.pluginUri, pluginUri) ? { ...e, enabled } : e),
+			undefined,
+		);
+	}
+
+	isMarketplaceTrusted(ref: IMarketplaceReference): boolean {
+		return this._trustedMarketplacesStore.get().includes(ref.canonicalId);
+	}
+
+	trustMarketplace(ref: IMarketplaceReference): void {
+		const current = this._trustedMarketplacesStore.get();
+		if (!current.includes(ref.canonicalId)) {
+			this._trustedMarketplacesStore.set([...current, ref.canonicalId], undefined);
+		}
+	}
+
+	// --- Periodic update check ------------------------------------------------
+
+	private _isAutoUpdateEnabled(): AutoUpdateConfigurationValue {
+		return this._configurationService.getValue<AutoUpdateConfigurationValue>(AutoUpdateConfigurationKey);
+	}
+
+	/**
+	 * (Re-)schedules the next periodic update check. Called on
+	 * construction and whenever the auto-update config changes.
+	 */
+	private _scheduleUpdateCheck(): void {
+		if (this._updateCheckTimer !== undefined) {
+			clearTimeout(this._updateCheckTimer);
+			this._updateCheckTimer = undefined;
+		}
+
+		if (!this._isAutoUpdateEnabled()) {
+			return;
+		}
+
+		const lastCheck = this._storageService.getNumber(
+			PLUGIN_UPDATE_LAST_CHECK_STORAGE_KEY,
+			StorageScope.APPLICATION,
+			0,
+		);
+		const elapsed = Date.now() - lastCheck;
+		const delay = Math.max(0, PLUGIN_UPDATE_CHECK_INTERVAL_MS - elapsed);
+
+		this._updateCheckTimer = setTimeout(() => this._runUpdateCheck(), delay);
+	}
+
+	private async _runUpdateCheck(): Promise<void> {
+		this._updateCheckTimer = undefined;
+
+		try {
+			const installed = this.installedPlugins.get().filter(e => e.enabled);
+			if (installed.length === 0) {
+				return;
+			}
+
+			const seenMarketplaces = new Set<string>();
+			let hasUpdates = false;
+
+			for (const entry of installed) {
+				const ref = entry.plugin.marketplaceReference;
+				if (seenMarketplaces.has(ref.canonicalId)) {
+					continue;
+				}
+				seenMarketplaces.add(ref.canonicalId);
+
+				try {
+					const behind = await this._pluginRepositoryService.fetchRepository(ref);
+					if (behind) {
+						hasUpdates = true;
+						break;
+					}
+				} catch (err) {
+					this._logService.debug(`[PluginMarketplaceService] Update check failed for ${ref.displayLabel}:`, err);
+				}
+			}
+
+			this._hasUpdatesAvailable.set(hasUpdates, undefined);
+			this._storageService.store(
+				PLUGIN_UPDATE_LAST_CHECK_STORAGE_KEY,
+				Date.now(),
+				StorageScope.APPLICATION,
+				StorageTarget.MACHINE,
+			);
+		} catch (err) {
+			this._logService.debug('[PluginMarketplaceService] Periodic update check failed:', err);
+		} finally {
+			// Reschedule for the next check
+			if (this._isAutoUpdateEnabled()) {
+				this._updateCheckTimer = setTimeout(() => this._runUpdateCheck(), PLUGIN_UPDATE_CHECK_INTERVAL_MS);
+			}
+		}
+	}
+
+	private async _fetchFromClonedRepo(reference: IMarketplaceReference, token: CancellationToken): Promise<IMarketplacePlugin[]> {
+		let repoDir: URI;
+		try {
+			repoDir = await this._pluginRepositoryService.ensureRepository(reference);
+		} catch (err) {
+			this._logService.debug(`[PluginMarketplaceService] Failed to prepare marketplace repository ${reference.rawValue}:`, err);
+			return [];
+		}
+
+		return this._readPluginsFromDirectory(repoDir, reference, token);
+	}
+
+	async readPluginsFromDirectory(repoDir: URI, reference: IMarketplaceReference): Promise<IMarketplacePlugin[]> {
+		return this._readPluginsFromDirectory(repoDir, reference);
+	}
+
+	private async _readPluginsFromDirectory(repoDir: URI, reference: IMarketplaceReference, token?: CancellationToken): Promise<IMarketplacePlugin[]> {
+		for (const def of MARKETPLACE_DEFINITIONS) {
+			if (token?.isCancellationRequested) {
+				return [];
+			}
+
+			const definitionUri = joinPath(repoDir, def.path);
+			let json: IMarketplaceJson | undefined;
+			try {
+				const contents = await this._fileService.readFile(definitionUri);
+				json = parseJSONC(contents.value.toString()) as IMarketplaceJson | undefined;
+			} catch {
+				continue;
+			}
+
+			if (!json?.plugins || !Array.isArray(json.plugins)) {
+				this._logService.debug(`[PluginMarketplaceService] ${definitionUri.toString()} did not contain a valid plugins array, skipping`);
+				continue;
+			}
+
+			return json.plugins
+				.filter((p): p is { name: string; description?: string; version?: string; source?: string | IJsonPluginSource } =>
+					typeof p.name === 'string' && !!p.name
+				)
+				.flatMap(p => {
+					const sourceDescriptor = parsePluginSource(p.source, json.metadata?.pluginRoot, {
+						pluginName: p.name,
+						logService: this._logService,
+						logPrefix: `[PluginMarketplaceService]`,
+					});
+					if (!sourceDescriptor) {
+						return [];
+					}
+
+					const source = sourceDescriptor.kind === PluginSourceKind.RelativePath ? sourceDescriptor.path : '';
+
+					return [{
+						name: p.name,
+						description: p.description ?? '',
+						version: p.version ?? '',
+						source,
+						sourceDescriptor,
+						marketplace: reference.displayLabel,
+						marketplaceReference: reference,
+						marketplaceType: def.type,
+						readmeUri: getMarketplaceReadmeFileUri(repoDir, source),
+					}];
+				});
+		}
+
+		this._logService.debug(`[PluginMarketplaceService] No marketplace.json found in ${reference.rawValue}`);
+		return [];
+	}
 }
 
 function normalizeMarketplacePath(value: string): string {
@@ -155,8 +788,190 @@ function resolvePluginSource(pluginRoot: string | undefined, source: string): st
 	return relativePath(repoRoot, resolvedUri) ?? undefined;
 }
 
+/**
+ * Parse a raw `source` field from marketplace.json into a structured
+ * {@link IPluginSourceDescriptor}. Accepts either a relative-path string
+ * or a JSON object with a `source` discriminant indicating the kind.
+ */
+export function parsePluginSource(
+	rawSource: string | IJsonPluginSource | undefined,
+	pluginRoot: string | undefined,
+	logContext: { pluginName: string; logService: ILogService; logPrefix: string },
+): IPluginSourceDescriptor | undefined {
+	if (rawSource === undefined || rawSource === null) {
+		// Treat missing source the same as empty string → pluginRoot or repo root.
+		const resolved = resolvePluginSource(pluginRoot, '');
+		if (resolved === undefined) {
+			return undefined;
+		}
+		return { kind: PluginSourceKind.RelativePath, path: resolved };
+	}
+
+	// String source → legacy relative-path behaviour.
+	if (typeof rawSource === 'string') {
+		const resolved = resolvePluginSource(pluginRoot, rawSource);
+		if (resolved === undefined) {
+			return undefined;
+		}
+		return { kind: PluginSourceKind.RelativePath, path: resolved };
+	}
+
+	// Object source → discriminated by `rawSource.source`.
+	if (typeof rawSource !== 'object' || typeof rawSource.source !== 'string') {
+		logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': source object is missing a 'source' discriminant`);
+		return undefined;
+	}
+
+	switch (rawSource.source) {
+		case 'github': {
+			if (typeof rawSource.repo !== 'string' || !rawSource.repo) {
+				logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': github source is missing required 'repo' field`);
+				return undefined;
+			}
+			if (!isValidGitHubRepo(rawSource.repo)) {
+				logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': github source repo must be in 'owner/repo' format`);
+				return undefined;
+			}
+			if (!isOptionalString(rawSource.ref)) {
+				logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': github source 'ref' must be a string when provided`);
+				return undefined;
+			}
+			if (!isOptionalGitSha(rawSource.sha)) {
+				logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': github source 'sha' must be a full 40-character commit hash when provided`);
+				return undefined;
+			}
+			return {
+				kind: PluginSourceKind.GitHub,
+				repo: rawSource.repo,
+				ref: rawSource.ref,
+				sha: rawSource.sha,
+			};
+		}
+		case 'url': {
+			if (typeof rawSource.url !== 'string' || !rawSource.url) {
+				logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': url source is missing required 'url' field`);
+				return undefined;
+			}
+			if (!rawSource.url.toLowerCase().endsWith('.git')) {
+				logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': url source must end with '.git'`);
+				return undefined;
+			}
+			if (!isOptionalString(rawSource.ref)) {
+				logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': url source 'ref' must be a string when provided`);
+				return undefined;
+			}
+			if (!isOptionalGitSha(rawSource.sha)) {
+				logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': url source 'sha' must be a full 40-character commit hash when provided`);
+				return undefined;
+			}
+			return {
+				kind: PluginSourceKind.GitUrl,
+				url: rawSource.url,
+				ref: rawSource.ref,
+				sha: rawSource.sha,
+			};
+		}
+		case 'npm': {
+			if (typeof rawSource.package !== 'string' || !rawSource.package) {
+				logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': npm source is missing required 'package' field`);
+				return undefined;
+			}
+			if (!isOptionalString(rawSource.version) || !isOptionalString(rawSource.registry)) {
+				logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': npm source 'version' and 'registry' must be strings when provided`);
+				return undefined;
+			}
+			return {
+				kind: PluginSourceKind.Npm,
+				package: rawSource.package,
+				version: rawSource.version,
+				registry: rawSource.registry,
+			};
+		}
+		case 'pip': {
+			if (typeof rawSource.package !== 'string' || !rawSource.package) {
+				logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': pip source is missing required 'package' field`);
+				return undefined;
+			}
+			if (!isOptionalString(rawSource.version) || !isOptionalString(rawSource.registry)) {
+				logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': pip source 'version' and 'registry' must be strings when provided`);
+				return undefined;
+			}
+			return {
+				kind: PluginSourceKind.Pip,
+				package: rawSource.package,
+				version: rawSource.version,
+				registry: rawSource.registry,
+			};
+		}
+		default:
+			logContext.logService.warn(`${logContext.logPrefix} Skipping plugin '${logContext.pluginName}': unknown source kind '${rawSource.source}'`);
+			return undefined;
+	}
+}
+
+function isOptionalString(value: unknown): value is string | undefined {
+	return value === undefined || typeof value === 'string';
+}
+
+function isOptionalGitSha(value: unknown): value is string | undefined {
+	return value === undefined || (typeof value === 'string' && /^[0-9a-fA-F]{40}$/.test(value));
+}
+
+function isValidGitHubRepo(repo: string): boolean {
+	return /^[A-Za-z0-9_.-]+\/[A-Za-z0-9_.-]+$/.test(repo);
+}
+
+/**
+ * Returns a human-readable label for a plugin source descriptor,
+ * suitable for error messages and UI display.
+ */
+export function getPluginSourceLabel(descriptor: IPluginSourceDescriptor): string {
+	switch (descriptor.kind) {
+		case PluginSourceKind.RelativePath:
+			return descriptor.path || '.';
+		case PluginSourceKind.GitHub:
+			return descriptor.repo;
+		case PluginSourceKind.GitUrl:
+			return descriptor.url;
+		case PluginSourceKind.Npm:
+			return descriptor.version ? `${descriptor.package}@${descriptor.version}` : descriptor.package;
+		case PluginSourceKind.Pip:
+			return descriptor.version ? `${descriptor.package}==${descriptor.version}` : descriptor.package;
+	}
+}
+
+/**
+ * Returns `true` when the marketplace source descriptor differs from the
+ * installed one — meaning an update should be performed.
+ */
+export function hasSourceChanged(installed: IPluginSourceDescriptor, marketplace: IPluginSourceDescriptor): boolean {
+	if (installed.kind !== marketplace.kind) {
+		return true;
+	}
+
+	switch (installed.kind) {
+		case PluginSourceKind.GitHub:
+			return installed.ref !== (marketplace as typeof installed).ref
+				|| installed.sha !== (marketplace as typeof installed).sha;
+		case PluginSourceKind.GitUrl:
+			return installed.ref !== (marketplace as typeof installed).ref
+				|| installed.sha !== (marketplace as typeof installed).sha;
+		case PluginSourceKind.Npm:
+			return installed.version !== (marketplace as typeof installed).version;
+		case PluginSourceKind.Pip:
+			return installed.version !== (marketplace as typeof installed).version;
+		default:
+			return false;
+	}
+}
+
 function getMarketplaceReadmeUri(repo: string, source: string): URI {
 	const normalizedSource = source.trim().replace(/^\.?\/+|\/+$/g, '');
 	const readmePath = normalizedSource ? `${normalizedSource}/README.md` : 'README.md';
 	return URI.parse(`https://github.com/${repo}/blob/main/${readmePath}`);
 }
+
+function getMarketplaceReadmeFileUri(repoDir: URI, source: string): URI {
+	const normalizedSource = source.trim().replace(/^\.?\/+|\/+$/g, '');
+	return normalizedSource ? joinPath(repoDir, normalizedSource, 'README.md') : joinPath(repoDir, 'README.md');
+}
diff --git a/src/vs/workbench/contrib/chat/common/plugins/pluginSource.ts b/src/vs/workbench/contrib/chat/common/plugins/pluginSource.ts
new file mode 100644
index 0000000000000..dd5cd8385807e
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/plugins/pluginSource.ts
@@ -0,0 +1,64 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { URI } from '../../../../../base/common/uri.js';
+import { IEnsureRepositoryOptions, IPullRepositoryOptions } from './agentPluginRepositoryService.js';
+import { IMarketplacePlugin, IPluginSourceDescriptor, PluginSourceKind } from './pluginMarketplaceService.js';
+
+/**
+ * Per-kind strategy that centralizes install-path computation, source
+ * provisioning, update, label formatting, and uninstall cleanup for a
+ * single {@link PluginSourceKind}.
+ *
+ * Implementations are created via {@link IInstantiationService} so they
+ * can dependency-inject any services they need (git commands, file service,
+ * terminal service, etc.).
+ */
+export interface IPluginSource {
+	readonly kind: PluginSourceKind;
+
+	/**
+	 * Compute the local cache URI where this source's plugin files live.
+	 * @param cacheRoot The root cache directory for all agent plugins.
+	 */
+	getInstallUri(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI;
+
+	/**
+	 * Ensure the plugin source is available locally (clone, npm install, etc.).
+	 * Returns the install directory URI.
+	 */
+	ensure(cacheRoot: URI, plugin: IMarketplacePlugin, options?: IEnsureRepositoryOptions): Promise<URI>;
+
+	/**
+	 * Update an already-installed plugin source (git pull, npm update, etc.).
+	 * Returns `true` if the update brought in new changes.
+	 */
+	update(cacheRoot: URI, plugin: IMarketplacePlugin, options?: IPullRepositoryOptions): Promise<boolean>;
+
+	/**
+	 * Returns the on-disk directory to delete when this plugin is
+	 * uninstalled, or `undefined` if no cleanup is needed.
+	 *
+	 * Marketplace-relative sources return `undefined` because they share
+	 * a marketplace repository cache. Direct sources (github, url, npm,
+	 * pip) return the directory they own.
+	 */
+	getCleanupTarget(cacheRoot: URI, descriptor: IPluginSourceDescriptor): URI | undefined;
+
+	/**
+	 * Returns a human-readable label for a source descriptor of this kind,
+	 * suitable for error messages and UI display.
+	 */
+	getLabel(descriptor: IPluginSourceDescriptor): string;
+
+	/**
+	 * For package-manager sources (npm, pip): run the terminal install
+	 * command and return the resulting plugin directory, or `undefined`
+	 * if the user cancelled or the command failed.
+	 *
+	 * Not implemented by non-package-manager sources.
+	 */
+	runInstall?(installDir: URI, pluginDir: URI, plugin: IMarketplacePlugin, options?: { silent?: boolean }): Promise<{ pluginDir: URI } | undefined>;
+}
diff --git a/src/vs/workbench/contrib/chat/common/plugins/workspacePluginSettingsService.ts b/src/vs/workbench/contrib/chat/common/plugins/workspacePluginSettingsService.ts
new file mode 100644
index 0000000000000..4ccf86b083c58
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/plugins/workspacePluginSettingsService.ts
@@ -0,0 +1,312 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { parse as parseJSONC } from '../../../../../base/common/json.js';
+import { RunOnceScheduler } from '../../../../../base/common/async.js';
+import { Disposable, DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { autorun, derived, IObservable, observableFromEvent, observableValue } from '../../../../../base/common/observable.js';
+import { joinPath } from '../../../../../base/common/resources.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { IFileService } from '../../../../../platform/files/common/files.js';
+import { createDecorator } from '../../../../../platform/instantiation/common/instantiation.js';
+import { ILogService } from '../../../../../platform/log/common/log.js';
+import { IWorkspaceContextService } from '../../../../../platform/workspace/common/workspace.js';
+import { CLAUDE_CONFIG_FOLDER } from '../promptSyntax/config/promptFileLocations.js';
+import { IMarketplaceReference, parseMarketplaceReference } from './marketplaceReference.js';
+
+const SETTINGS_FILENAME = 'settings.json';
+const SETTINGS_LOCAL_FILENAME = 'settings.local.json';
+
+/** Copilot CLI settings folder inside `.github/`. */
+const COPILOT_CONFIG_FOLDER = '.github/copilot';
+
+/**
+ * Minimal representation of a marketplace entry from `extraKnownMarketplaces`.
+ */
+export interface IWorkspaceMarketplaceEntry {
+	readonly name: string;
+	readonly reference: IMarketplaceReference;
+}
+
+export const IWorkspacePluginSettingsService = createDecorator<IWorkspacePluginSettingsService>('workspacePluginSettingsService');
+
+export interface IWorkspacePluginSettingsService {
+	readonly _serviceBrand: undefined;
+
+	/**
+	 * Marketplace references parsed from `extraKnownMarketplaces` in workspace
+	 * settings files (`.claude/settings.json`, `.github/copilot/settings.json`).
+	 */
+	readonly extraMarketplaces: IObservable<readonly IWorkspaceMarketplaceEntry[]>;
+
+	/**
+	 * Plugin recommendation map parsed from `enabledPlugins` in workspace
+	 * settings files.
+	 * Keys are `"pluginName@marketplaceName"`, values indicate recommendation.
+	 */
+	readonly enabledPlugins: IObservable<ReadonlyMap<string, boolean>>;
+}
+
+// --- Parsing helpers ---------------------------------------------------------
+
+interface IMarketplaceSourceJson {
+	readonly source?: string;
+	readonly repo?: string;
+	readonly url?: string;
+	readonly path?: string;
+}
+
+interface IExtraMarketplaceJson {
+	readonly source?: string | IMarketplaceSourceJson;
+	readonly repo?: string;
+	readonly url?: string;
+	readonly path?: string;
+}
+
+/**
+ * Converts a single `extraKnownMarketplaces` entry into an
+ * {@link IMarketplaceReference} by mapping the source format to
+ * existing marketplace reference parsing.
+ */
+function marketplaceEntryToReference(entry: IExtraMarketplaceJson): IMarketplaceReference | undefined {
+	// Two shapes supported:
+	// 1. { source: "github", repo: "owner/repo" }   →  GitHub shorthand
+	// 2. { source: { source: "github", repo: "owner/repo" } }  →  nested
+	// 3. { source: "git", url: "https://..." }       →  Git URI
+
+	let sourceType: string | undefined;
+	let repo: string | undefined;
+	let url: string | undefined;
+
+	if (typeof entry.source === 'object' && entry.source !== null) {
+		const nested = entry.source;
+		sourceType = nested.source;
+		repo = nested.repo;
+		url = nested.url;
+	} else {
+		sourceType = entry.source as string | undefined;
+		repo = entry.repo;
+		url = entry.url;
+	}
+
+	if (sourceType === 'github' && typeof repo === 'string') {
+		return parseMarketplaceReference(repo);
+	}
+
+	if (sourceType === 'git' && typeof url === 'string') {
+		return parseMarketplaceReference(url);
+	}
+
+	return undefined;
+}
+
+/**
+ * Parses `enabledPlugins` from a JSON object.
+ */
+function parseEnabledPlugins(json: unknown): ReadonlyMap<string, boolean> {
+	const result = new Map<string, boolean>();
+
+	if (!json || typeof json !== 'object' || Array.isArray(json)) {
+		return result;
+	}
+
+	const obj = json as Record<string, unknown>;
+	for (const [key, value] of Object.entries(obj)) {
+		if (typeof value === 'boolean') {
+			result.set(key, value);
+		}
+	}
+
+	return result;
+}
+
+/**
+ * Parses `extraKnownMarketplaces` from a JSON object.
+ */
+function parseExtraMarketplaces(json: unknown, logPrefix: string, logService: ILogService): readonly IWorkspaceMarketplaceEntry[] {
+	const entries: IWorkspaceMarketplaceEntry[] = [];
+
+	if (!json || typeof json !== 'object' || Array.isArray(json)) {
+		return entries;
+	}
+
+	const obj = json as Record<string, unknown>;
+	for (const [name, value] of Object.entries(obj)) {
+		if (!value || typeof value !== 'object') {
+			logService.debug(`${logPrefix} Ignoring non-object extraKnownMarketplaces entry: ${name}`);
+			continue;
+		}
+
+		const reference = marketplaceEntryToReference(value as IExtraMarketplaceJson);
+		if (!reference) {
+			logService.debug(`${logPrefix} Could not parse marketplace reference for: ${name}`);
+			continue;
+		}
+
+		// Override displayLabel with the user-chosen marketplace name so that
+		// fetched plugins use this name in their `marketplace` field, which is
+		// what `enabledPlugins` keys reference (e.g. "plugin@claude-settings").
+		entries.push({ name, reference: { ...reference, displayLabel: name } });
+	}
+
+	return entries;
+}
+
+// --- Settings reader (reusable per config folder) ----------------------------
+
+interface IWorkspaceSettingsData {
+	readonly marketplaces: readonly IWorkspaceMarketplaceEntry[];
+	readonly enabledPlugins: ReadonlyMap<string, boolean>;
+}
+
+const EMPTY_DATA: IWorkspaceSettingsData = { marketplaces: [], enabledPlugins: new Map() };
+
+/**
+ * Reads `enabledPlugins` and `extraKnownMarketplaces` from a pair of
+ * `settings.json` / `settings.local.json` files inside a given config
+ * folder (e.g. `.claude/` or `.github/copilot/`) across all workspace
+ * folders. Watches for changes and exposes results as an observable.
+ */
+class WorkspaceSettingsReader extends Disposable {
+
+	private readonly _data = observableValue<IWorkspaceSettingsData>('data', EMPTY_DATA);
+	readonly data: IObservable<IWorkspaceSettingsData> = this._data;
+
+	constructor(
+		/** Workspace-relative config folder (e.g. `.claude`). */
+		configFolder: string,
+		logPrefix: string,
+		fileService: IFileService,
+		workspaceContextService: IWorkspaceContextService,
+		private readonly _logService: ILogService,
+	) {
+		super();
+
+		const settingsDirs = observableFromEvent(
+			this,
+			workspaceContextService.onDidChangeWorkspaceFolders,
+			() => workspaceContextService.getWorkspace().folders.map(f => joinPath(f.uri, configFolder)),
+		);
+
+		const watcherStore = this._register(new DisposableStore());
+		this._register(autorun(reader => {
+			const dirs = settingsDirs.read(reader);
+			watcherStore.clear();
+
+			// Coalesce rapid file-change events into a single read.
+			const scheduler = new RunOnceScheduler(() => this._readSettings(dirs, logPrefix, fileService), 100);
+			watcherStore.add(scheduler);
+
+			for (const dir of dirs) {
+				const watcher = fileService.createWatcher(dir, { recursive: false, excludes: [] });
+				watcherStore.add(watcher);
+				watcherStore.add(watcher.onDidChange(e => {
+					if (e.affects(joinPath(dir, SETTINGS_FILENAME)) || e.affects(joinPath(dir, SETTINGS_LOCAL_FILENAME))) {
+						scheduler.schedule();
+					}
+				}));
+			}
+
+			// Perform initial read immediately.
+			this._readSettings(dirs, logPrefix, fileService);
+		}));
+	}
+
+	private async _readSettings(dirs: readonly URI[], logPrefix: string, fileService: IFileService): Promise<void> {
+		const allMarketplaces: IWorkspaceMarketplaceEntry[] = [];
+		const mergedEnabled = new Map<string, boolean>();
+
+		for (const dir of dirs) {
+			const sharedUri = joinPath(dir, SETTINGS_FILENAME);
+			const localUri = joinPath(dir, SETTINGS_LOCAL_FILENAME);
+
+			for (const uri of [sharedUri, localUri]) {
+				try {
+					const content = await fileService.readFile(uri);
+					const json = parseJSONC(content.value.toString());
+
+					if (!json || typeof json !== 'object') {
+						continue;
+					}
+
+					const root = json as Record<string, unknown>;
+
+					const marketplaces = parseExtraMarketplaces(root.extraKnownMarketplaces, logPrefix, this._logService);
+					for (const entry of marketplaces) {
+						if (!allMarketplaces.some(e => e.reference.canonicalId === entry.reference.canonicalId)) {
+							allMarketplaces.push(entry);
+						}
+					}
+
+					const enabled = parseEnabledPlugins(root.enabledPlugins);
+					for (const [key, value] of enabled) {
+						mergedEnabled.set(key, value);
+					}
+				} catch {
+					this._logService.debug(`${logPrefix} Could not read ${uri.toString()}`);
+				}
+			}
+		}
+
+		this._data.set({ marketplaces: allMarketplaces, enabledPlugins: mergedEnabled }, undefined);
+	}
+}
+
+// --- Aggregating service implementation --------------------------------------
+
+export class WorkspacePluginSettingsService extends Disposable implements IWorkspacePluginSettingsService {
+	declare readonly _serviceBrand: undefined;
+
+	readonly extraMarketplaces: IObservable<readonly IWorkspaceMarketplaceEntry[]>;
+	readonly enabledPlugins: IObservable<ReadonlyMap<string, boolean>>;
+
+	constructor(
+		@IFileService fileService: IFileService,
+		@IWorkspaceContextService workspaceContextService: IWorkspaceContextService,
+		@ILogService logService: ILogService,
+	) {
+		super();
+
+		const claudeReader = this._register(new WorkspaceSettingsReader(
+			CLAUDE_CONFIG_FOLDER, '[ClaudePluginSettings]',
+			fileService, workspaceContextService, logService,
+		));
+
+		const copilotReader = this._register(new WorkspaceSettingsReader(
+			COPILOT_CONFIG_FOLDER, '[CopilotPluginSettings]',
+			fileService, workspaceContextService, logService,
+		));
+
+		// Merge marketplaces from all readers, deduplicating by canonical ID.
+		this.extraMarketplaces = derived(reader => {
+			const claude = claudeReader.data.read(reader).marketplaces;
+			const copilot = copilotReader.data.read(reader).marketplaces;
+			const byCanonicalId = new Map<string, IWorkspaceMarketplaceEntry>();
+			for (const entry of [...claude, ...copilot]) {
+				if (!byCanonicalId.has(entry.reference.canonicalId)) {
+					byCanonicalId.set(entry.reference.canonicalId, entry);
+				}
+			}
+			return [...byCanonicalId.values()];
+		});
+
+		// Merge enabledPlugins from all readers. Claude entries take
+		// precedence for keys that exist in both (first-writer wins).
+		this.enabledPlugins = derived(reader => {
+			const claude = claudeReader.data.read(reader).enabledPlugins;
+			const copilot = copilotReader.data.read(reader).enabledPlugins;
+			const merged = new Map<string, boolean>();
+			for (const [key, value] of claude) {
+				merged.set(key, value);
+			}
+			for (const [key, value] of copilot) {
+				if (!merged.has(key)) {
+					merged.set(key, value);
+				}
+			}
+			return merged;
+		});
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/computeAutomaticInstructions.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/computeAutomaticInstructions.ts
index 62b01c294e54c..0cfdc0b14d324 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/computeAutomaticInstructions.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/computeAutomaticInstructions.ts
@@ -12,6 +12,7 @@ import { basename, dirname } from '../../../../../base/common/resources.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { localize } from '../../../../../nls.js';
 import { IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
+import { IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
 import { IFileService } from '../../../../../platform/files/common/files.js';
 import { ILabelService } from '../../../../../platform/label/common/label.js';
 import { ILogService } from '../../../../../platform/log/common/log.js';
@@ -24,6 +25,7 @@ import { PromptsConfig } from './config/config.js';
 import { isInClaudeAgentsFolder, isInClaudeRulesFolder, isPromptOrInstructionsFile } from './config/promptFileLocations.js';
 import { ParsedPromptFile } from './promptFileParser.js';
 import { AgentFileType, ICustomAgent, IPromptPath, IPromptsService } from './service/promptsService.js';
+import { AGENT_DEBUG_LOG_ENABLED_SETTING, AGENT_DEBUG_LOG_FILE_LOGGING_ENABLED_SETTING, TROUBLESHOOT_SKILL_PATH } from './promptTypes.js';
 import { OffsetRange } from '../../../../../editor/common/core/ranges/offsetRange.js';
 import { ChatConfiguration, ChatModeKind } from '../constants.js';
 import { UserSelectedTools } from '../participants/chatAgents.js';
@@ -63,11 +65,12 @@ export class ComputeAutomaticInstructions {
 		private readonly _modeKind: ChatModeKind,
 		private readonly _enabledTools: UserSelectedTools | undefined,
 		private readonly _enabledSubagents: (readonly string[]) | undefined,
-		private readonly _sessionId: string | undefined,
+		private readonly _sessionResource: URI | undefined,
 		@IPromptsService private readonly _promptsService: IPromptsService,
 		@ILogService public readonly _logService: ILogService,
 		@ILabelService private readonly _labelService: ILabelService,
 		@IConfigurationService private readonly _configurationService: IConfigurationService,
+		@IContextKeyService private readonly _contextKeyService: IContextKeyService,
 		@IWorkspaceContextService private readonly _workspaceService: IWorkspaceContextService,
 		@IFileService private readonly _fileService: IFileService,
 		@IRemoteAgentService private readonly _remoteAgentService: IRemoteAgentService,
@@ -93,7 +96,7 @@ export class ComputeAutomaticInstructions {
 
 	public async collect(variables: ChatRequestVariableSet, token: CancellationToken): Promise<void> {
 
-		const instructionFiles = await this._promptsService.getInstructionFiles(token, this._sessionId);
+		const instructionFiles = await this._promptsService.getInstructionFiles(token, this._sessionResource);
 
 		this._logService.trace(`[InstructionsContextComputer] ${instructionFiles.length} instruction files available.`);
 
@@ -109,9 +112,9 @@ export class ComputeAutomaticInstructions {
 		// get copilot instructions
 		await this._addAgentInstructions(variables, telemetryEvent, token);
 
-		const instructionsListVariable = await this._getInstructionsWithPatternsList(instructionFiles, variables, telemetryEvent, token);
-		if (instructionsListVariable) {
-			variables.add(instructionsListVariable);
+		const customizationsIndexVariable = await this._getCustomizationsIndex(instructionFiles, variables, telemetryEvent, token);
+		if (customizationsIndexVariable) {
+			variables.add(customizationsIndexVariable);
 			telemetryEvent.listedInstructionsCount++;
 		}
 
@@ -293,7 +296,7 @@ export class ComputeAutomaticInstructions {
 		return undefined;
 	}
 
-	private async _getInstructionsWithPatternsList(instructionFiles: readonly IPromptPath[], _existingVariables: ChatRequestVariableSet, telemetryEvent: InstructionsCollectionEvent, token: CancellationToken): Promise<IPromptTextVariableEntry | undefined> {
+	private async _getCustomizationsIndex(instructionFiles: readonly IPromptPath[], _existingVariables: ChatRequestVariableSet, telemetryEvent: InstructionsCollectionEvent, token: CancellationToken): Promise<IPromptTextVariableEntry | undefined> {
 		const readTool = this._getTool('readFile');
 		const runSubagentTool = this._getTool(VSCodeToolReference.runSubagent);
 
@@ -354,9 +357,24 @@ export class ComputeAutomaticInstructions {
 				entries.push('</instructions>', '', ''); // add trailing newline
 			}
 
-			const agentSkills = await this._promptsService.findAgentSkills(token, this._sessionId);
+			const agentSkills = await this._promptsService.findAgentSkills(token, this._sessionResource);
 			// Filter out skills with disableModelInvocation=true (they can only be triggered manually via /name)
-			const modelInvocableSkills = agentSkills?.filter(skill => !skill.disableModelInvocation);
+			// Also filter by `when` clause using the scoped context key service
+			// Also filter out the troubleshoot skill when the feature flags are disabled
+			const isDebugLogEnabled = this._configurationService.getValue<boolean>(AGENT_DEBUG_LOG_ENABLED_SETTING);
+			const isFileLoggingEnabled = this._configurationService.getValue<boolean>(AGENT_DEBUG_LOG_FILE_LOGGING_ENABLED_SETTING);
+			const modelInvocableSkills = agentSkills?.filter(skill => {
+				if (skill.disableModelInvocation) {
+					return false;
+				}
+				if (skill.when && !this._contextKeyService.contextMatchesRules(skill.when)) {
+					return false;
+				}
+				if ((!isDebugLogEnabled || !isFileLoggingEnabled) && skill.uri.path.includes(TROUBLESHOOT_SKILL_PATH)) {
+					return false;
+				}
+				return true;
+			});
 			if (modelInvocableSkills && modelInvocableSkills.length > 0) {
 				const useSkillAdherencePrompt = this._configurationService.getValue(PromptsConfig.USE_SKILL_ADHERENCE_PROMPT);
 				entries.push('<skills>');
@@ -400,7 +418,7 @@ export class ComputeAutomaticInstructions {
 					return (agent: ICustomAgent) => subagents.includes(agent.name);
 				}
 			})();
-			const agents = await this._promptsService.getCustomAgents(token, this._sessionId);
+			const agents = await this._promptsService.getCustomAgents(token, this._sessionResource);
 			if (agents.length > 0) {
 				entries.push('<agents>');
 				entries.push('Here is a list of agents that can be used when running a subagent.');
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/config/config.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/config/config.ts
index 1f0b9da69ca91..d72cc6b32a663 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/config/config.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/config/config.ts
@@ -115,6 +115,11 @@ export namespace PromptsConfig {
 	 */
 	export const USE_CLAUDE_HOOKS = 'chat.useClaudeHooks';
 
+	/**
+	 * Configuration key for enabling hooks defined in custom agent frontmatter.
+	 */
+	export const USE_CUSTOM_AGENT_HOOKS = 'chat.useCustomAgentHooks';
+
 	/**
 	 * Configuration key for enabling stronger skill adherence prompt (experimental).
 	 */
@@ -130,6 +135,11 @@ export namespace PromptsConfig {
 	 */
 	export const INCLUDE_REFERENCED_INSTRUCTIONS = 'chat.includeReferencedInstructions';
 
+	/**
+	 * Search for configuration files in parent repositories of the workspace folder
+	 */
+	export const USE_CUSTOMIZATIONS_IN_PARENT_REPOS = 'chat.useCustomizationsInParentRepositories';
+
 	/**
 	 * Get value of the `reusable prompt locations` configuration setting.
 	 * @see {@link PROMPT_LOCATIONS_CONFIG_KEY}, {@link INSTRUCTIONS_LOCATIONS_CONFIG_KEY}, {@link MODE_LOCATIONS_CONFIG_KEY}, {@link SKILLS_LOCATION_KEY}.
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/config/promptFileLocations.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/config/promptFileLocations.ts
index ed04e3aa641e2..6e360f9d8b351 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/config/promptFileLocations.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/config/promptFileLocations.ts
@@ -60,6 +60,10 @@ export const CLAUDE_CONFIG_FOLDER = '.claude';
  */
 export const COPILOT_CUSTOM_INSTRUCTIONS_FILENAME = 'copilot-instructions.md';
 
+/**
+ * GitHub configuration folder name.
+ */
+export const GITHUB_CONFIG_FOLDER = '.github';
 
 /**
  * Default reusable prompt files source folder.
@@ -86,6 +90,11 @@ export const AGENTS_SOURCE_FOLDER = '.github/agents';
  */
 export const CLAUDE_AGENTS_SOURCE_FOLDER = '.claude/agents';
 
+/**
+ * Copilot user agents folder.
+ */
+export const COPILOT_USER_AGENTS_SOURCE_FOLDER = '~/.copilot/agents';
+
 /**
  * Claude rules folder.
  */
@@ -111,6 +120,8 @@ export enum PromptFileSource {
 	ConfigPersonal = 'config-personal',
 	ExtensionContribution = 'extension-contribution',
 	ExtensionAPI = 'extension-api',
+	Plugin = 'plugin',
+	Internal = 'internal',
 }
 
 /**
@@ -127,6 +138,8 @@ export interface IPromptSourceFolder {
  */
 export interface IResolvedPromptSourceFolder {
 	readonly uri: URI;
+	readonly parent: URI; // matches the URI when no glob pattern is used
+	readonly filePattern: string | undefined; // the part of the path with the glob pattern, or undefined if no glob pattern is used
 	readonly source: PromptFileSource;
 	readonly storage: PromptsStorage;
 	/**
@@ -184,6 +197,8 @@ export const DEFAULT_PROMPT_SOURCE_FOLDERS: readonly IPromptSourceFolder[] = [
 export const DEFAULT_AGENT_SOURCE_FOLDERS: readonly IPromptSourceFolder[] = [
 	{ path: AGENTS_SOURCE_FOLDER, source: PromptFileSource.GitHubWorkspace, storage: PromptsStorage.local },
 	{ path: CLAUDE_AGENTS_SOURCE_FOLDER, source: PromptFileSource.ClaudeWorkspace, storage: PromptsStorage.local },
+	{ path: '~/' + CLAUDE_AGENTS_SOURCE_FOLDER, source: PromptFileSource.ClaudePersonal, storage: PromptsStorage.user },
+	{ path: COPILOT_USER_AGENTS_SOURCE_FOLDER, source: PromptFileSource.CopilotPersonal, storage: PromptsStorage.user },
 ];
 
 /**
@@ -194,6 +209,7 @@ export const DEFAULT_HOOK_FILE_PATHS: readonly IPromptSourceFolder[] = [
 	{ path: '.github/hooks', source: PromptFileSource.GitHubWorkspace, storage: PromptsStorage.local },
 	{ path: '.claude/settings.local.json', source: PromptFileSource.ClaudeWorkspaceLocal, storage: PromptsStorage.local },
 	{ path: '.claude/settings.json', source: PromptFileSource.ClaudeWorkspace, storage: PromptsStorage.local },
+	{ path: '~/.copilot/hooks', source: PromptFileSource.CopilotPersonal, storage: PromptsStorage.user },
 	{ path: '~/.claude/settings.json', source: PromptFileSource.ClaudePersonal, storage: PromptsStorage.user },
 ];
 
@@ -202,7 +218,7 @@ export const DEFAULT_HOOK_FILE_PATHS: readonly IPromptSourceFolder[] = [
  */
 function isInAgentsFolder(fileUri: URI): boolean {
 	const dir = dirname(fileUri.path);
-	return dir.endsWith('/' + AGENTS_SOURCE_FOLDER) || dir.endsWith('/' + CLAUDE_AGENTS_SOURCE_FOLDER);
+	return dir.endsWith('/' + AGENTS_SOURCE_FOLDER) || dir.endsWith('/' + CLAUDE_AGENTS_SOURCE_FOLDER) || isInCopilotAgentsFolder(fileUri);
 }
 
 /**
@@ -213,6 +229,14 @@ export function isInClaudeAgentsFolder(fileUri: URI): boolean {
 	return dir.endsWith('/' + CLAUDE_AGENTS_SOURCE_FOLDER);
 }
 
+/**
+ * Helper function to check if a file is directly in the ~/.copilot/agents/ folder.
+ */
+export function isInCopilotAgentsFolder(fileUri: URI): boolean {
+	const dir = dirname(fileUri.path);
+	return dir.endsWith(COPILOT_USER_AGENTS_SOURCE_FOLDER.substring(1));
+}
+
 /**
  * Helper function to check if a file is inside the .claude/rules/ folder (including subfolders).
  * Claude rules files (.md) in this folder are treated as instruction files.
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/hookClaudeCompat.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/hookClaudeCompat.ts
index eb567363a8ece..9311488d61c7e 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/hookClaudeCompat.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/hookClaudeCompat.ts
@@ -4,23 +4,11 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { URI } from '../../../../../base/common/uri.js';
-import { HookType, IHookCommand, toHookType, resolveHookCommand } from './hookSchema.js';
+import { toHookType, IHookCommand, extractHookCommandsFromItem } from './hookSchema.js';
+import { HOOKS_BY_TARGET, HookType } from './hookTypes.js';
+import { Target } from './promptTypes.js';
 
-/**
- * Maps Claude hook type names to our abstract HookType.
- * Claude uses PascalCase and slightly different names.
- * @see https://docs.anthropic.com/en/docs/claude-code/hooks
- */
-export const CLAUDE_HOOK_TYPE_MAP: Record<string, HookType> = {
-	'SessionStart': HookType.SessionStart,
-	'UserPromptSubmit': HookType.UserPromptSubmit,
-	'PreToolUse': HookType.PreToolUse,
-	'PostToolUse': HookType.PostToolUse,
-	'PreCompact': HookType.PreCompact,
-	'SubagentStart': HookType.SubagentStart,
-	'SubagentStop': HookType.SubagentStop,
-	'Stop': HookType.Stop,
-};
+export { extractHookCommandsFromItem };
 
 /**
  * Cached inverse mapping from HookType to Claude hook type name.
@@ -31,7 +19,7 @@ let _hookTypeToClaudeName: Map<HookType, string> | undefined;
 function getHookTypeToClaudeNameMap(): Map<HookType, string> {
 	if (!_hookTypeToClaudeName) {
 		_hookTypeToClaudeName = new Map();
-		for (const [claudeName, hookType] of Object.entries(CLAUDE_HOOK_TYPE_MAP)) {
+		for (const [claudeName, hookType] of Object.entries(HOOKS_BY_TARGET[Target.Claude])) {
 			_hookTypeToClaudeName.set(hookType, claudeName);
 		}
 	}
@@ -42,7 +30,7 @@ function getHookTypeToClaudeNameMap(): Map<HookType, string> {
  * Resolves a Claude hook type name to our abstract HookType.
  */
 export function resolveClaudeHookType(name: string): HookType | undefined {
-	return CLAUDE_HOOK_TYPE_MAP[name];
+	return HOOKS_BY_TARGET[Target.Claude][name];
 }
 
 /**
@@ -146,60 +134,4 @@ export function parseClaudeHooks(
 	return { hooks: result, disabledAllHooks: false };
 }
 
-/**
- * Helper to extract hook commands from an item that could be:
- * 1. A direct command object: { type: 'command', command: '...' }
- * 2. A nested structure with matcher (Claude style): { matcher: '...', hooks: [{ type: 'command', command: '...' }] }
- *
- * This allows Copilot format to handle Claude-style entries if pasted.
- * Also handles Claude's leniency where 'type' field can be omitted.
- */
-export function extractHookCommandsFromItem(
-	item: unknown,
-	workspaceRootUri: URI | undefined,
-	userHome: string
-): IHookCommand[] {
-	if (!item || typeof item !== 'object') {
-		return [];
-	}
-
-	const itemObj = item as Record<string, unknown>;
-	const commands: IHookCommand[] = [];
 
-	// Check for nested hooks with matcher (Claude style): { matcher: "...", hooks: [...] }
-	const nestedHooks = itemObj.hooks;
-	if (nestedHooks !== undefined && Array.isArray(nestedHooks)) {
-		for (const nestedHook of nestedHooks) {
-			if (!nestedHook || typeof nestedHook !== 'object') {
-				continue;
-			}
-			const normalized = normalizeForResolve(nestedHook as Record<string, unknown>);
-			const resolved = resolveHookCommand(normalized, workspaceRootUri, userHome);
-			if (resolved) {
-				commands.push(resolved);
-			}
-		}
-	} else {
-		// Direct command object
-		const normalized = normalizeForResolve(itemObj);
-		const resolved = resolveHookCommand(normalized, workspaceRootUri, userHome);
-		if (resolved) {
-			commands.push(resolved);
-		}
-	}
-
-	return commands;
-}
-
-/**
- * Normalizes a hook command object for resolving.
- * Claude format allows omitting the 'type' field, treating it as 'command'.
- * This ensures compatibility when Claude-style hooks are pasted into Copilot format.
- */
-function normalizeForResolve(raw: Record<string, unknown>): Record<string, unknown> {
-	// If type is missing or already 'command', ensure it's set to 'command'
-	if (raw.type === undefined || raw.type === 'command') {
-		return { ...raw, type: 'command' };
-	}
-	return raw;
-}
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/hookCompatibility.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/hookCompatibility.ts
index d00fd26cb1eef..64e46956b17ae 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/hookCompatibility.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/hookCompatibility.ts
@@ -5,9 +5,10 @@
 
 import { URI } from '../../../../../base/common/uri.js';
 import { basename, dirname } from '../../../../../base/common/path.js';
-import { HookType, IHookCommand, toHookType } from './hookSchema.js';
+import { IHookCommand, toHookType } from './hookSchema.js';
 import { parseClaudeHooks, extractHookCommandsFromItem } from './hookClaudeCompat.js';
 import { resolveCopilotCliHookType } from './hookCopilotCliCompat.js';
+import { HookType } from './hookTypes.js';
 
 /**
  * Represents a hook source with its original and normalized properties.
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/hookCopilotCliCompat.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/hookCopilotCliCompat.ts
index 16ca9a825ae81..9bf9c6b1076c1 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/hookCopilotCliCompat.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/hookCopilotCliCompat.ts
@@ -3,18 +3,10 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { HookType } from './hookSchema.js';
+import { HOOKS_BY_TARGET, HookType } from './hookTypes.js';
+import { Target } from './promptTypes.js';
 
-/**
- * Maps Copilot CLI hook type names to our abstract HookType.
- * Copilot CLI uses camelCase names.
- */
-export const COPILOT_CLI_HOOK_TYPE_MAP: Record<string, HookType> = {
-	'sessionStart': HookType.SessionStart,
-	'userPromptSubmitted': HookType.UserPromptSubmit,
-	'preToolUse': HookType.PreToolUse,
-	'postToolUse': HookType.PostToolUse,
-};
+const COPILOT_CLI_HOOK_TYPE_MAP: Record<string, HookType> = HOOKS_BY_TARGET[Target.GitHubCopilot];
 
 /**
  * Cached inverse mapping from HookType to Copilot CLI hook type name.
@@ -36,7 +28,7 @@ function getHookTypeToCopilotCliNameMap(): Map<HookType, string> {
  * Resolves a Copilot CLI hook type name to our abstract HookType.
  */
 export function resolveCopilotCliHookType(name: string): HookType | undefined {
-	return COPILOT_CLI_HOOK_TYPE_MAP[name];
+	return (COPILOT_CLI_HOOK_TYPE_MAP as Record<string, HookType>)[name];
 }
 
 /**
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/hookSchema.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/hookSchema.ts
index ccf368ed54a06..8025b3ea67598 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/hookSchema.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/hookSchema.ts
@@ -10,71 +10,9 @@ import { joinPath } from '../../../../../base/common/resources.js';
 import { isAbsolute } from '../../../../../base/common/path.js';
 import { untildify } from '../../../../../base/common/labels.js';
 import { OperatingSystem } from '../../../../../base/common/platform.js';
-
-/**
- * Enum of available hook types that can be configured in hooks .json
- */
-export enum HookType {
-	SessionStart = 'SessionStart',
-	UserPromptSubmit = 'UserPromptSubmit',
-	PreToolUse = 'PreToolUse',
-	PostToolUse = 'PostToolUse',
-	PreCompact = 'PreCompact',
-	SubagentStart = 'SubagentStart',
-	SubagentStop = 'SubagentStop',
-	Stop = 'Stop',
-}
-
-/**
- * String literal type derived from HookType enum values.
- */
-export type HookTypeValue = `${HookType}`;
-
-/**
- * Metadata for hook types including localized labels and descriptions
- */
-export const HOOK_TYPES = [
-	{
-		id: HookType.SessionStart,
-		label: nls.localize('hookType.sessionStart.label', "Session Start"),
-		description: nls.localize('hookType.sessionStart.description', "Executed when a new agent session begins.")
-	},
-	{
-		id: HookType.UserPromptSubmit,
-		label: nls.localize('hookType.userPromptSubmit.label', "User Prompt Submit"),
-		description: nls.localize('hookType.userPromptSubmit.description', "Executed when the user submits a prompt to the agent.")
-	},
-	{
-		id: HookType.PreToolUse,
-		label: nls.localize('hookType.preToolUse.label', "Pre-Tool Use"),
-		description: nls.localize('hookType.preToolUse.description', "Executed before the agent uses any tool.")
-	},
-	{
-		id: HookType.PostToolUse,
-		label: nls.localize('hookType.postToolUse.label', "Post-Tool Use"),
-		description: nls.localize('hookType.postToolUse.description', "Executed after a tool completes execution successfully.")
-	},
-	{
-		id: HookType.PreCompact,
-		label: nls.localize('hookType.preCompact.label', "Pre-Compact"),
-		description: nls.localize('hookType.preCompact.description', "Executed before the agent compacts the conversation context.")
-	},
-	{
-		id: HookType.SubagentStart,
-		label: nls.localize('hookType.subagentStart.label', "Subagent Start"),
-		description: nls.localize('hookType.subagentStart.description', "Executed when a subagent is started.")
-	},
-	{
-		id: HookType.SubagentStop,
-		label: nls.localize('hookType.subagentStop.label', "Subagent Stop"),
-		description: nls.localize('hookType.subagentStop.description', "Executed when a subagent stops.")
-	},
-	{
-		id: HookType.Stop,
-		label: nls.localize('hookType.stop.label', "Stop"),
-		description: nls.localize('hookType.stop.description', "Executed when the agent stops.")
-	}
-] as const;
+import { HookType, HOOKS_BY_TARGET, HOOK_METADATA } from './hookTypes.js';
+import { Target } from './promptTypes.js';
+import { IValue, IMapValue } from './promptFileParser.js';
 
 /**
  * A single hook command configuration.
@@ -105,22 +43,52 @@ export interface IHookCommand {
  * Collected hooks for a chat request, organized by hook type.
  * This is passed to the extension host so it knows what hooks are available.
  */
-export interface IChatRequestHooks {
-	readonly [HookType.SessionStart]?: readonly IHookCommand[];
-	readonly [HookType.UserPromptSubmit]?: readonly IHookCommand[];
-	readonly [HookType.PreToolUse]?: readonly IHookCommand[];
-	readonly [HookType.PostToolUse]?: readonly IHookCommand[];
-	readonly [HookType.PreCompact]?: readonly IHookCommand[];
-	readonly [HookType.SubagentStart]?: readonly IHookCommand[];
-	readonly [HookType.SubagentStop]?: readonly IHookCommand[];
-	readonly [HookType.Stop]?: readonly IHookCommand[];
+export type ChatRequestHooks = {
+	readonly [K in HookType]?: readonly IHookCommand[];
+};
+
+/**
+ * Merges two sets of hooks by concatenating the command arrays for each hook type.
+ * Additional hooks are appended after the base hooks.
+ */
+export function mergeHooks(base: ChatRequestHooks | undefined, additional: ChatRequestHooks): ChatRequestHooks {
+	if (!base) {
+		return additional;
+	}
+
+	const result: Partial<Record<HookType, readonly IHookCommand[]>> = { ...base };
+	for (const hookType of Object.values(HookType)) {
+		const baseArr = base[hookType];
+		const additionalArr = additional[hookType];
+		if (additionalArr && additionalArr.length > 0) {
+			result[hookType] = baseArr ? [...baseArr, ...additionalArr] : additionalArr;
+		}
+	}
+	return result as ChatRequestHooks;
 }
 
+/**
+ * Descriptions for hook command fields, used by both the JSON schema and the hover provider.
+ */
+export const HOOK_COMMAND_FIELD_DESCRIPTIONS: Record<string, string> = {
+	type: nls.localize('hook.type', 'Must be "command".'),
+	command: nls.localize('hook.command', 'The command to execute. This is the default cross-platform command.'),
+	windows: nls.localize('hook.windows', 'Windows-specific command. If specified and running on Windows, this overrides the "command" field.'),
+	linux: nls.localize('hook.linux', 'Linux-specific command. If specified and running on Linux, this overrides the "command" field.'),
+	osx: nls.localize('hook.osx', 'macOS-specific command. If specified and running on macOS, this overrides the "command" field.'),
+	bash: nls.localize('hook.bash', 'Bash command for Linux and macOS.'),
+	powershell: nls.localize('hook.powershell', 'PowerShell command for Windows.'),
+	cwd: nls.localize('hook.cwd', 'Working directory for the script (relative to repository root).'),
+	env: nls.localize('hook.env', 'Additional environment variables that are merged with the existing environment.'),
+	timeout: nls.localize('hook.timeout', 'Maximum execution time in seconds (default: 30).'),
+	timeoutSec: nls.localize('hook.timeoutSec', 'Maximum execution time in seconds (default: 10).'),
+};
+
 /**
  * JSON Schema for GitHub Copilot hook configuration files.
  * Hooks enable executing custom shell commands at strategic points in an agent's workflow.
  */
-const hookCommandSchema: IJSONSchema = {
+const vscodeHookCommandSchema: IJSONSchema = {
 	type: 'object',
 	additionalProperties: true,
 	required: ['type'],
@@ -137,46 +105,118 @@ const hookCommandSchema: IJSONSchema = {
 		type: {
 			type: 'string',
 			enum: ['command'],
-			description: nls.localize('hook.type', 'Must be "command".')
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.type
 		},
 		command: {
 			type: 'string',
-			description: nls.localize('hook.command', 'The command to execute. This is the default cross-platform command.')
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.command
 		},
 		windows: {
 			type: 'string',
-			description: nls.localize('hook.windows', 'Windows-specific command. If specified and running on Windows, this overrides the "command" field.')
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.windows
 		},
 		linux: {
 			type: 'string',
-			description: nls.localize('hook.linux', 'Linux-specific command. If specified and running on Linux, this overrides the "command" field.')
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.linux
 		},
 		osx: {
 			type: 'string',
-			description: nls.localize('hook.osx', 'macOS-specific command. If specified and running on macOS, this overrides the "command" field.')
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.osx
 		},
 		cwd: {
 			type: 'string',
-			description: nls.localize('hook.cwd', 'Working directory for the script (relative to repository root).')
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.cwd
 		},
 		env: {
 			type: 'object',
 			additionalProperties: { type: 'string' },
-			description: nls.localize('hook.env', 'Additional environment variables that are merged with the existing environment.')
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.env
 		},
 		timeout: {
 			type: 'number',
 			default: 30,
-			description: nls.localize('hook.timeout', 'Maximum execution time in seconds (default: 30).')
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.timeout
 		}
 	}
 };
 
 const hookArraySchema: IJSONSchema = {
 	type: 'array',
-	items: hookCommandSchema
+	items: vscodeHookCommandSchema
+};
+
+/**
+ * Builds JSON Schema hook properties for a given target by looking up
+ * the hook keys from HOOKS_BY_TARGET and descriptions from HOOK_METADATA.
+ */
+function buildHookProperties(target: Target, arraySchema: IJSONSchema): Record<string, IJSONSchema> {
+	return Object.fromEntries(
+		Object.entries(HOOKS_BY_TARGET[target]).map(([key, hookType]) => [
+			key,
+			{ ...arraySchema, description: HOOK_METADATA[hookType]?.description }
+		])
+	);
+}
+
+/**
+ * Hook properties for the VS Code format.
+ */
+const vscodeHookProperties: Record<string, IJSONSchema> = buildHookProperties(Target.VSCode, hookArraySchema);
+
+/**
+ * Hook command schema for the Copilot CLI format.
+ * Adds `bash`, `powershell`, and `timeoutSec` fields alongside the standard ones.
+ */
+const copilotCliHookCommandSchema: IJSONSchema = {
+	type: 'object',
+	additionalProperties: true,
+	required: ['type'],
+	anyOf: [
+		{ required: ['bash'] },
+		{ required: ['powershell'] }
+	],
+	errorMessage: nls.localize('hook.cliCommandRequired', 'At least one of "bash" or "powershell" must be specified.'),
+	properties: {
+		type: {
+			type: 'string',
+			enum: ['command'],
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.type
+		},
+		bash: {
+			type: 'string',
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.bash
+		},
+		powershell: {
+			type: 'string',
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.powershell
+		},
+		cwd: {
+			type: 'string',
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.cwd
+		},
+		env: {
+			type: 'object',
+			additionalProperties: { type: 'string' },
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.env
+		},
+		timeoutSec: {
+			type: 'number',
+			default: 10,
+			description: HOOK_COMMAND_FIELD_DESCRIPTIONS.timeoutSec
+		}
+	}
+};
+
+const copilotCliHookArraySchema: IJSONSchema = {
+	type: 'array',
+	items: copilotCliHookCommandSchema
 };
 
+/**
+ * Hook properties for the Copilot CLI format.
+ */
+const copilotCliHookProperties: Record<string, IJSONSchema> = buildHookProperties(Target.GitHubCopilot, copilotCliHookArraySchema);
+
 export const hookFileSchema: IJSONSchema = {
 	$schema: 'http://json-schema.org/draft-07/schema#',
 	type: 'object',
@@ -188,39 +228,33 @@ export const hookFileSchema: IJSONSchema = {
 			type: 'object',
 			description: nls.localize('hookFile.hooks', 'Hook definitions organized by type.'),
 			additionalProperties: true,
-			properties: {
-				SessionStart: {
-					...hookArraySchema,
-					description: nls.localize('hookFile.sessionStart', 'Executed when a new agent session begins. Use to initialize environments, log session starts, validate project state, or set up temporary resources.')
-				},
-				UserPromptSubmit: {
-					...hookArraySchema,
-					description: nls.localize('hookFile.userPromptSubmit', 'Executed when the user submits a prompt to the agent. Use to log user requests for auditing and usage analysis.')
-				},
-				PreToolUse: {
-					...hookArraySchema,
-					description: nls.localize('hookFile.preToolUse', 'Executed before the agent uses any tool. This is the most powerful hook as it can approve or deny tool executions. Use to block dangerous commands, enforce security policies, require approval for sensitive operations, or log tool usage.')
-				},
-				PostToolUse: {
-					...hookArraySchema,
-					description: nls.localize('hookFile.postToolUse', 'Executed after a tool completes execution successfully. Use to log execution results, track usage statistics, generate audit trails, or monitor performance.')
-				},
-				PreCompact: {
-					...hookArraySchema,
-					description: nls.localize('hookFile.preCompact', 'Executed before the agent compacts the conversation context. Use to save conversation state, export important information, or prepare for context reduction.')
-				},
-				SubagentStart: {
-					...hookArraySchema,
-					description: nls.localize('hookFile.subagentStart', 'Executed when a subagent is started. Use to log subagent spawning, track nested agent usage, or initialize subagent-specific resources.')
-				},
-				SubagentStop: {
-					...hookArraySchema,
-					description: nls.localize('hookFile.subagentStop', 'Executed when a subagent stops. Use to log subagent completion, cleanup subagent resources, or aggregate subagent results.')
-				},
-				Stop: {
-					...hookArraySchema,
-					description: nls.localize('hookFile.stop', 'Executed when the agent session stops. Use to cleanup resources, generate final reports, or send completion notifications.')
-				}
+		}
+	},
+	// Conditionally apply PascalCase or camelCase hook properties based on
+	// whether the file uses the Copilot CLI format (detected by the "version" field).
+	if: {
+		required: ['version'],
+		properties: {
+			version: { type: 'number' }
+		}
+	},
+	then: {
+		// Copilot CLI format: camelCase hook names, bash/powershell/timeoutSec fields
+		properties: {
+			version: {
+				type: 'number',
+				description: nls.localize('hookFile.version', 'Hook configuration format version.'),
+			},
+			hooks: {
+				properties: copilotCliHookProperties
+			}
+		}
+	},
+	else: {
+		// VS Code / PascalCase format
+		properties: {
+			hooks: {
+				properties: vscodeHookProperties
 			}
 		}
 	},
@@ -254,11 +288,6 @@ export const hookFileSchema: IJSONSchema = {
  */
 export const HOOK_SCHEMA_URI = 'vscode://schemas/hooks';
 
-/**
- * Glob pattern for hook files.
- */
-export const HOOK_FILE_GLOB = '.github/hooks/*.json';
-
 /**
  * Normalizes a raw hook type identifier to the canonical HookType enum value.
  * Only matches exact enum values. For tool-specific naming conventions (e.g., Claude, Copilot CLI),
@@ -408,13 +437,6 @@ export function formatHookCommandLabel(hook: IHookCommand, os: OperatingSystem):
 	if (!command) {
 		return '';
 	}
-
-	// Add platform badge if using platform-specific override
-	if (isUsingPlatformOverride(hook, os)) {
-		const platformLabel = getPlatformLabel(os);
-		return `[${platformLabel}] ${command}`;
-	}
-
 	return command;
 }
 
@@ -460,3 +482,155 @@ export function resolveHookCommand(raw: Record<string, unknown>, workspaceRootUr
 		...(normalized.timeout !== undefined && { timeout: normalized.timeout }),
 	};
 }
+
+/**
+ * Helper to extract hook commands from an item that could be:
+ * 1. A direct command object: { type: 'command', command: '...' }
+ * 2. A nested structure with matcher (Claude style): { matcher: '...', hooks: [{ type: 'command', command: '...' }] }
+ *
+ * This allows Copilot format to handle Claude-style entries if pasted.
+ * Also handles Claude's leniency where 'type' field can be omitted.
+ */
+export function extractHookCommandsFromItem(
+	item: unknown,
+	workspaceRootUri: URI | undefined,
+	userHome: string
+): IHookCommand[] {
+	if (!item || typeof item !== 'object') {
+		return [];
+	}
+
+	const itemObj = item as Record<string, unknown>;
+	const commands: IHookCommand[] = [];
+
+	// Check for nested hooks with matcher (Claude style): { matcher: "...", hooks: [...] }
+	const nestedHooks = itemObj.hooks;
+	if (nestedHooks !== undefined && Array.isArray(nestedHooks)) {
+		for (const nestedHook of nestedHooks) {
+			if (!nestedHook || typeof nestedHook !== 'object') {
+				continue;
+			}
+			const normalized = normalizeForResolve(nestedHook as Record<string, unknown>);
+			const resolved = resolveHookCommand(normalized, workspaceRootUri, userHome);
+			if (resolved) {
+				commands.push(resolved);
+			}
+		}
+	} else {
+		// Direct command object
+		const normalized = normalizeForResolve(itemObj);
+		const resolved = resolveHookCommand(normalized, workspaceRootUri, userHome);
+		if (resolved) {
+			commands.push(resolved);
+		}
+	}
+
+	return commands;
+}
+
+/**
+ * Normalizes a hook command object for resolving.
+ * Claude format allows omitting the 'type' field, treating it as 'command'.
+ * This ensures compatibility when Claude-style hooks are pasted into Copilot format.
+ */
+function normalizeForResolve(raw: Record<string, unknown>): Record<string, unknown> {
+	// If type is missing or already 'command', ensure it's set to 'command'
+	if (raw.type === undefined || raw.type === 'command') {
+		return { ...raw, type: 'command' };
+	}
+	return raw;
+}
+
+/**
+ * Converts an {@link IValue} YAML AST node into a plain JavaScript value
+ * (string, array, or object) suitable for passing to hook parsing helpers.
+ */
+function yamlValueToPlain(value: IValue): unknown {
+	switch (value.type) {
+		case 'scalar':
+			return value.value;
+		case 'sequence':
+			return value.items.map(yamlValueToPlain);
+		case 'map': {
+			const obj: Record<string, unknown> = {};
+			for (const prop of value.properties) {
+				obj[prop.key.value] = yamlValueToPlain(prop.value);
+			}
+			return obj;
+		}
+	}
+}
+
+/**
+ * Parses hooks from a subagent's YAML frontmatter `hooks` attribute.
+ *
+ * Supports two formats for hook entries:
+ *
+ * 1. **Direct command** (our format, without matcher):
+ * ```yaml
+ * hooks:
+ *   PreToolUse:
+ *     - type: command
+ *       command: "./scripts/validate.sh"
+ * ```
+ *
+ * 2. **Nested with matcher** (Claude Code format):
+ * ```yaml
+ * hooks:
+ *   PreToolUse:
+ *     - matcher: "Bash"
+ *       hooks:
+ *         - type: command
+ *           command: "./scripts/validate.sh"
+ * ```
+ *
+ * @param hooksMap The raw YAML map value from the `hooks` frontmatter attribute.
+ * @param workspaceRootUri Workspace root for resolving relative `cwd` paths.
+ * @param userHome User home directory path for tilde expansion.
+ * @param target The agent's target, used to resolve hook type names correctly.
+ * @returns Resolved hooks organized by hook type, ready for use in {@link ChatRequestHooks}.
+ */
+export function parseSubagentHooksFromYaml(
+	hooksMap: IMapValue,
+	workspaceRootUri: URI | undefined,
+	userHome: string,
+	target: Target = Target.Undefined,
+): ChatRequestHooks {
+	const result: Record<string, IHookCommand[]> = {};
+	const targetHookMap = HOOKS_BY_TARGET[target] ?? HOOKS_BY_TARGET[Target.Undefined];
+
+	for (const prop of hooksMap.properties) {
+		const hookTypeName = prop.key.value;
+
+		// Resolve hook type name using the target's own map first, then fall back to canonical names
+		const hookType = targetHookMap[hookTypeName] ?? toHookType(hookTypeName);
+		if (!hookType) {
+			continue;
+		}
+
+		// The value must be a sequence (array of hook entries)
+		if (prop.value.type !== 'sequence') {
+			continue;
+		}
+
+		const commands: IHookCommand[] = [];
+
+		for (const item of prop.value.items) {
+			// Convert the YAML AST node to a plain object so the existing
+			// extractHookCommandsFromItem helper can handle both direct
+			// commands and nested matcher structures.
+			const plainItem = yamlValueToPlain(item);
+			const extracted = extractHookCommandsFromItem(plainItem, workspaceRootUri, userHome);
+			commands.push(...extracted);
+		}
+
+		if (commands.length > 0) {
+			if (!result[hookType]) {
+				result[hookType] = [];
+			}
+			result[hookType].push(...commands);
+		}
+	}
+
+	return result as ChatRequestHooks;
+}
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/hookTypes.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/hookTypes.ts
new file mode 100644
index 0000000000000..66d28c22876eb
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/hookTypes.ts
@@ -0,0 +1,122 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as nls from '../../../../../nls.js';
+import { Target } from './promptTypes.js';
+
+/**
+ * Enum of hook types across all targets. For the set of supported hooks per target, see HOOKS_BY_TARGET.
+ */
+export enum HookType {
+	SessionStart = 'SessionStart',
+	SessionEnd = 'SessionEnd',
+	UserPromptSubmit = 'UserPromptSubmit',
+	PreToolUse = 'PreToolUse',
+	PostToolUse = 'PostToolUse',
+	PreCompact = 'PreCompact',
+	SubagentStart = 'SubagentStart',
+	SubagentStop = 'SubagentStop',
+	Stop = 'Stop',
+	ErrorOccurred = 'ErrorOccurred',
+}
+
+/**
+ * String literal type derived from HookType enum values.
+ */
+export type HookTypeValue = `${HookType}`;
+
+export const HOOKS_BY_TARGET: Record<Target, Record<string, HookType>> = {
+	// see https://code.visualstudio.com/docs/copilot/customization/hooks#_hook-lifecycle-events
+	[Target.VSCode]: {
+		'SessionStart': HookType.SessionStart,
+		'UserPromptSubmit': HookType.UserPromptSubmit,
+		'PreToolUse': HookType.PreToolUse,
+		'PostToolUse': HookType.PostToolUse,
+		'PreCompact': HookType.PreCompact,
+		'SubagentStart': HookType.SubagentStart,
+		'SubagentStop': HookType.SubagentStop,
+		'Stop': HookType.Stop,
+	},
+	// see https://docs.github.com/en/copilot/concepts/agents/coding-agent/about-hooks#types-of-hooks
+	[Target.GitHubCopilot]: {
+		'sessionStart': HookType.SessionStart,
+		'sessionEnd': HookType.SessionEnd,
+		'userPromptSubmitted': HookType.UserPromptSubmit,
+		'preToolUse': HookType.PreToolUse,
+		'postToolUse': HookType.PostToolUse,
+		'agentStop': HookType.Stop,
+		'subagentStop': HookType.SubagentStop,
+		'errorOccurred': HookType.ErrorOccurred
+	},
+	// see https://docs.anthropic.com/en/docs/claude-code/hooks
+	[Target.Claude]: {
+		'SessionStart': HookType.SessionStart,
+		'UserPromptSubmit': HookType.UserPromptSubmit,
+		'PreToolUse': HookType.PreToolUse,
+		'PostToolUse': HookType.PostToolUse,
+		'PreCompact': HookType.PreCompact,
+		'SubagentStart': HookType.SubagentStart,
+		'SubagentStop': HookType.SubagentStop,
+		'Stop': HookType.Stop,
+	},
+	// if no target, just list all known hook types.
+	[Target.Undefined]: Object.fromEntries(
+		Object.values(HookType).map(h => [h, h])
+	) as Record<string, HookType>
+};
+
+/**
+ * Metadata for a hook type including localized label and description.
+ */
+export interface IHookTypeMeta {
+	readonly label: string;
+	readonly description: string;
+}
+
+/**
+ * Metadata for hook types including localized labels and descriptions
+ */
+export const HOOK_METADATA: { [key in HookType]: IHookTypeMeta } = {
+	[HookType.SessionStart]: {
+		label: nls.localize('hookType.sessionStart.label', "Session Start"),
+		description: nls.localize('hookType.sessionStart.description', "Executed when a new agent session begins.")
+	},
+	[HookType.UserPromptSubmit]: {
+		label: nls.localize('hookType.userPromptSubmit.label', "User Prompt Submit"),
+		description: nls.localize('hookType.userPromptSubmit.description', "Executed when the user submits a prompt to the agent.")
+	},
+	[HookType.PreToolUse]: {
+		label: nls.localize('hookType.preToolUse.label', "Pre-Tool Use"),
+		description: nls.localize('hookType.preToolUse.description', "Executed before the agent uses any tool.")
+	},
+	[HookType.PostToolUse]: {
+		label: nls.localize('hookType.postToolUse.label', "Post-Tool Use"),
+		description: nls.localize('hookType.postToolUse.description', "Executed after a tool completes execution successfully.")
+	},
+	[HookType.PreCompact]: {
+		label: nls.localize('hookType.preCompact.label', "Pre-Compact"),
+		description: nls.localize('hookType.preCompact.description', "Executed before the agent compacts the conversation context.")
+	},
+	[HookType.SubagentStart]: {
+		label: nls.localize('hookType.subagentStart.label', "Subagent Start"),
+		description: nls.localize('hookType.subagentStart.description', "Executed when a subagent is started.")
+	},
+	[HookType.SubagentStop]: {
+		label: nls.localize('hookType.subagentStop.label', "Subagent Stop"),
+		description: nls.localize('hookType.subagentStop.description', "Executed when a subagent stops.")
+	},
+	[HookType.Stop]: {
+		label: nls.localize('hookType.stop.label', "Stop"),
+		description: nls.localize('hookType.stop.description', "Executed when the agent stops.")
+	},
+	[HookType.SessionEnd]: {
+		label: nls.localize('hookType.sessionEnd.label', "Session End"),
+		description: nls.localize('hookType.sessionEnd.description', "Executed when an agent session ends.")
+	},
+	[HookType.ErrorOccurred]: {
+		label: nls.localize('hookType.errorOccurred.label', "Error Occurred"),
+		description: nls.localize('hookType.errorOccurred.description', "Executed when an error occurs during the agent session.")
+	}
+};
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/internalCustomizations/internalCustomizations.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/internalCustomizations/internalCustomizations.ts
new file mode 100644
index 0000000000000..2d13b4be1f48a
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/internalCustomizations/internalCustomizations.ts
@@ -0,0 +1,75 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Disposable } from '../../../../../../base/common/lifecycle.js';
+import { URI } from '../../../../../../base/common/uri.js';
+import { IFileService } from '../../../../../../platform/files/common/files.js';
+import { IAgentSkill, IInternalPromptPath, PromptsStorage } from '../service/promptsService.js';
+import { PromptsType } from '../promptTypes.js';
+import { registerChatInternalFileSystem } from './internalPromptFileSystem.js';
+import { InternalSkill } from './internalSkill.js';
+export { InternalSkill } from './internalSkill.js';
+
+/**
+ * Manages built-in internal customizations (skills, instructions, agents, etc.)
+ * backed by a readonly virtual filesystem.
+ *
+ * To add a new internal skill, create an {@link InternalSkill} instance and
+ * register it in the constructor.
+ */
+export class ChatInternalCustomizations extends Disposable {
+
+	private readonly skills: readonly InternalSkill[];
+	private readonly skillsByUri = new Map<string, InternalSkill>();
+
+	constructor(fileService: IFileService) {
+		super();
+
+		const { provider, disposable: fsDisposable } = registerChatInternalFileSystem(fileService);
+		this._register(fsDisposable);
+
+		// --- Built-in skills (add new entries here) ---
+		this.skills = [];
+
+		for (const skill of this.skills) {
+			provider.registerFile(skill.uri, skill.content);
+			this.skillsByUri.set(skill.uri.toString(), skill);
+			this._register(skill);
+		}
+
+	}
+
+	/**
+	 * Returns the {@link IAgentSkill} metadata for all internal skills,
+	 * for injection into the skills list.
+	 */
+	getSkills(): readonly IAgentSkill[] {
+		return this.skills.map(s => s.skill);
+	}
+
+	/**
+	 * Looks up the {@link InternalSkill} instance for a given URI,
+	 * e.g. to check its {@link InternalSkill.when} clause.
+	 */
+	getInternalSkillByUri(uri: URI): InternalSkill | undefined {
+		return this.skillsByUri.get(uri.toString());
+	}
+
+	/**
+	 * Returns internal prompt file paths for a given customization type.
+	 */
+	getPromptPaths(type: PromptsType): readonly IInternalPromptPath[] {
+		if (type === PromptsType.skill) {
+			return this.skills.map(s => ({
+				uri: s.uri,
+				storage: PromptsStorage.internal as const,
+				type,
+				name: s.name,
+				description: s.description,
+			}));
+		}
+		return [];
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/internalCustomizations/internalPromptFileSystem.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/internalCustomizations/internalPromptFileSystem.ts
new file mode 100644
index 0000000000000..c75a1759b8a68
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/internalCustomizations/internalPromptFileSystem.ts
@@ -0,0 +1,129 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { VSBuffer } from '../../../../../../base/common/buffer.js';
+import { Event } from '../../../../../../base/common/event.js';
+import { Disposable, IDisposable } from '../../../../../../base/common/lifecycle.js';
+import { URI } from '../../../../../../base/common/uri.js';
+import { createFileSystemProviderError, FileSystemProviderCapabilities, FileSystemProviderErrorCode, FileType, IFileDeleteOptions, IFileOverwriteOptions, IFileService, IFileSystemProviderWithFileReadWriteCapability, IFileWriteOptions, IStat } from '../../../../../../platform/files/common/files.js';
+
+/**
+ * URI scheme for internal chat prompt files (skills, instructions, agents, etc.)
+ * backed by a readonly virtual filesystem.
+ */
+export const CHAT_INTERNAL_SCHEME = 'vscode-chat-internal';
+
+/**
+ * A readonly virtual filesystem provider for internal chat prompt files.
+ *
+ * Files are registered at startup via {@link registerFile} and cannot be
+ * modified or deleted afterwards.
+ */
+export class ChatInternalFileSystemProvider extends Disposable implements IFileSystemProviderWithFileReadWriteCapability {
+
+	private readonly files = new Map<string, Uint8Array>();
+
+	readonly onDidChangeCapabilities = Event.None;
+	readonly onDidChangeFile = Event.None;
+
+	readonly capabilities = FileSystemProviderCapabilities.FileReadWrite
+		| FileSystemProviderCapabilities.Readonly
+		| FileSystemProviderCapabilities.PathCaseSensitive;
+
+	/**
+	 * Register a file with static content. Must be called before the
+	 * file can be read. Typically called once at startup.
+	 */
+	registerFile(uri: URI, content: string): void {
+		this.files.set(uri.toString(), VSBuffer.fromString(content).buffer);
+	}
+
+	// --- IFileSystemProvider ---
+
+	watch(): IDisposable {
+		return Disposable.None;
+	}
+
+	async stat(resource: URI): Promise<IStat> {
+		const data = this.files.get(resource.toString());
+		if (data) {
+			return {
+				type: FileType.File,
+				ctime: 0,
+				mtime: 0,
+				size: data.byteLength,
+			};
+		}
+		// Check if this is a directory (any registered file has this as prefix)
+		const prefix = resource.toString() + '/';
+		for (const key of this.files.keys()) {
+			if (key.startsWith(prefix)) {
+				return { type: FileType.Directory, ctime: 0, mtime: 0, size: 0 };
+			}
+		}
+		throw createFileSystemProviderError('file not found', FileSystemProviderErrorCode.FileNotFound);
+	}
+
+	async mkdir(): Promise<void> {
+		throw createFileSystemProviderError('readonly filesystem', FileSystemProviderErrorCode.NoPermissions);
+	}
+
+	async readdir(resource: URI): Promise<[string, FileType][]> {
+		const prefix = resource.toString() + '/';
+		const entries = new Map<string, FileType>();
+		for (const key of this.files.keys()) {
+			if (key.startsWith(prefix)) {
+				const rest = key.substring(prefix.length);
+				const slash = rest.indexOf('/');
+				if (slash === -1) {
+					entries.set(rest, FileType.File);
+				} else {
+					entries.set(rest.substring(0, slash), FileType.Directory);
+				}
+			}
+		}
+		return [...entries.entries()];
+	}
+
+	async delete(_resource: URI, _opts: IFileDeleteOptions): Promise<void> {
+		throw createFileSystemProviderError('readonly filesystem', FileSystemProviderErrorCode.NoPermissions);
+	}
+
+	async rename(_from: URI, _to: URI, _opts: IFileOverwriteOptions): Promise<void> {
+		throw createFileSystemProviderError('readonly filesystem', FileSystemProviderErrorCode.NoPermissions);
+	}
+
+	async readFile(resource: URI): Promise<Uint8Array> {
+		const data = this.files.get(resource.toString());
+		if (data) {
+			return data;
+		}
+		throw createFileSystemProviderError('file not found', FileSystemProviderErrorCode.FileNotFound);
+	}
+
+	async writeFile(_resource: URI, _content: Uint8Array, _opts: IFileWriteOptions): Promise<void> {
+		throw createFileSystemProviderError('readonly filesystem', FileSystemProviderErrorCode.NoPermissions);
+	}
+}
+
+/**
+ * Registers the internal chat filesystem provider with the file service,
+ * populates it with built-in files, and returns both the provider (for
+ * event subscription) and a disposable for cleanup.
+ */
+export function registerChatInternalFileSystem(fileService: IFileService): { provider: ChatInternalFileSystemProvider; disposable: IDisposable } {
+	const provider = new ChatInternalFileSystemProvider();
+	const registration = fileService.registerProvider(CHAT_INTERNAL_SCHEME, provider);
+
+	return {
+		provider,
+		disposable: {
+			dispose() {
+				registration.dispose();
+				provider.dispose();
+			}
+		}
+	};
+}
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/internalCustomizations/internalSkill.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/internalCustomizations/internalSkill.ts
new file mode 100644
index 0000000000000..7303fceefa421
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/internalCustomizations/internalSkill.ts
@@ -0,0 +1,58 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Disposable } from '../../../../../../base/common/lifecycle.js';
+import { URI } from '../../../../../../base/common/uri.js';
+import { ContextKeyExpression } from '../../../../../../platform/contextkey/common/contextkey.js';
+import { IAgentSkill, PromptsStorage } from '../service/promptsService.js';
+import { CHAT_INTERNAL_SCHEME } from './internalPromptFileSystem.js';
+
+/**
+ * A built-in skill backed by the internal readonly virtual filesystem.
+ *
+ * To add a new internal skill, create an instance documenting the skill
+ * name, description and SKILL.md content, then add it to the
+ * {@link internalSkills} array in {@link internalCustomizations.ts}.
+ */
+export class InternalSkill extends Disposable {
+
+	/** Virtual filesystem URI for the SKILL.md file. */
+	readonly uri: URI;
+
+	/** The skill metadata exposed to the skills list and system prompt. */
+	readonly skill: IAgentSkill;
+
+	/**
+	 * Optional context key expression. When set, the skill is only included
+	 * in the system prompt when this expression evaluates to true.
+	 */
+	readonly when: ContextKeyExpression | undefined;
+
+	constructor(
+		readonly name: string,
+		readonly description: string,
+		readonly content: string,
+		options?: {
+			disableModelInvocation?: boolean;
+			userInvocable?: boolean;
+			when?: ContextKeyExpression;
+		},
+	) {
+		super();
+		this.uri = URI.from({
+			scheme: CHAT_INTERNAL_SCHEME,
+			path: `/skills/${name}/SKILL.md`,
+		});
+		this.skill = {
+			uri: this.uri,
+			storage: PromptsStorage.internal,
+			name,
+			description,
+			disableModelInvocation: options?.disableModelInvocation ?? false,
+			userInvocable: options?.userInvocable ?? true,
+		};
+		this.when = options?.when;
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/PromptHeaderDefinitionProvider.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/PromptHeaderDefinitionProvider.ts
index 8de8c06dfba12..b991d1d4db579 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/PromptHeaderDefinitionProvider.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/PromptHeaderDefinitionProvider.ts
@@ -9,8 +9,8 @@ import { Range } from '../../../../../../editor/common/core/range.js';
 import { Definition, DefinitionProvider } from '../../../../../../editor/common/languages.js';
 import { ITextModel } from '../../../../../../editor/common/model.js';
 import { IChatModeService } from '../../chatModes.js';
-import { getPromptsTypeForLanguageId } from '../promptTypes.js';
 import { PromptHeaderAttributes } from '../promptFileParser.js';
+import { getPromptsTypeForLanguageId } from '../promptTypes.js';
 import { IPromptsService } from '../service/promptsService.js';
 
 export class PromptHeaderDefinitionProvider implements DefinitionProvider {
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptCodeActions.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptCodeActions.ts
index 704d5cd620815..eba207145d155 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptCodeActions.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptCodeActions.ts
@@ -16,9 +16,10 @@ import { Selection } from '../../../../../../editor/common/core/selection.js';
 import { Lazy } from '../../../../../../base/common/lazy.js';
 import { LEGACY_MODE_FILE_EXTENSION } from '../config/promptFileLocations.js';
 import { IFileService } from '../../../../../../platform/files/common/files.js';
-import { getTarget, isVSCodeOrDefaultTarget, MARKERS_OWNER_ID } from './promptValidator.js';
+import { MARKERS_OWNER_ID } from './promptValidator.js';
 import { IMarkerData, IMarkerService } from '../../../../../../platform/markers/common/markers.js';
 import { CodeActionKind } from '../../../../../../editor/contrib/codeAction/common/types.js';
+import { getTarget, isVSCodeOrDefaultTarget } from './promptFileAttributes.js';
 
 export class PromptCodeActionProvider implements CodeActionProvider {
 	/**
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptDocumentSemanticTokensProvider.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptDocumentSemanticTokensProvider.ts
index 3fdf4aa385e58..8b5ffb7ae41e8 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptDocumentSemanticTokensProvider.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptDocumentSemanticTokensProvider.ts
@@ -8,7 +8,7 @@ import { DocumentSemanticTokensProvider, ProviderResult, SemanticTokens, Semanti
 import { ITextModel } from '../../../../../../editor/common/model.js';
 import { getPromptsTypeForLanguageId } from '../promptTypes.js';
 import { IPromptsService } from '../service/promptsService.js';
-import { getTarget, isVSCodeOrDefaultTarget } from './promptValidator.js';
+import { getTarget, isVSCodeOrDefaultTarget } from './promptFileAttributes.js';
 
 export class PromptDocumentSemanticTokensProvider implements DocumentSemanticTokensProvider {
 	/**
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptFileAttributes.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptFileAttributes.ts
new file mode 100644
index 0000000000000..a57216523c997
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptFileAttributes.ts
@@ -0,0 +1,440 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { dirname } from '../../../../../../base/common/resources.js';
+import { URI } from '../../../../../../base/common/uri.js';
+import { localize } from '../../../../../../nls.js';
+import { SpecedToolAliases } from '../../tools/languageModelToolsService.js';
+import { CLAUDE_AGENTS_SOURCE_FOLDER, isInClaudeRulesFolder } from '../config/promptFileLocations.js';
+import { PromptHeader, PromptHeaderAttributes } from '../promptFileParser.js';
+import { PromptsType, Target } from '../promptTypes.js';
+
+export namespace GithubPromptHeaderAttributes {
+	export const mcpServers = 'mcp-servers';
+	export const github = 'github';
+}
+
+export namespace ClaudeHeaderAttributes {
+	export const disallowedTools = 'disallowedTools';
+}
+
+export function isTarget(value: unknown): value is Target {
+	return value === Target.VSCode || value === Target.GitHubCopilot || value === Target.Claude || value === Target.Undefined;
+}
+
+
+interface IAttributeDefinition {
+	readonly type: string;
+	readonly description: string;
+	readonly defaults?: readonly string[];
+	readonly items?: readonly { name: string; description?: string }[];
+	readonly enums?: readonly { name: string; description?: string }[];
+}
+
+const booleanAttributeEnumValues: readonly IValueEntry[] = [
+	{ name: 'true' },
+	{ name: 'false' }
+];
+
+const targetAttributeEnumValues: readonly IValueEntry[] = [
+	{ name: 'vscode' },
+	{ name: 'github-copilot' },
+];
+
+// Attribute metadata for prompt files (`*.prompt.md`).
+export const promptFileAttributes: Record<string, IAttributeDefinition> = {
+	[PromptHeaderAttributes.name]: {
+		type: 'scalar',
+		description: localize('promptHeader.prompt.name', 'The name of the prompt. This is also the name of the slash command that will run this prompt.'),
+	},
+	[PromptHeaderAttributes.description]: {
+		type: 'scalar',
+		description: localize('promptHeader.prompt.description', 'The description of the reusable prompt, what it does and when to use it.'),
+	},
+	[PromptHeaderAttributes.argumentHint]: {
+		type: 'scalar',
+		description: localize('promptHeader.prompt.argumentHint', 'The argument-hint describes what inputs the prompt expects or supports.'),
+	},
+	[PromptHeaderAttributes.model]: {
+		type: 'scalar | sequence',
+		description: localize('promptHeader.prompt.model', 'The model to use in this prompt. Can also be a list of models. The first available model will be used.'),
+	},
+	[PromptHeaderAttributes.tools]: {
+		type: 'scalar | sequence',
+		description: localize('promptHeader.prompt.tools', 'The tools to use in this prompt.'),
+		defaults: ['[]', '[\'search\', \'edit\', \'web\']'],
+	},
+	[PromptHeaderAttributes.agent]: {
+		type: 'scalar',
+		description: localize('promptHeader.prompt.agent.description', 'The agent to use when running this prompt.'),
+	},
+	[PromptHeaderAttributes.mode]: {
+		type: 'scalar',
+		description: localize('promptHeader.prompt.agent.description', 'The agent to use when running this prompt.'),
+	},
+};
+
+// Attribute metadata for instructions files (`*.instructions.md`).
+export const instructionAttributes: Record<string, IAttributeDefinition> = {
+	[PromptHeaderAttributes.name]: {
+		type: 'scalar',
+		description: localize('promptHeader.instructions.name', 'The name of the instruction file as shown in the UI. If not set, the name is derived from the file name.'),
+	},
+	[PromptHeaderAttributes.description]: {
+		type: 'scalar',
+		description: localize('promptHeader.instructions.description', 'The description of the instruction file. It can be used to provide additional context or information about the instructions and is passed to the language model as part of the prompt.'),
+	},
+	[PromptHeaderAttributes.applyTo]: {
+		type: 'scalar',
+		description: localize('promptHeader.instructions.applyToRange', 'One or more glob pattern (separated by comma) that describe for which files the instructions apply to. Based on these patterns, the file is automatically included in the prompt, when the context contains a file that matches one or more of these patterns. Use `**` when you want this file to always be added.\nExample: `**/*.ts`, `**/*.js`, `client/**`'),
+		defaults: [
+			'\'**\'',
+			'\'**/*.ts, **/*.js\'',
+			'\'**/*.php\'',
+			'\'**/*.py\''
+		],
+	},
+	[PromptHeaderAttributes.excludeAgent]: {
+		type: 'scalar | sequence',
+		description: localize('promptHeader.instructions.excludeAgent', 'One or more agents to exclude from using this instruction file.'),
+	},
+};
+
+// Attribute metadata for custom agent files (`*.agent.md`).
+export const customAgentAttributes: Record<string, IAttributeDefinition> = {
+	[PromptHeaderAttributes.name]: {
+		type: 'scalar',
+		description: localize('promptHeader.agent.name', 'The name of the agent as shown in the UI.'),
+	},
+	[PromptHeaderAttributes.description]: {
+		type: 'scalar',
+		description: localize('promptHeader.agent.description', 'The description of the custom agent, what it does and when to use it.'),
+	},
+	[PromptHeaderAttributes.argumentHint]: {
+		type: 'scalar',
+		description: localize('promptHeader.agent.argumentHint', 'The argument-hint describes what inputs the custom agent expects or supports.'),
+	},
+	[PromptHeaderAttributes.model]: {
+		type: 'scalar | sequence',
+		description: localize('promptHeader.agent.model', 'Specify the model that runs this custom agent. Can also be a list of models. The first available model will be used.'),
+	},
+	[PromptHeaderAttributes.tools]: {
+		type: 'scalar | sequence',
+		description: localize('promptHeader.agent.tools', 'The set of tools that the custom agent has access to.'),
+		defaults: ['[]', '[search, edit, web]'],
+	},
+	[PromptHeaderAttributes.handOffs]: {
+		type: 'sequence',
+		description: localize('promptHeader.agent.handoffs', 'Possible handoff actions when the agent has completed its task.'),
+	},
+	[PromptHeaderAttributes.target]: {
+		type: 'scalar',
+		description: localize('promptHeader.agent.target', 'The target to which the header attributes like tools apply to. Possible values are `github-copilot` and `vscode`.'),
+		enums: targetAttributeEnumValues,
+	},
+	[PromptHeaderAttributes.infer]: {
+		type: 'scalar',
+		description: localize('promptHeader.agent.infer', 'Controls visibility of the agent.'),
+		enums: booleanAttributeEnumValues,
+	},
+	[PromptHeaderAttributes.agents]: {
+		type: 'sequence',
+		description: localize('promptHeader.agent.agents', 'One or more agents that this agent can use as subagents. Use \'*\' to specify all available agents.'),
+		defaults: ['["*"]'],
+	},
+	[PromptHeaderAttributes.userInvocable]: {
+		type: 'scalar',
+		description: localize('promptHeader.agent.userInvocable', 'Whether the agent can be selected and invoked by users in the UI.'),
+		enums: booleanAttributeEnumValues,
+	},
+	[PromptHeaderAttributes.userInvokable]: {
+		type: 'scalar',
+		description: localize('promptHeader.agent.userInvokable', 'Deprecated. Use user-invocable instead.'),
+		enums: booleanAttributeEnumValues,
+	},
+	[PromptHeaderAttributes.disableModelInvocation]: {
+		type: 'scalar',
+		description: localize('promptHeader.agent.disableModelInvocation', 'If true, prevents the agent from being invoked as a subagent.'),
+		enums: booleanAttributeEnumValues,
+	},
+	[PromptHeaderAttributes.advancedOptions]: {
+		type: 'map',
+		description: localize('promptHeader.agent.advancedOptions', 'Advanced options for custom agent behavior.'),
+	},
+	[GithubPromptHeaderAttributes.github]: {
+		type: 'map',
+		description: localize('promptHeader.agent.github', 'GitHub-specific configuration for the agent, such as token permissions.'),
+	},
+	[PromptHeaderAttributes.hooks]: {
+		type: 'map',
+		description: localize('promptHeader.agent.hooks', 'Lifecycle hooks scoped to this agent. Define hooks that run only while this agent is active.'),
+	},
+};
+
+// Attribute metadata for skill files (`SKILL.md`).
+export const skillAttributes: Record<string, IAttributeDefinition> = {
+	[PromptHeaderAttributes.name]: {
+		type: 'scalar',
+		description: localize('promptHeader.skill.name', 'The name of the skill.'),
+	},
+	[PromptHeaderAttributes.description]: {
+		type: 'scalar',
+		description: localize('promptHeader.skill.description', 'The description of the skill. The description is added to every request and will be used by the agent to decide when to load the skill.'),
+	},
+	[PromptHeaderAttributes.argumentHint]: {
+		type: 'scalar',
+		description: localize('promptHeader.skill.argumentHint', 'Hint shown during autocomplete to indicate expected arguments. Example: [issue-number] or [filename] [format]'),
+	},
+	[PromptHeaderAttributes.userInvocable]: {
+		type: 'scalar',
+		description: localize('promptHeader.skill.userInvocable', 'Set to false to hide from the / menu. Use for background knowledge users should not invoke directly. Default: true.'),
+		enums: booleanAttributeEnumValues,
+	},
+	[PromptHeaderAttributes.userInvokable]: {
+		type: 'scalar',
+		description: localize('promptHeader.skill.userInvokable', 'Deprecated. Use user-invocable instead.'),
+		enums: booleanAttributeEnumValues,
+	},
+	[PromptHeaderAttributes.disableModelInvocation]: {
+		type: 'scalar',
+		description: localize('promptHeader.skill.disableModelInvocation', 'Set to true to prevent the agent from automatically loading this skill. Use for workflows you want to trigger manually with /name. Default: false.'),
+		enums: booleanAttributeEnumValues,
+	},
+	[PromptHeaderAttributes.license]: {
+		type: 'scalar | map',
+		description: localize('promptHeader.skill.license', 'License information for the skill.'),
+	},
+	[PromptHeaderAttributes.compatibility]: {
+		type: 'scalar | map',
+		description: localize('promptHeader.skill.compatibility', 'Compatibility metadata for environments or runtimes.'),
+	},
+	[PromptHeaderAttributes.metadata]: {
+		type: 'map',
+		description: localize('promptHeader.skill.metadata', 'Additional metadata for the skill.'),
+	},
+};
+
+const allAttributeNames: Record<PromptsType, string[]> = {
+	[PromptsType.prompt]: Object.keys(promptFileAttributes),
+	[PromptsType.instructions]: Object.keys(instructionAttributes),
+	[PromptsType.agent]: Object.keys(customAgentAttributes),
+	[PromptsType.skill]: Object.keys(skillAttributes),
+	[PromptsType.hook]: [], // hooks are JSON files, not markdown with YAML frontmatter
+};
+const githubCopilotAgentAttributeNames = [PromptHeaderAttributes.name, PromptHeaderAttributes.description, PromptHeaderAttributes.tools, PromptHeaderAttributes.target, GithubPromptHeaderAttributes.mcpServers, GithubPromptHeaderAttributes.github, PromptHeaderAttributes.infer];
+const recommendedAttributeNames: Record<PromptsType, string[]> = {
+	[PromptsType.prompt]: allAttributeNames[PromptsType.prompt].filter(name => !isNonRecommendedAttribute(name)),
+	[PromptsType.instructions]: allAttributeNames[PromptsType.instructions].filter(name => !isNonRecommendedAttribute(name)),
+	[PromptsType.agent]: allAttributeNames[PromptsType.agent].filter(name => !isNonRecommendedAttribute(name)),
+	[PromptsType.skill]: allAttributeNames[PromptsType.skill].filter(name => !isNonRecommendedAttribute(name)),
+	[PromptsType.hook]: [], // hooks are JSON files, not markdown with YAML frontmatter
+};
+
+export function getValidAttributeNames(promptType: PromptsType, includeNonRecommended: boolean, target: Target): string[] {
+	if (target === Target.Claude) {
+		if (promptType === PromptsType.instructions) {
+			return Object.keys(claudeRulesAttributes);
+		}
+		return Object.keys(claudeAgentAttributes);
+	} else if (target === Target.GitHubCopilot) {
+		if (promptType === PromptsType.agent) {
+			return githubCopilotAgentAttributeNames;
+		}
+	}
+	return includeNonRecommended ? allAttributeNames[promptType] : recommendedAttributeNames[promptType];
+}
+
+export function isNonRecommendedAttribute(attributeName: string): boolean {
+	return attributeName === PromptHeaderAttributes.advancedOptions || attributeName === PromptHeaderAttributes.excludeAgent || attributeName === PromptHeaderAttributes.mode || attributeName === PromptHeaderAttributes.infer || attributeName === PromptHeaderAttributes.userInvokable;
+}
+
+export function getAttributeDefinition(attributeName: string, promptType: PromptsType, target: Target): IAttributeDefinition | undefined {
+	switch (promptType) {
+		case PromptsType.instructions:
+			if (target === Target.Claude) {
+				return claudeRulesAttributes[attributeName];
+			}
+			return instructionAttributes[attributeName];
+		case PromptsType.skill:
+			return skillAttributes[attributeName];
+		case PromptsType.agent:
+			if (target === Target.Claude) {
+				return claudeAgentAttributes[attributeName];
+			}
+			return customAgentAttributes[attributeName];
+		case PromptsType.prompt:
+			return promptFileAttributes[attributeName];
+		default:
+			return undefined;
+	}
+}
+
+// The list of tools known to be used by GitHub Copilot custom agents
+export const knownGithubCopilotTools = [
+	{ name: SpecedToolAliases.execute, description: localize('githubCopilot.execute', 'Execute commands') },
+	{ name: SpecedToolAliases.read, description: localize('githubCopilot.read', 'Read files') },
+	{ name: SpecedToolAliases.edit, description: localize('githubCopilot.edit', 'Edit files') },
+	{ name: SpecedToolAliases.search, description: localize('githubCopilot.search', 'Search files') },
+	{ name: SpecedToolAliases.agent, description: localize('githubCopilot.agent', 'Use subagents') },
+];
+
+export interface IValueEntry {
+	readonly name: string;
+	readonly description?: string;
+}
+
+export const knownClaudeTools = [
+	{ name: 'Bash', description: localize('claude.bash', 'Execute shell commands'), toolEquivalent: [SpecedToolAliases.execute] },
+	{ name: 'Edit', description: localize('claude.edit', 'Make targeted file edits'), toolEquivalent: ['edit/editNotebook', 'edit/editFiles'] },
+	{ name: 'Glob', description: localize('claude.glob', 'Find files by pattern'), toolEquivalent: ['search/fileSearch'] },
+	{ name: 'Grep', description: localize('claude.grep', 'Search file contents with regex'), toolEquivalent: ['search/textSearch'] },
+	{ name: 'Read', description: localize('claude.read', 'Read file contents'), toolEquivalent: ['read/readFile', 'read/getNotebookSummary'] },
+	{ name: 'Write', description: localize('claude.write', 'Create/overwrite files'), toolEquivalent: ['edit/createDirectory', 'edit/createFile', 'edit/createJupyterNotebook'] },
+	{ name: 'WebFetch', description: localize('claude.webFetch', 'Fetch URL content'), toolEquivalent: [SpecedToolAliases.web] },
+	{ name: 'WebSearch', description: localize('claude.webSearch', 'Perform web searches'), toolEquivalent: [SpecedToolAliases.web] },
+	{ name: 'Task', description: localize('claude.task', 'Run subagents for complex tasks'), toolEquivalent: [SpecedToolAliases.agent] },
+	{ name: 'Skill', description: localize('claude.skill', 'Execute skills'), toolEquivalent: [] },
+	{ name: 'LSP', description: localize('claude.lsp', 'Code intelligence (requires plugin)'), toolEquivalent: [] },
+	{ name: 'NotebookEdit', description: localize('claude.notebookEdit', 'Modify Jupyter notebooks'), toolEquivalent: ['edit/editNotebook'] },
+	{ name: 'AskUserQuestion', description: localize('claude.askUserQuestion', 'Ask multiple-choice questions'), toolEquivalent: ['vscode/askQuestions'] },
+	{ name: 'MCPSearch', description: localize('claude.mcpSearch', 'Searches for MCP tools when tool search is enabled'), toolEquivalent: [] }
+];
+
+export const knownClaudeModels = [
+	{ name: 'sonnet', description: localize('claude.sonnet', 'Latest Claude Sonnet'), modelEquivalent: 'Claude Sonnet 4.5 (copilot)' },
+	{ name: 'opus', description: localize('claude.opus', 'Latest Claude Opus'), modelEquivalent: 'Claude Opus 4.6 (copilot)' },
+	{ name: 'haiku', description: localize('claude.haiku', 'Latest Claude Haiku, fast for simple tasks'), modelEquivalent: 'Claude Haiku 4.5 (copilot)' },
+	{ name: 'inherit', description: localize('claude.inherit', 'Inherit model from parent agent or prompt'), modelEquivalent: undefined },
+];
+
+export function mapClaudeModels(claudeModelNames: readonly string[]): readonly string[] {
+	const result = [];
+	for (const name of claudeModelNames) {
+		const claudeModel = knownClaudeModels.find(model => model.name === name);
+		if (claudeModel && claudeModel.modelEquivalent) {
+			result.push(claudeModel.modelEquivalent);
+		}
+	}
+	return result;
+}
+
+/**
+ * Maps Claude tool names to their VS Code tool equivalents.
+ */
+export function mapClaudeTools(claudeToolNames: readonly string[]): string[] {
+	const result: string[] = [];
+	for (const name of claudeToolNames) {
+		const claudeTool = knownClaudeTools.find(tool => tool.name === name);
+		if (claudeTool) {
+			result.push(...claudeTool.toolEquivalent);
+		}
+	}
+	return result;
+}
+
+export const claudeAgentAttributes: Record<string, IAttributeDefinition> = {
+	'name': {
+		type: 'scalar',
+		description: localize('attribute.name', "Unique identifier using lowercase letters and hyphens (required)"),
+	},
+	'description': {
+		type: 'scalar',
+		description: localize('attribute.description', "When to delegate to this subagent (required)"),
+	},
+	'tools': {
+		type: 'sequence',
+		description: localize('attribute.tools', "Array of tools the subagent can use. Inherits all tools if omitted"),
+		defaults: ['Read, Edit, Bash'],
+		items: knownClaudeTools
+	},
+	'disallowedTools': {
+		type: 'sequence',
+		description: localize('attribute.disallowedTools', "Tools to deny, removed from inherited or specified list"),
+		defaults: ['Write, Edit, Bash'],
+		items: knownClaudeTools
+	},
+	'model': {
+		type: 'scalar',
+		description: localize('attribute.model', "Model to use: sonnet, opus, haiku, or inherit. Defaults to inherit."),
+		defaults: ['sonnet', 'opus', 'haiku', 'inherit'],
+		enums: knownClaudeModels
+	},
+	'permissionMode': {
+		type: 'scalar',
+		description: localize('attribute.permissionMode', "Permission mode: default, acceptEdits, dontAsk, bypassPermissions, or plan."),
+		defaults: ['default', 'acceptEdits', 'dontAsk', 'bypassPermissions', 'plan'],
+		enums: [
+			{ name: 'default', description: localize('claude.permissionMode.default', 'Standard behavior: prompts for permission on first use of each tool.') },
+			{ name: 'acceptEdits', description: localize('claude.permissionMode.acceptEdits', 'Automatically accepts file edit permissions for the session.') },
+			{ name: 'plan', description: localize('claude.permissionMode.plan', 'Plan Mode: Claude can analyze but not modify files or execute commands.') },
+			{ name: 'delegate', description: localize('claude.permissionMode.delegate', 'Coordination-only mode for agent team leads. Only available when an agent team is active.') },
+			{ name: 'dontAsk', description: localize('claude.permissionMode.dontAsk', 'Auto-denies tools unless pre-approved via /permissions or permissions.allow rules.') },
+			{ name: 'bypassPermissions', description: localize('claude.permissionMode.bypassPermissions', 'Skips all permission prompts (requires safe environment like containers).') }
+		]
+	},
+	'skills': {
+		type: 'sequence',
+		description: localize('attribute.skills', "Skills to load into the subagent's context at startup."),
+	},
+	'mcpServers': {
+		type: 'sequence',
+		description: localize('attribute.mcpServers', "MCP servers available to this subagent."),
+	},
+	'hooks': {
+		type: 'object',
+		description: localize('attribute.hooks', "Lifecycle hooks scoped to this subagent."),
+	},
+	'memory': {
+		type: 'scalar',
+		description: localize('attribute.memory', "Persistent memory scope: user, project, or local. Enables cross-session learning."),
+		defaults: ['user', 'project', 'local'],
+		enums: [
+			{ name: 'user', description: localize('claude.memory.user', "Remember learnings across all projects.") },
+			{ name: 'project', description: localize('claude.memory.project', "The subagent's knowledge is project-specific and shareable via version control.") },
+			{ name: 'local', description: localize('claude.memory.local', "The subagent's knowledge is project-specific but should not be checked into version control.") }
+		]
+	}
+};
+
+/**
+ * Attributes supported in Claude rules files (`.claude/rules/*.md`).
+ * Claude rules use `paths` instead of `applyTo` for glob patterns.
+ */
+export const claudeRulesAttributes: Record<string, IAttributeDefinition> = {
+	'description': {
+		type: 'scalar',
+		description: localize('attribute.rules.description', "A description of what this rule covers, used to provide context about when it applies."),
+	},
+	'paths': {
+		type: 'sequence',
+		description: localize('attribute.rules.paths', "Array of glob patterns that describe for which files the rule applies. Based on these patterns, the file is automatically included in the prompt when the context contains a file that matches.\nExample: `['src/**/*.ts', 'test/**']`"),
+	},
+};
+
+export function isVSCodeOrDefaultTarget(target: Target): boolean {
+	return target === Target.VSCode || target === Target.Undefined;
+}
+
+export function getTarget(promptType: PromptsType, header: PromptHeader | URI): Target {
+	const uri = header instanceof URI ? header : header.uri;
+	if (promptType === PromptsType.agent) {
+		const parentDir = dirname(uri);
+		if (parentDir.path.endsWith(`/${CLAUDE_AGENTS_SOURCE_FOLDER}`)) {
+			return Target.Claude;
+		}
+		if (!(header instanceof URI)) {
+			const target = header.target;
+			if (target === Target.GitHubCopilot || target === Target.VSCode) {
+				return target;
+			}
+		}
+		return Target.Undefined;
+	} else if (promptType === PromptsType.instructions) {
+		if (isInClaudeRulesFolder(uri)) {
+			return Target.Claude;
+		}
+	}
+	return Target.Undefined;
+}
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptHeaderAutocompletion.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptHeaderAutocompletion.ts
index 5e60a57cf89e0..de33bb91fd0ce 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptHeaderAutocompletion.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptHeaderAutocompletion.ts
@@ -12,14 +12,18 @@ import { ITextModel } from '../../../../../../editor/common/model.js';
 import { ILanguageModelChatMetadata, ILanguageModelsService } from '../../languageModels.js';
 import { ILanguageModelToolsService } from '../../tools/languageModelToolsService.js';
 import { IChatModeService } from '../../chatModes.js';
-import { getPromptsTypeForLanguageId, PromptsType } from '../promptTypes.js';
-import { IPromptsService, Target } from '../service/promptsService.js';
+import { getPromptsTypeForLanguageId, PromptsType, Target } from '../promptTypes.js';
+import { IPromptsService } from '../service/promptsService.js';
 import { Iterable } from '../../../../../../base/common/iterator.js';
-import { ClaudeHeaderAttributes, ISequenceValue, IValue, parseCommaSeparatedList, PromptHeader, PromptHeaderAttributes } from '../promptFileParser.js';
-import { getAttributeDescription, getTarget, getValidAttributeNames, claudeAgentAttributes, claudeRulesAttributes, knownClaudeTools, knownGithubCopilotTools, IValueEntry } from './promptValidator.js';
+import { IMapValue, ISequenceValue, IValue, IHeaderAttribute, parseCommaSeparatedList, PromptHeader, PromptHeaderAttributes } from '../promptFileParser.js';
+import { getAttributeDefinition, getTarget, getValidAttributeNames, knownClaudeTools, knownGithubCopilotTools, IValueEntry, ClaudeHeaderAttributes, } from './promptFileAttributes.js';
 import { localize } from '../../../../../../nls.js';
 import { formatArrayValue, getQuotePreference } from '../utils/promptEditHelper.js';
-
+import { HOOKS_BY_TARGET, HOOK_METADATA } from '../hookTypes.js';
+import { HOOK_COMMAND_FIELD_DESCRIPTIONS } from '../hookSchema.js';
+import { IWorkbenchEnvironmentService } from '../../../../../services/environment/common/environmentService.js';
+import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
+import { PromptsConfig } from '../config/config.js';
 
 export class PromptHeaderAutocompletion implements CompletionItemProvider {
 	/**
@@ -37,6 +41,8 @@ export class PromptHeaderAutocompletion implements CompletionItemProvider {
 		@ILanguageModelsService private readonly languageModelsService: ILanguageModelsService,
 		@ILanguageModelToolsService private readonly languageModelToolsService: ILanguageModelToolsService,
 		@IChatModeService private readonly chatModeService: IChatModeService,
+		@IWorkbenchEnvironmentService private readonly environmentService: IWorkbenchEnvironmentService,
+		@IConfigurationService private readonly configurationService: IConfigurationService,
 	) {
 	}
 
@@ -92,6 +98,33 @@ export class PromptHeaderAutocompletion implements CompletionItemProvider {
 		const colonPosition = colonIndex !== -1 ? new Position(position.lineNumber, colonIndex + 1) : undefined;
 
 		if (!colonPosition || position.isBeforeOrEqual(colonPosition)) {
+			// Check if the position is inside a multi-line attribute (e.g., hooks map).
+			// In that case, provide value completions for that attribute instead of attribute name completions.
+			let containingAttribute = header.attributes.find(({ range }) =>
+				range.startLineNumber < position.lineNumber && position.lineNumber <= range.endLineNumber);
+			if (!containingAttribute) {
+				// Handle trailing empty lines after a map-valued attribute:
+				// The YAML parser's range ends at the last parsed child, but logically
+				// an empty line before the next attribute still belongs to the map.
+				for (let i = header.attributes.length - 1; i >= 0; i--) {
+					const attr = header.attributes[i];
+					if (attr.range.endLineNumber < position.lineNumber && attr.value.type === 'map') {
+						const nextAttr = header.attributes[i + 1];
+						const nextStartLine = nextAttr ? nextAttr.range.startLineNumber : headerRange.endLineNumber;
+						if (position.lineNumber < nextStartLine) {
+							containingAttribute = attr;
+						}
+						break;
+					}
+				}
+			}
+			if (containingAttribute) {
+				const attrLineText = model.getLineContent(containingAttribute.range.startLineNumber);
+				const attrColonIndex = attrLineText.indexOf(':');
+				if (attrColonIndex !== -1) {
+					return this.provideValueCompletions(model, position, header, new Position(containingAttribute.range.startLineNumber, attrColonIndex + 1), promptType, containingAttribute);
+				}
+			}
 			return this.provideAttributeNameCompletions(model, position, header, colonPosition, promptType);
 		} else if (colonPosition && colonPosition.isBefore(position)) {
 			return this.provideValueCompletions(model, position, header, colonPosition, promptType);
@@ -110,6 +143,9 @@ export class PromptHeaderAutocompletion implements CompletionItemProvider {
 
 		const target = getTarget(promptType, header);
 		const attributesToPropose = new Set(getValidAttributeNames(promptType, false, target));
+		if (!this.configurationService.getValue<boolean>(PromptsConfig.USE_CUSTOM_AGENT_HOOKS)) {
+			attributesToPropose.delete(PromptHeaderAttributes.hooks);
+		}
 		for (const attr of header.attributes) {
 			attributesToPropose.delete(attr.key);
 		}
@@ -117,6 +153,11 @@ export class PromptHeaderAutocompletion implements CompletionItemProvider {
 			if (colonPosition) {
 				return key;
 			}
+			// For map-valued attributes, insert a snippet with the nested structure
+			if (key === PromptHeaderAttributes.hooks && promptType === PromptsType.agent && target !== Target.Claude) {
+				const hookNames = Object.keys(HOOKS_BY_TARGET[target] ?? HOOKS_BY_TARGET[Target.Undefined]);
+				return `${key}:\n  \${1|${hookNames.join(',')}|}:\n    - type: command\n      command: "$2"`;
+			}
 			const valueSuggestions = this.getValueSuggestions(promptType, key, target);
 			if (valueSuggestions.length > 0) {
 				return `${key}: \${0:${valueSuggestions[0].name}}`;
@@ -129,7 +170,7 @@ export class PromptHeaderAutocompletion implements CompletionItemProvider {
 		for (const attribute of attributesToPropose) {
 			const item: CompletionItem = {
 				label: attribute,
-				documentation: getAttributeDescription(attribute, promptType, target),
+				documentation: getAttributeDefinition(attribute, promptType, target)?.description,
 				kind: CompletionItemKind.Property,
 				insertText: getInsertText(attribute),
 				insertTextRules: CompletionItemInsertTextRule.InsertAsSnippet,
@@ -147,10 +188,11 @@ export class PromptHeaderAutocompletion implements CompletionItemProvider {
 		header: PromptHeader,
 		colonPosition: Position,
 		promptType: PromptsType,
+		preFoundAttribute?: IHeaderAttribute,
 	): Promise<CompletionList | undefined> {
 		const suggestions: CompletionItem[] = [];
 		const posLineNumber = position.lineNumber;
-		const attribute = header.attributes.find(({ range }) => range.startLineNumber <= posLineNumber && posLineNumber <= range.endLineNumber);
+		const attribute = preFoundAttribute ?? header.attributes.find(({ range }) => range.startLineNumber <= posLineNumber && posLineNumber <= range.endLineNumber);
 		if (!attribute) {
 			return undefined;
 		}
@@ -181,8 +223,8 @@ export class PromptHeaderAutocompletion implements CompletionItemProvider {
 				if (value.type === 'sequence') {
 					// if the position is inside the tools metadata, we provide tool name completions
 					const getValues = async () => {
-						if (target === Target.GitHubCopilot) {
-							// for GitHub Copilot agent files, we only suggest the known set of tools that are supported by GitHub Copilot, instead of all tools that the user has defined, because many tools won't work with GitHub Copilot and it would be frustrating for users to select a tool that doesn't work
+						if (target === Target.GitHubCopilot || this.environmentService.isSessionsWindow) {
+							// for GitHub Copilot targets and the Sessions Window, we only suggest the known set of tools that are supported by GitHub Copilot, instead of all tools that the user has defined, because many tools won't work in these contexts and it would be frustrating for users to select a tool that doesn't work
 							return knownGithubCopilotTools;
 						} else if (target === Target.Claude) {
 							return knownClaudeTools;
@@ -201,6 +243,18 @@ export class PromptHeaderAutocompletion implements CompletionItemProvider {
 				});
 			}
 		}
+		if (attribute.key === PromptHeaderAttributes.hooks) {
+			if (attribute.value.type === 'map') {
+				// Inside the hooks map — suggest hook event type names as sub-keys
+				return this.provideHookEventCompletions(model, position, attribute.value, target);
+			}
+			// When hooks value is not yet a map (e.g., user is mid-edit on a nested line),
+			// still provide hook event completions with no existing keys.
+			if (position.lineNumber !== attribute.range.startLineNumber) {
+				const emptyMap: IMapValue = { type: 'map', properties: [], range: attribute.value.range };
+				return this.provideHookEventCompletions(model, position, emptyMap, target);
+			}
+		}
 		const lineContent = model.getLineContent(attribute.range.startLineNumber);
 		const whilespaceAfterColon = (lineContent.substring(colonPosition.column).match(/^\s*/)?.[0].length) ?? 0;
 		const entries = this.getValueSuggestions(promptType, attribute.key, target);
@@ -230,32 +284,299 @@ export class PromptHeaderAutocompletion implements CompletionItemProvider {
 			};
 			suggestions.push(item);
 		}
+		if (attribute.key === PromptHeaderAttributes.hooks && promptType === PromptsType.agent) {
+			const hookSnippet = [
+				'',
+				'  ${1|' + Object.keys(HOOKS_BY_TARGET[target] ?? HOOKS_BY_TARGET[Target.Undefined]).join(',') + '|}:',
+				'    - type: command',
+				'      command: "$2"'
+			].join('\n');
+			const item: CompletionItem = {
+				label: localize('promptHeaderAutocompletion.newHook', "New Hook"),
+				kind: CompletionItemKind.Snippet,
+				insertText: whilespaceAfterColon === 0 ? ` ${hookSnippet}` : hookSnippet,
+				insertTextRules: CompletionItemInsertTextRule.InsertAsSnippet,
+				range: new Range(position.lineNumber, colonPosition.column + whilespaceAfterColon + 1, position.lineNumber, model.getLineMaxColumn(position.lineNumber)),
+			};
+			suggestions.push(item);
+		}
 		return { suggestions };
 	}
 
-	private getValueSuggestions(promptType: PromptsType, attribute: string, target: Target): IValueEntry[] {
-		if (target === Target.Claude) {
-			const attributeDesc = promptType === PromptsType.instructions ? claudeRulesAttributes[attribute] : claudeAgentAttributes[attribute];
-			if (attributeDesc) {
-				if (attributeDesc.enums) {
-					return attributeDesc.enums;
-				} else if (attributeDesc.defaults) {
-					return attributeDesc.defaults.map(value => ({ name: value }));
+	/**
+	 * Provides completions inside the `hooks:` map.
+	 * Determines what to suggest based on nesting depth:
+	 * - At hook event level: suggest event names (SessionStart, PreToolUse, etc.)
+	 * - Inside a command object: suggest command fields (type, command, timeout, etc.)
+	 */
+	private provideHookEventCompletions(
+		model: ITextModel,
+		position: Position,
+		hooksMap: IMapValue,
+		target: Target,
+	): CompletionList | undefined {
+		// Check if the cursor is on the value side of an existing hook event key (e.g., "SessionEnd:|")
+		// In that case, offer a command entry snippet instead of event name completions.
+		const hookEventOnLine = hooksMap.properties.find(p => p.key.range.startLineNumber === position.lineNumber);
+		if (hookEventOnLine) {
+			const lineText = model.getLineContent(position.lineNumber);
+			const colonIdx = lineText.indexOf(':');
+			if (colonIdx !== -1 && position.column > colonIdx + 1) {
+				const whilespaceAfterColon = (lineText.substring(colonIdx + 1).match(/^\s*/)?.[0].length) ?? 0;
+				const commandSnippet = [
+					'',
+					'  - type: command',
+					'    command: "$1"',
+				].join('\n');
+				return {
+					suggestions: [{
+						label: localize('promptHeaderAutocompletion.newCommand', "New Command"),
+						documentation: localize('promptHeaderAutocompletion.newCommand.description', "Add a new command entry to this hook."),
+						kind: CompletionItemKind.Snippet,
+						insertText: whilespaceAfterColon === 0 ? ` ${commandSnippet}` : commandSnippet,
+						insertTextRules: CompletionItemInsertTextRule.InsertAsSnippet,
+						range: new Range(position.lineNumber, colonIdx + 1 + whilespaceAfterColon + 1, position.lineNumber, model.getLineMaxColumn(position.lineNumber)),
+					}]
+				};
+			}
+		}
+
+		// Try to provide command field completions if cursor is inside a command object
+		const commandFieldCompletions = this.provideHookCommandFieldCompletions(model, position, hooksMap, target);
+		if (commandFieldCompletions) {
+			return commandFieldCompletions;
+		}
+
+		// Otherwise provide hook event name completions
+		const suggestions: CompletionItem[] = [];
+		const hooksByTarget = HOOKS_BY_TARGET[target] ?? HOOKS_BY_TARGET[Target.Undefined];
+
+		const lineText = model.getLineContent(position.lineNumber);
+		const firstNonWhitespace = lineText.search(/\S/);
+		const isEmptyLine = firstNonWhitespace === -1;
+		// Start the range after leading whitespace so VS Code's completion
+		// filtering matches the hook name prefix the user has typed.
+		const rangeStartColumn = isEmptyLine ? position.column : firstNonWhitespace + 1;
+
+		// Exclude hook keys on the current line so the user sees all options while editing a key
+		const existingKeys = new Set(
+			hooksMap.properties
+				.filter(p => p.key.range.startLineNumber !== position.lineNumber)
+				.map(p => p.key.value)
+		);
+
+		// Supplement with text-based scanning: when incomplete YAML causes the
+		// parser to drop subsequent keys, scan the model for lines that look
+		// like hook event entries (e.g., "  UserPromptSubmit:") at the expected
+		// indentation.
+		const expectedIndent = hooksMap.properties.length > 0
+			? hooksMap.properties[0].key.range.startColumn - 1
+			: -1;
+		if (expectedIndent >= 0) {
+			const scanEnd = model.getLineCount();
+			for (let lineNum = hooksMap.range.endLineNumber + 1; lineNum <= scanEnd; lineNum++) {
+				if (lineNum === position.lineNumber) {
+					continue;
+				}
+				const lt = model.getLineContent(lineNum);
+				const lineIndent = lt.search(/\S/);
+				if (lineIndent === -1) {
+					continue;
+				}
+				if (lineIndent < expectedIndent) {
+					break; // Left the hooks map scope
+				}
+				if (lineIndent === expectedIndent) {
+					const match = lt.match(/^\s+(\S+)\s*:/);
+					if (match) {
+						existingKeys.add(match[1]);
+					}
 				}
 			}
-			return [];
 		}
-		switch (attribute) {
-			case PromptHeaderAttributes.applyTo:
-				if (promptType === PromptsType.instructions) {
-					return [
-						{ name: `'**'` },
-						{ name: `'**/*.ts, **/*.js'` },
-						{ name: `'**/*.php'` },
-						{ name: `'**/*.py'` }
-					];
+
+		// Check whether the current line already has a colon (editing an existing key)
+		const lineHasColon = lineText.indexOf(':') !== -1;
+
+		for (const [hookName, hookType] of Object.entries(hooksByTarget)) {
+			if (existingKeys.has(hookName)) {
+				continue;
+			}
+			const meta = HOOK_METADATA[hookType];
+			let insertText: string;
+			if (isEmptyLine) {
+				// On empty lines, insert a full hook snippet with command placeholder
+				insertText = [
+					`${hookName}:`,
+					`  - type: command`,
+					`    command: "$1"`,
+				].join('\n');
+			} else if (lineHasColon) {
+				// On existing key lines, only replace the key name to preserve nested content
+				insertText = `${hookName}:`;
+			} else {
+				// Typing a new event name — omit the colon so the user can
+				// trigger the next completion (e.g., New Command snippet) by typing ':'
+				insertText = hookName;
+			}
+			suggestions.push({
+				label: hookName,
+				documentation: meta?.description,
+				kind: CompletionItemKind.Property,
+				insertText,
+				insertTextRules: CompletionItemInsertTextRule.InsertAsSnippet,
+				range: new Range(position.lineNumber, rangeStartColumn, position.lineNumber, model.getLineMaxColumn(position.lineNumber)),
+			});
+		}
+
+		return { suggestions };
+	}
+
+	/**
+	 * Provides completions for hook command fields (type, command, windows, etc.)
+	 * when the cursor is inside a command object within the hooks map.
+	 * Detects nesting by checking if the position falls within a sequence item
+	 * of a hook event's value.
+	 */
+	private provideHookCommandFieldCompletions(
+		model: ITextModel,
+		position: Position,
+		hooksMap: IMapValue,
+		target: Target,
+	): CompletionList | undefined {
+		// Find which hook event's command list the cursor is in
+		const containingCommandMap = this.findContainingCommandMap(model, position, hooksMap);
+		if (!containingCommandMap) {
+			return undefined;
+		}
+
+		const isCopilotCli = target === Target.GitHubCopilot;
+		const validFields = isCopilotCli
+			? ['type', 'bash', 'powershell', 'cwd', 'env', 'timeoutSec']
+			: ['type', 'command', 'windows', 'linux', 'osx', 'bash', 'powershell', 'cwd', 'env', 'timeout'];
+
+		const existingFields = new Set(
+			containingCommandMap.properties
+				.filter(p => p.key.range.startLineNumber !== position.lineNumber)
+				.map(p => p.key.value)
+		);
+
+		const lineText = model.getLineContent(position.lineNumber);
+		const firstNonWhitespace = lineText.search(/\S/);
+		const isEmptyLine = firstNonWhitespace === -1;
+		// Skip past the YAML sequence indicator `- ` so the range starts at the
+		// actual field name; otherwise VS Code's completion filter would see the
+		// `- ` prefix and reject valid field names.
+		const dashPrefixMatch = lineText.match(/^(\s*-\s+)/);
+		const fieldStart = dashPrefixMatch ? dashPrefixMatch[1].length : firstNonWhitespace;
+		const rangeStartColumn = isEmptyLine ? position.column : fieldStart + 1;
+		const colonIndex = lineText.indexOf(':');
+
+		const suggestions: CompletionItem[] = [];
+		for (const fieldName of validFields) {
+			if (existingFields.has(fieldName)) {
+				continue;
+			}
+			const desc = HOOK_COMMAND_FIELD_DESCRIPTIONS[fieldName];
+			const insertText = colonIndex !== -1 ? fieldName : `${fieldName}: $0`;
+			suggestions.push({
+				label: fieldName,
+				documentation: desc,
+				kind: CompletionItemKind.Property,
+				insertText,
+				insertTextRules: CompletionItemInsertTextRule.InsertAsSnippet,
+				range: new Range(position.lineNumber, rangeStartColumn, position.lineNumber, colonIndex !== -1 ? colonIndex + 1 : model.getLineMaxColumn(position.lineNumber)),
+			});
+		}
+
+		return suggestions.length > 0 ? { suggestions } : undefined;
+	}
+
+	/**
+	 * Walks the hooks map AST to find the command map object containing the position.
+	 * Handles both direct command objects and nested matcher format.
+	 * Also handles trailing lines after the last parsed property of a command map.
+	 */
+	private findContainingCommandMap(model: ITextModel, position: Position, hooksMap: IMapValue): IMapValue | undefined {
+		for (let i = 0; i < hooksMap.properties.length; i++) {
+			const prop = hooksMap.properties[i];
+			if (prop.value.type !== 'sequence') {
+				continue;
+			}
+			// Check if cursor is within the sequence's range, or on a trailing line after it
+			const seqRange = prop.value.range;
+			const nextProp = hooksMap.properties[i + 1];
+			const isInSeq = seqRange.containsPosition(position);
+			const isTrailingSeq = !isInSeq
+				&& seqRange.endLineNumber < position.lineNumber
+				&& (!nextProp || nextProp.key.range.startLineNumber > position.lineNumber);
+
+			if (isInSeq || isTrailingSeq) {
+				// For trailing lines, verify the cursor is indented deeper than
+				// the hook event key — otherwise it belongs to the parent map.
+				if (isTrailingSeq) {
+					const lineText = model.getLineContent(position.lineNumber);
+					const firstNonWs = lineText.search(/\S/);
+					const effectiveIndent = firstNonWs === -1 ? position.column - 1 : firstNonWs;
+					const hookKeyIndent = prop.key.range.startColumn - 1;
+					if (effectiveIndent <= hookKeyIndent) {
+						continue;
+					}
 				}
-				break;
+				const result = this.findCommandMapInSequence(position, prop.value);
+				if (result) {
+					return result;
+				}
+			}
+		}
+		return undefined;
+	}
+
+	private findCommandMapInSequence(position: Position, sequence: ISequenceValue): IMapValue | undefined {
+		for (let i = 0; i < sequence.items.length; i++) {
+			const item = sequence.items[i];
+			if (item.type !== 'map') {
+				// Handle partial typing: a scalar on the cursor line means the user
+				// is starting to type a command entry (e.g., "- t").
+				if (item.type === 'scalar' && item.range.startLineNumber === position.lineNumber) {
+					return { type: 'map', properties: [], range: item.range };
+				}
+				continue;
+			}
+
+			// Check if position is within or just after this map item's parsed range.
+			// The parser's range may not include a trailing line being typed.
+			const isInRange = item.range.containsPosition(position);
+			const isTrailing = !isInRange
+				&& item.range.endLineNumber < position.lineNumber
+				&& (i + 1 >= sequence.items.length || sequence.items[i + 1].range.startLineNumber > position.lineNumber);
+
+			if (!isInRange && !isTrailing) {
+				continue;
+			}
+
+			// Check for nested matcher format: { hooks: [...] }
+			const nestedHooks = item.properties.find(p => p.key.value === 'hooks');
+			if (nestedHooks?.value.type === 'sequence') {
+				const result = this.findCommandMapInSequence(position, nestedHooks.value);
+				if (result) {
+					return result;
+				}
+			}
+			return item;
+		}
+		return undefined;
+	}
+
+	private getValueSuggestions(promptType: PromptsType, attribute: string, target: Target): readonly IValueEntry[] {
+		const attributeDesc = getAttributeDefinition(attribute, promptType, target);
+		if (attributeDesc?.enums) {
+			return attributeDesc.enums;
+		}
+		if (attributeDesc?.defaults) {
+			return attributeDesc.defaults.map(value => ({ name: value }));
+		}
+		switch (attribute) {
 			case PromptHeaderAttributes.agent:
 			case PromptHeaderAttributes.mode:
 				if (promptType === PromptsType.prompt) {
@@ -268,47 +589,12 @@ export class PromptHeaderAutocompletion implements CompletionItemProvider {
 					return suggestions;
 				}
 				break;
-			case PromptHeaderAttributes.target:
-				if (promptType === PromptsType.agent) {
-					return [{ name: 'vscode' }, { name: 'github-copilot' }];
-				}
-				break;
-			case PromptHeaderAttributes.tools:
-				if (promptType === PromptsType.prompt || promptType === PromptsType.agent) {
-					return [
-						{ name: '[]' },
-						{ name: `['search', 'edit', 'web']` }
-					];
-				}
-				break;
 			case PromptHeaderAttributes.model:
 				if (promptType === PromptsType.prompt || promptType === PromptsType.agent) {
 					return this.getModelNames(promptType === PromptsType.agent);
 				}
 				break;
-			case PromptHeaderAttributes.infer:
-				if (promptType === PromptsType.agent) {
-					return [
-						{ name: 'true' },
-						{ name: 'false' }
-					];
-				}
-				break;
-			case PromptHeaderAttributes.agents:
-				if (promptType === PromptsType.agent) {
-					return [{ name: '["*"]' }];
-				}
-				break;
-			case PromptHeaderAttributes.userInvocable:
-				if (promptType === PromptsType.agent || promptType === PromptsType.skill) {
-					return [{ name: 'true' }, { name: 'false' }];
-				}
-				break;
-			case PromptHeaderAttributes.disableModelInvocation:
-				if (promptType === PromptsType.agent || promptType === PromptsType.skill) {
-					return [{ name: 'true' }, { name: 'false' }];
-				}
-				break;
+
 		}
 		return [];
 	}
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptHovers.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptHovers.ts
index 8fe87c45a10ad..e3d4b279cd93b 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptHovers.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptHovers.ts
@@ -13,10 +13,14 @@ import { localize } from '../../../../../../nls.js';
 import { ILanguageModelsService } from '../../languageModels.js';
 import { ILanguageModelToolsService, isToolSet, IToolSet } from '../../tools/languageModelToolsService.js';
 import { IChatModeService, isBuiltinChatMode } from '../../chatModes.js';
-import { getPromptsTypeForLanguageId, PromptsType } from '../promptTypes.js';
-import { IPromptsService, Target } from '../service/promptsService.js';
-import { ClaudeHeaderAttributes, IHeaderAttribute, parseCommaSeparatedList, PromptBody, PromptHeader, PromptHeaderAttributes } from '../promptFileParser.js';
-import { getAttributeDescription, getTarget, isVSCodeOrDefaultTarget, knownClaudeModels, knownClaudeTools } from './promptValidator.js';
+import { getPromptsTypeForLanguageId, PromptsType, Target } from '../promptTypes.js';
+import { IPromptsService } from '../service/promptsService.js';
+import { IHeaderAttribute, ISequenceValue, parseCommaSeparatedList, PromptBody, PromptHeader, PromptHeaderAttributes } from '../promptFileParser.js';
+import { ClaudeHeaderAttributes, getAttributeDefinition, getTarget, isVSCodeOrDefaultTarget, knownClaudeModels, knownClaudeTools } from './promptFileAttributes.js';
+import { HOOKS_BY_TARGET, HOOK_METADATA } from '../hookTypes.js';
+import { HOOK_COMMAND_FIELD_DESCRIPTIONS } from '../hookSchema.js';
+import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
+import { PromptsConfig } from '../config/config.js';
 
 export class PromptHoverProvider implements HoverProvider {
 	/**
@@ -29,6 +33,7 @@ export class PromptHoverProvider implements HoverProvider {
 		@ILanguageModelToolsService private readonly languageModelToolsService: ILanguageModelToolsService,
 		@ILanguageModelsService private readonly languageModelsService: ILanguageModelsService,
 		@IChatModeService private readonly chatModeService: IChatModeService,
+		@IConfigurationService private readonly configurationService: IConfigurationService,
 	) {
 	}
 
@@ -73,7 +78,7 @@ export class PromptHoverProvider implements HoverProvider {
 	private async provideHeaderHover(position: Position, promptType: PromptsType, header: PromptHeader, target: Target): Promise<Hover | undefined> {
 		for (const attribute of header.attributes) {
 			if (attribute.range.containsPosition(position)) {
-				const description = getAttributeDescription(attribute.key, promptType, target);
+				const description = getAttributeDefinition(attribute.key, promptType, target)?.description;
 				if (description) {
 					switch (attribute.key) {
 						case PromptHeaderAttributes.model:
@@ -86,6 +91,11 @@ export class PromptHoverProvider implements HoverProvider {
 							return this.getAgentHover(attribute, position, description);
 						case PromptHeaderAttributes.handOffs:
 							return this.getHandsOffHover(attribute, position, target);
+						case PromptHeaderAttributes.hooks:
+							if (!this.configurationService.getValue<boolean>(PromptsConfig.USE_CUSTOM_AGENT_HOOKS)) {
+								return undefined;
+							}
+							return this.getHooksHover(attribute, position, description, target);
 						case PromptHeaderAttributes.infer:
 							return this.createHover(description + '\n\n' + localize('promptHeader.attribute.infer.hover', 'Deprecated: Use `user-invocable` and `disable-model-invocation` instead.'), attribute.range);
 						default:
@@ -232,8 +242,64 @@ export class PromptHoverProvider implements HoverProvider {
 		return this.createHover(lines.join('\n'), agentAttribute.range);
 	}
 
+	private getHooksHover(attribute: IHeaderAttribute, position: Position, baseMessage: string, target: Target): Hover | undefined {
+		const value = attribute.value;
+		if (value.type === 'map') {
+			const hooksByTarget = HOOKS_BY_TARGET[target] ?? HOOKS_BY_TARGET[Target.Undefined];
+			for (const prop of value.properties) {
+				// Hover on a hook event name key (e.g., SessionStart, PreToolUse)
+				if (prop.key.range.containsPosition(position)) {
+					const hookType = hooksByTarget[prop.key.value];
+					if (hookType) {
+						const meta = HOOK_METADATA[hookType];
+						return this.createHover(`**${meta.label}**\n\n${meta.description}`, prop.key.range);
+					}
+				}
+				// Hover inside hook command entries
+				if (prop.value.type === 'sequence') {
+					const hover = this.getHookCommandItemHover(prop.value, position);
+					if (hover) {
+						return hover;
+					}
+				}
+			}
+		}
+		return this.createHover(baseMessage, attribute.range);
+	}
+
+	/**
+	 * Recursively searches hook command items for hover information.
+	 * Handles both direct command objects and nested matcher format
+	 * (e.g., `{ matcher: "...", hooks: [{ type: command, ... }] }`).
+	 */
+	private getHookCommandItemHover(sequence: ISequenceValue, position: Position): Hover | undefined {
+		for (const item of sequence.items) {
+			if (item.type !== 'map' || !item.range.containsPosition(position)) {
+				continue;
+			}
+			// Check for nested matcher format: { hooks: [...] }
+			const nestedHooks = item.properties.find(p => p.key.value === 'hooks');
+			if (nestedHooks && nestedHooks.value.type === 'sequence') {
+				const hover = this.getHookCommandItemHover(nestedHooks.value, position);
+				if (hover) {
+					return hover;
+				}
+			}
+			// Check fields of the command object itself
+			for (const field of item.properties) {
+				if (field.key.range.containsPosition(position) || field.value.range.containsPosition(position)) {
+					const desc = HOOK_COMMAND_FIELD_DESCRIPTIONS[field.key.value];
+					if (desc) {
+						return this.createHover(desc, field.key.range);
+					}
+				}
+			}
+		}
+		return undefined;
+	}
+
 	private getHandsOffHover(attribute: IHeaderAttribute, position: Position, target: Target): Hover | undefined {
-		const handoffsBaseMessage = getAttributeDescription(PromptHeaderAttributes.handOffs, PromptsType.agent, target)!;
+		const handoffsBaseMessage = getAttributeDefinition(PromptHeaderAttributes.handOffs, PromptsType.agent, target)?.description!;
 		if (!isVSCodeOrDefaultTarget(target)) {
 			return this.createHover(handoffsBaseMessage + '\n\n' + localize('promptHeader.agent.handoffs.githubCopilot', 'Note: This attribute is not used in GitHub Copilot or Claude targets.'), attribute.range);
 		}
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptValidator.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptValidator.ts
index a6058e2c47ec7..d814c0b866ad0 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptValidator.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/languageProviders/promptValidator.ts
@@ -15,19 +15,23 @@ import { ChatMode, IChatMode, IChatModeService } from '../../chatModes.js';
 import { ChatModeKind } from '../../constants.js';
 import { ILanguageModelChatMetadata, ILanguageModelsService } from '../../languageModels.js';
 import { ILanguageModelToolsService, SpecedToolAliases } from '../../tools/languageModelToolsService.js';
-import { getPromptsTypeForLanguageId, PromptsType } from '../promptTypes.js';
-import { GithubPromptHeaderAttributes, ISequenceValue, IHeaderAttribute, IScalarValue, parseCommaSeparatedList, ParsedPromptFile, PromptHeader, PromptHeaderAttributes, IValue } from '../promptFileParser.js';
+import { getPromptsTypeForLanguageId, PromptsType, Target } from '../promptTypes.js';
+import { ISequenceValue, IHeaderAttribute, IScalarValue, parseCommaSeparatedList, ParsedPromptFile, PromptHeader, IValue, PromptHeaderAttributes } from '../promptFileParser.js';
 import { Disposable, DisposableStore, toDisposable } from '../../../../../../base/common/lifecycle.js';
 import { Delayer } from '../../../../../../base/common/async.js';
 import { ResourceMap } from '../../../../../../base/common/map.js';
 import { IFileService } from '../../../../../../platform/files/common/files.js';
-import { IPromptsService, Target } from '../service/promptsService.js';
+import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
+import { IPromptsService } from '../service/promptsService.js';
 import { ILabelService } from '../../../../../../platform/label/common/label.js';
 import { AGENTS_SOURCE_FOLDER, CLAUDE_AGENTS_SOURCE_FOLDER, isInClaudeRulesFolder, LEGACY_MODE_FILE_EXTENSION } from '../config/promptFileLocations.js';
 import { Lazy } from '../../../../../../base/common/lazy.js';
 import { CancellationToken } from '../../../../../../base/common/cancellation.js';
 import { dirname } from '../../../../../../base/common/resources.js';
 import { URI } from '../../../../../../base/common/uri.js';
+import { HOOKS_BY_TARGET } from '../hookTypes.js';
+import { PromptsConfig } from '../config/config.js';
+import { GithubPromptHeaderAttributes } from './promptFileAttributes.js';
 
 export const MARKERS_OWNER_ID = 'prompts-diagnostics-provider';
 
@@ -38,7 +42,8 @@ export class PromptValidator {
 		@IChatModeService private readonly chatModeService: IChatModeService,
 		@IFileService private readonly fileService: IFileService,
 		@ILabelService private readonly labelService: ILabelService,
-		@IPromptsService private readonly promptsService: IPromptsService
+		@IPromptsService private readonly promptsService: IPromptsService,
+		@IConfigurationService private readonly configurationService: IConfigurationService
 	) { }
 
 	public async validate(promptAST: ParsedPromptFile, promptType: PromptsType, report: (markers: IMarkerData) => void): Promise<void> {
@@ -190,6 +195,9 @@ export class PromptValidator {
 				this.validateUserInvokable(attributes, report);
 				this.validateDisableModelInvocation(attributes, report);
 				this.validateTools(attributes, ChatModeKind.Agent, target, report);
+				if (this.configurationService.getValue<boolean>(PromptsConfig.USE_CUSTOM_AGENT_HOOKS)) {
+					this.validateHooks(attributes, target, report);
+				}
 				if (isVSCodeOrDefaultTarget(target)) {
 					this.validateModel(attributes, ChatModeKind.Agent, report);
 					this.validateHandoffs(attributes, report);
@@ -212,11 +220,21 @@ export class PromptValidator {
 	}
 
 	private checkForInvalidArguments(attributes: IHeaderAttribute[], promptType: PromptsType, target: Target, report: (markers: IMarkerData) => void): void {
-		const validAttributeNames = getValidAttributeNames(promptType, true, target);
+		let validAttributeNames = getValidAttributeNames(promptType, true, target);
+		if (!this.configurationService.getValue<boolean>(PromptsConfig.USE_CUSTOM_AGENT_HOOKS)) {
+			validAttributeNames = validAttributeNames.filter(name => name !== PromptHeaderAttributes.hooks);
+		}
+		const useCustomAgentHooks = this.configurationService.getValue<boolean>(PromptsConfig.USE_CUSTOM_AGENT_HOOKS);
 		const validGithubCopilotAttributeNames = new Lazy(() => new Set(getValidAttributeNames(promptType, false, Target.GitHubCopilot)));
 		for (const attribute of attributes) {
 			if (!validAttributeNames.includes(attribute.key)) {
-				const supportedNames = new Lazy(() => getValidAttributeNames(promptType, false, target).sort().join(', '));
+				const supportedNames = new Lazy(() => {
+					let names = getValidAttributeNames(promptType, false, target);
+					if (!useCustomAgentHooks) {
+						names = names.filter(name => name !== PromptHeaderAttributes.hooks);
+					}
+					return names.sort().join(', ');
+				});
 				switch (promptType) {
 					case PromptsType.prompt:
 						report(toMarker(localize('promptValidator.unknownAttribute.prompt', "Attribute '{0}' is not supported in prompt files. Supported: {1}.", attribute.key, supportedNames.value), attribute.range, MarkerSeverity.Warning));
@@ -544,6 +562,119 @@ export class PromptValidator {
 		}
 	}
 
+	private validateHooks(attributes: IHeaderAttribute[], target: Target, report: (markers: IMarkerData) => void): undefined {
+		const attribute = attributes.find(attr => attr.key === PromptHeaderAttributes.hooks);
+		if (!attribute) {
+			return;
+		}
+		if (attribute.value.type !== 'map') {
+			report(toMarker(localize('promptValidator.hooksMustBeMap', "The 'hooks' attribute must be a map of hook event types to command arrays."), attribute.value.range, MarkerSeverity.Error));
+			return;
+		}
+		const validHookNames = new Set(Object.keys(HOOKS_BY_TARGET[target] ?? HOOKS_BY_TARGET[Target.Undefined]));
+		for (const prop of attribute.value.properties) {
+			if (!validHookNames.has(prop.key.value)) {
+				report(toMarker(localize('promptValidator.unknownHookType', "Unknown hook event type '{0}'. Supported: {1}.", prop.key.value, Array.from(validHookNames).join(', ')), prop.key.range, MarkerSeverity.Warning));
+			}
+			if (prop.value.type !== 'sequence') {
+				report(toMarker(localize('promptValidator.hookValueMustBeArray', "Hook event '{0}' must have an array of command objects as its value.", prop.key.value), prop.value.range, MarkerSeverity.Error));
+				continue;
+			}
+			for (const item of prop.value.items) {
+				this.validateHookCommand(item, target, report);
+			}
+		}
+	}
+
+	private validateHookCommand(item: IValue, target: Target, report: (markers: IMarkerData) => void): void {
+		if (item.type !== 'map') {
+			report(toMarker(localize('promptValidator.hookCommandMustBeObject', "Each hook command must be an object."), item.range, MarkerSeverity.Error));
+			return;
+		}
+
+		// Detect nested matcher format: { matcher?: "...", hooks: [{ type: 'command', command: '...' }] }
+		const hooksProperty = item.properties.find(p => p.key.value === 'hooks');
+		if (hooksProperty) {
+			// Validate that only known matcher properties are present
+			for (const prop of item.properties) {
+				if (prop.key.value !== 'hooks' && prop.key.value !== 'matcher') {
+					report(toMarker(localize('promptValidator.unknownMatcherProperty', "Unknown property '{0}' in hook matcher.", prop.key.value), prop.key.range, MarkerSeverity.Warning));
+				}
+			}
+			if (hooksProperty.value.type !== 'sequence') {
+				report(toMarker(localize('promptValidator.nestedHooksMustBeArray', "The 'hooks' property in a matcher must be an array of command objects."), hooksProperty.value.range, MarkerSeverity.Error));
+				return;
+			}
+			for (const nestedItem of hooksProperty.value.items) {
+				this.validateHookCommand(nestedItem, target, report);
+			}
+			return;
+		}
+
+		const isCopilotCli = target === Target.GitHubCopilot;
+
+		// Determine valid and command-providing properties based on target
+		const validCommandFields = isCopilotCli
+			? new Set(['bash', 'powershell'])
+			: new Set(['command', 'windows', 'linux', 'osx', 'bash', 'powershell']);
+
+		const validProperties = isCopilotCli
+			? new Set(['type', 'bash', 'powershell', 'cwd', 'env', 'timeoutSec'])
+			: new Set(['type', 'command', 'windows', 'linux', 'osx', 'bash', 'powershell', 'cwd', 'env', 'timeout']);
+
+		let hasType = false;
+		let hasCommandField = false;
+
+		for (const prop of item.properties) {
+			const key = prop.key.value;
+
+			if (!validProperties.has(key)) {
+				report(toMarker(localize('promptValidator.unknownHookProperty', "Unknown property '{0}' in hook command.", key), prop.key.range, MarkerSeverity.Warning));
+			}
+
+			if (key === 'type') {
+				hasType = true;
+				if (prop.value.type !== 'scalar' || prop.value.value !== 'command') {
+					report(toMarker(localize('promptValidator.hookTypeMustBeCommand', "The 'type' property in a hook command must be 'command'."), prop.value.range, MarkerSeverity.Error));
+				}
+			} else if (validCommandFields.has(key)) {
+				hasCommandField = true;
+				if (prop.value.type !== 'scalar' || prop.value.value.trim().length === 0) {
+					report(toMarker(localize('promptValidator.hookCommandFieldMustBeNonEmptyString', "The '{0}' property in a hook command must be a non-empty string.", key), prop.value.range, MarkerSeverity.Error));
+				}
+			} else if (key === 'cwd') {
+				if (prop.value.type !== 'scalar') {
+					report(toMarker(localize('promptValidator.hookCwdMustBeString', "The 'cwd' property in a hook command must be a string."), prop.value.range, MarkerSeverity.Error));
+				}
+			} else if (key === 'env') {
+				if (prop.value.type !== 'map') {
+					report(toMarker(localize('promptValidator.hookEnvMustBeMap', "The 'env' property in a hook command must be a map of string values."), prop.value.range, MarkerSeverity.Error));
+				} else {
+					for (const envProp of prop.value.properties) {
+						if (envProp.value.type !== 'scalar') {
+							report(toMarker(localize('promptValidator.hookEnvValueMustBeString', "Environment variable '{0}' must have a string value.", envProp.key.value), envProp.value.range, MarkerSeverity.Error));
+						}
+					}
+				}
+			} else if (key === 'timeout' || key === 'timeoutSec') {
+				if (prop.value.type !== 'scalar' || isNaN(Number(prop.value.value))) {
+					report(toMarker(localize('promptValidator.hookTimeoutMustBeNumber', "The '{0}' property in a hook command must be a number.", key), prop.value.range, MarkerSeverity.Error));
+				}
+			}
+		}
+
+		if (!hasType) {
+			report(toMarker(localize('promptValidator.hookMissingType', "Hook command is missing required property 'type'."), item.range, MarkerSeverity.Error));
+		}
+		if (!hasCommandField) {
+			if (isCopilotCli) {
+				report(toMarker(localize('promptValidator.hookMissingCopilotCommand', "Hook command must specify at least one of 'bash' or 'powershell'."), item.range, MarkerSeverity.Error));
+			} else {
+				report(toMarker(localize('promptValidator.hookMissingCommand', "Hook command must specify at least one of 'command', 'windows', 'linux', or 'osx'."), item.range, MarkerSeverity.Error));
+			}
+		}
+	}
+
 	private validateHandoffs(attributes: IHeaderAttribute[], report: (markers: IMarkerData) => void): undefined {
 		const attribute = attributes.find(attr => attr.key === PromptHeaderAttributes.handOffs);
 		if (!attribute) {
@@ -760,7 +891,7 @@ function isTrueOrFalse(value: IValue): boolean {
 const allAttributeNames: Record<PromptsType, string[]> = {
 	[PromptsType.prompt]: [PromptHeaderAttributes.name, PromptHeaderAttributes.description, PromptHeaderAttributes.model, PromptHeaderAttributes.tools, PromptHeaderAttributes.mode, PromptHeaderAttributes.agent, PromptHeaderAttributes.argumentHint],
 	[PromptsType.instructions]: [PromptHeaderAttributes.name, PromptHeaderAttributes.description, PromptHeaderAttributes.applyTo, PromptHeaderAttributes.excludeAgent],
-	[PromptsType.agent]: [PromptHeaderAttributes.name, PromptHeaderAttributes.description, PromptHeaderAttributes.model, PromptHeaderAttributes.tools, PromptHeaderAttributes.advancedOptions, PromptHeaderAttributes.handOffs, PromptHeaderAttributes.argumentHint, PromptHeaderAttributes.target, PromptHeaderAttributes.infer, PromptHeaderAttributes.agents, PromptHeaderAttributes.userInvocable, PromptHeaderAttributes.userInvokable, PromptHeaderAttributes.disableModelInvocation, GithubPromptHeaderAttributes.github],
+	[PromptsType.agent]: [PromptHeaderAttributes.name, PromptHeaderAttributes.description, PromptHeaderAttributes.model, PromptHeaderAttributes.tools, PromptHeaderAttributes.advancedOptions, PromptHeaderAttributes.handOffs, PromptHeaderAttributes.argumentHint, PromptHeaderAttributes.target, PromptHeaderAttributes.infer, PromptHeaderAttributes.agents, PromptHeaderAttributes.hooks, PromptHeaderAttributes.userInvocable, PromptHeaderAttributes.userInvokable, PromptHeaderAttributes.disableModelInvocation, GithubPromptHeaderAttributes.github],
 	[PromptsType.skill]: [PromptHeaderAttributes.name, PromptHeaderAttributes.description, PromptHeaderAttributes.license, PromptHeaderAttributes.compatibility, PromptHeaderAttributes.metadata, PromptHeaderAttributes.argumentHint, PromptHeaderAttributes.userInvocable, PromptHeaderAttributes.userInvokable, PromptHeaderAttributes.disableModelInvocation],
 	[PromptsType.hook]: [], // hooks are JSON files, not markdown with YAML frontmatter
 };
@@ -845,6 +976,8 @@ export function getAttributeDescription(attributeName: string, promptType: Promp
 					return localize('promptHeader.agent.infer', 'Controls visibility of the agent.');
 				case PromptHeaderAttributes.agents:
 					return localize('promptHeader.agent.agents', 'One or more agents that this agent can use as subagents. Use \'*\' to specify all available agents.');
+				case PromptHeaderAttributes.hooks:
+					return localize('promptHeader.agent.hooks', 'Lifecycle hooks scoped to this agent. Define hooks that run only while this agent is active.');
 				case PromptHeaderAttributes.userInvocable:
 					return localize('promptHeader.agent.userInvocable', 'Whether the agent can be selected and invoked by users in the UI.');
 				case PromptHeaderAttributes.disableModelInvocation:
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/promptFileParser.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/promptFileParser.ts
index f6b160c7ee276..240265152cffc 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/promptFileParser.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/promptFileParser.ts
@@ -10,7 +10,6 @@ import { URI } from '../../../../../base/common/uri.js';
 import { parse, YamlNode, YamlParseError } from '../../../../../base/common/yaml.js';
 import { Range } from '../../../../../editor/common/core/range.js';
 import { PositionOffsetTransformer } from '../../../../../editor/common/core/text/positionToOffsetImpl.js';
-import { Target } from './service/promptsService.js';
 
 export class PromptFileParser {
 	constructor() {
@@ -85,19 +84,7 @@ export namespace PromptHeaderAttributes {
 	export const userInvokable = 'user-invokable';
 	export const userInvocable = 'user-invocable';
 	export const disableModelInvocation = 'disable-model-invocation';
-}
-
-export namespace GithubPromptHeaderAttributes {
-	export const mcpServers = 'mcp-servers';
-	export const github = 'github';
-}
-
-export namespace ClaudeHeaderAttributes {
-	export const disallowedTools = 'disallowedTools';
-}
-
-export function isTarget(value: unknown): value is Target {
-	return value === Target.VSCode || value === Target.GitHubCopilot || value === Target.Claude || value === Target.Undefined;
+	export const hooks = 'hooks';
 }
 
 export class PromptHeader {
@@ -331,6 +318,20 @@ export class PromptHeader {
 		return this.getBooleanAttribute(PromptHeaderAttributes.disableModelInvocation);
 	}
 
+	/**
+	 * Gets the raw 'hooks' attribute value from the header.
+	 * Returns the YAML map value if present, or undefined. The caller is
+	 * responsible for converting this to `ChatRequestHooks` via
+	 * {@link parseSubagentHooksFromYaml}.
+	 */
+	public get hooksRaw(): IMapValue | undefined {
+		const attr = this._parsedHeader.attributes.find(a => a.key === PromptHeaderAttributes.hooks);
+		if (attr?.value.type === 'map') {
+			return attr.value;
+		}
+		return undefined;
+	}
+
 	private getBooleanAttribute(key: string): boolean | undefined {
 		const attribute = this._parsedHeader.attributes.find(attr => attr.key === key);
 		if (attribute?.value.type === 'scalar') {
@@ -416,14 +417,66 @@ export class PromptBody {
 			const fileReferences: IBodyFileReference[] = [];
 			const variableReferences: IBodyVariableReference[] = [];
 			const bodyOffset = Iterable.reduce(Iterable.slice(this.linesWithEOL, 0, this.range.startLineNumber - 1), (len, line) => line.length + len, 0);
+			let inFencedCodeBlock = false;
+			let fencedCodeBlockFenceChar: string | undefined;
+			let fencedCodeBlockFenceLength = 0;
 			for (let i = this.range.startLineNumber - 1, lineStartOffset = bodyOffset; i < this.range.endLineNumber - 1; i++) {
 				const line = this.linesWithEOL[i];
+				const trimmedLine = line.trimStart();
+
+				// Detect fenced code block lines (``` or ~~~, 3 or more chars)
+				const fenceMatch = /^(?<fence>(`{3,}|~{3,}))/u.exec(trimmedLine);
+				if (fenceMatch) {
+					const fence = fenceMatch.groups!.fence;
+					const fenceChar = fence[0];
+					const fenceLength = fence.length;
+					const restOfLine = trimmedLine.slice(fence.length);
+
+					if (!inFencedCodeBlock) {
+						// Opening fence: record fence char/length and enter fenced code block
+						inFencedCodeBlock = true;
+						fencedCodeBlockFenceChar = fenceChar;
+						fencedCodeBlockFenceLength = fenceLength;
+						lineStartOffset += line.length;
+						continue;
+					}
+
+					// Potential closing fence: must match fence char and have at least the same length,
+					// and only whitespace is allowed after the fence.
+					if (fencedCodeBlockFenceChar === fenceChar && fenceLength >= fencedCodeBlockFenceLength && /^\s*$/.test(restOfLine)) {
+						inFencedCodeBlock = false;
+						fencedCodeBlockFenceChar = undefined;
+						fencedCodeBlockFenceLength = 0;
+						lineStartOffset += line.length;
+						continue;
+					}
+				}
+
+				// Skip all lines inside fenced code blocks
+				if (inFencedCodeBlock) {
+					lineStartOffset += line.length;
+					continue;
+				}
+
+				// Collect inline code spans (backtick-delimited) to exclude from matching
+				const inlineCodeRanges: { start: number; end: number }[] = [];
+				for (const inlineMatch of line.matchAll(/`[^`]+`/g)) {
+					inlineCodeRanges.push({ start: inlineMatch.index, end: inlineMatch.index + inlineMatch[0].length });
+				}
+
+				const isInsideInlineCode = (offset: number) => {
+					return inlineCodeRanges.some(r => offset >= r.start && offset < r.end);
+				};
+
 				// Match markdown links: [text](link)
 				const linkMatch = line.matchAll(/\[(.*?)\]\((.+?)\)/g);
 				for (const match of linkMatch) {
 					if (match.index > 0 && line[match.index - 1] === '!') {
 						continue; // skip image links
 					}
+					if (isInsideInlineCode(match.index)) {
+						continue; // skip matches inside inline code
+					}
 					const linkEndOffset = match.index + match[0].length - 1; // before the parenthesis
 					const linkStartOffset = match.index + match[0].length - match[2].length - 1;
 					const range = new Range(i + 1, linkStartOffset + 1, i + 1, linkEndOffset + 1);
@@ -440,6 +493,9 @@ export class PromptBody {
 					if (markdownLinkRanges.some(mdRange => Range.areIntersectingOrTouching(mdRange, fullRange))) {
 						continue;
 					}
+					if (isInsideInlineCode(match.index)) {
+						continue; // skip matches inside inline code
+					}
 					const contentMatch = match.groups?.['filePath'] || match.groups?.['toolName'];
 					if (!contentMatch) {
 						continue;
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/promptTypes.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/promptTypes.ts
index 8c4d0cbc58a87..c34350dcfb7af 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/promptTypes.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/promptTypes.ts
@@ -40,6 +40,31 @@ export const SKILL_LANGUAGE_ID = 'skill';
  */
 export const ALL_PROMPTS_LANGUAGE_SELECTOR: LanguageSelector = [PROMPT_LANGUAGE_ID, INSTRUCTIONS_LANGUAGE_ID, AGENT_LANGUAGE_ID, SKILL_LANGUAGE_ID];
 
+/**
+ * Configuration key for enabling the agent debug log feature.
+ */
+export const AGENT_DEBUG_LOG_ENABLED_SETTING = 'github.copilot.chat.agentDebugLog.enabled';
+
+/**
+ * Configuration key for enabling file logging for the agent debug log.
+ */
+export const AGENT_DEBUG_LOG_FILE_LOGGING_ENABLED_SETTING = 'github.copilot.chat.agentDebugLog.fileLogging.enabled';
+
+/**
+ * The name of the troubleshoot slash command / skill.
+ */
+export const TROUBLESHOOT_COMMAND_NAME = 'troubleshoot';
+
+/**
+ * URI scheme used by the Copilot extension for built-in skills.
+ */
+export const COPILOT_SKILL_URI_SCHEME = 'copilot-skill';
+
+/**
+ * Path fragment that identifies the troubleshoot skill in a URI.
+ */
+export const TROUBLESHOOT_SKILL_PATH = 'troubleshoot/SKILL.md';
+
 /**
  * The language id for a prompts type.
  */
@@ -92,3 +117,9 @@ export function isValidPromptType(type: string): type is PromptsType {
 	return Object.values(PromptsType).includes(type as PromptsType);
 }
 
+export enum Target {
+	VSCode = 'vscode',
+	GitHubCopilot = 'github-copilot',
+	Claude = 'claude',
+	Undefined = 'undefined',
+}
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/service/promptsService.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/service/promptsService.ts
index 23113daea69c1..84a2800ed78ad 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/service/promptsService.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/service/promptsService.ts
@@ -8,21 +8,22 @@ import { Event } from '../../../../../../base/common/event.js';
 import { IDisposable } from '../../../../../../base/common/lifecycle.js';
 import { URI } from '../../../../../../base/common/uri.js';
 import { ITextModel } from '../../../../../../editor/common/model.js';
+import { ContextKeyExpression } from '../../../../../../platform/contextkey/common/contextkey.js';
 import { ExtensionIdentifier, IExtensionDescription } from '../../../../../../platform/extensions/common/extensions.js';
 import { createDecorator } from '../../../../../../platform/instantiation/common/instantiation.js';
 import { IChatModeInstructions, IVariableReference } from '../../chatModes.js';
-import { PromptsType } from '../promptTypes.js';
+import { PromptsType, Target } from '../promptTypes.js';
 import { IHandOff, ParsedPromptFile } from '../promptFileParser.js';
 import { ResourceSet } from '../../../../../../base/common/map.js';
-import { IChatRequestHooks } from '../hookSchema.js';
 import { IResolvedPromptSourceFolder } from '../config/promptFileLocations.js';
+import { ChatRequestHooks } from '../hookSchema.js';
 
 /**
  * Entry emitted by the prompts service when discovery logging occurs.
  * A debug bridge (e.g. contribution) can listen and forward these to IChatDebugService.
  */
 export interface IPromptDiscoveryLogEntry {
-	readonly sessionId: string;
+	readonly sessionResource: URI;
 	readonly name: string;
 	readonly details?: string;
 	readonly category?: string;
@@ -72,7 +73,9 @@ export const IPromptsService = createDecorator<IPromptsService>('IPromptsService
 export enum PromptsStorage {
 	local = 'local',
 	user = 'user',
-	extension = 'extension'
+	extension = 'extension',
+	plugin = 'plugin',
+	internal = 'internal',
 }
 
 /**
@@ -87,7 +90,7 @@ export enum ExtensionAgentSourceType {
  * Represents a prompt path with its type.
  * This is used for both prompt files and prompt source folders.
  */
-export type IPromptPath = IExtensionPromptPath | ILocalPromptPath | IUserPromptPath;
+export type IPromptPath = IExtensionPromptPath | ILocalPromptPath | IUserPromptPath | IPluginPromptPath | IInternalPromptPath;
 
 
 export interface IPromptPathBase {
@@ -131,12 +134,26 @@ export interface IUserPromptPath extends IPromptPathBase {
 	readonly storage: PromptsStorage.user;
 }
 
+export interface IPluginPromptPath extends IPromptPathBase {
+	readonly storage: PromptsStorage.plugin;
+	readonly pluginUri: URI;
+}
+
+export interface IInternalPromptPath extends IPromptPathBase {
+	readonly storage: PromptsStorage.internal;
+}
+
 export type IAgentSource = {
 	readonly storage: PromptsStorage.extension;
 	readonly extensionId: ExtensionIdentifier;
 	readonly type: ExtensionAgentSourceType;
 } | {
 	readonly storage: PromptsStorage.local | PromptsStorage.user;
+} | {
+	readonly storage: PromptsStorage.plugin;
+	readonly pluginUri: URI;
+} | {
+	readonly storage: PromptsStorage.internal;
 };
 
 /**
@@ -159,13 +176,6 @@ export function isCustomAgentVisibility(obj: unknown): obj is ICustomAgentVisibi
 	return typeof v.userInvocable === 'boolean' && typeof v.agentInvocable === 'boolean';
 }
 
-export enum Target {
-	VSCode = 'vscode',
-	GitHubCopilot = 'github-copilot',
-	Claude = 'claude',
-	Undefined = 'undefined',
-}
-
 export interface ICustomAgent {
 	/**
 	 * URI of a custom agent file.
@@ -223,6 +233,11 @@ export interface ICustomAgent {
 	 */
 	readonly agents?: readonly string[];
 
+	/**
+	 * Lifecycle hooks scoped to this subagent.
+	 */
+	readonly hooks?: ChatRequestHooks;
+
 	/**
 	 * Where the agent was loaded from.
 	 */
@@ -241,6 +256,7 @@ export interface IChatPromptSlashCommand {
 	readonly argumentHint: string | undefined;
 	readonly promptPath: IPromptPath;
 	readonly parsedPromptFile: ParsedPromptFile;
+	readonly when: ContextKeyExpression | undefined;
 }
 
 export interface IAgentSkill {
@@ -258,6 +274,11 @@ export interface IAgentSkill {
 	 * Use for background knowledge users shouldn't invoke directly.
 	 */
 	readonly userInvocable: boolean;
+	/**
+	 * Optional context key expression. When set, the skill is only available
+	 * when this expression evaluates to true against a scoped context.
+	 */
+	readonly when?: ContextKeyExpression;
 }
 
 /**
@@ -297,7 +318,8 @@ export type PromptFileSkipReason =
 	| 'parse-error'
 	| 'disabled'
 	| 'all-hooks-disabled'
-	| 'claude-hooks-disabled';
+	| 'claude-hooks-disabled'
+	| 'workspace-untrusted';
 
 /**
  * Result of discovering a single prompt file.
@@ -326,12 +348,6 @@ export interface IPromptFileDiscoveryResult {
 export interface IPromptSourceFolderResult {
 	readonly uri: URI;
 	readonly storage: PromptsStorage;
-	/** Whether the folder exists on disk */
-	readonly exists: boolean;
-	/** Number of matching files found in this folder */
-	readonly fileCount: number;
-	/** Error message if resolution failed */
-	readonly errorMessage?: string;
 }
 
 /**
@@ -340,12 +356,12 @@ export interface IPromptSourceFolderResult {
 export interface IPromptDiscoveryInfo {
 	readonly type: PromptsType;
 	readonly files: readonly IPromptFileDiscoveryResult[];
-	/** Source folders that were searched, with their existence and file count */
+	/** Source folders that were searched */
 	readonly sourceFolders?: readonly IPromptSourceFolderResult[];
 }
 
 export interface IConfiguredHooksInfo {
-	readonly hooks: IChatRequestHooks;
+	readonly hooks: ChatRequestHooks;
 	readonly hasDisabledClaudeHooks: boolean;
 }
 
@@ -401,9 +417,9 @@ export interface IPromptsService extends IDisposable {
 
 	/**
 	 * Returns a prompt command if the command name is valid.
-	 * @param sessionId Optional session ID to scope debug logging to a specific session.
+	 * @param sessionResource Optional session resource to scope debug logging to a specific session.
 	 */
-	getPromptSlashCommands(token: CancellationToken, sessionId?: string): Promise<readonly IChatPromptSlashCommand[]>;
+	getPromptSlashCommands(token: CancellationToken, sessionResource?: URI): Promise<readonly IChatPromptSlashCommand[]>;
 
 	/**
 	 * Returns the prompt command name for the given URI.
@@ -415,11 +431,16 @@ export interface IPromptsService extends IDisposable {
 	 */
 	readonly onDidChangeCustomAgents: Event<void>;
 
+	/**
+	 * Event that is triggered when the list of instruction files changes.
+	 */
+	readonly onDidChangeInstructions: Event<void>;
+
 	/**
 	 * Finds all available custom agents
-	 * @param sessionId Optional session ID to scope debug logging to a specific session.
+	 * @param sessionResource Optional session resource to scope debug logging to a specific session.
 	 */
-	getCustomAgents(token: CancellationToken, sessionId?: string): Promise<readonly ICustomAgent[]>;
+	getCustomAgents(token: CancellationToken, sessionResource?: URI): Promise<readonly ICustomAgent[]>;
 
 	/**
 	 * Parses the provided URI
@@ -477,30 +498,27 @@ export interface IPromptsService extends IDisposable {
 
 	/**
 	 * Gets list of agent skills files.
-	 * @param sessionId Optional session ID to scope debug logging to a specific session.
+	 * @param sessionResource Optional session resource to scope debug logging to a specific session.
 	 */
-	findAgentSkills(token: CancellationToken, sessionId?: string): Promise<IAgentSkill[] | undefined>;
+	findAgentSkills(token: CancellationToken, sessionResource?: URI): Promise<IAgentSkill[] | undefined>;
 
 	/**
-	 * Gets detailed discovery information for a prompt type.
-	 * This includes all files found and their load/skip status with reasons.
-	 * Used for diagnostics and config-info displays.
-	 * @param sessionId Optional session ID to scope debug logging to a specific session.
+	 * Event that is triggered when the list of skills changes.
 	 */
-	getPromptDiscoveryInfo(type: PromptsType, token: CancellationToken, sessionId?: string): Promise<IPromptDiscoveryInfo>;
+	readonly onDidChangeSkills: Event<void>;
 
 	/**
 	 * Gets all hooks collected from hooks.json files.
 	 * The result is cached and invalidated when hook files change.
-	 * @param sessionId Optional session ID to scope debug logging to a specific session.
+	 * @param sessionResource Optional session resource to scope debug logging to a specific session.
 	 */
-	getHooks(token: CancellationToken, sessionId?: string): Promise<IConfiguredHooksInfo | undefined>;
+	getHooks(token: CancellationToken, sessionResource?: URI): Promise<IConfiguredHooksInfo | undefined>;
 
 	/**
 	 * Gets all instruction files, logging discovery info to the debug log.
-	 * @param sessionId Optional session ID to scope debug logging to a specific session.
+	 * @param sessionResource Optional session resource to scope debug logging to a specific session.
 	 */
-	getInstructionFiles(token: CancellationToken, sessionId?: string): Promise<readonly IPromptPath[]>;
+	getInstructionFiles(token: CancellationToken, sessionResource?: URI): Promise<readonly IPromptPath[]>;
 
 	/**
 	 * Fired when a discovery-related log entry is produced.
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/service/promptsServiceImpl.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/service/promptsServiceImpl.ts
index e42b4fde1f921..930c9390c2be3 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/service/promptsServiceImpl.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/service/promptsServiceImpl.ts
@@ -10,7 +10,7 @@ import { parse as parseJSONC } from '../../../../../../base/common/json.js';
 import { Disposable, DisposableStore, IDisposable } from '../../../../../../base/common/lifecycle.js';
 import { autorun, IReader } from '../../../../../../base/common/observable.js';
 import { ResourceMap, ResourceSet } from '../../../../../../base/common/map.js';
-import { basename, dirname, isEqual, joinPath } from '../../../../../../base/common/resources.js';
+import { basename, dirname, isEqual } from '../../../../../../base/common/resources.js';
 import { URI } from '../../../../../../base/common/uri.js';
 import { OffsetRange } from '../../../../../../editor/common/core/ranges/offsetRange.js';
 import { type ITextModel } from '../../../../../../editor/common/model.js';
@@ -29,21 +29,29 @@ import { ITelemetryService } from '../../../../../../platform/telemetry/common/t
 import { IUserDataProfileService } from '../../../../../services/userDataProfile/common/userDataProfile.js';
 import { IVariableReference } from '../../chatModes.js';
 import { PromptsConfig } from '../config/config.js';
-import { AGENT_MD_FILENAME, CLAUDE_CONFIG_FOLDER, CLAUDE_LOCAL_MD_FILENAME, CLAUDE_MD_FILENAME, getCleanPromptName, IResolvedPromptFile, IResolvedPromptSourceFolder, PromptFileSource } from '../config/promptFileLocations.js';
-import { PROMPT_LANGUAGE_ID, PromptsType, getPromptsTypeForLanguageId } from '../promptTypes.js';
-import { PromptFilesLocator } from '../utils/promptFilesLocator.js';
+import { AGENT_MD_FILENAME, CLAUDE_CONFIG_FOLDER, CLAUDE_LOCAL_MD_FILENAME, CLAUDE_MD_FILENAME, COPILOT_CUSTOM_INSTRUCTIONS_FILENAME, getCleanPromptName, GITHUB_CONFIG_FOLDER, IResolvedPromptFile, IResolvedPromptSourceFolder, PromptFileSource } from '../config/promptFileLocations.js';
+import { PROMPT_LANGUAGE_ID, PromptsType, Target, getPromptsTypeForLanguageId } from '../promptTypes.js';
+import {
+	IWorkspaceInstructionFile,
+	PromptFilesLocator
+} from '../utils/promptFilesLocator.js';
 import { PromptFileParser, ParsedPromptFile, PromptHeaderAttributes } from '../promptFileParser.js';
-import { IAgentInstructions, type IAgentSource, IChatPromptSlashCommand, IConfiguredHooksInfo, ICustomAgent, IExtensionPromptPath, ILocalPromptPath, IPromptPath, IPromptsService, IAgentSkill, IUserPromptPath, PromptsStorage, ExtensionAgentSourceType, CUSTOM_AGENT_PROVIDER_ACTIVATION_EVENT, INSTRUCTIONS_PROVIDER_ACTIVATION_EVENT, IPromptFileContext, IPromptFileResource, PROMPT_FILE_PROVIDER_ACTIVATION_EVENT, SKILL_PROVIDER_ACTIVATION_EVENT, IPromptDiscoveryInfo, IPromptFileDiscoveryResult, IPromptSourceFolderResult, ICustomAgentVisibility, IResolvedAgentFile, AgentFileType, Logger, Target, IPromptDiscoveryLogEntry } from './promptsService.js';
+import { IAgentInstructions, type IAgentSource, IChatPromptSlashCommand, IConfiguredHooksInfo, ICustomAgent, IExtensionPromptPath, ILocalPromptPath, IPluginPromptPath, IPromptPath, IPromptsService, IAgentSkill, IUserPromptPath, PromptsStorage, ExtensionAgentSourceType, CUSTOM_AGENT_PROVIDER_ACTIVATION_EVENT, INSTRUCTIONS_PROVIDER_ACTIVATION_EVENT, IPromptFileContext, IPromptFileResource, PROMPT_FILE_PROVIDER_ACTIVATION_EVENT, SKILL_PROVIDER_ACTIVATION_EVENT, IPromptDiscoveryInfo, IPromptFileDiscoveryResult, IPromptSourceFolderResult, ICustomAgentVisibility, IResolvedAgentFile, AgentFileType, Logger, IPromptDiscoveryLogEntry } from './promptsService.js';
 import { Delayer } from '../../../../../../base/common/async.js';
 import { Schemas } from '../../../../../../base/common/network.js';
-import { IChatRequestHooks, IHookCommand, HookType } from '../hookSchema.js';
+import { ChatRequestHooks, IHookCommand, parseSubagentHooksFromYaml } from '../hookSchema.js';
+import { HookType } from '../hookTypes.js';
 import { HookSourceFormat, getHookSourceFormat, parseHooksFromFile } from '../hookCompatibility.js';
 import { IWorkspaceContextService } from '../../../../../../platform/workspace/common/workspace.js';
+import { IWorkspaceTrustManagementService } from '../../../../../../platform/workspace/common/workspaceTrust.js';
 import { IPathService } from '../../../../../services/path/common/pathService.js';
-import { getTarget, mapClaudeModels, mapClaudeTools } from '../languageProviders/promptValidator.js';
+import { getTarget, mapClaudeModels, mapClaudeTools } from '../languageProviders/promptFileAttributes.js';
 import { StopWatch } from '../../../../../../base/common/stopwatch.js';
 import { ContextKeyExpr, IContextKeyService } from '../../../../../../platform/contextkey/common/contextkey.js';
 import { getCanonicalPluginCommandId, IAgentPlugin, IAgentPluginService } from '../../plugins/agentPluginService.js';
+import { isContributionEnabled } from '../../enablement.js';
+import { assertNever } from '../../../../../../base/common/assert.js';
+import { ChatInternalCustomizations } from '../internalCustomizations/internalCustomizations.js';
 
 /**
  * Error thrown when a skill file is missing the required name attribute.
@@ -87,6 +95,11 @@ export class PromptsService extends Disposable implements IPromptsService {
 	 */
 	private readonly fileLocator: PromptFilesLocator;
 
+	/**
+	 * Built-in internal customizations (skills, instructions, etc.).
+	 */
+	private readonly internalCustomizations: ChatInternalCustomizations;
+
 	/**
 	 * Cached custom agents. Caching only happens if the `onDidChangeCustomAgents` event is used.
 	 */
@@ -150,9 +163,10 @@ export class PromptsService extends Disposable implements IPromptsService {
 	private readonly _contributedWhenKeys = new Set<string>();
 	private readonly _contributedWhenClauses = new Map<string, string>();
 	private readonly _onDidContributedWhenChange = this._register(new Emitter<void>());
+	private readonly _onDidChangeInstructions = this._register(new Emitter<void>());
 	private readonly _onDidPluginPromptFilesChange = this._register(new Emitter<void>());
 	private readonly _onDidPluginHooksChange = this._register(new Emitter<void>());
-	private _pluginPromptFilesByType = new Map<PromptsType, readonly ILocalPromptPath[]>();
+	private _pluginPromptFilesByType = new Map<PromptsType, readonly IPluginPromptPath[]>();
 
 	constructor(
 		@ILogService public readonly logger: ILogService,
@@ -170,10 +184,15 @@ export class PromptsService extends Disposable implements IPromptsService {
 		@IPathService private readonly pathService: IPathService,
 		@IContextKeyService private readonly contextKeyService: IContextKeyService,
 		@IAgentPluginService private readonly agentPluginService: IAgentPluginService,
+		@IWorkspaceTrustManagementService private readonly workspaceTrustService: IWorkspaceTrustManagementService,
 	) {
 		super();
 
 		this.fileLocator = this.createPromptFilesLocator();
+
+		// Register the internal readonly customizations
+		this.internalCustomizations = this._register(new ChatInternalCustomizations(this.fileService));
+
 		this._register(this.modelService.onModelRemoved((model) => {
 			this.cachedParsedPromptFromModels.delete(model.uri);
 		}));
@@ -190,7 +209,13 @@ export class PromptsService extends Disposable implements IPromptsService {
 		const modelChangeEvent = this._register(new ModelChangeTracker(this.modelService)).onDidPromptChange;
 		this.cachedCustomAgents = this._register(new CachedPromise(
 			(token) => this.computeCustomAgents(token),
-			() => Event.any(this.getFileLocatorEvent(PromptsType.agent), Event.filter(modelChangeEvent, e => e.promptType === PromptsType.agent), this._onDidContributedWhenChange.event)
+			() => Event.any(
+				this.getFileLocatorEvent(PromptsType.agent),
+				Event.filter(modelChangeEvent, e => e.promptType === PromptsType.agent),
+				this._onDidContributedWhenChange.event,
+				Event.filter(this.configurationService.onDidChangeConfiguration, e => e.affectsConfiguration(PromptsConfig.USE_CUSTOM_AGENT_HOOKS)),
+				this._onDidPluginPromptFilesChange.event,
+			)
 		));
 
 		this.cachedSlashCommands = this._register(new CachedPromise(
@@ -215,6 +240,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 				this.getFileLocatorEvent(PromptsType.hook),
 				Event.filter(this.configurationService.onDidChangeConfiguration, e => e.affectsConfiguration(PromptsConfig.USE_CHAT_HOOKS) || e.affectsConfiguration(PromptsConfig.USE_CLAUDE_HOOKS)),
 				this._onDidPluginHooksChange.event,
+				this.workspaceTrustService.onDidChangeTrust,
 			)
 		));
 
@@ -230,11 +256,21 @@ export class PromptsService extends Disposable implements IPromptsService {
 			PromptsType.skill,
 			(plugin, reader) => plugin.skills.read(reader),
 		));
+		this._register(this.watchPluginPromptFilesForType(
+			PromptsType.agent,
+			(plugin, reader) => plugin.agents.read(reader),
+		));
+		this._register(this.watchPluginPromptFilesForType(
+			PromptsType.instructions,
+			(plugin, reader) => plugin.instructions.read(reader),
+		));
 
 		this._register(autorun(reader => {
 			const plugins = this.agentPluginService.plugins.read(reader);
 			for (const plugin of plugins) {
-				plugin.hooks.read(reader);
+				if (isContributionEnabled(plugin.enablement.read(reader))) {
+					plugin.hooks.read(reader);
+				}
 			}
 			this._onDidPluginHooksChange.fire();
 		}));
@@ -246,14 +282,18 @@ export class PromptsService extends Disposable implements IPromptsService {
 	) {
 		return autorun(reader => {
 			const plugins = this.agentPluginService.plugins.read(reader);
-			const nextFiles: ILocalPromptPath[] = [];
+			const nextFiles: IPluginPromptPath[] = [];
 			for (const plugin of plugins) {
+				if (!isContributionEnabled(plugin.enablement.read(reader))) {
+					continue;
+				}
 				for (const item of getItems(plugin, reader)) {
 					nextFiles.push({
 						uri: item.uri,
-						storage: PromptsStorage.local,
+						storage: PromptsStorage.plugin,
 						type,
 						name: getCanonicalPluginCommandId(plugin, item.name),
+						pluginUri: plugin.uri,
 					});
 				}
 			}
@@ -313,46 +353,18 @@ export class PromptsService extends Disposable implements IPromptsService {
 			this._pluginPromptFilesByType.get(type) ?? [],
 		]);
 
-		return [...prompts.flat()];
+		return [...prompts.flat(), ...this.internalCustomizations.getPromptPaths(type)];
 	}
 
 	/**
-	 * Collects diagnostic information about which source folders were searched
-	 * and whether they exist, for display in the debug panel.
+	 * Collects diagnostic information about which source folders were searched for display in the debug panel.
 	 */
-	private async _collectSourceFolderDiagnostics(type: PromptsType, foundFiles: readonly { uri: URI }[]): Promise<IPromptSourceFolderResult[]> {
+	private async _collectSourceFolderDiagnostics(type: PromptsType): Promise<IPromptSourceFolderResult[]> {
 		const resolvedFolders = await this.fileLocator.getSourceFoldersInDiscoveryOrder(type);
-		const results: IPromptSourceFolderResult[] = [];
-
-		for (const folder of resolvedFolders) {
-			const fileCount = foundFiles.filter(f => f.uri.path.startsWith(folder.uri.path + '/')).length;
-			let exists = fileCount > 0;
-			let errorMessage: string | undefined;
-
-			if (!exists) {
-				try {
-					const stat = await this.fileService.stat(folder.uri);
-					exists = stat.isDirectory;
-				} catch (e) {
-					if (e instanceof FileOperationError && e.fileOperationResult === FileOperationResult.FILE_NOT_FOUND) {
-						exists = false;
-					} else {
-						exists = false;
-						errorMessage = e instanceof Error ? e.message : String(e);
-					}
-				}
-			}
-
-			results.push({
-				uri: folder.uri,
-				storage: folder.storage,
-				exists,
-				fileCount,
-				errorMessage,
-			});
-		}
-
-		return results;
+		return resolvedFolders.map(folder => ({
+			uri: folder.uri,
+			storage: folder.storage,
+		}));
 	}
 
 	/**
@@ -410,6 +422,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 			this.cachedCustomAgents.refresh();
 		} else if (type === PromptsType.instructions) {
 			this.cachedFileLocations[PromptsType.instructions] = undefined;
+			this._onDidChangeInstructions.fire();
 		} else if (type === PromptsType.prompt) {
 			this.cachedFileLocations[PromptsType.prompt] = undefined;
 			this.cachedSlashCommands.refresh();
@@ -476,6 +489,10 @@ export class PromptsService extends Disposable implements IPromptsService {
 				return this.fileLocator.listFiles(type, PromptsStorage.local, token).then(uris => uris.map(uri => ({ uri, storage: PromptsStorage.local, type } satisfies ILocalPromptPath)));
 			case PromptsStorage.user:
 				return this.fileLocator.listFiles(type, PromptsStorage.user, token).then(uris => uris.map(uri => ({ uri, storage: PromptsStorage.user, type } satisfies IUserPromptPath)));
+			case PromptsStorage.plugin:
+				return this._pluginPromptFilesByType.get(type) ?? [];
+			case PromptsStorage.internal:
+				return this.internalCustomizations.getPromptPaths(type);
 			default:
 				throw new Error(`[listPromptFilesForStorage] Unsupported prompt storage type: ${storage}`);
 		}
@@ -526,12 +543,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 	public async getSourceFolders(type: PromptsType): Promise<readonly IPromptPath[]> {
 		const result: IPromptPath[] = [];
 
-		if (type === PromptsType.agent) {
-			const folders = await this.fileLocator.getAgentSourceFolders();
-			for (const uri of folders) {
-				result.push({ uri, storage: PromptsStorage.local, type });
-			}
-		} else if (type === PromptsType.hook) {
+		if (type === PromptsType.hook) {
 			// For hooks, return the Copilot hooks folder for creating new hooks
 			// (Claude paths are read-only and not included here)
 			const hooksFolders = await this.fileLocator.getHookSourceFolders();
@@ -566,8 +578,25 @@ export class PromptsService extends Disposable implements IPromptsService {
 		return this.cachedSlashCommands.onDidChange;
 	}
 
-	public async getPromptSlashCommands(token: CancellationToken, sessionId?: string): Promise<readonly IChatPromptSlashCommand[]> {
-		return await this.cachedSlashCommands.get(token);
+	public async getPromptSlashCommands(token: CancellationToken, sessionResource?: URI): Promise<readonly IChatPromptSlashCommand[]> {
+		const sw = StopWatch.create();
+		const result = await this.cachedSlashCommands.get(token);
+		if (sessionResource) {
+			const elapsed = sw.elapsed();
+			void this.getPromptSlashCommandDiscoveryInfo(token).catch(() => undefined).then(discoveryInfo => {
+				const details = result.length === 1
+					? localize("promptsService.resolvedSlashCommand", "Resolved {0} slash command in {1}ms", result.length, elapsed.toFixed(1))
+					: localize("promptsService.resolvedSlashCommands", "Resolved {0} slash commands in {1}ms", result.length, elapsed.toFixed(1));
+				this._onDidLogDiscovery.fire({
+					sessionResource,
+					name: localize("promptsService.loadSlashCommands", "Load Slash Commands"),
+					details,
+					discoveryInfo,
+					category: 'discovery',
+				});
+			});
+		}
+		return result;
 	}
 
 	private async computePromptSlashCommands(token: CancellationToken): Promise<readonly IChatPromptSlashCommand[]> {
@@ -613,12 +642,14 @@ export class PromptsService extends Disposable implements IPromptsService {
 	private asChatPromptSlashCommand(parsedPromptFile: ParsedPromptFile, promptPath: IPromptPath): IChatPromptSlashCommand {
 		let name = parsedPromptFile?.header?.name ?? promptPath.name ?? getCleanPromptName(promptPath.uri);
 		name = name.replace(/[^\p{L}\d_\-\.:]+/gu, '-'); // replace spaces with dashes
+		const internalSkill = this.internalCustomizations.getInternalSkillByUri(promptPath.uri);
 		return {
 			name: name,
 			description: parsedPromptFile?.header?.description ?? promptPath.description,
 			argumentHint: parsedPromptFile?.header?.argumentHint,
 			parsedPromptFile,
-			promptPath
+			promptPath,
+			when: internalSkill?.when,
 		};
 	}
 
@@ -640,21 +671,31 @@ export class PromptsService extends Disposable implements IPromptsService {
 		return this.cachedCustomAgents.onDidChange;
 	}
 
-	public async getCustomAgents(token: CancellationToken, sessionId?: string): Promise<readonly ICustomAgent[]> {
+	public get onDidChangeInstructions(): Event<void> {
+		return Event.any(
+			this.getFileLocatorEvent(PromptsType.instructions),
+			this._onDidContributedWhenChange.event,
+			this._onDidChangeInstructions.event,
+			this._onDidPluginPromptFilesChange.event,
+		);
+	}
+
+	public async getCustomAgents(token: CancellationToken, sessionResource?: URI): Promise<readonly ICustomAgent[]> {
 		const sw = StopWatch.create();
 		const result = await this.cachedCustomAgents.get(token);
-		if (sessionId) {
+		if (sessionResource) {
 			const elapsed = sw.elapsed();
-			const discoveryInfo = await this.getAgentDiscoveryInfo(token);
-			const details = result.length === 1
-				? localize("promptsService.resolvedAgent", "Resolved {0} agent in {1}ms", result.length, elapsed.toFixed(1))
-				: localize("promptsService.resolvedAgents", "Resolved {0} agents in {1}ms", result.length, elapsed.toFixed(1));
-			this._onDidLogDiscovery.fire({
-				sessionId,
-				name: localize("promptsService.loadAgents", "Load Agents"),
-				details,
-				discoveryInfo,
-				category: 'discovery',
+			void this.getAgentDiscoveryInfo(token).catch(() => undefined).then(discoveryInfo => {
+				const details = result.length === 1
+					? localize("promptsService.resolvedAgent", "Resolved {0} agent in {1}ms", result.length, elapsed.toFixed(1))
+					: localize("promptsService.resolvedAgents", "Resolved {0} agents in {1}ms", result.length, elapsed.toFixed(1));
+				this._onDidLogDiscovery.fire({
+					sessionResource,
+					name: localize("promptsService.loadAgents", "Load Agents"),
+					details,
+					discoveryInfo,
+					category: 'discovery',
+				});
 			});
 		}
 		return result;
@@ -664,6 +705,12 @@ export class PromptsService extends Disposable implements IPromptsService {
 		let agentFiles = await this.listPromptFiles(PromptsType.agent, token);
 		const disabledAgents = this.getDisabledPromptFiles(PromptsType.agent);
 		agentFiles = agentFiles.filter(promptPath => !disabledAgents.has(promptPath.uri));
+
+		// Get user home for tilde expansion in hook cwd paths
+		const userHomeUri = await this.pathService.userHome();
+		const userHome = userHomeUri.scheme === Schemas.file ? userHomeUri.fsPath : userHomeUri.path;
+		const defaultFolder = this.workspaceService.getWorkspace().folders[0];
+
 		const customAgentsResults = await Promise.allSettled(
 			agentFiles.map(async (promptPath): Promise<ICustomAgent> => {
 				const uri = promptPath.uri;
@@ -708,7 +755,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 				}
 				const visibility = {
 					userInvocable: ast.header.userInvocable !== false,
-					agentInvocable: ast.header.infer === true || ast.header.disableModelInvocation !== true,
+					agentInvocable: ast.header.infer !== undefined ? ast.header.infer === true : ast.header.disableModelInvocation !== true,
 				} satisfies ICustomAgentVisibility;
 
 				let model = ast.header.model;
@@ -719,7 +766,18 @@ export class PromptsService extends Disposable implements IPromptsService {
 				if (target === Target.Claude && tools) {
 					tools = mapClaudeTools(tools);
 				}
-				return { uri, name, description, model, tools, handOffs, argumentHint, target, visibility, agents, agentInstructions, source };
+
+				// Parse hooks from the frontmatter if present
+				let hooks: ChatRequestHooks | undefined;
+				const useCustomAgentHooks = this.configurationService.getValue<boolean>(PromptsConfig.USE_CUSTOM_AGENT_HOOKS);
+				const hooksRaw = ast.header.hooksRaw;
+				if (useCustomAgentHooks && hooksRaw) {
+					const hookWorkspaceFolder = this.workspaceService.getWorkspaceFolder(uri) ?? defaultFolder;
+					const workspaceRootUri = hookWorkspaceFolder?.uri;
+					hooks = parseSubagentHooksFromYaml(hooksRaw, workspaceRootUri, userHome, target);
+				}
+
+				return { uri, name, description, model, tools, handOffs, argumentHint, target, visibility, agents, hooks, agentInstructions, source };
 			})
 		);
 
@@ -832,7 +890,9 @@ export class PromptsService extends Disposable implements IPromptsService {
 			case PromptsStorage.extension: {
 				return localize('extension.with.id', 'Extension: {0}', promptPath.extension.displayName ?? promptPath.extension.id);
 			}
-			default: throw new Error('Unknown prompt storage type');
+			case PromptsStorage.plugin: return localize('plugin.capitalized', 'Plugin');
+			case PromptsStorage.internal: return localize('internal.builtIn', 'Built-in');
+			default: assertNever(promptPath, 'Unknown prompt storage type');
 		}
 	}
 
@@ -848,49 +908,42 @@ export class PromptsService extends Disposable implements IPromptsService {
 		return [];
 	}
 
-	public async listAgentMDs(token: CancellationToken, logger: Logger | undefined): Promise<IResolvedAgentFile[]> {
+	public async listAgentInstructions(token: CancellationToken, logger: Logger | undefined): Promise<IResolvedAgentFile[]> {
+		const resolvedAgentFiles: IResolvedAgentFile[] = [];
+		const promises: Promise<IResolvedAgentFile[]>[] = [];
+
+		const includeParents = this.configurationService.getValue(PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS) === true;
+		const rootFolders = await this.fileLocator.getWorkspaceFolderRoots(includeParents, logger);
+
+		const rootFiles: IWorkspaceInstructionFile[] = [];
 		const useAgentMD = this.configurationService.getValue(PromptsConfig.USE_AGENT_MD);
 		if (!useAgentMD) {
 			logger?.logInfo('Agent MD files are disabled via configuration.');
-			return [];
+		} else {
+			rootFiles.push({ fileName: AGENT_MD_FILENAME, type: AgentFileType.agentsMd });
 		}
-		return await this.fileLocator.findFilesInWorkspaceRoots(AGENT_MD_FILENAME, undefined, AgentFileType.agentsMd, token);
-	}
-
-	public async listClaudeMDs(token: CancellationToken, logger: Logger | undefined): Promise<IResolvedAgentFile[]> {
-		// see https://code.claude.com/docs/en/memory
 		const useClaudeMD = this.configurationService.getValue(PromptsConfig.USE_CLAUDE_MD);
 		if (!useClaudeMD) {
 			logger?.logInfo('Claude MD files are disabled via configuration.');
-			return [];
-		}
-		const results: IResolvedAgentFile[] = [];
-		const userHome = await this.pathService.userHome();
-		const userClaudeFolder = joinPath(userHome, CLAUDE_CONFIG_FOLDER);
-		await Promise.all([
-			this.fileLocator.findFilesInWorkspaceRoots(CLAUDE_MD_FILENAME, undefined, AgentFileType.claudeMd, token, results), // in workspace roots
-			this.fileLocator.findFilesInWorkspaceRoots(CLAUDE_LOCAL_MD_FILENAME, undefined, AgentFileType.claudeMd, token, results), // CLAUDE.local in workspace roots
-			this.fileLocator.findFilesInWorkspaceRoots(CLAUDE_MD_FILENAME, CLAUDE_CONFIG_FOLDER, AgentFileType.claudeMd, token, results), // in workspace/.claude folders
-			this.fileLocator.findFilesInRoots([userClaudeFolder], CLAUDE_MD_FILENAME, AgentFileType.claudeMd, token, results) // in ~/.claude folder
-		]);
-		return results.sort((a, b) => a.uri.toString().localeCompare(b.uri.toString()));
-	}
+		} else {
+			const claudeMdFile = { fileName: CLAUDE_MD_FILENAME, type: AgentFileType.claudeMd };
+			rootFiles.push(claudeMdFile); // CLAUDE.md in workspace root
+			rootFiles.push({ fileName: CLAUDE_LOCAL_MD_FILENAME, type: AgentFileType.claudeMd }); // CLAUDE.local.md in workspace root
 
-	public async listCopilotInstructionsMDs(token: CancellationToken, logger: Logger | undefined): Promise<IResolvedAgentFile[]> {
+			promises.push(this.fileLocator.findFilesInRoots(rootFolders, CLAUDE_CONFIG_FOLDER, [claudeMdFile], token, resolvedAgentFiles)); // CLAUDE.md in .claude folder under workspace root
+			promises.push(this.fileLocator.findFilesInRoots([await this.pathService.userHome()], CLAUDE_CONFIG_FOLDER, [claudeMdFile], token, resolvedAgentFiles)); // CLAUDE.md in in ~/.claude folder
+		}
 		const useCopilotInstructionsFiles = this.configurationService.getValue(PromptsConfig.USE_COPILOT_INSTRUCTION_FILES);
 		if (!useCopilotInstructionsFiles) {
 			logger?.logInfo('Copilot instructions files are disabled via configuration.');
-			return [];
+		} else {
+			const githubConfigFiles = [{ fileName: COPILOT_CUSTOM_INSTRUCTIONS_FILENAME, type: AgentFileType.copilotInstructionsMd }];
+			promises.push(this.fileLocator.findFilesInRoots(rootFolders, GITHUB_CONFIG_FOLDER, githubConfigFiles, token, resolvedAgentFiles));
 		}
-		return await this.fileLocator.findCopilotInstructionsMDsInWorkspace(token);
-	}
 
-	public async listAgentInstructions(token: CancellationToken, logger: Logger | undefined): Promise<IResolvedAgentFile[]> {
-		const [agentMDs, claudeMDs, copilotInstructionsMDs] = await Promise.all([
-			this.listAgentMDs(token, logger),
-			this.listClaudeMDs(token, logger),
-			this.listCopilotInstructionsMDs(token, logger)
-		]);
+		promises.push(this.fileLocator.findFilesInRoots(rootFolders, undefined, rootFiles, token, resolvedAgentFiles));
+
+		await Promise.all(promises);
 		if (token.isCancellationRequested) {
 			return [];
 		}
@@ -907,9 +960,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 			}
 			return true;
 		};
-		agentMDs.forEach(add);
-		claudeMDs.forEach(add);
-		copilotInstructionsMDs.forEach(add);
+		resolvedAgentFiles.forEach(add);
 		for (const symlink of symlinks) {
 			if (seenFileURI.has(symlink.realPath)) {
 				logger?.logInfo(`Skipping symlinked agent instructions file ${symlink.uri} as target already included: ${symlink.realPath}`);
@@ -918,7 +969,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 				seenFileURI.add(symlink.realPath);
 			}
 		}
-		return result;
+		return result.sort((a, b) => a.uri.toString().localeCompare(b.uri.toString()));
 	}
 
 	public getAgentFileURIFromModeFile(oldURI: URI): URI | undefined {
@@ -1033,7 +1084,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 		return this.cachedSkills.onDidChange;
 	}
 
-	public async findAgentSkills(token: CancellationToken, sessionId?: string): Promise<IAgentSkill[] | undefined> {
+	public async findAgentSkills(token: CancellationToken, sessionResource?: URI): Promise<IAgentSkill[] | undefined> {
 		const useAgentSkills = this.configurationService.getValue(PromptsConfig.USE_AGENT_SKILLS);
 		if (!useAgentSkills) {
 			return undefined;
@@ -1041,18 +1092,19 @@ export class PromptsService extends Disposable implements IPromptsService {
 
 		const sw = StopWatch.create();
 		const result = await this.cachedSkills.get(token);
-		if (sessionId) {
+		if (sessionResource) {
 			const elapsed = sw.elapsed();
-			const discoveryInfo = await this.getSkillDiscoveryInfo(token);
-			const details = result.length === 1
-				? localize("promptsService.resolvedSkill", "Resolved {0} skill in {1}ms", result.length, elapsed.toFixed(1))
-				: localize("promptsService.resolvedSkills", "Resolved {0} skills in {1}ms", result.length, elapsed.toFixed(1));
-			this._onDidLogDiscovery.fire({
-				sessionId,
-				name: localize("promptsService.loadSkills", "Load Skills"),
-				details,
-				discoveryInfo,
-				category: 'discovery',
+			void this.getSkillDiscoveryInfo(token).catch(() => undefined).then(discoveryInfo => {
+				const details = result.length === 1
+					? localize("promptsService.resolvedSkill", "Resolved {0} skill in {1}ms", result.length, elapsed.toFixed(1))
+					: localize("promptsService.resolvedSkills", "Resolved {0} skills in {1}ms", result.length, elapsed.toFixed(1));
+				this._onDidLogDiscovery.fire({
+					sessionResource,
+					name: localize("promptsService.loadSkills", "Load Skills"),
+					details,
+					discoveryInfo,
+					category: 'discovery',
+				});
 			});
 		}
 		return result;
@@ -1066,13 +1118,15 @@ export class PromptsService extends Disposable implements IPromptsService {
 		for (const file of files) {
 			if (file.status === 'loaded' && file.name) {
 				const sanitizedDescription = this.truncateAgentSkillDescription(file.description, file.uri);
+				const internalSkill = this.internalCustomizations.getInternalSkillByUri(file.uri);
 				result.push({
 					uri: file.uri,
 					storage: file.storage,
 					name: file.name,
 					description: sanitizedDescription,
 					disableModelInvocation: file.disableModelInvocation ?? false,
-					userInvocable: file.userInvocable ?? true
+					userInvocable: file.userInvocable ?? true,
+					when: internalSkill?.when,
 				});
 			}
 		}
@@ -1108,6 +1162,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 			configWorkspace: number;
 			extensionContribution: number;
 			extensionAPI: number;
+			plugin: number;
 			skippedDuplicateName: number;
 			skippedMissingName: number;
 			skippedMissingDescription: number;
@@ -1127,6 +1182,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 			configWorkspace: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'Number of custom configured workspace skills.' };
 			extensionContribution: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'Number of extension contributed skills.' };
 			extensionAPI: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'Number of extension API provided skills.' };
+			plugin: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'Number of plugin provided skills.' };
 			skippedDuplicateName: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'Number of skills skipped due to duplicate names.' };
 			skippedMissingName: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'Number of skills skipped due to missing name attribute.' };
 			skippedMissingDescription: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'Number of skills skipped due to missing description attribute.' };
@@ -1148,6 +1204,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 			configPersonal: skillsBySource.get(PromptFileSource.ConfigPersonal) ?? 0,
 			extensionContribution: skillsBySource.get(PromptFileSource.ExtensionContribution) ?? 0,
 			extensionAPI: skillsBySource.get(PromptFileSource.ExtensionAPI) ?? 0,
+			plugin: skillsBySource.get(PromptFileSource.Plugin) ?? 0,
 			skippedDuplicateName,
 			skippedMissingName,
 			skippedMissingDescription,
@@ -1158,42 +1215,44 @@ export class PromptsService extends Disposable implements IPromptsService {
 		return result;
 	}
 
-	public async getHooks(token: CancellationToken, sessionId?: string): Promise<IConfiguredHooksInfo | undefined> {
+	public async getHooks(token: CancellationToken, sessionResource?: URI): Promise<IConfiguredHooksInfo | undefined> {
 		const sw = StopWatch.create();
 		const result = await this.cachedHooks.get(token);
-		if (sessionId) {
+		if (sessionResource) {
 			const elapsed = sw.elapsed();
-			const hookCount = result ? Object.values(result.hooks).reduce((sum, arr) => sum + arr.length, 0) : 0;
-			const discoveryInfo = await this.getHookDiscoveryInfo(token);
-			const details = hookCount === 1
-				? localize("promptsService.resolvedHook", "Resolved {0} hook in {1}ms", hookCount, elapsed.toFixed(1))
-				: localize("promptsService.resolvedHooks", "Resolved {0} hooks in {1}ms", hookCount, elapsed.toFixed(1));
-			this._onDidLogDiscovery.fire({
-				sessionId,
-				name: localize("promptsService.loadHooks", "Load Hooks"),
-				details,
-				discoveryInfo,
-				category: 'discovery',
+			void this.getHookDiscoveryInfo(token).catch(() => undefined).then(discoveryInfo => {
+				const hookCount = result ? Object.values(result.hooks).reduce((sum, arr) => sum + arr.length, 0) : 0;
+				const details = hookCount === 1
+					? localize("promptsService.resolvedHook", "Resolved {0} hook in {1}ms", hookCount, elapsed.toFixed(1))
+					: localize("promptsService.resolvedHooks", "Resolved {0} hooks in {1}ms", hookCount, elapsed.toFixed(1));
+				this._onDidLogDiscovery.fire({
+					sessionResource,
+					name: localize("promptsService.loadHooks", "Load Hooks"),
+					details,
+					discoveryInfo,
+					category: 'discovery',
+				});
 			});
 		}
 		return result;
 	}
 
-	public async getInstructionFiles(token: CancellationToken, sessionId?: string): Promise<readonly IPromptPath[]> {
+	public async getInstructionFiles(token: CancellationToken, sessionResource?: URI): Promise<readonly IPromptPath[]> {
 		const sw = StopWatch.create();
 		const result = await this.listPromptFiles(PromptsType.instructions, token);
-		if (sessionId) {
+		if (sessionResource) {
 			const elapsed = sw.elapsed();
-			const discoveryInfo = await this.getInstructionsDiscoveryInfo(token);
-			const details = result.length === 1
-				? localize("promptsService.resolvedInstruction", "Resolved {0} instruction in {1}ms", result.length, elapsed.toFixed(1))
-				: localize("promptsService.resolvedInstructions", "Resolved {0} instructions in {1}ms", result.length, elapsed.toFixed(1));
-			this._onDidLogDiscovery.fire({
-				sessionId,
-				name: localize("promptsService.loadInstructions", "Load Instructions"),
-				details,
-				discoveryInfo,
-				category: 'discovery',
+			void this.getInstructionsDiscoveryInfo(token).catch(() => undefined).then(discoveryInfo => {
+				const details = result.length === 1
+					? localize("promptsService.resolvedInstruction", "Resolved {0} instruction in {1}ms", result.length, elapsed.toFixed(1))
+					: localize("promptsService.resolvedInstructions", "Resolved {0} instructions in {1}ms", result.length, elapsed.toFixed(1));
+				this._onDidLogDiscovery.fire({
+					sessionResource,
+					name: localize("promptsService.loadInstructions", "Load Instructions"),
+					details,
+					discoveryInfo,
+					category: 'discovery',
+				});
 			});
 		}
 		return result;
@@ -1205,6 +1264,10 @@ export class PromptsService extends Disposable implements IPromptsService {
 			return undefined;
 		}
 
+		if (!this.workspaceTrustService.isWorkspaceTrusted()) {
+			return undefined;
+		}
+
 		const useClaudeHooks = this.configurationService.getValue<boolean>(PromptsConfig.USE_CLAUDE_HOOKS);
 		const hookFiles = await this.listPromptFiles(PromptsType.hook, token);
 
@@ -1215,16 +1278,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 		const userHome = userHomeUri.scheme === Schemas.file ? userHomeUri.fsPath : userHomeUri.path;
 
 		let hasDisabledClaudeHooks = false;
-		const collectedHooks: Record<HookType, IHookCommand[]> = {
-			[HookType.SessionStart]: [],
-			[HookType.UserPromptSubmit]: [],
-			[HookType.PreToolUse]: [],
-			[HookType.PostToolUse]: [],
-			[HookType.PreCompact]: [],
-			[HookType.SubagentStart]: [],
-			[HookType.SubagentStop]: [],
-			[HookType.Stop]: [],
-		};
+		const collectedHooks = new Map<HookType, IHookCommand[]>();
 
 		const defaultFolder = this.workspaceService.getWorkspace().folders[0];
 
@@ -1259,7 +1313,12 @@ export class PromptsService extends Disposable implements IPromptsService {
 
 				for (const [hookType, { hooks: commands }] of hooks) {
 					for (const command of commands) {
-						collectedHooks[hookType].push(command);
+						let bucket = collectedHooks.get(hookType);
+						if (!bucket) {
+							bucket = [];
+							collectedHooks.set(hookType, bucket);
+						}
+						bucket.push(command);
 						this.logger.trace(`[PromptsService] Collected ${hookType} hook from ${hookFile.uri} (format: ${format})`);
 					}
 				}
@@ -1271,79 +1330,32 @@ export class PromptsService extends Disposable implements IPromptsService {
 		// Collect hooks from agent plugins
 		const plugins = this.agentPluginService.plugins.get();
 		for (const plugin of plugins) {
+			if (!isContributionEnabled(plugin.enablement.get())) {
+				continue;
+			}
 			for (const hook of plugin.hooks.get()) {
-				collectedHooks[hook.type].push(...hook.hooks);
+				let bucket = collectedHooks.get(hook.type);
+				if (!bucket) {
+					bucket = [];
+					collectedHooks.set(hook.type, bucket);
+				}
+				bucket.push(...hook.hooks);
 			}
 		}
 
 		// Check if any hooks were collected
-		const hasHooks = Object.values(collectedHooks).some(arr => arr.length > 0);
-		if (!hasHooks) {
+		if (collectedHooks.size === 0) {
 			this.logger.trace('[PromptsService] No valid hooks collected.');
 			return undefined;
 		}
 
-		// Build the result, only including hook types that have entries
-		const result: IChatRequestHooks = Object.fromEntries(
-			Object.entries(collectedHooks).filter(([_, commands]) => commands.length > 0)
-		) as IChatRequestHooks;
+		// Build the result
+		const result: ChatRequestHooks = Object.fromEntries(collectedHooks) as ChatRequestHooks;
 
 		this.logger.trace(`[PromptsService] Collected hooks: ${JSON.stringify(Object.keys(result))}`);
 		return { hooks: result, hasDisabledClaudeHooks };
 	}
 
-	public async getPromptDiscoveryInfo(type: PromptsType, token: CancellationToken, sessionId?: string): Promise<IPromptDiscoveryInfo> {
-		if (sessionId) {
-			this._onDidLogDiscovery.fire({
-				sessionId,
-				name: localize("promptsService.discoveryStart", "Discovery {0} (Start)", type),
-				category: 'discovery',
-			});
-		}
-		const files: IPromptFileDiscoveryResult[] = [];
-
-		let result: IPromptDiscoveryInfo;
-		if (type === PromptsType.skill) {
-			result = await this.getSkillDiscoveryInfo(token);
-		} else if (type === PromptsType.agent) {
-			result = await this.getAgentDiscoveryInfo(token);
-		} else if (type === PromptsType.prompt) {
-			result = await this.getPromptSlashCommandDiscoveryInfo(token);
-		} else if (type === PromptsType.instructions) {
-			result = await this.getInstructionsDiscoveryInfo(token);
-		} else if (type === PromptsType.hook) {
-			result = await this.getHookDiscoveryInfo(token);
-		} else {
-			result = { type, files };
-		}
-
-		const loadedCount = result.files.filter(f => f.status === 'loaded').length;
-		const skippedCount = result.files.filter(f => f.status === 'skipped').length;
-
-		// Add source folder diagnostics if not already present
-		if (!result.sourceFolders) {
-			const sourceFolders = await this._collectSourceFolderDiagnostics(type, result.files.filter(f => f.status === 'loaded'));
-			result = { ...result, sourceFolders };
-		}
-
-		if (sessionId) {
-			const details = localize(
-				"promptsService.discoveryResult",
-				"{0} loaded, {1} skipped",
-				loadedCount,
-				skippedCount,
-			);
-			this._onDidLogDiscovery.fire({
-				sessionId,
-				name: localize("promptsService.discoveryEnd", "Discovery {0} (End)", type),
-				details,
-				discoveryInfo: result,
-				category: 'discovery',
-			});
-		}
-		return result;
-	}
-
 	private async getSkillDiscoveryInfo(token: CancellationToken): Promise<IPromptDiscoveryInfo> {
 		const useAgentSkills = this.configurationService.getValue(PromptsConfig.USE_AGENT_SKILLS);
 
@@ -1357,13 +1369,12 @@ export class PromptsService extends Disposable implements IPromptsService {
 				skipReason: 'disabled' as const,
 				extensionId: promptPath.extension?.identifier?.value
 			}));
-			const sourceFolders = await this._collectSourceFolderDiagnostics(PromptsType.skill, []);
+			const sourceFolders = await this._collectSourceFolderDiagnostics(PromptsType.skill);
 			return { type: PromptsType.skill, files, sourceFolders };
 		}
 
 		const { files } = await this.computeSkillDiscoveryInfo(token);
-		const sourceFolders = await this._collectSourceFolderDiagnostics(PromptsType.skill, files.filter(f => f.status === 'loaded'));
-		return { type: PromptsType.skill, files, sourceFolders };
+		return { type: PromptsType.skill, files };
 	}
 
 	/**
@@ -1383,11 +1394,21 @@ export class PromptsService extends Disposable implements IPromptsService {
 		const allSkills: Array<IResolvedPromptFile> = [];
 		const discoveredSkills = await this.fileLocator.findAgentSkills(token);
 		const extensionSkills = await this.getExtensionPromptFiles(PromptsType.skill, token);
+		const pluginSkills = this._pluginPromptFilesByType.get(PromptsType.skill) ?? [];
 		allSkills.push(...discoveredSkills, ...extensionSkills.map((extPath) => ({
 			fileUri: extPath.uri,
 			storage: extPath.storage,
 			source: extPath.source === ExtensionAgentSourceType.contribution ? PromptFileSource.ExtensionContribution : PromptFileSource.ExtensionAPI
-		})));
+		})), ...pluginSkills.map((p) => ({
+			fileUri: p.uri,
+			storage: p.storage,
+			source: PromptFileSource.Plugin,
+		})), ...this.internalCustomizations.getSkills()
+			.map(s => ({
+				fileUri: s.uri,
+				storage: s.storage,
+				source: PromptFileSource.Internal,
+			})));
 
 		const getPriority = (skill: IResolvedPromptFile | IExtensionPromptPath): number => {
 			if (skill.storage === PromptsStorage.local) {
@@ -1396,13 +1417,16 @@ export class PromptsService extends Disposable implements IPromptsService {
 			if (skill.storage === PromptsStorage.user) {
 				return 1; // personal
 			}
+			if (skill.storage === PromptsStorage.plugin) {
+				return 2; // plugin
+			}
 			if (skill.source === PromptFileSource.ExtensionAPI) {
-				return 2;
+				return 3;
 			}
 			if (skill.source === PromptFileSource.ExtensionContribution) {
-				return 3;
+				return 4;
 			}
-			return 4;
+			return 5;
 		};
 		// Stable sort; we should keep order consistent to the order in the user's configuration object
 		allSkills.sort((a, b) => getPriority(a) - getPriority(b));
@@ -1507,7 +1531,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 			}
 		}
 
-		const sourceFolders = await this._collectSourceFolderDiagnostics(PromptsType.agent, files.filter(f => f.status === 'loaded'));
+		const sourceFolders = await this._collectSourceFolderDiagnostics(PromptsType.agent);
 		return { type: PromptsType.agent, files, sourceFolders };
 	}
 
@@ -1536,7 +1560,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 			}
 		}
 
-		const sourceFolders = await this._collectSourceFolderDiagnostics(PromptsType.prompt, files.filter(f => f.status === 'loaded'));
+		const sourceFolders = await this._collectSourceFolderDiagnostics(PromptsType.prompt);
 		return { type: PromptsType.prompt, files, sourceFolders };
 	}
 
@@ -1565,7 +1589,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 			}
 		}
 
-		const sourceFolders = await this._collectSourceFolderDiagnostics(PromptsType.instructions, files.filter(f => f.status === 'loaded'));
+		const sourceFolders = await this._collectSourceFolderDiagnostics(PromptsType.instructions);
 		return { type: PromptsType.instructions, files, sourceFolders };
 	}
 
@@ -1584,6 +1608,19 @@ export class PromptsService extends Disposable implements IPromptsService {
 			const extensionId = promptPath.extension?.identifier?.value;
 			const name = basename(uri);
 
+			// Ignored if workspace is untrusted
+			if (!this.workspaceTrustService.isWorkspaceTrusted()) {
+				files.push({
+					uri: promptPath.uri,
+					storage: promptPath.storage,
+					status: 'skipped',
+					skipReason: 'workspace-untrusted',
+					name: basename(promptPath.uri),
+					extensionId: promptPath.extension?.identifier?.value,
+				});
+				continue;
+			}
+
 			// Skip Claude hooks when the setting is disabled
 			if (getHookSourceFormat(uri) === HookSourceFormat.Claude && useClaudeHooks === false) {
 				files.push({
@@ -1651,7 +1688,7 @@ export class PromptsService extends Disposable implements IPromptsService {
 			}
 		}
 
-		const sourceFolders = await this._collectSourceFolderDiagnostics(PromptsType.hook, files.filter(f => f.status === 'loaded'));
+		const sourceFolders = await this._collectSourceFolderDiagnostics(PromptsType.hook);
 		return { type: PromptsType.hook, files, sourceFolders };
 	}
 }
@@ -1751,6 +1788,15 @@ namespace IAgentSource {
 				extensionId: promptPath.extension.identifier,
 				type: promptPath.source
 			};
+		} else if (promptPath.storage === PromptsStorage.plugin) {
+			return {
+				storage: PromptsStorage.plugin,
+				pluginUri: promptPath.pluginUri
+			};
+		} else if (promptPath.storage === PromptsStorage.internal) {
+			return {
+				storage: PromptsStorage.internal
+			};
 		} else {
 			return {
 				storage: promptPath.storage
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/utils/promptFilesLocator.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/utils/promptFilesLocator.ts
index c626f883a7438..21de3116a39d3 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/utils/promptFilesLocator.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/utils/promptFilesLocator.ts
@@ -9,28 +9,42 @@ import { ResourceSet } from '../../../../../../base/common/map.js';
 import * as nls from '../../../../../../nls.js';
 import { FileOperationError, FileOperationResult, IFileService } from '../../../../../../platform/files/common/files.js';
 import { getPromptFileLocationsConfigKey, isTildePath, PromptsConfig } from '../config/config.js';
-import { basename, dirname, isEqualOrParent, joinPath } from '../../../../../../base/common/resources.js';
+import { basename, dirname, isEqual, isEqualOrParent, joinPath, extname } from '../../../../../../base/common/resources.js';
 import { IWorkspaceContextService, IWorkspaceFolder } from '../../../../../../platform/workspace/common/workspace.js';
 import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
-import { COPILOT_CUSTOM_INSTRUCTIONS_FILENAME, AGENTS_SOURCE_FOLDER, getPromptFileExtension, getPromptFileType, LEGACY_MODE_FILE_EXTENSION, getCleanPromptName, AGENT_FILE_EXTENSION, getPromptFileDefaultLocations, SKILL_FILENAME, IPromptSourceFolder, DEFAULT_AGENT_SOURCE_FOLDERS, IResolvedPromptFile, IResolvedPromptSourceFolder, PromptFileSource, isInClaudeRulesFolder } from '../config/promptFileLocations.js';
+import { AGENTS_SOURCE_FOLDER, getPromptFileExtension, getPromptFileType, LEGACY_MODE_FILE_EXTENSION, getCleanPromptName, AGENT_FILE_EXTENSION, getPromptFileDefaultLocations, SKILL_FILENAME, IPromptSourceFolder, IResolvedPromptFile, IResolvedPromptSourceFolder, PromptFileSource } from '../config/promptFileLocations.js';
 import { PromptsType } from '../promptTypes.js';
 import { IWorkbenchEnvironmentService } from '../../../../../services/environment/common/environmentService.js';
 import { Schemas } from '../../../../../../base/common/network.js';
 import { getExcludes, IFileQuery, ISearchConfiguration, ISearchService, QueryType } from '../../../../../services/search/common/search.js';
-import { CancellationToken } from '../../../../../../base/common/cancellation.js';
+import { CancellationToken, CancellationTokenSource } from '../../../../../../base/common/cancellation.js';
 import { isCancellationError } from '../../../../../../base/common/errors.js';
-import { AgentFileType, IResolvedAgentFile, PromptsStorage } from '../service/promptsService.js';
+import { AgentFileType, IResolvedAgentFile, Logger, PromptsStorage } from '../service/promptsService.js';
 import { IUserDataProfileService } from '../../../../../services/userDataProfile/common/userDataProfile.js';
 import { Emitter, Event } from '../../../../../../base/common/event.js';
 import { DisposableStore } from '../../../../../../base/common/lifecycle.js';
 import { ILogService } from '../../../../../../platform/log/common/log.js';
 import { IPathService } from '../../../../../services/path/common/pathService.js';
+import { equalsIgnoreCase } from '../../../../../../base/common/strings.js';
+import { IWorkspaceTrustManagementService } from '../../../../../../platform/workspace/common/workspaceTrust.js';
+
+/**
+ * Maximum recursion depth when traversing subdirectories for instruction files.
+ */
+const MAX_INSTRUCTIONS_RECURSION_DEPTH = 5;
+
+export interface IWorkspaceInstructionFile {
+	readonly fileName: string;
+	readonly type: AgentFileType;
+}
 
 /**
  * Utility class to locate prompt files.
  */
 export class PromptFilesLocator {
 
+	private readonly userDataFolder: IResolvedPromptSourceFolder;
+
 	constructor(
 		@IFileService private readonly fileService: IFileService,
 		@IConfigurationService private readonly configService: IConfigurationService,
@@ -40,7 +54,19 @@ export class PromptFilesLocator {
 		@IUserDataProfileService private readonly userDataService: IUserDataProfileService,
 		@ILogService private readonly logService: ILogService,
 		@IPathService private readonly pathService: IPathService,
+		@IWorkspaceTrustManagementService private readonly workspaceTrustManagementService: IWorkspaceTrustManagementService,
 	) {
+
+		const userDataPromptsHome = this.userDataService.currentProfile.promptsHome;
+		this.userDataFolder = {
+			uri: userDataPromptsHome,
+			parent: userDataPromptsHome,
+			filePattern: undefined,
+			source: PromptFileSource.CopilotPersonal,
+			storage: PromptsStorage.user,
+			displayPath: nls.localize('promptsUserDataFolder', "User Data"),
+			isDefault: true
+		};
 	}
 
 	protected getWorkspaceFolders(): readonly IWorkspaceFolder[] {
@@ -55,26 +81,85 @@ export class PromptFilesLocator {
 		return Event.map(this.workspaceService.onDidChangeWorkspaceFolders, () => undefined);
 	}
 
+	public async getWorkspaceFolderRoots(includeParents: boolean, logger?: Logger): Promise<URI[]> {
+		const workspaceFolders = this.getWorkspaceFolders();
+		if (includeParents) {
+			const roots = new ResourceSet();
+			const userHome = await this.pathService.userHome();
+			for (const workspaceFolder of workspaceFolders) {
+				roots.add(workspaceFolder.uri);
+				// Walk up from the workspace folder to find the repository root
+				// (.git folder). Only include parent folders if a repo root is
+				// actually found; otherwise keep only the workspace folder.
+				const parents = await this.findParentRepoFolders(workspaceFolder.uri, userHome, roots, logger);
+				for (const parent of parents) {
+					roots.add(parent);
+				}
+			}
+			return [...roots];
+		}
+		return workspaceFolders.map(f => f.uri);
+	}
+
+	/**
+	 * Walks up from {@link folderUri} collecting parent folders until a
+	 * repository root (a folder containing `.git`) is found.  Returns the
+	 * intermediate parent folders only when a repo root is found; returns
+	 * an empty array when the walk reaches the filesystem root, the user
+	 * home directory, or a folder already present in {@link seen}.
+	 */
+	private async findParentRepoFolders(folderUri: URI, userHome: URI, seen: ResourceSet, logger?: Logger): Promise<URI[]> {
+		const candidates: URI[] = [];
+		let current = folderUri;
+		let parent = dirname(current);
+		do {
+			try {
+				const isRepoRoot = await this.fileService.exists(joinPath(current, '.git'));
+				if (isRepoRoot) {
+					if ((await this.workspaceTrustManagementService.getUriTrustInfo(current)).trusted) {
+						candidates.push(current);
+						return candidates;
+					}
+					logger?.logInfo(`Repository root found at ${current.toString()}, but it is not trusted. Skipping parent folder inclusion for this workspace folder.`);
+					return []; // if the repo root isn't trusted, don't include it or any parents
+				}
+			} catch (e) {
+				const msg = e instanceof Error ? e.message : String(e);
+				logger?.logInfo(`No repository root found for folder ${folderUri.toString()}. Error accessing ${joinPath(current, '.git')}: ${msg}.`);
+				return []; // if we can't access the folder, return an empty list to avoid treating it as a non-repository when we might just have a permission issue
+			}
+			candidates.push(current);
+			current = parent;
+			parent = dirname(current);
+		} while (!seen.has(current) && current.path !== '/' && !isEqual(userHome, current));
+		// no repo found
+		logger?.logInfo(`No repository root found for folder ${folderUri.toString()}.`);
+		return [];
+	}
+
 	/**
 	 * List all prompt files from the filesystem.
 	 *
 	 * @returns List of prompt files found in the workspace.
 	 */
 	public async listFiles(type: PromptsType, storage: PromptsStorage, token: CancellationToken): Promise<readonly URI[]> {
-		if (storage === PromptsStorage.local) {
-			return await this.listFilesInLocal(type, token);
-		} else if (storage === PromptsStorage.user) {
-			return await this.listFilesInUserData(type, token);
+		if (storage !== PromptsStorage.user && storage !== PromptsStorage.local) {
+			throw new Error(`Unsupported prompt file storage: ${storage}`);
+		}
+
+		const configuredLocations = PromptsConfig.promptSourceFolders(this.configService, type);
+		const absoluteLocations = await this.toAbsoluteLocations(type, configuredLocations.filter(loc => loc.storage === storage));
+
+		if (storage === PromptsStorage.user && (type === PromptsType.agent || type === PromptsType.instructions || type === PromptsType.prompt)) {
+			absoluteLocations.push(this.userDataFolder);
 		}
-		throw new Error(`Unsupported prompt file storage: ${storage}`);
-	}
 
-	private async listFilesInUserData(type: PromptsType, token: CancellationToken): Promise<readonly URI[]> {
-		const userStorageFolders = await this.getUserStorageFolders(type);
 		const paths = new ResourceSet();
 
-		for (const { uri } of userStorageFolders) {
-			const files = await this.resolveFilesAtLocation(uri, type, token);
+		for (const { parent, filePattern } of absoluteLocations) {
+			const files = (filePattern === undefined)
+				? await this.resolveFilesAtLocation(parent, type, token) // if the location does not contain a glob pattern, resolve the location directly
+				: await this.searchFilesInLocation(parent, filePattern, token);
 			for (const file of files) {
 				if (getPromptFileType(file) === type) {
 					paths.add(file);
@@ -84,123 +169,57 @@ export class PromptFilesLocator {
 				return [];
 			}
 		}
-
 		return [...paths];
 	}
 
-	/**
-	 * Gets all user storage folders for the given prompt type.
-	 * This includes configured tilde paths and the VS Code user data prompts folder.
-	 */
-	private async getUserStorageFolders(type: PromptsType): Promise<readonly IResolvedPromptSourceFolder[]> {
-		const userHome = await this.pathService.userHome();
-		const configuredLocations = PromptsConfig.promptSourceFolders(this.configService, type);
-		const absoluteLocations = this.toAbsoluteLocations(type, configuredLocations, userHome);
-
-		// Filter to only user storage locations
-		const result = absoluteLocations.filter(loc => loc.storage === PromptsStorage.user);
-
-		// Also include the VS Code user data prompts folder for certain types
-		if (type === PromptsType.agent || type === PromptsType.instructions || type === PromptsType.prompt) {
-			const userDataPromptsHome = this.userDataService.currentProfile.promptsHome;
-			return [
-				...result,
-				{
-					uri: userDataPromptsHome,
-					source: PromptFileSource.CopilotPersonal,
-					storage: PromptsStorage.user,
-					displayPath: nls.localize('promptsUserDataFolder', "User Data"),
-					isDefault: true
-				}
-			];
-		}
-
-		return result;
-	}
-
-	/**
-	 * Gets all source folder URIs for a prompt type (both workspace and user home).
-	 * This is used for file watching to detect changes in all relevant locations.
-	 */
-	private getSourceFoldersSync(type: PromptsType, userHome: URI): readonly URI[] {
-		const result: URI[] = [];
-		const folders = this.getWorkspaceFolders();
-		const defaultFileOrFolders = getPromptFileDefaultLocations(type);
-
-		const getFolderUri = (type: PromptsType, fileOrFolderPath: URI): URI => {
-			// For hooks, the paths are sometimes file paths, so get the parent directory in that case
-			if (type === PromptsType.hook && fileOrFolderPath.path.toLowerCase().endsWith('.json')) {
-				return dirname(fileOrFolderPath);
-			}
-			return fileOrFolderPath;
-		};
-
-		for (const sourceFileOrFolder of defaultFileOrFolders) {
-			let fileOrFolderPath: URI;
-			if (sourceFileOrFolder.storage === PromptsStorage.local) {
-				for (const workspaceFolder of folders) {
-					fileOrFolderPath = joinPath(workspaceFolder.uri, sourceFileOrFolder.path);
-					result.push(getFolderUri(type, fileOrFolderPath));
-				}
-			} else if (sourceFileOrFolder.storage === PromptsStorage.user) {
-				// For tilde paths, strip the ~/ prefix before joining with userHome
-				const relativePath = isTildePath(sourceFileOrFolder.path) ? sourceFileOrFolder.path.substring(2) : sourceFileOrFolder.path;
-				fileOrFolderPath = joinPath(userHome, relativePath);
-				result.push(getFolderUri(type, fileOrFolderPath));
-			}
-		}
-
-		return result;
-	}
-
 	public createFilesUpdatedEvent(type: PromptsType): { readonly event: Event<void>; dispose: () => void } {
 		const disposables = new DisposableStore();
 		const eventEmitter = disposables.add(new Emitter<void>());
+		const token = disposables.add(new CancellationTokenSource()).token; // track the disposal of the event listeners so we can cancel any in-flight async operations when the event is disposed
 
+		const externalFolderWatchers = disposables.add(new DisposableStore());
+		const key = getPromptFileLocationsConfigKey(type);
 		const userDataFolder = this.userDataService.currentProfile.promptsHome;
 
-		const key = getPromptFileLocationsConfigKey(type);
-		let parentFolders = this.getLocalParentFolders(type);
-		let allSourceFolders: URI[] = [];
+		let parentFolders: readonly IResolvedPromptSourceFolder[] = [];
 
-		const externalFolderWatchers = disposables.add(new DisposableStore());
 		const updateExternalFolderWatchers = () => {
 			externalFolderWatchers.clear();
 			for (const folder of parentFolders) {
 				if (!this.getWorkspaceFolder(folder.parent)) {
 					// if the folder is not part of the workspace, we need to watch it
-					const recursive = folder.filePattern !== undefined;
+					const recursive = folder.filePattern !== undefined || type === PromptsType.instructions; // instructions can be in subfolders, so watch recursively
 					externalFolderWatchers.add(this.fileService.watch(folder.parent, { recursive, excludes: [] }));
 				}
 			}
-			// Watch all source folders (including user home if applicable)
-			for (const folder of allSourceFolders) {
-				if (!this.getWorkspaceFolder(folder)) {
-					externalFolderWatchers.add(this.fileService.watch(folder, { recursive: true, excludes: [] }));
-				}
-			}
 		};
 
-		// Initialize source folders (async if type has userHome locations)
-		this.pathService.userHome().then(userHome => {
-			allSourceFolders = [...this.getSourceFoldersSync(type, userHome)];
-			updateExternalFolderWatchers();
-		});
+		const update = async (emitEvent: boolean) => {
+			try {
+				const configuredLocations = PromptsConfig.promptSourceFolders(this.configService, type);
+				parentFolders = await this.toAbsoluteLocations(type, configuredLocations, undefined);
 
+				if (token.isCancellationRequested) {
+					return;
+				}
+				updateExternalFolderWatchers();
+				if (emitEvent) {
+					eventEmitter.fire();
+				}
+			} catch (err) {
+				this.logService.error(`Error updating prompt file watchers after config change:`, err);
+			}
+		};
 		disposables.add(this.configService.onDidChangeConfiguration(e => {
 			if (e.affectsConfiguration(key)) {
-				parentFolders = this.getLocalParentFolders(type);
-				updateExternalFolderWatchers();
-				eventEmitter.fire();
+				void update(true);
 			}
 		}));
 		disposables.add(this.onDidChangeWorkspaceFolders()(() => {
-			parentFolders = this.getLocalParentFolders(type);
-			this.pathService.userHome().then(userHome => {
-				allSourceFolders = [...this.getSourceFoldersSync(type, userHome)];
-				updateExternalFolderWatchers();
-			});
-			eventEmitter.fire();
+			void update(true);
+		}));
+		disposables.add(this.workspaceTrustManagementService.onDidChangeTrustedFolders(() => {
+			void update(true);
 		}));
 		disposables.add(this.fileService.onDidFilesChange(e => {
 			if (e.affects(userDataFolder)) {
@@ -211,19 +230,12 @@ export class PromptFilesLocator {
 				eventEmitter.fire();
 				return;
 			}
-			if (allSourceFolders.some(folder => e.affects(folder))) {
-				eventEmitter.fire();
-				return;
-			}
 		}));
 		disposables.add(this.fileService.watch(userDataFolder));
 
-		return { event: eventEmitter.event, dispose: () => disposables.dispose() };
-	}
+		void update(false);
 
-	public async getAgentSourceFolders(): Promise<readonly URI[]> {
-		const userHome = await this.pathService.userHome();
-		return this.toAbsoluteLocations(PromptsType.agent, DEFAULT_AGENT_SOURCE_FOLDERS, userHome).map(l => l.uri);
+		return { event: eventEmitter.event, dispose: () => disposables.dispose() };
 	}
 
 	/**
@@ -231,7 +243,6 @@ export class PromptFilesLocator {
 	 * Returns folders from config, excluding user storage and Claude paths (which are read-only).
 	 */
 	public async getHookSourceFolders(): Promise<readonly URI[]> {
-		const userHome = await this.pathService.userHome();
 		const configuredLocations = PromptsConfig.promptSourceFolders(this.configService, PromptsType.hook);
 
 		// Ignore claude folders since they aren't first-class supported, so we don't want to create invalid formats
@@ -242,19 +253,13 @@ export class PromptFilesLocator {
 
 		// Convert to absolute URIs
 		const result = new ResourceSet();
-		const absoluteLocations = this.toAbsoluteLocations(PromptsType.hook, allowedHookFolders, userHome);
+		const absoluteLocations = await this.toAbsoluteLocations(PromptsType.hook, allowedHookFolders);
 
 		for (const location of absoluteLocations) {
 			// For hook configs, entries are directories unless the path ends with .json (specific file)
 			// Default entries have filePattern, user entries don't but are still directories
-			const isSpecificFile = location.uri.path.endsWith('.json');
-			if (isSpecificFile) {
-				// It's a specific file path (like .github/hooks/hooks.json), use parent directory
-				result.add(dirname(location.uri));
-			} else {
-				// It's a directory path (like .github/hooks or .github/books)
-				result.add(location.uri);
-			}
+			// location.parent points to the directory in both cases, so we can just use that
+			result.add(location.parent);
 		}
 
 		return [...result];
@@ -273,28 +278,28 @@ export class PromptFilesLocator {
 	 * @returns List of possible unambiguous prompt file folders.
 	 */
 	public async getConfigBasedSourceFolders(type: PromptsType): Promise<readonly URI[]> {
-		const userHome = await this.pathService.userHome();
 		const configuredLocations = PromptsConfig.promptSourceFolders(this.configService, type);
-		const absoluteLocations = this.toAbsoluteLocations(type, configuredLocations, userHome).map(l => l.uri);
+		const absoluteLocations = await this.toAbsoluteLocations(type, configuredLocations);
 
 		// For anything that doesn't support glob patterns, we can return
 		if (type !== PromptsType.prompt && type !== PromptsType.instructions) {
-			return absoluteLocations;
+			return absoluteLocations.map(l => l.uri);
 		}
 
 		// locations in the settings can contain glob patterns so we need
 		// to process them to get "clean" paths; the goal here is to have
 		// a list of unambiguous folder paths where prompt files are stored
 		const result = new ResourceSet();
-		for (let absoluteLocation of absoluteLocations) {
-			const baseName = basename(absoluteLocation);
+		for (const absoluteLocation of absoluteLocations) {
+			let location = absoluteLocation.uri;
+			const baseName = basename(location);
 
 			// if a path ends with a well-known "any file" pattern, remove
 			// it so we can get the dirname path of that setting value
 			const filePatterns = ['*.md', `*${getPromptFileExtension(type)}`];
 			for (const filePattern of filePatterns) {
 				if (baseName === filePattern) {
-					absoluteLocation = dirname(absoluteLocation);
+					location = dirname(location);
 					continue;
 				}
 			}
@@ -302,16 +307,16 @@ export class PromptFilesLocator {
 			// likewise, if the pattern ends with single `*` (any file name)
 			// remove it to get the dirname path of the setting value
 			if (baseName === '*') {
-				absoluteLocation = dirname(absoluteLocation);
+				location = dirname(location);
 			}
 
 			// if after replacing the "file name" glob pattern, the path
 			// still contains a glob pattern, then ignore the path
-			if (isValidGlob(absoluteLocation.path) === true) {
+			if (isValidGlob(location.path) === true) {
 				continue;
 			}
 
-			result.add(absoluteLocation);
+			result.add(location);
 		}
 
 		return [...result];
@@ -329,8 +334,10 @@ export class PromptFilesLocator {
 	 * @returns List of resolved source folders with metadata.
 	 */
 	public async getResolvedSourceFolders(type: PromptsType): Promise<readonly IResolvedPromptSourceFolder[]> {
-		const localFolders = await this.getLocalStorageFolders(type);
-		const userFolders = await this.getUserStorageFolders(type);
+		const absoluteLocations = await this.getLocalStorageFolders(type);
+
+		const localFolders = absoluteLocations.filter(loc => loc.storage === PromptsStorage.local);
+		const userFolders = absoluteLocations.filter(loc => loc.storage === PromptsStorage.user);
 		return this.dedupeSourceFolders([...localFolders, ...userFolders]);
 	}
 
@@ -341,8 +348,9 @@ export class PromptFilesLocator {
 	 * for debug/diagnostic output so the displayed order is accurate.
 	 */
 	public async getSourceFoldersInDiscoveryOrder(type: PromptsType): Promise<readonly IResolvedPromptSourceFolder[]> {
-		const userFolders = await this.getUserStorageFolders(type);
-		const localFolders = await this.getLocalStorageFolders(type);
+		const absoluteLocations = await this.getLocalStorageFolders(type);
+		const userFolders = absoluteLocations.filter(loc => loc.storage === PromptsStorage.user);
+		const localFolders = absoluteLocations.filter(loc => loc.storage === PromptsStorage.local);
 		return this.dedupeSourceFolders([...userFolders, ...localFolders]);
 	}
 
@@ -351,7 +359,6 @@ export class PromptFilesLocator {
 	 * This merges default folders with configured locations.
 	 */
 	private async getLocalStorageFolders(type: PromptsType): Promise<readonly IResolvedPromptSourceFolder[]> {
-		const userHome = await this.pathService.userHome();
 		const configuredLocations = PromptsConfig.promptSourceFolders(this.configService, type);
 		const defaultFolders = getPromptFileDefaultLocations(type);
 
@@ -361,7 +368,11 @@ export class PromptFilesLocator {
 			...configuredLocations.filter(loc => !defaultFolders.some(df => df.path === loc.path))
 		];
 
-		return this.toAbsoluteLocations(type, allFolders, userHome, defaultFolders);
+		const absoluteLocations = await this.toAbsoluteLocations(type, allFolders, defaultFolders);
+		if (type === PromptsType.agent || type === PromptsType.instructions || type === PromptsType.prompt) {
+			absoluteLocations.push(this.userDataFolder);
+		}
+		return absoluteLocations;
 	}
 
 	/**
@@ -379,39 +390,6 @@ export class PromptFilesLocator {
 		return result;
 	}
 
-	/**
-	 * Finds all existent prompt files in the configured local source folders.
-	 *
-	 * @returns List of prompt files found in the local source folders.
-	 */
-	private async listFilesInLocal(type: PromptsType, token: CancellationToken): Promise<readonly URI[]> {
-		// find all prompt files in the provided locations, then match
-		// the found file paths against (possible) glob patterns
-		const paths = new ResourceSet();
-
-		for (const { parent, filePattern } of this.getLocalParentFolders(type)) {
-			const files = (filePattern === undefined)
-				? await this.resolveFilesAtLocation(parent, type, token) // if the location does not contain a glob pattern, resolve the location directly
-				: await this.searchFilesInLocation(parent, filePattern, token);
-			for (const file of files) {
-				if (getPromptFileType(file) === type) {
-					paths.add(file);
-				}
-			}
-			if (token.isCancellationRequested) {
-				return [];
-			}
-		}
-
-		return [...paths];
-	}
-
-	private getLocalParentFolders(type: PromptsType): readonly { parent: URI; filePattern?: string }[] {
-		const configuredLocations = PromptsConfig.promptSourceFolders(this.configService, type);
-		const absoluteLocations = this.toAbsoluteLocations(type, configuredLocations, undefined);
-		return absoluteLocations.map((location) => firstNonGlobParentAndPattern(location.uri));
-	}
-
 	/**
 	 * Converts locations defined in `settings` to absolute filesystem path URIs with metadata.
 	 * This conversion is needed because locations in settings can be relative,
@@ -419,10 +397,12 @@ export class PromptFilesLocator {
 	 * If userHome is provided, paths starting with `~` will be expanded. Otherwise these paths are ignored.
 	 * Preserves the type and location properties from the source folder definitions.
 	 */
-	private toAbsoluteLocations(type: PromptsType, configuredLocations: readonly IPromptSourceFolder[], userHome: URI | undefined, defaultLocations?: readonly IPromptSourceFolder[]): readonly IResolvedPromptSourceFolder[] {
+	private async toAbsoluteLocations(type: PromptsType, configuredLocations: readonly IPromptSourceFolder[], defaultLocations?: readonly IPromptSourceFolder[]): Promise<IResolvedPromptSourceFolder[]> {
 		const result: IResolvedPromptSourceFolder[] = [];
 		const seen = new ResourceSet();
-		const folders = this.getWorkspaceFolders();
+
+		const userHome = await this.pathService.userHome();
+		const rootFolders = await this.getWorkspaceFolderRoots(this.configService.getValue(PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS) === true);
 
 		// Create a set of default paths for quick lookup
 		const defaultPaths = new Set(defaultLocations?.map(loc => loc.path));
@@ -455,13 +435,11 @@ export class PromptFilesLocator {
 			try {
 				// Handle tilde paths when userHome is provided
 				if (isTildePath(configuredLocation)) {
-					// If userHome is not provided, we cannot resolve tilde paths so we skip this entry
-					if (userHome) {
-						const uri = joinPath(userHome, configuredLocation.substring(2));
-						if (!seen.has(uri)) {
-							seen.add(uri);
-							result.push({ uri, source: sourceFolder.source, storage: sourceFolder.storage, displayPath: configuredLocation, isDefault });
-						}
+					const uri = joinPath(userHome, configuredLocation.substring(2));
+					if (!seen.has(uri)) {
+						seen.add(uri);
+						const { parent, filePattern } = getParentFolder(type, uri);
+						result.push({ uri, parent, filePattern, source: sourceFolder.source, storage: sourceFolder.storage, displayPath: configuredLocation, isDefault });
 					}
 					continue;
 				}
@@ -476,14 +454,16 @@ export class PromptFilesLocator {
 					}
 					if (!seen.has(uri)) {
 						seen.add(uri);
-						result.push({ uri, source: sourceFolder.source, storage: sourceFolder.storage, displayPath: configuredLocation, isDefault });
+						const { parent, filePattern } = getParentFolder(type, uri);
+						result.push({ uri, parent, filePattern, source: sourceFolder.source, storage: sourceFolder.storage, displayPath: configuredLocation, isDefault });
 					}
 				} else {
-					for (const workspaceFolder of folders) {
-						const absolutePath = joinPath(workspaceFolder.uri, configuredLocation);
+					for (const folder of rootFolders) {
+						const absolutePath = joinPath(folder, configuredLocation);
 						if (!seen.has(absolutePath)) {
 							seen.add(absolutePath);
-							result.push({ uri: absolutePath, source: sourceFolder.source, storage: sourceFolder.storage, displayPath: configuredLocation, isDefault });
+							const { parent, filePattern } = getParentFolder(type, absolutePath);
+							result.push({ uri: absolutePath, parent, filePattern, source: sourceFolder.source, storage: sourceFolder.storage, displayPath: configuredLocation, isDefault });
 						}
 					}
 				}
@@ -497,14 +477,23 @@ export class PromptFilesLocator {
 
 	/**
 	 * Uses the file service to resolve the provided location and return either the file at the location of files in the directory.
-	 * For claude rules folders (.claude/rules), this searches recursively to support subdirectories.
+	 * For instruction folders, this searches recursively (up to {@link MAX_INSTRUCTIONS_RECURSION_DEPTH} levels deep) provided
+	 * the location is not a workspace folder root and does not contain wildcards, to support subdirectories while avoiding
+	 * accidentally broad traversal.
 	 */
-	private async resolveFilesAtLocation(location: URI, type: PromptsType, token: CancellationToken): Promise<URI[]> {
+	private async resolveFilesAtLocation(location: URI, type: PromptsType, token: CancellationToken, depth: number = 0): Promise<URI[]> {
 		if (type === PromptsType.skill) {
 			return this.findAgentSkillsInFolder(location, token);
 		}
-		// Claude rules folders support subdirectories, so search recursively
-		const recursive = type === PromptsType.instructions && isInClaudeRulesFolder(joinPath(location, 'dummy.md'));
+		// Recurse into subdirectories for instruction folders, but only if:
+		// - the location is not a workspace folder root (to avoid full workspace traversal)
+		// - the path does not contain wildcards (already filtered upstream, but guard here too)
+		// - the recursion depth hasn't exceeded the limit
+		const isWorkspaceRoot = depth === 0 && this.getWorkspaceFolders().some(f => isEqual(f.uri, location));
+		const recursive = type === PromptsType.instructions
+			&& !isWorkspaceRoot
+			&& !hasGlobPattern(location.path)
+			&& depth < MAX_INSTRUCTIONS_RECURSION_DEPTH;
 		try {
 			const info = await this.fileService.resolve(location);
 			if (token.isCancellationRequested) {
@@ -518,8 +507,8 @@ export class PromptFilesLocator {
 					if (child.isFile) {
 						result.push(child.resource);
 					} else if (recursive && child.isDirectory) {
-						// Recursively search subdirectories for claude rules
-						const subFiles = await this.resolveFilesAtLocation(child.resource, type, token);
+						// Recursively search subdirectories for instructions
+						const subFiles = await this.resolveFilesAtLocation(child.resource, type, token, depth + 1);
 						result.push(...subFiles);
 					}
 				}
@@ -575,24 +564,6 @@ export class PromptFilesLocator {
 		return [];
 	}
 
-	public async findCopilotInstructionsMDsInWorkspace(token: CancellationToken): Promise<IResolvedAgentFile[]> {
-		const result: IResolvedAgentFile[] = [];
-		const folders = this.getWorkspaceFolders();
-		for (const folder of folders) {
-			const file = joinPath(folder.uri, `.github/` + COPILOT_CUSTOM_INSTRUCTIONS_FILENAME);
-			try {
-				const stat = await this.fileService.stat(file);
-				if (stat.isFile) {
-					const realPath = stat.isSymbolicLink ? await this.fileService.realpath(file) : undefined;
-					result.push({ uri: file, realPath, type: AgentFileType.copilotInstructionsMd });
-				}
-			} catch (error) {
-				this.logService.trace(`[PromptFilesLocator] Skipping copilot-instructions.md at ${file.toString()}: ${error}`);
-			}
-		}
-		return result;
-	}
-
 	/**
 	 * Gets list of `AGENTS.md` files anywhere in the workspace.
 	 */
@@ -674,29 +645,24 @@ export class PromptFilesLocator {
 		return result;
 	}
 
-	/**
-	 * Gets list of files at the root workspace folder(s).
-	 */
-	public async findFilesInWorkspaceRoots(fileName: string, folder: string | undefined, type: AgentFileType, token: CancellationToken, result: IResolvedAgentFile[] = []): Promise<IResolvedAgentFile[]> {
-		const folders = this.getWorkspaceFolders();
-		if (folder) {
-			return this.findFilesInRoots(folders.map(f => joinPath(f.uri, folder)), fileName, type, token, result);
-		}
-		return this.findFilesInRoots(folders.map(f => f.uri), fileName, type, token, result);
-	}
 
-	public async findFilesInRoots(roots: URI[], fileName: string, type: AgentFileType, token: CancellationToken, result: IResolvedAgentFile[] = []): Promise<IResolvedAgentFile[]> {
-		const fileNameLower = fileName.toLowerCase();
-		const resolvedRoots = await this.fileService.resolveAll(roots.map(uri => ({ resource: uri })));
+
+	public async findFilesInRoots(roots: URI[], folder: string | undefined, paths: IWorkspaceInstructionFile[], token: CancellationToken, result: IResolvedAgentFile[] = []): Promise<IResolvedAgentFile[]> {
+		const toResolve = roots.map(root => ({ resource: folder !== undefined ? joinPath(root, folder) : root }));
+		const resolvedRoots = await this.fileService.resolveAll(toResolve);
 		if (token.isCancellationRequested) {
 			return result;
 		}
 		for (const root of resolvedRoots) {
 			if (root.success && root.stat?.children) {
-				const file = root.stat.children.find(c => c.isFile && c.name.toLowerCase() === fileNameLower);
-				if (file) {
-					const realPath = file.isSymbolicLink ? await this.fileService.realpath(file.resource) : undefined;
-					result.push({ uri: file.resource, realPath, type });
+				for (const child of root.stat.children) {
+					if (child.isFile) {
+						const matchingPath = paths.find(p => equalsIgnoreCase(p.fileName, child.name));
+						if (matchingPath) {
+							const realPath = child.isSymbolicLink ? await this.fileService.realpath(child.resource) : undefined;
+							result.push({ uri: child.resource, realPath, type: matchingPath.type });
+						}
+					}
 				}
 			}
 		}
@@ -753,9 +719,8 @@ export class PromptFilesLocator {
 	 * Searches for skills in all configured locations.
 	 */
 	public async findAgentSkills(token: CancellationToken): Promise<IResolvedPromptFile[]> {
-		const userHome = await this.pathService.userHome();
 		const configuredLocations = PromptsConfig.promptSourceFolders(this.configService, PromptsType.skill);
-		const absoluteLocations = this.toAbsoluteLocations(PromptsType.skill, configuredLocations, userHome);
+		const absoluteLocations = await this.toAbsoluteLocations(PromptsType.skill, configuredLocations);
 		const allResults: IResolvedPromptFile[] = [];
 
 		for (const { uri, source, storage } of absoluteLocations) {
@@ -853,6 +818,11 @@ export function isValidGlob(pattern: string): boolean {
 	return false;
 }
 
+interface IParentFolderResult {
+	readonly parent: URI;
+	readonly filePattern?: string;
+}
+
 /**
  * Finds the first parent of the provided location that does not contain a `glob pattern`.
  *
@@ -862,13 +832,21 @@ export function isValidGlob(pattern: string): boolean {
  *
  * ```typescript
  * assert.strictDeepEqual(
- *     firstNonGlobParentAndPattern(URI.file('/home/user/{folder1,folder2}/file.md')).path,
+ *     getParentFolder(PromptsType.prompt, URI.file('/home/user/{folder1,folder2}/file.md')),
  *     { parent: URI.file('/home/user'), filePattern: '{folder1,folder2}/file.md' },
  *     'Must find correct non-glob parent dirname.',
  * );
  * ```
  */
-function firstNonGlobParentAndPattern(location: URI): { parent: URI; filePattern?: string } {
+function getParentFolder(type: PromptsType, location: URI): IParentFolderResult {
+	if (type === PromptsType.hook && extname(location) === '.json') {
+		location = dirname(location);
+	}
+	if (type !== PromptsType.instructions && type !== PromptsType.prompt) {
+		// only instructions and prompts support glob patterns, so we can return the location as is
+		return { parent: location };
+	}
+
 	const segments = location.path.split('/');
 	let i = 0;
 	while (i < segments.length && isValidGlob(segments[i]) === false) {
diff --git a/src/vs/workbench/contrib/chat/common/promptSyntax/utils/promptsServiceUtils.ts b/src/vs/workbench/contrib/chat/common/promptSyntax/utils/promptsServiceUtils.ts
index f458870f629cb..1e252f7aa8f87 100644
--- a/src/vs/workbench/contrib/chat/common/promptSyntax/utils/promptsServiceUtils.ts
+++ b/src/vs/workbench/contrib/chat/common/promptSyntax/utils/promptsServiceUtils.ts
@@ -6,6 +6,7 @@
 import { URI } from '../../../../../../base/common/uri.js';
 import { ExtensionIdentifier } from '../../../../../../platform/extensions/common/extensions.js';
 import { IProductService } from '../../../../../../platform/product/common/productService.js';
+import { IAgentSource, PromptsStorage } from '../service/promptsService.js';
 
 /**
  * Checks if a prompt file is organization-provided.
@@ -26,3 +27,19 @@ export function isOrganizationPromptFile(uri: URI, extensionId: ExtensionIdentif
 	const pathContainsGithub = uri.path.includes('/github/');
 	return isFromBuiltinChatExtension && pathContainsGithub;
 }
+
+/**
+ * Checks if a custom agent is considered "builtin" - i.e. shipped by the
+ * built-in chat extension and not organization-provided. Used for telemetry
+ * to decide whether the agent name is safe to send as-is.
+ */
+export function isBuiltinAgent(source: IAgentSource, uri: URI, productService: IProductService): boolean {
+	if (source.storage !== PromptsStorage.extension) {
+		return false;
+	}
+	const chatExtensionId = productService.defaultChatAgent?.chatExtensionId;
+	if (!chatExtensionId || !ExtensionIdentifier.equals(source.extensionId, chatExtensionId)) {
+		return false;
+	}
+	return !isOrganizationPromptFile(uri, source.extensionId, productService);
+}
diff --git a/src/vs/workbench/contrib/chat/common/requestParser/chatRequestParser.ts b/src/vs/workbench/contrib/chat/common/requestParser/chatRequestParser.ts
index 9ec0508a489f2..bf1214267a518 100644
--- a/src/vs/workbench/contrib/chat/common/requestParser/chatRequestParser.ts
+++ b/src/vs/workbench/contrib/chat/common/requestParser/chatRequestParser.ts
@@ -12,7 +12,7 @@ import { ChatAgentLocation, ChatModeKind } from '../constants.js';
 import { IChatAgentAttachmentCapabilities, IChatAgentData, IChatAgentService } from '../participants/chatAgents.js';
 import { IChatSlashCommandService } from '../participants/chatSlashCommands.js';
 import { IPromptsService } from '../promptSyntax/service/promptsService.js';
-import { IToolData, IToolSet, isToolSet } from '../tools/languageModelToolsService.js';
+import { IToolAndToolSetEnablementMap, IToolData, IToolSet, isToolSet } from '../tools/languageModelToolsService.js';
 import { ChatRequestAgentPart, ChatRequestAgentSubcommandPart, ChatRequestDynamicVariablePart, ChatRequestSlashCommandPart, ChatRequestSlashPromptPart, ChatRequestTextPart, ChatRequestToolPart, ChatRequestToolSetPart, IParsedChatRequest, IParsedChatRequestPart, chatAgentLeader, chatSubcommandLeader, chatVariableLeader } from './chatParserTypes.js';
 
 const agentReg = /^@([\w_\-\.]+)(?=(\s|$|\b))/i; // An @-agent
@@ -37,11 +37,16 @@ export class ChatRequestParser {
 	) { }
 
 	parseChatRequest(sessionResource: URI, message: string, location: ChatAgentLocation = ChatAgentLocation.Chat, context?: IChatParserContext): IParsedChatRequest {
-		const parts: IParsedChatRequestPart[] = [];
 		const references = this.variableService.getDynamicVariables(sessionResource); // must access this list before any async calls
+		const selectedToolAndToolSets = this.variableService.getSelectedToolAndToolSets(sessionResource);
+		return this.parseChatRequestWithReferences(references, selectedToolAndToolSets, message, location, context);
+	}
+
+	parseChatRequestWithReferences(references: ReadonlyArray<IDynamicVariable>, selectedToolAndToolSets: IToolAndToolSetEnablementMap, message: string, location: ChatAgentLocation = ChatAgentLocation.Chat, context?: IChatParserContext): IParsedChatRequest {
+		const parts: IParsedChatRequestPart[] = [];
 		const toolsByName = new Map<string, IToolData>();
 		const toolSetsByName = new Map<string, IToolSet>();
-		for (const [entry, enabled] of this.variableService.getSelectedToolAndToolSets(sessionResource)) {
+		for (const [entry, enabled] of selectedToolAndToolSets) {
 			if (enabled) {
 				if (isToolSet(entry)) {
 					toolSetsByName.set(entry.referenceName, entry);
diff --git a/src/vs/workbench/contrib/chat/common/tools/builtinTools/askQuestionsTool.ts b/src/vs/workbench/contrib/chat/common/tools/builtinTools/askQuestionsTool.ts
index 8c503de71cf21..d6897b61fdba9 100644
--- a/src/vs/workbench/contrib/chat/common/tools/builtinTools/askQuestionsTool.ts
+++ b/src/vs/workbench/contrib/chat/common/tools/builtinTools/askQuestionsTool.ts
@@ -8,11 +8,14 @@ import { CancellationError } from '../../../../../../base/common/errors.js';
 import { MarkdownString } from '../../../../../../base/common/htmlContent.js';
 import { IJSONSchema, IJSONSchemaMap } from '../../../../../../base/common/jsonSchema.js';
 import { Disposable } from '../../../../../../base/common/lifecycle.js';
+import { hasKey } from '../../../../../../base/common/types.js';
 import { generateUuid } from '../../../../../../base/common/uuid.js';
 import { localize } from '../../../../../../nls.js';
-import { IChatQuestion, IChatService } from '../../chatService/chatService.js';
+import { IChatQuestion, IChatQuestionAnswers, IChatQuestionAnswerValue, IChatMultiSelectAnswer, IChatService, IChatSingleSelectAnswer } from '../../chatService/chatService.js';
 import { ChatQuestionCarouselData } from '../../model/chatProgressTypes/chatQuestionCarouselData.js';
 import { IChatRequestModel } from '../../model/chatModel.js';
+import { ChatConfiguration, ChatPermissionLevel } from '../../constants.js';
+import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
 import { StopWatch } from '../../../../../../base/common/stopwatch.js';
 import { ILogService } from '../../../../../../platform/log/common/log.js';
 import { ITelemetryService } from '../../../../../../platform/telemetry/common/telemetry.js';
@@ -22,6 +25,12 @@ import { Codicon } from '../../../../../../base/common/codicons.js';
 import { raceCancellation } from '../../../../../../base/common/async.js';
 import { URI } from '../../../../../../base/common/uri.js';
 
+/**
+ * Response returned to the model when the user is not available (autopilot mode).
+ */
+export const AUTOPILOT_ASK_USER_RESPONSE =
+	'The user is not available to respond and will review your work later. Work autonomously and make good decisions.';
+
 // Use a distinct id to avoid clashing with extension-provided tools
 export const AskQuestionsToolId = 'vscode_askQuestions';
 
@@ -101,7 +110,7 @@ export function createAskQuestionsToolData(): IToolData {
 			},
 			allowFreeformInput: {
 				type: 'boolean',
-				description: 'Allow freeform text answers in addition to option selection.'
+				description: 'Allow freeform text answers in addition to option selection. Defaults to true; set to false to restrict to predefined options only.'
 			},
 			options: {
 				type: 'array',
@@ -145,11 +154,12 @@ export function createAskQuestionsToolData(): IToolData {
 	return {
 		id: AskQuestionsToolId,
 		toolReferenceName: 'askQuestions',
-		canBeReferencedInPrompt: true,
+		legacyToolReferenceFullNames: [AskQuestionsToolId, 'vscode/askQuestions'],
+		canBeReferencedInPrompt: false,
 		icon: ThemeIcon.fromId(Codicon.question.id),
 		displayName: localize('tool.askQuestions.displayName', 'Ask Clarifying Questions'),
 		userDescription: localize('tool.askQuestions.userDescription', 'Ask structured clarifying questions using single select, multi-select, or freeform inputs to collect task requirements before proceeding.'),
-		modelDescription: 'Use this tool to ask the user a small number of clarifying questions before proceeding. Provide the questions array with concise headers and prompts. Use options for fixed choices, set multiSelect when multiple selections are allowed, and set allowFreeformInput to let users supply their own answer.',
+		modelDescription: 'Use this tool to ask the user a small number of clarifying questions before proceeding. Provide the questions array with concise headers and prompts. Use options for fixed choices, set multiSelect when multiple selections are allowed. Users can always provide a freeform text answer alongside options unless you set allowFreeformInput to false.',
 		source: ToolDataSource.Internal,
 		inputSchema
 	};
@@ -163,6 +173,7 @@ export class AskQuestionsTool extends Disposable implements IToolImpl {
 		@IChatService private readonly chatService: IChatService,
 		@ITelemetryService private readonly telemetryService: ITelemetryService,
 		@ILogService private readonly logService: ILogService,
+		@IConfigurationService private readonly configService: IConfigurationService,
 	) {
 		super();
 	}
@@ -186,6 +197,19 @@ export class AskQuestionsTool extends Disposable implements IToolImpl {
 			return this.createSkippedResult(questions);
 		}
 
+		// In autopilot mode or when auto-reply is enabled, the user is not available —
+		// auto-respond instead of blocking. Still append a completed carousel so the
+		// user can see what was skipped.
+		if (request.modeInfo?.permissionLevel === ChatPermissionLevel.Autopilot || this.configService.getValue<boolean>(ChatConfiguration.AutoReply)) {
+			const reason = request.modeInfo?.permissionLevel === ChatPermissionLevel.Autopilot ? 'Autopilot mode' : 'Auto-reply enabled';
+			this.logService.info(`[AskQuestionsTool] ${reason}: auto-responding to questions`);
+			const { carousel, idToHeaderMap } = this.toQuestionCarousel(questions);
+			carousel.data = this.buildAutopilotCarouselAnswers(questions, carousel, idToHeaderMap);
+			carousel.isUsed = true;
+			this.chatService.appendProgress(request, carousel);
+			return this.createAutopilotResult(questions);
+		}
+
 		const { carousel, idToHeaderMap } = this.toQuestionCarousel(questions);
 		this.chatService.appendProgress(request, carousel);
 
@@ -313,11 +337,11 @@ export class AskQuestionsTool extends Disposable implements IToolImpl {
 				value: opt.label
 			})),
 			defaultValue,
-			allowFreeformInput: question.allowFreeformInput ?? false
+			allowFreeformInput: question.allowFreeformInput ?? true
 		};
 	}
 
-	protected convertCarouselAnswers(questions: IQuestion[], carouselAnswers: Record<string, unknown> | undefined, idToHeaderMap: Map<string, string>): IAnswerResult {
+	protected convertCarouselAnswers(questions: IQuestion[], carouselAnswers: IChatQuestionAnswers | undefined, idToHeaderMap: Map<string, string>): IAnswerResult {
 		const result: IAnswerResult = { answers: {} };
 
 		if (carouselAnswers) {
@@ -343,7 +367,7 @@ export class AskQuestionsTool extends Disposable implements IToolImpl {
 
 			// Look up the answer using the internal ID that was used in the carousel
 			const internalId = headerToIdMap.get(question.header);
-			const answer = internalId ? carouselAnswers[internalId] : undefined;
+			const answer: IChatQuestionAnswerValue | undefined = internalId ? carouselAnswers[internalId] : undefined;
 			this.logService.trace(`[AskQuestionsTool] Processing question "${question.header}" (internal ID: ${internalId}), raw answer: ${JSON.stringify(answer)}, type: ${typeof answer}`);
 
 			if (answer === undefined) {
@@ -372,67 +396,36 @@ export class AskQuestionsTool extends Disposable implements IToolImpl {
 					freeText: null,
 					skipped: false
 				};
-			} else if (typeof answer === 'object' && answer !== null) {
-				const answerObj = answer as Record<string, unknown>;
-				const freeformValue = typeof answerObj.freeformValue === 'string' && answerObj.freeformValue ? answerObj.freeformValue : null;
-				const selectedValues = Array.isArray(answerObj.selectedValues) ? answerObj.selectedValues.map(v => String(v)) : undefined;
-				const selectedValue = answerObj.selectedValue;
-				const label = typeof answerObj.label === 'string' ? answerObj.label : undefined;
-
-				if (selectedValues) {
+			} else if (typeof answer === 'object' && hasKey(answer, { selectedValues: true })) {
+				const { selectedValues, freeformValue } = answer as IChatMultiSelectAnswer;
+				result.answers[question.header] = {
+					selected: selectedValues,
+					freeText: freeformValue ?? null,
+					skipped: false
+				};
+			} else if (typeof answer === 'object' && (hasKey(answer, { selectedValue: true }) || hasKey(answer, { freeformValue: true }))) {
+				const { selectedValue, freeformValue } = answer as IChatSingleSelectAnswer;
+				if (freeformValue) {
 					result.answers[question.header] = {
-						selected: selectedValues,
+						selected: [],
 						freeText: freeformValue,
 						skipped: false
 					};
-				} else if (typeof selectedValue === 'string') {
+				} else if (selectedValue !== undefined) {
 					if (question.options?.some(opt => opt.label === selectedValue)) {
 						result.answers[question.header] = {
 							selected: [selectedValue],
-							freeText: freeformValue,
+							freeText: null,
 							skipped: false
 						};
 					} else {
 						result.answers[question.header] = {
 							selected: [],
-							freeText: freeformValue ?? selectedValue,
+							freeText: selectedValue,
 							skipped: false
 						};
 					}
-				} else if (Array.isArray(selectedValue)) {
-					result.answers[question.header] = {
-						selected: selectedValue.map(v => String(v)),
-						freeText: freeformValue,
-						skipped: false
-					};
-				} else if (selectedValue === undefined || selectedValue === null) {
-					if (freeformValue) {
-						result.answers[question.header] = {
-							selected: [],
-							freeText: freeformValue,
-							skipped: false
-						};
-					} else {
-						result.answers[question.header] = {
-							selected: [],
-							freeText: null,
-							skipped: true
-						};
-					}
-				} else if (freeformValue) {
-					result.answers[question.header] = {
-						selected: [],
-						freeText: freeformValue,
-						skipped: false
-					};
-				} else if (label) {
-					result.answers[question.header] = {
-						selected: [label],
-						freeText: null,
-						skipped: false
-					};
 				} else {
-					this.logService.warn(`[AskQuestionsTool] Unknown answer object format for "${question.header}": ${JSON.stringify(answer)}`);
 					result.answers[question.header] = {
 						selected: [],
 						freeText: null,
@@ -440,7 +433,7 @@ export class AskQuestionsTool extends Disposable implements IToolImpl {
 					};
 				}
 			} else {
-				this.logService.warn(`[AskQuestionsTool] Unknown answer format for "${question.header}": ${typeof answer}`);
+				this.logService.warn(`[AskQuestionsTool] Unknown answer format for "${question.header}": ${JSON.stringify(answer)}`);
 				result.answers[question.header] = {
 					selected: [],
 					freeText: null,
@@ -476,6 +469,63 @@ export class AskQuestionsTool extends Disposable implements IToolImpl {
 		};
 	}
 
+	private createAutopilotResult(questions: IQuestion[]): IToolResult {
+		const answers: Record<string, IQuestionAnswer> = {};
+		for (const question of questions) {
+			// Pick the recommended option if available, otherwise pick the first option
+			const recommended = question.options?.find(opt => opt.recommended);
+			const firstOption = question.options?.[0];
+			const selected = recommended?.label ?? firstOption?.label;
+			answers[question.header] = {
+				selected: selected ? [selected] : [],
+				freeText: selected ? null : AUTOPILOT_ASK_USER_RESPONSE,
+				skipped: false,
+			};
+		}
+		return {
+			content: [{ kind: 'text', value: JSON.stringify({ answers } satisfies IAnswerResult) }]
+		};
+	}
+
+	/**
+	 * Build carousel answer data keyed by carousel question IDs for rendering
+	 * the completed summary in the UI during autopilot mode.
+	 */
+	private buildAutopilotCarouselAnswers(questions: IQuestion[], carousel: ChatQuestionCarouselData, idToHeaderMap: Map<string, string>): IChatQuestionAnswers {
+		const data: IChatQuestionAnswers = {};
+		// Build reverse map: original header -> internal carousel question ID
+		const headerToIdMap = new Map<string, string>();
+		for (const [internalId, originalHeader] of idToHeaderMap) {
+			headerToIdMap.set(originalHeader, internalId);
+		}
+
+		for (const question of questions) {
+			const internalId = headerToIdMap.get(question.header);
+			if (!internalId) {
+				continue;
+			}
+
+			const chatQuestion = carousel.questions.find(q => q.id === internalId);
+			if (!chatQuestion) {
+				continue;
+			}
+
+			const recommended = question.options?.find(opt => opt.recommended);
+			const firstOption = question.options?.[0];
+			const selectedLabel = recommended?.label ?? firstOption?.label;
+
+			if (chatQuestion.type === 'text' || !selectedLabel) {
+				data[internalId] = AUTOPILOT_ASK_USER_RESPONSE;
+			} else if (chatQuestion.type === 'multiSelect') {
+				data[internalId] = { selectedValues: [selectedLabel] };
+			} else {
+				data[internalId] = { selectedValue: selectedLabel };
+			}
+		}
+
+		return data;
+	}
+
 	private sendTelemetry(requestId: string | undefined, questionCount: number, answeredCount: number, skippedCount: number, freeTextCount: number, recommendedAvailableCount: number, recommendedSelectedCount: number, duration: number): void {
 		this.telemetryService.publicLog2<AskQuestionsToolInvokedEvent, AskQuestionsToolInvokedClassification>('askQuestionsToolInvoked', {
 			requestId,
diff --git a/src/vs/workbench/contrib/chat/common/tools/builtinTools/chatExternalPathConfirmation.ts b/src/vs/workbench/contrib/chat/common/tools/builtinTools/chatExternalPathConfirmation.ts
index 9babb75b5bdb0..ee75a3bc056f5 100644
--- a/src/vs/workbench/contrib/chat/common/tools/builtinTools/chatExternalPathConfirmation.ts
+++ b/src/vs/workbench/contrib/chat/common/tools/builtinTools/chatExternalPathConfirmation.ts
@@ -3,17 +3,32 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { IDisposable } from '../../../../../../base/common/lifecycle.js';
 import { ResourceMap, ResourceSet } from '../../../../../../base/common/map.js';
 import { dirname, extUriBiasedIgnorePathCase } from '../../../../../../base/common/resources.js';
 import { URI } from '../../../../../../base/common/uri.js';
 import { localize } from '../../../../../../nls.js';
+import { ILabelService } from '../../../../../../platform/label/common/label.js';
+import { ObservableMemento, observableMemento } from '../../../../../../platform/observable/common/observableMemento.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../../../platform/storage/common/storage.js';
 import { ConfirmedReason, ToolConfirmKind } from '../../chatService/chatService.js';
 import {
 	ILanguageModelToolConfirmationActions,
 	ILanguageModelToolConfirmationContribution,
+	ILanguageModelToolConfirmationContributionQuickTreeItem,
 	ILanguageModelToolConfirmationRef
 } from '../languageModelToolsConfirmationService.js';
 
+const workspaceAllowlistMemento = observableMemento<readonly string[]>({
+	key: 'chat.externalPath.workspaceAllowlist',
+	defaultValue: [],
+	toStorage: value => JSON.stringify(value),
+	fromStorage: value => {
+		const parsed = JSON.parse(value);
+		return Array.isArray(parsed) ? parsed : [];
+	},
+});
+
 export interface IExternalPathInfo {
 	path: string;
 	isDirectory: boolean;
@@ -24,26 +39,59 @@ export interface IExternalPathInfo {
  * accessing paths outside the workspace, with an option to allow all access
  * from a containing folder for the current chat session.
  */
-export class ChatExternalPathConfirmationContribution implements ILanguageModelToolConfirmationContribution {
+export class ChatExternalPathConfirmationContribution implements ILanguageModelToolConfirmationContribution, IDisposable {
 	readonly canUseDefaultApprovals = false;
 
 	private readonly _sessionFolderAllowlist = new ResourceMap<ResourceSet>();
 	/** Cache of path URI -> resolved git root URI (or null if not in a repo) */
 	private readonly _gitRootCache = new ResourceMap<URI | null>();
+	private readonly _workspaceAllowlist?: ObservableMemento<readonly string[]>;
 
 	constructor(
 		private readonly _getPathInfo: (ref: ILanguageModelToolConfirmationRef) => IExternalPathInfo | undefined,
+		private readonly _labelService: ILabelService,
 		private readonly _findGitRoot?: (pathUri: URI) => Promise<URI | undefined>,
-	) { }
+		storageService?: IStorageService,
+		private readonly _pickFolder?: () => Promise<URI | undefined>,
+	) {
+		if (storageService) {
+			this._workspaceAllowlist = workspaceAllowlistMemento(StorageScope.WORKSPACE, StorageTarget.MACHINE, storageService);
+		}
+	}
 
-	getPreConfirmAction(ref: ILanguageModelToolConfirmationRef): ConfirmedReason | undefined {
-		const pathInfo = this._getPathInfo(ref);
-		if (!pathInfo || !ref.chatSessionResource) {
-			return undefined;
+	dispose(): void {
+		this._workspaceAllowlist?.dispose();
+	}
+
+	private _getWorkspaceFolders(): ResourceSet {
+		if (!this._workspaceAllowlist) {
+			return new ResourceSet();
+		}
+		const set = new ResourceSet();
+		for (const s of this._workspaceAllowlist.get()) {
+			try {
+				set.add(URI.parse(s));
+			} catch {
+				// ignore malformed URIs
+			}
 		}
+		return set;
+	}
+
+	private _setWorkspaceFolders(folders: ResourceSet): void {
+		if (!this._workspaceAllowlist) {
+			return;
+		}
+		const uriStrings: string[] = [];
+		for (const uri of folders) {
+			uriStrings.push(uri.toString());
+		}
+		this._workspaceAllowlist.set(uriStrings, undefined);
+	}
 
-		const allowedFolders = this._sessionFolderAllowlist.get(ref.chatSessionResource);
-		if (!allowedFolders || allowedFolders.size === 0) {
+	getPreConfirmAction(ref: ILanguageModelToolConfirmationRef): ConfirmedReason | undefined {
+		const pathInfo = this._getPathInfo(ref);
+		if (!pathInfo) {
 			return undefined;
 		}
 
@@ -55,13 +103,26 @@ export class ChatExternalPathConfirmationContribution implements ILanguageModelT
 			return undefined;
 		}
 
-		// Check if path is under any allowed folder
-		for (const folderUri of allowedFolders) {
+		// Check workspace-level allowlist
+		const workspaceFolders = this._getWorkspaceFolders();
+		for (const folderUri of workspaceFolders) {
 			if (extUriBiasedIgnorePathCase.isEqualOrParent(pathUri, folderUri)) {
 				return { type: ToolConfirmKind.UserAction };
 			}
 		}
 
+		// Check session-level allowlist
+		if (ref.chatSessionResource) {
+			const sessionFolders = this._sessionFolderAllowlist.get(ref.chatSessionResource);
+			if (sessionFolders) {
+				for (const folderUri of sessionFolders) {
+					if (extUriBiasedIgnorePathCase.isEqualOrParent(pathUri, folderUri)) {
+						return { type: ToolConfirmKind.UserAction };
+					}
+				}
+			}
+		}
+
 		return undefined;
 	}
 
@@ -149,4 +210,82 @@ export class ChatExternalPathConfirmationContribution implements ILanguageModelT
 
 		return actions;
 	}
+
+	getManageActions(): ILanguageModelToolConfirmationContributionQuickTreeItem[] {
+		const items: ILanguageModelToolConfirmationContributionQuickTreeItem[] = [];
+
+		// Workspace-level entries (persisted)
+		const workspaceFolders = this._getWorkspaceFolders();
+		for (const folderUri of workspaceFolders) {
+			items.push({
+				label: this._labelService.getUriLabel(folderUri),
+				description: localize('workspaceScope', "Workspace"),
+				checked: true,
+				onDidChangeChecked: (checked) => {
+					if (!checked) {
+						workspaceFolders.delete(folderUri);
+						this._setWorkspaceFolders(workspaceFolders);
+					} else {
+						workspaceFolders.add(folderUri);
+						this._setWorkspaceFolders(workspaceFolders);
+					}
+				},
+			});
+		}
+
+		// Session-level entries (ephemeral)
+		const allSessionFolders = new ResourceSet();
+		for (const [, folders] of this._sessionFolderAllowlist) {
+			for (const folder of folders) {
+				allSessionFolders.add(folder);
+			}
+		}
+		for (const folderUri of allSessionFolders) {
+			const wasInSessions = [...this._sessionFolderAllowlist].filter(([, folders]) => folders.has(folderUri));
+			items.push({
+				label: this._labelService.getUriLabel(folderUri),
+				description: localize('sessionScope', "Session"),
+				checked: true,
+				onDidChangeChecked: (checked) => {
+					if (!checked) {
+						for (const [, folders] of wasInSessions) {
+							folders.delete(folderUri);
+						}
+					} else {
+						for (const [, folders] of wasInSessions) {
+							folders.add(folderUri);
+						}
+					}
+				},
+			});
+		}
+
+		// "Add Path..." option to add a new workspace-level folder
+		if (this._pickFolder) {
+			const pickFolder = this._pickFolder;
+			items.push({
+				pickable: false,
+				label: localize('addPath', "Add Path..."),
+				description: localize('addPathDescription', "Allow a folder in this workspace"),
+				onDidOpen: async () => {
+					const uri = await pickFolder();
+					if (uri) {
+						const folders = this._getWorkspaceFolders();
+						folders.add(uri);
+						this._setWorkspaceFolders(folders);
+					}
+				}
+			});
+		}
+
+		return items;
+	}
+
+	reset(): void {
+		this._sessionFolderAllowlist.clear();
+		this._gitRootCache.clear();
+		if (this._workspaceAllowlist) {
+			this._workspaceAllowlist.set([], undefined);
+		}
+	}
 }
diff --git a/src/vs/workbench/contrib/chat/common/tools/builtinTools/confirmationTool.ts b/src/vs/workbench/contrib/chat/common/tools/builtinTools/confirmationTool.ts
index 7763b9f8b3d0e..2660841ac5b8e 100644
--- a/src/vs/workbench/contrib/chat/common/tools/builtinTools/confirmationTool.ts
+++ b/src/vs/workbench/contrib/chat/common/tools/builtinTools/confirmationTool.ts
@@ -5,11 +5,13 @@
 
 import { CancellationToken } from '../../../../../../base/common/cancellation.js';
 import { MarkdownString } from '../../../../../../base/common/htmlContent.js';
-import { IChatTerminalToolInvocationData } from '../../chatService/chatService.js';
+import { URI } from '../../../../../../base/common/uri.js';
+import { IChatModifiedFilesConfirmationData, IChatTerminalToolInvocationData } from '../../chatService/chatService.js';
 import { CountTokensCallback, IPreparedToolInvocation, IToolData, IToolImpl, IToolInvocation, IToolInvocationPreparationContext, IToolResult, ToolDataSource, ToolInvocationPresentation, ToolProgress } from '../languageModelToolsService.js';
 
 export const ConfirmationToolId = 'vscode_get_confirmation';
 export const ConfirmationToolWithOptionsId = 'vscode_get_confirmation_with_options';
+export const ModifiedFilesConfirmationToolId = 'vscode_get_modified_files_confirmation';
 
 export const ConfirmationToolData: IToolData = {
 	id: ConfirmationToolId,
@@ -69,6 +71,69 @@ export const ConfirmationToolWithOptionsData: IToolData = {
 	}
 };
 
+export const ModifiedFilesConfirmationToolData: IToolData = {
+	id: ModifiedFilesConfirmationToolId,
+	displayName: 'Modified Files Confirmation Tool',
+	modelDescription: 'A tool that shows a modified-files confirmation UI with a split primary button and a hardcoded cancel action.',
+	source: ToolDataSource.Internal,
+	inputSchema: {
+		type: 'object',
+		properties: {
+			title: {
+				type: 'string',
+				description: 'Title for the confirmation dialog'
+			},
+			message: {
+				type: 'string',
+				description: 'Message to show in the confirmation dialog'
+			},
+			options: {
+				type: 'array',
+				items: { type: 'string' },
+				minItems: 1,
+				description: 'Selectable option labels. The first option is used for the primary split button and the remaining options are placed in the dropdown menu.'
+			},
+			modifiedFiles: {
+				type: 'array',
+				items: {
+					type: 'object',
+					properties: {
+						uri: {
+							type: 'string',
+							description: 'URI of the modified file.'
+						},
+						originalUri: {
+							type: 'string',
+							description: 'Optional original URI used when opening a diff.'
+						},
+						insertions: {
+							type: 'number',
+							description: 'Optional number of lines added.'
+						},
+						deletions: {
+							type: 'number',
+							description: 'Optional number of lines removed.'
+						},
+						title: {
+							type: 'string',
+							description: 'Optional title shown in the file tooltip.'
+						},
+						description: {
+							type: 'string',
+							description: 'Optional secondary label shown for the file entry.'
+						}
+					},
+					required: ['uri'],
+					additionalProperties: false
+				},
+				description: 'Modified files to show in the confirmation UI.'
+			}
+		},
+		required: ['title', 'message', 'options', 'modifiedFiles'],
+		additionalProperties: false
+	}
+};
+
 export interface IConfirmationToolParams {
 	title: string;
 	message: string;
@@ -77,6 +142,20 @@ export interface IConfirmationToolParams {
 	buttons?: string[];
 }
 
+export interface IModifiedFilesConfirmationToolParams {
+	title: string;
+	message: string;
+	options: string[];
+	modifiedFiles: {
+		uri: string;
+		originalUri?: string;
+		insertions?: number;
+		deletions?: number;
+		title?: string;
+		description?: string;
+	}[];
+}
+
 export class ConfirmationTool implements IToolImpl {
 	async prepareToolInvocation(context: IToolInvocationPreparationContext, token: CancellationToken): Promise<IPreparedToolInvocation | undefined> {
 		const parameters = context.parameters as IConfirmationToolParams;
@@ -135,3 +214,59 @@ export class ConfirmationTool implements IToolImpl {
 		};
 	}
 }
+
+export class ModifiedFilesConfirmationTool implements IToolImpl {
+	async prepareToolInvocation(context: IToolInvocationPreparationContext, token: CancellationToken): Promise<IPreparedToolInvocation | undefined> {
+		const parameters = context.parameters as IModifiedFilesConfirmationToolParams;
+		if (!parameters.title || !parameters.message) {
+			throw new Error('Missing required parameters for ModifiedFilesConfirmationTool');
+		}
+
+		if (!parameters.options?.length) {
+			throw new Error('ModifiedFilesConfirmationTool requires at least one option');
+		}
+
+		const toolSpecificData: IChatModifiedFilesConfirmationData = {
+			kind: 'modifiedFilesConfirmation',
+			options: parameters.options,
+			modifiedFiles: parameters.modifiedFiles.map(file => ({
+				uri: URI.parse(file.uri).toJSON(),
+				originalUri: file.originalUri ? URI.parse(file.originalUri).toJSON() : undefined,
+				insertions: file.insertions,
+				deletions: file.deletions,
+				title: file.title,
+				description: file.description,
+			})),
+		};
+
+		return {
+			confirmationMessages: {
+				title: parameters.title,
+				message: new MarkdownString(parameters.message),
+				allowAutoConfirm: false,
+			},
+			toolSpecificData,
+			presentation: ToolInvocationPresentation.HiddenAfterComplete
+		};
+	}
+
+	async invoke(invocation: IToolInvocation, countTokens: CountTokensCallback, progress: ToolProgress, token: CancellationToken): Promise<IToolResult> {
+		// If a custom button was selected, return the button label
+		if (invocation.selectedCustomButton) {
+			return {
+				content: [{
+					kind: 'text',
+					value: invocation.selectedCustomButton
+				}]
+			};
+		}
+
+		// Default: return 'yes' for standard Allow confirmation
+		return {
+			content: [{
+				kind: 'text',
+				value: 'yes' // Consumers should check for this label to know whether the tool was confirmed or skipped
+			}]
+		};
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/common/tools/builtinTools/editFileTool.ts b/src/vs/workbench/contrib/chat/common/tools/builtinTools/editFileTool.ts
index f83c3c4e7a83d..addfc96f5d645 100644
--- a/src/vs/workbench/contrib/chat/common/tools/builtinTools/editFileTool.ts
+++ b/src/vs/workbench/contrib/chat/common/tools/builtinTools/editFileTool.ts
@@ -7,6 +7,7 @@ import { CancellationToken } from '../../../../../../base/common/cancellation.js
 import { MarkdownString } from '../../../../../../base/common/htmlContent.js';
 import { IDisposable } from '../../../../../../base/common/lifecycle.js';
 import { autorun } from '../../../../../../base/common/observable.js';
+import { isEqual } from '../../../../../../base/common/resources.js';
 import { URI, UriComponents } from '../../../../../../base/common/uri.js';
 import { CellUri } from '../../../../notebook/common/notebookCommon.js';
 import { INotebookService } from '../../../../notebook/common/notebookService.js';
@@ -118,7 +119,7 @@ export class EditTool implements IToolImpl {
 			dispose = autorun((r) => {
 
 				const entries = editSession.entries.read(r);
-				const currentFile = entries?.find((e) => e.modifiedURI.toString() === uri.toString());
+				const currentFile = entries?.find((e) => isEqual(e.modifiedURI, uri));
 				if (currentFile) {
 					if (currentFile.isCurrentlyBeingModifiedBy.read(r)) {
 						wasFileBeingModified = true;
diff --git a/src/vs/workbench/contrib/chat/common/tools/builtinTools/listDebugEventsTool.ts b/src/vs/workbench/contrib/chat/common/tools/builtinTools/listDebugEventsTool.ts
new file mode 100644
index 0000000000000..37baf2839d4e1
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/tools/builtinTools/listDebugEventsTool.ts
@@ -0,0 +1,98 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { CancellationToken } from '../../../../../../base/common/cancellation.js';
+import { localize } from '../../../../../../nls.js';
+import { ChatContextKeys } from '../../actions/chatContextKeys.js';
+import { IChatDebugEvent, IChatDebugService } from '../../chatDebugService.js';
+import { formatDebugEventsForContext, debugEventKindDescriptions, filterDebugEvents, debugEventFilterDescription } from '../../chatDebugEvents.js';
+import { CountTokensCallback, IPreparedToolInvocation, IToolData, IToolImpl, IToolInvocation, IToolInvocationPreparationContext, IToolResult, ToolDataSource, ToolProgress } from '../languageModelToolsService.js';
+
+export const ListDebugEventsToolId = 'vscode_listDebugEvents_internal';
+
+export const ListDebugEventsToolData: IToolData = {
+	id: ListDebugEventsToolId,
+	toolReferenceName: 'listDebugEvents',
+	displayName: localize('listDebugEvents.displayName', "List Debug Events"),
+	when: ChatContextKeys.chatSessionHasDebugTools,
+	canBeReferencedInPrompt: false,
+	modelDescription: 'Lists debug event summaries for the current chat session. Returns a compact log of events including timestamps, event IDs, and brief descriptions. Use this tool FIRST to get an overview of what happened, then call resolveDebugEventDetails on specific event IDs to get full details.\n\n'
+		+ 'Event types:\n'
+		+ Object.values(debugEventKindDescriptions).join('\n'),
+	source: ToolDataSource.Internal,
+	inputSchema: {
+		type: 'object',
+		properties: {
+			kind: {
+				type: 'string',
+				description: 'Filter by event kind: ' + Object.keys(debugEventKindDescriptions).join(', ') + '.',
+			},
+			filter: {
+				type: 'string',
+				description: debugEventFilterDescription,
+			},
+			limit: {
+				type: 'number',
+				description: 'Return only the N most recent matching events.',
+			},
+		},
+	},
+};
+
+export class ListDebugEventsTool implements IToolImpl {
+	constructor(
+		@IChatDebugService private readonly chatDebugService: IChatDebugService,
+	) { }
+
+	async prepareToolInvocation(_context: IToolInvocationPreparationContext, _token: CancellationToken): Promise<IPreparedToolInvocation | undefined> {
+		return {
+			invocationMessage: localize('listDebugEvents.invocationMessage', 'Listing debug events'),
+			pastTenseMessage: localize('listDebugEvents.pastTenseMessage', 'Listed debug events'),
+		};
+	}
+
+	async invoke(invocation: IToolInvocation, _countTokens: CountTokensCallback, _progress: ToolProgress, _token: CancellationToken): Promise<IToolResult> {
+		const sessionResource = invocation.context?.sessionResource;
+		if (!sessionResource) {
+			return {
+				content: [{ kind: 'text', value: 'Error: no chat session context available.' }],
+			};
+		}
+
+		// Ensure providers have been invoked so we have all events
+		if (!this.chatDebugService.hasInvokedProviders(sessionResource)) {
+			await this.chatDebugService.invokeProviders(sessionResource);
+		}
+
+		let events: readonly IChatDebugEvent[] = this.chatDebugService.getEvents(sessionResource);
+		if (events.length === 0) {
+			return {
+				content: [{ kind: 'text', value: 'No debug events found for this conversation.' }],
+			};
+		}
+
+		events = filterDebugEvents(events, {
+			kind: typeof invocation.parameters['kind'] === 'string' ? invocation.parameters['kind'] : undefined,
+			filter: typeof invocation.parameters['filter'] === 'string' ? invocation.parameters['filter'].toLowerCase() : undefined,
+			limit: typeof invocation.parameters['limit'] === 'number' ? invocation.parameters['limit'] : undefined,
+		});
+
+		if (events.length === 0) {
+			return {
+				content: [{ kind: 'text', value: 'No debug events matched the filter criteria.' }],
+			};
+		}
+
+		const summary = formatDebugEventsForContext(events);
+		return {
+			content: [{
+				kind: 'text',
+				value: 'Debug event log for this conversation. Each line is a summary — call resolveDebugEventDetails with the event ID (shown as [id=...]) to get full details.\n\n'
+					+ 'IMPORTANT: Do NOT mention event IDs or tool resolution steps in your response to the user.\n\n'
+					+ summary,
+			}],
+		};
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/common/tools/builtinTools/manageTodoListTool.ts b/src/vs/workbench/contrib/chat/common/tools/builtinTools/manageTodoListTool.ts
index e1ba741425ac1..193755bde2345 100644
--- a/src/vs/workbench/contrib/chat/common/tools/builtinTools/manageTodoListTool.ts
+++ b/src/vs/workbench/contrib/chat/common/tools/builtinTools/manageTodoListTool.ts
@@ -157,7 +157,11 @@ export class ManageTodoListTool extends Disposable implements IToolImpl {
 			status: todo.status
 		}));
 
+		const invocationLabel = message?.replace(/^(Starting|Completed): /i, '') ?? localize('todo.updatingList', "Updating todo list");
+		const invocationMessage = new MarkdownString(invocationLabel);
+
 		return {
+			invocationMessage,
 			pastTenseMessage: new MarkdownString(message ?? localize('todo.updatedList', "Updated todo list")),
 			toolSpecificData: {
 				kind: 'todoList',
diff --git a/src/vs/workbench/contrib/chat/common/tools/builtinTools/resolveDebugEventDetailsTool.ts b/src/vs/workbench/contrib/chat/common/tools/builtinTools/resolveDebugEventDetailsTool.ts
new file mode 100644
index 0000000000000..24bfed2d5576d
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/tools/builtinTools/resolveDebugEventDetailsTool.ts
@@ -0,0 +1,188 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { CancellationToken } from '../../../../../../base/common/cancellation.js';
+import { localize } from '../../../../../../nls.js';
+import { ChatContextKeys } from '../../actions/chatContextKeys.js';
+import { IChatDebugEvent, IChatDebugResolvedEventContent, IChatDebugService } from '../../chatDebugService.js';
+import { CountTokensCallback, IPreparedToolInvocation, IToolData, IToolImpl, IToolInvocation, IToolInvocationPreparationContext, IToolResult, ToolDataSource, ToolProgress } from '../languageModelToolsService.js';
+
+export const ResolveDebugEventDetailsToolId = 'vscode_resolveDebugEventDetails_internal';
+
+export const ResolveDebugEventDetailsToolData: IToolData = {
+	id: ResolveDebugEventDetailsToolId,
+	toolReferenceName: 'resolveDebugEventDetails',
+	displayName: localize('resolveDebugEventDetails.displayName', "Resolve Debug Event Details"),
+	when: ChatContextKeys.chatSessionHasDebugTools,
+	canBeReferencedInPrompt: false,
+	modelDescription: 'Resolves the full details for a specific chat debug event by its event ID. Use this tool to get detailed information about a debug event such as tool call input/output, model turn details, user message sections, or file lists. The event ID can be found in the debug event log summary provided in the conversation context.',
+	source: ToolDataSource.Internal,
+	inputSchema: {
+		type: 'object',
+		properties: {
+			eventId: {
+				type: 'string',
+				description: 'The ID of the debug event to resolve details for.',
+			},
+		},
+		required: ['eventId'],
+	},
+};
+
+function formatResolvedContent(content: IChatDebugResolvedEventContent): string {
+	switch (content.kind) {
+		case 'text':
+			return content.value;
+		case 'fileList': {
+			const lines: string[] = [`File list (${content.discoveryType}):`];
+			if (content.sourceFolders) {
+				for (const folder of content.sourceFolders) {
+					lines.push(`  Source folder: ${folder.uri.toString()} (${folder.storage})`);
+				}
+			}
+			for (const file of content.files) {
+				const status = file.status === 'loaded' ? 'loaded' : `skipped${file.skipReason ? `: ${file.skipReason}` : ''}`;
+				lines.push(`  ${file.uri.toString()} [${status}]`);
+			}
+			return lines.join('\n');
+		}
+		case 'message': {
+			const lines: string[] = [`${content.type === 'user' ? 'User' : 'Agent'} message: ${content.message}`];
+			for (const section of content.sections) {
+				lines.push(`--- ${section.name} ---`);
+				lines.push(section.content);
+			}
+			return lines.join('\n');
+		}
+		case 'toolCall': {
+			const lines: string[] = [`Tool call: ${content.toolName}`];
+			if (content.result) {
+				lines.push(`Result: ${content.result}`);
+			}
+			if (content.durationInMillis !== undefined) {
+				lines.push(`Duration: ${content.durationInMillis}ms`);
+			}
+			if (content.input) {
+				lines.push(`Input:\n${content.input}`);
+			}
+			if (content.output) {
+				lines.push(`Output:\n${content.output}`);
+			}
+			return lines.join('\n');
+		}
+		case 'modelTurn': {
+			const lines: string[] = [`Model turn: ${content.requestName}`];
+			if (content.model) {
+				lines.push(`Model: ${content.model}`);
+			}
+			if (content.status) {
+				lines.push(`Status: ${content.status}`);
+			}
+			if (content.durationInMillis !== undefined) {
+				lines.push(`Duration: ${content.durationInMillis}ms`);
+			}
+			if (content.inputTokens !== undefined || content.outputTokens !== undefined) {
+				lines.push(`Tokens: input=${content.inputTokens ?? '?'}, output=${content.outputTokens ?? '?'}, cached=${content.cachedTokens ?? '?'}, total=${content.totalTokens ?? '?'}`);
+			}
+			if (content.errorMessage) {
+				lines.push(`Error: ${content.errorMessage}`);
+			}
+			if (content.sections) {
+				for (const section of content.sections) {
+					lines.push(`--- ${section.name} ---`);
+					lines.push(section.content);
+				}
+			}
+			return lines.join('\n');
+		}
+		default: {
+			const _: never = content;
+			return JSON.stringify(_);
+		}
+	}
+}
+
+function truncate(text: string, maxLength = 30): string {
+	if (text.length <= maxLength) {
+		return text;
+	}
+	const lastSpace = text.lastIndexOf(' ', maxLength);
+	const cutoff = lastSpace > maxLength / 2 ? lastSpace : maxLength;
+	return text.substring(0, cutoff) + '\u2026';
+}
+
+function getEventLabel(event: IChatDebugEvent): string {
+	switch (event.kind) {
+		case 'generic': return event.name;
+		case 'toolCall': return event.toolName;
+		case 'modelTurn': return event.requestName ?? localize('debugEvent.modelTurn', "Model Turn");
+		case 'userMessage': return localize('debugEvent.userMessage', "User Message: {0}", truncate(event.message));
+		case 'agentResponse': return localize('debugEvent.agentResponse', "Agent Response: {0}", truncate(event.message));
+		case 'subagentInvocation': return event.agentName;
+	}
+}
+
+export class ResolveDebugEventDetailsTool implements IToolImpl {
+	constructor(
+		@IChatDebugService private readonly chatDebugService: IChatDebugService,
+	) { }
+
+	async prepareToolInvocation(context: IToolInvocationPreparationContext, _token: CancellationToken): Promise<IPreparedToolInvocation | undefined> {
+		const eventId = context.parameters?.eventId;
+		let eventLabel: string | undefined;
+		if (typeof eventId === 'string' && context.chatSessionResource) {
+			const events = this.chatDebugService.getEvents(context.chatSessionResource);
+			const event = events.find(e => e.id === eventId);
+			if (event) {
+				eventLabel = getEventLabel(event);
+			}
+		}
+
+		if (eventLabel) {
+			return {
+				invocationMessage: localize('resolveDebugEventDetails.invocationMessageNamed', 'Resolving details for "{0}"', eventLabel),
+				pastTenseMessage: localize('resolveDebugEventDetails.pastTenseMessageNamed', 'Resolved details for "{0}"', eventLabel),
+			};
+		}
+		return {
+			invocationMessage: localize('resolveDebugEventDetails.invocationMessage', 'Resolving debug event details'),
+			pastTenseMessage: localize('resolveDebugEventDetails.pastTenseMessage', 'Resolved debug event details'),
+		};
+	}
+
+	async invoke(invocation: IToolInvocation, _countTokens: CountTokensCallback, _progress: ToolProgress, _token: CancellationToken): Promise<IToolResult> {
+		const eventId = invocation.parameters['eventId'];
+		if (typeof eventId !== 'string' || !eventId) {
+			return {
+				content: [{ kind: 'text', value: 'Error: eventId parameter is required.' }],
+			};
+		}
+
+		const sessionResource = invocation.context?.sessionResource;
+		if (!sessionResource) {
+			return {
+				content: [{ kind: 'text', value: 'Error: no chat session context available.' }],
+			};
+		}
+
+		const sessionEvents = this.chatDebugService.getEvents(sessionResource);
+		if (!sessionEvents.some(e => e.id === eventId)) {
+			return {
+				content: [{ kind: 'text', value: `No event with ID "${eventId}" found in the current session.` }],
+			};
+		}
+
+		const resolved = await this.chatDebugService.resolveEvent(eventId);
+		if (!resolved) {
+			return {
+				content: [{ kind: 'text', value: `No details found for event ID: ${eventId}` }],
+			};
+		}
+
+		return {
+			content: [{ kind: 'text', value: formatResolvedContent(resolved) }],
+		};
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/common/tools/builtinTools/runSubagentTool.ts b/src/vs/workbench/contrib/chat/common/tools/builtinTools/runSubagentTool.ts
index fe31a470b1d6e..c5931a7d73213 100644
--- a/src/vs/workbench/contrib/chat/common/tools/builtinTools/runSubagentTool.ts
+++ b/src/vs/workbench/contrib/chat/common/tools/builtinTools/runSubagentTool.ts
@@ -15,16 +15,18 @@ import { localize } from '../../../../../../nls.js';
 import { IConfigurationChangeEvent, IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
 import { IInstantiationService } from '../../../../../../platform/instantiation/common/instantiation.js';
 import { ILogService } from '../../../../../../platform/log/common/log.js';
+import { IProductService } from '../../../../../../platform/product/common/productService.js';
 import { ChatRequestVariableSet } from '../../attachments/chatVariableEntries.js';
 import { IChatProgress, IChatService } from '../../chatService/chatService.js';
 import { ChatAgentLocation, ChatConfiguration, ChatModeKind } from '../../constants.js';
 import { ILanguageModelsService } from '../../languageModels.js';
 import { ChatModel, IChatRequestModeInstructions } from '../../model/chatModel.js';
-import { chatSessionResourceToId } from '../../model/chatUri.js';
 import { IChatAgentRequest, IChatAgentService } from '../../participants/chatAgents.js';
 import { ComputeAutomaticInstructions } from '../../promptSyntax/computeAutomaticInstructions.js';
-import { IChatRequestHooks } from '../../promptSyntax/hookSchema.js';
+import { ChatRequestHooks, mergeHooks } from '../../promptSyntax/hookSchema.js';
+import { HookType } from '../../promptSyntax/hookTypes.js';
 import { ICustomAgent, IPromptsService } from '../../promptSyntax/service/promptsService.js';
+import { isBuiltinAgent } from '../../promptSyntax/utils/promptsServiceUtils.js';
 import {
 	CountTokensCallback,
 	ILanguageModelToolsService,
@@ -75,6 +77,7 @@ export class RunSubagentTool extends Disposable implements IToolImpl {
 		@IConfigurationService private readonly configurationService: IConfigurationService,
 		@IPromptsService private readonly promptsService: IPromptsService,
 		@IInstantiationService private readonly instantiationService: IInstantiationService,
+		@IProductService private readonly productService: IProductService,
 	) {
 		super();
 		this.onDidUpdateToolData = Event.filter(this.configurationService.onDidChangeConfiguration, e => e.affectsConfiguration(ChatConfiguration.SubagentToolCustomAgents));
@@ -187,6 +190,7 @@ export class RunSubagentTool extends Disposable implements IToolImpl {
 						content: instructions.content,
 						toolReferences: this.toolsService.toToolReferences(instructions.toolReferences),
 						metadata: instructions.metadata,
+						isBuiltin: isBuiltinAgent(subagent.source, subagent.uri, this.productService),
 					};
 				} else {
 					throw new Error(`Requested agent '${subAgentName}' not found. Try again with the correct agent name, or omit the agentName to use the current agent.`);
@@ -245,19 +249,32 @@ export class RunSubagentTool extends Disposable implements IToolImpl {
 			}
 
 			const variableSet = new ChatRequestVariableSet();
-			const sessionId = chatSessionResourceToId(invocation.context.sessionResource);
-			const computer = this.instantiationService.createInstance(ComputeAutomaticInstructions, ChatModeKind.Agent, modeTools, undefined, sessionId); // agents can not call subagents
+			const computer = this.instantiationService.createInstance(ComputeAutomaticInstructions, ChatModeKind.Agent, modeTools, undefined, invocation.context.sessionResource); // agents can not call subagents
 			await computer.collect(variableSet, token);
 
 			// Collect hooks from hook .json files
-			let collectedHooks: IChatRequestHooks | undefined;
+			let collectedHooks: ChatRequestHooks | undefined;
 			try {
-				const info = await this.promptsService.getHooks(token, chatSessionResourceToId(invocation.context.sessionResource));
+				const info = await this.promptsService.getHooks(token, invocation.context.sessionResource);
 				collectedHooks = info?.hooks;
 			} catch (error) {
 				this.logService.warn('[ChatService] Failed to collect hooks:', error);
 			}
 
+			// Merge subagent-level hooks (from the agent's frontmatter) with global hooks.
+			// Remap Stop hooks to SubagentStop since the agent is running as a subagent.
+			if (subagent?.hooks) {
+				const remapped: ChatRequestHooks = { ...subagent.hooks };
+				if (remapped[HookType.Stop]) {
+					const stopHooks = remapped[HookType.Stop];
+					(remapped as Record<string, unknown>)[HookType.SubagentStop] = remapped[HookType.SubagentStop]
+						? [...remapped[HookType.SubagentStop], ...stopHooks]
+						: stopHooks;
+					(remapped as Record<string, unknown>)[HookType.Stop] = undefined;
+				}
+				collectedHooks = mergeHooks(collectedHooks, remapped);
+			}
+
 			// Build the agent request
 			const agentRequest: IChatAgentRequest = {
 				sessionResource: invocation.context.sessionResource,
diff --git a/src/vs/workbench/contrib/chat/common/tools/builtinTools/taskCompleteTool.ts b/src/vs/workbench/contrib/chat/common/tools/builtinTools/taskCompleteTool.ts
new file mode 100644
index 0000000000000..15094b0ce1adb
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/common/tools/builtinTools/taskCompleteTool.ts
@@ -0,0 +1,77 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { CancellationToken } from '../../../../../../base/common/cancellation.js';
+import { IPreparedToolInvocation, IToolData, IToolImpl, IToolInvocation, IToolInvocationPreparationContext, IToolResult, ToolDataSource, ToolInvocationPresentation, ToolProgress, CountTokensCallback } from '../languageModelToolsService.js';
+
+export const TaskCompleteToolId = 'task_complete';
+
+/**
+ * Message sent to the agent when the session goes idle without task completion.
+ */
+export const AUTOPILOT_CONTINUATION_MESSAGE =
+	'You have not yet marked the task as complete using the task_complete tool. ' +
+	'You MUST call task_complete when done — whether the task involved code changes, answering a question, or any other interaction.\n\n' +
+	'Do NOT repeat or restate your previous response. Pick up where you left off.\n\n' +
+	'If you were planning, stop planning and start implementing. ' +
+	'You are not done until you have fully completed the task.\n\n' +
+	'IMPORTANT: Do NOT call task_complete if:\n' +
+	'- You have open questions or ambiguities — make good decisions and keep working\n' +
+	'- You encountered an error — try to resolve it or find an alternative approach\n' +
+	'- There are remaining steps — complete them first\n\n' +
+	'When you ARE done, first provide a brief text summary of what was accomplished, then call task_complete. ' +
+	'Both the summary message and the tool call are required.\n\n' +
+	'Keep working autonomously until the task is truly finished, then call task_complete.';
+
+export const TaskCompleteToolData: IToolData = {
+	id: TaskCompleteToolId,
+	displayName: 'Task Complete',
+	modelDescription:
+		'Signal that the user\'s task is fully done. You MUST call this tool when your work is complete — ' +
+		'whether you made code changes, answered a question, or completed any other kind of task. ' +
+		'Provide a brief summary of what was accomplished. ' +
+		'Do not restate the summary in your message text — it is shown to the user directly.\n\n' +
+		'IMPORTANT: Before calling this tool, you MUST output a brief text message summarizing what was done. ' +
+		'The task is not complete until both your summary message AND this tool call are present.\n\n' +
+		'When to call:\n' +
+		'- After answering the user\'s question or completing a conversational request\n' +
+		'- After you have completed ALL requested changes\n' +
+		'- After verifying results: tests pass, terminal commands succeeded, tool calls returned expected output\n\n' +
+		'When NOT to call:\n' +
+		'- If a terminal command failed or produced unexpected output\n' +
+		'- If an MCP or external tool call returned an error\n' +
+		'- If you encountered errors you have not resolved\n' +
+		'- If there are remaining steps to complete\n' +
+		'- If you have not verified your changes work',
+	source: ToolDataSource.Internal,
+	inputSchema: {
+		type: 'object',
+		properties: {
+			summary: {
+				type: 'string',
+				description: 'Brief summary of what was accomplished. Omit for trivial interactions.',
+			},
+		},
+	},
+};
+
+export class TaskCompleteTool implements IToolImpl {
+	async prepareToolInvocation(_context: IToolInvocationPreparationContext, _token: CancellationToken): Promise<IPreparedToolInvocation | undefined> {
+		return {
+			presentation: ToolInvocationPresentation.Hidden,
+		};
+	}
+
+	async invoke(invocation: IToolInvocation, _countTokens: CountTokensCallback, _progress: ToolProgress, _token: CancellationToken): Promise<IToolResult> {
+		const params = invocation.parameters as { summary?: string };
+		const summary = params?.summary ?? 'All done!';
+		return {
+			content: [{
+				kind: 'text',
+				value: summary,
+			}],
+		};
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/common/tools/builtinTools/tools.ts b/src/vs/workbench/contrib/chat/common/tools/builtinTools/tools.ts
index 56a1b956acbe7..fe6be20ef6ddc 100644
--- a/src/vs/workbench/contrib/chat/common/tools/builtinTools/tools.ts
+++ b/src/vs/workbench/contrib/chat/common/tools/builtinTools/tools.ts
@@ -8,10 +8,13 @@ import { IInstantiationService } from '../../../../../../platform/instantiation/
 import { IWorkbenchContribution } from '../../../../../common/contributions.js';
 import { ILanguageModelToolsService } from '../languageModelToolsService.js';
 import { AskQuestionsTool, AskQuestionsToolData } from './askQuestionsTool.js';
-import { ConfirmationTool, ConfirmationToolData, ConfirmationToolWithOptionsData } from './confirmationTool.js';
+import { ConfirmationTool, ConfirmationToolData, ConfirmationToolWithOptionsData, ModifiedFilesConfirmationTool, ModifiedFilesConfirmationToolData } from './confirmationTool.js';
 import { EditTool, EditToolData } from './editFileTool.js';
 import { createManageTodoListToolData, ManageTodoListTool } from './manageTodoListTool.js';
+import { ResolveDebugEventDetailsTool, ResolveDebugEventDetailsToolData } from './resolveDebugEventDetailsTool.js';
+import { ListDebugEventsTool, ListDebugEventsToolData } from './listDebugEventsTool.js';
 import { RunSubagentTool } from './runSubagentTool.js';
+import { TaskCompleteTool, TaskCompleteToolData } from './taskCompleteTool.js';
 
 export class BuiltinToolsContribution extends Disposable implements IWorkbenchContribution {
 
@@ -28,17 +31,32 @@ export class BuiltinToolsContribution extends Disposable implements IWorkbenchCo
 
 		const askQuestionsTool = this._register(instantiationService.createInstance(AskQuestionsTool));
 		this._register(toolsService.registerTool(AskQuestionsToolData, askQuestionsTool));
-		this._register(toolsService.agentToolSet.addTool(AskQuestionsToolData));
+		this._register(toolsService.vscodeToolSet.addTool(AskQuestionsToolData));
 
 		const todoToolData = createManageTodoListToolData();
 		const manageTodoListTool = this._register(instantiationService.createInstance(ManageTodoListTool));
 		this._register(toolsService.registerTool(todoToolData, manageTodoListTool));
 
-		// Register the confirmation tool
 		const confirmationTool = instantiationService.createInstance(ConfirmationTool);
 		this._register(toolsService.registerTool(ConfirmationToolData, confirmationTool));
 		this._register(toolsService.registerTool(ConfirmationToolWithOptionsData, confirmationTool));
 
+		const modifiedFilesConfirmationTool = instantiationService.createInstance(ModifiedFilesConfirmationTool);
+		this._register(toolsService.registerTool(ModifiedFilesConfirmationToolData, modifiedFilesConfirmationTool));
+
+
+		const taskCompleteTool = instantiationService.createInstance(TaskCompleteTool);
+		this._register(toolsService.registerTool(TaskCompleteToolData, taskCompleteTool));
+
+		const resolveDebugEventDetailsTool = instantiationService.createInstance(ResolveDebugEventDetailsTool);
+		this._register(toolsService.registerTool(ResolveDebugEventDetailsToolData, resolveDebugEventDetailsTool));
+		this._register(toolsService.readToolSet.addTool(ResolveDebugEventDetailsToolData));
+
+		const listDebugEventsTool = instantiationService.createInstance(ListDebugEventsTool);
+		this._register(toolsService.registerTool(ListDebugEventsToolData, listDebugEventsTool));
+		this._register(toolsService.readToolSet.addTool(ListDebugEventsToolData));
+
+
 		const runSubagentTool = this._register(instantiationService.createInstance(RunSubagentTool));
 
 		let runSubagentRegistration: IDisposable | undefined;
diff --git a/src/vs/workbench/contrib/chat/common/tools/languageModelToolsConfirmationService.ts b/src/vs/workbench/contrib/chat/common/tools/languageModelToolsConfirmationService.ts
index d77bd07c0c0f5..2e3c66261b821 100644
--- a/src/vs/workbench/contrib/chat/common/tools/languageModelToolsConfirmationService.ts
+++ b/src/vs/workbench/contrib/chat/common/tools/languageModelToolsConfirmationService.ts
@@ -42,7 +42,7 @@ export interface ILanguageModelToolConfirmationActionProducer {
 export interface ILanguageModelToolConfirmationContributionQuickTreeItem extends IQuickTreeItem {
 	onDidTriggerItemButton?(button: IQuickInputButton): void;
 	onDidChangeChecked?(checked: boolean): void;
-	onDidOpen?(): void;
+	onDidOpen?(): void | Promise<void>;
 }
 
 /**
@@ -85,7 +85,7 @@ export interface ILanguageModelToolsConfirmationService extends ILanguageModelTo
 	readonly _serviceBrand: undefined;
 
 	/** Opens an IQuickTree to let the user manage their preferences.  */
-	manageConfirmationPreferences(tools: readonly IToolData[], options?: { defaultScope?: 'workspace' | 'profile' | 'session' }): void;
+	manageConfirmationPreferences(tools: readonly IToolData[], options?: { defaultScope?: 'workspace' | 'profile' | 'session'; focusToolId?: string }): void;
 
 	/**
 	 * Registers a contribution that provides more specific confirmation logic
@@ -93,6 +93,15 @@ export interface ILanguageModelToolsConfirmationService extends ILanguageModelTo
 	 */
 	registerConfirmationContribution(toolName: string, contribution: ILanguageModelToolConfirmationContribution): IDisposable;
 
+	/**
+	 * Returns true if the tool has confirmation that can be managed, either
+	 * because it has {@link IToolData.canRequestPreApproval} or
+	 * {@link IToolData.canRequestPostApproval} set, because a
+	 * {@link ILanguageModelToolConfirmationContribution} is registered for it,
+	 * or because it has stored auto-confirmation settings.
+	 */
+	toolCanManageConfirmation(tool: IToolData): boolean;
+
 	/** Resets all tool and server confirmation preferences */
 	resetToolAutoConfirmation(): void;
 }
diff --git a/src/vs/workbench/contrib/chat/common/tools/languageModelToolsService.ts b/src/vs/workbench/contrib/chat/common/tools/languageModelToolsService.ts
index d14a93696e08e..93be052e04b18 100644
--- a/src/vs/workbench/contrib/chat/common/tools/languageModelToolsService.ts
+++ b/src/vs/workbench/contrib/chat/common/tools/languageModelToolsService.ts
@@ -24,7 +24,7 @@ import { createDecorator } from '../../../../../platform/instantiation/common/in
 import { IProgress } from '../../../../../platform/progress/common/progress.js';
 import { ChatRequestToolReferenceEntry } from '../attachments/chatVariableEntries.js';
 import { IVariableReference } from '../chatModes.js';
-import { IChatExtensionsContent, IChatSimpleToolInvocationData, IChatSubagentToolInvocationData, IChatTodoListContent, IChatToolInputInvocationData, IChatToolInvocation, type IChatTerminalToolInvocationData } from '../chatService/chatService.js';
+import { IChatExtensionsContent, IChatModifiedFilesConfirmationData, IChatSimpleToolInvocationData, IChatSubagentToolInvocationData, IChatTodoListContent, IChatToolInputInvocationData, IChatToolInvocation, type IChatTerminalToolInvocationData } from '../chatService/chatService.js';
 import { ILanguageModelChatMetadata, LanguageModelPartAudience } from '../languageModels.js';
 import { UserSelectedTools } from '../participants/chatAgents.js';
 import { PromptElementJSON, stringifyPromptElementJSON } from './promptTsxTypes.js';
@@ -189,7 +189,7 @@ export interface IToolInvocation {
 	 * Lets us add some nicer UI to toolcalls that came from a sub-agent, but in the long run, this should probably just be rendered in a similar way to thinking text + tool call groups
 	 */
 	subAgentInvocationId?: string;
-	toolSpecificData?: IChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatSimpleToolInvocationData;
+	toolSpecificData?: IChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatSimpleToolInvocationData | IChatModifiedFilesConfirmationData;
 	modelId?: string;
 	userSelectedTools?: UserSelectedTools;
 	/** The label of the custom button selected by the user during confirmation, if custom buttons were used. */
@@ -241,6 +241,8 @@ export type ToolInputOutputReference = ToolInputOutputBase & { type: 'ref'; uri:
 
 export interface IToolResultInputOutputDetails {
 	readonly input: string;
+	/** Language identifier for syntax highlighting the input. Defaults to 'json'. */
+	readonly inputLanguage?: string;
 	readonly output: (ToolInputOutputEmbedded | ToolInputOutputReference)[];
 	readonly isError?: boolean;
 	/** Raw MCP tool result for MCP App UI rendering */
@@ -265,7 +267,7 @@ export interface IToolResult {
 	content: (IToolResultPromptTsxPart | IToolResultTextPart | IToolResultDataPart)[];
 	toolResultMessage?: string | IMarkdownString;
 	toolResultDetails?: Array<URI | Location> | IToolResultInputOutputDetails | IToolResultOutputDetails;
-	toolResultError?: string;
+	toolResultError?: string | boolean;
 	toolMetadata?: unknown;
 	/** Whether to ask the user to confirm these tool results. Overrides {@link IToolConfirmationMessages.confirmResults}. */
 	confirmResults?: boolean;
@@ -363,7 +365,7 @@ export interface IPreparedToolInvocation {
 	originMessage?: string | IMarkdownString;
 	confirmationMessages?: IToolConfirmationMessages;
 	presentation?: ToolInvocationPresentation;
-	toolSpecificData?: IChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatSimpleToolInvocationData;
+	toolSpecificData?: IChatTerminalToolInvocationData | IChatToolInputInvocationData | IChatExtensionsContent | IChatTodoListContent | IChatSubagentToolInvocationData | IChatSimpleToolInvocationData | IChatModifiedFilesConfirmationData;
 }
 
 export interface IToolImpl {
diff --git a/src/vs/workbench/contrib/chat/common/widget/annotations.ts b/src/vs/workbench/contrib/chat/common/widget/annotations.ts
index b43079b5add3a..c2fe2859e216a 100644
--- a/src/vs/workbench/contrib/chat/common/widget/annotations.ts
+++ b/src/vs/workbench/contrib/chat/common/widget/annotations.ts
@@ -57,9 +57,25 @@ export function annotateSpecialMarkdownContent(response: Iterable<IChatProgressR
 					result.push({ content: new MarkdownString(markdownText), inlineReferences: annotationMetadata, kind: 'markdownContent' });
 				}
 			}
-		} else if (item.kind === 'markdownContent' && previousItem?.kind === 'markdownContent' && canMergeMarkdownStrings(previousItem.content, item.content)) {
-			const merged = appendMarkdownString(previousItem.content, item.content);
-			result[previousItemIndex] = { ...previousItem, content: merged };
+		} else if (item.kind === 'markdownContent' && previousItem?.kind === 'markdownContent') {
+			if (canMergeMarkdownStrings(previousItem.content, item.content)) {
+				const merged = appendMarkdownString(previousItem.content, item.content);
+				result[previousItemIndex] = { ...previousItem, content: merged };
+			} else if (previousItem.inlineReferences && isContentRefOnly(previousItem.content.value)) {
+				// The previous item is a standalone inline reference whose MarkdownString
+				// was synthesized with default properties that don't match the incoming
+				// markdown (e.g., different isTrusted). Prepend the reference text and
+				// adopt the incoming item's properties so they render together in one block.
+				result[previousItemIndex] = {
+					...previousItem,
+					content: {
+						...item.content,
+						value: previousItem.content.value + item.content.value,
+					},
+				};
+			} else {
+				result.push(item);
+			}
 		} else if (item.kind === 'markdownVuln') {
 			const vulnText = encodeURIComponent(JSON.stringify(item.vulnerabilities));
 			const markdownText = `<vscode_annotation details='${vulnText}'>${item.content.value}</vscode_annotation>`;
@@ -88,6 +104,18 @@ export function annotateSpecialMarkdownContent(response: Iterable<IChatProgressR
 	return result;
 }
 
+const contentRefPattern = new RegExp(`^(\\[.*?\\]\\(${contentRefUrl}/\\d+\\))+$`);
+
+/**
+ * Returns true when the text consists entirely of synthesized content-ref
+ * links (e.g. `[file.ts](http://_vscodecontentref_/0)`), with no other
+ * markdown text mixed in. Used to decide whether the MarkdownString
+ * properties are "synthetic defaults" that can safely be replaced.
+ */
+function isContentRefOnly(text: string): boolean {
+	return contentRefPattern.test(text);
+}
+
 /**
  * Checks whether the end of a markdown string is inside a code context
  * (fenced code block or inline code span) where markdown link syntax
@@ -222,6 +250,10 @@ export function hasCodeblockUriTag(text: string): boolean {
 	return text.includes('<vscode_codeblock_uri');
 }
 
+export function hasEditCodeblockUriTag(text: string): boolean {
+	return text.includes('<vscode_codeblock_uri isEdit');
+}
+
 export function extractVulnerabilitiesFromText(text: string): { newText: string; vulnerabilities: IMarkdownVulnerability[] } {
 	const vulnerabilities: IMarkdownVulnerability[] = [];
 	let newText = text;
diff --git a/src/vs/workbench/contrib/chat/common/widget/chatResponseResourceFileSystemProvider.ts b/src/vs/workbench/contrib/chat/common/widget/chatResponseResourceFileSystemProvider.ts
index d1d069424dd20..6cab24df2d67e 100644
--- a/src/vs/workbench/contrib/chat/common/widget/chatResponseResourceFileSystemProvider.ts
+++ b/src/vs/workbench/contrib/chat/common/widget/chatResponseResourceFileSystemProvider.ts
@@ -6,21 +6,38 @@
 import { decodeBase64, VSBuffer } from '../../../../../base/common/buffer.js';
 import { Event } from '../../../../../base/common/event.js';
 import { Disposable, IDisposable } from '../../../../../base/common/lifecycle.js';
+import { ResourceMap, ResourceSet } from '../../../../../base/common/map.js';
 import { newWriteableStream, ReadableStreamEvents } from '../../../../../base/common/stream.js';
 import { URI } from '../../../../../base/common/uri.js';
-import { createFileSystemProviderError, FileSystemProviderCapabilities, FileSystemProviderErrorCode, FileType, IFileService, IFileSystemProviderWithFileAtomicReadCapability, IFileSystemProviderWithFileReadStreamCapability, IFileSystemProviderWithFileReadWriteCapability, IStat } from '../../../../../platform/files/common/files.js';
+import { generateUuid } from '../../../../../base/common/uuid.js';
+import { createDecorator } from '../../../../../platform/instantiation/common/instantiation.js';
+import { createFileSystemProviderError, FileSystemProviderCapabilities, FileSystemProviderErrorCode, FileType, IFileService, IFileSystemProvider, IFileSystemProviderWithFileAtomicReadCapability, IFileSystemProviderWithFileReadStreamCapability, IFileSystemProviderWithFileReadWriteCapability, IStat } from '../../../../../platform/files/common/files.js';
 import { IWorkbenchContribution } from '../../../../common/contributions.js';
 import { ChatResponseResource } from '../model/chatModel.js';
 import { IChatService, IChatToolInvocation, IChatToolInvocationSerialized } from '../chatService/chatService.js';
 import { isToolResultInputOutputDetails } from '../tools/languageModelToolsService.js';
 
+export const IChatResponseResourceFileSystemProvider = createDecorator<IChatResponseResourceFileSystemProvider>('chatResponseResourceFileSystemProvider');
+
+export interface IChatResponseResourceFileSystemProvider extends IFileSystemProvider {
+	readonly _serviceBrand: undefined;
+
+	/**
+	 * Associates arbitrary data with a URI in the chat response resource filesystem.
+	 * The data is scoped to the given session and automatically cleaned up when
+	 * the session is disposed.
+	 * Returns a URI that can later be read via the file service.
+	 */
+	associate(sessionResource: URI, data: Uint8Array | { base64: string }, name?: string): URI;
+}
+
 export class ChatResponseResourceFileSystemProvider extends Disposable implements
-	IWorkbenchContribution,
+	IChatResponseResourceFileSystemProvider,
 	IFileSystemProviderWithFileReadWriteCapability,
 	IFileSystemProviderWithFileAtomicReadCapability,
 	IFileSystemProviderWithFileReadStreamCapability {
 
-	public static readonly ID = 'workbench.contrib.chatResponseResourceFileSystemProvider';
+	declare readonly _serviceBrand: undefined;
 
 	public readonly onDidChangeCapabilities = Event.None;
 	public readonly onDidChangeFile = Event.None;
@@ -32,12 +49,46 @@ export class ChatResponseResourceFileSystemProvider extends Disposable implement
 		| FileSystemProviderCapabilities.FileAtomicRead
 		| FileSystemProviderCapabilities.FileReadWrite;
 
+	/** In-memory store for data associated via {@link associate}, keyed by URI. */
+	private readonly _associated = new ResourceMap<Uint8Array | { base64: string }>();
+
+	/** Tracks which associated URIs belong to which session, for cleanup on dispose. */
+	private readonly _sessionAssociations = new ResourceMap<ResourceSet>();
+
 	constructor(
 		@IChatService private readonly chatService: IChatService,
 		@IFileService private readonly _fileService: IFileService
 	) {
 		super();
-		this._register(this._fileService.registerProvider(ChatResponseResource.scheme, this));
+		this._register(this.chatService.onDidDisposeSession(e => {
+			for (const sessionResource of e.sessionResource) {
+				const uris = this._sessionAssociations.get(sessionResource);
+				if (uris) {
+					for (const uri of uris) {
+						this._associated.delete(uri);
+					}
+					this._sessionAssociations.delete(sessionResource);
+				}
+			}
+		}));
+	}
+
+	associate(sessionResource: URI, data: Uint8Array | { base64: string }, name?: string): URI {
+		const id = generateUuid();
+		const uri = URI.from({
+			scheme: ChatResponseResource.scheme,
+			path: `/assoc/${id}` + (name ? `/${name}` : ''),
+		});
+		this._associated.set(uri, data);
+
+		let set = this._sessionAssociations.get(sessionResource);
+		if (!set) {
+			set = new ResourceSet();
+			this._sessionAssociations.set(sessionResource, set);
+		}
+		set.add(uri);
+
+		return uri;
 	}
 
 	readFile(resource: URI): Promise<Uint8Array> {
@@ -108,6 +159,16 @@ export class ChatResponseResourceFileSystemProvider extends Disposable implement
 	}
 
 	private lookupURI(uri: URI): Uint8Array | Promise<Uint8Array> {
+		const associated = this._associated.get(uri);
+		if (associated) {
+			if (associated instanceof Uint8Array) {
+				return associated;
+			}
+			const decoded = decodeBase64(associated.base64).buffer;
+			this._associated.set(uri, decoded);
+			return decoded;
+		}
+
 		const { result, index } = this.findMatchingInvocation(uri);
 		const details = IChatToolInvocation.resultDetails(result);
 		if (!isToolResultInputOutputDetails(details)) {
@@ -126,3 +187,16 @@ export class ChatResponseResourceFileSystemProvider extends Disposable implement
 		return part.isText ? new TextEncoder().encode(part.value) : decodeBase64(part.value).buffer;
 	}
 }
+
+export class ChatResponseResourceWorkbenchContribution extends Disposable implements IWorkbenchContribution {
+
+	static readonly ID = 'chatResponseResourceWorkbenchContribution';
+
+	constructor(
+		@IChatResponseResourceFileSystemProvider chatResponseResourceFsProvider: IChatResponseResourceFileSystemProvider,
+		@IFileService fileService: IFileService,
+	) {
+		super();
+		this._register(fileService.registerProvider(ChatResponseResource.scheme, chatResponseResourceFsProvider));
+	}
+}
diff --git a/src/vs/workbench/contrib/chat/electron-browser/builtInTools/tools.ts b/src/vs/workbench/contrib/chat/electron-browser/builtInTools/tools.ts
index 3af7e138aeb54..1d1d822cc305a 100644
--- a/src/vs/workbench/contrib/chat/electron-browser/builtInTools/tools.ts
+++ b/src/vs/workbench/contrib/chat/electron-browser/builtInTools/tools.ts
@@ -6,8 +6,11 @@
 import { Disposable } from '../../../../../base/common/lifecycle.js';
 import { dirname, extUriBiasedIgnorePathCase } from '../../../../../base/common/resources.js';
 import { URI } from '../../../../../base/common/uri.js';
+import { IFileDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
 import { IFileService } from '../../../../../platform/files/common/files.js';
 import { IInstantiationService } from '../../../../../platform/instantiation/common/instantiation.js';
+import { ILabelService } from '../../../../../platform/label/common/label.js';
+import { IStorageService } from '../../../../../platform/storage/common/storage.js';
 import { IWorkbenchContribution } from '../../../../common/contributions.js';
 import { ChatExternalPathConfirmationContribution } from '../../common/tools/builtinTools/chatExternalPathConfirmation.js';
 import { ChatUrlFetchingConfirmationContribution } from '../../common/tools/builtinTools/chatUrlFetchingConfirmation.js';
@@ -25,6 +28,9 @@ export class NativeBuiltinToolsContribution extends Disposable implements IWorkb
 		@IInstantiationService instantiationService: IInstantiationService,
 		@ILanguageModelToolsConfirmationService confirmationService: ILanguageModelToolsConfirmationService,
 		@IFileService fileService: IFileService,
+		@IStorageService storageService: IStorageService,
+		@IFileDialogService fileDialogService: IFileDialogService,
+		@ILabelService labelService: ILabelService,
 	) {
 		super();
 
@@ -53,6 +59,7 @@ export class NativeBuiltinToolsContribution extends Disposable implements IWorkb
 				}
 				return undefined;
 			},
+			labelService,
 			async (pathUri: URI) => {
 				// Walk up from the path looking for a .git folder to find the repository root
 				let dir = dirname(pathUri);
@@ -71,8 +78,18 @@ export class NativeBuiltinToolsContribution extends Disposable implements IWorkb
 					dir = parent;
 				}
 				return undefined;
+			},
+			storageService,
+			async () => {
+				const result = await fileDialogService.showOpenDialog({
+					canSelectFolders: true,
+					canSelectFiles: false,
+					canSelectMany: false,
+				});
+				return result?.[0];
 			}
 		);
+		this._register(externalPathConfirmation);
 
 		this._register(confirmationService.registerConfirmationContribution(
 			'copilot_readFile',
diff --git a/src/vs/workbench/contrib/chat/electron-browser/chat.contribution.ts b/src/vs/workbench/contrib/chat/electron-browser/chat.contribution.ts
index 4ec33cc52a33a..8731979f149ee 100644
--- a/src/vs/workbench/contrib/chat/electron-browser/chat.contribution.ts
+++ b/src/vs/workbench/contrib/chat/electron-browser/chat.contribution.ts
@@ -146,7 +146,7 @@ class ChatLifecycleHandler extends Disposable {
 		}));
 
 		this._register(extensionService.onWillStop(e => {
-			e.veto(this.hasNonCloudSessionInProgress(), localize('chatRequestInProgress', "A chat request is in progress."));
+			e.veto(this.hasNonCloudSessionInProgress(), localize('chatRequestInProgress', "A session is in progress."));
 		}));
 	}
 
@@ -182,20 +182,20 @@ class ChatLifecycleHandler extends Disposable {
 		let detail: string;
 		switch (reason) {
 			case ShutdownReason.CLOSE:
-				message = localize('closeTheWindow.message', "A chat request is in progress. Are you sure you want to close the window?");
-				detail = localize('closeTheWindow.detail', "The chat request will stop if you close the window.");
+				message = localize('closeTheWindow.message', "A session is in progress. Are you sure you want to close the window?");
+				detail = localize('closeTheWindow.detail', "The session will stop if you close the window.");
 				break;
 			case ShutdownReason.LOAD:
-				message = localize('changeWorkspace.message', "A chat request is in progress. Are you sure you want to change the workspace?");
-				detail = localize('changeWorkspace.detail', "The chat request will stop if you change the workspace.");
+				message = localize('changeWorkspace.message', "A session is in progress. Are you sure you want to change the workspace?");
+				detail = localize('changeWorkspace.detail', "The session will stop if you change the workspace.");
 				break;
 			case ShutdownReason.RELOAD:
-				message = localize('reloadTheWindow.message', "A chat request is in progress. Are you sure you want to reload the window?");
-				detail = localize('reloadTheWindow.detail', "The chat request will stop if you reload the window.");
+				message = localize('reloadTheWindow.message', "A session is in progress. Are you sure you want to reload the window?");
+				detail = localize('reloadTheWindow.detail', "The session will stop if you reload the window.");
 				break;
 			default:
-				message = isMacintosh ? localize('quit.message', "A chat request is in progress. Are you sure you want to quit?") : localize('exit.message', "A chat request is in progress. Are you sure you want to exit?");
-				detail = isMacintosh ? localize('quit.detail', "The chat request will stop if you quit.") : localize('exit.detail', "The chat request will stop if you exit.");
+				message = isMacintosh ? localize('quit.message', "A session is in progress. Are you sure you want to quit?") : localize('exit.message', "A session is in progress. Are you sure you want to exit?");
+				detail = isMacintosh ? localize('quit.detail', "The session will stop if you quit.") : localize('exit.detail', "The session will stop if you exit.");
 				break;
 		}
 
diff --git a/src/vs/workbench/contrib/chat/test/browser/agentSessions/agentSessionApprovalModel.test.ts b/src/vs/workbench/contrib/chat/test/browser/agentSessions/agentSessionApprovalModel.test.ts
new file mode 100644
index 0000000000000..de54c6b14716d
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/browser/agentSessions/agentSessionApprovalModel.test.ts
@@ -0,0 +1,523 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { DisposableStore } from '../../../../../../base/common/lifecycle.js';
+import { ISettableObservable, observableValue } from '../../../../../../base/common/observable.js';
+import { URI } from '../../../../../../base/common/uri.js';
+import { MarkdownString } from '../../../../../../base/common/htmlContent.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { AgentSessionApprovalModel, IAgentSessionApprovalInfo } from '../../../browser/agentSessions/agentSessionApprovalModel.js';
+import { MockChatModel } from '../../common/model/mockChatModel.js';
+import { MockChatService } from '../../common/chatService/mockChatService.js';
+import { IChatToolInvocation, IChatTerminalToolInvocationData, ToolConfirmKind, ConfirmedReason } from '../../../common/chatService/chatService.js';
+import { IChatModel, IChatRequestModel, IChatResponseModel, IResponse, IChatProgressResponseContent } from '../../../common/model/chatModel.js';
+import { ILanguageService } from '../../../../../../editor/common/languages/language.js';
+
+function makeToolInvocationPart(options: {
+	state: IChatToolInvocation.State;
+	toolSpecificData?: IChatToolInvocation['toolSpecificData'];
+	invocationMessage?: string | MarkdownString;
+}): IChatToolInvocation {
+	return {
+		kind: 'toolInvocation',
+		presentation: undefined!,
+		originMessage: undefined,
+		invocationMessage: options.invocationMessage ?? 'Running tool...',
+		pastTenseMessage: undefined,
+		source: undefined!,
+		toolId: 'test-tool',
+		toolCallId: 'call-1',
+		state: observableValue('toolState', options.state),
+		toolSpecificData: options.toolSpecificData,
+		isAttachedToThinking: false,
+		toJSON: () => undefined!,
+	};
+}
+
+function makeTerminalToolData(overrides?: Partial<IChatTerminalToolInvocationData>): IChatTerminalToolInvocationData {
+	return {
+		kind: 'terminal',
+		commandLine: { original: 'echo hello' },
+		language: 'sh',
+		...overrides,
+	};
+}
+
+function makeWaitingState(confirm?: (reason: ConfirmedReason) => void): IChatToolInvocation.State {
+	return {
+		type: IChatToolInvocation.StateKind.WaitingForConfirmation,
+		parameters: {},
+		confirm: confirm ?? (() => { }),
+	} as IChatToolInvocation.State;
+}
+
+function makePostApprovalState(confirm?: (reason: ConfirmedReason) => void): IChatToolInvocation.State {
+	return {
+		type: IChatToolInvocation.StateKind.WaitingForPostApproval,
+		parameters: {},
+		confirmed: { type: ToolConfirmKind.UserAction },
+		resultDetails: undefined,
+		confirm: confirm ?? (() => { }),
+		contentForModel: [],
+	} as IChatToolInvocation.State;
+}
+
+function makeExecutingState(): IChatToolInvocation.State {
+	return {
+		type: IChatToolInvocation.StateKind.Executing,
+		parameters: {},
+		confirmed: { type: ToolConfirmKind.UserAction },
+		progress: observableValue('progress', { message: undefined, progress: undefined }),
+	} as IChatToolInvocation.State;
+}
+
+/** Creates a minimal mock that satisfies the response chain: lastRequest.response.response.value */
+function mockModelWithResponse(model: MockChatModel, parts: IChatProgressResponseContent[]): void {
+	const response: Partial<IChatResponseModel> = {
+		response: { value: parts, getMarkdown: () => '', toString: () => '' } satisfies IResponse,
+	};
+	const request: Partial<IChatRequestModel> = {
+		response: response as IChatResponseModel,
+	};
+	(model as { lastRequest: IChatRequestModel | undefined }).lastRequest = request as IChatRequestModel;
+}
+
+class MockLanguageService {
+	getLanguageIdByLanguageName(name: string): string | undefined {
+		switch (name) {
+			case 'bash': return 'sh';
+			case 'python': return 'python';
+			case 'powershell': return 'pwsh';
+			default: return name;
+		}
+	}
+}
+
+suite('AgentSessionApprovalModel', () => {
+
+	const disposables = new DisposableStore();
+	let chatService: MockChatService;
+	let chatModelsObs: ISettableObservable<Iterable<IChatModel>>;
+	let langservice: MockLanguageService;
+
+	setup(() => {
+		chatService = new MockChatService();
+		langservice = new MockLanguageService();
+		chatModelsObs = chatService.chatModels as ISettableObservable<Iterable<IChatModel>>;
+	});
+
+	teardown(() => {
+		disposables.clear();
+	});
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	function createModel(): AgentSessionApprovalModel {
+		const model = new AgentSessionApprovalModel(chatService, langservice as ILanguageService);
+		disposables.add(model);
+		return model;
+	}
+
+	function addChatModel(uri?: URI): MockChatModel {
+		const chatModel = disposables.add(new MockChatModel(uri ?? URI.parse(`test://session/${Math.random()}`)));
+		chatModelsObs.set([...Array.from(chatModelsObs.get()), chatModel], undefined);
+		return chatModel;
+	}
+
+	function getApproval(approvalModel: AgentSessionApprovalModel, chatModel: MockChatModel): IAgentSessionApprovalInfo | undefined {
+		return approvalModel.getApproval(chatModel.sessionResource).get();
+	}
+
+	test('returns undefined when no models exist', () => {
+		const approvalModel = createModel();
+		const result = approvalModel.getApproval(URI.parse('test://nonexistent')).get();
+		assert.strictEqual(result, undefined);
+	});
+
+	test('returns undefined when model has no requestNeedsInput', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+		assert.strictEqual(getApproval(approvalModel, chatModel), undefined);
+	});
+
+	test('returns undefined when requestNeedsInput is set but no response exists', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+		assert.strictEqual(getApproval(approvalModel, chatModel), undefined);
+	});
+
+	test('returns undefined when response has no tool invocation parts', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+		mockModelWithResponse(chatModel, []);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+		assert.strictEqual(getApproval(approvalModel, chatModel), undefined);
+	});
+
+	test('returns undefined when tool invocation is in Executing state', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const part = makeToolInvocationPart({ state: makeExecutingState() });
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		assert.strictEqual(getApproval(approvalModel, chatModel), undefined);
+	});
+
+	test('returns approval info for WaitingForConfirmation state with terminal data', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: makeTerminalToolData(),
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		const result = getApproval(approvalModel, chatModel);
+		assert.deepStrictEqual({
+			label: result?.label,
+			language: result?.languageId,
+		}, {
+			label: 'echo hello',
+			language: 'sh',
+		});
+	});
+
+	test('returns approval info for WaitingForPostApproval state', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const part = makeToolInvocationPart({
+			state: makePostApprovalState(),
+			toolSpecificData: makeTerminalToolData({ commandLine: { original: 'npm install' } }),
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		const result = getApproval(approvalModel, chatModel);
+		assert.deepStrictEqual({
+			label: result?.label,
+			language: result?.languageId,
+		}, {
+			label: 'npm install',
+			language: 'sh',
+		});
+	});
+
+	test('prefers presentationOverrides.commandLine and language', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: makeTerminalToolData({
+				commandLine: { original: 'python -c "print(1)"' },
+				language: 'sh',
+				presentationOverrides: { commandLine: 'print(1)', language: 'python' },
+			}),
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		const result = getApproval(approvalModel, chatModel);
+		assert.deepStrictEqual({
+			label: result?.label,
+			language: result?.languageId,
+		}, {
+			label: 'print(1)',
+			language: 'python',
+		});
+	});
+
+	test('uses forDisplay from commandLine when available', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: makeTerminalToolData({
+				commandLine: { original: 'echo raw', forDisplay: 'echo display' },
+			}),
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		assert.strictEqual(getApproval(approvalModel, chatModel)?.label, 'echo display');
+	});
+
+	test('uses userEdited from commandLine when forDisplay is not set', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: makeTerminalToolData({
+				commandLine: { original: 'orig', userEdited: 'user-edited' },
+			}),
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		assert.strictEqual(getApproval(approvalModel, chatModel)?.label, 'user-edited');
+	});
+
+	test('uses toolEdited from commandLine as fallback', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: makeTerminalToolData({
+				commandLine: { original: 'orig', toolEdited: 'tool-edited' },
+			}),
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		assert.strictEqual(getApproval(approvalModel, chatModel)?.label, 'tool-edited');
+	});
+
+	test('uses needsInput.detail when tool is not terminal', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const part = makeToolInvocationPart({ state: makeWaitingState() });
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test', detail: 'Custom detail message' }, undefined);
+
+		const result = getApproval(approvalModel, chatModel);
+		assert.deepStrictEqual({
+			label: result?.label,
+			language: result?.languageId,
+		}, {
+			label: 'Custom detail message',
+			language: undefined,
+		});
+	});
+
+	test('uses invocationMessage string when no terminal data and no detail', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(),
+			invocationMessage: 'Searching files...',
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		const result = getApproval(approvalModel, chatModel);
+		assert.deepStrictEqual({
+			label: result?.label,
+			language: result?.languageId,
+		}, {
+			label: 'Searching files...',
+			language: undefined,
+		});
+	});
+
+	test('uses invocationMessage MarkdownString when no terminal data and no detail', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(),
+			invocationMessage: new MarkdownString('**Running** tool'),
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		assert.strictEqual(getApproval(approvalModel, chatModel)?.label, 'Running tool');
+	});
+
+	test('confirm() delegates to tool state confirm with UserAction', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		let confirmedWith: ConfirmedReason | undefined;
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(reason => { confirmedWith = reason; }),
+			toolSpecificData: makeTerminalToolData(),
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		getApproval(approvalModel, chatModel)?.confirm();
+		assert.deepStrictEqual(confirmedWith, { type: ToolConfirmKind.UserAction });
+	});
+
+	test('reacts to requestNeedsInput becoming undefined', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: makeTerminalToolData(),
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+		assert.ok(getApproval(approvalModel, chatModel));
+
+		chatModel.requestNeedsInput.set(undefined, undefined);
+		assert.strictEqual(getApproval(approvalModel, chatModel), undefined);
+	});
+
+	test('reacts to tool state changing from waiting to executing', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const stateObs = observableValue<IChatToolInvocation.State>('toolState', makeWaitingState());
+		const part: IChatToolInvocation = {
+			...makeToolInvocationPart({ state: makeWaitingState(), toolSpecificData: makeTerminalToolData() }),
+			state: stateObs,
+		};
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+		assert.ok(getApproval(approvalModel, chatModel));
+
+		stateObs.set(makeExecutingState(), undefined);
+		assert.strictEqual(getApproval(approvalModel, chatModel), undefined);
+	});
+
+	test('tracks multiple models independently', () => {
+		const approvalModel = createModel();
+		const chatModel1 = addChatModel(URI.parse('test://session/1'));
+		const chatModel2 = addChatModel(URI.parse('test://session/2'));
+
+		const part1 = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: makeTerminalToolData({ commandLine: { original: 'cmd1' } }),
+		});
+		mockModelWithResponse(chatModel1, [part1]);
+		chatModel1.requestNeedsInput.set({ title: 'Session 1' }, undefined);
+
+		assert.strictEqual(getApproval(approvalModel, chatModel1)?.label, 'cmd1');
+		assert.strictEqual(getApproval(approvalModel, chatModel2), undefined);
+	});
+
+	test('clears approval when model is removed', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: makeTerminalToolData(),
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+		assert.ok(getApproval(approvalModel, chatModel));
+
+		// Remove model from chatModels
+		chatModelsObs.set([], undefined);
+		assert.strictEqual(getApproval(approvalModel, chatModel), undefined);
+	});
+
+	test('picks the first WaitingForConfirmation part when multiple parts exist', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const executingPart = makeToolInvocationPart({ state: makeExecutingState() });
+		const waitingPart = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: makeTerminalToolData({ commandLine: { original: 'second-cmd' } }),
+		});
+		mockModelWithResponse(chatModel, [executingPart, waitingPart]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		assert.strictEqual(getApproval(approvalModel, chatModel)?.label, 'second-cmd');
+	});
+
+	test('handles model added after approval model is created', () => {
+		const approvalModel = createModel();
+
+		// No models yet
+		const uri = URI.parse('test://session/late');
+		assert.strictEqual(approvalModel.getApproval(uri).get(), undefined);
+
+		// Add model later
+		const chatModel = addChatModel(uri);
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: makeTerminalToolData({ commandLine: { original: 'late-cmd' } }),
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		assert.strictEqual(getApproval(approvalModel, chatModel)?.label, 'late-cmd');
+	});
+
+	test('handles legacy terminal tool data', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		// Legacy format has `command` instead of `commandLine`
+		const legacyData = { kind: 'terminal' as const, command: 'legacy-cmd', language: 'bash' };
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: legacyData,
+		});
+		mockModelWithResponse(chatModel, [part]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		const result = getApproval(approvalModel, chatModel);
+		assert.deepStrictEqual({
+			label: result?.label,
+			language: result?.languageId,
+		}, {
+			label: 'legacy-cmd',
+			language: 'sh',
+		});
+	});
+
+	test('observable is reused for the same session resource', () => {
+		const approvalModel = createModel();
+		const uri = URI.parse('test://session/same');
+
+		const obs1 = approvalModel.getApproval(uri);
+		const obs2 = approvalModel.getApproval(uri);
+		assert.strictEqual(obs1, obs2);
+	});
+
+	test('skips non-toolInvocation parts', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		const markdownPart = { kind: 'markdownContent' as const, content: new MarkdownString('hello') };
+		const waitingPart = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: makeTerminalToolData({ commandLine: { original: 'the-cmd' } }),
+		});
+		mockModelWithResponse(chatModel, [markdownPart as unknown as IChatProgressResponseContent, waitingPart]);
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+
+		assert.strictEqual(getApproval(approvalModel, chatModel)?.label, 'the-cmd');
+	});
+
+	test('updating requestNeedsInput triggers re-evaluation', () => {
+		const approvalModel = createModel();
+		const chatModel = addChatModel();
+
+		// Initially no requestNeedsInput
+		const part = makeToolInvocationPart({
+			state: makeWaitingState(),
+			toolSpecificData: makeTerminalToolData(),
+		});
+		mockModelWithResponse(chatModel, [part]);
+		assert.strictEqual(getApproval(approvalModel, chatModel), undefined);
+
+		// Set requestNeedsInput
+		chatModel.requestNeedsInput.set({ title: 'Test' }, undefined);
+		assert.ok(getApproval(approvalModel, chatModel));
+
+		// Clear again
+		chatModel.requestNeedsInput.set(undefined, undefined);
+		assert.strictEqual(getApproval(approvalModel, chatModel), undefined);
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/browser/agentSessions/agentSessionViewModel.test.ts b/src/vs/workbench/contrib/chat/test/browser/agentSessions/agentSessionViewModel.test.ts
index 445feba0a2f77..1ffa63a0de010 100644
--- a/src/vs/workbench/contrib/chat/test/browser/agentSessions/agentSessionViewModel.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/agentSessions/agentSessionViewModel.test.ts
@@ -24,6 +24,20 @@ import { TestInstantiationService } from '../../../../../../platform/instantiati
 import { IStorageService, StorageScope, StorageTarget } from '../../../../../../platform/storage/common/storage.js';
 import { AgentSessionProviders, getAgentCanContinueIn, getAgentSessionProviderIcon, getAgentSessionProviderName } from '../../../browser/agentSessions/agentSessions.js';
 
+class StaticChatSessionItemController implements IChatSessionItemController {
+	readonly onDidChangeChatSessionItems = Event.None;
+
+	constructor(
+		private readonly sessionItems: readonly IChatSessionItem[],
+	) { }
+
+	get items(): readonly IChatSessionItem[] {
+		return this.sessionItems;
+	}
+
+	async refresh(): Promise<void> { }
+}
+
 
 suite('AgentSessions', () => {
 
@@ -63,21 +77,15 @@ suite('AgentSessions', () => {
 
 		test('should resolve sessions from controllers', async () => {
 			return runWithFakedTimers({}, async () => {
-				const chatSessionType = 'test-type';
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [
-							makeSimpleSessionItem('session-1', {
-								label: 'Test Session 1'
-							}),
-							makeSimpleSessionItem('session-2', {
-								label: 'Test Session 2'
-							})
-						];
-					}
-				};
+				const chatSessionType = chatSessionTestType;
+				const controller = new StaticChatSessionItemController([
+					makeSimpleSessionItem('session-1', {
+						label: 'Test Session 1'
+					}),
+					makeSimpleSessionItem('session-2', {
+						label: 'Test Session 2'
+					})
+				]);
 
 				mockChatSessionsService.registerChatSessionItemController(chatSessionType, controller);
 				viewModel = createViewModel();
@@ -85,30 +93,18 @@ suite('AgentSessions', () => {
 				await viewModel.resolve(undefined);
 
 				assert.strictEqual(viewModel.sessions.length, 2);
-				assert.strictEqual(viewModel.sessions[0].resource.toString(), 'test://session-1');
+				assert.strictEqual(viewModel.sessions[0].resource.toString(), `${chatSessionTestType}://session-1`);
 				assert.strictEqual(viewModel.sessions[0].label, 'Test Session 1');
-				assert.strictEqual(viewModel.sessions[1].resource.toString(), 'test://session-2');
+				assert.strictEqual(viewModel.sessions[1].resource.toString(), `${chatSessionTestType}://session-2`);
 				assert.strictEqual(viewModel.sessions[1].label, 'Test Session 2');
 			});
 		});
 
 		test('should resolve sessions from multiple controllers', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller1: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller1 = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				const controller2: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-2')];
-					}
-				};
+				const controller2 = new StaticChatSessionItemController([makeSimpleSessionItem('session-2')]);
 
 				mockChatSessionsService.registerChatSessionItemController('type-1', controller1);
 				mockChatSessionsService.registerChatSessionItemController('type-2', controller2);
@@ -118,20 +114,16 @@ suite('AgentSessions', () => {
 				await viewModel.resolve(undefined);
 
 				assert.strictEqual(viewModel.sessions.length, 2);
-				assert.strictEqual(viewModel.sessions[0].resource.toString(), 'test://session-1');
-				assert.strictEqual(viewModel.sessions[1].resource.toString(), 'test://session-2');
+				assert.strictEqual(viewModel.sessions[0].resource.toString(), `${chatSessionTestType}://session-1`);
+				assert.strictEqual(viewModel.sessions[1].resource.toString(), `${chatSessionTestType}://session-2`);
 			});
 		});
 
 		test('should fire onWillResolve and onDidResolve events', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() { return []; }
-				};
+				const controller = new StaticChatSessionItemController([]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = createViewModel();
 
 				let willResolveFired = false;
@@ -156,15 +148,9 @@ suite('AgentSessions', () => {
 
 		test('should fire onDidChangeSessions event after resolving', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = createViewModel();
 
 				let sessionsChangedFired = false;
@@ -183,24 +169,18 @@ suite('AgentSessions', () => {
 				const created = Date.now();
 				const lastRequestEnded = created + 1000;
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://session-1'),
-							label: 'Test Session',
-							description: new MarkdownString('**Bold** description'),
-							status: ChatSessionStatus.Completed,
-							tooltip: 'Session tooltip',
-							iconPath: ThemeIcon.fromId('check'),
-							timing: { created, lastRequestStarted: created, lastRequestEnded },
-							changes: { files: 1, insertions: 10, deletions: 5 }
-						}];
-					}
-				};
-
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://session-1'),
+					label: 'Test Session',
+					description: new MarkdownString('**Bold** description'),
+					status: ChatSessionStatus.Completed,
+					tooltip: 'Session tooltip',
+					iconPath: ThemeIcon.fromId('check'),
+					timing: { created, lastRequestStarted: created, lastRequestEnded },
+					changes: { files: 1, insertions: 10, deletions: 5 }
+				}]);
+
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = createViewModel();
 
 				await viewModel.resolve(undefined);
@@ -222,21 +202,9 @@ suite('AgentSessions', () => {
 
 		test('should handle resolve with specific provider', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller1: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller1 = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				const controller2: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-2')];
-					}
-				};
+				const controller2 = new StaticChatSessionItemController([makeSimpleSessionItem('session-2')]);
 
 				disposables.add(mockChatSessionsService.registerChatSessionItemController('type-1', controller1));
 				disposables.add(mockChatSessionsService.registerChatSessionItemController('type-2', controller2));
@@ -256,21 +224,9 @@ suite('AgentSessions', () => {
 
 		test('should handle resolve with multiple specific controllers', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller1: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller1 = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				const controller2: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-2')];
-					}
-				};
+				const controller2 = new StaticChatSessionItemController([makeSimpleSessionItem('session-2')]);
 
 				mockChatSessionsService.registerChatSessionItemController('type-1', controller1);
 				mockChatSessionsService.registerChatSessionItemController('type-2', controller2);
@@ -285,14 +241,8 @@ suite('AgentSessions', () => {
 
 		test('should respond to onDidChangeItemsProviders event', async () => {
 			return runWithFakedTimers({}, async () => {
-				const chatSessionType = 'test-type';
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const chatSessionType = chatSessionTestType;
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
 				mockChatSessionsService.registerChatSessionItemController(chatSessionType, controller);
 				viewModel = createViewModel();
@@ -311,15 +261,9 @@ suite('AgentSessions', () => {
 
 		test('should respond to onDidChangeAvailability event', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = createViewModel();
 
 				const sessionsChangedPromise = Event.toPromise(viewModel.onDidChangeSessions);
@@ -336,21 +280,16 @@ suite('AgentSessions', () => {
 
 		test('should respond to onDidChangeSessionItems event', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const testSession = makeSimpleSessionItem('session-1');
+				const controller = new StaticChatSessionItemController([testSession]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = createViewModel();
 
 				const sessionsChangedPromise = Event.toPromise(viewModel.onDidChangeSessions);
 
 				// Trigger event - this should automatically call resolve
-				mockChatSessionsService.fireDidChangeSessionItems('test-type');
+				mockChatSessionsService.fireDidChangeSessionItems({ addedOrUpdated: [testSession] });
 
 				// Wait for the sessions to be resolved
 				await sessionsChangedPromise;
@@ -361,33 +300,23 @@ suite('AgentSessions', () => {
 
 		test('should maintain provider reference in session view model', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = createViewModel();
 
 				await viewModel.resolve(undefined);
 
 				assert.strictEqual(viewModel.sessions.length, 1);
-				assert.strictEqual(viewModel.sessions[0].providerType, 'test-type');
+				assert.strictEqual(viewModel.sessions[0].providerType, chatSessionTestType);
 			});
 		});
 
 		test('should handle empty provider results', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() { return []; }
-				};
+				const controller = new StaticChatSessionItemController([]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = createViewModel();
 
 				await viewModel.resolve(undefined);
@@ -398,37 +327,28 @@ suite('AgentSessions', () => {
 
 		test('should handle sessions with different statuses', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [
-							{
-								id: 'session-failed',
-								resource: URI.parse('test://session-failed'),
-								label: 'Failed Session',
-								status: ChatSessionStatus.Failed,
-								timing: makeNewSessionTiming()
-							},
-							{
-								id: 'session-completed',
-								resource: URI.parse('test://session-completed'),
-								label: 'Completed Session',
-								status: ChatSessionStatus.Completed,
-								timing: makeNewSessionTiming()
-							},
-							{
-								id: 'session-inprogress',
-								resource: URI.parse('test://session-inprogress'),
-								label: 'In Progress Session',
-								status: ChatSessionStatus.InProgress,
-								timing: makeNewSessionTiming()
-							}
-						];
+				const controller = new StaticChatSessionItemController([
+					{
+						resource: URI.parse('test://session-failed'),
+						label: 'Failed Session',
+						status: ChatSessionStatus.Failed,
+						timing: makeNewSessionTiming()
+					},
+					{
+						resource: URI.parse('test://session-completed'),
+						label: 'Completed Session',
+						status: ChatSessionStatus.Completed,
+						timing: makeNewSessionTiming()
+					},
+					{
+						resource: URI.parse('test://session-inprogress'),
+						label: 'In Progress Session',
+						status: ChatSessionStatus.InProgress,
+						timing: makeNewSessionTiming()
 					}
-				};
+				]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = createViewModel();
 
 				await viewModel.resolve(undefined);
@@ -456,7 +376,7 @@ suite('AgentSessions', () => {
 					get items() { return _items; }
 				};
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = createViewModel();
 
 				await viewModel.resolve(undefined);
@@ -470,18 +390,11 @@ suite('AgentSessions', () => {
 
 		test('should handle local agent session type specially', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							id: 'local-session',
-							resource: LocalChatSessionUri.forSession('local-session'),
-							label: 'Local Session',
-							timing: makeNewSessionTiming()
-						}];
-					}
-				};
+				const controller = new StaticChatSessionItemController([{
+					resource: LocalChatSessionUri.forSession('local-session'),
+					label: 'Local Session',
+					timing: makeNewSessionTiming()
+				}]);
 
 				mockChatSessionsService.registerChatSessionItemController(localChatSessionType, controller);
 				viewModel = createViewModel();
@@ -497,19 +410,13 @@ suite('AgentSessions', () => {
 			return runWithFakedTimers({}, async () => {
 				const resource = URI.parse('custom://my-session/path');
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: resource,
-							label: 'Test Session',
-							timing: makeNewSessionTiming()
-						}];
-					}
-				};
+				const controller = new StaticChatSessionItemController([{
+					resource: resource,
+					label: 'Test Session',
+					timing: makeNewSessionTiming()
+				}]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = createViewModel();
 
 				await viewModel.resolve(undefined);
@@ -531,7 +438,7 @@ suite('AgentSessions', () => {
 					}
 				};
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				// Registering calls a refresh initially
 				assert.strictEqual(controllerCallCount, 1);
 
@@ -763,7 +670,7 @@ suite('AgentSessions', () => {
 
 		function createSession(overrides: Partial<IAgentSession> = {}): IAgentSession {
 			return {
-				providerType: 'test-type',
+				providerType: chatSessionTestType,
 				providerLabel: 'Test Provider',
 				icon: Codicon.chatSparkle,
 				resource: URI.parse('test://session'),
@@ -1046,11 +953,7 @@ suite('AgentSessions', () => {
 		});
 
 		test('should register provider filter actions', () => {
-			const controller: IChatSessionItemController = {
-				onDidChangeChatSessionItems: Event.None,
-				refresh: async () => { },
-				get items() { return []; }
-			};
+			const controller = new StaticChatSessionItemController([]);
 
 			mockChatSessionsService.registerChatSessionItemController('custom-type-1', controller);
 
@@ -1071,11 +974,7 @@ suite('AgentSessions', () => {
 			));
 
 			const chatSessionType = 'new-type';
-			const controller: IChatSessionItemController = {
-				onDidChangeChatSessionItems: Event.None,
-				refresh: async () => { },
-				get items() { return []; }
-			};
+			const controller = new StaticChatSessionItemController([]);
 
 			// Register provider after filter creation
 			mockChatSessionsService.registerChatSessionItemController(chatSessionType, controller);
@@ -1314,15 +1213,9 @@ suite('AgentSessions', () => {
 
 		test('should archive and unarchive sessions', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1342,15 +1235,9 @@ suite('AgentSessions', () => {
 
 		test('should fire onDidChangeSessions when archiving', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1368,15 +1255,9 @@ suite('AgentSessions', () => {
 
 		test('should not fire onDidChangeSessions when archiving with same value', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1397,20 +1278,14 @@ suite('AgentSessions', () => {
 
 		test('should preserve archived state from provider', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://session-1'),
-							label: 'Test Session',
-							archived: true,
-							timing: makeNewSessionTiming()
-						}];
-					}
-				};
-
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://session-1'),
+					label: 'Test Session',
+					archived: true,
+					timing: makeNewSessionTiming()
+				}]);
+
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1422,20 +1297,14 @@ suite('AgentSessions', () => {
 
 		test('should override provider archived state with user preference', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://session-1'),
-							label: 'Test Session',
-							archived: true,
-							timing: makeNewSessionTiming()
-						}];
-					}
-				};
-
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://session-1'),
+					label: 'Test Session',
+					archived: true,
+					timing: makeNewSessionTiming()
+				}]);
+
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1484,19 +1353,13 @@ suite('AgentSessions', () => {
 					lastRequestEnded: Date.UTC(2026, 1 /* February */, 2),
 				};
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://session-1'),
-							label: 'Session 1',
-							timing: futureSessionTiming,
-						}];
-					}
-				};
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://session-1'),
+					label: 'Session 1',
+					timing: futureSessionTiming,
+				}]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1515,15 +1378,9 @@ suite('AgentSessions', () => {
 
 		test('should fire onDidChangeSessions when marking as read', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1543,15 +1400,9 @@ suite('AgentSessions', () => {
 
 		test('should not fire onDidChangeSessions when marking as read with same value', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1572,15 +1423,9 @@ suite('AgentSessions', () => {
 
 		test('should preserve read state after re-resolve', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1605,19 +1450,13 @@ suite('AgentSessions', () => {
 					lastRequestEnded: Date.UTC(2025, 10 /* November */, 2),
 				};
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://old-session'),
-							label: 'Old Session',
-							timing: oldSessionTiming,
-						}];
-					}
-				};
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://old-session'),
+					label: 'Old Session',
+					timing: oldSessionTiming,
+				}]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1636,19 +1475,13 @@ suite('AgentSessions', () => {
 					lastRequestEnded: Date.UTC(2026, 1 /* February */, 2),
 				};
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://new-session'),
-							label: 'New Session',
-							timing: newSessionTiming,
-						}];
-					}
-				};
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://new-session'),
+					label: 'New Session',
+					timing: newSessionTiming,
+				}]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1668,19 +1501,13 @@ suite('AgentSessions', () => {
 					lastRequestEnded: Date.UTC(2026, 1 /* February */, 1),
 				};
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://session-with-endtime'),
-							label: 'Session With EndTime',
-							timing: sessionTiming,
-						}];
-					}
-				};
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://session-with-endtime'),
+					label: 'Session With EndTime',
+					timing: sessionTiming,
+				}]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1700,19 +1527,13 @@ suite('AgentSessions', () => {
 					lastRequestEnded: undefined,
 				};
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://session-no-endtime'),
-							label: 'Session Without EndTime',
-							timing: sessionTiming,
-						}];
-					}
-				};
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://session-no-endtime'),
+					label: 'Session Without EndTime',
+					timing: sessionTiming,
+				}]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1731,19 +1552,13 @@ suite('AgentSessions', () => {
 					lastRequestEnded: Date.UTC(2026, 1 /* February */, 2),
 				};
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://new-session'),
-							label: 'New Session',
-							timing: newSessionTiming,
-						}];
-					}
-				};
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://new-session'),
+					label: 'New Session',
+					timing: newSessionTiming,
+				}]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1770,19 +1585,13 @@ suite('AgentSessions', () => {
 					lastRequestEnded: Date.UTC(2026, 1 /* February */, 2),
 				};
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://new-session'),
-							label: 'New Session',
-							timing: newSessionTiming,
-						}];
-					}
-				};
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://new-session'),
+					label: 'New Session',
+					timing: newSessionTiming,
+				}]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1815,19 +1624,13 @@ suite('AgentSessions', () => {
 					lastRequestEnded: Date.UTC(2026, 1 /* February */, 2),
 				};
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://new-session'),
-							label: 'New Session',
-							timing: newSessionTiming,
-						}];
-					}
-				};
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://new-session'),
+					label: 'New Session',
+					timing: newSessionTiming,
+				}]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1857,18 +1660,12 @@ suite('AgentSessions', () => {
 					lastRequestEnded: Date.UTC(2025, 10 /* November */, 2),
 				};
 
-				const chatSessionType = 'test-type';
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://old-session'),
-							label: 'Old Session',
-							timing: oldSessionTiming,
-						}];
-					}
-				};
+				const chatSessionType = chatSessionTestType;
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://old-session'),
+					label: 'Old Session',
+					timing: oldSessionTiming,
+				}]);
 
 				mockChatSessionsService.registerChatSessionItemController(chatSessionType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
@@ -1931,7 +1728,7 @@ suite('AgentSessions', () => {
 					get items() { return _items; }
 				};
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -1961,7 +1758,7 @@ suite('AgentSessions', () => {
 					get items() { return _items; }
 				};
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				await viewModel.resolve(undefined);
@@ -2031,13 +1828,7 @@ suite('AgentSessions', () => {
 				instantiationService.stub(IChatSessionsService, mockChatSessionsService);
 				instantiationService.stub(ILifecycleService, disposables.add(new TestLifecycleService()));
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
 				mockChatSessionsService.registerChatSessionItemController(AgentSessionProviders.Local, controller);
 				const viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
@@ -2058,13 +1849,7 @@ suite('AgentSessions', () => {
 				instantiationService.stub(IChatSessionsService, mockChatSessionsService);
 				instantiationService.stub(ILifecycleService, disposables.add(new TestLifecycleService()));
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
 				mockChatSessionsService.registerChatSessionItemController(AgentSessionProviders.Background, controller);
 				const viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
@@ -2085,13 +1870,7 @@ suite('AgentSessions', () => {
 				instantiationService.stub(IChatSessionsService, mockChatSessionsService);
 				instantiationService.stub(ILifecycleService, disposables.add(new TestLifecycleService()));
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
 				mockChatSessionsService.registerChatSessionItemController(AgentSessionProviders.Cloud, controller);
 				const viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
@@ -2113,18 +1892,12 @@ suite('AgentSessions', () => {
 				instantiationService.stub(ILifecycleService, disposables.add(new TestLifecycleService()));
 
 				const customIcon = ThemeIcon.fromId('beaker');
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [{
-							resource: URI.parse('test://session-1'),
-							label: 'Test Session',
-							iconPath: customIcon,
-							timing: makeNewSessionTiming()
-						}];
-					}
-				};
+				const controller = new StaticChatSessionItemController([{
+					resource: URI.parse('test://session-1'),
+					label: 'Test Session',
+					iconPath: customIcon,
+					timing: makeNewSessionTiming()
+				}]);
 
 				mockChatSessionsService.registerChatSessionItemController('custom-type', controller);
 				const viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
@@ -2143,13 +1916,7 @@ suite('AgentSessions', () => {
 				instantiationService.stub(IChatSessionsService, mockChatSessionsService);
 				instantiationService.stub(ILifecycleService, disposables.add(new TestLifecycleService()));
 
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
 				mockChatSessionsService.registerChatSessionItemController('custom-type', controller);
 				const viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
@@ -2199,15 +1966,9 @@ suite('AgentSessions', () => {
 
 		test('should not resolve if lifecycle will shutdown', async () => {
 			return runWithFakedTimers({}, async () => {
-				const controller: IChatSessionItemController = {
-					onDidChangeChatSessionItems: Event.None,
-					refresh: async () => { },
-					get items() {
-						return [makeSimpleSessionItem('session-1')];
-					}
-				};
+				const controller = new StaticChatSessionItemController([makeSimpleSessionItem('session-1')]);
 
-				mockChatSessionsService.registerChatSessionItemController('test-type', controller);
+				mockChatSessionsService.registerChatSessionItemController(chatSessionTestType, controller);
 				viewModel = disposables.add(instantiationService.createInstance(AgentSessionsModel));
 
 				// Set willShutdown to true
@@ -2258,9 +2019,11 @@ suite('AgentSessions', () => {
 
 }); // End of Agent Sessions suite
 
+const chatSessionTestType = 'test-type';
+
 function makeSimpleSessionItem(id: string, overrides?: Partial<IChatSessionItem>): IChatSessionItem {
 	return {
-		resource: URI.parse(`test://${id}`),
+		resource: URI.parse(`${chatSessionTestType}://${id}`),
 		label: `Session ${id}`,
 		timing: makeNewSessionTiming(),
 		...overrides
diff --git a/src/vs/workbench/contrib/chat/test/browser/agentSessions/agentSessionsDataSource.test.ts b/src/vs/workbench/contrib/chat/test/browser/agentSessions/agentSessionsDataSource.test.ts
index 863ef9534237f..9a01e7d1df9dd 100644
--- a/src/vs/workbench/contrib/chat/test/browser/agentSessions/agentSessionsDataSource.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/agentSessions/agentSessionsDataSource.test.ts
@@ -6,7 +6,7 @@
 import assert from 'assert';
 import { URI } from '../../../../../../base/common/uri.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
-import { AgentSessionsDataSource, AgentSessionListItem, IAgentSessionsFilter, sessionDateFromNow } from '../../../browser/agentSessions/agentSessionsViewer.js';
+import { AgentSessionsDataSource, AgentSessionListItem, IAgentSessionsFilter, sessionDateFromNow, getRepositoryName } from '../../../browser/agentSessions/agentSessionsViewer.js';
 import { AgentSessionSection, IAgentSession, IAgentSessionSection, IAgentSessionsModel, isAgentSessionSection } from '../../../browser/agentSessions/agentSessionsModel.js';
 import { ChatSessionStatus } from '../../../common/chatSessionsService.js';
 import { ITreeSorter } from '../../../../../../base/browser/ui/tree/tree.js';
@@ -95,7 +95,7 @@ suite('sessionDateFromNow', () => {
 
 suite('AgentSessionsDataSource', () => {
 
-	ensureNoDisposablesAreLeakedInTestSuite();
+	const disposables = ensureNoDisposablesAreLeakedInTestSuite();
 
 	const ONE_DAY = 24 * 60 * 60 * 1000;
 	const WEEK_THRESHOLD = 7 * ONE_DAY; // 7 days
@@ -108,6 +108,8 @@ suite('AgentSessionsDataSource', () => {
 		hasChanges: boolean;
 		startTime: number;
 		endTime: number;
+		metadata: { [key: string]: unknown };
+		badge: string;
 	}> = {}): IAgentSession {
 		const now = Date.now();
 		return {
@@ -123,6 +125,8 @@ suite('AgentSessionsDataSource', () => {
 				lastRequestStarted: undefined,
 			},
 			changes: overrides.hasChanges ? { files: 1, insertions: 10, deletions: 5 } : undefined,
+			metadata: overrides.metadata,
+			badge: overrides.badge,
 			isArchived: () => overrides.isArchived ?? false,
 			setArchived: () => { },
 			isRead: () => overrides.isRead ?? true,
@@ -152,7 +156,9 @@ suite('AgentSessionsDataSource', () => {
 			onDidChange: Event.None,
 			groupResults: () => options.groupBy,
 			exclude: options.exclude ?? (() => false),
-			getExcludes: () => ({ providers: [], states: [], archived: false, read: options.excludeRead ?? false })
+			getExcludes: () => ({ providers: [], states: [], archived: false, read: options.excludeRead ?? false }),
+			isDefault: () => true,
+			reset: () => { },
 		};
 	}
 
@@ -182,7 +188,7 @@ suite('AgentSessionsDataSource', () => {
 
 			const filter = createMockFilter({ groupBy: undefined });
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -202,7 +208,7 @@ suite('AgentSessionsDataSource', () => {
 
 			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Date });
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -223,7 +229,7 @@ suite('AgentSessionsDataSource', () => {
 
 			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Date });
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -244,7 +250,7 @@ suite('AgentSessionsDataSource', () => {
 
 			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Date });
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -263,7 +269,7 @@ suite('AgentSessionsDataSource', () => {
 
 			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Date });
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -281,7 +287,7 @@ suite('AgentSessionsDataSource', () => {
 
 			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Date });
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -299,7 +305,7 @@ suite('AgentSessionsDataSource', () => {
 
 			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Date });
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -319,7 +325,7 @@ suite('AgentSessionsDataSource', () => {
 
 			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Date });
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -353,7 +359,7 @@ suite('AgentSessionsDataSource', () => {
 
 			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Date });
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -382,7 +388,7 @@ suite('AgentSessionsDataSource', () => {
 		test('empty sessions returns empty result', () => {
 			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Date });
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel([]);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -399,7 +405,7 @@ suite('AgentSessionsDataSource', () => {
 
 			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Date });
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -422,7 +428,7 @@ suite('AgentSessionsDataSource', () => {
 
 			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Date });
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -456,7 +462,7 @@ suite('AgentSessionsDataSource', () => {
 				excludeRead: true  // Filtering to show only unread sessions
 			});
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -481,7 +487,7 @@ suite('AgentSessionsDataSource', () => {
 				excludeRead: false  // Not filtering to unread only
 			});
 			const sorter = createMockSorter();
-			const dataSource = new AgentSessionsDataSource(filter, sorter);
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, sorter));
 
 			const mockModel = createMockModel(sessions);
 			const result = Array.from(dataSource.getChildren(mockModel));
@@ -494,4 +500,377 @@ suite('AgentSessionsDataSource', () => {
 			assert.strictEqual(sections[0].sessions.length, 2);
 		});
 	});
+
+	suite('groupSessionsByRepository', () => {
+
+		function sortedGroups(result: IAgentSessionSection[]) {
+			return result
+				.map(s => ({ label: s.label, count: s.sessions.length }))
+				.sort((a, b) => a.label.localeCompare(b.label));
+		}
+
+		test('groups sessions by metadata.owner + metadata.name (cloud sessions)', () => {
+			const now = Date.now();
+			const sessions = [
+				createMockSession({ id: '1', startTime: now, metadata: { owner: 'microsoft', name: 'vscode' } }),
+				createMockSession({ id: '2', startTime: now - 1, metadata: { owner: 'microsoft', name: 'vscode' } }),
+				createMockSession({ id: '3', startTime: now - 2, metadata: { owner: 'microsoft', name: 'typescript' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'typescript', count: 1 },
+				{ label: 'vscode', count: 2 },
+			]);
+		});
+
+		test('groups sessions by metadata.repositoryNwo', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { repositoryNwo: 'microsoft/vscode' } }),
+				createMockSession({ id: '2', metadata: { repositoryNwo: 'microsoft/vscode' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'vscode', count: 2 },
+			]);
+		});
+
+		test('groups sessions by metadata.repository (nwo format)', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { repository: 'microsoft/vscode' } }),
+				createMockSession({ id: '2', metadata: { repository: 'microsoft/vscode' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'vscode', count: 2 },
+			]);
+		});
+
+		test('groups sessions by metadata.repository (URL format)', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { repository: 'https://github.com/microsoft/vscode' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'vscode', count: 1 },
+			]);
+		});
+
+		test('strips .git suffix from repository URLs', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { repository: 'https://github.com/microsoft/vscode.git' } }),
+				createMockSession({ id: '2', metadata: { repositoryUrl: 'https://github.com/microsoft/vscode.git' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'vscode', count: 2 },
+			]);
+		});
+
+		test('handles git@ SSH URLs', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { repository: 'git@github.com:microsoft/vscode.git' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'vscode', count: 1 },
+			]);
+		});
+
+		test('groups sessions by metadata.repositoryUrl', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { repositoryUrl: 'https://github.com/microsoft/vscode' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'vscode', count: 1 },
+			]);
+		});
+
+		test('groups sessions by metadata.repositoryPath (basename)', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { repositoryPath: '/Users/user/Projects/vscode' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'vscode', count: 1 },
+			]);
+		});
+
+		test('groups sessions by metadata.worktreePath', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { worktreePath: '/Users/user/Projects/vscode.worktrees/my-branch' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'vscode', count: 1 },
+			]);
+		});
+
+		test('groups sessions by metadata.workingDirectoryPath', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { workingDirectoryPath: '/Users/user/Projects/vscode' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'vscode', count: 1 },
+			]);
+		});
+
+		test('resolves worktree paths to parent repo name', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { workingDirectoryPath: '/Users/user/Projects/vscode.worktrees/copilot-branch' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'vscode', count: 1 },
+			]);
+		});
+
+		test('groups sessions by badge with $(repo) prefix', () => {
+			const sessions = [
+				createMockSession({ id: '1', badge: '$(repo) vscode' }),
+				createMockSession({ id: '2', badge: '$(repo) vscode' }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'vscode', count: 2 },
+			]);
+		});
+
+		test('groups sessions by badge with $(folder) prefix', () => {
+			const sessions = [
+				createMockSession({ id: '1', badge: '$(folder) my-project' }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'my-project', count: 1 },
+			]);
+		});
+
+		test('cloud and local sessions for same repo merge into one group', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { owner: 'microsoft', name: 'vscode' } }),
+				createMockSession({ id: '2', metadata: { repositoryPath: '/Users/user/Projects/vscode' } }),
+				createMockSession({ id: '3', badge: '$(repo) vscode' }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'vscode', count: 3 },
+			]);
+		});
+
+		test('sessions without any repo info go to Other', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { isolationMode: 'workspace' } }),
+				createMockSession({ id: '2' }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(sortedGroups(result), [
+				{ label: 'Other', count: 2 },
+			]);
+		});
+
+		test('repo named "other" does not collide with the Other fallback group', () => {
+			const now = Date.now();
+			const sessions = [
+				createMockSession({ id: '1', startTime: now, metadata: { repositoryPath: '/path/other' } }),
+				createMockSession({ id: '2', startTime: now - 1 }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.strictEqual(result.length, 2, 'should have 2 separate groups');
+			const labels = result.map(s => s.label);
+			assert.ok(labels.includes('other'), 'should have a group for repo named "other"');
+			assert.ok(labels.includes('Other'), 'should have the fallback "Other" group');
+			assert.strictEqual(result.find(s => s.label === 'other')!.sessions.length, 1);
+			assert.strictEqual(result.find(s => s.label === 'Other')!.sessions.length, 1);
+		});
+
+		test('archived sessions go to Archived section', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { repositoryPath: '/path/vscode' } }),
+				createMockSession({ id: '2', isArchived: true, metadata: { repositoryPath: '/path/vscode' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(result.map(s => ({ label: s.label, section: s.section, count: s.sessions.length })), [
+				{ label: 'vscode', section: AgentSessionSection.Repository, count: 1 },
+				{ label: 'Archived', section: AgentSessionSection.Archived, count: 1 },
+			]);
+		});
+
+		test('metadata extraction priority: owner+name > repositoryNwo > repository > repositoryUrl > repositoryPath > workingDirectoryPath > badge', () => {
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+
+			// owner+name takes priority over repositoryNwo
+			const ds1 = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			assert.strictEqual(getSectionsFromResult(ds1.getChildren(createMockModel([
+				createMockSession({ id: '1', metadata: { owner: 'org', name: 'fromOwner', repositoryNwo: 'org/fromNwo' } }),
+			])))[0].label, 'fromOwner');
+
+			// repositoryNwo takes priority over repository
+			const ds2 = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			assert.strictEqual(getSectionsFromResult(ds2.getChildren(createMockModel([
+				createMockSession({ id: '2', metadata: { repositoryNwo: 'org/fromNwo', repository: 'org/fromRepo' } }),
+			])))[0].label, 'fromNwo');
+
+			// badge is used when no metadata fields match
+			const ds3 = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			assert.strictEqual(getSectionsFromResult(ds3.getChildren(createMockModel([
+				createMockSession({ id: '3', metadata: { isolationMode: 'workspace' }, badge: '$(repo) fromBadge' }),
+			])))[0].label, 'fromBadge');
+		});
+
+		test('empty string metadata values are treated as missing', () => {
+			const sessions = [
+				createMockSession({ id: '1', metadata: { repositoryNwo: '', repositoryPath: '/path/vscode' } }),
+			];
+
+			const filter = createMockFilter({ groupBy: AgentSessionsGrouping.Repository });
+			const dataSource = disposables.add(new AgentSessionsDataSource(filter, createMockSorter()));
+			const result = getSectionsFromResult(dataSource.getChildren(createMockModel(sessions)));
+
+			assert.deepStrictEqual(result.map(s => s.label), ['vscode']);
+		});
+	});
+
+	suite('getRepositoryName', () => {
+
+		test('returns metadata.name when owner and name are present', () => {
+			const session = createMockSession({ id: '1', metadata: { owner: 'microsoft', name: 'vscode' } });
+			assert.strictEqual(getRepositoryName(session), 'vscode');
+		});
+
+		test('returns repo from repositoryNwo', () => {
+			const session = createMockSession({ id: '1', metadata: { repositoryNwo: 'microsoft/vscode' } });
+			assert.strictEqual(getRepositoryName(session), 'vscode');
+		});
+
+		test('returns repo from repository URL', () => {
+			const session = createMockSession({ id: '1', metadata: { repository: 'https://github.com/microsoft/vscode' } });
+			assert.strictEqual(getRepositoryName(session), 'vscode');
+		});
+
+		test('returns repo from repositoryPath basename', () => {
+			const session = createMockSession({ id: '1', metadata: { repositoryPath: '/Users/user/Projects/vscode' } });
+			assert.strictEqual(getRepositoryName(session), 'vscode');
+		});
+
+		test('returns parent repo name from worktree path', () => {
+			const session = createMockSession({ id: '1', metadata: { worktreePath: '/Users/user/Projects/vscode.worktrees/my-branch' } });
+			assert.strictEqual(getRepositoryName(session), 'vscode');
+		});
+
+		test('returns name from badge with $(repo) prefix', () => {
+			const session = createMockSession({ id: '1', badge: '$(repo) vscode' });
+			assert.strictEqual(getRepositoryName(session), 'vscode');
+		});
+
+		test('returns name from badge with $(folder) prefix', () => {
+			const session = createMockSession({ id: '1', badge: '$(folder) my-project' });
+			assert.strictEqual(getRepositoryName(session), 'my-project');
+		});
+
+		test('metadata repo name takes priority over badge name', () => {
+			const session = createMockSession({ id: '1', metadata: { owner: 'microsoft', name: 'vscode' }, badge: '$(folder) copilot-worktree-branch' });
+			assert.strictEqual(getRepositoryName(session), 'vscode');
+		});
+
+		test('returns undefined when no repo info is available', () => {
+			const session = createMockSession({ id: '1' });
+			assert.strictEqual(getRepositoryName(session), undefined);
+		});
+
+		test('badge name can differ from metadata repo name (worktree scenario)', () => {
+			// This is the key scenario: a session in a worktree where the badge shows
+			// the worktree folder name but the repo name (from metadata) is different.
+			// The renderer uses this to decide whether to hide the badge when grouped by repo.
+			const session = createMockSession({
+				id: '1',
+				metadata: { repositoryPath: '/Users/user/Projects/vscode' },
+				badge: '$(folder) copilot-worktree-2026-03-13T00-27-32',
+			});
+			assert.strictEqual(getRepositoryName(session), 'vscode');
+			// Badge text shows a different name than the repo — renderer should NOT hide it
+		});
+
+		test('archived session still returns repo name from metadata', () => {
+			// Archived sessions are grouped under "Archived", not under a repo section,
+			// so the renderer must keep their badge visible even when the badge name
+			// matches the repo name. getRepositoryName still resolves normally.
+			const session = createMockSession({
+				id: '1',
+				isArchived: true,
+				metadata: { repositoryPath: '/Users/user/Projects/vscode' },
+				badge: '$(repo) vscode',
+			});
+			assert.strictEqual(getRepositoryName(session), 'vscode');
+		});
+	});
 });
diff --git a/src/vs/workbench/contrib/chat/test/browser/agentSessions/localAgentSessionsController.test.ts b/src/vs/workbench/contrib/chat/test/browser/agentSessions/localAgentSessionsController.test.ts
index 8113041814474..e8fc538290842 100644
--- a/src/vs/workbench/contrib/chat/test/browser/agentSessions/localAgentSessionsController.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/agentSessions/localAgentSessionsController.test.ts
@@ -8,19 +8,19 @@ import { CancellationToken } from '../../../../../../base/common/cancellation.js
 import { Codicon } from '../../../../../../base/common/codicons.js';
 import { Emitter, Event } from '../../../../../../base/common/event.js';
 import { DisposableStore } from '../../../../../../base/common/lifecycle.js';
-import { ISettableObservable, observableValue } from '../../../../../../base/common/observable.js';
+import { observableValue } from '../../../../../../base/common/observable.js';
 import { URI } from '../../../../../../base/common/uri.js';
 import { runWithFakedTimers } from '../../../../../../base/test/common/timeTravelScheduler.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
 import { TestInstantiationService } from '../../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
 import { workbenchInstantiationService } from '../../../../../test/browser/workbenchTestServices.js';
 import { LocalAgentsSessionsController } from '../../../browser/agentSessions/localAgentSessionsController.js';
+import { IChatService, ResponseModelState } from '../../../common/chatService/chatService.js';
+import { ChatSessionStatus, IChatSessionItem, IChatSessionsService, localChatSessionType } from '../../../common/chatSessionsService.js';
 import { ModifiedFileEntryState } from '../../../common/editing/chatEditingService.js';
 import { IChatModel, IChatRequestModel, IChatResponseModel } from '../../../common/model/chatModel.js';
-import { ChatRequestQueueKind, IChatDetail, IChatService, IChatSessionStartOptions, ResponseModelState } from '../../../common/chatService/chatService.js';
-import { ChatSessionStatus, IChatSessionItem, IChatSessionsService, localChatSessionType } from '../../../common/chatSessionsService.js';
 import { LocalChatSessionUri } from '../../../common/model/chatUri.js';
-import { ChatAgentLocation } from '../../../common/constants.js';
+import { MockChatService } from '../../common/chatService/mockChatService.js';
 import { MockChatSessionsService } from '../../common/mockChatSessionsService.js';
 
 function createTestTiming(options?: {
@@ -36,185 +36,6 @@ function createTestTiming(options?: {
 	};
 }
 
-class MockChatService implements IChatService {
-	private readonly _chatModels: ISettableObservable<Iterable<IChatModel>> = observableValue('chatModels', []);
-	readonly chatModels = this._chatModels;
-	requestInProgressObs = observableValue('name', false);
-	edits2Enabled: boolean = false;
-	_serviceBrand: undefined;
-	editingSessions = [];
-	transferredSessionResource = undefined;
-	readonly onDidSubmitRequest = Event.None;
-	readonly onDidCreateModel = Event.None;
-
-	private sessions = new Map<string, IChatModel>();
-	private liveSessionItems: IChatDetail[] = [];
-	private historySessionItems: IChatDetail[] = [];
-
-	private readonly _onDidDisposeSession = new Emitter<{ sessionResource: URI[]; reason: 'cleared' }>();
-	readonly onDidDisposeSession = this._onDidDisposeSession.event;
-
-	fireDidDisposeSession(sessionResource: URI[]): void {
-		this._onDidDisposeSession.fire({ sessionResource, reason: 'cleared' });
-	}
-
-	setSaveModelsEnabled(enabled: boolean): void {
-
-	}
-
-	processPendingRequests(sessionResource: URI): void {
-
-	}
-
-	setLiveSessionItems(items: IChatDetail[]): void {
-		this.liveSessionItems = items;
-	}
-
-	setHistorySessionItems(items: IChatDetail[]): void {
-		this.historySessionItems = items;
-	}
-
-	addSession(sessionResource: URI, session: IChatModel): void {
-		this.sessions.set(sessionResource.toString(), session);
-		// Update the chatModels observable
-		this._chatModels.set([...this.sessions.values()], undefined);
-	}
-
-	removeSession(sessionResource: URI): void {
-		this.sessions.delete(sessionResource.toString());
-		// Update the chatModels observable
-		this._chatModels.set([...this.sessions.values()], undefined);
-	}
-
-	isEnabled(_location: ChatAgentLocation): boolean {
-		return true;
-	}
-
-	hasSessions(): boolean {
-		return this.sessions.size > 0;
-	}
-
-	getProviderInfos() {
-		return [];
-	}
-
-	startNewLocalSession(_location: ChatAgentLocation, _options?: IChatSessionStartOptions): any {
-		throw new Error('Method not implemented.');
-	}
-
-	getSession(sessionResource: URI): IChatModel | undefined {
-		return this.sessions.get(sessionResource.toString());
-	}
-
-	getLatestRequest(): IChatRequestModel | undefined {
-		return undefined;
-	}
-
-	acquireOrRestoreSession(_sessionResource: URI): Promise<any> {
-		throw new Error('Method not implemented.');
-	}
-
-	getSessionTitle(_sessionResource: URI): string | undefined {
-		return undefined;
-	}
-
-	loadSessionFromData(_data: any): any {
-		throw new Error('Method not implemented.');
-	}
-
-	acquireOrLoadSession(_resource: URI, _position: ChatAgentLocation, _token: CancellationToken): Promise<any> {
-		throw new Error('Method not implemented.');
-	}
-
-	acquireExistingSession(_sessionResource: URI): any {
-		return undefined;
-	}
-
-	setSessionTitle(_sessionResource: URI, _title: string): void { }
-
-	appendProgress(_request: IChatRequestModel, _progress: any): void { }
-
-	sendRequest(_sessionResource: URI, _message: string): Promise<any> {
-		throw new Error('Method not implemented.');
-	}
-
-	resendRequest(_request: IChatRequestModel, _options?: any): Promise<void> {
-		throw new Error('Method not implemented.');
-	}
-
-	adoptRequest(_sessionResource: URI, _request: IChatRequestModel): Promise<void> {
-		throw new Error('Method not implemented.');
-	}
-
-	removeRequest(_sessionResource: URI, _requestId: string): Promise<void> {
-		throw new Error('Method not implemented.');
-	}
-
-	cancelCurrentRequestForSession(_sessionResource: URI): void { }
-
-	setYieldRequested(_sessionResource: URI): void { }
-
-	removePendingRequest(_sessionResource: URI, _requestId: string): void { }
-
-	setPendingRequests(_sessionResource: URI, _requests: readonly { requestId: string; kind: ChatRequestQueueKind }[]): void { }
-
-	addCompleteRequest(): void { }
-
-	async getLocalSessionHistory(): Promise<IChatDetail[]> {
-		return this.historySessionItems;
-	}
-
-	async clearAllHistoryEntries(): Promise<void> { }
-
-	async removeHistoryEntry(_resource: URI): Promise<void> { }
-
-	readonly onDidPerformUserAction = Event.None;
-
-	notifyUserAction(_event: any): void { }
-
-	readonly onDidReceiveQuestionCarouselAnswer = Event.None;
-
-	notifyQuestionCarouselAnswer(_requestId: string, _resolveId: string, _answers: Record<string, unknown> | undefined): void { }
-
-	async transferChatSession(): Promise<void> { }
-
-	setChatSessionTitle(): void { }
-
-	isEditingLocation(_location: ChatAgentLocation): boolean {
-		return false;
-	}
-
-	getChatStorageFolder(): URI {
-		return URI.file('/tmp');
-	}
-
-	logChatIndex(): void { }
-
-	activateDefaultAgent(_location: ChatAgentLocation): Promise<void> {
-		return Promise.resolve();
-	}
-
-	getChatSessionFromInternalUri(_sessionResource: URI): any {
-		return undefined;
-	}
-
-	async getLiveSessionItems(): Promise<IChatDetail[]> {
-		return this.liveSessionItems;
-	}
-
-	async getHistorySessionItems(): Promise<IChatDetail[]> {
-		return this.historySessionItems;
-	}
-
-	waitForModelDisposals(): Promise<void> {
-		return Promise.resolve();
-	}
-
-	getMetadataForSession(sessionResource: URI): Promise<IChatDetail | undefined> {
-		throw new Error('Method not implemented.');
-	}
-}
-
 function createMockChatModel(options: {
 	sessionResource: URI;
 	hasRequests?: boolean;
@@ -316,7 +137,10 @@ suite('LocalAgentsSessionsController', () => {
 	test('should register itself with chat sessions service', async () => {
 		const controller = createController();
 
-		const controllerResults = await mockChatSessionsService.getChatSessionItems(undefined, CancellationToken.None);
+		const controllerResults: { readonly chatSessionType: string; readonly items: readonly IChatSessionItem[] }[] = [];
+		for await (const result of mockChatSessionsService.getChatSessionItems(undefined, CancellationToken.None)) {
+			controllerResults.push(result);
+		}
 		assert.strictEqual(controllerResults.length, 1);
 		assert.strictEqual(controllerResults[0].chatSessionType, controller.chatSessionType);
 	});
@@ -345,7 +169,7 @@ suite('LocalAgentsSessionsController', () => {
 				timestamp: Date.now()
 			});
 
-			mockChatService.addSession(sessionResource, mockModel);
+			mockChatService.addSession(mockModel);
 			mockChatService.setLiveSessionItems([{
 				sessionResource,
 				title: 'Test Session',
@@ -396,7 +220,7 @@ suite('LocalAgentsSessionsController', () => {
 				hasRequests: true
 			});
 
-			mockChatService.addSession(sessionResource, mockModel);
+			mockChatService.addSession(mockModel);
 			mockChatService.setLiveSessionItems([{
 				sessionResource,
 				title: 'Live Session',
@@ -433,7 +257,7 @@ suite('LocalAgentsSessionsController', () => {
 					requestInProgress: true
 				});
 
-				mockChatService.addSession(sessionResource, mockModel);
+				mockChatService.addSession(mockModel);
 				mockChatService.setLiveSessionItems([{
 					sessionResource,
 					title: 'In Progress Session',
@@ -464,7 +288,7 @@ suite('LocalAgentsSessionsController', () => {
 					lastResponseHasError: false
 				});
 
-				mockChatService.addSession(sessionResource, mockModel);
+				mockChatService.addSession(mockModel);
 				mockChatService.setLiveSessionItems([{
 					sessionResource,
 					title: 'Completed Session',
@@ -494,7 +318,7 @@ suite('LocalAgentsSessionsController', () => {
 					lastResponseCanceled: true
 				});
 
-				mockChatService.addSession(sessionResource, mockModel);
+				mockChatService.addSession(mockModel);
 				mockChatService.setLiveSessionItems([{
 					sessionResource,
 					title: 'Canceled Session',
@@ -524,7 +348,7 @@ suite('LocalAgentsSessionsController', () => {
 					lastResponseHasError: true
 				});
 
-				mockChatService.addSession(sessionResource, mockModel);
+				mockChatService.addSession(mockModel);
 				mockChatService.setLiveSessionItems([{
 					sessionResource,
 					title: 'Error Session',
@@ -569,7 +393,7 @@ suite('LocalAgentsSessionsController', () => {
 					}
 				});
 
-				mockChatService.addSession(sessionResource, mockModel);
+				mockChatService.addSession(mockModel);
 				mockChatService.setLiveSessionItems([{
 					sessionResource,
 					title: 'Stats Session',
@@ -615,7 +439,7 @@ suite('LocalAgentsSessionsController', () => {
 					}
 				});
 
-				mockChatService.addSession(sessionResource, mockModel);
+				mockChatService.addSession(mockModel);
 				mockChatService.setLiveSessionItems([{
 					sessionResource,
 					title: 'No Stats Session',
@@ -646,7 +470,7 @@ suite('LocalAgentsSessionsController', () => {
 					timestamp: modelTimestamp
 				});
 
-				mockChatService.addSession(sessionResource, mockModel);
+				mockChatService.addSession(mockModel);
 				mockChatService.setLiveSessionItems([{
 					sessionResource,
 					title: 'Timing Session',
@@ -700,7 +524,7 @@ suite('LocalAgentsSessionsController', () => {
 					lastResponseCompletedAt: completedAt
 				});
 
-				mockChatService.addSession(sessionResource, mockModel);
+				mockChatService.addSession(mockModel);
 				mockChatService.setLiveSessionItems([{
 					sessionResource,
 					title: 'EndTime Session',
@@ -729,7 +553,7 @@ suite('LocalAgentsSessionsController', () => {
 					hasRequests: true
 				});
 
-				mockChatService.addSession(sessionResource, mockModel);
+				mockChatService.addSession(mockModel);
 				mockChatService.setLiveSessionItems([{
 					sessionResource,
 					title: 'Icon Session',
@@ -760,15 +584,26 @@ suite('LocalAgentsSessionsController', () => {
 				});
 
 				// Add the session first
-				mockChatService.addSession(sessionResource, mockModel);
+				mockChatService.addSession(mockModel);
+				mockChatService.setLiveSessionItems([{
+					sessionResource,
+					title: 'Test Session',
+					lastMessageDate: Date.now(),
+					isActive: true,
+					timing: createTestTiming(),
+					lastResponseState: ResponseModelState.Complete
+				}]);
 
 				let changeEventCount = 0;
 				disposables.add(controller.onDidChangeChatSessionItems(() => {
 					changeEventCount++;
 				}));
 
+				const onDidChangeChatSessionItems = Event.toPromise(controller.onDidChangeChatSessionItems);
+
 				// Simulate progress change by triggering the progress listener
-				mockChatSessionsService.triggerProgressEvent();
+				mockChatService.triggerProgressEvent(sessionResource);
+				await onDidChangeChatSessionItems;
 
 				assert.strictEqual(changeEventCount, 1);
 			});
@@ -786,16 +621,27 @@ suite('LocalAgentsSessionsController', () => {
 				});
 
 				// Add the session first
-				mockChatService.addSession(sessionResource, mockModel);
+				mockChatService.addSession(mockModel);
+				mockChatService.setLiveSessionItems([{
+					sessionResource,
+					title: 'Test Session',
+					lastMessageDate: Date.now(),
+					isActive: true,
+					timing: createTestTiming(),
+					lastResponseState: ResponseModelState.Complete
+				}]);
 
 				let changeEventCount = 0;
 				disposables.add(controller.onDidChangeChatSessionItems(() => {
 					changeEventCount++;
 				}));
 
+				const onDidChangeChatSessionItems = Event.toPromise(controller.onDidChangeChatSessionItems);
+
 				// Simulate progress change by triggering the progress listener
-				mockChatSessionsService.triggerProgressEvent();
+				mockChatService.triggerProgressEvent(sessionResource);
 
+				await onDidChangeChatSessionItems;
 				assert.strictEqual(changeEventCount, 1);
 			});
 		});
@@ -811,7 +657,7 @@ suite('LocalAgentsSessionsController', () => {
 				});
 
 				// Add the session first
-				mockChatService.addSession(sessionResource, mockModel);
+				mockChatService.addSession(mockModel);
 
 				// Now remove the session - the observable should trigger cleanup
 				mockChatService.removeSession(sessionResource);
diff --git a/src/vs/workbench/contrib/chat/test/browser/aiCustomization/aiCustomizationListWidget.test.ts b/src/vs/workbench/contrib/chat/test/browser/aiCustomization/aiCustomizationListWidget.test.ts
new file mode 100644
index 0000000000000..5723ae0a159a0
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/browser/aiCustomization/aiCustomizationListWidget.test.ts
@@ -0,0 +1,53 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { getCustomizationSecondaryText, truncateToFirstSentence } from '../../../browser/aiCustomization/aiCustomizationListWidgetUtils.js';
+import { PromptsType } from '../../../common/promptSyntax/promptTypes.js';
+
+suite('aiCustomizationListWidget', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	suite('truncateToFirstSentence', () => {
+		test('keeps first sentence when within max chars', () => {
+			assert.strictEqual(
+				truncateToFirstSentence('First sentence. Second sentence.'),
+				'First sentence.'
+			);
+		});
+
+		test('falls back to max chars when no sentence boundary is found', () => {
+			const longText = 'a'.repeat(140);
+			assert.strictEqual(
+				truncateToFirstSentence(longText),
+				`${'a'.repeat(120)}\u2026`
+			);
+		});
+	});
+
+	suite('getCustomizationSecondaryText', () => {
+		test('keeps hook descriptions intact', () => {
+			assert.strictEqual(
+				getCustomizationSecondaryText('echo "setup". echo "run".', 'hook.json', PromptsType.hook),
+				'echo "setup". echo "run".'
+			);
+		});
+
+		test('truncates non-hook descriptions to the first sentence', () => {
+			assert.strictEqual(
+				getCustomizationSecondaryText('Show the first sentence. Hide the rest.', 'prompt.md', PromptsType.prompt),
+				'Show the first sentence.'
+			);
+		});
+
+		test('falls back to filename when description is missing', () => {
+			assert.strictEqual(
+				getCustomizationSecondaryText(undefined, 'prompt.md', PromptsType.prompt),
+				'prompt.md'
+			);
+		});
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/browser/aiCustomization/applyStorageSourceFilter.test.ts b/src/vs/workbench/contrib/chat/test/browser/aiCustomization/applyStorageSourceFilter.test.ts
new file mode 100644
index 0000000000000..95988b49868b5
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/browser/aiCustomization/applyStorageSourceFilter.test.ts
@@ -0,0 +1,237 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { URI } from '../../../../../../base/common/uri.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { PromptsStorage } from '../../../common/promptSyntax/service/promptsService.js';
+import { applyStorageSourceFilter, IStorageSourceFilter } from '../../../common/aiCustomizationWorkspaceService.js';
+
+function item(path: string, storage: PromptsStorage): { uri: URI; storage: PromptsStorage } {
+	return { uri: URI.file(path), storage };
+}
+
+suite('applyStorageSourceFilter', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	suite('source filtering', () => {
+		test('keeps items matching sources', () => {
+			const items = [
+				item('/w/a.md', PromptsStorage.local),
+				item('/u/b.md', PromptsStorage.user),
+				item('/e/c.md', PromptsStorage.extension),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.local, PromptsStorage.user, PromptsStorage.extension],
+			};
+			assert.strictEqual(applyStorageSourceFilter(items, filter).length, 3);
+		});
+
+		test('removes items not in sources', () => {
+			const items = [
+				item('/w/a.md', PromptsStorage.local),
+				item('/u/b.md', PromptsStorage.user),
+				item('/e/c.md', PromptsStorage.extension),
+				item('/p/d.md', PromptsStorage.plugin),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.local],
+			};
+			const result = applyStorageSourceFilter(items, filter);
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual(result[0].uri.toString(), URI.file('/w/a.md').toString());
+		});
+
+		test('empty sources removes everything', () => {
+			const items = [
+				item('/w/a.md', PromptsStorage.local),
+				item('/u/b.md', PromptsStorage.user),
+			];
+			const filter: IStorageSourceFilter = { sources: [] };
+			assert.strictEqual(applyStorageSourceFilter(items, filter).length, 0);
+		});
+
+		test('empty items returns empty', () => {
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.local, PromptsStorage.user],
+			};
+			assert.strictEqual(applyStorageSourceFilter([], filter).length, 0);
+		});
+	});
+
+	suite('includedUserFileRoots filtering', () => {
+		test('undefined includedUserFileRoots keeps all user files', () => {
+			const items = [
+				item('/home/.copilot/a.md', PromptsStorage.user),
+				item('/home/.vscode/b.md', PromptsStorage.user),
+				item('/home/.claude/c.md', PromptsStorage.user),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.user],
+				// includedUserFileRoots not set = allow all
+			};
+			assert.strictEqual(applyStorageSourceFilter(items, filter).length, 3);
+		});
+
+		test('includedUserFileRoots filters user files by root', () => {
+			const items = [
+				item('/home/.copilot/instructions/a.md', PromptsStorage.user),
+				item('/home/.vscode/instructions/b.md', PromptsStorage.user),
+				item('/home/.claude/rules/c.md', PromptsStorage.user),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.user],
+				includedUserFileRoots: [URI.file('/home/.copilot'), URI.file('/home/.claude')],
+			};
+			const result = applyStorageSourceFilter(items, filter);
+			assert.strictEqual(result.length, 2);
+			assert.strictEqual(result[0].uri.toString(), URI.file('/home/.copilot/instructions/a.md').toString());
+			assert.strictEqual(result[1].uri.toString(), URI.file('/home/.claude/rules/c.md').toString());
+		});
+
+		test('includedUserFileRoots does not affect non-user items', () => {
+			const items = [
+				item('/w/a.md', PromptsStorage.local),
+				item('/e/b.md', PromptsStorage.extension),
+				item('/home/.copilot/c.md', PromptsStorage.user),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.local, PromptsStorage.extension, PromptsStorage.user],
+				includedUserFileRoots: [URI.file('/home/.copilot')],
+			};
+			const result = applyStorageSourceFilter(items, filter);
+			// local + extension kept (not affected by user root filter), user kept (matches root)
+			assert.strictEqual(result.length, 3);
+		});
+
+		test('empty includedUserFileRoots removes all user files', () => {
+			const items = [
+				item('/w/a.md', PromptsStorage.local),
+				item('/home/.copilot/b.md', PromptsStorage.user),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.local, PromptsStorage.user],
+				includedUserFileRoots: [], // explicit empty = no user files allowed
+			};
+			const result = applyStorageSourceFilter(items, filter);
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual(result[0].storage, PromptsStorage.local);
+		});
+
+		test('user file at exact root is included', () => {
+			const items = [
+				item('/home/.copilot', PromptsStorage.user),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.user],
+				includedUserFileRoots: [URI.file('/home/.copilot')],
+			};
+			assert.strictEqual(applyStorageSourceFilter(items, filter).length, 1);
+		});
+
+		test('user file outside all roots is excluded', () => {
+			const items = [
+				item('/other/path/a.md', PromptsStorage.user),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.user],
+				includedUserFileRoots: [URI.file('/home/.copilot'), URI.file('/home/.claude')],
+			};
+			assert.strictEqual(applyStorageSourceFilter(items, filter).length, 0);
+		});
+
+		test('deeply nested user file under root is included', () => {
+			const items = [
+				item('/home/.copilot/instructions/sub/deep/a.md', PromptsStorage.user),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.user],
+				includedUserFileRoots: [URI.file('/home/.copilot')],
+			};
+			assert.strictEqual(applyStorageSourceFilter(items, filter).length, 1);
+		});
+	});
+
+	suite('combined filtering', () => {
+		test('source filter + user root filter applied together', () => {
+			const items = [
+				item('/w/a.md', PromptsStorage.local),
+				item('/home/.copilot/b.md', PromptsStorage.user),
+				item('/home/.vscode/c.md', PromptsStorage.user),
+				item('/e/d.md', PromptsStorage.extension),
+				item('/p/e.md', PromptsStorage.plugin),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.local, PromptsStorage.user],
+				includedUserFileRoots: [URI.file('/home/.copilot')],
+			};
+			const result = applyStorageSourceFilter(items, filter);
+			// local (kept), .copilot user (kept), .vscode user (excluded by root),
+			// extension (excluded by source), plugin (excluded by source)
+			assert.strictEqual(result.length, 2);
+		});
+
+		test('sessions-like filter: hooks show only local', () => {
+			const items = [
+				item('/w/.github/hooks/pre.json', PromptsStorage.local),
+				item('/home/.claude/settings.json', PromptsStorage.user),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.local],
+			};
+			const result = applyStorageSourceFilter(items, filter);
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual(result[0].storage, PromptsStorage.local);
+		});
+
+		test('sessions-like filter: instructions show only CLI roots', () => {
+			const items = [
+				item('/w/.github/instructions/a.md', PromptsStorage.local),
+				item('/home/.copilot/instructions/b.md', PromptsStorage.user),
+				item('/home/.claude/rules/c.md', PromptsStorage.user),
+				item('/home/.vscode-profile/instructions/d.md', PromptsStorage.user),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.local, PromptsStorage.user],
+				includedUserFileRoots: [
+					URI.file('/home/.copilot'),
+					URI.file('/home/.claude'),
+					URI.file('/home/.agents'),
+				],
+			};
+			const result = applyStorageSourceFilter(items, filter);
+			// local + .copilot + .claude pass; .vscode-profile excluded
+			assert.strictEqual(result.length, 3);
+		});
+
+		test('core-like filter: show everything', () => {
+			const items = [
+				item('/w/a.md', PromptsStorage.local),
+				item('/u/b.md', PromptsStorage.user),
+				item('/e/c.md', PromptsStorage.extension),
+				item('/p/d.md', PromptsStorage.plugin),
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.local, PromptsStorage.user, PromptsStorage.extension, PromptsStorage.plugin],
+			};
+			assert.strictEqual(applyStorageSourceFilter(items, filter).length, 4);
+		});
+	});
+
+	suite('type safety', () => {
+		test('works with objects that have extra properties', () => {
+			const items = [
+				{ uri: URI.file('/w/a.md'), storage: PromptsStorage.local, name: 'A', extra: true },
+				{ uri: URI.file('/u/b.md'), storage: PromptsStorage.user, name: 'B', extra: false },
+			];
+			const filter: IStorageSourceFilter = {
+				sources: [PromptsStorage.local],
+			};
+			const result = applyStorageSourceFilter(items, filter);
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual((result[0] as typeof items[0]).name, 'A');
+		});
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/browser/aiCustomization/customizationCreatorService.test.ts b/src/vs/workbench/contrib/chat/test/browser/aiCustomization/customizationCreatorService.test.ts
new file mode 100644
index 0000000000000..0b5d81754fb01
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/browser/aiCustomization/customizationCreatorService.test.ts
@@ -0,0 +1,45 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { URI } from '../../../../../../base/common/uri.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { PromptsType } from '../../../common/promptSyntax/promptTypes.js';
+import { IPromptsService, PromptsStorage } from '../../../common/promptSyntax/service/promptsService.js';
+import { resolveUserTargetDirectory } from '../../../browser/aiCustomization/customizationCreatorService.js';
+
+suite('customizationCreatorService', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	function createMockPromptsService(userFolderUri?: URI): Pick<IPromptsService, 'getSourceFolders'> {
+		return {
+			getSourceFolders: () => Promise.resolve(
+				userFolderUri
+					? [{ uri: userFolderUri, storage: PromptsStorage.user, type: PromptsType.instructions }]
+					: []
+			),
+		} as Pick<IPromptsService, 'getSourceFolders'>;
+	}
+
+	suite('resolveUserTargetDirectory', () => {
+
+		test('returns user folder from getSourceFolders', async () => {
+			const userFolder = URI.file('/home/user/.copilot/instructions');
+			const result = await resolveUserTargetDirectory(
+				createMockPromptsService(userFolder) as IPromptsService,
+				PromptsType.instructions,
+			);
+			assert.strictEqual(result?.path, '/home/user/.copilot/instructions');
+		});
+
+		test('returns undefined when no user folder exists', async () => {
+			const result = await resolveUserTargetDirectory(
+				createMockPromptsService() as IPromptsService,
+				PromptsType.hook,
+			);
+			assert.strictEqual(result, undefined);
+		});
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/browser/attachments/chatVariables.test.ts b/src/vs/workbench/contrib/chat/test/browser/attachments/chatVariables.test.ts
new file mode 100644
index 0000000000000..59e05f0411bb7
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/browser/attachments/chatVariables.test.ts
@@ -0,0 +1,191 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { Range } from '../../../../../../editor/common/core/range.js';
+import { IDynamicVariable } from '../../../common/attachments/chatVariables.js';
+import { IChatWidget } from '../../../browser/chat.js';
+import { getDynamicVariablesForWidget, getSelectedToolAndToolSetsForWidget } from '../../../browser/attachments/chatVariables.js';
+import { ChatDynamicVariableModel } from '../../../browser/attachments/chatDynamicVariables.js';
+import { IChatRequestVariableEntry } from '../../../common/attachments/chatVariableEntries.js';
+import { IToolData, IToolSet, ToolDataSource } from '../../../common/tools/languageModelToolsService.js';
+import { observableValue } from '../../../../../../base/common/observable.js';
+
+function createMockVariable(overrides?: Partial<IDynamicVariable>): IDynamicVariable {
+	return {
+		id: 'var-1',
+		fullName: 'test-var',
+		range: new Range(1, 1, 1, 10),
+		data: 'test-data',
+		...overrides,
+	};
+}
+
+function createMockAttachment(overrides?: Partial<IChatRequestVariableEntry>): IChatRequestVariableEntry {
+	return {
+		id: 'attach-1',
+		name: 'test-attachment',
+		kind: 'file',
+		value: 'test-value',
+		...overrides,
+	} as IChatRequestVariableEntry;
+}
+
+function createMockWidget(options: {
+	hasViewModel?: boolean;
+	supportsFileReferences?: boolean;
+	contribVariables?: IDynamicVariable[];
+	editing?: boolean;
+	attachments?: IChatRequestVariableEntry[];
+	editorTextLength?: number;
+}): IChatWidget {
+	const {
+		hasViewModel = true,
+		supportsFileReferences = true,
+		contribVariables = [],
+		editing = false,
+		attachments = [],
+		editorTextLength = 100,
+	} = options;
+
+	const contribModel = {
+		id: ChatDynamicVariableModel.ID,
+		variables: contribVariables,
+	};
+
+	return {
+		viewModel: hasViewModel ? { editing: editing ? {} : undefined } : undefined,
+		supportsFileReferences,
+		getContrib: (id: string) => id === ChatDynamicVariableModel.ID ? contribModel : undefined,
+		input: {
+			attachmentModel: { attachments },
+		},
+		inputEditor: {
+			getModel: () => ({
+				getValueLength: () => editorTextLength,
+				getPositionAt: (offset: number) => ({ lineNumber: 1, column: offset + 1 }),
+			}),
+		},
+	} as unknown as IChatWidget;
+}
+
+suite('getDynamicVariablesForWidget', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('returns empty when no viewModel', () => {
+		const widget = createMockWidget({ hasViewModel: false });
+		assert.deepStrictEqual(getDynamicVariablesForWidget(widget), []);
+	});
+
+	test('returns empty when file references not supported', () => {
+		const widget = createMockWidget({ supportsFileReferences: false });
+		assert.deepStrictEqual(getDynamicVariablesForWidget(widget), []);
+	});
+
+	test('returns contrib model variables when not editing', () => {
+		const variables = [createMockVariable()];
+		const widget = createMockWidget({ contribVariables: variables });
+		assert.deepStrictEqual(getDynamicVariablesForWidget(widget), variables);
+	});
+
+	test('returns contrib model variables when editing with existing variables', () => {
+		const variables = [createMockVariable()];
+		const widget = createMockWidget({ editing: true, contribVariables: variables });
+		assert.deepStrictEqual(getDynamicVariablesForWidget(widget), variables);
+	});
+
+	test('converts attachments to dynamic variables when editing with attachments and no contrib variables', () => {
+		const attachments = [
+			createMockAttachment({
+				id: 'a1',
+				name: 'file.ts',
+				kind: 'file',
+				value: 'file-value',
+				range: { start: 0, endExclusive: 8 },
+			}),
+		];
+		const widget = createMockWidget({ editing: true, attachments, contribVariables: [] });
+		const result = getDynamicVariablesForWidget(widget);
+
+		assert.strictEqual(result.length, 1);
+		assert.strictEqual(result[0].id, 'a1');
+		assert.strictEqual(result[0].fullName, 'file.ts');
+		assert.strictEqual(result[0].isFile, true);
+		assert.strictEqual(result[0].isDirectory, false);
+		assert.strictEqual(result[0].data, 'file-value');
+	});
+
+	test('skips attachments without range when editing', () => {
+		const attachments = [createMockAttachment({ range: undefined })];
+		const widget = createMockWidget({ editing: true, attachments, contribVariables: [] });
+		const result = getDynamicVariablesForWidget(widget);
+
+		// No ranged attachments, falls back to contrib model variables (empty)
+		assert.deepStrictEqual(result, []);
+	});
+
+	test('skips attachments with empty range', () => {
+		const attachments = [createMockAttachment({ range: { start: 5, endExclusive: 5 } })];
+		const widget = createMockWidget({ editing: true, attachments, contribVariables: [] });
+		const result = getDynamicVariablesForWidget(widget);
+		assert.deepStrictEqual(result, []);
+	});
+
+	test('skips attachments with out-of-bounds range', () => {
+		const attachments = [createMockAttachment({ range: { start: 0, endExclusive: 200 } })];
+		const widget = createMockWidget({ editing: true, attachments, editorTextLength: 100, contribVariables: [] });
+		const result = getDynamicVariablesForWidget(widget);
+		assert.deepStrictEqual(result, []);
+	});
+
+	test('skips attachments with negative start', () => {
+		const attachments = [createMockAttachment({ range: { start: -1, endExclusive: 5 } })];
+		const widget = createMockWidget({ editing: true, attachments, contribVariables: [] });
+		const result = getDynamicVariablesForWidget(widget);
+		assert.deepStrictEqual(result, []);
+	});
+
+	test('sets isDirectory for directory attachments', () => {
+		const attachments = [
+			createMockAttachment({
+				kind: 'directory',
+				range: { start: 0, endExclusive: 5 },
+			}),
+		];
+		const widget = createMockWidget({ editing: true, attachments, contribVariables: [] });
+		const result = getDynamicVariablesForWidget(widget);
+
+		assert.strictEqual(result.length, 1);
+		assert.strictEqual(result[0].isFile, false);
+		assert.strictEqual(result[0].isDirectory, true);
+	});
+});
+
+suite('getSelectedToolAndToolSetsForWidget', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('returns the entriesMap from the selected tools model', () => {
+		const toolData: IToolData = {
+			id: 'tool-1',
+			toolReferenceName: 'myTool',
+			displayName: 'My Tool',
+			modelDescription: 'A test tool',
+			canBeReferencedInPrompt: true,
+			source: ToolDataSource.Internal,
+		};
+		const expectedMap = new Map<IToolData | IToolSet, boolean>([[toolData, true]]);
+		const entriesMap = observableValue('test', expectedMap);
+
+		const widget = {
+			input: {
+				selectedToolsModel: { entriesMap },
+			},
+		} as unknown as IChatWidget;
+
+		const result = getSelectedToolAndToolSetsForWidget(widget);
+		assert.strictEqual(result, expectedMap);
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/browser/chatDebugEventDetailRenderer.test.ts b/src/vs/workbench/contrib/chat/test/browser/chatDebugEventDetailRenderer.test.ts
index 3a0f01975d1f7..8d9a7d19bfda1 100644
--- a/src/vs/workbench/contrib/chat/test/browser/chatDebugEventDetailRenderer.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/chatDebugEventDetailRenderer.test.ts
@@ -60,17 +60,17 @@ suite('formatEventDetail', () => {
 			sessionResource: URI.parse('test://s1'),
 			created: new Date(),
 			model: 'gpt-4o',
-			inputTokens: 1000,
-			outputTokens: 500,
-			totalTokens: 1500,
-			durationInMillis: 3200,
+			inputTokens: 100,
+			outputTokens: 50,
+			totalTokens: 150,
+			durationInMillis: 320,
 		};
 		const result = formatEventDetail(event);
 		assert.ok(result.includes('gpt-4o'));
-		assert.ok(result.includes('1000'));
-		assert.ok(result.includes('500'));
-		assert.ok(result.includes('1500'));
-		assert.ok(result.includes('3200'));
+		assert.ok(result.includes('100'));
+		assert.ok(result.includes('50'));
+		assert.ok(result.includes('150'));
+		assert.ok(result.includes('320'));
 	});
 
 	test('generic event', () => {
@@ -118,7 +118,7 @@ suite('formatEventDetail', () => {
 			agentName: 'Data',
 			description: 'Querying KQL',
 			status: 'completed',
-			durationInMillis: 5000,
+			durationInMillis: 500,
 			toolCallCount: 3,
 			modelTurnCount: 2,
 		};
@@ -126,7 +126,7 @@ suite('formatEventDetail', () => {
 		assert.ok(result.includes('Data'));
 		assert.ok(result.includes('Querying KQL'));
 		assert.ok(result.includes('completed'));
-		assert.ok(result.includes('5000'));
+		assert.ok(result.includes('500'));
 		assert.ok(result.includes('3'));
 		assert.ok(result.includes('2'));
 	});
diff --git a/src/vs/workbench/contrib/chat/test/browser/chatDebugFilters.test.ts b/src/vs/workbench/contrib/chat/test/browser/chatDebugFilters.test.ts
new file mode 100644
index 0000000000000..db4550e736974
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/browser/chatDebugFilters.test.ts
@@ -0,0 +1,221 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { ChatDebugFilterState } from '../../browser/chatDebug/chatDebugFilters.js';
+import { parseTimeToken } from '../../common/chatDebugEvents.js';
+
+suite('ChatDebugFilterState', () => {
+	const disposables = ensureNoDisposablesAreLeakedInTestSuite();
+
+	suite('parseTimeToken', () => {
+
+		suite('before: prefix', () => {
+
+			test('year only — rounds to end of year', () => {
+				const result = parseTimeToken('before:2026', 'before');
+				assert.strictEqual(result, new Date(2026, 11, 31, 23, 59, 59, 999).getTime());
+			});
+
+			test('year-month — rounds to end of month', () => {
+				const result = parseTimeToken('before:2026-03', 'before');
+				// new Date(2026, 3, 0) gives last day of March
+				assert.strictEqual(result, new Date(2026, 3, 0, 23, 59, 59, 999).getTime());
+			});
+
+			test('year-month (February, non-leap) — rounds to end of Feb', () => {
+				const result = parseTimeToken('before:2025-02', 'before');
+				assert.strictEqual(result, new Date(2025, 2, 0, 23, 59, 59, 999).getTime());
+			});
+
+			test('year-month-day — rounds to end of day', () => {
+				const result = parseTimeToken('before:2026-03-03', 'before');
+				assert.strictEqual(result, new Date(2026, 2, 3, 23, 59, 59, 999).getTime());
+			});
+
+			test('date with hour only — rounds to end of hour', () => {
+				const result = parseTimeToken('before:2026-03-03t14', 'before');
+				assert.strictEqual(result, new Date(2026, 2, 3, 14, 59, 59, 999).getTime());
+			});
+
+			test('date with hour:minute — rounds to end of minute', () => {
+				const result = parseTimeToken('before:2026-03-03t14:30', 'before');
+				assert.strictEqual(result, new Date(2026, 2, 3, 14, 30, 59, 999).getTime());
+			});
+
+			test('full date-time with seconds', () => {
+				const result = parseTimeToken('before:2026-03-03t14:30:45', 'before');
+				assert.strictEqual(result, new Date(2026, 2, 3, 14, 30, 45, 999).getTime());
+			});
+		});
+
+		suite('after: prefix', () => {
+
+			test('year only — start of year', () => {
+				const result = parseTimeToken('after:2026', 'after');
+				assert.strictEqual(result, new Date(2026, 0, 1, 0, 0, 0, 0).getTime());
+			});
+
+			test('year-month — start of month', () => {
+				const result = parseTimeToken('after:2026-03', 'after');
+				assert.strictEqual(result, new Date(2026, 2, 1, 0, 0, 0, 0).getTime());
+			});
+
+			test('year-month-day — start of day', () => {
+				const result = parseTimeToken('after:2026-03-03', 'after');
+				assert.strictEqual(result, new Date(2026, 2, 3, 0, 0, 0, 0).getTime());
+			});
+
+			test('date with hour only — start of hour', () => {
+				const result = parseTimeToken('after:2026-03-03t14', 'after');
+				assert.strictEqual(result, new Date(2026, 2, 3, 14, 0, 0, 0).getTime());
+			});
+
+			test('date with hour:minute — start of minute', () => {
+				const result = parseTimeToken('after:2026-03-03t14:30', 'after');
+				assert.strictEqual(result, new Date(2026, 2, 3, 14, 30, 0, 0).getTime());
+			});
+
+			test('full date-time with seconds', () => {
+				const result = parseTimeToken('after:2026-03-03t14:30:45', 'after');
+				assert.strictEqual(result, new Date(2026, 2, 3, 14, 30, 45, 0).getTime());
+			});
+		});
+
+		suite('no match', () => {
+
+			test('returns undefined for empty string', () => {
+				assert.strictEqual(parseTimeToken('', 'before'), undefined);
+			});
+
+			test('returns undefined for unrelated text', () => {
+				assert.strictEqual(parseTimeToken('hello world', 'before'), undefined);
+			});
+
+			test('returns undefined for wrong prefix', () => {
+				assert.strictEqual(parseTimeToken('after:2026', 'before'), undefined);
+			});
+
+			test('returns undefined for bare time without date', () => {
+				assert.strictEqual(parseTimeToken('before:14:30', 'before'), undefined);
+			});
+		});
+
+		suite('embedded in text', () => {
+
+			test('extracts token from surrounding text', () => {
+				const result = parseTimeToken('some text before:2026-03-03 more text', 'before');
+				assert.strictEqual(result, new Date(2026, 2, 3, 23, 59, 59, 999).getTime());
+			});
+
+			test('handles both before and after in same string', () => {
+				const text = 'after:2026-01 before:2026-03';
+				const after = parseTimeToken(text, 'after');
+				const before = parseTimeToken(text, 'before');
+				assert.strictEqual(after, new Date(2026, 0, 1, 0, 0, 0, 0).getTime());
+				assert.strictEqual(before, new Date(2026, 3, 0, 23, 59, 59, 999).getTime());
+			});
+		});
+	});
+
+	suite('setTextFilter and timestamp parsing', () => {
+		let state: ChatDebugFilterState;
+
+		setup(() => {
+			state = disposables.add(new ChatDebugFilterState());
+		});
+
+		test('sets beforeTimestamp and afterTimestamp from text', () => {
+			state.setTextFilter('after:2026-01-01 before:2026-12-31');
+			assert.strictEqual(state.afterTimestamp, new Date(2026, 0, 1, 0, 0, 0, 0).getTime());
+			assert.strictEqual(state.beforeTimestamp, new Date(2026, 11, 31, 23, 59, 59, 999).getTime());
+		});
+
+		test('clears timestamps when tokens removed', () => {
+			state.setTextFilter('before:2026');
+			assert.ok(state.beforeTimestamp !== undefined);
+			state.setTextFilter('hello');
+			assert.strictEqual(state.beforeTimestamp, undefined);
+		});
+	});
+
+	suite('textFilterWithoutTimestamps', () => {
+		let state: ChatDebugFilterState;
+
+		setup(() => {
+			state = disposables.add(new ChatDebugFilterState());
+		});
+
+		test('strips year-only token', () => {
+			state.setTextFilter('before:2026 hello');
+			assert.strictEqual(state.textFilterWithoutTimestamps, 'hello');
+		});
+
+		test('strips year-month token', () => {
+			state.setTextFilter('after:2026-03 hello');
+			assert.strictEqual(state.textFilterWithoutTimestamps, 'hello');
+		});
+
+		test('strips full date-time token', () => {
+			state.setTextFilter('before:2026-03-03t14:30:45 hello');
+			assert.strictEqual(state.textFilterWithoutTimestamps, 'hello');
+		});
+
+		test('strips multiple tokens', () => {
+			state.setTextFilter('after:2026-01 hello before:2026-12');
+			assert.strictEqual(state.textFilterWithoutTimestamps, 'hello');
+		});
+
+		test('returns empty when only tokens', () => {
+			state.setTextFilter('before:2026');
+			assert.strictEqual(state.textFilterWithoutTimestamps, '');
+		});
+	});
+
+	suite('isTimestampVisible', () => {
+		let state: ChatDebugFilterState;
+
+		setup(() => {
+			state = disposables.add(new ChatDebugFilterState());
+		});
+
+		test('visible when no timestamp filters set', () => {
+			assert.strictEqual(state.isTimestampVisible(new Date(2026, 5, 15)), true);
+		});
+
+		test('hidden when after beforeTimestamp', () => {
+			state.setTextFilter('before:2026-03');
+			// April 1st is after end of March
+			assert.strictEqual(state.isTimestampVisible(new Date(2026, 3, 1)), false);
+		});
+
+		test('visible when before beforeTimestamp', () => {
+			state.setTextFilter('before:2026-03');
+			assert.strictEqual(state.isTimestampVisible(new Date(2026, 1, 15)), true);
+		});
+
+		test('hidden when before afterTimestamp', () => {
+			state.setTextFilter('after:2026-06');
+			assert.strictEqual(state.isTimestampVisible(new Date(2026, 4, 31)), false);
+		});
+
+		test('visible when after afterTimestamp', () => {
+			state.setTextFilter('after:2026-06');
+			assert.strictEqual(state.isTimestampVisible(new Date(2026, 6, 1)), true);
+		});
+
+		test('visible when within before/after range', () => {
+			state.setTextFilter('after:2026-03 before:2026-06');
+			assert.strictEqual(state.isTimestampVisible(new Date(2026, 3, 15)), true);
+		});
+
+		test('hidden when outside before/after range', () => {
+			state.setTextFilter('after:2026-03 before:2026-06');
+			assert.strictEqual(state.isTimestampVisible(new Date(2026, 0, 1)), false);
+			assert.strictEqual(state.isTimestampVisible(new Date(2026, 8, 1)), false);
+		});
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/browser/chatEditing/chatEditingCheckpointTimeline.test.ts b/src/vs/workbench/contrib/chat/test/browser/chatEditing/chatEditingCheckpointTimeline.test.ts
index 57478466f4f5f..f6f3af2a699e0 100644
--- a/src/vs/workbench/contrib/chat/test/browser/chatEditing/chatEditingCheckpointTimeline.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/chatEditing/chatEditingCheckpointTimeline.test.ts
@@ -1248,6 +1248,54 @@ suite('ChatEditingCheckpointTimeline', function () {
 		await timeline.navigateToCheckpoint(stop2NewCheckpointId);
 		assert.strictEqual(fileContents.get(uri), 'replacement edit', 'Content should still be correct after full timeline traversal');
 	});
+
+	test('undo/redo with multiple no-edit requests advances one request at a time', async function () {
+		// req1: no edits
+		timeline.createCheckpoint('req1', undefined, 'Start req1');
+
+		// req2: no edits
+		timeline.createCheckpoint('req2', undefined, 'Start req2');
+
+		// req3: no edits
+		timeline.createCheckpoint('req3', undefined, 'Start req3');
+
+		// req4: no edits
+		timeline.createCheckpoint('req4', undefined, 'Start req4');
+
+		// Undo should step one request at a time
+		assert.strictEqual(timeline.canUndo.get(), true);
+
+		await timeline.undoToLastCheckpoint();
+		assert.deepStrictEqual(timeline.requestDisablement.get().map(d => d.requestId), ['req4']);
+
+		await timeline.undoToLastCheckpoint();
+		assert.deepStrictEqual(timeline.requestDisablement.get().map(d => d.requestId), ['req4', 'req3']);
+
+		await timeline.undoToLastCheckpoint();
+		assert.deepStrictEqual(timeline.requestDisablement.get().map(d => d.requestId), ['req4', 'req3', 'req2']);
+
+		await timeline.undoToLastCheckpoint();
+		assert.deepStrictEqual(timeline.requestDisablement.get().map(d => d.requestId), ['req4', 'req3', 'req2', 'req1']);
+
+		assert.strictEqual(timeline.canUndo.get(), false);
+
+		// Redo should also step one request at a time (not skip all at once)
+		assert.strictEqual(timeline.canRedo.get(), true);
+
+		await timeline.redoToNextCheckpoint();
+		assert.deepStrictEqual(timeline.requestDisablement.get().map(d => d.requestId), ['req4', 'req3', 'req2']);
+
+		await timeline.redoToNextCheckpoint();
+		assert.deepStrictEqual(timeline.requestDisablement.get().map(d => d.requestId), ['req4', 'req3']);
+
+		await timeline.redoToNextCheckpoint();
+		assert.deepStrictEqual(timeline.requestDisablement.get().map(d => d.requestId), ['req4']);
+
+		await timeline.redoToNextCheckpoint();
+		assert.deepStrictEqual(timeline.requestDisablement.get().map(d => d.requestId), []);
+
+		assert.strictEqual(timeline.canRedo.get(), false);
+	});
 });
 
 // Mock notebook service for tests that don't need notebook functionality
diff --git a/src/vs/workbench/contrib/chat/test/browser/chatImageCarouselService.test.ts b/src/vs/workbench/contrib/chat/test/browser/chatImageCarouselService.test.ts
new file mode 100644
index 0000000000000..779a0d61b6d7d
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/browser/chatImageCarouselService.test.ts
@@ -0,0 +1,228 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { VSBuffer } from '../../../../../base/common/buffer.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { buildCollectionArgs, buildSingleImageArgs, collectCarouselSections, findClickedImageIndex, ICarouselSection } from '../../browser/chatImageCarouselService.js';
+import { IImageVariableEntry } from '../../common/attachments/chatVariableEntries.js';
+import { IChatRequestViewModel, IChatResponseViewModel } from '../../common/model/chatViewModel.js';
+
+suite('ChatImageCarouselService helpers', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	function makeRequest(id: string, variables: IChatRequestViewModel['variables'], messageText: string = 'Request'): IChatRequestViewModel {
+		return {
+			id,
+			sessionResource: URI.parse('chat-session://test/session'),
+			dataId: `data-${id}`,
+			username: 'test-user',
+			message: { text: messageText, parts: [] },
+			messageText,
+			attempt: 0,
+			variables,
+			currentRenderedHeight: undefined,
+			shouldBeRemovedOnSend: undefined,
+			isComplete: true,
+			isCompleteAddedRequest: true,
+			slashCommand: undefined,
+			agentOrSlashCommandDetected: false,
+			shouldBeBlocked: undefined!,
+			timestamp: 0,
+		} as unknown as IChatRequestViewModel;
+	}
+
+	function makeResponse(requestId: string, id: string = 'resp-1'): IChatResponseViewModel {
+		return {
+			id,
+			requestId,
+			sessionResource: URI.parse('chat-session://test/session'),
+			response: { value: [] },
+			session: { getItems: () => [] },
+		} as unknown as IChatResponseViewModel;
+	}
+
+	function makeImageVariableEntry(overrides: Partial<IImageVariableEntry> & Pick<IImageVariableEntry, 'value'>): IImageVariableEntry {
+		const { value, ...rest } = overrides;
+		return {
+			id: 'img-1',
+			kind: 'image',
+			name: 'cat.png',
+			value,
+			mimeType: 'image/png',
+			...rest,
+		};
+	}
+
+	function makeImage(id: string, name: string = 'img.png', mimeType: string = 'image/png'): { id: string; name: string; mimeType: string; data: Uint8Array } {
+		return { id, name, mimeType, data: new Uint8Array([1, 2, 3]) };
+	}
+
+	function makeSections(...imageCounts: number[]): ICarouselSection[] {
+		return imageCounts.map((count, sectionIdx) => ({
+			title: `Section ${sectionIdx}`,
+			images: Array.from({ length: count }, (_, imgIdx) =>
+				makeImage(URI.file(`/image_s${sectionIdx}_i${imgIdx}.png`).toString(), `image_s${sectionIdx}_i${imgIdx}.png`)
+			),
+		}));
+	}
+
+	suite('findClickedImageIndex', () => {
+
+		test('finds image by URI string match in first section', () => {
+			const sections = makeSections(3);
+			const targetUri = URI.parse(sections[0].images[1].id);
+			assert.strictEqual(findClickedImageIndex(sections, targetUri), 1);
+		});
+
+		test('finds image by URI string match in second section', () => {
+			const sections = makeSections(2, 3);
+			const targetUri = URI.parse(sections[1].images[2].id);
+			// globalOffset = 2 (first section) + 2 (third in second section) = 4
+			assert.strictEqual(findClickedImageIndex(sections, targetUri), 4);
+		});
+
+		test('returns -1 when no match found', () => {
+			const sections = makeSections(2, 2);
+			const unknownUri = URI.file('/nonexistent.png');
+			assert.strictEqual(findClickedImageIndex(sections, unknownUri), -1);
+		});
+
+		test('falls back to data buffer match', () => {
+			const sections: ICarouselSection[] = [{
+				title: 'Section',
+				images: [
+					{ id: 'custom-id-1', name: 'a.png', mimeType: 'image/png', data: new Uint8Array([10, 20]) },
+					{ id: 'custom-id-2', name: 'b.png', mimeType: 'image/png', data: new Uint8Array([30, 40]) },
+				],
+			}];
+			const unknownUri = URI.from({ scheme: 'data', path: 'b.png' });
+			assert.strictEqual(findClickedImageIndex(sections, unknownUri, new Uint8Array([30, 40])), 1);
+		});
+
+		test('returns -1 for empty sections', () => {
+			assert.strictEqual(findClickedImageIndex([], URI.file('/x.png')), -1);
+		});
+	});
+
+	suite('buildCollectionArgs', () => {
+
+		test('uses section title when single section', () => {
+			const sections = makeSections(2);
+			const result = buildCollectionArgs(sections, 0, URI.file('/session'));
+			assert.deepStrictEqual(result, {
+				collection: {
+					id: URI.file('/session').toString() + '_carousel',
+					title: 'Section 0',
+					sections,
+				},
+				startIndex: 0,
+			});
+		});
+
+		test('uses generic title for multiple sections', () => {
+			const sections = makeSections(1, 1);
+			const result = buildCollectionArgs(sections, 1, URI.file('/session'));
+			assert.strictEqual(result.collection.title, 'Conversation Images');
+			assert.strictEqual(result.startIndex, 1);
+		});
+	});
+
+	suite('buildSingleImageArgs', () => {
+
+		test('extracts name and mime from URI path', () => {
+			const uri = URI.file('/path/to/photo.jpg');
+			const data = new Uint8Array([1, 2, 3]);
+			assert.deepStrictEqual(buildSingleImageArgs(uri, data), {
+				name: 'photo.jpg',
+				mimeType: 'image/jpg',
+				data,
+				title: 'photo.jpg',
+			});
+		});
+
+		test('defaults mime to image/png for unknown extension', () => {
+			const uri = URI.file('/path/to/file.xyz');
+			const data = new Uint8Array([1]);
+			assert.strictEqual(buildSingleImageArgs(uri, data).mimeType, 'image/png');
+		});
+	});
+
+	suite('collectCarouselSections', () => {
+
+		test('collects request attachment images for pending requests', async () => {
+			const request = makeRequest('req-1', [
+				makeImageVariableEntry({ value: new Uint8Array([1, 2, 3]) }),
+			], 'Pending request');
+
+			const result = await collectCarouselSections([request], async () => new Uint8Array());
+
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual(result[0].title, 'Pending request');
+			assert.strictEqual(result[0].images.length, 1);
+			assert.deepStrictEqual({
+				id: result[0].images[0].id,
+				name: result[0].images[0].name,
+				mimeType: result[0].images[0].mimeType,
+				data: [...result[0].images[0].data],
+			}, {
+				id: URI.from({ scheme: 'data', path: 'cat.png' }).toString(),
+				name: 'cat.png',
+				mimeType: 'image/png',
+				data: [1, 2, 3],
+			});
+		});
+
+		test('collects request attachment images restored as plain objects', async () => {
+			const request = makeRequest('req-1', [
+				makeImageVariableEntry({ value: { 0: 4, 1: 5, 2: 6 } }),
+			], 'Pending request');
+
+			const result = await collectCarouselSections([request], async () => new Uint8Array());
+
+			assert.deepStrictEqual([...result[0].images[0].data], [4, 5, 6]);
+		});
+
+		test('merges request images into matching response section', async () => {
+			const request = makeRequest('req-1', [
+				makeImageVariableEntry({ value: new Uint8Array([1, 2, 3]) }),
+			], 'Show me images');
+			const response = makeResponse('req-1');
+
+			const result = await collectCarouselSections([request, response], async uri => VSBuffer.fromString(`data-for-${uri.path}`).buffer);
+
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual(result[0].title, 'Show me images');
+			assert.strictEqual(result[0].images.length, 1);
+			assert.strictEqual(result[0].images[0].name, 'cat.png');
+		});
+
+		test('prefers paired request message text over extracted response title', async () => {
+			const request = makeRequest('req-1', [
+				makeImageVariableEntry({ value: new Uint8Array([1, 2, 3]) }),
+			], 'Request title wins');
+			const response = makeResponse('req-1');
+
+			const result = await collectCarouselSections([request, response], async () => new Uint8Array());
+
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual(result[0].title, 'Request title wins');
+		});
+
+		test('does not duplicate request images when response exists', async () => {
+			const request = makeRequest('req-1', [
+				makeImageVariableEntry({ value: new Uint8Array([1, 2, 3]) }),
+			], 'Show me images');
+			const response = makeResponse('req-1');
+
+			const result = await collectCarouselSections([request, response], async () => new Uint8Array());
+
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual(result[0].images.length, 1);
+		});
+	});
+
+});
diff --git a/src/vs/workbench/contrib/chat/test/browser/chatTipService.test.ts b/src/vs/workbench/contrib/chat/test/browser/chatTipService.test.ts
index 5af2338c70289..dc13e3e902e82 100644
--- a/src/vs/workbench/contrib/chat/test/browser/chatTipService.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/chatTipService.test.ts
@@ -5,35 +5,39 @@
 
 import assert from 'assert';
 import { Emitter, Event } from '../../../../../base/common/event.js';
+import { MarkdownString } from '../../../../../base/common/htmlContent.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
 import { ICommandEvent, ICommandService } from '../../../../../platform/commands/common/commands.js';
 import { ConfigurationTarget, IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
 import { TestConfigurationService } from '../../../../../platform/configuration/test/common/testConfigurationService.js';
 import { ContextKeyExpression, IContextKeyService } from '../../../../../platform/contextkey/common/contextkey.js';
 import { TestInstantiationService } from '../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import { IKeybindingService } from '../../../../../platform/keybinding/common/keybinding.js';
 import { MockContextKeyService } from '../../../../../platform/keybinding/test/common/mockKeybindingService.js';
 import { ILogService, NullLogService } from '../../../../../platform/log/common/log.js';
 import { IProductService } from '../../../../../platform/product/common/productService.js';
 import { IStorageService, InMemoryStorageService, StorageScope, StorageTarget } from '../../../../../platform/storage/common/storage.js';
-import { ChatTipService, IChatTip, ITipDefinition, TipEligibilityTracker } from '../../browser/chatTipService.js';
+import { ChatTipService, CREATE_AGENT_INSTRUCTIONS_TRACKING_COMMAND, CREATE_AGENT_TRACKING_COMMAND, CREATE_PROMPT_TRACKING_COMMAND, CREATE_SKILL_TRACKING_COMMAND, FORK_CONVERSATION_TRACKING_COMMAND, IChatTip, ITipDefinition, TipEligibilityTracker } from '../../browser/chatTipService.js';
 import { AgentFileType, IPromptPath, IPromptsService, IResolvedAgentFile, PromptsStorage } from '../../common/promptSyntax/service/promptsService.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { ChatContextKeys } from '../../common/actions/chatContextKeys.js';
-import { ChatAgentLocation, ChatConfiguration, ChatModeKind } from '../../common/constants.js';
+import { ChatAgentLocation, ChatModeKind } from '../../common/constants.js';
 import { PromptsType } from '../../common/promptSyntax/promptTypes.js';
 import { ILanguageModelToolsService } from '../../common/tools/languageModelToolsService.js';
 import { MockLanguageModelToolsService } from '../common/tools/mockLanguageModelToolsService.js';
+import { ChatTipTier, TIP_CATALOG } from '../../browser/chatTipCatalog.js';
 import { ChatEntitlement, IChatEntitlementService } from '../../../../services/chat/common/chatEntitlementService.js';
 import { TestChatEntitlementService } from '../../../../test/common/workbenchTestServices.js';
 import { IChatService } from '../../common/chatService/chatService.js';
 import { MockChatService } from '../common/chatService/mockChatService.js';
 import { CreateSlashCommandsUsageTracker } from '../../browser/createSlashCommandsUsageTracker.js';
-import { ChatRequestSlashCommandPart } from '../../common/requestParser/chatParserTypes.js';
+import { ChatRequestDynamicVariablePart, ChatRequestSlashCommandPart, IParsedChatRequest } from '../../common/requestParser/chatParserTypes.js';
 import { OffsetRange } from '../../../../../editor/common/core/ranges/offsetRange.js';
 import { Range } from '../../../../../editor/common/core/range.js';
 import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
 import { NullTelemetryService } from '../../../../../platform/telemetry/common/telemetryUtils.js';
 import { localChatSessionType } from '../../common/chatSessionsService.js';
+import { GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID } from '../../browser/actions/chatActions.js';
 
 class MockContextKeyServiceWithRulesMatching extends MockContextKeyService {
 	override contextMatchesRules(rules: ContextKeyExpression): boolean {
@@ -79,9 +83,23 @@ suite('ChatTipService', () => {
 		return testDisposables.add(instantiationService.createInstance(ChatTipService));
 	}
 
+	/**
+	 * Creates a mock ITipDefinition with a buildMessage function.
+	 * Tests can provide any ITipDefinition properties except buildMessage.
+	 */
+	function createMockTip(overrides: Omit<Partial<ITipDefinition>, 'buildMessage'> & Pick<ITipDefinition, 'id'> & { message?: string }): ITipDefinition {
+		const { message, ...rest } = overrides;
+		return {
+			tier: ChatTipTier.Qol,
+			...rest,
+			buildMessage: () => new MarkdownString(message ?? 'test'),
+		};
+	}
+
 	setup(() => {
 		instantiationService = testDisposables.add(new TestInstantiationService());
 		contextKeyService = new MockContextKeyServiceWithRulesMatching();
+		contextKeyService.createKey(ChatContextKeys.foregroundSessionCount.key, 1);
 		configurationService = new TestConfigurationService();
 		commandExecutedEmitter = testDisposables.add(new Emitter<ICommandEvent>());
 		storageService = testDisposables.add(new InMemoryStorageService());
@@ -106,6 +124,9 @@ suite('ChatTipService', () => {
 		instantiationService.stub(IChatEntitlementService, chatEntitlementService);
 		instantiationService.stub(IChatService, new MockChatService());
 		instantiationService.stub(ITelemetryService, NullTelemetryService);
+		instantiationService.stub(IKeybindingService, {
+			lookupKeybinding: () => undefined,
+		} as Partial<IKeybindingService> as IKeybindingService);
 	});
 
 	test('returns a welcome tip', () => {
@@ -117,6 +138,233 @@ suite('ChatTipService', () => {
 		assert.ok(tip.content.value.length > 0, 'Tip should have content');
 	});
 
+	test('uses descriptive titles for tip command links', () => {
+		for (const tip of TIP_CATALOG) {
+			const markdown = tip.buildMessage({
+				keybindingService: {
+					lookupKeybinding: () => undefined,
+				} as Partial<IKeybindingService> as IKeybindingService,
+			}).value;
+
+			const commandLinkRegex = /\[[^\]]+\]\((command:[^)]+)\)/g;
+			let match: RegExpExecArray | null;
+			while ((match = commandLinkRegex.exec(markdown)) !== null) {
+				assert.ok(/\s"[^"]+"$/.test(match[1]), `Expected command link in ${tip.id} to include a descriptive title: ${match[0]}`);
+			}
+		}
+	});
+
+	test('records # file reference usage for attach files tip eligibility', () => {
+		const submitRequestEmitter = testDisposables.add(new Emitter<{ readonly chatSessionResource: URI; readonly message?: IParsedChatRequest }>());
+		instantiationService.stub(IChatService, {
+			onDidSubmitRequest: submitRequestEmitter.event,
+			getSession: () => undefined,
+		} as Partial<IChatService> as IChatService);
+
+		createService();
+
+		submitRequestEmitter.fire({
+			chatSessionResource: URI.parse('chat:session-attach-file'),
+			message: {
+				text: 'what does #file:README.md say',
+				parts: [new ChatRequestDynamicVariablePart(
+					new OffsetRange(10, 26),
+					new Range(1, 11, 1, 27),
+					'#file:README.md',
+					'file',
+					undefined,
+					URI.file('/workspace/README.md'),
+					undefined,
+					undefined,
+					true,
+					false,
+				)],
+			},
+		});
+
+		const executedCommands = JSON.parse(storageService.get('chat.tips.executedCommands', StorageScope.APPLICATION) ?? '[]') as string[];
+		assert.ok(executedCommands.includes('chat.tips.attachFiles.referenceUsed'));
+	});
+
+	test('records only matching create tip usage for submitted create command', () => {
+		const submitRequestEmitter = testDisposables.add(new Emitter<{ readonly chatSessionResource: URI; readonly message?: IParsedChatRequest }>());
+		instantiationService.stub(IChatService, {
+			onDidSubmitRequest: submitRequestEmitter.event,
+			getSession: () => undefined,
+		} as Partial<IChatService> as IChatService);
+
+		createService();
+
+		submitRequestEmitter.fire({
+			chatSessionResource: URI.parse('chat:session-create-prompt'),
+			message: {
+				text: '/create-prompt scaffold a reusable prompt',
+				parts: [],
+			},
+		});
+
+		const executedCommands = JSON.parse(storageService.get('chat.tips.executedCommands', StorageScope.APPLICATION) ?? '[]') as string[];
+		assert.ok(executedCommands.includes(CREATE_PROMPT_TRACKING_COMMAND));
+		assert.ok(!executedCommands.includes(CREATE_AGENT_INSTRUCTIONS_TRACKING_COMMAND));
+		assert.ok(!executedCommands.includes(CREATE_AGENT_TRACKING_COMMAND));
+		assert.ok(!executedCommands.includes(CREATE_SKILL_TRACKING_COMMAND));
+		assert.ok(!executedCommands.includes(FORK_CONVERSATION_TRACKING_COMMAND));
+	});
+
+	test('records init tip usage for submitted /init command', () => {
+		const submitRequestEmitter = testDisposables.add(new Emitter<{ readonly chatSessionResource: URI; readonly message?: IParsedChatRequest }>());
+		instantiationService.stub(IChatService, {
+			onDidSubmitRequest: submitRequestEmitter.event,
+			getSession: () => undefined,
+		} as Partial<IChatService> as IChatService);
+
+		createService();
+
+		submitRequestEmitter.fire({
+			chatSessionResource: URI.parse('chat:session-init'),
+			message: {
+				text: '/init',
+				parts: [],
+			},
+		});
+
+		const executedCommands = JSON.parse(storageService.get('chat.tips.executedCommands', StorageScope.APPLICATION) ?? '[]') as string[];
+		assert.ok(executedCommands.includes(CREATE_AGENT_INSTRUCTIONS_TRACKING_COMMAND));
+		assert.ok(!executedCommands.includes(CREATE_PROMPT_TRACKING_COMMAND));
+		assert.ok(!executedCommands.includes(CREATE_AGENT_TRACKING_COMMAND));
+		assert.ok(!executedCommands.includes(CREATE_SKILL_TRACKING_COMMAND));
+		assert.ok(!executedCommands.includes(FORK_CONVERSATION_TRACKING_COMMAND));
+	});
+
+
+	test('hides shown slash tip after submitted slash command without clicking tip link', () => {
+		const submitRequestEmitter = testDisposables.add(new Emitter<{ readonly chatSessionResource: URI; readonly message?: IParsedChatRequest }>());
+		instantiationService.stub(IChatService, {
+			onDidSubmitRequest: submitRequestEmitter.event,
+			getSession: () => undefined,
+		} as Partial<IChatService> as IChatService);
+
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, localChatSessionType);
+
+		let tip = service.getWelcomeTip(contextKeyService);
+		assert.ok(tip);
+
+		for (let i = 0; i < TIP_CATALOG.length && tip?.id !== 'tip.init'; i++) {
+			tip = service.navigateToNextTip();
+		}
+
+		assert.ok(tip);
+		assert.strictEqual(tip.id, 'tip.init', 'Expected to navigate to the init tip before submitting /init');
+
+		let didHide = false;
+		testDisposables.add(service.onDidHideTip(() => didHide = true));
+
+		submitRequestEmitter.fire({
+			chatSessionResource: URI.parse('chat:session-advance-init'),
+			message: {
+				text: '/init',
+				parts: [],
+			},
+		});
+
+		assert.ok(didHide, 'Expected slash tip to hide after submitting /init');
+		assert.notStrictEqual(service.getWelcomeTip(contextKeyService)?.id, 'tip.init', 'Expected init tip to stay excluded after slash usage');
+	});
+
+	test('removes slash tip from rotation after submitted slash command via eligibility tracking', () => {
+		const submitRequestEmitter = testDisposables.add(new Emitter<{ readonly chatSessionResource: URI; readonly message?: IParsedChatRequest }>());
+		instantiationService.stub(IChatService, {
+			onDidSubmitRequest: submitRequestEmitter.event,
+			getSession: () => undefined,
+		} as Partial<IChatService> as IChatService);
+
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, localChatSessionType);
+
+		let tip = service.getWelcomeTip(contextKeyService);
+		assert.ok(tip);
+
+		for (let i = 0; i < TIP_CATALOG.length && tip?.id !== 'tip.init'; i++) {
+			tip = service.navigateToNextTip();
+		}
+
+		assert.ok(tip);
+		assert.strictEqual(tip.id, 'tip.init');
+
+		submitRequestEmitter.fire({
+			chatSessionResource: URI.parse('chat:session-rotate-init'),
+			message: {
+				text: '/init',
+				parts: [],
+			},
+		});
+
+		for (let i = 0; i < TIP_CATALOG.length; i++) {
+			tip = service.navigateToNextTip();
+			if (!tip) {
+				break;
+			}
+			assert.notStrictEqual(tip.id, 'tip.init', 'Expected init tip to be removed from tip rotation');
+		}
+
+		const executedCommands = JSON.parse(storageService.get('chat.tips.executedCommands', StorageScope.APPLICATION) ?? '[]') as string[];
+		assert.ok(executedCommands.includes(CREATE_AGENT_INSTRUCTIONS_TRACKING_COMMAND), 'Expected slash usage to be tracked in executed command exclusions');
+	});
+
+	test('removes slash tip from rotation when slash usage is recorded before input transformation', () => {
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, localChatSessionType);
+
+		let tip = service.getWelcomeTip(contextKeyService);
+		assert.ok(tip);
+
+		for (let i = 0; i < TIP_CATALOG.length && tip?.id !== 'tip.init'; i++) {
+			tip = service.navigateToNextTip();
+		}
+
+		assert.ok(tip);
+		assert.strictEqual(tip.id, 'tip.init');
+
+		service.recordSlashCommandUsage('init');
+
+		for (let i = 0; i < TIP_CATALOG.length; i++) {
+			tip = service.navigateToNextTip();
+			if (!tip) {
+				break;
+			}
+			assert.notStrictEqual(tip.id, 'tip.init', 'Expected init tip to be removed from tip rotation');
+		}
+
+		const executedCommands = JSON.parse(storageService.get('chat.tips.executedCommands', StorageScope.APPLICATION) ?? '[]') as string[];
+		assert.ok(executedCommands.includes(CREATE_AGENT_INSTRUCTIONS_TRACKING_COMMAND), 'Expected slash usage to be tracked in executed command exclusions');
+	});
+
+	test('records fork tip usage for submitted /fork command', () => {
+		const submitRequestEmitter = testDisposables.add(new Emitter<{ readonly chatSessionResource: URI; readonly message?: IParsedChatRequest }>());
+		instantiationService.stub(IChatService, {
+			onDidSubmitRequest: submitRequestEmitter.event,
+			getSession: () => undefined,
+		} as Partial<IChatService> as IChatService);
+
+		createService();
+
+		submitRequestEmitter.fire({
+			chatSessionResource: URI.parse('chat:session-fork'),
+			message: {
+				text: '/fork',
+				parts: [],
+			},
+		});
+
+		const executedCommands = JSON.parse(storageService.get('chat.tips.executedCommands', StorageScope.APPLICATION) ?? '[]') as string[];
+		assert.ok(executedCommands.includes(FORK_CONVERSATION_TRACKING_COMMAND));
+		assert.ok(!executedCommands.includes(CREATE_AGENT_INSTRUCTIONS_TRACKING_COMMAND));
+		assert.ok(!executedCommands.includes(CREATE_PROMPT_TRACKING_COMMAND));
+		assert.ok(!executedCommands.includes(CREATE_AGENT_TRACKING_COMMAND));
+		assert.ok(!executedCommands.includes(CREATE_SKILL_TRACKING_COMMAND));
+	});
+
 	test('returns Auto switch tip when current model is gpt-4.1', () => {
 		const service = createService();
 		contextKeyService.createKey(ChatContextKeys.chatModelId.key, 'gpt-4.1');
@@ -125,6 +373,7 @@ suite('ChatTipService', () => {
 
 		assert.ok(tip);
 		assert.strictEqual(tip.id, 'tip.switchToAuto');
+		assert.ok(tip.content.value.includes('GPT-4.1'));
 	});
 
 	test('does not return Auto switch tip when current model is not gpt-4.1', () => {
@@ -177,6 +426,7 @@ suite('ChatTipService', () => {
 		assert.strictEqual(firstTip.id, 'tip.switchToAuto');
 
 		const switchedContextKeyService = new MockContextKeyServiceWithRulesMatching();
+		switchedContextKeyService.createKey(ChatContextKeys.foregroundSessionCount.key, 1);
 		switchedContextKeyService.createKey(ChatContextKeys.chatModelId.key, 'auto');
 		const nextTip = service.getWelcomeTip(switchedContextKeyService);
 
@@ -238,6 +488,30 @@ suite('ChatTipService', () => {
 		assert.strictEqual(tip, undefined, 'Should not return a tip in editor inline chat');
 	});
 
+	test('returns a tip when foreground session count is exactly one', () => {
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.foregroundSessionCount.key, 1);
+
+		const tip = service.getWelcomeTip(contextKeyService);
+		assert.ok(tip, 'Should return a tip when exactly one foreground chat session is visible');
+	});
+
+	test('returns undefined when foreground session count is zero', () => {
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.foregroundSessionCount.key, 0);
+
+		const tip = service.getWelcomeTip(contextKeyService);
+		assert.strictEqual(tip, undefined, 'Should not return a tip when no foreground chat sessions are visible');
+	});
+
+	test('returns undefined when foreground session count is greater than one', () => {
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.foregroundSessionCount.key, 2);
+
+		const tip = service.getWelcomeTip(contextKeyService);
+		assert.strictEqual(tip, undefined, 'Should not return a tip when multiple foreground chat sessions are visible');
+	});
+
 	test('dismissTip excludes the dismissed tip and allows a new one', () => {
 		const service = createService();
 
@@ -266,6 +540,155 @@ suite('ChatTipService', () => {
 		}
 	});
 
+	test('dismissTipForSession hides tips until resetSession', () => {
+		const service = createService();
+
+		const tip = service.getWelcomeTip(contextKeyService);
+		assert.ok(tip);
+
+		service.dismissTipForSession();
+
+		assert.strictEqual(service.getWelcomeTip(contextKeyService), undefined, 'Tips should stay hidden for the current session after dismissing');
+
+		service.resetSession();
+		assert.ok(service.getWelcomeTip(contextKeyService), 'Tips should reappear after resetting the session');
+	});
+
+	test('navigateToNextTip keeps foundational tips before QoL tips', () => {
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
+		contextKeyService.createKey(ChatContextKeys.chatModeName.key, 'Agent');
+		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, localChatSessionType);
+		contextKeyService.createKey(ChatContextKeys.chatModelId.key, 'auto');
+
+		const firstTip = service.getWelcomeTip(contextKeyService);
+		assert.ok(firstTip);
+		assert.strictEqual(firstTip.id, 'tip.planMode');
+
+		const secondTip = service.navigateToNextTip();
+		assert.ok(secondTip);
+		assert.strictEqual(secondTip.id, 'tip.createAgent', 'Expected next tip to remain in foundational tips before QoL tips');
+	});
+
+	test('navigateToPreviousTip follows reverse of preferred order', () => {
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
+		contextKeyService.createKey(ChatContextKeys.chatModeName.key, 'Agent');
+		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, localChatSessionType);
+		contextKeyService.createKey(ChatContextKeys.chatModelId.key, 'auto');
+
+		const firstTip = service.getWelcomeTip(contextKeyService);
+		assert.ok(firstTip);
+		assert.strictEqual(firstTip.id, 'tip.planMode');
+
+		const secondTip = service.navigateToNextTip();
+		assert.ok(secondTip);
+		assert.strictEqual(secondTip.id, 'tip.createAgent');
+
+		const previousTip = service.navigateToPreviousTip();
+		assert.ok(previousTip);
+		assert.strictEqual(previousTip.id, 'tip.planMode', 'Expected previous tip to reverse the preferred ordering');
+	});
+
+	test('getNextEligibleTip returns next tip even when only one remains', async () => {
+		const service = createService();
+
+		// Flush microtask queue so async file-check exclusions resolve
+		await new Promise<void>(r => queueMicrotask(r));
+
+		// Get the initial tip
+		const tip1 = service.getWelcomeTip(contextKeyService);
+		assert.ok(tip1, 'Should have an initial tip');
+
+		// Navigate to next tip
+		const tip2 = service.navigateToNextTip();
+		assert.ok(tip2, 'Should have a second tip');
+		assert.notStrictEqual(tip1.id, tip2.id, 'Second tip should be different');
+
+		// Dismiss all tips except tip1 by dismissing current tip and using getNextEligibleTip
+		const dismissedIds = new Set<string>();
+		dismissedIds.add(tip2.id);
+		service.dismissTip();
+
+		// Keep dismissing until we can't get any more tips
+		let nextTip = service.getNextEligibleTip();
+		while (nextTip && !dismissedIds.has(nextTip.id)) {
+			if (nextTip.id === tip1.id) {
+				// We found tip1 again - this is the expected behavior (bug fix verification)
+				break;
+			}
+			dismissedIds.add(nextTip.id);
+			service.dismissTip();
+			nextTip = service.getNextEligibleTip();
+		}
+
+		// The key assertion: getNextEligibleTip should return tip1 even if it's the only one left
+		assert.ok(nextTip, 'getNextEligibleTip should return the last remaining eligible tip');
+	});
+
+	test('getNextEligibleTip returns undefined when all tips are dismissed', async () => {
+		const service = createService();
+
+		// Flush microtask queue so async file-check exclusions resolve
+		await new Promise<void>(r => queueMicrotask(r));
+
+		// Dismiss all tips
+		for (let i = 0; i < 100; i++) {
+			const tip = service.getWelcomeTip(contextKeyService);
+			if (!tip) {
+				break;
+			}
+			service.dismissTip();
+		}
+
+		// After dismissing all, getNextEligibleTip should return undefined
+		const nextTip = service.getNextEligibleTip();
+		assert.strictEqual(nextTip, undefined, 'getNextEligibleTip should return undefined when all tips are dismissed');
+	});
+
+	test('getNextEligibleTip keeps preferred onboarding order after dismissing plan tip', () => {
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
+		contextKeyService.createKey(ChatContextKeys.chatModeName.key, 'Agent');
+		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, localChatSessionType);
+		contextKeyService.createKey(ChatContextKeys.chatModelId.key, 'auto');
+
+		const firstTip = service.getWelcomeTip(contextKeyService);
+		assert.ok(firstTip);
+		assert.strictEqual(firstTip.id, 'tip.planMode');
+
+		service.dismissTip();
+		const secondTip = service.getNextEligibleTip();
+		assert.ok(secondTip);
+		assert.strictEqual(secondTip.id, 'tip.createAgent', 'Expected next tip to follow preferred onboarding order before QoL tips');
+	});
+
+	test('getNextEligibleTip picks next relative to current tip after dismissing from middle of order', () => {
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
+		contextKeyService.createKey(ChatContextKeys.chatModeName.key, 'Agent');
+		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, localChatSessionType);
+		contextKeyService.createKey(ChatContextKeys.chatModelId.key, 'auto');
+
+		const firstTip = service.getWelcomeTip(contextKeyService);
+		assert.ok(firstTip);
+
+		const secondTip = service.navigateToNextTip();
+		assert.ok(secondTip);
+
+		const expectedNextAfterSecond = service.navigateToNextTip();
+		assert.ok(expectedNextAfterSecond, 'Expected at least three tips to validate relative ordering');
+
+		const backToSecond = service.navigateToPreviousTip();
+		assert.ok(backToSecond);
+		assert.strictEqual(backToSecond.id, secondTip.id);
+
+		service.dismissTip();
+		const actualNext = service.getNextEligibleTip();
+		assert.ok(actualNext);
+		assert.strictEqual(actualNext.id, expectedNextAfterSecond.id, 'Expected getNextEligibleTip to advance relative to current tip rather than restart from top priority tip');
+	});
+
 	test('dismissTip fires onDidDismissTip event', () => {
 		const service = createService();
 
@@ -374,6 +797,29 @@ suite('ChatTipService', () => {
 		assert.ok(storageService.get('chat.tip.dismissed', StorageScope.APPLICATION), 'Expected dismissed tips to migrate to application storage');
 	});
 
+	test('tip.undoChanges describes where to find restore checkpoint', () => {
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, localChatSessionType);
+		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
+
+		const tip = findTipById(service, 'tip.undoChanges');
+
+		assert.ok(tip);
+		assert.ok(tip.content.value.includes('Hover a previous request'));
+		assert.ok(tip.content.value.includes('Restore Checkpoint'));
+	});
+
+	test('tip.mermaid uses sentence punctuation in display text', () => {
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
+
+		const tip = findTipById(service, 'tip.mermaid');
+
+		assert.ok(tip);
+		assert.ok(tip.content.value.includes('flow chart. It can render Mermaid diagrams directly in chat.'));
+		assert.ok(!tip.content.value.includes('flow chart; it can render Mermaid diagrams directly in chat.'));
+	});
+
 	function createMockPromptsService(
 		agentInstructions: IResolvedAgentFile[] = [],
 		promptInstructions: IPromptPath[] = [],
@@ -391,11 +837,10 @@ suite('ChatTipService', () => {
 	}
 
 	test('excludes tip.undoChanges when restore checkpoint command has been executed', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.undoChanges',
-			message: 'test',
 			excludeWhenCommandsExecuted: ['workbench.action.chat.restoreCheckpoint'],
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -414,11 +859,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('persists executed command exclusions in application storage', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.undoChanges',
-			message: 'test',
 			excludeWhenCommandsExecuted: ['workbench.action.chat.restoreCheckpoint'],
-		};
+		});
 
 		testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -437,11 +881,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('migrates executed command exclusions from profile to application storage', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.undoChanges',
-			message: 'test',
 			excludeWhenCommandsExecuted: ['workbench.action.chat.restoreCheckpoint'],
-		};
+		});
 
 		storageService.store('chat.tips.executedCommands', JSON.stringify(['workbench.action.chat.restoreCheckpoint']), StorageScope.PROFILE, StorageTarget.MACHINE);
 
@@ -459,11 +902,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.customInstructions when copilot-instructions.md exists in workspace', async () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customInstructions',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.instructions, agentFileType: AgentFileType.copilotInstructionsMd, excludeUntilChecked: true },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -481,11 +923,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('does not exclude tip.customInstructions when only AGENTS.md exists', async () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customInstructions',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.instructions, agentFileType: AgentFileType.copilotInstructionsMd, excludeUntilChecked: true },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -503,11 +944,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.customInstructions when .instructions.md files exist in workspace', async () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customInstructions',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.instructions, agentFileType: AgentFileType.copilotInstructionsMd, excludeUntilChecked: true },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -525,11 +965,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('does not exclude tip.customInstructions when no instruction files exist', async () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customInstructions',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.instructions, agentFileType: AgentFileType.copilotInstructionsMd, excludeUntilChecked: true },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -547,11 +986,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.customInstructions when generate instructions command has been executed', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customInstructions',
-			message: 'test',
-			excludeWhenCommandsExecuted: ['workbench.action.chat.generateInstructions'],
-		};
+			excludeWhenCommandsExecuted: [GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID],
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -564,17 +1002,16 @@ suite('ChatTipService', () => {
 
 		assert.strictEqual(tracker.isExcluded(tip), false, 'Should not be excluded before command is executed');
 
-		commandExecutedEmitter.fire({ commandId: 'workbench.action.chat.generateInstructions', args: [] });
+		commandExecutedEmitter.fire({ commandId: GENERATE_AGENT_INSTRUCTIONS_COMMAND_ID, args: [] });
 
 		assert.strictEqual(tracker.isExcluded(tip), true, 'Should be excluded after generate instructions command is executed');
 	});
 
 	test('excludes tip.agentMode when agent mode has been used in workspace', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.agentMode',
-			message: 'test',
 			excludeWhenModesUsed: [ChatModeKind.Agent],
-		};
+		});
 
 		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
 		contextKeyService.createKey(ChatContextKeys.chatModeName.key, 'Agent');
@@ -596,11 +1033,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.planMode when Plan mode has been used in workspace', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.planMode',
-			message: 'test',
 			excludeWhenModesUsed: ['Plan'],
-		};
+		});
 
 		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
 		contextKeyService.createKey(ChatContextKeys.chatModeName.key, 'Plan');
@@ -622,11 +1058,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.planMode when open plan command has been executed', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.planMode',
-			message: 'test',
 			excludeWhenCommandsExecuted: ['workbench.action.chat.openPlan'],
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -645,11 +1080,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('persists command exclusions to workspace storage across tracker instances', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.undoChanges',
-			message: 'test',
 			excludeWhenCommandsExecuted: ['workbench.action.chat.restoreCheckpoint'],
-		};
+		});
 
 		const tracker1 = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -677,11 +1111,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('persists mode exclusions to workspace storage across tracker instances', () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.agentMode',
-			message: 'test',
 			excludeWhenModesUsed: [ChatModeKind.Agent],
-		};
+		});
 
 		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
 		contextKeyService.createKey(ChatContextKeys.chatModeName.key, 'Agent');
@@ -711,6 +1144,91 @@ suite('ChatTipService', () => {
 		assert.strictEqual(tracker2.isExcluded(tip), true, 'New tracker should read persisted mode exclusion from workspace storage');
 	});
 
+	test('prioritizes foundational tips over QoL tips when both are eligible', () => {
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
+		contextKeyService.createKey(ChatContextKeys.chatModeName.key, 'Agent');
+
+		const tip = service.getWelcomeTip(contextKeyService);
+
+		assert.ok(tip);
+		assert.strictEqual(tip.id, 'tip.planMode', 'Expected foundational tip to be prioritized before eligible QoL tips');
+	});
+
+	test('prioritizes preferred onboarding tips in requested order', () => {
+		const service = createService();
+		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
+		contextKeyService.createKey(ChatContextKeys.chatModeName.key, 'Agent');
+		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, localChatSessionType);
+		contextKeyService.createKey(ChatContextKeys.chatModelId.key, 'auto');
+
+		const seen: string[] = [];
+		for (let i = 0; i < 3; i++) {
+			const tip = service.getWelcomeTip(contextKeyService);
+			assert.ok(tip);
+			seen.push(tip.id);
+			service.dismissTip();
+		}
+
+		assert.deepStrictEqual(seen, ['tip.planMode', 'tip.createAgent', 'tip.createSkill']);
+	});
+
+	test('randomizes QoL tips when no foundational tips are eligible', () => {
+		const service = createService();
+		const modeKindKey = contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
+		const modeNameKey = contextKeyService.createKey<string>(ChatContextKeys.chatModeName.key, 'Plan');
+		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, 'cloud');
+		contextKeyService.createKey(ChatContextKeys.chatModelId.key, 'auto');
+
+		const originalRandom = Math.random;
+		try {
+			Math.random = () => 0;
+			const firstTip = service.getWelcomeTip(contextKeyService);
+
+			service.resetSession();
+
+			Math.random = () => 0.9999;
+			const secondTip = service.getWelcomeTip(contextKeyService);
+
+			assert.ok(firstTip);
+			assert.ok(secondTip);
+			assert.notStrictEqual(firstTip.id, secondTip.id, 'Expected different QoL tips for different random values');
+			assert.notStrictEqual(firstTip.id, 'tip.planMode');
+			assert.notStrictEqual(secondTip.id, 'tip.planMode');
+		} finally {
+			Math.random = originalRandom;
+			modeKindKey.set(ChatModeKind.Agent);
+			modeNameKey.set('Plan');
+		}
+	});
+
+	test('resetSession reevaluates foundational tips for the next chat session', () => {
+		const service = createService();
+		const modeKindKey = contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
+		const modeNameKey = contextKeyService.createKey<string>(ChatContextKeys.chatModeName.key, 'Plan');
+		const sessionTypeKey = contextKeyService.createKey<string>(ChatContextKeys.chatSessionType.key, 'cloud');
+		contextKeyService.createKey(ChatContextKeys.chatModelId.key, 'auto');
+
+		const originalRandom = Math.random;
+		try {
+			Math.random = () => 0.9999;
+			const qolTip = service.getWelcomeTip(contextKeyService);
+			assert.ok(qolTip);
+			assert.notStrictEqual(qolTip.id, 'tip.planMode');
+
+			service.resetSession();
+			modeNameKey.set('Agent');
+			sessionTypeKey.set(localChatSessionType);
+
+			const foundationalTip = service.getWelcomeTip(contextKeyService);
+			assert.ok(foundationalTip);
+			assert.strictEqual(foundationalTip.id, 'tip.createAgent', 'Expected foundational ordering to restart on new chat session');
+		} finally {
+			Math.random = originalRandom;
+			modeKindKey.set(ChatModeKind.Agent);
+		}
+	});
+
 	test('resetSession allows a new welcome tip', () => {
 		const service = createService();
 
@@ -747,11 +1265,10 @@ suite('ChatTipService', () => {
 
 	test('excludes tip when tracked tool has been invoked', () => {
 		const mockToolsService = createMockToolsService();
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.mermaid',
-			message: 'test',
 			excludeWhenToolsInvoked: ['renderMermaidDiagram'],
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -771,11 +1288,10 @@ suite('ChatTipService', () => {
 
 	test('persists tool exclusions to workspace storage across tracker instances', () => {
 		const mockToolsService = createMockToolsService();
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.subagents',
-			message: 'test',
 			excludeWhenToolsInvoked: ['runSubagent'],
-		};
+		});
 
 		const tracker1 = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -803,11 +1319,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('excludes tip.skill when skill files exist in workspace', async () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.skill',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.skill },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -825,11 +1340,10 @@ suite('ChatTipService', () => {
 	});
 
 	test('does not exclude tip.skill when no skill files exist', async () => {
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.skill',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.skill },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -846,132 +1360,59 @@ suite('ChatTipService', () => {
 		assert.strictEqual(tracker.isExcluded(tip), false, 'Should not be excluded when no skill files exist');
 	});
 
-	test('shows tip.createSlashCommands when context key is false', () => {
+	test('shows all create slash command tips in local chat sessions', () => {
 		const service = createService();
-		contextKeyService.createKey(ChatContextKeys.hasUsedCreateSlashCommands.key, false);
 		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, localChatSessionType);
 
-		// Dismiss tips until we find createSlashCommands or run out
-		let found = false;
+		const expectedCreateTips = new Set(['tip.init', 'tip.createPrompt', 'tip.createAgent', 'tip.createSkill']);
+		const seenCreateTips = new Set<string>();
 		for (let i = 0; i < 100; i++) {
 			const tip = service.getWelcomeTip(contextKeyService);
 			if (!tip) {
 				break;
 			}
-			if (tip.id === 'tip.createSlashCommands') {
-				found = true;
-				break;
+			if (expectedCreateTips.has(tip.id)) {
+				seenCreateTips.add(tip.id);
+				if (seenCreateTips.size === expectedCreateTips.size) {
+					break;
+				}
 			}
 			service.dismissTip();
 		}
 
-		assert.ok(found, 'Should eventually show tip.createSlashCommands when context key is false');
+		assert.deepStrictEqual([...seenCreateTips].sort(), [...expectedCreateTips].sort());
 	});
 
-	test('does not show tip.createSlashCommands in non-local chat sessions', () => {
+	test('does not show create slash command tips in non-local chat sessions', () => {
 		const service = createService();
-		contextKeyService.createKey(ChatContextKeys.hasUsedCreateSlashCommands.key, false);
 		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, 'cloud');
+		const createTipIds = new Set(['tip.init', 'tip.createPrompt', 'tip.createAgent', 'tip.createSkill']);
 
 		for (let i = 0; i < 100; i++) {
 			const tip = service.getWelcomeTip(contextKeyService);
 			if (!tip) {
 				break;
 			}
-			assert.notStrictEqual(tip.id, 'tip.createSlashCommands', 'Should not show tip.createSlashCommands in non-local sessions');
-			service.dismissTip();
-		}
-	});
-
-	test('does not show tip.createSlashCommands when context key is true', () => {
-		storageService.store('chat.tips.usedCreateSlashCommands', true, StorageScope.APPLICATION, StorageTarget.MACHINE);
-		const service = createService();
-
-		for (let i = 0; i < 100; i++) {
-			const tip = service.getWelcomeTip(contextKeyService);
-			if (!tip) {
-				break;
-			}
-			assert.notStrictEqual(tip.id, 'tip.createSlashCommands', 'Should not show tip.createSlashCommands when context key is true');
+			assert.ok(!createTipIds.has(tip.id), 'Should not show create slash command tips in non-local sessions');
 			service.dismissTip();
 		}
 	});
 
-	test('does not show tip.yoloMode after auto-approve has ever been enabled', () => {
+	test('does not show create prompt tip when create prompt was already used', () => {
+		storageService.store('chat.tips.executedCommands', JSON.stringify([CREATE_PROMPT_TRACKING_COMMAND]), StorageScope.APPLICATION, StorageTarget.MACHINE);
 		const service = createService();
-		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
-
-		// Enable auto-approve so the service records yoloModeEverEnabled
-		configurationService.setUserConfiguration(ChatConfiguration.GlobalAutoApprove, true);
-		(configurationService as TestConfigurationService).onDidChangeConfigurationEmitter.fire({
-			affectsConfiguration: (key: string) => key === ChatConfiguration.GlobalAutoApprove,
-			affectedKeys: new Set([ChatConfiguration.GlobalAutoApprove]),
-			change: { keys: [], overrides: [] },
-			source: ConfigurationTarget.USER,
-		});
-
-		// Turn auto-approve back off
-		configurationService.setUserConfiguration(ChatConfiguration.GlobalAutoApprove, false);
-
-		// The yoloMode tip should never appear since it was ever enabled
-		for (let i = 0; i < 100; i++) {
-			const tip = service.getWelcomeTip(contextKeyService);
-			if (!tip) {
-				break;
-			}
-			assert.notStrictEqual(tip.id, 'tip.yoloMode', 'tip.yoloMode should not be shown after auto-approve was ever enabled');
-			service.dismissTip();
-		}
-
-		// Verify the flag was persisted
-		assert.strictEqual(
-			storageService.getBoolean('chat.tip.yoloModeEverEnabled', StorageScope.APPLICATION, false),
-			true,
-			'yoloModeEverEnabled should be persisted in application storage',
-		);
-	});
-
-	test('does not show tip.yoloMode when yoloModeEverEnabled is already persisted in storage', () => {
-		// Simulate a previous session having set the flag
-		storageService.store('chat.tip.yoloModeEverEnabled', true, StorageScope.APPLICATION, StorageTarget.MACHINE);
-
-		const service = createService();
-		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
+		contextKeyService.createKey(ChatContextKeys.chatSessionType.key, localChatSessionType);
 
 		for (let i = 0; i < 100; i++) {
 			const tip = service.getWelcomeTip(contextKeyService);
 			if (!tip) {
 				break;
 			}
-			assert.notStrictEqual(tip.id, 'tip.yoloMode', 'tip.yoloMode should not be shown when yoloModeEverEnabled is already in storage');
+			assert.notStrictEqual(tip.id, 'tip.createPrompt', 'Should not show tip.createPrompt when create-prompt was used');
 			service.dismissTip();
 		}
 	});
 
-	test('does not show tip.yoloMode when policy restricts auto-approve', () => {
-		const policyConfigService = new TestConfigurationService();
-		const originalInspect = policyConfigService.inspect.bind(policyConfigService);
-		policyConfigService.inspect = <T>(key: string, overrides?: any) => {
-			if (key === ChatConfiguration.GlobalAutoApprove) {
-				return { ...originalInspect(key, overrides), policyValue: false } as unknown as T;
-			}
-			return originalInspect(key, overrides);
-		};
-		configurationService = policyConfigService;
-		instantiationService.stub(IConfigurationService, configurationService);
-
-		const service = createService();
-		contextKeyService.createKey(ChatContextKeys.chatModeKind.key, ChatModeKind.Agent);
-
-		for (let i = 0; i < 100; i++) {
-			const tip = service.getWelcomeTip(contextKeyService);
-			if (!tip) {
-				break;
-			}
-			assert.notStrictEqual(tip.id, 'tip.yoloMode', 'tip.yoloMode should not be shown when policy restricts auto-approve');
-			service.dismissTip();
-		}
-	});
 
 	function findTipById(service: ChatTipService, tipId: string, ckService: MockContextKeyServiceWithRulesMatching = contextKeyService): IChatTip | undefined {
 		for (let i = 0; i < 100; i++) {
@@ -999,7 +1440,6 @@ suite('ChatTipService', () => {
 	}
 
 	for (const { tipId, settingKey } of [
-		{ tipId: 'tip.yoloMode', settingKey: ChatConfiguration.GlobalAutoApprove },
 		{ tipId: 'tip.thinkingPhrases', settingKey: 'chat.agent.thinking.phrases' },
 		{ tipId: 'tip.agenticBrowser', settingKey: 'workbench.browser.enableChatTools' },
 	]) {
@@ -1025,7 +1465,6 @@ suite('ChatTipService', () => {
 	}
 
 	for (const tipId of [
-		'tip.yoloMode',
 		'tip.thinkingPhrases',
 		'tip.agenticBrowser',
 	]) {
@@ -1045,6 +1484,9 @@ suite('ChatTipService', () => {
 			commandExecutedEmitter.fire({ commandId: 'workbench.action.openSettings', args: [] });
 
 			assert.strictEqual(dismissed, true, `${tipId} should dismiss when its settings command is clicked`);
+			assert.strictEqual(service.getWelcomeTip(contextKeyService), undefined, 'Tips should hide for the rest of the session after actioning a tip');
+
+			service.resetSession();
 			assertTipNeverShown(service, tipId);
 		});
 	}
@@ -1209,11 +1651,10 @@ suite('ChatTipService', () => {
 		const agentChangeEmitter = testDisposables.add(new Emitter<void>());
 		let agentFiles: IPromptPath[] = [];
 
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customAgent',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.agent, excludeUntilChecked: true },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -1242,11 +1683,10 @@ suite('ChatTipService', () => {
 	test('refreshPromptFileExclusions re-checks instruction files after startup', async () => {
 		let instructionFiles: IPromptPath[] = [];
 
-		const tip: ITipDefinition = {
+		const tip = createMockTip({
 			id: 'tip.customInstructions',
-			message: 'test',
 			excludeWhenPromptFilesExist: { promptType: PromptsType.instructions, agentFileType: AgentFileType.copilotInstructionsMd, excludeUntilChecked: true },
-		};
+		});
 
 		const tracker = testDisposables.add(new TipEligibilityTracker(
 			[tip],
@@ -1269,36 +1709,6 @@ suite('ChatTipService', () => {
 		assert.strictEqual(tracker.isExcluded(tip), true, 'Should be excluded after refresh finds instruction files');
 	});
 
-	test('keeps tip.customInstructions excluded after instruction files were detected once', async () => {
-		const tip: ITipDefinition = {
-			id: 'tip.customInstructions',
-			message: 'test',
-			excludeWhenPromptFilesExist: { promptType: PromptsType.instructions, agentFileType: AgentFileType.copilotInstructionsMd, excludeUntilChecked: true },
-		};
-
-		const tracker1 = testDisposables.add(new TipEligibilityTracker(
-			[tip],
-			{ onDidExecuteCommand: Event.None, onWillExecuteCommand: Event.None } as Partial<ICommandService> as ICommandService,
-			storageService,
-			createMockPromptsService([], [{ uri: URI.file('/.github/instructions/coding.instructions.md'), storage: PromptsStorage.local, type: PromptsType.instructions }]) as IPromptsService,
-			createMockToolsService(),
-			new NullLogService(),
-		));
-
-		await new Promise(r => setTimeout(r, 0));
-		assert.strictEqual(tracker1.isExcluded(tip), true, 'Should be excluded when instruction files exist');
-
-		const tracker2 = testDisposables.add(new TipEligibilityTracker(
-			[tip],
-			{ onDidExecuteCommand: Event.None, onWillExecuteCommand: Event.None } as Partial<ICommandService> as ICommandService,
-			storageService,
-			createMockPromptsService() as IPromptsService,
-			createMockToolsService(),
-			new NullLogService(),
-		));
-
-		assert.strictEqual(tracker2.isExcluded(tip), true, 'Should remain excluded based on persisted detection signal');
-	});
 });
 
 suite('CreateSlashCommandsUsageTracker', () => {
@@ -1306,13 +1716,13 @@ suite('CreateSlashCommandsUsageTracker', () => {
 
 	let storageService: InMemoryStorageService;
 	let contextKeyService: MockContextKeyService;
-	let submitRequestEmitter: Emitter<{ readonly chatSessionResource: URI }>;
+	let submitRequestEmitter: Emitter<{ readonly chatSessionResource: URI; readonly message?: IParsedChatRequest }>;
 	let sessions: Map<string, { lastRequest: { message: { text: string; parts: readonly { kind: string }[] } } | undefined }>;
 
 	setup(() => {
 		storageService = testDisposables.add(new InMemoryStorageService());
 		contextKeyService = new MockContextKeyService();
-		submitRequestEmitter = testDisposables.add(new Emitter<{ readonly chatSessionResource: URI }>());
+		submitRequestEmitter = testDisposables.add(new Emitter<{ readonly chatSessionResource: URI; readonly message?: IParsedChatRequest }>());
 		sessions = new Map();
 	});
 
@@ -1348,7 +1758,7 @@ suite('CreateSlashCommandsUsageTracker', () => {
 		assert.strictEqual(value, true, 'Context key should be true when create commands have been used');
 	});
 
-	test('detects create-instruction slash command via text fallback', () => {
+	test('detects create-instructions slash command via text fallback', () => {
 		const sessionResource = URI.parse('chat:session1');
 		const tracker = createTracker();
 		tracker.syncContextKey(contextKeyService);
@@ -1356,7 +1766,7 @@ suite('CreateSlashCommandsUsageTracker', () => {
 		sessions.set(sessionResource.toString(), {
 			lastRequest: {
 				message: {
-					text: '/create-instruction test',
+					text: '/create-instructions test',
 					parts: [],
 				},
 			},
@@ -1365,7 +1775,7 @@ suite('CreateSlashCommandsUsageTracker', () => {
 		submitRequestEmitter.fire({ chatSessionResource: sessionResource });
 
 		const value = contextKeyService.getContextKeyValue(ChatContextKeys.hasUsedCreateSlashCommands.key);
-		assert.strictEqual(value, true, 'Context key should be true after /create-instruction is used');
+		assert.strictEqual(value, true, 'Context key should be true after /create-instructions is used');
 		assert.strictEqual(
 			storageService.getBoolean('chat.tips.usedCreateSlashCommands', StorageScope.APPLICATION, false),
 			true,
@@ -1425,6 +1835,26 @@ suite('CreateSlashCommandsUsageTracker', () => {
 		);
 	});
 
+	test('detects create command from submitted message payload when session has no last request', () => {
+		const sessionResource = URI.parse('chat:session-payload');
+		const tracker = createTracker();
+		tracker.syncContextKey(contextKeyService);
+
+		submitRequestEmitter.fire({
+			chatSessionResource: sessionResource,
+			message: {
+				text: '/create-prompt payload-test',
+				parts: [],
+			},
+		});
+
+		assert.strictEqual(
+			storageService.getBoolean('chat.tips.usedCreateSlashCommands', StorageScope.APPLICATION, false),
+			true,
+			'Storage should persist usage detected from submitted message payload',
+		);
+	});
+
 	test('does not mark used for non-create slash commands', () => {
 		const sessionResource = URI.parse('chat:session4');
 		const tracker = createTracker();
diff --git a/src/vs/workbench/contrib/chat/test/browser/plugins/agentPluginRepositoryService.test.ts b/src/vs/workbench/contrib/chat/test/browser/plugins/agentPluginRepositoryService.test.ts
new file mode 100644
index 0000000000000..91dbe03786d0e
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/browser/plugins/agentPluginRepositoryService.test.ts
@@ -0,0 +1,449 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { URI } from '../../../../../../base/common/uri.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { ICommandService } from '../../../../../../platform/commands/common/commands.js';
+import { IEnvironmentService } from '../../../../../../platform/environment/common/environment.js';
+import { IFileService } from '../../../../../../platform/files/common/files.js';
+import { TestInstantiationService } from '../../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import { ILogService, NullLogService } from '../../../../../../platform/log/common/log.js';
+import { INotificationService } from '../../../../../../platform/notification/common/notification.js';
+import { IProgressService } from '../../../../../../platform/progress/common/progress.js';
+import { IStorageService, InMemoryStorageService, StorageScope, StorageTarget } from '../../../../../../platform/storage/common/storage.js';
+import { AgentPluginRepositoryService } from '../../../browser/agentPluginRepositoryService.js';
+import { IMarketplacePlugin, MarketplaceType, parseMarketplaceReference, PluginSourceKind } from '../../../common/plugins/pluginMarketplaceService.js';
+
+suite('AgentPluginRepositoryService', () => {
+	const store = ensureNoDisposablesAreLeakedInTestSuite();
+
+	function createPlugin(marketplace: string, source: string): IMarketplacePlugin {
+		const marketplaceReference = parseMarketplaceReference(marketplace);
+		assert.ok(marketplaceReference);
+		if (!marketplaceReference) {
+			throw new Error('Expected marketplace reference to parse.');
+		}
+
+		return {
+			name: 'test-plugin',
+			description: '',
+			version: '',
+			source,
+			sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: source },
+			marketplace: marketplaceReference.displayLabel,
+			marketplaceReference,
+			marketplaceType: MarketplaceType.Copilot,
+		};
+	}
+
+	function createService(
+		onExists?: (resource: URI) => Promise<boolean>,
+		onExecuteCommand?: (id: string, ...args: unknown[]) => void,
+	): AgentPluginRepositoryService {
+		const instantiationService = store.add(new TestInstantiationService());
+
+		const fileService = {
+			exists: async (resource: URI) => onExists ? onExists(resource) : true,
+		} as unknown as IFileService;
+
+		const progressService = {
+			withProgress: async (_options: unknown, callback: (...args: unknown[]) => Promise<unknown>) => callback(),
+		} as unknown as IProgressService;
+
+		instantiationService.stub(ICommandService, {
+			executeCommand: async (id: string, ...args: unknown[]) => {
+				onExecuteCommand?.(id, ...args);
+				return undefined;
+			},
+		} as unknown as ICommandService);
+		instantiationService.stub(IEnvironmentService, { cacheHome: URI.file('/cache') } as unknown as IEnvironmentService);
+		instantiationService.stub(IFileService, fileService);
+		instantiationService.stub(ILogService, new NullLogService());
+		instantiationService.stub(INotificationService, { notify: () => undefined } as unknown as INotificationService);
+		instantiationService.stub(IProgressService, progressService);
+		instantiationService.stub(IStorageService, store.add(new InMemoryStorageService()));
+
+		return instantiationService.createInstance(AgentPluginRepositoryService);
+	}
+
+	test('uses cacheSegments path for GitHub shorthand plugin references', () => {
+		const service = createService();
+		const plugin = createPlugin('microsoft/vscode', 'plugins/myPlugin');
+		const uri = service.getRepositoryUri(plugin.marketplaceReference, plugin.marketplaceType);
+
+		assert.strictEqual(uri.path, '/cache/agentPlugins/github.com/microsoft/vscode');
+	});
+
+	test('uses marketplaces cache path for direct git URI plugin references', () => {
+		const service = createService();
+		const plugin = createPlugin('https://example.com/org/repo.git', 'plugins/myPlugin');
+		const uri = service.getRepositoryUri(plugin.marketplaceReference, plugin.marketplaceType);
+
+		assert.strictEqual(uri.path, '/cache/agentPlugins/example.com/org/repo');
+	});
+
+	test('uses same cache path for equivalent GitHub shorthand and URI references', () => {
+		const service = createService();
+		const shorthandPlugin = createPlugin('microsoft/vscode', 'plugins/myPlugin');
+		const uriPlugin = createPlugin('https://github.com/microsoft/vscode.git', 'plugins/myPlugin');
+
+		const shorthandUri = service.getRepositoryUri(shorthandPlugin.marketplaceReference, shorthandPlugin.marketplaceType);
+		const uriRefUri = service.getRepositoryUri(uriPlugin.marketplaceReference, uriPlugin.marketplaceType);
+
+		assert.strictEqual(shorthandUri.path, '/cache/agentPlugins/github.com/microsoft/vscode');
+		assert.strictEqual(uriRefUri.path, '/cache/agentPlugins/github.com/microsoft/vscode');
+	});
+
+	test('ensures plugin repositories via cacheSegments path', async () => {
+		let checkedPath: string | undefined;
+		const service = createService(async resource => {
+			checkedPath = resource.path;
+			return true;
+		});
+		const plugin = createPlugin('microsoft/vscode', 'plugins/myPlugin');
+		const uri = await service.ensureRepository(plugin.marketplaceReference, { marketplaceType: plugin.marketplaceType });
+
+		assert.strictEqual(checkedPath, '/cache/agentPlugins/github.com/microsoft/vscode');
+		assert.strictEqual(uri.path, '/cache/agentPlugins/github.com/microsoft/vscode');
+	});
+
+	test('concurrent ensureRepository calls for the same marketplace clone only once', async () => {
+		let cloneCount = 0;
+		const instantiationService = store.add(new TestInstantiationService());
+
+		// Track whether the repo exists (set to true after the first clone completes)
+		let repoExists = false;
+		const fileService = {
+			exists: async (_resource: URI) => repoExists,
+			createFolder: async () => undefined,
+		} as unknown as IFileService;
+
+		const progressService = {
+			withProgress: async (_options: unknown, callback: (...args: unknown[]) => Promise<unknown>) => callback(),
+		} as unknown as IProgressService;
+
+		instantiationService.stub(ICommandService, {
+			executeCommand: async (id: string) => {
+				if (id === '_git.cloneRepository') {
+					cloneCount++;
+					// Simulate async clone by yielding, then mark repo as existing
+					await new Promise<void>(r => setTimeout(r, 0));
+					repoExists = true;
+				}
+				return undefined;
+			},
+		} as unknown as ICommandService);
+		instantiationService.stub(IEnvironmentService, { cacheHome: URI.file('/cache') } as unknown as IEnvironmentService);
+		instantiationService.stub(IFileService, fileService);
+		instantiationService.stub(ILogService, new NullLogService());
+		instantiationService.stub(INotificationService, { notify: () => undefined } as unknown as INotificationService);
+		instantiationService.stub(IProgressService, progressService);
+		instantiationService.stub(IStorageService, store.add(new InMemoryStorageService()));
+
+		const service = instantiationService.createInstance(AgentPluginRepositoryService);
+		const plugin = createPlugin('microsoft/vscode', 'plugins/myPlugin');
+
+		// Fire two concurrent ensureRepository calls for the same marketplace
+		const [uri1, uri2] = await Promise.all([
+			service.ensureRepository(plugin.marketplaceReference, { marketplaceType: plugin.marketplaceType }),
+			service.ensureRepository(plugin.marketplaceReference, { marketplaceType: plugin.marketplaceType }),
+		]);
+
+		assert.strictEqual(cloneCount, 1);
+		assert.strictEqual(uri1.path, '/cache/agentPlugins/github.com/microsoft/vscode');
+		assert.strictEqual(uri2.path, '/cache/agentPlugins/github.com/microsoft/vscode');
+	});
+
+	test('builds install URI from source inside repository root', () => {
+		const service = createService();
+		const plugin = createPlugin('microsoft/vscode', 'plugins/myPlugin');
+		const uri = service.getPluginInstallUri(plugin);
+
+		assert.strictEqual(uri.path, '/cache/agentPlugins/github.com/microsoft/vscode/plugins/myPlugin');
+	});
+
+	test('uses indexed repository URI when available', () => {
+		const storage = store.add(new InMemoryStorageService());
+		storage.store('chat.plugins.marketplaces.index.v1', JSON.stringify({
+			'github:microsoft/vscode': {
+				repositoryUri: URI.file('/cache/agentPlugins/indexed/microsoft/vscode'),
+				marketplaceType: MarketplaceType.Copilot,
+			},
+		}), StorageScope.APPLICATION, StorageTarget.MACHINE);
+
+		const instantiationService = store.add(new TestInstantiationService());
+		instantiationService.stub(ICommandService, { executeCommand: async () => undefined } as unknown as ICommandService);
+		instantiationService.stub(IEnvironmentService, { cacheHome: URI.file('/cache') } as unknown as IEnvironmentService);
+		instantiationService.stub(IFileService, { exists: async () => true } as unknown as IFileService);
+		instantiationService.stub(ILogService, new NullLogService());
+		instantiationService.stub(INotificationService, { notify: () => undefined } as unknown as INotificationService);
+		instantiationService.stub(IProgressService, { withProgress: async (_options: unknown, callback: (...args: unknown[]) => Promise<unknown>) => callback() } as unknown as IProgressService);
+		instantiationService.stub(IStorageService, storage);
+
+		const service = instantiationService.createInstance(AgentPluginRepositoryService);
+		const plugin = createPlugin('microsoft/vscode', 'plugins/myPlugin');
+		const uri = service.getRepositoryUri(plugin.marketplaceReference, plugin.marketplaceType);
+
+		assert.strictEqual(uri.path, '/cache/agentPlugins/indexed/microsoft/vscode');
+	});
+
+	test('rejects plugin source paths that escape repository root', () => {
+		const service = createService();
+		const plugin = createPlugin('microsoft/vscode', '../outside');
+
+		assert.throws(() => service.getPluginInstallUri(plugin));
+	});
+
+	test('uses local repository URI for file marketplace references', () => {
+		const service = createService();
+		const plugin = createPlugin('file:///tmp/marketplace-repo', 'plugins/myPlugin');
+		const uri = service.getRepositoryUri(plugin.marketplaceReference, plugin.marketplaceType);
+
+		assert.strictEqual(uri.scheme, 'file');
+		assert.strictEqual(uri.path, '/tmp/marketplace-repo');
+	});
+
+	test('does not invoke clone command when ensuring existing local file repository', async () => {
+		let commandInvocationCount = 0;
+		const service = createService(async () => true, () => {
+			commandInvocationCount++;
+		});
+		const plugin = createPlugin('file:///tmp/marketplace-repo', 'plugins/myPlugin');
+
+		const uri = await service.ensureRepository(plugin.marketplaceReference, { marketplaceType: plugin.marketplaceType });
+
+		assert.strictEqual(uri.path, '/tmp/marketplace-repo');
+		assert.strictEqual(commandInvocationCount, 0);
+	});
+
+	test('builds revision-aware install URI for github plugin sources', () => {
+		const service = createService();
+		const uri = service.getPluginSourceInstallUri({
+			kind: PluginSourceKind.GitHub,
+			repo: 'owner/repo',
+			ref: 'release/v1',
+		});
+
+		assert.strictEqual(uri.path, '/cache/agentPlugins/github.com/owner/repo/ref_release_v1');
+	});
+
+	test('updates git plugin source by pulling and checking out requested revision', async () => {
+		const commands: string[] = [];
+		const service = createService(async () => true, (id: string) => {
+			commands.push(id);
+		});
+
+		await service.updatePluginSource({
+			name: 'my-plugin',
+			description: '',
+			version: '',
+			source: '',
+			sourceDescriptor: {
+				kind: PluginSourceKind.GitHub,
+				repo: 'owner/repo',
+				sha: 'a1b2c3d4e5f6a7b8c9d0e1f2a3b4c5d6e7f8a9b0',
+			},
+			marketplace: 'owner/repo',
+			marketplaceReference: parseMarketplaceReference('owner/repo')!,
+			marketplaceType: MarketplaceType.Copilot,
+		}, {
+			pluginName: 'my-plugin',
+			failureLabel: 'my-plugin',
+			marketplaceType: MarketplaceType.Copilot,
+		});
+
+		assert.deepStrictEqual(commands, ['git.openRepository', '_git.revParse', 'git.fetch', '_git.checkout', '_git.revParse']);
+	});
+
+	// =========================================================================
+	// cleanupPluginSource — issue #297251 regression
+	// =========================================================================
+
+	suite('cleanupPluginSource', () => {
+
+		function createServiceWithDel(
+			onDel: (resource: URI) => void,
+			options?: { resolve?: (resource: URI) => { children?: unknown[] } },
+		) {
+			const instantiationService = store.add(new TestInstantiationService());
+			instantiationService.stub(ICommandService, { executeCommand: async () => undefined } as unknown as ICommandService);
+			instantiationService.stub(IEnvironmentService, { cacheHome: URI.file('/cache') } as unknown as IEnvironmentService);
+			instantiationService.stub(IFileService, {
+				exists: async () => true,
+				del: async (resource: URI) => { onDel(resource); },
+				createFolder: async () => undefined,
+				resolve: async (resource: URI) => options?.resolve?.(resource) ?? { children: [] },
+			} as unknown as IFileService);
+			instantiationService.stub(ILogService, new NullLogService());
+			instantiationService.stub(INotificationService, { notify: () => undefined } as unknown as INotificationService);
+			instantiationService.stub(IProgressService, { withProgress: async (_o: unknown, cb: (...a: unknown[]) => Promise<unknown>) => cb() } as unknown as IProgressService);
+			instantiationService.stub(IStorageService, store.add(new InMemoryStorageService()));
+			return instantiationService.createInstance(AgentPluginRepositoryService);
+		}
+
+		test('does not delete files for relative-path (marketplace) plugin', async () => {
+			const deleted: string[] = [];
+			const service = createServiceWithDel(r => deleted.push(r.path));
+
+			await service.cleanupPluginSource({
+				name: 'marketplace-plugin',
+				description: '',
+				version: '',
+				source: 'plugins/foo',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/foo' },
+				marketplace: 'microsoft/vscode',
+				marketplaceReference: parseMarketplaceReference('microsoft/vscode')!,
+				marketplaceType: MarketplaceType.Copilot,
+			});
+
+			assert.strictEqual(deleted.length, 0);
+		});
+
+		test('deletes cache for github plugin source', async () => {
+			const deleted: string[] = [];
+			const service = createServiceWithDel(r => deleted.push(r.path));
+
+			await service.cleanupPluginSource({
+				name: 'gh-plugin',
+				description: '',
+				version: '',
+				source: '',
+				sourceDescriptor: { kind: PluginSourceKind.GitHub, repo: 'owner/repo' },
+				marketplace: 'owner/marketplace',
+				marketplaceReference: parseMarketplaceReference('owner/marketplace')!,
+				marketplaceType: MarketplaceType.Copilot,
+			});
+
+			assert.ok(deleted.length >= 1);
+			assert.ok(deleted[0].includes('github.com/owner/repo'));
+		});
+
+		test('deletes parent cache dir for npm plugin source', async () => {
+			const deleted: string[] = [];
+			const service = createServiceWithDel(r => deleted.push(r.path));
+
+			await service.cleanupPluginSource({
+				name: 'npm-plugin',
+				description: '',
+				version: '',
+				source: '',
+				sourceDescriptor: { kind: PluginSourceKind.Npm, package: '@acme/plugin' },
+				marketplace: 'owner/marketplace',
+				marketplaceReference: parseMarketplaceReference('owner/marketplace')!,
+				marketplaceType: MarketplaceType.Copilot,
+			});
+
+			assert.ok(deleted.length >= 1);
+			// First delete should be the npm/<sanitized-package> cache dir
+			assert.ok(deleted[0].includes('/npm/'), `Expected npm path, got: ${deleted[0]}`);
+		});
+
+		test('deletes cache for pip plugin source', async () => {
+			const deleted: string[] = [];
+			const service = createServiceWithDel(r => deleted.push(r.path));
+
+			await service.cleanupPluginSource({
+				name: 'pip-plugin',
+				description: '',
+				version: '',
+				source: '',
+				sourceDescriptor: { kind: PluginSourceKind.Pip, package: 'my-pip-pkg' },
+				marketplace: 'owner/marketplace',
+				marketplaceReference: parseMarketplaceReference('owner/marketplace')!,
+				marketplaceType: MarketplaceType.Copilot,
+			});
+
+			assert.ok(deleted.length >= 1);
+			assert.ok(deleted[0].includes('pip/my-pip-pkg'));
+		});
+
+		test('does not throw when delete fails', async () => {
+			const instantiationService = store.add(new TestInstantiationService());
+			instantiationService.stub(ICommandService, { executeCommand: async () => undefined } as unknown as ICommandService);
+			instantiationService.stub(IEnvironmentService, { cacheHome: URI.file('/cache') } as unknown as IEnvironmentService);
+			instantiationService.stub(IFileService, {
+				exists: async () => true,
+				del: async () => { throw new Error('permission denied'); },
+				createFolder: async () => undefined,
+				resolve: async () => ({ children: [] }),
+			} as unknown as IFileService);
+			instantiationService.stub(ILogService, new NullLogService());
+			instantiationService.stub(INotificationService, { notify: () => undefined } as unknown as INotificationService);
+			instantiationService.stub(IProgressService, { withProgress: async (_o: unknown, cb: (...a: unknown[]) => Promise<unknown>) => cb() } as unknown as IProgressService);
+			instantiationService.stub(IStorageService, store.add(new InMemoryStorageService()));
+			const service = instantiationService.createInstance(AgentPluginRepositoryService);
+
+			// Should not throw — cleanup is best-effort
+			await service.cleanupPluginSource({
+				name: 'gh-plugin',
+				description: '',
+				version: '',
+				source: '',
+				sourceDescriptor: { kind: PluginSourceKind.GitHub, repo: 'owner/repo' },
+				marketplace: 'owner/marketplace',
+				marketplaceReference: parseMarketplaceReference('owner/marketplace')!,
+				marketplaceType: MarketplaceType.Copilot,
+			});
+		});
+
+		test('prunes empty parent directories up to cache root', async () => {
+			// After deleting github.com/owner/repo, the "owner" dir is empty
+			// and should also be removed.
+			const deleted: string[] = [];
+			const service = createServiceWithDel(
+				r => deleted.push(r.path),
+				{ resolve: () => ({ children: [] }) },
+			);
+
+			await service.cleanupPluginSource({
+				name: 'gh-plugin',
+				description: '',
+				version: '',
+				source: '',
+				sourceDescriptor: { kind: PluginSourceKind.GitHub, repo: 'owner/repo' },
+				marketplace: 'owner/marketplace',
+				marketplaceReference: parseMarketplaceReference('owner/marketplace')!,
+				marketplaceType: MarketplaceType.Copilot,
+			});
+
+			// Should have deleted the repo dir + empty parents (owner, github.com)
+			assert.ok(deleted.length >= 2, `Expected at least 2 deletions (repo + parent), got ${deleted.length}: ${deleted.join(', ')}`);
+			assert.ok(deleted[0].includes('github.com/owner/repo'), 'First delete should be the repo dir');
+			assert.ok(deleted.some(p => p.endsWith('/owner')), 'Should prune empty owner directory');
+		});
+
+		test('stops pruning at non-empty parent', async () => {
+			const deleted: string[] = [];
+			const service = createServiceWithDel(
+				r => deleted.push(r.path),
+				{
+					resolve: (resource: URI) => {
+						// owner dir still has another repo
+						if (resource.path.endsWith('/owner')) {
+							return { children: [{ name: 'other-repo' }] };
+						}
+						return { children: [] };
+					},
+				},
+			);
+
+			await service.cleanupPluginSource({
+				name: 'gh-plugin',
+				description: '',
+				version: '',
+				source: '',
+				sourceDescriptor: { kind: PluginSourceKind.GitHub, repo: 'owner/repo' },
+				marketplace: 'owner/marketplace',
+				marketplaceReference: parseMarketplaceReference('owner/marketplace')!,
+				marketplaceType: MarketplaceType.Copilot,
+			});
+
+			// Should only delete the repo dir, stop at non-empty owner dir
+			assert.strictEqual(deleted.length, 1);
+			assert.ok(deleted[0].includes('github.com/owner/repo'));
+		});
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/browser/plugins/pluginInstallService.test.ts b/src/vs/workbench/contrib/chat/test/browser/plugins/pluginInstallService.test.ts
new file mode 100644
index 0000000000000..c721a9e146fed
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/browser/plugins/pluginInstallService.test.ts
@@ -0,0 +1,952 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { URI } from '../../../../../../base/common/uri.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { IDialogService } from '../../../../../../platform/dialogs/common/dialogs.js';
+import { IFileService } from '../../../../../../platform/files/common/files.js';
+import { TestInstantiationService } from '../../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import { ILogService, NullLogService } from '../../../../../../platform/log/common/log.js';
+import { INotificationService } from '../../../../../../platform/notification/common/notification.js';
+import { IProgressService } from '../../../../../../platform/progress/common/progress.js';
+import { IQuickInputService } from '../../../../../../platform/quickinput/common/quickInput.js';
+import { ITerminalService } from '../../../../terminal/browser/terminal.js';
+import { PluginInstallService } from '../../../browser/pluginInstallService.js';
+import { IAgentPluginRepositoryService, IEnsureRepositoryOptions, IPullRepositoryOptions } from '../../../common/plugins/agentPluginRepositoryService.js';
+import { IMarketplacePlugin, IMarketplaceReference, IPluginMarketplaceService, IPluginSourceDescriptor, MarketplaceType, parseMarketplaceReference, PluginSourceKind } from '../../../common/plugins/pluginMarketplaceService.js';
+import { IPluginSource } from '../../../common/plugins/pluginSource.js';
+
+suite('PluginInstallService', () => {
+	const store = ensureNoDisposablesAreLeakedInTestSuite();
+
+	// --- Factory helpers -------------------------------------------------------
+
+	function makeMarketplaceRef(marketplace: string): IMarketplaceReference {
+		const ref = parseMarketplaceReference(marketplace);
+		assert.ok(ref);
+		return ref!;
+	}
+
+	function createPlugin(overrides: Partial<IMarketplacePlugin> & { sourceDescriptor: IPluginSourceDescriptor }): IMarketplacePlugin {
+		return {
+			name: overrides.name ?? 'test-plugin',
+			description: overrides.description ?? '',
+			version: overrides.version ?? '',
+			source: overrides.source ?? '',
+			sourceDescriptor: overrides.sourceDescriptor,
+			marketplace: overrides.marketplace ?? 'microsoft/vscode',
+			marketplaceReference: overrides.marketplaceReference ?? makeMarketplaceRef('microsoft/vscode'),
+			marketplaceType: overrides.marketplaceType ?? MarketplaceType.Copilot,
+			readmeUri: overrides.readmeUri,
+		};
+	}
+
+	// --- Mock tracking types ---------------------------------------------------
+
+	interface MockState {
+		notifications: { severity: number; message: string }[];
+		addedPlugins: { uri: string; plugin: IMarketplacePlugin }[];
+		dialogConfirmResult: boolean;
+		fileExistsResult: boolean | ((uri: URI) => Promise<boolean>);
+		ensureRepositoryResult: URI;
+		ensurePluginSourceResult: URI;
+		/** Plugin source install URI, per kind */
+		pluginSourceInstallUris: Map<string, URI>;
+		/** The commands that were sent to the terminal */
+		terminalCommands: string[];
+		/** Simulated exit code from terminal */
+		terminalExitCode: number;
+		/** Whether the terminal resolves the command completion at all */
+		terminalCompletes: boolean;
+		pullRepositoryCalls: { marketplace: IMarketplaceReference; options?: IPullRepositoryOptions }[];
+		updatePluginSourceCalls: { plugin: IMarketplacePlugin; options?: IPullRepositoryOptions }[];
+		/** Whether the marketplace is already trusted */
+		marketplaceTrusted: boolean;
+		/** Canonical IDs that were trusted via trustMarketplace() */
+		trustedMarketplaces: string[];
+		/** Plugins returned by readPluginsFromDirectory */
+		readPluginsResult: IMarketplacePlugin[];
+		/** Result of the quick pick dialog */
+		quickPickResult: { label: string } | undefined;
+		/** Result of the quick input dialog */
+		quickInputResult: string | undefined;
+	}
+
+	function createDefaults(): MockState {
+		return {
+			notifications: [],
+			addedPlugins: [],
+			dialogConfirmResult: true,
+			fileExistsResult: true,
+			ensureRepositoryResult: URI.file('/cache/agentPlugins/github.com/microsoft/vscode'),
+			ensurePluginSourceResult: URI.file('/cache/agentPlugins/npm/my-package'),
+			pluginSourceInstallUris: new Map(),
+			terminalCommands: [],
+			terminalExitCode: 0,
+			terminalCompletes: true,
+			pullRepositoryCalls: [],
+			updatePluginSourceCalls: [],
+			marketplaceTrusted: true,
+			trustedMarketplaces: [],
+			readPluginsResult: [],
+			quickPickResult: undefined,
+			quickInputResult: undefined,
+		};
+	}
+
+	function createService(stateOverrides?: Partial<MockState>): { service: PluginInstallService; state: MockState } {
+		const state: MockState = { ...createDefaults(), ...stateOverrides };
+		const instantiationService = store.add(new TestInstantiationService());
+
+		// IFileService
+		instantiationService.stub(IFileService, {
+			exists: async (resource: URI) => {
+				if (typeof state.fileExistsResult === 'function') {
+					return state.fileExistsResult(resource);
+				}
+				return state.fileExistsResult;
+			},
+		} as unknown as IFileService);
+
+		// INotificationService
+		instantiationService.stub(INotificationService, {
+			notify: (notification: { severity: number; message: string }) => {
+				state.notifications.push({ severity: notification.severity, message: notification.message });
+				return undefined;
+			},
+		} as unknown as INotificationService);
+
+		// IDialogService
+		instantiationService.stub(IDialogService, {
+			confirm: async () => ({ confirmed: state.dialogConfirmResult }),
+		} as unknown as IDialogService);
+
+		// ITerminalService — the mock coordinates runCommand and onCommandFinished
+		// so the command ID matches, just like a real terminal would.
+		instantiationService.stub(ITerminalService, {
+			createTerminal: async () => {
+				let finishedCallback: ((cmd: { id: string; exitCode: number }) => void) | undefined;
+				return {
+					processReady: Promise.resolve(),
+					dispose: () => { },
+					runCommand: (command: string, _addNewLine?: boolean) => {
+						state.terminalCommands.push(command);
+						// Simulate command completing after runCommand is called
+						if (finishedCallback) {
+							finishedCallback({ id: 'command', exitCode: state.terminalExitCode });
+						}
+					},
+					capabilities: {
+						get: () => state.terminalCompletes ? {
+							onCommandFinished: (callback: (cmd: { id: string; exitCode: number }) => void) => {
+								finishedCallback = callback;
+								return { dispose() { } };
+							},
+						} : undefined,
+						onDidAddCommandDetectionCapability: () => ({ dispose() { } }),
+					},
+				};
+			},
+			setActiveInstance: () => { },
+		} as unknown as ITerminalService);
+
+		// IProgressService
+		instantiationService.stub(IProgressService, {
+			withProgress: async (_options: unknown, callback: (...args: unknown[]) => Promise<unknown>) => callback(),
+		} as unknown as IProgressService);
+
+		// ILogService
+		instantiationService.stub(ILogService, new NullLogService());
+
+		// IAgentPluginRepositoryService
+		// Build mock source repositories for npm/pip that simulate terminal-based install
+		const makeMockPackageRepo = (kind: PluginSourceKind): IPluginSource => ({
+			kind,
+			getCleanupTarget: () => URI.file('/mock-cleanup'),
+			getInstallUri: () => URI.file('/mock'),
+			ensure: async () => state.ensurePluginSourceResult,
+			update: async () => true,
+			getLabel: (d) => kind === PluginSourceKind.Npm ? (d as { package: string }).package : (d as { package: string }).package,
+			runInstall: async (_installDir: URI, pluginDir: URI, plugin: IMarketplacePlugin) => {
+				// Simulate confirmation dialog
+				if (!state.dialogConfirmResult) {
+					return undefined;
+				}
+
+				// Simulate building and running the command
+				const descriptor = plugin.sourceDescriptor;
+				let args: string[];
+				if (kind === PluginSourceKind.Npm) {
+					const npm = descriptor as { package: string; version?: string; registry?: string };
+					const packageSpec = npm.version ? `${npm.package}@${npm.version}` : npm.package;
+					args = ['npm', 'install', '--prefix', _installDir.fsPath, packageSpec];
+					if (npm.registry) {
+						args.push('--registry', npm.registry);
+					}
+				} else {
+					const pip = descriptor as { package: string; version?: string; registry?: string };
+					const packageSpec = pip.version ? `${pip.package}==${pip.version}` : pip.package;
+					args = ['pip', 'install', '--target', _installDir.fsPath, packageSpec];
+					if (pip.registry) {
+						args.push('--index-url', pip.registry);
+					}
+				}
+				const command = args.join(' ');
+				state.terminalCommands.push(command);
+
+				if (state.terminalExitCode !== 0) {
+					state.notifications.push({ severity: 3, message: `Plugin installation command failed: Command exited with code ${state.terminalExitCode}` });
+					return undefined;
+				}
+
+				// Check if plugin dir exists
+				const exists = typeof state.fileExistsResult === 'function'
+					? await state.fileExistsResult(pluginDir)
+					: state.fileExistsResult;
+				if (!exists) {
+					const label = kind === PluginSourceKind.Npm ? 'npm' : 'pip';
+					const pkg = (descriptor as { package: string }).package;
+					state.notifications.push({ severity: 3, message: `${label} package '${pkg}' was not found after installation.` });
+					return undefined;
+				}
+
+				return { pluginDir };
+			},
+		});
+
+		const mockSourceRepos = new Map<PluginSourceKind, IPluginSource>([
+			[PluginSourceKind.RelativePath, { kind: PluginSourceKind.RelativePath, getCleanupTarget: () => undefined, getInstallUri: () => { throw new Error(); }, ensure: async () => { throw new Error(); }, update: async () => { throw new Error(); }, getLabel: (d) => (d as { path: string }).path || '.' }],
+			[PluginSourceKind.GitHub, { kind: PluginSourceKind.GitHub, getCleanupTarget: () => URI.file('/mock'), getInstallUri: () => URI.file('/mock'), ensure: async () => URI.file('/mock'), update: async () => true, getLabel: (d) => (d as { repo: string }).repo }],
+			[PluginSourceKind.GitUrl, { kind: PluginSourceKind.GitUrl, getCleanupTarget: () => URI.file('/mock'), getInstallUri: () => URI.file('/mock'), ensure: async () => URI.file('/mock'), update: async () => true, getLabel: (d) => (d as { url: string }).url }],
+			[PluginSourceKind.Npm, makeMockPackageRepo(PluginSourceKind.Npm)],
+			[PluginSourceKind.Pip, makeMockPackageRepo(PluginSourceKind.Pip)],
+		]);
+
+		instantiationService.stub(IAgentPluginRepositoryService, {
+			getPluginInstallUri: (plugin: IMarketplacePlugin) => {
+				return URI.joinPath(state.ensureRepositoryResult, plugin.source);
+			},
+			getRepositoryUri: () => state.ensureRepositoryResult,
+			ensureRepository: async (_marketplace: IMarketplaceReference, _options?: IEnsureRepositoryOptions) => {
+				return state.ensureRepositoryResult;
+			},
+			pullRepository: async (marketplace: IMarketplaceReference, options?: IPullRepositoryOptions) => {
+				state.pullRepositoryCalls.push({ marketplace, options });
+			},
+			getPluginSourceInstallUri: (descriptor: IPluginSourceDescriptor) => {
+				const key = descriptor.kind;
+				return state.pluginSourceInstallUris.get(key) ?? URI.file(`/cache/agentPlugins/${key}/default`);
+			},
+			ensurePluginSource: async () => state.ensurePluginSourceResult,
+			updatePluginSource: async (plugin: IMarketplacePlugin, options?: IPullRepositoryOptions) => {
+				state.updatePluginSourceCalls.push({ plugin, options });
+			},
+			getPluginSource: (kind: PluginSourceKind) => mockSourceRepos.get(kind)!,
+			cleanupPluginSource: async () => { },
+		} as unknown as IAgentPluginRepositoryService);
+
+		// IPluginMarketplaceService
+		instantiationService.stub(IPluginMarketplaceService, {
+			addInstalledPlugin: (uri: URI, plugin: IMarketplacePlugin) => {
+				state.addedPlugins.push({ uri: uri.toString(), plugin });
+			},
+			isMarketplaceTrusted: () => state.marketplaceTrusted,
+			trustMarketplace: (ref: IMarketplaceReference) => {
+				state.trustedMarketplaces.push(ref.canonicalId);
+			},
+			readPluginsFromDirectory: async () => state.readPluginsResult,
+		} as unknown as IPluginMarketplaceService);
+
+		// IQuickInputService
+		instantiationService.stub(IQuickInputService, {
+			input: async () => state.quickInputResult,
+			pick: async (picks: { label: string }[]) => {
+				if (!state.quickPickResult) {
+					return undefined;
+				}
+				return picks.find(p => p.label === state.quickPickResult!.label);
+			},
+		} as unknown as IQuickInputService);
+
+		const service = instantiationService.createInstance(PluginInstallService);
+		return { service, state };
+	}
+
+	// =========================================================================
+	// getPluginInstallUri
+	// =========================================================================
+
+	suite('getPluginInstallUri', () => {
+
+		test('delegates to getPluginInstallUri for relative-path plugins', () => {
+			const { service } = createService();
+			const plugin = createPlugin({
+				source: 'plugins/myPlugin',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/myPlugin' },
+			});
+			const uri = service.getPluginInstallUri(plugin);
+			assert.strictEqual(uri.path, '/cache/agentPlugins/github.com/microsoft/vscode/plugins/myPlugin');
+		});
+
+		test('delegates to getPluginSourceInstallUri for npm plugins', () => {
+			const npmUri = URI.file('/cache/agentPlugins/npm/my-pkg/node_modules/my-pkg');
+			const { service } = createService({
+				pluginSourceInstallUris: new Map([['npm', npmUri]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Npm, package: 'my-pkg' },
+			});
+			const uri = service.getPluginInstallUri(plugin);
+			assert.strictEqual(uri.path, npmUri.path);
+		});
+
+		test('delegates to getPluginSourceInstallUri for pip plugins', () => {
+			const pipUri = URI.file('/cache/agentPlugins/pip/my-pkg');
+			const { service } = createService({
+				pluginSourceInstallUris: new Map([['pip', pipUri]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Pip, package: 'my-pkg' },
+			});
+			const uri = service.getPluginInstallUri(plugin);
+			assert.strictEqual(uri.path, pipUri.path);
+		});
+
+		test('delegates to getPluginSourceInstallUri for github plugins', () => {
+			const ghUri = URI.file('/cache/agentPlugins/github.com/owner/repo');
+			const { service } = createService({
+				pluginSourceInstallUris: new Map([['github', ghUri]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.GitHub, repo: 'owner/repo' },
+			});
+			const uri = service.getPluginInstallUri(plugin);
+			assert.strictEqual(uri.path, ghUri.path);
+		});
+	});
+
+	// =========================================================================
+	// installPlugin — relative path
+	// =========================================================================
+
+	suite('installPlugin — relative path', () => {
+
+		test('installs a relative-path plugin when directory exists', async () => {
+			const { service, state } = createService();
+			const plugin = createPlugin({
+				source: 'plugins/myPlugin',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/myPlugin' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.addedPlugins.length, 1);
+			assert.ok(state.addedPlugins[0].uri.includes('plugins/myPlugin'));
+			assert.strictEqual(state.notifications.length, 0);
+		});
+
+		test('notifies error when plugin directory does not exist', async () => {
+			const { service, state } = createService({ fileExistsResult: false });
+			const plugin = createPlugin({
+				source: 'plugins/missing',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/missing' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.addedPlugins.length, 0);
+			assert.strictEqual(state.notifications.length, 1);
+			assert.ok(state.notifications[0].message.includes('not found'));
+		});
+
+		test('does not install when ensureRepository throws', async () => {
+			const { state } = createService();
+			// Override ensureRepository to throw
+			const instantiationService = store.add(new TestInstantiationService());
+			const repoService = {
+				ensureRepository: async () => { throw new Error('clone failed'); },
+				getPluginInstallUri: () => URI.file('/x'),
+				getPluginSourceInstallUri: () => URI.file('/x'),
+			};
+			instantiationService.stub(IAgentPluginRepositoryService, repoService as unknown as IAgentPluginRepositoryService);
+			instantiationService.stub(IFileService, { exists: async () => true } as unknown as IFileService);
+			instantiationService.stub(INotificationService, { notify: (n: { severity: number; message: string }) => { state.notifications.push(n); } } as unknown as INotificationService);
+			instantiationService.stub(IDialogService, { confirm: async () => ({ confirmed: true }) } as unknown as IDialogService);
+			instantiationService.stub(ITerminalService, {} as unknown as ITerminalService);
+			instantiationService.stub(IProgressService, { withProgress: async (_o: unknown, cb: () => Promise<unknown>) => cb() } as unknown as IProgressService);
+			instantiationService.stub(ILogService, new NullLogService());
+			instantiationService.stub(IPluginMarketplaceService, { addInstalledPlugin: () => { } } as unknown as IPluginMarketplaceService);
+			instantiationService.stub(IPluginMarketplaceService, 'isMarketplaceTrusted', () => true);
+			instantiationService.stub(IPluginMarketplaceService, 'trustMarketplace', () => { });
+			const svc = instantiationService.createInstance(PluginInstallService);
+
+			const plugin = createPlugin({
+				source: 'plugins/myPlugin',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/myPlugin' },
+			});
+			await svc.installPlugin(plugin);
+
+			// Should return without installing or crashing
+			assert.strictEqual(state.addedPlugins.length, 0);
+		});
+	});
+
+	// =========================================================================
+	// installPlugin — GitHub / GitUrl
+	// =========================================================================
+
+	suite('installPlugin — git sources', () => {
+
+		test('installs a GitHub plugin when source exists after clone', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/github.com/owner/repo'),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.GitHub, repo: 'owner/repo' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.addedPlugins.length, 1);
+			assert.strictEqual(state.notifications.length, 0);
+		});
+
+		test('installs a GitUrl plugin when source exists after clone', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/example.com/repo'),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.GitUrl, url: 'https://example.com/repo.git' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.addedPlugins.length, 1);
+			assert.strictEqual(state.notifications.length, 0);
+		});
+
+		test('notifies error when cloned directory does not exist', async () => {
+			const { service, state } = createService({
+				fileExistsResult: false,
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/github.com/owner/repo'),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.GitHub, repo: 'owner/repo' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.addedPlugins.length, 0);
+			assert.strictEqual(state.notifications.length, 1);
+			assert.ok(state.notifications[0].message.includes('not found'));
+		});
+	});
+
+	// =========================================================================
+	// installPlugin — npm
+	// =========================================================================
+
+	suite('installPlugin — npm', () => {
+
+		test('runs npm install and registers plugin on success', async () => {
+			const npmInstallUri = URI.file('/cache/agentPlugins/npm/my-pkg/node_modules/my-pkg');
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/npm/my-pkg'),
+				pluginSourceInstallUris: new Map([['npm', npmInstallUri]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Npm, package: 'my-pkg' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.terminalCommands.length, 1);
+			assert.ok(state.terminalCommands[0].includes('npm'));
+			assert.ok(state.terminalCommands[0].includes('install'));
+			assert.ok(state.terminalCommands[0].includes('my-pkg'));
+			assert.strictEqual(state.addedPlugins.length, 1);
+			assert.strictEqual(state.notifications.length, 0);
+		});
+
+		test('includes version in npm install command', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/npm/my-pkg'),
+				pluginSourceInstallUris: new Map([['npm', URI.file('/cache/agentPlugins/npm/my-pkg/node_modules/my-pkg')]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Npm, package: 'my-pkg', version: '1.2.3' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.terminalCommands.length, 1);
+			assert.ok(state.terminalCommands[0].includes('my-pkg@1.2.3'));
+		});
+
+		test('includes registry in npm install command', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/npm/my-pkg'),
+				pluginSourceInstallUris: new Map([['npm', URI.file('/cache/agentPlugins/npm/my-pkg/node_modules/my-pkg')]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Npm, package: 'my-pkg', registry: 'https://custom.registry.com' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.terminalCommands.length, 1);
+			assert.ok(state.terminalCommands[0].includes('--registry'));
+			assert.ok(state.terminalCommands[0].includes('https://custom.registry.com'));
+		});
+
+		test('does not install when user declines confirmation', async () => {
+			const { service, state } = createService({ dialogConfirmResult: false });
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Npm, package: 'my-pkg' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.terminalCommands.length, 0);
+			assert.strictEqual(state.addedPlugins.length, 0);
+		});
+
+		test('notifies error when npm package directory not found after install', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/npm/my-pkg'),
+				// exists returns true for ensurePluginSource but false for the final check
+				fileExistsResult: false,
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Npm, package: 'my-pkg' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.addedPlugins.length, 0);
+			assert.strictEqual(state.notifications.length, 1);
+			assert.ok(state.notifications[0].message.includes('not found'));
+		});
+
+		test('notifies error when terminal command fails with non-zero exit code', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/npm/my-pkg'),
+				terminalExitCode: 1,
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Npm, package: 'my-pkg' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.addedPlugins.length, 0);
+			assert.strictEqual(state.notifications.length, 1);
+			assert.ok(state.notifications[0].message.includes('failed'));
+		});
+	});
+
+	// =========================================================================
+	// installPlugin — pip
+	// =========================================================================
+
+	suite('installPlugin — pip', () => {
+
+		test('runs pip install and registers plugin on success', async () => {
+			const pipInstallUri = URI.file('/cache/agentPlugins/pip/my-pkg');
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/pip/my-pkg'),
+				pluginSourceInstallUris: new Map([['pip', pipInstallUri]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Pip, package: 'my-pkg' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.terminalCommands.length, 1);
+			assert.ok(state.terminalCommands[0].includes('pip'));
+			assert.ok(state.terminalCommands[0].includes('install'));
+			assert.ok(state.terminalCommands[0].includes('my-pkg'));
+			assert.strictEqual(state.addedPlugins.length, 1);
+			assert.strictEqual(state.notifications.length, 0);
+		});
+
+		test('includes version with == syntax in pip install command', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/pip/my-pkg'),
+				pluginSourceInstallUris: new Map([['pip', URI.file('/cache/agentPlugins/pip/my-pkg')]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Pip, package: 'my-pkg', version: '2.0.0' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.terminalCommands.length, 1);
+			assert.ok(state.terminalCommands[0].includes('my-pkg==2.0.0'));
+		});
+
+		test('includes registry with --index-url in pip install command', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/pip/my-pkg'),
+				pluginSourceInstallUris: new Map([['pip', URI.file('/cache/agentPlugins/pip/my-pkg')]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Pip, package: 'my-pkg', registry: 'https://pypi.custom.com/simple' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.terminalCommands.length, 1);
+			assert.ok(state.terminalCommands[0].includes('--index-url'));
+			assert.ok(state.terminalCommands[0].includes('https://pypi.custom.com/simple'));
+		});
+
+		test('does not install when user declines confirmation', async () => {
+			const { service, state } = createService({ dialogConfirmResult: false });
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Pip, package: 'my-pkg' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.terminalCommands.length, 0);
+			assert.strictEqual(state.addedPlugins.length, 0);
+		});
+
+		test('notifies error when pip package directory not found after install', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/pip/my-pkg'),
+				fileExistsResult: false,
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Pip, package: 'my-pkg' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.addedPlugins.length, 0);
+			assert.strictEqual(state.notifications.length, 1);
+			assert.ok(state.notifications[0].message.includes('not found'));
+		});
+	});
+
+	// =========================================================================
+	// updatePlugin
+	// =========================================================================
+
+	suite('updatePlugin', () => {
+
+		test('calls updatePluginSource for relative-path plugins', async () => {
+			const { service, state } = createService();
+			const plugin = createPlugin({
+				source: 'plugins/myPlugin',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/myPlugin' },
+			});
+
+			await service.updatePlugin(plugin);
+
+			assert.strictEqual(state.updatePluginSourceCalls.length, 1);
+		});
+
+		test('calls updatePluginSource for GitHub plugins', async () => {
+			const { service, state } = createService();
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.GitHub, repo: 'owner/repo' },
+			});
+
+			await service.updatePlugin(plugin);
+
+			assert.strictEqual(state.updatePluginSourceCalls.length, 1);
+		});
+
+		test('calls updatePluginSource for GitUrl plugins', async () => {
+			const { service, state } = createService();
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.GitUrl, url: 'https://example.com/repo.git' },
+			});
+
+			await service.updatePlugin(plugin);
+
+			assert.strictEqual(state.updatePluginSourceCalls.length, 1);
+		});
+
+		test('re-installs for npm plugin updates', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/npm/my-pkg'),
+				pluginSourceInstallUris: new Map([['npm', URI.file('/cache/agentPlugins/npm/my-pkg/node_modules/my-pkg')]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Npm, package: 'my-pkg' },
+			});
+
+			await service.updatePlugin(plugin);
+
+			// npm update goes through the same install flow
+			assert.strictEqual(state.terminalCommands.length, 1);
+			assert.ok(state.terminalCommands[0].includes('npm'));
+		});
+
+		test('does not report npm plugin as updated when install is declined', async () => {
+			const { service, state } = createService({
+				dialogConfirmResult: false,
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/npm/my-pkg'),
+				pluginSourceInstallUris: new Map([['npm', URI.file('/cache/agentPlugins/npm/my-pkg/node_modules/my-pkg')]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Npm, package: 'my-pkg' },
+			});
+
+			const updated = await service.updatePlugin(plugin);
+
+			assert.strictEqual(updated, false);
+			assert.strictEqual(state.terminalCommands.length, 0);
+			assert.strictEqual(state.addedPlugins.length, 0);
+		});
+
+		test('re-installs for pip plugin updates', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/pip/my-pkg'),
+				pluginSourceInstallUris: new Map([['pip', URI.file('/cache/agentPlugins/pip/my-pkg')]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Pip, package: 'my-pkg' },
+			});
+
+			await service.updatePlugin(plugin);
+
+			assert.strictEqual(state.terminalCommands.length, 1);
+			assert.ok(state.terminalCommands[0].includes('pip'));
+		});
+
+		test('does not report pip plugin as updated when install is declined', async () => {
+			const { service, state } = createService({
+				dialogConfirmResult: false,
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/pip/my-pkg'),
+				pluginSourceInstallUris: new Map([['pip', URI.file('/cache/agentPlugins/pip/my-pkg')]]),
+			});
+			const plugin = createPlugin({
+				sourceDescriptor: { kind: PluginSourceKind.Pip, package: 'my-pkg' },
+			});
+
+			const updated = await service.updatePlugin(plugin);
+
+			assert.strictEqual(updated, false);
+			assert.strictEqual(state.terminalCommands.length, 0);
+			assert.strictEqual(state.addedPlugins.length, 0);
+		});
+	});
+
+	// =========================================================================
+	// installPlugin — marketplace trust
+	// =========================================================================
+
+	suite('installPlugin — marketplace trust', () => {
+
+		test('skips trust prompt when marketplace is already trusted', async () => {
+			const { service, state } = createService({ marketplaceTrusted: true });
+			const plugin = createPlugin({
+				source: 'plugins/myPlugin',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/myPlugin' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.addedPlugins.length, 1);
+			assert.strictEqual(state.trustedMarketplaces.length, 0, 'should not re-trust');
+		});
+
+		test('shows trust prompt and installs when user confirms', async () => {
+			const { service, state } = createService({ marketplaceTrusted: false, dialogConfirmResult: true });
+			const plugin = createPlugin({
+				source: 'plugins/myPlugin',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/myPlugin' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.trustedMarketplaces.length, 1);
+			assert.strictEqual(state.addedPlugins.length, 1);
+		});
+
+		test('does not install when user declines trust', async () => {
+			const { service, state } = createService({ marketplaceTrusted: false, dialogConfirmResult: false });
+			const plugin = createPlugin({
+				source: 'plugins/myPlugin',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/myPlugin' },
+			});
+
+			await service.installPlugin(plugin);
+
+			assert.strictEqual(state.trustedMarketplaces.length, 0);
+			assert.strictEqual(state.addedPlugins.length, 0);
+		});
+
+		test('trust prompt applies to all source kinds', async () => {
+			const { service, state } = createService({ marketplaceTrusted: false, dialogConfirmResult: false });
+
+			const kinds: IPluginSourceDescriptor[] = [
+				{ kind: PluginSourceKind.RelativePath, path: 'p' },
+				{ kind: PluginSourceKind.GitHub, repo: 'owner/repo' },
+				{ kind: PluginSourceKind.GitUrl, url: 'https://example.com/repo.git' },
+				{ kind: PluginSourceKind.Npm, package: 'my-pkg' },
+				{ kind: PluginSourceKind.Pip, package: 'my-pkg' },
+			];
+
+			for (const sourceDescriptor of kinds) {
+				await service.installPlugin(createPlugin({ sourceDescriptor }));
+			}
+
+			assert.strictEqual(state.addedPlugins.length, 0, 'no plugins should be installed when trust is declined');
+		});
+	});
+
+	// =========================================================================
+	// installPluginFromSource
+	// =========================================================================
+
+	suite('installPluginFromSource', () => {
+
+		test('rejects invalid source strings', async () => {
+			const { service, state } = createService();
+			await service.installPluginFromSource('not a valid source');
+			assert.strictEqual(state.addedPlugins.length, 0);
+			assert.strictEqual(state.notifications.length, 1);
+		});
+
+		test('rejects local file URIs', async () => {
+			const { service, state } = createService();
+			await service.installPluginFromSource('file:///some/local/path');
+			assert.strictEqual(state.addedPlugins.length, 0);
+			assert.strictEqual(state.notifications.length, 1);
+		});
+
+		test('installs single plugin from GitHub shorthand with marketplace.json', async () => {
+			const ref = makeMarketplaceRef('owner/my-plugin');
+			const discoveredPlugin = createPlugin({
+				name: 'my-discovered-plugin',
+				description: 'A discovered plugin',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: '' },
+				marketplace: ref.displayLabel,
+				marketplaceReference: ref,
+				marketplaceType: MarketplaceType.OpenPlugin,
+			});
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/github.com/owner/my-plugin'),
+				readPluginsResult: [discoveredPlugin],
+			});
+
+			await service.installPluginFromSource('owner/my-plugin');
+
+			assert.strictEqual(state.addedPlugins.length, 1);
+			assert.strictEqual(state.addedPlugins[0].plugin.name, 'my-discovered-plugin');
+		});
+
+		test('installs repo-root plugin when no marketplace.json found', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/github.com/owner/cool-tool'),
+				readPluginsResult: [],
+			});
+
+			await service.installPluginFromSource('owner/cool-tool');
+
+			assert.strictEqual(state.addedPlugins.length, 1);
+			assert.strictEqual(state.addedPlugins[0].plugin.name, 'cool-tool');
+			assert.strictEqual(state.addedPlugins[0].plugin.sourceDescriptor.kind, PluginSourceKind.GitHub);
+		});
+
+		test('shows quick pick for multi-plugin repos', async () => {
+			const ref = makeMarketplaceRef('owner/multi-repo');
+			const pluginA = createPlugin({
+				name: 'plugin-a',
+				source: 'plugins/a',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/a' },
+				marketplace: ref.displayLabel,
+				marketplaceReference: ref,
+			});
+			const pluginB = createPlugin({
+				name: 'plugin-b',
+				source: 'plugins/b',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/b' },
+				marketplace: ref.displayLabel,
+				marketplaceReference: ref,
+			});
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/github.com/owner/multi-repo'),
+				readPluginsResult: [pluginA, pluginB],
+				quickPickResult: { label: 'plugin-b' },
+			});
+
+			await service.installPluginFromSource('owner/multi-repo');
+
+			assert.strictEqual(state.addedPlugins.length, 1);
+			assert.strictEqual(state.addedPlugins[0].plugin.name, 'plugin-b');
+			assert.ok(state.addedPlugins[0].uri.includes('plugins/b'));
+		});
+
+		test('does not install when quick pick is cancelled', async () => {
+			const ref = makeMarketplaceRef('owner/multi-repo');
+			const pluginA = createPlugin({
+				name: 'plugin-a',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/a' },
+				marketplace: ref.displayLabel,
+				marketplaceReference: ref,
+			});
+			const pluginB = createPlugin({
+				name: 'plugin-b',
+				sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/b' },
+				marketplace: ref.displayLabel,
+				marketplaceReference: ref,
+			});
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/github.com/owner/multi-repo'),
+				readPluginsResult: [pluginA, pluginB],
+				quickPickResult: undefined,
+			});
+
+			await service.installPluginFromSource('owner/multi-repo');
+
+			assert.strictEqual(state.addedPlugins.length, 0);
+		});
+
+		test('does not install when trust is declined', async () => {
+			const { service, state } = createService({
+				marketplaceTrusted: false,
+				dialogConfirmResult: false,
+				readPluginsResult: [],
+			});
+
+			await service.installPluginFromSource('owner/repo');
+
+			assert.strictEqual(state.addedPlugins.length, 0);
+		});
+
+		test('installs from full git URL', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/github.com/owner/my-tool'),
+				readPluginsResult: [],
+			});
+
+			await service.installPluginFromSource('https://github.com/owner/my-tool.git');
+
+			assert.strictEqual(state.addedPlugins.length, 1);
+			assert.strictEqual(state.addedPlugins[0].plugin.name, 'my-tool');
+			assert.strictEqual(state.addedPlugins[0].plugin.sourceDescriptor.kind, PluginSourceKind.GitUrl);
+		});
+
+		test('shows error when clone directory does not exist', async () => {
+			const { service, state } = createService({
+				ensurePluginSourceResult: URI.file('/cache/agentPlugins/github.com/owner/missing'),
+				fileExistsResult: false,
+			});
+
+			await service.installPluginFromSource('owner/missing');
+
+			assert.strictEqual(state.addedPlugins.length, 0);
+			assert.strictEqual(state.notifications.length, 1);
+		});
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/browser/promptSyntax/hookUtils.test.ts b/src/vs/workbench/contrib/chat/test/browser/promptSyntax/hookUtils.test.ts
index d75ce8adbb8a9..33cbbd85c1aae 100644
--- a/src/vs/workbench/contrib/chat/test/browser/promptSyntax/hookUtils.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/promptSyntax/hookUtils.test.ts
@@ -5,7 +5,7 @@
 
 import assert from 'assert';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
-import { findHookCommandSelection } from '../../../browser/promptSyntax/hookUtils.js';
+import { findHookCommandInYaml, findHookCommandSelection } from '../../../browser/promptSyntax/hookUtils.js';
 import { ITextEditorSelection } from '../../../../../../platform/editor/common/editor.js';
 import { buildNewHookEntry, HookSourceFormat } from '../../../common/promptSyntax/hookCompatibility.js';
 
@@ -722,4 +722,232 @@ suite('hookUtils', () => {
 			});
 		});
 	});
+
+	suite('findHookCommandInYaml', () => {
+
+		test('finds unquoted command value', () => {
+			const content = [
+				'---',
+				'hooks:',
+				'  sessionStart:',
+				'    - command: echo hello',
+				'---',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'echo hello');
+			assert.ok(result);
+			assert.strictEqual(getSelectedText(content, result), 'echo hello');
+			assert.deepStrictEqual(result, {
+				startLineNumber: 4,
+				startColumn: 16,
+				endLineNumber: 4,
+				endColumn: 26
+			});
+		});
+
+		test('finds double-quoted command value', () => {
+			const content = [
+				'---',
+				'hooks:',
+				'  sessionStart:',
+				'    - command: "echo hello"',
+				'---',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'echo hello');
+			assert.ok(result);
+			assert.strictEqual(getSelectedText(content, result), 'echo hello');
+		});
+
+		test('finds single-quoted command value', () => {
+			const content = [
+				'---',
+				'hooks:',
+				'  sessionStart:',
+				`    - command: 'echo hello'`,
+				'---',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'echo hello');
+			assert.ok(result);
+			assert.strictEqual(getSelectedText(content, result), 'echo hello');
+		});
+
+		test('finds command without list prefix', () => {
+			const content = [
+				'---',
+				'hooks:',
+				'  sessionStart:',
+				'    command: run-lint',
+				'---',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'run-lint');
+			assert.ok(result);
+			assert.strictEqual(getSelectedText(content, result), 'run-lint');
+		});
+
+		test('does not match substring of a longer command', () => {
+			const content = [
+				'---',
+				'hooks:',
+				'  sessionStart:',
+				'    - command: echo hello-world',
+				'---',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'echo hello');
+			assert.strictEqual(result, undefined);
+		});
+
+		test('returns undefined when command is not found', () => {
+			const content = [
+				'---',
+				'hooks:',
+				'  sessionStart:',
+				'    - command: echo hello',
+				'---',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'echo goodbye');
+			assert.strictEqual(result, undefined);
+		});
+
+		test('returns undefined when no command lines exist', () => {
+			const content = [
+				'---',
+				'name: my-agent',
+				'description: An agent',
+				'---',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'echo hello');
+			assert.strictEqual(result, undefined);
+		});
+
+		test('returns undefined for empty content', () => {
+			const result = findHookCommandInYaml('', 'echo hello');
+			assert.strictEqual(result, undefined);
+		});
+
+		test('finds first matching command when multiple exist', () => {
+			const content = [
+				'---',
+				'hooks:',
+				'  sessionStart:',
+				'    - command: echo hello',
+				'  userPromptSubmit:',
+				'    - command: echo hello',
+				'---',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'echo hello');
+			assert.ok(result);
+			assert.strictEqual(result.startLineNumber, 4);
+		});
+
+		test('ignores lines that are not command fields', () => {
+			const content = [
+				'---',
+				'description: run command echo hello',
+				'hooks:',
+				'  sessionStart:',
+				'    - command: echo hello',
+				'---',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'echo hello');
+			assert.ok(result);
+			assert.strictEqual(result.startLineNumber, 5);
+		});
+
+		test('handles command with special characters', () => {
+			const content = [
+				'---',
+				'hooks:',
+				'  preToolUse:',
+				'    - command: echo "foo" > /tmp/out.txt',
+				'---',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'echo "foo" > /tmp/out.txt');
+			assert.ok(result);
+			assert.strictEqual(getSelectedText(content, result), 'echo "foo" > /tmp/out.txt');
+		});
+
+		test('matches command followed by trailing whitespace', () => {
+			const content = [
+				'---',
+				'hooks:',
+				'  sessionStart:',
+				'    - command: echo hello   ',
+				'---',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'echo hello');
+			assert.ok(result);
+			assert.strictEqual(getSelectedText(content, result), 'echo hello');
+		});
+
+		test('finds short command that is a substring of the key name', () => {
+			const content = [
+				'hooks:',
+				'  Stop:',
+				'    - timeout: 10',
+				'      command: "a"',
+				'      type: command',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'a');
+			assert.ok(result);
+			assert.strictEqual(getSelectedText(content, result), 'a');
+			assert.strictEqual(result.startLineNumber, 4);
+		});
+
+		test('finds short command in bash field that is a substring of the key name', () => {
+			const content = [
+				'hooks:',
+				'  sessionStart:',
+				'    - bash: "a"',
+				'      type: command',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'a');
+			assert.ok(result);
+			assert.strictEqual(getSelectedText(content, result), 'a');
+			assert.strictEqual(result.startLineNumber, 3);
+		});
+
+		test('finds command in powershell field', () => {
+			const content = [
+				'hooks:',
+				'  sessionStart:',
+				'    - powershell: "echo hello"',
+				'      type: command',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'echo hello');
+			assert.ok(result);
+			assert.strictEqual(getSelectedText(content, result), 'echo hello');
+			assert.strictEqual(result.startLineNumber, 3);
+		});
+
+		test('finds command in windows field', () => {
+			const content = [
+				'hooks:',
+				'  sessionStart:',
+				'    - windows: "dir"',
+				'      type: command',
+			].join('\n');
+			const result = findHookCommandInYaml(content, 'dir');
+			assert.ok(result);
+			assert.strictEqual(getSelectedText(content, result), 'dir');
+			assert.strictEqual(result.startLineNumber, 3);
+		});
+
+		test('finds command in linux and osx fields', () => {
+			const content = [
+				'hooks:',
+				'  sessionStart:',
+				'    - linux: "ls"',
+				'      osx: "ls -G"',
+				'      type: command',
+			].join('\n');
+			const linuxResult = findHookCommandInYaml(content, 'ls');
+			assert.ok(linuxResult);
+			assert.strictEqual(getSelectedText(content, linuxResult), 'ls');
+			assert.strictEqual(linuxResult.startLineNumber, 3);
+
+			const osxResult = findHookCommandInYaml(content, 'ls -G');
+			assert.ok(osxResult);
+			assert.strictEqual(getSelectedText(content, osxResult), 'ls -G');
+			assert.strictEqual(osxResult.startLineNumber, 4);
+		});
+	});
 });
diff --git a/src/vs/workbench/contrib/chat/test/browser/promptSyntax/languageProviders/promptHeaderAutocompletion.test.ts b/src/vs/workbench/contrib/chat/test/browser/promptSyntax/languageProviders/promptHeaderAutocompletion.test.ts
index 8fdd981ea7186..101e3235aeabe 100644
--- a/src/vs/workbench/contrib/chat/test/browser/promptSyntax/languageProviders/promptHeaderAutocompletion.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/promptSyntax/languageProviders/promptHeaderAutocompletion.test.ts
@@ -19,12 +19,12 @@ import { ILanguageModelToolsService, IToolData, ToolDataSource } from '../../../
 import { ILanguageModelChatMetadata, ILanguageModelsService } from '../../../../common/languageModels.js';
 import { IChatModeService } from '../../../../common/chatModes.js';
 import { PromptHeaderAutocompletion } from '../../../../common/promptSyntax/languageProviders/promptHeaderAutocompletion.js';
-import { ICustomAgent, IPromptsService, PromptsStorage, Target } from '../../../../common/promptSyntax/service/promptsService.js';
+import { ICustomAgent, IPromptsService, PromptsStorage } from '../../../../common/promptSyntax/service/promptsService.js';
+import { getLanguageIdForPromptsType, PromptsType, Target } from '../../../../common/promptSyntax/promptTypes.js';
 import { createTextModel } from '../../../../../../../editor/test/common/testTextModel.js';
 import { URI } from '../../../../../../../base/common/uri.js';
 import { PromptFileParser } from '../../../../common/promptSyntax/promptFileParser.js';
 import { ITextModel } from '../../../../../../../editor/common/model.js';
-import { getLanguageIdForPromptsType, PromptsType } from '../../../../common/promptSyntax/promptTypes.js';
 import { getPromptFileExtension } from '../../../../common/promptSyntax/config/promptFileLocations.js';
 import { Range } from '../../../../../../../editor/common/core/range.js';
 
@@ -37,6 +37,7 @@ suite('PromptHeaderAutocompletion', () => {
 	setup(async () => {
 		const testConfigService = new TestConfigurationService();
 		testConfigService.setUserConfiguration(ChatConfiguration.ExtensionToolsEnabled, true);
+		testConfigService.setUserConfiguration('chat.useCustomAgentHooks', true);
 		instaService = workbenchInstantiationService({
 			contextKeyService: () => disposables.add(new ContextKeyService(testConfigService)),
 			configurationService: () => testConfigService
@@ -143,6 +144,7 @@ suite('PromptHeaderAutocompletion', () => {
 				{ label: 'disable-model-invocation', result: 'disable-model-invocation: ${0:true}' },
 				{ label: 'github', result: 'github: $0' },
 				{ label: 'handoffs', result: 'handoffs: $0' },
+				{ label: 'hooks', result: 'hooks:\n  ${1|SessionStart,SessionEnd,UserPromptSubmit,PreToolUse,PostToolUse,PreCompact,SubagentStart,SubagentStop,Stop,ErrorOccurred|}:\n    - type: command\n      command: "$2"' },
 				{ label: 'model', result: 'model: ${0:MAE 4 (olama)}' },
 				{ label: 'name', result: 'name: $0' },
 				{ label: 'target', result: 'target: ${0:vscode}' },
@@ -390,6 +392,249 @@ suite('PromptHeaderAutocompletion', () => {
 			const labels = actual.map(a => a.label);
 			assert.ok(!labels.includes('BG Agent Model (copilot)'), 'Models with targetChatSessionType should be excluded from agent model array completions');
 		});
+
+		test('complete hooks value with New Hook snippet', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks: |',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			assert.deepStrictEqual(actual, [
+				{
+					label: 'New Hook',
+					result: 'hooks: \n  ${1|SessionStart,SessionEnd,UserPromptSubmit,PreToolUse,PostToolUse,PreCompact,SubagentStart,SubagentStop,Stop,ErrorOccurred|}:\n    - type: command\n      command: "$2"'
+				},
+			]);
+		});
+
+		test('complete hooks value with New Hook snippet for vscode target', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'target: vscode',
+				'hooks: |',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			assert.deepStrictEqual(actual, [
+				{
+					label: 'New Hook',
+					result: 'hooks: \n  ${1|SessionStart,UserPromptSubmit,PreToolUse,PostToolUse,PreCompact,SubagentStart,SubagentStop,Stop|}:\n    - type: command\n      command: "$2"'
+				},
+			]);
+		});
+
+		test('complete hook event names inside hooks map', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: command',
+				'      command: "echo hi"',
+				'  |',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			const labels = actual.map(a => a.label).sort();
+			// SessionStart should be excluded since it already exists
+			assert.ok(!labels.includes('SessionStart'), 'SessionStart should not be suggested when already present');
+			assert.ok(labels.includes('SessionEnd'), 'SessionEnd should be suggested');
+			assert.ok(labels.includes('PreToolUse'), 'PreToolUse should be suggested');
+			assert.ok(labels.includes('Stop'), 'Stop should be suggested');
+		});
+
+		test('complete hook event names for vscode target excludes existing hooks', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'target: vscode',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: command',
+				'      command: "echo hi"',
+				'  PreToolUse:',
+				'    - type: command',
+				'      command: "lint"',
+				'  |',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			const labels = actual.map(a => a.label).sort();
+			assert.ok(!labels.includes('SessionStart'), 'SessionStart should not be suggested when already present');
+			assert.ok(!labels.includes('PreToolUse'), 'PreToolUse should not be suggested when already present');
+			assert.ok(labels.includes('UserPromptSubmit'), 'UserPromptSubmit should be suggested');
+			assert.ok(labels.includes('PostToolUse'), 'PostToolUse should be suggested');
+			// SessionEnd is not available for vscode target
+			assert.ok(!labels.includes('SessionEnd'), 'SessionEnd should not be available for vscode target');
+		});
+
+		test('complete hook event names on empty line before existing hooks', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  |',
+				'  SessionStart:',
+				'    - type: command',
+				'      command: "echo hi"',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			const labels = actual.map(a => a.label).sort();
+			assert.ok(!labels.includes('SessionStart'), 'SessionStart should not be suggested when already present');
+			assert.ok(labels.includes('SessionEnd'), 'SessionEnd should be suggested');
+			assert.ok(labels.includes('PreToolUse'), 'PreToolUse should be suggested');
+		});
+
+		test('complete hook event names while editing existing key name', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  S|:',
+				'    - type: command',
+				'      command: "echo hi"',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			const labels = actual.map(a => a.label).sort();
+			assert.ok(labels.includes('SessionStart'), 'SessionStart should be suggested');
+			assert.ok(labels.includes('SubagentStart'), 'SubagentStart should be suggested');
+			assert.ok(labels.includes('Stop'), 'Stop should be suggested');
+			// Verify insertText only replaces the key (no full snippet)
+			const sessionStartItem = actual.find(a => a.label === 'SessionStart');
+			assert.ok(sessionStartItem);
+			assert.strictEqual(sessionStartItem.result, '  SessionStart:');
+		});
+
+		test('hooks: cursor right after colon triggers New Hook snippet', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks: |',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			const labels = actual.map(a => a.label);
+			assert.ok(labels.includes('New Hook'), 'New Hook snippet should be suggested');
+		});
+
+		test('hooks: typing event name on next line triggers hook events', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  S|',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			const labels = actual.map(a => a.label);
+			assert.ok(labels.includes('SessionStart'), 'SessionStart should be suggested');
+			assert.ok(labels.includes('SessionEnd'), 'SessionEnd should be suggested');
+			assert.ok(labels.includes('Stop'), 'Stop should be suggested');
+		});
+
+		test('typing field name in first command entry triggers command fields', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionEnd:',
+				'    - t|',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			const labels = actual.map(a => a.label);
+			assert.ok(labels.includes('type'), 'type should be suggested');
+			assert.ok(labels.includes('command'), 'command should be suggested');
+			assert.ok(labels.includes('timeout'), 'timeout should be suggested');
+		});
+
+		test('typing field name after existing field triggers remaining command fields', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionEnd:',
+				'    - type: command',
+				'      c|',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			const labels = actual.map(a => a.label);
+			assert.ok(labels.includes('command'), 'command should be suggested');
+			assert.ok(labels.includes('cwd'), 'cwd should be suggested');
+			assert.ok(!labels.includes('type'), 'type should not be suggested when already present');
+		});
+
+		test('typing event name after existing hook triggers hook events', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionEnd:',
+				'    - type: command',
+				'      command: echo "Session ended."',
+				'  U|',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			const labels = actual.map(a => a.label);
+			assert.ok(labels.includes('UserPromptSubmit'), 'UserPromptSubmit should be suggested');
+			assert.ok(!labels.includes('SessionEnd'), 'SessionEnd should not be suggested when already present');
+		});
+
+		test('typing event name between existing hooks triggers hook events', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionEnd:',
+				'    - type: command',
+				'      command: echo "Session ended."',
+				'  S|',
+				'  UserPromptSubmit:',
+				'    - type: command',
+				'      command: echo "User submitted."',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			const labels = actual.map(a => a.label);
+			assert.ok(labels.includes('SessionStart'), 'SessionStart should be suggested');
+			assert.ok(labels.includes('Stop'), 'Stop should be suggested');
+			assert.ok(!labels.includes('SessionEnd'), 'SessionEnd should not be suggested when already present');
+			assert.ok(!labels.includes('UserPromptSubmit'), 'UserPromptSubmit should not be suggested when already present');
+		});
+
+		test('cursor after hook event colon triggers New Command snippet', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionEnd: |',
+				'---',
+			].join('\n');
+
+			const actual = await getCompletions(content, PromptsType.agent);
+			const labels = actual.map(a => a.label);
+			assert.ok(labels.includes('New Command'), 'New Command snippet should be suggested');
+			assert.strictEqual(actual.length, 1, 'Only one suggestion should be returned');
+		});
 	});
 
 	suite('claude agent header completions', () => {
diff --git a/src/vs/workbench/contrib/chat/test/browser/promptSyntax/languageProviders/promptHovers.test.ts b/src/vs/workbench/contrib/chat/test/browser/promptSyntax/languageProviders/promptHovers.test.ts
index f8042fe069e53..ab2a3b4067c0d 100644
--- a/src/vs/workbench/contrib/chat/test/browser/promptSyntax/languageProviders/promptHovers.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/promptSyntax/languageProviders/promptHovers.test.ts
@@ -18,14 +18,14 @@ import { ChatAgentLocation, ChatConfiguration } from '../../../../common/constan
 import { ILanguageModelToolsService, IToolData, ToolDataSource } from '../../../../common/tools/languageModelToolsService.js';
 import { ILanguageModelChatMetadata, ILanguageModelsService } from '../../../../common/languageModels.js';
 import { PromptHoverProvider } from '../../../../common/promptSyntax/languageProviders/promptHovers.js';
-import { IPromptsService, PromptsStorage, Target } from '../../../../common/promptSyntax/service/promptsService.js';
+import { IPromptsService, PromptsStorage } from '../../../../common/promptSyntax/service/promptsService.js';
+import { getLanguageIdForPromptsType, PromptsType, Target } from '../../../../common/promptSyntax/promptTypes.js';
 import { MockChatModeService } from '../../../common/mockChatModeService.js';
 import { createTextModel } from '../../../../../../../editor/test/common/testTextModel.js';
 import { URI } from '../../../../../../../base/common/uri.js';
 import { PromptFileParser } from '../../../../common/promptSyntax/promptFileParser.js';
 import { ITextModel } from '../../../../../../../editor/common/model.js';
 import { MarkdownString } from '../../../../../../../base/common/htmlContent.js';
-import { getLanguageIdForPromptsType, PromptsType } from '../../../../common/promptSyntax/promptTypes.js';
 import { getPromptFileExtension } from '../../../../common/promptSyntax/config/promptFileLocations.js';
 
 suite('PromptHoverProvider', () => {
@@ -37,6 +37,7 @@ suite('PromptHoverProvider', () => {
 	setup(async () => {
 		const testConfigService = new TestConfigurationService();
 		testConfigService.setUserConfiguration(ChatConfiguration.ExtensionToolsEnabled, true);
+		testConfigService.setUserConfiguration('chat.useCustomAgentHooks', true);
 		instaService = workbenchInstantiationService({
 			contextKeyService: () => disposables.add(new ContextKeyService(testConfigService)),
 			configurationService: () => testConfigService
@@ -405,7 +406,7 @@ suite('PromptHoverProvider', () => {
 				'The agent to use when running this prompt.',
 				'',
 				'**Built-in agents:**',
-				'- `agent`: Describe what to build next',
+				'- `agent`: Describe what to build',
 				'- `ask`: Explore and understand your code',
 				'- `edit`: Edit or refactor selected code',
 				'',
diff --git a/src/vs/workbench/contrib/chat/test/browser/promptSyntax/languageProviders/promptValidator.test.ts b/src/vs/workbench/contrib/chat/test/browser/promptSyntax/languageProviders/promptValidator.test.ts
index e3cc440de6346..be2df9c04566b 100644
--- a/src/vs/workbench/contrib/chat/test/browser/promptSyntax/languageProviders/promptValidator.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/promptSyntax/languageProviders/promptValidator.test.ts
@@ -23,9 +23,9 @@ import { ILanguageModelToolsService, IToolData, ToolDataSource } from '../../../
 import { ILanguageModelChatMetadata, ILanguageModelsService } from '../../../../common/languageModels.js';
 import { getPromptFileExtension } from '../../../../common/promptSyntax/config/promptFileLocations.js';
 import { PromptValidator } from '../../../../common/promptSyntax/languageProviders/promptValidator.js';
-import { PromptsType } from '../../../../common/promptSyntax/promptTypes.js';
+import { PromptsType, Target } from '../../../../common/promptSyntax/promptTypes.js';
 import { PromptFileParser } from '../../../../common/promptSyntax/promptFileParser.js';
-import { ICustomAgent, IPromptsService, PromptsStorage, Target } from '../../../../common/promptSyntax/service/promptsService.js';
+import { ICustomAgent, IPromptsService, PromptsStorage } from '../../../../common/promptSyntax/service/promptsService.js';
 import { MockChatModeService } from '../../../common/mockChatModeService.js';
 import { MockPromptsService } from '../../../common/promptSyntax/service/mockPromptsService.js';
 
@@ -41,6 +41,7 @@ suite('PromptValidator', () => {
 
 		const testConfigService = new TestConfigurationService();
 		testConfigService.setUserConfiguration(ChatConfiguration.ExtensionToolsEnabled, true);
+		testConfigService.setUserConfiguration('chat.useCustomAgentHooks', true);
 		instaService = workbenchInstantiationService({
 			contextKeyService: () => disposables.add(new ContextKeyService(testConfigService)),
 			configurationService: () => testConfigService
@@ -551,7 +552,7 @@ suite('PromptValidator', () => {
 			assert.deepStrictEqual(
 				markers.map(m => ({ severity: m.severity, message: m.message })),
 				[
-					{ severity: MarkerSeverity.Warning, message: `Attribute 'applyTo' is not supported in VS Code agent files. Supported: agents, argument-hint, description, disable-model-invocation, github, handoffs, model, name, target, tools, user-invocable.` },
+					{ severity: MarkerSeverity.Warning, message: `Attribute 'applyTo' is not supported in VS Code agent files. Supported: agents, argument-hint, description, disable-model-invocation, github, handoffs, hooks, model, name, target, tools, user-invocable.` },
 				]
 			);
 		});
@@ -1416,6 +1417,358 @@ suite('PromptValidator', () => {
 				assert.strictEqual(markers[0].message, `The 'disable-model-invocation' attribute must be 'true' or 'false'.`);
 			}
 		});
+
+		test('hooks - valid hook commands', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: command',
+				'      command: echo hello',
+				'  PreToolUse:',
+				'    - type: command',
+				'      command: ./validate.sh',
+				'      cwd: scripts',
+				'      timeout: 30',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(markers, []);
+		});
+
+		test('hooks - must be a map', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks: invalid',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `The 'hooks' attribute must be a map of hook event types to command arrays.` },
+				]
+			);
+		});
+
+		test('hooks - unknown hook event type', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  UnknownEvent:',
+				'    - type: command',
+				'      command: echo hello',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Warning, message: `Unknown hook event type 'UnknownEvent'. Supported: SessionStart, SessionEnd, UserPromptSubmit, PreToolUse, PostToolUse, PreCompact, SubagentStart, SubagentStop, Stop, ErrorOccurred.` },
+				]
+			);
+		});
+
+		test('hooks - hook value must be array', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart: invalid',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `Hook event 'SessionStart' must have an array of command objects as its value.` },
+				]
+			);
+		});
+
+		test('hooks - command item must be object', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - just a string',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `Each hook command must be an object.` },
+				]
+			);
+		});
+
+		test('hooks - missing type property', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - command: echo hello',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `Hook command is missing required property 'type'.` },
+				]
+			);
+		});
+
+		test('hooks - type must be command', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: script',
+				'      command: echo hello',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `The 'type' property in a hook command must be 'command'.` },
+				]
+			);
+		});
+
+		test('hooks - missing command field', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: command',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `Hook command must specify at least one of 'command', 'windows', 'linux', or 'osx'.` },
+				]
+			);
+		});
+
+		test('hooks - empty command string', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: command',
+				'      command: ""',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `The 'command' property in a hook command must be a non-empty string.` },
+				]
+			);
+		});
+
+		test('hooks - platform-specific commands are valid', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: command',
+				'      windows: echo hello',
+				'      linux: echo hello',
+				'      osx: echo hello',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(markers, []);
+		});
+
+		test('hooks - env must be a map with string values', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: command',
+				'      command: echo hello',
+				'      env: invalid',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `The 'env' property in a hook command must be a map of string values.` },
+				]
+			);
+		});
+
+		test('hooks - valid env map', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: command',
+				'      command: echo hello',
+				'      env:',
+				'        NODE_ENV: production',
+				'        DEBUG: "true"',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(markers, []);
+		});
+
+		test('hooks - unknown property warns', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: command',
+				'      command: echo hello',
+				'      unknownProp: value',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Warning, message: `Unknown property 'unknownProp' in hook command.` },
+				]
+			);
+		});
+
+		test('hooks - timeout must be number', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: command',
+				'      command: echo hello',
+				'      timeout: not-a-number',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `The 'timeout' property in a hook command must be a number.` },
+				]
+			);
+		});
+
+		test('hooks - cwd must be string', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: command',
+				'      command: echo hello',
+				'      cwd:',
+				'        - array',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `The 'cwd' property in a hook command must be a string.` },
+				]
+			);
+		});
+
+		test('hooks - multiple errors in one command', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  SessionStart:',
+				'    - type: script',
+				'      unknownProp: value',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `The 'type' property in a hook command must be 'command'.` },
+					{ severity: MarkerSeverity.Warning, message: `Unknown property 'unknownProp' in hook command.` },
+					{ severity: MarkerSeverity.Error, message: `Hook command must specify at least one of 'command', 'windows', 'linux', or 'osx'.` },
+				]
+			);
+		});
+
+		test('hooks - nested matcher format is valid', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  UserPromptSubmit:',
+				'    - hooks:',
+				'        - type: command',
+				'          command: "echo foo"',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(markers, []);
+		});
+
+		test('hooks - nested matcher validates inner commands', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  PreToolUse:',
+				'    - matcher: Bash',
+				'      hooks:',
+				'        - type: script',
+				'          command: "echo foo"',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `The 'type' property in a hook command must be 'command'.` },
+				]
+			);
+		});
+
+		test('hooks - nested hooks must be array', async () => {
+			const content = [
+				'---',
+				'description: "Test"',
+				'hooks:',
+				'  PreToolUse:',
+				'    - hooks: invalid',
+				'---',
+			].join('\n');
+			const markers = await validate(content, PromptsType.agent);
+			assert.deepStrictEqual(
+				markers.map(m => ({ severity: m.severity, message: m.message })),
+				[
+					{ severity: MarkerSeverity.Error, message: `The 'hooks' property in a matcher must be an array of command objects.` },
+				]
+			);
+		});
 	});
 
 	suite('instructions', () => {
diff --git a/src/vs/workbench/contrib/chat/test/browser/promptsDebugContribution.test.ts b/src/vs/workbench/contrib/chat/test/browser/promptsDebugContribution.test.ts
index 2233f9cd99294..b7a4694c4e5cd 100644
--- a/src/vs/workbench/contrib/chat/test/browser/promptsDebugContribution.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/promptsDebugContribution.test.ts
@@ -10,6 +10,7 @@ import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/tes
 import { TestInstantiationService } from '../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
 import { ChatDebugLogLevel, IChatDebugEvent, IChatDebugGenericEvent, IChatDebugService } from '../../common/chatDebugService.js';
 import { ChatDebugServiceImpl } from '../../common/chatDebugServiceImpl.js';
+import { LocalChatSessionUri } from '../../common/model/chatUri.js';
 import { PromptsDebugContribution } from '../../browser/promptsDebugContribution.js';
 import { IPromptDiscoveryLogEntry, IPromptDiscoveryInfo, IPromptsService, PromptsStorage } from '../../common/promptSyntax/service/promptsService.js';
 import { PromptsType } from '../../common/promptSyntax/promptTypes.js';
@@ -38,7 +39,7 @@ suite('PromptsDebugContribution', () => {
 		disposables.add(chatDebugService.onDidAddEvent(e => firedEvents.push(e)));
 
 		promptsOnDidLogDiscovery.fire({
-			sessionId: 'session-1',
+			sessionResource: LocalChatSessionUri.forSession('session-1'),
 			name: 'Load Instructions',
 			details: 'Resolved 3 instructions in 12.5ms',
 			category: 'discovery',
@@ -70,13 +71,11 @@ suite('PromptsDebugContribution', () => {
 			sourceFolders: [{
 				uri: URI.file('/workspace/.github/instructions'),
 				storage: PromptsStorage.local,
-				exists: true,
-				fileCount: 1,
 			}],
 		};
 
 		promptsOnDidLogDiscovery.fire({
-			sessionId: 'session-1',
+			sessionResource: LocalChatSessionUri.forSession('session-1'),
 			name: 'Discovery End',
 			details: '1 loaded, 0 skipped',
 			category: 'discovery',
@@ -96,7 +95,6 @@ suite('PromptsDebugContribution', () => {
 			assert.strictEqual(resolved.files[0].name, 'test.instructions.md');
 			assert.strictEqual(resolved.files[0].status, 'loaded');
 			assert.strictEqual(resolved.sourceFolders?.length, 1);
-			assert.strictEqual(resolved.sourceFolders?.[0].exists, true);
 		}
 	});
 
@@ -114,7 +112,7 @@ suite('PromptsDebugContribution', () => {
 		disposables.add(chatDebugService.onDidAddEvent(e => firedEvents.push(e)));
 
 		promptsOnDidLogDiscovery.fire({
-			sessionId: 'session-1',
+			sessionResource: LocalChatSessionUri.forSession('session-1'),
 			name: 'Discovery Start',
 			category: 'discovery',
 		});
@@ -149,7 +147,7 @@ suite('PromptsDebugContribution', () => {
 		};
 
 		promptsOnDidLogDiscovery.fire({
-			sessionId: 'session-1',
+			sessionResource: LocalChatSessionUri.forSession('session-1'),
 			name: 'Discovery End',
 			discoveryInfo,
 		});
@@ -172,7 +170,7 @@ suite('PromptsDebugContribution', () => {
 		disposables.add(chatDebugService.onDidAddEvent(e => firedEvents.push(e)));
 
 		promptsOnDidLogDiscovery.fire({
-			sessionId: 'session-1',
+			sessionResource: LocalChatSessionUri.forSession('session-1'),
 			name: 'Test',
 		});
 
diff --git a/src/vs/workbench/contrib/chat/test/browser/tools/languageModelToolsService.test.ts b/src/vs/workbench/contrib/chat/test/browser/tools/languageModelToolsService.test.ts
index f642745892e92..4689f30c00a3d 100644
--- a/src/vs/workbench/contrib/chat/test/browser/tools/languageModelToolsService.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/tools/languageModelToolsService.test.ts
@@ -24,7 +24,7 @@ import { workbenchInstantiationService } from '../../../../../test/browser/workb
 import { LanguageModelToolsService } from '../../../browser/tools/languageModelToolsService.js';
 import { ChatModel, IChatModel } from '../../../common/model/chatModel.js';
 import { IChatService, IChatToolInputInvocationData, IChatToolInvocation, ToolConfirmKind } from '../../../common/chatService/chatService.js';
-import { ChatConfiguration } from '../../../common/constants.js';
+import { ChatConfiguration, ChatPermissionLevel } from '../../../common/constants.js';
 import { SpecedToolAliases, isToolResultInputOutputDetails, IToolData, IToolImpl, IToolInvocation, ToolDataSource, ToolSet, IToolResultTextPart } from '../../../common/tools/languageModelToolsService.js';
 import { MockChatService } from '../../common/chatService/mockChatService.js';
 import { ChatToolInvocation } from '../../../common/model/chatProgressTypes/chatToolInvocation.js';
@@ -83,13 +83,13 @@ function registerToolForTest(service: LanguageModelToolsService, store: any, id:
 	};
 }
 
-function stubGetSession(chatService: MockChatService, sessionId: string, options?: { requestId?: string; capture?: { invocation?: any } }): IChatModel {
+function stubGetSession(chatService: MockChatService, sessionId: string, options?: { requestId?: string; capture?: { invocation?: any }; modeInfo?: { permissionLevel?: ChatPermissionLevel } }): IChatModel {
 	const requestId = options?.requestId ?? 'requestId';
 	const capture = options?.capture;
 	const fakeModel = {
 		sessionId,
 		sessionResource: LocalChatSessionUri.forSession(sessionId),
-		getRequests: () => [{ id: requestId, modelId: 'test-model' }],
+		getRequests: () => [{ id: requestId, modelId: 'test-model', modeInfo: options?.modeInfo }],
 	} as ChatModel;
 	chatService.addSession(fakeModel);
 	chatService.appendProgress = (request, progress) => {
@@ -592,6 +592,48 @@ suite('LanguageModelToolsService', () => {
 		await promise;
 	});
 
+	test('skipping modified-files confirmation returns the shared skip message and does not invoke the tool', async () => {
+		let invoked = false;
+		const tool = registerToolForTest(service, store, 'testModifiedFilesConfirmationSkip', {
+			prepareToolInvocation: async () => ({
+				confirmationMessages: {
+					title: 'Confirm',
+					message: 'Choose',
+					allowAutoConfirm: false,
+				},
+				toolSpecificData: {
+					kind: 'modifiedFilesConfirmation',
+					options: ['Copy Changes', 'Move Changes'],
+					modifiedFiles: [{
+						uri: URI.parse('file:///workspace/file1.ts')
+					}]
+				}
+			}),
+			invoke: async () => {
+				invoked = true;
+				return { content: [{ kind: 'text', value: 'should not run' }] };
+			},
+		});
+
+		const sessionId = 'sessionId-modified-files-skip';
+		const capture: { invocation?: any } = {};
+		stubGetSession(chatService, sessionId, { requestId: 'requestId-modified-files-skip', capture });
+
+		const dto = tool.makeDto({ x: 1 }, { sessionId });
+		const promise = service.invokeTool(dto, async () => 0, CancellationToken.None);
+		const published = await waitForPublishedInvocation(capture);
+		assert.ok(published, 'expected ChatToolInvocation to be published');
+
+		IChatToolInvocation.confirmWith(published, { type: ToolConfirmKind.Skipped });
+		const result = await promise;
+
+		assert.strictEqual(invoked, false);
+		assert.deepStrictEqual(result.content, [{
+			kind: 'text',
+			value: 'The user chose to skip the tool call, they want to proceed without running it'
+		}]);
+	});
+
 	test('cancel tool call', async () => {
 		const toolBarrier = new Barrier();
 		const tool = registerToolForTest(service, store, 'testTool', {
@@ -1453,6 +1495,144 @@ suite('LanguageModelToolsService', () => {
 		assert.strictEqual(testAccessibilitySignalService.signalPlayedCalls.length, 0, 'accessibility signal should not be played when auto-approve is enabled');
 	});
 
+	test('autopilot permission level bypasses global auto-approve check', async () => {
+		// When autopilot is on, tools should auto-approve without needing global auto-approve enabled
+		const { service: testService, chatService: testChatService } = createTestToolsService(store, {
+			configureServices: config => {
+				config.setUserConfiguration('chat.tools.global.autoApprove', false); // Global OFF
+			}
+		});
+
+		const tool = registerToolForTest(testService, store, 'autopilotTool', {
+			prepareToolInvocation: async () => ({ confirmationMessages: { title: 'Confirm?', message: 'Should be auto-approved by autopilot' } }),
+			invoke: async () => ({ content: [{ kind: 'text', value: 'autopilot approved' }] })
+		});
+
+		const sessionId = 'test-autopilot';
+		stubGetSession(testChatService, sessionId, {
+			requestId: 'req1',
+			modeInfo: { permissionLevel: ChatPermissionLevel.Autopilot },
+		});
+
+		// Tool should be auto-approved even though global auto-approve is off
+		const result = await testService.invokeTool(
+			tool.makeDto({ test: 1 }, { sessionId }),
+			async () => 0,
+			CancellationToken.None
+		);
+		assert.strictEqual(result.content[0].value, 'autopilot approved');
+	});
+
+	test('autopilot finds correct request by chatRequestId', async () => {
+		// When chatRequestId is provided, the exact request should be matched
+		const { service: testService, chatService: testChatService } = createTestToolsService(store, {
+			configureServices: config => {
+				config.setUserConfiguration('chat.tools.global.autoApprove', false);
+			}
+		});
+
+		const tool = registerToolForTest(testService, store, 'autopilotIdTool', {
+			prepareToolInvocation: async () => ({ confirmationMessages: { title: 'Confirm?', message: 'Test' } }),
+			invoke: async () => ({ content: [{ kind: 'text', value: 'found by id' }] })
+		});
+
+		const sessionId = 'test-autopilot-id';
+		const fakeModel = {
+			sessionId,
+			sessionResource: LocalChatSessionUri.forSession(sessionId),
+			getRequests: () => [
+				{ id: 'req-old', modelId: 'test-model', modeInfo: undefined },
+				{ id: 'req-autopilot', modelId: 'test-model', modeInfo: { permissionLevel: ChatPermissionLevel.Autopilot } },
+			],
+		} as ChatModel;
+		testChatService.addSession(fakeModel);
+
+		const dto = tool.makeDto({ test: 1 }, { sessionId });
+		dto.chatRequestId = 'req-autopilot';
+
+		const result = await testService.invokeTool(dto, async () => 0, CancellationToken.None);
+		assert.strictEqual(result.content[0].value, 'found by id');
+	});
+
+	test('autopilot auto-approves terminal tool with confirmation messages', async () => {
+		// Terminal tools always return confirmationMessages when their own auto-approve is off.
+		// In autopilot mode, shouldAutoConfirm should still auto-approve the tool.
+		const { service: testService, chatService: testChatService } = createTestToolsService(store, {
+			configureServices: config => {
+				config.setUserConfiguration('chat.tools.global.autoApprove', false);
+			}
+		});
+
+		const tool = registerToolForTest(testService, store, 'terminalTool', {
+			prepareToolInvocation: async () => ({
+				confirmationMessages: {
+					title: 'Run shell command?',
+					message: 'echo hello',
+				},
+				toolSpecificData: {
+					kind: 'terminal' as const,
+					terminalToolSessionId: 'test',
+					terminalCommandId: 'cmd-1',
+					commandLine: { original: 'echo hello' },
+					language: 'sh',
+				},
+			}),
+			invoke: async () => ({ content: [{ kind: 'text', value: 'terminal executed' }] })
+		});
+
+		const sessionId = 'test-autopilot-terminal';
+		stubGetSession(testChatService, sessionId, {
+			requestId: 'req1',
+			modeInfo: { permissionLevel: ChatPermissionLevel.Autopilot },
+		});
+
+		// Terminal tool should be auto-approved by autopilot even without terminal auto-approve enabled
+		const result = await testService.invokeTool(
+			tool.makeDto({ command: 'echo hello', explanation: 'test', goal: 'test', isBackground: false }, { sessionId }),
+			async () => 0,
+			CancellationToken.None
+		);
+		assert.strictEqual(result.content[0].value, 'terminal executed');
+	});
+
+	test('bypass approvals auto-approves terminal tool with confirmation messages', async () => {
+		const { service: testService, chatService: testChatService } = createTestToolsService(store, {
+			configureServices: config => {
+				config.setUserConfiguration('chat.tools.global.autoApprove', false);
+			}
+		});
+
+		const tool = registerToolForTest(testService, store, 'terminalToolBypass', {
+			prepareToolInvocation: async () => ({
+				confirmationMessages: {
+					title: 'Run shell command?',
+					message: 'ls -la',
+				},
+				toolSpecificData: {
+					kind: 'terminal' as const,
+					terminalToolSessionId: 'test',
+					terminalCommandId: 'cmd-2',
+					commandLine: { original: 'ls -la' },
+					language: 'sh',
+				},
+			}),
+			invoke: async () => ({ content: [{ kind: 'text', value: 'bypass executed' }] })
+		});
+
+		const sessionId = 'test-bypass-terminal';
+		stubGetSession(testChatService, sessionId, {
+			requestId: 'req1',
+			modeInfo: { permissionLevel: ChatPermissionLevel.AutoApprove },
+		});
+
+		const result = await testService.invokeTool(
+			tool.makeDto({ command: 'ls -la', explanation: 'test', goal: 'test', isBackground: false }, { sessionId }),
+			async () => 0,
+			CancellationToken.None
+		);
+		assert.strictEqual(result.content[0].value, 'bypass executed');
+	});
+
 	test('shouldAutoConfirm with basic configuration', async () => {
 		// Test basic shouldAutoConfirm behavior with simple configuration
 		const { service: testService, chatService: testChatService } = createTestToolsService(store, {
@@ -3905,7 +4085,7 @@ suite('LanguageModelToolsService', () => {
 
 			// Verify error result returned
 			assert.ok(result.toolResultError);
-			assert.ok(result.toolResultError.includes('Destructive operations require approval'));
+			assert.ok((result.toolResultError as string).includes('Destructive operations require approval'));
 			assert.strictEqual(result.content[0].kind, 'text');
 			assert.ok((result.content[0] as IToolResultTextPart).value.includes('Tool execution denied'));
 
diff --git a/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatQuestionCarouselPart.test.ts b/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatQuestionCarouselPart.test.ts
index 2d91102c1e1b0..7bc6a6c04129f 100644
--- a/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatQuestionCarouselPart.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatQuestionCarouselPart.test.ts
@@ -9,8 +9,9 @@ import { MarkdownString } from '../../../../../../../base/common/htmlContent.js'
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../../base/test/common/utils.js';
 import { workbenchInstantiationService } from '../../../../../../test/browser/workbenchTestServices.js';
 import { ChatQuestionCarouselPart, IChatQuestionCarouselOptions } from '../../../../browser/widget/chatContentParts/chatQuestionCarouselPart.js';
-import { IChatQuestionCarousel } from '../../../../common/chatService/chatService.js';
+import { IChatQuestionAnswerValue, IChatQuestionCarousel } from '../../../../common/chatService/chatService.js';
 import { IChatContentPartRenderContext } from '../../../../browser/widget/chatContentParts/chatContentParts.js';
+import { ChatQuestionCarouselData } from '../../../../common/model/chatProgressTypes/chatQuestionCarouselData.js';
 
 function createMockCarousel(questions: IChatQuestionCarousel['questions'], allowSkip: boolean = true): IChatQuestionCarousel {
 	return {
@@ -28,7 +29,7 @@ suite('ChatQuestionCarouselPart', () => {
 	const store = ensureNoDisposablesAreLeakedInTestSuite();
 
 	let widget: ChatQuestionCarouselPart;
-	let submittedAnswers: Map<string, unknown> | undefined | null = null;
+	let submittedAnswers: Map<string, IChatQuestionAnswerValue> | undefined | null = null;
 
 	function createWidget(carousel: IChatQuestionCarousel): ChatQuestionCarouselPart {
 		const instantiationService = workbenchInstantiationService(undefined, store);
@@ -59,7 +60,6 @@ suite('ChatQuestionCarouselPart', () => {
 			assert.ok(widget.domNode.classList.contains('chat-question-carousel-container'));
 			assert.ok(widget.domNode.querySelector('.chat-question-header-row'));
 			assert.ok(widget.domNode.querySelector('.chat-question-carousel-content'));
-			assert.ok(widget.domNode.querySelector('.chat-question-carousel-nav'));
 		});
 
 		test('renders question title', () => {
@@ -100,9 +100,22 @@ suite('ChatQuestionCarouselPart', () => {
 			const title = widget.domNode.querySelector('.chat-question-title');
 			assert.ok(title, 'title element should exist');
 			assert.ok(title?.querySelector('.rendered-markdown'), 'markdown content should be rendered');
-			assert.strictEqual(title?.textContent?.includes('**details**'), false, 'markdown syntax should not be shown as raw text');
-			const link = title?.querySelector('a') as HTMLAnchorElement | null;
-			assert.ok(link, 'markdown link should render as anchor');
+		});
+
+		test('renders plain string question message as text', () => {
+			const carousel = createMockCarousel([
+				{
+					id: 'q1',
+					type: 'text',
+					title: 'Question',
+					message: 'Please review **details** in [docs](https://example.com)'
+				}
+			]);
+			createWidget(carousel);
+
+			const title = widget.domNode.querySelector('.chat-question-title');
+			assert.ok(title, 'title element should exist');
+			assert.ok(title?.textContent?.includes('details'), 'content should be rendered');
 		});
 
 		test('renders progress indicator correctly', () => {
@@ -119,6 +132,23 @@ suite('ChatQuestionCarouselPart', () => {
 			assert.ok(stepIndicator?.textContent?.includes('1'));
 			assert.ok(stepIndicator?.textContent?.includes('3'));
 		});
+
+		test('renders close button in title row for multi-question carousels', () => {
+			const carousel = createMockCarousel([
+				{ id: 'q1', type: 'text', title: 'Question 1' },
+				{ id: 'q2', type: 'text', title: 'Question 2' }
+			], true);
+			createWidget(carousel);
+
+			const titleRow = widget.domNode.querySelector('.chat-question-title-row');
+			assert.ok(titleRow, 'title row should exist');
+
+			const closeContainer = titleRow?.querySelector('.chat-question-close-container');
+			assert.ok(closeContainer, 'close button container should be rendered in the title row');
+
+			const directChildCloseContainer = widget.domNode.querySelector(':scope > .chat-question-close-container');
+			assert.strictEqual(directChildCloseContainer, null, 'close button container should not be positioned as a direct child of the carousel container');
+		});
 	});
 
 	suite('Question Types', () => {
@@ -173,7 +203,7 @@ suite('ChatQuestionCarouselPart', () => {
 			assert.strictEqual(checkboxes.length, 3, 'Should have 3 checkboxes');
 		});
 
-		test('freeform textarea is always rendered for singleSelect', () => {
+		test('freeform textarea is rendered for singleSelect by default', () => {
 			const carousel = createMockCarousel([
 				{
 					id: 'q1',
@@ -187,10 +217,10 @@ suite('ChatQuestionCarouselPart', () => {
 			createWidget(carousel);
 
 			const freeformTextarea = widget.domNode.querySelector('.chat-question-freeform-textarea');
-			assert.ok(freeformTextarea, 'Freeform textarea should always be rendered for singleSelect');
+			assert.ok(freeformTextarea, 'Freeform textarea should be rendered by default for singleSelect');
 		});
 
-		test('freeform textarea is always rendered for multiSelect', () => {
+		test('freeform textarea is rendered for multiSelect by default', () => {
 			const carousel = createMockCarousel([
 				{
 					id: 'q1',
@@ -204,7 +234,45 @@ suite('ChatQuestionCarouselPart', () => {
 			createWidget(carousel);
 
 			const freeformTextarea = widget.domNode.querySelector('.chat-question-freeform-textarea');
-			assert.ok(freeformTextarea, 'Freeform textarea should always be rendered for multiSelect');
+			assert.ok(freeformTextarea, 'Freeform textarea should be rendered by default for multiSelect');
+		});
+
+		test('freeform textarea is hidden when allowFreeformInput is false for singleSelect', () => {
+			const carousel = createMockCarousel([
+				{
+					id: 'q1',
+					type: 'singleSelect',
+					title: 'Choose one',
+					allowFreeformInput: false,
+					options: [
+						{ id: 'a', label: 'Option A', value: 'a' },
+						{ id: 'b', label: 'Option B', value: 'b' }
+					]
+				}
+			]);
+			createWidget(carousel);
+
+			const freeformTextarea = widget.domNode.querySelector('.chat-question-freeform-textarea');
+			assert.strictEqual(freeformTextarea, null, 'Freeform textarea should not be rendered when allowFreeformInput is false');
+		});
+
+		test('freeform textarea is hidden when allowFreeformInput is false for multiSelect', () => {
+			const carousel = createMockCarousel([
+				{
+					id: 'q1',
+					type: 'multiSelect',
+					title: 'Choose multiple',
+					allowFreeformInput: false,
+					options: [
+						{ id: 'a', label: 'Option A', value: 'a' },
+						{ id: 'b', label: 'Option B', value: 'b' }
+					]
+				}
+			]);
+			createWidget(carousel);
+
+			const freeformTextarea = widget.domNode.querySelector('.chat-question-freeform-textarea');
+			assert.strictEqual(freeformTextarea, null, 'Freeform textarea should not be rendered when allowFreeformInput is false');
 		});
 
 		test('default options are pre-selected for singleSelect', () => {
@@ -258,22 +326,41 @@ suite('ChatQuestionCarouselPart', () => {
 			]);
 			createWidget(carousel);
 
-			// Use dedicated class selectors for stability
-			const prevButton = widget.domNode.querySelector('.chat-question-nav-prev') as HTMLButtonElement;
+			const navArrows = widget.domNode.querySelectorAll('.chat-question-nav-arrow') as NodeListOf<HTMLButtonElement>;
+			const prevButton = navArrows[0];
 			assert.ok(prevButton, 'Previous button should exist');
 			assert.ok(prevButton.classList.contains('disabled') || prevButton.disabled, 'Previous button should be disabled on first question');
 		});
 
-		test('next button shows submit icon on last question', () => {
+		test('next button stays as arrow and is disabled on last question', () => {
 			const carousel = createMockCarousel([
-				{ id: 'q1', type: 'text', title: 'Only Question' }
+				{ id: 'q1', type: 'text', title: 'Only Question' },
+				{ id: 'q2', type: 'text', title: 'Question 2' }
 			]);
 			createWidget(carousel);
 
-			// Use dedicated class selector for stability
-			const nextButton = widget.domNode.querySelector('.chat-question-nav-next') as HTMLElement;
+			// Navigate to last question
+			widget.navigateToNextQuestion();
+
+			const navArrows = widget.domNode.querySelectorAll('.chat-question-nav-arrow') as NodeListOf<HTMLButtonElement>;
+			const nextButton = navArrows[1];
 			assert.ok(nextButton, 'Next button should exist');
-			assert.strictEqual(nextButton.getAttribute('aria-label'), 'Submit', 'Next button should have Submit aria-label on last question');
+			assert.ok(nextButton.classList.contains('disabled') || nextButton.disabled, 'Next button should be disabled on last question');
+		});
+
+		test('submit button is shown on last question', () => {
+			const carousel = createMockCarousel([
+				{ id: 'q1', type: 'text', title: 'Question 1' },
+				{ id: 'q2', type: 'text', title: 'Question 2' }
+			]);
+			createWidget(carousel);
+
+			// Navigate to last question
+			widget.navigateToNextQuestion();
+
+			const submitButton = widget.domNode.querySelector('.chat-question-submit-button') as HTMLButtonElement;
+			assert.ok(submitButton, 'Submit button should exist');
+			assert.notStrictEqual(submitButton.style.display, 'none', 'Submit button should be visible on last question');
 		});
 	});
 
@@ -546,6 +633,69 @@ suite('ChatQuestionCarouselPart', () => {
 	});
 
 	suite('Used Carousel Summary', () => {
+		test('retains current question after navigation without editing', () => {
+			const carousel = new ChatQuestionCarouselData([
+				{ id: 'q1', type: 'text', title: 'Question 1' },
+				{ id: 'q2', type: 'text', title: 'Question 2' }
+			], true);
+
+			const firstWidget = createWidget(carousel);
+			const nextButton = firstWidget.domNode.querySelector('.chat-question-nav-next') as HTMLElement | null;
+			assert.ok(nextButton, 'next button should exist');
+			nextButton.dispatchEvent(new MouseEvent('click', { bubbles: true }));
+
+			firstWidget.dispose();
+			firstWidget.domNode.remove();
+
+			const recreatedWidget = createWidget(carousel);
+			const stepIndicator = recreatedWidget.domNode.querySelector('.chat-question-step-indicator');
+			assert.strictEqual(stepIndicator?.textContent, '2/2', 'should restore the current question index after navigation');
+
+			const title = recreatedWidget.domNode.querySelector('.chat-question-title');
+			assert.ok(title?.textContent?.includes('Question 2'), 'should restore to the second question view');
+		});
+
+		test('retains draft answers and current question after widget recreation', () => {
+			const carousel = new ChatQuestionCarouselData([
+				{ id: 'q1', type: 'text', title: 'Question 1' },
+				{ id: 'q2', type: 'text', title: 'Question 2' }
+			], true);
+
+			const firstWidget = createWidget(carousel);
+			const firstInput = firstWidget.domNode.querySelector('.monaco-inputbox input') as HTMLInputElement | null;
+			assert.ok(firstInput, 'first question input should exist');
+			firstInput.value = 'first draft answer';
+			firstInput.dispatchEvent(new Event('input', { bubbles: true }));
+
+			const nextButton = firstWidget.domNode.querySelector('.chat-question-nav-next') as HTMLElement | null;
+			assert.ok(nextButton, 'next button should exist');
+			nextButton.dispatchEvent(new MouseEvent('click', { bubbles: true }));
+
+			const secondInput = firstWidget.domNode.querySelector('.monaco-inputbox input') as HTMLInputElement | null;
+			assert.ok(secondInput, 'second question input should exist');
+			secondInput.value = 'second draft answer';
+			secondInput.dispatchEvent(new Event('input', { bubbles: true }));
+
+			firstWidget.dispose();
+			firstWidget.domNode.remove();
+
+			const recreatedWidget = createWidget(carousel);
+			const stepIndicator = recreatedWidget.domNode.querySelector('.chat-question-step-indicator');
+			assert.strictEqual(stepIndicator?.textContent, '2/2', 'should restore the current question index');
+
+			const recreatedSecondInput = recreatedWidget.domNode.querySelector('.monaco-inputbox input') as HTMLInputElement | null;
+			assert.ok(recreatedSecondInput, 'recreated second question input should exist');
+			assert.strictEqual(recreatedSecondInput.value, 'second draft answer', 'should restore draft input for current question');
+
+			const prevButton = recreatedWidget.domNode.querySelector('.chat-question-nav-prev') as HTMLElement | null;
+			assert.ok(prevButton, 'previous button should exist');
+			prevButton.dispatchEvent(new MouseEvent('click', { bubbles: true }));
+
+			const recreatedFirstInput = recreatedWidget.domNode.querySelector('.monaco-inputbox input') as HTMLInputElement | null;
+			assert.ok(recreatedFirstInput, 'recreated first question input should exist');
+			assert.strictEqual(recreatedFirstInput.value, 'first draft answer', 'should restore draft input for previous question');
+		});
+
 		test('shows summary with answers after skip()', () => {
 			const carousel = createMockCarousel([
 				{ id: 'q1', type: 'text', title: 'Question 1', defaultValue: 'default answer' }
@@ -615,4 +765,163 @@ suite('ChatQuestionCarouselPart', () => {
 			assert.ok(skippedMessage, 'Should show skipped message when no data');
 		});
 	});
+
+	suite('Description and Message', () => {
+		test('renders question description when provided', () => {
+			const carousel = createMockCarousel([
+				{ id: 'q1', type: 'text', title: 'Email', description: 'Enter your email address' }
+			]);
+			createWidget(carousel);
+
+			const desc = widget.domNode.querySelector('.chat-question-description');
+			assert.ok(desc, 'Description element should be rendered');
+			assert.strictEqual(desc?.textContent, 'Enter your email address');
+		});
+
+		test('does not render description element when not provided', () => {
+			const carousel = createMockCarousel([
+				{ id: 'q1', type: 'text', title: 'Name' }
+			]);
+			createWidget(carousel);
+
+			const desc = widget.domNode.querySelector('.chat-question-description');
+			assert.strictEqual(desc, null, 'Description element should not exist when not provided');
+		});
+
+		test('renders carousel-level message on first question', () => {
+			const carousel = createMockCarousel([
+				{ id: 'q1', type: 'text', title: 'Name' },
+				{ id: 'q2', type: 'text', title: 'Email' }
+			]);
+			carousel.message = 'Please fill in the following:';
+			createWidget(carousel);
+
+			const message = widget.domNode.querySelector('.chat-question-carousel-message');
+			assert.ok(message, 'Carousel message should be rendered');
+			assert.ok(message?.textContent?.includes('Please fill in the following:'));
+		});
+
+		test('renders carousel-level message as markdown', () => {
+			const carousel = createMockCarousel([
+				{ id: 'q1', type: 'text', title: 'Name' }
+			]);
+			carousel.message = new MarkdownString('**Important:** Fill this form');
+			createWidget(carousel);
+
+			const message = widget.domNode.querySelector('.chat-question-carousel-message');
+			assert.ok(message, 'Carousel message should be rendered');
+			assert.ok(message?.querySelector('.rendered-markdown'), 'Message should be rendered as markdown');
+		});
+
+		test('shows required indicator on required questions', () => {
+			const carousel = createMockCarousel([
+				{ id: 'q1', type: 'text', title: 'Name', required: true }
+			]);
+			createWidget(carousel);
+
+			const title = widget.domNode.querySelector('.chat-question-title');
+			assert.ok(title?.textContent?.includes('*'), 'Required indicator (*) should be shown');
+		});
+
+		test('does not show required indicator on optional questions', () => {
+			const carousel = createMockCarousel([
+				{ id: 'q1', type: 'text', title: 'Nickname' }
+			]);
+			createWidget(carousel);
+
+			const title = widget.domNode.querySelector('.chat-question-title');
+			assert.ok(title?.textContent);
+			assert.ok(!title?.textContent?.includes('*'), 'Required indicator should not be shown');
+		});
+	});
+
+	suite('Validation', () => {
+		test('renders validation message element', () => {
+			const carousel = createMockCarousel([
+				{
+					id: 'q1',
+					type: 'text',
+					title: 'Email',
+					validation: { format: 'email' }
+				}
+			]);
+			createWidget(carousel);
+
+			const validationMsg = widget.domNode.querySelector('.chat-question-validation-message') as HTMLElement | null;
+			assert.ok(validationMsg, 'Validation message element should exist');
+			assert.strictEqual(validationMsg?.style.display, 'none', 'Validation message should be hidden initially');
+		});
+
+		test('blocks submit on required empty text field', () => {
+			const carousel = createMockCarousel([
+				{ id: 'q1', type: 'text', title: 'Name', required: true }
+			]);
+			createWidget(carousel);
+
+			// Try to submit without entering a value
+			const submitButton = widget.domNode.querySelector('.chat-question-submit-button') as HTMLButtonElement;
+			assert.ok(submitButton, 'Submit button should exist');
+			submitButton.click();
+
+			// Should show validation error and not submit
+			const validationMsg = widget.domNode.querySelector('.chat-question-validation-message');
+			assert.ok(validationMsg?.textContent, 'Validation error should be shown');
+			assert.strictEqual(submittedAnswers, null, 'Should not have submitted');
+		});
+
+		test('next button is disabled when required text field is empty', () => {
+			const carousel = createMockCarousel([
+				{ id: 'q1', type: 'text', title: 'Name', required: true },
+				{ id: 'q2', type: 'text', title: 'Age' }
+			]);
+			createWidget(carousel);
+
+			// Next button should be disabled since required field has no answer
+			const nextButton = widget.domNode.querySelector('.chat-question-nav-next') as HTMLButtonElement;
+			assert.ok(nextButton, 'Next button should exist');
+			assert.ok(nextButton.classList.contains('disabled'), 'Next button should be disabled when required field is empty');
+		});
+
+		test('allows submit on required field with value', () => {
+			const carousel = createMockCarousel([
+				{ id: 'q1', type: 'text', title: 'Name', required: true }
+			]);
+			createWidget(carousel);
+
+			// Enter a value in the text input
+			const inputBox = widget.domNode.querySelector('.monaco-inputbox input') as HTMLInputElement;
+			assert.ok(inputBox, 'Input should exist');
+			inputBox.value = 'John';
+			inputBox.dispatchEvent(new Event('input', { bubbles: true }));
+
+			// Submit
+			const submitButton = widget.domNode.querySelector('.chat-question-submit-button') as HTMLButtonElement;
+			submitButton.click();
+
+			assert.ok(submittedAnswers !== null, 'Should have submitted');
+		});
+
+		test('validates required field across questions on submit', () => {
+			const carousel = createMockCarousel([
+				{ id: 'q1', type: 'text', title: 'Optional' },
+				{ id: 'q2', type: 'text', title: 'Required', required: true }
+			]);
+			createWidget(carousel);
+
+			// Navigate to q2 without filling q1 (optional, so allowed)
+			widget.navigateToNextQuestion();
+
+			// Go back to q1 and try to submit (q2 required but empty)
+			widget.navigateToPreviousQuestion();
+
+			// Cmd+Enter should check all required fields
+			const submitButton = widget.domNode.querySelector('.chat-question-submit-button') as HTMLButtonElement;
+			if (submitButton) {
+				submitButton.click();
+			}
+
+			// Should not submit because q2 is required but empty
+			assert.strictEqual(submittedAnswers, null, 'Should not submit when required field is empty');
+		});
+	});
 });
diff --git a/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatSubagentContentPart.test.ts b/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatSubagentContentPart.test.ts
index 9afc036351101..f141f1a1830ab 100644
--- a/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatSubagentContentPart.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatSubagentContentPart.test.ts
@@ -13,7 +13,7 @@ import { mainWindow } from '../../../../../../../base/browser/window.js';
 import { workbenchInstantiationService } from '../../../../../../test/browser/workbenchTestServices.js';
 import { ChatSubagentContentPart } from '../../../../browser/widget/chatContentParts/chatSubagentContentPart.js';
 import { IChatMarkdownContent, IChatSubagentToolInvocationData, IChatToolInvocation, IChatToolInvocationSerialized, ToolConfirmKind } from '../../../../common/chatService/chatService.js';
-import { IChatContentPartRenderContext } from '../../../../browser/widget/chatContentParts/chatContentParts.js';
+import { IChatContentPartRenderContext, InlineTextModelCollection } from '../../../../browser/widget/chatContentParts/chatContentParts.js';
 import { IChatResponseViewModel } from '../../../../common/model/chatViewModel.js';
 import { IChatMarkdownAnchorService } from '../../../../browser/widget/chatContentParts/chatMarkdownAnchorService.js';
 import { IMarkdownRenderer } from '../../../../../../../platform/markdown/browser/markdownRenderer.js';
@@ -55,6 +55,7 @@ suite('ChatSubagentContentPart', () => {
 
 		return {
 			element: mockElement as IChatResponseViewModel,
+			inlineTextModels: {} as InlineTextModelCollection,
 			elementIndex: 0,
 			container: mainWindow.document.createElement('div'),
 			content: [],
@@ -150,6 +151,7 @@ suite('ChatSubagentContentPart', () => {
 			toolCallId: toolCallId,
 			subAgentInvocationId: options.subAgentInvocationId,
 			state: observableValue('state', stateValue),
+			isAttachedToThinking: false,
 			kind: 'toolInvocation',
 			toJSON: () => createMockSerializedToolInvocation({
 				toolId: options.toolId ?? RunSubagentTool.Id,
diff --git a/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatThinkingContentPart.test.ts b/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatThinkingContentPart.test.ts
index 15aa7762d9f3e..f11478cebc5d4 100644
--- a/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatThinkingContentPart.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/widget/chatContentParts/chatThinkingContentPart.test.ts
@@ -15,7 +15,7 @@ import { IConfigurationService } from '../../../../../../../platform/configurati
 import { TestConfigurationService } from '../../../../../../../platform/configuration/test/common/testConfigurationService.js';
 import { ChatThinkingContentPart } from '../../../../browser/widget/chatContentParts/chatThinkingContentPart.js';
 import { IChatMarkdownContent, IChatThinkingPart } from '../../../../common/chatService/chatService.js';
-import { IChatContentPartRenderContext } from '../../../../browser/widget/chatContentParts/chatContentParts.js';
+import { IChatContentPartRenderContext, InlineTextModelCollection } from '../../../../browser/widget/chatContentParts/chatContentParts.js';
 import { IChatRendererContent, IChatResponseViewModel } from '../../../../common/model/chatViewModel.js';
 import { IChatMarkdownAnchorService } from '../../../../browser/widget/chatContentParts/chatMarkdownAnchorService.js';
 import { IMarkdownRenderer } from '../../../../../../../platform/markdown/browser/markdownRenderer.js';
@@ -49,6 +49,7 @@ suite('ChatThinkingContentPart', () => {
 
 		return {
 			element: mockElement as IChatResponseViewModel,
+			inlineTextModels: {} as InlineTextModelCollection,
 			elementIndex: 0,
 			container: mainWindow.document.createElement('div'),
 			content: [],
diff --git a/src/vs/workbench/contrib/chat/test/browser/widget/chatMarkdownTableScrolling.test.ts b/src/vs/workbench/contrib/chat/test/browser/widget/chatMarkdownTableScrolling.test.ts
new file mode 100644
index 0000000000000..4a25f74f0b388
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/browser/widget/chatMarkdownTableScrolling.test.ts
@@ -0,0 +1,144 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as assert from 'assert';
+import { Lazy } from '../../../../../../base/common/lazy.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { wrapTablesWithScrollable } from '../../../browser/widget/chatContentParts/chatMarkdownTableScrolling.js';
+
+/** Builds an HTMLElement containing one or more tables from markdown-style 2-D arrays. */
+function buildContainer(tables: string[][][]): HTMLDivElement {
+	const container = document.createElement('div');
+	for (const rows of tables) {
+		const table = document.createElement('table');
+		rows.forEach((rowData, rowIndex) => {
+			const section = rowIndex === 0
+				? table.createTHead()
+				: (table.tBodies[0] ?? table.createTBody());
+			const tr = section.insertRow();
+			for (const text of rowData) {
+				const cell = rowIndex === 0 ? document.createElement('th') : tr.insertCell();
+				cell.textContent = text;
+				if (rowIndex === 0) {
+					tr.appendChild(cell);
+				}
+			}
+		});
+		container.appendChild(table);
+	}
+	return container;
+}
+
+suite('wrapTablesWithScrollable', () => {
+	const store = ensureNoDisposablesAreLeakedInTestSuite();
+
+	function wrap(container: HTMLDivElement): { layoutParticipants: Set<() => void> } {
+		const layoutParticipants = new Set<() => void>();
+		store.add(wrapTablesWithScrollable(container, new Lazy(() => layoutParticipants)));
+		return { layoutParticipants };
+	}
+
+	test('replaces each table with a scroll wrapper in the DOM', () => {
+		const container = buildContainer([[
+			['ID', 'Name'],
+			['001', 'Alice'],
+		]]);
+		// Before: direct child is <table>
+		assert.strictEqual(container.children[0].tagName, 'TABLE');
+
+		wrap(container);
+
+		// After: direct child is the monaco-scrollable-element wrapper
+		const wrapper = container.children[0];
+		assert.ok(wrapper.classList.contains('rendered-markdown-table-scroll-wrapper'),
+			'outer node should have the scroll wrapper class');
+	});
+
+	test('table is preserved inside the scroll wrapper', () => {
+		const container = buildContainer([[['A', 'BB'], ['C', 'DD']]]);
+		wrap(container);
+
+		// The table must still be in the document, nested inside the wrapper
+		const table = container.querySelector('table');
+		assert.ok(table, 'table should still exist in DOM');
+		assert.ok(container.contains(table), 'table should be inside container');
+		assert.ok(!container.children[0].isSameNode(table), 'table should not be a direct child anymore');
+	});
+
+	test('registers a layout participant for each table', () => {
+		const container = buildContainer([
+			[['H1', 'H2'], ['a', 'bb']],
+			[['X', 'YY'], ['c', 'dd']],
+		]);
+		const { layoutParticipants } = wrap(container);
+		assert.strictEqual(layoutParticipants.size, 2, 'one layout participant registered per table');
+	});
+
+	test('sets column min-width capped at 3ch', () => {
+		const container = buildContainer([[
+			['ID', 'Name'],
+			['001', 'Alice'],
+			['002', 'Longer Name'],
+		]]);
+		wrap(container);
+
+		const table = container.querySelector('table')!;
+		// min-width is set only on the first row; other rows are untouched
+		// col 0 max = 3 chars -> 3ch; col 1 max = 11 chars -> capped at 3ch
+		assert.deepStrictEqual(
+			Array.from(table.rows[0].cells).map(cell => cell.style.minWidth),
+			['3ch', '3ch']
+		);
+		assert.deepStrictEqual(
+			Array.from(table.rows[1].cells).map(cell => cell.style.minWidth),
+			['', '']
+		);
+	});
+
+	test('uses actual char count when below the 3ch cap', () => {
+		const container = buildContainer([[['AB', 'C'], ['DE', 'F']]]);
+		wrap(container);
+
+		const table = container.querySelector('table')!;
+		// col 0 max=2 -> 2ch; col 1 max=1 -> no min-width
+		assert.strictEqual(table.rows[0].cells[0].style.minWidth, '2ch');
+		assert.strictEqual(table.rows[0].cells[1].style.minWidth, '');
+	});
+
+	test('does not set min-width on single-character columns', () => {
+		const container = buildContainer([[['X', 'hello'], ['Y', 'world']]]);
+		wrap(container);
+
+		const table = container.querySelector('table')!;
+		assert.strictEqual(table.rows[0].cells[0].style.minWidth, '', 'single-char column should have no min-width');
+	});
+
+	test('handles multiple tables independently', () => {
+		const container = buildContainer([
+			[['AB', 'C'], ['DE', 'F']],
+			[['X', 'YYY'], ['Z', 'WWW']],
+		]);
+		wrap(container);
+
+		const tables = container.querySelectorAll('table');
+		assert.strictEqual(tables.length, 2);
+
+		// Table 1: col 0 max=2, col 1 max=1 -> only col 0 gets min-width
+		assert.strictEqual(tables[0].rows[0].cells[0].style.minWidth, '2ch');
+		assert.strictEqual(tables[0].rows[0].cells[1].style.minWidth, '');
+
+		// Table 2: col 0 max=1, col 1 max=3 -> only col 1 gets min-width
+		assert.strictEqual(tables[1].rows[0].cells[0].style.minWidth, '');
+		assert.strictEqual(tables[1].rows[0].cells[1].style.minWidth, '3ch');
+	});
+
+	test('no-ops on a container with no tables', () => {
+		const container = document.createElement('div');
+		container.innerHTML = '<p>hello</p>';
+		const { layoutParticipants } = wrap(container);
+		assert.strictEqual(layoutParticipants.size, 0);
+		assert.strictEqual(container.querySelector('table'), null);
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelPicker.test.ts b/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelPicker.test.ts
index e39c5df086f98..e729526f6cb79 100644
--- a/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelPicker.test.ts
+++ b/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelPicker.test.ts
@@ -10,9 +10,8 @@ import { IStringDictionary } from '../../../../../../../base/common/collections.
 import { MarkdownString } from '../../../../../../../base/common/htmlContent.js';
 import { ActionListItemKind, IActionListItem } from '../../../../../../../platform/actionWidget/browser/actionList.js';
 import { IActionWidgetDropdownAction } from '../../../../../../../platform/actionWidget/browser/actionWidgetDropdown.js';
-import { ICommandService } from '../../../../../../../platform/commands/common/commands.js';
 import { StateType } from '../../../../../../../platform/update/common/update.js';
-import { buildModelPickerItems } from '../../../../browser/widget/input/chatModelPicker.js';
+import { buildModelPickerItems, getModelPickerAccessibilityProvider } from '../../../../browser/widget/input/chatModelPicker.js';
 import { ILanguageModelChatMetadata, ILanguageModelChatMetadataAndIdentifier, IModelControlEntry } from '../../../../common/languageModels.js';
 import { ChatEntitlement, IChatEntitlementService } from '../../../../../../services/chat/common/chatEntitlementService.js';
 
@@ -48,13 +47,6 @@ function createAutoModel(): ILanguageModelChatMetadataAndIdentifier {
 	return createModel('auto', 'Auto', 'copilot');
 }
 
-const stubCommandService: ICommandService = {
-	_serviceBrand: undefined,
-	onWillExecuteCommand: () => ({ dispose() { } }),
-	onDidExecuteCommand: () => ({ dispose() { } }),
-	executeCommand: () => Promise.resolve(undefined),
-};
-
 function getActionItems(items: IActionListItem<IActionWidgetDropdownAction>[]): IActionListItem<IActionWidgetDropdownAction>[] {
 	return items.filter(i => i.kind === ActionListItemKind.Action);
 }
@@ -67,6 +59,16 @@ function getSeparatorCount(items: IActionListItem<IActionWidgetDropdownAction>[]
 	return items.filter(i => i.kind === ActionListItemKind.Separator).length;
 }
 
+const stubManageModelsAction: IActionWidgetDropdownAction = {
+	id: 'manageModels',
+	enabled: true,
+	checked: false,
+	class: undefined,
+	tooltip: 'Manage Language Models',
+	label: 'Manage Models...',
+	run: () => { }
+};
+
 function callBuild(
 	models: ILanguageModelChatMetadataAndIdentifier[],
 	opts: {
@@ -78,6 +80,8 @@ function callBuild(
 		updateStateType?: StateType;
 		manageSettingsUrl?: string;
 		anonymous?: boolean;
+		showUnavailableFeatured?: boolean;
+		showFeatured?: boolean;
 	} = {},
 ): IActionListItem<IActionWidgetDropdownAction>[] {
 	const onSelect = () => { };
@@ -95,8 +99,10 @@ function callBuild(
 		onSelect,
 		opts.manageSettingsUrl,
 		true,
-		stubCommandService,
+		stubManageModelsAction,
 		entitlementService,
+		opts.showUnavailableFeatured ?? true,
+		opts.showFeatured ?? true,
 	);
 }
 
@@ -104,6 +110,13 @@ suite('buildModelPickerItems', () => {
 
 	ensureNoDisposablesAreLeakedInTestSuite();
 
+	test('accessibility provider uses radio semantics for model items', () => {
+		const provider = getModelPickerAccessibilityProvider();
+		assert.strictEqual(provider.getRole({ kind: ActionListItemKind.Action } as IActionListItem<IActionWidgetDropdownAction>), 'menuitemradio');
+		assert.strictEqual(provider.getRole({ kind: ActionListItemKind.Separator } as IActionListItem<IActionWidgetDropdownAction>), 'separator');
+		assert.strictEqual(provider.getWidgetRole(), 'menu');
+	});
+
 	test('auto model always appears first', () => {
 		const auto = createAutoModel();
 		const modelA = createModel('gpt-4o', 'GPT-4o');
@@ -374,6 +387,22 @@ suite('buildModelPickerItems', () => {
 		assert.strictEqual(gptItem.disabled, true);
 	});
 
+	test('Other Models places unavailable models after available models', () => {
+		const auto = createAutoModel();
+		const availableModel = createModel('zeta', 'Zeta');
+		const unavailableModel = createModel('alpha', 'Alpha');
+		const items = callBuild([auto, availableModel, unavailableModel], {
+			controlModels: {
+				'alpha': { label: 'Alpha', minVSCodeVersion: '2.0.0', exists: true },
+			},
+			currentVSCodeVersion: '1.90.0',
+		});
+		const actions = getActionItems(items);
+		const otherModelLabels = actions.slice(2).map(a => a.label!).filter(l => !l.includes('Manage Models'));
+		assert.deepStrictEqual(otherModelLabels, ['Zeta', 'Alpha']);
+		assert.strictEqual(actions.find(a => a.label === 'Alpha')?.disabled, true);
+	});
+
 	test('no duplicate models across sections', () => {
 		const auto = createAutoModel();
 		const modelA = createModel('gpt-4o', 'GPT-4o');
@@ -447,8 +476,10 @@ suite('buildModelPickerItems', () => {
 			onSelect,
 			undefined,
 			true,
-			stubCommandService,
+			undefined,
 			stubChatEntitlementService,
+			true,
+			true,
 		);
 		const gptItem = getActionItems(items).find(a => a.label === 'GPT-4o');
 		assert.ok(gptItem?.item);
@@ -529,8 +560,10 @@ suite('buildModelPickerItems', () => {
 			() => { },
 			'https://aka.ms/github-copilot-settings',
 			true,
-			stubCommandService,
+			undefined,
 			stubChatEntitlementService,
+			true,
+			true,
 		);
 
 		const adminItem = getActionItems(items).find(a => a.label === 'Missing Model');
@@ -557,7 +590,7 @@ suite('buildModelPickerItems', () => {
 		assert.strictEqual(unavailable.group?.icon?.id, Codicon.blank.id);
 	});
 
-	test('anonymous user sees upgrade description only on first unavailable model', () => {
+	test('anonymous user sees upgrade description on each unavailable model', () => {
 		const auto = createAutoModel();
 		const items = callBuild([auto], {
 			recentModelIds: ['model-a', 'model-b'],
@@ -573,10 +606,11 @@ suite('buildModelPickerItems', () => {
 		assert.strictEqual(disabledItems.length, 2);
 		assert.ok(disabledItems[0].description instanceof MarkdownString);
 		assert.ok(disabledItems[0].description.value.includes('Upgrade'));
-		assert.strictEqual(disabledItems[1].description, undefined);
+		assert.ok(disabledItems[1].description instanceof MarkdownString);
+		assert.ok(disabledItems[1].description.value.includes('Upgrade'));
 	});
 
-	test('free user sees upgrade description only on first unavailable model', () => {
+	test('free user sees upgrade description on each unavailable model', () => {
 		const auto = createAutoModel();
 		const items = callBuild([auto], {
 			recentModelIds: ['model-a', 'model-b'],
@@ -591,7 +625,8 @@ suite('buildModelPickerItems', () => {
 		assert.strictEqual(disabledItems.length, 2);
 		assert.ok(disabledItems[0].description instanceof MarkdownString);
 		assert.ok(disabledItems[0].description.value.includes('Upgrade'));
-		assert.strictEqual(disabledItems[1].description, undefined);
+		assert.ok(disabledItems[1].description instanceof MarkdownString);
+		assert.ok(disabledItems[1].description.value.includes('Upgrade'));
 	});
 
 	test('anonymous user model selection triggers onSelect normally', () => {
@@ -610,12 +645,80 @@ suite('buildModelPickerItems', () => {
 			onSelect,
 			undefined,
 			true,
-			stubCommandService,
+			undefined,
 			anonymousEntitlementService,
+			true,
+			true,
 		);
 		const gptItem = getActionItems(items).find(a => a.label === 'GPT-4o');
 		assert.ok(gptItem?.item);
 		gptItem.item.run();
 		assert.strictEqual(selectedModel?.identifier, modelA.identifier);
 	});
+
+	test('showFeatured=false omits featured models from promoted section', () => {
+		const auto = createAutoModel();
+		const modelA = createModel('gpt-4o', 'GPT-4o');
+		const modelB = createModel('claude', 'Claude');
+		const items = callBuild([auto, modelA, modelB], {
+			controlModels: {
+				'gpt-4o': { label: 'GPT-4o', featured: true, exists: true },
+			},
+			showFeatured: false,
+		});
+		const actions = getActionItems(items);
+		// Auto first, then Other Models toggle, then models in other section
+		assert.strictEqual(actions[0].label, 'Auto');
+		// GPT-4o should NOT be promoted — it should be in Other Models
+		const promotedLabels = actions.filter(a => !a.isSectionToggle && a.section !== 'other' && a.item?.id !== 'manageModels').map(a => a.label);
+		assert.ok(!promotedLabels.includes('GPT-4o'), 'GPT-4o should not be in promoted section when showFeatured=false');
+	});
+
+	test('showUnavailableFeatured=false omits unavailable featured models from promoted section', () => {
+		const auto = createAutoModel();
+		const items = callBuild([auto], {
+			controlModels: {
+				'premium-model': { label: 'Premium Model', featured: true, exists: false },
+			},
+			entitlement: ChatEntitlement.Free,
+			showUnavailableFeatured: false,
+		});
+		const actions = getActionItems(items);
+		// Premium Model should not appear at all
+		const premiumItem = actions.find(a => a.label === 'Premium Model');
+		assert.strictEqual(premiumItem, undefined, 'Unavailable featured model should not appear when showUnavailableFeatured=false');
+	});
+
+	test('showUnavailableFeatured=false still shows available featured models', () => {
+		const auto = createAutoModel();
+		const modelA = createModel('gpt-4o', 'GPT-4o');
+		const items = callBuild([auto, modelA], {
+			controlModels: {
+				'gpt-4o': { label: 'GPT-4o', featured: true, exists: true },
+			},
+			showUnavailableFeatured: false,
+		});
+		const actions = getActionItems(items);
+		// GPT-4o is available and featured, so it should still appear in promoted
+		const gptItem = actions.find(a => a.label === 'GPT-4o');
+		assert.ok(gptItem, 'Available featured model should appear even when showUnavailableFeatured=false');
+	});
+
+	test('showUnavailableFeatured=false with version-gated model allows it in Other Models', () => {
+		const auto = createAutoModel();
+		const modelA = createModel('gpt-4o', 'GPT-4o');
+		const items = callBuild([auto, modelA], {
+			controlModels: {
+				'gpt-4o': { label: 'GPT-4o', featured: true, minVSCodeVersion: '2.0.0', exists: true },
+			},
+			showUnavailableFeatured: false,
+		});
+		const actions = getActionItems(items);
+		// Version-gated model should not be in promoted section as unavailable
+		const promotedGpt = actions.find(a => a.label === 'GPT-4o' && a.section !== 'other');
+		assert.strictEqual(promotedGpt?.disabled, undefined, 'Version-gated featured model should not appear as unavailable in promoted when showUnavailableFeatured=false');
+		// It should still appear in Other Models since it was not placed
+		const otherGpt = actions.find(a => a.label === 'GPT-4o' && a.section === 'other');
+		assert.ok(otherGpt, 'Version-gated featured model should appear in Other Models when showUnavailableFeatured=false');
+	});
 });
diff --git a/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelSelectionLogic.test.ts b/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelSelectionLogic.test.ts
new file mode 100644
index 0000000000000..581f0db3fb30e
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/browser/widget/input/chatModelSelectionLogic.test.ts
@@ -0,0 +1,1548 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../../base/test/common/utils.js';
+import { ExtensionIdentifier } from '../../../../../../../platform/extensions/common/extensions.js';
+import { ChatAgentLocation, ChatModeKind } from '../../../../common/constants.js';
+import { ILanguageModelChatMetadata, ILanguageModelChatMetadataAndIdentifier } from '../../../../common/languageModels.js';
+import {
+	filterModelsForSession,
+	findDefaultModel,
+	hasModelsTargetingSession,
+	isModelSupportedForInlineChat,
+	isModelSupportedForMode,
+	isModelValidForSession,
+	mergeModelsWithCache,
+	resolveModelFromSyncState,
+	shouldResetModelToDefault,
+	shouldResetOnModelListChange,
+	shouldRestoreLateArrivingModel,
+	shouldRestorePersistedModel,
+} from '../../../../browser/widget/input/chatModelSelectionLogic.js';
+
+/**
+ * Test helper that composes the full startup pipeline: merge live+cache → sort → filter by session/mode.
+ * This mirrors what `chatInputPart.getModels()` does, but without the storage side effects.
+ */
+function computeAvailableModels(
+	liveModels: ILanguageModelChatMetadataAndIdentifier[],
+	cachedModels: ILanguageModelChatMetadataAndIdentifier[],
+	contributedVendors: Set<string>,
+	sessionType: string | undefined,
+	currentModeKind: ChatModeKind,
+	location: ChatAgentLocation,
+	isInlineChatV2Enabled: boolean,
+): ILanguageModelChatMetadataAndIdentifier[] {
+	const merged = mergeModelsWithCache(liveModels, cachedModels, contributedVendors);
+	merged.sort((a, b) => a.metadata.name.localeCompare(b.metadata.name));
+	return filterModelsForSession(merged, sessionType, currentModeKind, location, isInlineChatV2Enabled);
+}
+
+function createModel(
+	id: string,
+	name: string,
+	overrides?: Partial<ILanguageModelChatMetadata>,
+): ILanguageModelChatMetadataAndIdentifier {
+	return {
+		identifier: `copilot/${id}`,
+		metadata: {
+			extension: new ExtensionIdentifier('test.ext'),
+			id,
+			name,
+			vendor: 'copilot',
+			version: '1.0',
+			family: 'copilot',
+			maxInputTokens: 128000,
+			maxOutputTokens: 4096,
+			isDefaultForLocation: {},
+			isUserSelectable: true,
+			modelPickerCategory: undefined,
+			capabilities: { toolCalling: true, agentMode: true },
+			...overrides,
+		} as ILanguageModelChatMetadata,
+	};
+}
+
+function createDefaultModelForLocation(
+	id: string,
+	name: string,
+	location: ChatAgentLocation,
+	overrides?: Partial<ILanguageModelChatMetadata>,
+): ILanguageModelChatMetadataAndIdentifier {
+	return createModel(id, name, {
+		isDefaultForLocation: { [location]: true },
+		...overrides,
+	});
+}
+
+function createSessionModel(
+	id: string,
+	name: string,
+	sessionType: string,
+	overrides?: Partial<ILanguageModelChatMetadata>,
+): ILanguageModelChatMetadataAndIdentifier {
+	return createModel(id, name, {
+		targetChatSessionType: sessionType,
+		...overrides,
+	});
+}
+
+suite('ChatModelSelectionLogic', () => {
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	suite('isModelSupportedForMode', () => {
+
+		test('any model is supported in Ask mode', () => {
+			const model = createModel('basic', 'Basic', { capabilities: undefined });
+			assert.strictEqual(isModelSupportedForMode(model, ChatModeKind.Ask), true);
+		});
+
+		test('any model is supported in Edit mode', () => {
+			const model = createModel('basic', 'Basic', { capabilities: undefined });
+			assert.strictEqual(isModelSupportedForMode(model, ChatModeKind.Edit), true);
+		});
+
+		test('model with tool calling and agent mode is supported in Agent mode', () => {
+			const model = createModel('agent-capable', 'Agent-Capable', {
+				capabilities: { toolCalling: true, agentMode: true },
+			});
+			assert.strictEqual(isModelSupportedForMode(model, ChatModeKind.Agent), true);
+		});
+
+		test('model with tool calling but agentMode=undefined is supported in Agent mode', () => {
+			const model = createModel('tool-only', 'Tool-Only', {
+				capabilities: { toolCalling: true },
+			});
+			assert.strictEqual(isModelSupportedForMode(model, ChatModeKind.Agent), true);
+		});
+
+		test('model without tool calling is NOT supported in Agent mode', () => {
+			const model = createModel('no-tools', 'No-Tools', {
+				capabilities: { toolCalling: false },
+			});
+			assert.strictEqual(isModelSupportedForMode(model, ChatModeKind.Agent), false);
+		});
+
+		test('model with agentMode=false is NOT supported in Agent mode', () => {
+			const model = createModel('no-agent', 'No-Agent', {
+				capabilities: { toolCalling: true, agentMode: false },
+			});
+			assert.strictEqual(isModelSupportedForMode(model, ChatModeKind.Agent), false);
+		});
+
+		test('model with no capabilities is NOT supported in Agent mode', () => {
+			const model = createModel('no-caps', 'No-Caps', { capabilities: undefined });
+			assert.strictEqual(isModelSupportedForMode(model, ChatModeKind.Agent), false);
+		});
+	});
+
+	suite('isModelSupportedForInlineChat', () => {
+
+		test('any model is supported when not in EditorInline location', () => {
+			const model = createModel('basic', 'Basic', { capabilities: undefined });
+			assert.strictEqual(isModelSupportedForInlineChat(model, ChatAgentLocation.Chat, true), true);
+			assert.strictEqual(isModelSupportedForInlineChat(model, ChatAgentLocation.Terminal, true), true);
+			assert.strictEqual(isModelSupportedForInlineChat(model, ChatAgentLocation.Notebook, true), true);
+		});
+
+		test('any model is supported in EditorInline when V2 is disabled', () => {
+			const model = createModel('basic', 'Basic', { capabilities: undefined });
+			assert.strictEqual(isModelSupportedForInlineChat(model, ChatAgentLocation.EditorInline, false), true);
+		});
+
+		test('model with tool calling is supported in EditorInline with V2', () => {
+			const model = createModel('tools', 'Tools', {
+				capabilities: { toolCalling: true },
+			});
+			assert.strictEqual(isModelSupportedForInlineChat(model, ChatAgentLocation.EditorInline, true), true);
+		});
+
+		test('model without tool calling is NOT supported in EditorInline with V2', () => {
+			const model = createModel('no-tools', 'No-Tools', {
+				capabilities: { toolCalling: false },
+			});
+			assert.strictEqual(isModelSupportedForInlineChat(model, ChatAgentLocation.EditorInline, true), false);
+		});
+
+		test('model with no capabilities is NOT supported in EditorInline with V2', () => {
+			const model = createModel('no-caps', 'No-Caps', { capabilities: undefined });
+			assert.strictEqual(isModelSupportedForInlineChat(model, ChatAgentLocation.EditorInline, true), false);
+		});
+	});
+
+	suite('filterModelsForSession', () => {
+
+		const gpt4o = createModel('gpt-4o', 'GPT-4o');
+		const claude = createModel('claude', 'Claude');
+		const notSelectable = createModel('hidden', 'Hidden', { isUserSelectable: false });
+		const cloudModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+		const noToolsModel = createModel('no-tools', 'No-Tools', {
+			capabilities: { toolCalling: false, agentMode: false },
+		});
+
+		test('returns user-selectable general models when no session type set', () => {
+			const result = filterModelsForSession(
+				[gpt4o, claude, notSelectable],
+				undefined,
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['gpt-4o', 'claude']);
+		});
+
+		test('returns user-selectable general models for local session type', () => {
+			const result = filterModelsForSession(
+				[gpt4o, claude, notSelectable],
+				'local',
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['gpt-4o', 'claude']);
+		});
+
+		test('excludes models targeting a specific session type when in general session', () => {
+			const result = filterModelsForSession(
+				[gpt4o, claude, cloudModel],
+				undefined,
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['gpt-4o', 'claude']);
+		});
+
+		test('returns only session-targeted models for a specific session type', () => {
+			const result = filterModelsForSession(
+				[gpt4o, claude, cloudModel],
+				'cloud',
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['cloud-gpt']);
+		});
+
+		test('filters out models incompatible with Agent mode in general session', () => {
+			const result = filterModelsForSession(
+				[gpt4o, noToolsModel],
+				undefined,
+				ChatModeKind.Agent,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['gpt-4o']);
+		});
+
+		test.skip('filters by mode for session-targeted models', () => {
+			const cloudNoTools = createSessionModel('cloud-basic', 'Cloud Basic', 'cloud', {
+				capabilities: { toolCalling: false, agentMode: false },
+			});
+			const result = filterModelsForSession(
+				[gpt4o, cloudModel, cloudNoTools],
+				'cloud',
+				ChatModeKind.Agent,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			// Session-type filtering also checks mode and inline chat support
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['cloud-gpt']);
+		});
+
+		test('excludes non-selectable models from session-targeted results', () => {
+			const cloudHidden = createSessionModel('cloud-hidden', 'Cloud Hidden', 'cloud', {
+				isUserSelectable: false,
+			});
+			const result = filterModelsForSession(
+				[cloudModel, cloudHidden],
+				'cloud',
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['cloud-gpt']);
+		});
+
+		test('falls back to general models when no models target the session type', () => {
+			const result = filterModelsForSession(
+				[gpt4o, claude],
+				'cloud',
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['gpt-4o', 'claude']);
+		});
+
+		test('filters inline chat incompatible models in EditorInline with V2', () => {
+			const noToolsSelectable = createModel('no-tools-selectable', 'No-Tools-Selectable', {
+				capabilities: { toolCalling: false },
+			});
+			const result = filterModelsForSession(
+				[gpt4o, noToolsSelectable],
+				undefined,
+				ChatModeKind.Ask,
+				ChatAgentLocation.EditorInline,
+				true,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['gpt-4o']);
+		});
+	});
+
+	suite('hasModelsTargetingSession', () => {
+
+		test('returns false when session type is undefined', () => {
+			const models = [createModel('gpt', 'GPT')];
+			assert.strictEqual(hasModelsTargetingSession(models, undefined), false);
+		});
+
+		test('returns false when no models target the session type', () => {
+			const models = [createModel('gpt', 'GPT')];
+			assert.strictEqual(hasModelsTargetingSession(models, 'cloud'), false);
+		});
+
+		test('returns true when a model targets the session type', () => {
+			const models = [
+				createModel('gpt', 'GPT'),
+				createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud'),
+			];
+			assert.strictEqual(hasModelsTargetingSession(models, 'cloud'), true);
+		});
+
+		test('returns false for different session type', () => {
+			const models = [createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud')];
+			assert.strictEqual(hasModelsTargetingSession(models, 'enterprise'), false);
+		});
+	});
+
+	suite('isModelValidForSession', () => {
+
+		test('general model is valid when no models target the session', () => {
+			const generalModel = createModel('gpt', 'GPT');
+			const allModels = [generalModel];
+			assert.strictEqual(isModelValidForSession(generalModel, allModels, 'cloud'), true);
+		});
+
+		test('session-targeted model is NOT valid when no models target the session type in pool', () => {
+			const sessionModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const generalModel = createModel('gpt', 'GPT');
+			assert.strictEqual(isModelValidForSession(sessionModel, [generalModel], undefined), false);
+		});
+
+		test('session-targeted model IS valid when pool has models targeting that session', () => {
+			const sessionModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const allModels = [createModel('gpt', 'GPT'), sessionModel];
+			assert.strictEqual(isModelValidForSession(sessionModel, allModels, 'cloud'), true);
+		});
+
+		test('general model is NOT valid when pool has models targeting the session', () => {
+			const generalModel = createModel('gpt', 'GPT');
+			const sessionModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const allModels = [generalModel, sessionModel];
+			assert.strictEqual(isModelValidForSession(generalModel, allModels, 'cloud'), false);
+		});
+
+		test('model targeting wrong session is NOT valid', () => {
+			const wrongSessionModel = createSessionModel('ent-gpt', 'Enterprise GPT', 'enterprise');
+			const cloudModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const allModels = [wrongSessionModel, cloudModel];
+			assert.strictEqual(isModelValidForSession(wrongSessionModel, allModels, 'cloud'), false);
+		});
+
+		test('general model is valid when session type is undefined', () => {
+			const generalModel = createModel('gpt', 'GPT');
+			assert.strictEqual(isModelValidForSession(generalModel, [generalModel], undefined), true);
+		});
+	});
+
+	suite('findDefaultModel', () => {
+
+		test('returns model marked as default for location', () => {
+			const regular = createModel('gpt', 'GPT');
+			const defaultModel = createDefaultModelForLocation('claude', 'Claude', ChatAgentLocation.Chat);
+			const result = findDefaultModel([regular, defaultModel], ChatAgentLocation.Chat);
+			assert.strictEqual(result?.metadata.id, 'claude');
+		});
+
+		test('falls back to first model when no default for location', () => {
+			const modelA = createModel('gpt', 'GPT');
+			const modelB = createModel('claude', 'Claude');
+			const result = findDefaultModel([modelA, modelB], ChatAgentLocation.Chat);
+			assert.strictEqual(result?.metadata.id, 'gpt');
+		});
+
+		test('returns undefined for empty models array', () => {
+			const result = findDefaultModel([], ChatAgentLocation.Chat);
+			assert.strictEqual(result, undefined);
+		});
+
+		test('returns location-specific default when multiple defaults exist', () => {
+			const chatDefault = createDefaultModelForLocation('chat-default', 'Chat Default', ChatAgentLocation.Chat);
+			const terminalDefault = createDefaultModelForLocation('terminal-default', 'Terminal Default', ChatAgentLocation.Terminal);
+			const result = findDefaultModel([chatDefault, terminalDefault], ChatAgentLocation.Chat);
+			assert.strictEqual(result?.metadata.id, 'chat-default');
+		});
+
+		test('does not pick terminal default when looking for chat default', () => {
+			const terminalDefault = createDefaultModelForLocation('terminal-default', 'Terminal Default', ChatAgentLocation.Terminal);
+			const regular = createModel('gpt', 'GPT');
+			const result = findDefaultModel([terminalDefault, regular], ChatAgentLocation.Chat);
+			// Falls back to first model since none is default for Chat
+			assert.strictEqual(result?.metadata.id, 'terminal-default');
+		});
+	});
+
+	suite('shouldRestorePersistedModel', () => {
+
+		test('restores model that was explicitly chosen (not default)', () => {
+			const model = createModel('gpt', 'GPT');
+			const result = shouldRestorePersistedModel('copilot/gpt', false, [model], ChatAgentLocation.Chat);
+			assert.strictEqual(result.shouldRestore, true);
+			assert.strictEqual(result.model?.identifier, 'copilot/gpt');
+		});
+
+		test('restores model that was default and is still default', () => {
+			const model = createDefaultModelForLocation('gpt', 'GPT', ChatAgentLocation.Chat);
+			const result = shouldRestorePersistedModel('copilot/gpt', true, [model], ChatAgentLocation.Chat);
+			assert.strictEqual(result.shouldRestore, true);
+		});
+
+		test('does NOT restore model that was default but is no longer default', () => {
+			const model = createModel('gpt', 'GPT');
+			const result = shouldRestorePersistedModel('copilot/gpt', true, [model], ChatAgentLocation.Chat);
+			assert.strictEqual(result.shouldRestore, false);
+			assert.strictEqual(result.model?.identifier, 'copilot/gpt');
+		});
+
+		test('does NOT restore model that no longer exists', () => {
+			const otherModel = createModel('claude', 'Claude');
+			const result = shouldRestorePersistedModel('copilot/gpt', false, [otherModel], ChatAgentLocation.Chat);
+			assert.strictEqual(result.shouldRestore, false);
+			assert.strictEqual(result.model, undefined);
+		});
+
+		test('handles empty models list', () => {
+			const result = shouldRestorePersistedModel('copilot/gpt', false, [], ChatAgentLocation.Chat);
+			assert.strictEqual(result.shouldRestore, false);
+			assert.strictEqual(result.model, undefined);
+		});
+
+		test('user choice is preserved when default changes to a different model', () => {
+			// User explicitly chose GPT-4o, default used to be Claude, now default is something else
+			const gpt = createModel('gpt-4o', 'GPT-4o');
+			const claude = createModel('claude', 'Claude');
+			const result = shouldRestorePersistedModel('copilot/gpt-4o', false, [gpt, claude], ChatAgentLocation.Chat);
+			assert.strictEqual(result.shouldRestore, true);
+			assert.strictEqual(result.model?.metadata.id, 'gpt-4o');
+		});
+
+		test('default tracking: follows new default when user never explicitly chose', () => {
+			// Old default was GPT-4o (persisted as default), now Claude is the default
+			const gpt = createModel('gpt-4o', 'GPT-4o');
+			const claude = createDefaultModelForLocation('claude', 'Claude', ChatAgentLocation.Chat);
+			const result = shouldRestorePersistedModel('copilot/gpt-4o', true, [gpt, claude], ChatAgentLocation.Chat);
+			// Should NOT restore because GPT-4o is no longer default and was stored as default
+			assert.strictEqual(result.shouldRestore, false);
+		});
+	});
+
+	suite('shouldResetModelToDefault', () => {
+
+		const defaultContext = {
+			location: ChatAgentLocation.Chat,
+			currentModeKind: ChatModeKind.Ask,
+			isInlineChatV2Enabled: false,
+			sessionType: undefined,
+		};
+
+		test('should reset when current model is undefined', () => {
+			assert.strictEqual(shouldResetModelToDefault(undefined, [], defaultContext, []), true);
+		});
+
+		test('should reset when model is no longer available', () => {
+			const model = createModel('gpt', 'GPT');
+			assert.strictEqual(shouldResetModelToDefault(model, [], defaultContext, [model]), true);
+		});
+
+		test('should NOT reset when model is available and compatible', () => {
+			const model = createModel('gpt', 'GPT');
+			assert.strictEqual(shouldResetModelToDefault(model, [model], defaultContext, [model]), false);
+		});
+
+		test('should reset when model is not supported for current mode', () => {
+			const model = createModel('no-tools', 'No-Tools', {
+				capabilities: { toolCalling: false, agentMode: false },
+			});
+			const context = { ...defaultContext, currentModeKind: ChatModeKind.Agent };
+			assert.strictEqual(shouldResetModelToDefault(model, [model], context, [model]), true);
+		});
+
+		test('should reset when model is not supported for inline chat', () => {
+			const model = createModel('no-tools', 'No-Tools', {
+				capabilities: { toolCalling: false },
+			});
+			const context = {
+				...defaultContext,
+				location: ChatAgentLocation.EditorInline,
+				isInlineChatV2Enabled: true,
+			};
+			assert.strictEqual(shouldResetModelToDefault(model, [model], context, [model]), true);
+		});
+
+		test('should reset when model is not valid for session', () => {
+			const generalModel = createModel('gpt', 'GPT');
+			const sessionModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const allModels = [generalModel, sessionModel];
+			const context = { ...defaultContext, sessionType: 'cloud' };
+			assert.strictEqual(shouldResetModelToDefault(generalModel, [generalModel], context, allModels), true);
+		});
+
+		test('should NOT reset session model in matching session', () => {
+			const sessionModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const context = { ...defaultContext, sessionType: 'cloud' };
+			assert.strictEqual(shouldResetModelToDefault(sessionModel, [sessionModel], context, [sessionModel]), false);
+		});
+	});
+
+	suite('resolveModelFromSyncState', () => {
+
+		test('keeps current model when same as state model', () => {
+			const model = createModel('gpt', 'GPT');
+			const result = resolveModelFromSyncState(model, model, [model], undefined);
+			assert.strictEqual(result.action, 'keep');
+		});
+
+		test('applies state model when different and valid', () => {
+			const current = createModel('gpt', 'GPT');
+			const stateModel = createModel('claude', 'Claude');
+			const result = resolveModelFromSyncState(stateModel, current, [current, stateModel], undefined);
+			assert.strictEqual(result.action, 'apply');
+		});
+
+		test('uses default when state model not valid for session', () => {
+			const current = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const stateModel = createModel('gpt', 'GPT'); // general model, not valid for cloud session
+			const allModels = [current, stateModel];
+			const result = resolveModelFromSyncState(stateModel, current, allModels, 'cloud');
+			assert.strictEqual(result.action, 'default');
+		});
+
+		test('applies when current model is undefined', () => {
+			const stateModel = createModel('gpt', 'GPT');
+			const result = resolveModelFromSyncState(stateModel, undefined, [stateModel], undefined);
+			assert.strictEqual(result.action, 'apply');
+		});
+
+		test('applies session model when valid for matching session', () => {
+			const sessionModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const generalModel = createModel('gpt', 'GPT');
+			const allModels = [generalModel, sessionModel];
+			const result = resolveModelFromSyncState(sessionModel, generalModel, allModels, 'cloud');
+			assert.strictEqual(result.action, 'apply');
+		});
+
+		test('returns default when state model does not support current mode', () => {
+			const current = createModel('gpt', 'GPT');
+			const stateModel = createModel('no-tools', 'No-Tools', {
+				capabilities: { toolCalling: false, agentMode: false },
+			});
+			const result = resolveModelFromSyncState(stateModel, current, [current, stateModel], undefined, {
+				location: ChatAgentLocation.Chat,
+				currentModeKind: ChatModeKind.Agent,
+				isInlineChatV2Enabled: false,
+				sessionType: undefined,
+			});
+			assert.strictEqual(result.action, 'default');
+		});
+
+		test('returns default when state model does not support inline chat V2', () => {
+			const current = createModel('gpt', 'GPT');
+			const stateModel = createModel('no-tools', 'No-Tools', {
+				capabilities: { toolCalling: false },
+			});
+			const result = resolveModelFromSyncState(stateModel, current, [current, stateModel], undefined, {
+				location: ChatAgentLocation.EditorInline,
+				currentModeKind: ChatModeKind.Ask,
+				isInlineChatV2Enabled: true,
+				sessionType: undefined,
+			});
+			assert.strictEqual(result.action, 'default');
+		});
+
+		test('applies when state model supports current mode with context', () => {
+			const current = createModel('gpt', 'GPT');
+			const stateModel = createModel('agent-model', 'Agent Model', {
+				capabilities: { toolCalling: true, agentMode: true },
+			});
+			const result = resolveModelFromSyncState(stateModel, current, [current, stateModel], undefined, {
+				location: ChatAgentLocation.Chat,
+				currentModeKind: ChatModeKind.Agent,
+				isInlineChatV2Enabled: false,
+				sessionType: undefined,
+			});
+			assert.strictEqual(result.action, 'apply');
+		});
+	});
+
+	suite('mergeModelsWithCache', () => {
+
+		test('uses live models when available', () => {
+			const liveModel = createModel('gpt', 'GPT');
+			const cachedModel = createModel('cached-gpt', 'Cached GPT');
+			const result = mergeModelsWithCache([liveModel], [cachedModel], new Set(['copilot']));
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual(result[0].metadata.id, 'gpt');
+		});
+
+		test('falls back to cached models when no live models', () => {
+			const cachedModel = createModel('cached-gpt', 'Cached GPT');
+			const result = mergeModelsWithCache([], [cachedModel], new Set(['copilot']));
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual(result[0].metadata.id, 'cached-gpt');
+		});
+
+		test('merges cached models from vendors not yet resolved', () => {
+			const liveModel = createModel('gpt', 'GPT');
+			const cachedOtherVendor = createModel('other-model', 'Other Model', { vendor: 'other-vendor' });
+			const result = mergeModelsWithCache(
+				[liveModel],
+				[cachedOtherVendor],
+				new Set(['copilot', 'other-vendor']),
+			);
+			assert.strictEqual(result.length, 2);
+			assert.deepStrictEqual(result.map(m => m.metadata.id).sort(), ['gpt', 'other-model']);
+		});
+
+		test('evicts cached models from vendors no longer contributed', () => {
+			const liveModel = createModel('gpt', 'GPT');
+			const cachedRemovedVendor = createModel('removed-model', 'Removed Model', { vendor: 'removed-vendor' });
+			const result = mergeModelsWithCache(
+				[liveModel],
+				[cachedRemovedVendor],
+				new Set(['copilot']), // removed-vendor is NOT contributed
+			);
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual(result[0].metadata.id, 'gpt');
+		});
+
+		test('does not duplicate models from same vendor', () => {
+			const liveModel = createModel('gpt', 'GPT');
+			const cachedSameVendor = createModel('cached-gpt', 'Cached GPT');
+			const result = mergeModelsWithCache(
+				[liveModel],
+				[cachedSameVendor],
+				new Set(['copilot']),
+			);
+			// Both are vendor 'copilot', live vendor takes priority
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual(result[0].metadata.id, 'gpt');
+		});
+
+		test('handles empty cache and empty live models', () => {
+			const result = mergeModelsWithCache([], [], new Set());
+			assert.deepStrictEqual(result, []);
+		});
+
+		test('handles multiple vendors with partial resolution', () => {
+			const liveA = createModel('a-model', 'A Model', { vendor: 'vendor-a' });
+			const cachedB = createModel('b-model', 'B Model', { vendor: 'vendor-b' });
+			const cachedC = createModel('c-model', 'C Model', { vendor: 'vendor-c' });
+			const result = mergeModelsWithCache(
+				[liveA],
+				[cachedB, cachedC],
+				new Set(['vendor-a', 'vendor-b']), // vendor-c not contributed
+			);
+			assert.strictEqual(result.length, 2);
+			assert.deepStrictEqual(result.map(m => m.metadata.vendor).sort(), ['vendor-a', 'vendor-b']);
+		});
+	});
+
+	suite('model switching scenarios', () => {
+
+		test('switching from Ask to Agent mode should reset model without tool support', () => {
+			const noToolsModel = createModel('no-tools', 'No-Tools', {
+				capabilities: { toolCalling: false, agentMode: false },
+			});
+			const toolModel = createModel('tool-model', 'Tool Model');
+			const allModels = [noToolsModel, toolModel];
+
+			// In Ask mode, model is fine
+			assert.strictEqual(
+				shouldResetModelToDefault(noToolsModel, allModels, {
+					location: ChatAgentLocation.Chat,
+					currentModeKind: ChatModeKind.Ask,
+					isInlineChatV2Enabled: false,
+					sessionType: undefined,
+				}, allModels),
+				false,
+			);
+
+			// After switching to Agent mode, model should be reset
+			assert.strictEqual(
+				shouldResetModelToDefault(noToolsModel, allModels, {
+					location: ChatAgentLocation.Chat,
+					currentModeKind: ChatModeKind.Agent,
+					isInlineChatV2Enabled: false,
+					sessionType: undefined,
+				}, allModels),
+				true,
+			);
+		});
+
+		test('switching sessions should reject model from wrong session pool', () => {
+			const cloudModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const generalModel = createModel('gpt', 'GPT');
+			const allModels = [generalModel, cloudModel];
+
+			// Cloud model is valid in cloud session
+			assert.strictEqual(
+				isModelValidForSession(cloudModel, allModels, 'cloud'),
+				true,
+			);
+
+			// Cloud model is NOT valid in general session (no session type)
+			assert.strictEqual(
+				isModelValidForSession(cloudModel, allModels, undefined),
+				false,
+			);
+
+			// General model is NOT valid in cloud session (when cloud models exist)
+			assert.strictEqual(
+				isModelValidForSession(generalModel, allModels, 'cloud'),
+				false,
+			);
+
+			// General model IS valid in general session
+			assert.strictEqual(
+				isModelValidForSession(generalModel, allModels, undefined),
+				true,
+			);
+		});
+
+		test('model removal should trigger reset', () => {
+			const gpt = createModel('gpt', 'GPT');
+			const claude = createModel('claude', 'Claude');
+
+			// Initially both available, GPT is selected
+			assert.strictEqual(
+				shouldResetModelToDefault(gpt, [gpt, claude], {
+					location: ChatAgentLocation.Chat,
+					currentModeKind: ChatModeKind.Ask,
+					isInlineChatV2Enabled: false,
+					sessionType: undefined,
+				}, [gpt, claude]),
+				false,
+			);
+
+			// GPT is removed from available models
+			assert.strictEqual(
+				shouldResetModelToDefault(gpt, [claude], {
+					location: ChatAgentLocation.Chat,
+					currentModeKind: ChatModeKind.Ask,
+					isInlineChatV2Enabled: false,
+					sessionType: undefined,
+				}, [claude]),
+				true,
+			);
+		});
+
+		test('syncing model from state respects session boundaries', () => {
+			const cloudModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const generalModel = createModel('gpt', 'GPT');
+			const allModels = [generalModel, cloudModel];
+
+			// State has a cloud model, but we are in a general session
+			const result = resolveModelFromSyncState(cloudModel, generalModel, allModels, undefined);
+			assert.strictEqual(result.action, 'default');
+		});
+
+		test('syncing model from state applies model when switching to matching session', () => {
+			const cloudModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const generalModel = createModel('gpt', 'GPT');
+			const allModels = [generalModel, cloudModel];
+
+			// State has a cloud model and we are in a cloud session
+			const result = resolveModelFromSyncState(cloudModel, generalModel, allModels, 'cloud');
+			assert.strictEqual(result.action, 'apply');
+		});
+
+		test('persisted model selection survives when model is still default', () => {
+			const model = createDefaultModelForLocation('gpt-4o', 'GPT-4o', ChatAgentLocation.Chat);
+			const result = shouldRestorePersistedModel('copilot/gpt-4o', true, [model], ChatAgentLocation.Chat);
+			assert.strictEqual(result.shouldRestore, true);
+		});
+
+		test('persisted model selection does NOT restore when a new default is assigned', () => {
+			// GPT-4o was the old default (persisted as default=true), but it's no longer default
+			const gpt4o = createModel('gpt-4o', 'GPT-4o');
+			const newDefault = createDefaultModelForLocation('claude', 'Claude', ChatAgentLocation.Chat);
+			const result = shouldRestorePersistedModel('copilot/gpt-4o', true, [gpt4o, newDefault], ChatAgentLocation.Chat);
+			assert.strictEqual(result.shouldRestore, false);
+		});
+
+		test('user explicit model choice persists even when default changes', () => {
+			// User explicitly picked Claude (persistedAsDefault=false), default was GPT-4o
+			// Now default switches to something else — Claude should still be restored
+			const claude = createModel('claude', 'Claude');
+			const newDefault = createDefaultModelForLocation('new-model', 'New Model', ChatAgentLocation.Chat);
+			const result = shouldRestorePersistedModel('copilot/claude', false, [claude, newDefault], ChatAgentLocation.Chat);
+			assert.strictEqual(result.shouldRestore, true);
+			assert.strictEqual(result.model?.metadata.id, 'claude');
+		});
+
+		test('combining mode switch + session switch validates correctly', () => {
+			const cloudToolModel = createSessionModel('cloud-tool', 'Cloud Tool', 'cloud', {
+				capabilities: { toolCalling: true, agentMode: true },
+			});
+			const cloudNoToolModel = createSessionModel('cloud-basic', 'Cloud Basic', 'cloud', {
+				capabilities: { toolCalling: false, agentMode: false },
+			});
+			const allCloudModels = [cloudToolModel, cloudNoToolModel];
+
+			// In cloud session, Agent mode — tool model is valid
+			assert.strictEqual(
+				shouldResetModelToDefault(cloudToolModel, allCloudModels, {
+					location: ChatAgentLocation.Chat,
+					currentModeKind: ChatModeKind.Agent,
+					isInlineChatV2Enabled: false,
+					sessionType: 'cloud',
+				}, allCloudModels),
+				false,
+			);
+
+			// The no-tool model should be reset in Agent mode
+			// Both filterModelsForSession and shouldResetModelToDefault enforce mode support
+			assert.strictEqual(
+				shouldResetModelToDefault(cloudNoToolModel, allCloudModels, {
+					location: ChatAgentLocation.Chat,
+					currentModeKind: ChatModeKind.Agent,
+					isInlineChatV2Enabled: false,
+					sessionType: 'cloud',
+				}, allCloudModels),
+				true,
+			);
+		});
+	});
+
+	suite('onDidChangeLanguageModels race conditions', () => {
+
+		test('model temporarily removed then re-added loses user choice', () => {
+			const gpt = createModel('gpt', 'GPT');
+			const claude = createModel('claude', 'Claude');
+
+			// Step 1: User has GPT selected, both models available
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', [gpt, claude]), false);
+
+			// Step 2: Extension reloads, GPT temporarily disappears from model list
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', [claude]), true);
+			// → ChatInputPart resets to default (Claude)
+
+			// Step 3: GPT comes back — but the handler just checks if current is still valid.
+			// By now the current is Claude (from step 2), so it stays.
+			assert.strictEqual(shouldResetOnModelListChange('copilot/claude', [gpt, claude]), false);
+			// → User's original GPT choice is lost! This is the "random switch" bug pattern.
+		});
+
+		test('model stays when model list refreshes with it still present', () => {
+			const gpt = createModel('gpt', 'GPT');
+			const claude = createModel('claude', 'Claude');
+
+			// Model list refreshes but GPT is still there
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', [gpt, claude]), false);
+		});
+
+		test('reset when current model identifier is undefined', () => {
+			const gpt = createModel('gpt', 'GPT');
+			assert.strictEqual(shouldResetOnModelListChange(undefined, [gpt]), true);
+		});
+
+		test('reset when models list is empty', () => {
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', []), true);
+		});
+
+		test('cache bridges the gap when live models temporarily unavailable', () => {
+			const cachedGpt = createModel('gpt', 'GPT');
+			const cachedClaude = createModel('claude', 'Claude');
+
+			// Step 1: Extension unloaded, no live models. Cache fills the gap.
+			const merged = mergeModelsWithCache([], [cachedGpt, cachedClaude], new Set(['copilot']));
+			assert.strictEqual(merged.length, 2);
+
+			// Selected model is still found in the cached list
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', merged), false);
+		});
+
+		test('cache kept even for uncontributed vendors when no live models exist', () => {
+			const cachedGpt = createModel('gpt', 'GPT');
+
+			// When liveModels is empty, mergeModelsWithCache returns ALL cached
+			// because it can't distinguish "startup not ready" from "vendor removed"
+			const merged = mergeModelsWithCache([], [cachedGpt], new Set());
+			assert.strictEqual(merged.length, 1);
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', merged), false);
+		});
+
+		test('cache evicted for uncontributed vendor once live models arrive', () => {
+			const cachedGpt = createModel('gpt', 'GPT');
+			const liveOther = createModel('other', 'Other', { vendor: 'other-vendor' });
+
+			// Once live models exist, the vendor filter kicks in
+			const merged = mergeModelsWithCache([liveOther], [cachedGpt], new Set(['other-vendor']));
+			assert.strictEqual(merged.length, 1);
+			assert.strictEqual(merged[0].metadata.id, 'other');
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', merged), true);
+		});
+	});
+
+	suite('late-arriving model restoration', () => {
+
+		test('restores explicitly-chosen model that arrives late', () => {
+			const model = createModel('gpt', 'GPT');
+			assert.strictEqual(
+				shouldRestoreLateArrivingModel('copilot/gpt', false, model, ChatAgentLocation.Chat),
+				true,
+			);
+		});
+
+		test('restores model that was default and is still default for location', () => {
+			const model = createDefaultModelForLocation('gpt', 'GPT', ChatAgentLocation.Chat);
+			assert.strictEqual(
+				shouldRestoreLateArrivingModel('copilot/gpt', true, model, ChatAgentLocation.Chat),
+				true,
+			);
+		});
+
+		test('does NOT restore model that was default but is no longer default', () => {
+			const model = createModel('gpt', 'GPT'); // not default for any location
+			assert.strictEqual(
+				shouldRestoreLateArrivingModel('copilot/gpt', true, model, ChatAgentLocation.Chat),
+				false,
+			);
+		});
+
+		test('does NOT restore model that is not user-selectable', () => {
+			const model = createModel('internal', 'Internal', { isUserSelectable: false });
+			assert.strictEqual(
+				shouldRestoreLateArrivingModel('copilot/internal', false, model, ChatAgentLocation.Chat),
+				false,
+			);
+		});
+
+		test('does NOT restore model with isUserSelectable=undefined (treated as falsy)', () => {
+			const model = createModel('undef-sel', 'Undef-Sel', { isUserSelectable: undefined });
+			assert.strictEqual(
+				shouldRestoreLateArrivingModel('copilot/undef-sel', false, model, ChatAgentLocation.Chat),
+				false,
+			);
+		});
+
+		test('restores model arriving late at a different location where it is default', () => {
+			const model = createDefaultModelForLocation('gpt', 'GPT', ChatAgentLocation.Terminal);
+			// User is in Terminal — model is default there
+			assert.strictEqual(
+				shouldRestoreLateArrivingModel('copilot/gpt', true, model, ChatAgentLocation.Terminal),
+				true,
+			);
+			// But not in Chat
+			assert.strictEqual(
+				shouldRestoreLateArrivingModel('copilot/gpt', true, model, ChatAgentLocation.Chat),
+				false,
+			);
+		});
+	});
+
+	suite('full startup pipeline (computeAvailableModels)', () => {
+
+		test('startup with only cached models returns filtered cache', () => {
+			const cached = createModel('gpt', 'GPT');
+			const result = computeAvailableModels(
+				[], // no live models yet
+				[cached],
+				new Set(['copilot']),
+				undefined,
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['gpt']);
+		});
+
+		test('startup with cached models from removed vendor still returns them (no live to compare)', () => {
+			const cached = createModel('gpt', 'GPT');
+			// When liveModels is empty, mergeModelsWithCache returns ALL cached
+			// because it cannot tell startup-delay from vendor removal
+			const result = computeAvailableModels(
+				[], // no live models
+				[cached],
+				new Set(), // vendor no longer contributed
+				undefined,
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['gpt']);
+		});
+
+		test('live models supersede cached models from same vendor', () => {
+			const live = createModel('gpt-new', 'GPT New');
+			const cached = createModel('gpt-old', 'GPT Old');
+			const result = computeAvailableModels(
+				[live],
+				[cached],
+				new Set(['copilot']),
+				undefined,
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['gpt-new']);
+		});
+
+		test('partial vendor resolution keeps unresolved vendors from cache', () => {
+			const liveA = createModel('a-model', 'A Model', { vendor: 'vendor-a' });
+			const cachedB = createModel('b-model', 'B Model', { vendor: 'vendor-b' });
+			const result = computeAvailableModels(
+				[liveA],
+				[cachedB],
+				new Set(['vendor-a', 'vendor-b']),
+				undefined,
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id).sort(), ['a-model', 'b-model']);
+		});
+
+		test('results are sorted alphabetically by name', () => {
+			const modelC = createModel('c', 'Charlie');
+			const modelA = createModel('a', 'Alpha');
+			const modelB = createModel('b', 'Bravo');
+			const result = computeAvailableModels(
+				[modelC, modelA, modelB],
+				[],
+				new Set(['copilot']),
+				undefined,
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.name), ['Alpha', 'Bravo', 'Charlie']);
+		});
+
+		test('session-targeted models excluded from general session startup', () => {
+			const general = createModel('gpt', 'GPT');
+			const cloudOnly = createSessionModel('cloud', 'Cloud', 'cloud');
+			const result = computeAvailableModels(
+				[general, cloudOnly],
+				[],
+				new Set(['copilot']),
+				undefined,
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['gpt']);
+		});
+
+		test('only session-targeted models returned for cloud session startup', () => {
+			const general = createModel('gpt', 'GPT');
+			const cloudOnly = createSessionModel('cloud', 'Cloud', 'cloud');
+			const result = computeAvailableModels(
+				[general, cloudOnly],
+				[],
+				new Set(['copilot']),
+				'cloud',
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['cloud']);
+		});
+
+		test('agent mode filters non-tool models during startup', () => {
+			const toolModel = createModel('tool', 'Tool Model');
+			const noToolModel = createModel('no-tool', 'No Tool', {
+				capabilities: { toolCalling: false, agentMode: false },
+			});
+			const result = computeAvailableModels(
+				[toolModel, noToolModel],
+				[],
+				new Set(['copilot']),
+				undefined,
+				ChatModeKind.Agent,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			assert.deepStrictEqual(result.map(m => m.metadata.id), ['tool']);
+		});
+	});
+
+	suite('_syncFromModel edge cases', () => {
+
+		test('sync state with undefined selectedModel keeps current', () => {
+			const current = createModel('gpt', 'GPT');
+			// When state has no selectedModel, _syncFromModel skips the model sync
+			// (the code checks `if (state?.selectedModel)`)
+			// This means the current model stays — test that resolveModelFromSyncState
+			// correctly identifies "keep" for same model
+			const result = resolveModelFromSyncState(current, current, [current], undefined);
+			assert.strictEqual(result.action, 'keep');
+		});
+
+		test('sync state model from different session does not apply', () => {
+			// Scenario: User is in session A with cloud model, switches to session B (general)
+			// Session B's state still has the cloud model reference
+			const cloudModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const generalModel = createModel('gpt', 'GPT');
+			const allModels = [generalModel, cloudModel];
+
+			const result = resolveModelFromSyncState(cloudModel, generalModel, allModels, undefined);
+			assert.strictEqual(result.action, 'default');
+		});
+
+		test('sync state with model matching different session type falls back to default', () => {
+			const enterpriseModel = createSessionModel('ent-gpt', 'Enterprise GPT', 'enterprise');
+			const cloudModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const allModels = [cloudModel, enterpriseModel];
+
+			// State has enterprise model, but we're in cloud session
+			const result = resolveModelFromSyncState(enterpriseModel, cloudModel, allModels, 'cloud');
+			assert.strictEqual(result.action, 'default');
+		});
+
+		test('sync identical model reference returns keep', () => {
+			const model = createModel('gpt', 'GPT');
+			// Same object reference
+			const result = resolveModelFromSyncState(model, model, [model], undefined);
+			assert.strictEqual(result.action, 'keep');
+		});
+
+		test('sync same identifier but different object returns keep', () => {
+			const model1 = createModel('gpt', 'GPT');
+			const model2 = createModel('gpt', 'GPT');
+			// Different objects, same identifier
+			const result = resolveModelFromSyncState(model1, model2, [model1, model2], undefined);
+			assert.strictEqual(result.action, 'keep');
+		});
+	});
+
+	suite('checkModelSupported interaction patterns', () => {
+
+		const askContext = {
+			location: ChatAgentLocation.Chat,
+			currentModeKind: ChatModeKind.Ask,
+			isInlineChatV2Enabled: false,
+			sessionType: undefined,
+		};
+
+		const agentContext = {
+			...askContext,
+			currentModeKind: ChatModeKind.Agent,
+		};
+
+		test('initSelectedModel → checkModelSupported: restored model passes Agent check', () => {
+			const agentModel = createModel('agent-model', 'Agent Model', {
+				capabilities: { toolCalling: true, agentMode: true },
+			});
+
+			// 1. shouldRestorePersistedModel says "restore"
+			const restoreResult = shouldRestorePersistedModel('copilot/agent-model', false, [agentModel], ChatAgentLocation.Chat);
+			assert.strictEqual(restoreResult.shouldRestore, true);
+
+			// 2. Immediately after, checkModelSupported runs with Agent mode
+			assert.strictEqual(shouldResetModelToDefault(agentModel, [agentModel], agentContext, [agentModel]), false);
+		});
+
+		test('initSelectedModel → checkModelSupported: restored model FAILS Agent check', () => {
+			const askOnlyModel = createModel('ask-only', 'Ask Only', {
+				capabilities: { toolCalling: false, agentMode: false },
+			});
+			const agentModel = createModel('agent-model', 'Agent Model');
+
+			// 1. shouldRestorePersistedModel says "restore"
+			const restoreResult = shouldRestorePersistedModel('copilot/ask-only', false, [askOnlyModel, agentModel], ChatAgentLocation.Chat);
+			assert.strictEqual(restoreResult.shouldRestore, true);
+
+			// 2. checkModelSupported runs with Agent mode → should reset
+			assert.strictEqual(shouldResetModelToDefault(askOnlyModel, [askOnlyModel, agentModel], agentContext, [askOnlyModel, agentModel]), true);
+
+			// 3. findDefaultModel picks replacement from models filtered for Agent mode
+			const agentCompatibleModels = filterModelsForSession(
+				[askOnlyModel, agentModel], undefined, ChatModeKind.Agent, ChatAgentLocation.Chat, false
+			);
+			const defaultModel = findDefaultModel(agentCompatibleModels, ChatAgentLocation.Chat);
+			assert.strictEqual(defaultModel?.metadata.id, 'agent-model');
+		});
+
+		test('mode switch triggers checkModelSupported which resets incompatible model', () => {
+			const noToolModel = createModel('no-tool', 'No Tool', {
+				capabilities: { toolCalling: false },
+			});
+			const toolModel = createModel('tool', 'Tool');
+
+			// In Ask mode: fine
+			assert.strictEqual(shouldResetModelToDefault(noToolModel, [noToolModel, toolModel], askContext, [noToolModel, toolModel]), false);
+
+			// Switch to Agent mode: not fine
+			assert.strictEqual(shouldResetModelToDefault(noToolModel, [noToolModel, toolModel], agentContext, [noToolModel, toolModel]), true);
+		});
+
+		test('double reset is idempotent', () => {
+			const defaultModel = createDefaultModelForLocation('default', 'Default', ChatAgentLocation.Chat);
+			const otherModel = createModel('other', 'Other');
+			const allModels = [defaultModel, otherModel];
+
+			// First reset: picks default
+			const result1 = findDefaultModel(allModels, ChatAgentLocation.Chat);
+			assert.strictEqual(result1?.metadata.id, 'default');
+
+			// "Second reset" — same call, same result
+			const result2 = findDefaultModel(allModels, ChatAgentLocation.Chat);
+			assert.strictEqual(result2?.metadata.id, 'default');
+
+			// Default model continues to pass validation
+			assert.strictEqual(shouldResetModelToDefault(result1!, allModels, askContext, allModels), false);
+		});
+	});
+
+	suite('multiple session types and cross-contamination', () => {
+
+		test('model from session A rejected in session B', () => {
+			const cloudModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const enterpriseModel = createSessionModel('ent-gpt', 'Enterprise GPT', 'enterprise');
+			const generalModel = createModel('gpt', 'GPT');
+			const allModels = [generalModel, cloudModel, enterpriseModel];
+
+			// Cloud model not valid in enterprise session
+			assert.strictEqual(isModelValidForSession(cloudModel, allModels, 'enterprise'), false);
+			// Enterprise model not valid in cloud session
+			assert.strictEqual(isModelValidForSession(enterpriseModel, allModels, 'cloud'), false);
+			// General model not valid when session-targeted models exist
+			assert.strictEqual(isModelValidForSession(generalModel, allModels, 'cloud'), false);
+		});
+
+		test('general model is valid when session type has no targeted models', () => {
+			const cloudModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const generalModel = createModel('gpt', 'GPT');
+			const allModels = [generalModel, cloudModel];
+
+			// 'enterprise' session has no targeted models
+			assert.strictEqual(isModelValidForSession(generalModel, allModels, 'enterprise'), true);
+		});
+
+		test('filterModelsForSession isolates session types correctly', () => {
+			const general = createModel('gpt', 'GPT');
+			const cloud = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const enterprise = createSessionModel('ent-gpt', 'Enterprise GPT', 'enterprise');
+			const allModels = [general, cloud, enterprise];
+
+			const cloudFiltered = filterModelsForSession(allModels, 'cloud', ChatModeKind.Ask, ChatAgentLocation.Chat, false);
+			assert.deepStrictEqual(cloudFiltered.map(m => m.metadata.id), ['cloud-gpt']);
+
+			const entFiltered = filterModelsForSession(allModels, 'enterprise', ChatModeKind.Ask, ChatAgentLocation.Chat, false);
+			assert.deepStrictEqual(entFiltered.map(m => m.metadata.id), ['ent-gpt']);
+
+			const generalFiltered = filterModelsForSession(allModels, undefined, ChatModeKind.Ask, ChatAgentLocation.Chat, false);
+			assert.deepStrictEqual(generalFiltered.map(m => m.metadata.id), ['gpt']);
+		});
+
+		test('switching from cloud to general session resets cloud model', () => {
+			const cloudModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud');
+			const generalModel = createModel('gpt', 'GPT');
+			const allModels = [generalModel, cloudModel];
+
+			// In cloud session, cloud model is valid
+			assert.strictEqual(shouldResetModelToDefault(cloudModel, [cloudModel], {
+				location: ChatAgentLocation.Chat,
+				currentModeKind: ChatModeKind.Ask,
+				isInlineChatV2Enabled: false,
+				sessionType: 'cloud',
+			}, allModels), false);
+
+			// Switch to general session — cloud model should be reset
+			assert.strictEqual(shouldResetModelToDefault(cloudModel, [generalModel], {
+				location: ChatAgentLocation.Chat,
+				currentModeKind: ChatModeKind.Ask,
+				isInlineChatV2Enabled: false,
+				sessionType: undefined,
+			}, allModels), true);
+		});
+	});
+
+	suite('mode with forced model (mode.model property)', () => {
+
+		test('mode forces model — simulating switchModelByQualifiedName success', () => {
+			const gpt = createModel('gpt-4o', 'GPT-4o');
+			const claude = createModel('claude', 'Claude');
+			const allModels = [gpt, claude];
+
+			// The autorun calls switchModelByQualifiedName which checks ILanguageModelChatMetadata.matchesQualifiedName
+			// Simulate: mode wants "GPT-4o (copilot)"
+			const qualifiedName = 'GPT-4o (copilot)';
+			const match = allModels.find(m => ILanguageModelChatMetadata.matchesQualifiedName(qualifiedName, m.metadata));
+			assert.strictEqual(match?.metadata.id, 'gpt-4o');
+		});
+
+		test('mode forces model — copilot vendor shorthand works', () => {
+			const gpt = createModel('gpt-4o', 'GPT-4o');
+			// For copilot vendor, just the name works
+			const match = [gpt].find(m => ILanguageModelChatMetadata.matchesQualifiedName('GPT-4o', m.metadata));
+			assert.strictEqual(match?.metadata.id, 'gpt-4o');
+		});
+
+		test('mode forces model — nonexistent model gracefully misses', () => {
+			const gpt = createModel('gpt-4o', 'GPT-4o');
+			const match = [gpt].find(m => ILanguageModelChatMetadata.matchesQualifiedName('NonExistent (copilot)', m.metadata));
+			assert.strictEqual(match, undefined);
+		});
+
+		test('mode forces model that is then checked for support', () => {
+			// Mode forces a model, then checkModelSupported runs
+			const forcedModel = createModel('forced', 'Forced', {
+				capabilities: { toolCalling: false, agentMode: false },
+			});
+
+			// Mode forced this model but we're in Agent mode — should be reset
+			assert.strictEqual(shouldResetModelToDefault(forcedModel, [forcedModel], {
+				location: ChatAgentLocation.Chat,
+				currentModeKind: ChatModeKind.Agent,
+				isInlineChatV2Enabled: false,
+				sessionType: undefined,
+			}, [forcedModel]), true);
+		});
+	});
+
+	suite('EditorInline + mode combined scenarios', () => {
+
+		test('EditorInline + Agent + V2 requires both agentMode and toolCalling', () => {
+			const partialModel = createModel('partial', 'Partial', {
+				capabilities: { toolCalling: true, agentMode: false },
+			});
+			// Fails Agent mode check
+			assert.strictEqual(isModelSupportedForMode(partialModel, ChatModeKind.Agent), false);
+			// Passes inline chat check (has toolCalling)
+			assert.strictEqual(isModelSupportedForInlineChat(partialModel, ChatAgentLocation.EditorInline, true), true);
+
+			// Combined: should reset because Agent mode fails
+			assert.strictEqual(shouldResetModelToDefault(partialModel, [partialModel], {
+				location: ChatAgentLocation.EditorInline,
+				currentModeKind: ChatModeKind.Agent,
+				isInlineChatV2Enabled: true,
+				sessionType: undefined,
+			}, [partialModel]), true);
+		});
+
+		test('EditorInline + Ask + V2 only requires toolCalling', () => {
+			const toolModel = createModel('tool', 'Tool');
+			assert.strictEqual(shouldResetModelToDefault(toolModel, [toolModel], {
+				location: ChatAgentLocation.EditorInline,
+				currentModeKind: ChatModeKind.Ask,
+				isInlineChatV2Enabled: true,
+				sessionType: undefined,
+			}, [toolModel]), false);
+		});
+
+		test('EditorInline + Ask + V2 rejects model without toolCalling', () => {
+			const noToolModel = createModel('no-tool', 'No Tool', {
+				capabilities: {},
+			});
+			assert.strictEqual(shouldResetModelToDefault(noToolModel, [noToolModel], {
+				location: ChatAgentLocation.EditorInline,
+				currentModeKind: ChatModeKind.Ask,
+				isInlineChatV2Enabled: true,
+				sessionType: undefined,
+			}, [noToolModel]), true);
+		});
+	});
+
+	suite('findDefaultModel edge cases', () => {
+
+		test('when all models are session-targeted and none is default, first model wins', () => {
+			const m1 = createSessionModel('s1', 'Session 1', 'cloud');
+			const m2 = createSessionModel('s2', 'Session 2', 'cloud');
+			const result = findDefaultModel([m1, m2], ChatAgentLocation.Chat);
+			assert.strictEqual(result?.metadata.id, 's1');
+		});
+
+		test('default for one location does not leak to another', () => {
+			const chatDefault = createDefaultModelForLocation('chat-def', 'Chat Default', ChatAgentLocation.Chat);
+			const noDefault = createModel('no-def', 'No Default');
+
+			// For Chat: chatDefault wins
+			assert.strictEqual(findDefaultModel([noDefault, chatDefault], ChatAgentLocation.Chat)?.metadata.id, 'chat-def');
+			// For Terminal: no model is default, so first model wins
+			assert.strictEqual(findDefaultModel([noDefault, chatDefault], ChatAgentLocation.Terminal)?.metadata.id, 'no-def');
+		});
+	});
+
+	suite('realistic multi-step race simulations', () => {
+
+		test('startup: cached model → live models arrive → user choice preserved', () => {
+			const cachedGpt = createModel('gpt', 'GPT');
+			const cachedClaude = createModel('claude', 'Claude');
+
+			// Step 1: Startup with only cache. User had GPT selected.
+			const cachedModels = computeAvailableModels(
+				[],
+				[cachedGpt, cachedClaude],
+				new Set(['copilot']),
+				undefined,
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			// GPT is in the cached list
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', cachedModels), false);
+
+			// Step 2: Live models arrive (same models)
+			const liveModels = computeAvailableModels(
+				[cachedGpt, cachedClaude],
+				[cachedGpt, cachedClaude],
+				new Set(['copilot']),
+				undefined,
+				ChatModeKind.Ask,
+				ChatAgentLocation.Chat,
+				false,
+			);
+			// GPT still in the list — no reset needed
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', liveModels), false);
+		});
+
+		test('startup: no cache → models arrive late → persisted choice restored', () => {
+			// Step 1: No models available at all
+			const emptyModels = computeAvailableModels([], [], new Set(['copilot']), undefined, ChatModeKind.Ask, ChatAgentLocation.Chat, false);
+			assert.strictEqual(emptyModels.length, 0);
+
+			// initSelectedModel: model not found, enters _waitForPersistedLanguageModel path
+			const restoreResult = shouldRestorePersistedModel('copilot/gpt', false, emptyModels, ChatAgentLocation.Chat);
+			assert.strictEqual(restoreResult.shouldRestore, false);
+			assert.strictEqual(restoreResult.model, undefined);
+
+			// Step 2: Models arrive via onDidChangeLanguageModels
+			const arrivedModel = createModel('gpt', 'GPT');
+			assert.strictEqual(
+				shouldRestoreLateArrivingModel('copilot/gpt', false, arrivedModel, ChatAgentLocation.Chat),
+				true,
+			);
+		});
+
+		test('extension reload: selected model flickers out then back', () => {
+			const gpt = createModel('gpt', 'GPT');
+			const claude = createModel('claude', 'Claude');
+
+			// Step 1: GPT is selected
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', [gpt, claude]), false);
+
+			// Step 2: Extension reloads, copilot vendor has no live models
+			// But cache bridges the gap
+			const duringReload = mergeModelsWithCache([], [gpt, claude], new Set(['copilot']));
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', duringReload), false);
+
+			// Step 3: Extension finishes loading, live models back
+			const afterReload = mergeModelsWithCache([gpt, claude], [gpt, claude], new Set(['copilot']));
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', afterReload), false);
+		});
+
+		test('extension reload without cache: model lost', () => {
+			const gpt = createModel('gpt', 'GPT');
+
+			// Step 1: GPT selected, no cache
+			// Step 2: Extension reloads with no models and no cache
+			const duringReload = mergeModelsWithCache([], [], new Set(['copilot']));
+			assert.strictEqual(duringReload.length, 0);
+			assert.strictEqual(shouldResetOnModelListChange('copilot/gpt', duringReload), true);
+			// → Model is lost, reset to default
+
+			// Step 3: Models come back but user's choice is already gone
+			const afterReload = mergeModelsWithCache([gpt], [], new Set(['copilot']));
+			assert.strictEqual(afterReload.length, 1);
+			// User's selection was already reset to something else
+			// This is expected behavior — cache is the mitigation
+		});
+
+		test('session switch race: mode + session change together', () => {
+			const generalDefault = createDefaultModelForLocation('gpt', 'GPT', ChatAgentLocation.Chat);
+			const cloudModel = createSessionModel('cloud-gpt', 'Cloud GPT', 'cloud', {
+				capabilities: { toolCalling: true, agentMode: true },
+			});
+			const allModels = [generalDefault, cloudModel];
+
+			// User is in general session with GPT in Agent mode
+			assert.strictEqual(shouldResetModelToDefault(generalDefault, [generalDefault], {
+				location: ChatAgentLocation.Chat,
+				currentModeKind: ChatModeKind.Agent,
+				isInlineChatV2Enabled: false,
+				sessionType: undefined,
+			}, allModels), false);
+
+			// Switch to cloud session — general model should be reset
+			assert.strictEqual(shouldResetModelToDefault(generalDefault, [cloudModel], {
+				location: ChatAgentLocation.Chat,
+				currentModeKind: ChatModeKind.Agent,
+				isInlineChatV2Enabled: false,
+				sessionType: 'cloud',
+			}, allModels), true);
+
+			// The default for cloud session should be the cloud model
+			const cloudDefault = findDefaultModel([cloudModel], ChatAgentLocation.Chat);
+			assert.strictEqual(cloudDefault?.metadata.id, 'cloud-gpt');
+		});
+
+		test('rapid mode changes: ask → agent → ask preserves compatible model', () => {
+			const model = createModel('gpt', 'GPT'); // Compatible with all modes
+			const allModels = [model];
+
+			// Ask mode: fine
+			assert.strictEqual(shouldResetModelToDefault(model, allModels, {
+				location: ChatAgentLocation.Chat, currentModeKind: ChatModeKind.Ask,
+				isInlineChatV2Enabled: false, sessionType: undefined,
+			}, allModels), false);
+
+			// → Agent mode: model has toolCalling, still fine
+			assert.strictEqual(shouldResetModelToDefault(model, allModels, {
+				location: ChatAgentLocation.Chat, currentModeKind: ChatModeKind.Agent,
+				isInlineChatV2Enabled: false, sessionType: undefined,
+			}, allModels), false);
+
+			// → Back to Ask: still fine
+			assert.strictEqual(shouldResetModelToDefault(model, allModels, {
+				location: ChatAgentLocation.Chat, currentModeKind: ChatModeKind.Ask,
+				isInlineChatV2Enabled: false, sessionType: undefined,
+			}, allModels), false);
+		});
+
+		test('rapid mode changes: ask → agent resets incompatible, then agent → ask does not restore', () => {
+			const noToolModel = createModel('no-tool', 'No Tool', {
+				capabilities: { toolCalling: false },
+			});
+			const toolModel = createDefaultModelForLocation('tool', 'Tool', ChatAgentLocation.Chat);
+			const allModels = [noToolModel, toolModel];
+
+			// Ask mode with noToolModel: fine
+			assert.strictEqual(shouldResetModelToDefault(noToolModel, allModels, {
+				location: ChatAgentLocation.Chat, currentModeKind: ChatModeKind.Ask,
+				isInlineChatV2Enabled: false, sessionType: undefined,
+			}, allModels), false);
+
+			// → Agent mode: noToolModel fails, reset picks default (toolModel)
+			assert.strictEqual(shouldResetModelToDefault(noToolModel, allModels, {
+				location: ChatAgentLocation.Chat, currentModeKind: ChatModeKind.Agent,
+				isInlineChatV2Enabled: false, sessionType: undefined,
+			}, allModels), true);
+			const defaultAfterReset = findDefaultModel(allModels, ChatAgentLocation.Chat);
+			assert.strictEqual(defaultAfterReset?.metadata.id, 'tool');
+
+			// → Back to Ask: toolModel is fine in Ask mode, stays as toolModel
+			// The original noToolModel is NOT restored — this is expected and matches ChatInputPart behavior
+			assert.strictEqual(shouldResetModelToDefault(toolModel, allModels, {
+				location: ChatAgentLocation.Chat, currentModeKind: ChatModeKind.Ask,
+				isInlineChatV2Enabled: false, sessionType: undefined,
+			}, allModels), false);
+		});
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/common/chatDebugEvents.test.ts b/src/vs/workbench/contrib/chat/test/common/chatDebugEvents.test.ts
new file mode 100644
index 0000000000000..ae69da089de53
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/common/chatDebugEvents.test.ts
@@ -0,0 +1,327 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { URI } from '../../../../../base/common/uri.js';
+import { ChatDebugLogLevel, IChatDebugEvent, IChatDebugGenericEvent, IChatDebugModelTurnEvent, IChatDebugSubagentInvocationEvent, IChatDebugToolCallEvent, IChatDebugUserMessageEvent, IChatDebugAgentResponseEvent } from '../../common/chatDebugService.js';
+import { debugEventMatchesText, filterDebugEvents, filterDebugEventsByText, parseTimeToken, stripTimestampTokens } from '../../common/chatDebugEvents.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+
+const sessionResource = URI.parse('vscode-chat-session://local/test');
+
+function makeGenericEvent(overrides: Partial<IChatDebugGenericEvent> = {}): IChatDebugGenericEvent {
+	return {
+		kind: 'generic',
+		sessionResource,
+		created: new Date('2026-03-10T12:00:00Z'),
+		name: 'test-event',
+		level: ChatDebugLogLevel.Info,
+		...overrides,
+	};
+}
+
+function makeToolCallEvent(overrides: Partial<IChatDebugToolCallEvent> = {}): IChatDebugToolCallEvent {
+	return {
+		kind: 'toolCall',
+		sessionResource,
+		created: new Date('2026-03-10T12:01:00Z'),
+		toolName: 'readFile',
+		...overrides,
+	};
+}
+
+function makeModelTurnEvent(overrides: Partial<IChatDebugModelTurnEvent> = {}): IChatDebugModelTurnEvent {
+	return {
+		kind: 'modelTurn',
+		sessionResource,
+		created: new Date('2026-03-10T12:02:00Z'),
+		model: 'gpt-4o',
+		requestName: 'chat-request',
+		...overrides,
+	};
+}
+
+function makeSubagentEvent(overrides: Partial<IChatDebugSubagentInvocationEvent> = {}): IChatDebugSubagentInvocationEvent {
+	return {
+		kind: 'subagentInvocation',
+		sessionResource,
+		created: new Date('2026-03-10T12:03:00Z'),
+		agentName: 'explorer',
+		...overrides,
+	};
+}
+
+function makeUserMessageEvent(overrides: Partial<IChatDebugUserMessageEvent> = {}): IChatDebugUserMessageEvent {
+	return {
+		kind: 'userMessage',
+		sessionResource,
+		created: new Date('2026-03-10T12:04:00Z'),
+		message: 'hello world',
+		sections: [],
+		...overrides,
+	};
+}
+
+function makeAgentResponseEvent(overrides: Partial<IChatDebugAgentResponseEvent> = {}): IChatDebugAgentResponseEvent {
+	return {
+		kind: 'agentResponse',
+		sessionResource,
+		created: new Date('2026-03-10T12:05:00Z'),
+		message: 'Here is the answer',
+		sections: [],
+		...overrides,
+	};
+}
+
+suite('chatDebugEvents', () => {
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	suite('debugEventMatchesText', () => {
+		test('matches event kind', () => {
+			assert.strictEqual(debugEventMatchesText(makeToolCallEvent(), 'toolcall'), true);
+			assert.strictEqual(debugEventMatchesText(makeToolCallEvent(), 'generic'), false);
+		});
+
+		test('matches toolCall tool name', () => {
+			assert.strictEqual(debugEventMatchesText(makeToolCallEvent({ toolName: 'readFile' }), 'readfile'), true);
+			assert.strictEqual(debugEventMatchesText(makeToolCallEvent({ toolName: 'readFile' }), 'writefile'), false);
+		});
+
+		test('matches toolCall input and output', () => {
+			const event = makeToolCallEvent({ input: 'path/to/file.ts', output: 'file contents' });
+			assert.strictEqual(debugEventMatchesText(event, 'path/to'), true);
+			assert.strictEqual(debugEventMatchesText(event, 'contents'), true);
+			assert.strictEqual(debugEventMatchesText(event, 'missing'), false);
+		});
+
+		test('matches modelTurn model and requestName', () => {
+			assert.strictEqual(debugEventMatchesText(makeModelTurnEvent({ model: 'gpt-4o' }), 'gpt-4o'), true);
+			assert.strictEqual(debugEventMatchesText(makeModelTurnEvent({ requestName: 'chat-request' }), 'chat-request'), true);
+		});
+
+		test('matches generic event name, details, and category', () => {
+			const event = makeGenericEvent({ name: 'discovery', details: 'loaded 5 files', category: 'instructions' });
+			assert.strictEqual(debugEventMatchesText(event, 'discovery'), true);
+			assert.strictEqual(debugEventMatchesText(event, 'loaded'), true);
+			assert.strictEqual(debugEventMatchesText(event, 'instructions'), true);
+			assert.strictEqual(debugEventMatchesText(event, 'missing'), false);
+		});
+
+		test('matches subagentInvocation agent name and description', () => {
+			const event = makeSubagentEvent({ agentName: 'explorer', description: 'search codebase' });
+			assert.strictEqual(debugEventMatchesText(event, 'explorer'), true);
+			assert.strictEqual(debugEventMatchesText(event, 'codebase'), true);
+		});
+
+		test('matches userMessage message and sections', () => {
+			const event = makeUserMessageEvent({
+				message: 'fix the bug',
+				sections: [{ name: 'system', content: 'you are a helpful assistant' }],
+			});
+			assert.strictEqual(debugEventMatchesText(event, 'fix'), true);
+			assert.strictEqual(debugEventMatchesText(event, 'system'), true);
+			assert.strictEqual(debugEventMatchesText(event, 'helpful'), true);
+		});
+
+		test('matches agentResponse message and sections', () => {
+			const event = makeAgentResponseEvent({
+				message: 'done',
+				sections: [{ name: 'result', content: 'applied 3 edits' }],
+			});
+			assert.strictEqual(debugEventMatchesText(event, 'done'), true);
+			assert.strictEqual(debugEventMatchesText(event, 'result'), true);
+			assert.strictEqual(debugEventMatchesText(event, 'edits'), true);
+		});
+	});
+
+	suite('parseTimeToken', () => {
+		test('parses year-only before token', () => {
+			const result = parseTimeToken('before:2026', 'before');
+			assert.strictEqual(result, new Date(2026, 11, 31, 23, 59, 59, 999).getTime());
+		});
+
+		test('parses year-month before token', () => {
+			const result = parseTimeToken('before:2026-03', 'before');
+			// End of March 2026
+			assert.strictEqual(result, new Date(2026, 3, 0, 23, 59, 59, 999).getTime());
+		});
+
+		test('parses full date before token', () => {
+			const result = parseTimeToken('before:2026-03-10', 'before');
+			assert.strictEqual(result, new Date(2026, 2, 10, 23, 59, 59, 999).getTime());
+		});
+
+		test('parses year-only after token', () => {
+			const result = parseTimeToken('after:2026', 'after');
+			assert.strictEqual(result, new Date(2026, 0, 1, 0, 0, 0, 0).getTime());
+		});
+
+		test('parses full date after token', () => {
+			const result = parseTimeToken('after:2026-03-10', 'after');
+			assert.strictEqual(result, new Date(2026, 2, 10, 0, 0, 0, 0).getTime());
+		});
+
+		test('returns undefined when token is absent', () => {
+			assert.strictEqual(parseTimeToken('some text', 'before'), undefined);
+			assert.strictEqual(parseTimeToken('some text', 'after'), undefined);
+		});
+	});
+
+	suite('stripTimestampTokens', () => {
+		test('strips before token', () => {
+			assert.strictEqual(stripTimestampTokens('before:2026-03 hello'), 'hello');
+		});
+
+		test('strips after token', () => {
+			assert.strictEqual(stripTimestampTokens('after:2026-03-10 hello'), 'hello');
+		});
+
+		test('strips both tokens', () => {
+			assert.strictEqual(stripTimestampTokens('after:2026-03 before:2026-04 hello'), 'hello');
+		});
+
+		test('returns text unchanged when no tokens', () => {
+			assert.strictEqual(stripTimestampTokens('hello world'), 'hello world');
+		});
+	});
+
+	suite('filterDebugEventsByText', () => {
+		// parseTimeToken uses local-time Date constructors, so event timestamps
+		// must also be in local time to produce predictable comparisons.
+		const events: readonly IChatDebugEvent[] = [
+			makeGenericEvent({ name: 'discovery', category: 'instructions', created: new Date(2026, 2, 10, 10, 0, 0) }),
+			makeToolCallEvent({ toolName: 'readFile', created: new Date(2026, 2, 10, 11, 0, 0) }),
+			makeToolCallEvent({ toolName: 'writeFile', created: new Date(2026, 2, 10, 12, 0, 0) }),
+			makeModelTurnEvent({ model: 'gpt-4o', created: new Date(2026, 2, 10, 13, 0, 0) }),
+		];
+
+		test('filters by inclusion term', () => {
+			const result = filterDebugEventsByText(events, 'readfile');
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual((result[0] as IChatDebugToolCallEvent).toolName, 'readFile');
+		});
+
+		test('filters by exclusion term', () => {
+			const result = filterDebugEventsByText(events, '!readfile');
+			assert.strictEqual(result.length, 3);
+		});
+
+		test('handles comma-separated terms as OR', () => {
+			const result = filterDebugEventsByText(events, 'readfile, writefile');
+			assert.strictEqual(result.length, 2);
+		});
+
+		test('combines inclusion and exclusion', () => {
+			const result = filterDebugEventsByText(events, 'toolcall, !readfile');
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual((result[0] as IChatDebugToolCallEvent).toolName, 'writeFile');
+		});
+
+		test('filters by before timestamp', () => {
+			const result = filterDebugEventsByText(events, 'before:2026-03-10t11');
+			assert.strictEqual(result.length, 2); // 10:00 and 11:00 (before rounds up to 11:59:59)
+		});
+
+		test('filters by after timestamp', () => {
+			const result = filterDebugEventsByText(events, 'after:2026-03-10t12');
+			assert.strictEqual(result.length, 2); // 12:00 and 13:00
+		});
+
+		test('combines timestamp and text filters', () => {
+			const result = filterDebugEventsByText(events, 'after:2026-03-10t11 toolcall');
+			assert.strictEqual(result.length, 2); // writeFile at 12:00 and readFile at 11:00
+		});
+
+		test('returns all events with empty filter', () => {
+			const result = filterDebugEventsByText(events, '');
+			assert.strictEqual(result.length, 4);
+		});
+	});
+
+	suite('filterDebugEvents', () => {
+		const events: readonly IChatDebugEvent[] = [
+			makeGenericEvent({ name: 'event-1', created: new Date('2026-03-10T10:00:00Z') }),
+			makeToolCallEvent({ toolName: 'readFile', created: new Date('2026-03-10T11:00:00Z') }),
+			makeToolCallEvent({ toolName: 'writeFile', created: new Date('2026-03-10T12:00:00Z') }),
+			makeModelTurnEvent({ model: 'gpt-4o', created: new Date('2026-03-10T13:00:00Z') }),
+			makeSubagentEvent({ agentName: 'explorer', created: new Date('2026-03-10T14:00:00Z') }),
+		];
+
+		test('returns all events with empty options', () => {
+			assert.deepStrictEqual(filterDebugEvents(events, {}), events);
+		});
+
+		test('filters by kind', () => {
+			const result = filterDebugEvents(events, { kind: 'toolCall' });
+			assert.strictEqual(result.length, 2);
+			assert.ok(result.every(e => e.kind === 'toolCall'));
+		});
+
+		test('filters by kind with no matches', () => {
+			const result = filterDebugEvents(events, { kind: 'userMessage' });
+			assert.strictEqual(result.length, 0);
+		});
+
+		test('filters by text', () => {
+			const result = filterDebugEvents(events, { filter: 'readfile' });
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual((result[0] as IChatDebugToolCallEvent).toolName, 'readFile');
+		});
+
+		test('limits to N most recent', () => {
+			const result = filterDebugEvents(events, { limit: 2 });
+			assert.strictEqual(result.length, 2);
+			assert.strictEqual(result[0].kind, 'modelTurn');
+			assert.strictEqual(result[1].kind, 'subagentInvocation');
+		});
+
+		test('limit larger than event count returns all', () => {
+			const result = filterDebugEvents(events, { limit: 100 });
+			assert.strictEqual(result.length, 5);
+		});
+
+		test('limit of 0 returns all', () => {
+			const result = filterDebugEvents(events, { limit: 0 });
+			assert.strictEqual(result.length, 5);
+		});
+
+		test('limit of negative returns all', () => {
+			const result = filterDebugEvents(events, { limit: -1 });
+			assert.strictEqual(result.length, 5);
+		});
+
+		test('combines kind and text filters', () => {
+			const result = filterDebugEvents(events, { kind: 'toolCall', filter: 'readfile' });
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual((result[0] as IChatDebugToolCallEvent).toolName, 'readFile');
+		});
+
+		test('combines kind and limit', () => {
+			const result = filterDebugEvents(events, { kind: 'toolCall', limit: 1 });
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual((result[0] as IChatDebugToolCallEvent).toolName, 'writeFile');
+		});
+
+		test('combines text filter and limit', () => {
+			const result = filterDebugEvents(events, { filter: 'toolcall', limit: 1 });
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual((result[0] as IChatDebugToolCallEvent).toolName, 'writeFile');
+		});
+
+		test('combines all three filters', () => {
+			const allToolCalls: readonly IChatDebugEvent[] = [
+				makeToolCallEvent({ toolName: 'readFile', created: new Date('2026-03-10T10:00:00Z') }),
+				makeToolCallEvent({ toolName: 'writeFile', created: new Date('2026-03-10T11:00:00Z') }),
+				makeToolCallEvent({ toolName: 'listDir', created: new Date('2026-03-10T12:00:00Z') }),
+				makeGenericEvent({ name: 'unrelated', created: new Date('2026-03-10T13:00:00Z') }),
+			];
+			// kind=toolCall, exclude readFile, limit=1 → should get the most recent non-readFile toolCall (listDir)
+			const result = filterDebugEvents(allToolCalls, { kind: 'toolCall', filter: '!readfile', limit: 1 });
+			assert.strictEqual(result.length, 1);
+			assert.strictEqual((result[0] as IChatDebugToolCallEvent).toolName, 'listDir');
+		});
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/common/chatDebugServiceImpl.test.ts b/src/vs/workbench/contrib/chat/test/common/chatDebugServiceImpl.test.ts
index a0df375b4c3d8..b3ca676d7290b 100644
--- a/src/vs/workbench/contrib/chat/test/common/chatDebugServiceImpl.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/chatDebugServiceImpl.test.ts
@@ -9,6 +9,7 @@ import { URI } from '../../../../../base/common/uri.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
 import { ChatDebugLogLevel, IChatDebugEvent, IChatDebugGenericEvent, IChatDebugLogProvider, IChatDebugModelTurnEvent, IChatDebugResolvedEventContent, IChatDebugToolCallEvent } from '../../common/chatDebugService.js';
 import { ChatDebugServiceImpl } from '../../common/chatDebugServiceImpl.js';
+import { LocalChatSessionUri } from '../../common/model/chatUri.js';
 
 suite('ChatDebugServiceImpl', () => {
 	const disposables = ensureNoDisposablesAreLeakedInTestSuite();
@@ -17,9 +18,10 @@ suite('ChatDebugServiceImpl', () => {
 
 	const session1 = URI.parse('vscode-chat-session://local/session-1');
 	const session2 = URI.parse('vscode-chat-session://local/session-2');
-	const sessionA = URI.parse('vscode-chat-session://local/a');
-	const sessionB = URI.parse('vscode-chat-session://local/b');
+	const sessionA = LocalChatSessionUri.forSession('a');
+	const sessionB = LocalChatSessionUri.forSession('b');
 	const sessionGeneric = URI.parse('vscode-chat-session://local/session');
+	const nonLocalSession = URI.parse('vscode-chat-session://remote-provider/session-1');
 
 	setup(() => {
 		service = disposables.add(new ChatDebugServiceImpl());
@@ -145,6 +147,16 @@ suite('ChatDebugServiceImpl', () => {
 			assert.strictEqual(event.category, 'testing');
 			assert.strictEqual(event.parentEventId, 'parent-1');
 		});
+
+		test('should not log events for non-local sessions', () => {
+			const firedEvents: IChatDebugEvent[] = [];
+			disposables.add(service.onDidAddEvent(e => firedEvents.push(e)));
+
+			service.log(nonLocalSession, 'should-be-skipped', 'details');
+
+			assert.strictEqual(firedEvents.length, 0);
+			assert.strictEqual(service.getEvents(nonLocalSession).length, 0);
+		});
 	});
 
 	suite('getSessionResources', () => {
@@ -173,21 +185,61 @@ suite('ChatDebugServiceImpl', () => {
 		});
 	});
 
-	suite('MAX_EVENTS cap', () => {
-		test('should evict oldest events when exceeding cap', () => {
-			// The max is 10_000. Add more than that and verify trimming.
-			// We'll test with a smaller count by adding events and checking boundary behavior.
+	suite('MAX_EVENTS_PER_SESSION cap', () => {
+		test('should evict oldest events when exceeding per-session cap', () => {
+			// The max per session is 10_000. Add more than that to a single session.
 			for (let i = 0; i < 10_001; i++) {
 				service.addEvent({ kind: 'generic', sessionResource: sessionGeneric, created: new Date(), name: `event-${i}`, level: ChatDebugLogLevel.Info });
 			}
 
 			const events = service.getEvents();
-			assert.ok(events.length <= 10_000, 'Should not exceed MAX_EVENTS');
+			assert.ok(events.length <= 10_000, 'Should not exceed MAX_EVENTS_PER_SESSION');
 			// The first event should have been evicted
 			assert.ok(!(events as IChatDebugGenericEvent[]).find(e => e.name === 'event-0'), 'Event-0 should have been evicted');
 			// The last event should be present
 			assert.ok((events as IChatDebugGenericEvent[]).find(e => e.name === 'event-10000'), 'Last event should be present');
 		});
+
+		test('should evict oldest session when exceeding MAX_SESSIONS', () => {
+			// MAX_SESSIONS is 5 — add events to 6 different sessions
+			const sessions: URI[] = [];
+			for (let i = 0; i < 6; i++) {
+				const uri = URI.parse(`vscode-chat-session://local/session-lru-${i}`);
+				sessions.push(uri);
+				service.addEvent({ kind: 'generic', sessionResource: uri, created: new Date(), name: `event-${i}`, level: ChatDebugLogLevel.Info });
+			}
+
+			const resources = service.getSessionResources();
+			assert.strictEqual(resources.length, 5, 'Should not exceed MAX_SESSIONS');
+			// The first session should have been evicted
+			assert.ok(!resources.some(r => r.toString() === sessions[0].toString()), 'Session-0 should have been evicted');
+			assert.strictEqual(service.getEvents(sessions[0]).length, 0, 'Events from evicted session should be gone');
+			// The last session should be present
+			assert.ok(resources.some(r => r.toString() === sessions[5].toString()), 'Session-5 should be present');
+		});
+
+		test('should use LRU eviction — recently-used sessions are kept', () => {
+			// Fill to MAX_SESSIONS (5)
+			const sessions: URI[] = [];
+			for (let i = 0; i < 5; i++) {
+				const uri = URI.parse(`vscode-chat-session://local/session-lru2-${i}`);
+				sessions.push(uri);
+				service.addEvent({ kind: 'generic', sessionResource: uri, created: new Date(), name: `init-${i}`, level: ChatDebugLogLevel.Info });
+			}
+
+			// Touch session-0 so it moves to the back of the LRU order
+			service.addEvent({ kind: 'generic', sessionResource: sessions[0], created: new Date(), name: 'touch', level: ChatDebugLogLevel.Info });
+
+			// Add a 6th session — session-1 (the true LRU) should be evicted, not session-0
+			const session6 = URI.parse('vscode-chat-session://local/session-lru2-5');
+			service.addEvent({ kind: 'generic', sessionResource: session6, created: new Date(), name: 'new', level: ChatDebugLogLevel.Info });
+
+			const resources = service.getSessionResources();
+			assert.strictEqual(resources.length, 5);
+			assert.ok(resources.some(r => r.toString() === sessions[0].toString()), 'Session-0 should be kept (recently used)');
+			assert.ok(!resources.some(r => r.toString() === sessions[1].toString()), 'Session-1 should be evicted (LRU)');
+			assert.ok(resources.some(r => r.toString() === session6.toString()), 'Session-5 should be present');
+		});
 	});
 
 	suite('activeSessionResource', () => {
@@ -202,6 +254,44 @@ suite('ChatDebugServiceImpl', () => {
 		});
 	});
 
+	suite('markDebugDataAttached', () => {
+		test('should track attached debug data per session', () => {
+			assert.strictEqual(service.hasAttachedDebugData(sessionGeneric), false);
+
+			const fired: URI[] = [];
+			disposables.add(service.onDidAttachDebugData(uri => fired.push(uri)));
+
+			service.markDebugDataAttached(sessionGeneric);
+			assert.strictEqual(service.hasAttachedDebugData(sessionGeneric), true);
+			assert.strictEqual(fired.length, 1);
+			assert.strictEqual(fired[0].toString(), sessionGeneric.toString());
+
+			// Idempotent — second call should not fire again
+			service.markDebugDataAttached(sessionGeneric);
+			assert.strictEqual(fired.length, 1);
+
+			// Other sessions remain unaffected
+			assert.strictEqual(service.hasAttachedDebugData(sessionA), false);
+		});
+
+		test('should clear attached debug data on endSession', () => {
+			service.markDebugDataAttached(sessionGeneric);
+			assert.strictEqual(service.hasAttachedDebugData(sessionGeneric), true);
+
+			service.endSession(sessionGeneric);
+			assert.strictEqual(service.hasAttachedDebugData(sessionGeneric), false);
+		});
+
+		test('should clear attached debug data on clear', () => {
+			service.markDebugDataAttached(sessionA);
+			service.markDebugDataAttached(sessionB);
+
+			service.clear();
+			assert.strictEqual(service.hasAttachedDebugData(sessionA), false);
+			assert.strictEqual(service.hasAttachedDebugData(sessionB), false);
+		});
+	});
+
 	suite('registerProvider', () => {
 		test('should register and unregister a provider', async () => {
 			const extSession = URI.parse('vscode-chat-session://local/ext-session');
@@ -300,6 +390,32 @@ suite('ChatDebugServiceImpl', () => {
 			assert.strictEqual(firstToken.isCancellationRequested, true);
 		});
 
+		test('should fire onDidClearProviderEvents when clearing provider events', async () => {
+			const clearedSessions: URI[] = [];
+			disposables.add(service.onDidClearProviderEvents(sessionResource => clearedSessions.push(sessionResource)));
+
+			const provider: IChatDebugLogProvider = {
+				provideChatDebugLog: async (sessionResource) => [{
+					kind: 'generic',
+					sessionResource,
+					created: new Date(),
+					name: 'provider-event',
+					level: ChatDebugLogLevel.Info,
+				}],
+			};
+
+			disposables.add(service.registerProvider(provider));
+
+			// First invocation clears empty set and fires clear event
+			await service.invokeProviders(sessionGeneric);
+			assert.strictEqual(clearedSessions.length, 1, 'Clear event should fire on first invocation');
+
+			// Second invocation clears provider events from first invocation
+			await service.invokeProviders(sessionGeneric);
+			assert.strictEqual(clearedSessions.length, 2, 'Clear event should fire on second invocation');
+			assert.strictEqual(clearedSessions[1].toString(), sessionGeneric.toString());
+		});
+
 		test('should not cancel invocations for different sessions', async () => {
 			const tokens: Map<string, CancellationToken> = new Map();
 
@@ -319,6 +435,29 @@ suite('ChatDebugServiceImpl', () => {
 			assert.strictEqual(tokenA.isCancellationRequested, false, 'session-a token should not be cancelled');
 		});
 
+		test('should not invoke providers for non-local sessions', async () => {
+			let providerCalled = false;
+
+			const provider: IChatDebugLogProvider = {
+				provideChatDebugLog: async () => {
+					providerCalled = true;
+					return [{
+						kind: 'generic',
+						sessionResource: nonLocalSession,
+						created: new Date(),
+						name: 'should-not-appear',
+						level: ChatDebugLogLevel.Info,
+					}];
+				},
+			};
+
+			disposables.add(service.registerProvider(provider));
+			await service.invokeProviders(nonLocalSession);
+
+			assert.strictEqual(providerCalled, false);
+			assert.strictEqual(service.getEvents(nonLocalSession).length, 0);
+		});
+
 		test('newly registered provider should be invoked for active sessions', async () => {
 			// Start an invocation before the provider is registered
 			const firstProvider: IChatDebugLogProvider = {
diff --git a/src/vs/workbench/contrib/chat/test/common/chatImageExtraction.test.ts b/src/vs/workbench/contrib/chat/test/common/chatImageExtraction.test.ts
new file mode 100644
index 0000000000000..e3e4014a76256
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/common/chatImageExtraction.test.ts
@@ -0,0 +1,490 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { VSBuffer } from '../../../../../base/common/buffer.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { IImageVariableEntry } from '../../common/attachments/chatVariableEntries.js';
+import { IChatProgressResponseContent } from '../../common/model/chatModel.js';
+import { IChatRequestViewModel, IChatResponseViewModel } from '../../common/model/chatViewModel.js';
+import { IChatContentInlineReference, IChatToolInvocationSerialized, IToolResultOutputDetailsSerialized } from '../../common/chatService/chatService.js';
+import { IToolResultInputOutputDetails } from '../../common/tools/languageModelToolsService.js';
+import { extractImagesFromChatRequest, extractImagesFromChatResponse, extractImagesFromToolInvocationMessages } from '../../common/chatImageExtraction.js';
+
+function makeToolInvocation(overrides: Partial<IChatToolInvocationSerialized> = {}): IChatToolInvocationSerialized {
+	return {
+		kind: 'toolInvocationSerialized',
+		toolCallId: 'call_1',
+		toolId: 'test-tool',
+		invocationMessage: 'Running tool',
+		originMessage: undefined,
+		pastTenseMessage: 'Ran tool',
+		isConfirmed: true,
+		isComplete: true,
+		source: undefined,
+		presentation: undefined,
+		resultDetails: undefined,
+		...overrides,
+	};
+}
+
+function makeInlineReference(uri: URI, name?: string): IChatContentInlineReference {
+	return {
+		kind: 'inlineReference',
+		inlineReference: uri,
+		name,
+	};
+}
+
+function makeResponse(items: ReadonlyArray<IChatProgressResponseContent>, opts: {
+	sessionResource?: URI;
+	requestId?: string;
+	id?: string;
+	requestMessageText?: string;
+	noMatchingRequest?: boolean;
+} = {}): IChatResponseViewModel {
+	const sessionResource = opts.sessionResource ?? URI.parse('chat-session://test/session');
+	const requestId = opts.requestId ?? 'req-1';
+	const responseId = opts.id ?? 'resp-1';
+	const requestMessageText = opts.requestMessageText ?? 'Show me images';
+
+	return {
+		id: responseId,
+		requestId,
+		sessionResource,
+		response: { value: items },
+		session: {
+			getItems: () => opts.noMatchingRequest ? [] : [{
+				id: requestId,
+				messageText: requestMessageText,
+				message: { parts: [], text: requestMessageText },
+			}],
+		},
+	} as unknown as IChatResponseViewModel;
+}
+
+const fakeReadFile = (uri: URI) => Promise.resolve(VSBuffer.fromString(`data-for-${uri.path}`));
+
+function makeRequest(variables: IChatRequestViewModel['variables'], opts: { id?: string; messageText?: string } = {}): IChatRequestViewModel {
+	return {
+		id: opts.id ?? 'req-1',
+		sessionResource: URI.parse('chat-session://test/session'),
+		dataId: 'data-1',
+		username: 'test-user',
+		message: { text: opts.messageText ?? 'Show me images', parts: [] },
+		messageText: opts.messageText ?? 'Show me images',
+		attempt: 0,
+		variables,
+		currentRenderedHeight: undefined,
+		shouldBeRemovedOnSend: undefined,
+		isComplete: true,
+		isCompleteAddedRequest: true,
+		slashCommand: undefined,
+		agentOrSlashCommandDetected: false,
+		shouldBeBlocked: undefined!,
+		timestamp: 0,
+	} as unknown as IChatRequestViewModel;
+}
+
+function makeImageVariableEntry(overrides: Partial<IImageVariableEntry> & Pick<IImageVariableEntry, 'value'>): IImageVariableEntry {
+	const { value, ...rest } = overrides;
+	return {
+		id: 'img-1',
+		kind: 'image',
+		name: 'cat.png',
+		value,
+		mimeType: 'image/png',
+		...rest,
+	};
+}
+
+suite('extractImagesFromChatResponse', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('returns empty images when response has no items', async () => {
+		const response = makeResponse([]);
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+		assert.deepStrictEqual(result, {
+			id: response.sessionResource.toString() + '_' + response.id,
+			title: 'Show me images',
+			images: [],
+		});
+	});
+
+	test('uses default title when no matching request is found', async () => {
+		const response = makeResponse([], { noMatchingRequest: true });
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+		assert.strictEqual(result.title, 'Images');
+	});
+
+	test('extracts image from tool invocation with IToolResultOutputDetails', async () => {
+		const resultDetails: IToolResultOutputDetailsSerialized = {
+			output: { type: 'data', mimeType: 'image/png', base64Data: 'AQID' },
+		};
+		const toolInvocation = makeToolInvocation({
+			toolCallId: 'call_img',
+			toolId: 'screenshot-tool',
+			pastTenseMessage: 'Took a screenshot',
+			resultDetails,
+		});
+
+		const response = makeResponse([toolInvocation]);
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+
+		assert.strictEqual(result.images.length, 1);
+		assert.strictEqual(result.images[0].id, 'call_img_0');
+		assert.strictEqual(result.images[0].mimeType, 'image/png');
+		assert.ok(result.images[0].source.includes('screenshot-tool'));
+		assert.strictEqual(result.images[0].caption, 'Took a screenshot');
+	});
+
+	test('extracts multiple images from tool invocation with IToolResultInputOutputDetails', async () => {
+		const resultDetails: IToolResultInputOutputDetails = {
+			input: '',
+			output: [
+				{ type: 'embed', mimeType: 'image/png', value: 'AQID', isText: false },
+				{ type: 'embed', mimeType: 'text/plain', value: 'text', isText: true },
+				{ type: 'embed', mimeType: 'image/jpeg', value: 'BAUG', isText: false },
+			],
+		};
+		const toolInvocation = makeToolInvocation({
+			toolCallId: 'call_multi',
+			toolId: 'multi-tool',
+			pastTenseMessage: 'Generated images',
+			resultDetails,
+		});
+
+		const response = makeResponse([toolInvocation]);
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+
+		assert.strictEqual(result.images.length, 2);
+		assert.strictEqual(result.images[0].id, 'call_multi_0');
+		assert.strictEqual(result.images[0].mimeType, 'image/png');
+		assert.strictEqual(result.images[1].id, 'call_multi_2');
+		assert.strictEqual(result.images[1].mimeType, 'image/jpeg');
+	});
+
+	test('skips tool invocations without image results', async () => {
+		const resultDetails: IToolResultOutputDetailsSerialized = {
+			output: { type: 'data', mimeType: 'text/plain', base64Data: 'aGVsbG8=' },
+		};
+		const toolInvocation = makeToolInvocation({ resultDetails });
+
+		const response = makeResponse([toolInvocation]);
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+		assert.strictEqual(result.images.length, 0);
+	});
+
+	test('extracts image from inline reference URI when readFile is provided', async () => {
+		const imageUri = URI.file('/photos/cat.png');
+		const inlineRef = makeInlineReference(imageUri, 'cat.png');
+
+		const response = makeResponse([inlineRef]);
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+
+		assert.strictEqual(result.images.length, 1);
+		assert.strictEqual(result.images[0].uri.toString(), imageUri.toString());
+		assert.strictEqual(result.images[0].name, 'cat.png');
+		assert.strictEqual(result.images[0].mimeType, 'image/png');
+		assert.strictEqual(result.images[0].source, 'File');
+	});
+
+	test('extracts image from inline reference Location', async () => {
+		const imageUri = URI.file('/photos/dog.jpg');
+		const inlineRef: IChatContentInlineReference = {
+			kind: 'inlineReference',
+			inlineReference: { uri: imageUri, range: { startLineNumber: 1, startColumn: 1, endLineNumber: 1, endColumn: 1 } },
+		};
+
+		const response = makeResponse([inlineRef]);
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+
+		assert.strictEqual(result.images.length, 1);
+		assert.strictEqual(result.images[0].uri.toString(), imageUri.toString());
+	});
+
+	test('skips non-image inline references', async () => {
+		const codeUri = URI.file('/src/main.ts');
+		const inlineRef = makeInlineReference(codeUri);
+
+		const response = makeResponse([inlineRef]);
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+		assert.strictEqual(result.images.length, 0);
+	});
+
+	test('uses filename from URI path when name is not provided', async () => {
+		const imageUri = URI.file('/assets/banner.gif');
+		const inlineRef = makeInlineReference(imageUri);
+
+		const response = makeResponse([inlineRef]);
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+
+		assert.strictEqual(result.images.length, 1);
+		assert.strictEqual(result.images[0].name, 'banner.gif');
+	});
+
+	test('preserves interleaved order of tool and inline reference images', async () => {
+		const toolInvocation = makeToolInvocation({
+			toolCallId: 'call_first',
+			toolId: 'tool-1',
+			resultDetails: {
+				output: { type: 'data', mimeType: 'image/png', base64Data: 'AQID' },
+			} satisfies IToolResultOutputDetailsSerialized,
+		});
+
+		const inlineRef = makeInlineReference(URI.file('/middle.png'), 'middle.png');
+
+		const toolInvocation2 = makeToolInvocation({
+			toolCallId: 'call_last',
+			toolId: 'tool-2',
+			resultDetails: {
+				output: { type: 'data', mimeType: 'image/jpeg', base64Data: 'BAUG' },
+			} satisfies IToolResultOutputDetailsSerialized,
+		});
+
+		const response = makeResponse([toolInvocation, inlineRef, toolInvocation2]);
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+
+		assert.strictEqual(result.images.length, 3);
+		assert.strictEqual(result.images[0].id, 'call_first_0');
+		assert.strictEqual(result.images[1].name, 'middle.png');
+		assert.strictEqual(result.images[2].id, 'call_last_0');
+	});
+
+	test('collection id combines sessionResource and response id', async () => {
+		const sessionResource = URI.parse('chat-session://test/my-session');
+		const response = makeResponse([], { sessionResource, id: 'response-42' });
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+		assert.strictEqual(result.id, sessionResource.toString() + '_response-42');
+	});
+
+	test('skips inline reference when readFile fails', async () => {
+		const imageUri = URI.file('/photos/missing.png');
+		const inlineRef = makeInlineReference(imageUri, 'missing.png');
+		const failingReadFile = (_uri: URI) => Promise.reject(new Error('File not found'));
+
+		const response = makeResponse([inlineRef]);
+		const result = await extractImagesFromChatResponse(response, failingReadFile);
+		assert.strictEqual(result.images.length, 0);
+	});
+
+	test('extracts images from tool invocation message URIs', async () => {
+		const imageUri = URI.file('/screenshots/result.png');
+		const toolInvocation = makeToolInvocation({
+			toolCallId: 'call_msg',
+			toolId: 'screenshot-tool',
+			pastTenseMessage: { value: 'Took a screenshot', isTrusted: false, uris: { '0': imageUri.toJSON() } },
+		});
+
+		const response = makeResponse([toolInvocation]);
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+
+		assert.strictEqual(result.images.length, 1);
+		assert.strictEqual(result.images[0].uri.toString(), imageUri.toString());
+		assert.strictEqual(result.images[0].name, 'result.png');
+		assert.strictEqual(result.images[0].mimeType, 'image/png');
+		assert.strictEqual(result.images[0].caption, 'Took a screenshot');
+	});
+
+	test('combines output details images and message URI images', async () => {
+		const imageUri = URI.file('/screenshots/msg-image.jpg');
+		const resultDetails: IToolResultOutputDetailsSerialized = {
+			output: { type: 'data', mimeType: 'image/png', base64Data: 'AQID' },
+		};
+		const toolInvocation = makeToolInvocation({
+			toolCallId: 'call_both',
+			toolId: 'combo-tool',
+			pastTenseMessage: { value: 'Ran combo tool', isTrusted: false, uris: { '0': imageUri.toJSON() } },
+			resultDetails,
+		});
+
+		const response = makeResponse([toolInvocation]);
+		const result = await extractImagesFromChatResponse(response, fakeReadFile);
+
+		assert.strictEqual(result.images.length, 2);
+		assert.strictEqual(result.images[0].id, 'call_both_0');
+		assert.strictEqual(result.images[1].uri.toString(), imageUri.toString());
+	});
+});
+
+suite('extractImagesFromToolInvocationMessages', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('returns empty when message is undefined', async () => {
+		const toolInvocation = makeToolInvocation({
+			pastTenseMessage: undefined,
+			invocationMessage: undefined,
+		});
+		const result = await extractImagesFromToolInvocationMessages(toolInvocation, fakeReadFile);
+		assert.deepStrictEqual(result, []);
+	});
+
+	test('returns empty when message is a string', async () => {
+		const toolInvocation = makeToolInvocation({
+			pastTenseMessage: 'some string message',
+		});
+		const result = await extractImagesFromToolInvocationMessages(toolInvocation, fakeReadFile);
+		assert.deepStrictEqual(result, []);
+	});
+
+	test('returns empty when message has no uris', async () => {
+		const toolInvocation = makeToolInvocation({
+			pastTenseMessage: { value: 'No URIs here', isTrusted: false },
+		});
+		const result = await extractImagesFromToolInvocationMessages(toolInvocation, fakeReadFile);
+		assert.deepStrictEqual(result, []);
+	});
+
+	test('returns empty when message uris are empty', async () => {
+		const toolInvocation = makeToolInvocation({
+			pastTenseMessage: { value: 'Empty URIs', isTrusted: false, uris: {} },
+		});
+		const result = await extractImagesFromToolInvocationMessages(toolInvocation, fakeReadFile);
+		assert.deepStrictEqual(result, []);
+	});
+
+	test('skips non-image URIs', async () => {
+		const toolInvocation = makeToolInvocation({
+			pastTenseMessage: { value: 'Code file', isTrusted: false, uris: { '0': URI.file('/src/main.ts').toJSON() } },
+		});
+		const result = await extractImagesFromToolInvocationMessages(toolInvocation, fakeReadFile);
+		assert.deepStrictEqual(result, []);
+	});
+
+	test('extracts image from message URI', async () => {
+		const imageUri = URI.file('/screenshots/capture.png');
+		const toolInvocation = makeToolInvocation({
+			toolCallId: 'call_uri',
+			toolId: 'screenshot-tool',
+			pastTenseMessage: { value: 'Captured screenshot', isTrusted: false, uris: { '0': imageUri.toJSON() } },
+		});
+
+		const result = await extractImagesFromToolInvocationMessages(toolInvocation, fakeReadFile);
+
+		assert.strictEqual(result.length, 1);
+		assert.strictEqual(result[0].uri.toString(), imageUri.toString());
+		assert.strictEqual(result[0].name, 'capture.png');
+		assert.strictEqual(result[0].mimeType, 'image/png');
+		assert.strictEqual(result[0].caption, 'Captured screenshot');
+		assert.ok(result[0].source.includes('screenshot-tool'));
+	});
+
+	test('extracts multiple images from message URIs', async () => {
+		const uri1 = URI.file('/img/a.png');
+		const uri2 = URI.file('/img/b.jpg');
+		const toolInvocation = makeToolInvocation({
+			pastTenseMessage: {
+				value: 'Generated images',
+				isTrusted: false,
+				uris: { '0': uri1.toJSON(), '1': uri2.toJSON() },
+			},
+		});
+
+		const result = await extractImagesFromToolInvocationMessages(toolInvocation, fakeReadFile);
+
+		assert.strictEqual(result.length, 2);
+		assert.strictEqual(result[0].mimeType, 'image/png');
+		assert.strictEqual(result[1].mimeType, 'image/jpg');
+	});
+
+	test('continues when readFile fails for one URI', async () => {
+		const goodUri = URI.file('/img/good.png');
+		const badUri = URI.file('/img/bad.png');
+		const failingReadFile = (uri: URI) => {
+			if (uri.path.includes('bad')) {
+				return Promise.reject(new Error('File not found'));
+			}
+			return Promise.resolve(VSBuffer.fromString('image-data'));
+		};
+		const toolInvocation = makeToolInvocation({
+			pastTenseMessage: {
+				value: 'Mixed results',
+				isTrusted: false,
+				uris: { '0': badUri.toJSON(), '1': goodUri.toJSON() },
+			},
+		});
+
+		const result = await extractImagesFromToolInvocationMessages(toolInvocation, failingReadFile);
+
+		assert.strictEqual(result.length, 1);
+		assert.strictEqual(result[0].uri.toString(), goodUri.toString());
+	});
+
+	test('falls back to invocationMessage when pastTenseMessage is undefined', async () => {
+		const imageUri = URI.file('/img/fallback.png');
+		const toolInvocation = makeToolInvocation({
+			pastTenseMessage: undefined,
+			invocationMessage: { value: 'Running tool', isTrusted: false, uris: { '0': imageUri.toJSON() } },
+		});
+
+		const result = await extractImagesFromToolInvocationMessages(toolInvocation, fakeReadFile);
+
+		assert.strictEqual(result.length, 1);
+		assert.strictEqual(result[0].caption, 'Running tool');
+	});
+});
+
+suite('extractImagesFromChatRequest', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('extracts image attachment from Uint8Array', () => {
+		const request = makeRequest([
+			makeImageVariableEntry({ value: new Uint8Array([1, 2, 3]) }),
+		]);
+
+		const result = extractImagesFromChatRequest(request);
+
+		assert.strictEqual(result.length, 1);
+		assert.strictEqual(result[0].name, 'cat.png');
+		assert.strictEqual(result[0].mimeType, 'image/png');
+		assert.deepStrictEqual([...result[0].data.buffer], [1, 2, 3]);
+	});
+
+	test('extracts image attachment from ArrayBuffer', () => {
+		const request = makeRequest([
+			makeImageVariableEntry({ value: new Uint8Array([4, 5, 6]).buffer }),
+		]);
+
+		const result = extractImagesFromChatRequest(request);
+
+		assert.strictEqual(result.length, 1);
+		assert.deepStrictEqual([...result[0].data.buffer], [4, 5, 6]);
+	});
+
+	test('extracts restored image attachment from plain object bytes', () => {
+		const request = makeRequest([
+			makeImageVariableEntry({ value: { 0: 7, 1: 8, 2: 9 } }),
+		]);
+
+		const result = extractImagesFromChatRequest(request);
+
+		assert.strictEqual(result.length, 1);
+		assert.deepStrictEqual([...result[0].data.buffer], [7, 8, 9]);
+	});
+
+	test('extracts restored image attachment from reordered plain object bytes', () => {
+		const request = makeRequest([
+			makeImageVariableEntry({ value: { 2: 9, 0: 7, 1: 8 } }),
+		]);
+
+		const result = extractImagesFromChatRequest(request);
+
+		assert.strictEqual(result.length, 1);
+		assert.deepStrictEqual([...result[0].data.buffer], [7, 8, 9]);
+	});
+
+	test('uses attachment resource URI when available', () => {
+		const uri = URI.file('/tmp/cat.png');
+		const request = makeRequest([
+			makeImageVariableEntry({ value: new Uint8Array([1]), references: [{ kind: 'reference', reference: uri }] }),
+		]);
+
+		const result = extractImagesFromChatRequest(request);
+
+		assert.strictEqual(result.length, 1);
+		assert.strictEqual(result[0].uri.toString(), uri.toString());
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/common/chatModeService.test.ts b/src/vs/workbench/contrib/chat/test/common/chatModeService.test.ts
index f7745a0b6fa9f..c8e5aa2740401 100644
--- a/src/vs/workbench/contrib/chat/test/common/chatModeService.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/chatModeService.test.ts
@@ -19,8 +19,9 @@ import { TestStorageService } from '../../../../test/common/workbenchTestService
 import { IChatAgentService } from '../../common/participants/chatAgents.js';
 import { ChatMode, ChatModeService } from '../../common/chatModes.js';
 import { ChatModeKind } from '../../common/constants.js';
-import { IAgentSource, ICustomAgent, IPromptsService, PromptsStorage, Target } from '../../common/promptSyntax/service/promptsService.js';
+import { IAgentSource, ICustomAgent, IPromptsService, PromptsStorage } from '../../common/promptSyntax/service/promptsService.js';
 import { MockPromptsService } from './promptSyntax/service/mockPromptsService.js';
+import { Target } from '../../common/promptSyntax/promptTypes.js';
 
 class TestChatAgentService implements Partial<IChatAgentService> {
 	_serviceBrand: undefined;
diff --git a/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_can_deserialize.0.snap b/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_can_deserialize.0.snap
index 643e3727914e6..374c04da9975c 100644
--- a/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_can_deserialize.0.snap
+++ b/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_can_deserialize.0.snap
@@ -75,6 +75,7 @@
       confirmation: undefined,
       editedFileEvents: undefined,
       modelId: undefined,
+      modeInfo: undefined,
       responseId: undefined,
       result: { metadata: { metadataKey: "value" } },
       responseMarkdownInfo: undefined,
diff --git a/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_can_deserialize_with_response.0.snap b/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_can_deserialize_with_response.0.snap
index f0e423320ddae..3119761173f4d 100644
--- a/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_can_deserialize_with_response.0.snap
+++ b/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_can_deserialize_with_response.0.snap
@@ -75,6 +75,7 @@
       confirmation: undefined,
       editedFileEvents: undefined,
       modelId: undefined,
+      modeInfo: undefined,
       responseId: undefined,
       result: { errorDetails: { message: "No activated agent with id \"ChatProviderWithUsedContext\"" } },
       responseMarkdownInfo: undefined,
diff --git a/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_can_serialize.1.snap b/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_can_serialize.1.snap
index 3e5c32aa740cc..a3d39df663c7f 100644
--- a/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_can_serialize.1.snap
+++ b/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_can_serialize.1.snap
@@ -77,6 +77,7 @@
       confirmation: undefined,
       editedFileEvents: undefined,
       modelId: undefined,
+      modeInfo: undefined,
       responseId: undefined,
       result: { metadata: { metadataKey: "value" } },
       responseMarkdownInfo: undefined,
@@ -162,6 +163,7 @@
       confirmation: undefined,
       editedFileEvents: undefined,
       modelId: undefined,
+      modeInfo: undefined,
       responseId: undefined,
       result: {  },
       responseMarkdownInfo: undefined,
diff --git a/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_sendRequest_fails.0.snap b/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_sendRequest_fails.0.snap
index 9a7073212a2b7..5fc5d409eb3d4 100644
--- a/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_sendRequest_fails.0.snap
+++ b/src/vs/workbench/contrib/chat/test/common/chatService/__snapshots__/ChatService_sendRequest_fails.0.snap
@@ -77,6 +77,7 @@
       confirmation: undefined,
       editedFileEvents: undefined,
       modelId: undefined,
+      modeInfo: undefined,
       responseId: undefined,
       result: { errorDetails: { message: "No activated agent with id \"ChatProviderWithUsedContext\"" } },
       responseMarkdownInfo: undefined,
diff --git a/src/vs/workbench/contrib/chat/test/common/chatService/chatService.test.ts b/src/vs/workbench/contrib/chat/test/common/chatService/chatService.test.ts
index 9adc29af139d9..70fa3572eb8c7 100644
--- a/src/vs/workbench/contrib/chat/test/common/chatService/chatService.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/chatService/chatService.test.ts
@@ -5,6 +5,7 @@
 
 import assert from 'assert';
 import { DeferredPromise } from '../../../../../../base/common/async.js';
+import { CancellationToken } from '../../../../../../base/common/cancellation.js';
 import { Event } from '../../../../../../base/common/event.js';
 import { MarkdownString } from '../../../../../../base/common/htmlContent.js';
 import { DisposableStore } from '../../../../../../base/common/lifecycle.js';
@@ -12,6 +13,7 @@ import { constObservable, observableValue } from '../../../../../../base/common/
 import { URI } from '../../../../../../base/common/uri.js';
 import { assertSnapshot } from '../../../../../../base/test/common/snapshot.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { runWithFakedTimers } from '../../../../../../base/test/common/timeTravelScheduler.js';
 import { Range } from '../../../../../../editor/common/core/range.js';
 import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
 import { TestConfigurationService } from '../../../../../../platform/configuration/test/common/testConfigurationService.js';
@@ -22,38 +24,39 @@ import { ServiceCollection } from '../../../../../../platform/instantiation/comm
 import { TestInstantiationService } from '../../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
 import { MockContextKeyService } from '../../../../../../platform/keybinding/test/common/mockKeybindingService.js';
 import { ILogService, NullLogService } from '../../../../../../platform/log/common/log.js';
-import { IStorageService } from '../../../../../../platform/storage/common/storage.js';
+import { IStorageService, StorageScope } from '../../../../../../platform/storage/common/storage.js';
 import { ITelemetryService } from '../../../../../../platform/telemetry/common/telemetry.js';
 import { NullTelemetryService } from '../../../../../../platform/telemetry/common/telemetryUtils.js';
 import { IUserDataProfilesService, toUserDataProfile } from '../../../../../../platform/userDataProfile/common/userDataProfile.js';
 import { IWorkspaceContextService } from '../../../../../../platform/workspace/common/workspace.js';
 import { IWorkbenchAssignmentService } from '../../../../../services/assignment/common/assignmentService.js';
 import { NullWorkbenchAssignmentService } from '../../../../../services/assignment/test/common/nullAssignmentService.js';
+import { IChatEntitlementService } from '../../../../../services/chat/common/chatEntitlementService.js';
 import { IExtensionService, nullExtensionDescription } from '../../../../../services/extensions/common/extensions.js';
 import { ILifecycleService } from '../../../../../services/lifecycle/common/lifecycle.js';
 import { IViewsService } from '../../../../../services/views/common/viewsService.js';
 import { IWorkspaceEditingService } from '../../../../../services/workspaces/common/workspaceEditing.js';
-import { IChatEntitlementService } from '../../../../../services/chat/common/chatEntitlementService.js';
 import { InMemoryTestFileService, mock, TestChatEntitlementService, TestContextService, TestExtensionService, TestStorageService } from '../../../../../test/common/workbenchTestServices.js';
 import { IMcpService } from '../../../../mcp/common/mcpTypes.js';
 import { TestMcpService } from '../../../../mcp/test/common/testMcpService.js';
-import { ChatAgentService, IChatAgent, IChatAgentData, IChatAgentImplementation, IChatAgentService } from '../../../common/participants/chatAgents.js';
+import { IChatVariablesService } from '../../../common/attachments/chatVariables.js';
+import { IChatDebugService } from '../../../common/chatDebugService.js';
+import { ChatDebugServiceImpl } from '../../../common/chatDebugServiceImpl.js';
+import { ChatRequestQueueKind, ChatSendResult, IChatFollowup, IChatModelReference, IChatService, ResponseModelState } from '../../../common/chatService/chatService.js';
+import { ChatService } from '../../../common/chatService/chatServiceImpl.js';
+import { ChatAgentLocation, ChatModeKind } from '../../../common/constants.js';
 import { IChatEditingService, IChatEditingSession } from '../../../common/editing/chatEditingService.js';
 import { ChatModel, IChatModel, ISerializableChatData } from '../../../common/model/chatModel.js';
-import { ChatRequestQueueKind, ChatSendResult, IChatFollowup, IChatModelReference, IChatService } from '../../../common/chatService/chatService.js';
-import { ChatService } from '../../../common/chatService/chatServiceImpl.js';
+import { ChatAgentService, IChatAgent, IChatAgentData, IChatAgentImplementation, IChatAgentService } from '../../../common/participants/chatAgents.js';
 import { ChatSlashCommandService, IChatSlashCommandService } from '../../../common/participants/chatSlashCommands.js';
-import { IChatVariablesService } from '../../../common/attachments/chatVariables.js';
-import { ChatAgentLocation, ChatModeKind } from '../../../common/constants.js';
-import { MockChatService } from './mockChatService.js';
+import { IConfiguredHooksInfo, IPromptsService } from '../../../common/promptSyntax/service/promptsService.js';
+import { ILanguageModelToolsService } from '../../../common/tools/languageModelToolsService.js';
 import { MockChatVariablesService } from '../mockChatVariables.js';
-import { IPromptsService } from '../../../common/promptSyntax/service/promptsService.js';
 import { MockPromptsService } from '../promptSyntax/service/mockPromptsService.js';
-import { IChatDebugService } from '../../../common/chatDebugService.js';
-import { ChatDebugServiceImpl } from '../../../common/chatDebugServiceImpl.js';
-import { CancellationToken } from '../../../../../../base/common/cancellation.js';
-import { ILanguageModelToolsService } from '../../../common/tools/languageModelToolsService.js';
 import { MockLanguageModelToolsService } from '../tools/mockLanguageModelToolsService.js';
+import { MockChatService } from './mockChatService.js';
+import { IChatSessionsService } from '../../../common/chatSessionsService.js';
+import { MockChatSessionsService } from '../mockChatSessionsService.js';
 
 const chatAgentWithUsedContextId = 'ChatProviderWithUsedContext';
 const chatAgentWithUsedContext: IChatAgent = {
@@ -479,6 +482,455 @@ suite('ChatService', () => {
 		completeRequest.complete();
 		await response.data.responseCompletePromise;
 	});
+
+	test('multiple steering messages are combined into a single request', async () => {
+		const requestStarted = new DeferredPromise<void>();
+		const completeRequest = new DeferredPromise<void>();
+		const invokedRequests: string[] = [];
+
+		const slowAgent: IChatAgentImplementation = {
+			async invoke(request, progress, history, token) {
+				invokedRequests.push(request.message);
+				if (invokedRequests.length === 1) {
+					requestStarted.complete();
+					await completeRequest.p;
+				}
+				return {};
+			},
+		};
+
+		testDisposables.add(chatAgentService.registerAgent('slowAgent', { ...getAgentData('slowAgent'), isDefault: true }));
+		testDisposables.add(chatAgentService.registerAgentImplementation('slowAgent', slowAgent));
+
+		const testService = createChatService();
+		const modelRef = testDisposables.add(startSessionModel(testService));
+		const model = modelRef.object;
+
+		// Start a request that will wait
+		const response = await testService.sendRequest(model.sessionResource, 'first request', { agentId: 'slowAgent' });
+		ChatSendResult.assertSent(response);
+
+		// Wait for the agent to start processing
+		await requestStarted.p;
+
+		// Queue 3 steering messages while the first request is in progress
+		const steering1 = await testService.sendRequest(model.sessionResource, 'steering1', { agentId: 'slowAgent', queue: ChatRequestQueueKind.Steering });
+		const steering2 = await testService.sendRequest(model.sessionResource, 'steering2', { agentId: 'slowAgent', queue: ChatRequestQueueKind.Steering });
+		const steering3 = await testService.sendRequest(model.sessionResource, 'steering3', { agentId: 'slowAgent', queue: ChatRequestQueueKind.Steering });
+		assert.ok(ChatSendResult.isQueued(steering1));
+		assert.ok(ChatSendResult.isQueued(steering2));
+		assert.ok(ChatSendResult.isQueued(steering3));
+
+		// Complete the first request - should trigger processing of combined steering requests
+		completeRequest.complete();
+		await response.data.responseCompletePromise;
+
+		// Wait for all deferred promises to resolve
+		await steering1.deferred;
+		await steering2.deferred;
+		await steering3.deferred;
+
+		// Should have only invoked 2 requests: the initial and the combined steering
+		assert.strictEqual(invokedRequests.length, 2, 'Should have only 2 invocations (initial + combined steering)');
+		// The combined message includes all steering texts joined with \n\n
+		assert.ok(invokedRequests[1].includes('steering1'), 'Combined message should include steering1');
+		assert.ok(invokedRequests[1].includes('steering2'), 'Combined message should include steering2');
+		assert.ok(invokedRequests[1].includes('steering3'), 'Combined message should include steering3');
+		assert.ok(invokedRequests[1].includes('\n\n'), 'Combined message should use \\n\\n as separator');
+	});
+
+	test('disabled Claude hooks hint is shown once per workspace (fix for #295079)', async () => {
+		// Set up a prompts service that reports disabled Claude hooks
+		const mockPromptsService = new class extends MockPromptsService {
+			override getHooks(_token: CancellationToken, _sessionResource?: URI): Promise<IConfiguredHooksInfo> {
+				return Promise.resolve({ hooks: {}, hasDisabledClaudeHooks: true });
+			}
+		}();
+		instantiationService.stub(IPromptsService, mockPromptsService);
+
+		const storageService = instantiationService.get(IStorageService);
+		const disabledHintsKey = 'chat.disabledClaudeHooks.notification';
+
+		// Before any request, the storage key should not be set
+		assert.strictEqual(storageService.getBoolean(disabledHintsKey, StorageScope.WORKSPACE), undefined);
+
+		const testService = createChatService();
+		const modelRef = testDisposables.add(startSessionModel(testService));
+		const model = modelRef.object;
+
+		// Disabled hooks are reported for every request, but the hint should only be shown once per workspace.
+		const response = await testService.sendRequest(model.sessionResource, 'test request');
+		ChatSendResult.assertSent(response);
+		await response.data.responseCompletePromise;
+
+		// The hint should have been shown, and the key set to true
+		assert.strictEqual(storageService.getBoolean(disabledHintsKey, StorageScope.WORKSPACE), true, 'Flag should be set after showing the hint');
+
+		// Verify the response contains the disabledClaudeHooks part
+		const requests = model.getRequests();
+		assert.strictEqual(requests.length, 1);
+		const responseParts = requests[0].response?.response.value ?? [];
+		const hasHookHint = responseParts.some(part => part.kind === 'disabledClaudeHooks');
+		assert.ok(hasHookHint, 'Response should contain the disabledClaudeHooks hint');
+
+		// Sending another request should NOT show the hint again (shown only once per workspace)
+		const response2 = await testService.sendRequest(model.sessionResource, 'second request');
+		ChatSendResult.assertSent(response2);
+		await response2.data.responseCompletePromise;
+
+		const requests2 = model.getRequests();
+		assert.strictEqual(requests2.length, 2);
+		const responseParts2 = requests2[1].response?.response.value ?? [];
+		const hasHookHint2 = responseParts2.some(part => part.kind === 'disabledClaudeHooks');
+		assert.ok(!hasHookHint2, 'Response should NOT contain the disabledClaudeHooks hint on second request');
+	});
+
+	test('disabled Claude hooks hint is not consumed when no disabled hooks (fix for #295079)', async () => {
+		// Set up a prompts service that simulates the setup agent first pass (no disabled hooks)
+		// followed by the real resent request (with disabled hooks).
+		const mockPromptsService = new class extends MockPromptsService {
+			private _callCount = 0;
+			override getHooks(_token: CancellationToken, _sessionResource?: URI): Promise<IConfiguredHooksInfo> {
+				this._callCount++;
+				// First call (setup agent): no disabled hooks
+				// Second call (real request after resend): disabled hooks present
+				return Promise.resolve({ hooks: {}, hasDisabledClaudeHooks: this._callCount > 1 });
+			}
+		}();
+		instantiationService.stub(IPromptsService, mockPromptsService);
+
+		const storageService = instantiationService.get(IStorageService);
+		const disabledHintsKey = 'chat.disabledClaudeHooks.notification';
+
+		// First request: no disabled hooks (simulates setup agent pass)
+		const testService = createChatService();
+		const modelRef = testDisposables.add(startSessionModel(testService));
+		const model = modelRef.object;
+
+		const response = await testService.sendRequest(model.sessionResource, 'first request');
+		ChatSendResult.assertSent(response);
+		await response.data.responseCompletePromise;
+
+		// Flag should NOT be set because no hint was shown
+		assert.strictEqual(storageService.getBoolean(disabledHintsKey, StorageScope.WORKSPACE), undefined, 'Flag should not be set when no disabled hooks');
+
+		const firstRequest = model.getRequests()[0];
+		assert.ok(firstRequest, 'Expected the initial request to exist before resend');
+
+		// Resend the original request: now disabled hooks are present (simulates resend after setup)
+		await testService.resendRequest(firstRequest);
+
+		// Now the flag should be set and the hint shown
+		assert.strictEqual(storageService.getBoolean(disabledHintsKey, StorageScope.WORKSPACE), true, 'Flag should be set after showing the hint');
+
+		const requests = model.getRequests();
+		assert.strictEqual(requests.length, 1, 'Resend should replace the original request');
+		const responseParts2 = requests[0].response?.response.value ?? [];
+		const hasHookHint2 = responseParts2.some(part => part.kind === 'disabledClaudeHooks');
+		assert.ok(hasHookHint2, 'Response should contain the disabledClaudeHooks hint on second request');
+	});
+	test('cancelCurrentRequestForSession waits for response completion', async () => {
+		const requestStarted = new DeferredPromise<void>();
+		const completeRequest = new DeferredPromise<void>();
+
+		const slowAgent: IChatAgentImplementation = {
+			async invoke(request, progress, history, token) {
+				requestStarted.complete();
+				const listener = token.onCancellationRequested(() => {
+					listener.dispose();
+					// Simulate some cleanup delay before completing
+					setTimeout(() => completeRequest.complete(), 10);
+				});
+				await completeRequest.p;
+				return {};
+			},
+		};
+
+		testDisposables.add(chatAgentService.registerAgent('slowAgent', { ...getAgentData('slowAgent'), isDefault: true }));
+		testDisposables.add(chatAgentService.registerAgentImplementation('slowAgent', slowAgent));
+
+		const testService = createChatService();
+		const modelRef = testDisposables.add(startSessionModel(testService));
+		const model = modelRef.object;
+
+		const response = await testService.sendRequest(model.sessionResource, 'test request', { agentId: 'slowAgent' });
+		ChatSendResult.assertSent(response);
+
+		await requestStarted.p;
+
+		// Cancel and await - should wait for the response to complete
+		await testService.cancelCurrentRequestForSession(model.sessionResource, 'test');
+
+		// After cancel resolves, the response model should have a result
+		const lastRequest = model.getRequests()[0];
+		assert.ok(lastRequest.response, 'Response should exist after cancellation completes');
+		assert.strictEqual(lastRequest.response.state, ResponseModelState.Cancelled, 'Response should be in Cancelled state');
+	});
+
+	test('cancelCurrentRequestForSession returns after timeout if response does not complete', async () => {
+		const requestStarted = new DeferredPromise<void>();
+		const completeRequest = new DeferredPromise<void>();
+
+		const hangingAgent: IChatAgentImplementation = {
+			async invoke(request, progress, history, token) {
+				requestStarted.complete();
+				// Wait for external signal, ignoring cancellation to simulate a hung agent
+				await completeRequest.p;
+				return {};
+			},
+		};
+
+		testDisposables.add(chatAgentService.registerAgent('hangingAgent', { ...getAgentData('hangingAgent'), isDefault: true }));
+		testDisposables.add(chatAgentService.registerAgentImplementation('hangingAgent', hangingAgent));
+
+		const testService = createChatService();
+		const modelRef = testDisposables.add(startSessionModel(testService));
+		const model = modelRef.object;
+
+		const response = await testService.sendRequest(model.sessionResource, 'test request', { agentId: 'hangingAgent' });
+		ChatSendResult.assertSent(response);
+
+		await requestStarted.p;
+
+		// Cancel should return after timeout even though the agent has not completed.
+		// Use faked timers so raceTimeout's 1s setTimeout fires instantly.
+		await runWithFakedTimers({ useFakeTimers: true }, async () => {
+			await testService.cancelCurrentRequestForSession(model.sessionResource, 'test');
+		});
+
+		// Let the agent finish so the test cleans up properly
+		completeRequest.complete();
+		await response.data.responseCompletePromise;
+	});
+
+	test('pending requests can be removed from one session and re-sent on another', async () => {
+		const requestStarted = new DeferredPromise<void>();
+		const completeRequest = new DeferredPromise<void>();
+		const invokedMessages: string[] = [];
+
+		const slowAgent: IChatAgentImplementation = {
+			async invoke(request, progress, history, token) {
+				invokedMessages.push(request.message);
+				if (invokedMessages.length === 1) {
+					requestStarted.complete();
+					await completeRequest.p;
+				}
+				return {};
+			},
+		};
+
+		testDisposables.add(chatAgentService.registerAgent('slowAgent', { ...getAgentData('slowAgent'), isDefault: true }));
+		testDisposables.add(chatAgentService.registerAgentImplementation('slowAgent', slowAgent));
+
+		const testService = createChatService();
+		const sourceRef = testDisposables.add(startSessionModel(testService));
+		const source = sourceRef.object;
+
+		// Start a blocking request on source
+		const response = await testService.sendRequest(source.sessionResource, 'first request', { agentId: 'slowAgent' });
+		ChatSendResult.assertSent(response);
+		await requestStarted.p;
+
+		// Queue a request while the first is in progress
+		const queued = await testService.sendRequest(source.sessionResource, 'queued request', { agentId: 'slowAgent', queue: ChatRequestQueueKind.Queued });
+		assert.ok(ChatSendResult.isQueued(queued));
+
+		// Remove the queued request from source
+		const pendingId = source.getPendingRequests()[0].request.id;
+		testService.removePendingRequest(source.sessionResource, pendingId);
+		assert.strictEqual(source.getPendingRequests().length, 0);
+
+		// Re-send it on a new target session through the normal queue path
+		const targetRef = testDisposables.add(startSessionModel(testService));
+		const target = targetRef.object;
+		const resent = await testService.sendRequest(target.sessionResource, 'queued request', { agentId: 'slowAgent', queue: ChatRequestQueueKind.Queued, pauseQueue: true });
+		assert.ok(ChatSendResult.isQueued(resent));
+		assert.strictEqual(target.getPendingRequests().length, 1);
+
+		// Complete the first request so the source loop finishes
+		completeRequest.complete();
+		await response.data.responseCompletePromise;
+
+		// Process the target queue — the re-sent request should be invoked
+		testService.processPendingRequests(target.sessionResource);
+		const result = await resent.deferred;
+		assert.ok(ChatSendResult.isSent(result));
+
+		// The agent should have been invoked twice: first request + re-sent queued request
+		assert.strictEqual(invokedMessages.length, 2);
+		assert.ok(invokedMessages[1].includes('queued request'));
+	});
+
+	test('race condition: processNextPendingRequest dequeues before commit handler runs', async () => {
+		// This reproduces the race where:
+		// 1. Request 1 completes → .finally() calls processNextPendingRequest immediately
+		// 2. processNextPendingRequest dequeues queued-request-1 and starts it on the OLD session
+		// 3. Commit event arrives later → only sees remaining queued requests (one was already dequeued)
+		// The fix: detect the in-flight request on the old session, cancel it, and re-send on the new session.
+
+		const invocationOrder: string[] = [];
+		const firstRequestStarted = new DeferredPromise<void>();
+		const firstRequestGate = new DeferredPromise<void>();
+
+		const slowAgent: IChatAgentImplementation = {
+			async invoke(request, progress, history, token) {
+				invocationOrder.push(request.message);
+
+				if (invocationOrder.length === 1) {
+					// First request — block until we say go
+					firstRequestStarted.complete();
+					await firstRequestGate.p;
+				}
+				// All subsequent requests complete immediately
+				return {};
+			},
+		};
+
+		testDisposables.add(chatAgentService.registerAgent('slowAgent', { ...getAgentData('slowAgent'), isDefault: true }));
+		testDisposables.add(chatAgentService.registerAgentImplementation('slowAgent', slowAgent));
+
+		const testService = createChatService();
+		const sourceRef = testDisposables.add(startSessionModel(testService));
+		const source = sourceRef.object;
+
+		// Step 1: Send request 1 (blocks on firstRequestGate)
+		const response1 = await testService.sendRequest(source.sessionResource, 'request-1', { agentId: 'slowAgent' });
+		ChatSendResult.assertSent(response1);
+		await firstRequestStarted.p;
+
+		// Step 2: Queue 3 more requests while request 1 is in progress
+		const q1 = await testService.sendRequest(source.sessionResource, 'queued-1', { agentId: 'slowAgent', queue: ChatRequestQueueKind.Queued });
+		const q2 = await testService.sendRequest(source.sessionResource, 'queued-2', { agentId: 'slowAgent', queue: ChatRequestQueueKind.Queued });
+		const q3 = await testService.sendRequest(source.sessionResource, 'queued-3', { agentId: 'slowAgent', queue: ChatRequestQueueKind.Queued });
+		assert.ok(ChatSendResult.isQueued(q1));
+		assert.ok(ChatSendResult.isQueued(q2));
+		assert.ok(ChatSendResult.isQueued(q3));
+		assert.strictEqual(source.getPendingRequests().length, 3);
+		assert.strictEqual(source.getRequests().length, 1, 'Only request-1 should be a real request');
+
+		// Step 3: Complete request 1 → .finally() runs processNextPendingRequest
+		// This dequeues "queued-1" and starts it on the source (old) session
+		firstRequestGate.complete();
+		await response1.data.responseCompletePromise;
+
+		// processNextPendingRequest dequeued one from the queue synchronously
+		assert.strictEqual(source.getPendingRequests().length, 2, 'Should have 2 remaining after auto-dequeue');
+
+		// Yield to let the dequeued request's async chain progress (extension activation, addRequest, etc.)
+		await new Promise(resolve => setTimeout(resolve, 0));
+
+		// Step 4: Simulate what _resendPendingRequests does (the commit handler)
+		// This is the recovery: cancel the in-flight, remove remaining, re-send all on target
+		const targetRef = testDisposables.add(startSessionModel(testService));
+		const target = targetRef.object;
+
+		// Cancel whatever is in-flight on the old session
+		await testService.cancelCurrentRequestForSession(source.sessionResource);
+
+		// Remove remaining pending requests from old session
+		const remaining = [...source.getPendingRequests()];
+		for (const p of remaining) {
+			testService.removePendingRequest(source.sessionResource, p.request.id);
+		}
+		assert.strictEqual(source.getPendingRequests().length, 0);
+
+		// Re-send ALL 3 on the target through the normal queue path
+		const resent1 = await testService.sendRequest(target.sessionResource, 'queued-1', { agentId: 'slowAgent', queue: ChatRequestQueueKind.Queued, pauseQueue: true });
+		const resent2 = await testService.sendRequest(target.sessionResource, 'queued-2', { agentId: 'slowAgent', queue: ChatRequestQueueKind.Queued, pauseQueue: true });
+		const resent3 = await testService.sendRequest(target.sessionResource, 'queued-3', { agentId: 'slowAgent', queue: ChatRequestQueueKind.Queued, pauseQueue: true });
+		assert.ok(ChatSendResult.isQueued(resent1));
+		assert.ok(ChatSendResult.isQueued(resent2));
+		assert.ok(ChatSendResult.isQueued(resent3));
+		assert.strictEqual(target.getPendingRequests().length, 3, 'Target should have all 3 queued requests');
+
+		// Step 5: Process the target queue and verify all 3 get sent
+		testService.processPendingRequests(target.sessionResource);
+		const result1 = await resent1.deferred;
+		assert.ok(ChatSendResult.isSent(result1));
+		await result1.data.responseCompletePromise;
+
+		const result2 = await resent2.deferred;
+		assert.ok(ChatSendResult.isSent(result2));
+		await result2.data.responseCompletePromise;
+
+		const result3 = await resent3.deferred;
+		assert.ok(ChatSendResult.isSent(result3));
+
+		// Verify the agent received all 3 queued messages on the target session
+		const queuedInvocations = invocationOrder.filter(m => m.includes('queued-'));
+		assert.ok(queuedInvocations.length >= 3, `Expected at least 3 queued invocations, got ${queuedInvocations.length}`);
+		const lastThree = queuedInvocations.slice(-3);
+		assert.ok(lastThree[0].includes('queued-1'));
+		assert.ok(lastThree[1].includes('queued-2'));
+		assert.ok(lastThree[2].includes('queued-3'));
+	});
+
+	test('sendRequest on untitled remote session propagates initialSessionOptions to new model', async () => {
+		const remoteScheme = 'remoteProvider';
+		const untitledResource = URI.from({ scheme: remoteScheme, path: '/untitled-test-session' });
+		const realResource = URI.from({ scheme: remoteScheme, path: '/real-session-123' });
+
+		// Set up the mock chat sessions service
+		const mockSessionsService = new MockChatSessionsService();
+
+		// Register a content provider so loadRemoteSession can resolve sessions
+		testDisposables.add(mockSessionsService.registerChatSessionContentProvider(remoteScheme, {
+			provideChatSessionContent: (_resource: URI, _token: CancellationToken) => {
+				return Promise.resolve({
+					sessionResource: _resource,
+					history: [],
+					onWillDispose: Event.None,
+					dispose: () => { },
+				});
+			},
+		}));
+
+		// Set session options for the untitled resource
+		mockSessionsService.setSessionOption(untitledResource, 'model', 'claude-3.5-sonnet');
+		mockSessionsService.setSessionOption(untitledResource, 'repo', 'my-repo');
+
+		// Override createNewChatSessionItem to return a real resource
+		mockSessionsService.createNewChatSessionItem = async () => ({
+			resource: realResource,
+			label: 'Test Session',
+			timing: { created: Date.now(), lastRequestStarted: undefined, lastRequestEnded: undefined },
+		});
+
+		instantiationService.stub(IChatSessionsService, mockSessionsService);
+
+		// Register the remote agent
+		const remoteAgent: IChatAgentImplementation = {
+			async invoke(request, progress, history, token) {
+				return {};
+			},
+		};
+		testDisposables.add(chatAgentService.registerAgent(remoteScheme, { ...getAgentData(remoteScheme), isDefault: true }));
+		testDisposables.add(chatAgentService.registerAgentImplementation(remoteScheme, remoteAgent));
+
+		const testService = createChatService();
+
+		// Load the untitled session to create the initial model
+		const untitledRef = await testService.acquireOrLoadSession(untitledResource, ChatAgentLocation.Chat, CancellationToken.None);
+		assert.ok(untitledRef, 'Should load untitled session');
+		testDisposables.add(untitledRef);
+
+		// Send a request - this triggers the untitled → real session conversion
+		const response = await testService.sendRequest(untitledResource, 'hello', { agentId: remoteScheme });
+		ChatSendResult.assertSent(response);
+		await response.data.responseCompletePromise;
+
+		// The new model (with real resource) should have initialSessionOptions set
+		const newModel = testService.getSession(realResource) as ChatModel;
+		assert.ok(newModel, 'New model should exist at the real resource');
+		assert.ok(newModel.contributedChatSession, 'New model should have contributedChatSession');
+		assert.deepStrictEqual(
+			newModel.contributedChatSession?.initialSessionOptions?.map(o => ({ optionId: o.optionId, value: o.value })),
+			[
+				{ optionId: 'model', value: 'claude-3.5-sonnet' },
+				{ optionId: 'repo', value: 'my-repo' },
+			]
+		);
+	});
 });
 
 
diff --git a/src/vs/workbench/contrib/chat/test/common/chatService/mockChatService.ts b/src/vs/workbench/contrib/chat/test/common/chatService/mockChatService.ts
index 8fb1d803deea2..52c097fac48f8 100644
--- a/src/vs/workbench/contrib/chat/test/common/chatService/mockChatService.ts
+++ b/src/vs/workbench/contrib/chat/test/common/chatService/mockChatService.ts
@@ -4,165 +4,209 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { CancellationToken } from '../../../../../../base/common/cancellation.js';
-import { Event } from '../../../../../../base/common/event.js';
+import { Emitter, Event } from '../../../../../../base/common/event.js';
+import { IDisposable } from '../../../../../../base/common/lifecycle.js';
 import { ResourceMap } from '../../../../../../base/common/map.js';
-import { IObservable, observableValue } from '../../../../../../base/common/observable.js';
+import { ISettableObservable, observableValue } from '../../../../../../base/common/observable.js';
 import { URI } from '../../../../../../base/common/uri.js';
-import { IChatModel, IChatRequestModel, IChatRequestVariableData, ISerializableChatData } from '../../../common/model/chatModel.js';
-import { IParsedChatRequest } from '../../../common/requestParser/chatParserTypes.js';
-import { ChatRequestQueueKind, ChatSendResult, IChatCompleteResponse, IChatDetail, IChatModelReference, IChatProgress, IChatProviderInfo, IChatSendRequestOptions, IChatService, IChatSessionContext, IChatSessionStartOptions, IChatUserActionEvent } from '../../../common/chatService/chatService.js';
+import { ChatRequestQueueKind, ChatSendResult, IChatDetail, IChatModelReference, IChatProgress, IChatSendRequestOptions, IChatService, IChatSessionContext, IChatSessionStartOptions, IChatUserActionEvent } from '../../../common/chatService/chatService.js';
 import { ChatAgentLocation } from '../../../common/constants.js';
+import { IChatModel, IChatRequestModel, IExportableChatData, ISerializableChatData } from '../../../common/model/chatModel.js';
 
 export class MockChatService implements IChatService {
-	chatModels: IObservable<Iterable<IChatModel>> = observableValue('chatModels', []);
+	private readonly _chatModels: ISettableObservable<Iterable<IChatModel>> = observableValue('chatModels', []);
+	readonly chatModels = this._chatModels;
 	requestInProgressObs = observableValue('name', false);
-	edits2Enabled: boolean = false;
 	_serviceBrand: undefined;
 	editingSessions = [];
-	transferredSessionResource: URI | undefined;
-	readonly onDidSubmitRequest: Event<{ readonly chatSessionResource: URI }> = Event.None;
-	readonly onDidCreateModel: Event<IChatModel> = Event.None;
+	transferredSessionResource = undefined;
+	readonly onDidSubmitRequest = Event.None;
+	readonly onDidCreateModel = Event.None;
 
-	private sessions = new ResourceMap<IChatModel>();
+	private readonly sessions = new ResourceMap<IChatModel>();
+	private liveSessionItems: IChatDetail[] = [];
+	private historySessionItems: IChatDetail[] = [];
 
-	setSaveModelsEnabled(enabled: boolean): void {
+	private readonly _onDidDisposeSession = new Emitter<{ sessionResource: URI[]; reason: 'cleared' }>();
+	readonly onDidDisposeSession = this._onDidDisposeSession.event;
 
+	fireDidDisposeSession(sessionResource: URI[]): void {
+		this._onDidDisposeSession.fire({ sessionResource, reason: 'cleared' });
 	}
-	isEnabled(location: ChatAgentLocation): boolean {
-		throw new Error('Method not implemented.');
+
+	setSaveModelsEnabled(enabled: boolean): void {
+
 	}
-	hasSessions(): boolean {
-		throw new Error('Method not implemented.');
+
+	processPendingRequests(sessionResource: URI): void {
+
 	}
-	getProviderInfos(): IChatProviderInfo[] {
-		throw new Error('Method not implemented.');
+
+	setLiveSessionItems(items: IChatDetail[]): void {
+		this.liveSessionItems = items;
 	}
-	startNewLocalSession(location: ChatAgentLocation, options?: IChatSessionStartOptions): IChatModelReference {
-		throw new Error('Method not implemented.');
+
+	setHistorySessionItems(items: IChatDetail[]): void {
+		this.historySessionItems = items;
 	}
+
 	addSession(session: IChatModel): void {
 		this.sessions.set(session.sessionResource, session);
+		// Update the chatModels observable
+		this._chatModels.set([...this.sessions.values()], undefined);
 	}
-	getSession(sessionResource: URI): IChatModel | undefined {
-		// eslint-disable-next-line local/code-no-dangerous-type-assertions
-		return this.sessions.get(sessionResource) ?? {} as IChatModel;
+
+	removeSession(sessionResource: URI): void {
+		this.sessions.delete(sessionResource);
+		// Update the chatModels observable
+		this._chatModels.set([...this.sessions.values()], undefined);
 	}
-	getLatestRequest(): IChatRequestModel | undefined {
-		return undefined;
+
+	isEnabled(_location: ChatAgentLocation): boolean {
+		return true;
 	}
-	async acquireOrRestoreSession(sessionResource: URI): Promise<IChatModelReference | undefined> {
-		throw new Error('Method not implemented.');
+
+	hasSessions(): boolean {
+		return this.sessions.size > 0;
 	}
-	getSessionTitle(sessionResource: URI): string | undefined {
-		throw new Error('Method not implemented.');
+
+	getProviderInfos() {
+		return [];
 	}
-	loadSessionFromData(data: ISerializableChatData): IChatModelReference {
+
+	startNewLocalSession(_location: ChatAgentLocation, _options?: IChatSessionStartOptions): IChatModelReference {
 		throw new Error('Method not implemented.');
 	}
-	acquireOrLoadSession(resource: URI, position: ChatAgentLocation, token: CancellationToken): Promise<IChatModelReference | undefined> {
-		throw new Error('Method not implemented.');
+
+	getSession(sessionResource: URI): IChatModel | undefined {
+		return this.sessions.get(sessionResource);
 	}
-	acquireExistingSession(sessionResource: URI): IChatModelReference | undefined {
+
+	getLatestRequest(): IChatRequestModel | undefined {
 		return undefined;
 	}
-	setSessionTitle(sessionResource: URI, title: string): void {
+
+	acquireOrRestoreSession(_sessionResource: URI): Promise<IChatModelReference | undefined> {
 		throw new Error('Method not implemented.');
 	}
-	appendProgress(request: IChatRequestModel, progress: IChatProgress): void {
 
+	getSessionTitle(_sessionResource: URI): string | undefined {
+		return undefined;
 	}
-	processPendingRequests(sessionResource: URI): void {
 
-	}
-	/**
-	 * Returns whether the request was accepted.
-	 */
-	sendRequest(sessionResource: URI, message: string): Promise<ChatSendResult> {
+	loadSessionFromData(data: IExportableChatData | ISerializableChatData): IChatModelReference {
 		throw new Error('Method not implemented.');
 	}
-	resendRequest(request: IChatRequestModel, options?: IChatSendRequestOptions | undefined): Promise<void> {
-		throw new Error('Method not implemented.');
-	}
-	adoptRequest(sessionResource: URI, request: IChatRequestModel): Promise<void> {
-		throw new Error('Method not implemented.');
-	}
-	removeRequest(sessionResource: URI, requestId: string): Promise<void> {
+
+	acquireOrLoadSession(_resource: URI, _position: ChatAgentLocation, _token: CancellationToken): Promise<IChatModelReference | undefined> {
 		throw new Error('Method not implemented.');
 	}
-	cancelCurrentRequestForSession(sessionResource: URI): void {
-		throw new Error('Method not implemented.');
+
+	acquireExistingSession(_sessionResource: URI): IChatModelReference | undefined {
+		return undefined;
 	}
-	setYieldRequested(sessionResource: URI): void {
+
+	setSessionTitle(_sessionResource: URI, _title: string): void { }
+
+	appendProgress(_request: IChatRequestModel, _progress: IChatProgress): void { }
+
+	sendRequest(_sessionResource: URI, _message: string): Promise<ChatSendResult> {
 		throw new Error('Method not implemented.');
 	}
-	removePendingRequest(sessionResource: URI, requestId: string): void {
+
+	resendRequest(_request: IChatRequestModel, _options?: IChatSendRequestOptions): Promise<void> {
 		throw new Error('Method not implemented.');
 	}
-	setPendingRequests(sessionResource: URI, requests: readonly { requestId: string; kind: ChatRequestQueueKind }[]): void {
+
+	adoptRequest(_sessionResource: URI, _request: IChatRequestModel): Promise<void> {
 		throw new Error('Method not implemented.');
 	}
-	addCompleteRequest(sessionResource: URI, message: IParsedChatRequest | string, variableData: IChatRequestVariableData | undefined, attempt: number | undefined, response: IChatCompleteResponse): void {
+
+	removeRequest(_sessionResource: URI, _requestId: string): Promise<void> {
 		throw new Error('Method not implemented.');
 	}
+
+	async cancelCurrentRequestForSession(_sessionResource: URI, _source?: string): Promise<void> { }
+
+	migrateRequests(_originalResource: URI, _targetResource: URI): void { }
+
+	setYieldRequested(_sessionResource: URI): void { }
+
+	removePendingRequest(_sessionResource: URI, _requestId: string): void { }
+
+	setPendingRequests(_sessionResource: URI, _requests: readonly { requestId: string; kind: ChatRequestQueueKind }[]): void { }
+
+	addCompleteRequest(): void { }
+
 	async getLocalSessionHistory(): Promise<IChatDetail[]> {
-		throw new Error('Method not implemented.');
-	}
-	async clearAllHistoryEntries() {
-		throw new Error('Method not implemented.');
-	}
-	async removeHistoryEntry(resource: URI) {
-		throw new Error('Method not implemented.');
+		return this.historySessionItems;
 	}
 
-	readonly onDidPerformUserAction: Event<IChatUserActionEvent> = undefined!;
-	notifyUserAction(event: IChatUserActionEvent): void {
-		throw new Error('Method not implemented.');
-	}
-	readonly onDidReceiveQuestionCarouselAnswer: Event<{ requestId: string; resolveId: string; answers: Record<string, unknown> | undefined }> = undefined!;
-	notifyQuestionCarouselAnswer(requestId: string, resolveId: string, answers: Record<string, unknown> | undefined): void {
-		throw new Error('Method not implemented.');
-	}
-	readonly onDidDisposeSession: Event<{ sessionResource: URI[]; reason: 'cleared' }> = undefined!;
+	async clearAllHistoryEntries(): Promise<void> { }
 
-	async transferChatSession(transferredSessionResource: URI, toWorkspace: URI): Promise<void> {
-		throw new Error('Method not implemented.');
-	}
+	async removeHistoryEntry(_resource: URI): Promise<void> { }
 
-	setChatSessionTitle(sessionResource: URI, title: string): void {
-		throw new Error('Method not implemented.');
-	}
+	readonly onDidPerformUserAction = Event.None;
 
-	isEditingLocation(location: ChatAgentLocation): boolean {
-		throw new Error('Method not implemented.');
+	notifyUserAction(_event: IChatUserActionEvent): void { }
+
+	readonly onDidReceiveQuestionCarouselAnswer = Event.None;
+
+	notifyQuestionCarouselAnswer(_requestId: string, _resolveId: string, _answers: Record<string, unknown> | undefined): void { }
+
+	async transferChatSession(): Promise<void> { }
+
+	setChatSessionTitle(): void { }
+
+	isEditingLocation(_location: ChatAgentLocation): boolean {
+		return false;
 	}
 
 	getChatStorageFolder(): URI {
-		throw new Error('Method not implemented.');
+		return URI.file('/tmp');
 	}
 
-	logChatIndex(): void {
-		throw new Error('Method not implemented.');
-	}
+	logChatIndex(): void { }
 
-	activateDefaultAgent(location: ChatAgentLocation): Promise<void> {
-		throw new Error('Method not implemented.');
+	activateDefaultAgent(_location: ChatAgentLocation): Promise<void> {
+		return Promise.resolve();
 	}
 
-	getChatSessionFromInternalUri(sessionResource: URI): IChatSessionContext | undefined {
-		throw new Error('Method not implemented.');
+	getChatSessionFromInternalUri(_sessionResource: URI): IChatSessionContext | undefined {
+		return undefined;
 	}
 
 	async getLiveSessionItems(): Promise<IChatDetail[]> {
-		throw new Error('Method not implemented.');
+		return this.liveSessionItems;
 	}
-	getHistorySessionItems(): Promise<IChatDetail[]> {
-		throw new Error('Method not implemented.');
+
+	async getHistorySessionItems(): Promise<IChatDetail[]> {
+		return this.historySessionItems;
 	}
 
 	waitForModelDisposals(): Promise<void> {
-		throw new Error('Method not implemented.');
+		return Promise.resolve();
 	}
+
 	getMetadataForSession(sessionResource: URI): Promise<IChatDetail | undefined> {
 		throw new Error('Method not implemented.');
 	}
+
+
+	private onChange?: (sessionResource: URI) => void;
+
+	registerChatModelChangeListeners(chatSessionType: string, onChange: (sessionResource: URI) => void): IDisposable {
+		// Store the emitter so tests can trigger it
+		this.onChange = onChange;
+		return {
+			dispose: () => {
+				this.onChange = undefined;
+			}
+		};
+	}
+
+	// Helper method for tests to trigger progress events
+	triggerProgressEvent(sessionResource: URI): void {
+		this.onChange?.(sessionResource);
+	}
 }
diff --git a/src/vs/workbench/contrib/chat/test/common/languageModels.test.ts b/src/vs/workbench/contrib/chat/test/common/languageModels.test.ts
index ddac0e86cc3dc..5790fab95ddc0 100644
--- a/src/vs/workbench/contrib/chat/test/common/languageModels.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/languageModels.test.ts
@@ -160,7 +160,7 @@ suite('LanguageModels', function () {
 				}));
 				return modelMetadataAndIdentifier;
 			},
-			sendChatRequest: async (modelId: string, messages: IChatMessage[], _from: ExtensionIdentifier, _options: { [name: string]: any }, token: CancellationToken) => {
+			sendChatRequest: async (modelId: string, messages: IChatMessage[], _from: ExtensionIdentifier | undefined, _options: { [name: string]: any }, token: CancellationToken) => {
 				// const message = messages.at(-1);
 
 				const defer = new DeferredPromise();
diff --git a/src/vs/workbench/contrib/chat/test/common/languageModels.ts b/src/vs/workbench/contrib/chat/test/common/languageModels.ts
index 77b874be830d0..8ead7eab0a9b0 100644
--- a/src/vs/workbench/contrib/chat/test/common/languageModels.ts
+++ b/src/vs/workbench/contrib/chat/test/common/languageModels.ts
@@ -67,7 +67,7 @@ export class NullLanguageModelsService implements ILanguageModelsService {
 	}
 
 	// eslint-disable-next-line @typescript-eslint/no-explicit-any
-	sendChatRequest(identifier: string, from: ExtensionIdentifier, messages: IChatMessage[], options: { [name: string]: any }, token: CancellationToken): Promise<ILanguageModelChatResponse> {
+	sendChatRequest(identifier: string, from: ExtensionIdentifier | undefined, messages: IChatMessage[], options: { [name: string]: any }, token: CancellationToken): Promise<ILanguageModelChatResponse> {
 		throw new Error('Method not implemented.');
 	}
 
diff --git a/src/vs/workbench/contrib/chat/test/common/mockChatSessionsService.ts b/src/vs/workbench/contrib/chat/test/common/mockChatSessionsService.ts
index bbeaa0b4c058a..bae11e420fb6b 100644
--- a/src/vs/workbench/contrib/chat/test/common/mockChatSessionsService.ts
+++ b/src/vs/workbench/contrib/chat/test/common/mockChatSessionsService.ts
@@ -9,11 +9,10 @@ import { IDisposable } from '../../../../../base/common/lifecycle.js';
 import { ResourceMap } from '../../../../../base/common/map.js';
 import { ThemeIcon } from '../../../../../base/common/themables.js';
 import { URI } from '../../../../../base/common/uri.js';
-import { IChatAgentAttachmentCapabilities, IChatAgentRequest } from '../../common/participants/chatAgents.js';
+import { IChatAgentAttachmentCapabilities } from '../../common/participants/chatAgents.js';
 import { IChatModel } from '../../common/model/chatModel.js';
-import { IChatService } from '../../common/chatService/chatService.js';
-import { IChatSession, IChatSessionContentProvider, IChatSessionItemController, IChatSessionItem, IChatSessionOptionsWillNotifyExtensionEvent, IChatSessionProviderOptionGroup, IChatSessionProviderOptionItem, IChatSessionsExtensionPoint, IChatSessionsService } from '../../common/chatSessionsService.js';
-import { Target } from '../../common/promptSyntax/service/promptsService.js';
+import { IChatNewSessionRequest, IChatSession, IChatSessionContentProvider, IChatSessionItemController, IChatSessionItem, IChatSessionOptionsWillNotifyExtensionEvent, IChatSessionProviderOptionGroup, IChatSessionProviderOptionItem, IChatSessionsExtensionPoint, IChatSessionsService, ResolvedChatSessionsExtensionPoint, IChatSessionItemsDelta } from '../../common/chatSessionsService.js';
+import { Target } from '../../common/promptSyntax/promptTypes.js';
 
 export class MockChatSessionsService implements IChatSessionsService {
 	_serviceBrand: undefined;
@@ -23,7 +22,7 @@ export class MockChatSessionsService implements IChatSessionsService {
 	private readonly _onDidChangeItemsProviders = new Emitter<{ readonly chatSessionType: string }>();
 	readonly onDidChangeItemsProviders = this._onDidChangeItemsProviders.event;
 
-	private readonly _onDidChangeSessionItems = new Emitter<{ readonly chatSessionType: string }>();
+	private readonly _onDidChangeSessionItems = new Emitter<IChatSessionItemsDelta>();
 	readonly onDidChangeSessionItems = this._onDidChangeSessionItems.event;
 
 	private readonly _onDidChangeAvailability = new Emitter<void>();
@@ -47,15 +46,14 @@ export class MockChatSessionsService implements IChatSessionsService {
 	private optionGroups = new Map<string, IChatSessionProviderOptionGroup[]>();
 	private sessionOptions = new ResourceMap<Map<string, string>>();
 	private inProgress = new Map<string, number>();
-	private onChange = () => { };
 
 	// For testing: allow triggering events
 	fireDidChangeItemsProviders(event: { chatSessionType: string }): void {
 		this._onDidChangeItemsProviders.fire(event);
 	}
 
-	fireDidChangeSessionItems(chatSessionType: string): void {
-		this._onDidChangeSessionItems.fire({ chatSessionType });
+	fireDidChangeSessionItems(event: IChatSessionItemsDelta): void {
+		this._onDidChangeSessionItems.fire(event);
 	}
 
 	fireDidChangeAvailability(): void {
@@ -75,12 +73,24 @@ export class MockChatSessionsService implements IChatSessionsService {
 		};
 	}
 
-	getAllChatSessionContributions(): IChatSessionsExtensionPoint[] {
-		return this.contributions;
+	getAllChatSessionContributions(): ResolvedChatSessionsExtensionPoint[] {
+		return this.contributions.map(contribution => this.resolveContribution(contribution));
 	}
 
-	getChatSessionContribution(chatSessionType: string): IChatSessionsExtensionPoint | undefined {
-		return this.contributions.find(contrib => contrib.type === chatSessionType);
+	getChatSessionContribution(chatSessionType: string): ResolvedChatSessionsExtensionPoint | undefined {
+		const contribution = this.contributions.find(c => c.type === chatSessionType);
+		if (!contribution) {
+			return undefined;
+		}
+
+		return this.resolveContribution(contribution);
+	}
+
+	private resolveContribution(contribution: IChatSessionsExtensionPoint): ResolvedChatSessionsExtensionPoint {
+		return {
+			...contribution,
+			icon: contribution.icon && typeof contribution.icon === 'string' ? ThemeIcon.fromId(contribution.icon) : undefined,
+		};
 	}
 
 	setContributions(contributions: IChatSessionsExtensionPoint[]): void {
@@ -91,34 +101,16 @@ export class MockChatSessionsService implements IChatSessionsService {
 		// Noop, nothing to activate
 	}
 
-	getIconForSessionType(chatSessionType: string): ThemeIcon | URI | undefined {
-		const contribution = this.contributions.find(c => c.type === chatSessionType);
-		return contribution?.icon && typeof contribution.icon === 'string' ? ThemeIcon.fromId(contribution.icon) : undefined;
-	}
-
-	getWelcomeTitleForSessionType(chatSessionType: string): string | undefined {
-		return this.contributions.find(c => c.type === chatSessionType)?.welcomeTitle;
-	}
-
-	getWelcomeMessageForSessionType(chatSessionType: string): string | undefined {
-		return this.contributions.find(c => c.type === chatSessionType)?.welcomeMessage;
-	}
-
-	getInputPlaceholderForSessionType(chatSessionType: string): string | undefined {
-		return this.contributions.find(c => c.type === chatSessionType)?.inputPlaceholder;
-	}
-
-	getChatSessionItems(providerTypeFilter: readonly string[] | undefined, token: CancellationToken): Promise<Array<{ readonly chatSessionType: string; readonly items: readonly IChatSessionItem[] }>> {
-		return Promise.all(
-			Array.from(this.sessionItemControllers.entries())
-				.filter(([chatSessionType]) => !providerTypeFilter || providerTypeFilter.includes(chatSessionType))
-				.map(async ([chatSessionType, controllerEntry]) => {
-					await controllerEntry.initialRefresh; // ensure initial refresh is done
-					return ({
-						chatSessionType: chatSessionType,
-						items: controllerEntry.controller.items
-					});
-				}));
+	async *getChatSessionItems(providerTypeFilter: readonly string[] | undefined, token: CancellationToken): AsyncIterable<{ readonly chatSessionType: string; readonly items: readonly IChatSessionItem[] }> {
+		for (const [chatSessionType, controllerEntry] of this.sessionItemControllers.entries()) {
+			if (!providerTypeFilter || providerTypeFilter.includes(chatSessionType)) {
+				await controllerEntry.initialRefresh; // ensure initial refresh is done
+				yield {
+					chatSessionType: chatSessionType,
+					items: controllerEntry.controller.items
+				};
+			}
+		}
 	}
 
 	async refreshChatSessionItems(providerTypeFilter: readonly string[] | undefined, token: CancellationToken): Promise<void> {
@@ -161,8 +153,8 @@ export class MockChatSessionsService implements IChatSessionsService {
 		return provider.provideChatSessionContent(sessionResource, token);
 	}
 
-	async canResolveChatSession(chatSessionResource: URI): Promise<boolean> {
-		return this.contentProviders.has(chatSessionResource.scheme);
+	async canResolveChatSession(sessionType: string): Promise<boolean> {
+		return this.contentProviders.has(sessionType);
 	}
 
 	getOptionGroupsForSessionType(chatSessionType: string): IChatSessionProviderOptionGroup[] | undefined {
@@ -177,10 +169,23 @@ export class MockChatSessionsService implements IChatSessionsService {
 		}
 	}
 
+	getNewSessionOptionsForSessionType(_chatSessionType: string): Record<string, string | IChatSessionProviderOptionItem> | undefined {
+		return undefined;
+	}
+
+	setNewSessionOptionsForSessionType(_chatSessionType: string, _options: Record<string, string | IChatSessionProviderOptionItem>): void {
+		// noop
+	}
+
 	async notifySessionOptionsChange(sessionResource: URI, updates: ReadonlyArray<{ optionId: string; value: string | IChatSessionProviderOptionItem }>): Promise<void> {
 		await this._onRequestNotifyExtension.fireAsync({ sessionResource, updates }, CancellationToken.None);
 	}
 
+	getSessionOptions(sessionResource: URI): Map<string, string> | undefined {
+		const options = this.sessionOptions.get(sessionResource);
+		return options && options.size > 0 ? options : undefined;
+	}
+
 	getSessionOption(sessionResource: URI, optionId: string): string | undefined {
 		return this.sessionOptions.get(sessionResource)?.get(optionId);
 	}
@@ -217,23 +222,11 @@ export class MockChatSessionsService implements IChatSessionsService {
 		return undefined;
 	}
 
-	async createNewChatSessionItem(_chatSessionType: string, _request: IChatAgentRequest, _token: CancellationToken): Promise<IChatSessionItem | undefined> {
+	async createNewChatSessionItem(_chatSessionType: string, _request: IChatNewSessionRequest, _token: CancellationToken): Promise<IChatSessionItem | undefined> {
 		return undefined;
 	}
 
-	registerChatModelChangeListeners(chatService: IChatService, chatSessionType: string, onChange: () => void): IDisposable {
-		// Store the emitter so tests can trigger it
-		this.onChange = onChange;
-		return {
-			dispose: () => {
-			}
-		};
-	}
-
-	// Helper method for tests to trigger progress events
-	triggerProgressEvent(): void {
-		if (this.onChange) {
-			this.onChange();
-		}
+	registerSessionResourceAlias(_untitledResource: URI, _realResource: URI): void {
+		// noop
 	}
 }
diff --git a/src/vs/workbench/contrib/chat/test/common/model/chatModel.test.ts b/src/vs/workbench/contrib/chat/test/common/model/chatModel.test.ts
index c0800d4b46d91..e89b504b22411 100644
--- a/src/vs/workbench/contrib/chat/test/common/model/chatModel.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/model/chatModel.test.ts
@@ -25,10 +25,10 @@ import { TestExtensionService, TestStorageService } from '../../../../../test/co
 import { CellUri } from '../../../../notebook/common/notebookCommon.js';
 import { IChatRequestImplicitVariableEntry, IChatRequestStringVariableEntry, IChatRequestFileEntry, StringChatContextValue } from '../../../common/attachments/chatVariableEntries.js';
 import { ChatAgentService, IChatAgentService } from '../../../common/participants/chatAgents.js';
-import { ChatModel, ChatRequestModel, IExportableChatData, ISerializableChatData1, ISerializableChatData2, ISerializableChatData3, isExportableSessionData, isSerializableSessionData, normalizeSerializableChatData, Response } from '../../../common/model/chatModel.js';
+import { ChatModel, ChatRequestModel, IChatRequestModeInfo, IExportableChatData, ISerializableChatData1, ISerializableChatData2, ISerializableChatData3, isExportableSessionData, isSerializableSessionData, normalizeSerializableChatData, Response } from '../../../common/model/chatModel.js';
 import { ChatRequestTextPart } from '../../../common/requestParser/chatParserTypes.js';
 import { ChatRequestQueueKind, IChatService, IChatToolInvocation } from '../../../common/chatService/chatService.js';
-import { ChatAgentLocation } from '../../../common/constants.js';
+import { ChatAgentLocation, ChatModeKind } from '../../../common/constants.js';
 import { MockChatService } from '../chatService/mockChatService.js';
 
 suite('ChatModel', () => {
@@ -274,6 +274,52 @@ suite('ChatModel', () => {
 		// Should keep file attachments and implicit attachments with URI values
 		assert.deepStrictEqual(serialized.attachments, [fileAttachment, implicitWithUri]);
 	});
+
+	test('modeInfo roundtrips through serialization', async () => {
+		const modeInfo: IChatRequestModeInfo = {
+			kind: ChatModeKind.Agent,
+			isBuiltin: false,
+			modeId: 'custom',
+			modeInstructions: {
+				name: 'plan',
+				content: 'You are a planning agent',
+				toolReferences: [],
+			},
+			applyCodeBlockSuggestionId: undefined,
+		};
+
+		const serializableData: ISerializableChatData3 = {
+			version: 3,
+			sessionId: 'test-modeinfo-session',
+			creationDate: Date.now(),
+			customTitle: undefined,
+			initialLocation: ChatAgentLocation.Chat,
+			responderUsername: 'bot',
+			requests: [{
+				requestId: 'req1',
+				message: { text: 'plan something', parts: [] },
+				variableData: { variables: [] },
+				response: [{ value: 'Here is my plan', isTrusted: false }],
+				modelState: { value: 1 /* ResponseModelState.Complete */, completedAt: Date.now() },
+				modeInfo,
+			}],
+		};
+
+		const model = testDisposables.add(instantiationService.createInstance(
+			ChatModel,
+			{ value: serializableData, serializer: undefined! },
+			{ initialLocation: ChatAgentLocation.Chat, canUseTools: true }
+		));
+
+		const requests = model.getRequests();
+		assert.strictEqual(requests.length, 1);
+		assert.deepStrictEqual(requests[0].modeInfo, modeInfo);
+
+		// Verify roundtrip through toExport
+		const exported = model.toExport();
+		assert.strictEqual(exported.requests.length, 1);
+		assert.deepStrictEqual(exported.requests[0].modeInfo, modeInfo);
+	});
 });
 
 suite('Response', () => {
diff --git a/src/vs/workbench/contrib/chat/test/common/model/chatQuestionCarouselData.test.ts b/src/vs/workbench/contrib/chat/test/common/model/chatQuestionCarouselData.test.ts
index 1c022960b237a..5707ebbe4ab63 100644
--- a/src/vs/workbench/contrib/chat/test/common/model/chatQuestionCarouselData.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/model/chatQuestionCarouselData.test.ts
@@ -52,6 +52,8 @@ suite('ChatQuestionCarouselData', () => {
 
 	test('toJSON strips the completion promise', () => {
 		const carousel = new ChatQuestionCarouselData(createQuestions(), true, 'test-resolve-id', { q1: 'saved' }, true);
+		carousel.draftAnswers = { q2: 'draft' };
+		carousel.draftCurrentIndex = 1;
 
 		const json = carousel.toJSON();
 
@@ -60,6 +62,8 @@ suite('ChatQuestionCarouselData', () => {
 		assert.deepStrictEqual(json.data, { q1: 'saved' });
 		assert.strictEqual(json.isUsed, true);
 		assert.strictEqual((json as { completion?: unknown }).completion, undefined, 'toJSON should not include completion');
+		assert.strictEqual((json as { draftAnswers?: unknown }).draftAnswers, undefined, 'toJSON should not include draftAnswers');
+		assert.strictEqual((json as { draftCurrentIndex?: unknown }).draftCurrentIndex, undefined, 'toJSON should not include draftCurrentIndex');
 	});
 
 	test('multiple carousels can have independent completion promises', async () => {
diff --git a/src/vs/workbench/contrib/chat/test/common/plugins/agentPluginFormatDetection.test.ts b/src/vs/workbench/contrib/chat/test/common/plugins/agentPluginFormatDetection.test.ts
new file mode 100644
index 0000000000000..a86a2a37e6302
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/common/plugins/agentPluginFormatDetection.test.ts
@@ -0,0 +1,934 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { VSBuffer } from '../../../../../../base/common/buffer.js';
+import { Schemas } from '../../../../../../base/common/network.js';
+import { waitForState } from '../../../../../../base/common/observable.js';
+import { URI } from '../../../../../../base/common/uri.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { runWithFakedTimers } from '../../../../../../base/test/common/timeTravelScheduler.js';
+import { FileService } from '../../../../../../platform/files/common/fileService.js';
+import { IFileService } from '../../../../../../platform/files/common/files.js';
+import { InMemoryFileSystemProvider } from '../../../../../../platform/files/common/inMemoryFilesystemProvider.js';
+import { IInstantiationService } from '../../../../../../platform/instantiation/common/instantiation.js';
+import { TestInstantiationService } from '../../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import { ILogService, NullLogService } from '../../../../../../platform/log/common/log.js';
+import { IWorkspaceContextService } from '../../../../../../platform/workspace/common/workspace.js';
+import { testWorkspace } from '../../../../../../platform/workspace/test/common/testWorkspace.js';
+import { TestContextService } from '../../../../../test/common/workbenchTestServices.js';
+import { IPathService } from '../../../../../services/path/common/pathService.js';
+import { AbstractAgentPluginDiscovery } from '../../../common/plugins/agentPluginServiceImpl.js';
+import { ContributionEnablementState, IEnablementModel } from '../../../common/enablement.js';
+
+/**
+ * Concrete discovery subclass that returns a fixed list of plugin URIs,
+ * allowing format detection and content reading to be tested in isolation.
+ */
+class TestPluginDiscovery extends AbstractAgentPluginDiscovery {
+	private _sources: URI[] = [];
+
+	constructor(
+		fileService: IFileService,
+		pathService: IPathService,
+		logService: ILogService,
+		instantiationService: IInstantiationService,
+	) {
+		super(fileService, pathService, logService, instantiationService);
+	}
+
+	start(enablementModel: IEnablementModel): void {
+		this._enablementModel = enablementModel;
+	}
+
+	/** Set plugin sources and trigger a refresh. */
+	async setSourcesAndRefresh(uris: URI[]): Promise<void> {
+		this._sources = uris;
+		await this._refreshPlugins();
+	}
+
+	protected override async _discoverPluginSources() {
+		return this._sources.map(uri => ({
+			uri,
+			fromMarketplace: undefined,
+			remove: () => { },
+		}));
+	}
+}
+
+suite('AgentPlugin format detection', () => {
+	const store = ensureNoDisposablesAreLeakedInTestSuite();
+	const logService = new NullLogService();
+
+	let fileService: FileService;
+	let instantiationService: TestInstantiationService;
+	const workspaceRoot = URI.from({ scheme: Schemas.inMemory, path: '/workspace' });
+
+	setup(() => {
+		const contextService = new TestContextService(testWorkspace(workspaceRoot));
+
+		fileService = store.add(new FileService(logService));
+		store.add(fileService.registerProvider(Schemas.inMemory, store.add(new InMemoryFileSystemProvider())));
+
+		instantiationService = store.add(new TestInstantiationService());
+		instantiationService.stub(IFileService, fileService);
+		instantiationService.stub(ILogService, logService);
+		instantiationService.stub(IWorkspaceContextService, contextService);
+		instantiationService.stub(IPathService, {
+			userHome: async () => URI.file('/home/testuser'),
+		} as Partial<IPathService> as IPathService);
+		instantiationService.stub(IInstantiationService, instantiationService);
+	});
+
+	const mockEnablementModel: IEnablementModel = {
+		readEnabled: () => ContributionEnablementState.EnabledProfile,
+		setEnabled: () => { },
+	};
+
+	function createDiscovery(): TestPluginDiscovery {
+		return store.add(new TestPluginDiscovery(
+			fileService,
+			instantiationService.get(IPathService),
+			logService,
+			instantiationService,
+		));
+	}
+
+	async function writeFile(path: string, content: string): Promise<void> {
+		const uri = URI.from({ scheme: Schemas.inMemory, path });
+		await fileService.writeFile(uri, VSBuffer.fromString(content));
+	}
+
+	function pluginUri(path: string): URI {
+		return URI.from({ scheme: Schemas.inMemory, path });
+	}
+
+	test('detects Open Plugin format when .plugin/plugin.json exists', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/my-open-plugin');
+		await writeFile('/plugins/my-open-plugin/.plugin/plugin.json', JSON.stringify({ name: 'my-open-plugin' }));
+		await writeFile('/plugins/my-open-plugin/commands/hello.md', '# Hello');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		// Verify the plugin read commands from the standard commands/ directory
+		await waitForState(plugins[0].commands, cmds => cmds.length > 0);
+		assert.strictEqual(plugins[0].commands.get()[0].name, 'hello');
+	}));
+
+	test('detects Claude format when .claude-plugin/plugin.json exists', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/my-claude-plugin');
+		await writeFile('/plugins/my-claude-plugin/.claude-plugin/plugin.json', JSON.stringify({ name: 'my-claude-plugin' }));
+		await writeFile('/plugins/my-claude-plugin/commands/greet.md', '# Greet');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+		await waitForState(plugins[0].commands, cmds => cmds.length > 0);
+		assert.strictEqual(plugins[0].commands.get()[0].name, 'greet');
+	}));
+
+	test('falls back to Copilot format when no vendor manifest exists', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/my-copilot-plugin');
+		await writeFile('/plugins/my-copilot-plugin/plugin.json', JSON.stringify({ name: 'my-copilot-plugin' }));
+		await writeFile('/plugins/my-copilot-plugin/commands/run.md', '# Run');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+		await waitForState(plugins[0].commands, cmds => cmds.length > 0);
+		assert.strictEqual(plugins[0].commands.get()[0].name, 'run');
+	}));
+
+	test('Open Plugin format takes priority over Claude format', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		// Plugin has both .plugin/plugin.json and .claude-plugin/plugin.json —
+		// the open plugin manifest should be detected first.
+		const uri = pluginUri('/plugins/dual-plugin');
+		await writeFile('/plugins/dual-plugin/.plugin/plugin.json', JSON.stringify({ name: 'dual-plugin' }));
+		await writeFile('/plugins/dual-plugin/.claude-plugin/plugin.json', JSON.stringify({ name: 'dual-plugin' }));
+
+		// Write inline MCP into the open-plugin manifest to verify it's used.
+		await writeFile('/plugins/dual-plugin/.plugin/plugin.json', JSON.stringify({
+			name: 'dual-plugin',
+			mcpServers: { 'open-server': { command: 'echo', args: ['open'] } },
+		}));
+		// Claude manifest defines a different server to prove it's NOT read.
+		await writeFile('/plugins/dual-plugin/.claude-plugin/plugin.json', JSON.stringify({
+			name: 'dual-plugin',
+			mcpServers: { 'claude-server': { command: 'echo', args: ['claude'] } },
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].mcpServerDefinitions, defs => defs.length > 0);
+		const mcpDefs = plugins[0].mcpServerDefinitions.get();
+		assert.strictEqual(mcpDefs.length, 1);
+		assert.strictEqual(mcpDefs[0].name, 'open-server');
+	}));
+
+	test('Open Plugin reads MCP definitions from .plugin/plugin.json inline', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/mcp-plugin');
+		await writeFile('/plugins/mcp-plugin/.plugin/plugin.json', JSON.stringify({
+			name: 'mcp-plugin',
+			mcpServers: {
+				'my-server': { command: 'node', args: ['server.js'] },
+			},
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].mcpServerDefinitions, defs => defs.length > 0);
+		const mcpDefs = plugins[0].mcpServerDefinitions.get();
+		assert.deepStrictEqual(mcpDefs.map(d => d.name), ['my-server']);
+	}));
+
+	test('Open Plugin reads MCP definitions from standalone .mcp.json', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/mcp-standalone');
+		await writeFile('/plugins/mcp-standalone/.plugin/plugin.json', JSON.stringify({ name: 'mcp-standalone' }));
+		await writeFile('/plugins/mcp-standalone/.mcp.json', JSON.stringify({
+			mcpServers: {
+				'standalone-server': { command: 'python', args: ['serve.py'] },
+			},
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].mcpServerDefinitions, defs => defs.length > 0);
+		assert.strictEqual(plugins[0].mcpServerDefinitions.get()[0].name, 'standalone-server');
+	}));
+
+	test('reads skills from skills/ subdirectories', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/skills-plugin');
+		await writeFile('/plugins/skills-plugin/.plugin/plugin.json', JSON.stringify({ name: 'skills-plugin' }));
+		await writeFile('/plugins/skills-plugin/skills/deploy/SKILL.md', '# Deploy skill');
+		await writeFile('/plugins/skills-plugin/skills/lint/SKILL.md', '# Lint skill');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].skills, s => s.length > 0);
+		const skillNames = plugins[0].skills.get().map(s => s.name).sort();
+		assert.deepStrictEqual(skillNames, ['deploy', 'lint']);
+	}));
+
+	test('reads root-level SKILL.md as a fallback skill', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/root-skill');
+		await writeFile('/plugins/root-skill/.plugin/plugin.json', JSON.stringify({ name: 'root-skill' }));
+		await writeFile('/plugins/root-skill/SKILL.md', '# Visual Explainer');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].skills, s => s.length > 0);
+		assert.deepStrictEqual(
+			plugins[0].skills.get().map(s => s.name),
+			['root-skill'],
+		);
+	}));
+
+	test('root-level SKILL.md is ignored when skills/ has content', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/root-skill-ignored');
+		await writeFile('/plugins/root-skill-ignored/.plugin/plugin.json', JSON.stringify({ name: 'root-skill-ignored' }));
+		await writeFile('/plugins/root-skill-ignored/SKILL.md', '# Root skill');
+		await writeFile('/plugins/root-skill-ignored/skills/real/SKILL.md', '# Real skill');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].skills, s => s.length > 0);
+		assert.deepStrictEqual(
+			plugins[0].skills.get().map(s => s.name),
+			['real'],
+		);
+	}));
+
+	test('reads agents from agents/ directory', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/agents-plugin');
+		await writeFile('/plugins/agents-plugin/.plugin/plugin.json', JSON.stringify({ name: 'agents-plugin' }));
+		await writeFile('/plugins/agents-plugin/agents/reviewer.md', '---\nname: reviewer\n---\nYou review code.');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].agents, a => a.length > 0);
+		assert.strictEqual(plugins[0].agents.get()[0].name, 'reviewer');
+	}));
+
+	test('manifest skills field adds supplemental skill directories', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/custom-skills');
+		await writeFile('/plugins/custom-skills/.plugin/plugin.json', JSON.stringify({
+			name: 'custom-skills',
+			skills: './extra-skills/',
+		}));
+		await writeFile('/plugins/custom-skills/skills/default-skill/SKILL.md', '# Default skill');
+		await writeFile('/plugins/custom-skills/extra-skills/bonus-skill/SKILL.md', '# Bonus skill');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].skills, s => s.length >= 2);
+		assert.deepStrictEqual(
+			plugins[0].skills.get().map(s => s.name).sort(),
+			['bonus-skill', 'default-skill'],
+		);
+	}));
+
+	test('manifest skills field with exclusive mode skips default directory', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/exclusive-skills');
+		await writeFile('/plugins/exclusive-skills/.plugin/plugin.json', JSON.stringify({
+			name: 'exclusive-skills',
+			skills: { paths: ['./only-here/'], exclusive: true },
+		}));
+		await writeFile('/plugins/exclusive-skills/skills/ignored/SKILL.md', '# Should be ignored');
+		await writeFile('/plugins/exclusive-skills/only-here/visible/SKILL.md', '# Should be visible');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].skills, s => s.length > 0);
+		assert.deepStrictEqual(
+			plugins[0].skills.get().map(s => s.name),
+			['visible'],
+		);
+	}));
+
+	test('manifest commands field with string array scans multiple directories', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/multi-commands');
+		await writeFile('/plugins/multi-commands/.plugin/plugin.json', JSON.stringify({
+			name: 'multi-commands',
+			commands: ['./cmd1/', './cmd2/'],
+		}));
+		await writeFile('/plugins/multi-commands/commands/default.md', '# Default');
+		await writeFile('/plugins/multi-commands/cmd1/alpha.md', '# Alpha');
+		await writeFile('/plugins/multi-commands/cmd2/beta.md', '# Beta');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].commands, c => c.length >= 3);
+		assert.deepStrictEqual(
+			plugins[0].commands.get().map(c => c.name).sort(),
+			['alpha', 'beta', 'default'],
+		);
+	}));
+
+	test('manifest agents field adds supplemental agent directories', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/custom-agents');
+		await writeFile('/plugins/custom-agents/.plugin/plugin.json', JSON.stringify({
+			name: 'custom-agents',
+			agents: './extra-agents/',
+		}));
+		await writeFile('/plugins/custom-agents/agents/default-agent.md', '# Default');
+		await writeFile('/plugins/custom-agents/extra-agents/bonus-agent.md', '# Bonus');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].agents, a => a.length >= 2);
+		assert.deepStrictEqual(
+			plugins[0].agents.get().map(a => a.name).sort(),
+			['bonus-agent', 'default-agent'],
+		);
+	}));
+
+	test('path traversal in manifest is rejected', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/traversal');
+		await writeFile('/plugins/traversal/.plugin/plugin.json', JSON.stringify({
+			name: 'traversal',
+			skills: '../outside/',
+		}));
+		await writeFile('/plugins/outside/evil/SKILL.md', '# Evil skill');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		// Only default skills/ directory should be scanned; the traversal path is rejected.
+		// Since there are no skills in skills/, result should be empty.
+		await waitForState(plugins[0].skills, () => true);
+		assert.deepStrictEqual(plugins[0].skills.get(), []);
+	}));
+
+	test('duplicate names across directories deduplicate (first wins)', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/dedup');
+		await writeFile('/plugins/dedup/.plugin/plugin.json', JSON.stringify({
+			name: 'dedup',
+			commands: './extra-commands/',
+		}));
+		await writeFile('/plugins/dedup/commands/shared.md', '# Default version');
+		await writeFile('/plugins/dedup/extra-commands/shared.md', '# Custom version');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].commands, c => c.length > 0);
+		const cmds = plugins[0].commands.get();
+		assert.strictEqual(cmds.length, 1);
+		assert.strictEqual(cmds[0].name, 'shared');
+		// The default directory is scanned first, so the URI should come from commands/
+		assert.ok(cmds[0].uri.path.includes('/commands/shared.md'));
+	}));
+
+	test('discovers components without a manifest', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/no-manifest');
+		await writeFile('/plugins/no-manifest/commands/hello.md', '# Hello');
+		await writeFile('/plugins/no-manifest/skills/my-skill/SKILL.md', '# My skill');
+		await writeFile('/plugins/no-manifest/agents/helper.md', '# Helper');
+		await writeFile('/plugins/no-manifest/rules/prefer-const.mdc', '---\ndescription: Prefer const\n---\nUse const.');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+		assert.strictEqual(plugins[0].label, 'no-manifest');
+
+		await waitForState(plugins[0].commands, c => c.length > 0);
+		assert.strictEqual(plugins[0].commands.get()[0].name, 'hello');
+
+		await waitForState(plugins[0].skills, s => s.length > 0);
+		assert.strictEqual(plugins[0].skills.get()[0].name, 'my-skill');
+
+		await waitForState(plugins[0].agents, a => a.length > 0);
+		assert.strictEqual(plugins[0].agents.get()[0].name, 'helper');
+
+		await waitForState(plugins[0].instructions, i => i.length > 0);
+		assert.strictEqual(plugins[0].instructions.get()[0].name, 'prefer-const');
+	}));
+
+	test('reads hooks from default hooks/hooks.json', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/hooks-default');
+		await writeFile('/plugins/hooks-default/.plugin/plugin.json', JSON.stringify({ name: 'hooks-default' }));
+		await writeFile('/plugins/hooks-default/hooks/hooks.json', JSON.stringify({
+			hooks: {
+				PostToolUse: [{ matcher: 'Write', hooks: [{ type: 'command', command: 'echo done' }] }],
+			},
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+		await waitForState(plugins[0].hooks, h => h.length > 0);
+		assert.strictEqual(plugins[0].hooks.get().length, 1);
+	}));
+
+	test('reads inline hooks from manifest', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/hooks-inline');
+		await writeFile('/plugins/hooks-inline/.plugin/plugin.json', JSON.stringify({
+			name: 'hooks-inline',
+			hooks: {
+				hooks: {
+					SessionStart: [{ hooks: [{ type: 'command', command: 'echo start' }] }],
+				},
+			},
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+		await waitForState(plugins[0].hooks, h => h.length > 0);
+		assert.strictEqual(plugins[0].hooks.get().length, 1);
+	}));
+
+	test('reads hooks from custom path in manifest', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/hooks-custom');
+		await writeFile('/plugins/hooks-custom/.plugin/plugin.json', JSON.stringify({
+			name: 'hooks-custom',
+			hooks: './config/my-hooks.json',
+		}));
+		await writeFile('/plugins/hooks-custom/config/my-hooks.json', JSON.stringify({
+			hooks: {
+				PostToolUse: [{ matcher: 'Edit', hooks: [{ type: 'command', command: 'echo edited' }] }],
+			},
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+		await waitForState(plugins[0].hooks, h => h.length > 0);
+		assert.strictEqual(plugins[0].hooks.get().length, 1);
+	}));
+
+	test('reads MCP from custom path in manifest', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/mcp-custom');
+		await writeFile('/plugins/mcp-custom/.plugin/plugin.json', JSON.stringify({
+			name: 'mcp-custom',
+			mcpServers: './config/servers.json',
+		}));
+		await writeFile('/plugins/mcp-custom/config/servers.json', JSON.stringify({
+			mcpServers: {
+				'custom-server': { command: 'node', args: ['custom.js'] },
+			},
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+		await waitForState(plugins[0].mcpServerDefinitions, d => d.length > 0);
+		assert.strictEqual(plugins[0].mcpServerDefinitions.get()[0].name, 'custom-server');
+	}));
+
+	test('inline MCP in manifest takes priority over standalone .mcp.json', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/mcp-merged');
+		await writeFile('/plugins/mcp-merged/.plugin/plugin.json', JSON.stringify({
+			name: 'mcp-merged',
+			mcpServers: {
+				'inline-server': { command: 'echo', args: ['inline'] },
+			},
+		}));
+		await writeFile('/plugins/mcp-merged/.mcp.json', JSON.stringify({
+			mcpServers: {
+				'file-server': { command: 'echo', args: ['file'] },
+			},
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		// When inline mcpServers is an object in the manifest, it is treated as
+		// embedded configuration and the default .mcp.json file is not read.
+		// Wait for the inline server to appear (manifest loads asynchronously).
+		await waitForState(plugins[0].mcpServerDefinitions, d =>
+			[...d].some(s => s.name === 'inline-server'));
+		assert.deepStrictEqual(
+			plugins[0].mcpServerDefinitions.get().map(d => d.name),
+			['inline-server'],
+		);
+	}));
+
+	test('PLUGIN_ROOT expansion in hook commands', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/root-expansion');
+		await writeFile('/plugins/root-expansion/.plugin/plugin.json', JSON.stringify({
+			name: 'root-expansion',
+			hooks: {
+				hooks: {
+					PostToolUse: [{
+						hooks: [{
+							type: 'command',
+							command: '${PLUGIN_ROOT}/scripts/format.sh',
+						}],
+					}],
+				},
+			},
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+		await waitForState(plugins[0].hooks, h => h.length > 0);
+
+		const hookCommands = plugins[0].hooks.get()[0].hooks;
+		assert.ok(hookCommands.length > 0);
+		// ${PLUGIN_ROOT} should be expanded to the plugin's fsPath
+		const command = hookCommands[0].command;
+		assert.ok(command && !command.includes('${PLUGIN_ROOT}'), `Expected PLUGIN_ROOT to be expanded, got: ${command}`);
+	}));
+
+	test('manifest commands field pointing to a specific file', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/cmd-file');
+		await writeFile('/plugins/cmd-file/.plugin/plugin.json', JSON.stringify({
+			name: 'cmd-file',
+			commands: './special/deploy.md',
+		}));
+		await writeFile('/plugins/cmd-file/commands/default.md', '# Default');
+		await writeFile('/plugins/cmd-file/special/deploy.md', '# Deploy');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].commands, c => c.length >= 2);
+		assert.deepStrictEqual(
+			plugins[0].commands.get().map(c => c.name).sort(),
+			['default', 'deploy'],
+		);
+	}));
+
+	test('manifest commands field with array of specific files', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/cmd-files');
+		await writeFile('/plugins/cmd-files/.plugin/plugin.json', JSON.stringify({
+			name: 'cmd-files',
+			commands: ['./extras/alpha.md', './extras/beta.md'],
+		}));
+		await writeFile('/plugins/cmd-files/extras/alpha.md', '# Alpha');
+		await writeFile('/plugins/cmd-files/extras/beta.md', '# Beta');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].commands, c => c.length >= 2);
+		assert.deepStrictEqual(
+			plugins[0].commands.get().map(c => c.name).sort(),
+			['alpha', 'beta'],
+		);
+	}));
+
+	test('manifest agents field pointing to a specific file', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/agent-file');
+		await writeFile('/plugins/agent-file/.plugin/plugin.json', JSON.stringify({
+			name: 'agent-file',
+			agents: './custom/specialist.md',
+		}));
+		await writeFile('/plugins/agent-file/agents/default.md', '# Default');
+		await writeFile('/plugins/agent-file/custom/specialist.md', '# Specialist');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].agents, a => a.length >= 2);
+		assert.deepStrictEqual(
+			plugins[0].agents.get().map(a => a.name).sort(),
+			['default', 'specialist'],
+		);
+	}));
+
+	test('manifest skills field pointing to a specific skill directory', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/skill-dir');
+		await writeFile('/plugins/skill-dir/.plugin/plugin.json', JSON.stringify({
+			name: 'skill-dir',
+			skills: './custom/my-skill',
+		}));
+		await writeFile('/plugins/skill-dir/custom/my-skill/SKILL.md', '# My Skill');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].skills, s => s.length > 0);
+		assert.deepStrictEqual(
+			plugins[0].skills.get().map(s => s.name),
+			['my-skill'],
+		);
+	}));
+
+	test('manifest hooks field pointing to a specific file', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/hook-file');
+		await writeFile('/plugins/hook-file/.plugin/plugin.json', JSON.stringify({
+			name: 'hook-file',
+			hooks: './config/custom-hooks.json',
+		}));
+		await writeFile('/plugins/hook-file/config/custom-hooks.json', JSON.stringify({
+			hooks: {
+				SessionStart: [{ hooks: [{ type: 'command', command: 'echo hi' }] }],
+			},
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+		await waitForState(plugins[0].hooks, h => h.length > 0);
+		assert.strictEqual(plugins[0].hooks.get().length, 1);
+	}));
+
+	test('manifest mcpServers field pointing to a specific file', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/mcp-file');
+		await writeFile('/plugins/mcp-file/.plugin/plugin.json', JSON.stringify({
+			name: 'mcp-file',
+			mcpServers: './config/servers.json',
+		}));
+		await writeFile('/plugins/mcp-file/config/servers.json', JSON.stringify({
+			mcpServers: {
+				'custom-server': { command: 'node', args: ['serve.js'] },
+			},
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+		await waitForState(plugins[0].mcpServerDefinitions, d => d.length > 0);
+		assert.strictEqual(plugins[0].mcpServerDefinitions.get()[0].name, 'custom-server');
+	}));
+
+	test('reads rules from rules/ directory with .mdc extension', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/rules-plugin');
+		await writeFile('/plugins/rules-plugin/.plugin/plugin.json', JSON.stringify({ name: 'rules-plugin' }));
+		await writeFile('/plugins/rules-plugin/rules/prefer-const.mdc', '---\ndescription: Prefer const\n---\nUse const.');
+		await writeFile('/plugins/rules-plugin/rules/error-handling.mdc', '---\ndescription: Error handling\n---\nAlways handle errors.');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].instructions, i => i.length >= 2);
+		assert.deepStrictEqual(
+			plugins[0].instructions.get().map(i => i.name).sort(),
+			['error-handling', 'prefer-const'],
+		);
+	}));
+
+	test('reads rules with .md and .instructions.md extensions', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/rules-mixed');
+		await writeFile('/plugins/rules-mixed/.plugin/plugin.json', JSON.stringify({ name: 'rules-mixed' }));
+		await writeFile('/plugins/rules-mixed/rules/rule-a.mdc', 'Rule A');
+		await writeFile('/plugins/rules-mixed/rules/rule-b.md', 'Rule B');
+		await writeFile('/plugins/rules-mixed/rules/rule-c.instructions.md', 'Rule C');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].instructions, i => i.length >= 3);
+		assert.deepStrictEqual(
+			plugins[0].instructions.get().map(i => i.name).sort(),
+			['rule-a', 'rule-b', 'rule-c'],
+		);
+	}));
+
+	test('manifest rules field adds supplemental rule directories', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/custom-rules');
+		await writeFile('/plugins/custom-rules/.plugin/plugin.json', JSON.stringify({
+			name: 'custom-rules',
+			rules: './extra-rules/',
+		}));
+		await writeFile('/plugins/custom-rules/rules/default-rule.mdc', 'Default rule');
+		await writeFile('/plugins/custom-rules/extra-rules/bonus-rule.mdc', 'Bonus rule');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].instructions, i => i.length >= 2);
+		assert.deepStrictEqual(
+			plugins[0].instructions.get().map(i => i.name).sort(),
+			['bonus-rule', 'default-rule'],
+		);
+	}));
+
+	test('manifest rules field with exclusive mode skips default directory', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/exclusive-rules');
+		await writeFile('/plugins/exclusive-rules/.plugin/plugin.json', JSON.stringify({
+			name: 'exclusive-rules',
+			rules: { paths: ['./only-here/'], exclusive: true },
+		}));
+		await writeFile('/plugins/exclusive-rules/rules/ignored.mdc', 'Should be ignored');
+		await writeFile('/plugins/exclusive-rules/only-here/visible.mdc', 'Should be visible');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].instructions, i => i.length === 1 && i[0].name === 'visible');
+		assert.deepStrictEqual(
+			plugins[0].instructions.get().map(i => i.name),
+			['visible'],
+		);
+	}));
+
+	test('rule name strips longest matching suffix first', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/suffix-rules');
+		await writeFile('/plugins/suffix-rules/.plugin/plugin.json', JSON.stringify({ name: 'suffix-rules' }));
+		await writeFile('/plugins/suffix-rules/rules/coding-standards.instructions.md', 'Standards');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].instructions, i => i.length > 0);
+		// Should strip '.instructions.md' (longest match), not just '.md'
+		assert.strictEqual(plugins[0].instructions.get()[0].name, 'coding-standards');
+	}));
+
+	test('deduplicates rules with the same base name', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/dup-rules');
+		await writeFile('/plugins/dup-rules/.plugin/plugin.json', JSON.stringify({
+			name: 'dup-rules',
+			rules: './extra/',
+		}));
+		// Default directory has 'my-rule.mdc', supplemental has 'my-rule.md' — first wins
+		await writeFile('/plugins/dup-rules/rules/my-rule.mdc', 'From default');
+		await writeFile('/plugins/dup-rules/extra/my-rule.md', 'From extra');
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].instructions, i => i.length > 0);
+		assert.strictEqual(plugins[0].instructions.get().length, 1);
+		const instruction = plugins[0].instructions.get()[0];
+		assert.strictEqual(instruction.name, 'my-rule');
+		assert.ok(instruction.uri.path.endsWith('/rules/my-rule.mdc'));
+	}));
+
+	test('PLUGIN_ROOT expansion in inline MCP server definitions', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/mcp-root');
+		await writeFile('/plugins/mcp-root/.plugin/plugin.json', JSON.stringify({
+			name: 'mcp-root',
+			mcpServers: {
+				'my-server': {
+					command: '${PLUGIN_ROOT}/bin/server',
+					args: ['--config', '${PLUGIN_ROOT}/config.json'],
+					cwd: '${PLUGIN_ROOT}',
+					env: { 'CONFIG_DIR': '${PLUGIN_ROOT}/etc' },
+				},
+			},
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].mcpServerDefinitions, d => d.length > 0);
+		const server = plugins[0].mcpServerDefinitions.get()[0];
+		assert.strictEqual(server.name, 'my-server');
+		const config: any = server.configuration;
+		assert.ok(!config.command.includes('${PLUGIN_ROOT}'), `Expected PLUGIN_ROOT to be expanded in command, got: ${config.command}`);
+		assert.ok(!config.args[1].includes('${PLUGIN_ROOT}'), `Expected PLUGIN_ROOT to be expanded in args, got: ${config.args[1]}`);
+		assert.ok(!config.cwd.includes('${PLUGIN_ROOT}'), `Expected PLUGIN_ROOT to be expanded in cwd, got: ${config.cwd}`);
+		assert.ok(!config.env['CONFIG_DIR'].includes('${PLUGIN_ROOT}'), `Expected PLUGIN_ROOT to be expanded in env, got: ${config.env['CONFIG_DIR']}`);
+		assert.strictEqual(config.env['PLUGIN_ROOT'], uri.fsPath, 'Expected PLUGIN_ROOT env var to be set');
+	}));
+
+	test('CLAUDE_PLUGIN_ROOT expansion in MCP server definitions from .mcp.json', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const uri = pluginUri('/plugins/claude-mcp-root');
+		await writeFile('/plugins/claude-mcp-root/.claude-plugin/plugin.json', JSON.stringify({ name: 'claude-mcp-root' }));
+		await writeFile('/plugins/claude-mcp-root/.mcp.json', JSON.stringify({
+			mcpServers: {
+				'claude-server': {
+					command: '${CLAUDE_PLUGIN_ROOT}/run.sh',
+					args: ['--dir', '${CLAUDE_PLUGIN_ROOT}/data'],
+				},
+			},
+		}));
+
+		const discovery = createDiscovery();
+		discovery.start(mockEnablementModel);
+		await discovery.setSourcesAndRefresh([uri]);
+
+		const plugins = discovery.plugins.get();
+		assert.strictEqual(plugins.length, 1);
+
+		await waitForState(plugins[0].mcpServerDefinitions, d => d.length > 0);
+		const server = plugins[0].mcpServerDefinitions.get()[0];
+		const config: any = server.configuration;
+		assert.ok(!config.command.includes('${CLAUDE_PLUGIN_ROOT}'), `Expected CLAUDE_PLUGIN_ROOT to be expanded in command, got: ${config.command}`);
+		assert.ok(!config.args[1].includes('${CLAUDE_PLUGIN_ROOT}'), `Expected CLAUDE_PLUGIN_ROOT to be expanded in args, got: ${config.args[1]}`);
+		assert.strictEqual(config.env['CLAUDE_PLUGIN_ROOT'], uri.fsPath, 'Expected CLAUDE_PLUGIN_ROOT env var to be set');
+	}));
+});
diff --git a/src/vs/workbench/contrib/chat/test/common/plugins/pluginMarketplaceService.test.ts b/src/vs/workbench/contrib/chat/test/common/plugins/pluginMarketplaceService.test.ts
new file mode 100644
index 0000000000000..35a2c79c2f600
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/common/plugins/pluginMarketplaceService.test.ts
@@ -0,0 +1,358 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { Event } from '../../../../../../base/common/event.js';
+import { observableValue } from '../../../../../../base/common/observable.js';
+import { URI } from '../../../../../../base/common/uri.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
+import { TestConfigurationService } from '../../../../../../platform/configuration/test/common/testConfigurationService.js';
+import { IFileService } from '../../../../../../platform/files/common/files.js';
+import { TestInstantiationService } from '../../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import { ILogService, NullLogService } from '../../../../../../platform/log/common/log.js';
+import { IRequestService } from '../../../../../../platform/request/common/request.js';
+import { IStorageService, InMemoryStorageService } from '../../../../../../platform/storage/common/storage.js';
+import { IWorkspaceTrustManagementService } from '../../../../../../platform/workspace/common/workspaceTrust.js';
+import { ChatConfiguration } from '../../../common/constants.js';
+import { IAgentPluginRepositoryService } from '../../../common/plugins/agentPluginRepositoryService.js';
+import { MarketplaceReferenceKind, MarketplaceType, PluginMarketplaceService, PluginSourceKind, getPluginSourceLabel, parseMarketplaceReference, parseMarketplaceReferences, parsePluginSource } from '../../../common/plugins/pluginMarketplaceService.js';
+import { IWorkspacePluginSettingsService } from '../../../common/plugins/workspacePluginSettingsService.js';
+
+suite('PluginMarketplaceService', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('parses GitHub shorthand marketplace', () => {
+		const parsed = parseMarketplaceReference('microsoft/vscode');
+		assert.ok(parsed);
+		if (!parsed) {
+			return;
+		}
+		assert.strictEqual(parsed.kind, MarketplaceReferenceKind.GitHubShorthand);
+		assert.strictEqual(parsed.cloneUrl, 'https://github.com/microsoft/vscode.git');
+		assert.strictEqual(parsed.canonicalId, 'github:microsoft/vscode');
+		assert.strictEqual(parsed.displayLabel, 'microsoft/vscode');
+		assert.deepStrictEqual(parsed.cacheSegments, ['github.com', 'microsoft', 'vscode']);
+	});
+
+	test('parses direct HTTPS and SSH marketplaces ending in .git', () => {
+		const https = parseMarketplaceReference('https://example.com/org/repo.git');
+		assert.ok(https);
+		if (!https) {
+			return;
+		}
+		assert.strictEqual(https.kind, MarketplaceReferenceKind.GitUri);
+		assert.strictEqual(https.displayLabel, 'https://example.com/org/repo.git');
+		assert.deepStrictEqual(https.cacheSegments, ['example.com', 'org', 'repo']);
+
+		const ssh = parseMarketplaceReference('ssh://git@example.com/org/repo.git');
+		assert.ok(ssh);
+		if (!ssh) {
+			return;
+		}
+		assert.strictEqual(ssh.kind, MarketplaceReferenceKind.GitUri);
+		assert.deepStrictEqual(ssh.cacheSegments, ['git@example.com', 'org', 'repo']);
+	});
+
+	test('parses scp-like git URI marketplaces', () => {
+		const parsed = parseMarketplaceReference('git@example.com:org/repo.git');
+		assert.ok(parsed);
+		if (!parsed) {
+			return;
+		}
+		assert.strictEqual(parsed.kind, MarketplaceReferenceKind.GitUri);
+		assert.strictEqual(parsed.cloneUrl, 'git@example.com:org/repo.git');
+		assert.strictEqual(parsed.canonicalId, 'git:example.com/org/repo.git');
+		assert.deepStrictEqual(parsed.cacheSegments, ['example.com', 'org', 'repo']);
+	});
+
+	test('parses local file marketplace references', () => {
+		const parsed = parseMarketplaceReference('file:///tmp/marketplace-repo');
+		assert.ok(parsed);
+		if (!parsed) {
+			return;
+		}
+		assert.strictEqual(parsed.kind, MarketplaceReferenceKind.LocalFileUri);
+		assert.strictEqual(parsed.localRepositoryUri?.scheme, 'file');
+		assert.strictEqual(parsed.cloneUrl, 'file:///tmp/marketplace-repo');
+		assert.deepStrictEqual(parsed.cacheSegments, []);
+	});
+
+	test('accepts HTTPS and SSH marketplace entries without .git suffix', () => {
+		const https = parseMarketplaceReference('https://example.com/org/repo');
+		assert.ok(https);
+		assert.strictEqual(https?.kind, MarketplaceReferenceKind.GitUri);
+		assert.strictEqual(https?.canonicalId, 'git:example.com/org/repo.git');
+		assert.deepStrictEqual(https?.cacheSegments, ['example.com', 'org', 'repo']);
+
+		const ssh = parseMarketplaceReference('ssh://git@example.com/org/repo');
+		assert.ok(ssh);
+		assert.strictEqual(ssh?.kind, MarketplaceReferenceKind.GitUri);
+		assert.strictEqual(ssh?.canonicalId, 'git:git@example.com/org/repo.git');
+
+		// SCP-style (git@host:path) still requires .git because the colon-path syntax is
+		// unambiguous only for traditional git SSH URLs where .git is conventional.
+		assert.strictEqual(parseMarketplaceReference('git@example.com:org/repo'), undefined);
+	});
+
+	test('parses Azure DevOps HTTPS clone URLs without .git suffix', () => {
+		const parsed = parseMarketplaceReference('https://dev.azure.com/org/project/_git/repo');
+		assert.ok(parsed);
+		assert.strictEqual(parsed?.kind, MarketplaceReferenceKind.GitUri);
+		assert.strictEqual(parsed?.cloneUrl, 'https://dev.azure.com/org/project/_git/repo');
+		assert.strictEqual(parsed?.canonicalId, 'git:dev.azure.com/org/project/_git/repo.git');
+		assert.deepStrictEqual(parsed?.cacheSegments, ['dev.azure.com', 'org', 'project', '_git', 'repo']);
+	});
+
+	test('deduplicates Azure DevOps URLs with and without .git suffix', () => {
+		const parsed = parseMarketplaceReferences([
+			'https://dev.azure.com/org/project/_git/repo',
+			'https://dev.azure.com/org/project/_git/repo.git',
+		]);
+		assert.strictEqual(parsed.length, 1);
+		assert.strictEqual(parsed[0].canonicalId, 'git:dev.azure.com/org/project/_git/repo.git');
+	});
+
+	test('parses HTTPS URI with trailing slash after .git', () => {
+		const parsed = parseMarketplaceReference('https://example.com/org/repo.git/');
+		assert.ok(parsed);
+		if (!parsed) {
+			return;
+		}
+		assert.strictEqual(parsed.kind, MarketplaceReferenceKind.GitUri);
+		assert.strictEqual(parsed.canonicalId, 'git:example.com/org/repo.git');
+		assert.deepStrictEqual(parsed.cacheSegments, ['example.com', 'org', 'repo']);
+	});
+
+	test('deduplicates equivalent Git URI forms but keeps shorthand distinct', () => {
+		const parsed = parseMarketplaceReferences([
+			'microsoft/vscode',
+			'https://github.com/microsoft/vscode.git',
+			'git@github.com:microsoft/vscode.git',
+		]);
+
+		assert.deepStrictEqual(parsed.map(r => r.canonicalId), [
+			'github:microsoft/vscode',
+			'git:github.com/microsoft/vscode.git',
+		]);
+	});
+
+	test('parseMarketplaceReferences ignores non-string entries', () => {
+		const parsed = parseMarketplaceReferences([null, 42, {}, 'microsoft/vscode']);
+		assert.strictEqual(parsed.length, 1);
+		assert.strictEqual(parsed[0].canonicalId, 'github:microsoft/vscode');
+	});
+});
+
+suite('PluginMarketplaceService - getMarketplacePluginMetadata', () => {
+	const store = ensureNoDisposablesAreLeakedInTestSuite();
+
+	const marketplaceRef = parseMarketplaceReference('microsoft/plugins')!;
+
+	function createService(): PluginMarketplaceService {
+		const instantiationService = store.add(new TestInstantiationService());
+
+		instantiationService.stub(IConfigurationService, new TestConfigurationService({
+			[ChatConfiguration.PluginMarketplaces]: ['microsoft/plugins'],
+			[ChatConfiguration.PluginsEnabled]: true,
+		}));
+		instantiationService.stub(IFileService, {} as unknown as IFileService);
+		instantiationService.stub(IAgentPluginRepositoryService, {} as unknown as IAgentPluginRepositoryService);
+		instantiationService.stub(ILogService, new NullLogService());
+		instantiationService.stub(IRequestService, {} as unknown as IRequestService);
+		instantiationService.stub(IStorageService, store.add(new InMemoryStorageService()));
+		instantiationService.stub(IWorkspacePluginSettingsService, {
+			extraMarketplaces: observableValue('test.extraMarketplaces', []),
+			enabledPlugins: observableValue('test.enabledPlugins', new Map()),
+		} as Partial<IWorkspacePluginSettingsService> as IWorkspacePluginSettingsService);
+		instantiationService.stub(IWorkspaceTrustManagementService, {
+			isWorkspaceTrusted: () => true,
+			onDidChangeTrust: Event.None,
+		} as Partial<IWorkspaceTrustManagementService> as IWorkspaceTrustManagementService);
+
+		return store.add(instantiationService.createInstance(PluginMarketplaceService));
+	}
+
+	test('returns metadata for an installed plugin', () => {
+		const service = createService();
+		const pluginUri = URI.file('/cache/agentPlugins/my-plugin');
+		const plugin = {
+			name: 'my-plugin',
+			description: 'A test plugin',
+			version: '2.0.0',
+			source: 'plugins/my-plugin',
+			sourceDescriptor: { kind: PluginSourceKind.RelativePath, path: 'plugins/my-plugin' } as const,
+			marketplace: marketplaceRef.displayLabel,
+			marketplaceReference: marketplaceRef,
+			marketplaceType: MarketplaceType.Copilot,
+		};
+
+		service.addInstalledPlugin(pluginUri, plugin);
+		const result = service.getMarketplacePluginMetadata(pluginUri);
+
+		assert.deepStrictEqual(result, plugin);
+	});
+
+	test('returns undefined for a URI that is not installed', () => {
+		const service = createService();
+		const result = service.getMarketplacePluginMetadata(URI.file('/some/other/path'));
+		assert.strictEqual(result, undefined);
+	});
+
+	test('returns undefined when no plugins are installed', () => {
+		const service = createService();
+		const result = service.getMarketplacePluginMetadata(URI.file('/any/path'));
+		assert.strictEqual(result, undefined);
+	});
+});
+
+suite('parsePluginSource', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	const logContext = {
+		pluginName: 'test',
+		logService: new NullLogService(),
+		logPrefix: '[test]',
+	};
+
+	test('parses string source as RelativePath', () => {
+		const result = parsePluginSource('./my-plugin', undefined, logContext);
+		assert.deepStrictEqual(result, { kind: PluginSourceKind.RelativePath, path: 'my-plugin' });
+	});
+
+	test('parses string source with pluginRoot', () => {
+		const result = parsePluginSource('sub', 'plugins', logContext);
+		assert.deepStrictEqual(result, { kind: PluginSourceKind.RelativePath, path: 'plugins/sub' });
+	});
+
+	test('parses undefined source as RelativePath using pluginRoot', () => {
+		const result = parsePluginSource(undefined, 'root', logContext);
+		assert.deepStrictEqual(result, { kind: PluginSourceKind.RelativePath, path: 'root' });
+	});
+
+	test('parses empty string source as RelativePath using pluginRoot', () => {
+		const result = parsePluginSource('', 'base', logContext);
+		assert.deepStrictEqual(result, { kind: PluginSourceKind.RelativePath, path: 'base' });
+	});
+
+	test('returns undefined for empty source without pluginRoot', () => {
+		assert.strictEqual(parsePluginSource('', undefined, logContext), undefined);
+	});
+
+	test('parses github object source', () => {
+		const result = parsePluginSource({ source: 'github', repo: 'owner/repo' }, undefined, logContext);
+		assert.deepStrictEqual(result, { kind: PluginSourceKind.GitHub, repo: 'owner/repo', ref: undefined, sha: undefined });
+	});
+
+	test('parses github object source with ref and sha', () => {
+		const result = parsePluginSource({ source: 'github', repo: 'owner/repo', ref: 'v2.0.0', sha: 'a1b2c3d4e5f6a7b8c9d0e1f2a3b4c5d6e7f8a9b0' }, undefined, logContext);
+		assert.deepStrictEqual(result, { kind: PluginSourceKind.GitHub, repo: 'owner/repo', ref: 'v2.0.0', sha: 'a1b2c3d4e5f6a7b8c9d0e1f2a3b4c5d6e7f8a9b0' });
+	});
+
+	test('returns undefined for github source missing repo', () => {
+		assert.strictEqual(parsePluginSource({ source: 'github' }, undefined, logContext), undefined);
+	});
+
+	test('returns undefined for github source with invalid repo format', () => {
+		assert.strictEqual(parsePluginSource({ source: 'github', repo: 'owner' }, undefined, logContext), undefined);
+	});
+
+	test('returns undefined for github source with invalid sha', () => {
+		assert.strictEqual(parsePluginSource({ source: 'github', repo: 'owner/repo', sha: 'abc123' }, undefined, logContext), undefined);
+	});
+
+	test('parses url object source', () => {
+		const result = parsePluginSource({ source: 'url', url: 'https://gitlab.com/team/plugin.git' }, undefined, logContext);
+		assert.deepStrictEqual(result, { kind: PluginSourceKind.GitUrl, url: 'https://gitlab.com/team/plugin.git', ref: undefined, sha: undefined });
+	});
+
+	test('returns undefined for url source missing url field', () => {
+		assert.strictEqual(parsePluginSource({ source: 'url' }, undefined, logContext), undefined);
+	});
+
+	test('returns undefined for url source not ending in .git', () => {
+		assert.strictEqual(parsePluginSource({ source: 'url', url: 'https://gitlab.com/team/plugin' }, undefined, logContext), undefined);
+	});
+
+	test('parses npm object source', () => {
+		const result = parsePluginSource({ source: 'npm', package: '@acme/claude-plugin' }, undefined, logContext);
+		assert.deepStrictEqual(result, { kind: PluginSourceKind.Npm, package: '@acme/claude-plugin', version: undefined, registry: undefined });
+	});
+
+	test('parses npm object source with version and registry', () => {
+		const result = parsePluginSource({ source: 'npm', package: '@acme/claude-plugin', version: '2.1.0', registry: 'https://npm.example.com' }, undefined, logContext);
+		assert.deepStrictEqual(result, { kind: PluginSourceKind.Npm, package: '@acme/claude-plugin', version: '2.1.0', registry: 'https://npm.example.com' });
+	});
+
+	test('returns undefined for npm source missing package', () => {
+		assert.strictEqual(parsePluginSource({ source: 'npm' }, undefined, logContext), undefined);
+	});
+
+	test('returns undefined for npm source with non-string version', () => {
+		assert.strictEqual(parsePluginSource({ source: 'npm', package: '@acme/claude-plugin', version: 123 } as never, undefined, logContext), undefined);
+	});
+
+	test('parses pip object source', () => {
+		const result = parsePluginSource({ source: 'pip', package: 'my-plugin' }, undefined, logContext);
+		assert.deepStrictEqual(result, { kind: PluginSourceKind.Pip, package: 'my-plugin', version: undefined, registry: undefined });
+	});
+
+	test('parses pip object source with version and registry', () => {
+		const result = parsePluginSource({ source: 'pip', package: 'my-plugin', version: '1.0.0', registry: 'https://pypi.example.com' }, undefined, logContext);
+		assert.deepStrictEqual(result, { kind: PluginSourceKind.Pip, package: 'my-plugin', version: '1.0.0', registry: 'https://pypi.example.com' });
+	});
+
+	test('returns undefined for pip source missing package', () => {
+		assert.strictEqual(parsePluginSource({ source: 'pip' }, undefined, logContext), undefined);
+	});
+
+	test('returns undefined for pip source with non-string registry', () => {
+		assert.strictEqual(parsePluginSource({ source: 'pip', package: 'my-plugin', registry: 42 } as never, undefined, logContext), undefined);
+	});
+
+	test('returns undefined for unknown source kind', () => {
+		assert.strictEqual(parsePluginSource({ source: 'unknown' }, undefined, logContext), undefined);
+	});
+
+	test('returns undefined for object source without source discriminant', () => {
+		assert.strictEqual(parsePluginSource({ package: 'test' } as never, undefined, logContext), undefined);
+	});
+});
+
+suite('getPluginSourceLabel', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('formats relative path', () => {
+		assert.strictEqual(getPluginSourceLabel({ kind: PluginSourceKind.RelativePath, path: 'plugins/foo' }), 'plugins/foo');
+	});
+
+	test('formats empty relative path', () => {
+		assert.strictEqual(getPluginSourceLabel({ kind: PluginSourceKind.RelativePath, path: '' }), '.');
+	});
+
+	test('formats github source', () => {
+		assert.strictEqual(getPluginSourceLabel({ kind: PluginSourceKind.GitHub, repo: 'owner/repo' }), 'owner/repo');
+	});
+
+	test('formats url source', () => {
+		assert.strictEqual(getPluginSourceLabel({ kind: PluginSourceKind.GitUrl, url: 'https://example.com/repo.git' }), 'https://example.com/repo.git');
+	});
+
+	test('formats npm source without version', () => {
+		assert.strictEqual(getPluginSourceLabel({ kind: PluginSourceKind.Npm, package: '@acme/plugin' }), '@acme/plugin');
+	});
+
+	test('formats npm source with version', () => {
+		assert.strictEqual(getPluginSourceLabel({ kind: PluginSourceKind.Npm, package: '@acme/plugin', version: '1.0.0' }), '@acme/plugin@1.0.0');
+	});
+
+	test('formats pip source without version', () => {
+		assert.strictEqual(getPluginSourceLabel({ kind: PluginSourceKind.Pip, package: 'my-plugin' }), 'my-plugin');
+	});
+
+	test('formats pip source with version', () => {
+		assert.strictEqual(getPluginSourceLabel({ kind: PluginSourceKind.Pip, package: 'my-plugin', version: '2.0' }), 'my-plugin==2.0');
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/common/plugins/shellQuotePluginRootInCommand.test.ts b/src/vs/workbench/contrib/chat/test/common/plugins/shellQuotePluginRootInCommand.test.ts
new file mode 100644
index 0000000000000..de66a7f4b5cac
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/common/plugins/shellQuotePluginRootInCommand.test.ts
@@ -0,0 +1,126 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { shellQuotePluginRootInCommand } from '../../../common/plugins/agentPluginServiceImpl.js';
+
+suite('shellQuotePluginRootInCommand', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	const TOKEN = '${PLUGIN_ROOT}';
+
+	test('returns command unchanged when token is not present', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('echo hello', '/safe/path', TOKEN),
+			'echo hello',
+		);
+	});
+
+	test('plain replacement when path has no special characters', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('${PLUGIN_ROOT}/run.sh', '/safe/path', TOKEN),
+			'/safe/path/run.sh',
+		);
+	});
+
+	test('plain replacement for multiple occurrences with safe path', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('${PLUGIN_ROOT}/a && ${PLUGIN_ROOT}/b', '/safe', TOKEN),
+			'/safe/a && /safe/b',
+		);
+	});
+
+	test('quotes path with spaces', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('${PLUGIN_ROOT}/run.sh', '/path with spaces', TOKEN),
+			'"/path with spaces/run.sh"',
+		);
+	});
+
+	test('quotes path with ampersand', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('${PLUGIN_ROOT}/run.sh', '/path&dir', TOKEN),
+			'"/path&dir/run.sh"',
+		);
+	});
+
+	test('quotes multiple occurrences with unsafe path', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('${PLUGIN_ROOT}/a && ${PLUGIN_ROOT}/b', '/my dir', TOKEN),
+			'"/my dir/a" && "/my dir/b"',
+		);
+	});
+
+	test('does not double-quote when already in double quotes', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('"${PLUGIN_ROOT}/run.sh"', '/my dir', TOKEN),
+			'"/my dir/run.sh"',
+		);
+	});
+
+	test('does not double-quote when already in single quotes', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand(`'\${PLUGIN_ROOT}/run.sh'`, '/my dir', TOKEN),
+			`'/my dir/run.sh'`,
+		);
+	});
+
+	test('escapes embedded double-quote characters in path', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('${PLUGIN_ROOT}/run.sh', '/path"with"quotes', TOKEN),
+			'"/path\\"with\\"quotes/run.sh"',
+		);
+	});
+
+	test('handles token without trailing path suffix', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('cd ${PLUGIN_ROOT} && run', '/my dir', TOKEN),
+			'cd "/my dir" && run',
+		);
+	});
+
+	test('does not consume shell operators adjacent to token', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('cd ${PLUGIN_ROOT}&& echo ok', '/my dir', TOKEN),
+			'cd "/my dir"&& echo ok',
+		);
+	});
+
+	test('handles token at start, middle and end of command', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('${PLUGIN_ROOT}/a ${PLUGIN_ROOT}/b ${PLUGIN_ROOT}/c', '/sp ace', TOKEN),
+			'"/sp ace/a" "/sp ace/b" "/sp ace/c"',
+		);
+	});
+
+	test('uses default CLAUDE_PLUGIN_ROOT token when not specified', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('${CLAUDE_PLUGIN_ROOT}/run.sh', '/safe/path', '${CLAUDE_PLUGIN_ROOT}'),
+			'/safe/path/run.sh',
+		);
+	});
+
+	test('uses default CLAUDE_PLUGIN_ROOT token with quoting', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('${CLAUDE_PLUGIN_ROOT}/run.sh', '/my dir', '${CLAUDE_PLUGIN_ROOT}'),
+			'"/my dir/run.sh"',
+		);
+	});
+
+	test('handles Windows-style paths with spaces', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('${PLUGIN_ROOT}\\scripts\\run.bat', 'C:\\Program Files\\plugin', TOKEN),
+			'"C:\\Program Files\\plugin\\scripts\\run.bat"',
+		);
+	});
+
+	test('handles path with parentheses', () => {
+		assert.strictEqual(
+			shellQuotePluginRootInCommand('${PLUGIN_ROOT}/run.sh', '/path(1)', TOKEN),
+			'"/path(1)/run.sh"',
+		);
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/common/plugins/workspacePluginSettingsService.test.ts b/src/vs/workbench/contrib/chat/test/common/plugins/workspacePluginSettingsService.test.ts
new file mode 100644
index 0000000000000..0a1434d439db2
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/common/plugins/workspacePluginSettingsService.test.ts
@@ -0,0 +1,246 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { VSBuffer } from '../../../../../../base/common/buffer.js';
+import { Schemas } from '../../../../../../base/common/network.js';
+import { URI } from '../../../../../../base/common/uri.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { runWithFakedTimers } from '../../../../../../base/test/common/timeTravelScheduler.js';
+import { waitForState } from '../../../../../../base/common/observable.js';
+import { FileService } from '../../../../../../platform/files/common/fileService.js';
+import { InMemoryFileSystemProvider } from '../../../../../../platform/files/common/inMemoryFilesystemProvider.js';
+import { NullLogService } from '../../../../../../platform/log/common/log.js';
+import { TestContextService } from '../../../../../test/common/workbenchTestServices.js';
+import { testWorkspace } from '../../../../../../platform/workspace/test/common/testWorkspace.js';
+import { WorkspacePluginSettingsService } from '../../../common/plugins/workspacePluginSettingsService.js';
+
+suite('WorkspacePluginSettingsService', () => {
+	const store = ensureNoDisposablesAreLeakedInTestSuite();
+	const logService = new NullLogService();
+
+	let fileService: FileService;
+	let workspaceContextService: TestContextService;
+	const workspaceRoot = URI.from({ scheme: Schemas.inMemory, path: '/workspace' });
+
+	setup(() => {
+		workspaceContextService = new TestContextService(testWorkspace(workspaceRoot));
+		fileService = store.add(new FileService(logService));
+		store.add(fileService.registerProvider(Schemas.inMemory, store.add(new InMemoryFileSystemProvider())));
+	});
+
+	function createService(): WorkspacePluginSettingsService {
+		return store.add(new WorkspacePluginSettingsService(
+			fileService,
+			workspaceContextService,
+			logService,
+		));
+	}
+
+	async function writeClaudeSettings(content: string): Promise<void> {
+		const uri = URI.from({ scheme: Schemas.inMemory, path: '/workspace/.claude/settings.json' });
+		await fileService.writeFile(uri, VSBuffer.fromString(content));
+	}
+
+	async function writeClaudeLocalSettings(content: string): Promise<void> {
+		const uri = URI.from({ scheme: Schemas.inMemory, path: '/workspace/.claude/settings.local.json' });
+		await fileService.writeFile(uri, VSBuffer.fromString(content));
+	}
+
+	async function writeCopilotSettings(content: string): Promise<void> {
+		const uri = URI.from({ scheme: Schemas.inMemory, path: '/workspace/.github/copilot/settings.json' });
+		await fileService.writeFile(uri, VSBuffer.fromString(content));
+	}
+
+	// --- enabledPlugins parsing ---
+
+	test('parses enabledPlugins from Claude settings', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		await writeClaudeSettings(JSON.stringify({
+			enabledPlugins: {
+				'my-plugin@my-marketplace': true,
+				'disabled-plugin@my-marketplace': false,
+			}
+		}));
+
+		const service = createService();
+		await waitForState(service.enabledPlugins, v => v.size > 0);
+
+		const enabled = service.enabledPlugins.get();
+		assert.strictEqual(enabled.get('my-plugin@my-marketplace'), true);
+		assert.strictEqual(enabled.get('disabled-plugin@my-marketplace'), false);
+		assert.strictEqual(enabled.size, 2);
+	}));
+
+	test('settings.local.json overrides settings.json for enabledPlugins', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		await writeClaudeSettings(JSON.stringify({
+			enabledPlugins: {
+				'my-plugin@mp': true,
+				'other-plugin@mp': true,
+			}
+		}));
+		await writeClaudeLocalSettings(JSON.stringify({
+			enabledPlugins: {
+				'my-plugin@mp': false,
+			}
+		}));
+
+		const service = createService();
+		await waitForState(service.enabledPlugins, v => v.size > 0);
+
+		const enabled = service.enabledPlugins.get();
+		assert.strictEqual(enabled.get('my-plugin@mp'), false, 'local should override shared');
+		assert.strictEqual(enabled.get('other-plugin@mp'), true, 'non-overridden key preserved');
+	}));
+
+	test('merges enabledPlugins from Claude and Copilot settings', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		await writeClaudeSettings(JSON.stringify({
+			enabledPlugins: { 'from-claude@mp': true }
+		}));
+		await writeCopilotSettings(JSON.stringify({
+			enabledPlugins: { 'from-copilot@mp': true }
+		}));
+
+		const service = createService();
+		await waitForState(service.enabledPlugins, v => v.size >= 2);
+
+		const enabled = service.enabledPlugins.get();
+		assert.strictEqual(enabled.get('from-claude@mp'), true);
+		assert.strictEqual(enabled.get('from-copilot@mp'), true);
+	}));
+
+	test('Claude enabledPlugins take precedence over Copilot for same key', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		await writeClaudeSettings(JSON.stringify({
+			enabledPlugins: { 'shared-plugin@mp': false }
+		}));
+		await writeCopilotSettings(JSON.stringify({
+			enabledPlugins: { 'shared-plugin@mp': true }
+		}));
+
+		const service = createService();
+		await waitForState(service.enabledPlugins, v => v.size > 0);
+
+		const enabled = service.enabledPlugins.get();
+		assert.strictEqual(enabled.get('shared-plugin@mp'), false, 'Claude should win');
+	}));
+
+	// --- extraKnownMarketplaces parsing ---
+
+	test('parses GitHub shorthand from extraKnownMarketplaces', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		await writeClaudeSettings(JSON.stringify({
+			extraKnownMarketplaces: {
+				'my-marketplace': {
+					source: 'github',
+					repo: 'owner/repo',
+				}
+			}
+		}));
+
+		const service = createService();
+		await waitForState(service.extraMarketplaces, v => v.length > 0);
+
+		const marketplaces = service.extraMarketplaces.get();
+		assert.strictEqual(marketplaces.length, 1);
+		assert.strictEqual(marketplaces[0].name, 'my-marketplace');
+		assert.strictEqual(marketplaces[0].reference.displayLabel, 'my-marketplace');
+		assert.strictEqual(marketplaces[0].reference.githubRepo, 'owner/repo');
+	}));
+
+	test('parses nested source object from extraKnownMarketplaces', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		await writeClaudeSettings(JSON.stringify({
+			extraKnownMarketplaces: {
+				'nested-mp': {
+					source: {
+						source: 'github',
+						repo: 'nested-owner/nested-repo',
+					}
+				}
+			}
+		}));
+
+		const service = createService();
+		await waitForState(service.extraMarketplaces, v => v.length > 0);
+
+		const marketplaces = service.extraMarketplaces.get();
+		assert.strictEqual(marketplaces.length, 1);
+		assert.strictEqual(marketplaces[0].reference.githubRepo, 'nested-owner/nested-repo');
+		assert.strictEqual(marketplaces[0].reference.displayLabel, 'nested-mp');
+	}));
+
+	test('deduplicates marketplaces across Claude and Copilot by canonical ID', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		await writeClaudeSettings(JSON.stringify({
+			extraKnownMarketplaces: {
+				'claude-name': { source: 'github', repo: 'owner/repo' }
+			}
+		}));
+		await writeCopilotSettings(JSON.stringify({
+			extraKnownMarketplaces: {
+				'copilot-name': { source: 'github', repo: 'owner/repo' }
+			}
+		}));
+
+		const service = createService();
+		await waitForState(service.extraMarketplaces, v => v.length > 0);
+
+		const marketplaces = service.extraMarketplaces.get();
+		assert.strictEqual(marketplaces.length, 1, 'should deduplicate by canonical ID');
+		assert.strictEqual(marketplaces[0].name, 'claude-name', 'Claude entry should win');
+	}));
+
+	// --- Invalid input handling ---
+
+	test('ignores invalid enabledPlugins shapes', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		await writeClaudeSettings(JSON.stringify({
+			enabledPlugins: 'not-an-object'
+		}));
+
+		const service = createService();
+		// Give the async read a chance to complete with faked timers.
+		await new Promise<void>(r => queueMicrotask(r));
+
+		assert.strictEqual(service.enabledPlugins.get().size, 0);
+	}));
+
+	test('ignores non-boolean values in enabledPlugins', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		await writeClaudeSettings(JSON.stringify({
+			enabledPlugins: {
+				'valid@mp': true,
+				'number@mp': 42,
+				'string@mp': 'yes',
+			}
+		}));
+
+		const service = createService();
+		await waitForState(service.enabledPlugins, v => v.size > 0);
+
+		const enabled = service.enabledPlugins.get();
+		assert.strictEqual(enabled.size, 1);
+		assert.strictEqual(enabled.get('valid@mp'), true);
+	}));
+
+	test('ignores non-object marketplace entries', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		await writeClaudeSettings(JSON.stringify({
+			extraKnownMarketplaces: {
+				'valid': { source: 'github', repo: 'owner/repo' },
+				'invalid-string': 'not-valid',
+				'invalid-number': 42,
+			}
+		}));
+
+		const service = createService();
+		await waitForState(service.extraMarketplaces, v => v.length > 0);
+
+		const marketplaces = service.extraMarketplaces.get();
+		assert.strictEqual(marketplaces.length, 1);
+		assert.strictEqual(marketplaces[0].name, 'valid');
+	}));
+
+	test('returns empty observables when no settings files exist', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		const service = createService();
+		await new Promise<void>(r => queueMicrotask(r));
+
+		assert.strictEqual(service.enabledPlugins.get().size, 0);
+		assert.strictEqual(service.extraMarketplaces.get().length, 0);
+	}));
+});
diff --git a/src/vs/workbench/contrib/chat/test/common/promptSyntax/computeAutomaticInstructions.test.ts b/src/vs/workbench/contrib/chat/test/common/promptSyntax/computeAutomaticInstructions.test.ts
index 8a0dcd1bef3e0..7576f57cfad29 100644
--- a/src/vs/workbench/contrib/chat/test/common/promptSyntax/computeAutomaticInstructions.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/promptSyntax/computeAutomaticInstructions.test.ts
@@ -24,9 +24,10 @@ import { ILogService, NullLogService } from '../../../../../../platform/log/comm
 import { ITelemetryService } from '../../../../../../platform/telemetry/common/telemetry.js';
 import { NullTelemetryService } from '../../../../../../platform/telemetry/common/telemetryUtils.js';
 import { IWorkspaceContextService } from '../../../../../../platform/workspace/common/workspace.js';
+import { IWorkspaceTrustManagementService } from '../../../../../../platform/workspace/common/workspaceTrust.js';
 import { testWorkspace } from '../../../../../../platform/workspace/test/common/testWorkspace.js';
 import { IUserDataProfileService } from '../../../../../services/userDataProfile/common/userDataProfile.js';
-import { TestContextService, TestUserDataProfileService } from '../../../../../test/common/workbenchTestServices.js';
+import { TestContextService, TestUserDataProfileService, TestWorkspaceTrustManagementService } from '../../../../../test/common/workbenchTestServices.js';
 import { ChatRequestVariableSet, isPromptFileVariableEntry, isPromptTextVariableEntry, toFileVariableEntry } from '../../../common/attachments/chatVariableEntries.js';
 import { ComputeAutomaticInstructions, getFilePath, InstructionsCollectionEvent } from '../../../common/promptSyntax/computeAutomaticInstructions.js';
 import { PromptsConfig } from '../../../common/promptSyntax/config/config.js';
@@ -59,6 +60,7 @@ suite('ComputeAutomaticInstructions', () => {
 	let fileService: IFileService;
 	let toolsService: ILanguageModelToolsService;
 	let fileSystemProvider: TestInMemoryFileSystemProviderWithRealPath;
+	let workspaceTrustService: TestWorkspaceTrustManagementService;
 
 	setup(async () => {
 		instaService = disposables.add(new TestInstantiationService());
@@ -75,6 +77,7 @@ suite('ComputeAutomaticInstructions', () => {
 		testConfigService.setUserConfiguration(PromptsConfig.USE_AGENT_SKILLS, true);
 		testConfigService.setUserConfiguration(PromptsConfig.INCLUDE_APPLYING_INSTRUCTIONS, true);
 		testConfigService.setUserConfiguration(PromptsConfig.INCLUDE_REFERENCED_INSTRUCTIONS, true);
+		testConfigService.setUserConfiguration(PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS, false);
 		testConfigService.setUserConfiguration(PromptsConfig.INSTRUCTIONS_LOCATION_KEY, { [INSTRUCTIONS_DEFAULT_SOURCE_FOLDER]: true, [CLAUDE_RULES_SOURCE_FOLDER]: true });
 		testConfigService.setUserConfiguration(PromptsConfig.PROMPT_LOCATIONS_KEY, { [PROMPT_DEFAULT_SOURCE_FOLDER]: true });
 		testConfigService.setUserConfiguration(PromptsConfig.MODE_LOCATION_KEY, { [LEGACY_MODE_DEFAULT_SOURCE_FOLDER]: true });
@@ -90,6 +93,9 @@ suite('ComputeAutomaticInstructions', () => {
 			activateByEvent: () => Promise.resolve()
 		});
 
+		workspaceTrustService = disposables.add(new TestWorkspaceTrustManagementService());
+		instaService.stub(IWorkspaceTrustManagementService, workspaceTrustService);
+
 		fileService = disposables.add(instaService.createInstance(FileService));
 		instaService.stub(IFileService, fileService);
 
@@ -183,8 +189,7 @@ suite('ComputeAutomaticInstructions', () => {
 
 		instaService.stub(IAgentPluginService, {
 			plugins: observableValue('testPlugins', []),
-			allPlugins: observableValue('testAllPlugins', []),
-			setPluginEnabled: () => { },
+			enablementModel: { readEnabled: () => 2 /* EnabledProfile */, setEnabled: () => { } },
 		});
 
 		service = disposables.add(instaService.createInstance(PromptsService));
@@ -1626,6 +1631,126 @@ suite('ComputeAutomaticInstructions', () => {
 		assert.ok(!paths.includes(`${rootFolder}/.claude/CLAUDE.md`), 'Should not include .claude/CLAUDE.md when disabled');
 	});
 
+	test('should collect parent folder CLAUDE configurations when includeWorkspaceFolderParents is enabled', async () => {
+		const parentFolderName = 'collect-claude-parent-test';
+		const parentFolder = `/${parentFolderName}`;
+		const rootFolder = `${parentFolder}/repo`;
+		const rootFolderUri = URI.file(rootFolder);
+
+		workspaceContextService.setWorkspace(testWorkspace(rootFolderUri));
+
+		await mockFiles(fileService, [
+			{
+				path: `${parentFolder}/.git/HEAD`,
+				contents: ['ref: refs/heads/main'],
+			},
+			{
+				path: `${parentFolder}/CLAUDE.md`,
+				contents: ['Parent Claude guidelines'],
+			},
+			{
+				path: `${parentFolder}/.claude/CLAUDE.md`,
+				contents: ['Parent .claude Claude guidelines'],
+			},
+			{
+				path: `${rootFolder}/src/file.ts`,
+				contents: ['console.log("test");'],
+			},
+		]);
+
+		testConfigService.setUserConfiguration(PromptsConfig.USE_CLAUDE_MD, true);
+		testConfigService.setUserConfiguration(PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS, false);
+
+		await workspaceTrustService.setTrustedUris([URI.file(parentFolder)]);
+
+		const disabledParentContextComputer = instaService.createInstance(ComputeAutomaticInstructions, ChatModeKind.Agent, undefined, undefined, undefined);
+		const disabledParentVariables = new ChatRequestVariableSet();
+		disabledParentVariables.add(toFileVariableEntry(URI.joinPath(rootFolderUri, 'src/file.ts')));
+
+		await disabledParentContextComputer.collect(disabledParentVariables, CancellationToken.None);
+
+		let paths = disabledParentVariables.asArray()
+			.filter(v => isPromptFileVariableEntry(v))
+			.map(i => isPromptFileVariableEntry(i) ? i.value.path : undefined);
+		assert.ok(!paths.includes(`${parentFolder}/CLAUDE.md`), 'Should not include parent CLAUDE.md when parent search is disabled');
+		assert.ok(!paths.includes(`${parentFolder}/.claude/CLAUDE.md`), 'Should not include parent .claude/CLAUDE.md when parent search is disabled');
+
+		// Parent folder settings should allow finding both root and .claude CLAUDE files above the workspace folder.
+		testConfigService.setUserConfiguration(PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS, true);
+
+		const enabledParentContextComputer = instaService.createInstance(ComputeAutomaticInstructions, ChatModeKind.Agent, undefined, undefined, undefined);
+		const enabledParentVariables = new ChatRequestVariableSet();
+		enabledParentVariables.add(toFileVariableEntry(URI.joinPath(rootFolderUri, 'src/file.ts')));
+
+		await enabledParentContextComputer.collect(enabledParentVariables, CancellationToken.None);
+
+		paths = enabledParentVariables.asArray()
+			.filter(v => isPromptFileVariableEntry(v))
+			.map(i => isPromptFileVariableEntry(i) ? i.value.path : undefined);
+		assert.ok(paths.includes(`${parentFolder}/CLAUDE.md`), 'Should include parent CLAUDE.md when parent search is enabled');
+		assert.ok(paths.includes(`${parentFolder}/.claude/CLAUDE.md`), 'Should include parent .claude/CLAUDE.md when parent search is enabled');
+	});
+
+	test('should collect parent folder copilot-instructions.md and AGENTS.md when includeWorkspaceFolderParents is enabled', async () => {
+		const parentFolderName = 'collect-agent-parent-test';
+		const parentFolder = `/${parentFolderName}`;
+		const rootFolder = `${parentFolder}/repo`;
+		const rootFolderUri = URI.file(rootFolder);
+
+		workspaceContextService.setWorkspace(testWorkspace(rootFolderUri));
+
+		await mockFiles(fileService, [
+			{
+				path: `${parentFolder}/.git/HEAD`,
+				contents: ['ref: refs/heads/main'],
+			},
+			{
+				path: `${parentFolder}/.github/copilot-instructions.md`,
+				contents: ['Parent copilot instructions'],
+			},
+			{
+				path: `${parentFolder}/AGENTS.md`,
+				contents: ['Parent agent guidelines'],
+			},
+			{
+				path: `${rootFolder}/src/file.ts`,
+				contents: ['console.log("test");'],
+			},
+		]);
+
+		testConfigService.setUserConfiguration(PromptsConfig.USE_COPILOT_INSTRUCTION_FILES, true);
+		testConfigService.setUserConfiguration(PromptsConfig.USE_AGENT_MD, true);
+		testConfigService.setUserConfiguration(PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS, false);
+
+		await workspaceTrustService.setTrustedUris([URI.file(parentFolder)]);
+
+		const disabledParentContextComputer = instaService.createInstance(ComputeAutomaticInstructions, ChatModeKind.Agent, undefined, undefined, undefined);
+		const disabledParentVariables = new ChatRequestVariableSet();
+		disabledParentVariables.add(toFileVariableEntry(URI.joinPath(rootFolderUri, 'src/file.ts')));
+
+		await disabledParentContextComputer.collect(disabledParentVariables, CancellationToken.None);
+
+		let paths = disabledParentVariables.asArray()
+			.filter(v => isPromptFileVariableEntry(v))
+			.map(i => isPromptFileVariableEntry(i) ? i.value.path : undefined);
+		assert.ok(!paths.includes(`${parentFolder}/.github/copilot-instructions.md`), 'Should not include parent copilot-instructions.md when parent search is disabled');
+		assert.ok(!paths.includes(`${parentFolder}/AGENTS.md`), 'Should not include parent AGENTS.md when parent search is disabled');
+
+		testConfigService.setUserConfiguration(PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS, true);
+
+		const enabledParentContextComputer = instaService.createInstance(ComputeAutomaticInstructions, ChatModeKind.Agent, undefined, undefined, undefined);
+		const enabledParentVariables = new ChatRequestVariableSet();
+		enabledParentVariables.add(toFileVariableEntry(URI.joinPath(rootFolderUri, 'src/file.ts')));
+
+		await enabledParentContextComputer.collect(enabledParentVariables, CancellationToken.None);
+
+		paths = enabledParentVariables.asArray()
+			.filter(v => isPromptFileVariableEntry(v))
+			.map(i => isPromptFileVariableEntry(i) ? i.value.path : undefined);
+		assert.ok(paths.includes(`${parentFolder}/.github/copilot-instructions.md`), 'Should include parent copilot-instructions.md when parent search is enabled');
+		assert.ok(paths.includes(`${parentFolder}/AGENTS.md`), 'Should include parent AGENTS.md when parent search is enabled');
+	});
+
 	test('should collect ~/.claude/CLAUDE.md when enabled', async () => {
 		const rootFolderName = 'collect-claude-home-test';
 		const rootFolder = `/${rootFolderName}`;
diff --git a/src/vs/workbench/contrib/chat/test/common/promptSyntax/config/promptFileLocations.test.ts b/src/vs/workbench/contrib/chat/test/common/promptSyntax/config/promptFileLocations.test.ts
index f6d859e9f2736..f7e22613dee3b 100644
--- a/src/vs/workbench/contrib/chat/test/common/promptSyntax/config/promptFileLocations.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/promptSyntax/config/promptFileLocations.test.ts
@@ -48,6 +48,36 @@ suite('promptFileLocations', function () {
 			assert.strictEqual(getPromptFileType(uri), undefined);
 		});
 
+		test('.md files in .claude/agents/ subfolder should NOT be recognized as agent files', () => {
+			const uri = URI.file('/workspace/.claude/agents/subfolder/test.md');
+			assert.strictEqual(getPromptFileType(uri), undefined);
+		});
+
+		test('.md files in ~/.copilot/agents/ subfolder should NOT be recognized as agent files', () => {
+			const uri = URI.file('/home/user/.copilot/agents/subfolder/test.md');
+			assert.strictEqual(getPromptFileType(uri), undefined);
+		});
+
+		test('.md files in .claude/agents/ folder should be recognized as agent files', () => {
+			const uri = URI.file('/workspace/.claude/agents/demonstrate.md');
+			assert.strictEqual(getPromptFileType(uri), PromptsType.agent);
+		});
+
+		test('README.md in .claude/agents/ should NOT be recognized as agent file', () => {
+			const uri = URI.file('/workspace/.claude/agents/README.md');
+			assert.strictEqual(getPromptFileType(uri), undefined);
+		});
+
+		test('.md files in ~/.copilot/agents/ folder should be recognized as agent files', () => {
+			const uri = URI.file('/home/user/.copilot/agents/my-agent.md');
+			assert.strictEqual(getPromptFileType(uri), PromptsType.agent);
+		});
+
+		test('README.md in ~/.copilot/agents/ should NOT be recognized as agent file', () => {
+			const uri = URI.file('/home/user/.copilot/agents/README.md');
+			assert.strictEqual(getPromptFileType(uri), undefined);
+		});
+
 		test('.md files outside .github/agents/ should not be recognized as agent files', () => {
 			const uri = URI.file('/workspace/test/foo.md');
 			assert.strictEqual(getPromptFileType(uri), undefined);
@@ -130,6 +160,16 @@ suite('promptFileLocations', function () {
 			assert.strictEqual(getCleanPromptName(uri), 'demonstrate');
 		});
 
+		test('removes .md extension for files in .claude/agents/', () => {
+			const uri = URI.file('/workspace/.claude/agents/claude-agent.md');
+			assert.strictEqual(getCleanPromptName(uri), 'claude-agent');
+		});
+
+		test('removes .md extension for files in ~/.copilot/agents/', () => {
+			const uri = URI.file('/home/user/.copilot/agents/my-agent.md');
+			assert.strictEqual(getCleanPromptName(uri), 'my-agent');
+		});
+
 		test('README.md in .github/agents/ should keep .md extension', () => {
 			const uri = URI.file('/workspace/.github/agents/README.md');
 			assert.strictEqual(getCleanPromptName(uri), 'README.md');
diff --git a/src/vs/workbench/contrib/chat/test/common/promptSyntax/hookClaudeCompat.test.ts b/src/vs/workbench/contrib/chat/test/common/promptSyntax/hookClaudeCompat.test.ts
index 76b2ac54b072c..2ba30ef5848aa 100644
--- a/src/vs/workbench/contrib/chat/test/common/promptSyntax/hookClaudeCompat.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/promptSyntax/hookClaudeCompat.test.ts
@@ -5,7 +5,7 @@
 
 import assert from 'assert';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
-import { HookType } from '../../../common/promptSyntax/hookSchema.js';
+import { HookType } from '../../../common/promptSyntax/hookTypes.js';
 import { parseClaudeHooks, resolveClaudeHookType, getClaudeHookTypeName, extractHookCommandsFromItem } from '../../../common/promptSyntax/hookClaudeCompat.js';
 import { getHookSourceFormat, HookSourceFormat, buildNewHookEntry } from '../../../common/promptSyntax/hookCompatibility.js';
 import { URI } from '../../../../../../base/common/uri.js';
diff --git a/src/vs/workbench/contrib/chat/test/common/promptSyntax/hookCompatibility.test.ts b/src/vs/workbench/contrib/chat/test/common/promptSyntax/hookCompatibility.test.ts
index ede5eeb5e52c8..7fd7eee9304d6 100644
--- a/src/vs/workbench/contrib/chat/test/common/promptSyntax/hookCompatibility.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/promptSyntax/hookCompatibility.test.ts
@@ -5,7 +5,7 @@
 
 import assert from 'assert';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
-import { HookType } from '../../../common/promptSyntax/hookSchema.js';
+import { HookType } from '../../../common/promptSyntax/hookTypes.js';
 import { parseCopilotHooks, parseHooksFromFile, HookSourceFormat } from '../../../common/promptSyntax/hookCompatibility.js';
 import { URI } from '../../../../../../base/common/uri.js';
 
diff --git a/src/vs/workbench/contrib/chat/test/common/promptSyntax/hookSchema.test.ts b/src/vs/workbench/contrib/chat/test/common/promptSyntax/hookSchema.test.ts
index 63bcf59c0049f..ee30e3f60dc08 100644
--- a/src/vs/workbench/contrib/chat/test/common/promptSyntax/hookSchema.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/promptSyntax/hookSchema.test.ts
@@ -5,9 +5,11 @@
 
 import assert from 'assert';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
-import { resolveHookCommand, resolveEffectiveCommand, formatHookCommandLabel, IHookCommand } from '../../../common/promptSyntax/hookSchema.js';
+import { resolveHookCommand, resolveEffectiveCommand, formatHookCommandLabel, IHookCommand, parseSubagentHooksFromYaml } from '../../../common/promptSyntax/hookSchema.js';
 import { URI } from '../../../../../../base/common/uri.js';
 import { OperatingSystem } from '../../../../../../base/common/platform.js';
+import { HookType } from '../../../common/promptSyntax/hookTypes.js';
+import { Range } from '../../../../../../editor/common/core/range.js';
 
 suite('HookSchema', () => {
 	ensureNoDisposablesAreLeakedInTestSuite();
@@ -461,7 +463,7 @@ suite('HookSchema', () => {
 			assert.strictEqual(formatHookCommandLabel(hook, OperatingSystem.Windows), '');
 		});
 
-		test('applies platform override for display with platform badge', () => {
+		test('applies platform override for display', () => {
 			const hook: IHookCommand = {
 				type: 'command',
 				command: 'default-command',
@@ -469,10 +471,10 @@ suite('HookSchema', () => {
 				linux: 'linux-command',
 				osx: 'osx-command'
 			};
-			// Should include platform badge when using platform-specific override
-			assert.strictEqual(formatHookCommandLabel(hook, OperatingSystem.Windows), '[Windows] win-command');
-			assert.strictEqual(formatHookCommandLabel(hook, OperatingSystem.Macintosh), '[macOS] osx-command');
-			assert.strictEqual(formatHookCommandLabel(hook, OperatingSystem.Linux), '[Linux] linux-command');
+			// Should resolve to platform-specific command
+			assert.strictEqual(formatHookCommandLabel(hook, OperatingSystem.Windows), 'win-command');
+			assert.strictEqual(formatHookCommandLabel(hook, OperatingSystem.Macintosh), 'osx-command');
+			assert.strictEqual(formatHookCommandLabel(hook, OperatingSystem.Linux), 'linux-command');
 		});
 
 		test('no platform badge when falling back to default command', () => {
@@ -485,4 +487,162 @@ suite('HookSchema', () => {
 			assert.strictEqual(formatHookCommandLabel(hook, OperatingSystem.Windows), 'default-command');
 		});
 	});
+
+	suite('parseSubagentHooksFromYaml', () => {
+
+		const workspaceRoot = URI.file('/workspace');
+		const userHome = '/home/user';
+
+		const dummyRange = new Range(1, 1, 1, 1);
+
+		function makeScalar(value: string): import('../../../common/promptSyntax/promptFileParser.js').IScalarValue {
+			return { type: 'scalar', value, range: dummyRange, format: 'none' };
+		}
+
+		function makeMap(entries: Record<string, import('../../../common/promptSyntax/promptFileParser.js').IValue>): import('../../../common/promptSyntax/promptFileParser.js').IMapValue {
+			const properties = Object.entries(entries).map(([key, value]) => ({
+				key: makeScalar(key),
+				value,
+			}));
+			return { type: 'map', properties, range: dummyRange };
+		}
+
+		function makeSequence(items: import('../../../common/promptSyntax/promptFileParser.js').IValue[]): import('../../../common/promptSyntax/promptFileParser.js').ISequenceValue {
+			return { type: 'sequence', items, range: dummyRange };
+		}
+
+		test('parses direct command format (without matcher)', () => {
+			// hooks:
+			//   PreToolUse:
+			//     - type: command
+			//       command: "./scripts/validate.sh"
+			const hooksMap = makeMap({
+				'PreToolUse': makeSequence([
+					makeMap({
+						'type': makeScalar('command'),
+						'command': makeScalar('./scripts/validate.sh'),
+					}),
+				]),
+			});
+
+			const result = parseSubagentHooksFromYaml(hooksMap, workspaceRoot, userHome);
+
+			assert.strictEqual(result[HookType.PreToolUse]?.length, 1);
+			assert.strictEqual(result[HookType.PreToolUse]![0].command, './scripts/validate.sh');
+		});
+
+		test('parses Claude format (with matcher)', () => {
+			// hooks:
+			//   PreToolUse:
+			//     - matcher: "Bash"
+			//       hooks:
+			//         - type: command
+			//           command: "./scripts/validate-readonly.sh"
+			const hooksMap = makeMap({
+				'PreToolUse': makeSequence([
+					makeMap({
+						'matcher': makeScalar('Bash'),
+						'hooks': makeSequence([
+							makeMap({
+								'type': makeScalar('command'),
+								'command': makeScalar('./scripts/validate-readonly.sh'),
+							}),
+						]),
+					}),
+				]),
+			});
+
+			const result = parseSubagentHooksFromYaml(hooksMap, workspaceRoot, userHome);
+
+			assert.strictEqual(result[HookType.PreToolUse]?.length, 1);
+			assert.strictEqual(result[HookType.PreToolUse]![0].command, './scripts/validate-readonly.sh');
+		});
+
+		test('parses multiple hook types', () => {
+			const hooksMap = makeMap({
+				'PreToolUse': makeSequence([
+					makeMap({
+						'type': makeScalar('command'),
+						'command': makeScalar('./scripts/pre.sh'),
+					}),
+				]),
+				'PostToolUse': makeSequence([
+					makeMap({
+						'matcher': makeScalar('Edit|Write'),
+						'hooks': makeSequence([
+							makeMap({
+								'type': makeScalar('command'),
+								'command': makeScalar('./scripts/lint.sh'),
+							}),
+						]),
+					}),
+				]),
+			});
+
+			const result = parseSubagentHooksFromYaml(hooksMap, workspaceRoot, userHome);
+
+			assert.strictEqual(result[HookType.PreToolUse]?.length, 1);
+			assert.strictEqual(result[HookType.PreToolUse]![0].command, './scripts/pre.sh');
+			assert.strictEqual(result[HookType.PostToolUse]?.length, 1);
+			assert.strictEqual(result[HookType.PostToolUse]![0].command, './scripts/lint.sh');
+		});
+
+		test('skips unknown hook types', () => {
+			const hooksMap = makeMap({
+				'UnknownHook': makeSequence([
+					makeMap({
+						'type': makeScalar('command'),
+						'command': makeScalar('echo "ignored"'),
+					}),
+				]),
+			});
+
+			const result = parseSubagentHooksFromYaml(hooksMap, workspaceRoot, userHome);
+
+			assert.strictEqual(result[HookType.PreToolUse], undefined);
+			assert.strictEqual(result[HookType.PostToolUse], undefined);
+		});
+
+		test('handles command without type field', () => {
+			const hooksMap = makeMap({
+				'PreToolUse': makeSequence([
+					makeMap({
+						'command': makeScalar('./scripts/validate.sh'),
+					}),
+				]),
+			});
+
+			const result = parseSubagentHooksFromYaml(hooksMap, workspaceRoot, userHome);
+
+			assert.strictEqual(result[HookType.PreToolUse]?.length, 1);
+			assert.strictEqual(result[HookType.PreToolUse]![0].command, './scripts/validate.sh');
+		});
+
+		test('resolves cwd relative to workspace', () => {
+			const hooksMap = makeMap({
+				'SessionStart': makeSequence([
+					makeMap({
+						'type': makeScalar('command'),
+						'command': makeScalar('echo "start"'),
+						'cwd': makeScalar('src'),
+					}),
+				]),
+			});
+
+			const result = parseSubagentHooksFromYaml(hooksMap, workspaceRoot, userHome);
+
+			assert.strictEqual(result[HookType.SessionStart]?.length, 1);
+			assert.deepStrictEqual(result[HookType.SessionStart]![0].cwd, URI.file('/workspace/src'));
+		});
+
+		test('skips non-sequence hook values', () => {
+			const hooksMap = makeMap({
+				'PreToolUse': makeScalar('not-a-sequence'),
+			});
+
+			const result = parseSubagentHooksFromYaml(hooksMap, workspaceRoot, userHome);
+
+			assert.strictEqual(result[HookType.PreToolUse], undefined);
+		});
+	});
 });
diff --git a/src/vs/workbench/contrib/chat/test/common/promptSyntax/service/mockPromptsService.ts b/src/vs/workbench/contrib/chat/test/common/promptSyntax/service/mockPromptsService.ts
index d222b92eb6817..d9ef7bdde738b 100644
--- a/src/vs/workbench/contrib/chat/test/common/promptSyntax/service/mockPromptsService.ts
+++ b/src/vs/workbench/contrib/chat/test/common/promptSyntax/service/mockPromptsService.ts
@@ -18,8 +18,8 @@ export class MockPromptsService implements IPromptsService {
 
 	_serviceBrand: undefined;
 
-	private readonly _onDidChangeCustomChatModes = new Emitter<void>();
-	readonly onDidChangeCustomAgents = this._onDidChangeCustomChatModes.event;
+	private readonly _onDidChangeCustomAgents = new Emitter<void>();
+	readonly onDidChangeCustomAgents = this._onDidChangeCustomAgents.event;
 
 	private readonly _onDidLogDiscovery = new Emitter<IPromptDiscoveryLogEntry>();
 	readonly onDidLogDiscovery: Event<IPromptDiscoveryLogEntry> = this._onDidLogDiscovery.event;
@@ -28,10 +28,10 @@ export class MockPromptsService implements IPromptsService {
 
 	setCustomModes(modes: ICustomAgent[]): void {
 		this._customModes = modes;
-		this._onDidChangeCustomChatModes.fire();
+		this._onDidChangeCustomAgents.fire();
 	}
 
-	async getCustomAgents(token: CancellationToken, sessionId?: string): Promise<readonly ICustomAgent[]> {
+	async getCustomAgents(token: CancellationToken, sessionResource?: URI): Promise<readonly ICustomAgent[]> {
 		return this._customModes;
 	}
 
@@ -50,7 +50,7 @@ export class MockPromptsService implements IPromptsService {
 	resolvePromptSlashCommand(command: string, _token: CancellationToken): Promise<any> { throw new Error('Not implemented'); }
 	get onDidChangeSlashCommands(): Event<void> { throw new Error('Not implemented'); }
 	// eslint-disable-next-line @typescript-eslint/no-explicit-any
-	getPromptSlashCommands(_token: CancellationToken, _sessionId?: string): Promise<any[]> { throw new Error('Not implemented'); }
+	getPromptSlashCommands(_token: CancellationToken, _sessionResource?: URI): Promise<any[]> { throw new Error('Not implemented'); }
 	getPromptSlashCommandName(uri: URI, _token: CancellationToken): Promise<string> { throw new Error('Not implemented'); }
 	// eslint-disable-next-line @typescript-eslint/no-explicit-any
 	parse(_uri: URI, _type: any, _token: CancellationToken): Promise<any> { throw new Error('Not implemented'); }
@@ -65,11 +65,12 @@ export class MockPromptsService implements IPromptsService {
 	getDisabledPromptFiles(type: PromptsType): ResourceSet { throw new Error('Method not implemented.'); }
 	setDisabledPromptFiles(type: PromptsType, uris: ResourceSet): void { throw new Error('Method not implemented.'); }
 	registerPromptFileProvider(extension: IExtensionDescription, type: PromptsType, provider: { providePromptFiles: (context: IPromptFileContext, token: CancellationToken) => Promise<IPromptFileResource[] | undefined> }): IDisposable { throw new Error('Method not implemented.'); }
-	findAgentSkills(token: CancellationToken, sessionId?: string): Promise<IAgentSkill[] | undefined> { throw new Error('Method not implemented.'); }
+	findAgentSkills(token: CancellationToken, sessionResource?: URI): Promise<IAgentSkill[] | undefined> { throw new Error('Method not implemented.'); }
 	// eslint-disable-next-line @typescript-eslint/no-explicit-any
-	getPromptDiscoveryInfo(_type: any, _token: CancellationToken, _sessionId?: string): Promise<any> { throw new Error('Method not implemented.'); }
-	// eslint-disable-next-line @typescript-eslint/no-explicit-any
-	getHooks(_token: CancellationToken): Promise<any> { throw new Error('Method not implemented.'); }
-	getInstructionFiles(_token: CancellationToken, _sessionId?: string): Promise<readonly IPromptPath[]> { throw new Error('Method not implemented.'); }
+	getHooks(_token: CancellationToken, _sessionResource?: URI): Promise<any> { throw new Error('Method not implemented.'); }
+	getInstructionFiles(_token: CancellationToken, _sessionResource?: URI): Promise<readonly IPromptPath[]> { throw new Error('Method not implemented.'); }
 	dispose(): void { }
+	onDidChangeInstructions: Event<void> = Event.None;
+	onDidChangePromptFiles: Event<void> = Event.None;
+	onDidChangeSkills: Event<void> = Event.None;
 }
diff --git a/src/vs/workbench/contrib/chat/test/common/promptSyntax/service/promptFileParser.test.ts b/src/vs/workbench/contrib/chat/test/common/promptSyntax/service/promptFileParser.test.ts
index 136ed9195ccac..d50fa8b4fe2fa 100644
--- a/src/vs/workbench/contrib/chat/test/common/promptSyntax/service/promptFileParser.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/promptSyntax/service/promptFileParser.test.ts
@@ -239,6 +239,183 @@ suite('PromptFileParser', () => {
 		assert.deepEqual(result.header.tools, ['search', 'terminal']);
 	});
 
+	test('ignores links and variables inside inline code and fenced code blocks', async () => {
+		const uri = URI.parse('file:///test/prompt3.md');
+		const content = [
+			'---',
+			`description: "Prompt with markdown code"`,
+			'---',
+			'Outside #tool:outside and [outside](./outside.md).',
+			'Inline code: `#tool:inline and [inline](./inline.md)` should be ignored.',
+			'```ts',
+			'#tool:block and #file:./inside-block.md and [block](./block.md)',
+			'```',
+			'After block #file:./after.md and [after](./after-link.md).',
+		].join('\n');
+
+		const result = new PromptFileParser().parse(uri, content);
+		assert.ok(result.body);
+		assert.deepEqual(result.body.fileReferences.map(reference => ({ content: reference.content, isMarkdownLink: reference.isMarkdownLink })), [
+			{ content: './outside.md', isMarkdownLink: true },
+			{ content: './after.md', isMarkdownLink: false },
+			{ content: './after-link.md', isMarkdownLink: true }
+		]);
+		assert.deepEqual(result.body.variableReferences.map(reference => reference.name), ['outside']);
+	});
+
+	test('ignores references in multiple inline code spans on the same line', async () => {
+		const uri = URI.parse('file:///test/prompt-inline.md');
+		const content = [
+			'---',
+			'description: "test"',
+			'---',
+			'Before `#tool:ignored1` middle #tool:visible `[link](./ignored.md)` after [real](./real.md).',
+		].join('\n');
+
+		const result = new PromptFileParser().parse(uri, content);
+		assert.ok(result.body);
+		assert.deepEqual(result.body.fileReferences.map(r => ({ content: r.content, isMarkdownLink: r.isMarkdownLink })), [
+			{ content: './real.md', isMarkdownLink: true },
+		]);
+		assert.deepEqual(result.body.variableReferences.map(r => r.name), ['visible']);
+	});
+
+	test('handles fenced code block without language specifier', async () => {
+		const uri = URI.parse('file:///test/prompt-fence.md');
+		const content = [
+			'---',
+			'description: "test"',
+			'---',
+			'```',
+			'#file:./ignored.md',
+			'[link](./ignored-link.md)',
+			'```',
+			'#file:./visible.md',
+		].join('\n');
+
+		const result = new PromptFileParser().parse(uri, content);
+		assert.ok(result.body);
+		assert.deepEqual(result.body.fileReferences.map(r => ({ content: r.content, isMarkdownLink: r.isMarkdownLink })), [
+			{ content: './visible.md', isMarkdownLink: false },
+		]);
+		assert.deepEqual(result.body.variableReferences, []);
+	});
+
+	test('handles multiple fenced code blocks', async () => {
+		const uri = URI.parse('file:///test/prompt-multi-fence.md');
+		const content = [
+			'---',
+			'description: "test"',
+			'---',
+			'#tool:before',
+			'```js',
+			'#tool:ignored1',
+			'```',
+			'#tool:between',
+			'```python',
+			'#tool:ignored2',
+			'```',
+			'#tool:after',
+		].join('\n');
+
+		const result = new PromptFileParser().parse(uri, content);
+		assert.ok(result.body);
+		assert.deepEqual(result.body.variableReferences.map(r => r.name), ['before', 'between', 'after']);
+	});
+
+	test('unclosed fenced code block ignores all remaining lines', async () => {
+		const uri = URI.parse('file:///test/prompt-unclosed.md');
+		const content = [
+			'---',
+			'description: "test"',
+			'---',
+			'#tool:visible',
+			'```',
+			'#tool:ignored',
+			'#file:./ignored.md',
+		].join('\n');
+
+		const result = new PromptFileParser().parse(uri, content);
+		assert.ok(result.body);
+		assert.deepEqual(result.body.variableReferences.map(r => r.name), ['visible']);
+		assert.deepEqual(result.body.fileReferences, []);
+	});
+
+	test('adjacent inline code does not suppress outside references', async () => {
+		const uri = URI.parse('file:///test/prompt-adjacent.md');
+		const content = [
+			'---',
+			'description: "test"',
+			'---',
+			'`code`#tool:attached `more`[link](./file.md)',
+		].join('\n');
+
+		const result = new PromptFileParser().parse(uri, content);
+		assert.ok(result.body);
+		// #tool:attached starts right after the closing backtick, so it's outside inline code
+		assert.deepEqual(result.body.variableReferences.map(r => r.name), ['attached']);
+		// [link](./file.md) starts after the second inline code span
+		assert.deepEqual(result.body.fileReferences.map(r => ({ content: r.content, isMarkdownLink: r.isMarkdownLink })), [
+			{ content: './file.md', isMarkdownLink: true },
+		]);
+	});
+
+	test('indented fenced code block is still detected', async () => {
+		const uri = URI.parse('file:///test/prompt-indent.md');
+		const content = [
+			'---',
+			'description: "test"',
+			'---',
+			'  ```ts',
+			'  #tool:ignored',
+			'  ```',
+			'#tool:visible',
+		].join('\n');
+
+		const result = new PromptFileParser().parse(uri, content);
+		assert.ok(result.body);
+		assert.deepEqual(result.body.variableReferences.map(r => r.name), ['visible']);
+	});
+
+	test('fenced code block with 4 backticks', async () => {
+		const uri = URI.parse('file:///test/prompt-4tick.md');
+		const content = [
+			'---',
+			'description: "test"',
+			'---',
+			'````',
+			'#tool:ignored and [link](./ignored.md)',
+			'````',
+			'#tool:visible',
+		].join('\n');
+
+		const result = new PromptFileParser().parse(uri, content);
+		assert.ok(result.body);
+		assert.deepEqual(result.body.variableReferences.map(r => r.name), ['visible']);
+		assert.deepEqual(result.body.fileReferences, []);
+	});
+
+	test('fenced code block with tilde fence (~~~)', async () => {
+		const uri = URI.parse('file:///test/prompt-tilde.md');
+		const content = [
+			'---',
+			'description: "test"',
+			'---',
+			'~~~',
+			'#file:./ignored.md and [link](./ignored-link.md)',
+			'#tool:ignored',
+			'~~~',
+			'[real](./real.md)',
+		].join('\n');
+
+		const result = new PromptFileParser().parse(uri, content);
+		assert.ok(result.body);
+		assert.deepEqual(result.body.fileReferences.map(r => ({ content: r.content, isMarkdownLink: r.isMarkdownLink })), [
+			{ content: './real.md', isMarkdownLink: true },
+		]);
+		assert.deepEqual(result.body.variableReferences, []);
+	});
+
 
 	test('agent with agents', async () => {
 		const uri = URI.parse('file:///test/test.agent.md');
diff --git a/src/vs/workbench/contrib/chat/test/common/promptSyntax/service/promptsService.test.ts b/src/vs/workbench/contrib/chat/test/common/promptSyntax/service/promptsService.test.ts
index 5a784486c3200..162a1a65b9b2c 100644
--- a/src/vs/workbench/contrib/chat/test/common/promptSyntax/service/promptsService.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/promptSyntax/service/promptsService.test.ts
@@ -11,7 +11,7 @@ import { match } from '../../../../../../../base/common/glob.js';
 import { ResourceSet } from '../../../../../../../base/common/map.js';
 import { Schemas } from '../../../../../../../base/common/network.js';
 import { ISettableObservable, observableValue } from '../../../../../../../base/common/observable.js';
-import { relativePath } from '../../../../../../../base/common/resources.js';
+import { basename, relativePath } from '../../../../../../../base/common/resources.js';
 import { URI } from '../../../../../../../base/common/uri.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../../base/test/common/utils.js';
 import { Range } from '../../../../../../../editor/common/core/range.js';
@@ -35,13 +35,13 @@ import { IWorkbenchEnvironmentService } from '../../../../../../services/environ
 import { IFilesConfigurationService } from '../../../../../../services/filesConfiguration/common/filesConfigurationService.js';
 import { IUserDataProfileService } from '../../../../../../services/userDataProfile/common/userDataProfile.js';
 import { toUserDataProfile } from '../../../../../../../platform/userDataProfile/common/userDataProfile.js';
-import { TestContextService, TestUserDataProfileService } from '../../../../../../test/common/workbenchTestServices.js';
+import { TestContextService, TestUserDataProfileService, TestWorkspaceTrustManagementService } from '../../../../../../test/common/workbenchTestServices.js';
 import { ChatRequestVariableSet, isPromptFileVariableEntry, toFileVariableEntry } from '../../../../common/attachments/chatVariableEntries.js';
 import { ComputeAutomaticInstructions, newInstructionsCollectionEvent } from '../../../../common/promptSyntax/computeAutomaticInstructions.js';
 import { PromptsConfig } from '../../../../common/promptSyntax/config/config.js';
 import { AGENTS_SOURCE_FOLDER, CLAUDE_CONFIG_FOLDER, HOOKS_SOURCE_FOLDER, INSTRUCTION_FILE_EXTENSION, INSTRUCTIONS_DEFAULT_SOURCE_FOLDER, LEGACY_MODE_DEFAULT_SOURCE_FOLDER, PROMPT_DEFAULT_SOURCE_FOLDER, PROMPT_FILE_EXTENSION } from '../../../../common/promptSyntax/config/promptFileLocations.js';
-import { INSTRUCTIONS_LANGUAGE_ID, PROMPT_LANGUAGE_ID, PromptsType } from '../../../../common/promptSyntax/promptTypes.js';
-import { ExtensionAgentSourceType, ICustomAgent, IPromptFileContext, IPromptsService, PromptsStorage, Target } from '../../../../common/promptSyntax/service/promptsService.js';
+import { INSTRUCTIONS_LANGUAGE_ID, PROMPT_LANGUAGE_ID, PromptsType, Target } from '../../../../common/promptSyntax/promptTypes.js';
+import { ExtensionAgentSourceType, ICustomAgent, IPromptFileContext, IPromptsService, PromptsStorage } from '../../../../common/promptSyntax/service/promptsService.js';
 import { PromptsService } from '../../../../common/promptSyntax/service/promptsServiceImpl.js';
 import { mockFiles } from '../testUtils/mockFilesystem.js';
 import { InMemoryStorageService, IStorageService } from '../../../../../../../platform/storage/common/storage.js';
@@ -50,10 +50,11 @@ import { IFileMatch, IFileQuery, ISearchService } from '../../../../../../servic
 import { IExtensionService } from '../../../../../../services/extensions/common/extensions.js';
 import { IRemoteAgentService } from '../../../../../../services/remote/common/remoteAgentService.js';
 import { ChatModeKind } from '../../../../common/constants.js';
-import { HookType } from '../../../../common/promptSyntax/hookSchema.js';
+import { HookType } from '../../../../common/promptSyntax/hookTypes.js';
 import { IContextKeyService, IContextKeyChangeEvent } from '../../../../../../../platform/contextkey/common/contextkey.js';
 import { MockContextKeyService } from '../../../../../../../platform/keybinding/test/common/mockKeybindingService.js';
-import { IAgentPlugin, IAgentPluginCommand, IAgentPluginHook, IAgentPluginMcpServerDefinition, IAgentPluginService, IAgentPluginSkill } from '../../../../common/plugins/agentPluginService.js';
+import { IAgentPlugin, IAgentPluginAgent, IAgentPluginCommand, IAgentPluginHook, IAgentPluginInstruction, IAgentPluginMcpServerDefinition, IAgentPluginService, IAgentPluginSkill } from '../../../../common/plugins/agentPluginService.js';
+import { IWorkspaceTrustManagementService } from '../../../../../../../platform/workspace/common/workspaceTrust.js';
 
 suite('PromptsService', () => {
 	const disposables = ensureNoDisposablesAreLeakedInTestSuite();
@@ -64,7 +65,7 @@ suite('PromptsService', () => {
 	let testConfigService: TestConfigurationService;
 	let fileService: IFileService;
 	let testPluginsObservable: ISettableObservable<readonly IAgentPlugin[]>;
-	let testAllPluginsObservable: ISettableObservable<readonly IAgentPlugin[]>;
+	let workspaceTrustService: TestWorkspaceTrustManagementService;
 
 	setup(async () => {
 		instaService = disposables.add(new TestInstantiationService());
@@ -79,6 +80,7 @@ suite('PromptsService', () => {
 		testConfigService.setUserConfiguration(PromptsConfig.USE_NESTED_AGENT_MD, false);
 		testConfigService.setUserConfiguration(PromptsConfig.INCLUDE_REFERENCED_INSTRUCTIONS, true);
 		testConfigService.setUserConfiguration(PromptsConfig.INCLUDE_APPLYING_INSTRUCTIONS, true);
+		testConfigService.setUserConfiguration(PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS, false);
 		testConfigService.setUserConfiguration(PromptsConfig.INSTRUCTIONS_LOCATION_KEY, { [INSTRUCTIONS_DEFAULT_SOURCE_FOLDER]: true });
 		testConfigService.setUserConfiguration(PromptsConfig.PROMPT_LOCATIONS_KEY, { [PROMPT_DEFAULT_SOURCE_FOLDER]: true });
 		testConfigService.setUserConfiguration(PromptsConfig.MODE_LOCATION_KEY, { [LEGACY_MODE_DEFAULT_SOURCE_FOLDER]: true });
@@ -166,13 +168,15 @@ suite('PromptsService', () => {
 
 		instaService.stub(IContextKeyService, new MockContextKeyService());
 
+		workspaceTrustService = disposables.add(new TestWorkspaceTrustManagementService());
+		workspaceTrustService.getUriTrustInfo = (uri: URI) => Promise.resolve({ trusted: true, uri });
+		instaService.stub(IWorkspaceTrustManagementService, workspaceTrustService);
+
 		testPluginsObservable = observableValue<readonly IAgentPlugin[]>('testPlugins', []);
-		testAllPluginsObservable = observableValue<readonly IAgentPlugin[]>('testAllPlugins', []);
 
 		instaService.stub(IAgentPluginService, {
 			plugins: testPluginsObservable,
-			allPlugins: testAllPluginsObservable,
-			setPluginEnabled: () => { },
+			enablementModel: { readEnabled: () => 2 /* EnabledProfile */, setEnabled: () => { } },
 		});
 
 		service = disposables.add(instaService.createInstance(PromptsService));
@@ -794,6 +798,7 @@ suite('PromptsService', () => {
 					target: Target.Undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
 					agents: undefined,
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.github/agents/agent1.agent.md'),
 					source: { storage: PromptsStorage.local }
 				},
@@ -850,6 +855,7 @@ suite('PromptsService', () => {
 					target: Target.Undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
 					agents: undefined,
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.github/agents/agent1.agent.md'),
 					source: { storage: PromptsStorage.local },
 				},
@@ -925,6 +931,7 @@ suite('PromptsService', () => {
 					target: Target.Undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
 					agents: undefined,
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.github/agents/agent1.agent.md'),
 					source: { storage: PromptsStorage.local }
 				},
@@ -943,6 +950,7 @@ suite('PromptsService', () => {
 					target: Target.Undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
 					agents: undefined,
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.github/agents/agent2.agent.md'),
 					source: { storage: PromptsStorage.local }
 				},
@@ -1013,6 +1021,7 @@ suite('PromptsService', () => {
 					argumentHint: undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
 					agents: undefined,
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.github/agents/github-agent.agent.md'),
 					source: { storage: PromptsStorage.local }
 				},
@@ -1031,6 +1040,7 @@ suite('PromptsService', () => {
 					tools: undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
 					agents: undefined,
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.github/agents/vscode-agent.agent.md'),
 					source: { storage: PromptsStorage.local }
 				},
@@ -1049,6 +1059,7 @@ suite('PromptsService', () => {
 					target: Target.Undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
 					agents: undefined,
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.github/agents/generic-agent.agent.md'),
 					source: { storage: PromptsStorage.local }
 				},
@@ -1126,6 +1137,7 @@ suite('PromptsService', () => {
 					argumentHint: undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
 					agents: undefined,
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.github/agents/copilot-agent.agent.md'),
 					source: { storage: PromptsStorage.local }
 				},
@@ -1146,6 +1158,7 @@ suite('PromptsService', () => {
 					argumentHint: undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
 					agents: undefined,
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.claude/agents/claude-agent.md'),
 					source: { storage: PromptsStorage.local }
 				},
@@ -1165,6 +1178,7 @@ suite('PromptsService', () => {
 					argumentHint: undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
 					agents: undefined,
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.claude/agents/claude-agent2.md'),
 					source: { storage: PromptsStorage.local }
 				},
@@ -1177,6 +1191,7 @@ suite('PromptsService', () => {
 			);
 		});
 
+
 		test('agents with .md extension should be recognized, except README.md', async () => {
 			const rootFolderName = 'custom-agents-md-extension';
 			const rootFolder = `/${rootFolderName}`;
@@ -1220,6 +1235,7 @@ suite('PromptsService', () => {
 					target: Target.Undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
 					agents: undefined,
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.github/agents/demonstrate.md'),
 					source: { storage: PromptsStorage.local }
 				}
@@ -1290,6 +1306,7 @@ suite('PromptsService', () => {
 					argumentHint: undefined,
 					target: Target.Undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.github/agents/restricted-agent.agent.md'),
 					source: { storage: PromptsStorage.local }
 				},
@@ -1308,6 +1325,7 @@ suite('PromptsService', () => {
 					tools: undefined,
 					target: Target.Undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.github/agents/no-access-agent.agent.md'),
 					source: { storage: PromptsStorage.local }
 				},
@@ -1326,6 +1344,7 @@ suite('PromptsService', () => {
 					tools: undefined,
 					target: Target.Undefined,
 					visibility: { userInvocable: true, agentInvocable: true },
+					hooks: undefined,
 					uri: URI.joinPath(rootFolderUri, '.github/agents/full-access-agent.agent.md'),
 					source: { storage: PromptsStorage.local }
 				},
@@ -1338,6 +1357,60 @@ suite('PromptsService', () => {
 			);
 		});
 
+		test('header with infer: false sets agentInvocable to false', async () => {
+			const rootFolderName = 'custom-agents-infer-false';
+			const rootFolder = `/${rootFolderName}`;
+			const rootFolderUri = URI.file(rootFolder);
+
+			workspaceContextService.setWorkspace(testWorkspace(rootFolderUri));
+
+			await mockFiles(fileService, [
+				{
+					path: `${rootFolder}/.github/agents/agent-infer-false.agent.md`,
+					contents: [
+						'---',
+						'description: \'Agent with infer: false.\'',
+						'infer: false',
+						'---',
+						'I should not be invocable by the model.',
+					]
+				},
+				{
+					path: `${rootFolder}/.github/agents/agent-infer-true.agent.md`,
+					contents: [
+						'---',
+						'description: \'Agent with infer: true.\'',
+						'infer: true',
+						'---',
+						'I should be invocable by the model.',
+					]
+				},
+				{
+					path: `${rootFolder}/.github/agents/agent-no-infer.agent.md`,
+					contents: [
+						'---',
+						'description: \'Agent without infer.\'',
+						'---',
+						'I should default to being invocable by the model.',
+					]
+				}
+			]);
+
+			const result = (await service.getCustomAgents(CancellationToken.None)).map(agent => ({ ...agent, uri: URI.from(agent.uri) }));
+
+			const inferFalseAgent = result.find(a => a.name === 'agent-infer-false');
+			assert.ok(inferFalseAgent, 'Should find agent with infer: false');
+			assert.strictEqual(inferFalseAgent.visibility.agentInvocable, false, 'infer: false should set agentInvocable to false');
+
+			const inferTrueAgent = result.find(a => a.name === 'agent-infer-true');
+			assert.ok(inferTrueAgent, 'Should find agent with infer: true');
+			assert.strictEqual(inferTrueAgent.visibility.agentInvocable, true, 'infer: true should set agentInvocable to true');
+
+			const noInferAgent = result.find(a => a.name === 'agent-no-infer');
+			assert.ok(noInferAgent, 'Should find agent without infer');
+			assert.strictEqual(noInferAgent.visibility.agentInvocable, true, 'missing infer should default agentInvocable to true');
+		});
+
 		test('agents from user data folder', async () => {
 			const rootFolderName = 'custom-agents-user-data';
 			const rootFolder = `/${rootFolderName}`;
@@ -1360,7 +1433,8 @@ suite('PromptsService', () => {
 			};
 			instaService.stub(IUserDataProfileService, customUserDataProfileService);
 
-			// Recreate the service with the new stub
+			// Recreate the service with the new stub (dispose existing to avoid duplicate filesystem registration)
+			service.dispose();
 			const testService = disposables.add(instaService.createInstance(PromptsService));
 
 			// Create agent files in both workspace and user data folder
@@ -1442,7 +1516,8 @@ suite('PromptsService', () => {
 			};
 			instaService.stub(IUserDataProfileService, customUserDataProfileService);
 
-			// Recreate the service with the new stub
+			// Recreate the service with the new stub (dispose existing to avoid duplicate filesystem registration)
+			service.dispose();
 			const testService = disposables.add(instaService.createInstance(PromptsService));
 
 			// Create prompt files in both workspace and user data folder
@@ -1507,7 +1582,8 @@ suite('PromptsService', () => {
 			};
 			instaService.stub(IUserDataProfileService, customUserDataProfileService);
 
-			// Recreate the service with the new stub
+			// Recreate the service with the new stub (dispose existing to avoid duplicate filesystem registration)
+			service.dispose();
 			const testService = disposables.add(instaService.createInstance(PromptsService));
 
 			// Create instructions files in both workspace and user data folder
@@ -1589,7 +1665,7 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.listPromptFiles(PromptsType.skill, CancellationToken.None);
+			const result = (await service.listPromptFiles(PromptsType.skill, CancellationToken.None)).filter(s => s.storage !== PromptsStorage.internal);
 
 			assert.strictEqual(result.length, 2, 'Should find 2 skills');
 
@@ -1680,7 +1756,7 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.listPromptFiles(PromptsType.skill, CancellationToken.None);
+			const result = (await service.listPromptFiles(PromptsType.skill, CancellationToken.None)).filter(s => s.storage !== PromptsStorage.internal);
 
 			assert.strictEqual(result.length, 0, 'Should not find any skills in non-skill locations');
 		});
@@ -1766,7 +1842,7 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.listPromptFiles(PromptsType.skill, CancellationToken.None);
+			const result = (await service.listPromptFiles(PromptsType.skill, CancellationToken.None)).filter(s => s.storage !== PromptsStorage.internal);
 
 			assert.strictEqual(result.length, 1, 'Should find only 1 skill (from enabled folder)');
 			assert.ok(result[0].uri.path.includes('.claude/skills'), 'Should only find skill from .claude/skills');
@@ -1802,7 +1878,7 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.listPromptFiles(PromptsType.skill, CancellationToken.None);
+			const result = (await service.listPromptFiles(PromptsType.skill, CancellationToken.None)).filter(s => s.storage !== PromptsStorage.internal);
 
 			assert.strictEqual(result.length, 1, 'Should find 1 skill from tilde-expanded path');
 			assert.ok(result[0].uri.path.includes('/home/user/my-custom-skills'), 'Path should be expanded from tilde');
@@ -1944,6 +2020,7 @@ suite('PromptsService', () => {
 				}
 			}();
 			instaService.stub(IContextKeyService, testContextKeyService);
+			service.dispose();
 			const testService = disposables.add(instaService.createInstance(PromptsService));
 
 			const registered = testService.registerContributedFile(
@@ -1973,6 +2050,156 @@ suite('PromptsService', () => {
 		});
 	});
 
+	suite('listPromptFiles - parent repo folder', () => {
+		test('should find prompts, instructions, and agents in a parent repo folder', async () => {
+			const parentFolder = '/repos/collect-prompt-parent-test';
+			const rootFolder = `${parentFolder}/repo`;
+			const rootFolderUri = URI.file(rootFolder);
+
+			workspaceContextService.setWorkspace(testWorkspace(rootFolderUri));
+
+			await mockFiles(fileService, [
+				// .git in parent marks it as a repo root
+				{
+					path: `${parentFolder}/.git/HEAD`,
+					contents: ['ref: refs/heads/main'],
+				},
+				// Applying instruction in parent
+				{
+					path: `${parentFolder}/.github/instructions/typescript.instructions.md`,
+					contents: [
+						'---',
+						'description: \'Parent TypeScript instructions\'',
+						'applyTo: "**/*.ts"',
+						'---',
+						'Parent TypeScript coding standards',
+					]
+				},
+				// Prompt file in parent
+				{
+					path: `${parentFolder}/.github/prompts/help.prompt.md`,
+					contents: [
+						'---',
+						'description: \'Parent help prompt\'',
+						'---',
+						'Help the user with their question',
+					]
+				},
+				// Agent file in parent
+				{
+					path: `${parentFolder}/.github/agents/reviewer.agent.md`,
+					contents: [
+						'---',
+						'description: \'Parent code reviewer agent\'',
+						'---',
+						'You are a code reviewer',
+					]
+				},
+				{
+					path: `${rootFolder}/src/file.ts`,
+					contents: ['console.log("test");'],
+				},
+			]);
+
+			testConfigService.setUserConfiguration(PromptsConfig.INCLUDE_APPLYING_INSTRUCTIONS, true);
+			testConfigService.setUserConfiguration(PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS, false);
+
+			// With parent search disabled, should not find parent files
+			let promptFiles = await service.listPromptFiles(PromptsType.prompt, CancellationToken.None);
+			let agentFiles = await service.listPromptFiles(PromptsType.agent, CancellationToken.None);
+			let instructionFiles = await service.listPromptFiles(PromptsType.instructions, CancellationToken.None);
+
+			assert.ok(!promptFiles.some(f => f.uri.path.includes(parentFolder)), 'Should not find parent prompt files when parent search is disabled');
+			assert.ok(!agentFiles.some(f => f.uri.path.includes(parentFolder)), 'Should not find parent agent files when parent search is disabled');
+			assert.ok(!instructionFiles.some(f => f.uri.path.includes(parentFolder)), 'Should not find parent instruction files when parent search is disabled');
+
+			// With parent search enabled, should find parent files
+			testConfigService.setUserConfiguration(PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS, true);
+
+			promptFiles = await service.listPromptFiles(PromptsType.prompt, CancellationToken.None);
+			agentFiles = await service.listPromptFiles(PromptsType.agent, CancellationToken.None);
+			instructionFiles = await service.listPromptFiles(PromptsType.instructions, CancellationToken.None);
+
+			const promptPaths = promptFiles.map(f => f.uri.path);
+			const agentPaths = agentFiles.map(f => f.uri.path);
+			const instructionPaths = instructionFiles.map(f => f.uri.path);
+
+			assert.ok(promptPaths.includes(`${parentFolder}/.github/prompts/help.prompt.md`), 'Should find parent prompt file when parent search is enabled');
+			assert.ok(agentPaths.includes(`${parentFolder}/.github/agents/reviewer.agent.md`), 'Should find parent agent file when parent search is enabled');
+			assert.ok(instructionPaths.includes(`${parentFolder}/.github/instructions/typescript.instructions.md`), 'Should find parent instruction file when parent search is enabled');
+		});
+
+		test('should not find files in an untrusted parent repo folder', async () => {
+			const parentFolder = '/repos/untrusted-parent-test';
+			const rootFolder = `${parentFolder}/repo`;
+			const rootFolderUri = URI.file(rootFolder);
+
+			workspaceContextService.setWorkspace(testWorkspace(rootFolderUri));
+
+			await mockFiles(fileService, [
+				// .git in parent marks it as a repo root
+				{
+					path: `${parentFolder}/.git/HEAD`,
+					contents: ['ref: refs/heads/main'],
+				},
+				// Applying instruction in parent
+				{
+					path: `${parentFolder}/.github/instructions/typescript.instructions.md`,
+					contents: [
+						'---',
+						'description: \'Parent TypeScript instructions\'',
+						'applyTo: "**/*.ts"',
+						'---',
+						'Parent TypeScript coding standards',
+					]
+				},
+				// Prompt file in parent
+				{
+					path: `${parentFolder}/.github/prompts/help.prompt.md`,
+					contents: [
+						'---',
+						'description: \'Parent help prompt\'',
+						'---',
+						'Help the user with their question',
+					]
+				},
+				// Agent file in parent
+				{
+					path: `${parentFolder}/.github/agents/reviewer.agent.md`,
+					contents: [
+						'---',
+						'description: \'Parent code reviewer agent\'',
+						'---',
+						'You are a code reviewer',
+					]
+				},
+				{
+					path: `${rootFolder}/src/file.ts`,
+					contents: ['console.log("test");'],
+				},
+			]);
+
+			testConfigService.setUserConfiguration(PromptsConfig.INCLUDE_APPLYING_INSTRUCTIONS, true);
+			testConfigService.setUserConfiguration(PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS, true);
+
+			// Mark the parent repo root as untrusted
+			workspaceTrustService.getUriTrustInfo = (uri: URI) => {
+				if (uri.path === parentFolder) {
+					return Promise.resolve({ trusted: false, uri });
+				}
+				return Promise.resolve({ trusted: true, uri });
+			};
+
+			const promptFiles = await service.listPromptFiles(PromptsType.prompt, CancellationToken.None);
+			const agentFiles = await service.listPromptFiles(PromptsType.agent, CancellationToken.None);
+			const instructionFiles = await service.listPromptFiles(PromptsType.instructions, CancellationToken.None);
+
+			assert.ok(!promptFiles.some(f => f.uri.path.includes(parentFolder)), 'Should not find parent prompt files when parent repo is untrusted');
+			assert.ok(!agentFiles.some(f => f.uri.path.includes(parentFolder)), 'Should not find parent agent files when parent repo is untrusted');
+			assert.ok(!instructionFiles.some(f => f.uri.path.includes(parentFolder)), 'Should not find parent instruction files when parent repo is untrusted');
+		});
+	});
+
 	test('Instructions provider', async () => {
 		const instructionUri = URI.parse('file://extensions/my-extension/myInstruction.instructions.md');
 		const extension = {
@@ -2196,9 +2423,10 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.findAgentSkills(CancellationToken.None);
+			const allResult = await service.findAgentSkills(CancellationToken.None);
 
-			assert.ok(result, 'Should return results when agent skills are enabled');
+			assert.ok(allResult, 'Should return results when agent skills are enabled');
+			const result = allResult.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(result.length, 4, 'Should find 4 skills total');
 
 			// Check project skills (both from .github/skills and .claude/skills)
@@ -2264,10 +2492,11 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.findAgentSkills(CancellationToken.None);
+			const allResult = await service.findAgentSkills(CancellationToken.None);
 
 			// Should still return the valid skill, even if one has parsing errors
-			assert.ok(result, 'Should return results even with parsing errors');
+			assert.ok(allResult, 'Should return results even with parsing errors');
+			const result = allResult.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(result.length, 1, 'Should find 1 valid skill');
 			assert.strictEqual(result[0].name, 'Valid Skill');
 			assert.strictEqual(result[0].storage, PromptsStorage.local);
@@ -2285,9 +2514,10 @@ suite('PromptsService', () => {
 			// Create empty mock filesystem
 			await mockFiles(fileService, []);
 
-			const result = await service.findAgentSkills(CancellationToken.None);
+			const allResult = await service.findAgentSkills(CancellationToken.None);
 
-			assert.ok(result, 'Should return results array');
+			assert.ok(allResult, 'Should return results array');
+			const result = allResult.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(result.length, 0, 'Should find no skills');
 		});
 
@@ -2319,9 +2549,10 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.findAgentSkills(CancellationToken.None);
+			const allResult = await service.findAgentSkills(CancellationToken.None);
 
-			assert.ok(result, 'Should return results');
+			assert.ok(allResult, 'Should return results');
+			const result = allResult.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(result.length, 1, 'Should find 1 skill');
 			assert.strictEqual(result[0].name.length, 64, 'Name should be truncated to 64 characters');
 			assert.strictEqual(result[0].description?.length, 1024, 'Description should be truncated to 1024 characters');
@@ -2351,9 +2582,10 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.findAgentSkills(CancellationToken.None);
+			const allResult = await service.findAgentSkills(CancellationToken.None);
 
-			assert.ok(result, 'Should return results');
+			assert.ok(allResult, 'Should return results');
+			const result = allResult.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(result.length, 1, 'Should find 1 skill');
 			assert.strictEqual(result[0].name, 'Skill with XML tags', 'XML tags should be removed from name');
 			assert.strictEqual(result[0].description, 'Description with HTML and other tags', 'XML tags should be removed from description');
@@ -2387,9 +2619,10 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.findAgentSkills(CancellationToken.None);
+			const allResult = await service.findAgentSkills(CancellationToken.None);
 
-			assert.ok(result, 'Should return results');
+			assert.ok(allResult, 'Should return results');
+			const result = allResult.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(result.length, 1, 'Should find 1 skill');
 			// XML tags are removed first, then truncation happens
 			assert.ok(!result[0].name.includes('<'), 'Name should not contain XML tags');
@@ -2445,9 +2678,10 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.findAgentSkills(CancellationToken.None);
+			const allResult = await service.findAgentSkills(CancellationToken.None);
 
-			assert.ok(result, 'Should return results');
+			assert.ok(allResult, 'Should return results');
+			const result = allResult.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(result.length, 2, 'Should find 2 skills (duplicate skipped)');
 
 			const duplicateSkill = result.find(s => s.name === 'Duplicate Skill');
@@ -2493,9 +2727,10 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.findAgentSkills(CancellationToken.None);
+			const allResult = await service.findAgentSkills(CancellationToken.None);
 
-			assert.ok(result, 'Should return results');
+			assert.ok(allResult, 'Should return results');
+			const result = allResult.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(result.length, 1, 'Should find 1 skill (duplicates resolved by priority)');
 			assert.strictEqual(result[0].description, 'Workspace version - highest priority', 'Workspace should win over user');
 			assert.strictEqual(result[0].storage, PromptsStorage.local);
@@ -2536,9 +2771,10 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.findAgentSkills(CancellationToken.None);
+			const allResult = await service.findAgentSkills(CancellationToken.None);
 
-			assert.ok(result, 'Should return results');
+			assert.ok(allResult, 'Should return results');
+			const result = allResult.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(result.length, 1, 'Should find only 1 skill (mismatched one skipped)');
 			assert.strictEqual(result[0].name, 'Valid Skill', 'Should only find the valid skill');
 		});
@@ -2575,9 +2811,10 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const result = await service.findAgentSkills(CancellationToken.None);
+			const allResult = await service.findAgentSkills(CancellationToken.None);
 
-			assert.ok(result, 'Should return results');
+			assert.ok(allResult, 'Should return results');
+			const result = allResult.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(result.length, 1, 'Should find only 1 skill (one without name skipped)');
 			assert.strictEqual(result[0].name, 'Valid Named Skill', 'Should only find skill with name attribute');
 		});
@@ -2630,9 +2867,10 @@ suite('PromptsService', () => {
 
 			const registered = service.registerPromptFileProvider(extension, PromptsType.skill, provider);
 
-			const result = await service.findAgentSkills(CancellationToken.None);
+			const allResult = await service.findAgentSkills(CancellationToken.None);
 
-			assert.ok(result, 'Should return results');
+			assert.ok(allResult, 'Should return results');
+			const result = allResult.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(result.length, 2, 'Should find 2 skills (workspace + extension)');
 
 			const workspaceSkill = result.find(s => s.name === 'Workspace Skill');
@@ -2692,9 +2930,10 @@ suite('PromptsService', () => {
 				'A contributed skill from extension'
 			);
 
-			const result = await service.findAgentSkills(CancellationToken.None);
+			const allResult = await service.findAgentSkills(CancellationToken.None);
 
-			assert.ok(result, 'Should return results');
+			assert.ok(allResult, 'Should return results');
+			const result = allResult.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(result.length, 2, 'Should find 2 skills (local + contributed)');
 
 			const localSkill = result.find(s => s.name === 'Local Skill');
@@ -2708,7 +2947,7 @@ suite('PromptsService', () => {
 			registered.dispose();
 
 			// After disposal, only local skill should remain
-			const resultAfterDispose = await service.findAgentSkills(CancellationToken.None);
+			const resultAfterDispose = (await service.findAgentSkills(CancellationToken.None))?.filter(s => s.storage !== PromptsStorage.internal);
 			assert.strictEqual(resultAfterDispose?.length, 1, 'Should find 1 skill after disposal');
 			assert.strictEqual(resultAfterDispose?.[0].name, 'Local Skill');
 		});
@@ -3382,7 +3621,7 @@ suite('PromptsService', () => {
 				},
 			]);
 
-			const slashCommands = await service.getPromptSlashCommands(CancellationToken.None);
+			const slashCommands = (await service.getPromptSlashCommands(CancellationToken.None)).filter(c => c.promptPath.storage !== PromptsStorage.internal);
 
 			// All commands should be present in the raw list
 			assert.strictEqual(slashCommands.length, 4, 'Should find all 4 commands');
@@ -3440,20 +3679,25 @@ suite('PromptsService', () => {
 
 	suite('hooks', () => {
 		const createTestPlugin = (path: string, initialHooks: readonly IAgentPluginHook[]): { plugin: IAgentPlugin; hooks: ISettableObservable<readonly IAgentPluginHook[]> } => {
-			const enabled = observableValue<boolean>('testPluginEnabled', true);
+			const enablement = observableValue('testPluginEnablement', 2 /* ContributionEnablementState.EnabledProfile */);
 			const hooks = observableValue<readonly IAgentPluginHook[]>('testPluginHooks', initialHooks);
 			const commands = observableValue<readonly IAgentPluginCommand[]>('testPluginCommands', []);
 			const skills = observableValue<readonly IAgentPluginSkill[]>('testPluginSkills', []);
+			const agents = observableValue<readonly IAgentPluginAgent[]>('testPluginAgents', []);
+			const instructions = observableValue<readonly IAgentPluginInstruction[]>('testPluginInstructions', []);
 			const mcpServerDefinitions = observableValue<readonly IAgentPluginMcpServerDefinition[]>('testPluginMcpServerDefinitions', []);
 
 			return {
 				plugin: {
 					uri: URI.file(path),
-					enabled,
-					setEnabled: () => { },
+					label: basename(URI.file(path)),
+					enablement,
+					remove: () => { },
 					hooks,
 					commands,
 					skills,
+					agents,
+					instructions,
 					mcpServerDefinitions,
 				},
 				hooks,
@@ -3522,7 +3766,6 @@ suite('PromptsService', () => {
 			}]);
 
 			testPluginsObservable.set([plugin], undefined);
-			testAllPluginsObservable.set([plugin], undefined);
 
 			const result = await service.getHooks(CancellationToken.None);
 			assert.ok(result, 'Expected hooks result');
@@ -3544,7 +3787,6 @@ suite('PromptsService', () => {
 			}]);
 
 			testPluginsObservable.set([plugin], undefined);
-			testAllPluginsObservable.set([plugin], undefined);
 
 			const before = await service.getHooks(CancellationToken.None);
 			assert.ok(before, 'Expected hooks result before plugin update');
@@ -3560,5 +3802,165 @@ suite('PromptsService', () => {
 			assert.ok(after, 'Expected hooks result after plugin update');
 			assert.deepStrictEqual(after.hooks[HookType.PreToolUse], [{ type: 'command', command: 'echo after' }]);
 		});
+
+		test('returns undefined when workspace is untrusted', async function () {
+			workspaceContextService.setWorkspace(testWorkspace(URI.file('/test-workspace')));
+			testConfigService.setUserConfiguration(PromptsConfig.USE_CHAT_HOOKS, true);
+			testConfigService.setUserConfiguration(PromptsConfig.HOOKS_LOCATION_KEY, { [HOOKS_SOURCE_FOLDER]: true });
+
+			await mockFiles(fileService, [
+				{
+					path: '/test-workspace/.github/hooks/my-hook.json',
+					contents: [
+						JSON.stringify({
+							hooks: {
+								[HookType.PreToolUse]: [
+									{ type: 'command', command: 'echo test' },
+								],
+							},
+						}),
+					],
+				},
+			]);
+
+			// Trusted workspace should return hooks
+			const trustedResult = await service.getHooks(CancellationToken.None);
+			assert.ok(trustedResult, 'Expected hooks when workspace is trusted');
+			assert.strictEqual(trustedResult.hooks[HookType.PreToolUse]?.length, 1);
+
+			// Untrusted workspace should return undefined
+			await workspaceTrustService.setWorkspaceTrust(false);
+			const untrustedResult = await service.getHooks(CancellationToken.None);
+			assert.strictEqual(untrustedResult, undefined, 'Expected undefined hooks when workspace is untrusted');
+
+			// Re-trusting should return hooks again
+			await workspaceTrustService.setWorkspaceTrust(true);
+			const reTrustedResult = await service.getHooks(CancellationToken.None);
+			assert.ok(reTrustedResult, 'Expected hooks after workspace becomes trusted again');
+			assert.strictEqual(reTrustedResult.hooks[HookType.PreToolUse]?.length, 1);
+		});
+
+		test('suppresses plugin hooks when workspace is untrusted', async function () {
+			testConfigService.setUserConfiguration(PromptsConfig.USE_CHAT_HOOKS, true);
+			testConfigService.setUserConfiguration(PromptsConfig.HOOKS_LOCATION_KEY, {});
+
+			const { plugin } = createTestPlugin('/plugins/test-plugin', [{
+				type: HookType.PreToolUse,
+				originalId: 'plugin-pre-tool-use',
+				hooks: [{ type: 'command', command: 'echo from-plugin' }],
+			}]);
+
+			testPluginsObservable.set([plugin], undefined);
+
+			await workspaceTrustService.setWorkspaceTrust(false);
+			const result = await service.getHooks(CancellationToken.None);
+			assert.strictEqual(result, undefined, 'Expected undefined hooks when workspace is untrusted, even with plugin hooks');
+		});
+	});
+
+	suite('plugin instructions', () => {
+		function createPluginWithInstructions(
+			path: string,
+			initialInstructions: readonly IAgentPluginInstruction[],
+		): { plugin: IAgentPlugin; instructions: ISettableObservable<readonly IAgentPluginInstruction[]> } {
+			const enablement = observableValue('testPluginEnablement', 2 /* ContributionEnablementState.EnabledProfile */);
+			const hooks = observableValue<readonly IAgentPluginHook[]>('testPluginHooks', []);
+			const commands = observableValue<readonly IAgentPluginCommand[]>('testPluginCommands', []);
+			const skills = observableValue<readonly IAgentPluginSkill[]>('testPluginSkills', []);
+			const agents = observableValue<readonly IAgentPluginAgent[]>('testPluginAgents', []);
+			const instructions = observableValue<readonly IAgentPluginInstruction[]>('testPluginInstructions', initialInstructions);
+			const mcpServerDefinitions = observableValue<readonly IAgentPluginMcpServerDefinition[]>('testPluginMcpServerDefinitions', []);
+
+			return {
+				plugin: {
+					uri: URI.file(path),
+					label: basename(URI.file(path)),
+					enablement,
+					remove: () => { },
+					hooks,
+					commands,
+					skills,
+					agents,
+					instructions,
+					mcpServerDefinitions,
+				},
+				instructions,
+			};
+		}
+
+		test('lists plugin instructions via listPromptFiles', async function () {
+			const ruleUri = URI.file('/plugins/test-plugin/rules/prefer-const.mdc');
+			const { plugin } = createPluginWithInstructions('/plugins/test-plugin', [
+				{ uri: ruleUri, name: 'prefer-const' },
+			]);
+
+			testPluginsObservable.set([plugin], undefined);
+
+			const result = await service.listPromptFiles(PromptsType.instructions, CancellationToken.None);
+			const pluginInstruction = result.find(p => p.uri.toString() === ruleUri.toString());
+			assert.ok(pluginInstruction, 'Plugin instruction should appear in listPromptFiles');
+			assert.strictEqual(pluginInstruction!.storage, PromptsStorage.plugin);
+		});
+
+		test('updates listed instructions when plugin instructions change', async function () {
+			const ruleUri1 = URI.file('/plugins/test-plugin/rules/rule-a.mdc');
+			const ruleUri2 = URI.file('/plugins/test-plugin/rules/rule-b.mdc');
+			const { plugin, instructions } = createPluginWithInstructions('/plugins/test-plugin', [
+				{ uri: ruleUri1, name: 'rule-a' },
+			]);
+
+			testPluginsObservable.set([plugin], undefined);
+
+			const before = await service.listPromptFiles(PromptsType.instructions, CancellationToken.None);
+			const beforePlugin = before.filter(p => p.storage === PromptsStorage.plugin);
+			assert.strictEqual(beforePlugin.length, 1);
+
+			const eventFired = new Promise<void>(resolve => {
+				const disposable = service.onDidChangeInstructions(() => {
+					disposable.dispose();
+					resolve();
+				});
+			});
+
+			instructions.set([
+				{ uri: ruleUri1, name: 'rule-a' },
+				{ uri: ruleUri2, name: 'rule-b' },
+			], undefined);
+
+			await eventFired;
+
+			const after = await service.listPromptFiles(PromptsType.instructions, CancellationToken.None);
+			const afterPlugin = after.filter(p => p.storage === PromptsStorage.plugin);
+			assert.strictEqual(afterPlugin.length, 2);
+		});
+
+		test('removes instructions when plugin is removed', async function () {
+			const ruleUri = URI.file('/plugins/test-plugin/rules/rule-a.mdc');
+			const { plugin } = createPluginWithInstructions('/plugins/test-plugin', [
+				{ uri: ruleUri, name: 'rule-a' },
+			]);
+
+			testPluginsObservable.set([plugin], undefined);
+			const withPlugin = await service.listPromptFiles(PromptsType.instructions, CancellationToken.None);
+			assert.ok(withPlugin.some(p => p.storage === PromptsStorage.plugin));
+
+			testPluginsObservable.set([], undefined);
+			const withoutPlugin = await service.listPromptFiles(PromptsType.instructions, CancellationToken.None);
+			assert.ok(!withoutPlugin.some(p => p.storage === PromptsStorage.plugin));
+		});
+
+		test('namespaces plugin instruction names with plugin folder', async function () {
+			const ruleUri = URI.file('/plugins/deploy-tools/rules/lint-check.mdc');
+			const { plugin } = createPluginWithInstructions('/plugins/deploy-tools', [
+				{ uri: ruleUri, name: 'lint-check' },
+			]);
+
+			testPluginsObservable.set([plugin], undefined);
+
+			const result = await service.listPromptFiles(PromptsType.instructions, CancellationToken.None);
+			const pluginInstruction = result.find(p => p.uri.toString() === ruleUri.toString());
+			assert.ok(pluginInstruction, 'Plugin instruction should be listed');
+			assert.strictEqual(pluginInstruction!.name, 'deploy-tools:lint-check');
+		});
 	});
 });
diff --git a/src/vs/workbench/contrib/chat/test/common/promptSyntax/utils/promptFilesLocator.test.ts b/src/vs/workbench/contrib/chat/test/common/promptSyntax/utils/promptFilesLocator.test.ts
index 5d9664f790735..757eeca3a0dc5 100644
--- a/src/vs/workbench/contrib/chat/test/common/promptSyntax/utils/promptFilesLocator.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/promptSyntax/utils/promptFilesLocator.test.ts
@@ -25,11 +25,12 @@ import { IPathService } from '../../../../../../services/path/common/pathService
 import { PromptsConfig } from '../../../../common/promptSyntax/config/config.js';
 import { PromptsType } from '../../../../common/promptSyntax/promptTypes.js';
 import { hasGlobPattern, isValidGlob, isValidPromptFolderPath, PromptFilesLocator } from '../../../../common/promptSyntax/utils/promptFilesLocator.js';
-import { IMockFileEntry, IMockFolder, MockFilesystem } from '../testUtils/mockFilesystem.js';
+import { mockFiles } from '../testUtils/mockFilesystem.js';
 import { mockService } from './mock.js';
-import { TestUserDataProfileService } from '../../../../../../test/common/workbenchTestServices.js';
+import { TestUserDataProfileService, TestWorkspaceTrustManagementService } from '../../../../../../test/common/workbenchTestServices.js';
 import { PromptsStorage } from '../../../../common/promptSyntax/service/promptsService.js';
 import { runWithFakedTimers } from '../../../../../../../base/test/common/timeTravelScheduler.js';
+import { IWorkspaceTrustManagementService } from '../../../../../../../platform/workspace/common/workspaceTrust.js';
 
 /**
  * Mocked instance of {@link IConfigurationService}.
@@ -77,46 +78,57 @@ suite('PromptFilesLocator', () => {
 	const disposables = ensureNoDisposablesAreLeakedInTestSuite();
 
 	let instantiationService: TestInstantiationService;
+	let fileService: IFileService;
+	const configValues: Record<string, unknown> = {};
+	let workspaceTrustService: TestWorkspaceTrustManagementService;
+
+	// Sets all prompt file location config keys to the same value
+	const setLocations = (value: unknown) => {
+		configValues[PromptsConfig.PROMPT_LOCATIONS_KEY] = value;
+		configValues[PromptsConfig.INSTRUCTIONS_LOCATION_KEY] = value;
+		configValues[PromptsConfig.MODE_LOCATION_KEY] = value;
+		configValues[PromptsConfig.SKILLS_LOCATION_KEY] = value;
+	};
+
+	// Stubs workspace context service with the given folder paths
+	const setWorkspaceFolders = (paths: string[]) => {
+		const workspaceFolders = paths.map((path, index) => {
+			const uri = URI.file(path);
+			return new class extends mock<IWorkspaceFolder>() {
+				override uri = uri;
+				override name = basename(uri);
+				override index = index;
+			};
+		});
+		instantiationService.stub(IWorkspaceContextService, mockWorkspaceService(workspaceFolders));
+	};
+
 	setup(async () => {
 		instantiationService = disposables.add(new TestInstantiationService());
 		instantiationService.stub(ILogService, new NullLogService());
 
-		const fileService = disposables.add(instantiationService.createInstance(FileService));
+		fileService = disposables.add(instantiationService.createInstance(FileService));
 		const fileSystemProvider = disposables.add(new InMemoryFileSystemProvider());
 		disposables.add(fileService.registerProvider(Schemas.file, fileSystemProvider));
-
 		instantiationService.stub(IFileService, fileService);
-	});
-
-	/**
-	 * Create a new instance of {@link PromptFilesLocator} with provided mocked
-	 * values for configuration and workspace services.
-	 */
-	const createPromptsLocator = async (configValue: unknown, workspaceFolderPaths: string[], filesystem: IMockFolder[]) => {
 
-		const mockFs = instantiationService.createInstance(MockFilesystem, filesystem);
-		await mockFs.mock();
+		workspaceTrustService = disposables.add(new TestWorkspaceTrustManagementService());
+		instantiationService.stub(IWorkspaceTrustManagementService, workspaceTrustService);
 
-		instantiationService.stub(IConfigurationService, mockConfigService({
+		// Reset config values to defaults
+		for (const key of Object.keys(configValues)) {
+			delete configValues[key];
+		}
+		Object.assign(configValues, {
 			'explorer.excludeGitIgnore': false,
 			'files.exclude': {},
 			'search.exclude': {},
-			[PromptsConfig.PROMPT_LOCATIONS_KEY]: configValue,
-			[PromptsConfig.INSTRUCTIONS_LOCATION_KEY]: configValue,
-			[PromptsConfig.MODE_LOCATION_KEY]: configValue,
-			[PromptsConfig.SKILLS_LOCATION_KEY]: configValue,
-		}));
+			[PromptsConfig.USE_CUSTOMIZATIONS_IN_PARENT_REPOS]: false,
+		});
+		instantiationService.stub(IConfigurationService, mockConfigService(configValues));
 
-		const workspaceFolders = workspaceFolderPaths.map((path, index) => {
-			const uri = URI.file(path);
+		setWorkspaceFolders([]);
 
-			return new class extends mock<IWorkspaceFolder>() {
-				override uri = uri;
-				override name = basename(uri);
-				override index = index;
-			};
-		});
-		instantiationService.stub(IWorkspaceContextService, mockWorkspaceService(workspaceFolders));
 		instantiationService.stub(IWorkbenchEnvironmentService, {} as IWorkbenchEnvironmentService);
 		instantiationService.stub(IUserDataProfileService, new TestUserDataProfileService());
 		instantiationService.stub(ISearchService, {
@@ -124,11 +136,9 @@ suite('PromptFilesLocator', () => {
 				return true;
 			},
 			async fileSearch(query: IFileQuery) {
-				// mock the search service
-				const fs = instantiationService.get(IFileService);
 				const findFilesInLocation = async (location: URI, results: URI[] = []) => {
 					try {
-						const resolve = await fs.resolve(location);
+						const resolve = await fileService.resolve(location);
 						if (resolve.isFile) {
 							results.push(resolve.resource);
 						} else if (resolve.isDirectory && resolve.children) {
@@ -149,7 +159,6 @@ suite('PromptFilesLocator', () => {
 							results.push({ resource });
 						}
 					}
-
 				}
 				return { results, messages: [] };
 			}
@@ -163,134 +172,112 @@ suite('PromptFilesLocator', () => {
 				return Promise.resolve(uri);
 			}
 		} as IPathService);
-
-		const locator = instantiationService.createInstance(PromptFilesLocator);
-
-		return {
-			async listFiles(type: PromptsType, storage: PromptsStorage, token: CancellationToken): Promise<readonly URI[]> {
-				return locator.listFiles(type, storage, token);
-			},
-			async getConfigBasedSourceFolders(type: PromptsType): Promise<readonly URI[]> {
-				return await locator.getConfigBasedSourceFolders(type);
-			},
-			async findAgentSkills(token: CancellationToken) {
-				return await locator.findAgentSkills(token);
-			},
-			async disposeAsync(): Promise<void> {
-				await mockFs.delete();
-			}
-		};
-	};
+	});
 
 	suite('empty workspace', () => {
 		const EMPTY_WORKSPACE: string[] = [];
 
 		suite('empty filesystem', () => {
 			testT('no config value', async () => {
-				const locator = await createPromptsLocator(undefined, EMPTY_WORKSPACE, []);
+				setLocations(undefined);
+				setWorkspaceFolders(EMPTY_WORKSPACE);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				assertOutcome(
 					await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
 					[],
 					'No prompts must be found.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('object config value', async () => {
-				const locator = await createPromptsLocator({
+				setLocations({
 					'/Users/legomushroom/repos/prompts/': true,
 					'/tmp/prompts/': false,
-				}, EMPTY_WORKSPACE, []);
+				});
+				setWorkspaceFolders(EMPTY_WORKSPACE);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				assertOutcome(
 					await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
 					[],
 					'No prompts must be found.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('array config value', async () => {
-				const locator = await createPromptsLocator([
+				setLocations([
 					'relative/path/to/prompts/',
 					'/abs/path',
-				], EMPTY_WORKSPACE, []);
+				]);
+				setWorkspaceFolders(EMPTY_WORKSPACE);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				assertOutcome(
 					await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
 					[],
 					'No prompts must be found.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('null config value', async () => {
-				const locator = await createPromptsLocator(null, EMPTY_WORKSPACE, []);
+				setLocations(null);
+				setWorkspaceFolders(EMPTY_WORKSPACE);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				assertOutcome(
 					await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
 					[],
 					'No prompts must be found.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('string config value', async () => {
-				const locator = await createPromptsLocator('/etc/hosts/prompts', EMPTY_WORKSPACE, []);
+				setLocations('/etc/hosts/prompts');
+				setWorkspaceFolders(EMPTY_WORKSPACE);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				assertOutcome(
 					await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
 					[],
 					'No prompts must be found.',
 				);
-				await locator.disposeAsync();
 			});
 		});
 
 		suite('non-empty filesystem', () => {
 			testT('core logic', async () => {
-				const locator = await createPromptsLocator(
+				setLocations({
+					'/Users/legomushroom/repos/prompts': true,
+					'/tmp/prompts/': true,
+					'/absolute/path/prompts': false,
+					'.copilot/prompts': true,
+				});
+				setWorkspaceFolders(EMPTY_WORKSPACE);
+				await mockFiles(fileService, [
 					{
-						'/Users/legomushroom/repos/prompts': true,
-						'/tmp/prompts/': true,
-						'/absolute/path/prompts': false,
-						'.copilot/prompts': true,
+						path: '/Users/legomushroom/repos/prompts/test.prompt.md',
+						contents: ['Hello, World!'],
 					},
-					EMPTY_WORKSPACE,
-					[
-						{
-							name: '/Users/legomushroom/repos/prompts',
-							children: [
-								{
-									name: 'test.prompt.md',
-									contents: 'Hello, World!',
-								},
-								{
-									name: 'refactor-tests.prompt.md',
-									contents: 'some file content goes here',
-								},
-							],
-						},
-						{
-							name: '/tmp/prompts',
-							children: [
-								{
-									name: 'translate.to-rust.prompt.md',
-									contents: 'some more random file contents',
-								},
-							],
-						},
-						{
-							name: '/absolute/path/prompts',
-							children: [
-								{
-									name: 'some-prompt-file.prompt.md',
-									contents: 'hey hey hey',
-								},
-							],
-						},
-					]);
+					{
+						path: '/Users/legomushroom/repos/prompts/refactor-tests.prompt.md',
+						contents: ['some file content goes here'],
+					},
+					{
+						path: '/tmp/prompts/translate.to-rust.prompt.md',
+						contents: ['some more random file contents'],
+					},
+					{
+						path: '/absolute/path/prompts/some-prompt-file.prompt.md',
+						contents: ['hey hey hey'],
+					},
+				]);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				assertOutcome(
 					await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -301,7 +288,6 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must find correct prompts.',
 				);
-				await locator.disposeAsync();
 			});
 
 			suite('absolute', () => {
@@ -326,47 +312,31 @@ suite('PromptFilesLocator', () => {
 					];
 
 					for (const setting of settings) {
-						const locator = await createPromptsLocator(
-							{ [setting]: true },
-							EMPTY_WORKSPACE,
-							[
-								{
-									name: '/Users/legomushroom/repos/vscode',
-									children: [
-										{
-											name: 'deps/text',
-											children: [
-												{
-													name: 'my.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'nested',
-													children: [
-														{
-															name: 'specific.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'unspecific1.prompt.md',
-															contents: 'oh hi, robot!',
-														},
-														{
-															name: 'unspecific2.prompt.md',
-															contents: 'oh hi, rabot!',
-														},
-														{
-															name: 'readme.md',
-															contents: 'non prompt file',
-														},
-													],
-												}
-											],
-										},
-									],
-								},
-							],
-						);
+						setLocations({ [setting]: true });
+						setWorkspaceFolders(EMPTY_WORKSPACE);
+						await mockFiles(fileService, [
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/my.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/specific.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/unspecific1.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/unspecific2.prompt.md',
+								contents: ['oh hi, rabot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/readme.md',
+								contents: ['non prompt file'],
+							},
+						]);
+						const locator = instantiationService.createInstance(PromptFilesLocator);
 
 						assertOutcome(
 							await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -378,7 +348,6 @@ suite('PromptFilesLocator', () => {
 							],
 							'Must find correct prompts.',
 						);
-						await locator.disposeAsync();
 					}
 				});
 
@@ -480,51 +449,35 @@ suite('PromptFilesLocator', () => {
 							vscodeSettings[setting] = true;
 						}
 
-						const locator = await createPromptsLocator(
-							vscodeSettings,
-							EMPTY_WORKSPACE,
-							[
-								{
-									name: '/Users/legomushroom/repos/vscode',
-									children: [
-										{
-											name: 'deps/text',
-											children: [
-												{
-													name: 'my.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'nested',
-													children: [
-														{
-															name: 'default.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'specific.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'unspecific1.prompt.md',
-															contents: 'oh hi, robot!',
-														},
-														{
-															name: 'unspecific2.prompt.md',
-															contents: 'oh hi, rawbot!',
-														},
-														{
-															name: 'readme.md',
-															contents: 'non prompt file',
-														},
-													],
-												}
-											],
-										},
-									],
-								},
-							],
-						);
+						setLocations(vscodeSettings);
+						setWorkspaceFolders(EMPTY_WORKSPACE);
+						await mockFiles(fileService, [
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/my.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/default.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/specific.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/unspecific1.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/unspecific2.prompt.md',
+								contents: ['oh hi, rawbot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/readme.md',
+								contents: ['non prompt file'],
+							},
+						]);
+						const locator = instantiationService.createInstance(PromptFilesLocator);
 
 						assertOutcome(
 							await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -535,7 +488,6 @@ suite('PromptFilesLocator', () => {
 							],
 							'Must find correct prompts.',
 						);
-						await locator.disposeAsync();
 					}
 				});
 			});
@@ -566,47 +518,31 @@ suite('PromptFilesLocator', () => {
 					];
 
 					for (const setting of testSettings) {
-						const locator = await createPromptsLocator(
-							{ [setting]: true },
-							['/Users/legomushroom/repos/vscode'],
-							[
-								{
-									name: '/Users/legomushroom/repos/vscode',
-									children: [
-										{
-											name: 'deps/text',
-											children: [
-												{
-													name: 'my.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'nested',
-													children: [
-														{
-															name: 'specific.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'unspecific1.prompt.md',
-															contents: 'oh hi, robot!',
-														},
-														{
-															name: 'unspecific2.prompt.md',
-															contents: 'oh hi, rabot!',
-														},
-														{
-															name: 'readme.md',
-															contents: 'non prompt file',
-														},
-													],
-												}
-											],
-										},
-									],
-								},
-							],
-						);
+						setLocations({ [setting]: true });
+						setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+						await mockFiles(fileService, [
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/my.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/specific.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/unspecific1.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/unspecific2.prompt.md',
+								contents: ['oh hi, rabot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/readme.md',
+								contents: ['non prompt file'],
+							},
+						]);
+						const locator = instantiationService.createInstance(PromptFilesLocator);
 
 						assertOutcome(
 							await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -618,7 +554,6 @@ suite('PromptFilesLocator', () => {
 							],
 							'Must find correct prompts.',
 						);
-						await locator.disposeAsync();
 
 					}
 				});
@@ -721,51 +656,35 @@ suite('PromptFilesLocator', () => {
 							vscodeSettings[setting] = true;
 						}
 
-						const locator = await createPromptsLocator(
-							vscodeSettings,
-							['/Users/legomushroom/repos/vscode'],
-							[
-								{
-									name: '/Users/legomushroom/repos/vscode',
-									children: [
-										{
-											name: 'deps/text',
-											children: [
-												{
-													name: 'my.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'nested',
-													children: [
-														{
-															name: 'default.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'specific.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'unspecific1.prompt.md',
-															contents: 'oh hi, robot!',
-														},
-														{
-															name: 'unspecific2.prompt.md',
-															contents: 'oh hi, rawbot!',
-														},
-														{
-															name: 'readme.md',
-															contents: 'non prompt file',
-														},
-													],
-												}
-											],
-										},
-									],
-								},
-							],
-						);
+						setLocations(vscodeSettings);
+						setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+						await mockFiles(fileService, [
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/my.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/default.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/specific.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/unspecific1.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/unspecific2.prompt.md',
+								contents: ['oh hi, rawbot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/readme.md',
+								contents: ['non prompt file'],
+							},
+						]);
+						const locator = instantiationService.createInstance(PromptFilesLocator);
 
 						assertOutcome(
 							await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -776,7 +695,6 @@ suite('PromptFilesLocator', () => {
 							],
 							'Must find correct prompts.',
 						);
-						await locator.disposeAsync();
 					}
 				});
 			});
@@ -804,47 +722,31 @@ suite('PromptFilesLocator', () => {
 
 					for (const setting of settings) {
 
-						const locator = await createPromptsLocator(
-							{ [setting]: true },
-							['/Users/legomushroom/repos/vscode'],
-							[
-								{
-									name: '/Users/legomushroom/repos/vscode',
-									children: [
-										{
-											name: 'deps/text',
-											children: [
-												{
-													name: 'my.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'nested',
-													children: [
-														{
-															name: 'specific.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'unspecific1.prompt.md',
-															contents: 'oh hi, robot!',
-														},
-														{
-															name: 'unspecific2.prompt.md',
-															contents: 'oh hi, rabot!',
-														},
-														{
-															name: 'readme.md',
-															contents: 'non prompt file',
-														},
-													],
-												}
-											],
-										},
-									],
-								},
-							],
-						);
+						setLocations({ [setting]: true });
+						setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+						await mockFiles(fileService, [
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/my.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/specific.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/unspecific1.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/unspecific2.prompt.md',
+								contents: ['oh hi, rabot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/readme.md',
+								contents: ['non prompt file'],
+							},
+						]);
+						const locator = instantiationService.createInstance(PromptFilesLocator);
 
 						assertOutcome(
 							await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -856,7 +758,6 @@ suite('PromptFilesLocator', () => {
 							],
 							'Must find correct prompts.',
 						);
-						await locator.disposeAsync();
 
 					}
 				});
@@ -959,51 +860,35 @@ suite('PromptFilesLocator', () => {
 							vscodeSettings[setting] = true;
 						}
 
-						const locator = await createPromptsLocator(
-							vscodeSettings,
-							['/Users/legomushroom/repos/vscode'],
-							[
-								{
-									name: '/Users/legomushroom/repos/vscode',
-									children: [
-										{
-											name: 'deps/text',
-											children: [
-												{
-													name: 'my.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'nested',
-													children: [
-														{
-															name: 'default.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'specific.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'unspecific1.prompt.md',
-															contents: 'oh hi, robot!',
-														},
-														{
-															name: 'unspecific2.prompt.md',
-															contents: 'oh hi, rawbot!',
-														},
-														{
-															name: 'readme.md',
-															contents: 'non prompt file',
-														},
-													],
-												}
-											],
-										},
-									],
-								},
-							],
-						);
+						setLocations(vscodeSettings);
+						setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+						await mockFiles(fileService, [
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/my.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/default.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/specific.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/unspecific1.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/unspecific2.prompt.md',
+								contents: ['oh hi, rawbot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/deps/text/nested/readme.md',
+								contents: ['non prompt file'],
+							},
+						]);
+						const locator = instantiationService.createInstance(PromptFilesLocator);
 
 						assertOutcome(
 							await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -1014,7 +899,6 @@ suite('PromptFilesLocator', () => {
 							],
 							'Must find correct prompts.',
 						);
-						await locator.disposeAsync();
 
 					}
 				});
@@ -1023,72 +907,42 @@ suite('PromptFilesLocator', () => {
 	});
 
 	testT('core logic', async () => {
-		const locator = await createPromptsLocator(
+		setLocations({
+			'/Users/legomushroom/repos/prompts': true,
+			'/tmp/prompts/': true,
+			'/absolute/path/prompts': false,
+			'.copilot/prompts': true,
+		});
+		setWorkspaceFolders([
+			'/Users/legomushroom/repos/vscode',
+		]);
+		await mockFiles(fileService, [
 			{
-				'/Users/legomushroom/repos/prompts': true,
-				'/tmp/prompts/': true,
-				'/absolute/path/prompts': false,
-				'.copilot/prompts': true,
+				path: '/Users/legomushroom/repos/prompts/test.prompt.md',
+				contents: ['Hello, World!'],
 			},
-			[
-				'/Users/legomushroom/repos/vscode',
-			],
-			[
-				{
-					name: '/Users/legomushroom/repos/prompts',
-					children: [
-						{
-							name: 'test.prompt.md',
-							contents: 'Hello, World!',
-						},
-						{
-							name: 'refactor-tests.prompt.md',
-							contents: 'some file content goes here',
-						},
-					],
-				},
-				{
-					name: '/tmp/prompts',
-					children: [
-						{
-							name: 'translate.to-rust.prompt.md',
-							contents: 'some more random file contents',
-						},
-					],
-				},
-				{
-					name: '/absolute/path/prompts',
-					children: [
-						{
-							name: 'some-prompt-file.prompt.md',
-							contents: 'hey hey hey',
-						},
-					],
-				},
-				{
-					name: '/Users/legomushroom/repos/vscode',
-					children: [
-						{
-							name: '.copilot/prompts',
-							children: [
-								{
-									name: 'default.prompt.md',
-									contents: 'oh hi, robot!',
-								},
-							],
-						},
-						{
-							name: '.github/prompts',
-							children: [
-								{
-									name: 'my.prompt.md',
-									contents: 'oh hi, bot!',
-								},
-							],
-						},
-					],
-				},
-			]);
+			{
+				path: '/Users/legomushroom/repos/prompts/refactor-tests.prompt.md',
+				contents: ['some file content goes here'],
+			},
+			{
+				path: '/tmp/prompts/translate.to-rust.prompt.md',
+				contents: ['some more random file contents'],
+			},
+			{
+				path: '/absolute/path/prompts/some-prompt-file.prompt.md',
+				contents: ['hey hey hey'],
+			},
+			{
+				path: '/Users/legomushroom/repos/vscode/.copilot/prompts/default.prompt.md',
+				contents: ['oh hi, robot!'],
+			},
+			{
+				path: '/Users/legomushroom/repos/vscode/.github/prompts/my.prompt.md',
+				contents: ['oh hi, bot!'],
+			},
+		]);
+		const locator = instantiationService.createInstance(PromptFilesLocator);
 
 		assertOutcome(
 			await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -1101,81 +955,50 @@ suite('PromptFilesLocator', () => {
 			],
 			'Must find correct prompts.',
 		);
-		await locator.disposeAsync();
 	});
 
 	testT('with disabled `.github/prompts` location', async () => {
-		const locator = await createPromptsLocator(
+		setLocations({
+			'/Users/legomushroom/repos/prompts': true,
+			'/tmp/prompts/': true,
+			'/absolute/path/prompts': false,
+			'.copilot/prompts': true,
+			'.github/prompts': false,
+		});
+		setWorkspaceFolders([
+			'/Users/legomushroom/repos/vscode',
+		]);
+		await mockFiles(fileService, [
 			{
-				'/Users/legomushroom/repos/prompts': true,
-				'/tmp/prompts/': true,
-				'/absolute/path/prompts': false,
-				'.copilot/prompts': true,
-				'.github/prompts': false,
+				path: '/Users/legomushroom/repos/prompts/test.prompt.md',
+				contents: ['Hello, World!'],
 			},
-			[
-				'/Users/legomushroom/repos/vscode',
-			],
-			[
-				{
-					name: '/Users/legomushroom/repos/prompts',
-					children: [
-						{
-							name: 'test.prompt.md',
-							contents: 'Hello, World!',
-						},
-						{
-							name: 'refactor-tests.prompt.md',
-							contents: 'some file content goes here',
-						},
-					],
-				},
-				{
-					name: '/tmp/prompts',
-					children: [
-						{
-							name: 'translate.to-rust.prompt.md',
-							contents: 'some more random file contents',
-						},
-					],
-				},
-				{
-					name: '/absolute/path/prompts',
-					children: [
-						{
-							name: 'some-prompt-file.prompt.md',
-							contents: 'hey hey hey',
-						},
-					],
-				},
-				{
-					name: '/Users/legomushroom/repos/vscode',
-					children: [
-						{
-							name: '.copilot/prompts',
-							children: [
-								{
-									name: 'default.prompt.md',
-									contents: 'oh hi, robot!',
-								},
-							],
-						},
-						{
-							name: '.github/prompts',
-							children: [
-								{
-									name: 'my.prompt.md',
-									contents: 'oh hi, bot!',
-								},
-								{
-									name: 'your.prompt.md',
-									contents: 'oh hi, bot!',
-								},
-							],
-						},
-					],
-				},
-			]);
+			{
+				path: '/Users/legomushroom/repos/prompts/refactor-tests.prompt.md',
+				contents: ['some file content goes here'],
+			},
+			{
+				path: '/tmp/prompts/translate.to-rust.prompt.md',
+				contents: ['some more random file contents'],
+			},
+			{
+				path: '/absolute/path/prompts/some-prompt-file.prompt.md',
+				contents: ['hey hey hey'],
+			},
+			{
+				path: '/Users/legomushroom/repos/vscode/.copilot/prompts/default.prompt.md',
+				contents: ['oh hi, robot!'],
+			},
+			{
+				path: '/Users/legomushroom/repos/vscode/.github/prompts/my.prompt.md',
+				contents: ['oh hi, bot!'],
+			},
+			{
+				path: '/Users/legomushroom/repos/vscode/.github/prompts/your.prompt.md',
+				contents: ['oh hi, bot!'],
+			},
+		]);
+		const locator = instantiationService.createInstance(PromptFilesLocator);
 
 		assertOutcome(
 			await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -1187,116 +1010,64 @@ suite('PromptFilesLocator', () => {
 			],
 			'Must find correct prompts.',
 		);
-		await locator.disposeAsync();
 	});
 
 	suite('multi-root workspace', () => {
 		suite('core logic', () => {
 			testT('without top-level `.github` folder', async () => {
-				const locator = await createPromptsLocator(
+				setLocations({
+					'/Users/legomushroom/repos/prompts': true,
+					'/tmp/prompts/': true,
+					'/absolute/path/prompts': false,
+					'.copilot/prompts': false,
+				});
+				setWorkspaceFolders([
+					'/Users/legomushroom/repos/vscode',
+					'/Users/legomushroom/repos/node',
+				]);
+				await mockFiles(fileService, [
 					{
-						'/Users/legomushroom/repos/prompts': true,
-						'/tmp/prompts/': true,
-						'/absolute/path/prompts': false,
-						'.copilot/prompts': false,
+						path: '/Users/legomushroom/repos/prompts/test.prompt.md',
+						contents: ['Hello, World!'],
 					},
-					[
-						'/Users/legomushroom/repos/vscode',
-						'/Users/legomushroom/repos/node',
-					],
-					[
-						{
-							name: '/Users/legomushroom/repos/prompts',
-							children: [
-								{
-									name: 'test.prompt.md',
-									contents: 'Hello, World!',
-								},
-								{
-									name: 'refactor-tests.prompt.md',
-									contents: 'some file content goes here',
-								},
-							],
-						},
-						{
-							name: '/tmp/prompts',
-							children: [
-								{
-									name: 'translate.to-rust.prompt.md',
-									contents: 'some more random file contents',
-								},
-							],
-						},
-						{
-							name: '/absolute/path/prompts',
-							children: [
-								{
-									name: 'some-prompt-file.prompt.md',
-									contents: 'hey hey hey',
-								},
-							],
-						},
-						{
-							name: '/Users/legomushroom/repos/vscode',
-							children: [
-								{
-									name: '.copilot/prompts',
-									children: [
-										{
-											name: 'prompt1.prompt.md',
-											contents: 'oh hi, robot!',
-										},
-									],
-								},
-								{
-									name: '.github/prompts',
-									children: [
-										{
-											name: 'default.prompt.md',
-											contents: 'oh hi, bot!',
-										},
-									],
-								},
-							],
-						},
-						{
-							name: '/Users/legomushroom/repos/node',
-							children: [
-								{
-									name: '.copilot/prompts',
-									children: [
-										{
-											name: 'prompt5.prompt.md',
-											contents: 'oh hi, robot!',
-										},
-									],
-								},
-								{
-									name: '.github/prompts',
-									children: [
-										{
-											name: 'refactor-static-classes.prompt.md',
-											contents: 'file contents',
-										},
-									],
-								},
-							],
-						},
-						// note! this folder is not part of the workspace, so prompt files are `ignored`
-						{
-							name: '/Users/legomushroom/repos/.github/prompts',
-							children: [
-								{
-									name: 'prompt-name.prompt.md',
-									contents: 'oh hi, robot!',
-								},
-								{
-									name: 'name-of-the-prompt.prompt.md',
-									contents: 'oh hi, raw bot!',
-								},
-							],
-						},
-					]);
+					{
+						path: '/Users/legomushroom/repos/prompts/refactor-tests.prompt.md',
+						contents: ['some file content goes here'],
+					},
+					{
+						path: '/tmp/prompts/translate.to-rust.prompt.md',
+						contents: ['some more random file contents'],
+					},
+					{
+						path: '/absolute/path/prompts/some-prompt-file.prompt.md',
+						contents: ['hey hey hey'],
+					},
+					{
+						path: '/Users/legomushroom/repos/vscode/.copilot/prompts/prompt1.prompt.md',
+						contents: ['oh hi, robot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/vscode/.github/prompts/default.prompt.md',
+						contents: ['oh hi, bot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/node/.copilot/prompts/prompt5.prompt.md',
+						contents: ['oh hi, robot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/node/.github/prompts/refactor-static-classes.prompt.md',
+						contents: ['file contents'],
+					},
+					{
+						path: '/Users/legomushroom/repos/.github/prompts/prompt-name.prompt.md',
+						contents: ['oh hi, robot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/.github/prompts/name-of-the-prompt.prompt.md',
+						contents: ['oh hi, raw bot!'],
+					},
+				]);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				assertOutcome(
 					await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -1309,115 +1080,63 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must find correct prompts.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('with top-level `.github` folder', async () => {
-				const locator = await createPromptsLocator(
+				setLocations({
+					'/Users/legomushroom/repos/prompts': true,
+					'/tmp/prompts/': true,
+					'/absolute/path/prompts': false,
+					'.copilot/prompts': false,
+				});
+				setWorkspaceFolders([
+					'/Users/legomushroom/repos/vscode',
+					'/Users/legomushroom/repos/node',
+					'/var/shared/prompts',
+				]);
+				await mockFiles(fileService, [
 					{
-						'/Users/legomushroom/repos/prompts': true,
-						'/tmp/prompts/': true,
-						'/absolute/path/prompts': false,
-						'.copilot/prompts': false,
+						path: '/Users/legomushroom/repos/prompts/test.prompt.md',
+						contents: ['Hello, World!'],
 					},
-					[
-						'/Users/legomushroom/repos/vscode',
-						'/Users/legomushroom/repos/node',
-						'/var/shared/prompts',
-					],
-					[
-						{
-							name: '/Users/legomushroom/repos/prompts',
-							children: [
-								{
-									name: 'test.prompt.md',
-									contents: 'Hello, World!',
-								},
-								{
-									name: 'refactor-tests.prompt.md',
-									contents: 'some file content goes here',
-								},
-							],
-						},
-						{
-							name: '/tmp/prompts',
-							children: [
-								{
-									name: 'translate.to-rust.prompt.md',
-									contents: 'some more random file contents',
-								},
-							],
-						},
-						{
-							name: '/absolute/path/prompts',
-							children: [
-								{
-									name: 'some-prompt-file.prompt.md',
-									contents: 'hey hey hey',
-								},
-							],
-						},
-						{
-							name: '/Users/legomushroom/repos/vscode',
-							children: [
-								{
-									name: '.copilot/prompts',
-									children: [
-										{
-											name: 'prompt1.prompt.md',
-											contents: 'oh hi, robot!',
-										},
-									],
-								},
-								{
-									name: '.github/prompts',
-									children: [
-										{
-											name: 'default.prompt.md',
-											contents: 'oh hi, bot!',
-										},
-									],
-								},
-							],
-						},
-						{
-							name: '/Users/legomushroom/repos/node',
-							children: [
-								{
-									name: '.copilot/prompts',
-									children: [
-										{
-											name: 'prompt5.prompt.md',
-											contents: 'oh hi, robot!',
-										},
-									],
-								},
-								{
-									name: '.github/prompts',
-									children: [
-										{
-											name: 'refactor-static-classes.prompt.md',
-											contents: 'file contents',
-										},
-									],
-								},
-							],
-						},
-						// note! this folder is part of the workspace, so prompt files are `included`
-						{
-							name: '/var/shared/prompts/.github/prompts',
-							children: [
-								{
-									name: 'prompt-name.prompt.md',
-									contents: 'oh hi, robot!',
-								},
-								{
-									name: 'name-of-the-prompt.prompt.md',
-									contents: 'oh hi, raw bot!',
-								},
-							],
-						},
-					]);
+					{
+						path: '/Users/legomushroom/repos/prompts/refactor-tests.prompt.md',
+						contents: ['some file content goes here'],
+					},
+					{
+						path: '/tmp/prompts/translate.to-rust.prompt.md',
+						contents: ['some more random file contents'],
+					},
+					{
+						path: '/absolute/path/prompts/some-prompt-file.prompt.md',
+						contents: ['hey hey hey'],
+					},
+					{
+						path: '/Users/legomushroom/repos/vscode/.copilot/prompts/prompt1.prompt.md',
+						contents: ['oh hi, robot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/vscode/.github/prompts/default.prompt.md',
+						contents: ['oh hi, bot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/node/.copilot/prompts/prompt5.prompt.md',
+						contents: ['oh hi, robot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/node/.github/prompts/refactor-static-classes.prompt.md',
+						contents: ['file contents'],
+					},
+					{
+						path: '/var/shared/prompts/.github/prompts/prompt-name.prompt.md',
+						contents: ['oh hi, robot!'],
+					},
+					{
+						path: '/var/shared/prompts/.github/prompts/name-of-the-prompt.prompt.md',
+						contents: ['oh hi, raw bot!'],
+					},
+				]);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				assertOutcome(
 					await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -1432,116 +1151,64 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must find correct prompts.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('with disabled `.github/prompts` location', async () => {
-				const locator = await createPromptsLocator(
+				setLocations({
+					'/Users/legomushroom/repos/prompts': true,
+					'/tmp/prompts/': true,
+					'/absolute/path/prompts': false,
+					'.copilot/prompts': false,
+					'.github/prompts': false,
+				});
+				setWorkspaceFolders([
+					'/Users/legomushroom/repos/vscode',
+					'/Users/legomushroom/repos/node',
+					'/var/shared/prompts',
+				]);
+				await mockFiles(fileService, [
 					{
-						'/Users/legomushroom/repos/prompts': true,
-						'/tmp/prompts/': true,
-						'/absolute/path/prompts': false,
-						'.copilot/prompts': false,
-						'.github/prompts': false,
+						path: '/Users/legomushroom/repos/prompts/test.prompt.md',
+						contents: ['Hello, World!'],
 					},
-					[
-						'/Users/legomushroom/repos/vscode',
-						'/Users/legomushroom/repos/node',
-						'/var/shared/prompts',
-					],
-					[
-						{
-							name: '/Users/legomushroom/repos/prompts',
-							children: [
-								{
-									name: 'test.prompt.md',
-									contents: 'Hello, World!',
-								},
-								{
-									name: 'refactor-tests.prompt.md',
-									contents: 'some file content goes here',
-								},
-							],
-						},
-						{
-							name: '/tmp/prompts',
-							children: [
-								{
-									name: 'translate.to-rust.prompt.md',
-									contents: 'some more random file contents',
-								},
-							],
-						},
-						{
-							name: '/absolute/path/prompts',
-							children: [
-								{
-									name: 'some-prompt-file.prompt.md',
-									contents: 'hey hey hey',
-								},
-							],
-						},
-						{
-							name: '/Users/legomushroom/repos/vscode',
-							children: [
-								{
-									name: '.copilot/prompts',
-									children: [
-										{
-											name: 'prompt1.prompt.md',
-											contents: 'oh hi, robot!',
-										},
-									],
-								},
-								{
-									name: '.github/prompts',
-									children: [
-										{
-											name: 'default.prompt.md',
-											contents: 'oh hi, bot!',
-										},
-									],
-								},
-							],
-						},
-						{
-							name: '/Users/legomushroom/repos/node',
-							children: [
-								{
-									name: '.copilot/prompts',
-									children: [
-										{
-											name: 'prompt5.prompt.md',
-											contents: 'oh hi, robot!',
-										},
-									],
-								},
-								{
-									name: '.github/prompts',
-									children: [
-										{
-											name: 'refactor-static-classes.prompt.md',
-											contents: 'file contents',
-										},
-									],
-								},
-							],
-						},
-						// note! this folder is part of the workspace, so prompt files are `included`
-						{
-							name: '/var/shared/prompts/.github/prompts',
-							children: [
-								{
-									name: 'prompt-name.prompt.md',
-									contents: 'oh hi, robot!',
-								},
-								{
-									name: 'name-of-the-prompt.prompt.md',
-									contents: 'oh hi, raw bot!',
-								},
-							],
-						},
-					]);
+					{
+						path: '/Users/legomushroom/repos/prompts/refactor-tests.prompt.md',
+						contents: ['some file content goes here'],
+					},
+					{
+						path: '/tmp/prompts/translate.to-rust.prompt.md',
+						contents: ['some more random file contents'],
+					},
+					{
+						path: '/absolute/path/prompts/some-prompt-file.prompt.md',
+						contents: ['hey hey hey'],
+					},
+					{
+						path: '/Users/legomushroom/repos/vscode/.copilot/prompts/prompt1.prompt.md',
+						contents: ['oh hi, robot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/vscode/.github/prompts/default.prompt.md',
+						contents: ['oh hi, bot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/node/.copilot/prompts/prompt5.prompt.md',
+						contents: ['oh hi, robot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/node/.github/prompts/refactor-static-classes.prompt.md',
+						contents: ['file contents'],
+					},
+					{
+						path: '/var/shared/prompts/.github/prompts/prompt-name.prompt.md',
+						contents: ['oh hi, robot!'],
+					},
+					{
+						path: '/var/shared/prompts/.github/prompts/name-of-the-prompt.prompt.md',
+						contents: ['oh hi, raw bot!'],
+					},
+				]);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				assertOutcome(
 					await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -1552,119 +1219,67 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must find correct prompts.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('mixed', async () => {
-				const locator = await createPromptsLocator(
+				setLocations({
+					'/Users/legomushroom/repos/**/*test*': true,
+					'.copilot/prompts': false,
+					'.github/prompts': true,
+					'/absolute/path/prompts/some-prompt-file.prompt.md': true,
+				});
+				setWorkspaceFolders([
+					'/Users/legomushroom/repos/vscode',
+					'/Users/legomushroom/repos/node',
+					'/var/shared/prompts',
+				]);
+				await mockFiles(fileService, [
 					{
-						'/Users/legomushroom/repos/**/*test*': true,
-						'.copilot/prompts': false,
-						'.github/prompts': true,
-						'/absolute/path/prompts/some-prompt-file.prompt.md': true,
+						path: '/Users/legomushroom/repos/prompts/test.prompt.md',
+						contents: ['Hello, World!'],
 					},
-					[
-						'/Users/legomushroom/repos/vscode',
-						'/Users/legomushroom/repos/node',
-						'/var/shared/prompts',
-					],
-					[
-						{
-							name: '/Users/legomushroom/repos/prompts',
-							children: [
-								{
-									name: 'test.prompt.md',
-									contents: 'Hello, World!',
-								},
-								{
-									name: 'refactor-tests.prompt.md',
-									contents: 'some file content goes here',
-								},
-								{
-									name: 'elf.prompt.md',
-									contents: 'haalo!',
-								},
-							],
-						},
-						{
-							name: '/tmp/prompts',
-							children: [
-								{
-									name: 'translate.to-rust.prompt.md',
-									contents: 'some more random file contents',
-								},
-							],
-						},
-						{
-							name: '/absolute/path/prompts',
-							children: [
-								{
-									name: 'some-prompt-file.prompt.md',
-									contents: 'hey hey hey',
-								},
-							],
-						},
-						{
-							name: '/Users/legomushroom/repos/vscode',
-							children: [
-								{
-									name: '.copilot/prompts',
-									children: [
-										{
-											name: 'prompt1.prompt.md',
-											contents: 'oh hi, robot!',
-										},
-									],
-								},
-								{
-									name: '.github/prompts',
-									children: [
-										{
-											name: 'default.prompt.md',
-											contents: 'oh hi, bot!',
-										},
-									],
-								},
-							],
-						},
-						{
-							name: '/Users/legomushroom/repos/node',
-							children: [
-								{
-									name: '.copilot/prompts',
-									children: [
-										{
-											name: 'prompt5.prompt.md',
-											contents: 'oh hi, robot!',
-										},
-									],
-								},
-								{
-									name: '.github/prompts',
-									children: [
-										{
-											name: 'refactor-static-classes.prompt.md',
-											contents: 'file contents',
-										},
-									],
-								},
-							],
-						},
-						// note! this folder is part of the workspace, so prompt files are `included`
-						{
-							name: '/var/shared/prompts/.github/prompts',
-							children: [
-								{
-									name: 'prompt-name.prompt.md',
-									contents: 'oh hi, robot!',
-								},
-								{
-									name: 'name-of-the-prompt.prompt.md',
-									contents: 'oh hi, raw bot!',
-								},
-							],
-						},
-					]);
+					{
+						path: '/Users/legomushroom/repos/prompts/refactor-tests.prompt.md',
+						contents: ['some file content goes here'],
+					},
+					{
+						path: '/Users/legomushroom/repos/prompts/elf.prompt.md',
+						contents: ['haalo!'],
+					},
+					{
+						path: '/tmp/prompts/translate.to-rust.prompt.md',
+						contents: ['some more random file contents'],
+					},
+					{
+						path: '/absolute/path/prompts/some-prompt-file.prompt.md',
+						contents: ['hey hey hey'],
+					},
+					{
+						path: '/Users/legomushroom/repos/vscode/.copilot/prompts/prompt1.prompt.md',
+						contents: ['oh hi, robot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/vscode/.github/prompts/default.prompt.md',
+						contents: ['oh hi, bot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/node/.copilot/prompts/prompt5.prompt.md',
+						contents: ['oh hi, robot!'],
+					},
+					{
+						path: '/Users/legomushroom/repos/node/.github/prompts/refactor-static-classes.prompt.md',
+						contents: ['file contents'],
+					},
+					{
+						path: '/var/shared/prompts/.github/prompts/prompt-name.prompt.md',
+						contents: ['oh hi, robot!'],
+					},
+					{
+						path: '/var/shared/prompts/.github/prompts/name-of-the-prompt.prompt.md',
+						contents: ['oh hi, raw bot!'],
+					},
+				]);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				assertOutcome(
 					await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -1682,7 +1297,6 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must find correct prompts.',
 				);
-				await locator.disposeAsync();
 			});
 		});
 
@@ -1714,72 +1328,46 @@ suite('PromptFilesLocator', () => {
 
 					for (const setting of testSettings) {
 
-						const locator = await createPromptsLocator(
-							{ [setting]: true },
-							[
-								'/Users/legomushroom/repos/vscode',
-								'/Users/legomushroom/repos/prompts',
-							],
-							[
-								{
-									name: '/Users/legomushroom/repos/vscode',
-									children: [
-										{
-											name: 'gen/text',
-											children: [
-												{
-													name: 'my.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'nested',
-													children: [
-														{
-															name: 'specific.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'unspecific1.prompt.md',
-															contents: 'oh hi, robot!',
-														},
-														{
-															name: 'unspecific2.prompt.md',
-															contents: 'oh hi, rabot!',
-														},
-														{
-															name: 'readme.md',
-															contents: 'non prompt file',
-														},
-													],
-												}
-											],
-										},
-									],
-								},
-								{
-									name: '/Users/legomushroom/repos/prompts',
-									children: [
-										{
-											name: 'general',
-											children: [
-												{
-													name: 'common.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'uncommon-10.prompt.md',
-													contents: 'oh hi, robot!',
-												},
-												{
-													name: 'license.md',
-													contents: 'non prompt file',
-												},
-											],
-										}
-									],
-								},
-							],
-						);
+						setLocations({ [setting]: true });
+						setWorkspaceFolders([
+							'/Users/legomushroom/repos/vscode',
+							'/Users/legomushroom/repos/prompts',
+						]);
+						await mockFiles(fileService, [
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/my.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/specific.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/unspecific1.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/unspecific2.prompt.md',
+								contents: ['oh hi, rabot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/readme.md',
+								contents: ['non prompt file'],
+							},
+							{
+								path: '/Users/legomushroom/repos/prompts/general/common.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/prompts/general/uncommon-10.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/prompts/general/license.md',
+								contents: ['non prompt file'],
+							},
+						]);
+						const locator = instantiationService.createInstance(PromptFilesLocator);
 
 						assertOutcome(
 							await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -1794,7 +1382,6 @@ suite('PromptFilesLocator', () => {
 							],
 							'Must find correct prompts.',
 						);
-						await locator.disposeAsync();
 
 					}
 				});
@@ -1919,72 +1506,46 @@ suite('PromptFilesLocator', () => {
 							vscodeSettings[setting] = true;
 						}
 
-						const locator = await createPromptsLocator(
-							vscodeSettings,
-							[
-								'/Users/legomushroom/repos/vscode',
-								'/Users/legomushroom/repos/prompts',
-							],
-							[
-								{
-									name: '/Users/legomushroom/repos/vscode',
-									children: [
-										{
-											name: 'gen/text',
-											children: [
-												{
-													name: 'my.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'nested',
-													children: [
-														{
-															name: 'specific.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'unspecific1.prompt.md',
-															contents: 'oh hi, robot!',
-														},
-														{
-															name: 'unspecific2.prompt.md',
-															contents: 'oh hi, rabot!',
-														},
-														{
-															name: 'readme.md',
-															contents: 'non prompt file',
-														},
-													],
-												}
-											],
-										},
-									],
-								},
-								{
-									name: '/Users/legomushroom/repos/prompts',
-									children: [
-										{
-											name: 'general',
-											children: [
-												{
-													name: 'common.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'uncommon-10.prompt.md',
-													contents: 'oh hi, robot!',
-												},
-												{
-													name: 'license.md',
-													contents: 'non prompt file',
-												},
-											],
-										}
-									],
-								},
-							],
-						);
+						setLocations(vscodeSettings);
+						setWorkspaceFolders([
+							'/Users/legomushroom/repos/vscode',
+							'/Users/legomushroom/repos/prompts',
+						]);
+						await mockFiles(fileService, [
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/my.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/specific.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/unspecific1.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/unspecific2.prompt.md',
+								contents: ['oh hi, rabot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/readme.md',
+								contents: ['non prompt file'],
+							},
+							{
+								path: '/Users/legomushroom/repos/prompts/general/common.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/prompts/general/uncommon-10.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/prompts/general/license.md',
+								contents: ['non prompt file'],
+							},
+						]);
+						const locator = instantiationService.createInstance(PromptFilesLocator);
 
 						assertOutcome(
 							await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -1999,7 +1560,6 @@ suite('PromptFilesLocator', () => {
 							],
 							'Must find correct prompts.',
 						);
-						await locator.disposeAsync();
 
 					}
 				});
@@ -2043,72 +1603,46 @@ suite('PromptFilesLocator', () => {
 					];
 
 					for (const setting of testSettings) {
-						const locator = await createPromptsLocator(
-							{ [setting]: true },
-							[
-								'/Users/legomushroom/repos/vscode',
-								'/Users/legomushroom/repos/prompts',
-							],
-							[
-								{
-									name: '/Users/legomushroom/repos/vscode',
-									children: [
-										{
-											name: 'gen/text',
-											children: [
-												{
-													name: 'my.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'nested',
-													children: [
-														{
-															name: 'specific.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'unspecific1.prompt.md',
-															contents: 'oh hi, robot!',
-														},
-														{
-															name: 'unspecific2.prompt.md',
-															contents: 'oh hi, rabot!',
-														},
-														{
-															name: 'readme.md',
-															contents: 'non prompt file',
-														},
-													],
-												}
-											],
-										},
-									],
-								},
-								{
-									name: '/Users/legomushroom/repos/prompts',
-									children: [
-										{
-											name: 'general',
-											children: [
-												{
-													name: 'common.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'uncommon-10.prompt.md',
-													contents: 'oh hi, robot!',
-												},
-												{
-													name: 'license.md',
-													contents: 'non prompt file',
-												},
-											],
-										}
-									],
-								},
-							],
-						);
+						setLocations({ [setting]: true });
+						setWorkspaceFolders([
+							'/Users/legomushroom/repos/vscode',
+							'/Users/legomushroom/repos/prompts',
+						]);
+						await mockFiles(fileService, [
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/my.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/specific.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/unspecific1.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/unspecific2.prompt.md',
+								contents: ['oh hi, rabot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/readme.md',
+								contents: ['non prompt file'],
+							},
+							{
+								path: '/Users/legomushroom/repos/prompts/general/common.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/prompts/general/uncommon-10.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/prompts/general/license.md',
+								contents: ['non prompt file'],
+							},
+						]);
+						const locator = instantiationService.createInstance(PromptFilesLocator);
 
 						assertOutcome(
 							await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -2123,7 +1657,6 @@ suite('PromptFilesLocator', () => {
 							],
 							'Must find correct prompts.',
 						);
-						await locator.disposeAsync();
 
 					}
 				});
@@ -2278,72 +1811,46 @@ suite('PromptFilesLocator', () => {
 							vscodeSettings[setting] = true;
 						}
 
-						const locator = await createPromptsLocator(
-							vscodeSettings,
-							[
-								'/Users/legomushroom/repos/vscode',
-								'/Users/legomushroom/repos/prompts',
-							],
-							[
-								{
-									name: '/Users/legomushroom/repos/vscode',
-									children: [
-										{
-											name: 'gen/text',
-											children: [
-												{
-													name: 'my.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'nested',
-													children: [
-														{
-															name: 'specific.prompt.md',
-															contents: 'oh hi, bot!',
-														},
-														{
-															name: 'unspecific1.prompt.md',
-															contents: 'oh hi, robot!',
-														},
-														{
-															name: 'unspecific2.prompt.md',
-															contents: 'oh hi, rabot!',
-														},
-														{
-															name: 'readme.md',
-															contents: 'non prompt file',
-														},
-													],
-												}
-											],
-										},
-									],
-								},
-								{
-									name: '/Users/legomushroom/repos/prompts',
-									children: [
-										{
-											name: 'general',
-											children: [
-												{
-													name: 'common.prompt.md',
-													contents: 'oh hi, bot!',
-												},
-												{
-													name: 'uncommon-10.prompt.md',
-													contents: 'oh hi, robot!',
-												},
-												{
-													name: 'license.md',
-													contents: 'non prompt file',
-												},
-											],
-										}
-									],
-								},
-							],
-						);
+						setLocations(vscodeSettings);
+						setWorkspaceFolders([
+							'/Users/legomushroom/repos/vscode',
+							'/Users/legomushroom/repos/prompts',
+						]);
+						await mockFiles(fileService, [
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/my.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/specific.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/unspecific1.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/unspecific2.prompt.md',
+								contents: ['oh hi, rabot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/vscode/gen/text/nested/readme.md',
+								contents: ['non prompt file'],
+							},
+							{
+								path: '/Users/legomushroom/repos/prompts/general/common.prompt.md',
+								contents: ['oh hi, bot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/prompts/general/uncommon-10.prompt.md',
+								contents: ['oh hi, robot!'],
+							},
+							{
+								path: '/Users/legomushroom/repos/prompts/general/license.md',
+								contents: ['non prompt file'],
+							},
+						]);
+						const locator = instantiationService.createInstance(PromptFilesLocator);
 
 						assertOutcome(
 							await locator.listFiles(PromptsType.prompt, PromptsStorage.local, CancellationToken.None),
@@ -2358,7 +1865,6 @@ suite('PromptFilesLocator', () => {
 							],
 							'Must find correct prompts.',
 						);
-						await locator.disposeAsync();
 
 					}
 				});
@@ -2366,44 +1872,69 @@ suite('PromptFilesLocator', () => {
 		});
 	});
 
+	suite('instructions', () => {
+		testT('finds instructions files in subdirectories of .github/instructions', async () => {
+			setLocations({
+				'.github/instructions': true,
+				'.claude/rules': false,
+				'~/.copilot/instructions': false,
+			});
+			setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+			await mockFiles(fileService, [
+				{
+					path: '/Users/legomushroom/repos/vscode/.github/instructions/root.instructions.md',
+					contents: ['root instructions'],
+				},
+				{
+					path: '/Users/legomushroom/repos/vscode/.github/instructions/frontend/react.instructions.md',
+					contents: ['react instructions'],
+				},
+				{
+					path: '/Users/legomushroom/repos/vscode/.github/instructions/frontend/css.instructions.md',
+					contents: ['css instructions'],
+				},
+				{
+					path: '/Users/legomushroom/repos/vscode/.github/instructions/backend/api.instructions.md',
+					contents: ['api instructions'],
+				},
+			]);
+			const locator = instantiationService.createInstance(PromptFilesLocator);
+
+			assertOutcome(
+				await locator.listFiles(PromptsType.instructions, PromptsStorage.local, CancellationToken.None),
+				[
+					'/Users/legomushroom/repos/vscode/.github/instructions/root.instructions.md',
+					'/Users/legomushroom/repos/vscode/.github/instructions/frontend/react.instructions.md',
+					'/Users/legomushroom/repos/vscode/.github/instructions/frontend/css.instructions.md',
+					'/Users/legomushroom/repos/vscode/.github/instructions/backend/api.instructions.md',
+				],
+				'Must find instructions files recursively in subdirectories of .github/instructions.',
+			);
+		});
+	});
+
 	suite('skills', () => {
 		suite('findAgentSkills', () => {
 			testT('finds skill files in configured locations', async () => {
-				const locator = await createPromptsLocator(
+				setLocations({
+					'.claude/skills': true,
+					// disable other defaults
+					'.github/skills': false,
+					'~/.copilot/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+				await mockFiles(fileService, [
 					{
-						'.claude/skills': true,
-						// disable other defaults
-						'.github/skills': false,
-						'~/.copilot/skills': false,
-						'~/.claude/skills': false,
+						path: '/Users/legomushroom/repos/vscode/.claude/skills/pptx/SKILL.md',
+						contents: ['# PPTX Skill'],
 					},
-					['/Users/legomushroom/repos/vscode'],
-					[
-						{
-							name: '/Users/legomushroom/repos/vscode/.claude/skills',
-							children: [
-								{
-									name: 'pptx',
-									children: [
-										{
-											name: 'SKILL.md',
-											contents: '# PPTX Skill',
-										},
-									],
-								},
-								{
-									name: 'excel',
-									children: [
-										{
-											name: 'SKILL.md',
-											contents: '# Excel Skill',
-										},
-									],
-								},
-							],
-						},
-					],
-				);
+					{
+						path: '/Users/legomushroom/repos/vscode/.claude/skills/excel/SKILL.md',
+						contents: ['# Excel Skill'],
+					},
+				]);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const skills = await locator.findAgentSkills(CancellationToken.None);
 				assertOutcome(
@@ -2414,54 +1945,32 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must find skill files.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('ignores folders without SKILL.md', async () => {
-				const locator = await createPromptsLocator(
+				setLocations({
+					'.claude/skills': true,
+					// disable other defaults
+					'.github/skills': false,
+					'~/.copilot/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+				await mockFiles(fileService, [
 					{
-						'.claude/skills': true,
-						// disable other defaults
-						'.github/skills': false,
-						'~/.copilot/skills': false,
-						'~/.claude/skills': false,
+						path: '/Users/legomushroom/repos/vscode/.claude/skills/valid-skill/SKILL.md',
+						contents: ['# Valid Skill'],
 					},
-					['/Users/legomushroom/repos/vscode'],
-					[
-						{
-							name: '/Users/legomushroom/repos/vscode/.claude/skills',
-							children: [
-								{
-									name: 'valid-skill',
-									children: [
-										{
-											name: 'SKILL.md',
-											contents: '# Valid Skill',
-										},
-									],
-								},
-								{
-									name: 'invalid-skill',
-									children: [
-										{
-											name: 'readme.md',
-											contents: 'Not a skill file',
-										},
-									],
-								},
-								{
-									name: 'another-invalid',
-									children: [
-										{
-											name: 'index.js',
-											contents: 'console.log("not a skill")',
-										},
-									],
-								},
-							],
-						},
-					],
-				);
+					{
+						path: '/Users/legomushroom/repos/vscode/.claude/skills/invalid-skill/readme.md',
+						contents: ['Not a skill file'],
+					},
+					{
+						path: '/Users/legomushroom/repos/vscode/.claude/skills/another-invalid/index.js',
+						contents: ['console.log("not a skill")'],
+					},
+				]);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const skills = await locator.findAgentSkills(CancellationToken.None);
 				assertOutcome(
@@ -2471,26 +1980,19 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must only find folders with SKILL.md.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('returns empty array when no skills exist', async () => {
-				const locator = await createPromptsLocator(
-					{
-						'.claude/skills': true,
-						// disable other defaults
-						'.github/skills': false,
-						'~/.copilot/skills': false,
-						'~/.claude/skills': false,
-					},
-					['/Users/legomushroom/repos/vscode'],
-					[
-						{
-							name: '/Users/legomushroom/repos/vscode/.claude/skills',
-							children: [],
-						},
-					],
-				);
+				setLocations({
+					'.claude/skills': true,
+					// disable other defaults
+					'.github/skills': false,
+					'~/.copilot/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const skills = await locator.findAgentSkills(CancellationToken.None);
 				assertOutcome(
@@ -2498,21 +2000,19 @@ suite('PromptFilesLocator', () => {
 					[],
 					'Must return empty array when no skills exist.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('returns empty array when skill folder does not exist', async () => {
-				const locator = await createPromptsLocator(
-					{
-						'.claude/skills': true,
-						// disable other defaults
-						'.github/skills': false,
-						'~/.copilot/skills': false,
-						'~/.claude/skills': false,
-					},
-					['/Users/legomushroom/repos/vscode'],
-					[], // empty filesystem
-				);
+				setLocations({
+					'.claude/skills': true,
+					// disable other defaults
+					'.github/skills': false,
+					'~/.copilot/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const skills = await locator.findAgentSkills(CancellationToken.None);
 				assertOutcome(
@@ -2520,53 +2020,31 @@ suite('PromptFilesLocator', () => {
 					[],
 					'Must return empty array when folder does not exist.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('finds skills across multiple workspace folders', async () => {
-				const locator = await createPromptsLocator(
+				setLocations({
+					'.claude/skills': true,
+					// disable other defaults
+					'.github/skills': false,
+					'~/.copilot/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders([
+					'/Users/legomushroom/repos/vscode',
+					'/Users/legomushroom/repos/node',
+				]);
+				await mockFiles(fileService, [
 					{
-						'.claude/skills': true,
-						// disable other defaults
-						'.github/skills': false,
-						'~/.copilot/skills': false,
-						'~/.claude/skills': false,
+						path: '/Users/legomushroom/repos/vscode/.claude/skills/skill-a/SKILL.md',
+						contents: ['# Skill A'],
 					},
-					[
-						'/Users/legomushroom/repos/vscode',
-						'/Users/legomushroom/repos/node',
-					],
-					[
-						{
-							name: '/Users/legomushroom/repos/vscode/.claude/skills',
-							children: [
-								{
-									name: 'skill-a',
-									children: [
-										{
-											name: 'SKILL.md',
-											contents: '# Skill A',
-										},
-									],
-								},
-							],
-						},
-						{
-							name: '/Users/legomushroom/repos/node/.claude/skills',
-							children: [
-								{
-									name: 'skill-b',
-									children: [
-										{
-											name: 'SKILL.md',
-											contents: '# Skill B',
-										},
-									],
-								},
-							],
-						},
-					],
-				);
+					{
+						path: '/Users/legomushroom/repos/node/.claude/skills/skill-b/SKILL.md',
+						contents: ['# Skill B'],
+					},
+				]);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const skills = await locator.findAgentSkills(CancellationToken.None);
 				assertOutcome(
@@ -2577,38 +2055,26 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must find skills across all workspace folders.',
 				);
-				await locator.disposeAsync();
 			});
 		});
 
 		suite('listFiles with PromptsType.skill', () => {
 			testT('does not list skills when location is disabled', async () => {
-				const locator = await createPromptsLocator(
+				setLocations({
+					'.claude/skills': false,
+					// disable other defaults
+					'.github/skills': false,
+					'~/.copilot/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+				await mockFiles(fileService, [
 					{
-						'.claude/skills': false,
-						// disable other defaults
-						'.github/skills': false,
-						'~/.copilot/skills': false,
-						'~/.claude/skills': false,
+						path: '/Users/legomushroom/repos/vscode/.claude/skills/pptx/SKILL.md',
+						contents: ['# PPTX Skill'],
 					},
-					['/Users/legomushroom/repos/vscode'],
-					[
-						{
-							name: '/Users/legomushroom/repos/vscode/.claude/skills',
-							children: [
-								{
-									name: 'pptx',
-									children: [
-										{
-											name: 'SKILL.md',
-											contents: '# PPTX Skill',
-										},
-									],
-								},
-							],
-						},
-					],
-				);
+				]);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const files = await locator.listFiles(PromptsType.skill, PromptsStorage.local, CancellationToken.None);
 				assertOutcome(
@@ -2616,28 +2082,26 @@ suite('PromptFilesLocator', () => {
 					[],
 					'Must not list skills when location is disabled.',
 				);
-				await locator.disposeAsync();
 			});
 		});
 
 		suite('toAbsoluteLocationsForSkills path validation', () => {
 			testT('rejects glob patterns in skill paths via getConfigBasedSourceFolders', async () => {
-				const locator = await createPromptsLocator(
-					{
-						'skills/**': true,
-						'skills/*': true,
-						'**/skills': true,
-						// disable defaults
-						'.github/skills': false,
-						'.agents/skills': false,
-						'.claude/skills': false,
-						'~/.copilot/skills': false,
-						'~/.agents/skills': false,
-						'~/.claude/skills': false,
-					},
-					['/Users/legomushroom/repos/vscode'],
-					[],
-				);
+				setLocations({
+					'skills/**': true,
+					'skills/*': true,
+					'**/skills': true,
+					// disable defaults
+					'.github/skills': false,
+					'.agents/skills': false,
+					'.claude/skills': false,
+					'~/.copilot/skills': false,
+					'~/.agents/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const folders = await locator.getConfigBasedSourceFolders(PromptsType.skill);
 				assertOutcome(
@@ -2645,24 +2109,22 @@ suite('PromptFilesLocator', () => {
 					[],
 					'Must reject glob patterns in skill paths.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('rejects absolute paths in skill paths via getConfigBasedSourceFolders', async () => {
-				const locator = await createPromptsLocator(
-					{
-						'/absolute/path/skills': true,
-						// disable defaults
-						'.github/skills': false,
-						'.agents/skills': false,
-						'.claude/skills': false,
-						'~/.copilot/skills': false,
-						'~/.agents/skills': false,
-						'~/.claude/skills': false,
-					},
-					['/Users/legomushroom/repos/vscode'],
-					[],
-				);
+				setLocations({
+					'/absolute/path/skills': true,
+					// disable defaults
+					'.github/skills': false,
+					'.agents/skills': false,
+					'.claude/skills': false,
+					'~/.copilot/skills': false,
+					'~/.agents/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const folders = await locator.getConfigBasedSourceFolders(PromptsType.skill);
 				assertOutcome(
@@ -2670,25 +2132,23 @@ suite('PromptFilesLocator', () => {
 					[],
 					'Must reject absolute paths in skill paths.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('accepts relative paths in skill paths via getConfigBasedSourceFolders', async () => {
-				const locator = await createPromptsLocator(
-					{
-						'./my-skills': true,
-						'custom/skills': true,
-						// disable defaults
-						'.github/skills': false,
-						'.agents/skills': false,
-						'.claude/skills': false,
-						'~/.copilot/skills': false,
-						'~/.agents/skills': false,
-						'~/.claude/skills': false,
-					},
-					['/Users/legomushroom/repos/vscode'],
-					[],
-				);
+				setLocations({
+					'./my-skills': true,
+					'custom/skills': true,
+					// disable defaults
+					'.github/skills': false,
+					'.agents/skills': false,
+					'.claude/skills': false,
+					'~/.copilot/skills': false,
+					'~/.agents/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const folders = await locator.getConfigBasedSourceFolders(PromptsType.skill);
 				assertOutcome(
@@ -2699,24 +2159,22 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must accept relative paths in skill paths.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('accepts parent relative paths for monorepos via getConfigBasedSourceFolders', async () => {
-				const locator = await createPromptsLocator(
-					{
-						'../shared-skills': true,
-						// disable defaults
-						'.github/skills': false,
-						'.agents/skills': false,
-						'.claude/skills': false,
-						'~/.copilot/skills': false,
-						'~/.agents/skills': false,
-						'~/.claude/skills': false,
-					},
-					['/Users/legomushroom/repos/vscode'],
-					[],
-				);
+				setLocations({
+					'../shared-skills': true,
+					// disable defaults
+					'.github/skills': false,
+					'.agents/skills': false,
+					'.claude/skills': false,
+					'~/.copilot/skills': false,
+					'~/.agents/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const folders = await locator.getConfigBasedSourceFolders(PromptsType.skill);
 				assertOutcome(
@@ -2726,24 +2184,22 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must accept parent relative paths for monorepos.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('accepts tilde paths for user home skills', async () => {
-				const locator = await createPromptsLocator(
-					{
-						'~/my-skills': true,
-						// disable defaults
-						'.github/skills': false,
-						'.agents/skills': false,
-						'.claude/skills': false,
-						'~/.copilot/skills': false,
-						'~/.agents/skills': false,
-						'~/.claude/skills': false,
-					},
-					['/Users/legomushroom/repos/vscode'],
-					[],
-				);
+				setLocations({
+					'~/my-skills': true,
+					// disable defaults
+					'.github/skills': false,
+					'.agents/skills': false,
+					'.claude/skills': false,
+					'~/.copilot/skills': false,
+					'~/.agents/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const folders = await locator.getConfigBasedSourceFolders(PromptsType.skill);
 				assertOutcome(
@@ -2753,29 +2209,27 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must accept tilde paths for user home skills.',
 				);
-				await locator.disposeAsync();
 			});
 		});
 
 		suite('getConfigBasedSourceFolders for skills', () => {
 			testT('returns source folders without glob processing', async () => {
-				const locator = await createPromptsLocator(
-					{
-						'.claude/skills': true,
-						'custom-skills': true,
-						// explicitly disable other defaults we don't want for this test
-						'.github/skills': false,
-						'.agents/skills': false,
-						'~/.copilot/skills': false,
-						'~/.agents/skills': false,
-						'~/.claude/skills': false,
-					},
-					[
-						'/Users/legomushroom/repos/vscode',
-						'/Users/legomushroom/repos/node',
-					],
-					[],
-				);
+				setLocations({
+					'.claude/skills': true,
+					'custom-skills': true,
+					// explicitly disable other defaults we don't want for this test
+					'.github/skills': false,
+					'.agents/skills': false,
+					'~/.copilot/skills': false,
+					'~/.agents/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders([
+					'/Users/legomushroom/repos/vscode',
+					'/Users/legomushroom/repos/node',
+				]);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const folders = await locator.getConfigBasedSourceFolders(PromptsType.skill);
 				assertOutcome(
@@ -2788,25 +2242,23 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must return skill source folders without glob processing.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('filters out invalid skill paths from source folders', async () => {
-				const locator = await createPromptsLocator(
-					{
-						'.claude/skills': true,
-						'skills/**': true, // glob - should be filtered out
-						'/absolute/skills': true, // absolute - should be filtered out
-						// explicitly disable other defaults we don't want for this test
-						'.github/skills': false,
-						'.agents/skills': false,
-						'~/.copilot/skills': false,
-						'~/.agents/skills': false,
-						'~/.claude/skills': false,
-					},
-					['/Users/legomushroom/repos/vscode'],
-					[],
-				);
+				setLocations({
+					'.claude/skills': true,
+					'skills/**': true, // glob - should be filtered out
+					'/absolute/skills': true, // absolute - should be filtered out
+					// explicitly disable other defaults we don't want for this test
+					'.github/skills': false,
+					'.agents/skills': false,
+					'~/.copilot/skills': false,
+					'~/.agents/skills': false,
+					'~/.claude/skills': false,
+				});
+				setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const folders = await locator.getConfigBasedSourceFolders(PromptsType.skill);
 				assertOutcome(
@@ -2816,17 +2268,15 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must filter out invalid skill paths.',
 				);
-				await locator.disposeAsync();
 			});
 
 			testT('includes default skill source folders from defaults', async () => {
-				const locator = await createPromptsLocator(
-					{
-						'custom-skills': true,
-					},
-					['/Users/legomushroom/repos/vscode'],
-					[],
-				);
+				setLocations({
+					'custom-skills': true,
+				});
+				setWorkspaceFolders(['/Users/legomushroom/repos/vscode']);
+				await mockFiles(fileService, []);
+				const locator = instantiationService.createInstance(PromptFilesLocator);
 
 				const folders = await locator.getConfigBasedSourceFolders(PromptsType.skill);
 				assertOutcome(
@@ -2844,7 +2294,6 @@ suite('PromptFilesLocator', () => {
 					],
 					'Must include default skill source folders.',
 				);
-				await locator.disposeAsync();
 			});
 		});
 	});
@@ -3149,23 +2598,22 @@ suite('PromptFilesLocator', () => {
 
 	suite('getConfigBasedSourceFolders', () => {
 		testT('gets unambiguous list of folders', async () => {
-			const locator = await createPromptsLocator(
-				{
-					'.github/prompts': true,
-					'/Users/**/repos/**': true,
-					'gen/text/**': true,
-					'gen/text/nested/*.prompt.md': true,
-					'general/*': true,
-					'/Users/legomushroom/repos/vscode/my-prompts': true,
-					'/Users/legomushroom/repos/vscode/your-prompts/*.md': true,
-					'/Users/legomushroom/repos/prompts/shared-prompts/*': true,
-				},
-				[
-					'/Users/legomushroom/repos/vscode',
-					'/Users/legomushroom/repos/prompts',
-				],
-				[],
-			);
+			setLocations({
+				'.github/prompts': true,
+				'/Users/**/repos/**': true,
+				'gen/text/**': true,
+				'gen/text/nested/*.prompt.md': true,
+				'general/*': true,
+				'/Users/legomushroom/repos/vscode/my-prompts': true,
+				'/Users/legomushroom/repos/vscode/your-prompts/*.md': true,
+				'/Users/legomushroom/repos/prompts/shared-prompts/*': true,
+			});
+			setWorkspaceFolders([
+				'/Users/legomushroom/repos/vscode',
+				'/Users/legomushroom/repos/prompts',
+			]);
+			await mockFiles(fileService, []);
+			const locator = instantiationService.createInstance(PromptFilesLocator);
 
 			assertOutcome(
 				await locator.getConfigBasedSourceFolders(PromptsType.prompt),
@@ -3182,29 +2630,25 @@ suite('PromptFilesLocator', () => {
 				],
 				'Must find correct prompts.',
 			);
-			await locator.disposeAsync();
 		});
 	});
 
 	suite('findAgentMDsInWorkspace', () => {
 		testT('finds AGENTS.md files using FileSearchProvider', async () => {
-			const locator = await createPromptsLocatorForAgentMD(
-				{},
-				['/Users/legomushroom/repos/workspace'],
-				[
-					{
-						path: '/Users/legomushroom/repos/workspace/AGENTS.md',
-						contents: ['# Root agents']
-					},
-					{
-						path: '/Users/legomushroom/repos/workspace/src/AGENTS.md',
-						contents: ['# Src agents']
-					}
-				],
-				true // has FileSearchProvider
-			);
+			setWorkspaceFolders(['/Users/legomushroom/repos/workspace']);
+			await mockFiles(fileService, [
+				{
+					path: '/Users/legomushroom/repos/workspace/AGENTS.md',
+					contents: ['# Root agents']
+				},
+				{
+					path: '/Users/legomushroom/repos/workspace/src/AGENTS.md',
+					contents: ['# Src agents']
+				}
+			]);
+			const locator = instantiationService.createInstance(PromptFilesLocator);
 
-			const result = await locator.findAgentMDsInWorkspace(CancellationToken.None);
+			const result = (await locator.findAgentMDsInWorkspace(CancellationToken.None)).map(f => f.uri);
 			assertOutcome(
 				result,
 				[
@@ -3213,31 +2657,31 @@ suite('PromptFilesLocator', () => {
 				],
 				'Must find all AGENTS.md files using search service.'
 			);
-			await locator.disposeAsync();
 		});
 
 		testT('finds AGENTS.md files using file service fallback', async () => {
-			const locator = await createPromptsLocatorForAgentMD(
-				{},
-				['/Users/legomushroom/repos/workspace'],
-				[
-					{
-						path: '/Users/legomushroom/repos/workspace/AGENTS.md',
-						contents: ['# Root agents']
-					},
-					{
-						path: '/Users/legomushroom/repos/workspace/src/AGENTS.md',
-						contents: ['# Src agents']
-					},
-					{
-						path: '/Users/legomushroom/repos/workspace/src/nested/AGENTS.md',
-						contents: ['# Nested agents']
-					}
-				],
-				false // no FileSearchProvider - should use file service fallback
-			);
+			setWorkspaceFolders(['/Users/legomushroom/repos/workspace']);
+			await mockFiles(fileService, [
+				{
+					path: '/Users/legomushroom/repos/workspace/AGENTS.md',
+					contents: ['# Root agents']
+				},
+				{
+					path: '/Users/legomushroom/repos/workspace/src/AGENTS.md',
+					contents: ['# Src agents']
+				},
+				{
+					path: '/Users/legomushroom/repos/workspace/src/nested/AGENTS.md',
+					contents: ['# Nested agents']
+				}
+			]);
+			instantiationService.stub(ISearchService, {
+				schemeHasFileSearchProvider: () => false,
+				async fileSearch() { throw new Error('FileSearchProvider not available'); }
+			});
+			const locator = instantiationService.createInstance(PromptFilesLocator);
 
-			const result = await locator.findAgentMDsInWorkspace(CancellationToken.None);
+			const result = (await locator.findAgentMDsInWorkspace(CancellationToken.None)).map(f => f.uri);
 			assertOutcome(
 				result,
 				[
@@ -3247,120 +2691,110 @@ suite('PromptFilesLocator', () => {
 				],
 				'Must find all AGENTS.md files using file service fallback.'
 			);
-			await locator.disposeAsync();
 		});
 
 		testT('handles cancellation token in file service fallback', async () => {
-			const locator = await createPromptsLocatorForAgentMD(
-				{},
-				['/Users/legomushroom/repos/workspace'],
-				[
-					{
-						path: '/Users/legomushroom/repos/workspace/AGENTS.md',
-						contents: ['# Root agents']
-					}
-				],
-				false // no FileSearchProvider
-			);
+			setWorkspaceFolders(['/Users/legomushroom/repos/workspace']);
+			await mockFiles(fileService, [
+				{
+					path: '/Users/legomushroom/repos/workspace/AGENTS.md',
+					contents: ['# Root agents']
+				}
+			]);
+			instantiationService.stub(ISearchService, {
+				schemeHasFileSearchProvider: () => false,
+				async fileSearch() { throw new Error('FileSearchProvider not available'); }
+			});
+			const locator = instantiationService.createInstance(PromptFilesLocator);
 
 			const source = new CancellationTokenSource();
 			// Cancel immediately
 			source.cancel();
-			const result = await locator.findAgentMDsInWorkspace(source.token);
+			const result = (await locator.findAgentMDsInWorkspace(source.token)).map(f => f.uri);
 			assertOutcome(
 				result,
 				[],
 				'Must return empty array when cancelled.'
 			);
-			await locator.disposeAsync();
 		});
 
-		const createPromptsLocatorForAgentMD = async (
-			configValue: unknown,
-			workspaceFolderPaths: string[],
-			filesystem: IMockFileEntry[],
-			hasFileSearchProvider: boolean
-		) => {
-			const mockFs = instantiationService.createInstance(MockFilesystem, filesystem);
-			await mockFs.mock();
-
-			instantiationService.stub(IConfigurationService, mockConfigService({
-				'explorer.excludeGitIgnore': false,
-				'files.exclude': {},
-				'search.exclude': {}
-			}));
-
-			const workspaceFolders = workspaceFolderPaths.map((path, index) => {
-				const uri = URI.file(path);
-
-				return new class extends mock<IWorkspaceFolder>() {
-					override uri = uri;
-					override name = basename(uri);
-					override index = index;
-				};
-			});
-			instantiationService.stub(IWorkspaceContextService, mockWorkspaceService(workspaceFolders));
-			instantiationService.stub(IWorkbenchEnvironmentService, {} as IWorkbenchEnvironmentService);
-			instantiationService.stub(IUserDataProfileService, new TestUserDataProfileService());
-			instantiationService.stub(ISearchService, {
-				schemeHasFileSearchProvider(scheme: string): boolean {
-					return hasFileSearchProvider;
-				},
-				async fileSearch(query: IFileQuery) {
-					if (!hasFileSearchProvider) {
-						throw new Error('FileSearchProvider not available');
-					}
-					// mock the search service
-					const fs = instantiationService.get(IFileService);
-					const findFilesInLocation = async (location: URI, results: URI[] = []) => {
-						try {
-							const resolve = await fs.resolve(location);
-							if (resolve.isFile) {
-								results.push(resolve.resource);
-							} else if (resolve.isDirectory && resolve.children) {
-								for (const child of resolve.children) {
-									await findFilesInLocation(child.resource, results);
-								}
-							}
-						} catch (error) {
-						}
-						return results;
-					};
-					const results: IFileMatch[] = [];
-					for (const folderQuery of query.folderQueries) {
-						const allFiles = await findFilesInLocation(folderQuery.folder);
-						for (const resource of allFiles) {
-							const pathInFolder = relativePath(folderQuery.folder, resource) ?? '';
-							if (query.filePattern === undefined || match(query.filePattern, pathInFolder)) {
-								results.push({ resource });
-							}
-						}
-
-					}
-					return { results, messages: [] };
-				}
-			});
-			instantiationService.stub(IPathService, {
-				userHome(options?: { preferLocal: boolean }): URI | Promise<URI> {
-					const uri = URI.file('/Users/legomushroom');
-					if (options?.preferLocal) {
-						return uri;
-					}
-					return Promise.resolve(uri);
-				}
-			} as IPathService);
+	});
 
-			const locator = instantiationService.createInstance(PromptFilesLocator);
+	suite('getWorkspaceFolderRoots', () => {
+		let locator: PromptFilesLocator;
 
-			return {
-				async findAgentMDsInWorkspace(token: CancellationToken): Promise<URI[]> {
-					return (await locator.findAgentMDsInWorkspace(token)).map(f => f.uri);
-				},
-				async disposeAsync(): Promise<void> {
-					await mockFs.delete();
-				}
-			};
+		// Override setWorkspaceFolders to also create the locator
+		const setWorkspaceFoldersForRoots = (paths: string[]) => {
+			setWorkspaceFolders(paths);
+			locator = instantiationService.createInstance(PromptFilesLocator);
 		};
+
+		testT('returns only workspace folder when it has .git', async () => {
+			setWorkspaceFoldersForRoots(['/repos/my-project']);
+			await mockFiles(fileService, [
+				{ path: '/repos/my-project/.git/HEAD', contents: ['ref: refs/heads/main'] },
+				{ path: '/repos/my-project/src/index.ts', contents: ['export {};'] },
+			]);
+
+			const roots = await locator.getWorkspaceFolderRoots(true);
+			assert.deepStrictEqual(
+				roots.map(r => r.path),
+				['/repos/my-project'],
+				'Should only return the workspace folder itself when it has .git',
+			);
+		});
+
+		testT('walks up to parent with .git when workspace folder has no .git', async () => {
+			setWorkspaceFoldersForRoots(['/repos/monorepo/packages/my-app']);
+			await mockFiles(fileService, [
+				{ path: '/repos/monorepo/.git/HEAD', contents: ['ref: refs/heads/main'] },
+				{ path: '/repos/monorepo/packages/my-app/src/index.ts', contents: ['export {};'] },
+			]);
+
+			workspaceTrustService.setTrustedUris([URI.file('/repos/monorepo')]);
+
+			const roots = await locator.getWorkspaceFolderRoots(true);
+			assert.deepStrictEqual(
+				roots.map(r => r.path).sort(),
+				[
+					'/repos/monorepo',
+					'/repos/monorepo/packages',
+					'/repos/monorepo/packages/my-app',
+				].sort(),
+				'Should include workspace folder and all parents up to the one with .git',
+			);
+		});
+
+		testT('does not walk up when includeParents is false', async () => {
+			setWorkspaceFoldersForRoots(['/repos/monorepo/packages/my-app']);
+			await mockFiles(fileService, [
+				{ path: '/repos/monorepo/.git/HEAD', contents: ['ref: refs/heads/main'] },
+				{ path: '/repos/monorepo/packages/my-app/src/index.ts', contents: ['export {};'] },
+			]);
+
+			workspaceTrustService.setTrustedUris([URI.file('/repos/monorepo')]);
+
+			const roots = await locator.getWorkspaceFolderRoots(false);
+			assert.deepStrictEqual(
+				roots.map(r => r.path),
+				['/repos/monorepo/packages/my-app'],
+				'Should only return workspace folders when includeParents is false',
+			);
+		});
+
+		testT('returns only workspace folder when no .git is found', async () => {
+			setWorkspaceFoldersForRoots(['/Users/legomushroom/my-project']);
+			await mockFiles(fileService, [
+				{ path: '/Users/legomushroom/my-project/src/index.ts', contents: ['export {};'] },
+			]);
+
+			const roots = await locator.getWorkspaceFolderRoots(true);
+			assert.deepStrictEqual(
+				roots.map(r => r.path),
+				['/Users/legomushroom/my-project'],
+				'Should only return the workspace folder when no .git is found in any parent',
+			);
+		});
 	});
 });
 
diff --git a/src/vs/workbench/contrib/chat/test/common/requestParser/chatRequestParser.test.ts b/src/vs/workbench/contrib/chat/test/common/requestParser/chatRequestParser.test.ts
index 96e754d368887..fa6cc7ac06553 100644
--- a/src/vs/workbench/contrib/chat/test/common/requestParser/chatRequestParser.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/requestParser/chatRequestParser.test.ts
@@ -6,6 +6,7 @@
 import { mockObject } from '../../../../../../base/test/common/mock.js';
 import { assertSnapshot } from '../../../../../../base/test/common/snapshot.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { Event } from '../../../../../../base/common/event.js';
 import { IContextKeyService } from '../../../../../../platform/contextkey/common/contextkey.js';
 import { TestInstantiationService } from '../../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
 import { MockContextKeyService } from '../../../../../../platform/keybinding/test/common/mockKeybindingService.js';
@@ -70,10 +71,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('slash command', async () => {
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([{ command: 'fix' }]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const text = '/fix this';
@@ -82,10 +82,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('invalid slash command', async () => {
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([{ command: 'fix' }]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const text = '/explain this';
@@ -94,10 +93,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('multiple slash commands', async () => {
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([{ command: 'fix' }]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const text = '/fix /fix';
@@ -106,10 +104,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('slash command not first', async () => {
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([{ command: 'fix' }]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const text = 'Hello /fix';
@@ -118,10 +115,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('slash command after whitespace', async () => {
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([{ command: 'fix' }]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const text = '    /fix';
@@ -130,17 +126,15 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('prompt slash command', async () => {
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([{ command: 'fix' }]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
-		const promptSlashCommandService = mockObject<IPromptsService>()({});
+		const promptSlashCommandService = mockObject<IPromptsService>()({ _serviceBrand: undefined });
 		promptSlashCommandService.isValidSlashCommandName.callsFake((command: string) => {
 			return !!command.match(/^[\w_\-\.]+$/);
 		});
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IPromptsService, promptSlashCommandService as any);
+		instantiationService.stub(IPromptsService, promptSlashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const text = '    /prompt';
@@ -149,17 +143,15 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('prompt slash command after text', async () => {
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([{ command: 'fix' }]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
-		const promptSlashCommandService = mockObject<IPromptsService>()({});
+		const promptSlashCommandService = mockObject<IPromptsService>()({ _serviceBrand: undefined });
 		promptSlashCommandService.isValidSlashCommandName.callsFake((command: string) => {
 			return !!command.match(/^[\w_\-\.]+$/);
 		});
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IPromptsService, promptSlashCommandService as any);
+		instantiationService.stub(IPromptsService, promptSlashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const text = 'handle the / route and the request of /search-option';
@@ -168,18 +160,16 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('prompt slash command after slash', async () => {
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([{ command: 'fix' }]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
-		const promptSlashCommandService = mockObject<IPromptsService>()({});
+		const promptSlashCommandService = mockObject<IPromptsService>()({ _serviceBrand: undefined });
 		promptSlashCommandService.isValidSlashCommandName.callsFake((command: string) => {
 			return !!command.match(/^[\w_\-\.]+$/);
 
 		});
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IPromptsService, promptSlashCommandService as any);
+		instantiationService.stub(IPromptsService, promptSlashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const text = '/ route and the request of /search-option';
@@ -188,17 +178,15 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('prompt slash command with numbers', async () => {
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([{ command: 'fix' }]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
-		const promptSlashCommandService = mockObject<IPromptsService>()({});
+		const promptSlashCommandService = mockObject<IPromptsService>()({ _serviceBrand: undefined });
 		promptSlashCommandService.isValidSlashCommandName.callsFake((command: string) => {
 			return !!command.match(/^[\w_\-\.]+$/);
 		});
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IPromptsService, promptSlashCommandService as any);
+		instantiationService.stub(IPromptsService, promptSlashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const text = '/001-sample this is a test';
@@ -240,10 +228,9 @@ suite('ChatRequestParser', () => {
 	};
 
 	test('agent with subcommand after text', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([{ name: 'subCommand', description: '' }])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const result = parser.parseChatRequest(testSessionUri, '@agent Please do /subCommand thanks');
@@ -251,10 +238,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('agents, subCommand', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([{ name: 'subCommand', description: '' }])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const result = parser.parseChatRequest(testSessionUri, '@agent /subCommand Please do thanks');
@@ -262,10 +248,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('agent but edit mode', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const result = parser.parseChatRequest(testSessionUri, '@agent hello', undefined, { mode: ChatModeKind.Edit });
@@ -273,10 +258,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('agent with question mark', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([{ name: 'subCommand', description: '' }])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const result = parser.parseChatRequest(testSessionUri, '@agent? Are you there');
@@ -284,10 +268,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('agent and subcommand with leading whitespace', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([{ name: 'subCommand', description: '' }])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const result = parser.parseChatRequest(testSessionUri, '    \r\n\t   @agent \r\n\t   /subCommand Thanks');
@@ -295,10 +278,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('agent and subcommand after newline', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([{ name: 'subCommand', description: '' }])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const result = parser.parseChatRequest(testSessionUri, '    \n@agent\n/subCommand Thanks');
@@ -306,10 +288,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('agent not first', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([{ name: 'subCommand', description: '' }])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const result = parser.parseChatRequest(testSessionUri, 'Hello Mr. @agent');
@@ -317,10 +298,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('agents and tools and multiline', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([{ name: 'subCommand', description: '' }])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
 		variableService.setSelectedToolAndToolSets(testSessionUri, new Map([
 			[{ id: 'get_selection', toolReferenceName: 'selection', canBeReferencedInPrompt: true, displayName: '', modelDescription: '', source: ToolDataSource.Internal }, true],
@@ -333,10 +313,9 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('agents and tools and multiline, part2', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([{ name: 'subCommand', description: '' }])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
 		variableService.setSelectedToolAndToolSets(testSessionUri, new Map([
 			[{ id: 'get_selection', toolReferenceName: 'selection', canBeReferencedInPrompt: true, displayName: '', modelDescription: '', source: ToolDataSource.Internal }, true],
@@ -349,22 +328,19 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('prompt slash command with agent and supportsPromptAttachments', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([{ name: 'subCommand', description: '' }])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
-		const promptSlashCommandService = mockObject<IPromptsService>()({});
+		const promptSlashCommandService = mockObject<IPromptsService>()({ _serviceBrand: undefined });
 		promptSlashCommandService.isValidSlashCommandName.callsFake((command: string) => {
 			return !!command.match(/^[\w_\-\.]+$/);
 		});
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IPromptsService, promptSlashCommandService as any);
+		instantiationService.stub(IPromptsService, promptSlashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const result = parser.parseChatRequest(testSessionUri, '@agent /myPrompt do something', undefined, {
@@ -374,22 +350,19 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('prompt slash command with agent but no supportsPromptAttachments', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([{ name: 'subCommand', description: '' }])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
-		const promptSlashCommandService = mockObject<IPromptsService>()({});
+		const promptSlashCommandService = mockObject<IPromptsService>()({ _serviceBrand: undefined });
 		promptSlashCommandService.isValidSlashCommandName.callsFake((command: string) => {
 			return !!command.match(/^[\w_\-\.]+$/);
 		});
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IPromptsService, promptSlashCommandService as any);
+		instantiationService.stub(IPromptsService, promptSlashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const result = parser.parseChatRequest(testSessionUri, '@agent /myPrompt do something', undefined, {
@@ -399,22 +372,19 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('agent subcommand still takes priority with supportsPromptAttachments', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([{ name: 'subCommand', description: '' }])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
-		const promptSlashCommandService = mockObject<IPromptsService>()({});
+		const promptSlashCommandService = mockObject<IPromptsService>()({ _serviceBrand: undefined });
 		promptSlashCommandService.isValidSlashCommandName.callsFake((command: string) => {
 			return !!command.match(/^[\w_\-\.]+$/);
 		});
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IPromptsService, promptSlashCommandService as any);
+		instantiationService.stub(IPromptsService, promptSlashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const result = parser.parseChatRequest(testSessionUri, '@agent /subCommand do something', undefined, {
@@ -424,15 +394,13 @@ suite('ChatRequestParser', () => {
 	});
 
 	test('slash command with agent and supportsPromptAttachments', async () => {
-		const agentsService = mockObject<IChatAgentService>()({});
+		const agentsService = mockObject<IChatAgentService>()({ _serviceBrand: undefined, hasToolsAgent: false, onDidChangeAgents: Event.None });
 		agentsService.getAgentsByName.returns([getAgentWithSlashCommands([{ name: 'subCommand', description: '' }])]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatAgentService, agentsService as any);
+		instantiationService.stub(IChatAgentService, agentsService);
 
-		const slashCommandService = mockObject<IChatSlashCommandService>()({});
+		const slashCommandService = mockObject<IChatSlashCommandService>()({ _serviceBrand: undefined });
 		slashCommandService.getCommands.returns([{ command: 'fix' }]);
-		// eslint-disable-next-line local/code-no-any-casts
-		instantiationService.stub(IChatSlashCommandService, slashCommandService as any);
+		instantiationService.stub(IChatSlashCommandService, slashCommandService);
 
 		parser = instantiationService.createInstance(ChatRequestParser);
 		const result = parser.parseChatRequest(testSessionUri, '@agent /fix this', undefined, {
diff --git a/src/vs/workbench/contrib/chat/test/common/tools/builtinTools/askQuestionsTool.test.ts b/src/vs/workbench/contrib/chat/test/common/tools/builtinTools/askQuestionsTool.test.ts
index f82b6bbe55dbd..015fde819ab20 100644
--- a/src/vs/workbench/contrib/chat/test/common/tools/builtinTools/askQuestionsTool.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/tools/builtinTools/askQuestionsTool.test.ts
@@ -4,14 +4,15 @@
  *--------------------------------------------------------------------------------------------*/
 
 import assert from 'assert';
-import { NullTelemetryService } from '../../../../../../../platform/telemetry/common/telemetryUtils.js';
-import { NullLogService } from '../../../../../../../platform/log/common/log.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../../base/test/common/utils.js';
+import { NullLogService } from '../../../../../../../platform/log/common/log.js';
+import { NullTelemetryService } from '../../../../../../../platform/telemetry/common/telemetryUtils.js';
+import { TestConfigurationService } from '../../../../../../../platform/configuration/test/common/testConfigurationService.js';
+import { IChatQuestionAnswers, IChatService } from '../../../../common/chatService/chatService.js';
 import { AskQuestionsTool, IAnswerResult, IQuestion, IQuestionAnswer } from '../../../../common/tools/builtinTools/askQuestionsTool.js';
-import { IChatService } from '../../../../common/chatService/chatService.js';
 
 class TestableAskQuestionsTool extends AskQuestionsTool {
-	public testConvertCarouselAnswers(questions: IQuestion[], carouselAnswers: Record<string, unknown> | undefined): IAnswerResult {
+	public testConvertCarouselAnswers(questions: IQuestion[], carouselAnswers: IChatQuestionAnswers | undefined): IAnswerResult {
 		// Create an identity map where each header is also the internal ID
 		// This simulates the simple case for testing the answer conversion logic
 		const idToHeaderMap = new Map<string, string>();
@@ -30,7 +31,8 @@ suite('AskQuestionsTool - convertCarouselAnswers', () => {
 		tool = store.add(new TestableAskQuestionsTool(
 			null! as IChatService,
 			NullTelemetryService,
-			new NullLogService()
+			new NullLogService(),
+			new TestConfigurationService()
 		));
 	});
 
@@ -70,7 +72,7 @@ suite('AskQuestionsTool - convertCarouselAnswers', () => {
 			{ header: 'Features', question: 'Pick features', multiSelect: true, options: [{ label: 'A' }, { label: 'B' }] }
 		];
 
-		const result = tool.testConvertCarouselAnswers(questions, { Features: ['A', 'B'] });
+		const result = tool.testConvertCarouselAnswers(questions, { Features: { selectedValues: ['A', 'B'] } });
 
 		assert.deepStrictEqual(result.answers['Features'], { selected: ['A', 'B'], freeText: null, skipped: false });
 	});
@@ -131,7 +133,7 @@ suite('AskQuestionsTool - convertCarouselAnswers', () => {
 		const result = tool.testConvertCarouselAnswers(questions, {
 			Q1: 'text',
 			Q2: { selectedValue: 'A' },
-			Q3: ['x', 'y']
+			Q3: { selectedValues: ['x', 'y'] }
 		});
 
 		assert.strictEqual(result.answers['Q1'].freeText, 'text');
diff --git a/src/vs/workbench/contrib/chat/test/common/tools/builtinTools/modifiedFilesConfirmationTool.test.ts b/src/vs/workbench/contrib/chat/test/common/tools/builtinTools/modifiedFilesConfirmationTool.test.ts
new file mode 100644
index 0000000000000..19655689064e3
--- /dev/null
+++ b/src/vs/workbench/contrib/chat/test/common/tools/builtinTools/modifiedFilesConfirmationTool.test.ts
@@ -0,0 +1,67 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { CancellationToken } from '../../../../../../../base/common/cancellation.js';
+import { URI } from '../../../../../../../base/common/uri.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../../base/test/common/utils.js';
+import { ModifiedFilesConfirmationTool, ModifiedFilesConfirmationToolData } from '../../../../common/tools/builtinTools/confirmationTool.js';
+
+suite('ModifiedFilesConfirmationTool', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('tool data exposes the expected schema', () => {
+		assert.strictEqual(ModifiedFilesConfirmationToolData.id, 'vscode_get_modified_files_confirmation');
+		assert.ok(ModifiedFilesConfirmationToolData.inputSchema);
+		assert.deepStrictEqual(ModifiedFilesConfirmationToolData.inputSchema?.required, ['title', 'message', 'options', 'modifiedFiles']);
+		assert.ok(ModifiedFilesConfirmationToolData.inputSchema?.properties?.options);
+		assert.ok(ModifiedFilesConfirmationToolData.inputSchema?.properties?.modifiedFiles);
+	});
+
+	test('prepareToolInvocation parses file data and disables auto confirm', async () => {
+		const tool = new ModifiedFilesConfirmationTool();
+
+		const result = await tool.prepareToolInvocation({
+			parameters: {
+				title: 'Review modified files',
+				message: 'Choose how to continue.',
+				options: ['Copy Changes', 'Move Changes'],
+				modifiedFiles: [{
+					uri: 'file:///workspace/src/file1.ts',
+					originalUri: 'file:///workspace/src/file1.original.ts',
+					insertions: 10,
+					deletions: 3,
+					title: 'File 1'
+				}]
+			},
+			toolCallId: 'call-1',
+			chatSessionResource: URI.parse('vscode-chat://session'),
+		}, CancellationToken.None);
+
+		assert.ok(result);
+		assert.strictEqual(result?.confirmationMessages?.allowAutoConfirm, false);
+		assert.strictEqual(result?.toolSpecificData?.kind, 'modifiedFilesConfirmation');
+
+		assert.deepStrictEqual(result.toolSpecificData.options, ['Copy Changes', 'Move Changes']);
+		assert.strictEqual(URI.revive(result.toolSpecificData.modifiedFiles[0].uri).toString(), 'file:///workspace/src/file1.ts');
+		assert.strictEqual(result.toolSpecificData.modifiedFiles[0].originalUri ? URI.revive(result.toolSpecificData.modifiedFiles[0].originalUri).toString() : undefined, 'file:///workspace/src/file1.original.ts');
+		assert.strictEqual(result.toolSpecificData.modifiedFiles[0].insertions, 10);
+		assert.strictEqual(result.toolSpecificData.modifiedFiles[0].deletions, 3);
+	});
+
+	test('invoke returns the selected option', async () => {
+		const tool = new ModifiedFilesConfirmationTool();
+
+		const result = await tool.invoke({
+			callId: 'call-1',
+			toolId: 'vscode_get_modified_files_confirmation',
+			parameters: {},
+			selectedCustomButton: 'Move Changes',
+			context: undefined,
+		}, async () => 0, { report: () => undefined }, CancellationToken.None);
+
+		assert.deepStrictEqual(result.content, [{ kind: 'text', value: 'Move Changes' }]);
+	});
+});
diff --git a/src/vs/workbench/contrib/chat/test/common/tools/builtinTools/runSubagentTool.test.ts b/src/vs/workbench/contrib/chat/test/common/tools/builtinTools/runSubagentTool.test.ts
index df306a3ef3ad0..79d99695eb588 100644
--- a/src/vs/workbench/contrib/chat/test/common/tools/builtinTools/runSubagentTool.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/tools/builtinTools/runSubagentTool.test.ts
@@ -15,7 +15,9 @@ import { IChatAgentService } from '../../../../common/participants/chatAgents.js
 import { IChatService } from '../../../../common/chatService/chatService.js';
 import { ILanguageModelChatMetadata, ILanguageModelChatMetadataAndIdentifier, ILanguageModelsService } from '../../../../common/languageModels.js';
 import { IInstantiationService } from '../../../../../../../platform/instantiation/common/instantiation.js';
-import { ICustomAgent, PromptsStorage, Target } from '../../../../common/promptSyntax/service/promptsService.js';
+import { IProductService } from '../../../../../../../platform/product/common/productService.js';
+import { ICustomAgent, PromptsStorage } from '../../../../common/promptSyntax/service/promptsService.js';
+import { Target } from '../../../../common/promptSyntax/promptTypes.js';
 import { MockPromptsService } from '../../promptSyntax/service/mockPromptsService.js';
 import { ExtensionIdentifier } from '../../../../../../../platform/extensions/common/extensions.js';
 
@@ -70,6 +72,7 @@ suite('RunSubagentTool', () => {
 				configService,
 				promptsService,
 				{} as IInstantiationService,
+				{} as IProductService,
 			));
 
 			const result = await tool.prepareToolInvocation(
@@ -113,6 +116,7 @@ suite('RunSubagentTool', () => {
 				configService,
 				promptsService,
 				{} as IInstantiationService,
+				{} as IProductService,
 			));
 
 			const toolData = tool.getToolData();
@@ -141,6 +145,7 @@ suite('RunSubagentTool', () => {
 				configService,
 				promptsService,
 				{} as IInstantiationService,
+				{} as IProductService,
 			));
 
 			const toolData = tool.getToolData();
@@ -261,6 +266,7 @@ suite('RunSubagentTool', () => {
 				configService,
 				promptsService,
 				{} as IInstantiationService,
+				{} as IProductService,
 			));
 
 			return tool;
diff --git a/src/vs/workbench/contrib/chat/test/common/tools/mockLanguageModelToolsConfirmationService.ts b/src/vs/workbench/contrib/chat/test/common/tools/mockLanguageModelToolsConfirmationService.ts
index e8d3da161cbd2..d3ce0affbf835 100644
--- a/src/vs/workbench/contrib/chat/test/common/tools/mockLanguageModelToolsConfirmationService.ts
+++ b/src/vs/workbench/contrib/chat/test/common/tools/mockLanguageModelToolsConfirmationService.ts
@@ -9,12 +9,15 @@ import { ILanguageModelToolConfirmationActions, ILanguageModelToolConfirmationCo
 import { IToolData } from '../../../common/tools/languageModelToolsService.js';
 
 export class MockLanguageModelToolsConfirmationService implements ILanguageModelToolsConfirmationService {
-	manageConfirmationPreferences(tools: readonly IToolData[], options?: { defaultScope?: 'workspace' | 'profile' | 'session' }): void {
+	manageConfirmationPreferences(tools: readonly IToolData[], options?: { defaultScope?: 'workspace' | 'profile' | 'session'; focusToolId?: string }): void {
 		throw new Error('Method not implemented.');
 	}
 	registerConfirmationContribution(toolName: string, contribution: ILanguageModelToolConfirmationContribution): IDisposable {
 		throw new Error('Method not implemented.');
 	}
+	toolCanManageConfirmation(): boolean {
+		return false;
+	}
 	resetToolAutoConfirmation(): void {
 
 	}
diff --git a/src/vs/workbench/contrib/chat/test/common/widget/annotations.test.ts b/src/vs/workbench/contrib/chat/test/common/widget/annotations.test.ts
index f41859e6977e7..d25bd70b94c5c 100644
--- a/src/vs/workbench/contrib/chat/test/common/widget/annotations.test.ts
+++ b/src/vs/workbench/contrib/chat/test/common/widget/annotations.test.ts
@@ -9,7 +9,7 @@ import { URI } from '../../../../../../base/common/uri.js';
 import { assertSnapshot } from '../../../../../../base/test/common/snapshot.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
 import { IChatMarkdownContent, IChatResponseCodeblockUriPart } from '../../../common/chatService/chatService.js';
-import { annotateSpecialMarkdownContent, extractCodeblockUrisFromText, extractSubAgentInvocationIdFromText, extractVulnerabilitiesFromText, isInsideCodeContext } from '../../../common/widget/annotations.js';
+import { annotateSpecialMarkdownContent, extractCodeblockUrisFromText, extractSubAgentInvocationIdFromText, extractVulnerabilitiesFromText, hasEditCodeblockUriTag, isInsideCodeContext } from '../../../common/widget/annotations.js';
 
 function content(str: string): IChatMarkdownContent {
 	return { kind: 'markdownContent', content: new MarkdownString(str) };
@@ -239,5 +239,80 @@ suite('Annotations', function () {
 			assert.ok(!md.content.value.includes('_vscodecontentref_'));
 			assert.ok(md.content.value.endsWith('index.ts'));
 		});
+
+		test('inline reference at start of block merges with following markdown', () => {
+			const result = annotateSpecialMarkdownContent([
+				{ kind: 'inlineReference', inlineReference: URI.parse('file:///index.ts'), name: 'index.ts' },
+				{ kind: 'markdownContent', content: new MarkdownString(' is the entry point', { isTrusted: true, supportThemeIcons: true }) },
+			]);
+
+			assert.strictEqual(result.length, 1);
+			const md = result[0] as IChatMarkdownContent;
+			assert.ok(md.content.value.includes('[index.ts]'));
+			assert.ok(md.content.value.includes('_vscodecontentref_'));
+			assert.ok(md.content.value.endsWith(' is the entry point'));
+			assert.ok(md.inlineReferences);
+			assert.strictEqual(md.content.isTrusted, true);
+			assert.strictEqual(md.content.supportThemeIcons, true);
+		});
+
+		test('inline reference after regular text does not force-merge incompatible markdown', () => {
+			const result = annotateSpecialMarkdownContent([
+				content('See '),
+				{ kind: 'inlineReference', inlineReference: URI.parse('file:///index.ts'), name: 'index.ts' },
+				{ kind: 'markdownContent', content: new MarkdownString(' more info', { isTrusted: true, supportThemeIcons: true }) },
+			]);
+
+			// The first item has "See [index.ts](...)" with default markdown properties,
+			// the second item has different properties - they must stay separate.
+			assert.strictEqual(result.length, 2);
+			const first = result[0] as IChatMarkdownContent;
+			assert.ok(first.content.value.startsWith('See '));
+			assert.ok(first.inlineReferences);
+			const second = result[1] as IChatMarkdownContent;
+			assert.strictEqual(second.content.value, ' more info');
+			assert.strictEqual(second.content.isTrusted, true);
+		});
+	});
+
+	suite('hasEditCodeblockUriTag', () => {
+		test('returns true for edit codeblock URI tags', () => {
+			const editTag = '<vscode_codeblock_uri isEdit>file:///test.ts</vscode_codeblock_uri>';
+			assert.strictEqual(hasEditCodeblockUriTag(editTag), true);
+		});
+
+		test('returns false for non-edit codeblock URI tags', () => {
+			const nonEditTag = '<vscode_codeblock_uri>file:///test.ts</vscode_codeblock_uri>';
+			assert.strictEqual(hasEditCodeblockUriTag(nonEditTag), false);
+		});
+
+		test('returns true for edit codeblock URI tags with subAgentInvocationId', () => {
+			const editTagWithSubAgent = '<vscode_codeblock_uri isEdit subAgentInvocationId="agent-123">file:///test.ts</vscode_codeblock_uri>';
+			assert.strictEqual(hasEditCodeblockUriTag(editTagWithSubAgent), true);
+		});
+
+		test('returns false for non-edit codeblock URI tags with subAgentInvocationId', () => {
+			const nonEditTagWithSubAgent = '<vscode_codeblock_uri subAgentInvocationId="agent-123">file:///test.ts</vscode_codeblock_uri>';
+			assert.strictEqual(hasEditCodeblockUriTag(nonEditTagWithSubAgent), false);
+		});
+
+		test('returns false for text without codeblock URI tags', () => {
+			assert.strictEqual(hasEditCodeblockUriTag('some plain text'), false);
+		});
+
+		test('returns false for text with only partial tag prefix', () => {
+			assert.strictEqual(hasEditCodeblockUriTag('<vscode_codebloc'), false);
+		});
+
+		test('returns true for text containing multiple edit codeblock URI tags', () => {
+			const multipleEditTags = 'some text <vscode_codeblock_uri isEdit>file:///test.ts</vscode_codeblock_uri> more <vscode_codeblock_uri isEdit>file:///other.ts</vscode_codeblock_uri>';
+			assert.strictEqual(hasEditCodeblockUriTag(multipleEditTags), true);
+		});
+
+		test('returns false for text containing only non-edit codeblock URI tags', () => {
+			const multipleNonEditTags = 'some text <vscode_codeblock_uri>file:///test.ts</vscode_codeblock_uri> more <vscode_codeblock_uri>file:///other.ts</vscode_codeblock_uri>';
+			assert.strictEqual(hasEditCodeblockUriTag(multipleNonEditTags), false);
+		});
+
 	});
 });
diff --git a/src/vs/workbench/contrib/codeEditor/browser/accessibility/accessibility.css b/src/vs/workbench/contrib/codeEditor/browser/accessibility/accessibility.css
index cda82e4a99866..6767728af164d 100644
--- a/src/vs/workbench/contrib/codeEditor/browser/accessibility/accessibility.css
+++ b/src/vs/workbench/contrib/codeEditor/browser/accessibility/accessibility.css
@@ -7,7 +7,7 @@
 	position: absolute;
 	background-color: var(--vscode-editorWidget-background);
 	color: var(--vscode-editorWidget-foreground);
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	border: 2px solid var(--vscode-focusBorder);
 	border-radius: 6px;
 	margin-top: -1px;
diff --git a/src/vs/workbench/contrib/codeEditor/browser/dictation/editorDictation.css b/src/vs/workbench/contrib/codeEditor/browser/dictation/editorDictation.css
index 0a8d982123f12..b002f8c148dd9 100644
--- a/src/vs/workbench/contrib/codeEditor/browser/dictation/editorDictation.css
+++ b/src/vs/workbench/contrib/codeEditor/browser/dictation/editorDictation.css
@@ -9,7 +9,7 @@
 	border-radius: 8px;
 	display: flex;
 	align-items: center;
-	box-shadow: 0 4px 8px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	z-index: 1000;
 	min-height: var(--vscode-editor-dictation-widget-height);
 	line-height: var(--vscode-editor-dictation-widget-height);
diff --git a/src/vs/workbench/contrib/codeEditor/browser/editorFindAccessibilityHelp.ts b/src/vs/workbench/contrib/codeEditor/browser/editorFindAccessibilityHelp.ts
index 32b0152643dbf..c0cef1433a2d9 100644
--- a/src/vs/workbench/contrib/codeEditor/browser/editorFindAccessibilityHelp.ts
+++ b/src/vs/workbench/contrib/codeEditor/browser/editorFindAccessibilityHelp.ts
@@ -300,6 +300,7 @@ class EditorFindAccessibilityHelpProvider extends Disposable implements IAccessi
 			content.push(localize('find.settingSeed', "- `editor.find.seedSearchStringFromSelection`: Controls when selection text is used to seed Find."));
 			content.push(localize('find.settingAutoSelection', "- `editor.find.autoFindInSelection`: Automatically enables Find in Selection based on selection type."));
 			content.push(localize('find.settingLoop', "- `editor.find.loop`: Wraps search at the beginning or end of the file."));
+			content.push(localize('find.settingCloseOnResult', "- `editor.find.closeOnResult`: Closes the Find dialog after an explicit find navigation command lands on a match."));
 			content.push(localize('find.settingExtraSpace', "- `editor.find.addExtraSpaceOnTop`: Adds extra scroll space so matches are not hidden behind the Find dialog."));
 			content.push(localize('find.settingHistory', "- `editor.find.history`: Controls whether Find search history is stored."));
 			content.push(localize('find.settingOccurrences', "- `editor.occurrencesHighlight`: Highlights other occurrences of the current symbol."));
diff --git a/src/vs/workbench/contrib/codeEditor/browser/find/simpleFindWidget.css b/src/vs/workbench/contrib/codeEditor/browser/find/simpleFindWidget.css
index 5f1597b9de23d..6fb4864cf8723 100644
--- a/src/vs/workbench/contrib/codeEditor/browser/find/simpleFindWidget.css
+++ b/src/vs/workbench/contrib/codeEditor/browser/find/simpleFindWidget.css
@@ -30,7 +30,7 @@
 	transition: top 200ms linear;
 	background-color: var(--vscode-editorWidget-background) !important;
 	color: var(--vscode-editorWidget-foreground);
-	box-shadow: 0 0 8px 2px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	border: 1px solid var(--vscode-widget-border);
 	border-bottom-left-radius: 4px;
 	border-bottom-right-radius: 4px;
diff --git a/src/vs/workbench/contrib/debug/browser/debugActionViewItems.ts b/src/vs/workbench/contrib/debug/browser/debugActionViewItems.ts
index 43c4dba2f34b6..1028ec8992eb8 100644
--- a/src/vs/workbench/contrib/debug/browser/debugActionViewItems.ts
+++ b/src/vs/workbench/contrib/debug/browser/debugActionViewItems.ts
@@ -198,12 +198,14 @@ export class StartDebugActionViewItem extends BaseActionViewItem {
 		const inWorkspace = this.contextService.getWorkbenchState() === WorkbenchState.WORKSPACE;
 		let lastGroup: string | undefined;
 		const disabledIdxs: number[] = [];
+		const separatorIdxs: number[] = [];
 		manager.getAllConfigurations().forEach(({ launch, name, presentation }) => {
 			if (lastGroup !== presentation?.group) {
 				lastGroup = presentation?.group;
 				if (this.debugOptions.length) {
 					this.debugOptions.push({ label: SeparatorSelectOption.text, handler: () => Promise.resolve(false) });
 					disabledIdxs.push(this.debugOptions.length - 1);
+					separatorIdxs.push(this.debugOptions.length - 1);
 				}
 			}
 			if (name === manager.selectedConfiguration.name && launch === manager.selectedConfiguration.launch) {
@@ -239,6 +241,7 @@ export class StartDebugActionViewItem extends BaseActionViewItem {
 
 		this.debugOptions.push({ label: SeparatorSelectOption.text, handler: () => Promise.resolve(false) });
 		disabledIdxs.push(this.debugOptions.length - 1);
+		separatorIdxs.push(this.debugOptions.length - 1);
 
 		this.providers.forEach(p => {
 
@@ -265,7 +268,11 @@ export class StartDebugActionViewItem extends BaseActionViewItem {
 			});
 		});
 
-		this.selectBox.setOptions(this.debugOptions.map((data, index): ISelectOptionItem => ({ text: data.label, isDisabled: disabledIdxs.indexOf(index) !== -1 })), this.selected);
+		this.selectBox.setOptions(this.debugOptions.map((data, index): ISelectOptionItem => ({
+			text: data.label,
+			isDisabled: disabledIdxs.indexOf(index) !== -1,
+			isSeparator: separatorIdxs.indexOf(index) !== -1,
+		})), this.selected);
 	}
 
 	private _setAriaLabel(title: string): void {
diff --git a/src/vs/workbench/contrib/debug/browser/debugToolBar.ts b/src/vs/workbench/contrib/debug/browser/debugToolBar.ts
index 2e54d39fb8ebe..a801205ecc74a 100644
--- a/src/vs/workbench/contrib/debug/browser/debugToolBar.ts
+++ b/src/vs/workbench/contrib/debug/browser/debugToolBar.ts
@@ -30,7 +30,7 @@ import { IInstantiationService } from '../../../../platform/instantiation/common
 import { INotificationService } from '../../../../platform/notification/common/notification.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
-import { widgetBorder, widgetShadow } from '../../../../platform/theme/common/colorRegistry.js';
+import { widgetBorder } from '../../../../platform/theme/common/colorRegistry.js';
 import { IThemeService, Themable } from '../../../../platform/theme/common/themeService.js';
 import { getTitleBarStyle, TitlebarStyle } from '../../../../platform/window/common/window.js';
 import { IWorkbenchContribution } from '../../../common/contributions.js';
@@ -259,9 +259,6 @@ export class DebugToolBar extends Themable implements IWorkbenchContribution {
 		if (this.$el) {
 			this.$el.style.backgroundColor = this.getColor(debugToolBarBackground) || '';
 
-			const widgetShadowColor = this.getColor(widgetShadow);
-			this.$el.style.boxShadow = widgetShadowColor ? `0 0 8px 2px ${widgetShadowColor}` : '';
-
 			const contrastBorderColor = this.getColor(widgetBorder);
 			const borderColor = this.getColor(debugToolBarBorder);
 
diff --git a/src/vs/workbench/contrib/debug/browser/media/debugHover.css b/src/vs/workbench/contrib/debug/browser/media/debugHover.css
index 3a862adbe9fdb..f8e51e2e4de03 100644
--- a/src/vs/workbench/contrib/debug/browser/media/debugHover.css
+++ b/src/vs/workbench/contrib/debug/browser/media/debugHover.css
@@ -12,6 +12,8 @@
 	-webkit-user-select: text;
 	word-break: break-all;
 	white-space: pre;
+	border-radius: var(--vscode-cornerRadius-large);
+	box-shadow: var(--vscode-shadow-lg);
 }
 
 .monaco-editor .debug-hover-widget .complex-value {
diff --git a/src/vs/workbench/contrib/debug/browser/media/debugToolBar.css b/src/vs/workbench/contrib/debug/browser/media/debugToolBar.css
index 090c53e7f9844..ca34e6f77ba14 100644
--- a/src/vs/workbench/contrib/debug/browser/media/debugToolBar.css
+++ b/src/vs/workbench/contrib/debug/browser/media/debugToolBar.css
@@ -9,10 +9,11 @@
 	height: 28px;
 	display: flex;
 	padding-left: 2px;
-	border-radius: 5px;
+	border-radius: var(--vscode-cornerRadius-large);
 	left: 0;
 	top: 0;
 	-webkit-app-region: no-drag;
+	box-shadow: var(--vscode-shadow-lg);
 }
 
 .monaco-workbench .debug-toolbar .monaco-action-bar .action-item {
diff --git a/src/vs/workbench/contrib/debug/browser/media/debugViewlet.css b/src/vs/workbench/contrib/debug/browser/media/debugViewlet.css
index f6ca5b3900c8d..4a627af1f786c 100644
--- a/src/vs/workbench/contrib/debug/browser/media/debugViewlet.css
+++ b/src/vs/workbench/contrib/debug/browser/media/debugViewlet.css
@@ -57,6 +57,7 @@
 	line-height: inherit;
 	padding-top: 0;
 	padding-bottom: 0;
+	border-radius: 0 var(--vscode-cornerRadius-small) var(--vscode-cornerRadius-small) 0;
 
 	/* The debug view title is crowded, let this one get narrower than others */
 	min-width: 90px;
diff --git a/src/vs/workbench/contrib/debug/common/debugModel.ts b/src/vs/workbench/contrib/debug/common/debugModel.ts
index 9c943348a9737..5de69ed78ca80 100644
--- a/src/vs/workbench/contrib/debug/common/debugModel.ts
+++ b/src/vs/workbench/contrib/debug/common/debugModel.ts
@@ -246,7 +246,8 @@ function handleSetResponse(expression: ExpressionContainer, response: DebugProto
 		expression.reference = response.body.variablesReference;
 		expression.namedVariables = response.body.namedVariables;
 		expression.indexedVariables = response.body.indexedVariables;
-		// todo @weinand: the set responses contain most properties, but not memory references. Should they?
+		expression.memoryReference = response.body.memoryReference;
+		expression.valueLocationReference = response.body.valueLocationReference;
 	}
 }
 
diff --git a/src/vs/workbench/contrib/emergencyAlert/electron-browser/emergencyAlert.contribution.ts b/src/vs/workbench/contrib/emergencyAlert/electron-browser/emergencyAlert.contribution.ts
index f8e3072a4743e..85eeeee5438dc 100644
--- a/src/vs/workbench/contrib/emergencyAlert/electron-browser/emergencyAlert.contribution.ts
+++ b/src/vs/workbench/contrib/emergencyAlert/electron-browser/emergencyAlert.contribution.ts
@@ -69,7 +69,7 @@ export class EmergencyAlert extends Disposable implements IWorkbenchContribution
 	}
 
 	private async doFetchAlerts(url: string): Promise<void> {
-		const requestResult = await this.requestService.request({ type: 'GET', url, disableCache: true, timeout: 20000 }, CancellationToken.None);
+		const requestResult = await this.requestService.request({ type: 'GET', url, disableCache: true, timeout: 20000, callSite: 'emergencyAlert.doFetchAlerts' }, CancellationToken.None);
 
 		if (requestResult.res.statusCode !== 200) {
 			throw new Error(`Failed to fetch emergency alerts: HTTP ${requestResult.res.statusCode}`);
diff --git a/src/vs/workbench/contrib/extensions/browser/extensions.contribution.ts b/src/vs/workbench/contrib/extensions/browser/extensions.contribution.ts
index 37e6e916e167c..6e2b340903c4b 100644
--- a/src/vs/workbench/contrib/extensions/browser/extensions.contribution.ts
+++ b/src/vs/workbench/contrib/extensions/browser/extensions.contribution.ts
@@ -62,6 +62,7 @@ import { IPreferencesService } from '../../../services/preferences/common/prefer
 import { CONTEXT_SYNC_ENABLEMENT } from '../../../services/userDataSync/common/userDataSync.js';
 import { IViewsService } from '../../../services/views/common/viewsService.js';
 import { WORKSPACE_TRUST_EXTENSION_SUPPORT } from '../../../services/workspaces/common/workspaceTrust.js';
+import { IPluginInstallService } from '../../chat/common/plugins/pluginInstallService.js';
 import { ILanguageModelToolsService } from '../../chat/common/tools/languageModelToolsService.js';
 import { CONTEXT_KEYBINDINGS_EDITOR } from '../../preferences/common/preferences.js';
 import { IWebview } from '../../webview/browser/webview.js';
@@ -557,6 +558,7 @@ class ExtensionsContributions extends Disposable implements IWorkbenchContributi
 		@IDialogService private readonly dialogService: IDialogService,
 		@ICommandService private readonly commandService: ICommandService,
 		@IProductService private readonly productService: IProductService,
+		@IPluginInstallService private readonly pluginInstallService: IPluginInstallService,
 	) {
 		super();
 		const hasLocalServerContext = CONTEXT_HAS_LOCAL_SERVER.bindTo(contextKeyService);
@@ -698,11 +700,14 @@ class ExtensionsContributions extends Disposable implements IWorkbenchContributi
 				order: 1
 			}],
 			run: async () => {
-				await this.extensionsWorkbenchService.checkForUpdates();
+				const [, pluginResult] = await Promise.all([
+					this.extensionsWorkbenchService.checkForUpdates(),
+					this.pluginInstallService.updateAllPlugins({ silent: true }, CancellationToken.None),
+				]);
 				const outdated = this.extensionsWorkbenchService.outdated;
 				if (outdated.length) {
 					return this.extensionsWorkbenchService.openSearch('@outdated ');
-				} else {
+				} else if (pluginResult.updatedNames.length === 0 && pluginResult.failedNames.length === 0) {
 					return this.dialogService.info(localize('noUpdatesAvailable', "All extensions are up to date."));
 				}
 			}
diff --git a/src/vs/workbench/contrib/extensions/browser/extensionsActions.ts b/src/vs/workbench/contrib/extensions/browser/extensionsActions.ts
index d1dacd0dc6184..e80687f73e29d 100644
--- a/src/vs/workbench/contrib/extensions/browser/extensionsActions.ts
+++ b/src/vs/workbench/contrib/extensions/browser/extensionsActions.ts
@@ -1752,6 +1752,7 @@ export class DisableGloballyAction extends ExtensionAction {
 		if (this.extension && this.extension.local && !this.extension.isWorkspaceScoped && this.extensionService.extensions.some(e => areSameExtensions({ id: e.identifier.value, uuid: e.uuid }, this.extension!.identifier))) {
 			this.enabled = this.extension.state === ExtensionState.Installed
 				&& (this.extension.enablementState === EnablementState.EnabledGlobally || this.extension.enablementState === EnablementState.EnabledWorkspace)
+				&& !this.extensionEnablementService.isDisabledGlobally(this.extension.local)
 				&& this.extensionEnablementService.canChangeEnablement(this.extension.local);
 		}
 	}
diff --git a/src/vs/workbench/contrib/extensions/browser/media/extensionsViewlet.css b/src/vs/workbench/contrib/extensions/browser/media/extensionsViewlet.css
index fd3aa7ae144bd..3031aeba46db9 100644
--- a/src/vs/workbench/contrib/extensions/browser/media/extensionsViewlet.css
+++ b/src/vs/workbench/contrib/extensions/browser/media/extensionsViewlet.css
@@ -161,6 +161,11 @@
 
 .extensions-viewlet > .extensions .extension-list-item {
 	position: absolute;
+	box-shadow: var(--vscode-shadow-sm);
+}
+
+.extensions-viewlet > .extensions .extension-list-item:hover {
+	box-shadow: var(--vscode-shadow-md);
 }
 
 .extensions-viewlet > .extensions .extension-list-item.loading {
diff --git a/src/vs/workbench/contrib/extensions/electron-browser/extensionsSlowActions.ts b/src/vs/workbench/contrib/extensions/electron-browser/extensionsSlowActions.ts
index 46120a9e645e1..77c1661c677ed 100644
--- a/src/vs/workbench/contrib/extensions/electron-browser/extensionsSlowActions.ts
+++ b/src/vs/workbench/contrib/extensions/electron-browser/extensionsSlowActions.ts
@@ -100,7 +100,7 @@ export async function createSlowExtensionAction(
 	const url = `https://api.github.com/search/issues?q=is:issue+state:open+in:title+repo:${info.owner}/${info.repo}+%22Extension+causes+high+cpu+load%22`;
 	let res: IRequestContext;
 	try {
-		res = await requestService.request({ url }, CancellationToken.None);
+		res = await requestService.request({ url, callSite: 'extensionsSlowActions.getSlowExtensionAction' }, CancellationToken.None);
 	} catch {
 		return undefined;
 	}
diff --git a/src/vs/workbench/contrib/extensions/test/electron-browser/extensionsActions.test.ts b/src/vs/workbench/contrib/extensions/test/electron-browser/extensionsActions.test.ts
index 14745b971ecb0..c9a2bc80df17f 100644
--- a/src/vs/workbench/contrib/extensions/test/electron-browser/extensionsActions.test.ts
+++ b/src/vs/workbench/contrib/extensions/test/electron-browser/extensionsActions.test.ts
@@ -963,6 +963,27 @@ suite('ExtensionsActions', () => {
 			});
 	});
 
+	test('Test DisableGloballyAction when extension is disabled globally and enabled for workspace', async () => {
+		const local = aLocalExtension('a');
+		const enablementService = instantiationService.get(IWorkbenchExtensionEnablementService);
+		await enablementService.setEnablement([local], EnablementState.DisabledGlobally);
+		await enablementService.setEnablement([local], EnablementState.EnabledWorkspace);
+
+		instantiationService.stubPromise(IExtensionManagementService, 'getInstalled', [local]);
+		instantiationService.stub(IExtensionService, {
+			extensions: [toExtensionDescription(local)],
+			onDidChangeExtensions: Event.None,
+			whenInstalledExtensionsRegistered: () => Promise.resolve(true)
+		});
+
+		return instantiationService.get(IExtensionsWorkbenchService).queryLocal()
+			.then(extensions => {
+				const testObject: ExtensionsActions.DisableGloballyAction = disposables.add(instantiationService.createInstance(ExtensionsActions.DisableGloballyAction));
+				testObject.extension = extensions[0];
+				assert.ok(!testObject.enabled);
+			});
+	});
+
 });
 
 suite('ExtensionRuntimeStateAction', () => {
diff --git a/src/vs/workbench/contrib/git/browser/gitService.ts b/src/vs/workbench/contrib/git/browser/gitService.ts
index 2406d972a3bde..ca34f506015b9 100644
--- a/src/vs/workbench/contrib/git/browser/gitService.ts
+++ b/src/vs/workbench/contrib/git/browser/gitService.ts
@@ -7,7 +7,7 @@ import { CancellationToken } from '../../../../base/common/cancellation.js';
 import { BugIndicatingError } from '../../../../base/common/errors.js';
 import { Disposable, IDisposable, toDisposable } from '../../../../base/common/lifecycle.js';
 import { URI } from '../../../../base/common/uri.js';
-import { IGitService, IGitExtensionDelegate, GitRef, GitRefQuery, IGitRepository, GitRepositoryState } from '../common/gitService.js';
+import { IGitService, IGitExtensionDelegate, GitRef, GitRefQuery, IGitRepository, GitRepositoryState, GitDiffChange } from '../common/gitService.js';
 import { ISettableObservable, observableValueOpts } from '../../../../base/common/observable.js';
 import { structuralEquals } from '../../../../base/common/equals.js';
 import { AutoOpenBarrier } from '../../../../base/common/async.js';
@@ -81,4 +81,8 @@ export class GitRepository extends Disposable implements IGitRepository {
 	async getRefs(query: GitRefQuery, token?: CancellationToken): Promise<GitRef[]> {
 		return this.delegate.getRefs(this.rootUri, query, token);
 	}
+
+	async diffBetweenWithStats(ref1: string, ref2: string, path?: string): Promise<GitDiffChange[]> {
+		return this.delegate.diffBetweenWithStats(this.rootUri, ref1, ref2, path);
+	}
 }
diff --git a/src/vs/workbench/contrib/git/common/gitService.ts b/src/vs/workbench/contrib/git/common/gitService.ts
index 353686d452ab5..ce605402b6ff4 100644
--- a/src/vs/workbench/contrib/git/common/gitService.ts
+++ b/src/vs/workbench/contrib/git/common/gitService.ts
@@ -29,16 +29,37 @@ export interface GitRefQuery {
 	readonly sort?: 'alphabetically' | 'committerdate' | 'creatordate';
 }
 
+export interface GitChange {
+	readonly uri: URI;
+	readonly originalUri: URI | undefined;
+	readonly modifiedUri: URI | undefined;
+}
+
+export interface GitDiffChange extends GitChange {
+	readonly insertions: number;
+	readonly deletions: number;
+}
+
 export interface GitRepositoryState {
 	readonly HEAD?: GitBranch;
+	readonly mergeChanges: readonly GitChange[];
+	readonly indexChanges: readonly GitChange[];
+	readonly workingTreeChanges: readonly GitChange[];
+	readonly untrackedChanges: readonly GitChange[];
 }
 
 export interface GitBranch extends GitRef {
+	readonly base?: GitBaseRef;
 	readonly upstream?: GitUpstreamRef;
 	readonly ahead?: number;
 	readonly behind?: number;
 }
 
+export interface GitBaseRef {
+	readonly name: string;
+	readonly isProtected: boolean;
+}
+
 export interface GitUpstreamRef {
 	readonly remote: string;
 	readonly name: string;
@@ -52,6 +73,7 @@ export interface IGitRepository {
 	updateState(state: GitRepositoryState): void;
 
 	getRefs(query: GitRefQuery, token?: CancellationToken): Promise<GitRef[]>;
+	diffBetweenWithStats(ref1: string, ref2: string, path?: string): Promise<GitDiffChange[]>;
 }
 
 export interface IGitExtensionDelegate {
@@ -59,6 +81,7 @@ export interface IGitExtensionDelegate {
 	openRepository(uri: URI): Promise<IGitRepository | undefined>;
 
 	getRefs(root: URI, query?: GitRefQuery, token?: CancellationToken): Promise<GitRef[]>;
+	diffBetweenWithStats(root: URI, ref1: string, ref2: string, path?: string): Promise<GitDiffChange[]>;
 }
 
 export const IGitService = createDecorator<IGitService>('gitService');
diff --git a/src/vs/workbench/contrib/imageCarousel/AGENTS.md b/src/vs/workbench/contrib/imageCarousel/AGENTS.md
new file mode 100644
index 0000000000000..202db937fb34d
--- /dev/null
+++ b/src/vs/workbench/contrib/imageCarousel/AGENTS.md
@@ -0,0 +1,48 @@
+# Image Carousel
+
+A generic workbench editor for viewing collections of images in a carousel/slideshow UI. Opens as a modal editor pane with navigation arrows, a caption, and a thumbnail strip.
+
+## Architecture
+
+The image carousel is a self-contained workbench contribution that follows the **custom editor** pattern:
+
+- **URI scheme**: `vscode-image-carousel` (registered in `Schemas` in `src/vs/base/common/network.ts`) — used for `EditorInput.resource` identity.
+- **Direct editor input**: Callers create `ImageCarouselEditorInput` with a collection and open it directly via `IEditorService.openEditor()`.
+- **Image extraction**: Chat integration builds a **sections-based** collection from chat request/response items. A section can include user-attached request images alongside response-derived images (tool invocations and inline references). For paired request/response items, the section title prefers the user's chat request message; pending requests with image attachments form their own section.
+
+## How to open the carousel
+
+### From code (generic)
+
+```ts
+const collection: IImageCarouselCollection = { id, title, sections: [{ title: '', images: [...] }] };
+const input = new ImageCarouselEditorInput(collection, startIndex);
+await editorService.openEditor(input, { pinned: true }, MODAL_GROUP);
+```
+
+### From chat (via click handler)
+
+Clicking an image attachment pill in chat (when `chat.imageCarousel.enabled` is true) executes the `workbench.action.chat.openImageInCarousel` command, which collects request attachment images together with response-derived images for the current chat session and opens them in the carousel. MIME types are resolved via `getMediaMime()` from `src/vs/base/common/mime.ts`.
+
+## Key design decisions
+
+### Editor & lifecycle
+
+- **Modal editor**: Opens in `MODAL_GROUP` (-4) as an overlay.
+- **Not restorable**: `canSerialize()` returns `false` — image data is in-memory only.
+- **Collection ID = chat session identity**: `sessionResource + '_carousel'` for stable dedup via `EditorInput.matches()`.
+- **Preview-gated**: `chat.imageCarousel.enabled` (default `false`, tagged `preview`). When off, clicks fall through to `openResource()`.
+- **Exact image matching**: Finds the clicked image within the constructed collection by URI first, then falls back to byte equality when needed.
+
+### DOM & rendering
+
+- **DOM construction**: Uses the `h()` helper from `vs/base/browser/dom` with `@name` references for declarative DOM — no imperative `document.createElement` calls.
+- **Bottom bar**: Caption and thumbnail sections are wrapped in a `div.bottom-bar` flex column below the image area.
+- **Stable DOM skeleton**: Builds DOM once per `setInput()`, updates only changing parts to avoid flash on navigation.
+- **Blob URL lifecycle**: Main image URLs tracked in `_imageDisposables` (revoked on nav), thumbnails in `_contentDisposables` (revoked on `clearInput()`).
+- **Focus border suppressed**: The slideshow container uses `outline: none !important` on `:focus` / `:focus-visible` to override the workbench's global `[tabindex="0"]` focus styles.
+
+### Keyboard & focus
+
+- **Keyboard parity**: Uses `registerOpenEditorListeners` (click, double-click, Enter, Space) matching other attachment widgets.
+- **Arrow key navigation**: Handled via DOM `keydown` listener with `stopPropagation()` — not Action2 keybindings, because the modal editor's `KEY_DOWN` handler blocks `workbench.*` commands not in its allowlist. The editor overrides `focus()` to forward focus to the slideshow container so arrow keys work immediately without clicking.
diff --git a/src/vs/workbench/contrib/imageCarousel/browser/imageCarousel.contribution.ts b/src/vs/workbench/contrib/imageCarousel/browser/imageCarousel.contribution.ts
new file mode 100644
index 0000000000000..e298bc3f20e40
--- /dev/null
+++ b/src/vs/workbench/contrib/imageCarousel/browser/imageCarousel.contribution.ts
@@ -0,0 +1,323 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import './media/imageCarousel.css';
+import { localize, localize2 } from '../../../../nls.js';
+import { SyncDescriptor } from '../../../../platform/instantiation/common/descriptors.js';
+import { ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
+import { Registry } from '../../../../platform/registry/common/platform.js';
+import { EditorPaneDescriptor, IEditorPaneRegistry } from '../../../browser/editor.js';
+import { EditorExtensions, IEditorFactoryRegistry, IEditorSerializer } from '../../../common/editor.js';
+import { IEditorService, MODAL_GROUP } from '../../../services/editor/common/editorService.js';
+import { VSBuffer } from '../../../../base/common/buffer.js';
+import { generateUuid } from '../../../../base/common/uuid.js';
+import { ImageCarouselEditor } from './imageCarouselEditor.js';
+import { ImageCarouselEditorInput } from './imageCarouselEditorInput.js';
+import { ICarouselImage, IImageCarouselCollection } from './imageCarouselTypes.js';
+import { Action2, MenuId, registerAction2 } from '../../../../platform/actions/common/actions.js';
+import { ContextKeyExpr } from '../../../../platform/contextkey/common/contextkey.js';
+import { ExplorerFolderContext } from '../../files/common/files.js';
+import { IExplorerService } from '../../files/browser/files.js';
+import { ResourceContextKey } from '../../../common/contextkeys.js';
+import { IFileService } from '../../../../platform/files/common/files.js';
+import { getMediaMime } from '../../../../base/common/mime.js';
+import { URI } from '../../../../base/common/uri.js';
+import { basename, dirname, extname } from '../../../../base/common/resources.js';
+import { ResourceSet } from '../../../../base/common/map.js';
+import { INotificationService } from '../../../../platform/notification/common/notification.js';
+import { IWorkspaceContextService } from '../../../../platform/workspace/common/workspace.js';
+import { Extensions as ConfigurationExtensions, IConfigurationRegistry } from '../../../../platform/configuration/common/configurationRegistry.js';
+import { Limiter } from '../../../../base/common/async.js';
+
+// --- Configuration ---
+
+Registry.as<IConfigurationRegistry>(ConfigurationExtensions.Configuration).registerConfiguration({
+	id: 'imageCarousel',
+	title: localize('imageCarouselConfigurationTitle', "Image Carousel"),
+	type: 'object',
+	properties: {
+		'imageCarousel.explorerContextMenu.enabled': {
+			type: 'boolean',
+			default: false,
+			markdownDescription: localize('imageCarousel.explorerContextMenu.enabled', "Controls whether the **Open Images in Carousel** option appears in the Explorer context menu. This is an experimental feature."),
+			tags: ['experimental'],
+		},
+	}
+});
+
+// --- Editor Pane Registration ---
+
+Registry.as<IEditorPaneRegistry>(EditorExtensions.EditorPane).registerEditorPane(
+	EditorPaneDescriptor.create(
+		ImageCarouselEditor,
+		ImageCarouselEditor.ID,
+		localize('imageCarouselEditor', "Image Carousel")
+	),
+	[
+		new SyncDescriptor(ImageCarouselEditorInput)
+	]
+);
+
+// --- Serializer ---
+
+class ImageCarouselEditorInputSerializer implements IEditorSerializer {
+	canSerialize(): boolean {
+		return false;
+	}
+
+	serialize(): string | undefined {
+		return undefined;
+	}
+
+	deserialize(): ImageCarouselEditorInput | undefined {
+		return undefined;
+	}
+}
+
+Registry.as<IEditorFactoryRegistry>(EditorExtensions.EditorFactory)
+	.registerEditorSerializer(ImageCarouselEditorInput.ID, ImageCarouselEditorInputSerializer);
+
+// --- Args Types ---
+
+interface IOpenCarouselCollectionArgs {
+	readonly collection: IImageCarouselCollection;
+	readonly startIndex: number;
+}
+
+interface IOpenCarouselSingleImageArgs {
+	readonly name: string;
+	readonly mimeType: string;
+	readonly data: Uint8Array;
+	readonly title?: string;
+}
+
+function isCollectionArgs(args: unknown): args is IOpenCarouselCollectionArgs {
+	return typeof args === 'object' && args !== null
+		&& typeof (args as IOpenCarouselCollectionArgs).collection === 'object'
+		&& typeof (args as IOpenCarouselCollectionArgs).startIndex === 'number';
+}
+
+function isSingleImageArgs(args: unknown): args is IOpenCarouselSingleImageArgs {
+	return typeof args === 'object' && args !== null
+		&& typeof (args as IOpenCarouselSingleImageArgs).name === 'string'
+		&& typeof (args as IOpenCarouselSingleImageArgs).mimeType === 'string'
+		&& (args as IOpenCarouselSingleImageArgs).data instanceof Uint8Array;
+}
+
+// --- Actions ---
+
+class OpenImageInCarouselAction extends Action2 {
+	constructor() {
+		super({
+			id: 'workbench.action.chat.openImageInCarousel',
+			title: localize2('openImageInCarousel', "Open Image in Carousel"),
+			f1: false
+		});
+	}
+
+	async run(accessor: ServicesAccessor, args?: unknown): Promise<void> {
+		const editorService = accessor.get(IEditorService);
+
+		let collection: IImageCarouselCollection;
+		let startIndex: number;
+
+		if (isCollectionArgs(args)) {
+			collection = args.collection;
+			startIndex = args.startIndex;
+		} else if (isSingleImageArgs(args)) {
+			collection = {
+				id: generateUuid(),
+				title: args.title ?? localize('imageCarousel.title', "Image Carousel"),
+				sections: [{
+					title: '',
+					images: [{
+						id: generateUuid(),
+						name: args.name,
+						mimeType: args.mimeType,
+						data: VSBuffer.wrap(args.data),
+					}],
+				}],
+			};
+			startIndex = 0;
+		} else {
+			return;
+		}
+
+		const input = new ImageCarouselEditorInput(collection, startIndex);
+		await editorService.openEditor(input, { pinned: true }, MODAL_GROUP);
+	}
+}
+
+registerAction2(OpenImageInCarouselAction);
+
+// --- Explorer Context Menu Integration ---
+
+/** Supported image extensions for the carousel explorer context menu. */
+const IMAGE_EXTENSION_REGEX = /^\.(png|jpg|jpeg|jpe|gif|webp|svg|bmp|ico)$/i;
+
+function isImageResource(uri: URI): boolean {
+	return IMAGE_EXTENSION_REGEX.test(extname(uri));
+}
+
+async function collectImageFilesFromFolder(fileService: IFileService, folderUri: URI): Promise<URI[]> {
+	const stat = await fileService.resolve(folderUri);
+	const imageUris: URI[] = [];
+	if (stat.children) {
+		for (const child of stat.children) {
+			if (child.isFile && isImageResource(child.resource)) {
+				imageUris.push(child.resource);
+			}
+		}
+	}
+	imageUris.sort((a, b) => basename(a).localeCompare(basename(b)));
+	return imageUris;
+}
+
+async function readImageFiles(fileService: IFileService, uris: URI[]): Promise<ICarouselImage[]> {
+	const limiter = new Limiter<ICarouselImage | undefined>(10);
+	const results = await Promise.all(
+		uris.map(uri => limiter.queue(async () => {
+			try {
+				const content = await fileService.readFile(uri);
+				const mimeType = getMediaMime(uri.path) ?? 'image/png';
+				return {
+					id: generateUuid(),
+					name: basename(uri),
+					mimeType,
+					data: content.value,
+					uri,
+				};
+			} catch {
+				return undefined;
+			}
+		}))
+	);
+	return results.filter((r): r is ICarouselImage => r !== undefined);
+}
+
+class OpenImagesInCarouselFromExplorerAction extends Action2 {
+	constructor() {
+		super({
+			id: 'workbench.action.openImagesInCarousel',
+			title: localize2('openImagesInCarousel', "Open Images in Carousel"),
+			f1: false,
+			menu: [{
+				id: MenuId.ExplorerContext,
+				group: 'navigation',
+				order: 25,
+				when: ContextKeyExpr.and(
+					ContextKeyExpr.has('config.imageCarousel.explorerContextMenu.enabled'),
+					ContextKeyExpr.or(
+						ExplorerFolderContext,
+						ContextKeyExpr.regex(ResourceContextKey.Extension.key, IMAGE_EXTENSION_REGEX),
+					),
+				),
+			}],
+		});
+	}
+
+	async run(accessor: ServicesAccessor, resource?: URI): Promise<void> {
+		const explorerService = accessor.get(IExplorerService);
+		const fileService = accessor.get(IFileService);
+		const editorService = accessor.get(IEditorService);
+		const notificationService = accessor.get(INotificationService);
+		const contextService = accessor.get(IWorkspaceContextService);
+
+		const context = explorerService.getContext(true);
+
+		let imageUris: URI[] = [];
+		let startUri: URI | undefined;
+
+		try {
+			if (context.length === 0) {
+				// Empty-space right-click: the explorer passes the workspace root
+				// as the resource argument. Fall back to the first workspace folder
+				// when no resource is available.
+				let folderUri: URI | undefined;
+				if (URI.isUri(resource)) {
+					folderUri = resource;
+				} else {
+					const folders = contextService.getWorkspace().folders;
+					if (folders.length > 0) {
+						folderUri = folders[0].uri;
+					}
+				}
+
+				if (folderUri) {
+					imageUris = await collectImageFilesFromFolder(fileService, folderUri);
+				}
+			} else {
+				const hasSingleImageFile = context.length === 1 && !context[0].isDirectory && isImageResource(context[0].resource);
+
+				if (hasSingleImageFile) {
+					// Single image: show all sibling images in the same folder with
+					// the selected image focused
+					startUri = context[0].resource;
+					const parentUri = dirname(context[0].resource);
+					imageUris = await collectImageFilesFromFolder(fileService, parentUri);
+				} else {
+					// Multiple items or a folder: collect images from selection,
+					// deduplicating in case a folder and its children are both selected
+					const seen = new ResourceSet();
+					for (const item of context) {
+						if (item.isDirectory) {
+							const folderImages = await collectImageFilesFromFolder(fileService, item.resource);
+							for (const uri of folderImages) {
+								if (!seen.has(uri)) {
+									seen.add(uri);
+									imageUris.push(uri);
+								}
+							}
+						} else if (isImageResource(item.resource)) {
+							if (!seen.has(item.resource)) {
+								seen.add(item.resource);
+								imageUris.push(item.resource);
+								if (!startUri) {
+									startUri = item.resource;
+								}
+							}
+						}
+					}
+				}
+			}
+		} catch {
+			notificationService.error(localize('folderReadError', "Could not read folder contents."));
+			return;
+		}
+
+		if (imageUris.length === 0) {
+			notificationService.info(localize('noImagesFound', "No images found in this folder."));
+			return;
+		}
+
+		const images = await readImageFiles(fileService, imageUris);
+		if (images.length === 0) {
+			notificationService.error(localize('imageReadError', "Could not read the selected images."));
+			return;
+		}
+
+		let startIndex = 0;
+		if (startUri) {
+			const idx = images.findIndex(img => img.uri?.toString() === startUri!.toString());
+			if (idx >= 0) {
+				startIndex = idx;
+			}
+		}
+
+		const collection: IImageCarouselCollection = {
+			id: generateUuid(),
+			title: localize('imageCarousel.explorerTitle', "Image Carousel"),
+			sections: [{
+				title: '',
+				images,
+			}],
+		};
+
+		const input = new ImageCarouselEditorInput(collection, startIndex);
+		await editorService.openEditor(input, { pinned: true }, MODAL_GROUP);
+	}
+}
+
+registerAction2(OpenImagesInCarouselFromExplorerAction);
diff --git a/src/vs/workbench/contrib/imageCarousel/browser/imageCarouselEditor.ts b/src/vs/workbench/contrib/imageCarousel/browser/imageCarouselEditor.ts
new file mode 100644
index 0000000000000..07077b4b3e3e7
--- /dev/null
+++ b/src/vs/workbench/contrib/imageCarousel/browser/imageCarouselEditor.ts
@@ -0,0 +1,296 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { addDisposableListener, clearNode, Dimension, EventType, h } from '../../../../base/browser/dom.js';
+import { StandardKeyboardEvent } from '../../../../base/browser/keyboardEvent.js';
+import { KeyCode } from '../../../../base/common/keyCodes.js';
+import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { DisposableStore } from '../../../../base/common/lifecycle.js';
+import { localize } from '../../../../nls.js';
+import { IEditorOptions } from '../../../../platform/editor/common/editor.js';
+import { IThemeService } from '../../../../platform/theme/common/themeService.js';
+import { EditorPane } from '../../../browser/parts/editor/editorPane.js';
+import { IEditorOpenContext } from '../../../common/editor.js';
+import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
+import { IStorageService } from '../../../../platform/storage/common/storage.js';
+import { IEditorGroup } from '../../../services/editor/common/editorGroupsService.js';
+import { ImageCarouselEditorInput } from './imageCarouselEditorInput.js';
+import { ICarouselImage, ICarouselSection } from './imageCarouselTypes.js';
+
+/**
+ * A flat entry referencing a specific image within a section, used
+ * for global index-based navigation across all sections.
+ */
+interface IFlatImageEntry {
+	readonly sectionIndex: number;
+	readonly imageIndexInSection: number;
+	readonly image: ICarouselImage;
+}
+
+export class ImageCarouselEditor extends EditorPane {
+	static readonly ID = 'workbench.editor.imageCarousel';
+
+	private _container: HTMLElement | undefined;
+	private _currentIndex: number = 0;
+	private _sections: ReadonlyArray<ICarouselSection> = [];
+	private _flatImages: IFlatImageEntry[] = [];
+	private readonly _contentDisposables = this._register(new DisposableStore());
+	private readonly _imageDisposables = this._register(new DisposableStore());
+
+	private _elements: {
+		root: HTMLElement;
+		mainImage: HTMLImageElement;
+		caption: HTMLElement;
+		prevBtn: HTMLButtonElement;
+		nextBtn: HTMLButtonElement;
+		sectionsContainer: HTMLElement;
+	} | undefined;
+	private _thumbnailElements: HTMLElement[] = [];
+
+	constructor(
+		group: IEditorGroup,
+		@ITelemetryService telemetryService: ITelemetryService,
+		@IThemeService themeService: IThemeService,
+		@IStorageService storageService: IStorageService
+	) {
+		super(ImageCarouselEditor.ID, group, telemetryService, themeService, storageService);
+	}
+
+	protected override createEditor(parent: HTMLElement): void {
+		this._container = h('div.image-carousel-editor').root;
+		parent.appendChild(this._container);
+	}
+
+	override async setInput(input: ImageCarouselEditorInput, options: IEditorOptions | undefined, context: IEditorOpenContext, token: CancellationToken): Promise<void> {
+		await super.setInput(input, options, context, token);
+
+		this._sections = input.collection.sections;
+		this._flatImages = [];
+		for (let s = 0; s < this._sections.length; s++) {
+			for (let i = 0; i < this._sections[s].images.length; i++) {
+				this._flatImages.push({ sectionIndex: s, imageIndexInSection: i, image: this._sections[s].images[i] });
+			}
+		}
+		this._currentIndex = Math.min(input.startIndex, Math.max(0, this._flatImages.length - 1));
+		this.buildSlideshow();
+	}
+
+	override clearInput(): void {
+		this._contentDisposables.clear();
+		this._imageDisposables.clear();
+		if (this._container) {
+			clearNode(this._container);
+		}
+		this._elements = undefined;
+		this._thumbnailElements = [];
+		super.clearInput();
+	}
+
+	/**
+	 * Build the full DOM skeleton. Called once per setInput.
+	 */
+	private buildSlideshow(): void {
+		if (!this._container) {
+			return;
+		}
+
+		this._contentDisposables.clear();
+		this._imageDisposables.clear();
+		clearNode(this._container);
+
+		if (this._flatImages.length === 0) {
+			const empty = h('div.empty-message');
+			empty.root.textContent = localize('imageCarousel.noImages', "No images to display");
+			this._container.appendChild(empty.root);
+			return;
+		}
+
+		const elements = h('div.slideshow-container', [
+			h('div.image-area@imageArea', [
+				h('div.main-image-container', [
+					h('img.main-image@mainImage'),
+				]),
+				h('button.nav-arrow.prev-arrow@prevBtn', { ariaLabel: localize('imageCarousel.previousImage', "Previous image") }, [
+					h('span.codicon.codicon-chevron-left'),
+				]),
+				h('button.nav-arrow.next-arrow@nextBtn', { ariaLabel: localize('imageCarousel.nextImage', "Next image") }, [
+					h('span.codicon.codicon-chevron-right'),
+				]),
+			]),
+			h('div.bottom-bar@bottomBar', [
+				h('div.image-caption@caption'),
+				h('div.sections-container@sectionsContainer'),
+			]),
+		]);
+
+		this._elements = {
+			root: elements.root,
+			mainImage: elements.mainImage as HTMLImageElement,
+			caption: elements.caption,
+			prevBtn: elements.prevBtn as HTMLButtonElement,
+			nextBtn: elements.nextBtn as HTMLButtonElement,
+			sectionsContainer: elements.sectionsContainer,
+		};
+
+		// Navigation listeners
+		this._contentDisposables.add(addDisposableListener(this._elements.prevBtn, 'click', () => {
+			if (this._currentIndex > 0) {
+				this._currentIndex--;
+				this.updateCurrentImage();
+			}
+		}));
+		this._contentDisposables.add(addDisposableListener(this._elements.nextBtn, 'click', () => {
+			if (this._currentIndex < this._flatImages.length - 1) {
+				this._currentIndex++;
+				this.updateCurrentImage();
+			}
+		}));
+
+		// Keyboard navigation
+		this._contentDisposables.add(addDisposableListener(elements.root, EventType.KEY_DOWN, e => {
+			const event = new StandardKeyboardEvent(e);
+			if (event.keyCode === KeyCode.LeftArrow) {
+				this.previous();
+				event.stopPropagation();
+				event.preventDefault();
+			} else if (event.keyCode === KeyCode.RightArrow) {
+				this.next();
+				event.stopPropagation();
+				event.preventDefault();
+			}
+		}));
+		elements.root.tabIndex = 0;
+
+		// Build section thumbnails
+		this._thumbnailElements = [];
+		let flatIndex = 0;
+		for (let s = 0; s < this._sections.length; s++) {
+			const section = this._sections[s];
+
+			// Add separator between sections (not before the first)
+			if (s > 0 && this._sections.length > 1) {
+				this._elements.sectionsContainer.appendChild(h('div.thumbnail-separator').root);
+			}
+
+			for (let i = 0; i < section.images.length; i++) {
+				const image = section.images[i];
+				const currentFlatIndex = flatIndex;
+				const thumbnail = h('button.thumbnail@root', [
+					h('img.thumbnail-image@img'),
+				]);
+
+				const btn = thumbnail.root as HTMLButtonElement;
+				btn.ariaLabel = localize('imageCarousel.thumbnailLabel', "Image {0} of {1}", currentFlatIndex + 1, this._flatImages.length);
+
+				const img = thumbnail.img as HTMLImageElement;
+				const blob = new Blob([image.data.buffer.slice(0)], { type: image.mimeType });
+				const url = URL.createObjectURL(blob);
+				img.src = url;
+				img.alt = image.name;
+				this._contentDisposables.add({ dispose: () => URL.revokeObjectURL(url) });
+
+				this._contentDisposables.add(addDisposableListener(btn, 'click', () => {
+					this._currentIndex = currentFlatIndex;
+					this.updateCurrentImage();
+				}));
+
+				this._elements.sectionsContainer.appendChild(btn);
+				this._thumbnailElements.push(btn);
+				flatIndex++;
+			}
+		}
+
+		this._container.appendChild(elements.root);
+
+		// Set initial image
+		this.updateCurrentImage();
+	}
+
+	/**
+	 * Update only the changing parts: main image src, caption, button states, thumbnail selection.
+	 * No DOM teardown/rebuild — eliminates the blank flash.
+	 */
+	private updateCurrentImage(): void {
+		if (!this._elements) {
+			return;
+		}
+
+		// Swap main image blob URL
+		this._imageDisposables.clear();
+		const entry = this._flatImages[this._currentIndex];
+		const currentImage = entry.image;
+		const blob = new Blob([currentImage.data.buffer.slice(0)], { type: currentImage.mimeType });
+		const url = URL.createObjectURL(blob);
+		this._elements.mainImage.src = url;
+		this._elements.mainImage.alt = currentImage.name;
+		this._imageDisposables.add({ dispose: () => URL.revokeObjectURL(url) });
+
+		// Update caption
+		if (currentImage.caption) {
+			this._elements.caption.textContent = currentImage.caption;
+			this._elements.caption.style.display = '';
+		} else {
+			this._elements.caption.textContent = '';
+			this._elements.caption.style.display = 'none';
+		}
+
+		// Update button states
+		this._elements.prevBtn.disabled = this._currentIndex === 0;
+		this._elements.nextBtn.disabled = this._currentIndex === this._flatImages.length - 1;
+
+		// Update thumbnail selection
+		for (let i = 0; i < this._thumbnailElements.length; i++) {
+			const isActive = i === this._currentIndex;
+			const thumbnail = this._thumbnailElements[i];
+			thumbnail.classList.toggle('active', isActive);
+			if (isActive) {
+				thumbnail.setAttribute('aria-current', 'page');
+				// Scroll only the thumbnail strip, not the entire editor
+				const container = this._elements.sectionsContainer;
+				const containerRect = container.getBoundingClientRect();
+				const thumbRect = thumbnail.getBoundingClientRect();
+				if (thumbRect.left < containerRect.left) {
+					container.scrollLeft += thumbRect.left - containerRect.left;
+				} else if (thumbRect.right > containerRect.right) {
+					container.scrollLeft += thumbRect.right - containerRect.right;
+				}
+			} else {
+				thumbnail.removeAttribute('aria-current');
+			}
+		}
+
+		// Update editor title to reflect current section
+		if (this.input instanceof ImageCarouselEditorInput) {
+			const currentSection = this._sections[entry.sectionIndex];
+			this.input.setName(currentSection.title || this.input.collection.title);
+		}
+	}
+
+	previous(): void {
+		if (this._currentIndex > 0) {
+			this._currentIndex--;
+			this.updateCurrentImage();
+		}
+	}
+
+	next(): void {
+		if (this._currentIndex < this._flatImages.length - 1) {
+			this._currentIndex++;
+			this.updateCurrentImage();
+		}
+	}
+
+	override focus(): void {
+		super.focus();
+		this._elements?.root.focus();
+	}
+
+	override layout(dimension: Dimension): void {
+		if (this._container) {
+			this._container.style.width = `${dimension.width}px`;
+			this._container.style.height = `${dimension.height}px`;
+		}
+	}
+}
diff --git a/src/vs/workbench/contrib/imageCarousel/browser/imageCarouselEditorInput.ts b/src/vs/workbench/contrib/imageCarousel/browser/imageCarouselEditorInput.ts
new file mode 100644
index 0000000000000..5d0b17ba2e524
--- /dev/null
+++ b/src/vs/workbench/contrib/imageCarousel/browser/imageCarouselEditorInput.ts
@@ -0,0 +1,55 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { EditorInput } from '../../../common/editor/editorInput.js';
+import { IUntypedEditorInput } from '../../../common/editor.js';
+import { URI } from '../../../../base/common/uri.js';
+import { Schemas } from '../../../../base/common/network.js';
+import { IImageCarouselCollection } from './imageCarouselTypes.js';
+
+export class ImageCarouselEditorInput extends EditorInput {
+	static readonly ID = 'workbench.input.imageCarousel';
+
+	private _resource: URI;
+	private _name: string;
+
+	constructor(
+		public readonly collection: IImageCarouselCollection,
+		public readonly startIndex: number = 0
+	) {
+		super();
+		this._resource = URI.from({
+			scheme: Schemas.vscodeImageCarousel,
+			path: `/${encodeURIComponent(collection.id)}`,
+		});
+		this._name = collection.title;
+	}
+
+	get typeId(): string {
+		return ImageCarouselEditorInput.ID;
+	}
+
+	get resource(): URI {
+		return this._resource;
+	}
+
+	override getName(): string {
+		return this._name;
+	}
+
+	setName(name: string): void {
+		if (this._name !== name) {
+			this._name = name;
+			this._onDidChangeLabel.fire();
+		}
+	}
+
+	override matches(other: EditorInput | IUntypedEditorInput): boolean {
+		if (other instanceof ImageCarouselEditorInput) {
+			return other.collection.id === this.collection.id;
+		}
+		return false;
+	}
+}
diff --git a/src/vs/workbench/contrib/imageCarousel/browser/imageCarouselTypes.ts b/src/vs/workbench/contrib/imageCarousel/browser/imageCarouselTypes.ts
new file mode 100644
index 0000000000000..cda9d2b23d8e1
--- /dev/null
+++ b/src/vs/workbench/contrib/imageCarousel/browser/imageCarouselTypes.ts
@@ -0,0 +1,28 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { URI } from '../../../../base/common/uri.js';
+import { VSBuffer } from '../../../../base/common/buffer.js';
+
+export interface ICarouselImage {
+	readonly id: string;
+	readonly name: string;
+	readonly mimeType: string;
+	readonly data: VSBuffer;
+	readonly uri?: URI;
+	readonly source?: string;
+	readonly caption?: string;
+}
+
+export interface ICarouselSection {
+	readonly title: string;
+	readonly images: ReadonlyArray<ICarouselImage>;
+}
+
+export interface IImageCarouselCollection {
+	readonly id: string;
+	readonly title: string;
+	readonly sections: ReadonlyArray<ICarouselSection>;
+}
diff --git a/src/vs/workbench/contrib/imageCarousel/browser/media/imageCarousel.css b/src/vs/workbench/contrib/imageCarousel/browser/media/imageCarousel.css
new file mode 100644
index 0000000000000..e555288162fe9
--- /dev/null
+++ b/src/vs/workbench/contrib/imageCarousel/browser/media/imageCarousel.css
@@ -0,0 +1,196 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+.image-carousel-editor {
+	width: 100%;
+	height: 100%;
+	display: flex;
+	flex-direction: column;
+	overflow: hidden;
+}
+
+.image-carousel-editor .empty-message {
+	display: flex;
+	align-items: center;
+	justify-content: center;
+	height: 100%;
+	color: var(--vscode-descriptionForeground);
+	font-size: 14px;
+}
+
+.image-carousel-editor .slideshow-container {
+	display: flex;
+	flex-direction: column;
+	height: 100%;
+	padding: 12px;
+	gap: 8px;
+	overflow: hidden;
+}
+
+.image-carousel-editor .slideshow-container:focus,
+.image-carousel-editor .slideshow-container:focus-visible {
+	outline: none !important;
+}
+
+/* Image viewing area */
+.image-carousel-editor .image-area {
+	flex: 1;
+	min-height: 0;
+	position: relative;
+	display: flex;
+	align-items: center;
+	justify-content: center;
+	overflow: hidden;
+	background-color: var(--vscode-editorWidget-background);
+	border-radius: 6px;
+}
+
+.image-carousel-editor .main-image-container {
+	width: 100%;
+	height: 100%;
+	display: flex;
+	align-items: center;
+	justify-content: center;
+	padding: 24px 48px;
+}
+
+.image-carousel-editor .main-image {
+	max-width: 100%;
+	max-height: 100%;
+	object-fit: contain;
+	border-radius: 4px;
+}
+
+/* Overlay navigation arrows */
+.image-carousel-editor .nav-arrow {
+	position: absolute;
+	top: 50%;
+	transform: translateY(-50%);
+	width: 32px;
+	height: 32px;
+	display: flex;
+	align-items: center;
+	justify-content: center;
+	background: var(--vscode-button-secondaryBackground);
+	color: var(--vscode-button-secondaryForeground);
+	border: none;
+	border-radius: 50%;
+	cursor: pointer;
+	opacity: 0;
+	transition: opacity 0.15s ease;
+	z-index: 1;
+}
+
+.monaco-workbench.monaco-reduce-motion .image-carousel-editor .nav-arrow {
+	transition: none;
+}
+.image-carousel-editor .image-area:hover .nav-arrow:not(:disabled) {
+	opacity: 0.8;
+}
+
+.image-carousel-editor .nav-arrow:hover:not(:disabled) {
+	opacity: 1 !important;
+	background: var(--vscode-button-background);
+	color: var(--vscode-button-foreground);
+}
+
+.image-carousel-editor .nav-arrow:disabled {
+	opacity: 0 !important;
+	cursor: default;
+	pointer-events: none;
+}
+
+.image-carousel-editor .nav-arrow.prev-arrow {
+	left: 8px;
+}
+
+.image-carousel-editor .nav-arrow.next-arrow {
+	right: 8px;
+}
+
+/* Bottom bar: caption + counter + thumbnails */
+.image-carousel-editor .bottom-bar {
+	display: flex;
+	flex-direction: column;
+	align-items: center;
+	gap: 2px;
+	padding: 4px 0 8px;
+	flex-shrink: 0;
+	min-width: 0;
+	max-width: 100%;
+}
+
+/* Extra gap before thumbnails */
+.image-carousel-editor .bottom-bar .sections-container {
+	margin-top: 4px;
+}
+
+/* Caption */
+.image-carousel-editor .image-caption {
+	text-align: center;
+	color: var(--vscode-descriptionForeground);
+	font-size: 12px;
+	padding: 0 24px;
+}
+
+/* Sections container — flat horizontal thumbnail strip */
+.image-carousel-editor .sections-container {
+	display: flex;
+	flex-direction: row;
+	align-items: center;
+	gap: 6px;
+	overflow-x: auto;
+	justify-content: center;
+	justify-content: safe center;
+	padding: 0;
+	flex-shrink: 0;
+	min-width: 0;
+	max-width: 100%;
+	scrollbar-width: none;
+}
+
+.image-carousel-editor .sections-container::-webkit-scrollbar {
+	display: none;
+}
+
+/* Subtle separator between sections */
+.image-carousel-editor .thumbnail-separator {
+	width: 1px;
+	height: 24px;
+	background: var(--vscode-editorWidget-border, var(--vscode-widget-border));
+	opacity: 0.4;
+	flex-shrink: 0;
+	margin: 0 6px;
+}
+
+.image-carousel-editor .thumbnail {
+	width: 48px;
+	height: 48px;
+	border: 2px solid transparent;
+	border-radius: 4px;
+	overflow: hidden;
+	cursor: pointer;
+	transition: border-color 0.15s ease, opacity 0.15s ease;
+	flex-shrink: 0;
+	opacity: 0.6;
+	padding: 0;
+	background: none;
+}
+
+.image-carousel-editor .thumbnail:hover {
+	opacity: 1;
+	border-color: var(--vscode-focusBorder);
+}
+
+.image-carousel-editor .thumbnail.active {
+	opacity: 1;
+	border-color: var(--vscode-focusBorder);
+}
+
+.image-carousel-editor .thumbnail-image {
+	width: 100%;
+	height: 100%;
+	object-fit: cover;
+}
diff --git a/src/vs/workbench/contrib/imageCarousel/test/browser/imageCarousel.contribution.test.ts b/src/vs/workbench/contrib/imageCarousel/test/browser/imageCarousel.contribution.test.ts
new file mode 100644
index 0000000000000..fc95cb683955d
--- /dev/null
+++ b/src/vs/workbench/contrib/imageCarousel/test/browser/imageCarousel.contribution.test.ts
@@ -0,0 +1,390 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { URI } from '../../../../../base/common/uri.js';
+import { VSBuffer } from '../../../../../base/common/buffer.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { TestInstantiationService } from '../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import { workbenchInstantiationService } from '../../../../test/browser/workbenchTestServices.js';
+import { NullFilesConfigurationService, createFileStat } from '../../../../test/common/workbenchTestServices.js';
+import { IExplorerService } from '../../../files/browser/files.js';
+import { ExplorerItem } from '../../../files/common/explorerModel.js';
+import { IFileService, IFileStat, IFileContent } from '../../../../../platform/files/common/files.js';
+import { IEditorService, MODAL_GROUP } from '../../../../services/editor/common/editorService.js';
+import { ImageCarouselEditorInput } from '../../browser/imageCarouselEditorInput.js';
+import { TestConfigurationService } from '../../../../../platform/configuration/test/common/testConfigurationService.js';
+import { INotificationService } from '../../../../../platform/notification/common/notification.js';
+import { IWorkspaceContextService } from '../../../../../platform/workspace/common/workspace.js';
+
+// Importing the contribution registers the actions
+import '../../browser/imageCarousel.contribution.js';
+
+function createExplorerItem(
+	path: string,
+	isFolder: boolean,
+	fileService: IFileService,
+	configService: TestConfigurationService,
+	parent?: ExplorerItem,
+): ExplorerItem {
+	return new ExplorerItem(
+		URI.file(path),
+		fileService,
+		configService,
+		NullFilesConfigurationService,
+		parent,
+		isFolder,
+	);
+}
+
+suite('OpenImagesInCarouselFromExplorerAction', () => {
+	const disposables = ensureNoDisposablesAreLeakedInTestSuite();
+
+	let instantiationService: TestInstantiationService;
+	let configService: TestConfigurationService;
+	let openedInputs: { input: ImageCarouselEditorInput; group: typeof MODAL_GROUP }[];
+	let infoMessages: string[];
+	let errorMessages: string[];
+
+	setup(() => {
+		openedInputs = [];
+		infoMessages = [];
+		errorMessages = [];
+		configService = new TestConfigurationService();
+		instantiationService = workbenchInstantiationService(undefined, disposables);
+	});
+
+	function stubFileService(resolveMap: Map<string, IFileStat>, fileContents: Map<string, VSBuffer>): void {
+		instantiationService.stub(IFileService, 'resolve', async (resource: URI) => {
+			const stat = resolveMap.get(resource.path);
+			if (!stat) {
+				throw new Error(`File not found: ${resource.path}`);
+			}
+			return stat;
+		});
+
+		instantiationService.stub(IFileService, 'readFile', async (resource: URI) => {
+			const content = fileContents.get(resource.path);
+			if (!content) {
+				throw new Error(`Cannot read: ${resource.path}`);
+			}
+			return { resource, value: content } as IFileContent;
+		});
+	}
+
+	function stubExplorerService(items: ExplorerItem[]): void {
+		instantiationService.stub(IExplorerService, {
+			getContext: () => items,
+		});
+	}
+
+	function stubEditorService(): void {
+		instantiationService.stub(IEditorService, 'openEditor', async (input: unknown, _options: unknown, group: unknown) => {
+			if (input instanceof ImageCarouselEditorInput) {
+				openedInputs.push({ input, group: group as typeof MODAL_GROUP });
+				disposables.add(input);
+			}
+			return undefined;
+		});
+	}
+
+	function stubNotificationService(): void {
+		instantiationService.stub(INotificationService, 'info', (message: string) => {
+			infoMessages.push(message);
+		});
+		instantiationService.stub(INotificationService, 'error', (message: string) => {
+			errorMessages.push(message);
+		});
+	}
+
+	test('single image file opens carousel with sibling images', async () => {
+		const fileService = instantiationService.get(IFileService);
+		const parent = createExplorerItem('/workspace/images', true, fileService, configService);
+		const imageItem = createExplorerItem('/workspace/images/photo.png', false, fileService, configService, parent);
+
+		const pngData = VSBuffer.fromString('fake-png');
+		const jpgData = VSBuffer.fromString('fake-jpg');
+		const txtData = VSBuffer.fromString('text file');
+
+		const resolveMap = new Map<string, IFileStat>();
+		resolveMap.set('/workspace/images', createFileStat(
+			URI.file('/workspace/images'), false, false, true, false, [
+			{ resource: URI.file('/workspace/images/photo.png'), isFile: true },
+			{ resource: URI.file('/workspace/images/other.jpg'), isFile: true },
+			{ resource: URI.file('/workspace/images/readme.txt'), isFile: true },
+			{ resource: URI.file('/workspace/images/subfolder'), isDirectory: true, isFile: false },
+		]
+		));
+
+		const fileContents = new Map<string, VSBuffer>();
+		fileContents.set('/workspace/images/photo.png', pngData);
+		fileContents.set('/workspace/images/other.jpg', jpgData);
+		fileContents.set('/workspace/images/readme.txt', txtData);
+
+		stubFileService(resolveMap, fileContents);
+		stubExplorerService([imageItem]);
+		stubEditorService();
+
+		const { CommandsRegistry } = await import('../../../../../platform/commands/common/commands.js');
+		const command = CommandsRegistry.getCommand('workbench.action.openImagesInCarousel');
+		assert.ok(command, 'Command should be registered');
+
+		await instantiationService.invokeFunction(command.handler);
+
+		assert.strictEqual(openedInputs.length, 1, 'Should open one editor');
+		const input = openedInputs[0].input;
+		assert.strictEqual(input.collection.sections.length, 1);
+
+		const images = input.collection.sections[0].images;
+		assert.strictEqual(images.length, 2, 'Should include 2 image siblings (png + jpg), not txt');
+		// Images are sorted by basename: other.jpg before photo.png
+		assert.strictEqual(images[0].name, 'other.jpg');
+		assert.strictEqual(images[1].name, 'photo.png');
+
+		// Start index should be the selected image (photo.png = index 1 after sorting)
+		assert.strictEqual(input.startIndex, 1);
+	});
+
+	test('folder opens carousel with all contained images', async () => {
+		const fileService = instantiationService.get(IFileService);
+		const folderItem = createExplorerItem('/workspace/images', true, fileService, configService);
+
+		const gifData = VSBuffer.fromString('fake-gif');
+		const webpData = VSBuffer.fromString('fake-webp');
+
+		const resolveMap = new Map<string, IFileStat>();
+		resolveMap.set('/workspace/images', createFileStat(
+			URI.file('/workspace/images'), false, false, true, false, [
+			{ resource: URI.file('/workspace/images/anim.gif'), isFile: true },
+			{ resource: URI.file('/workspace/images/photo.webp'), isFile: true },
+			{ resource: URI.file('/workspace/images/script.js'), isFile: true },
+		]
+		));
+
+		const fileContents = new Map<string, VSBuffer>();
+		fileContents.set('/workspace/images/anim.gif', gifData);
+		fileContents.set('/workspace/images/photo.webp', webpData);
+
+		stubFileService(resolveMap, fileContents);
+		stubExplorerService([folderItem]);
+		stubEditorService();
+
+		const { CommandsRegistry } = await import('../../../../../platform/commands/common/commands.js');
+		const command = CommandsRegistry.getCommand('workbench.action.openImagesInCarousel');
+		assert.ok(command);
+
+		await instantiationService.invokeFunction(command.handler);
+
+		assert.strictEqual(openedInputs.length, 1);
+		const images = openedInputs[0].input.collection.sections[0].images;
+		assert.strictEqual(images.length, 2, 'Should include 2 images (gif + webp), not js');
+		assert.strictEqual(images[0].name, 'anim.gif');
+		assert.strictEqual(images[1].name, 'photo.webp');
+	});
+
+	test('multiple selected images open in carousel', async () => {
+		const fileService = instantiationService.get(IFileService);
+		const img1 = createExplorerItem('/workspace/a.png', false, fileService, configService);
+		const img2 = createExplorerItem('/workspace/b.svg', false, fileService, configService);
+		const txtFile = createExplorerItem('/workspace/notes.txt', false, fileService, configService);
+
+		const pngData = VSBuffer.fromString('fake-png');
+		const svgData = VSBuffer.fromString('<svg></svg>');
+
+		const resolveMap = new Map<string, IFileStat>();
+
+		const fileContents = new Map<string, VSBuffer>();
+		fileContents.set('/workspace/a.png', pngData);
+		fileContents.set('/workspace/b.svg', svgData);
+
+		stubFileService(resolveMap, fileContents);
+		stubExplorerService([img1, img2, txtFile]);
+		stubEditorService();
+
+		const { CommandsRegistry } = await import('../../../../../platform/commands/common/commands.js');
+		const command = CommandsRegistry.getCommand('workbench.action.openImagesInCarousel');
+		assert.ok(command);
+
+		await instantiationService.invokeFunction(command.handler);
+
+		assert.strictEqual(openedInputs.length, 1);
+		const images = openedInputs[0].input.collection.sections[0].images;
+		assert.strictEqual(images.length, 2, 'Should include only image files');
+		assert.strictEqual(images[0].name, 'a.png');
+		assert.strictEqual(images[1].name, 'b.svg');
+	});
+
+	test('empty selection with resource argument opens carousel from that folder', async () => {
+		const pngData = VSBuffer.fromString('fake-png');
+		const jpgData = VSBuffer.fromString('fake-jpg');
+
+		const folderUri = URI.file('/workspace/photos');
+		const resolveMap = new Map<string, IFileStat>();
+		resolveMap.set('/workspace/photos', createFileStat(
+			folderUri, false, false, true, false, [
+			{ resource: URI.file('/workspace/photos/sunset.png'), isFile: true },
+			{ resource: URI.file('/workspace/photos/mountain.jpg'), isFile: true },
+			{ resource: URI.file('/workspace/photos/notes.txt'), isFile: true },
+		]
+		));
+
+		const fileContents = new Map<string, VSBuffer>();
+		fileContents.set('/workspace/photos/sunset.png', pngData);
+		fileContents.set('/workspace/photos/mountain.jpg', jpgData);
+
+		stubFileService(resolveMap, fileContents);
+		stubExplorerService([]);
+		stubEditorService();
+
+		const { CommandsRegistry } = await import('../../../../../platform/commands/common/commands.js');
+		const command = CommandsRegistry.getCommand('workbench.action.openImagesInCarousel');
+		assert.ok(command);
+
+		// Pass the folder URI as the resource argument (as explorer does for empty-space click)
+		await instantiationService.invokeFunction(command.handler, folderUri);
+
+		assert.strictEqual(openedInputs.length, 1, 'Should open carousel using resource argument fallback');
+		const images = openedInputs[0].input.collection.sections[0].images;
+		assert.strictEqual(images.length, 2, 'Should include 2 images from the folder');
+	});
+
+	test('empty selection without resource falls back to first workspace folder', async () => {
+		const pngData = VSBuffer.fromString('fake-png');
+
+		// Derive the workspace root from IWorkspaceContextService so the test
+		// works on all platforms (the path differs on Windows vs Unix).
+		const contextService = instantiationService.get(IWorkspaceContextService);
+		const wsRoot = contextService.getWorkspace().folders[0].uri;
+		const logoUri = URI.joinPath(wsRoot, 'logo.png');
+		const readmeUri = URI.joinPath(wsRoot, 'readme.md');
+
+		const resolveMap = new Map<string, IFileStat>();
+		resolveMap.set(wsRoot.path, createFileStat(
+			wsRoot, false, false, true, false, [
+			{ resource: logoUri, isFile: true },
+			{ resource: readmeUri, isFile: true },
+		]
+		));
+
+		const fileContents = new Map<string, VSBuffer>();
+		fileContents.set(logoUri.path, pngData);
+
+		stubFileService(resolveMap, fileContents);
+		stubExplorerService([]);
+		stubEditorService();
+
+		const { CommandsRegistry } = await import('../../../../../platform/commands/common/commands.js');
+		const command = CommandsRegistry.getCommand('workbench.action.openImagesInCarousel');
+		assert.ok(command);
+
+		// No resource argument — should fall back to workspace root
+		await instantiationService.invokeFunction(command.handler);
+
+		assert.strictEqual(openedInputs.length, 1, 'Should open carousel using workspace root fallback');
+		const images = openedInputs[0].input.collection.sections[0].images;
+		assert.strictEqual(images.length, 1, 'Should include image from workspace root');
+		assert.strictEqual(images[0].name, 'logo.png');
+	});
+
+	test('empty selection with no images shows notification', async () => {
+		const folderUri = URI.file('/workspace/docs');
+		const resolveMap = new Map<string, IFileStat>();
+		resolveMap.set('/workspace/docs', createFileStat(
+			folderUri, false, false, true, false, [
+			{ resource: URI.file('/workspace/docs/readme.md'), isFile: true },
+		]
+		));
+
+		stubFileService(resolveMap, new Map());
+		stubExplorerService([]);
+		stubEditorService();
+		stubNotificationService();
+
+		const { CommandsRegistry } = await import('../../../../../platform/commands/common/commands.js');
+		const command = CommandsRegistry.getCommand('workbench.action.openImagesInCarousel');
+		assert.ok(command);
+
+		await instantiationService.invokeFunction(command.handler, folderUri);
+
+		assert.strictEqual(openedInputs.length, 0, 'Should not open carousel when folder has no images');
+		assert.strictEqual(infoMessages.length, 1, 'Should show notification');
+	});
+
+	test('folder with no images shows notification', async () => {
+		const fileService = instantiationService.get(IFileService);
+		const folderItem = createExplorerItem('/workspace/docs', true, fileService, configService);
+
+		const resolveMap = new Map<string, IFileStat>();
+		resolveMap.set('/workspace/docs', createFileStat(
+			URI.file('/workspace/docs'), false, false, true, false, [
+			{ resource: URI.file('/workspace/docs/readme.md'), isFile: true },
+			{ resource: URI.file('/workspace/docs/notes.txt'), isFile: true },
+		]
+		));
+
+		stubFileService(resolveMap, new Map());
+		stubExplorerService([folderItem]);
+		stubEditorService();
+		stubNotificationService();
+
+		const { CommandsRegistry } = await import('../../../../../platform/commands/common/commands.js');
+		const command = CommandsRegistry.getCommand('workbench.action.openImagesInCarousel');
+		assert.ok(command);
+
+		await instantiationService.invokeFunction(command.handler);
+
+		assert.strictEqual(openedInputs.length, 0, 'Should not open carousel when folder has no images');
+		assert.strictEqual(infoMessages.length, 1, 'Should show notification about no images');
+	});
+
+	test('folder read error shows error notification', async () => {
+		const fileService = instantiationService.get(IFileService);
+		const folderItem = createExplorerItem('/workspace/restricted', true, fileService, configService);
+
+		// resolve throws to simulate a permission error
+		const resolveMap = new Map<string, IFileStat>();
+		stubFileService(resolveMap, new Map());
+		stubExplorerService([folderItem]);
+		stubEditorService();
+		stubNotificationService();
+
+		const { CommandsRegistry } = await import('../../../../../platform/commands/common/commands.js');
+		const command = CommandsRegistry.getCommand('workbench.action.openImagesInCarousel');
+		assert.ok(command);
+
+		await instantiationService.invokeFunction(command.handler);
+
+		assert.strictEqual(openedInputs.length, 0, 'Should not open carousel on folder read error');
+		assert.strictEqual(errorMessages.length, 1, 'Should show error notification');
+		assert.strictEqual(infoMessages.length, 0, 'Should not show info notification');
+	});
+
+	test('all image reads failing shows error notification', async () => {
+		const folderUri = URI.file('/workspace/broken');
+
+		const resolveMap = new Map<string, IFileStat>();
+		resolveMap.set('/workspace/broken', createFileStat(
+			folderUri, false, false, true, false, [
+			{ resource: URI.file('/workspace/broken/corrupt.png'), isFile: true },
+			{ resource: URI.file('/workspace/broken/missing.jpg'), isFile: true },
+		]
+		));
+
+		// No file contents → all readFile calls will fail
+		stubFileService(resolveMap, new Map());
+		stubExplorerService([]);
+		stubEditorService();
+		stubNotificationService();
+
+		const { CommandsRegistry } = await import('../../../../../platform/commands/common/commands.js');
+		const command = CommandsRegistry.getCommand('workbench.action.openImagesInCarousel');
+		assert.ok(command);
+
+		await instantiationService.invokeFunction(command.handler, folderUri);
+
+		assert.strictEqual(openedInputs.length, 0, 'Should not open carousel when all reads fail');
+		assert.strictEqual(errorMessages.length, 1, 'Should show error notification for read failures');
+	});
+});
diff --git a/src/vs/workbench/contrib/inlineChat/browser/inlineChat.contribution.ts b/src/vs/workbench/contrib/inlineChat/browser/inlineChat.contribution.ts
index 2220f7d147462..e5ad9450dc1e0 100644
--- a/src/vs/workbench/contrib/inlineChat/browser/inlineChat.contribution.ts
+++ b/src/vs/workbench/contrib/inlineChat/browser/inlineChat.contribution.ts
@@ -30,6 +30,8 @@ registerAction2(InlineChatActions.KeepSessionAction2);
 registerAction2(InlineChatActions.UndoSessionAction2);
 registerAction2(InlineChatActions.UndoAndCloseSessionAction2);
 registerAction2(InlineChatActions.CancelSessionAction);
+registerAction2(InlineChatActions.ContinueInlineChatInChatViewAction);
+registerAction2(InlineChatActions.RephraseInlineChatSessionAction);
 
 // --- browser
 
@@ -96,6 +98,7 @@ registerAction2(InlineChatActions.SubmitInlineChatInputAction);
 registerAction2(InlineChatActions.QueueInChatAction);
 registerAction2(InlineChatActions.HideInlineChatInputAction);
 registerAction2(InlineChatActions.FixDiagnosticsAction);
+registerAction2(InlineChatActions.DismissEditorAffordanceAction);
 
 
 const workbenchContributionsRegistry = Registry.as<IWorkbenchContributionsRegistry>(WorkbenchExtensions.Workbench);
diff --git a/src/vs/workbench/contrib/inlineChat/browser/inlineChatActions.ts b/src/vs/workbench/contrib/inlineChat/browser/inlineChatActions.ts
index 3007bac0d9158..e9b4077989b1a 100644
--- a/src/vs/workbench/contrib/inlineChat/browser/inlineChatActions.ts
+++ b/src/vs/workbench/contrib/inlineChat/browser/inlineChatActions.ts
@@ -11,12 +11,12 @@ import { EmbeddedDiffEditorWidget } from '../../../../editor/browser/widget/diff
 import { EmbeddedCodeEditorWidget } from '../../../../editor/browser/widget/codeEditor/embeddedCodeEditorWidget.js';
 import { EditorContextKeys } from '../../../../editor/common/editorContextKeys.js';
 import { InlineChatController, InlineChatRunOptions } from './inlineChatController.js';
-import { ACTION_ACCEPT_CHANGES, ACTION_ASK_IN_CHAT, CTX_INLINE_CHAT_FOCUSED, CTX_INLINE_CHAT_VISIBLE, CTX_INLINE_CHAT_OUTER_CURSOR_POSITION, CTX_INLINE_CHAT_POSSIBLE, ACTION_START, CTX_INLINE_CHAT_V2_ENABLED, CTX_INLINE_CHAT_V1_ENABLED, CTX_HOVER_MODE, CTX_INLINE_CHAT_INPUT_HAS_TEXT, CTX_INLINE_CHAT_FILE_BELONGS_TO_CHAT, CTX_INLINE_CHAT_INPUT_WIDGET_FOCUSED, InlineChatConfigKeys, CTX_FIX_DIAGNOSTICS_ENABLED } from '../common/inlineChat.js';
+import { ACTION_ACCEPT_CHANGES, ACTION_ASK_IN_CHAT, CTX_INLINE_CHAT_FOCUSED, CTX_INLINE_CHAT_VISIBLE, CTX_INLINE_CHAT_OUTER_CURSOR_POSITION, CTX_INLINE_CHAT_POSSIBLE, ACTION_START, CTX_INLINE_CHAT_V2_ENABLED, CTX_INLINE_CHAT_V1_ENABLED, CTX_HOVER_MODE, CTX_INLINE_CHAT_INPUT_HAS_TEXT, CTX_INLINE_CHAT_FILE_BELONGS_TO_CHAT, CTX_INLINE_CHAT_INPUT_WIDGET_FOCUSED, CTX_INLINE_CHAT_PENDING_CONFIRMATION, CTX_INLINE_CHAT_TERMINATED, InlineChatConfigKeys, CTX_FIX_DIAGNOSTICS_ENABLED, CTX_INLINE_CHAT_AFFORDANCE_VISIBLE } from '../common/inlineChat.js';
 import { ctxHasEditorModification, ctxHasRequestInProgress } from '../../chat/browser/chatEditing/chatEditingEditorContextKeys.js';
 import { localize, localize2 } from '../../../../nls.js';
 import { Action2, IAction2Options, MenuId, MenuRegistry } from '../../../../platform/actions/common/actions.js';
 import { ContextKeyExpr, IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
-import { IInstantiationService, ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
+import { ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
 import { KeybindingWeight } from '../../../../platform/keybinding/common/keybindingsRegistry.js';
 import { IEditorService } from '../../../services/editor/common/editorService.js';
 import { ICodeEditorService } from '../../../../editor/browser/services/codeEditorService.js';
@@ -29,6 +29,7 @@ import { IConfigurationService } from '../../../../platform/configuration/common
 import { IChatEditingService } from '../../chat/common/editing/chatEditingService.js';
 import { IChatWidgetService } from '../../chat/browser/chat.js';
 import { ChatRequestQueueKind } from '../../chat/common/chatService/chatService.js';
+import { ChatEntitlementContextKeys } from '../../../services/chat/common/chatEntitlementService.js';
 
 
 CommandsRegistry.registerCommandAlias('interactiveEditor.start', 'inlineChat.start');
@@ -37,16 +38,6 @@ CommandsRegistry.registerCommandAlias('interactive.acceptChanges', ACTION_ACCEPT
 
 export const START_INLINE_CHAT = registerIcon('start-inline-chat', Codicon.sparkle, localize('startInlineChat', 'Icon which spawns the inline chat from the editor toolbar.'));
 
-// some gymnastics to enable hold for speech without moving the StartSessionAction into the electron-layer
-
-export interface IHoldForSpeech {
-	(accessor: ServicesAccessor, controller: InlineChatController, source: Action2): void;
-}
-let _holdForSpeech: IHoldForSpeech | undefined = undefined;
-export function setHoldForSpeech(holdForSpeech: IHoldForSpeech) {
-	_holdForSpeech = holdForSpeech;
-}
-
 const inlineChatContextKey = ContextKeyExpr.and(
 	ContextKeyExpr.or(CTX_INLINE_CHAT_V1_ENABLED, CTX_INLINE_CHAT_V2_ENABLED),
 	CTX_INLINE_CHAT_POSSIBLE,
@@ -114,10 +105,6 @@ export class StartSessionAction extends Action2 {
 			return;
 		}
 
-		if (_holdForSpeech) {
-			accessor.get(IInstantiationService).invokeFunction(_holdForSpeech, ctrl, this);
-		}
-
 		let options: InlineChatRunOptions | undefined;
 		const arg = args[0];
 		if (arg && InlineChatRunOptions.isInlineChatRunOptions(arg)) {
@@ -144,7 +131,7 @@ export class StartSessionAction extends Action2 {
 MenuRegistry.appendMenuItem(MenuId.InlineChatEditorAffordance, {
 	group: '0_chat',
 	order: 1,
-	when: ContextKeyExpr.and(EditorContextKeys.writable, EditorContextKeys.hasNonEmptySelection, CTX_INLINE_CHAT_FILE_BELONGS_TO_CHAT.negate()),
+	when: ContextKeyExpr.and(EditorContextKeys.writable, EditorContextKeys.hasNonEmptySelection, CTX_INLINE_CHAT_FILE_BELONGS_TO_CHAT.negate(), ChatEntitlementContextKeys.Setup.hidden.negate()),
 	command: {
 		id: ACTION_START,
 		title: localize('editCode', "Ask for Edits"),
@@ -253,7 +240,7 @@ export class FixDiagnosticsAction extends AbstractInlineChatAction {
 			id: 'inlineChat.fixDiagnostics',
 			title: localize2('fix', 'Fix'),
 			icon: Codicon.editSparkle,
-			precondition: ContextKeyExpr.and(inlineChatContextKey, CTX_FIX_DIAGNOSTICS_ENABLED, EditorContextKeys.selectionHasDiagnostics, CTX_INLINE_CHAT_FILE_BELONGS_TO_CHAT.negate()),
+			precondition: ContextKeyExpr.and(CTX_FIX_DIAGNOSTICS_ENABLED, EditorContextKeys.selectionHasDiagnostics, CTX_INLINE_CHAT_FILE_BELONGS_TO_CHAT.negate()),
 			menu: [{
 				id: MenuId.InlineChatEditorAffordance,
 				group: '1_quickfix',
@@ -269,6 +256,7 @@ export class FixDiagnosticsAction extends AbstractInlineChatAction {
 	}
 
 	override runInlineChatCommand(_accessor: ServicesAccessor, ctrl: InlineChatController, _editor: ICodeEditor, ..._args: unknown[]): void {
+		ctrl.inputWidget.hide();
 		ctrl.run({ autoSend: true, attachDiagnostics: true });
 	}
 }
@@ -364,7 +352,7 @@ export class UndoAndCloseSessionAction2 extends KeepOrUndoSessionAction {
 			title: localize2('close2', "Close"),
 			f1: true,
 			icon: Codicon.close,
-			precondition: ContextKeyExpr.and(CTX_INLINE_CHAT_VISIBLE, CTX_HOVER_MODE.negate()),
+			precondition: ContextKeyExpr.and(CTX_INLINE_CHAT_VISIBLE),
 			keybinding: [{
 				when: ContextKeyExpr.or(
 					ContextKeyExpr.and(EditorContextKeys.focus, ctxHasEditorModification.negate()),
@@ -379,7 +367,8 @@ export class UndoAndCloseSessionAction2 extends KeepOrUndoSessionAction {
 				order: 100,
 				when: ContextKeyExpr.or(
 					CTX_HOVER_MODE.negate(),
-					ContextKeyExpr.and(CTX_HOVER_MODE, ctxHasEditorModification.negate(), ctxHasRequestInProgress.negate())
+					ContextKeyExpr.and(CTX_HOVER_MODE, ctxHasEditorModification.negate(), ctxHasRequestInProgress.negate()),
+					ContextKeyExpr.and(CTX_HOVER_MODE, CTX_INLINE_CHAT_PENDING_CONFIRMATION)
 				)
 			}]
 		});
@@ -405,10 +394,53 @@ export class CancelSessionAction extends KeepOrUndoSessionAction {
 				id: MenuId.ChatEditorInlineExecute,
 				group: 'navigation',
 				order: 100,
-				when: ctxHasRequestInProgress
+				when: ContextKeyExpr.and(CTX_HOVER_MODE, ctxHasRequestInProgress)
+			}]
+		});
+	}
+}
+
+export class ContinueInlineChatInChatViewAction extends AbstractInlineChatAction {
+
+	constructor() {
+		super({
+			id: 'inlineChat2.continueInChat',
+			title: localize2('continueInChat', "Ask in Chat"),
+			icon: Codicon.chatSparkle,
+			precondition: ContextKeyExpr.and(CTX_INLINE_CHAT_VISIBLE, CTX_HOVER_MODE, CTX_INLINE_CHAT_TERMINATED),
+			menu: [{
+				id: MenuId.ChatEditorInlineExecute,
+				group: 'navigation',
+				order: 2,
+				when: ContextKeyExpr.and(CTX_HOVER_MODE, CTX_INLINE_CHAT_TERMINATED)
 			}]
 		});
 	}
+
+	override async runInlineChatCommand(_accessor: ServicesAccessor, ctrl: InlineChatController, _editor: ICodeEditor): Promise<void> {
+		await ctrl.continueSessionInChat();
+	}
+}
+
+export class RephraseInlineChatSessionAction extends AbstractInlineChatAction {
+
+	constructor() {
+		super({
+			id: 'inlineChat2.rephrase',
+			title: localize2('rephrase', "Rephrase"),
+			precondition: ContextKeyExpr.and(CTX_INLINE_CHAT_VISIBLE, CTX_HOVER_MODE, CTX_INLINE_CHAT_TERMINATED),
+			menu: [{
+				id: MenuId.ChatEditorInlineExecute,
+				group: 'navigation',
+				order: 1,
+				when: ContextKeyExpr.and(CTX_HOVER_MODE, CTX_INLINE_CHAT_TERMINATED)
+			}]
+		});
+	}
+
+	override async runInlineChatCommand(_accessor: ServicesAccessor, ctrl: InlineChatController, _editor: ICodeEditor): Promise<void> {
+		await ctrl.rephraseSession();
+	}
 }
 
 export class SubmitInlineChatInputAction extends AbstractInlineChatAction {
@@ -505,6 +537,26 @@ export class AskInChatAction extends EditorAction2 {
 	}
 }
 
+export class DismissEditorAffordanceAction extends EditorAction2 {
+
+	constructor() {
+		super({
+			id: 'inlineChat.dismissEditorAffordance',
+			title: localize2('dismissAffordance', "Dismiss Editor Affordance"),
+			precondition: ContextKeyExpr.and(CTX_INLINE_CHAT_AFFORDANCE_VISIBLE, ContextKeyExpr.equals('config.inlineChat.affordance', 'editor')),
+			keybinding: {
+				when: EditorContextKeys.editorTextFocus,
+				weight: KeybindingWeight.EditorContrib,
+				primary: KeyCode.Escape,
+			}
+		});
+	}
+
+	override runEditorCommand(_accessor: ServicesAccessor, editor: ICodeEditor): void {
+		InlineChatController.get(editor)?.inputOverlayWidget.dismiss();
+	}
+}
+
 export class QueueInChatAction extends AbstractInlineChatAction {
 
 
diff --git a/src/vs/workbench/contrib/inlineChat/browser/inlineChatAffordance.ts b/src/vs/workbench/contrib/inlineChat/browser/inlineChatAffordance.ts
index 4e3cf4c660003..9b849b7de8b0a 100644
--- a/src/vs/workbench/contrib/inlineChat/browser/inlineChatAffordance.ts
+++ b/src/vs/workbench/contrib/inlineChat/browser/inlineChatAffordance.ts
@@ -9,7 +9,7 @@ import { ICodeEditor } from '../../../../editor/browser/editorBrowser.js';
 import { observableCodeEditor } from '../../../../editor/browser/observableCodeEditor.js';
 import { ScrollType } from '../../../../editor/common/editorCommon.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
-import { InlineChatConfigKeys } from '../common/inlineChat.js';
+import { InlineChatConfigKeys, CTX_INLINE_CHAT_AFFORDANCE_VISIBLE } from '../common/inlineChat.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { observableConfigValue } from '../../../../platform/observable/common/platformObservableUtils.js';
 import { IChatEntitlementService } from '../../../services/chat/common/chatEntitlementService.js';
@@ -24,6 +24,7 @@ import { CodeActionController } from '../../../../editor/contrib/codeAction/brow
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
 import { generateUuid } from '../../../../base/common/uuid.js';
 import { Event } from '../../../../base/common/event.js';
+import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
 
 type InlineChatAffordanceEvent = {
 	mode: string;
@@ -44,7 +45,8 @@ export class InlineChatAffordance extends Disposable {
 	readonly #editor: ICodeEditor;
 	readonly #inputWidget: InlineChatInputWidget;
 	readonly #instantiationService: IInstantiationService;
-	readonly #menuData = observableValue<{ rect: DOMRect; above: boolean; lineNumber: number; placeholder: string } | undefined>(this, undefined);
+	readonly #menuData = observableValue<{ rect: DOMRect; above: boolean; lineNumber: number; placeholder: string; value?: string } | undefined>(this, undefined);
+	readonly #selectionData = observableValue<Selection | undefined>(this, undefined);
 
 	constructor(
 		editor: ICodeEditor,
@@ -54,6 +56,7 @@ export class InlineChatAffordance extends Disposable {
 		@IChatEntitlementService chatEntiteldService: IChatEntitlementService,
 		@IInlineChatSessionService inlineChatSessionService: IInlineChatSessionService,
 		@ITelemetryService telemetryService: ITelemetryService,
+		@IContextKeyService contextKeyService: IContextKeyService,
 	) {
 		super();
 		this.#editor = editor;
@@ -64,7 +67,10 @@ export class InlineChatAffordance extends Disposable {
 		const affordance = observableConfigValue<'off' | 'gutter' | 'editor'>(InlineChatConfigKeys.Affordance, 'off', configurationService);
 		const debouncedSelection = debouncedObservable(editorObs.cursorSelection, 500);
 
-		const selectionData = observableValue<Selection | undefined>(this, undefined);
+		const selectionData = this.#selectionData;
+
+		const ctxAffordanceVisible = CTX_INLINE_CHAT_AFFORDANCE_VISIBLE.bindTo(contextKeyService);
+		this._store.add({ dispose: () => ctxAffordanceVisible.reset() });
 
 		let explicitSelection = false;
 		let affordanceId: string | undefined;
@@ -114,6 +120,19 @@ export class InlineChatAffordance extends Disposable {
 			selectionData.set(undefined, undefined);
 		}));
 
+		// Hide when the editor loses focus (e.g., switching tabs in notebooks)
+		this._store.add(autorun(r => {
+			if (!editorObs.isFocused.read(r)) {
+				selectionData.set(undefined, undefined);
+			}
+		}));
+
+		this._store.add(autorun(r => {
+			const sel = selectionData.read(r);
+			const mode = affordance.read(r);
+			ctxAffordanceVisible.set(sel !== undefined && (mode === 'editor' || mode === 'gutter'));
+		}));
+
 		const gutterAffordance = this._store.add(this.#instantiationService.createInstance(
 			InlineChatGutterAffordance,
 			editorObs,
@@ -156,7 +175,7 @@ export class InlineChatAffordance extends Disposable {
 			const left = data.rect.left - editorRect.left;
 
 			// Show the overlay widget
-			this.#inputWidget.show(data.lineNumber, left, data.above, data.placeholder);
+			this.#inputWidget.show(data.lineNumber, left, data.above, data.placeholder, data.value);
 		}));
 
 		this._store.add(autorun(r => {
@@ -167,7 +186,11 @@ export class InlineChatAffordance extends Disposable {
 		}));
 	}
 
-	async showMenuAtSelection(placeholder: string): Promise<void> {
+	dismiss(): void {
+		this.#selectionData.set(undefined, undefined);
+	}
+
+	async showMenuAtSelection(placeholder: string, value?: string): Promise<void> {
 		assertType(this.#editor.hasModel());
 
 		const direction = this.#editor.getSelection().getDirection();
@@ -182,7 +205,8 @@ export class InlineChatAffordance extends Disposable {
 			rect: new DOMRect(x, y, 0, scrolledPosition.height),
 			above: direction === SelectionDirection.RTL,
 			lineNumber: position.lineNumber,
-			placeholder
+			placeholder,
+			value
 		}, undefined);
 
 		await waitForState(this.#inputWidget.position, pos => pos === null);
diff --git a/src/vs/workbench/contrib/inlineChat/browser/inlineChatController.ts b/src/vs/workbench/contrib/inlineChat/browser/inlineChatController.ts
index 8cbb1326de4e2..00280f3828d18 100644
--- a/src/vs/workbench/contrib/inlineChat/browser/inlineChatController.ts
+++ b/src/vs/workbench/contrib/inlineChat/browser/inlineChatController.ts
@@ -51,10 +51,10 @@ import { isNotebookContainingCellEditor as isNotebookWithCellEditor } from '../.
 import { INotebookEditorService } from '../../notebook/browser/services/notebookEditorService.js';
 import { CellUri, ICellEditOperation } from '../../notebook/common/notebookCommon.js';
 import { INotebookService } from '../../notebook/common/notebookService.js';
-import { CTX_INLINE_CHAT_FILE_BELONGS_TO_CHAT, CTX_INLINE_CHAT_VISIBLE, InlineChatConfigKeys } from '../common/inlineChat.js';
+import { CTX_INLINE_CHAT_FILE_BELONGS_TO_CHAT, CTX_INLINE_CHAT_PENDING_CONFIRMATION, CTX_INLINE_CHAT_TERMINATED, CTX_INLINE_CHAT_VISIBLE, InlineChatConfigKeys } from '../common/inlineChat.js';
 import { InlineChatAffordance } from './inlineChatAffordance.js';
 import { InlineChatInputWidget, InlineChatSessionOverlayWidget } from './inlineChatOverlayWidget.js';
-import { IInlineChatSession2, IInlineChatSessionService } from './inlineChatSessionService.js';
+import { continueInPanelChat, IInlineChatSession2, IInlineChatSessionService } from './inlineChatSessionService.js';
 import { EditorBasedInlineChatWidget } from './inlineChatWidget.js';
 import { InlineChatZoneWidget } from './inlineChatZoneWidget.js';
 
@@ -157,6 +157,8 @@ export class InlineChatController implements IEditorContribution {
 
 		const ctxInlineChatVisible = CTX_INLINE_CHAT_VISIBLE.bindTo(contextKeyService);
 		const ctxFileBelongsToChat = CTX_INLINE_CHAT_FILE_BELONGS_TO_CHAT.bindTo(contextKeyService);
+		const ctxPendingConfirmation = CTX_INLINE_CHAT_PENDING_CONFIRMATION.bindTo(contextKeyService);
+		const ctxTerminated = CTX_INLINE_CHAT_TERMINATED.bindTo(contextKeyService);
 		const notebookAgentConfig = observableConfigValue(InlineChatConfigKeys.notebookAgent, false, this._configurationService);
 		this._renderMode = observableConfigValue(InlineChatConfigKeys.RenderMode, 'zone', this._configurationService);
 
@@ -320,6 +322,11 @@ export class InlineChatController implements IEditorContribution {
 				: localize('placeholderWithSelection', "Modify selected code");
 		});
 
+		this._store.add(autorun(r => {
+			const session = visibleSessionObs.read(r);
+			ctxTerminated.set(!!session?.terminationState.read(r));
+		}));
+
 
 		this._store.add(autorun(r => {
 
@@ -354,16 +361,21 @@ export class InlineChatController implements IEditorContribution {
 			const session = visibleSessionObs.read(r);
 			const renderMode = this._renderMode.read(r);
 			if (!session || renderMode !== 'hover') {
+				ctxPendingConfirmation.set(false);
 				sessionOverlayWidget.hide();
 				return;
 			}
 			const lastRequest = session.chatModel.lastRequestObs.read(r);
 			const isInProgress = lastRequest?.response?.isInProgress.read(r);
+			const isPendingConfirmation = !!lastRequest?.response?.isPendingConfirmation.read(r);
+			const isError = !!lastRequest?.response?.result?.errorDetails;
+			const isTerminated = !!session.terminationState.read(r);
+			ctxPendingConfirmation.set(isPendingConfirmation);
 			const entry = session.editingSession.readEntry(session.uri, r);
 			// When there's no entry (no changes made) and the response is complete, the widget should be hidden.
 			// When there's an entry in Modified state, it needs to be settled (accepted/rejected).
 			const isNotSettled = entry ? entry.state.read(r) === ModifiedFileEntryState.Modified : false;
-			if (isInProgress || isNotSettled) {
+			if (isInProgress || isNotSettled || isPendingConfirmation || isError || isTerminated) {
 				sessionOverlayWidget.show(session);
 			} else {
 				sessionOverlayWidget.hide();
@@ -410,7 +422,9 @@ export class InlineChatController implements IEditorContribution {
 
 
 		this._store.add(autorun(r => {
+			const session = visibleSessionObs.read(r);
 			const response = lastResponseObs.read(r);
+			const terminationState = session?.terminationState.read(r);
 
 			this._zone.rawValue?.widget.updateInfo('');
 
@@ -420,6 +434,8 @@ export class InlineChatController implements IEditorContribution {
 					// ERROR case
 					this._zone.rawValue?.widget.updateInfo(`$(error) ${response.result.errorDetails.message}`);
 					alert(response.result.errorDetails.message);
+				} else if (terminationState) {
+					this._zone.rawValue?.widget.updateInfo(`$(info) ${renderAsPlaintext(terminationState)}`);
 				}
 
 				// no response or not in progress
@@ -600,11 +616,40 @@ export class InlineChatController implements IEditorContribution {
 		if (!session) {
 			return;
 		}
-		this._chatService.cancelCurrentRequestForSession(session.chatModel.sessionResource);
+		await this._chatService.cancelCurrentRequestForSession(session.chatModel.sessionResource, 'inlineChatReject');
 		await session.editingSession.reject();
 		session.dispose();
 	}
 
+	async continueSessionInChat(): Promise<void> {
+		const session = this._currentSession.get();
+		if (!session) {
+			return;
+		}
+
+		await this._instaService.invokeFunction(continueInPanelChat, session);
+	}
+
+	async rephraseSession(): Promise<void> {
+		const session = this._currentSession.get();
+		if (!session) {
+			return;
+		}
+
+		const requestText = session.chatModel.getRequests().at(-1)?.message.text;
+		session.dispose();
+
+		if (!requestText) {
+			return;
+		}
+
+		const selection = this._editor.getSelection();
+		const placeholder = selection && !selection.isEmpty()
+			? localize('placeholderWithSelectionHover', "Describe how to change this")
+			: localize('placeholderNoSelectionHover', "Describe what to generate");
+		await this.inputOverlayWidget.showMenuAtSelection(placeholder, requestText);
+	}
+
 	private async _selectVendorDefaultModel(session: IInlineChatSession2): Promise<void> {
 		const model = this._zone.value.widget.chatWidget.input.selectedLanguageModel.get();
 		if (model && !model.metadata.isDefaultForLocation[session.chatModel.initialLocation]) {
diff --git a/src/vs/workbench/contrib/inlineChat/browser/inlineChatOverlayWidget.ts b/src/vs/workbench/contrib/inlineChat/browser/inlineChatOverlayWidget.ts
index 486d0bc4442b1..434a4b2e7fe11 100644
--- a/src/vs/workbench/contrib/inlineChat/browser/inlineChatOverlayWidget.ts
+++ b/src/vs/workbench/contrib/inlineChat/browser/inlineChatOverlayWidget.ts
@@ -7,13 +7,16 @@ import './media/inlineChatOverlayWidget.css';
 import * as dom from '../../../../base/browser/dom.js';
 import { DEFAULT_FONT_FAMILY } from '../../../../base/browser/fonts.js';
 import { StandardKeyboardEvent } from '../../../../base/browser/keyboardEvent.js';
-import { renderAsPlaintext } from '../../../../base/browser/markdownRenderer.js';
+import { renderAsPlaintext, renderMarkdown } from '../../../../base/browser/markdownRenderer.js';
 import { ActionBar, ActionsOrientation } from '../../../../base/browser/ui/actionbar/actionbar.js';
 import { BaseActionViewItem } from '../../../../base/browser/ui/actionbar/actionViewItems.js';
+import { DomScrollableElement } from '../../../../base/browser/ui/scrollbar/scrollableElement.js';
 import { Codicon } from '../../../../base/common/codicons.js';
+import { MarkdownString } from '../../../../base/common/htmlContent.js';
 import { KeyCode } from '../../../../base/common/keyCodes.js';
 import { Disposable, DisposableStore, toDisposable } from '../../../../base/common/lifecycle.js';
 import { autorun, constObservable, derived, IObservable, observableFromEvent, observableFromEventOpts, observableValue } from '../../../../base/common/observable.js';
+import { ScrollbarVisibility } from '../../../../base/common/scrollable.js';
 import { ThemeIcon } from '../../../../base/common/themables.js';
 import { URI } from '../../../../base/common/uri.js';
 import { IActiveCodeEditor, IOverlayWidgetPosition } from '../../../../editor/browser/editorBrowser.js';
@@ -32,6 +35,7 @@ import { ChatEditingAcceptRejectActionViewItem } from '../../chat/browser/chatEd
 import { CTX_INLINE_CHAT_INPUT_HAS_TEXT, CTX_INLINE_CHAT_INPUT_WIDGET_FOCUSED } from '../common/inlineChat.js';
 import { StickyScrollController } from '../../../../editor/contrib/stickyScroll/browser/stickyScrollController.js';
 import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { getSimpleEditorOptions } from '../../codeEditor/browser/simpleEditorOptions.js';
 import { PlaceholderTextContribution } from '../../../../editor/contrib/placeholderText/browser/placeholderTextContribution.js';
@@ -256,12 +260,12 @@ export class InlineChatInputWidget extends Disposable {
 	 * @param left Left offset relative to editor
 	 * @param anchorAbove Whether to anchor above the position (widget grows upward)
 	 */
-	show(lineNumber: number, left: number, anchorAbove: boolean, placeholder: string): void {
+	show(lineNumber: number, left: number, anchorAbove: boolean, placeholder: string, value?: string): void {
 		this._showStore.clear();
 
 		// Clear input state
 		this._input.updateOptions({ wordWrap: 'off', placeholder });
-		this._input.getModel().setValue('');
+		this._input.getModel().setValue(value ?? '');
 
 		// Store anchor info for scroll updates
 		this._anchorLineNumber = lineNumber;
@@ -299,7 +303,12 @@ export class InlineChatInputWidget extends Disposable {
 		}));
 
 		// Focus the input editor
-		setTimeout(() => this._input.focus(), 0);
+		setTimeout(() => {
+			this._input.focus();
+			if (value) {
+				this._input.setSelection(this._input.getModel().getFullModelRange());
+			}
+		}, 0);
 	}
 
 	private _updatePosition(): void {
@@ -354,6 +363,10 @@ export class InlineChatSessionOverlayWidget extends Disposable {
 
 	private readonly _domNode: HTMLElement = document.createElement('div');
 	private readonly _container: HTMLElement;
+	private readonly _markdownContainer: HTMLElement;
+	private readonly _markdownMessage: HTMLElement;
+	private readonly _markdownScrollable: DomScrollableElement;
+	private readonly _contentRow: HTMLElement;
 	private readonly _statusNode: HTMLElement;
 	private readonly _icon: HTMLElement;
 	private readonly _message: HTMLElement;
@@ -369,6 +382,7 @@ export class InlineChatSessionOverlayWidget extends Disposable {
 		private readonly _editorObs: ObservableCodeEditor,
 		@IInstantiationService private readonly _instaService: IInstantiationService,
 		@IKeybindingService private readonly _keybindingService: IKeybindingService,
+		@ILogService private readonly _logService: ILogService,
 	) {
 		super();
 
@@ -378,12 +392,29 @@ export class InlineChatSessionOverlayWidget extends Disposable {
 		this._domNode.appendChild(this._container);
 		this._container.classList.add('inline-chat-session-overlay-container');
 
+		this._markdownContainer = document.createElement('div');
+		this._markdownContainer.classList.add('markdown-scroll-container');
+
+		this._markdownMessage = document.createElement('div');
+		this._markdownMessage.classList.add('markdown-message');
+		this._markdownContainer.appendChild(this._markdownMessage);
+		this._markdownScrollable = this._store.add(new DomScrollableElement(this._markdownContainer, {
+			consumeMouseWheelIfScrollbarIsNeeded: true,
+			horizontal: ScrollbarVisibility.Hidden,
+			vertical: ScrollbarVisibility.Auto,
+		}));
+		this._container.appendChild(this._markdownScrollable.getDomNode());
+
+		this._contentRow = document.createElement('div');
+		this._contentRow.classList.add('content-row');
+		this._container.appendChild(this._contentRow);
+
 		// Create status node with icon and message
 		this._statusNode = document.createElement('div');
 		this._statusNode.classList.add('status');
 		this._icon = dom.append(this._statusNode, dom.$('span'));
 		this._message = dom.append(this._statusNode, dom.$('span.message'));
-		this._container.appendChild(this._statusNode);
+		this._contentRow.appendChild(this._statusNode);
 
 		// Create toolbar node
 		this._toolbarNode = document.createElement('div');
@@ -408,6 +439,14 @@ export class InlineChatSessionOverlayWidget extends Disposable {
 				return undefined;
 			}
 
+			const terminationState = session.terminationState.read(r);
+			if (terminationState) {
+				return {
+					markdown: terminationState,
+					icon: Codicon.info
+				};
+			}
+
 			const response = chatModel.lastRequestObs.read(r)?.response;
 			if (!response) {
 				return { message: localize('working', "Working..."), icon: ThemeIcon.modify(Codicon.loading, 'spin') };
@@ -434,6 +473,14 @@ export class InlineChatSessionOverlayWidget extends Disposable {
 				};
 			}
 
+			const pendingConfirmation = response.isPendingConfirmation.read(r);
+			if (pendingConfirmation) {
+				return {
+					message: localize('needsApproval', "Sorry, but an expected error happened"),
+					icon: Codicon.error
+				};
+			}
+
 			const lastPart = observableFromEventOpts({ equalsFn: () => false }, response.onDidChange, () => response.response.value)
 				.read(r)
 				.filter(part => part.kind === 'progressMessage' || part.kind === 'toolInvocation')
@@ -448,20 +495,56 @@ export class InlineChatSessionOverlayWidget extends Disposable {
 			}
 		});
 
+		const markdownStore = this._showStore.add(new DisposableStore());
+
 		this._showStore.add(autorun(r => {
 			const value = requestMessage.read(r);
 			if (value) {
-				this._message.innerText = renderAsPlaintext(value.message);
-				this._icon.className = '';
-				this._icon.classList.add(...ThemeIcon.asClassNameArray(value.icon));
+				if (value.message && value.icon) {
+					this._message.innerText = renderAsPlaintext(value.message);
+					this._icon.className = '';
+					this._icon.classList.add(...ThemeIcon.asClassNameArray(value.icon));
+					this._statusNode.classList.remove('hidden');
+					this._contentRow.classList.remove('status-hidden');
+				} else {
+					this._message.innerText = '';
+					this._icon.className = '';
+					this._statusNode.classList.add('hidden');
+					this._contentRow.classList.add('status-hidden');
+				}
+				markdownStore.clear();
+				this._markdownMessage.replaceChildren();
+				if (value.markdown) {
+					this._markdownScrollable.getDomNode().classList.remove('hidden');
+					const markdown = typeof value.markdown === 'string' ? new MarkdownString(value.markdown) : value.markdown;
+					const rendered = markdownStore.add(renderMarkdown(markdown));
+					this._markdownMessage.appendChild(rendered.element);
+					this._markdownScrollable.scanDomNode();
+				} else {
+					this._markdownScrollable.getDomNode().classList.add('hidden');
+				}
 			} else {
 				this._message.innerText = '';
 				this._icon.className = '';
+				this._statusNode.classList.add('hidden');
+				this._contentRow.classList.add('status-hidden');
+				markdownStore.clear();
+				this._markdownMessage.replaceChildren();
+				this._markdownScrollable.getDomNode().classList.add('hidden');
+			}
+		}));
+
+		// Log when pending confirmation changes
+		this._showStore.add(autorun(r => {
+			const response = session.chatModel.lastRequestObs.read(r)?.response;
+			const pending = response?.isPendingConfirmation.read(r);
+			if (pending) {
+				this._logService.info(`[InlineChat] UNEXPECTED approval needed: ${pending.detail ?? 'unknown'}`);
 			}
 		}));
 
 		// Add toolbar
-		this._container.appendChild(this._toolbarNode);
+		this._contentRow.appendChild(this._toolbarNode);
 		this._showStore.add(toDisposable(() => this._toolbarNode.remove()));
 
 		const that = this;
@@ -475,7 +558,7 @@ export class InlineChatSessionOverlayWidget extends Disposable {
 			},
 			menuOptions: { renderShortTitle: true },
 			actionViewItemProvider: (action, options) => {
-				const primaryActions = ['inlineChat2.cancel', 'inlineChat2.keep'];
+				const primaryActions = ['inlineChat2.cancel', 'inlineChat2.keep', 'inlineChat2.rephrase'];
 				const labeledActions = primaryActions.concat(['inlineChat2.undo']);
 
 				if (!labeledActions.includes(action.id)) {
@@ -504,8 +587,12 @@ export class InlineChatSessionOverlayWidget extends Disposable {
 			const padding = Math.round(lineHeight.read(r) * 2 / 3);
 
 			// Cap max-width to the editor viewport (content area)
-			const maxWidth = layoutInfo.contentWidth - 2 * padding;
+			const maxWidth = Math.min(400, layoutInfo.contentWidth - 2 * padding);
+			const maxHeight = Math.min(150, Math.floor(layoutInfo.height / 3));
 			this._domNode.style.maxWidth = `${maxWidth}px`;
+			this._markdownScrollable.getDomNode().style.maxHeight = `${maxHeight}px`;
+			this._markdownContainer.style.maxHeight = `${maxHeight}px`;
+			this._markdownScrollable.scanDomNode();
 
 			// Position: top right, below sticky scroll with padding, left of minimap and scrollbar
 			const top = stickyScrollHeight + padding;
diff --git a/src/vs/workbench/contrib/inlineChat/browser/inlineChatSessionService.ts b/src/vs/workbench/contrib/inlineChat/browser/inlineChatSessionService.ts
index 1e54c82cb2ffd..3bcfdd27cb7ff 100644
--- a/src/vs/workbench/contrib/inlineChat/browser/inlineChatSessionService.ts
+++ b/src/vs/workbench/contrib/inlineChat/browser/inlineChatSessionService.ts
@@ -3,6 +3,8 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 import { Event } from '../../../../base/common/event.js';
+import { IMarkdownString } from '../../../../base/common/htmlContent.js';
+import { IObservable } from '../../../../base/common/observable.js';
 import { URI } from '../../../../base/common/uri.js';
 import { IActiveCodeEditor, ICodeEditor } from '../../../../editor/browser/editorBrowser.js';
 import { Position } from '../../../../editor/common/core/position.js';
@@ -12,17 +14,21 @@ import { IChatWidgetService } from '../../chat/browser/chat.js';
 import { IChatEditingSession } from '../../chat/common/editing/chatEditingService.js';
 import { IChatModel, IChatModelInputState, IChatRequestModel } from '../../chat/common/model/chatModel.js';
 import { IChatService } from '../../chat/common/chatService/chatService.js';
-import { ChatAgentLocation } from '../../chat/common/constants.js';
+import { ChatAgentLocation, ChatModeKind } from '../../chat/common/constants.js';
 
 
 export const IInlineChatSessionService = createDecorator<IInlineChatSessionService>('IInlineChatSessionService');
 
+export type InlineChatSessionTerminationState = string | IMarkdownString;
+
 export interface IInlineChatSession2 {
 	readonly initialPosition: Position;
 	readonly initialSelection: Selection;
 	readonly uri: URI;
 	readonly chatModel: IChatModel;
 	readonly editingSession: IChatEditingSession;
+	readonly terminationState: IObservable<InlineChatSessionTerminationState | undefined>;
+	setTerminationState(state: InlineChatSessionTerminationState | undefined): void;
 	dispose(): void;
 }
 
@@ -74,10 +80,35 @@ export async function askInPanelChat(accessor: ServicesAccessor, request: IChatR
 	const newModelRef = chatService.startNewLocalSession(ChatAgentLocation.Chat);
 	const newModel = newModelRef.object;
 
-	newModel.inputModel.setState({ ...state });
+	newModel.inputModel.setState({
+		...state,
+		mode: { id: 'agent', kind: ChatModeKind.Agent }
+	});
 
 	const widget = await widgetService.openSession(newModelRef.object.sessionResource);
 
 	newModelRef.dispose(); // can be freed after opening because the widget also holds a reference
 	widget?.acceptInput(request.message.text);
 }
+
+export async function continueInPanelChat(accessor: ServicesAccessor, session: IInlineChatSession2): Promise<void> {
+	const request = session.chatModel.getRequests().at(-1);
+	if (!request) {
+		return;
+	}
+
+	await askInPanelChat(accessor, request, session.chatModel.inputModel.state.get());
+	session.dispose();
+}
+
+export function rephraseInlineChat(accessor: ServicesAccessor, session: IInlineChatSession2): string | undefined {
+	const request = session.chatModel.getRequests().at(-1);
+	if (!request) {
+		return undefined;
+	}
+
+	accessor.get(IChatService).removeRequest(session.chatModel.sessionResource, request.id);
+	session.chatModel.inputModel.setState({ inputText: request.message.text });
+	session.setTerminationState(undefined);
+	return request.message.text;
+}
diff --git a/src/vs/workbench/contrib/inlineChat/browser/inlineChatSessionServiceImpl.ts b/src/vs/workbench/contrib/inlineChat/browser/inlineChatSessionServiceImpl.ts
index 52ea6e4631636..2aa1b591c1882 100644
--- a/src/vs/workbench/contrib/inlineChat/browser/inlineChatSessionServiceImpl.ts
+++ b/src/vs/workbench/contrib/inlineChat/browser/inlineChatSessionServiceImpl.ts
@@ -5,7 +5,7 @@
 import { Emitter, Event } from '../../../../base/common/event.js';
 import { Disposable, dispose, DisposableStore, toDisposable } from '../../../../base/common/lifecycle.js';
 import { ResourceMap } from '../../../../base/common/map.js';
-import { autorun, observableFromEvent } from '../../../../base/common/observable.js';
+import { autorun, observableFromEvent, observableValue } from '../../../../base/common/observable.js';
 import { isEqual } from '../../../../base/common/resources.js';
 import { URI } from '../../../../base/common/uri.js';
 import { IActiveCodeEditor, isCodeEditor, isCompositeEditor, isDiffEditor } from '../../../../editor/browser/editorBrowser.js';
@@ -27,7 +27,7 @@ import { IChatService } from '../../chat/common/chatService/chatService.js';
 import { ChatAgentLocation } from '../../chat/common/constants.js';
 import { ILanguageModelToolsService, IToolData, ToolDataSource } from '../../chat/common/tools/languageModelToolsService.js';
 import { CTX_INLINE_CHAT_HAS_AGENT2, CTX_INLINE_CHAT_HAS_NOTEBOOK_AGENT, CTX_INLINE_CHAT_POSSIBLE, InlineChatConfigKeys } from '../common/inlineChat.js';
-import { askInPanelChat, IInlineChatSession2, IInlineChatSessionService } from './inlineChatSessionService.js';
+import { continueInPanelChat, IInlineChatSession2, IInlineChatSessionService, InlineChatSessionTerminationState, rephraseInlineChat } from './inlineChatSessionService.js';
 
 export class InlineChatError extends Error {
 	static readonly code = 'InlineChatError';
@@ -83,10 +83,11 @@ export class InlineChatSessionServiceImpl implements IInlineChatSessionService {
 		const chatModelRef = this._chatService.startNewLocalSession(ChatAgentLocation.EditorInline, { canUseTools: false /* SEE https://github.com/microsoft/vscode/issues/279946 */ });
 		const chatModel = chatModelRef.object;
 		chatModel.startEditingSession(false);
+		const terminationState = observableValue<InlineChatSessionTerminationState | undefined>(this, undefined);
 
 		const store = new DisposableStore();
 		store.add(toDisposable(() => {
-			this._chatService.cancelCurrentRequestForSession(chatModel.sessionResource);
+			void this._chatService.cancelCurrentRequestForSession(chatModel.sessionResource, 'inlineChatSession');
 			chatModel.editingSession?.reject();
 			this._sessions.delete(uri);
 			this._onDidChangeSessions.fire(this);
@@ -136,6 +137,11 @@ export class InlineChatSessionServiceImpl implements IInlineChatSessionService {
 			initialSelection: editor.getSelection(),
 			chatModel,
 			editingSession: chatModel.editingSession!,
+			terminationState,
+			setTerminationState: state => {
+				terminationState.set(state, undefined);
+				this._onDidChangeSessions.fire(this);
+			},
 			dispose: store.dispose.bind(store)
 		};
 		this._sessions.set(uri, result);
@@ -235,7 +241,18 @@ export class InlineChatEscapeToolContribution extends Disposable {
 		canBeReferencedInPrompt: false,
 		alwaysDisplayInputOutput: false,
 		displayName: localize('name', "Inline Chat to Panel Chat"),
-		modelDescription: 'Moves the inline chat session to the richer panel chat which supports edits across files, creating and deleting files, multi-turn conversations between the user and the assistant, and access to more IDE tools, like retrieve problems, interact with source control, run terminal commands etc.',
+		modelDescription: 'Show a short textual response when not being able to make code changes and when not having been asked for code changes. Can also be used to move the request to the richer panel chat which supports edits across files, creating and deleting files, multi-turn conversations between the user and the assistant, and access to more IDE tools, like retrieve problems, interact with source control, run terminal commands etc.',
+		inputSchema: {
+			type: 'object',
+			additionalProperties: false,
+			properties: {
+				response: {
+					type: 'string',
+					description: localize('response.description', "Optional brief response for inline chat. Keep it at 10 words or fewer."),
+					maxLength: 200,
+				}
+			}
+		}
 	};
 
 	constructor(
@@ -243,6 +260,7 @@ export class InlineChatEscapeToolContribution extends Disposable {
 		@IInlineChatSessionService inlineChatSessionService: IInlineChatSessionService,
 		@IDialogService dialogService: IDialogService,
 		@ICodeEditorService codeEditorService: ICodeEditorService,
+		@IConfigurationService configurationService: IConfigurationService,
 		@IChatService chatService: IChatService,
 		@ILogService logService: ILogService,
 		@IStorageService storageService: IStorageService,
@@ -268,6 +286,22 @@ export class InlineChatEscapeToolContribution extends Disposable {
 					return { content: [{ kind: 'text', value: 'Cancel' }] };
 				}
 
+				const lastRequest = session.chatModel.getRequests().at(-1);
+				if (!lastRequest) {
+					logService.warn(`InlineChatEscapeToolContribution: no request found for id ${sessionResource}`);
+					return { content: [{ kind: 'text', value: 'Cancel' }], toolResultMessage: localize('tool.cancel', "Cancel") };
+				}
+
+				if (configurationService.getValue<string>(InlineChatConfigKeys.RenderMode) === 'hover') {
+
+					const response = typeof invocation.parameters?.response === 'string' && invocation.parameters.response.trim().length > 0
+						? invocation.parameters.response.trim()
+						: localize('terminated.message', "Inline chat is designed for making single-file code changes. Continue your request in the Chat view or rephrase it for inline chat.");
+
+					session.setTerminationState(response);
+					return { content: [{ kind: 'text', value: 'Success' }] };
+				}
+
 				const dontAskAgain = storageService.getBoolean(InlineChatEscapeToolContribution.DONT_ASK_AGAIN_KEY, StorageScope.PROFILE);
 
 				let result: { confirmed: boolean; checkboxChecked?: boolean };
@@ -290,14 +324,11 @@ export class InlineChatEscapeToolContribution extends Disposable {
 
 				if (!editor || result.confirmed) {
 					logService.trace('InlineChatEscapeToolContribution: moving session to panel chat');
-					await instaService.invokeFunction(askInPanelChat, session.chatModel.getRequests().at(-1)!, session.chatModel.inputModel.state.get());
-					session.dispose();
+					await instaService.invokeFunction(continueInPanelChat, session);
 
 				} else {
 					logService.trace('InlineChatEscapeToolContribution: rephrase prompt');
-					const lastRequest = session.chatModel.getRequests().at(-1)!;
-					chatService.removeRequest(session.chatModel.sessionResource, lastRequest.id);
-					session.chatModel.inputModel.setState({ inputText: lastRequest.message.text });
+					instaService.invokeFunction(rephraseInlineChat, session);
 				}
 
 				if (result.checkboxChecked) {
diff --git a/src/vs/workbench/contrib/inlineChat/browser/media/inlineChat.css b/src/vs/workbench/contrib/inlineChat/browser/media/inlineChat.css
index da1e670cf8bc7..6556757c59cc4 100644
--- a/src/vs/workbench/contrib/inlineChat/browser/media/inlineChat.css
+++ b/src/vs/workbench/contrib/inlineChat/browser/media/inlineChat.css
@@ -6,9 +6,9 @@
 
 .monaco-workbench .inline-chat {
 	color: inherit;
-	border-radius: 4px;
+	border-radius: var(--vscode-cornerRadius-large);
 	border: 1px solid var(--vscode-inlineChat-border);
-	box-shadow: 0 2px 4px 0 var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	background: var(--vscode-inlineChat-background);
 	padding-top: 3px;
 	position: relative;
diff --git a/src/vs/workbench/contrib/inlineChat/browser/media/inlineChatEditorAffordance.css b/src/vs/workbench/contrib/inlineChat/browser/media/inlineChatEditorAffordance.css
index 37d4268342add..de36a936fd329 100644
--- a/src/vs/workbench/contrib/inlineChat/browser/media/inlineChatEditorAffordance.css
+++ b/src/vs/workbench/contrib/inlineChat/browser/media/inlineChatEditorAffordance.css
@@ -9,7 +9,7 @@
 	border-radius: 8px;
 	display: flex;
 	align-items: center;
-	box-shadow: 0 4px 8px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	cursor: pointer;
 	min-width: var(--vscode-inline-chat-affordance-height);
 	min-height: var(--vscode-inline-chat-affordance-height);
diff --git a/src/vs/workbench/contrib/inlineChat/browser/media/inlineChatOverlayWidget.css b/src/vs/workbench/contrib/inlineChat/browser/media/inlineChatOverlayWidget.css
index 9acc9ecf81703..68424c910247a 100644
--- a/src/vs/workbench/contrib/inlineChat/browser/media/inlineChatOverlayWidget.css
+++ b/src/vs/workbench/contrib/inlineChat/browser/media/inlineChatOverlayWidget.css
@@ -8,8 +8,8 @@
 .inline-chat-gutter-menu {
 	background: var(--vscode-panel-background);
 	border: 1px solid var(--vscode-menu-border, var(--vscode-widget-border));
-	border-radius: 8px;
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	border-radius: var(--vscode-cornerRadius-large);
+	box-shadow: var(--vscode-shadow-lg);
 	z-index: 100;
 }
 
@@ -98,29 +98,81 @@
 }
 
 .inline-chat-session-overlay-container {
-	padding: 2px 4px;
+	padding: 4px;
 	color: var(--vscode-foreground);
 	background-color: var(--vscode-editorWidget-background);
 	border-radius: 6px;
 	border: 1px solid var(--vscode-contrastBorder);
 	display: flex;
-	align-items: center;
+	flex-direction: column;
+	align-items: stretch;
 	justify-content: center;
-	gap: 4px;
+	gap: 8px;
 	z-index: 10;
-	box-shadow: 0 2px 8px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	overflow: hidden;
 }
 
+.inline-chat-session-overlay-container .markdown-message {
+	padding: 5px;
+	font-size: 12px;
+	line-height: 1.45;
+}
+
+.inline-chat-session-overlay-container > .monaco-scrollable-element {
+	width: 100%;
+}
+
+.inline-chat-session-overlay-container > .monaco-scrollable-element.hidden {
+	display: none;
+}
+
+.inline-chat-session-overlay-container .markdown-scroll-container {
+	width: 100%;
+}
+
+.inline-chat-session-overlay-container .markdown-message DIV P {
+	margin: 0;
+}
+
+.inline-chat-session-overlay-container .markdown-message DIV P code {
+	font-family: var(--monaco-monospace-font);
+	font-size: var(--vscode-chat-font-size-body-xs);
+	color: var(--vscode-textPreformat-foreground);
+	background-color: var(--vscode-textPreformat-background);
+	padding: 1px 3px;
+	border-radius: 4px;
+	border: 1px solid var(--vscode-textPreformat-border);
+	white-space: pre-wrap;
+}
+
+
+.inline-chat-session-overlay-container .content-row {
+	display: flex;
+	align-items: center;
+	justify-content: space-between;
+	gap: 4px;
+	min-width: 0;
+}
+
+.inline-chat-session-overlay-container .content-row.status-hidden {
+	justify-content: flex-end;
+}
+
 .inline-chat-session-overlay-container .status {
 	align-items: center;
 	display: inline-flex;
+	flex: 1;
 	padding: 5px 0 5px 5px;
 	font-size: 12px;
 	overflow: hidden;
 	gap: 6px;
 }
 
+.inline-chat-session-overlay-container .status.hidden {
+	display: none;
+}
+
 .inline-chat-session-overlay-container .status .message {
 	white-space: nowrap;
 	overflow: hidden;
diff --git a/src/vs/workbench/contrib/inlineChat/common/inlineChat.ts b/src/vs/workbench/contrib/inlineChat/common/inlineChat.ts
index 5eb1312bd5a33..692399181b623 100644
--- a/src/vs/workbench/contrib/inlineChat/common/inlineChat.ts
+++ b/src/vs/workbench/contrib/inlineChat/common/inlineChat.ts
@@ -15,7 +15,6 @@ import { NOTEBOOK_IS_ACTIVE_EDITOR } from '../../notebook/common/notebookContext
 
 export const enum InlineChatConfigKeys {
 	FinishOnType = 'inlineChat.finishOnType',
-	HoldToSpeech = 'inlineChat.holdToSpeech',
 	/** @deprecated do not read on client */
 	EnableV2 = 'inlineChat.enableV2',
 	notebookAgent = 'inlineChat.notebookAgent',
@@ -33,11 +32,6 @@ Registry.as<IConfigurationRegistry>(Extensions.Configuration).registerConfigurat
 			default: false,
 			type: 'boolean'
 		},
-		[InlineChatConfigKeys.HoldToSpeech]: {
-			description: localize('holdToSpeech', "Whether holding the inline chat keybinding will automatically enable speech recognition."),
-			default: true,
-			type: 'boolean'
-		},
 		[InlineChatConfigKeys.EnableV2]: {
 			description: localize('enableV2', "Whether to use the next version of inline chat."),
 			default: false,
@@ -73,7 +67,7 @@ Registry.as<IConfigurationRegistry>(Extensions.Configuration).registerConfigurat
 		},
 		[InlineChatConfigKeys.RenderMode]: {
 			description: localize('renderMode', "Controls how inline chat is rendered."),
-			default: 'zone',
+			default: 'hover',
 			type: 'string',
 			enum: ['zone', 'hover'],
 			enumDescriptions: [
@@ -87,7 +81,7 @@ Registry.as<IConfigurationRegistry>(Extensions.Configuration).registerConfigurat
 		},
 		[InlineChatConfigKeys.FixDiagnostics]: {
 			description: localize('fixDiagnostics', "Controls whether the Fix action is shown for diagnostics in the editor."),
-			default: false,
+			default: true,
 			type: 'boolean',
 			experiment: {
 				mode: 'auto'
@@ -129,6 +123,9 @@ export const CTX_INLINE_CHAT_CHANGE_SHOWS_DIFF = new RawContextKey<boolean>('inl
 export const CTX_INLINE_CHAT_REQUEST_IN_PROGRESS = new RawContextKey<boolean>('inlineChatRequestInProgress', false, localize('inlineChatRequestInProgress', "Whether an inline chat request is currently in progress"));
 export const CTX_INLINE_CHAT_RESPONSE_TYPE = new RawContextKey<InlineChatResponseType>('inlineChatResponseType', InlineChatResponseType.None, localize('inlineChatResponseTypes', "What type was the responses have been receieved, nothing yet, just messages, or messaged and local edits"));
 export const CTX_INLINE_CHAT_FILE_BELONGS_TO_CHAT = new RawContextKey<boolean>('inlineChatFileBelongsToChat', false, localize('inlineChatFileBelongsToChat', "Whether the current file belongs to a chat editing session"));
+export const CTX_INLINE_CHAT_PENDING_CONFIRMATION = new RawContextKey<boolean>('inlineChatPendingConfirmation', false, localize('inlineChatPendingConfirmation', "Whether an inline chat request is pending user confirmation"));
+export const CTX_INLINE_CHAT_TERMINATED = new RawContextKey<boolean>('inlineChatTerminated', false, localize('inlineChatTerminated', "Whether the current inline chat session is terminated"));
+export const CTX_INLINE_CHAT_AFFORDANCE_VISIBLE = new RawContextKey<boolean>('inlineChatAffordanceVisible', false, localize('inlineChatAffordanceVisible', "Whether an inline chat affordance widget is visible"));
 
 export const CTX_INLINE_CHAT_V1_ENABLED = ContextKeyExpr.or(
 	ContextKeyExpr.and(NOTEBOOK_IS_ACTIVE_EDITOR, CTX_INLINE_CHAT_HAS_NOTEBOOK_INLINE)
diff --git a/src/vs/workbench/contrib/inlineChat/electron-browser/inlineChatActions.ts b/src/vs/workbench/contrib/inlineChat/electron-browser/inlineChatActions.ts
deleted file mode 100644
index 0a9c91d1859df..0000000000000
--- a/src/vs/workbench/contrib/inlineChat/electron-browser/inlineChatActions.ts
+++ /dev/null
@@ -1,83 +0,0 @@
-/*---------------------------------------------------------------------------------------------
- *  Copyright (c) Microsoft Corporation. All rights reserved.
- *  Licensed under the MIT License. See License.txt in the project root for license information.
- *--------------------------------------------------------------------------------------------*/
-import { KeyCode, KeyMod } from '../../../../base/common/keyCodes.js';
-import { ICodeEditor } from '../../../../editor/browser/editorBrowser.js';
-import { ContextKeyExpr } from '../../../../platform/contextkey/common/contextkey.js';
-import { ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
-import { KeybindingWeight } from '../../../../platform/keybinding/common/keybindingsRegistry.js';
-import { InlineChatController } from '../browser/inlineChatController.js';
-import { AbstractInlineChatAction, setHoldForSpeech } from '../browser/inlineChatActions.js';
-import { disposableTimeout } from '../../../../base/common/async.js';
-import { EditorContextKeys } from '../../../../editor/common/editorContextKeys.js';
-import { ICommandService } from '../../../../platform/commands/common/commands.js';
-import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
-import { StartVoiceChatAction, StopListeningAction, VOICE_KEY_HOLD_THRESHOLD } from '../../chat/electron-browser/actions/voiceChatActions.js';
-import { IChatExecuteActionContext } from '../../chat/browser/actions/chatExecuteActions.js';
-import { CTX_INLINE_CHAT_VISIBLE, InlineChatConfigKeys } from '../common/inlineChat.js';
-import { HasSpeechProvider, ISpeechService } from '../../speech/common/speechService.js';
-import { localize2 } from '../../../../nls.js';
-import { Action2 } from '../../../../platform/actions/common/actions.js';
-import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
-import { EditorAction2 } from '../../../../editor/browser/editorExtensions.js';
-
-export class HoldToSpeak extends EditorAction2 {
-
-	constructor() {
-		super({
-			id: 'inlineChat.holdForSpeech',
-			category: AbstractInlineChatAction.category,
-			precondition: ContextKeyExpr.and(HasSpeechProvider, CTX_INLINE_CHAT_VISIBLE),
-			title: localize2('holdForSpeech', "Hold for Speech"),
-			keybinding: {
-				when: EditorContextKeys.textInputFocus,
-				weight: KeybindingWeight.WorkbenchContrib,
-				primary: KeyMod.CtrlCmd | KeyCode.KeyI,
-			},
-		});
-	}
-
-	override runEditorCommand(accessor: ServicesAccessor, editor: ICodeEditor, ..._args: unknown[]) {
-		const ctrl = InlineChatController.get(editor);
-		if (ctrl) {
-			holdForSpeech(accessor, ctrl, this);
-		}
-	}
-}
-
-function holdForSpeech(accessor: ServicesAccessor, ctrl: InlineChatController, action: Action2): void {
-
-	const configService = accessor.get(IConfigurationService);
-	const speechService = accessor.get(ISpeechService);
-	const keybindingService = accessor.get(IKeybindingService);
-	const commandService = accessor.get(ICommandService);
-
-	// enabled or possible?
-	if (!configService.getValue<boolean>(InlineChatConfigKeys.HoldToSpeech || !speechService.hasSpeechProvider)) {
-		return;
-	}
-
-	const holdMode = keybindingService.enableKeybindingHoldMode(action.desc.id);
-	if (!holdMode) {
-		return;
-	}
-	let listening = false;
-	const handle = disposableTimeout(() => {
-		// start VOICE input
-		commandService.executeCommand(StartVoiceChatAction.ID, { voice: { disableTimeout: true } } satisfies IChatExecuteActionContext);
-		listening = true;
-	}, VOICE_KEY_HOLD_THRESHOLD);
-
-	holdMode.finally(() => {
-		if (listening) {
-			commandService.executeCommand(StopListeningAction.ID).finally(() => {
-				ctrl.widget.chatWidget.acceptInput();
-			});
-		}
-		handle.dispose();
-	});
-}
-
-// make this accessible to the chat actions from the browser layer
-setHoldForSpeech(holdForSpeech);
diff --git a/src/vs/workbench/contrib/inlineChat/test/browser/inlineChatAffordance.test.ts b/src/vs/workbench/contrib/inlineChat/test/browser/inlineChatAffordance.test.ts
new file mode 100644
index 0000000000000..85719bf152cf6
--- /dev/null
+++ b/src/vs/workbench/contrib/inlineChat/test/browser/inlineChatAffordance.test.ts
@@ -0,0 +1,153 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { DisposableStore } from '../../../../../base/common/lifecycle.js';
+import { observableValue } from '../../../../../base/common/observable.js';
+import { Selection } from '../../../../../editor/common/core/selection.js';
+import { CursorChangeReason } from '../../../../../editor/common/cursorEvents.js';
+import { CursorState } from '../../../../../editor/common/cursorCommon.js';
+import { createTextModel } from '../../../../../editor/test/common/testTextModel.js';
+import { instantiateTestCodeEditor, ITestCodeEditor } from '../../../../../editor/test/browser/testCodeEditor.js';
+import { TestConfigurationService } from '../../../../../platform/configuration/test/common/testConfigurationService.js';
+import { ITelemetryService } from '../../../../../platform/telemetry/common/telemetry.js';
+import { IInlineChatSessionService } from '../../browser/inlineChatSessionService.js';
+import { Event } from '../../../../../base/common/event.js';
+import { InlineChatAffordance } from '../../browser/inlineChatAffordance.js';
+import { InlineChatInputWidget } from '../../browser/inlineChatOverlayWidget.js';
+import { runWithFakedTimers } from '../../../../../base/test/common/timeTravelScheduler.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { timeout } from '../../../../../base/common/async.js';
+import { TestInstantiationService } from '../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import { ITextModel } from '../../../../../editor/common/model.js';
+import { InlineChatConfigKeys } from '../../common/inlineChat.js';
+import { workbenchInstantiationService } from '../../../../test/browser/workbenchTestServices.js';
+import { IConfigurationChangeEvent, IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
+import { mock } from '../../../../../base/test/common/mock.js';
+
+function createMockInputWidget(): InlineChatInputWidget {
+	return new class extends mock<InlineChatInputWidget>() {
+		override readonly position = observableValue('test.position', null);
+		override show() { }
+		override hide() { }
+		override dispose() { }
+	};
+}
+
+suite('InlineChatAffordance - Telemetry', () => {
+
+	const store = new DisposableStore();
+	let editor: ITestCodeEditor;
+	let model: ITextModel;
+	let instantiationService: TestInstantiationService;
+	let configurationService: TestConfigurationService;
+	let telemetryEvents: { eventName: string; data: Record<string, unknown> }[];
+
+	setup(() => {
+		telemetryEvents = [];
+
+		instantiationService = workbenchInstantiationService({
+			configurationService: () => new TestConfigurationService({
+				[InlineChatConfigKeys.Affordance]: 'editor',
+			}),
+		}, store);
+
+		configurationService = instantiationService.get(IConfigurationService) as TestConfigurationService;
+
+		instantiationService.stub(ITelemetryService, new class extends mock<ITelemetryService>() {
+			override publicLog2(eventName: string, data?: Record<string, unknown>) {
+				telemetryEvents.push({ eventName, data: data ?? {} });
+			}
+		});
+
+		instantiationService.stub(IInlineChatSessionService, new class extends mock<IInlineChatSessionService>() {
+			override readonly onWillStartSession = Event.None;
+			override readonly onDidChangeSessions = Event.None;
+			override getSessionByTextModel() { return undefined; }
+			override getSessionBySessionUri() { return undefined; }
+		});
+
+		model = store.add(createTextModel('hello world\nfoo bar\nbaz qux'));
+		editor = store.add(instantiateTestCodeEditor(instantiationService, model));
+	});
+
+	teardown(() => {
+		store.clear();
+	});
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	function setExplicitSelection(sel: Selection): void {
+		editor.getViewModel()!.setCursorStates(
+			'test',
+			CursorChangeReason.Explicit,
+			[CursorState.fromModelSelection(sel)]
+		);
+	}
+
+	test('shown event includes mode "editor"', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		store.add(instantiationService.createInstance(InlineChatAffordance, editor, createMockInputWidget()));
+
+		setExplicitSelection(new Selection(1, 1, 1, 6));
+		await timeout(600);
+
+		const shown = telemetryEvents.filter(e => e.eventName === 'inlineChatAffordance/shown');
+		assert.strictEqual(shown.length, 1);
+		assert.strictEqual(shown[0].data.mode, 'editor');
+		assert.ok(typeof shown[0].data.id === 'string');
+		assert.strictEqual(shown[0].data.commandId, '');
+	}));
+
+	test('shown event does NOT fire when mode is off', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		configurationService.setUserConfiguration(InlineChatConfigKeys.Affordance, 'off');
+		configurationService.onDidChangeConfigurationEmitter.fire(new class extends mock<IConfigurationChangeEvent>() {
+			override affectsConfiguration(key: string) { return key === InlineChatConfigKeys.Affordance; }
+		});
+
+		store.add(instantiationService.createInstance(InlineChatAffordance, editor, createMockInputWidget()));
+
+		setExplicitSelection(new Selection(1, 1, 1, 6));
+		await timeout(600);
+
+		assert.strictEqual(telemetryEvents.filter(e => e.eventName === 'inlineChatAffordance/shown').length, 0);
+	}));
+
+	test('shown event does NOT fire for whitespace-only selection', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		model.setValue('   \nhello');
+
+		store.add(instantiationService.createInstance(InlineChatAffordance, editor, createMockInputWidget()));
+
+		setExplicitSelection(new Selection(1, 1, 1, 4));
+		await timeout(600);
+
+		assert.strictEqual(telemetryEvents.filter(e => e.eventName === 'inlineChatAffordance/shown').length, 0);
+	}));
+
+	test('shown event does NOT fire for empty selection', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		store.add(instantiationService.createInstance(InlineChatAffordance, editor, createMockInputWidget()));
+
+		setExplicitSelection(new Selection(1, 1, 1, 1));
+		await timeout(600);
+
+		assert.strictEqual(telemetryEvents.filter(e => e.eventName === 'inlineChatAffordance/shown').length, 0);
+	}));
+
+	test('each selection gets a unique affordanceId', () => runWithFakedTimers({ useFakeTimers: true }, async () => {
+		store.add(instantiationService.createInstance(InlineChatAffordance, editor, createMockInputWidget()));
+
+		setExplicitSelection(new Selection(1, 1, 1, 6));
+		await timeout(600);
+
+		// Clear selection, then make a new one
+		setExplicitSelection(new Selection(2, 1, 2, 1));
+		await timeout(100);
+		setExplicitSelection(new Selection(2, 1, 2, 4));
+		await timeout(600);
+
+		const shown = telemetryEvents.filter(e => e.eventName === 'inlineChatAffordance/shown');
+		assert.strictEqual(shown.length, 2);
+		assert.notStrictEqual(shown[0].data.id, shown[1].data.id);
+	}));
+});
diff --git a/src/vs/workbench/contrib/mcp/browser/mcpCommands.ts b/src/vs/workbench/contrib/mcp/browser/mcpCommands.ts
index 71fd9bcd6c820..a6d8c584080b7 100644
--- a/src/vs/workbench/contrib/mcp/browser/mcpCommands.ts
+++ b/src/vs/workbench/contrib/mcp/browser/mcpCommands.ts
@@ -61,10 +61,11 @@ import { TEXT_FILE_EDITOR_ID } from '../../files/common/files.js';
 import { McpCommandIds } from '../common/mcpCommandIds.js';
 import { McpContextKeys } from '../common/mcpContextKeys.js';
 import { IMcpRegistry } from '../common/mcpRegistryTypes.js';
-import { HasInstalledMcpServersContext, IMcpSamplingService, IMcpServer, IMcpServerStartOpts, IMcpService, InstalledMcpServersViewId, LazyCollectionState, McpCapability, McpCollectionDefinition, McpConnectionState, McpDefinitionReference, mcpPromptPrefix, McpServerCacheState, McpStartServerInteraction } from '../common/mcpTypes.js';
+import { HasInstalledMcpServersContext, IMcpSamplingService, IMcpServer, IMcpServerStartOpts, IMcpService, IMcpWorkbenchService, InstalledMcpServersViewId, LazyCollectionState, McpCapability, McpCollectionDefinition, McpConnectionState, McpDefinitionReference, mcpPromptPrefix, McpServerCacheState, McpStartServerInteraction } from '../common/mcpTypes.js';
 import { McpAddConfigurationCommand, McpInstallFromManifestCommand } from './mcpCommandsAddConfiguration.js';
 import { McpResourceQuickAccess, McpResourceQuickPick } from './mcpResourceQuickAccess.js';
 import { startServerAndWaitForLiveTools } from '../common/mcpTypesUtils.js';
+import { isContributionDisabled } from '../../chat/common/enablement.js';
 import './media/mcpServerAction.css';
 import { openPanelChatAndGetWidget } from './openPanelChatAndGetWidget.js';
 
@@ -104,6 +105,7 @@ export class ListMcpServerCommand extends Action2 {
 		const mcpService = accessor.get(IMcpService);
 		const commandService = accessor.get(ICommandService);
 		const quickInput = accessor.get(IQuickInputService);
+		const mcpWorkbenchService = accessor.get(IMcpWorkbenchService);
 
 		type ItemType = { id: string } & IQuickPickItem;
 
@@ -122,11 +124,16 @@ export class ListMcpServerCommand extends Action2 {
 				{ id: '$add', label: localize('mcp.addServer', 'Add Server'), description: localize('mcp.addServer.description', 'Add a new server configuration'), alwaysShow: true, iconClass: ThemeIcon.asClassName(Codicon.add) },
 				...Object.values(servers).filter(s => s!.length).flatMap((servers): (ItemType | IQuickPickSeparator)[] => [
 					{ type: 'separator', label: servers![0].collection.label, id: servers![0].collection.id },
-					...servers!.map(server => ({
-						id: server.definition.id,
-						label: server.definition.label,
-						description: McpConnectionState.toString(server.connectionState.read(reader)),
-					})),
+					...servers!.map(server => {
+						const disabled = isContributionDisabled(server.enablement.read(reader));
+						return {
+							id: server.definition.id,
+							label: server.definition.label,
+							description: disabled
+								? localize('mcp.disabled', 'Disabled')
+								: McpConnectionState.toString(server.connectionState.read(reader)),
+						};
+					}),
 				]),
 			];
 
@@ -153,7 +160,15 @@ export class ListMcpServerCommand extends Action2 {
 		} else if (picked.id === '$add') {
 			commandService.executeCommand(McpCommandIds.AddConfiguration);
 		} else {
-			commandService.executeCommand(McpCommandIds.ServerOptions, picked.id);
+			const server = mcpService.servers.get().find(s => s.definition.id === picked.id);
+			if (server && isContributionDisabled(server.enablement.get())) {
+				const workbenchServer = mcpWorkbenchService.local.find(s => s.id === picked.id);
+				if (workbenchServer) {
+					mcpWorkbenchService.open(workbenchServer);
+				}
+			} else {
+				commandService.executeCommand(McpCommandIds.ServerOptions, picked.id);
+			}
 		}
 	}
 }
@@ -550,9 +565,10 @@ export class MCPServerActionRendering extends Disposable implements IWorkbenchCo
 
 				protected override getHoverContents({ state, servers } = displayedStateCurrent.get()): string | undefined | IManagedHoverTooltipHTMLElement {
 					const link = (s: IMcpServer) => createMarkdownCommandLink({
-						title: s.definition.label,
+						text: s.definition.label,
 						id: McpCommandIds.ServerOptions,
 						arguments: [s.definition.id],
+						tooltip: localize('mcp.server.options.tooltip', 'Show server options for {0}', s.definition.label),
 					});
 
 					const single = servers.length === 1;
diff --git a/src/vs/workbench/contrib/mcp/browser/mcpElicitationService.ts b/src/vs/workbench/contrib/mcp/browser/mcpElicitationService.ts
index 622dc36f19850..0e64866bd27b4 100644
--- a/src/vs/workbench/contrib/mcp/browser/mcpElicitationService.ts
+++ b/src/vs/workbench/contrib/mcp/browser/mcpElicitationService.ts
@@ -12,13 +12,15 @@ import { DisposableStore } from '../../../../base/common/lifecycle.js';
 import { autorun } from '../../../../base/common/observable.js';
 import { isDefined } from '../../../../base/common/types.js';
 import { URI } from '../../../../base/common/uri.js';
+import { generateUuid } from '../../../../base/common/uuid.js';
 import { localize } from '../../../../nls.js';
 import { INotificationService, Severity } from '../../../../platform/notification/common/notification.js';
 import { IOpenerService } from '../../../../platform/opener/common/opener.js';
 import { IQuickInputService, IQuickPick, IQuickPickItem } from '../../../../platform/quickinput/common/quickInput.js';
 import { ChatElicitationRequestPart } from '../../chat/common/model/chatProgressTypes/chatElicitationRequestPart.js';
+import { ChatQuestionCarouselData } from '../../chat/common/model/chatProgressTypes/chatQuestionCarouselData.js';
 import { ChatModel } from '../../chat/common/model/chatModel.js';
-import { ElicitationState, IChatService } from '../../chat/common/chatService/chatService.js';
+import { ElicitationState, IChatQuestion, IChatQuestionAnswers, IChatQuestionValidation, IChatService } from '../../chat/common/chatService/chatService.js';
 import { ElicitationKind, ElicitResult, IFormModeElicitResult, IMcpElicitationService, IMcpServer, IMcpToolCallContext, IUrlModeElicitResult, McpConnectionState, MpcResponseError } from '../common/mcpTypes.js';
 import { mcpServerToSourceData } from '../common/mcpTypesUtils.js';
 import { MCP } from '../common/modelContextProtocol.js';
@@ -88,41 +90,52 @@ export class McpElicitationService implements IMcpElicitationService {
 			if (chatModel instanceof ChatModel) {
 				const request = chatModel.getRequests().at(-1);
 				if (request) {
-					const part = new ChatElicitationRequestPart(
-						localize('mcp.elicit.title', 'Request for Input'),
-						elicitation.message,
-						localize('msg.subtitle', "{0} (MCP Server)", server.definition.label),
-						localize('mcp.elicit.accept', 'Respond'),
-						localize('mcp.elicit.reject', 'Cancel'),
-						async () => {
-							const p = this._doElicitForm(elicitation, token);
-							resolve(p);
-							const result = await p;
-							part.acceptedResult = result.content;
-							return result.action === 'accept' ? ElicitationState.Accepted : ElicitationState.Rejected;
-						},
-						() => {
-							resolve({ action: 'decline' });
-							return Promise.resolve(ElicitationState.Rejected);
-						},
-						mcpServerToSourceData(server),
+					const { questions, idToPropertyMap } = this._convertSchemaToQuestions(elicitation);
+					const carousel = new ChatQuestionCarouselData(
+						questions,
+						/* allowSkip */ true,
+						/* resolveId */ undefined,
+						/* data */ undefined,
+						/* isUsed */ undefined,
+						/* message */ new MarkdownString(elicitation.message),
+						/* source */ mcpServerToSourceData(server),
 					);
-					chatModel.acceptResponseProgress(request, part);
+
+					chatModel.acceptResponseProgress(request, carousel);
+
+					store.add(token.onCancellationRequested(() => {
+						carousel.completion.complete({ answers: undefined });
+					}));
+
+					carousel.completion.p.then(result => {
+						if (!result.answers) {
+							resolve({ action: 'cancel' });
+						} else {
+							const content = this._convertCarouselAnswersToElicitResult(
+								result.answers,
+								idToPropertyMap,
+								elicitation.requestedSchema.properties,
+							);
+							resolve({ action: 'accept', content });
+						}
+					});
+					return;
 				}
-			} else {
-				const handle = this._notificationService.notify({
-					message: elicitation.message,
-					source: localize('mcp.elicit.source', 'MCP Server ({0})', server.definition.label),
-					severity: Severity.Info,
-					actions: {
-						primary: [store.add(new Action('mcp.elicit.give', localize('mcp.elicit.give', 'Respond'), undefined, true, () => resolve(this._doElicitForm(elicitation, token))))],
-						secondary: [store.add(new Action('mcp.elicit.cancel', localize('mcp.elicit.cancel', 'Cancel'), undefined, true, () => resolve({ action: 'decline' })))],
-					}
-				});
-				store.add(handle.onDidClose(() => resolve({ action: 'cancel' })));
-				store.add(token.onCancellationRequested(() => resolve({ action: 'cancel' })));
 			}
 
+			// Fallback: no chat session → notification + quickpick
+			const handle = this._notificationService.notify({
+				message: elicitation.message,
+				source: localize('mcp.elicit.source', 'MCP Server ({0})', server.definition.label),
+				severity: Severity.Info,
+				actions: {
+					primary: [store.add(new Action('mcp.elicit.give', localize('mcp.elicit.give', 'Respond'), undefined, true, () => resolve(this._doElicitForm(elicitation, token))))],
+					secondary: [store.add(new Action('mcp.elicit.cancel', localize('mcp.elicit.cancel', 'Cancel'), undefined, true, () => resolve({ action: 'decline' })))],
+				}
+			});
+			store.add(handle.onDidClose(() => resolve({ action: 'cancel' })));
+			store.add(token.onCancellationRequested(() => resolve({ action: 'cancel' })));
+
 		}).finally(() => store.dispose());
 
 		return { kind: ElicitationKind.Form, value, dispose: () => { } };
@@ -518,4 +531,191 @@ export class McpElicitationService implements IMcpElicitationService {
 		}
 		return { isValid: true, parsedValue: parsed };
 	}
+
+	/**
+	 * Converts an MCP elicitation schema into IChatQuestion[] for the carousel UI.
+	 * Returns the questions and a map from question ID to schema property name.
+	 */
+	private _convertSchemaToQuestions(elicitation: MCP.ElicitRequestFormParams | Pre20251125ElicitationParams): { questions: IChatQuestion[]; idToPropertyMap: Map<string, string> } {
+		const properties = Object.entries(elicitation.requestedSchema.properties);
+		const requiredFields = new Set(elicitation.requestedSchema.required || []);
+		const questions: IChatQuestion[] = [];
+		const idToPropertyMap = new Map<string, string>();
+
+		for (const [propertyName, schema] of properties) {
+			const id = generateUuid();
+			idToPropertyMap.set(id, propertyName);
+
+			const title = schema.title || propertyName;
+			const description = schema.description;
+			const isRequired = requiredFields.has(propertyName);
+
+			if (schema.type === 'boolean') {
+				questions.push({
+					id,
+					type: 'singleSelect',
+					title,
+					description,
+					required: isRequired,
+					allowFreeformInput: false,
+					options: [
+						{ id: 'true', label: localize('mcp.elicit.true', 'True'), value: 'true' },
+						{ id: 'false', label: localize('mcp.elicit.false', 'False'), value: 'false' },
+					],
+					defaultValue: schema.default !== undefined ? String(schema.default) : undefined,
+				});
+			} else if (isLegacyTitledEnumSchema(schema)) {
+				questions.push({
+					id,
+					type: 'singleSelect',
+					title,
+					description,
+					required: isRequired,
+					allowFreeformInput: false,
+					options: schema.enum.map((v, i) => ({
+						id: v,
+						label: schema.enumNames[i] ? `${v} - ${schema.enumNames[i]}` : v,
+						value: v,
+					})),
+					defaultValue: schema.default,
+				});
+			} else if (isTitledSingleEnumSchema(schema)) {
+				questions.push({
+					id,
+					type: 'singleSelect',
+					title,
+					description,
+					required: isRequired,
+					allowFreeformInput: false,
+					options: schema.oneOf.map(({ const: value, title: optTitle }) => ({
+						id: value,
+						label: optTitle ? `${value} - ${optTitle}` : value,
+						value,
+					})),
+					defaultValue: schema.default,
+				});
+			} else if (isUntitledEnumSchema(schema)) {
+				questions.push({
+					id,
+					type: 'singleSelect',
+					title,
+					description,
+					required: isRequired,
+					allowFreeformInput: false,
+					options: schema.enum.map(v => ({ id: v, label: v, value: v })),
+					defaultValue: schema.default,
+				});
+			} else if (isTitledMultiEnumSchema(schema)) {
+				questions.push({
+					id,
+					type: 'multiSelect',
+					title,
+					description,
+					required: isRequired,
+					allowFreeformInput: false,
+					options: schema.items.anyOf.map(({ const: value, title: optTitle }) => ({
+						id: value,
+						label: optTitle ? `${value} - ${optTitle}` : value,
+						value,
+					})),
+					defaultValue: schema.default,
+				});
+			} else if (isUntitledMultiEnumSchema(schema)) {
+				questions.push({
+					id,
+					type: 'multiSelect',
+					title,
+					description,
+					required: isRequired,
+					allowFreeformInput: false,
+					options: schema.items.enum.map(v => ({ id: v, label: v, value: v })),
+					defaultValue: schema.default,
+				});
+			} else {
+				// String, number, integer → text input with validation
+				const validation: IChatQuestionValidation = {};
+				if (schema.type === 'string') {
+					if (schema.minLength !== undefined) { validation.minLength = schema.minLength; }
+					if (schema.maxLength !== undefined) { validation.maxLength = schema.maxLength; }
+					if (schema.format) { validation.format = schema.format; }
+				} else if (schema.type === 'number' || schema.type === 'integer') {
+					if (schema.minimum !== undefined) { validation.minimum = schema.minimum; }
+					if (schema.maximum !== undefined) { validation.maximum = schema.maximum; }
+					if (schema.type === 'integer') { validation.isInteger = true; }
+				}
+
+				questions.push({
+					id,
+					type: 'text',
+					title,
+					description,
+					required: isRequired,
+					defaultValue: schema.default !== undefined ? String(schema.default) : undefined,
+					validation: Object.keys(validation).length > 0 ? validation : undefined,
+				});
+			}
+		}
+
+		return { questions, idToPropertyMap };
+	}
+
+	/**
+	 * Converts carousel answers (keyed by question ID) back into the
+	 * MCP ElicitResult content format (keyed by schema property names),
+	 * coercing types as needed.
+	 */
+	private _convertCarouselAnswersToElicitResult(
+		answers: IChatQuestionAnswers,
+		idToPropertyMap: Map<string, string>,
+		schemaProperties: Record<string, MCP.PrimitiveSchemaDefinition>,
+	): Record<string, string | number | boolean | string[]> {
+		const content: Record<string, string | number | boolean | string[]> = {};
+
+		for (const [questionId, answer] of Object.entries(answers)) {
+			const propertyName = idToPropertyMap.get(questionId);
+			if (!propertyName) {
+				continue;
+			}
+
+			const schema = schemaProperties[propertyName];
+			if (!schema) {
+				continue;
+			}
+
+			// Extract the raw value from structured answers
+			let rawValue: unknown = answer;
+			if (typeof answer === 'object' && answer !== null) {
+				const obj = answer as Record<string, unknown>;
+				if ('selectedValue' in obj) {
+					rawValue = obj.selectedValue;
+				} else if ('selectedValues' in obj) {
+					rawValue = obj.selectedValues;
+				} else if ('freeformValue' in obj && obj.freeformValue) {
+					rawValue = obj.freeformValue;
+				}
+			}
+
+			if (rawValue === undefined || rawValue === null) {
+				continue;
+			}
+
+			// Type coercion based on schema
+			if (schema.type === 'boolean') {
+				content[propertyName] = rawValue === 'true' || rawValue === true;
+			} else if (schema.type === 'number' || schema.type === 'integer') {
+				const num = Number(rawValue);
+				if (!isNaN(num)) {
+					content[propertyName] = num;
+				}
+			} else if (schema.type === 'array') {
+				if (Array.isArray(rawValue)) {
+					content[propertyName] = rawValue.map(v => String(v));
+				}
+			} else {
+				content[propertyName] = String(rawValue);
+			}
+		}
+
+		return content;
+	}
 }
diff --git a/src/vs/workbench/contrib/mcp/browser/mcpGatewayService.ts b/src/vs/workbench/contrib/mcp/browser/mcpGatewayService.ts
index 49bb014e5d979..4d2d9df2c4914 100644
--- a/src/vs/workbench/contrib/mcp/browser/mcpGatewayService.ts
+++ b/src/vs/workbench/contrib/mcp/browser/mcpGatewayService.ts
@@ -5,6 +5,7 @@
 
 import { URI } from '../../../../base/common/uri.js';
 import { ProxyChannel } from '../../../../base/parts/ipc/common/ipc.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
 import { IMcpGatewayService, McpGatewayChannelName } from '../../../../platform/mcp/common/mcpGateway.js';
 import { IRemoteAgentService } from '../../../services/remote/common/remoteAgentService.js';
 import { IMcpGatewayResult, IWorkbenchMcpGatewayService } from '../common/mcpGatewayService.js';
@@ -23,28 +24,36 @@ export class BrowserMcpGatewayService implements IWorkbenchMcpGatewayService {
 
 	constructor(
 		@IRemoteAgentService private readonly _remoteAgentService: IRemoteAgentService,
+		@ILogService private readonly _logService: ILogService,
 	) { }
 
 	async createGateway(inRemote: boolean): Promise<IMcpGatewayResult | undefined> {
+		this._logService.debug(`[McpGateway][BrowserWorkbench] createGateway requested (inRemote=${inRemote})`);
+
 		// Browser can only create gateways in remote environment
 		if (!inRemote) {
+			this._logService.info('[McpGateway][BrowserWorkbench] Cannot create local gateway in browser environment');
 			return undefined;
 		}
 
 		const connection = this._remoteAgentService.getConnection();
 		if (!connection) {
-			// Serverless web environment - no gateway available
+			this._logService.info('[McpGateway][BrowserWorkbench] No remote connection available (serverless web)');
 			return undefined;
 		}
 
+		this._logService.info('[McpGateway][BrowserWorkbench] Creating remote gateway via remote server');
 		// Use the remote server's gateway service
 		return connection.withChannel(McpGatewayChannelName, async channel => {
 			const service = ProxyChannel.toService<IMcpGatewayService>(channel);
 			const info = await service.createGateway(undefined);
+			const address = URI.revive(info.address);
+			this._logService.info(`[McpGateway][BrowserWorkbench] Remote gateway created: ${address}`);
 
 			return {
-				address: URI.revive(info.address),
+				address,
 				dispose: () => {
+					this._logService.info(`[McpGateway][BrowserWorkbench] Disposing remote gateway: ${info.gatewayId}`);
 					service.disposeGateway(info.gatewayId);
 				}
 			};
diff --git a/src/vs/workbench/contrib/mcp/browser/mcpGatewayToolBrokerContribution.ts b/src/vs/workbench/contrib/mcp/browser/mcpGatewayToolBrokerContribution.ts
index 175bb839214a9..4c041d05f4770 100644
--- a/src/vs/workbench/contrib/mcp/browser/mcpGatewayToolBrokerContribution.ts
+++ b/src/vs/workbench/contrib/mcp/browser/mcpGatewayToolBrokerContribution.ts
@@ -4,6 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { IWorkbenchContribution } from '../../../common/contributions.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
 import { McpGatewayToolBrokerChannelName } from '../../../../platform/mcp/common/mcpGateway.js';
 import { IRemoteAgentService } from '../../../services/remote/common/remoteAgentService.js';
 import { IMcpService } from '../common/mcpTypes.js';
@@ -13,7 +14,8 @@ export class McpGatewayToolBrokerContribution implements IWorkbenchContribution
 	constructor(
 		@IRemoteAgentService remoteAgentService: IRemoteAgentService,
 		@IMcpService mcpService: IMcpService,
+		@ILogService logService: ILogService,
 	) {
-		remoteAgentService.getConnection()?.registerChannel(McpGatewayToolBrokerChannelName, new McpGatewayToolBrokerChannel(mcpService));
+		remoteAgentService.getConnection()?.registerChannel(McpGatewayToolBrokerChannelName, new McpGatewayToolBrokerChannel(mcpService, logService));
 	}
 }
diff --git a/src/vs/workbench/contrib/mcp/browser/mcpLanguageFeatures.ts b/src/vs/workbench/contrib/mcp/browser/mcpLanguageFeatures.ts
index 254537d67c9a2..285e27f037057 100644
--- a/src/vs/workbench/contrib/mcp/browser/mcpLanguageFeatures.ts
+++ b/src/vs/workbench/contrib/mcp/browser/mcpLanguageFeatures.ts
@@ -388,9 +388,9 @@ export class McpLanguageFeatures extends Disposable implements IWorkbenchContrib
 
 		function pushAnnotation(savedId: string, offset: number, saved: IResolvedValue): InlayHint {
 			const tooltip = new MarkdownString([
-				createMarkdownCommandLink({ id: McpCommandIds.EditStoredInput, title: localize('edit', 'Edit'), arguments: [savedId, model.uri, mcpConfigurationSection, inConfig!.target] }),
-				createMarkdownCommandLink({ id: McpCommandIds.RemoveStoredInput, title: localize('clear', 'Clear'), arguments: [inConfig!.scope, savedId] }),
-				createMarkdownCommandLink({ id: McpCommandIds.RemoveStoredInput, title: localize('clearAll', 'Clear All'), arguments: [inConfig!.scope] }),
+				createMarkdownCommandLink({ id: McpCommandIds.EditStoredInput, text: localize('edit', 'Edit'), arguments: [savedId, model.uri, mcpConfigurationSection, inConfig!.target], tooltip: localize('edit.savedValue.tooltip', 'Edit saved value') }),
+				createMarkdownCommandLink({ id: McpCommandIds.RemoveStoredInput, text: localize('clear', 'Clear'), arguments: [inConfig!.scope, savedId], tooltip: localize('clear.savedValue.tooltip', 'Clear saved value') }),
+				createMarkdownCommandLink({ id: McpCommandIds.RemoveStoredInput, text: localize('clearAll', 'Clear All'), arguments: [inConfig!.scope], tooltip: localize('clearAll.savedValues.tooltip', 'Clear all saved values') }),
 			].join(' | '), { isTrusted: true });
 
 			const hint: InlayHint = {
diff --git a/src/vs/workbench/contrib/mcp/browser/mcpServerActions.ts b/src/vs/workbench/contrib/mcp/browser/mcpServerActions.ts
index 10f62eb9c831e..25152d40926d1 100644
--- a/src/vs/workbench/contrib/mcp/browser/mcpServerActions.ts
+++ b/src/vs/workbench/contrib/mcp/browser/mcpServerActions.ts
@@ -37,6 +37,7 @@ import { ExtensionAction } from '../../extensions/browser/extensionsActions.js';
 import { ActionWithDropdownActionViewItem, IActionWithDropdownActionViewItemOptions } from '../../../../base/browser/ui/dropdown/dropdownActionViewItem.js';
 import { IContextMenuProvider } from '../../../../base/browser/contextmenu.js';
 import Severity from '../../../../base/common/severity.js';
+import { ContributionEnablementState, isContributionDisabled, isContributionEnabled } from '../../chat/common/enablement.js';
 
 export interface IMcpServerActionChangeEvent extends IActionChangeEvent {
 	readonly hidden?: boolean;
@@ -133,10 +134,12 @@ export class ButtonWithDropDownExtensionAction extends McpServerAction {
 		this._onDidChange.fire({ menuActions: this._menuActions });
 
 		if (this.primaryAction) {
+			this.hidden = false;
 			this.enabled = this.primaryAction.enabled;
 			this.label = this.getLabel(this.primaryAction as ExtensionAction);
 			this.tooltip = this.primaryAction.tooltip;
 		} else {
+			this.hidden = true;
 			this.enabled = false;
 		}
 	}
@@ -508,6 +511,174 @@ export class UninstallAction extends McpServerAction {
 	}
 }
 
+export class EnableMcpServerGloballyAction extends McpServerAction {
+
+	static readonly ID = 'mcpServer.enableGlobally';
+
+	constructor(
+		@IMcpService private readonly mcpService: IMcpService,
+	) {
+		super(EnableMcpServerGloballyAction.ID, localize('enableGlobally', "Enable"), McpServerAction.LABEL_ACTION_CLASS);
+		this.tooltip = localize('enableGloballyTooltip', "Enable this MCP server");
+		this.update();
+	}
+
+	update(): void {
+		this.enabled = false;
+		if (!this.mcpServer?.local) {
+			return;
+		}
+		const server = this.mcpService.servers.get().find(s => s.definition.id === this.mcpServer?.id);
+		if (!server) {
+			return;
+		}
+		const enablement = server.enablement.get();
+		this.enabled = isContributionDisabled(enablement);
+	}
+
+	override async run(): Promise<void> {
+		if (!this.mcpServer) {
+			return;
+		}
+		this.mcpService.enablementModel.setEnabled(this.mcpServer.id, ContributionEnablementState.EnabledProfile);
+	}
+}
+
+export class EnableMcpServerForWorkspaceAction extends McpServerAction {
+
+	static readonly ID = 'mcpServer.enableForWorkspace';
+
+	constructor(
+		@IMcpService private readonly mcpService: IMcpService,
+		@IWorkspaceContextService private readonly workspaceService: IWorkspaceContextService,
+	) {
+		super(EnableMcpServerForWorkspaceAction.ID, localize('enableForWorkspace', "Enable (Workspace)"), McpServerAction.LABEL_ACTION_CLASS);
+		this.tooltip = localize('enableForWorkspaceTooltip', "Enable this MCP server only in this workspace");
+		this.update();
+	}
+
+	update(): void {
+		this.enabled = false;
+		if (!this.mcpServer?.local) {
+			return;
+		}
+		if (this.workspaceService.getWorkbenchState() === WorkbenchState.EMPTY) {
+			return;
+		}
+		const server = this.mcpService.servers.get().find(s => s.definition.id === this.mcpServer?.id);
+		if (!server) {
+			return;
+		}
+		const enablement = server.enablement.get();
+		this.enabled = isContributionDisabled(enablement);
+	}
+
+	override async run(): Promise<void> {
+		if (!this.mcpServer) {
+			return;
+		}
+		this.mcpService.enablementModel.setEnabled(this.mcpServer.id, ContributionEnablementState.EnabledWorkspace);
+	}
+}
+
+export class DisableMcpServerGloballyAction extends McpServerAction {
+
+	static readonly ID = 'mcpServer.disableGlobally';
+
+	constructor(
+		@IMcpService private readonly mcpService: IMcpService,
+	) {
+		super(DisableMcpServerGloballyAction.ID, localize('disableGlobally', "Disable"), McpServerAction.LABEL_ACTION_CLASS);
+		this.tooltip = localize('disableGloballyTooltip', "Disable this MCP server");
+		this.update();
+	}
+
+	update(): void {
+		this.enabled = false;
+		if (!this.mcpServer?.local) {
+			return;
+		}
+		const server = this.mcpService.servers.get().find(s => s.definition.id === this.mcpServer?.id);
+		if (!server) {
+			return;
+		}
+		const enablement = server.enablement.get();
+		this.enabled = isContributionEnabled(enablement);
+	}
+
+	override async run(): Promise<void> {
+		if (!this.mcpServer) {
+			return;
+		}
+		this.mcpService.enablementModel.setEnabled(this.mcpServer.id, ContributionEnablementState.DisabledProfile);
+	}
+}
+
+export class DisableMcpServerForWorkspaceAction extends McpServerAction {
+
+	static readonly ID = 'mcpServer.disableForWorkspace';
+
+	constructor(
+		@IMcpService private readonly mcpService: IMcpService,
+		@IWorkspaceContextService private readonly workspaceService: IWorkspaceContextService,
+	) {
+		super(DisableMcpServerForWorkspaceAction.ID, localize('disableForWorkspace', "Disable (Workspace)"), McpServerAction.LABEL_ACTION_CLASS);
+		this.tooltip = localize('disableForWorkspaceTooltip', "Disable this MCP server only in this workspace");
+		this.update();
+	}
+
+	update(): void {
+		this.enabled = false;
+		if (!this.mcpServer?.local) {
+			return;
+		}
+		if (this.workspaceService.getWorkbenchState() === WorkbenchState.EMPTY) {
+			return;
+		}
+		const server = this.mcpService.servers.get().find(s => s.definition.id === this.mcpServer?.id);
+		if (!server) {
+			return;
+		}
+		const enablement = server.enablement.get();
+		this.enabled = isContributionEnabled(enablement);
+	}
+
+	override async run(): Promise<void> {
+		if (!this.mcpServer) {
+			return;
+		}
+		this.mcpService.enablementModel.setEnabled(this.mcpServer.id, ContributionEnablementState.DisabledWorkspace);
+	}
+}
+
+export class EnableMcpDropDownAction extends ButtonWithDropDownExtensionAction {
+
+	constructor(
+		@IInstantiationService instantiationService: IInstantiationService,
+	) {
+		super('mcpServer.enable', McpServerAction.LABEL_ACTION_CLASS, [
+			[
+				instantiationService.createInstance(EnableMcpServerGloballyAction),
+				instantiationService.createInstance(EnableMcpServerForWorkspaceAction),
+			]
+		]);
+	}
+}
+
+export class DisableMcpDropDownAction extends ButtonWithDropDownExtensionAction {
+
+	constructor(
+		@IInstantiationService instantiationService: IInstantiationService,
+	) {
+		super('mcpServer.disable', McpServerAction.LABEL_ACTION_CLASS, [
+			[
+				instantiationService.createInstance(DisableMcpServerGloballyAction),
+				instantiationService.createInstance(DisableMcpServerForWorkspaceAction),
+			]
+		]);
+	}
+}
+
 export function getContextMenuActions(mcpServer: IWorkbenchMcpServer, isEditorAction: boolean, instantiationService: IInstantiationService): IAction[][] {
 	return instantiationService.invokeFunction(accessor => {
 		const workspaceService = accessor.get(IWorkspaceContextService);
@@ -524,6 +695,12 @@ export function getContextMenuActions(mcpServer: IWorkbenchMcpServer, isEditorAc
 				instantiationService.createInstance(StopServerAction),
 				instantiationService.createInstance(RestartServerAction),
 			]);
+			groups.push([
+				instantiationService.createInstance(EnableMcpServerGloballyAction),
+				instantiationService.createInstance(EnableMcpServerForWorkspaceAction),
+				instantiationService.createInstance(DisableMcpServerGloballyAction),
+				instantiationService.createInstance(DisableMcpServerForWorkspaceAction),
+			]);
 			groups.push([
 				instantiationService.createInstance(AuthServerAction),
 			]);
diff --git a/src/vs/workbench/contrib/mcp/browser/mcpServerEditor.ts b/src/vs/workbench/contrib/mcp/browser/mcpServerEditor.ts
index 034985bdf4466..1f0f633be661a 100644
--- a/src/vs/workbench/contrib/mcp/browser/mcpServerEditor.ts
+++ b/src/vs/workbench/contrib/mcp/browser/mcpServerEditor.ts
@@ -38,7 +38,7 @@ import { IExtensionService } from '../../../services/extensions/common/extension
 import { IHoverService } from '../../../../platform/hover/browser/hover.js';
 import { IMcpServerContainer, IMcpServerEditorOptions, IMcpWorkbenchService, IWorkbenchMcpServer, McpServerContainers, McpServerInstallState } from '../common/mcpTypes.js';
 import { StarredWidget, McpServerIconWidget, McpServerStatusWidget, McpServerWidget, onClick, PublisherWidget, McpServerScopeBadgeWidget, LicenseWidget } from './mcpServerWidgets.js';
-import { ButtonWithDropDownExtensionAction, ButtonWithDropdownExtensionActionViewItem, DropDownAction, InstallAction, InstallingLabelAction, InstallInRemoteAction, InstallInWorkspaceAction, ManageMcpServerAction, McpServerStatusAction, UninstallAction } from './mcpServerActions.js';
+import { ButtonWithDropDownExtensionAction, ButtonWithDropdownExtensionActionViewItem, DisableMcpDropDownAction, DropDownAction, EnableMcpDropDownAction, InstallAction, InstallingLabelAction, InstallInRemoteAction, InstallInWorkspaceAction, ManageMcpServerAction, McpServerStatusAction, UninstallAction } from './mcpServerActions.js';
 import { McpServerEditorInput } from './mcpServerEditorInput.js';
 import { ILocalMcpServer, IGalleryMcpServerConfiguration, IMcpServerPackage, IMcpServerKeyValueInput, RegistryType } from '../../../../platform/mcp/common/mcpManagement.js';
 import { IActionViewItemOptions } from '../../../../base/browser/ui/actionbar/actionViewItems.js';
@@ -251,6 +251,8 @@ export class McpServerEditor extends EditorPane {
 					this.instantiationService.createInstance(InstallInRemoteAction, false)
 				]
 			]),
+			this.instantiationService.createInstance(EnableMcpDropDownAction),
+			this.instantiationService.createInstance(DisableMcpDropDownAction),
 			this.instantiationService.createInstance(ManageMcpServerAction, true),
 		];
 
diff --git a/src/vs/workbench/contrib/mcp/browser/mcpServersView.ts b/src/vs/workbench/contrib/mcp/browser/mcpServersView.ts
index 9e82f119e8830..864cc4f5f8cbe 100644
--- a/src/vs/workbench/contrib/mcp/browser/mcpServersView.ts
+++ b/src/vs/workbench/contrib/mcp/browser/mcpServersView.ts
@@ -270,7 +270,7 @@ export class McpServersListView extends AbstractExtensionsListView<IWorkbenchMcp
 		const title = dom.append(welcomeContent, dom.$('.mcp-welcome-title'));
 		title.textContent = localize('mcp.welcome.title', "MCP Servers");
 
-		const settingsCommandLink = createMarkdownCommandLink({ id: 'workbench.action.openSettings', arguments: [`@id:${mcpGalleryServiceEnablementConfig}`], title: mcpGalleryServiceEnablementConfig, tooltip: localize('mcp.welcome.settings.tooltip', "Open Settings") }).toString();
+		const settingsCommandLink = createMarkdownCommandLink({ id: 'workbench.action.openSettings', arguments: [`@id:${mcpGalleryServiceEnablementConfig}`], text: mcpGalleryServiceEnablementConfig, tooltip: localize('mcp.welcome.settings.tooltip', "Open Settings") }).toString();
 		const description = dom.append(welcomeContent, dom.$('.mcp-welcome-description'));
 		const markdownResult = this._register(this.markdownRendererService.render(
 			new MarkdownString(
diff --git a/src/vs/workbench/contrib/mcp/browser/mcpWorkbenchService.ts b/src/vs/workbench/contrib/mcp/browser/mcpWorkbenchService.ts
index a87f598400655..342092dbd7299 100644
--- a/src/vs/workbench/contrib/mcp/browser/mcpWorkbenchService.ts
+++ b/src/vs/workbench/contrib/mcp/browser/mcpWorkbenchService.ts
@@ -37,11 +37,12 @@ import { IRemoteAgentService } from '../../../services/remote/common/remoteAgent
 import { mcpConfigurationSection } from '../common/mcpConfiguration.js';
 import { McpServerInstallData, McpServerInstallClassification } from '../common/mcpServer.js';
 import { HasInstalledMcpServersContext, IMcpConfigPath, IMcpService, IMcpWorkbenchService, IWorkbenchMcpServer, McpCollectionSortOrder, McpServerEnablementState, McpServerInstallState, McpServerEnablementStatus, McpServersGalleryStatusContext } from '../common/mcpTypes.js';
+import { ContributionEnablementState } from '../../chat/common/enablement.js';
 import { McpServerEditorInput } from './mcpServerEditorInput.js';
 import { IMcpGalleryManifestService } from '../../../../platform/mcp/common/mcpGalleryManifest.js';
 import { IIterativePager, IIterativePage } from '../../../../base/common/paging.js';
 import { IExtensionsWorkbenchService } from '../../extensions/common/extensions.js';
-import { runOnChange } from '../../../../base/common/observable.js';
+import { autorun, runOnChange } from '../../../../base/common/observable.js';
 import Severity from '../../../../base/common/severity.js';
 import { Queue } from '../../../../base/common/async.js';
 
@@ -221,6 +222,14 @@ export class McpWorkbenchService extends Disposable implements IMcpWorkbenchServ
 			this._local = this.sort(this._local);
 			this._onChange.fire(undefined);
 		}));
+
+		// React to enablement changes on individual servers
+		this._register(autorun(reader => {
+			for (const server of mcpService.servers.read(reader)) {
+				server.enablement.read(reader);
+			}
+			this._onChange.fire(undefined);
+		}));
 	}
 
 	private async onDidChangeProfile() {
@@ -743,10 +752,31 @@ export class McpWorkbenchService extends Disposable implements IMcpWorkbenchServ
 			return enablementStatus;
 		}
 
-		if (!this.mcpService.servers.get().find(s => s.definition.id === mcpServer.id)) {
+		const server = this.mcpService.servers.get().find(s => s.definition.id === mcpServer.id);
+		if (!server) {
 			return { state: McpServerEnablementState.Disabled };
 		}
 
+		const enablement = server.enablement.get();
+		if (enablement === ContributionEnablementState.DisabledProfile) {
+			return {
+				state: McpServerEnablementState.DisabledProfile,
+				message: {
+					severity: Severity.Info,
+					text: new MarkdownString(localize('disabled globally', "This MCP server is disabled."))
+				}
+			};
+		}
+		if (enablement === ContributionEnablementState.DisabledWorkspace) {
+			return {
+				state: McpServerEnablementState.DisabledWorkspace,
+				message: {
+					severity: Severity.Info,
+					text: new MarkdownString(localize('disabled in workspace', "This MCP server is disabled for this workspace."))
+				}
+			};
+		}
+
 		return undefined;
 	}
 
diff --git a/src/vs/workbench/contrib/mcp/common/discovery/installedMcpServersDiscovery.ts b/src/vs/workbench/contrib/mcp/common/discovery/installedMcpServersDiscovery.ts
index 601ce1eff09bb..c3d16718ad3b2 100644
--- a/src/vs/workbench/contrib/mcp/common/discovery/installedMcpServersDiscovery.ts
+++ b/src/vs/workbench/contrib/mcp/common/discovery/installedMcpServersDiscovery.ts
@@ -96,6 +96,7 @@ export class InstalledMcpServersDiscovery extends Disposable implements IMcpDisc
 					env: config.env || {},
 					envFile: config.envFile,
 					cwd: config.cwd,
+					sandbox: server.rootSandbox
 				};
 
 				definitions[1].push({
@@ -103,7 +104,6 @@ export class InstalledMcpServersDiscovery extends Disposable implements IMcpDisc
 					label: server.name,
 					launch,
 					sandboxEnabled: config.type === 'http' ? undefined : config.sandboxEnabled,
-					sandbox: config.type === 'http' || !config.sandboxEnabled ? undefined : config.sandbox,
 					cacheNonce: await McpServerLaunch.hash(launch),
 					roots: mcpConfigPath?.workspaceFolder ? [mcpConfigPath.workspaceFolder.uri] : undefined,
 					variableReplacement: {
diff --git a/src/vs/workbench/contrib/mcp/common/discovery/nativeMcpDiscoveryAdapters.ts b/src/vs/workbench/contrib/mcp/common/discovery/nativeMcpDiscoveryAdapters.ts
index 3287e0347e7ca..fe7aca88798d1 100644
--- a/src/vs/workbench/contrib/mcp/common/discovery/nativeMcpDiscoveryAdapters.ts
+++ b/src/vs/workbench/contrib/mcp/common/discovery/nativeMcpDiscoveryAdapters.ts
@@ -49,6 +49,7 @@ export async function claudeConfigToServerDefinition(idPrefix: string, contents:
 			env: server.env || {},
 			envFile: undefined,
 			cwd: cwd?.fsPath,
+			sandbox: undefined
 		};
 
 		return {
diff --git a/src/vs/workbench/contrib/mcp/common/discovery/pluginMcpDiscovery.ts b/src/vs/workbench/contrib/mcp/common/discovery/pluginMcpDiscovery.ts
index 6c4f50fea5c1f..7cb6a6efebdd5 100644
--- a/src/vs/workbench/contrib/mcp/common/discovery/pluginMcpDiscovery.ts
+++ b/src/vs/workbench/contrib/mcp/common/discovery/pluginMcpDiscovery.ts
@@ -8,7 +8,6 @@ import { Disposable, DisposableResourceMap } from '../../../../../base/common/li
 import { ResourceSet } from '../../../../../base/common/map.js';
 import { Schemas } from '../../../../../base/common/network.js';
 import { autorun } from '../../../../../base/common/observable.js';
-import { basename } from '../../../../../base/common/resources.js';
 import { isDefined } from '../../../../../base/common/types.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { ConfigurationTarget } from '../../../../../platform/configuration/common/configuration.js';
@@ -19,6 +18,7 @@ import {
 	IAgentPluginMcpServerDefinition,
 	IAgentPluginService
 } from '../../../chat/common/plugins/agentPluginService.js';
+import { isContributionEnabled } from '../../../chat/common/enablement.js';
 import { IMcpRegistry } from '../mcpRegistryTypes.js';
 import { McpCollectionSortOrder, McpServerDefinition, McpServerLaunch, McpServerTransportType, McpServerTrust } from '../mcpTypes.js';
 import { IMcpDiscovery } from './mcpDiscovery.js';
@@ -40,6 +40,9 @@ export class PluginMcpDiscovery extends Disposable implements IMcpDiscovery {
 			const plugins = this._agentPluginService.plugins.read(reader);
 			const seen = new ResourceSet();
 			for (const plugin of plugins) {
+				if (!isContributionEnabled(plugin.enablement.read(reader))) {
+					continue;
+				}
 				seen.add(plugin.uri);
 
 				let collectionState = this._collections.get(plugin.uri);
@@ -61,16 +64,16 @@ export class PluginMcpDiscovery extends Disposable implements IMcpDiscovery {
 		const collectionId = `plugin.${plugin.uri}`;
 		return this._mcpRegistry.registerCollection({
 			id: collectionId,
-			label: `${basename(plugin.uri)}/.mcp.json`,
+			label: `${plugin.label} (Agent Plugin)`,
 			remoteAuthority: plugin.uri.scheme === Schemas.vscodeRemote ? plugin.uri.authority : null,
 			configTarget: ConfigurationTarget.USER,
 			scope: StorageScope.PROFILE,
-			trustBehavior: McpServerTrust.Kind.TrustedOnNonce,
+			trustBehavior: McpServerTrust.Kind.Trusted,
 			serverDefinitions: plugin.mcpServerDefinitions.map(defs =>
 				defs.map(d => this._toServerDefinition(collectionId, d)).filter(isDefined)),
 			presentation: {
 				origin: plugin.uri,
-				order: McpCollectionSortOrder.Filesystem + 1,
+				order: McpCollectionSortOrder.Plugin,
 			},
 		});
 	}
@@ -101,6 +104,7 @@ export class PluginMcpDiscovery extends Disposable implements IMcpDiscovery {
 				env: config.env ? { ...config.env } : {},
 				envFile: config.envFile,
 				cwd: config.cwd,
+				sandbox: undefined,
 			};
 		}
 
diff --git a/src/vs/workbench/contrib/mcp/common/mcpConfiguration.ts b/src/vs/workbench/contrib/mcp/common/mcpConfiguration.ts
index e74c8948c3cc2..fce88654401e4 100644
--- a/src/vs/workbench/contrib/mcp/common/mcpConfiguration.ts
+++ b/src/vs/workbench/contrib/mcp/common/mcpConfiguration.ts
@@ -185,20 +185,23 @@ export const mcpServerSchema: IJSONSchema = {
 	additionalProperties: false,
 	properties: {
 		sandbox: {
-			description: localize('app.mcp.json.sandbox', "Default sandbox settings for running servers."),
+			description: localize('app.mcp.json.sandbox', "Sandbox config that determines file system and network access. Sandboxing is enabled when sandboxEnabled property is set at the server level on Mac OS and Linux only."),
 			type: 'object',
 			additionalProperties: false,
 			properties: {
 				network: {
+					description: localize('app.mcp.json.sandbox.network', "Network access settings for the sandboxed server."),
 					type: 'object',
 					additionalProperties: false,
 					properties: {
 						allowedDomains: {
+							description: localize('app.mcp.json.sandbox.network.allowedDomains', "List of domains that the server is allowed to access. Wildcards are supported, e.g. `*.example.com`."),
 							type: 'array',
 							items: { type: 'string' },
 							default: []
 						},
 						deniedDomains: {
+							description: localize('app.mcp.json.sandbox.network.deniedDomains', "List of domains that the server is not allowed to access. e.g. `invalid.example.com`."),
 							type: 'array',
 							items: { type: 'string' },
 							default: []
@@ -206,20 +209,24 @@ export const mcpServerSchema: IJSONSchema = {
 					}
 				},
 				filesystem: {
+					description: localize('app.mcp.json.sandbox.filesystem', "Filesystem access settings for the sandboxed server. Glob patterns are supported for Mac OS only."),
 					type: 'object',
 					additionalProperties: false,
 					properties: {
 						denyRead: {
+							description: localize('app.mcp.json.sandbox.filesystem.denyRead', "List of file paths that the server is not allowed to read. By default, all files are allowed to be read. e.g. `~/src/secrets`."),
 							type: 'array',
 							items: { type: 'string' },
 							default: []
 						},
 						allowWrite: {
+							description: localize('app.mcp.json.sandbox.filesystem.allowWrite', "List of file paths that the server is allowed to write to. e.g. `~/src/`."),
 							type: 'array',
 							items: { type: 'string' },
 							default: []
 						},
 						denyWrite: {
+							description: localize('app.mcp.json.sandbox.filesystem.denyWrite', "List of file paths that the server is not allowed to write to. e.g. `~/src/auth/`."),
 							type: 'array',
 							items: { type: 'string' },
 							default: []
diff --git a/src/vs/workbench/contrib/mcp/common/mcpGatewayToolBrokerChannel.ts b/src/vs/workbench/contrib/mcp/common/mcpGatewayToolBrokerChannel.ts
index 88a1da8b4b6d8..7e4e2c186918b 100644
--- a/src/vs/workbench/contrib/mcp/common/mcpGatewayToolBrokerChannel.ts
+++ b/src/vs/workbench/contrib/mcp/common/mcpGatewayToolBrokerChannel.ts
@@ -8,6 +8,7 @@ import { Emitter, Event } from '../../../../base/common/event.js';
 import { Disposable } from '../../../../base/common/lifecycle.js';
 import { autorun } from '../../../../base/common/observable.js';
 import { IServerChannel } from '../../../../base/parts/ipc/common/ipc.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
 import { IGatewayCallToolResult, IGatewayServerResources, IGatewayServerResourceTemplates } from '../../../../platform/mcp/common/mcpGateway.js';
 import { MCP } from '../../../../platform/mcp/common/modelContextProtocol.js';
 import { McpServer } from './mcpServer.js';
@@ -30,10 +31,25 @@ export class McpGatewayToolBrokerChannel extends Disposable implements IServerCh
 	private readonly _serverIdMap = new Map<string, number>();
 	private _nextServerIndex = 0;
 
+	/**
+	 * Per-server promise that races server startup against the grace period timeout.
+	 * Once set for a server, subsequent list calls await the already-resolved promise
+	 * and return immediately instead of waiting again.
+	 *
+	 * The `resolved` flag tracks whether the promise has settled. If a server's
+	 * cacheState regresses to Unknown/Outdated after the promise resolved (e.g.
+	 * after a cache reset), `_waitForStartup` discards the stale entry and creates
+	 * a fresh race so the server gets another chance to start.
+	 */
+	private readonly _startupGrace = new Map<string, { promise: Promise<boolean>; resolved: boolean }>();
+
 	constructor(
 		private readonly _mcpService: IMcpService,
+		private readonly _logService: ILogService,
+		private readonly _startupGracePeriodMs = 5000,
 	) {
 		super();
+		this._logService.debug('[McpGateway][ToolBroker] Initialized');
 
 		let toolsInitialized = false;
 		this._register(autorun(reader => {
@@ -42,6 +58,7 @@ export class McpGatewayToolBrokerChannel extends Disposable implements IServerCh
 			}
 
 			if (toolsInitialized) {
+				this._logService.debug('[McpGateway][ToolBroker] Tools changed, firing onDidChangeTools');
 				this._onDidChangeTools.fire();
 			} else {
 				toolsInitialized = true;
@@ -55,6 +72,7 @@ export class McpGatewayToolBrokerChannel extends Disposable implements IServerCh
 			}
 
 			if (resourcesInitialized) {
+				this._logService.debug('[McpGateway][ToolBroker] Resources changed, firing onDidChangeResources');
 				this._onDidChangeResources.fire();
 			} else {
 				resourcesInitialized = true;
@@ -81,6 +99,50 @@ export class McpGatewayToolBrokerChannel extends Disposable implements IServerCh
 		return undefined;
 	}
 
+	private _waitForStartup(server: IMcpServer): Promise<boolean> {
+		const id = server.definition.id;
+		const existing = this._startupGrace.get(id);
+		// If the previous grace promise already resolved but the server is still
+		// Unknown/Outdated, the entry is stale (e.g. caches were reset). Discard
+		// it so we create a fresh race below.
+		if (existing?.resolved) {
+			const state = server.cacheState.get();
+			if (state === McpServerCacheState.Unknown || state === McpServerCacheState.Outdated) {
+				this._startupGrace.delete(id);
+			}
+		}
+		if (!this._startupGrace.has(id)) {
+			const entry: { promise: Promise<boolean>; resolved: boolean } = {
+				promise: Promise.race([
+					this._ensureServerReady(server),
+					new Promise<boolean>(resolve => setTimeout(() => resolve(false), this._startupGracePeriodMs)),
+				]),
+				resolved: false,
+			};
+			entry.promise.then(() => { entry.resolved = true; });
+			this._startupGrace.set(id, entry);
+		}
+		return this._startupGrace.get(id)!.promise;
+	}
+
+	private async _shouldUseCachedData(server: IMcpServer): Promise<boolean> {
+		const cacheState = server.cacheState.get();
+		if (cacheState === McpServerCacheState.Unknown || cacheState === McpServerCacheState.Outdated) {
+			// On first list call: wait up to the grace period for the server to start.
+			// On subsequent calls: the stored promise is already resolved, returns immediately.
+			// Outdated servers get the same grace period as Unknown — a prior fast startup
+			// does not guarantee a fast restart.
+			await this._waitForStartup(server);
+			const newState = server.cacheState.get();
+			return newState === McpServerCacheState.Live
+				|| newState === McpServerCacheState.Cached
+				|| newState === McpServerCacheState.RefreshingFromCached;
+		}
+		return cacheState === McpServerCacheState.Live
+			|| cacheState === McpServerCacheState.Cached
+			|| cacheState === McpServerCacheState.RefreshingFromCached;
+	}
+
 	listen<T>(_ctx: unknown, event: string): Event<T> {
 		switch (event) {
 			case 'onDidChangeTools':
@@ -93,6 +155,8 @@ export class McpGatewayToolBrokerChannel extends Disposable implements IServerCh
 	}
 
 	async call<T>(_ctx: unknown, command: string, arg?: unknown, cancellationToken?: CancellationToken): Promise<T> {
+		this._logService.debug(`[McpGateway][ToolBroker] IPC call: ${command}`);
+
 		switch (command) {
 			case 'listTools': {
 				const tools = await this._listTools();
@@ -122,80 +186,94 @@ export class McpGatewayToolBrokerChannel extends Disposable implements IServerCh
 	}
 
 	private async _listTools(): Promise<readonly MCP.Tool[]> {
-		const mcpTools: MCP.Tool[] = [];
 		const servers = this._mcpService.servers.get();
-		await Promise.all(servers.map(server => this._ensureServerReady(server)));
-
-		for (const server of servers) {
-			const cacheState = server.cacheState.get();
-			if (cacheState !== McpServerCacheState.Live && cacheState !== McpServerCacheState.Cached && cacheState !== McpServerCacheState.RefreshingFromCached) {
-				continue;
+		const perServer = await Promise.all(servers.map(async server => {
+			if (!await this._shouldUseCachedData(server)) {
+				this._logService.debug(`[McpGateway][ToolBroker] Server '${server.definition.id}' not ready, skipping tool listing`);
+				return [] as MCP.Tool[];
 			}
+			return server.tools.get()
+				.filter(t => t.visibility & McpToolVisibility.Model)
+				.map(t => t.definition);
+		}));
 
-			for (const tool of server.tools.get()) {
-				if (!(tool.visibility & McpToolVisibility.Model)) {
-					continue;
-				}
-
-				mcpTools.push(tool.definition);
-			}
-		}
+		const mcpTools = perServer.flat();
+		this._logService.debug(`[McpGateway][ToolBroker] listTools result: ${mcpTools.length} tool(s): [${mcpTools.map(t => t.name).join(', ')}]`);
 
 		return mcpTools;
 	}
 
 	private async _callTool(name: string, args: Record<string, unknown>, token: CancellationToken = CancellationToken.None): Promise<IGatewayCallToolResult> {
+		this._logService.debug(`[McpGateway][ToolBroker] callTool '${name}' with args: ${JSON.stringify(args)}`);
+
 		for (const server of this._mcpService.servers.get()) {
 			const tool = server.tools.get().find(t =>
 				t.definition.name === name && (t.visibility & McpToolVisibility.Model)
 			);
 
 			if (tool) {
+				this._logService.debug(`[McpGateway][ToolBroker] Found tool '${name}' on server '${server.definition.id}' (index=${this._getServerIndex(server)})`);
 				const result = await tool.call(args, undefined, token);
+				this._logService.debug(`[McpGateway][ToolBroker] Tool '${name}' completed (isError=${result.isError ?? false}, content blocks=${result.content.length})`);
 				return { result, serverIndex: this._getServerIndex(server) };
 			}
 		}
 
+		this._logService.warn(`[McpGateway][ToolBroker] Tool '${name}' not found on any server`);
 		throw new Error(`Unknown tool: ${name}`);
 	}
 
 	private async _listResources(): Promise<readonly IGatewayServerResources[]> {
 		const results: IGatewayServerResources[] = [];
 		const servers = this._mcpService.servers.get();
+		this._logService.debug(`[McpGateway][ToolBroker] listResources: ${servers.length} server(s) known`);
+
 		await Promise.all(servers.map(async server => {
-			await this._ensureServerReady(server);
+			if (!await this._shouldUseCachedData(server)) {
+				return;
+			}
 
 			const capabilities = server.capabilities.get();
 			if (!capabilities || !(capabilities & McpCapability.Resources)) {
+				this._logService.debug(`[McpGateway][ToolBroker] Server '${server.definition.id}' has no resource capability, skipping`);
 				return;
 			}
 
 			try {
 				const resources = await McpServer.callOn(server, h => h.listResources());
+				this._logService.debug(`[McpGateway][ToolBroker] Server '${server.definition.id}' (index=${this._getServerIndex(server)}) listed ${resources.length} resource(s)`);
 				results.push({ serverIndex: this._getServerIndex(server), resources });
-			} catch {
-				// Server failed; skip
+			} catch (error) {
+				this._logService.warn(`[McpGateway][ToolBroker] Server '${server.definition.id}' failed to list resources`, error);
 			}
 		}));
 
+		this._logService.debug(`[McpGateway][ToolBroker] listResources result: ${results.length} server(s) with resources`);
 		return results;
 	}
 
 	private async _readResource(serverIndex: number, uri: string, token: CancellationToken = CancellationToken.None): Promise<MCP.ReadResourceResult> {
 		const server = this._getServerByIndex(serverIndex);
 		if (!server) {
+			this._logService.warn(`[McpGateway][ToolBroker] readResource: unknown server index ${serverIndex}`);
 			throw new Error(`Unknown server index: ${serverIndex}`);
 		}
 
-		return McpServer.callOn(server, h => h.readResource({ uri }, token), token);
+		this._logService.debug(`[McpGateway][ToolBroker] readResource '${uri}' from server '${server.definition.id}' (index=${serverIndex})`);
+		const result = await McpServer.callOn(server, h => h.readResource({ uri }, token), token);
+		this._logService.debug(`[McpGateway][ToolBroker] readResource returned ${result.contents.length} content(s)`);
+		return result;
 	}
 
 	private async _listResourceTemplates(): Promise<readonly IGatewayServerResourceTemplates[]> {
 		const results: IGatewayServerResourceTemplates[] = [];
 		const servers = this._mcpService.servers.get();
+		this._logService.debug(`[McpGateway][ToolBroker] listResourceTemplates: ${servers.length} server(s) known`);
 
 		await Promise.all(servers.map(async server => {
-			await this._ensureServerReady(server);
+			if (!await this._shouldUseCachedData(server)) {
+				return;
+			}
 
 			const capabilities = server.capabilities.get();
 			if (!capabilities || !(capabilities & McpCapability.Resources)) {
@@ -204,12 +282,14 @@ export class McpGatewayToolBrokerChannel extends Disposable implements IServerCh
 
 			try {
 				const resourceTemplates = await McpServer.callOn(server, h => h.listResourceTemplates());
+				this._logService.debug(`[McpGateway][ToolBroker] Server '${server.definition.id}' (index=${this._getServerIndex(server)}) listed ${resourceTemplates.length} resource template(s)`);
 				results.push({ serverIndex: this._getServerIndex(server), resourceTemplates });
-			} catch {
-				// Server failed; skip
+			} catch (error) {
+				this._logService.warn(`[McpGateway][ToolBroker] Server '${server.definition.id}' failed to list resource templates`, error);
 			}
 		}));
 
+		this._logService.debug(`[McpGateway][ToolBroker] listResourceTemplates result: ${results.length} server(s) with templates`);
 		return results;
 	}
 
@@ -219,12 +299,16 @@ export class McpGatewayToolBrokerChannel extends Disposable implements IServerCh
 			return true;
 		}
 
+		this._logService.debug(`[McpGateway][ToolBroker] Server '${server.definition.id}' not ready (cacheState=${cacheState}), starting...`);
 		try {
-			return await startServerAndWaitForLiveTools(server, {
+			const ready = await startServerAndWaitForLiveTools(server, {
 				promptType: 'all-untrusted',
 				errorOnUserInteraction: true,
 			});
-		} catch {
+			this._logService.debug(`[McpGateway][ToolBroker] Server '${server.definition.id}' ready=${ready}`);
+			return ready;
+		} catch (error) {
+			this._logService.warn(`[McpGateway][ToolBroker] Server '${server.definition.id}' failed to start`, error);
 			return false;
 		}
 	}
diff --git a/src/vs/workbench/contrib/mcp/common/mcpLanguageModelToolContribution.ts b/src/vs/workbench/contrib/mcp/common/mcpLanguageModelToolContribution.ts
index 9ef7cf37e5f6e..28400d12acfd6 100644
--- a/src/vs/workbench/contrib/mcp/common/mcpLanguageModelToolContribution.ts
+++ b/src/vs/workbench/contrib/mcp/common/mcpLanguageModelToolContribution.ts
@@ -23,6 +23,7 @@ import { mcpAppsEnabledConfig } from '../../../../platform/mcp/common/mcpManagem
 import { IProductService } from '../../../../platform/product/common/productService.js';
 import { StorageScope } from '../../../../platform/storage/common/storage.js';
 import { IWorkbenchContribution } from '../../../common/contributions.js';
+import { isContributionEnabled } from '../../chat/common/enablement.js';
 import { ChatResponseResource, getAttachableImageExtension } from '../../chat/common/model/chatModel.js';
 import { LanguageModelPartAudience } from '../../chat/common/languageModels.js';
 import { CountTokensCallback, ILanguageModelToolsService, IPreparedToolInvocation, IToolConfirmationMessages, IToolData, IToolImpl, IToolInvocation, IToolInvocationPreparationContext, IToolResult, IToolResultInputOutputDetails, ToolDataSource, ToolProgress, ToolSet } from '../../chat/common/tools/languageModelToolsService.js';
@@ -59,6 +60,11 @@ export class McpLanguageModelToolContribution extends Disposable implements IWor
 
 			const toDelete = new Set(previous.keys());
 			for (const server of servers) {
+				// Skip disabled servers — don't register their tools.
+				if (!isContributionEnabled(server.enablement.read(reader))) {
+					continue;
+				}
+
 				const previousRec = previous.get(server);
 				if (previousRec) {
 					toDelete.delete(server);
diff --git a/src/vs/workbench/contrib/mcp/common/mcpRegistry.ts b/src/vs/workbench/contrib/mcp/common/mcpRegistry.ts
index 20500e68f87a8..d9ff9dad84aa0 100644
--- a/src/vs/workbench/contrib/mcp/common/mcpRegistry.ts
+++ b/src/vs/workbench/contrib/mcp/common/mcpRegistry.ts
@@ -26,6 +26,7 @@ import { observableConfigValue } from '../../../../platform/observable/common/pl
 import { IQuickInputButton, IQuickInputService, IQuickPickItem } from '../../../../platform/quickinput/common/quickInput.js';
 import { StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
 import { IWorkspaceFolderData } from '../../../../platform/workspace/common/workspace.js';
+import { IWorkspaceTrustManagementService, IWorkspaceTrustRequestService } from '../../../../platform/workspace/common/workspaceTrust.js';
 import { IConfigurationResolverService } from '../../../services/configurationResolver/common/configurationResolver.js';
 import { ConfigurationResolverExpression, IResolvedValue } from '../../../services/configurationResolver/common/configurationResolverExpression.js';
 import { AUX_WINDOW_GROUP, IEditorService } from '../../../services/editor/common/editorService.js';
@@ -87,6 +88,8 @@ export class McpRegistry extends Disposable implements IMcpRegistry {
 		@ILabelService private readonly _labelService: ILabelService,
 		@ILogService private readonly _logService: ILogService,
 		@IMcpSandboxService private readonly _mcpSandboxService: IMcpSandboxService,
+		@IWorkspaceTrustManagementService private readonly _workspaceTrustManagementService: IWorkspaceTrustManagementService,
+		@IWorkspaceTrustRequestService private readonly _workspaceTrustRequestService: IWorkspaceTrustRequestService,
 	) {
 		super();
 		this._mcpAccessValue = observableConfigValue(mcpAccessConfig, McpAccessValue.All, configurationService);
@@ -215,6 +218,14 @@ export class McpRegistry extends Disposable implements IMcpRegistry {
 		autoTrustChanges = false,
 		errorOnUserInteraction = false,
 	}: IMcpResolveConnectionOptions) {
+		if (collection.scope === StorageScope.WORKSPACE && !this._workspaceTrustManagementService.isWorkspaceTrusted()) {
+			if (errorOnUserInteraction) {
+				throw new UserInteractionRequiredError('workspaceTrust');
+			} else if (!await this._workspaceTrustRequestService.requestWorkspaceTrust({ message: localize('runTrust', "This MCP server definition is defined in your workspace files.") })) {
+				return false;
+			}
+		}
+
 		if (collection.trustBehavior === McpServerTrust.Kind.Trusted) {
 			this._logService.trace(`MCP server ${definition.id} is trusted, no trust prompt needed`);
 			return true;
diff --git a/src/vs/workbench/contrib/mcp/common/mcpSamplingService.ts b/src/vs/workbench/contrib/mcp/common/mcpSamplingService.ts
index 317b4a0473bd5..363f8a12c5f26 100644
--- a/src/vs/workbench/contrib/mcp/common/mcpSamplingService.ts
+++ b/src/vs/workbench/contrib/mcp/common/mcpSamplingService.ts
@@ -15,10 +15,9 @@ import { localize } from '../../../../nls.js';
 import { ICommandService } from '../../../../platform/commands/common/commands.js';
 import { ConfigurationTarget, getConfigValueInTarget, IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { IDialogService } from '../../../../platform/dialogs/common/dialogs.js';
-import { ExtensionIdentifier } from '../../../../platform/extensions/common/extensions.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { INotificationService, Severity } from '../../../../platform/notification/common/notification.js';
-import { ChatAgentLocation, ChatConfiguration } from '../../chat/common/constants.js';
+import { ChatConfiguration } from '../../chat/common/constants.js';
 import { ChatImageMimeType, ChatMessageRole, IChatMessage, IChatMessagePart, ILanguageModelsService } from '../../chat/common/languageModels.js';
 import { McpCommandIds } from './mcpCommandIds.js';
 import { IMcpServerSamplingConfiguration, mcpServerSamplingSection } from './mcpConfiguration.js';
@@ -80,8 +79,7 @@ export class McpSamplingService extends Disposable implements IMcpSamplingServic
 		}
 
 		const model = await this._modelSequencer.queue(() => this._getMatchingModel(opts));
-		// todo@connor4312: nullExtensionDescription.identifier -> undefined with API update
-		const response = await this._languageModelsService.sendChatRequest(model, new ExtensionIdentifier('core'), messages, {}, token);
+		const response = await this._languageModelsService.sendChatRequest(model, undefined, messages, {}, token);
 
 		let responseText = '';
 
@@ -243,11 +241,8 @@ export class McpSamplingService extends Disposable implements IMcpSamplingServic
 			return config.allowedOutsideChat === undefined ? ModelMatch.UnsureAllowedOutsideChat : ModelMatch.NotAllowed;
 		}
 
-		// 2. Get the configured models, or the default model(s)
-		const foundModelIdsDeep = config.allowedModels?.filter(m => !!this._languageModelsService.lookupLanguageModel(m)) || this._languageModelsService.getLanguageModelIds().filter(m => this._languageModelsService.lookupLanguageModel(m)?.isDefaultForLocation[ChatAgentLocation.Chat]);
-
-		const foundModelIds = foundModelIdsDeep.flat().sort((a, b) => b.length - a.length); // Sort by length to prefer most specific
-
+		// 2. Get the configured models, or the default free model(s)
+		const foundModelIds = config.allowedModels?.filter(m => !!this._languageModelsService.lookupLanguageModel(m)) || this._getDefaultModels();
 		if (!foundModelIds.length) {
 			return ModelMatch.NoMatchingModel;
 		}
@@ -263,6 +258,20 @@ export class McpSamplingService extends Disposable implements IMcpSamplingServic
 		return foundModelIds[0]; // Return the first matching model
 	}
 
+	private _getDefaultModels() {
+		const candidates = this._languageModelsService.getLanguageModelIds().map(m => {
+			const model = this._languageModelsService.lookupLanguageModel(m);
+			return model && !model.multiplierNumeric && !model.targetChatSessionType ? { model, id: m } : undefined;
+		}).filter(isDefined);
+
+		const someDefault = candidates.findIndex(c => Object.values(c.model.isDefaultForLocation).some(Boolean));
+		if (someDefault !== -1) {
+			[candidates[0], candidates[someDefault]] = [candidates[someDefault], candidates[0]];
+		}
+
+		return candidates.map(c => c.id);
+	}
+
 	private _configKey(server: IMcpServer) {
 		return `${server.collection.label}: ${server.definition.label}`;
 	}
diff --git a/src/vs/workbench/contrib/mcp/common/mcpSandboxService.ts b/src/vs/workbench/contrib/mcp/common/mcpSandboxService.ts
index f4cf13707d20c..0776dcd3bffea 100644
--- a/src/vs/workbench/contrib/mcp/common/mcpSandboxService.ts
+++ b/src/vs/workbench/contrib/mcp/common/mcpSandboxService.ts
@@ -10,15 +10,18 @@ import { dirname, posix, win32 } from '../../../../base/common/path.js';
 import { OperatingSystem, OS } from '../../../../base/common/platform.js';
 import { URI } from '../../../../base/common/uri.js';
 import { generateUuid } from '../../../../base/common/uuid.js';
+import { localize } from '../../../../nls.js';
 import { ConfigurationTarget, ConfigurationTargetToString } from '../../../../platform/configuration/common/configuration.js';
 import { IEnvironmentService } from '../../../../platform/environment/common/environment.js';
 import { IFileService } from '../../../../platform/files/common/files.js';
 import { createDecorator } from '../../../../platform/instantiation/common/instantiation.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
+import { IMcpResourceScannerService, McpResourceTarget } from '../../../../platform/mcp/common/mcpResourceScannerService.js';
 import { IRemoteAgentEnvironment } from '../../../../platform/remote/common/remoteAgentEnvironment.js';
 import { IRemoteAgentService } from '../../../services/remote/common/remoteAgentService.js';
 import { IMcpSandboxConfiguration } from '../../../../platform/mcp/common/mcpPlatformTypes.js';
-import { McpServerDefinition, McpServerLaunch, McpServerTransportType } from './mcpTypes.js';
+import { IMcpPotentialSandboxBlock, McpServerDefinition, McpServerLaunch, McpServerTransportStdio, McpServerTransportType } from './mcpTypes.js';
+
 
 export const IMcpSandboxService = createDecorator<IMcpSandboxService>('mcpSandboxService');
 
@@ -26,11 +29,24 @@ export interface IMcpSandboxService {
 	readonly _serviceBrand: undefined;
 	launchInSandboxIfEnabled(serverDef: McpServerDefinition, launch: McpServerLaunch, remoteAuthority: string | undefined, configTarget: ConfigurationTarget): Promise<McpServerLaunch>;
 	isEnabled(serverDef: McpServerDefinition, serverLabel?: string): Promise<boolean>;
+	getSandboxConfigSuggestionMessage(serverLabel: string, potentialBlocks: readonly IMcpPotentialSandboxBlock[], existingSandboxConfig?: IMcpSandboxConfiguration): SandboxConfigSuggestionResult | undefined;
+	applySandboxConfigSuggestion(serverDef: McpServerDefinition, mcpResource: URI, configTarget: ConfigurationTarget, potentialBlocks: readonly IMcpPotentialSandboxBlock[], suggestedSandboxConfig?: IMcpSandboxConfiguration): Promise<boolean>;
 }
 
+type SandboxConfigSuggestions = {
+	allowWrite: readonly string[];
+	allowedDomains: readonly string[];
+};
+
+type SandboxConfigSuggestionResult = {
+	message: string;
+	sandboxConfig: IMcpSandboxConfiguration;
+};
+
 type SandboxLaunchDetails = {
 	execPath: string | undefined;
 	srtPath: string | undefined;
+	rgPath: string | undefined;
 	sandboxConfigPath: string | undefined;
 	tempDir: URI | undefined;
 };
@@ -40,13 +56,15 @@ export class McpSandboxService extends Disposable implements IMcpSandboxService
 
 	private _sandboxSettingsId: string | undefined;
 	private _remoteEnvDetailsPromise: Promise<IRemoteAgentEnvironment | null>;
-	private readonly _defaultAllowedDomains: readonly string[] = ['*.npmjs.org'];
+	private readonly _defaultAllowedDomains: readonly string[] = ['registry.npmjs.org']; // Default allowed domains that are commonly needed for MCP servers, even if the user doesn't specify them in their sandbox config
+	private _defaultAllowWritePaths: string[] = ['~/.npm'];
 	private _sandboxConfigPerConfigurationTarget: Map<string, string> = new Map();
 
 	constructor(
 		@IFileService private readonly _fileService: IFileService,
 		@IEnvironmentService private readonly _environmentService: IEnvironmentService,
 		@ILogService private readonly _logService: ILogService,
+		@IMcpResourceScannerService private readonly _mcpResourceScannerService: IMcpResourceScannerService,
 		@IRemoteAgentService private readonly _remoteAgentService: IRemoteAgentService,
 	) {
 		super();
@@ -69,17 +87,18 @@ export class McpSandboxService extends Disposable implements IMcpSandboxService
 		}
 		if (await this.isEnabled(serverDef, remoteAuthority)) {
 			this._logService.trace(`McpSandboxService: Launching with config target ${configTarget}`);
-			const launchDetails = await this._resolveSandboxLaunchDetails(configTarget, remoteAuthority, serverDef.sandbox);
-			const sandboxArgs = this._getSandboxCommandArgs(launch.command, launch.args, launchDetails.sandboxConfigPath);
-			const sandboxEnv = this._getSandboxEnvVariables(launchDetails.tempDir, remoteAuthority);
+			const launchDetails = await this._resolveSandboxLaunchDetails(configTarget, remoteAuthority, launch.sandbox, launch.cwd);
+			const quotedCommand = this._quoteShellArgument(launch.command);
+			const quotedArgs = launch.args.map(arg => this._quoteShellArgument(arg));
+			const sandboxArgs = this._getSandboxCommandArgs(quotedCommand, quotedArgs, launchDetails.sandboxConfigPath);
+			const sandboxEnv = await this._getSandboxEnvVariables(launch.env, launchDetails.tempDir, launchDetails.rgPath, remoteAuthority);
 			if (launchDetails.srtPath) {
-				const envWithSandbox = sandboxEnv ? { ...launch.env, ...sandboxEnv } : launch.env;
 				if (launchDetails.execPath) {
 					return {
 						...launch,
 						command: launchDetails.execPath,
 						args: [launchDetails.srtPath, ...sandboxArgs],
-						env: envWithSandbox,
+						env: sandboxEnv,
 						type: McpServerTransportType.Stdio,
 					};
 				} else {
@@ -87,7 +106,7 @@ export class McpSandboxService extends Disposable implements IMcpSandboxService
 						...launch,
 						command: launchDetails.srtPath,
 						args: sandboxArgs,
-						env: envWithSandbox,
+						env: sandboxEnv,
 						type: McpServerTransportType.Stdio,
 					};
 				}
@@ -100,19 +119,154 @@ export class McpSandboxService extends Disposable implements IMcpSandboxService
 		return launch;
 	}
 
-	private async _resolveSandboxLaunchDetails(configTarget: ConfigurationTarget, remoteAuthority?: string, sandboxConfig?: IMcpSandboxConfiguration): Promise<SandboxLaunchDetails> {
+	public getSandboxConfigSuggestionMessage(serverLabel: string, potentialBlocks: readonly IMcpPotentialSandboxBlock[], existingSandboxConfig?: IMcpSandboxConfiguration): SandboxConfigSuggestionResult | undefined {
+		const suggestions = this._getSandboxConfigSuggestions(potentialBlocks, existingSandboxConfig);
+		if (!suggestions) {
+			return undefined;
+		}
+
+		const allowWriteList = suggestions.allowWrite;
+		const allowedDomainsList = suggestions.allowedDomains;
+		const suggestionLines: string[] = [];
+
+		if (allowedDomainsList.length) {
+			const shown = allowedDomainsList.map(domain => `"${domain}"`).join(', ');
+			suggestionLines.push(localize('mcpSandboxSuggestion.allowedDomains', "Add to `sandbox.network.allowedDomains`: {0}", shown));
+		}
+
+		if (allowWriteList.length) {
+			const shown = allowWriteList.map(path => `"${path}"`).join(', ');
+			suggestionLines.push(localize('mcpSandboxSuggestion.allowWrite', "Add to `sandbox.filesystem.allowWrite`: {0}", shown));
+		}
+
+		const sandboxConfig: IMcpSandboxConfiguration = {};
+		if (allowedDomainsList.length) {
+			sandboxConfig.network = { allowedDomains: [...allowedDomainsList] };
+		}
+		if (allowWriteList.length) {
+			sandboxConfig.filesystem = { allowWrite: [...allowWriteList] };
+		}
+
+		return {
+			message: localize(
+				'mcpSandboxSuggestion.message',
+				"The MCP server {0} reported potential sandbox blocks. VS Code found possible sandbox configuration updates:\n{1}",
+				serverLabel,
+				suggestionLines.join('\n')
+			),
+			sandboxConfig,
+		};
+	}
+
+	public async applySandboxConfigSuggestion(serverDef: McpServerDefinition, mcpResource: URI, configTarget: ConfigurationTarget, potentialBlocks: readonly IMcpPotentialSandboxBlock[], suggestedSandboxConfig?: IMcpSandboxConfiguration): Promise<boolean> {
+		const scanTarget = this._toMcpResourceTarget(configTarget);
+		let didChange = false;
+
+		await this._mcpResourceScannerService.updateSandboxConfig(data => {
+			const existingSandbox = data.sandbox;
+			const suggestedAllowedDomains = suggestedSandboxConfig?.network?.allowedDomains ?? [];
+			const suggestedAllowWrite = suggestedSandboxConfig?.filesystem?.allowWrite ?? [];
+
+			const currentAllowedDomains = new Set(existingSandbox?.network?.allowedDomains ?? []);
+			for (const domain of suggestedAllowedDomains) {
+				if (domain && !currentAllowedDomains.has(domain)) {
+					currentAllowedDomains.add(domain);
+				}
+			}
+
+			const currentAllowWrite = new Set(existingSandbox?.filesystem?.allowWrite ?? []);
+			for (const path of suggestedAllowWrite) {
+				if (path && !currentAllowWrite.has(path)) {
+					currentAllowWrite.add(path);
+				}
+			}
+
+			if (suggestedAllowedDomains.length === 0 && suggestedAllowWrite.length === 0) {
+				return data;
+			}
+
+			didChange = true;
+			const nextSandboxConfig: IMcpSandboxConfiguration = {};
+			if (currentAllowedDomains.size > 0) {
+				nextSandboxConfig.network = {
+					...existingSandbox?.network,
+					allowedDomains: [...currentAllowedDomains]
+				};
+			}
+			if (currentAllowWrite.size > 0) {
+				nextSandboxConfig.filesystem = {
+					...existingSandbox?.filesystem,
+					allowWrite: [...currentAllowWrite],
+				};
+			}
+			return {
+				...data,
+				sandbox: nextSandboxConfig,
+			};
+		}, mcpResource, scanTarget);
+
+		return didChange;
+	}
+
+	private _getSandboxConfigSuggestions(potentialBlocks: readonly IMcpPotentialSandboxBlock[], existingSandboxConfig?: IMcpSandboxConfiguration): SandboxConfigSuggestions | undefined {
+		if (!potentialBlocks.length) {
+			return undefined;
+		}
+
+		const allowWrite = new Set<string>();
+		const allowedDomains = new Set<string>();
+		const existingAllowWrite = new Set(existingSandboxConfig?.filesystem?.allowWrite ?? []);
+		const existingAllowedDomains = new Set(existingSandboxConfig?.network?.allowedDomains ?? []);
+
+		for (const block of potentialBlocks) {
+			if (block.kind === 'network' && block.host && !existingAllowedDomains.has(block.host)) {
+				allowedDomains.add(block.host);
+			}
+
+			if (block.kind === 'filesystem' && block.path && !existingAllowWrite.has(block.path)) {
+				allowWrite.add(block.path);
+			}
+		}
+
+		if (!allowWrite.size && !allowedDomains.size) {
+			return undefined;
+		}
+
+		return {
+			allowWrite: [...allowWrite],
+			allowedDomains: [...allowedDomains],
+		};
+	}
+
+	private _toMcpResourceTarget(configTarget: ConfigurationTarget): McpResourceTarget {
+		switch (configTarget) {
+			case ConfigurationTarget.USER:
+			case ConfigurationTarget.USER_LOCAL:
+			case ConfigurationTarget.USER_REMOTE:
+				return ConfigurationTarget.USER;
+			case ConfigurationTarget.WORKSPACE:
+				return ConfigurationTarget.WORKSPACE;
+			case ConfigurationTarget.WORKSPACE_FOLDER:
+				return ConfigurationTarget.WORKSPACE_FOLDER;
+			default:
+				return ConfigurationTarget.USER;
+		}
+	}
+
+	private async _resolveSandboxLaunchDetails(configTarget: ConfigurationTarget, remoteAuthority?: string, sandboxConfig?: IMcpSandboxConfiguration, launchCwd?: string): Promise<SandboxLaunchDetails> {
 		const os = await this._getOperatingSystem(remoteAuthority);
 		if (os === OperatingSystem.Windows) {
-			return { execPath: undefined, srtPath: undefined, sandboxConfigPath: undefined, tempDir: undefined };
+			return { execPath: undefined, srtPath: undefined, rgPath: undefined, sandboxConfigPath: undefined, tempDir: undefined };
 		}
 
 		const appRoot = await this._getAppRoot(remoteAuthority);
 		const execPath = await this._getExecPath(os, appRoot, remoteAuthority);
 		const tempDir = await this._getTempDir(remoteAuthority);
 		const srtPath = this._pathJoin(os, appRoot, 'node_modules', '@anthropic-ai', 'sandbox-runtime', 'dist', 'cli.js');
-		const sandboxConfigPath = tempDir ? await this._updateSandboxConfig(tempDir, configTarget, sandboxConfig) : undefined;
+		const rgPath = this._pathJoin(os, appRoot, 'node_modules', '@vscode', 'ripgrep', 'bin', 'rg');
+		const sandboxConfigPath = tempDir ? await this._updateSandboxConfig(tempDir, configTarget, sandboxConfig, launchCwd) : undefined;
 		this._logService.debug(`McpSandboxService: Updated sandbox config path: ${sandboxConfigPath}`);
-		return { execPath, srtPath, sandboxConfigPath, tempDir };
+		return { execPath, srtPath, rgPath, sandboxConfigPath, tempDir };
 	}
 
 	private async _getExecPath(os: OperatingSystem, appRoot: string, remoteAuthority?: string): Promise<string | undefined> {
@@ -122,10 +276,13 @@ export class McpSandboxService extends Disposable implements IMcpSandboxService
 		return undefined; // Use Electron executable as the default exec path for local development, which will run the sandbox runtime wrapper with Electron in node mode. For remote, we need to specify the node executable to ensure it runs with Node.js.
 	}
 
-	private _getSandboxEnvVariables(tempDir: URI | undefined, remoteAuthority?: string): Record<string, string | null> | undefined {
-		let env: Record<string, string | null> = {};
+	private async _getSandboxEnvVariables(baseEnv: McpServerTransportStdio['env'], tempDir: URI | undefined, rgPath: string | undefined, remoteAuthority?: string): Promise<McpServerTransportStdio['env']> {
+		let env: McpServerTransportStdio['env'] = { ...baseEnv };
 		if (tempDir) {
-			env = { TMPDIR: tempDir.path, SRT_DEBUG: 'true' };
+			env = { ...env, TMPDIR: tempDir.path, SRT_DEBUG: 'true', NODE_USE_ENV_PROXY: '1' };
+		}
+		if (rgPath) {
+			env = { ...env, PATH: env['PATH'] ? `${env['PATH']}${await this._getPathDelimiter(remoteAuthority)}${dirname(rgPath)}` : dirname(rgPath) };
 		}
 		if (!remoteAuthority) {
 			// Add any remote-specific environment variables here
@@ -140,6 +297,7 @@ export class McpSandboxService extends Disposable implements IMcpSandboxService
 		const result: string[] = [];
 		if (sandboxConfigPath) {
 			result.push('--settings', sandboxConfigPath);
+			result.push('--');
 		}
 		result.push(command, ...args);
 		return result;
@@ -181,8 +339,8 @@ export class McpSandboxService extends Disposable implements IMcpSandboxService
 		return tempDir;
 	}
 
-	private async _updateSandboxConfig(tempDir: URI, configTarget: ConfigurationTarget, sandboxConfig?: IMcpSandboxConfiguration): Promise<string> {
-		const normalizedSandboxConfig = this._withDefaultSandboxConfig(sandboxConfig);
+	private async _updateSandboxConfig(tempDir: URI, configTarget: ConfigurationTarget, sandboxConfig?: IMcpSandboxConfiguration, launchCwd?: string): Promise<string> {
+		const normalizedSandboxConfig = this._withDefaultSandboxConfig(sandboxConfig, launchCwd);
 		let configFileUri: URI;
 		const configTargetKey = ConfigurationTargetToString(configTarget);
 		if (this._sandboxConfigPerConfigurationTarget.has(configTargetKey)) {
@@ -197,9 +355,9 @@ export class McpSandboxService extends Disposable implements IMcpSandboxService
 
 	// this method merges the default allowWrite paths and allowedDomains with the ones provided in the sandbox config, to ensure that the default necessary paths and domains are always included in the sandbox config used for launching,
 	//  even if they are not explicitly specified in the config provided by the user or the MCP server config.
-	private _withDefaultSandboxConfig(sandboxConfig?: IMcpSandboxConfiguration): IMcpSandboxConfiguration {
+	private _withDefaultSandboxConfig(sandboxConfig?: IMcpSandboxConfiguration, launchCwd?: string): IMcpSandboxConfiguration {
 		const mergedAllowWrite = new Set(sandboxConfig?.filesystem?.allowWrite ?? []);
-		for (const defaultAllowWrite of this._getDefaultAllowWrite()) {
+		for (const defaultAllowWrite of this._getDefaultAllowWrite(launchCwd ? [launchCwd] : undefined)) {
 			if (defaultAllowWrite) {
 				mergedAllowWrite.add(defaultAllowWrite);
 			}
@@ -226,10 +384,14 @@ export class McpSandboxService extends Disposable implements IMcpSandboxService
 		};
 	}
 
-	private _getDefaultAllowWrite(): readonly string[] {
-		return [
-			'~/.npm'
-		];
+	private _getDefaultAllowWrite(directories?: string[]): readonly string[] {
+		for (const launchCwd of directories ?? []) {
+			const trimmed = launchCwd.trim();
+			if (trimmed) {
+				this._defaultAllowWritePaths.push(trimmed);
+			}
+		}
+		return this._defaultAllowWritePaths;
 	}
 
 	private _pathJoin = (os: OperatingSystem, ...segments: string[]) => {
@@ -237,4 +399,13 @@ export class McpSandboxService extends Disposable implements IMcpSandboxService
 		return path.join(...segments);
 	};
 
+	private _getPathDelimiter = async (remoteAuthority?: string) => {
+		const os = await this._getOperatingSystem(remoteAuthority);
+		return os === OperatingSystem.Windows ? win32.delimiter : posix.delimiter;
+	};
+
+	private _quoteShellArgument(value: string): string {
+		return `'${value.replace(/'/g, `'\\''`)}'`;
+	}
+
 }
diff --git a/src/vs/workbench/contrib/mcp/common/mcpServer.ts b/src/vs/workbench/contrib/mcp/common/mcpServer.ts
index 49743c1f10a06..9f93c186e584e 100644
--- a/src/vs/workbench/contrib/mcp/common/mcpServer.ts
+++ b/src/vs/workbench/contrib/mcp/common/mcpServer.ts
@@ -8,7 +8,7 @@ import { CancellationToken, CancellationTokenSource } from '../../../../base/com
 import { Iterable } from '../../../../base/common/iterator.js';
 import * as json from '../../../../base/common/json.js';
 import { normalizeDriveLetter } from '../../../../base/common/labels.js';
-import { Disposable, DisposableStore, IDisposable, toDisposable } from '../../../../base/common/lifecycle.js';
+import { Disposable, DisposableStore, IDisposable, MutableDisposable, toDisposable } from '../../../../base/common/lifecycle.js';
 import { LRUCache } from '../../../../base/common/map.js';
 import { Schemas } from '../../../../base/common/network.js';
 import { mapValues } from '../../../../base/common/objects.js';
@@ -19,6 +19,7 @@ import { createURITransformer } from '../../../../base/common/uriTransformer.js'
 import { generateUuid } from '../../../../base/common/uuid.js';
 import { localize } from '../../../../nls.js';
 import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IDialogService } from '../../../../platform/dialogs/common/dialogs.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { ILogger, ILoggerService } from '../../../../platform/log/common/log.js';
 import { INotificationService, IPromptChoice, Severity } from '../../../../platform/notification/common/notification.js';
@@ -36,9 +37,11 @@ import { mcpActivationEvent } from './mcpConfiguration.js';
 import { McpDevModeServerAttache } from './mcpDevMode.js';
 import { McpIcons, parseAndValidateMcpIcon, StoredMcpIcons } from './mcpIcons.js';
 import { IMcpRegistry } from './mcpRegistryTypes.js';
+import { IMcpSandboxService } from './mcpSandboxService.js';
 import { McpServerRequestHandler } from './mcpServerRequestHandler.js';
 import { McpTaskManager } from './mcpTaskManager.js';
-import { ElicitationKind, extensionMcpCollectionPrefix, IMcpElicitationService, IMcpIcons, IMcpPrompt, IMcpPromptMessage, IMcpResource, IMcpResourceTemplate, IMcpSamplingService, IMcpServer, IMcpServerConnection, IMcpServerStartOpts, IMcpTool, IMcpToolCallContext, McpCapability, McpCollectionDefinition, McpCollectionReference, McpConnectionFailedError, McpConnectionState, McpDefinitionReference, mcpPromptReplaceSpecialChars, McpResourceURI, McpServerCacheState, McpServerDefinition, McpServerStaticToolAvailability, McpServerTransportType, McpToolName, McpToolVisibility, MpcResponseError, UserInteractionRequiredError } from './mcpTypes.js';
+import { ElicitationKind, extensionMcpCollectionPrefix, IMcpElicitationService, IMcpIcons, IMcpPotentialSandboxBlock, IMcpPrompt, IMcpPromptMessage, IMcpResource, IMcpResourceTemplate, IMcpSamplingService, IMcpServer, IMcpServerConnection, IMcpServerStartOpts, IMcpTool, IMcpToolCallContext, McpCapability, McpCollectionDefinition, McpCollectionReference, McpConnectionFailedError, McpConnectionState, McpDefinitionReference, mcpPromptReplaceSpecialChars, McpResourceURI, McpServerCacheState, McpServerDefinition, McpServerStaticToolAvailability, McpServerTransportType, McpToolName, McpToolVisibility, MpcResponseError, UserInteractionRequiredError } from './mcpTypes.js';
+import { ContributionEnablementState, IEnablementModel } from '../../chat/common/enablement.js';
 import { MCP } from './modelContextProtocol.js';
 import { McpApps } from './modelContextProtocolApps.js';
 import { UriTemplate } from './uriTemplate.js';
@@ -415,9 +418,15 @@ export class McpServer extends Disposable implements IMcpServer {
 	private readonly _loggerId: string;
 	private readonly _logger: ILogger;
 	private _lastModeDebugged = false;
+	private _isQuietStart = false;
+	private _isSandboxSuggestionDialogVisible = false;
+	private _potentialSandboxBlocks: IMcpPotentialSandboxBlock[] = [];
+	private _potentialSandboxBlockListener = this._register(new MutableDisposable<IDisposable>());
 	/** Count of running tool calls, used to detect if sampling is during an LM call */
 	public runningToolCalls = new Set<IMcpToolCallContext>();
 
+	public readonly enablement: IObservable<ContributionEnablementState>;
+
 	constructor(
 		initialCollection: McpCollectionDefinition,
 		public readonly definition: McpDefinitionReference,
@@ -425,6 +434,7 @@ export class McpServer extends Disposable implements IMcpServer {
 		private readonly _requiresExtensionActivation: boolean | undefined,
 		private readonly _primitiveCache: McpServerMetadataCache,
 		toolPrefix: string,
+		enablementModel: IEnablementModel,
 		@IMcpRegistry private readonly _mcpRegistry: IMcpRegistry,
 		@IWorkspaceContextService workspacesService: IWorkspaceContextService,
 		@IExtensionService private readonly _extensionService: IExtensionService,
@@ -433,16 +443,19 @@ export class McpServer extends Disposable implements IMcpServer {
 		@ITelemetryService private readonly _telemetryService: ITelemetryService,
 		@ICommandService private readonly _commandService: ICommandService,
 		@IInstantiationService private readonly _instantiationService: IInstantiationService,
+		@IDialogService private readonly _dialogService: IDialogService,
 		@INotificationService private readonly _notificationService: INotificationService,
 		@IOpenerService private readonly _openerService: IOpenerService,
 		@IMcpSamplingService private readonly _samplingService: IMcpSamplingService,
 		@IMcpElicitationService private readonly _elicitationService: IMcpElicitationService,
+		@IMcpSandboxService private readonly _mcpSandboxService: IMcpSandboxService,
 		@IWorkbenchEnvironmentService environmentService: IWorkbenchEnvironmentService,
 	) {
 		super();
 
 		this.collection = initialCollection;
 		this._fullDefinitions = this._mcpRegistry.getServerDefinition(this.collection, this.definition);
+		this.enablement = derived(r => enablementModel.readEnabled(definition.id, r));
 		this._loggerId = `mcpServer.${definition.id}`;
 		this._logger = this._register(_loggerService.createLogger(this._loggerId, { hidden: true, name: `MCP: ${definition.label}` }));
 
@@ -493,6 +506,11 @@ export class McpServer extends Disposable implements IMcpServer {
 			}
 		}));
 
+		this._register(autorun(reader => {
+			const cnx = this._connection.read(reader);
+			this._potentialSandboxBlockListener.value = cnx?.onPotentialSandboxBlock(block => this.recordPotentialSandboxBlock(block));
+		}));
+
 		const staticMetadata = derived(reader => {
 			const def = this._fullDefinitions.read(reader).server;
 			return def && def.cacheNonce !== this._tools.fromCache?.nonce ? def.staticMetadata : undefined;
@@ -589,6 +607,7 @@ export class McpServer extends Disposable implements IMcpServer {
 			}
 
 			let connection = this._connection.get();
+			this._isQuietStart = !!errorOnUserInteraction;
 			if (connection && McpConnectionState.canBeStarted(connection.state.get().state)) {
 				connection.dispose();
 				connection = undefined;
@@ -629,6 +648,8 @@ export class McpServer extends Disposable implements IMcpServer {
 				}
 			}
 
+			this._potentialSandboxBlocks.length = 0;
+
 			const start = Date.now();
 			let state = await connection.start({
 				createMessageRequestHandler: (params, token) => this._samplingService.sample({
@@ -656,10 +677,6 @@ export class McpServer extends Disposable implements IMcpServer {
 				time: Date.now() - start,
 			});
 
-			if (state.state === McpConnectionState.Kind.Error) {
-				this.showInteractiveError(connection, state, debug);
-			}
-
 			// MCP servers that need auth can 'start' but will stop with an interaction-needed
 			// error they first make a request. In this case, wait until the handler fully
 			// initializes before resolving (throwing if it ends up needing auth)
@@ -684,6 +701,23 @@ export class McpServer extends Disposable implements IMcpServer {
 				}).finally(() => disposable.dispose());
 			}
 
+			if (state.state === McpConnectionState.Kind.Error) {
+				let disposable: IDisposable;
+				state = await new Promise<McpConnectionState>((resolve, reject) => {
+					disposable = autorun(reader => {
+						const cnx = this._connection.read(reader);
+						const state = cnx?.state.read(reader);
+						if (cnx && state?.state === McpConnectionState.Kind.Error) {
+							if (!this._isQuietStart) {
+								this.showInteractiveError(cnx, state, this._lastModeDebugged);
+							} else {
+								reject(new UserInteractionRequiredError('start'));
+							}
+						}
+					});
+				}).finally(() => disposable.dispose());
+			}
+
 			return state;
 		}).finally(() => {
 			interaction?.participants.set(this.definition.id, { s: 'resolved' });
@@ -691,6 +725,12 @@ export class McpServer extends Disposable implements IMcpServer {
 	}
 
 	private showInteractiveError(cnx: IMcpServerConnection, error: McpConnectionState.Error, debug?: boolean) {
+		if (cnx.definition.sandboxEnabled) {
+			if (!this.showSandboxConfigSuggestionFromPotentialBlocks(cnx, this._potentialSandboxBlocks)) {
+				this._notificationService.warn(localize('mcpServerError', 'The MCP server {0} could not be started: {1}', cnx.definition.label, error.message));
+			}
+			return;
+		}
 		if (error.code === 'ENOENT' && cnx.launchDefinition.type === McpServerTransportType.Stdio) {
 			let docsLink: string | undefined;
 			switch (cnx.launchDefinition.command) {
@@ -734,6 +774,82 @@ export class McpServer extends Disposable implements IMcpServer {
 		}
 	}
 
+	public showSandboxConfigSuggestionFromPotentialBlocks(cnx: IMcpServerConnection, potentialBlocks: readonly IMcpPotentialSandboxBlock[]): boolean {
+		if (!cnx.definition.sandboxEnabled || !potentialBlocks.length || this._isSandboxSuggestionDialogVisible) {
+			return false;
+		}
+		if (this._isQuietStart) {
+			throw new UserInteractionRequiredError('sandbox-suggestion');
+		}
+
+		const existingSandboxConfig = this._fullDefinitions.get().collection?.sandbox;
+		const suggestion = this._mcpSandboxService.getSandboxConfigSuggestionMessage(cnx.definition.label, potentialBlocks, existingSandboxConfig);
+		if (!suggestion) {
+			// clear potential blocks as there are no suggestions for them.
+			this._removePotentialSandboxBlocks(potentialBlocks);
+			return false;
+		}
+
+		this._confirmAndApplySandboxConfigSuggestion(cnx, potentialBlocks, suggestion);
+		return true;
+	}
+
+	private _confirmAndApplySandboxConfigSuggestion(cnx: IMcpServerConnection, potentialBlocks: readonly IMcpPotentialSandboxBlock[], suggestion: NonNullable<ReturnType<IMcpSandboxService['getSandboxConfigSuggestionMessage']>>): void {
+		const mcpResource = cnx.definition.presentation?.origin?.uri ?? this.collection.presentation?.origin;
+		const configTarget = this._fullDefinitions.get().collection?.configTarget;
+		this._isSandboxSuggestionDialogVisible = true;
+
+		void this._dialogService.confirm({
+			type: 'warning',
+			message: localize('mcpSandboxSuggestion.confirm.message', "Update sandbox configuration in mcp.json for {0}?", cnx.definition.label),
+			detail: suggestion.message,
+			primaryButton: localize('mcpSandboxSuggestion.confirm.yes', "Yes"),
+			cancelButton: localize('mcpSandboxSuggestion.confirm.no', "No"),
+		}).then(async result => {
+			if (!result.confirmed) {
+				return;
+			}
+
+			if (!mcpResource || configTarget === undefined) {
+				this._notificationService.warn(localize('mcpSandboxSuggestion.apply.unavailable', "Couldn't determine where to update sandbox configuration for {0}.", cnx.definition.label));
+				return;
+			}
+
+			try {
+				const updated = await this._mcpSandboxService.applySandboxConfigSuggestion(cnx.definition, mcpResource, configTarget, potentialBlocks, suggestion.sandboxConfig);
+				if (updated) {
+					this._removePotentialSandboxBlocks(potentialBlocks);
+					this._notificationService.info(localize('mcpSandboxSuggestion.apply.success', "Updated sandbox configuration for {0} in mcp.json. Restart server.", cnx.definition.label));
+				}
+			} catch (e) {
+				this._notificationService.error(localize('mcpSandboxSuggestion.apply.error', "Failed to update sandbox configuration for {0}: {1}", cnx.definition.label, e instanceof Error ? e.message : String(e)));
+			}
+		}).finally(() => {
+			this._isSandboxSuggestionDialogVisible = false;
+		});
+	}
+
+	public recordPotentialSandboxBlock(block: IMcpPotentialSandboxBlock): void {
+		this._potentialSandboxBlocks.push(block);
+		if (this._potentialSandboxBlocks.length > 200) {
+			this._potentialSandboxBlocks.splice(0, this._potentialSandboxBlocks.length - 200);
+		}
+
+		const connection = this._connection.get();
+		if (connection?.state.get().state === McpConnectionState.Kind.Running) {
+			this.showSandboxConfigSuggestionFromPotentialBlocks(connection, this._potentialSandboxBlocks);
+		}
+	}
+
+	private _removePotentialSandboxBlocks(blocks: readonly IMcpPotentialSandboxBlock[]): void {
+		if (!blocks.length || !this._potentialSandboxBlocks.length) {
+			return;
+		}
+
+		const toRemove = new Set(blocks);
+		this._potentialSandboxBlocks = this._potentialSandboxBlocks.filter(block => !toRemove.has(block));
+	}
+
 	public stop(): Promise<void> {
 		return this._connection.get()?.stop() || Promise.resolve();
 	}
@@ -793,6 +909,13 @@ export class McpServer extends Disposable implements IMcpServer {
 			tool.name = tool.name.replace(toolInvalidCharRe, '_');
 		}
 
+		// Per MCP spec, properties is optional. But JSON Schema Draft 7 requires
+		// it for object types. Normalize the schema to include an empty properties
+		// object if not present. https://github.com/microsoft/vscode/issues/251723
+		if (tool.inputSchema && !tool.inputSchema.properties) {
+			tool.inputSchema = { ...tool.inputSchema, properties: {} };
+		}
+
 		type JsonDiagnostic = { message: string; range: { line: number; character: number }[] };
 
 		let diagnostics: JsonDiagnostic[] = [];
@@ -1087,7 +1210,7 @@ export class McpTool implements IMcpTool {
 					arguments: params,
 					task: shouldUseTask ? {} : undefined,
 					_meta: meta,
-				}, token);
+				}, token, progress ? (message) => progress.report({ message }) : undefined);
 
 				// Wait for tools to refresh for dynamic servers (#261611)
 				await this._server.awaitToolRefresh();
diff --git a/src/vs/workbench/contrib/mcp/common/mcpServerConnection.ts b/src/vs/workbench/contrib/mcp/common/mcpServerConnection.ts
index 7adde629336ff..5ab7cdc20d88f 100644
--- a/src/vs/workbench/contrib/mcp/common/mcpServerConnection.ts
+++ b/src/vs/workbench/contrib/mcp/common/mcpServerConnection.ts
@@ -5,6 +5,7 @@
 
 import { CancellationTokenSource } from '../../../../base/common/cancellation.js';
 import { CancellationError } from '../../../../base/common/errors.js';
+import { Emitter } from '../../../../base/common/event.js';
 import { Disposable, DisposableStore, IReference, MutableDisposable, toDisposable } from '../../../../base/common/lifecycle.js';
 import { autorun, IObservable, observableValue } from '../../../../base/common/observable.js';
 import { localize } from '../../../../nls.js';
@@ -13,15 +14,17 @@ import { ILogger, log, LogLevel } from '../../../../platform/log/common/log.js';
 import { IMcpHostDelegate, IMcpMessageTransport } from './mcpRegistryTypes.js';
 import { McpServerRequestHandler } from './mcpServerRequestHandler.js';
 import { McpTaskManager } from './mcpTaskManager.js';
-import { IMcpClientMethods, IMcpServerConnection, McpCollectionDefinition, McpConnectionState, McpServerDefinition, McpServerLaunch } from './mcpTypes.js';
+import { IMcpClientMethods, IMcpPotentialSandboxBlock, IMcpServerConnection, McpCollectionDefinition, McpConnectionState, McpServerDefinition, McpServerLaunch } from './mcpTypes.js';
 
 export class McpServerConnection extends Disposable implements IMcpServerConnection {
 	private readonly _launch = this._register(new MutableDisposable<IReference<IMcpMessageTransport>>());
 	private readonly _state = observableValue<McpConnectionState>('mcpServerState', { state: McpConnectionState.Kind.Stopped });
 	private readonly _requestHandler = observableValue<McpServerRequestHandler | undefined>('mcpServerRequestHandler', undefined);
+	private readonly _onPotentialSandboxBlock = this._register(new Emitter<IMcpPotentialSandboxBlock>());
 
 	public readonly state: IObservable<McpConnectionState> = this._state;
 	public readonly handler: IObservable<McpServerRequestHandler | undefined> = this._requestHandler;
+	public readonly onPotentialSandboxBlock = this._onPotentialSandboxBlock.event;
 
 	constructor(
 		private readonly _collection: McpCollectionDefinition,
@@ -69,6 +72,10 @@ export class McpServerConnection extends Disposable implements IMcpServerConnect
 		store.add(launch);
 		store.add(launch.onDidLog(({ level, message }) => {
 			log(this._logger, level, message);
+			const potentialBlock = this._toPotentialSandboxBlock(message);
+			if (potentialBlock) {
+				this._onPotentialSandboxBlock.fire(potentialBlock);
+			}
 		}));
 
 		let didStart = false;
@@ -141,4 +148,48 @@ export class McpServerConnection extends Disposable implements IMcpServerConnect
 			});
 		});
 	}
+
+	private _toPotentialSandboxBlock(message: string): IMcpPotentialSandboxBlock | undefined {
+		if (!this.definition.sandboxEnabled) {
+			return undefined;
+		}
+
+		if (/No matching config rule, denying:/i.test(message)) {
+			return {
+				kind: 'network',
+				message,
+				host: this._extractSandboxHost(message),
+			};
+		}
+
+		if (/(?:\b(?:EACCES|EPERM|ENOENT|EROFS|fail(?:ed|ure)?)\b|not accessible|read[- ]only)/i.test(message)) {
+			return {
+				kind: 'filesystem',
+				message,
+				path: this._extractSandboxPath(message),
+			};
+		}
+
+		return undefined;
+	}
+
+	private _extractSandboxPath(line: string): string | undefined {
+		const bracketedPath = line.match(/\[(\/[^\]\r\n]+)\]/);
+		if (bracketedPath?.[1]) {
+			return bracketedPath[1].trim();
+		}
+
+		const quotedPath = line.match(/["'`](\/[^"'`]+)["'`]/);
+		if (quotedPath?.[1]) {
+			return quotedPath[1];
+		}
+
+		const trailingPath = line.match(/(\/[\w.\-~/ ]+)$/);
+		return trailingPath?.[1]?.trim();
+	}
+
+	private _extractSandboxHost(value: string): string | undefined {
+		const match = value.match(/No matching config rule, denying:\s+(?<host>[^:\s]+):\d+\.?$/i);
+		return match?.groups?.host;
+	}
 }
diff --git a/src/vs/workbench/contrib/mcp/common/mcpServerRequestHandler.ts b/src/vs/workbench/contrib/mcp/common/mcpServerRequestHandler.ts
index 218f3ab72c888..55c0519c291e5 100644
--- a/src/vs/workbench/contrib/mcp/common/mcpServerRequestHandler.ts
+++ b/src/vs/workbench/contrib/mcp/common/mcpServerRequestHandler.ts
@@ -514,11 +514,11 @@ export class McpServerRequestHandler extends Disposable {
 	/**
 	 * Call a specific tool. Supports tasks automatically if `task` is set on the request.
 	 */
-	async callTool(params: MCP.CallToolRequest['params'] & MCP.Request['params'], token?: CancellationToken): Promise<MCP.CallToolResult> {
+	async callTool(params: MCP.CallToolRequest['params'] & MCP.Request['params'], token?: CancellationToken, onStatusMessage?: (message: string) => void): Promise<MCP.CallToolResult> {
 		const response = await this.sendRequest<MCP.CallToolRequest, MCP.CallToolResult | MCP.CreateTaskResult>({ method: 'tools/call', params }, token);
 
 		if (isTaskResult(response)) {
-			const task = new McpTask<MCP.CallToolResult>(response.task, token);
+			const task = new McpTask<MCP.CallToolResult>(response.task, token, onStatusMessage);
 			this._taskManager.adoptClientTask(task);
 			task.setHandler(this);
 			return task.result.finally(() => {
@@ -603,7 +603,8 @@ export class McpTask<T extends MCP.Result> extends Disposable implements IMcpTas
 
 	constructor(
 		private readonly _task: MCP.Task,
-		_token: CancellationToken = CancellationToken.None
+		_token: CancellationToken = CancellationToken.None,
+		private readonly _onStatusMessage?: (message: string) => void,
 	) {
 		super();
 
@@ -735,6 +736,9 @@ export class McpTask<T extends MCP.Result> extends Disposable implements IMcpTas
 
 	onDidUpdateState(task: MCP.Task) {
 		this._lastTaskState.set(task, undefined);
+		if (task.statusMessage && this._onStatusMessage) {
+			this._onStatusMessage(task.statusMessage);
+		}
 	}
 
 	setHandler(handler: McpServerRequestHandler | undefined): void {
diff --git a/src/vs/workbench/contrib/mcp/common/mcpService.ts b/src/vs/workbench/contrib/mcp/common/mcpService.ts
index f994ad463e17d..940704772ae02 100644
--- a/src/vs/workbench/contrib/mcp/common/mcpService.ts
+++ b/src/vs/workbench/contrib/mcp/common/mcpService.ts
@@ -11,7 +11,8 @@ import { IConfigurationService } from '../../../../platform/configuration/common
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
 import { mcpAutoStartConfig, McpAutoStartValue } from '../../../../platform/mcp/common/mcpManagement.js';
-import { StorageScope } from '../../../../platform/storage/common/storage.js';
+import { IStorageService, StorageScope } from '../../../../platform/storage/common/storage.js';
+import { EnablementModel, isContributionEnabled } from '../../chat/common/enablement.js';
 import { IMcpRegistry } from './mcpRegistryTypes.js';
 import { McpServer, McpServerMetadataCache } from './mcpServer.js';
 import { IAutostartResult, IMcpServer, IMcpService, McpCollectionDefinition, McpConnectionState, McpDefinitionReference, McpServerCacheState, McpServerDefinition, McpStartServerInteraction, McpToolName, UserInteractionRequiredError } from './mcpTypes.js';
@@ -29,6 +30,8 @@ export class McpService extends Disposable implements IMcpService {
 
 	public get lazyCollectionState() { return this._mcpRegistry.lazyCollectionState; }
 
+	public readonly enablementModel: EnablementModel;
+
 	protected readonly userCache: McpServerMetadataCache;
 	protected readonly workspaceCache: McpServerMetadataCache;
 
@@ -36,10 +39,13 @@ export class McpService extends Disposable implements IMcpService {
 		@IInstantiationService private readonly _instantiationService: IInstantiationService,
 		@IMcpRegistry private readonly _mcpRegistry: IMcpRegistry,
 		@ILogService private readonly _logService: ILogService,
-		@IConfigurationService private readonly configurationService: IConfigurationService
+		@IConfigurationService private readonly configurationService: IConfigurationService,
+		@IStorageService storageService: IStorageService,
 	) {
 		super();
 
+		this.enablementModel = this._register(new EnablementModel('mcp.enablement', storageService));
+
 		this.userCache = this._register(_instantiationService.createInstance(McpServerMetadataCache, StorageScope.PROFILE));
 		this.workspaceCache = this._register(_instantiationService.createInstance(McpServerMetadataCache, StorageScope.WORKSPACE));
 
@@ -96,8 +102,11 @@ export class McpService extends Disposable implements IMcpService {
 			return;
 		}
 
-		// don't try re-running errored servers, let the user choose if they want that
-		const candidates = this.servers.get().filter(s => s.connectionState.get().state !== McpConnectionState.Kind.Error);
+		// don't try re-running errored servers or disabled servers
+		const candidates = this.servers.get().filter(s =>
+			s.connectionState.get().state !== McpConnectionState.Kind.Error
+			&& isContributionEnabled(s.enablement.get())
+		);
 
 		let todo = new Set<IMcpServer>();
 		if (autoStartConfig === McpAutoStartValue.OnlyNew) {
@@ -203,6 +212,7 @@ export class McpService extends Disposable implements IMcpService {
 				!!def.collectionDefinition.lazy,
 				def.collectionDefinition.scope === StorageScope.WORKSPACE ? this.workspaceCache : this.userCache,
 				def.toolPrefix,
+				this.enablementModel,
 			);
 
 			nextServers.push({ object, toolPrefix: def.toolPrefix });
diff --git a/src/vs/workbench/contrib/mcp/common/mcpTypes.ts b/src/vs/workbench/contrib/mcp/common/mcpTypes.ts
index 5b26c5133c29a..4877aa5d706ee 100644
--- a/src/vs/workbench/contrib/mcp/common/mcpTypes.ts
+++ b/src/vs/workbench/contrib/mcp/common/mcpTypes.ts
@@ -23,11 +23,12 @@ import { IEditorOptions } from '../../../../platform/editor/common/editor.js';
 import { ExtensionIdentifier } from '../../../../platform/extensions/common/extensions.js';
 import { createDecorator } from '../../../../platform/instantiation/common/instantiation.js';
 import { McpGalleryManifestStatus } from '../../../../platform/mcp/common/mcpGalleryManifest.js';
-import { IGalleryMcpServer, IInstallableMcpServer, IGalleryMcpServerConfiguration, IQueryOptions } from '../../../../platform/mcp/common/mcpManagement.js';
+import { IGalleryMcpServer, IGalleryMcpServerConfiguration, IInstallableMcpServer, IQueryOptions } from '../../../../platform/mcp/common/mcpManagement.js';
 import { IMcpDevModeConfig, IMcpSandboxConfiguration, IMcpServerConfiguration } from '../../../../platform/mcp/common/mcpPlatformTypes.js';
 import { StorageScope } from '../../../../platform/storage/common/storage.js';
 import { IWorkspaceFolder, IWorkspaceFolderData } from '../../../../platform/workspace/common/workspace.js';
 import { IWorkbenchLocalMcpServer, IWorkbencMcpServerInstallOptions } from '../../../services/mcp/common/mcpWorkbenchManagementService.js';
+import { ContributionEnablementState, IEnablementModel } from '../../chat/common/enablement.js';
 import { ToolProgress } from '../../chat/common/tools/languageModelToolsService.js';
 import { IMcpServerSamplingConfiguration } from './mcpConfiguration.js';
 import { McpServerRequestHandler } from './mcpServerRequestHandler.js';
@@ -62,6 +63,8 @@ export interface McpCollectionDefinition {
 	readonly scope: StorageScope;
 	/** Configuration target where configuration related to this server should be stored. */
 	readonly configTarget: ConfigurationTarget;
+	/** Root-level sandbox settings from the mcp config file. */
+	readonly sandbox?: IMcpSandboxConfiguration;
 
 	/** Resolves a server definition. If present, always called before a server starts. */
 	resolveServerLanch?(definition: McpServerDefinition): Promise<McpServerLaunch | undefined>;
@@ -91,6 +94,7 @@ export const enum McpCollectionSortOrder {
 	Workspace = 100,
 	User = 200,
 	Extension = 300,
+	Plugin = 350,
 	Filesystem = 400,
 
 	RemoteBoost = -50,
@@ -111,7 +115,8 @@ export namespace McpCollectionDefinition {
 		return a.id === b.id
 			&& a.remoteAuthority === b.remoteAuthority
 			&& a.label === b.label
-			&& a.trustBehavior === b.trustBehavior;
+			&& a.trustBehavior === b.trustBehavior
+			&& objectsEqual(a.sandbox, b.sandbox);
 	}
 }
 
@@ -134,8 +139,6 @@ export interface McpServerDefinition {
 	readonly staticMetadata?: McpServerStaticMetadata;
 	/** Indicates if the sandbox is enabled for this server. */
 	readonly sandboxEnabled?: boolean;
-	/** Sandbox configuration to apply for this server. */
-	readonly sandbox?: IMcpSandboxConfiguration;
 
 
 	readonly presentation?: {
@@ -169,7 +172,6 @@ export namespace McpServerDefinition {
 		readonly variableReplacement?: McpServerDefinitionVariableReplacement.Serialized;
 		readonly staticMetadata?: McpServerStaticMetadata;
 		readonly sandboxEnabled?: boolean;
-		readonly sandbox?: IMcpSandboxConfiguration;
 	}
 
 	export function toSerialized(def: McpServerDefinition): McpServerDefinition.Serialized {
@@ -184,7 +186,6 @@ export namespace McpServerDefinition {
 			staticMetadata: def.staticMetadata,
 			launch: McpServerLaunch.fromSerialized(def.launch),
 			sandboxEnabled: def.sandboxEnabled,
-			sandbox: def.sandboxEnabled ? def.sandbox : undefined,
 			variableReplacement: def.variableReplacement ? McpServerDefinitionVariableReplacement.fromSerialized(def.variableReplacement) : undefined,
 		};
 	}
@@ -198,8 +199,8 @@ export namespace McpServerDefinition {
 			&& objectsEqual(a.presentation, b.presentation)
 			&& objectsEqual(a.variableReplacement, b.variableReplacement)
 			&& objectsEqual(a.devMode, b.devMode)
-			&& a.sandboxEnabled === b.sandboxEnabled
-			&& objectsEqual(a.sandbox, b.sandbox);
+			&& a.sandboxEnabled === b.sandboxEnabled;
+
 	}
 }
 
@@ -245,6 +246,9 @@ export interface IMcpService {
 	_serviceBrand: undefined;
 	readonly servers: IObservable<readonly IMcpServer[]>;
 
+	/** The enablement model for MCP servers. */
+	readonly enablementModel: IEnablementModel;
+
 	/** Resets the cached tools. */
 	resetCaches(): void;
 
@@ -329,6 +333,7 @@ export namespace McpServerTrust {
 export interface IMcpServer extends IDisposable {
 	readonly collection: McpCollectionReference;
 	readonly definition: McpDefinitionReference;
+	readonly enablement: IObservable<ContributionEnablementState>;
 	readonly connection: IObservable<IMcpServerConnection | undefined>;
 	readonly connectionState: IObservable<McpConnectionState>;
 	readonly serverMetadata: IObservable<{
@@ -515,6 +520,7 @@ export interface McpServerTransportStdio {
 	readonly args: readonly string[];
 	readonly env: Record<string, string | number | null>;
 	readonly envFile: string | undefined;
+	readonly sandbox: IMcpSandboxConfiguration | undefined;
 }
 
 export interface McpServerTransportHTTPAuthentication {
@@ -547,7 +553,7 @@ export type McpServerLaunch =
 export namespace McpServerLaunch {
 	export type Serialized =
 		| { type: McpServerTransportType.HTTP; uri: UriComponents; headers: [string, string][]; authentication?: McpServerTransportHTTPAuthentication }
-		| { type: McpServerTransportType.Stdio; cwd: string | undefined; command: string; args: readonly string[]; env: Record<string, string | number | null>; envFile: string | undefined };
+		| { type: McpServerTransportType.Stdio; cwd: string | undefined; command: string; args: readonly string[]; env: Record<string, string | number | null>; envFile: string | undefined; sandbox: IMcpSandboxConfiguration | undefined };
 
 	export function toSerialized(launch: McpServerLaunch): McpServerLaunch.Serialized {
 		return launch;
@@ -565,6 +571,7 @@ export namespace McpServerLaunch {
 					args: launch.args,
 					env: launch.env,
 					envFile: launch.envFile,
+					sandbox: launch.sandbox
 				};
 		}
 	}
@@ -580,10 +587,18 @@ export namespace McpServerLaunch {
  * stopped, and restarted. Once started and in a running state, it will
  * eventually build a {@link IMcpServerConnection.handler}.
  */
+export interface IMcpPotentialSandboxBlock {
+	readonly kind: 'network' | 'filesystem';
+	readonly message: string;
+	readonly host?: string;
+	readonly path?: string;
+}
+
 export interface IMcpServerConnection extends IDisposable {
 	readonly definition: McpServerDefinition;
 	readonly state: IObservable<McpConnectionState>;
 	readonly handler: IObservable<McpServerRequestHandler | undefined>;
+	readonly onPotentialSandboxBlock: Event<IMcpPotentialSandboxBlock>;
 
 	/**
 	 * Resolved launch definition. Might not match the `definition.launch` due to
@@ -732,6 +747,8 @@ export interface IMcpServerEditorOptions extends IEditorOptions {
 export const enum McpServerEnablementState {
 	Disabled,
 	DisabledByAccess,
+	DisabledProfile,
+	DisabledWorkspace,
 	Enabled,
 }
 
diff --git a/src/vs/workbench/contrib/mcp/electron-browser/mcpGatewayService.ts b/src/vs/workbench/contrib/mcp/electron-browser/mcpGatewayService.ts
index 2af2c0b4adf0d..71d0dcdc64b08 100644
--- a/src/vs/workbench/contrib/mcp/electron-browser/mcpGatewayService.ts
+++ b/src/vs/workbench/contrib/mcp/electron-browser/mcpGatewayService.ts
@@ -6,6 +6,7 @@
 import { URI } from '../../../../base/common/uri.js';
 import { ProxyChannel } from '../../../../base/parts/ipc/common/ipc.js';
 import { IMainProcessService } from '../../../../platform/ipc/common/mainProcessService.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
 import { IMcpGatewayService, McpGatewayChannelName } from '../../../../platform/mcp/common/mcpGateway.js';
 import { IRemoteAgentService } from '../../../services/remote/common/remoteAgentService.js';
 import { IMcpGatewayResult, IWorkbenchMcpGatewayService } from '../common/mcpGatewayService.js';
@@ -24,6 +25,7 @@ export class WorkbenchMcpGatewayService implements IWorkbenchMcpGatewayService {
 	constructor(
 		@IMainProcessService mainProcessService: IMainProcessService,
 		@IRemoteAgentService private readonly _remoteAgentService: IRemoteAgentService,
+		@ILogService private readonly _logService: ILogService,
 	) {
 		this._localPlatformService = ProxyChannel.toService<IMcpGatewayService>(
 			mainProcessService.getChannel(McpGatewayChannelName)
@@ -31,6 +33,7 @@ export class WorkbenchMcpGatewayService implements IWorkbenchMcpGatewayService {
 	}
 
 	async createGateway(inRemote: boolean): Promise<IMcpGatewayResult | undefined> {
+		this._logService.debug(`[McpGateway][Workbench] createGateway requested (inRemote=${inRemote})`);
 		if (inRemote) {
 			return this._createRemoteGateway();
 		} else {
@@ -39,11 +42,15 @@ export class WorkbenchMcpGatewayService implements IWorkbenchMcpGatewayService {
 	}
 
 	private async _createLocalGateway(): Promise<IMcpGatewayResult> {
+		this._logService.info('[McpGateway][Workbench] Creating local gateway via main process');
 		const info = await this._localPlatformService.createGateway(undefined);
+		const address = URI.revive(info.address);
+		this._logService.info(`[McpGateway][Workbench] Local gateway created: ${address}`);
 
 		return {
-			address: URI.revive(info.address),
+			address,
 			dispose: () => {
+				this._logService.info(`[McpGateway][Workbench] Disposing local gateway: ${info.gatewayId}`);
 				this._localPlatformService.disposeGateway(info.gatewayId);
 			}
 		};
@@ -52,17 +59,21 @@ export class WorkbenchMcpGatewayService implements IWorkbenchMcpGatewayService {
 	private async _createRemoteGateway(): Promise<IMcpGatewayResult | undefined> {
 		const connection = this._remoteAgentService.getConnection();
 		if (!connection) {
-			// No remote connection - cannot create remote gateway
+			this._logService.info('[McpGateway][Workbench] No remote connection available for remote gateway');
 			return undefined;
 		}
 
+		this._logService.info('[McpGateway][Workbench] Creating remote gateway via remote server');
 		return connection.withChannel(McpGatewayChannelName, async channel => {
 			const service = ProxyChannel.toService<IMcpGatewayService>(channel);
 			const info = await service.createGateway(undefined);
+			const address = URI.revive(info.address);
+			this._logService.info(`[McpGateway][Workbench] Remote gateway created: ${address}`);
 
 			return {
-				address: URI.revive(info.address),
+				address,
 				dispose: () => {
+					this._logService.info(`[McpGateway][Workbench] Disposing remote gateway: ${info.gatewayId}`);
 					service.disposeGateway(info.gatewayId);
 				}
 			};
diff --git a/src/vs/workbench/contrib/mcp/electron-browser/mcpGatewayToolBrokerContribution.ts b/src/vs/workbench/contrib/mcp/electron-browser/mcpGatewayToolBrokerContribution.ts
index af994c82fe31a..778d53de5f644 100644
--- a/src/vs/workbench/contrib/mcp/electron-browser/mcpGatewayToolBrokerContribution.ts
+++ b/src/vs/workbench/contrib/mcp/electron-browser/mcpGatewayToolBrokerContribution.ts
@@ -5,6 +5,7 @@
 
 import { IWorkbenchContribution } from '../../../common/contributions.js';
 import { IMainProcessService } from '../../../../platform/ipc/common/mainProcessService.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
 import { McpGatewayToolBrokerChannelName } from '../../../../platform/mcp/common/mcpGateway.js';
 import { IMcpService } from '../common/mcpTypes.js';
 import { McpGatewayToolBrokerChannel } from '../common/mcpGatewayToolBrokerChannel.js';
@@ -13,7 +14,8 @@ export class McpGatewayToolBrokerContribution implements IWorkbenchContribution
 	constructor(
 		@IMainProcessService mainProcessService: IMainProcessService,
 		@IMcpService mcpService: IMcpService,
+		@ILogService logService: ILogService,
 	) {
-		mainProcessService.registerChannel(McpGatewayToolBrokerChannelName, new McpGatewayToolBrokerChannel(mcpService));
+		mainProcessService.registerChannel(McpGatewayToolBrokerChannelName, new McpGatewayToolBrokerChannel(mcpService, logService));
 	}
 }
diff --git a/src/vs/workbench/contrib/mcp/test/common/mcpGatewayToolBrokerChannel.test.ts b/src/vs/workbench/contrib/mcp/test/common/mcpGatewayToolBrokerChannel.test.ts
index 53124c8acc37f..e0dcab8d7f18d 100644
--- a/src/vs/workbench/contrib/mcp/test/common/mcpGatewayToolBrokerChannel.test.ts
+++ b/src/vs/workbench/contrib/mcp/test/common/mcpGatewayToolBrokerChannel.test.ts
@@ -6,7 +6,10 @@
 import assert from 'assert';
 import { CancellationToken } from '../../../../../base/common/cancellation.js';
 import { observableValue } from '../../../../../base/common/observable.js';
+import { runWithFakedTimers } from '../../../../../base/test/common/timeTravelScheduler.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { ContributionEnablementState } from '../../../chat/common/enablement.js';
+import { NullLogService } from '../../../../../platform/log/common/log.js';
 import { IGatewayCallToolResult } from '../../../../../platform/mcp/common/mcpGateway.js';
 import { MCP } from '../../common/modelContextProtocol.js';
 import { McpGatewayToolBrokerChannel } from '../../common/mcpGatewayToolBrokerChannel.js';
@@ -18,7 +21,7 @@ suite('McpGatewayToolBrokerChannel', () => {
 
 	test('lists model-visible tools with namespaced identities', async () => {
 		const mcpService = new TestMcpService();
-		const channel = new McpGatewayToolBrokerChannel(mcpService);
+		const channel = new McpGatewayToolBrokerChannel(mcpService, new NullLogService());
 
 		const serverA = createServer('collectionA', 'serverA', [
 			createTool('mcp_serverA_echo', async () => ({ content: [{ type: 'text', text: 'A' }] })),
@@ -43,7 +46,7 @@ suite('McpGatewayToolBrokerChannel', () => {
 
 	test('routes tool calls by namespaced identity', async () => {
 		const mcpService = new TestMcpService();
-		const channel = new McpGatewayToolBrokerChannel(mcpService);
+		const channel = new McpGatewayToolBrokerChannel(mcpService, new NullLogService());
 
 		const invoked: string[] = [];
 		const serverA = createServer('collectionA', 'serverA', [
@@ -79,7 +82,7 @@ suite('McpGatewayToolBrokerChannel', () => {
 
 	test('emits onDidChangeTools when tool lists change', async () => {
 		const mcpService = new TestMcpService();
-		const channel = new McpGatewayToolBrokerChannel(mcpService);
+		const channel = new McpGatewayToolBrokerChannel(mcpService, new NullLogService());
 		const server = createServer('collectionA', 'serverA', [
 			createTool('echo', async () => ({ content: [{ type: 'text', text: 'A' }] })),
 		]);
@@ -104,7 +107,7 @@ suite('McpGatewayToolBrokerChannel', () => {
 
 	test('does not start server when cache state is live', async () => {
 		const mcpService = new TestMcpService();
-		const channel = new McpGatewayToolBrokerChannel(mcpService);
+		const channel = new McpGatewayToolBrokerChannel(mcpService, new NullLogService());
 
 		const server = createServer(
 			'collectionA',
@@ -122,7 +125,7 @@ suite('McpGatewayToolBrokerChannel', () => {
 
 	test('starts server when cache state is unknown', async () => {
 		const mcpService = new TestMcpService();
-		const channel = new McpGatewayToolBrokerChannel(mcpService);
+		const channel = new McpGatewayToolBrokerChannel(mcpService, new NullLogService());
 
 		const server = createServer(
 			'collectionA',
@@ -132,11 +135,121 @@ suite('McpGatewayToolBrokerChannel', () => {
 		);
 
 		mcpService.servers.set([server], undefined);
-		await channel.call<readonly MCP.Tool[]>(undefined, 'listTools');
+		const tools = await channel.call<readonly MCP.Tool[]>(undefined, 'listTools');
+
+		// Server started during the grace period; tools are now available.
+		assert.strictEqual(server.startCalls, 1);
+		assert.deepStrictEqual(tools.map(t => t.name), ['echo']);
+		channel.dispose();
+	});
+
+	test('starts server and waits within grace period when cache state is outdated', async () => {
+		const mcpService = new TestMcpService();
+		const channel = new McpGatewayToolBrokerChannel(mcpService, new NullLogService());
+
+		const server = createServer(
+			'collectionA',
+			'serverA',
+			[createTool('echo', async () => ({ content: [{ type: 'text', text: 'A' }] }))],
+			McpServerCacheState.Outdated,
+		);
 
+		mcpService.servers.set([server], undefined);
+		const tools = await channel.call<readonly MCP.Tool[]>(undefined, 'listTools');
+
+		// Outdated server gets the same grace period as Unknown — started and tools returned.
 		assert.strictEqual(server.startCalls, 1);
+		assert.deepStrictEqual(tools.map(t => t.name), ['echo']);
 		channel.dispose();
 	});
+
+	test('returns empty tools and does not re-wait if server does not start within grace period', () => {
+		return runWithFakedTimers({ useFakeTimers: true }, async () => {
+			const mcpService = new TestMcpService();
+			const channel = new McpGatewayToolBrokerChannel(mcpService, new NullLogService(), 100);
+
+			const server = createNeverStartingServer(
+				'collectionA',
+				'serverA',
+				[createTool('echo', async () => ({ content: [{ type: 'text', text: 'A' }] }))],
+			);
+
+			mcpService.servers.set([server], undefined);
+
+			// First call: waits up to the grace period, server never starts → empty result.
+			const tools = await channel.call<readonly MCP.Tool[]>(undefined, 'listTools');
+			assert.deepStrictEqual(tools, []);
+
+			// Second call: grace-period promise already resolved; returns immediately without re-waiting.
+			const tools2 = await channel.call<readonly MCP.Tool[]>(undefined, 'listTools');
+			assert.deepStrictEqual(tools2, []);
+
+			channel.dispose();
+		});
+	});
+
+	test('invalidates stale grace entry when cacheState regresses to Unknown after timeout', () => {
+		return runWithFakedTimers({ useFakeTimers: true }, async () => {
+			const mcpService = new TestMcpService();
+			const channel = new McpGatewayToolBrokerChannel(mcpService, new NullLogService(), 100);
+
+			const server = createNeverStartingServer(
+				'collectionA',
+				'serverA',
+				[createTool('echo', async () => ({ content: [{ type: 'text', text: 'A' }] }))],
+			);
+
+			mcpService.servers.set([server], undefined);
+
+			// First call: grace period elapses, server never starts → empty.
+			const tools1 = await channel.call<readonly MCP.Tool[]>(undefined, 'listTools');
+			assert.deepStrictEqual(tools1, []);
+			assert.strictEqual(server.startCalls, 1);
+
+			// Simulate a cache reset: server goes back to Unknown.
+			server.cacheStateValue.set(McpServerCacheState.Unknown, undefined);
+
+			// Make the server succeed this time.
+			server.startBehavior = 'succeed';
+
+			// Second call: stale grace entry should be discarded, a new grace race starts,
+			// and the server successfully starts → tools returned.
+			const tools2 = await channel.call<readonly MCP.Tool[]>(undefined, 'listTools');
+			assert.deepStrictEqual(tools2.map(t => t.name), ['echo']);
+			assert.strictEqual(server.startCalls, 2);
+
+			channel.dispose();
+		});
+	});
+
+	test('does not invalidate grace entry when cacheState is not Unknown/Outdated', () => {
+		return runWithFakedTimers({ useFakeTimers: true }, async () => {
+			const mcpService = new TestMcpService();
+			const channel = new McpGatewayToolBrokerChannel(mcpService, new NullLogService(), 100);
+
+			const server = createServer(
+				'collectionA',
+				'serverA',
+				[createTool('echo', async () => ({ content: [{ type: 'text', text: 'A' }] }))],
+				McpServerCacheState.Unknown,
+			);
+
+			mcpService.servers.set([server], undefined);
+
+			// First call: server starts successfully during grace period.
+			const tools1 = await channel.call<readonly MCP.Tool[]>(undefined, 'listTools');
+			assert.deepStrictEqual(tools1.map(t => t.name), ['echo']);
+			assert.strictEqual(server.startCalls, 1);
+
+			// Second call: cacheState is now Live (server started), grace entry should NOT
+			// be invalidated, so no additional start call is made.
+			const tools2 = await channel.call<readonly MCP.Tool[]>(undefined, 'listTools');
+			assert.deepStrictEqual(tools2.map(t => t.name), ['echo']);
+			assert.strictEqual(server.startCalls, 1);
+
+			channel.dispose();
+		});
+	});
 });
 
 function createServer(
@@ -156,6 +269,7 @@ function createServer(
 		definition: { id: definitionId, label: definitionId },
 		connection: observableValue(owner, undefined),
 		connectionState,
+		enablement: observableValue(owner, ContributionEnablementState.EnabledProfile),
 		serverMetadata: observableValue(owner, undefined),
 		readDefinitions: () => observableValue(owner, { server: undefined, collection: undefined }),
 		showOutput: async () => { },
@@ -177,6 +291,52 @@ function createServer(
 	};
 }
 
+function createNeverStartingServer(
+	collectionId: string,
+	definitionId: string,
+	initialTools: readonly IMcpTool[],
+): IMcpServer & { startCalls: number; startBehavior: 'hang' | 'succeed'; cacheStateValue: ReturnType<typeof observableValue<McpServerCacheState>> } {
+	const owner = {};
+	const tools = observableValue<readonly IMcpTool[]>(owner, initialTools);
+	const connectionState = observableValue<McpConnectionState>(owner, { state: McpConnectionState.Kind.Running });
+	const cacheState = observableValue<McpServerCacheState>(owner, McpServerCacheState.Unknown);
+	let startCalls = 0;
+	let startBehavior: 'hang' | 'succeed' = 'hang';
+
+	const result: IMcpServer & { startCalls: number; startBehavior: 'hang' | 'succeed'; cacheStateValue: ReturnType<typeof observableValue<McpServerCacheState>> } = {
+		collection: { id: collectionId, label: collectionId },
+		definition: { id: definitionId, label: definitionId },
+		connection: observableValue(owner, undefined),
+		connectionState,
+		enablement: observableValue(owner, ContributionEnablementState.EnabledProfile),
+		serverMetadata: observableValue(owner, undefined),
+		readDefinitions: () => observableValue(owner, { server: undefined, collection: undefined }),
+		showOutput: async () => { },
+		start: async () => {
+			startCalls++;
+			if (result.startBehavior === 'succeed') {
+				cacheState.set(McpServerCacheState.Live, undefined);
+				return { state: McpConnectionState.Kind.Running };
+			}
+			// Never resolves — simulates a server that hangs on startup.
+			return new Promise<McpConnectionState>(() => { });
+		},
+		stop: async () => { },
+		cacheState,
+		tools,
+		prompts: observableValue(owner, []),
+		capabilities: observableValue(owner, undefined),
+		resources: () => (async function* () { })(),
+		resourceTemplates: async () => [],
+		dispose: () => { },
+		get startCalls() { return startCalls; },
+		get startBehavior() { return startBehavior; },
+		set startBehavior(v) { startBehavior = v; },
+		cacheStateValue: cacheState,
+	};
+	return result;
+}
+
 function createTool(name: string, call: (params: Record<string, unknown>) => Promise<MCP.CallToolResult>, visibility: McpToolVisibility = McpToolVisibility.Model): IMcpTool {
 	const definition: MCP.Tool = {
 		name,
diff --git a/src/vs/workbench/contrib/mcp/test/common/mcpIcons.test.ts b/src/vs/workbench/contrib/mcp/test/common/mcpIcons.test.ts
index 7cdb2b661d0d2..90430507be1b5 100644
--- a/src/vs/workbench/contrib/mcp/test/common/mcpIcons.test.ts
+++ b/src/vs/workbench/contrib/mcp/test/common/mcpIcons.test.ts
@@ -22,7 +22,8 @@ const createStdioLaunch = (): McpServerTransportStdio => ({
 	command: 'cmd',
 	args: [],
 	env: {},
-	envFile: undefined
+	envFile: undefined,
+	sandbox: undefined
 });
 
 suite('MCP Icons', () => {
diff --git a/src/vs/workbench/contrib/mcp/test/common/mcpRegistry.test.ts b/src/vs/workbench/contrib/mcp/test/common/mcpRegistry.test.ts
index e48fa86019459..722a4ee2fe77f 100644
--- a/src/vs/workbench/contrib/mcp/test/common/mcpRegistry.test.ts
+++ b/src/vs/workbench/contrib/mcp/test/common/mcpRegistry.test.ts
@@ -8,6 +8,7 @@ import * as sinon from 'sinon';
 import { timeout } from '../../../../../base/common/async.js';
 import { Disposable } from '../../../../../base/common/lifecycle.js';
 import { ISettableObservable, observableValue } from '../../../../../base/common/observable.js';
+import { URI } from '../../../../../base/common/uri.js';
 import { upcast } from '../../../../../base/common/types.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
 import { ConfigurationTarget, IConfigurationChangeEvent, IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
@@ -17,6 +18,7 @@ import { ServiceCollection } from '../../../../../platform/instantiation/common/
 import { TestInstantiationService } from '../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
 import { ILogger, ILoggerService, ILogService, NullLogger, NullLogService } from '../../../../../platform/log/common/log.js';
 import { mcpAccessConfig, McpAccessValue } from '../../../../../platform/mcp/common/mcpManagement.js';
+import { IMcpSandboxConfiguration } from '../../../../../platform/mcp/common/mcpPlatformTypes.js';
 import { INotificationService } from '../../../../../platform/notification/common/notification.js';
 import { TestNotificationService } from '../../../../../platform/notification/test/common/testNotificationService.js';
 import { IProductService } from '../../../../../platform/product/common/productService.js';
@@ -33,7 +35,7 @@ import { IMcpHostDelegate, IMcpMessageTransport } from '../../common/mcpRegistry
 import { IMcpSandboxService } from '../../common/mcpSandboxService.js';
 import { McpServerConnection } from '../../common/mcpServerConnection.js';
 import { McpTaskManager } from '../../common/mcpTaskManager.js';
-import { LazyCollectionState, McpCollectionDefinition, McpServerDefinition, McpServerLaunch, McpServerTransportStdio, McpServerTransportType, McpServerTrust, McpStartServerInteraction } from '../../common/mcpTypes.js';
+import { IMcpPotentialSandboxBlock, LazyCollectionState, McpCollectionDefinition, McpServerDefinition, McpServerLaunch, McpServerTransportStdio, McpServerTransportType, McpServerTrust, McpStartServerInteraction } from '../../common/mcpTypes.js';
 import { TestMcpMessageTransport } from './mcpRegistryTypes.js';
 
 class TestConfigurationResolverService {
@@ -161,6 +163,14 @@ class TestMcpSandboxService implements IMcpSandboxService {
 	isEnabled(serverDef: McpServerDefinition): Promise<boolean> {
 		return Promise.resolve(this.enabled);
 	}
+
+	getSandboxConfigSuggestionMessage(_serverLabel: string, _potentialBlocks: readonly IMcpPotentialSandboxBlock[], _existingSandboxConfig?: IMcpSandboxConfiguration): { message: string; sandboxConfig: IMcpSandboxConfiguration } | undefined {
+		return undefined;
+	}
+
+	applySandboxConfigSuggestion(_serverDef: McpServerDefinition, _mcpResource: URI, _configTarget: ConfigurationTarget, _potentialBlocks: readonly IMcpPotentialSandboxBlock[], _suggestedSandboxConfig?: IMcpSandboxConfiguration): Promise<boolean> {
+		return Promise.resolve(false);
+	}
 }
 
 suite('Workbench - MCP - Registry', () => {
@@ -229,6 +239,7 @@ suite('Workbench - MCP - Registry', () => {
 				env: {},
 				envFile: undefined,
 				cwd: '/test',
+				sandbox: undefined
 			}
 		};
 	});
@@ -291,6 +302,7 @@ suite('Workbench - MCP - Registry', () => {
 				},
 				envFile: undefined,
 				cwd: '/test',
+				sandbox: undefined
 			},
 			variableReplacement: {
 				section: 'mcp',
@@ -371,11 +383,15 @@ suite('Workbench - MCP - Registry', () => {
 
 	test('resolveConnection calls launchInSandboxIfEnabled with expected arguments when sandboxing is enabled', async () => {
 		testMcpSandboxService.enabled = true;
+		const mcpResource = URI.file('/test/mcp.json');
 
 		const sandboxCollection: McpCollectionDefinition & { serverDefinitions: ISettableObservable<McpServerDefinition[]> } = {
 			...testCollection,
 			id: 'sandbox-collection',
 			remoteAuthority: 'ssh-remote+test',
+			presentation: {
+				origin: mcpResource,
+			},
 		};
 
 		const definition: McpServerDefinition = {
@@ -388,6 +404,7 @@ suite('Workbench - MCP - Registry', () => {
 				env: {},
 				envFile: undefined,
 				cwd: '/test',
+				sandbox: undefined
 			},
 		};
 
@@ -712,6 +729,7 @@ suite('Workbench - MCP - Registry', () => {
 					env: {},
 					envFile: undefined,
 					cwd: '/test',
+					sandbox: undefined
 				}
 			};
 		}
diff --git a/src/vs/workbench/contrib/mcp/test/common/mcpRegistryTypes.ts b/src/vs/workbench/contrib/mcp/test/common/mcpRegistryTypes.ts
index 2648adedeb4c9..69b07fdf55f6f 100644
--- a/src/vs/workbench/contrib/mcp/test/common/mcpRegistryTypes.ts
+++ b/src/vs/workbench/contrib/mcp/test/common/mcpRegistryTypes.ts
@@ -171,7 +171,7 @@ export class TestMcpRegistry implements IMcpRegistry {
 		serverDefinitions: observableValue(this, [{
 			id: 'test-server',
 			label: 'Test Server',
-			launch: { type: McpServerTransportType.Stdio, command: 'echo', args: ['Hello MCP'], env: {}, envFile: undefined, cwd: undefined },
+			launch: { type: McpServerTransportType.Stdio, command: 'echo', args: ['Hello MCP'], env: {}, envFile: undefined, cwd: undefined, sandbox: undefined },
 			cacheNonce: 'a',
 		} satisfies McpServerDefinition]),
 		trustBehavior: McpServerTrust.Kind.Trusted,
diff --git a/src/vs/workbench/contrib/mcp/test/common/mcpResourceFilesystem.test.ts b/src/vs/workbench/contrib/mcp/test/common/mcpResourceFilesystem.test.ts
index 543ab09965b69..e546b5f5153ff 100644
--- a/src/vs/workbench/contrib/mcp/test/common/mcpResourceFilesystem.test.ts
+++ b/src/vs/workbench/contrib/mcp/test/common/mcpResourceFilesystem.test.ts
@@ -35,9 +35,10 @@ suite('Workbench - MCP - ResourceFilesystem', () => {
 	let fs: McpResourceFilesystem;
 
 	setup(() => {
+		const storageService = ds.add(new TestStorageService());
 		const services = new ServiceCollection(
 			[IFileService, { registerProvider: () => { } }],
-			[IStorageService, ds.add(new TestStorageService())],
+			[IStorageService, storageService],
 			[ILoggerService, ds.add(new TestLoggerService())],
 			[IWorkspaceContextService, new TestContextService()],
 			[IWorkbenchEnvironmentService, {}],
@@ -49,7 +50,7 @@ suite('Workbench - MCP - ResourceFilesystem', () => {
 		const registry = new TestMcpRegistry(parentInsta1);
 
 		const parentInsta2 = ds.add(parentInsta1.createChild(new ServiceCollection([IMcpRegistry, registry])));
-		const mcpService = ds.add(new McpService(parentInsta2, registry, new NullLogService(), new TestConfigurationService()));
+		const mcpService = ds.add(new McpService(parentInsta2, registry, new NullLogService(), new TestConfigurationService(), storageService));
 		mcpService.updateCollectedServers();
 
 		const instaService = ds.add(parentInsta2.createChild(new ServiceCollection(
diff --git a/src/vs/workbench/contrib/mcp/test/common/mcpServerConnection.test.ts b/src/vs/workbench/contrib/mcp/test/common/mcpServerConnection.test.ts
index 33114bc70d42b..518481fb12320 100644
--- a/src/vs/workbench/contrib/mcp/test/common/mcpServerConnection.test.ts
+++ b/src/vs/workbench/contrib/mcp/test/common/mcpServerConnection.test.ts
@@ -108,7 +108,8 @@ suite('Workbench - MCP - ServerConnection', () => {
 				args: [],
 				env: {},
 				envFile: undefined,
-				cwd: '/test'
+				cwd: '/test',
+				sandbox: undefined
 			}
 		};
 	});
@@ -337,6 +338,153 @@ suite('Workbench - MCP - ServerConnection', () => {
 		await timeout(10);
 	});
 
+	test('should emit a sandbox filesystem block for read-only errors with backtick paths', async () => {
+		const sandboxedDefinition: McpServerDefinition = {
+			...serverDefinition,
+			sandboxEnabled: true,
+		};
+
+		const connection = instantiationService.createInstance(
+			McpServerConnection,
+			collection,
+			sandboxedDefinition,
+			delegate,
+			sandboxedDefinition.launch,
+			new NullLogger(),
+			false,
+			store.add(new McpTaskManager()),
+		);
+		store.add(connection);
+
+		const message = 'error: failed to open file `/test-for-sandbox/.git`: Read-only file system (os error 30)';
+		const sandboxBlock = Event.toPromise(connection.onPotentialSandboxBlock);
+		const startPromise = connection.start({});
+
+		transport.simulateLog(message);
+		transport.setConnectionState({ state: McpConnectionState.Kind.Running });
+
+		assert.deepStrictEqual(await sandboxBlock, {
+			kind: 'filesystem',
+			message,
+			path: '/test-for-sandbox/.git',
+		});
+
+		await startPromise;
+
+		connection.dispose();
+		await timeout(10);
+	});
+
+	test('should emit a sandbox filesystem block for read-only errors with double-quoted paths', async () => {
+		const sandboxedDefinition: McpServerDefinition = {
+			...serverDefinition,
+			sandboxEnabled: true,
+		};
+
+		const connection = instantiationService.createInstance(
+			McpServerConnection,
+			collection,
+			sandboxedDefinition,
+			delegate,
+			sandboxedDefinition.launch,
+			new NullLogger(),
+			false,
+			store.add(new McpTaskManager()),
+		);
+		store.add(connection);
+
+		const message = 'error: failed to open file `/test-for-sandbox/.testfile`: Read-only file system (os error 30)';
+		const sandboxBlock = Event.toPromise(connection.onPotentialSandboxBlock);
+		const startPromise = connection.start({});
+
+		transport.simulateLog(message);
+		transport.setConnectionState({ state: McpConnectionState.Kind.Running });
+
+		assert.deepStrictEqual(await sandboxBlock, {
+			kind: 'filesystem',
+			message,
+			path: '/test-for-sandbox/.testfile',
+		});
+
+		await startPromise;
+
+		connection.dispose();
+		await timeout(10);
+	});
+
+	test('should emit a sandbox filesystem block for read-only at-path errors with double-quoted paths', async () => {
+		const sandboxedDefinition: McpServerDefinition = {
+			...serverDefinition,
+			sandboxEnabled: true,
+		};
+
+		const connection = instantiationService.createInstance(
+			McpServerConnection,
+			collection,
+			sandboxedDefinition,
+			delegate,
+			sandboxedDefinition.launch,
+			new NullLogger(),
+			false,
+			store.add(new McpTaskManager()),
+		);
+		store.add(connection);
+
+		const message = 'error: Read-only file system (os error 30) at path "/test-for-sandbox/.testfile"';
+		const sandboxBlock = Event.toPromise(connection.onPotentialSandboxBlock);
+		const startPromise = connection.start({});
+
+		transport.simulateLog(message);
+		transport.setConnectionState({ state: McpConnectionState.Kind.Running });
+
+		assert.deepStrictEqual(await sandboxBlock, {
+			kind: 'filesystem',
+			message,
+			path: '/test-for-sandbox/.testfile',
+		});
+
+		await startPromise;
+
+		connection.dispose();
+		await timeout(10);
+	});
+
+	test('should emit a sandbox network block with the denied host', async () => {
+		const sandboxedDefinition: McpServerDefinition = {
+			...serverDefinition,
+			sandboxEnabled: true,
+		};
+
+		const connection = instantiationService.createInstance(
+			McpServerConnection,
+			collection,
+			sandboxedDefinition,
+			delegate,
+			sandboxedDefinition.launch,
+			new NullLogger(),
+			false,
+			store.add(new McpTaskManager()),
+		);
+		store.add(connection);
+
+		const sandboxBlock = Event.toPromise(connection.onPotentialSandboxBlock);
+		const startPromise = connection.start({});
+
+		transport.simulateLog('No matching config rule, denying: api.example.com:443.');
+		transport.setConnectionState({ state: McpConnectionState.Kind.Running });
+
+		assert.deepStrictEqual(await sandboxBlock, {
+			kind: 'network',
+			message: 'No matching config rule, denying: api.example.com:443.',
+			host: 'api.example.com',
+		});
+
+		await startPromise;
+
+		connection.dispose();
+		await timeout(10);
+	});
+
 	test('should correctly handle transitions to and from error state', async () => {
 		// Create server connection
 		const connection = instantiationService.createInstance(
diff --git a/src/vs/workbench/contrib/mcp/test/common/mcpTypes.test.ts b/src/vs/workbench/contrib/mcp/test/common/mcpTypes.test.ts
index b73a1d48fb5f0..d7a6d11283b50 100644
--- a/src/vs/workbench/contrib/mcp/test/common/mcpTypes.test.ts
+++ b/src/vs/workbench/contrib/mcp/test/common/mcpTypes.test.ts
@@ -40,7 +40,8 @@ suite('MCP Types', () => {
 				command: 'test-command',
 				args: [],
 				env: {},
-				envFile: undefined
+				envFile: undefined,
+				sandbox: undefined
 			},
 			...overrides
 		});
@@ -89,7 +90,8 @@ suite('MCP Types', () => {
 					command: 'command1',
 					args: [],
 					env: {},
-					envFile: undefined
+					envFile: undefined,
+					sandbox: undefined
 				}
 			});
 			const def2 = createBasicDefinition({
@@ -99,7 +101,8 @@ suite('MCP Types', () => {
 					command: 'command2',
 					args: [],
 					env: {},
-					envFile: undefined
+					envFile: undefined,
+					sandbox: undefined
 				}
 			});
 			assert.strictEqual(McpServerDefinition.equals(def1, def2), false);
diff --git a/src/vs/workbench/contrib/mcp/test/common/testMcpService.ts b/src/vs/workbench/contrib/mcp/test/common/testMcpService.ts
index 8479338a5b3d6..004220e587639 100644
--- a/src/vs/workbench/contrib/mcp/test/common/testMcpService.ts
+++ b/src/vs/workbench/contrib/mcp/test/common/testMcpService.ts
@@ -4,11 +4,20 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { observableValue } from '../../../../../base/common/observable.js';
+import { ContributionEnablementState, IEnablementModel } from '../../../chat/common/enablement.js';
 import { IAutostartResult, IMcpServer, IMcpService, LazyCollectionState } from '../../common/mcpTypes.js';
 
+export class TestEnablementModel implements IEnablementModel {
+	readEnabled(_key: string): ContributionEnablementState {
+		return ContributionEnablementState.EnabledProfile;
+	}
+	setEnabled(_key: string, _state: ContributionEnablementState): void { }
+}
+
 export class TestMcpService implements IMcpService {
 	declare readonly _serviceBrand: undefined;
 	public servers = observableValue<readonly IMcpServer[]>(this, []);
+	public readonly enablementModel: IEnablementModel = new TestEnablementModel();
 	resetCaches(): void {
 
 	}
diff --git a/src/vs/workbench/contrib/mcp/test/node/mcpStdioStateHandler.test.ts b/src/vs/workbench/contrib/mcp/test/node/mcpStdioStateHandler.test.ts
index e759a24cec497..7a5e0d28c0529 100644
--- a/src/vs/workbench/contrib/mcp/test/node/mcpStdioStateHandler.test.ts
+++ b/src/vs/workbench/contrib/mcp/test/node/mcpStdioStateHandler.test.ts
@@ -26,7 +26,7 @@ suite('McpStdioStateHandler', () => {
 			processId: new Promise<number>((resolve) => {
 				child.on('spawn', () => resolve(child.pid!));
 			}),
-			output: new Promise<string>((resolve) => {
+			output: new Promise<string>((resolve, reject) => {
 				let output = '';
 				child.stderr.setEncoding('utf-8').on('data', (data) => {
 					output += data.toString();
@@ -34,6 +34,7 @@ suite('McpStdioStateHandler', () => {
 				child.stdout.setEncoding('utf-8').on('data', (data) => {
 					output += data.toString();
 				});
+				child.on('error', reject);
 				child.on('close', () => resolve(output));
 			}),
 		};
diff --git a/src/vs/workbench/contrib/notebook/browser/contrib/find/notebookFindReplaceWidget.css b/src/vs/workbench/contrib/notebook/browser/contrib/find/notebookFindReplaceWidget.css
index 65208ad34b04e..4bd8e44bf11cc 100644
--- a/src/vs/workbench/contrib/notebook/browser/contrib/find/notebookFindReplaceWidget.css
+++ b/src/vs/workbench/contrib/notebook/browser/contrib/find/notebookFindReplaceWidget.css
@@ -16,7 +16,7 @@
 	visibility: hidden;
 	background-color: var(--vscode-editorWidget-background) !important;
 	color: var(--vscode-editorWidget-foreground);
-	box-shadow: 0 0 8px 2px var(--vscode-widget-shadow);
+	box-shadow: var(--vscode-shadow-lg);
 	border-bottom-left-radius: 4px;
 	border-bottom-right-radius: 4px;
 }
diff --git a/src/vs/workbench/contrib/notebook/browser/media/notebook.css b/src/vs/workbench/contrib/notebook/browser/media/notebook.css
index dff9db0ecce6f..01010edd2afc5 100644
--- a/src/vs/workbench/contrib/notebook/browser/media/notebook.css
+++ b/src/vs/workbench/contrib/notebook/browser/media/notebook.css
@@ -294,10 +294,12 @@
 	left: 0px;
 	top: 0px;
 	bottom: 0px;
+	border-radius: var(--vscode-cornerRadius-medium);
 	outline-offset: -1px;
 	display: block;
 	position: absolute;
 	pointer-events: none;
+	box-shadow: inset var(--vscode-shadow-sm);
 }
 
 .monaco-workbench .notebookOverlay .monaco-list .monaco-list-row .cell-insertion-indicator-top {
@@ -375,7 +377,17 @@
 .notebookOverlay .cell-drag-image .cell-editor-container > div {
 	background: var(--vscode-editor-background) !important;
 }
-.notebookOverlay .monaco-list-row .cell-title-toolbar,
+
+.notebookOverlay .cell-bottom-toolbar-container .action-item {
+	border-radius: var(--vscode-cornerRadius-small);
+}
+
+.notebookOverlay .monaco-list-row .cell-title-toolbar {
+	border-radius: var(--vscode-cornerRadius-medium);
+	box-shadow: var(--vscode-shadow-sm);
+	background-color: var(--vscode-editorWidget-background);
+}
+
 .notebookOverlay .monaco-list-row.cell-drag-image,
 .notebookOverlay .cell-bottom-toolbar-container .action-item,
 .notebookOverlay .cell-list-top-cell-toolbar-container .action-item {
diff --git a/src/vs/workbench/contrib/notebook/browser/notebookExtensionPoint.ts b/src/vs/workbench/contrib/notebook/browser/notebookExtensionPoint.ts
index 6de1d23298e3f..e0c53ce067c5b 100644
--- a/src/vs/workbench/contrib/notebook/browser/notebookExtensionPoint.ts
+++ b/src/vs/workbench/contrib/notebook/browser/notebookExtensionPoint.ts
@@ -158,7 +158,7 @@ const notebookRendererContribution: IJSONSchema = {
 						],
 						enumDescriptions: [
 							nls.localize('contributes.notebook.renderer.requiresMessaging.always', 'Messaging is required. The renderer will only be used when it\'s part of an extension that can be run in an extension host.'),
-							nls.localize('contributes.notebook.renderer.requiresMessaging.optional', 'The renderer is better with messaging available, but it\'s not requried.'),
+							nls.localize('contributes.notebook.renderer.requiresMessaging.optional', 'The renderer is better with messaging available, but it\'s not required.'),
 							nls.localize('contributes.notebook.renderer.requiresMessaging.never', 'The renderer does not require messaging.'),
 						],
 						description: nls.localize('contributes.notebook.renderer.requiresMessaging', 'Defines how and if the renderer needs to communicate with an extension host, via `createRendererMessaging`. Renderers with stronger messaging requirements may not work in all environments.'),
diff --git a/src/vs/workbench/contrib/preferences/browser/keybindingWidgets.ts b/src/vs/workbench/contrib/preferences/browser/keybindingWidgets.ts
index 18206f1ab62ec..b6a6170b071b3 100644
--- a/src/vs/workbench/contrib/preferences/browser/keybindingWidgets.ts
+++ b/src/vs/workbench/contrib/preferences/browser/keybindingWidgets.ts
@@ -20,7 +20,7 @@ import { IKeybindingService } from '../../../../platform/keybinding/common/keybi
 import { IContextViewService } from '../../../../platform/contextview/browser/contextView.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
 import { ICodeEditor, IOverlayWidget, IOverlayWidgetPosition } from '../../../../editor/browser/editorBrowser.js';
-import { asCssVariable, editorWidgetBackground, editorWidgetForeground, widgetShadow } from '../../../../platform/theme/common/colorRegistry.js';
+import { asCssVariable, editorWidgetBackground, editorWidgetForeground } from '../../../../platform/theme/common/colorRegistry.js';
 import { ScrollType } from '../../../../editor/common/editorCommon.js';
 import { SearchWidget, SearchOptions } from './preferencesWidgets.js';
 import { Promises, timeout } from '../../../../base/common/async.js';
@@ -171,7 +171,6 @@ export class DefineKeybindingWidget extends Widget {
 
 		this._domNode.domNode.style.backgroundColor = asCssVariable(editorWidgetBackground);
 		this._domNode.domNode.style.color = asCssVariable(editorWidgetForeground);
-		this._domNode.domNode.style.boxShadow = `0 2px 8px ${asCssVariable(widgetShadow)}`;
 
 		this._keybindingInputWidget = this._register(this.instantiationService.createInstance(KeybindingsSearchWidget, this._domNode.domNode, { ariaLabel: message, history: new Set([]), inputBoxStyles: defaultInputBoxStyles }));
 		this._keybindingInputWidget.startRecordingKeys();
diff --git a/src/vs/workbench/contrib/preferences/browser/keybindingsEditor.ts b/src/vs/workbench/contrib/preferences/browser/keybindingsEditor.ts
index 5ac483ffef20a..6fce0410f8468 100644
--- a/src/vs/workbench/contrib/preferences/browser/keybindingsEditor.ts
+++ b/src/vs/workbench/contrib/preferences/browser/keybindingsEditor.ts
@@ -15,7 +15,6 @@ import { HighlightedLabel } from '../../../../base/browser/ui/highlightedlabel/h
 import { KeybindingLabel } from '../../../../base/browser/ui/keybindingLabel/keybindingLabel.js';
 import { IAction, Action, Separator } from '../../../../base/common/actions.js';
 import { ActionBar } from '../../../../base/browser/ui/actionbar/actionbar.js';
-import { Button } from '../../../../base/browser/ui/button/button.js';
 import { EditorPane } from '../../../browser/parts/editor/editorPane.js';
 import { IEditorOpenContext } from '../../../common/editor.js';
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
@@ -43,13 +42,13 @@ import { Emitter, Event } from '../../../../base/common/event.js';
 import { MenuRegistry, MenuId, isIMenuItem } from '../../../../platform/actions/common/actions.js';
 import { IListAccessibilityProvider } from '../../../../base/browser/ui/list/listWidget.js';
 import { WORKBENCH_BACKGROUND } from '../../../common/theme.js';
-import { IKeybindingItemEntry, IKeybindingsEditorPane, IPreferencesService } from '../../../services/preferences/common/preferences.js';
+import { IKeybindingItemEntry, IKeybindingsEditorPane } from '../../../services/preferences/common/preferences.js';
 import { keybindingsRecordKeysIcon, keybindingsSortIcon, keybindingsAddIcon, preferencesClearInputIcon, keybindingsEditIcon } from './preferencesIcons.js';
 import { ITableRenderer, ITableVirtualDelegate } from '../../../../base/browser/ui/table/table.js';
 import { KeybindingsEditorInput } from '../../../services/preferences/browser/keybindingsEditorInput.js';
 import { IEditorOptions } from '../../../../platform/editor/common/editor.js';
 import { ToolBar } from '../../../../base/browser/ui/toolbar/toolbar.js';
-import { defaultButtonStyles, defaultKeybindingLabelStyles, defaultToggleStyles, getInputBoxStyle } from '../../../../platform/theme/browser/defaultStyles.js';
+import { defaultKeybindingLabelStyles, defaultToggleStyles, getInputBoxStyle } from '../../../../platform/theme/browser/defaultStyles.js';
 import { IExtensionsWorkbenchService } from '../../extensions/common/extensions.js';
 import { StandardKeyboardEvent } from '../../../../base/browser/keyboardEvent.js';
 import { isString } from '../../../../base/common/types.js';
@@ -131,8 +130,7 @@ export class KeybindingsEditor extends EditorPane<IKeybindingsEditorMemento> imp
 		@IEditorService private readonly editorService: IEditorService,
 		@IStorageService storageService: IStorageService,
 		@IConfigurationService private readonly configurationService: IConfigurationService,
-		@IAccessibilityService private readonly accessibilityService: IAccessibilityService,
-		@IPreferencesService private readonly preferencesService: IPreferencesService
+		@IAccessibilityService private readonly accessibilityService: IAccessibilityService
 	) {
 		super(KeybindingsEditor.ID, group, telemetryService, themeService, storageService);
 		this.delayedFiltering = this._register(new Delayer<void>(300));
@@ -366,8 +364,7 @@ export class KeybindingsEditor extends EditorPane<IKeybindingsEditorMemento> imp
 
 		const clearInputAction = this._register(new Action(KEYBINDINGS_EDITOR_COMMAND_CLEAR_SEARCH_RESULTS, localize('clearInput', "Clear Keybindings Search Input"), ThemeIcon.asClassName(preferencesClearInputIcon), false, async () => this.clearSearchResults()));
 
-		const searchRowContainer = DOM.append(this.headerContainer, $('.search-row-container'));
-		const searchContainer = DOM.append(searchRowContainer, $('.search-container'));
+		const searchContainer = DOM.append(this.headerContainer, $('.search-container'));
 		this.searchWidget = this._register(this.instantiationService.createInstance(KeybindingsSearchWidget, searchContainer, {
 			ariaLabel: fullTextSearchPlaceholder,
 			placeholder: fullTextSearchPlaceholder,
@@ -429,11 +426,6 @@ export class KeybindingsEditor extends EditorPane<IKeybindingsEditorMemento> imp
 		}));
 		toolBar.setActions(actions);
 		this._register(this.keybindingsService.onDidUpdateKeybindings(() => toolBar.setActions(actions)));
-
-		const openKeybindingsJsonContainer = DOM.append(searchRowContainer, $('.open-keybindings-json'));
-		const openKeybindingsJsonButton = this._register(new Button(openKeybindingsJsonContainer, { secondary: true, title: true, ...defaultButtonStyles }));
-		openKeybindingsJsonButton.label = localize('openKeybindingsJson', "Edit as JSON");
-		this._register(openKeybindingsJsonButton.onDidClick(() => this.preferencesService.openGlobalKeybindingSettings(true, { groupId: this.group.id })));
 	}
 
 	private updateSearchOptions(): void {
diff --git a/src/vs/workbench/contrib/preferences/browser/media/keybindings.css b/src/vs/workbench/contrib/preferences/browser/media/keybindings.css
index e77553529e87f..482f819ee58b3 100644
--- a/src/vs/workbench/contrib/preferences/browser/media/keybindings.css
+++ b/src/vs/workbench/contrib/preferences/browser/media/keybindings.css
@@ -5,7 +5,10 @@
 
 .defineKeybindingWidget {
 	padding: 10px;
+	border-radius: var(--vscode-cornerRadius-large);
 	position: absolute;
+	box-shadow: var(--vscode-shadow-lg);
+	border: 1px solid var(--vscode-editorWidget-border);
 }
 
 .defineKeybindingWidget .message {
diff --git a/src/vs/workbench/contrib/preferences/browser/media/keybindingsEditor.css b/src/vs/workbench/contrib/preferences/browser/media/keybindingsEditor.css
index f93706d61206b..96a94b07cdeaa 100644
--- a/src/vs/workbench/contrib/preferences/browser/media/keybindingsEditor.css
+++ b/src/vs/workbench/contrib/preferences/browser/media/keybindingsEditor.css
@@ -23,13 +23,11 @@
 	padding: 0px 10px 11px 0;
 }
 
-.keybindings-editor > .keybindings-header > .search-row-container > .search-container {
+.keybindings-editor > .keybindings-header > .search-container {
 	position: relative;
-	flex: 1;
-	min-width: 0;
 }
 
-.keybindings-editor > .keybindings-header > .search-row-container > .search-container > .keybindings-search-actions-container {
+.keybindings-editor > .keybindings-header > .search-container > .keybindings-search-actions-container {
 	position: absolute;
 	top: 0;
 	right: 10px;
@@ -37,22 +35,22 @@
 	display: flex;
 }
 
-.keybindings-editor > .keybindings-header > .search-row-container > .search-container > .keybindings-search-actions-container > .recording-badge {
+.keybindings-editor > .keybindings-header > .search-container > .keybindings-search-actions-container > .recording-badge {
 	margin-right: 8px;
 	padding: 4px;
 }
 
-.keybindings-editor > .keybindings-header.small > .search-row-container > .search-container > .keybindings-search-actions-container > .recording-badge,
-.keybindings-editor > .keybindings-header > .search-row-container > .search-container > .keybindings-search-actions-container > .recording-badge.disabled {
+.keybindings-editor > .keybindings-header.small > .search-container > .keybindings-search-actions-container > .recording-badge,
+.keybindings-editor > .keybindings-header > .search-container > .keybindings-search-actions-container > .recording-badge.disabled {
 	display: none;
 }
 
-.keybindings-editor > .keybindings-header > .search-row-container > .search-container > .keybindings-search-actions-container .monaco-action-bar .action-item > .icon {
+.keybindings-editor > .keybindings-header > .search-container > .keybindings-search-actions-container .monaco-action-bar .action-item > .icon {
 	width: 16px;
 	height: 18px;
 }
 
-.keybindings-editor > .keybindings-header > .search-row-container > .search-container > .keybindings-search-actions-container .monaco-action-bar .action-item {
+.keybindings-editor > .keybindings-header > .search-container > .keybindings-search-actions-container .monaco-action-bar .action-item {
 	margin-right: 4px;
 }
 
@@ -88,21 +86,6 @@
 	opacity: 1;
 }
 
-.keybindings-editor > .keybindings-header > .search-row-container {
-	display: flex;
-	align-items: center;
-	gap: 8px;
-}
-
-.keybindings-editor > .keybindings-header > .search-row-container > .open-keybindings-json {
-	flex-shrink: 0;
-}
-
-.keybindings-editor > .keybindings-header > .search-row-container > .open-keybindings-json > .monaco-button {
-	padding: 2px 8px;
-	line-height: 18px;
-}
-
 /** Table styling **/
 
 .keybindings-editor > .keybindings-body .keybindings-table-container {
diff --git a/src/vs/workbench/contrib/preferences/browser/media/settingsEditor2.css b/src/vs/workbench/contrib/preferences/browser/media/settingsEditor2.css
index 280ae562aceb0..f254088220625 100644
--- a/src/vs/workbench/contrib/preferences/browser/media/settingsEditor2.css
+++ b/src/vs/workbench/contrib/preferences/browser/media/settingsEditor2.css
@@ -62,6 +62,7 @@
 .settings-editor > .settings-header > .search-container > .search-container-widgets > .settings-count-widget {
 	margin-right: 3px;
 	padding-bottom: 3px;
+	color: var(--vscode-descriptionForeground);
 }
 
 .settings-editor > .settings-header > .search-container > .search-container-widgets > .settings-count-widget:empty {
@@ -95,13 +96,6 @@
 	flex: auto;
 }
 
-.settings-editor > .settings-header > .settings-header-controls > .settings-right-controls {
-	display: flex;
-	align-items: center;
-	gap: 8px;
-	padding-bottom: 4px;
-}
-
 .settings-editor > .settings-header > .settings-header-controls .settings-tabs-widget .action-label {
 	opacity: 0.9;
 	border-radius: 0;
@@ -295,6 +289,7 @@
 	pointer-events: none;
 	z-index: 10;
 	position: absolute;
+	box-shadow: var(--vscode-shadow-sm);
 }
 
 .settings-editor > .settings-body .settings-toc-container .monaco-list {
diff --git a/src/vs/workbench/contrib/preferences/browser/preferences.contribution.ts b/src/vs/workbench/contrib/preferences/browser/preferences.contribution.ts
index c1bd907895e4c..3f491f41b3ad4 100644
--- a/src/vs/workbench/contrib/preferences/browser/preferences.contribution.ts
+++ b/src/vs/workbench/contrib/preferences/browser/preferences.contribution.ts
@@ -835,6 +835,12 @@ class PreferencesActionsContribution extends Disposable implements IWorkbenchCon
 							group: 'navigation',
 							order: 1,
 						},
+						{
+							id: MenuId.ModalEditorEditorTitle,
+							when: ResourceContextKey.Resource.isEqualTo(that.userDataProfileService.currentProfile.keybindingsResource.toString()),
+							group: 'navigation',
+							order: 1,
+						},
 						{
 							id: MenuId.GlobalActivity,
 							group: '2_configuration',
@@ -883,6 +889,11 @@ class PreferencesActionsContribution extends Disposable implements IWorkbenchCon
 							id: MenuId.EditorTitle,
 							when: ContextKeyExpr.and(CONTEXT_KEYBINDINGS_EDITOR),
 							group: 'navigation',
+						},
+						{
+							id: MenuId.ModalEditorEditorTitle,
+							when: ContextKeyExpr.and(CONTEXT_KEYBINDINGS_EDITOR),
+							group: 'navigation',
 						}
 					]
 				});
@@ -1246,13 +1257,24 @@ class PreferencesActionsContribution extends Disposable implements IWorkbenchCon
 		const commandId = '_workbench.openWorkspaceSettingsEditor';
 		if (this.workspaceContextService.getWorkbenchState() === WorkbenchState.WORKSPACE && !CommandsRegistry.getCommand(commandId)) {
 			CommandsRegistry.registerCommand(commandId, () => this.preferencesService.openWorkspaceSettings({ jsonEditor: false }));
+			const when = ContextKeyExpr.and(ResourceContextKey.Resource.isEqualTo(this.preferencesService.workspaceSettingsResource!.toString()), WorkbenchStateContext.isEqualTo('workspace'), ContextKeyExpr.not('isInDiffEditor'));
 			MenuRegistry.appendMenuItem(MenuId.EditorTitle, {
 				command: {
 					id: commandId,
 					title: OPEN_USER_SETTINGS_UI_TITLE,
 					icon: preferencesOpenSettingsIcon
 				},
-				when: ContextKeyExpr.and(ResourceContextKey.Resource.isEqualTo(this.preferencesService.workspaceSettingsResource!.toString()), WorkbenchStateContext.isEqualTo('workspace'), ContextKeyExpr.not('isInDiffEditor')),
+				when,
+				group: 'navigation',
+				order: 1
+			});
+			MenuRegistry.appendMenuItem(MenuId.ModalEditorEditorTitle, {
+				command: {
+					id: commandId,
+					title: OPEN_USER_SETTINGS_UI_TITLE,
+					icon: preferencesOpenSettingsIcon
+				},
+				when,
 				group: 'navigation',
 				order: 1
 			});
@@ -1272,13 +1294,24 @@ class PreferencesActionsContribution extends Disposable implements IWorkbenchCon
 						return this.preferencesService.openFolderSettings({ folderUri: folder.uri, jsonEditor: false, groupId });
 					}
 				});
+				const when = ContextKeyExpr.and(ResourceContextKey.Resource.isEqualTo(this.preferencesService.getFolderSettingsResource(folder.uri)!.toString()), ContextKeyExpr.not('isInDiffEditor'));
 				MenuRegistry.appendMenuItem(MenuId.EditorTitle, {
 					command: {
 						id: commandId,
 						title: OPEN_USER_SETTINGS_UI_TITLE,
 						icon: preferencesOpenSettingsIcon
 					},
-					when: ContextKeyExpr.and(ResourceContextKey.Resource.isEqualTo(this.preferencesService.getFolderSettingsResource(folder.uri)!.toString()), ContextKeyExpr.not('isInDiffEditor')),
+					when,
+					group: 'navigation',
+					order: 1
+				});
+				MenuRegistry.appendMenuItem(MenuId.ModalEditorEditorTitle, {
+					command: {
+						id: commandId,
+						title: OPEN_USER_SETTINGS_UI_TITLE,
+						icon: preferencesOpenSettingsIcon
+					},
+					when,
 					group: 'navigation',
 					order: 1
 				});
@@ -1320,6 +1353,11 @@ class SettingsEditorTitleContribution extends Disposable implements IWorkbenchCo
 							when: openUserSettingsEditorWhen,
 							group: 'navigation',
 							order: 1
+						}, {
+							id: MenuId.ModalEditorEditorTitle,
+							when: openUserSettingsEditorWhen,
+							group: 'navigation',
+							order: 1
 						}]
 					});
 				}
@@ -1349,6 +1387,11 @@ class SettingsEditorTitleContribution extends Disposable implements IWorkbenchCo
 						when: openSettingsJsonWhen,
 						group: 'navigation',
 						order: 1
+					}, {
+						id: MenuId.ModalEditorEditorTitle,
+						when: openSettingsJsonWhen,
+						group: 'navigation',
+						order: 1
 					}]
 				});
 			}
diff --git a/src/vs/workbench/contrib/preferences/browser/preferencesWidgets.ts b/src/vs/workbench/contrib/preferences/browser/preferencesWidgets.ts
index 8c40f80dbe2e2..e33e0d1413ded 100644
--- a/src/vs/workbench/contrib/preferences/browser/preferencesWidgets.ts
+++ b/src/vs/workbench/contrib/preferences/browser/preferencesWidgets.ts
@@ -363,7 +363,7 @@ export class SettingsTargetsWidget extends Widget {
 	private async update(): Promise<void> {
 		this.settingsSwitcherBar.domNode.classList.toggle('empty-workbench', this.contextService.getWorkbenchState() === WorkbenchState.EMPTY);
 		this.userRemoteSettings.enabled = !!(this.options.enableRemoteSettings && this.environmentService.remoteAuthority);
-		this.workspaceSettings.enabled = this.contextService.getWorkbenchState() !== WorkbenchState.EMPTY;
+		this.workspaceSettings.enabled = this.contextService.getWorkbenchState() !== WorkbenchState.EMPTY && !this.environmentService.isSessionsWindow;
 		this.folderSettings.action.enabled = this.contextService.getWorkbenchState() === WorkbenchState.WORKSPACE && this.contextService.getWorkspace().folders.length > 0;
 
 		this.workspaceSettings.tooltip = localize('workspaceSettings', "Workspace");
diff --git a/src/vs/workbench/contrib/preferences/browser/settingsEditor2.ts b/src/vs/workbench/contrib/preferences/browser/settingsEditor2.ts
index 19d8730711092..17e5663deb81a 100644
--- a/src/vs/workbench/contrib/preferences/browser/settingsEditor2.ts
+++ b/src/vs/workbench/contrib/preferences/browser/settingsEditor2.ts
@@ -44,7 +44,7 @@ import { Registry } from '../../../../platform/registry/common/platform.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
 import { defaultButtonStyles, defaultToggleStyles } from '../../../../platform/theme/browser/defaultStyles.js';
-import { asCssVariable, asCssVariableWithDefault, badgeBackground, badgeForeground, contrastBorder, editorForeground, inputBackground } from '../../../../platform/theme/common/colorRegistry.js';
+import { asCssVariable, editorForeground } from '../../../../platform/theme/common/colorRegistry.js';
 import { IThemeService } from '../../../../platform/theme/common/themeService.js';
 import { IUserDataSyncEnablementService, IUserDataSyncService, SyncStatus } from '../../../../platform/userDataSync/common/userDataSync.js';
 import { IWorkspaceTrustManagementService } from '../../../../platform/workspace/common/workspaceTrust.js';
@@ -783,15 +783,8 @@ export class SettingsEditor2 extends EditorPane {
 			}
 		}));
 
-		const headerRightControlsContainer = DOM.append(headerControlsContainer, $('.settings-right-controls'));
-
-		const openSettingsJsonContainer = DOM.append(headerRightControlsContainer, $('.open-settings-json'));
-		const openSettingsJsonButton = this._register(new Button(openSettingsJsonContainer, { secondary: true, title: true, ...defaultButtonStyles }));
-		openSettingsJsonButton.label = localize('openSettingsJson', "Edit as JSON");
-		this._register(openSettingsJsonButton.onDidClick(() => this.openSettingsFile()));
-
 		if (this.userDataSyncWorkbenchService.enabled && this.userDataSyncEnablementService.canToggleEnablement()) {
-			const syncControls = this._register(this.instantiationService.createInstance(SyncControls, this.window, headerRightControlsContainer));
+			const syncControls = this._register(this.instantiationService.createInstance(SyncControls, this.window, headerControlsContainer));
 			this._register(syncControls.onDidChangeLastSyncedLabel(lastSyncedLabel => {
 				this.lastSyncedLabel = lastSyncedLabel;
 				this.updateInputAriaLabel();
@@ -801,9 +794,6 @@ export class SettingsEditor2 extends EditorPane {
 		this.controlsElement = DOM.append(this.searchContainer, DOM.$('.search-container-widgets'));
 
 		this.countElement = DOM.append(this.controlsElement, DOM.$('.settings-count-widget.monaco-count-badge.long'));
-		this.countElement.style.backgroundColor = asCssVariable(badgeBackground);
-		this.countElement.style.color = asCssVariable(badgeForeground);
-		this.countElement.style.border = `1px solid ${asCssVariableWithDefault(contrastBorder, asCssVariable(inputBackground))}`;
 
 		this.searchInputActionBar = this._register(new ActionBar(this.controlsElement, {
 			actionViewItemProvider: (action, options) => {
@@ -2166,9 +2156,10 @@ class SyncControls extends Disposable {
 	) {
 		super();
 
-		const turnOnSyncButtonContainer = DOM.append(container, $('.turn-on-sync'));
+		const headerRightControlsContainer = DOM.append(container, $('.settings-right-controls'));
+		const turnOnSyncButtonContainer = DOM.append(headerRightControlsContainer, $('.turn-on-sync'));
 		this.turnOnSyncButton = this._register(new Button(turnOnSyncButtonContainer, { title: true, ...defaultButtonStyles }));
-		this.lastSyncedLabel = DOM.append(container, $('.last-synced-label'));
+		this.lastSyncedLabel = DOM.append(headerRightControlsContainer, $('.last-synced-label'));
 		DOM.hide(this.lastSyncedLabel);
 
 		this.turnOnSyncButton.enabled = true;
diff --git a/src/vs/workbench/contrib/preferences/browser/settingsLayout.ts b/src/vs/workbench/contrib/preferences/browser/settingsLayout.ts
index 6e6f22ce61a26..5d1c11fac9048 100644
--- a/src/vs/workbench/contrib/preferences/browser/settingsLayout.ts
+++ b/src/vs/workbench/contrib/preferences/browser/settingsLayout.ts
@@ -156,6 +156,11 @@ export const tocData: ITOCEntry<string> = {
 					id: 'workbench/screencastmode',
 					label: localize('screencastMode', "Screencast Mode"),
 					settings: ['screencastMode.*']
+				},
+				{
+					id: 'workbench/browser',
+					label: localize('browser', "Browser"),
+					settings: ['workbench.browser.*']
 				}
 			]
 		},
@@ -232,8 +237,7 @@ export const tocData: ITOCEntry<string> = {
 					label: localize('chatTools', "Tools"),
 					settings: [
 						'chat.tools.*',
-						'chat.extensionTools.*',
-						'chat.edits2.enabled'
+						'chat.extensionTools.*'
 					]
 				},
 				{
diff --git a/src/vs/workbench/contrib/preferences/browser/settingsWidgets.ts b/src/vs/workbench/contrib/preferences/browser/settingsWidgets.ts
index 1322fca29ed23..6d6f60085f73e 100644
--- a/src/vs/workbench/contrib/preferences/browser/settingsWidgets.ts
+++ b/src/vs/workbench/contrib/preferences/browser/settingsWidgets.ts
@@ -659,6 +659,7 @@ export class ListSettingWidget<TListDataItem extends IListDataItem> extends Abst
 			} else if (e.equals(KeyCode.Escape)) {
 				this.cancelEdit();
 				e.preventDefault();
+				e.stopPropagation();
 			}
 			rowElement?.focus();
 		};
@@ -1198,6 +1199,7 @@ export class ObjectSettingDropdownWidget extends AbstractListSettingWidget<IObje
 			} else if (e.equals(KeyCode.Escape)) {
 				this.cancelEdit();
 				e.preventDefault();
+				e.stopPropagation();
 			}
 		};
 
diff --git a/src/vs/workbench/contrib/scm/browser/media/scm.css b/src/vs/workbench/contrib/scm/browser/media/scm.css
index 20c78c396f13e..408b771f84c24 100644
--- a/src/vs/workbench/contrib/scm/browser/media/scm.css
+++ b/src/vs/workbench/contrib/scm/browser/media/scm.css
@@ -38,6 +38,7 @@
 	height: 100%;
 	align-items: center;
 	flex-flow: nowrap;
+	box-shadow: var(--vscode-shadow-sm);
 }
 
 .scm-view.hide-provider-counts .scm-provider > .count,
diff --git a/src/vs/workbench/contrib/scm/browser/scmInput.ts b/src/vs/workbench/contrib/scm/browser/scmInput.ts
index bcc312c6ba2c3..a35d479e1a84d 100644
--- a/src/vs/workbench/contrib/scm/browser/scmInput.ts
+++ b/src/vs/workbench/contrib/scm/browser/scmInput.ts
@@ -261,6 +261,7 @@ class SCMInputWidgetEditorOptions {
 					e.affectsConfiguration('editor.cursorWidth') ||
 					e.affectsConfiguration('editor.emptySelectionClipboard') ||
 					e.affectsConfiguration('editor.fontFamily') ||
+					e.affectsConfiguration('editor.roundedSelection') ||
 					e.affectsConfiguration('editor.rulers') ||
 					e.affectsConfiguration('editor.wordWrap') ||
 					e.affectsConfiguration('editor.wordSegmenterLocales') ||
@@ -304,8 +305,9 @@ class SCMInputWidgetEditorOptions {
 		const cursorStyle = this.configurationService.getValue<IEditorOptions['cursorStyle']>('editor.cursorStyle');
 		const cursorWidth = this.configurationService.getValue<IEditorOptions['cursorWidth']>('editor.cursorWidth') ?? 1;
 		const emptySelectionClipboard = this.configurationService.getValue<boolean>('editor.emptySelectionClipboard') === true;
+		const roundedSelection = this.configurationService.getValue<boolean>('editor.roundedSelection') === true;
 
-		return { ...this._getEditorLanguageConfiguration(), accessibilitySupport, cursorBlinking, cursorStyle, cursorWidth, fontFamily, fontSize, lineHeight, emptySelectionClipboard, wordSegmenterLocales };
+		return { ...this._getEditorLanguageConfiguration(), accessibilitySupport, cursorBlinking, cursorStyle, cursorWidth, fontFamily, fontSize, lineHeight, emptySelectionClipboard, roundedSelection, wordSegmenterLocales };
 	}
 
 	private _getEditorFontFamily(): string {
diff --git a/src/vs/workbench/contrib/tags/electron-browser/workspaceTagsService.ts b/src/vs/workbench/contrib/tags/electron-browser/workspaceTagsService.ts
index 12f8e73bc273c..e22f45b9dfb6a 100644
--- a/src/vs/workbench/contrib/tags/electron-browser/workspaceTagsService.ts
+++ b/src/vs/workbench/contrib/tags/electron-browser/workspaceTagsService.ts
@@ -30,7 +30,14 @@ const MetaModulesToLookFor = [
 ];
 
 const ModulesToLookFor = [
-	// Packages that suggest a node server
+	// Platform-related type definition packages
+	'@types/vscode',
+	'@vscode/dts',
+	'@types/node',
+	'@types/bun',
+	'bun-types',
+	'@types/web',
+	// Packages that suggest a JS-based backend server
 	'express',
 	'sails',
 	'koa',
@@ -42,18 +49,36 @@ const ModulesToLookFor = [
 	'@nestjs/core',
 	'strapi',
 	'gatsby',
+	'fastify',
+	'hono',
 	// JS frameworks
 	'react',
 	'react-native',
 	'react-native-macos',
 	'react-native-windows',
 	'rnpm-plugin-windows',
+	'@types/react',
 	'@angular/core',
 	'@ionic',
 	'vue',
 	'tns-core-modules',
 	'@nativescript/core',
 	'electron',
+	'@remix-run/react',
+	'@remix-run/express',
+	'@remix-run/node',
+	'@remix-run/dev',
+	'@sveltejs/kit',
+	'preact',
+	'@preact/signals',
+	'@builder.io/qwik',
+	'alpinejs',
+	'astro',
+	'htmx.org',
+	'solid-js',
+	'svelte',
+	'lit-html',
+	'vuepress',
 	// Other interesting packages
 	'aws-sdk',
 	'aws-amplify',
@@ -61,6 +86,7 @@ const ModulesToLookFor = [
 	'azure-storage',
 	'chroma',
 	'deepseek-js',
+	'docusaurus',
 	'faiss',
 	'firebase',
 	'@google-cloud/common',
@@ -71,6 +97,43 @@ const ModulesToLookFor = [
 	'pinecone',
 	'praisonai',
 	'qdrant',
+	'typescript',
+	'@typescript/native-preview',
+	'tslib',
+	'eslint',
+	'oxlint',
+	'oxfmt',
+	'typescript-eslint',
+	'prettier',
+	'dprint',
+	'@dprint/formatter',
+	'@babel/cli',
+	'@babel/core',
+	'@swc/cli',
+	'@swc/core',
+	'vite',
+	'esbuild',
+	'rollup',
+	'rolldown',
+	'nx',
+	'turbo',
+	'webpack',
+	'parcel',
+	'@biomejs/biome',
+	'@rspack/core',
+	'@rspack/cli',
+	'@trpc/client',
+	'@trpc/server',
+	'zod',
+	'pyright',
+	'ts-morph',
+	'oxc-minify',
+	'oxc-transform',
+	'oxc-resolver',
+	'vue-tsc',
+	'svelte-check',
+	'tsup',
+	'tsdown',
 	// Office and Sharepoint packages
 	'@microsoft/teams-js',
 	'@microsoft/office-js',
@@ -96,13 +159,17 @@ const ModulesToLookFor = [
 	'playwright-firefox',
 	'playwright-webkit',
 	// Other interesting browser testing packages
+	'chai',
 	'cypress',
+	'gherkin',
+	'jest',
+	'mocha',
 	'nightwatch',
 	'protractor',
 	'puppeteer',
 	'selenium-webdriver',
+	'vitest',
 	'webdriverio',
-	'gherkin',
 	// AzureSDK packages
 	'@azure/app-configuration',
 	'@azure/cosmos-sign',
@@ -183,6 +250,7 @@ const ModulesToLookFor = [
 	'@azure/arm-hybridkubernetes',
 	'@azure/arm-kubernetesconfiguration',
 	//AI and vector db dev packages
+	'ai',
 	'@anthropic-ai/sdk',
 	'@anthropic-ai/tokenizer',
 	'@arizeai/openinference-instrumentation-langchain',
@@ -615,6 +683,73 @@ export class WorkspaceTagsService implements IWorkspaceTagsService {
 			"workspace.npm.tika" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
 			"workspace.npm.webdriverio" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
 			"workspace.npm.gherkin" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@types/vscode" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@vscode/dts" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@types/node" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@types/bun" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.bun-types" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@types/web" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.fastify" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.hono" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@types/react" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@remix-run/react" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@remix-run/express" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@remix-run/node" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@remix-run/dev" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@sveltejs/kit" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.preact" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@preact/signals" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@builder.io/qwik" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.alpinejs" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.astro" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.htmx.org" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.solid-js" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.svelte" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.lit-html" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.vuepress" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.docusaurus" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.typescript" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@typescript/native-preview" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.tslib" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.eslint" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.oxlint" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.oxfmt" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.typescript-eslint" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.prettier" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.dprint" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@dprint/formatter" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@babel/cli" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@babel/core" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@swc/cli" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@swc/core" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.vite" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.esbuild" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.rollup" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.rolldown" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.nx" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.turbo" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.webpack" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.parcel" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@biomejs/biome" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@rspack/core" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@rspack/cli" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@trpc/client" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.@trpc/server" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.zod" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.pyright" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.ts-morph" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.oxc-minify" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.oxc-transform" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.oxc-resolver" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.vue-tsc" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.svelte-check" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.tsup" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.tsdown" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.chai" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.jest" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.mocha" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.vitest" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
+			"workspace.npm.ai" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
 			"workspace.npm.@azure/app-configuration" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
 			"workspace.npm.@azure/cosmos-sign" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
 			"workspace.npm.@azure/cosmos-language-service" : { "classification": "SystemMetaData", "purpose": "FeatureInsight", "isMeasurement": true },
diff --git a/src/vs/workbench/contrib/tasks/common/jsonSchema_v2.ts b/src/vs/workbench/contrib/tasks/common/jsonSchema_v2.ts
index 8d937a1e5b5fc..56eb132182a68 100644
--- a/src/vs/workbench/contrib/tasks/common/jsonSchema_v2.ts
+++ b/src/vs/workbench/contrib/tasks/common/jsonSchema_v2.ts
@@ -384,8 +384,8 @@ const runOptions: IJSONSchema = {
 		},
 		runOn: {
 			type: 'string',
-			enum: ['default', 'folderOpen'],
-			description: nls.localize('JsonSchema.tasks.runOn', 'Configures when the task should be run. If set to folderOpen, then the task will be run automatically when the folder is opened.'),
+			enum: ['default', 'folderOpen', 'worktreeCreated'],
+			description: nls.localize('JsonSchema.tasks.runOn', 'Configures when the task should be run. If set to folderOpen, then the task will be run automatically when the folder is opened. If set to worktreeCreated, then the task will be run automatically when an Agent Session worktree is created.'),
 			default: 'default'
 		},
 		instanceLimit: {
diff --git a/src/vs/workbench/contrib/tasks/common/taskConfiguration.ts b/src/vs/workbench/contrib/tasks/common/taskConfiguration.ts
index e90a90ea3b9de..a6f14097d8f66 100644
--- a/src/vs/workbench/contrib/tasks/common/taskConfiguration.ts
+++ b/src/vs/workbench/contrib/tasks/common/taskConfiguration.ts
@@ -716,6 +716,8 @@ export namespace RunOnOptions {
 		switch (value.toLowerCase()) {
 			case 'folderopen':
 				return Tasks.RunOnOptions.folderOpen;
+			case 'worktreecreated':
+				return Tasks.RunOnOptions.worktreeCreated;
 			case 'default':
 			default:
 				return Tasks.RunOnOptions.default;
diff --git a/src/vs/workbench/contrib/tasks/common/tasks.ts b/src/vs/workbench/contrib/tasks/common/tasks.ts
index c7b6427e5510e..5e6ab55221678 100644
--- a/src/vs/workbench/contrib/tasks/common/tasks.ts
+++ b/src/vs/workbench/contrib/tasks/common/tasks.ts
@@ -586,7 +586,8 @@ export interface IConfigurationProperties {
 
 export enum RunOnOptions {
 	default = 1,
-	folderOpen = 2
+	folderOpen = 2,
+	worktreeCreated = 3
 }
 
 export const enum InstancePolicy {
diff --git a/src/vs/workbench/contrib/terminal/browser/chatTerminalCommandMirror.ts b/src/vs/workbench/contrib/terminal/browser/chatTerminalCommandMirror.ts
index 64715a47835cd..6d39991038882 100644
--- a/src/vs/workbench/contrib/terminal/browser/chatTerminalCommandMirror.ts
+++ b/src/vs/workbench/contrib/terminal/browser/chatTerminalCommandMirror.ts
@@ -308,12 +308,10 @@ export class DetachedTerminalCommandMirror extends Disposable implements IDetach
 			// if we blindly append.
 			const canAppend = !!this._lastVT && vt.text.length >= this._lastVT.length && this._vtBoundaryMatches(vt.text, this._lastVT.length);
 			if (!canAppend) {
-				// Reset the terminal if we had previous content (can't append, need full rewrite)
-				if (this._lastVT) {
-					detached.xterm.reset();
-				}
-				if (vt.text) {
-					detached.xterm.write(vt.text, resolve);
+				// Use \x1bc (RIS) + new content in one write to avoid a blank frame
+				const payload = this._lastVT ? `\x1bc${vt.text}` : vt.text;
+				if (payload) {
+					detached.xterm.write(payload, resolve);
 				} else {
 					resolve();
 				}
@@ -542,12 +540,10 @@ export class DetachedTerminalCommandMirror extends Disposable implements IDetach
 		const canAppend = !!this._lastVT && startLine >= previousCursor && vt.text.length >= this._lastVT.length && this._vtBoundaryMatches(vt.text, this._lastVT.length);
 		await new Promise<void>(resolve => {
 			if (!canAppend) {
-				// Reset the terminal if we had previous content (can't append, need full rewrite)
-				if (this._lastVT) {
-					detachedRaw.reset();
-				}
-				if (vt.text) {
-					detachedRaw.write(vt.text, resolve);
+				// Use \x1bc (RIS) + new content in one write to avoid a blank frame
+				const payload = this._lastVT ? `\x1bc${vt.text}` : vt.text;
+				if (payload) {
+					detachedRaw.write(payload, resolve);
 				} else {
 					resolve();
 				}
diff --git a/src/vs/workbench/contrib/terminal/browser/media/terminal.css b/src/vs/workbench/contrib/terminal/browser/media/terminal.css
index 9370b48b871f6..58400159f85ce 100644
--- a/src/vs/workbench/contrib/terminal/browser/media/terminal.css
+++ b/src/vs/workbench/contrib/terminal/browser/media/terminal.css
@@ -63,7 +63,7 @@
 }
 
 .monaco-workbench .terminal-editor .terminal-wrapper {
-	background-color: var(--vscode-terminal-background, var(--vscode-editorPane-background));
+	background-color: var(--vscode-editor-background);
 }
 .monaco-workbench .terminal-editor .terminal-wrapper,
 .monaco-workbench .pane-body.integrated-terminal .terminal-wrapper {
diff --git a/src/vs/workbench/contrib/terminal/browser/terminal.ts b/src/vs/workbench/contrib/terminal/browser/terminal.ts
index a730051c4e7b9..b54f86b3ad3ac 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminal.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminal.ts
@@ -520,6 +520,12 @@ export interface ITerminalService extends ITerminalInstanceHost {
 	 * @param forceSaveState Used when the window is shutting down and we need to reveal and save hideFromUser terminals
 	 */
 	showBackgroundTerminal(instance: ITerminalInstance, suppressSetActive?: boolean): Promise<void>;
+	/**
+	 * Moves a visible terminal instance to the background. The terminal process
+	 * remains alive but the instance is removed from its group/editor and tracked
+	 * internally so it can later be shown again via {@link showBackgroundTerminal}.
+	 */
+	moveToBackground(instance: ITerminalInstance): void;
 	revealActiveTerminal(preserveFocus?: boolean): Promise<void>;
 	moveToEditor(source: ITerminalInstance, group?: GroupIdentifier | SIDE_GROUP_TYPE | ACTIVE_GROUP_TYPE | AUX_WINDOW_GROUP_TYPE): void;
 	moveIntoNewEditor(source: ITerminalInstance): void;
diff --git a/src/vs/workbench/contrib/terminal/browser/terminalActions.ts b/src/vs/workbench/contrib/terminal/browser/terminalActions.ts
index 79023c406f44a..4d881d9cb1b23 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminalActions.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminalActions.ts
@@ -1671,7 +1671,7 @@ async function pickTerminalCwd(accessor: ServicesAccessor, cancel?: Cancellation
 	const folderPicks: Item[] = shrinkedPairs.map(pair => {
 		const label = pair.folder.name;
 		const description = pair.isOverridden
-			? localize('workbench.action.terminal.overriddenCwdDescription', "(Overriden) {0}", labelService.getUriLabel(pair.cwd, { relative: !pair.isAbsolute }))
+			? localize('workbench.action.terminal.overriddenCwdDescription', "(Overridden) {0}", labelService.getUriLabel(pair.cwd, { relative: !pair.isAbsolute }))
 			: labelService.getUriLabel(dirname(pair.cwd), { relative: true });
 
 		return {
diff --git a/src/vs/workbench/contrib/terminal/browser/terminalEditor.ts b/src/vs/workbench/contrib/terminal/browser/terminalEditor.ts
index 8b40d46937553..b158684ae0ea3 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminalEditor.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminalEditor.ts
@@ -13,6 +13,7 @@ import { IContextKeyService } from '../../../../platform/contextkey/common/conte
 import { IContextMenuService } from '../../../../platform/contextview/browser/contextView.js';
 import { IEditorOptions } from '../../../../platform/editor/common/editor.js';
 import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
+import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { IStorageService } from '../../../../platform/storage/common/storage.js';
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
 import { IThemeService } from '../../../../platform/theme/common/themeService.js';
@@ -60,6 +61,7 @@ export class TerminalEditor extends EditorPane {
 		@ITerminalProfileResolverService private readonly _terminalProfileResolverService: ITerminalProfileResolverService,
 		@ITerminalService private readonly _terminalService: ITerminalService,
 		@ITerminalConfigurationService private readonly _terminalConfigurationService: ITerminalConfigurationService,
+		@IConfigurationService private readonly _configurationService: IConfigurationService,
 		@IContextKeyService contextKeyService: IContextKeyService,
 		@IMenuService menuService: IMenuService,
 		@IInstantiationService private readonly _instantiationService: IInstantiationService,
@@ -156,7 +158,7 @@ export class TerminalEditor extends EditorPane {
 
 	private _updateTabActionBar(profiles: ITerminalProfile[]): void {
 		this._disposableStore.clear();
-		const actions = getTerminalActionBarArgs(TerminalLocation.Editor, profiles, this._getDefaultProfileName(), this._terminalProfileService.contributedProfiles, this._terminalService, this._dropdownMenu, this._disposableStore);
+		const actions = getTerminalActionBarArgs(TerminalLocation.Editor, profiles, this._getDefaultProfileName(), this._terminalProfileService.contributedProfiles, this._terminalService, this._dropdownMenu, this._disposableStore, this._configurationService);
 		this._newDropdown.value?.update(actions.dropdownAction, actions.dropdownMenuActions);
 	}
 
@@ -180,7 +182,7 @@ export class TerminalEditor extends EditorPane {
 				if (action instanceof MenuItemAction) {
 					const location = { viewColumn: ACTIVE_GROUP };
 					this._disposableStore.clear();
-					const actions = getTerminalActionBarArgs(location, this._terminalProfileService.availableProfiles, this._getDefaultProfileName(), this._terminalProfileService.contributedProfiles, this._terminalService, this._dropdownMenu, this._disposableStore);
+					const actions = getTerminalActionBarArgs(location, this._terminalProfileService.availableProfiles, this._getDefaultProfileName(), this._terminalProfileService.contributedProfiles, this._terminalService, this._dropdownMenu, this._disposableStore, this._configurationService);
 					this._newDropdown.value = this._instantiationService.createInstance(DropdownWithPrimaryActionViewItem, action, actions.dropdownAction, actions.dropdownMenuActions, actions.className, { hoverDelegate: options.hoverDelegate });
 					this._newDropdown.value?.update(actions.dropdownAction, actions.dropdownMenuActions);
 					return this._newDropdown.value;
diff --git a/src/vs/workbench/contrib/terminal/browser/terminalEditorInput.ts b/src/vs/workbench/contrib/terminal/browser/terminalEditorInput.ts
index d0c3a794561d2..f7ce1dab62b91 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminalEditorInput.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminalEditorInput.ts
@@ -60,7 +60,7 @@ export class TerminalEditorInput extends EditorInput implements IEditorCloseHand
 	}
 
 	override get capabilities(): EditorInputCapabilities {
-		return EditorInputCapabilities.Readonly | EditorInputCapabilities.Singleton | EditorInputCapabilities.CanDropIntoEditor | EditorInputCapabilities.ForceDescription;
+		return EditorInputCapabilities.Readonly | EditorInputCapabilities.ForceReveal | EditorInputCapabilities.CanDropIntoEditor | EditorInputCapabilities.ForceDescription;
 	}
 
 	setTerminalInstance(instance: ITerminalInstance): void {
diff --git a/src/vs/workbench/contrib/terminal/browser/terminalInstance.ts b/src/vs/workbench/contrib/terminal/browser/terminalInstance.ts
index f78a087fbd854..93a50146bc1a9 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminalInstance.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminalInstance.ts
@@ -2812,13 +2812,13 @@ export class TerminalInstanceColorProvider implements IXtermColorProvider {
 	}
 
 	getBackgroundColor(theme: IColorTheme) {
+		if (this._target.object === TerminalLocation.Editor) {
+			return theme.getColor(editorBackground);
+		}
 		const terminalBackground = theme.getColor(TERMINAL_BACKGROUND_COLOR);
 		if (terminalBackground) {
 			return terminalBackground;
 		}
-		if (this._target.object === TerminalLocation.Editor) {
-			return theme.getColor(editorBackground);
-		}
 		const location = this._viewDescriptorService.getViewLocationById(TERMINAL_VIEW_ID)!;
 		if (location === ViewContainerLocation.Panel) {
 			return theme.getColor(PANEL_BACKGROUND);
diff --git a/src/vs/workbench/contrib/terminal/browser/terminalMenus.ts b/src/vs/workbench/contrib/terminal/browser/terminalMenus.ts
index b0860ecc69cae..281d624fcec37 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminalMenus.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminalMenus.ts
@@ -8,6 +8,7 @@ import { Codicon } from '../../../../base/common/codicons.js';
 import { Schemas } from '../../../../base/common/network.js';
 import { localize, localize2 } from '../../../../nls.js';
 import { IMenu, MenuId, MenuRegistry } from '../../../../platform/actions/common/actions.js';
+import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
 import { ContextKeyExpr } from '../../../../platform/contextkey/common/contextkey.js';
 import { IExtensionTerminalProfile, ITerminalProfile, TerminalLocation, TerminalSettingId } from '../../../../platform/terminal/common/terminal.js';
 import { ResourceContextKey } from '../../../common/contextkeys.js';
@@ -781,12 +782,20 @@ export function setupTerminalMenus(): void {
 	}
 }
 
-export function getTerminalActionBarArgs(location: ITerminalLocationOptions, profiles: ITerminalProfile[], defaultProfileName: string, contributedProfiles: readonly IExtensionTerminalProfile[], terminalService: ITerminalService, dropdownMenu: IMenu, disposableStore: DisposableStore): {
+export function getTerminalActionBarArgs(location: ITerminalLocationOptions, profiles: ITerminalProfile[], defaultProfileName: string, contributedProfiles: readonly IExtensionTerminalProfile[], terminalService: ITerminalService, dropdownMenu: IMenu, disposableStore: DisposableStore, configurationService: IConfigurationService): {
 	dropdownAction: IAction;
 	dropdownMenuActions: IAction[];
 	className: string;
 	dropdownIcon?: string;
 } {
+	const shouldElevateAiProfiles = configurationService.getValue<boolean>(TerminalSettingId.ExperimentalAiProfileGrouping);
+	profiles = profiles.filter(e => !e.isAutoDetected);
+	const [aiProfiles, otherProfiles] = shouldElevateAiProfiles
+		? splitProfiles(profiles)
+		: [[], profiles];
+	const [aiContributedProfiles, otherContributedProfiles] = shouldElevateAiProfiles
+		? splitContributedProfiles(contributedProfiles)
+		: [[], contributedProfiles];
 	const dropdownActions: IAction[] = [];
 	const submenuActions: IAction[] = [];
 	const splitLocation = (location === TerminalLocation.Editor || (typeof location === 'object' && hasKey(location, { viewColumn: true }) && location.viewColumn === ACTIVE_GROUP)) ? { viewColumn: SIDE_GROUP } : { splitActiveTerminal: true };
@@ -806,40 +815,22 @@ export function getTerminalActionBarArgs(location: ITerminalLocationOptions, pro
 		location: splitLocation
 	}))));
 	dropdownActions.push(new Separator());
+	for (const p of aiProfiles) {
+		addProfileActions(p, defaultProfileName, location, splitLocation, terminalService, dropdownActions, submenuActions, disposableStore);
+	}
+	for (const contributed of aiContributedProfiles) {
+		addContributedProfileActions(contributed, defaultProfileName, location, splitLocation, terminalService, dropdownActions, submenuActions, disposableStore);
+	}
+	if ((aiProfiles.length > 0 || aiContributedProfiles.length > 0) && (otherProfiles.length > 0 || otherContributedProfiles.length > 0)) {
+		dropdownActions.push(new Separator());
+	}
 
-	profiles = profiles.filter(e => !e.isAutoDetected);
-	for (const p of profiles) {
-		const isDefault = p.profileName === defaultProfileName;
-		const options: ICreateTerminalOptions = { config: p, location };
-		const splitOptions: ICreateTerminalOptions = { config: p, location: splitLocation };
-		const sanitizedProfileName = p.profileName.replace(/[\n\r\t]/g, '');
-		dropdownActions.push(disposableStore.add(new Action(TerminalCommandId.NewWithProfile, isDefault ? localize('defaultTerminalProfile', "{0} (Default)", sanitizedProfileName) : sanitizedProfileName, undefined, true, async () => {
-			await terminalService.createAndFocusTerminal(options);
-		})));
-		submenuActions.push(disposableStore.add(new Action(TerminalCommandId.Split, isDefault ? localize('defaultTerminalProfile', "{0} (Default)", sanitizedProfileName) : sanitizedProfileName, undefined, true, async () => {
-			await terminalService.createAndFocusTerminal(splitOptions);
-		})));
+	for (const p of otherProfiles) {
+		addProfileActions(p, defaultProfileName, location, splitLocation, terminalService, dropdownActions, submenuActions, disposableStore);
 	}
 
-	for (const contributed of contributedProfiles) {
-		const isDefault = contributed.title === defaultProfileName;
-		const title = isDefault ? localize('defaultTerminalProfile', "{0} (Default)", contributed.title.replace(/[\n\r\t]/g, '')) : contributed.title.replace(/[\n\r\t]/g, '');
-		dropdownActions.push(disposableStore.add(new Action('contributed', title, undefined, true, () => terminalService.createAndFocusTerminal({
-			config: {
-				extensionIdentifier: contributed.extensionIdentifier,
-				id: contributed.id,
-				title
-			},
-			location
-		}))));
-		submenuActions.push(disposableStore.add(new Action('contributed-split', title, undefined, true, () => terminalService.createAndFocusTerminal({
-			config: {
-				extensionIdentifier: contributed.extensionIdentifier,
-				id: contributed.id,
-				title
-			},
-			location: splitLocation
-		}))));
+	for (const contributed of otherContributedProfiles) {
+		addContributedProfileActions(contributed, defaultProfileName, location, splitLocation, terminalService, dropdownActions, submenuActions, disposableStore);
 	}
 
 	if (dropdownActions.length > 0) {
@@ -852,3 +843,95 @@ export function getTerminalActionBarArgs(location: ITerminalLocationOptions, pro
 	const dropdownAction = disposableStore.add(new Action('refresh profiles', localize('launchProfile', 'Launch Profile...'), 'codicon-chevron-down', true));
 	return { dropdownAction, dropdownMenuActions: dropdownActions, className: `terminal-tab-actions-${terminalService.resolveLocation(location)}` };
 }
+
+function splitProfiles(profiles: readonly ITerminalProfile[]): [ITerminalProfile[], ITerminalProfile[]] {
+	const aiProfiles: ITerminalProfile[] = [];
+	const otherProfiles: ITerminalProfile[] = [];
+	for (const profile of profiles) {
+		if (isAiProfileName(profile.profileName)) {
+			aiProfiles.push(profile);
+		} else {
+			otherProfiles.push(profile);
+		}
+	}
+	return [aiProfiles, otherProfiles];
+}
+
+function splitContributedProfiles(contributedProfiles: readonly IExtensionTerminalProfile[]): [IExtensionTerminalProfile[], IExtensionTerminalProfile[]] {
+	const aiContributedProfiles: IExtensionTerminalProfile[] = [];
+	const otherContributedProfiles: IExtensionTerminalProfile[] = [];
+	for (const profile of contributedProfiles) {
+		if (isAiContributedProfile(profile)) {
+			aiContributedProfiles.push(profile);
+		} else {
+			otherContributedProfiles.push(profile);
+		}
+	}
+	return [aiContributedProfiles, otherContributedProfiles];
+}
+
+function isAiContributedProfile(profile: IExtensionTerminalProfile): boolean {
+	const extensionIdentifier = profile.extensionIdentifier.toLowerCase();
+	if (extensionIdentifier === 'github.copilot-chat' || extensionIdentifier === 'anthropic.claude-code') {
+		return true;
+	}
+
+	return isAiProfileName(profile.title);
+}
+
+function isAiProfileName(name: string): boolean {
+	const lowerCaseName = name.toLowerCase();
+	return lowerCaseName.includes('copilot') || lowerCaseName.includes('claude');
+}
+
+function addProfileActions(
+	profile: ITerminalProfile,
+	defaultProfileName: string,
+	location: ITerminalLocationOptions,
+	splitLocation: ITerminalLocationOptions,
+	terminalService: ITerminalService,
+	dropdownActions: IAction[],
+	submenuActions: IAction[],
+	disposableStore: DisposableStore
+): void {
+	const isDefault = profile.profileName === defaultProfileName;
+	const options: ICreateTerminalOptions = { config: profile, location };
+	const splitOptions: ICreateTerminalOptions = { config: profile, location: splitLocation };
+	const sanitizedProfileName = profile.profileName.replace(/[\n\r\t]/g, '');
+	dropdownActions.push(disposableStore.add(new Action(TerminalCommandId.NewWithProfile, isDefault ? localize('defaultTerminalProfile', "{0} (Default)", sanitizedProfileName) : sanitizedProfileName, undefined, true, async () => {
+		await terminalService.createAndFocusTerminal(options);
+	})));
+	submenuActions.push(disposableStore.add(new Action(TerminalCommandId.Split, isDefault ? localize('defaultTerminalProfile', "{0} (Default)", sanitizedProfileName) : sanitizedProfileName, undefined, true, async () => {
+		await terminalService.createAndFocusTerminal(splitOptions);
+	})));
+}
+
+function addContributedProfileActions(
+	contributed: IExtensionTerminalProfile,
+	defaultProfileName: string,
+	location: ITerminalLocationOptions,
+	splitLocation: ITerminalLocationOptions,
+	terminalService: ITerminalService,
+	dropdownActions: IAction[],
+	submenuActions: IAction[],
+	disposableStore: DisposableStore
+): void {
+	const isDefault = contributed.title === defaultProfileName;
+	const title = isDefault ? localize('defaultTerminalProfile', "{0} (Default)", contributed.title.replace(/[\n\r\t]/g, '')) : contributed.title.replace(/[\n\r\t]/g, '');
+	dropdownActions.push(disposableStore.add(new Action('contributed', title, undefined, true, () => terminalService.createAndFocusTerminal({
+		config: {
+			extensionIdentifier: contributed.extensionIdentifier,
+			id: contributed.id,
+			title
+		},
+		location
+	}))));
+	submenuActions.push(disposableStore.add(new Action('contributed-split', title, undefined, true, () => terminalService.createAndFocusTerminal({
+		config: {
+			extensionIdentifier: contributed.extensionIdentifier,
+			id: contributed.id,
+			title
+		},
+		location: splitLocation
+	}))));
+}
diff --git a/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts b/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts
index 2cc3d43b763cc..1733e24d83e37 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminalProcessManager.ts
@@ -261,7 +261,12 @@ export class TerminalProcessManager extends Disposable implements ITerminalProce
 			this.backend = backend;
 
 			// Create variable resolver
-			const variableResolver = terminalEnvironment.createVariableResolver(this._cwdWorkspaceFolder, await this._terminalProfileResolverService.getEnvironment(this.remoteAuthority), this._configurationResolverService);
+			// Start with the full base environment so that all standard variables (e.g. PATH) are
+			// available, then overlay the shell environment on top so that launch configuration
+			// variables and shell-profile modifications take precedence.
+			const envForResolver = { ...await this._terminalProfileResolverService.getEnvironment(this.remoteAuthority) };
+			terminalEnvironment.mergeEnvironments(envForResolver, await backend.getShellEnvironment());
+			const variableResolver = terminalEnvironment.createVariableResolver(this._cwdWorkspaceFolder, envForResolver, this._configurationResolverService);
 
 			// resolvedUserHome is needed here as remote resolvers can launch local terminals before
 			// they're connected to the remote.
diff --git a/src/vs/workbench/contrib/terminal/browser/terminalService.ts b/src/vs/workbench/contrib/terminal/browser/terminalService.ts
index 6107058afad2d..421ba3cb758f1 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminalService.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminalService.ts
@@ -1220,6 +1220,10 @@ export class TerminalService extends Disposable implements ITerminalService {
 	}
 
 	private _evaluateLocalCwd(shellLaunchConfig: IShellLaunchConfig) {
+		if (this._environmentService.isSessionsWindow) {
+			return;
+		}
+
 		// Add welcome message and title annotation for local terminals launched within remote or
 		// virtual workspaces
 		if (!isString(shellLaunchConfig.cwd) && shellLaunchConfig.cwd?.scheme === Schemas.file) {
@@ -1233,6 +1237,45 @@ export class TerminalService extends Disposable implements ITerminalService {
 		}
 	}
 
+	moveToBackground(instance: ITerminalInstance): void {
+		// Already backgrounded
+		if (this._backgroundedTerminalInstances.some(bg => bg.instance === instance)) {
+			return;
+		}
+
+		// Remove from its current location (panel group or editor)
+		if (instance.target === TerminalLocation.Editor) {
+			this._terminalEditorService.detachInstance(instance);
+		} else {
+			const group = this._terminalGroupService.getGroupForInstance(instance);
+			if (!group) {
+				return;
+			}
+			group.removeInstance(instance);
+		}
+
+		instance.detachFromElement();
+
+		// Track in background
+		this._backgroundedTerminalInstances.push({ instance, terminalLocationOptions: instance.target === TerminalLocation.Editor ? { viewColumn: ACTIVE_GROUP } : undefined });
+		this._backgroundedTerminalDisposables.set(instance.instanceId, [
+			instance.onDisposed(instance => {
+				const idx = this._backgroundedTerminalInstances.findIndex(bg => bg.instance === instance);
+				if (idx !== -1) {
+					this._backgroundedTerminalInstances.splice(idx, 1);
+				}
+				const disposables = this._backgroundedTerminalDisposables.get(instance.instanceId);
+				if (disposables) {
+					dispose(disposables);
+				}
+				this._backgroundedTerminalDisposables.delete(instance.instanceId);
+				this._onDidDisposeInstance.fire(instance);
+			})
+		]);
+
+		this._onDidChangeInstances.fire();
+	}
+
 	public async showBackgroundTerminal(instance: ITerminalInstance, suppressSetActive?: boolean): Promise<void> {
 		const index = this._backgroundedTerminalInstances.findIndex(bg => bg.instance === instance);
 		if (index === -1) {
diff --git a/src/vs/workbench/contrib/terminal/browser/terminalTelemetry.ts b/src/vs/workbench/contrib/terminal/browser/terminalTelemetry.ts
index 9351985ccb889..45914710aaa8c 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminalTelemetry.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminalTelemetry.ts
@@ -80,6 +80,8 @@ export class TerminalTelemetryContribution extends Disposable implements IWorkbe
 			shellIntegrationInjected: boolean;
 			shellIntegrationInjectionFailureReason: ShellIntegrationInjectionFailureReason | undefined;
 
+			imageAddonLoaded: boolean;
+
 			terminalSessionId: string;
 		};
 		type TerminalCreationTelemetryClassification = {
@@ -101,6 +103,8 @@ export class TerminalTelemetryContribution extends Disposable implements IWorkbe
 			shellIntegrationInjected: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Whether the shell integration script was injected.' };
 			shellIntegrationInjectionFailureReason: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Info about shell integration injection.' };
 
+			imageAddonLoaded: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Whether the xterm.js image addon was loaded.' };
+
 			terminalSessionId: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The session ID of the terminal instance.' };
 		};
 		this._telemetryService.publicLog2<TerminalCreationTelemetryData, TerminalCreationTelemetryClassification>('terminal/createInstance', {
@@ -122,6 +126,7 @@ export class TerminalTelemetryContribution extends Disposable implements IWorkbe
 			shellIntegrationQuality: commandDetection?.hasRichCommandDetection ? 2 : commandDetection ? 1 : 0,
 			shellIntegrationInjected: instance.usedShellIntegrationInjection,
 			shellIntegrationInjectionFailureReason: instance.shellIntegrationInjectionFailureReason,
+			imageAddonLoaded: instance.xterm?.isImageAddonLoaded ?? false,
 			terminalSessionId: instance.sessionId,
 		});
 	}
diff --git a/src/vs/workbench/contrib/terminal/browser/terminalView.ts b/src/vs/workbench/contrib/terminal/browser/terminalView.ts
index 9a7457274151e..01632bee153f7 100644
--- a/src/vs/workbench/contrib/terminal/browser/terminalView.ts
+++ b/src/vs/workbench/contrib/terminal/browser/terminalView.ts
@@ -289,7 +289,7 @@ export class TerminalViewPane extends ViewPane {
 			case TerminalCommandId.New: {
 				if (action instanceof MenuItemAction) {
 					this._disposableStore.clear();
-					const actions = getTerminalActionBarArgs(TerminalLocation.Panel, this._terminalProfileService.availableProfiles, this._getDefaultProfileName(), this._terminalProfileService.contributedProfiles, this._terminalService, this._dropdownMenu, this._disposableStore);
+					const actions = getTerminalActionBarArgs(TerminalLocation.Panel, this._terminalProfileService.availableProfiles, this._getDefaultProfileName(), this._terminalProfileService.contributedProfiles, this._terminalService, this._dropdownMenu, this._disposableStore, this._configurationService);
 					this._newDropdown.value = this._instantiationService.createInstance(DropdownWithPrimaryActionViewItem, action, actions.dropdownAction, actions.dropdownMenuActions, actions.className, {
 						hoverDelegate: options.hoverDelegate,
 						getKeyBinding: (action: IAction) => this._keybindingService.lookupKeybinding(action.id, this._contextKeyService)
@@ -318,8 +318,15 @@ export class TerminalViewPane extends ViewPane {
 
 	private _updateTabActionBar(profiles: ITerminalProfile[]): void {
 		this._disposableStore.clear();
-		const actions = getTerminalActionBarArgs(TerminalLocation.Panel, profiles, this._getDefaultProfileName(), this._terminalProfileService.contributedProfiles, this._terminalService, this._dropdownMenu, this._disposableStore);
+		const actions = getTerminalActionBarArgs(TerminalLocation.Panel, profiles, this._getDefaultProfileName(), this._terminalProfileService.contributedProfiles, this._terminalService, this._dropdownMenu, this._disposableStore, this._configurationService);
 		this._newDropdown.value?.update(actions.dropdownAction, actions.dropdownMenuActions);
+
+		this._disposableStore.add(this._configurationService.onDidChangeConfiguration(e => {
+			if (e.affectsConfiguration(TerminalSettingId.ExperimentalAiProfileGrouping)) {
+				const updatedActions = getTerminalActionBarArgs(TerminalLocation.Panel, profiles, this._getDefaultProfileName(), this._terminalProfileService.contributedProfiles, this._terminalService, this._dropdownMenu, this._disposableStore, this._configurationService);
+				this._newDropdown.value?.update(updatedActions.dropdownAction, updatedActions.dropdownMenuActions);
+			}
+		}));
 	}
 
 	override focus() {
diff --git a/src/vs/workbench/contrib/terminal/browser/xterm/xtermTerminal.ts b/src/vs/workbench/contrib/terminal/browser/xterm/xtermTerminal.ts
index be33e2b306bf8..b043728acf3dc 100644
--- a/src/vs/workbench/contrib/terminal/browser/xterm/xtermTerminal.ts
+++ b/src/vs/workbench/contrib/terminal/browser/xterm/xtermTerminal.ts
@@ -47,6 +47,7 @@ import type { IProgressState } from '@xterm/addon-progress';
 import type { CommandDetectionCapability } from '../../../../../platform/terminal/common/capabilities/commandDetectionCapability.js';
 import { URI } from '../../../../../base/common/uri.js';
 import { isNumber } from '../../../../../base/common/types.js';
+import { clamp } from '../../../../../base/common/numbers.js';
 
 const enum RenderConstants {
 	SmoothScrollDuration = 125
@@ -141,6 +142,7 @@ export class XtermTerminal extends Disposable implements IXtermTerminal, IDetach
 
 	get isStdinDisabled(): boolean { return !!this.raw.options.disableStdin; }
 	get isGpuAccelerated(): boolean { return !!this._webglAddon; }
+	get isImageAddonLoaded(): boolean { return !!this._imageAddon; }
 
 	private readonly _onDidRequestRunCommand = this._register(new Emitter<{ command: ITerminalCommand; noNewLine?: boolean }>());
 	readonly onDidRequestRunCommand = this._onDidRequestRunCommand.event;
@@ -916,6 +918,18 @@ export class XtermTerminal extends Disposable implements IXtermTerminal, IDetach
 				const AddonCtor = await this._xtermAddonLoader.importAddon('image');
 				this._imageAddon = new AddonCtor();
 				this.raw.loadAddon(this._imageAddon);
+				type TerminalImageAddonActivatedClassification = {
+					owner: 'anthonykim1';
+					comment: 'Tracks when the xterm.js image addon is loaded, including dynamic enablement';
+				};
+				this._telemetryService.publicLog2<{}, TerminalImageAddonActivatedClassification>('terminal/imageAddonActivated');
+				this._register(this._imageAddon.onImageAdded(() => {
+					type TerminalImageAddedClassification = {
+						owner: 'anthonykim1';
+						comment: 'Tracks when an image is added to the terminal via the image addon';
+					};
+					this._telemetryService.publicLog2<{}, TerminalImageAddedClassification>('terminal/imageAdded');
+				}));
 			}
 		} else {
 			try {
@@ -951,16 +965,21 @@ export class XtermTerminal extends Disposable implements IXtermTerminal, IDetach
 			this.raw.loadAddon(this._serializeAddon);
 		}
 
+		const lastLine = this.raw.buffer.active.length - 1;
+		if (lastLine < 0) {
+			return '';
+		}
+
 		const hasValidEndMarker = isNumber(endMarker?.line);
-		const start = isNumber(startMarker?.line) && startMarker?.line > -1 ? startMarker.line : 0;
+		const start = clamp(isNumber(startMarker?.line) && startMarker.line > -1 ? startMarker.line : 0, 0, lastLine);
 		let end = hasValidEndMarker ? endMarker.line : this.raw.buffer.active.length - 1;
 		if (skipLastLine && hasValidEndMarker) {
 			end = end - 1;
 		}
-		end = Math.max(end, start);
+		end = clamp(Math.max(end, start), start, lastLine);
 		return this._serializeAddon.serialize({
 			range: {
-				start: startMarker?.line ?? 0,
+				start,
 				end
 			}
 		});
diff --git a/src/vs/workbench/contrib/terminal/common/remote/remoteTerminalChannel.ts b/src/vs/workbench/contrib/terminal/common/remote/remoteTerminalChannel.ts
index 6b6e849e3444d..6cdd98743ab35 100644
--- a/src/vs/workbench/contrib/terminal/common/remote/remoteTerminalChannel.ts
+++ b/src/vs/workbench/contrib/terminal/common/remote/remoteTerminalChannel.ts
@@ -8,6 +8,7 @@ import { URI, UriComponents } from '../../../../../base/common/uri.js';
 import { IChannel } from '../../../../../base/parts/ipc/common/ipc.js';
 import { IWorkbenchConfigurationService } from '../../../../services/configuration/common/configuration.js';
 import { IRemoteAuthorityResolverService } from '../../../../../platform/remote/common/remoteAuthorityResolver.js';
+import { IWorkbenchEnvironmentService } from '../../../../services/environment/common/environmentService.js';
 import { IWorkspaceContextService } from '../../../../../platform/workspace/common/workspace.js';
 import { serializeEnvironmentDescriptionMap, serializeEnvironmentVariableCollection } from '../../../../../platform/terminal/common/environmentVariableShared.js';
 import { IConfigurationResolverService } from '../../../../services/configurationResolver/common/configurationResolver.js';
@@ -111,6 +112,7 @@ export class RemoteTerminalChannelClient implements IPtyHostController {
 		@ITerminalLogService private readonly _logService: ITerminalLogService,
 		@IEditorService private readonly _editorService: IEditorService,
 		@ILabelService private readonly _labelService: ILabelService,
+		@IWorkbenchEnvironmentService private readonly _environmentService: IWorkbenchEnvironmentService,
 	) { }
 
 	restartPtyHost(): Promise<void> {
@@ -152,7 +154,13 @@ export class RemoteTerminalChannelClient implements IPtyHostController {
 		}
 
 		const resolverResult = await this._remoteAuthorityResolverService.resolveAuthority(this._remoteAuthority);
-		const resolverEnv = resolverResult.options && resolverResult.options.extensionHostEnv;
+		const resolverEnv = {
+			/**
+			 * If the extension host was spawned via a launch configuration,
+			 * include the environment provided by that launch configuration.
+			 */
+			...(this._environmentService.debugExtensionHost.env ?? {}), ...resolverResult.options?.extensionHostEnv
+		};
 
 		const workspace = this._workspaceContextService.getWorkspace();
 		const workspaceFolders = workspace.folders;
diff --git a/src/vs/workbench/contrib/terminal/common/scripts/shellIntegration.ps1 b/src/vs/workbench/contrib/terminal/common/scripts/shellIntegration.ps1
index a16eaa8534254..afeac192274aa 100644
--- a/src/vs/workbench/contrib/terminal/common/scripts/shellIntegration.ps1
+++ b/src/vs/workbench/contrib/terminal/common/scripts/shellIntegration.ps1
@@ -176,13 +176,29 @@ elseif ((Test-Path variable:global:GitPromptSettings) -and $Global:GitPromptSett
 }
 
 if ($Global:__VSCodeState.IsA11yMode -eq "1") {
-	if (-not (Get-Module -Name PSReadLine)) {
-		$scriptRoot = Split-Path -Parent $MyInvocation.MyCommand.Path
-		$specialPsrlPath = Join-Path $scriptRoot 'psreadline'
-		Import-Module $specialPsrlPath
+	# Check if the loaded PSReadLine already supports EnableScreenReaderMode
+	$hasScreenReaderParam = (Get-Module -Name PSReadLine) -and (Get-Command Set-PSReadLineOption).Parameters.ContainsKey('EnableScreenReaderMode')
+
+	if (-not $hasScreenReaderParam) {
+		# The loaded PSReadLine lacks EnableScreenReaderMode (only available in 2.4.4-beta4+).
+		# PowerShell 7.0+ skips autoloading PSReadLine when the OS reports a screen reader active.
+		# When only VS Code's accessibility mode is enabled (no OS screen reader),
+		# it's still loaded and must be removed to load our bundled copy.
 		if (Get-Module -Name PSReadLine) {
-			Set-PSReadLineOption -EnableScreenReaderMode
+			Remove-Module PSReadLine -Force
+		}
+
+		# Import VS Code's bundled PSReadLine 2.4.3 which has EnableScreenReaderMode
+		$specialPsrlPath = Join-Path (Split-Path -Parent $MyInvocation.MyCommand.Path) 'psreadline'
+		if (Test-Path $specialPsrlPath) {
+			Import-Module $specialPsrlPath
 		}
+
+		$hasScreenReaderParam = (Get-Module -Name PSReadLine) -and (Get-Command Set-PSReadLineOption).Parameters.ContainsKey('EnableScreenReaderMode')
+	}
+
+	if ($hasScreenReaderParam) {
+		Set-PSReadLineOption -EnableScreenReaderMode
 	}
 }
 
diff --git a/src/vs/workbench/contrib/terminal/common/terminalConfiguration.ts b/src/vs/workbench/contrib/terminal/common/terminalConfiguration.ts
index 632938e0d5dd9..132db6d298270 100644
--- a/src/vs/workbench/contrib/terminal/common/terminalConfiguration.ts
+++ b/src/vs/workbench/contrib/terminal/common/terminalConfiguration.ts
@@ -604,6 +604,15 @@ const terminalConfiguration: IStringDictionary<IConfigurationPropertySchema> = {
 			mode: 'auto'
 		}
 	},
+	[TerminalSettingId.ExperimentalAiProfileGrouping]: {
+		markdownDescription: localize('terminal.integrated.experimental.aiProfileGrouping', "Whether to elevate AI-contributed terminal profiles (for example Copilot CLI and Claude Agent) in the new terminal dropdown."),
+		type: 'boolean',
+		default: false,
+		tags: ['experimental'],
+		experiment: {
+			mode: 'auto'
+		}
+	},
 	[TerminalSettingId.ShellIntegrationEnabled]: {
 		restricted: true,
 		markdownDescription: localize('terminal.integrated.shellIntegration.enabled', "Determines whether or not shell integration is auto-injected to support features like enhanced command tracking and current working directory detection. \n\nShell integration works by injecting the shell with a startup script. The script gives VS Code insight into what is happening within the terminal.\n\nSupported shells:\n\n- Linux/macOS: bash, fish, pwsh, zsh\n - Windows: pwsh, git bash\n\nThis setting applies only when terminals are created, so you will need to restart your terminals for it to take effect.\n\n Note that the script injection may not work if you have custom arguments defined in the terminal profile, have enabled {1}, have a [complex bash `PROMPT_COMMAND`](https://code.visualstudio.com/docs/editor/integrated-terminal#_complex-bash-promptcommand), or other unsupported setup. To disable decorations, see {0}", '`#terminal.integrated.shellIntegration.decorationsEnabled#`', '`#editor.accessibilitySupport#`'),
diff --git a/src/vs/workbench/contrib/terminal/electron-browser/localTerminalBackend.ts b/src/vs/workbench/contrib/terminal/electron-browser/localTerminalBackend.ts
index 4435552b283f7..e30e2c69b465e 100644
--- a/src/vs/workbench/contrib/terminal/electron-browser/localTerminalBackend.ts
+++ b/src/vs/workbench/contrib/terminal/electron-browser/localTerminalBackend.ts
@@ -37,6 +37,7 @@ import { IStatusbarService } from '../../../services/statusbar/browser/statusbar
 import { memoize } from '../../../../base/common/decorators.js';
 import { StopWatch } from '../../../../base/common/stopwatch.js';
 import { IRemoteAgentService } from '../../../services/remote/common/remoteAgentService.js';
+import { INativeWorkbenchEnvironmentService } from '../../../services/environment/electron-browser/environmentService.js';
 import { shouldUseEnvironmentVariableCollection } from '../../../../platform/terminal/common/terminalEnvironment.js';
 import { DisposableStore, MutableDisposable } from '../../../../base/common/lifecycle.js';
 
@@ -95,6 +96,7 @@ class LocalTerminalBackend extends BaseTerminalBackend implements ITerminalBacke
 		@INativeHostService private readonly _nativeHostService: INativeHostService,
 		@IStatusbarService statusBarService: IStatusbarService,
 		@IRemoteAgentService private readonly _remoteAgentService: IRemoteAgentService,
+		@INativeWorkbenchEnvironmentService private readonly _environmentService: INativeWorkbenchEnvironmentService,
 	) {
 		super(_localPtyService, logService, historyService, _configurationResolverService, statusBarService, workspaceContextService);
 
@@ -294,7 +296,14 @@ class LocalTerminalBackend extends BaseTerminalBackend implements ITerminalBacke
 
 	@memoize
 	async getShellEnvironment(): Promise<IProcessEnvironment> {
-		return this._shellEnvironmentService.getShellEnv();
+		const env = { ... await this._shellEnvironmentService.getShellEnv() };
+
+		// If running in the context of an extension development host, include the environment derived from the launch configuration
+		if (this._environmentService.debugExtensionHost.env) {
+			terminalEnvironment.mergeEnvironments(env, this._environmentService.debugExtensionHost.env);
+		}
+
+		return env;
 	}
 
 	async getWslPath(original: string, direction: 'unix-to-win' | 'win-to-unix'): Promise<string> {
diff --git a/src/vs/workbench/contrib/terminal/electron-browser/terminal.contribution.ts b/src/vs/workbench/contrib/terminal/electron-browser/terminal.contribution.ts
index b439e425bd324..4b39ed78c2398 100644
--- a/src/vs/workbench/contrib/terminal/electron-browser/terminal.contribution.ts
+++ b/src/vs/workbench/contrib/terminal/electron-browser/terminal.contribution.ts
@@ -6,6 +6,7 @@
 import { InstantiationType, registerSingleton } from '../../../../platform/instantiation/common/extensions.js';
 import { registerMainProcessRemoteService } from '../../../../platform/ipc/electron-browser/services.js';
 import { Registry } from '../../../../platform/registry/common/platform.js';
+import '../../../../platform/sandbox/electron-browser/sandboxHelperService.js';
 import { ILocalPtyService, TerminalIpcChannels } from '../../../../platform/terminal/common/terminal.js';
 import { IWorkbenchContributionsRegistry, WorkbenchPhase, Extensions as WorkbenchExtensions, registerWorkbenchContribution2 } from '../../../common/contributions.js';
 import { ITerminalProfileResolverService } from '../common/terminal.js';
diff --git a/src/vs/workbench/contrib/terminal/test/browser/chatTerminalCommandMirror.test.ts b/src/vs/workbench/contrib/terminal/test/browser/chatTerminalCommandMirror.test.ts
index 851c3d5f70297..9a30e722fe252 100644
--- a/src/vs/workbench/contrib/terminal/test/browser/chatTerminalCommandMirror.test.ts
+++ b/src/vs/workbench/contrib/terminal/test/browser/chatTerminalCommandMirror.test.ts
@@ -202,6 +202,17 @@ suite('Workbench - ChatTerminalCommandMirror', () => {
 			strictEqual(mirrorText.includes('before'), false);
 		});
 
+		test('disposed start marker does not throw in VT serialization', async () => {
+			const source = await createXterm();
+			await write(source, 'line 1\r\nline 2');
+
+			const startMarker = source.raw.registerMarker(0)!;
+			startMarker.dispose();
+
+			const vt = await source.getRangeAsVT(startMarker, undefined, true);
+			strictEqual(typeof vt, 'string');
+		});
+
 		test('incremental mirroring appends correctly', async () => {
 			const source = await createXterm();
 			const marker = source.raw.registerMarker(0)!;
@@ -261,10 +272,8 @@ suite('Workbench - ChatTerminalCommandMirror', () => {
 			// Boundary should NOT match because the prefix diverged
 			strictEqual(boundaryMatches, false, 'Boundary check should detect divergence');
 
-			// When boundary doesn't match, the fix does a full reset + rewrite
-			// instead of corrupting the output by blind slicing
-			mirror.raw.reset();
-			await write(mirror, vt2);
+			// Use \x1bc (RIS) + new content in one write to avoid a blank frame
+			await write(mirror, `\x1bc${vt2}`);
 
 			// Final content should be the complete new VT, not corrupted
 			strictEqual(getBufferText(mirror), 'DifferentPrefixLine3');
diff --git a/src/vs/workbench/contrib/terminal/test/browser/terminalProcessManager.test.ts b/src/vs/workbench/contrib/terminal/test/browser/terminalProcessManager.test.ts
index 70ed6a4426e8f..f029f371a9072 100644
--- a/src/vs/workbench/contrib/terminal/test/browser/terminalProcessManager.test.ts
+++ b/src/vs/workbench/contrib/terminal/test/browser/terminalProcessManager.test.ts
@@ -69,7 +69,8 @@ class TestTerminalInstanceService implements Partial<ITerminalInstanceService> {
 				options: any,
 				shouldPersist: boolean
 			) => new TestTerminalChildProcess(shouldPersist),
-			getLatency: () => Promise.resolve([])
+			getLatency: () => Promise.resolve([]),
+			getShellEnvironment: () => Promise.resolve({})
 		} as unknown as ITerminalBackend;
 	}
 }
diff --git a/src/vs/workbench/contrib/terminalContrib/chat/browser/terminalChatWidget.ts b/src/vs/workbench/contrib/terminalContrib/chat/browser/terminalChatWidget.ts
index 946f14bcbcd06..be4f138c4eaf1 100644
--- a/src/vs/workbench/contrib/terminalContrib/chat/browser/terminalChatWidget.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chat/browser/terminalChatWidget.ts
@@ -412,7 +412,7 @@ export class TerminalChatWidget extends Disposable {
 		if (!model?.sessionResource) {
 			return;
 		}
-		this._chatService.cancelCurrentRequestForSession(model?.sessionResource);
+		void this._chatService.cancelCurrentRequestForSession(model?.sessionResource, 'terminalChat');
 	}
 
 	async viewInChat(): Promise<void> {
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/runInTerminalHelpers.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/runInTerminalHelpers.ts
index 7cbf89ca9f38d..4edc69a5fad9a 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/runInTerminalHelpers.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/runInTerminalHelpers.ts
@@ -77,6 +77,14 @@ export function sanitizeTerminalOutput(output: string): string {
 	return sanitized;
 }
 
+/**
+ * Normalizes command text for UI display by removing unnecessary quote and forward slash
+ * escaping artifacts (for example: \" \' \/) commonly produced in streamed tool-call JSON.
+ */
+export function normalizeTerminalCommandForDisplay(commandLine: string): string {
+	return commandLine.replace(/\\(["'\/])/g, '$1');
+}
+
 export function generateAutoApproveActions(commandLine: string, subCommands: string[], autoApproveResult: { subCommandResults: ICommandApprovalResultWithReason[]; commandLineResult: ICommandApprovalResultWithReason }): ToolConfirmationAction[] {
 	const actions: ToolConfirmationAction[] = [];
 
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/runInTerminalToolTelemetry.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/runInTerminalToolTelemetry.ts
index 047c59fab3975..260165d655600 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/runInTerminalToolTelemetry.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/runInTerminalToolTelemetry.ts
@@ -19,7 +19,7 @@ export class RunInTerminalToolTelemetry {
 		subCommands: string[];
 		autoApproveAllowed: 'allowed' | 'needsOptIn' | 'off';
 		autoApproveResult: 'approved' | 'denied' | 'manual';
-		autoApproveReason: 'subCommand' | 'commandLine' | undefined;
+		autoApproveReason: 'subCommand' | 'commandLine' | 'session' | undefined;
 		autoApproveDefault: boolean | undefined;
 	}) {
 		const subCommandsSanitized = state.subCommands.map(e => {
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/commandLineAnalyzer/commandLineAnalyzer.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/commandLineAnalyzer/commandLineAnalyzer.ts
index b18edd0b7b373..599f0f93b8ca8 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/commandLineAnalyzer/commandLineAnalyzer.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/commandLineAnalyzer/commandLineAnalyzer.ts
@@ -65,4 +65,13 @@ export interface ICommandLineAnalyzerResult {
 	readonly customActions?: ToolConfirmationAction[];
 	// Indicates that auto approval should be forced (e.g. sandboxed commands).
 	readonly forceAutoApproval?: boolean;
+	/**
+	 * Optional denial details when this analyzer explicitly denied auto-execution.
+	 */
+	readonly denialDetails?: {
+		readonly scope: 'subCommand' | 'commandLine';
+		readonly deniedCommand: string;
+		readonly reason: string;
+		readonly ruleSourceText?: string;
+	};
 }
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/commandLineAnalyzer/commandLineAutoApproveAnalyzer.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/commandLineAnalyzer/commandLineAutoApproveAnalyzer.ts
index dfd1d5d8d3c35..03818e588b2fa 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/commandLineAnalyzer/commandLineAutoApproveAnalyzer.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/commandLineAnalyzer/commandLineAutoApproveAnalyzer.ts
@@ -51,20 +51,9 @@ export class CommandLineAutoApproveAnalyzer extends Disposable implements IComma
 	}
 
 	async analyze(options: ICommandLineAnalyzerOptions): Promise<ICommandLineAnalyzerResult> {
-		if (options.chatSessionResource && this._terminalChatService.hasChatSessionAutoApproval(options.chatSessionResource)) {
-			this._log('Session has auto approval enabled, auto approving command');
-			const disableUri = createCommandUri(TerminalChatCommandId.DisableSessionAutoApproval, options.chatSessionResource);
-			const mdTrustSettings = {
-				isTrusted: {
-					enabledCommands: [TerminalChatCommandId.DisableSessionAutoApproval]
-				}
-			};
-			return {
-				isAutoApproved: true,
-				isAutoApproveAllowed: true,
-				disclaimers: [],
-				autoApproveInfo: new MarkdownString(`${localize('autoApprove.session', 'Auto approved for this session')} ([${localize('autoApprove.session.disable', 'Disable')}](${disableUri.toString()}))`, mdTrustSettings),
-			};
+		const hasSessionAutoApproval = options.chatSessionResource && this._terminalChatService.hasChatSessionAutoApproval(options.chatSessionResource);
+		if (hasSessionAutoApproval) {
+			this._log('Session has auto approval enabled');
 		}
 
 		const trimmedCommandLine = options.commandLine.trimStart();
@@ -97,26 +86,44 @@ export class CommandLineAutoApproveAnalyzer extends Disposable implements IComma
 		];
 
 		let isDenied = false;
-		let autoApproveReason: 'subCommand' | 'commandLine' | undefined;
+		let autoApproveReason: 'subCommand' | 'commandLine' | 'session' | undefined;
 		let autoApproveDefault: boolean | undefined;
+		let denialDetails: ICommandLineAnalyzerResult['denialDetails'];
 
-		const deniedSubCommandResult = subCommandResults.find(e => e.result === 'denied');
+		const deniedSubCommandResultIndex = subCommandResults.findIndex(e => e.result === 'denied');
+		const deniedSubCommandResult = deniedSubCommandResultIndex !== -1 ? subCommandResults[deniedSubCommandResultIndex] : undefined;
 		if (deniedSubCommandResult) {
 			this._log('Sub-command DENIED auto approval');
 			isDenied = true;
 			autoApproveDefault = isAutoApproveRule(deniedSubCommandResult.rule) ? deniedSubCommandResult.rule.isDefaultRule : undefined;
 			autoApproveReason = 'subCommand';
+			denialDetails = {
+				scope: 'subCommand',
+				deniedCommand: subCommands[deniedSubCommandResultIndex] ?? trimmedCommandLine,
+				reason: deniedSubCommandResult.reason,
+				ruleSourceText: isAutoApproveRule(deniedSubCommandResult.rule) ? deniedSubCommandResult.rule.sourceText : undefined,
+			};
 		} else if (commandLineResult.result === 'denied') {
 			this._log('Command line DENIED auto approval');
 			isDenied = true;
 			autoApproveDefault = isAutoApproveRule(commandLineResult.rule) ? commandLineResult.rule.isDefaultRule : undefined;
 			autoApproveReason = 'commandLine';
+			denialDetails = {
+				scope: 'commandLine',
+				deniedCommand: trimmedCommandLine,
+				reason: commandLineResult.reason,
+				ruleSourceText: isAutoApproveRule(commandLineResult.rule) ? commandLineResult.rule.sourceText : undefined,
+			};
 		} else {
 			if (subCommandResults.every(e => e.result === 'approved')) {
 				this._log('All sub-commands auto-approved');
 				isAutoApproved = true;
 				autoApproveReason = 'subCommand';
 				autoApproveDefault = subCommandResults.every(e => isAutoApproveRule(e.rule) && e.rule.isDefaultRule);
+			} else if (hasSessionAutoApproval) {
+				this._log('Session auto approval - approving non-denied command');
+				isAutoApproved = true;
+				autoApproveReason = 'session';
 			} else {
 				this._log('All sub-commands NOT auto-approved');
 				if (commandLineResult.result === 'approved') {
@@ -138,7 +145,15 @@ export class CommandLineAutoApproveAnalyzer extends Disposable implements IComma
 		// Apply auto approval or force it off depending on enablement/opt-in state
 		const isAutoApproveEnabled = this._configurationService.getValue(TerminalChatAgentToolsSettingId.EnableAutoApprove) === true;
 		const isAutoApproveWarningAccepted = this._storageService.getBoolean(TerminalToolConfirmationStorageKeys.TerminalAutoApproveWarningAccepted, StorageScope.APPLICATION, false);
-		if (isAutoApproveEnabled && isAutoApproved) {
+		if (hasSessionAutoApproval && isAutoApproved) {
+			const disableUri = createCommandUri(TerminalChatCommandId.DisableSessionAutoApproval, options.chatSessionResource!);
+			const mdTrustSettings = {
+				isTrusted: {
+					enabledCommands: [TerminalChatCommandId.DisableSessionAutoApproval]
+				}
+			};
+			autoApproveInfo = new MarkdownString(`${localize('autoApprove.session', 'Auto approved for this session')} ([${localize('autoApprove.session.disable', 'Disable')}](${disableUri.toString()}))`, mdTrustSettings);
+		} else if (isAutoApproveEnabled && isAutoApproved) {
 			autoApproveInfo = this._createAutoApproveInfo(
 				isAutoApproved,
 				isDenied,
@@ -195,13 +210,14 @@ export class CommandLineAutoApproveAnalyzer extends Disposable implements IComma
 			disclaimers,
 			autoApproveInfo,
 			customActions,
+			denialDetails,
 		};
 	}
 
 	private _createAutoApproveInfo(
 		isAutoApproved: boolean,
 		isDenied: boolean,
-		autoApproveReason: 'subCommand' | 'commandLine' | undefined,
+		autoApproveReason: 'subCommand' | 'commandLine' | 'session' | undefined,
 		subCommandResults: ICommandApprovalResultWithReason[],
 		commandLineResult: ICommandApprovalResultWithReason,
 	): IMarkdownString | undefined {
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/commandLineRewriter/commandLineSandboxRewriter.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/commandLineRewriter/commandLineSandboxRewriter.ts
index 030afe5a76ab2..3fb9dbfbf9843 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/commandLineRewriter/commandLineSandboxRewriter.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/commandLineRewriter/commandLineSandboxRewriter.ts
@@ -19,14 +19,11 @@ export class CommandLineSandboxRewriter extends Disposable implements ICommandLi
 			return undefined;
 		}
 
-		// Ensure sandbox config is initialized before wrapping
-		const sandboxConfigPath = await this._sandboxService.getSandboxConfigPath();
-		if (!sandboxConfigPath) {
-			// If no sandbox config is available, run without sandboxing
+		const wrappedCommand = await this._sandboxService.wrapCommand(options.commandLine);
+		if (wrappedCommand === options.commandLine) {
+			// If the sandbox service returns the same command, it means it didn't actually wrap it for some reason. In that case, we should return undefined to allow other rewriters to run, instead of returning a result that claims the command was rewritten but doesn't actually change anything.
 			return undefined;
 		}
-
-		const wrappedCommand = this._sandboxService.wrapCommand(options.commandLine);
 		return {
 			rewritten: wrappedCommand,
 			reasoning: 'Wrapped command for sandbox execution',
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/monitoring/outputMonitor.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/monitoring/outputMonitor.ts
index 085c43ed463e9..43fd431122103 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/monitoring/outputMonitor.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/monitoring/outputMonitor.ts
@@ -13,13 +13,12 @@ import { Disposable, MutableDisposable, type IDisposable } from '../../../../../
 import { isObject, isString } from '../../../../../../../base/common/types.js';
 import { URI } from '../../../../../../../base/common/uri.js';
 import { localize } from '../../../../../../../nls.js';
-import { ExtensionIdentifier } from '../../../../../../../platform/extensions/common/extensions.js';
 import { IChatWidgetService } from '../../../../../chat/browser/chat.js';
 import { ChatElicitationRequestPart } from '../../../../../chat/common/model/chatProgressTypes/chatElicitationRequestPart.js';
 import { ChatModel } from '../../../../../chat/common/model/chatModel.js';
 import { ElicitationState, IChatService } from '../../../../../chat/common/chatService/chatService.js';
-import { ChatAgentLocation } from '../../../../../chat/common/constants.js';
-import { ChatMessageRole, getTextResponseFromStream, ILanguageModelsService } from '../../../../../chat/common/languageModels.js';
+import { ChatAgentLocation, ChatPermissionLevel } from '../../../../../chat/common/constants.js';
+import { ChatMessageRole, getTextResponseFromStream, type ILanguageModelChatSelector, ILanguageModelsService } from '../../../../../chat/common/languageModels.js';
 import { IToolInvocationContext } from '../../../../../chat/common/tools/languageModelToolsService.js';
 import { ITaskService } from '../../../../../tasks/common/taskService.js';
 import { ILinkLocation } from '../../taskHelpers.js';
@@ -109,6 +108,9 @@ export class OutputMonitor extends Disposable implements IOutputMonitor {
 	private readonly _onDidFinishCommand = this._register(new Emitter<void>());
 	readonly onDidFinishCommand: Event<void> = this._onDidFinishCommand.event;
 
+	/** The chat session resource for this tool invocation, used to check permission level. */
+	private readonly _sessionResource: URI | undefined;
+
 	constructor(
 		private readonly _execution: IExecution,
 		private readonly _pollFn: ((execution: IExecution, token: CancellationToken, taskService: ITaskService) => Promise<IPollingResult | undefined>) | undefined,
@@ -125,6 +127,8 @@ export class OutputMonitor extends Disposable implements IOutputMonitor {
 	) {
 		super();
 
+		this._sessionResource = invocationContext?.sessionResource;
+
 		// Start async to ensure listeners are set up
 		timeout(0).then(() => {
 			this._startMonitoring(command, invocationContext, token);
@@ -226,19 +230,26 @@ export class OutputMonitor extends Disposable implements IOutputMonitor {
 		}
 
 		// Check for VS Code's task finish messages (like "press any key to close the terminal").
-		// These should only be ignored if it's a task AND the task is finished.
-		// Otherwise, "press any key to continue" from scripts should prompt the user.
+		// If the execution is a task and the output contains a VS Code task finish message,
+		// always treat it as a stop signal regardless of task active state (which can be stale).
 		const isTask = this._execution.task !== undefined;
-		const isTaskInactive = this._execution.isActive ? !(await this._execution.isActive()) : true;
-		if (isTask && isTaskInactive && detectsVSCodeTaskFinishMessage(output)) {
-			this._logService.trace('OutputMonitor: Idle -> VS Code task finish message detected for inactive task, stopping');
+		if (isTask && detectsVSCodeTaskFinishMessage(output)) {
+			this._logService.trace('OutputMonitor: Idle -> VS Code task finish message detected, stopping');
 			// Task is finished, ignore the "press any key to close" message
 			return { shouldContinuePollling: false, output };
 		}
 
 		// Check for generic "press any key" prompts from scripts.
-		if ((!isTask || !isTaskInactive) && detectsGenericPressAnyKeyPattern(output)) {
-			this._logService.trace('OutputMonitor: Idle -> generic "press any key" detected, requesting free-form input');
+		// Only shown for non-task executions since task finish messages are handled above.
+		if (!isTask && detectsGenericPressAnyKeyPattern(output)) {
+			this._logService.trace('OutputMonitor: Idle -> generic "press any key" detected');
+			const autoReply = this._configurationService.getValue(TerminalChatAgentToolsSettingId.AutoReplyToPrompts) || this._isAutopilotMode();
+			if (autoReply) {
+				this._logService.trace('OutputMonitor: Auto-reply enabled -> not showing free-form prompt for "press any key", stopping');
+				this._cleanupIdleInputListener();
+				return { shouldContinuePollling: false, output };
+			}
+			this._logService.trace('OutputMonitor: Requesting free-form input for "press any key"');
 			// Register a marker to track this prompt position so we don't re-detect it
 			const currentMarker = this._execution.instance.registerMarker();
 			if (currentMarker) {
@@ -287,17 +298,11 @@ export class OutputMonitor extends Disposable implements IOutputMonitor {
 				this._cleanupIdleInputListener();
 				return { shouldContinuePollling: true };
 			}
-			const autoReply = this._configurationService.getValue(TerminalChatAgentToolsSettingId.AutoReplyToPrompts);
-			if (autoReply && !this._isSensitivePrompt(confirmationPrompt.prompt)) {
-				const explicitInput = confirmationPrompt.suggestedInput ?? this._extractExplicitInputFromPrompt(confirmationPrompt.prompt);
-				const normalizedInput = this._normalizeAutoReplyInput(explicitInput);
-				if (normalizedInput !== undefined) {
-					this._logService.trace('OutputMonitor: Auto-replying to free-form prompt');
-					await this._execution.instance.sendText(normalizedInput, true);
-					this._outputMonitorTelemetryCounters.inputToolAutoAcceptCount++;
-					this._outputMonitorTelemetryCounters.inputToolAutoChars += normalizedInput.length;
-					return { shouldContinuePollling: true };
-				}
+			const autoReply = this._configurationService.getValue(TerminalChatAgentToolsSettingId.AutoReplyToPrompts) || this._isAutopilotMode();
+			if (autoReply) {
+				this._logService.trace('OutputMonitor: Auto-reply enabled -> not propagating free-form prompt, stopping');
+				this._cleanupIdleInputListener();
+				return { shouldContinuePollling: false, output };
 			}
 			// Clean up the input listener now - the prompt will set up its own
 			this._cleanupIdleInputListener();
@@ -469,11 +474,12 @@ export class OutputMonitor extends Disposable implements IOutputMonitor {
 		const model = await this._getLanguageModel();
 		if (!model) {
 			return 'No models available';
+
 		}
 
 		const response = await this._languageModelsService.sendChatRequest(
 			model,
-			new ExtensionIdentifier('core'),
+			undefined,
 			[{ role: ChatMessageRole.User, content: [{ type: 'text', value: `Evaluate this terminal output to determine if there were errors. If there are errors, return them. Otherwise, return undefined: ${buffer}.` }] }],
 			{},
 			token
@@ -546,7 +552,7 @@ export class OutputMonitor extends Disposable implements IOutputMonitor {
 			${lastLines}
 			`;
 
-		const response = await this._languageModelsService.sendChatRequest(model, new ExtensionIdentifier('core'), [{ role: ChatMessageRole.User, content: [{ type: 'text', value: promptText }] }], {}, token);
+		const response = await this._languageModelsService.sendChatRequest(model, undefined, [{ role: ChatMessageRole.User, content: [{ type: 'text', value: promptText }] }], {}, token);
 		const responseText = await getTextResponseFromStream(response);
 		try {
 			const match = responseText.match(/\{[\s\S]*\}/);
@@ -589,35 +595,25 @@ export class OutputMonitor extends Disposable implements IOutputMonitor {
 		return /(password|passphrase|token|api\s*key|secret)/i.test(prompt);
 	}
 
-	private _normalizeAutoReplyInput(input: string | undefined): string | undefined {
-		if (!input) {
-			return undefined;
-		}
-		const trimmed = input.trim();
-		if (!trimmed) {
-			return undefined;
-		}
-		const lowered = trimmed.toLowerCase();
-		if (lowered === '\\r' || lowered === '\\n' || lowered === 'enter' || lowered === 'return') {
-			return '';
-		}
-		return trimmed;
-	}
-
-	private _extractExplicitInputFromPrompt(prompt: string): string | undefined {
-		const normalizedPrompt = prompt.trim();
-		if (!normalizedPrompt) {
-			return undefined;
-		}
-		const directCommandMatch = normalizedPrompt.match(/\b(?:type|enter|input)\s+["'`]([^"'`]+)["'`]/i);
-		if (directCommandMatch?.[1]) {
-			return directCommandMatch[1];
+	/**
+	 * Returns true if the current session is in Autopilot mode (not Bypass Approvals).
+	 * In Autopilot, terminal prompts should be auto-replied to so the agent can
+	 * work autonomously from start to finish.
+	 */
+	private _isAutopilotMode(): boolean {
+		if (!this._sessionResource) {
+			return false;
 		}
-		const bareCommandMatch = normalizedPrompt.match(/\b(?:type|enter|input)\s+([\w.-]+)\b/i);
-		if (bareCommandMatch?.[1]) {
-			return bareCommandMatch[1];
+		// Check the live widget picker level
+		const widget = this._chatWidgetService.getWidgetBySessionResource(this._sessionResource)
+			?? this._chatWidgetService.lastFocusedWidget;
+		if (widget?.input.currentModeInfo.permissionLevel === ChatPermissionLevel.Autopilot) {
+			return true;
 		}
-		return undefined;
+		// Fall back to the request-stamped level
+		const model = this._chatService.getSession(this._sessionResource);
+		const request = model?.getRequests().at(-1);
+		return request?.modeInfo?.permissionLevel === ChatPermissionLevel.Autopilot;
 	}
 
 	private async _selectAndHandleOption(
@@ -627,14 +623,14 @@ export class OutputMonitor extends Disposable implements IOutputMonitor {
 		if (!confirmationPrompt?.options.length) {
 			return undefined;
 		}
-		const model = this._chatWidgetService.getWidgetsByLocations(ChatAgentLocation.Chat)[0]?.input.currentLanguageModel;
-		if (!model) {
-			return undefined;
+		const autoReply = this._configurationService.getValue(TerminalChatAgentToolsSettingId.AutoReplyToPrompts) || this._isAutopilotMode();
+		let model = this._chatWidgetService.getWidgetsByLocations(ChatAgentLocation.Chat)[0]?.input.currentLanguageModel;
+		if (model) {
+			const models = await this._safeSelectLanguageModels({ vendor: 'copilot', family: model.replaceAll('copilot/', '') });
+			model = models[0];
 		}
-
-		const models = await this._languageModelsService.selectLanguageModels({ vendor: 'copilot', family: model.replaceAll('copilot/', '') });
-		if (!models.length) {
-			return undefined;
+		if (!model) {
+			model = await this._getLanguageModel();
 		}
 		const prompt = confirmationPrompt.prompt;
 		const options = confirmationPrompt.options;
@@ -648,13 +644,22 @@ export class OutputMonitor extends Disposable implements IOutputMonitor {
 		this._lastPromptMarker = currentMarker;
 		this._lastPrompt = prompt;
 
-		const promptText = `Given the following confirmation prompt and options from a terminal output, which option is the default?\nPrompt: "${prompt}"\nOptions: ${JSON.stringify(options)}\nRespond with only the option string.`;
-		const response = await this._languageModelsService.sendChatRequest(models[0], new ExtensionIdentifier('core'), [
-			{ role: ChatMessageRole.User, content: [{ type: 'text', value: promptText }] }
-		], {}, token);
+		let suggestedOption = '';
+		if (model) {
+			try {
+				const promptText = `Given the following confirmation prompt and options from a terminal output, which option is the default?\nPrompt: "${prompt}"\nOptions: ${JSON.stringify(options)}\nRespond with only the option string.`;
+				const response = await this._languageModelsService.sendChatRequest(model, undefined, [
+					{ role: ChatMessageRole.User, content: [{ type: 'text', value: promptText }] }
+				], {}, token);
+
+				suggestedOption = (await getTextResponseFromStream(response)).trim();
+			} catch (err) {
+				this._logService.trace('OutputMonitor: Failed to get suggested option from model', err);
+			}
+		} else if (!autoReply) {
+			return undefined;
+		}
 
-		const suggestedOption = (await getTextResponseFromStream(response)).trim();
-		const autoReply = this._configurationService.getValue(TerminalChatAgentToolsSettingId.AutoReplyToPrompts);
 		let validOption: string;
 		let index: number;
 
@@ -923,8 +928,35 @@ export class OutputMonitor extends Disposable implements IOutputMonitor {
 	}
 
 	private async _getLanguageModel(): Promise<string | undefined> {
-		const models = await this._languageModelsService.selectLanguageModels({ vendor: 'copilot', id: 'copilot-fast' });
-		return models.length ? models[0] : undefined;
+		const fastModels = await this._safeSelectLanguageModels({ vendor: 'copilot', id: 'copilot-fast' });
+		if (fastModels.length) {
+			return fastModels[0];
+		}
+
+		const widget = this._chatWidgetService.lastFocusedWidget ?? this._chatWidgetService.getWidgetsByLocations(ChatAgentLocation.Chat)[0];
+		const currentModel = widget?.input.currentLanguageModel;
+		if (currentModel) {
+			const currentFamilyModels = await this._safeSelectLanguageModels({ vendor: 'copilot', family: currentModel.replaceAll('copilot/', '') });
+			if (currentFamilyModels.length) {
+				return currentFamilyModels[0];
+			}
+		}
+
+		const copilotModels = await this._safeSelectLanguageModels({ vendor: 'copilot' });
+		if (copilotModels.length) {
+			return copilotModels[0];
+		}
+
+		return undefined;
+	}
+
+	private async _safeSelectLanguageModels(selector: ILanguageModelChatSelector): Promise<string[]> {
+		try {
+			return await this._languageModelsService.selectLanguageModels(selector);
+		} catch (error) {
+			this._logService.trace('OutputMonitor: selectLanguageModels failed', { selector, error });
+			return [];
+		}
 	}
 }
 
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/runInTerminalTool.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/runInTerminalTool.ts
index 93f3b0c40d045..32bcba19f567c 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/runInTerminalTool.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/runInTerminalTool.ts
@@ -9,15 +9,17 @@ import { CancellationToken, CancellationTokenSource } from '../../../../../../ba
 import { Codicon } from '../../../../../../base/common/codicons.js';
 import { CancellationError } from '../../../../../../base/common/errors.js';
 import { Event } from '../../../../../../base/common/event.js';
-import { MarkdownString, type IMarkdownString } from '../../../../../../base/common/htmlContent.js';
-import { Disposable, DisposableStore } from '../../../../../../base/common/lifecycle.js';
+import { escapeMarkdownSyntaxTokens, MarkdownString, type IMarkdownString } from '../../../../../../base/common/htmlContent.js';
+import { Disposable, DisposableStore, MutableDisposable } from '../../../../../../base/common/lifecycle.js';
 import { ResourceMap } from '../../../../../../base/common/map.js';
+import { getMediaMime } from '../../../../../../base/common/mime.js';
 import { basename, posix, win32 } from '../../../../../../base/common/path.js';
 import { OperatingSystem, OS } from '../../../../../../base/common/platform.js';
 import { count } from '../../../../../../base/common/strings.js';
 import { generateUuid } from '../../../../../../base/common/uuid.js';
 import { localize } from '../../../../../../nls.js';
 import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
+import { IFileService } from '../../../../../../platform/files/common/files.js';
 import { IInstantiationService, type ServicesAccessor } from '../../../../../../platform/instantiation/common/instantiation.js';
 import { ILabelService } from '../../../../../../platform/label/common/label.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../../../platform/storage/common/storage.js';
@@ -26,7 +28,7 @@ import { ITerminalLogService, ITerminalProfile } from '../../../../../../platfor
 import { IRemoteAgentService } from '../../../../../services/remote/common/remoteAgentService.js';
 import { TerminalToolConfirmationStorageKeys } from '../../../../chat/browser/widget/chatContentParts/toolInvocationParts/chatTerminalToolConfirmationSubPart.js';
 import { IChatService, type IChatTerminalToolInvocationData } from '../../../../chat/common/chatService/chatService.js';
-import { CountTokensCallback, ILanguageModelToolsService, IPreparedToolInvocation, IToolData, IToolImpl, IToolInvocation, IToolInvocationPreparationContext, IToolResult, ToolDataSource, ToolInvocationPresentation, ToolProgress } from '../../../../chat/common/tools/languageModelToolsService.js';
+import { CountTokensCallback, ILanguageModelToolsService, IPreparedToolInvocation, IStreamedToolInvocation, IToolData, IToolImpl, IToolInvocation, IToolInvocationPreparationContext, IToolInvocationStreamContext, IToolResult, ToolDataSource, ToolInvocationPresentation, ToolProgress } from '../../../../chat/common/tools/languageModelToolsService.js';
 import { ITerminalChatService, ITerminalService, type ITerminalInstance } from '../../../../terminal/browser/terminal.js';
 import { ITerminalProfileResolverService } from '../../../../terminal/common/terminal.js';
 import { TerminalChatAgentToolsSettingId } from '../../common/terminalChatAgentToolsConfiguration.js';
@@ -36,7 +38,7 @@ import type { ITerminalExecuteStrategy, ITerminalExecuteStrategyResult } from '.
 import { NoneExecuteStrategy } from '../executeStrategy/noneExecuteStrategy.js';
 import { RichExecuteStrategy } from '../executeStrategy/richExecuteStrategy.js';
 import { getOutput } from '../outputHelpers.js';
-import { extractCdPrefix, isFish, isPowerShell, isWindowsPowerShell, isZsh } from '../runInTerminalHelpers.js';
+import { extractCdPrefix, isFish, isPowerShell, isWindowsPowerShell, isZsh, normalizeTerminalCommandForDisplay } from '../runInTerminalHelpers.js';
 import type { ICommandLinePresenter } from './commandLinePresenter/commandLinePresenter.js';
 import { NodeCommandLinePresenter } from './commandLinePresenter/nodeCommandLinePresenter.js';
 import { PythonCommandLinePresenter } from './commandLinePresenter/pythonCommandLinePresenter.js';
@@ -45,7 +47,7 @@ import { SandboxedCommandLinePresenter } from './commandLinePresenter/sandboxedC
 import { RunInTerminalToolTelemetry } from '../runInTerminalToolTelemetry.js';
 import { ShellIntegrationQuality, ToolTerminalCreator, type IToolTerminal } from '../toolTerminalCreator.js';
 import { TreeSitterCommandParser, TreeSitterCommandParserLanguage } from '../treeSitterCommandParser.js';
-import { type ICommandLineAnalyzer, type ICommandLineAnalyzerOptions } from './commandLineAnalyzer/commandLineAnalyzer.js';
+import { type ICommandLineAnalyzer, type ICommandLineAnalyzerOptions, type ICommandLineAnalyzerResult } from './commandLineAnalyzer/commandLineAnalyzer.js';
 import { CommandLineAutoApproveAnalyzer } from './commandLineAnalyzer/commandLineAutoApproveAnalyzer.js';
 import { CommandLineFileWriteAnalyzer } from './commandLineAnalyzer/commandLineFileWriteAnalyzer.js';
 import { CommandLineSandboxAnalyzer } from './commandLineAnalyzer/commandLineSandboxAnalyzer.js';
@@ -63,12 +65,13 @@ import { IWorkspaceContextService } from '../../../../../../platform/workspace/c
 import { IHistoryService } from '../../../../../services/history/common/history.js';
 import { TerminalCommandArtifactCollector } from './terminalCommandArtifactCollector.js';
 import { isNumber, isString } from '../../../../../../base/common/types.js';
-import { ChatConfiguration } from '../../../../chat/common/constants.js';
+import { ChatConfiguration, isAutoApproveLevel } from '../../../../chat/common/constants.js';
 import { IChatWidgetService } from '../../../../chat/browser/chat.js';
 import { TerminalChatCommandId } from '../../../chat/browser/terminalChat.js';
 import { clamp } from '../../../../../../base/common/numbers.js';
 import { IOutputAnalyzer } from './outputAnalyzer.js';
 import { SandboxOutputAnalyzer } from './sandboxOutputAnalyzer.js';
+import { IAgentSessionsService } from '../../../../chat/browser/agentSessions/agentSessionsService.js';
 
 // #region Tool data
 
@@ -308,6 +311,8 @@ const telemetryIgnoredSequences = [
 ];
 
 const altBufferMessage = '\n' + localize('runInTerminalTool.altBufferMessage', "The command opened the alternate buffer.");
+const deniedCommandCircuitBreakerThreshold = 3;
+type DenialDetails = NonNullable<ICommandLineAnalyzerResult['denialDetails']>;
 
 
 export class RunInTerminalTool extends Disposable implements IToolImpl {
@@ -322,8 +327,12 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 	private readonly _commandLineAnalyzers: ICommandLineAnalyzer[];
 	private readonly _commandLinePresenters: ICommandLinePresenter[];
 	private readonly _outputAnalyzers: IOutputAnalyzer[];
+	private readonly _archivedSessionListener = this._register(new MutableDisposable());
 
 	protected readonly _sessionTerminalAssociations = new ResourceMap<IToolTerminal>();
+	protected readonly _sessionTerminalInstances = new ResourceMap<Set<ITerminalInstance>>();
+	private readonly _sessionDeniedCommandCounts = new ResourceMap<Map<string, number>>();
+	private readonly _terminalsBeingDisposedBySessionCleanup = new Set<ITerminalInstance>();
 
 	// Immutable window state
 	protected readonly _osBackend: Promise<OperatingSystem>;
@@ -362,6 +371,7 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 	constructor(
 		@IChatService protected readonly _chatService: IChatService,
 		@IConfigurationService private readonly _configurationService: IConfigurationService,
+		@IFileService private readonly _fileService: IFileService,
 		@IHistoryService private readonly _historyService: IHistoryService,
 		@IInstantiationService private readonly _instantiationService: IInstantiationService,
 		@ILabelService private readonly _labelService: ILabelService,
@@ -373,6 +383,7 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 		@ITerminalService private readonly _terminalService: ITerminalService,
 		@IWorkspaceContextService private readonly _workspaceContextService: IWorkspaceContextService,
 		@IChatWidgetService private readonly _chatWidgetService: IChatWidgetService,
+		@IAgentSessionsService private readonly _agentSessionsService: IAgentSessionsService,
 	) {
 		super();
 
@@ -417,11 +428,7 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 		// Restore terminal associations from storage
 		this._restoreTerminalAssociations();
 		this._register(this._terminalService.onDidDisposeInstance(e => {
-			for (const [sessionResource, toolTerminal] of this._sessionTerminalAssociations.entries()) {
-				if (e === toolTerminal.instance) {
-					this._sessionTerminalAssociations.delete(sessionResource);
-				}
-			}
+			this._removeTerminalAssociations(e);
 		}));
 
 		// Listen for chat session disposal to clean up associated terminals
@@ -430,6 +437,23 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 				this._cleanupSessionTerminals(resource);
 			}
 		}));
+
+	}
+
+	async handleToolStream(context: IToolInvocationStreamContext, _token: CancellationToken): Promise<IStreamedToolInvocation | undefined> {
+		const partialInput = context.rawInput as Partial<IRunInTerminalInputParams> | undefined;
+		if (partialInput && typeof partialInput === 'object' && partialInput.command) {
+			const normalizedCommand = normalizeTerminalCommandForDisplay(partialInput.command).replace(/\r\n|\r|\n/g, ' ');
+			const truncatedCommand = normalizedCommand.length > 80
+				? normalizedCommand.substring(0, 77) + '...'
+				: normalizedCommand;
+			const escapedCommand = escapeMarkdownSyntaxTokens(truncatedCommand);
+			const invocationMessage = partialInput.isBackground
+				? new MarkdownString(localize('runInTerminal.streaming.background', "Running `{0}` in background", escapedCommand))
+				: new MarkdownString(localize('runInTerminal.streaming', "Running `{0}`", escapedCommand));
+			return { invocationMessage };
+		}
+		return { invocationMessage: localize('runInTerminal.streaming.default', "Running command") };
 	}
 
 	async prepareToolInvocation(context: IToolInvocationPreparationContext, token: CancellationToken): Promise<IPreparedToolInvocation | undefined> {
@@ -485,7 +509,7 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 			commandLine: {
 				original: args.command,
 				toolEdited: rewrittenCommand === args.command ? undefined : rewrittenCommand,
-				forDisplay: forDisplayCommand,
+				forDisplay: forDisplayCommand ?? normalizeTerminalCommandForDisplay(rewrittenCommand ?? args.command),
 			},
 			cwd,
 			language,
@@ -585,7 +609,7 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 		}
 
 		// Extract cd prefix for display - show directory in title, command suffix in editor
-		const commandToDisplay = (toolSpecificData.commandLine.userEdited ?? toolSpecificData.commandLine.toolEdited ?? toolSpecificData.commandLine.original).trimStart();
+		const commandToDisplay = (toolSpecificData.commandLine.forDisplay ?? toolSpecificData.commandLine.userEdited ?? toolSpecificData.commandLine.toolEdited ?? toolSpecificData.commandLine.original).trimStart();
 		const extractedCd = extractCdPrefix(commandToDisplay, shell, os);
 		let confirmationTitle: string;
 		if (extractedCd && cwd) {
@@ -644,8 +668,34 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 			}
 		}
 
+		// Check if the session's permission level (Autopilot/Bypass Approvals) auto-approves all tools.
+		// When active, skip terminal confirmation entirely since the user has opted into full auto-approval.
+		const isSessionAutoApproved = chatSessionResource && this._isSessionAutoApproveLevel(chatSessionResource);
+		const deniedAnalyzerResult = commandLineAnalyzerResults.find(e => e.isAutoApproved === false && e.denialDetails);
+
+		// In auto-approval session mode, fail closed for policy-denied commands instead of showing
+		// a confirmation that may block unattended runs.
+		if (isSessionAutoApproved && deniedAnalyzerResult?.denialDetails && context.forceConfirmationReason === undefined) {
+			const denial = deniedAnalyzerResult.denialDetails;
+			const deniedRule = denial.ruleSourceText
+				? ` Rule: \`${escapeMarkdownSyntaxTokens(denial.ruleSourceText)}\`.`
+				: '';
+			const deniedAttempts = this._recordDeniedCommandAttempt(chatSessionResource!, denial);
+			const shouldCircuitBreak = deniedAttempts >= deniedCommandCircuitBreakerThreshold;
+			toolSpecificData.alternativeRecommendation = shouldCircuitBreak
+				? `POLICY_DENIED_CIRCUIT_BREAKER: Command was blocked ${deniedAttempts} times in this session and will not be retried. Scope: ${denial.scope}. Command: \`${escapeMarkdownSyntaxTokens(denial.deniedCommand)}\`. Reason: ${denial.reason}.${deniedRule}`
+				: `POLICY_DENIED: Command was not executed in auto-approval session mode. Scope: ${denial.scope}. Command: \`${escapeMarkdownSyntaxTokens(denial.deniedCommand)}\`. Reason: ${denial.reason}.${deniedRule}`;
+			return {
+				confirmationMessages: undefined,
+				toolSpecificData,
+			};
+		}
+		if (isSessionAutoApproved && chatSessionResource) {
+			this._sessionDeniedCommandCounts.delete(chatSessionResource);
+		}
+
 		// If forceConfirmationReason is set, always show confirmation regardless of auto-approval
-		const shouldShowConfirmation = !isFinalAutoApproved || context.forceConfirmationReason !== undefined;
+		const shouldShowConfirmation = (!isFinalAutoApproved && !isSessionAutoApproved) || context.forceConfirmationReason !== undefined;
 		const confirmationMessages = shouldShowConfirmation ? {
 			title: confirmationTitle,
 			message: new MarkdownString(localize('runInTerminal.confirmationMessage', "Explanation: {0}\n\nGoal: {1}", args.explanation, args.goal)),
@@ -653,12 +703,50 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 			terminalCustomActions: customActions,
 		} : undefined;
 
+		const rawDisplayCommand = toolSpecificData.commandLine.forDisplay ?? toolSpecificData.commandLine.toolEdited ?? toolSpecificData.commandLine.original;
+		const displayCommand = rawDisplayCommand.length > 80
+			? rawDisplayCommand.substring(0, 77) + '...'
+			: rawDisplayCommand;
+		const escapedDisplayCommand = escapeMarkdownSyntaxTokens(displayCommand);
+		const invocationMessage = args.isBackground
+			? new MarkdownString(localize('runInTerminal.invocation.background', "Running `{0}` in background", escapedDisplayCommand))
+			: new MarkdownString(localize('runInTerminal.invocation', "Running `{0}`", escapedDisplayCommand));
+
 		return {
+			invocationMessage,
 			confirmationMessages,
 			toolSpecificData,
 		};
 	}
 
+	/**
+	 * Returns true if the chat session's permission level (Autopilot/Bypass Approvals)
+	 * auto-approves all tool calls, unless enterprise policy restricts it.
+	 * Checks both the request-stamped level and the live picker level.
+	 */
+	private _isSessionAutoApproveLevel(chatSessionResource: URI): boolean {
+		const inspected = this._configurationService.inspect<boolean>(ChatConfiguration.GlobalAutoApprove);
+		if (inspected.policyValue === false) {
+			return false;
+		}
+		// Check the terminal chat service's session auto-approval state
+		if (this._terminalChatService.hasChatSessionAutoApproval(chatSessionResource)) {
+			return true;
+		}
+		// Check the live widget picker level (handles mid-session switches).
+		// Fall back to lastFocusedWidget if the session-specific widget isn't found
+		// (e.g., widget was backgrounded or URI mismatch).
+		const widget = this._chatWidgetService.getWidgetBySessionResource(chatSessionResource)
+			?? this._chatWidgetService.lastFocusedWidget;
+		if (widget && isAutoApproveLevel(widget.input.currentModeInfo.permissionLevel)) {
+			return true;
+		}
+		// Fall back to the request-stamped level
+		const model = this._chatService.getSession(chatSessionResource);
+		const request = model?.getRequests().at(-1);
+		return isAutoApproveLevel(request?.modeInfo?.permissionLevel);
+	}
+
 	async invoke(invocation: IToolInvocation, _countTokens: CountTokensCallback, _progress: ToolProgress, token: CancellationToken): Promise<IToolResult> {
 		const toolSpecificData = invocation.toolSpecificData as IChatTerminalToolInvocationData | undefined;
 		if (!toolSpecificData) {
@@ -850,9 +938,12 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 					resultText += `\n\ The command is still running, with output:\n${pollingResult.output}`;
 				}
 
+				const endCwd = await toolTerminal.instance.getCwdResource();
 				return {
 					toolMetadata: {
-						exitCode: undefined // Background processes don't have immediate exit codes
+						exitCode: undefined, // Background processes don't have immediate exit codes
+						id: termId,
+						cwd: endCwd?.toString(),
 					},
 					content: [{
 						kind: 'text',
@@ -888,10 +979,13 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 						toolResultMessage = altBufferMessage;
 						outputLineCount = 0;
 						error = executeResult.error ?? 'alternateBuffer';
+						const altBufferCwd = await toolTerminal.instance.getCwdResource();
 						altBufferResult = {
 							toolResultMessage,
 							toolMetadata: {
-								exitCode: undefined
+								exitCode: undefined,
+								id: termId,
+								cwd: altBufferCwd?.toString(),
 							},
 							content: [{
 								kind: 'text',
@@ -1028,23 +1122,93 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 		resultText.push(terminalResult);
 
 		const isError = exitCode !== undefined && exitCode !== 0;
+		const endCwd = await toolTerminal.instance.getCwdResource();
+
+		const imageContent = await this._extractImagesFromOutput(terminalResult, endCwd);
+
 		return {
 			toolResultMessage,
 			toolMetadata: {
-				exitCode: exitCode
+				exitCode: exitCode,
+				id: termId,
+				cwd: endCwd?.toString(),
 			},
 			toolResultDetails: isError ? {
 				input: command,
 				output: [{ type: 'embed', isText: true, value: terminalResult }],
 				isError: true
 			} : undefined,
-			content: [{
-				kind: 'text',
-				value: resultText.join(''),
-			}]
+			content: [
+				{
+					kind: 'text',
+					value: resultText.join(''),
+				},
+				...imageContent,
+			]
 		};
 	}
 
+	private static readonly _maxImageFileSize = 5 * 1024 * 1024;
+
+	/**
+	 * Scans terminal output for file paths that point to images and reads them.
+	 * Returns data content parts for any found images that exist on disk.
+	 */
+	private async _extractImagesFromOutput(output: string, cwd: URI | undefined): Promise<IToolResult['content']> {
+		const normalizedOutput = output.replace(/\r?\n/g, '');
+
+		// Match paths ending with image extensions. A leading / or \ is sufficient
+		// to identify a path segment; the full path up to the extension is captured.
+		const pathPattern = /(?:[^\s]*[\/\\][^\s]*\.(?:png|jpe?g|gif|webp|bmp))/gi;
+
+		const matches = new Set<string>();
+		for (const match of normalizedOutput.matchAll(pathPattern)) {
+			matches.add(match[0]);
+		}
+
+		if (matches.size === 0) {
+			return [];
+		}
+
+		const results: IToolResult['content'] = [];
+		for (const filePath of matches) {
+			try {
+				const mimeType = getMediaMime(filePath);
+				if (!mimeType || !mimeType.startsWith('image/')) {
+					continue;
+				}
+
+				// Resolve the URI - check for absolute path (Unix / or Windows drive letter)
+				let fileUri: URI;
+				if (/^\/|^[A-Za-z]:[\\\/]/.test(filePath)) {
+					fileUri = URI.file(filePath);
+				} else if (cwd) {
+					fileUri = URI.joinPath(cwd, filePath);
+				} else {
+					continue;
+				}
+
+				const stat = await this._fileService.stat(fileUri).catch(() => undefined);
+				if (!stat || stat.isDirectory || stat.size > RunInTerminalTool._maxImageFileSize) {
+					continue;
+				}
+
+				const fileContent = await this._fileService.readFile(fileUri);
+				results.push({
+					kind: 'data',
+					value: {
+						mimeType,
+						data: fileContent.value,
+					},
+				});
+			} catch {
+				// Ignore files that can't be read
+			}
+		}
+
+		return results;
+	}
+
 	private _handleTerminalVisibility(toolTerminal: IToolTerminal, chatSessionResource: URI) {
 		const chatSessionOpenInWidget = !!this._chatWidgetService.getWidgetBySessionResource(chatSessionResource);
 		if (this._configurationService.getValue(TerminalChatAgentToolsSettingId.OutputLocation) === 'terminal' && chatSessionOpenInWidget) {
@@ -1080,7 +1244,7 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 		this._terminalChatService.registerTerminalInstanceWithToolSession(terminalToolSessionId, toolTerminal.instance);
 		this._terminalChatService.registerTerminalInstanceWithChatSession(chatSessionResource, toolTerminal.instance);
 		this._registerInputListener(toolTerminal);
-		this._sessionTerminalAssociations.set(chatSessionResource, toolTerminal);
+		this._addSessionTerminalAssociation(chatSessionResource, toolTerminal);
 		if (token.isCancellationRequested) {
 			toolTerminal.instance.dispose();
 			throw new CancellationError();
@@ -1121,7 +1285,7 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 							shellIntegrationQuality: association.shellIntegrationQuality,
 							isBackground: association.isBackground
 						};
-						this._sessionTerminalAssociations.set(chatSessionResource, toolTerminal);
+						this._addSessionTerminalAssociation(chatSessionResource, toolTerminal);
 						this._terminalChatService.registerTerminalInstanceWithChatSession(chatSessionResource, instance);
 
 						// Listen for terminal disposal to clean up storage
@@ -1192,23 +1356,96 @@ export class RunInTerminalTool extends Disposable implements IToolImpl {
 	}
 
 	private _cleanupSessionTerminals(chatSessionResource: URI): void {
+		const sessionTerminals = this._sessionTerminalInstances.get(chatSessionResource);
 		const toolTerminal = this._sessionTerminalAssociations.get(chatSessionResource);
-		if (toolTerminal) {
-			this._logService.debug(`RunInTerminalTool: Cleaning up terminal for disposed chat session ${chatSessionResource}`);
+		const terminalsToDispose = sessionTerminals ?? (toolTerminal ? new Set([toolTerminal.instance]) : undefined);
+		if (!terminalsToDispose || terminalsToDispose.size === 0) {
+			return;
+		}
 
-			this._sessionTerminalAssociations.delete(chatSessionResource);
-			toolTerminal.instance.dispose();
+		this._logService.debug(`RunInTerminalTool: Cleaning up ${terminalsToDispose.size} terminal(s) for ended chat session ${chatSessionResource}`);
 
-			// Clean up any active executions associated with this session
-			const terminalToRemove: string[] = [];
-			for (const [termId, execution] of RunInTerminalTool._activeExecutions.entries()) {
-				if (execution.instance === toolTerminal.instance) {
-					execution.dispose();
-					terminalToRemove.push(termId);
-				}
+		this._sessionTerminalAssociations.delete(chatSessionResource);
+		this._sessionTerminalInstances.delete(chatSessionResource);
+		this._sessionDeniedCommandCounts.delete(chatSessionResource);
+
+		for (const terminal of terminalsToDispose) {
+			// Skip redundant map walks in onDidDispose since this session has already been removed.
+			this._terminalsBeingDisposedBySessionCleanup.add(terminal);
+			terminal.dispose();
+		}
+
+		// Clean up any active executions associated with this session
+		const terminalToRemove: string[] = [];
+		for (const [termId, execution] of RunInTerminalTool._activeExecutions.entries()) {
+			if (terminalsToDispose.has(execution.instance)) {
+				execution.dispose();
+				terminalToRemove.push(termId);
 			}
-			for (const termId of terminalToRemove) {
-				RunInTerminalTool._activeExecutions.delete(termId);
+		}
+		for (const termId of terminalToRemove) {
+			RunInTerminalTool._activeExecutions.delete(termId);
+		}
+	}
+
+	private _recordDeniedCommandAttempt(chatSessionResource: URI, denial: DenialDetails): number {
+		let sessionCounts = this._sessionDeniedCommandCounts.get(chatSessionResource);
+		if (!sessionCounts) {
+			sessionCounts = new Map<string, number>();
+			this._sessionDeniedCommandCounts.set(chatSessionResource, sessionCounts);
+		}
+		const signature = JSON.stringify([denial.scope, denial.deniedCommand, denial.ruleSourceText ?? denial.reason]);
+		const attempts = (sessionCounts.get(signature) ?? 0) + 1;
+		sessionCounts.set(signature, attempts);
+		return attempts;
+	}
+
+	private _addSessionTerminalAssociation(chatSessionResource: URI, toolTerminal: IToolTerminal): void {
+		this._ensureArchivedSessionListener();
+
+		let sessionTerminals = this._sessionTerminalInstances.get(chatSessionResource);
+		if (!sessionTerminals) {
+			sessionTerminals = new Set<ITerminalInstance>();
+			this._sessionTerminalInstances.set(chatSessionResource, sessionTerminals);
+		}
+		sessionTerminals.add(toolTerminal.instance);
+
+		if (!toolTerminal.isBackground) {
+			this._sessionTerminalAssociations.set(chatSessionResource, toolTerminal);
+		}
+	}
+
+	private _ensureArchivedSessionListener(): void {
+		if (this._archivedSessionListener.value) {
+			return;
+		}
+
+		// Archiving a session does not fire onDidDisposeSession, but we still need to dispose
+		// any terminals associated with the archived session to avoid process accumulation.
+		this._archivedSessionListener.value = this._agentSessionsService.onDidChangeSessionArchivedState(session => {
+			if (session.isArchived()) {
+				this._cleanupSessionTerminals(session.resource);
+			}
+		});
+	}
+
+	private _removeTerminalAssociations(terminal: ITerminalInstance): void {
+		if (this._terminalsBeingDisposedBySessionCleanup.delete(terminal)) {
+			return;
+		}
+
+		for (const [sessionResource, toolTerminal] of this._sessionTerminalAssociations.entries()) {
+			if (terminal === toolTerminal.instance) {
+				this._sessionTerminalAssociations.delete(sessionResource);
+			}
+		}
+
+		for (const [sessionResource, sessionTerminals] of this._sessionTerminalInstances.entries()) {
+			if (!sessionTerminals.delete(terminal)) {
+				continue;
+			}
+			if (sessionTerminals.size === 0) {
+				this._sessionTerminalInstances.delete(sessionResource);
 			}
 		}
 	}
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/sandboxOutputAnalyzer.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/sandboxOutputAnalyzer.ts
index adb2d2dd24e92..f83f92f3abd30 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/sandboxOutputAnalyzer.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/browser/tools/sandboxOutputAnalyzer.ts
@@ -3,14 +3,20 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { posix } from '../../../../../../base/common/path.js';
+import { URI } from '../../../../../../base/common/uri.js';
 import { localize } from '../../../../../../nls.js';
 import { Disposable } from '../../../../../../base/common/lifecycle.js';
+import { IFileService } from '../../../../../../platform/files/common/files.js';
 import { ITerminalSandboxService } from '../../common/terminalSandboxService.js';
 import type { IOutputAnalyzer, IOutputAnalyzerOptions } from './outputAnalyzer.js';
 import { TerminalChatAgentToolsSettingId } from '../../common/terminalChatAgentToolsConfiguration.js';
 
 export class SandboxOutputAnalyzer extends Disposable implements IOutputAnalyzer {
+	private static readonly _filesystemPermissionPattern = /(?:\b(?:EACCES|EPERM|ENOENT|EROFS|fail(?:ed|ure)?)\b|not accessible|read[- ]only|fatal:)/i;
+
 	constructor(
+		@IFileService private readonly _fileService: IFileService,
 		@ITerminalSandboxService private readonly _sandboxService: ITerminalSandboxService,
 	) {
 		super();
@@ -24,6 +30,18 @@ export class SandboxOutputAnalyzer extends Disposable implements IOutputAnalyzer
 			return undefined;
 		}
 
+		const filesystemPermissionLine = options.exitResult.split(/\r?\n/).find(line => SandboxOutputAnalyzer._filesystemPermissionPattern.test(line));
+		const sandboxPath = filesystemPermissionLine ? await this._getSandboxPathToAllow(filesystemPermissionLine) : undefined;
+
+		if (sandboxPath && await this._sandboxService.promptToAllowWritePath(sandboxPath)) {
+			return localize(
+				'runInTerminalTool.sandboxWritePathAllowed',
+				"Write access to {0} was added to the terminal sandbox allow list. Retry the command.",
+				sandboxPath
+			);
+		}
+
+
 		return localize(
 			'runInTerminalTool.sandboxCommandFailed',
 			"Command failed while running in sandboxed mode. Use the command result to determine the scenario. If the issue is filesystem permissions, update allowWrite in {0} (Linux) or {1} (macOS). If the issue is domain/network related, add the required domains to {2}.allowedDomains.",
@@ -32,4 +50,43 @@ export class SandboxOutputAnalyzer extends Disposable implements IOutputAnalyzer
 			TerminalChatAgentToolsSettingId.TerminalSandboxNetwork
 		);
 	}
+
+	private _extractSandboxPath(line: string): string | undefined {
+		// Matches paths wrapped in square brackets, e.g. "[/tmp/file.txt]".
+		const bracketedPath = line.match(/\[(\/[^\]\r\n]+)\]/);
+		if (bracketedPath?.[1]) {
+			return bracketedPath[1].trim();
+		}
+
+		// Matches quoted absolute paths, e.g. "'/tmp/file.txt'" or '"/tmp/file.txt"'.
+		const quotedPath = line.match(/["'`](\/.+?)["'`]/);
+		if (quotedPath?.[1]) {
+			return quotedPath[1];
+		}
+
+		// Matches unquoted absolute paths followed by ": " message text, plain whitespace text,
+		// or end of line, e.g. "/home/user/file.txt: Warning..." or "/home/user/file.txt Warning...".
+		const inlinePath = line.match(/(\/[^\s:\r\n]+)(?=:\s|\s|$)/);
+		if (inlinePath?.[1]) {
+			return inlinePath[1].trim();
+		}
+
+		// Matches a trailing absolute path at the end of the line, e.g. "... open /tmp/file.txt".
+		const trailingPath = line.match(/(\/[\w.\-~/ ]+)$/);
+		return trailingPath?.[1]?.trim();
+	}
+
+	private async _getSandboxPathToAllow(line: string): Promise<string | undefined> {
+		const extractedPath = this._extractSandboxPath(line);
+		if (!extractedPath) {
+			return undefined;
+		}
+
+		if (await this._fileService.exists(URI.file(extractedPath))) {
+			return extractedPath;
+		}
+
+		const parentPath = posix.dirname(extractedPath);
+		return parentPath && parentPath !== extractedPath ? parentPath : extractedPath;
+	}
 }
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/common/terminalChatAgentToolsConfiguration.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/common/terminalChatAgentToolsConfiguration.ts
index aafc4af0856d6..f50dfea219f57 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/common/terminalChatAgentToolsConfiguration.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/common/terminalChatAgentToolsConfiguration.ts
@@ -519,6 +519,9 @@ export const terminalChatAgentToolsConfiguration: IStringDictionary<IConfigurati
 		default: false,
 		tags: ['preview'],
 		restricted: true,
+		experiment: {
+			mode: 'auto'
+		}
 	},
 	[TerminalChatAgentToolsSettingId.TerminalSandboxNetwork]: {
 		markdownDescription: localize('terminalSandbox.networkSetting', "Note: this setting is applicable only when {0} is enabled. Controls network access in the terminal sandbox.", `\`#${TerminalChatAgentToolsSettingId.TerminalSandboxEnabled}#\``),
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/common/terminalSandboxService.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/common/terminalSandboxService.ts
index 54d5a7899a809..17b71ff1030b6 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/common/terminalSandboxService.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/common/terminalSandboxService.ts
@@ -3,82 +3,68 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { VSBuffer } from '../../../../../base/common/buffer.js';
 import { Event } from '../../../../../base/common/event.js';
-import { Disposable } from '../../../../../base/common/lifecycle.js';
-import { FileAccess } from '../../../../../base/common/network.js';
-import { dirname, posix, win32 } from '../../../../../base/common/path.js';
+import { Disposable, MutableDisposable } from '../../../../../base/common/lifecycle.js';
 import { OperatingSystem, OS } from '../../../../../base/common/platform.js';
-import { URI } from '../../../../../base/common/uri.js';
-import { generateUuid } from '../../../../../base/common/uuid.js';
-import { IConfigurationChangeEvent, IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
-import { IEnvironmentService } from '../../../../../platform/environment/common/environment.js';
-import { IFileService } from '../../../../../platform/files/common/files.js';
+import { ConfigurationTarget, IConfigurationChangeEvent, IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
+import { IDialogService } from '../../../../../platform/dialogs/common/dialogs.js';
 import { createDecorator } from '../../../../../platform/instantiation/common/instantiation.js';
 import { ILogService } from '../../../../../platform/log/common/log.js';
+import { IWorkspaceContextService } from '../../../../../platform/workspace/common/workspace.js';
+import { ProxyChannel } from '../../../../../base/parts/ipc/common/ipc.js';
+import { SandboxHelperChannelName, type ISandboxPermissionRequest, type ISandboxRuntimeConfig } from '../../../../../platform/sandbox/common/sandboxHelperIpc.js';
+import { ISandboxHelperService } from '../../../../../platform/sandbox/common/sandboxHelperService.js';
 import { ITerminalSandboxNetworkSettings } from './terminalSandbox.js';
 import { IRemoteAgentService } from '../../../../services/remote/common/remoteAgentService.js';
 import { TerminalChatAgentToolsSettingId } from './terminalChatAgentToolsConfiguration.js';
 import { IRemoteAgentEnvironment } from '../../../../../platform/remote/common/remoteAgentEnvironment.js';
 import { ITrustedDomainService } from '../../../url/common/trustedDomainService.js';
+import { localize } from '../../../../../nls.js';
+
+type ISandboxHelperChannel = {
+	readonly onDidRequestSandboxPermission: Event<ISandboxPermissionRequest>;
+	resetSandbox(): Promise<void>;
+	resolveSandboxPermissionRequest(requestId: string, allowed: boolean): Promise<void>;
+	wrapWithSandbox(runtimeConfig: ISandboxRuntimeConfig, command: string): Promise<string>;
+};
 
 export const ITerminalSandboxService = createDecorator<ITerminalSandboxService>('terminalSandboxService');
 
 export interface ITerminalSandboxService {
 	readonly _serviceBrand: undefined;
 	isEnabled(): Promise<boolean>;
-	wrapCommand(command: string): string;
-	getSandboxConfigPath(forceRefresh?: boolean): Promise<string | undefined>;
-	getTempDir(): URI | undefined;
-	setNeedsForceUpdateConfigFile(): void;
+	promptToAllowWritePath(path: string): Promise<boolean>;
+	wrapWithSandbox(runtimeConfig: ISandboxRuntimeConfig, command: string): Promise<string>;
+	wrapCommand(command: string): Promise<string>;
 }
 
+type ITerminalSandboxFilesystemSettings = {
+	denyRead?: string[];
+	allowWrite?: string[];
+	denyWrite?: string[];
+};
+
 export class TerminalSandboxService extends Disposable implements ITerminalSandboxService {
 	readonly _serviceBrand: undefined;
-	private _srtPath: string | undefined;
-	private _rgPath: string | undefined;
-	private _srtPathResolved = false;
-	private _execPath?: string;
-	private _sandboxConfigPath: string | undefined;
-	private _needsForceUpdateConfigFile = true;
-	private _tempDir: URI | undefined;
-	private _sandboxSettingsId: string | undefined;
 	private _remoteEnvDetailsPromise: Promise<IRemoteAgentEnvironment | null>;
 	private _remoteEnvDetails: IRemoteAgentEnvironment | null = null;
-	private _appRoot: string;
 	private _os: OperatingSystem = OS;
+	private _defaultWritePaths: string[] = ['~/.npm'];
+	private readonly _sandboxPermissionRequestListener = this._register(new MutableDisposable());
+	private _sandboxHelperSource: string | undefined;
 
 	constructor(
 		@IConfigurationService private readonly _configurationService: IConfigurationService,
-		@IFileService private readonly _fileService: IFileService,
-		@IEnvironmentService private readonly _environmentService: IEnvironmentService,
+		@IDialogService private readonly _dialogService: IDialogService,
 		@ILogService private readonly _logService: ILogService,
+		@IWorkspaceContextService private readonly _workspaceContextService: IWorkspaceContextService,
 		@IRemoteAgentService private readonly _remoteAgentService: IRemoteAgentService,
+		@ISandboxHelperService private readonly _localSandboxHelperService: ISandboxHelperService,
 		@ITrustedDomainService private readonly _trustedDomainService: ITrustedDomainService,
 	) {
 		super();
-		this._appRoot = dirname(FileAccess.asFileUri('').path);
-		// Get the node executable path from native environment service if available (Electron's execPath with ELECTRON_RUN_AS_NODE)
-		const nativeEnv = this._environmentService as IEnvironmentService & { execPath?: string };
-		this._execPath = nativeEnv.execPath;
-		this._sandboxSettingsId = generateUuid();
 		this._remoteEnvDetailsPromise = this._remoteAgentService.getEnvironment();
-
-		this._register(Event.runAndSubscribe(this._configurationService.onDidChangeConfiguration, (e: IConfigurationChangeEvent | undefined) => {
-			// If terminal sandbox settings changed, update sandbox config.
-			if (
-				e?.affectsConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxEnabled) ||
-				e?.affectsConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxNetwork) ||
-				e?.affectsConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxLinuxFileSystem) ||
-				e?.affectsConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxMacFileSystem)
-			) {
-				this.setNeedsForceUpdateConfigFile();
-			}
-		}));
-
-		this._register(this._trustedDomainService.onDidChangeTrustedDomains(() => {
-			this.setNeedsForceUpdateConfigFile();
-		}));
+		this._register(this._configurationService.onDidChangeConfiguration(e => this._handleSandboxConfigurationChange(e)));
 	}
 
 	public async isEnabled(): Promise<boolean> {
@@ -90,125 +76,220 @@ export class TerminalSandboxService extends Disposable implements ITerminalSandb
 		return this._configurationService.getValue<boolean>(TerminalChatAgentToolsSettingId.TerminalSandboxEnabled);
 	}
 
-	public wrapCommand(command: string): string {
-		if (!this._sandboxConfigPath || !this._tempDir) {
-			throw new Error('Sandbox config path or temp dir not initialized');
+	public async wrapWithSandbox(runtimeConfig: ISandboxRuntimeConfig, command: string): Promise<string> {
+		try {
+			const service = this._getSandboxHelperService();
+			return service.wrapWithSandbox(runtimeConfig, command);
+		} catch (error) {
+			this._logService.error('TerminalSandboxService: Failed to wrap command with sandbox', error);
+			return command;
 		}
-		if (!this._execPath) {
-			throw new Error('Executable path not set to run sandbox commands');
+	}
+
+	public async promptToAllowWritePath(path: string): Promise<boolean> {
+		if (!(await this.isEnabled())) {
+			return false;
 		}
-		if (!this._srtPath) {
-			throw new Error('Sandbox runtime path not resolved');
+
+		const sandboxPath = path.trim();
+		const settingsKey = this._getFileSystemSettingsKey();
+		if (!sandboxPath || !settingsKey) {
+			return false;
 		}
-		if (!this._rgPath) {
-			throw new Error('Ripgrep path not resolved');
+
+		const target = this._getSandboxConfigurationTarget();
+		const inspectedValue = this._configurationService.inspect<ITerminalSandboxFilesystemSettings>(settingsKey);
+		const currentSettings = target === ConfigurationTarget.USER_REMOTE ? inspectedValue.userRemoteValue : inspectedValue.userValue;
+		const allowWrite = new Set(currentSettings?.allowWrite ?? []);
+		const denyWrite = currentSettings?.denyWrite ?? [];
+
+		if (allowWrite.has(sandboxPath) && !denyWrite.includes(sandboxPath)) {
+			return false;
 		}
-		// Use ELECTRON_RUN_AS_NODE=1 to make Electron executable behave as Node.js
-		// TMPDIR must be set as environment variable before the command
-		// Use -c to pass the command string directly (like sh -c), avoiding argument parsing issues
-		const wrappedCommand = `PATH="$PATH:${dirname(this._rgPath)}" TMPDIR="${this._tempDir.path}" "${this._execPath}" "${this._srtPath}" --settings "${this._sandboxConfigPath}" -c "${command}"`;
-		if (this._remoteEnvDetails) {
-			return `${wrappedCommand}`;
+
+		const { confirmed } = await this._dialogService.confirm({
+			type: 'warning',
+			message: localize('terminalSandboxAllowWritePathMessage', "Allow Sandboxed File Write?"),
+			detail: localize('terminalSandboxAllowWritePathDetail', "The sandboxed terminal command was blocked from writing to {0}. Add this path to {1}.allowWrite?", sandboxPath, settingsKey),
+			primaryButton: localize('terminalSandboxAllowWritePathPrimary', "&&Allow"),
+			cancelButton: localize('terminalSandboxAllowWritePathCancel', "&&Deny")
+		});
+
+		if (!confirmed) {
+			return false;
 		}
-		return `ELECTRON_RUN_AS_NODE=1 ${wrappedCommand}`;
-	}
 
-	public getTempDir(): URI | undefined {
-		return this._tempDir;
+		allowWrite.add(sandboxPath);
+		await this._configurationService.updateValue(settingsKey, {
+			...currentSettings,
+			allowWrite: Array.from(allowWrite),
+			denyWrite: denyWrite.filter(value => value !== sandboxPath),
+		}, target);
+		return true;
 	}
 
-	public setNeedsForceUpdateConfigFile(): void {
-		this._needsForceUpdateConfigFile = true;
+	public async promptForSandboxPermission(request: ISandboxPermissionRequest): Promise<boolean> {
+		const target = request.port === undefined ? request.host : `${request.host}:${request.port}`;
+		const { confirmed } = await this._dialogService.confirm({
+			type: 'warning',
+			message: localize('terminalSandboxPermissionRequestMessage', "Allow Sandboxed Network Access?"),
+			detail: localize('terminalSandboxPermissionRequestDetail', "The sandboxed terminal command requested access to {0}.", target),
+			primaryButton: localize('terminalSandboxPermissionAllow', "&&Allow"),
+			cancelButton: localize('terminalSandboxPermissionDeny', "&&Deny")
+		});
+
+		return confirmed;
 	}
 
-	public async getSandboxConfigPath(forceRefresh: boolean = false): Promise<string | undefined> {
-		await this._resolveSrtPath();
-		if (!this._sandboxConfigPath || forceRefresh || this._needsForceUpdateConfigFile) {
-			this._sandboxConfigPath = await this._createSandboxConfig();
-			this._needsForceUpdateConfigFile = false;
+	public async wrapCommand(command: string): Promise<string> {
+		const sandboxSettings = await this._getSandboxSettings();
+		if (!sandboxSettings) {
+			throw new Error('Sandbox settings not initialized');
 		}
-		return this._sandboxConfigPath;
+
+		return this.wrapWithSandbox(sandboxSettings, command);
+	}
+
+	private async _resetSandbox(): Promise<void> {
+		const service = this._getSandboxHelperService();
+		await service.resetSandbox();
 	}
 
-	private async _resolveSrtPath(): Promise<void> {
-		if (this._srtPathResolved) {
+	private _handleSandboxConfigurationChange(e: IConfigurationChangeEvent): void {
+		if (!this._affectsSandboxConfiguration(e)) {
 			return;
 		}
-		this._srtPathResolved = true;
-		const remoteEnv = this._remoteEnvDetails || await this._remoteEnvDetailsPromise;
-		if (remoteEnv) {
 
-			this._appRoot = remoteEnv.appRoot.path;
-			this._execPath = this._pathJoin(this._appRoot, 'node');
-		}
-		this._srtPath = this._pathJoin(this._appRoot, 'node_modules', '@anthropic-ai', 'sandbox-runtime', 'dist', 'cli.js');
-		this._rgPath = this._pathJoin(this._appRoot, 'node_modules', '@vscode', 'ripgrep', 'bin', 'rg');
+		this._resetSandbox().catch(error => {
+			this._logService.error('TerminalSandboxService: Failed to reset sandbox after configuration change', error);
+		});
 	}
 
-	private async _createSandboxConfig(): Promise<string | undefined> {
+	private async _getSandboxSettings(): Promise<ISandboxRuntimeConfig | undefined> {
+		const networkSetting = this._configurationService.getValue<ITerminalSandboxNetworkSettings>(TerminalChatAgentToolsSettingId.TerminalSandboxNetwork) ?? {};
+		const linuxFileSystemSetting = this._os === OperatingSystem.Linux
+			? this._configurationService.getValue<ITerminalSandboxFilesystemSettings>(TerminalChatAgentToolsSettingId.TerminalSandboxLinuxFileSystem) ?? {}
+			: {};
+		const macFileSystemSetting = this._os === OperatingSystem.Macintosh
+			? this._configurationService.getValue<ITerminalSandboxFilesystemSettings>(TerminalChatAgentToolsSettingId.TerminalSandboxMacFileSystem) ?? {}
+			: {};
+		const linuxAllowWrite = this._resolveAllowWritePaths(linuxFileSystemSetting.allowWrite);
+		const macAllowWrite = this._resolveAllowWritePaths(macFileSystemSetting.allowWrite);
 
-		if (await this.isEnabled() && !this._tempDir) {
-			await this._initTempDir();
+		let allowedDomains = networkSetting.allowedDomains ?? [];
+		if (networkSetting.allowTrustedDomains) {
+			allowedDomains = this._addTrustedDomainsToAllowedDomains(allowedDomains);
 		}
-		if (this._tempDir) {
-			const networkSetting = this._configurationService.getValue<ITerminalSandboxNetworkSettings>(TerminalChatAgentToolsSettingId.TerminalSandboxNetwork) ?? {};
-			const linuxFileSystemSetting = this._os === OperatingSystem.Linux
-				? this._configurationService.getValue<{ denyRead?: string[]; allowWrite?: string[]; denyWrite?: string[] }>(TerminalChatAgentToolsSettingId.TerminalSandboxLinuxFileSystem) ?? {}
-				: {};
-			const macFileSystemSetting = this._os === OperatingSystem.Macintosh
-				? this._configurationService.getValue<{ denyRead?: string[]; allowWrite?: string[]; denyWrite?: string[] }>(TerminalChatAgentToolsSettingId.TerminalSandboxMacFileSystem) ?? {}
-				: {};
-			const configFileUri = URI.joinPath(this._tempDir, `vscode-sandbox-settings-${this._sandboxSettingsId}.json`);
 
-			const allowedDomainsSet = new Set(networkSetting.allowedDomains ?? []);
-			if (networkSetting.allowTrustedDomains) {
-				for (const domain of this._trustedDomainService.trustedDomains) {
-					// Filter out sole wildcard '*' as sandbox runtime doesn't allow it
-					// Wildcards like '*.github.com' are OK
-					if (domain !== '*') {
-						allowedDomainsSet.add(domain);
-					}
-				}
+		return {
+			network: {
+				allowedDomains,
+				deniedDomains: networkSetting.deniedDomains ?? []
+			},
+			filesystem: {
+				denyRead: (this._os === OperatingSystem.Macintosh ? macFileSystemSetting.denyRead : linuxFileSystemSetting.denyRead) || [],
+				allowWrite: (this._os === OperatingSystem.Macintosh ? macAllowWrite : linuxAllowWrite) || [],
+				denyWrite: (this._os === OperatingSystem.Macintosh ? macFileSystemSetting.denyWrite : linuxFileSystemSetting.denyWrite) || [],
 			}
-			const allowedDomains = Array.from(allowedDomainsSet);
-
-			const sandboxSettings = {
-				network: {
-					allowedDomains,
-					deniedDomains: networkSetting.deniedDomains ?? []
-				},
-				filesystem: {
-					denyRead: this._os === OperatingSystem.Macintosh ? macFileSystemSetting.denyRead : linuxFileSystemSetting.denyRead,
-					allowWrite: this._os === OperatingSystem.Macintosh ? macFileSystemSetting.allowWrite : linuxFileSystemSetting.allowWrite,
-					denyWrite: this._os === OperatingSystem.Macintosh ? macFileSystemSetting.denyWrite : linuxFileSystemSetting.denyWrite,
+		};
+	}
+
+	private _resolveAllowWritePaths(configuredAllowWrite: string[] | undefined): string[] {
+		const workspaceFolderPaths = this._workspaceContextService.getWorkspace().folders.map(folder => folder.uri.path);
+		return [...new Set([...workspaceFolderPaths, ...this._defaultWritePaths, ...(configuredAllowWrite ?? [])])];
+	}
+
+	private _addTrustedDomainsToAllowedDomains(allowedDomains: string[]): string[] {
+		const allowedDomainsSet = new Set(allowedDomains);
+		for (const domain of this._trustedDomainService.trustedDomains) {
+			try {
+				const uri = new URL(domain);
+				allowedDomainsSet.add(uri.hostname);
+			} catch {
+				if (domain !== '*') {
+					allowedDomainsSet.add(domain);
 				}
-			};
-			this._sandboxConfigPath = configFileUri.path;
-			await this._fileService.createFile(configFileUri, VSBuffer.fromString(JSON.stringify(sandboxSettings, null, '\t')), { overwrite: true });
-			return this._sandboxConfigPath;
+			}
+		}
+		return Array.from(allowedDomainsSet);
+	}
+
+	private _getSandboxConfigurationTarget(): ConfigurationTarget {
+		return this._remoteAgentService.getConnection() ? ConfigurationTarget.USER_REMOTE : ConfigurationTarget.USER;
+	}
+
+	private _affectsSandboxConfiguration(e: IConfigurationChangeEvent): boolean {
+		return e.affectsConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxEnabled)
+			|| e.affectsConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxNetwork)
+			|| e.affectsConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxLinuxFileSystem)
+			|| e.affectsConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxMacFileSystem);
+	}
+
+	private _getFileSystemSettingsKey(): string | undefined {
+		if (this._os === OperatingSystem.Linux) {
+			return TerminalChatAgentToolsSettingId.TerminalSandboxLinuxFileSystem;
+		}
+
+		if (this._os === OperatingSystem.Macintosh) {
+			return TerminalChatAgentToolsSettingId.TerminalSandboxMacFileSystem;
 		}
+
 		return undefined;
 	}
 
-	// Joins path segments according to the current OS.
-	private _pathJoin = (...segments: string[]) => {
-		const path = this._os === OperatingSystem.Windows ? win32 : posix;
-		return path.join(...segments);
-	};
-
-	private async _initTempDir(): Promise<void> {
-		if (await this.isEnabled()) {
-			this._needsForceUpdateConfigFile = true;
-			const remoteEnv = this._remoteEnvDetails || await this._remoteEnvDetailsPromise;
-			if (remoteEnv) {
-				this._tempDir = remoteEnv.tmpDir;
-			} else {
-				const environmentService = this._environmentService as IEnvironmentService & { tmpDir?: URI };
-				this._tempDir = environmentService.tmpDir;
-			}
-			if (!this._tempDir) {
-				this._logService.warn('TerminalSandboxService: Cannot create sandbox settings file because no tmpDir is available in this environment');
+	private _getSandboxHelperService(): ISandboxHelperChannel {
+		const connection = this._remoteAgentService.getConnection();
+		const service = connection
+			? ProxyChannel.toService<ISandboxHelperChannel>(connection.getChannel(SandboxHelperChannelName))
+			: this._localSandboxHelperService;
+		const source = connection ? `remote:${connection.remoteAuthority}` : 'local';
+
+		if (this._sandboxHelperSource !== source) {
+			this._sandboxHelperSource = source;
+			this._sandboxPermissionRequestListener.value = service.onDidRequestSandboxPermission(request => {
+				void this._handleSandboxPermissionRequest(service, request);
+			});
+		}
+
+		return service;
+	}
+
+	private async _handleSandboxPermissionRequest(service: ISandboxHelperChannel, request: ISandboxPermissionRequest): Promise<void> {
+		let allowed = false;
+
+		try {
+			allowed = await this.promptForSandboxPermission(request);
+			if (allowed) {
+				await this._persistAllowedSandboxDomain(request.host);
 			}
+		} catch (error) {
+			this._logService.error('TerminalSandboxService: Failed to prompt for sandbox permission', error);
 		}
+
+		try {
+			await service.resolveSandboxPermissionRequest(request.requestId, allowed);
+		} catch (error) {
+			this._logService.error('TerminalSandboxService: Failed to resolve sandbox permission request', error);
+		}
+	}
+
+	private async _persistAllowedSandboxDomain(host: string): Promise<void> {
+		const target = this._getSandboxConfigurationTarget();
+		const inspectedValue = this._configurationService.inspect<ITerminalSandboxNetworkSettings>(TerminalChatAgentToolsSettingId.TerminalSandboxNetwork);
+		const currentSettings = target === ConfigurationTarget.USER_REMOTE ? inspectedValue.userRemoteValue : inspectedValue.userValue;
+		const allowedDomains = new Set(currentSettings?.allowedDomains ?? []);
+		const deniedDomains = (currentSettings?.deniedDomains ?? []).filter(domain => domain !== host);
+
+		if (allowedDomains.has(host) && deniedDomains.length === (currentSettings?.deniedDomains ?? []).length) {
+			return;
+		}
+
+		allowedDomains.add(host);
+
+		await this._configurationService.updateValue(TerminalChatAgentToolsSettingId.TerminalSandboxNetwork, {
+			...currentSettings,
+			allowedDomains: Array.from(allowedDomains),
+			deniedDomains,
+		}, target);
 	}
 }
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/outputMonitor.test.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/outputMonitor.test.ts
index cb4aa2c1dc081..f4f34ecd4e943 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/outputMonitor.test.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/outputMonitor.test.ts
@@ -5,7 +5,7 @@
 
 import * as assert from 'assert';
 import { detectsGenericPressAnyKeyPattern, detectsInputRequiredPattern, detectsNonInteractiveHelpPattern, detectsVSCodeTaskFinishMessage, matchTerminalPromptOption, OutputMonitor } from '../../browser/tools/monitoring/outputMonitor.js';
-import { CancellationTokenSource } from '../../../../../../base/common/cancellation.js';
+import { CancellationToken, CancellationTokenSource } from '../../../../../../base/common/cancellation.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
 import { IExecution, IPollingResult, OutputMonitorState } from '../../browser/tools/monitoring/types.js';
 import { TestInstantiationService } from '../../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
@@ -19,6 +19,10 @@ import { runWithFakedTimers } from '../../../../../../base/test/common/timeTrave
 import { IToolInvocationContext } from '../../../../chat/common/tools/languageModelToolsService.js';
 import { LocalChatSessionUri } from '../../../../chat/common/model/chatUri.js';
 import { isNumber } from '../../../../../../base/common/types.js';
+import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
+import { TestConfigurationService } from '../../../../../../platform/configuration/test/common/testConfigurationService.js';
+import { TerminalChatAgentToolsSettingId } from '../../common/terminalChatAgentToolsConfiguration.js';
+import { IChatWidgetService } from '../../../../chat/browser/chat.js';
 
 suite('OutputMonitor', () => {
 	const store = ensureNoDisposablesAreLeakedInTestSuite();
@@ -27,17 +31,22 @@ suite('OutputMonitor', () => {
 	let cts: CancellationTokenSource;
 	let instantiationService: TestInstantiationService;
 	let sendTextCalled: boolean;
+	let sentText: string | undefined;
 	let dataEmitter: Emitter<string>;
 
 	setup(() => {
 		sendTextCalled = false;
+		sentText = undefined;
 		dataEmitter = new Emitter<string>();
 		execution = {
 			getOutput: () => 'test output',
 			isActive: async () => false,
 			instance: {
 				instanceId: 1,
-				sendText: async () => { sendTextCalled = true; },
+				sendText: async (text?: string) => {
+					sendTextCalled = true;
+					sentText = text;
+				},
 				onDidInputData: dataEmitter.event,
 				onDisposed: Event.None,
 				onData: dataEmitter.event,
@@ -73,6 +82,12 @@ suite('OutputMonitor', () => {
 			}
 		);
 		instantiationService.stub(ITerminalLogService, new NullLogService());
+		instantiationService.stub(IConfigurationService, new TestConfigurationService({
+			[TerminalChatAgentToolsSettingId.AutoReplyToPrompts]: false
+		}));
+		instantiationService.stub(IChatWidgetService, {
+			getWidgetsByLocations: () => []
+		});
 		cts = new CancellationTokenSource();
 	});
 
@@ -204,6 +219,131 @@ suite('OutputMonitor', () => {
 		});
 	});
 
+	test('auto reply sends first option when model lookup is unavailable', async () => {
+		instantiationService.stub(IConfigurationService, new TestConfigurationService({
+			[TerminalChatAgentToolsSettingId.AutoReplyToPrompts]: true
+		}));
+		instantiationService.stub(ILanguageModelsService, {
+			selectLanguageModels: async () => []
+		});
+
+		const monitorCts = new CancellationTokenSource();
+		monitorCts.cancel();
+		monitor = store.add(instantiationService.createInstance(OutputMonitor, execution, undefined, createTestContext('1'), monitorCts.token, 'test command'));
+
+		const outputMonitorWithPrivateMethod = monitor as unknown as {
+			[key: string]: ((prompt: { prompt: string; options: string[]; detectedRequestForFreeFormInput: boolean }, token: CancellationToken) => Promise<{ suggestedOption: string | { description: string; option: string }; sentToTerminal: boolean } | undefined>) | undefined;
+		};
+		const optionResult = await outputMonitorWithPrivateMethod['_selectAndHandleOption']!({
+			prompt: 'Continue?',
+			options: ['y', 'n'],
+			detectedRequestForFreeFormInput: false
+		}, CancellationToken.None);
+		await Event.toPromise(monitor.onDidFinishCommand);
+		monitorCts.dispose();
+
+		assert.strictEqual(sendTextCalled, true, 'sendText should be called when auto reply is enabled');
+		assert.strictEqual(optionResult?.sentToTerminal, true, 'option should be auto-sent');
+		assert.strictEqual(optionResult?.suggestedOption, 'y', 'first option should be used as fallback');
+	});
+
+	test('auto reply uses fallback model to derive suggested option', async () => {
+		instantiationService.stub(IConfigurationService, new TestConfigurationService({
+			[TerminalChatAgentToolsSettingId.AutoReplyToPrompts]: true
+		}));
+
+		let fallbackModelRequested = false;
+		instantiationService.stub(ILanguageModelsService, {
+			selectLanguageModels: async (selector: { id?: string }) => {
+				if (selector.id === 'copilot-fast') {
+					fallbackModelRequested = true;
+					return ['copilot-fast'];
+				}
+				return [];
+			},
+			sendChatRequest: async () => ({
+				stream: (async function* () {
+					yield { type: 'text', value: 'n' };
+				})(),
+				result: Promise.resolve(undefined)
+			})
+		});
+
+		const monitorCts = new CancellationTokenSource();
+		monitorCts.cancel();
+		monitor = store.add(instantiationService.createInstance(OutputMonitor, execution, undefined, createTestContext('1'), monitorCts.token, 'test command'));
+
+		const outputMonitorWithPrivateMethod = monitor as unknown as {
+			[key: string]: ((prompt: { prompt: string; options: string[]; detectedRequestForFreeFormInput: boolean }, token: CancellationToken) => Promise<{ suggestedOption: string | { description: string; option: string }; sentToTerminal: boolean } | undefined>) | undefined;
+		};
+		const optionResult = await outputMonitorWithPrivateMethod['_selectAndHandleOption']!({
+			prompt: 'Continue?',
+			options: ['y', 'n'],
+			detectedRequestForFreeFormInput: false
+		}, CancellationToken.None);
+		await Event.toPromise(monitor.onDidFinishCommand);
+		monitorCts.dispose();
+
+		assert.strictEqual(fallbackModelRequested, true, 'fallback model should be requested via _getLanguageModel');
+		assert.strictEqual(sendTextCalled, true, 'sendText should be called when auto reply is enabled');
+		assert.strictEqual(optionResult?.sentToTerminal, true, 'option should be auto-sent');
+		assert.strictEqual(optionResult?.suggestedOption, 'n', 'suggested option should be derived from fallback model response');
+	});
+
+	test('auto reply stops on generic press any key prompts', async () => {
+		instantiationService.stub(IConfigurationService, new TestConfigurationService({
+			[TerminalChatAgentToolsSettingId.AutoReplyToPrompts]: true
+		}));
+
+		execution.getOutput = () => 'Press any key to continue...';
+		const monitorCts = new CancellationTokenSource();
+		monitorCts.cancel();
+		monitor = store.add(instantiationService.createInstance(OutputMonitor, execution, undefined, createTestContext('1'), monitorCts.token, 'test command'));
+
+		const outputMonitorWithPrivateMethod = monitor as unknown as {
+			[key: string]: ((token: CancellationToken) => Promise<{ shouldContinuePollling: boolean }>) | undefined;
+		};
+		const idleResult = await outputMonitorWithPrivateMethod['_handleIdleState']!(CancellationToken.None);
+		await Event.toPromise(monitor.onDidFinishCommand);
+		monitorCts.dispose();
+
+		assert.strictEqual(sendTextCalled, false, 'sendText should not be called when auto reply is enabled for free-form prompts');
+		assert.strictEqual(sentText, undefined, 'no terminal input should be sent');
+		assert.strictEqual(idleResult.shouldContinuePollling, false, 'monitor should stop polling for free-form prompts in auto reply mode');
+	});
+
+	test('auto reply does not propagate free-form input requests without explicit input', async () => {
+		instantiationService.stub(IConfigurationService, new TestConfigurationService({
+			[TerminalChatAgentToolsSettingId.AutoReplyToPrompts]: true
+		}));
+
+		const monitorCts = new CancellationTokenSource();
+		monitorCts.cancel();
+		monitor = store.add(instantiationService.createInstance(OutputMonitor, execution, undefined, createTestContext('1'), monitorCts.token, 'test command'));
+
+		const outputMonitorWithPrivateMethod = monitor as unknown as {
+			[key: string]: unknown;
+		};
+		let freeFormRequestShown = false;
+		outputMonitorWithPrivateMethod['_determineUserInputOptions'] = async () => ({
+			prompt: 'Password:',
+			options: [],
+			detectedRequestForFreeFormInput: true
+		});
+		outputMonitorWithPrivateMethod['_requestFreeFormTerminalInput'] = async () => {
+			freeFormRequestShown = true;
+			return true;
+		};
+
+		const idleResult = await (outputMonitorWithPrivateMethod['_handleIdleState'] as (token: CancellationToken) => Promise<{ shouldContinuePollling: boolean }>)(CancellationToken.None);
+		await Event.toPromise(monitor.onDidFinishCommand);
+		monitorCts.dispose();
+
+		assert.strictEqual(freeFormRequestShown, false, 'free-form elicitation should not be shown when auto reply is enabled');
+		assert.strictEqual(sendTextCalled, false, 'sensitive free-form prompt should not be auto-replied');
+		assert.strictEqual(idleResult.shouldContinuePollling, false, 'monitor should stop instead of propagating free-form prompt');
+	});
+
 	suite('detectsInputRequiredPattern', () => {
 		test('detects yes/no confirmation prompts (pairs and variants)', () => {
 			assert.strictEqual(detectsInputRequiredPattern('Continue? (y/N) '), true);
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/runInTerminalHelpers.test.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/runInTerminalHelpers.test.ts
index 0e6ede9ea6fd1..49735c067970d 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/runInTerminalHelpers.test.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/runInTerminalHelpers.test.ts
@@ -4,7 +4,7 @@
  *--------------------------------------------------------------------------------------------*/
 
 import { ok, strictEqual } from 'assert';
-import { generateAutoApproveActions, TRUNCATION_MESSAGE, dedupeRules, isPowerShell, sanitizeTerminalOutput, truncateOutputKeepingTail, extractCdPrefix } from '../../browser/runInTerminalHelpers.js';
+import { generateAutoApproveActions, TRUNCATION_MESSAGE, dedupeRules, isPowerShell, sanitizeTerminalOutput, truncateOutputKeepingTail, extractCdPrefix, normalizeTerminalCommandForDisplay } from '../../browser/runInTerminalHelpers.js';
 import { OperatingSystem } from '../../../../../../base/common/platform.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
 import { ConfigurationTarget } from '../../../../../../platform/configuration/common/configuration.js';
@@ -293,6 +293,25 @@ suite('sanitizeTerminalOutput', () => {
 	});
 });
 
+suite('normalizeTerminalCommandForDisplay', () => {
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('removes escaped single and double quotes', () => {
+		const input = 'git rev-parse \\\'stash@{0}\\\' && echo \\\"done\\\"';
+		strictEqual(normalizeTerminalCommandForDisplay(input), 'git rev-parse \'stash@{0}\' && echo "done"');
+	});
+
+	test('normalizes escaped forward slashes', () => {
+		const input = 'echo \\/Users\\/me\\/project';
+		strictEqual(normalizeTerminalCommandForDisplay(input), 'echo /Users/me/project');
+	});
+
+	test('preserves non-quote escapes', () => {
+		const input = 'echo path\\ with\\ spaces';
+		strictEqual(normalizeTerminalCommandForDisplay(input), input);
+	});
+});
+
 suite('generateAutoApproveActions', () => {
 	ensureNoDisposablesAreLeakedInTestSuite();
 
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/sandboxOutputAnalyzer.test.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/sandboxOutputAnalyzer.test.ts
new file mode 100644
index 0000000000000..d5d255633fe03
--- /dev/null
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/sandboxOutputAnalyzer.test.ts
@@ -0,0 +1,141 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { ok, strictEqual } from 'assert';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
+import { IFileService } from '../../../../../../platform/files/common/files.js';
+import type { TestInstantiationService } from '../../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import { workbenchInstantiationService } from '../../../../../test/browser/workbenchTestServices.js';
+import { SandboxOutputAnalyzer } from '../../browser/tools/sandboxOutputAnalyzer.js';
+import { ITerminalSandboxService } from '../../common/terminalSandboxService.js';
+
+suite('SandboxOutputAnalyzer', () => {
+	const store = ensureNoDisposablesAreLeakedInTestSuite();
+	let instantiationService: TestInstantiationService;
+
+	function createAnalyzer(options: { sandboxService?: Partial<ITerminalSandboxService>; existingPaths?: string[] } = {}) {
+		instantiationService = workbenchInstantiationService({}, store);
+		const existingPaths = new Set(options.existingPaths ?? []);
+		instantiationService.stub(IFileService, {
+			_serviceBrand: undefined,
+			exists: async resource => existingPaths.has(resource.path),
+		});
+		instantiationService.stub(ITerminalSandboxService, {
+			_serviceBrand: undefined,
+			isEnabled: async () => true,
+			promptToAllowWritePath: async () => false,
+			wrapWithSandbox: async (_runtimeConfig, command) => command,
+			wrapCommand: async command => command,
+			...options.sandboxService,
+		});
+		return store.add(instantiationService.createInstance(SandboxOutputAnalyzer));
+	}
+
+	test('should prompt to allow a denied existing write path and ask for retry', async () => {
+		const requestedPaths: string[] = [];
+		const analyzer = createAnalyzer({
+			existingPaths: ['/tmp/blocked.txt'],
+			sandboxService: {
+				promptToAllowWritePath: async path => {
+					requestedPaths.push(path);
+					return true;
+				}
+			}
+		});
+
+		const result = await analyzer.analyze({
+			exitCode: 1,
+			// eslint-disable-next-line local/code-no-unexternalized-strings
+			exitResult: "Error: EPERM: operation not permitted, open '/tmp/blocked.txt'",
+			commandLine: 'touch /tmp/blocked.txt'
+		});
+
+		strictEqual(requestedPaths[0], '/tmp/blocked.txt');
+		ok(/Retry the command\./.test(result ?? ''));
+		ok(/\/tmp\/blocked\.txt/.test(result ?? ''));
+	});
+
+	test('should fall back to the parent path when the extracted path does not exist', async () => {
+		const requestedPaths: string[] = [];
+		const analyzer = createAnalyzer({
+			sandboxService: {
+				promptToAllowWritePath: async path => {
+					requestedPaths.push(path);
+					return true;
+				}
+			}
+		});
+
+		const result = await analyzer.analyze({
+			exitCode: 1,
+			// eslint-disable-next-line local/code-no-unexternalized-strings
+			exitResult: "Error: EPERM: operation not permitted, open '/tmp/new-folder/file.txt'",
+			commandLine: 'mkdir -p /tmp/new-folder && touch /tmp/new-folder/file.txt'
+		});
+
+		strictEqual(requestedPaths[0], '/tmp/new-folder');
+		ok(/\/tmp\/new-folder/.test(result ?? ''));
+	});
+
+	test('should return generic sandbox guidance when write path approval is declined', async () => {
+		const analyzer = createAnalyzer({
+			sandboxService: {
+				promptToAllowWritePath: async () => false,
+			}
+		});
+
+		const result = await analyzer.analyze({
+			exitCode: 1,
+			// eslint-disable-next-line local/code-no-unexternalized-strings
+			exitResult: "Error: EPERM: operation not permitted, open '/tmp/blocked.txt'",
+			commandLine: 'touch /tmp/blocked.txt'
+		});
+
+		ok(/Command failed while running in sandboxed mode\./.test(result ?? ''));
+		ok(/allowWrite/.test(result ?? ''));
+	});
+
+	test('should extract an inline path followed by warning text', async () => {
+		const requestedPaths: string[] = [];
+		const analyzer = createAnalyzer({
+			sandboxService: {
+				promptToAllowWritePath: async path => {
+					requestedPaths.push(path);
+					return true;
+				}
+			}
+		});
+
+		const result = await analyzer.analyze({
+			exitCode: 1,
+			exitResult: 'Warning: Failed to create the file /home/testing/openai-api-docs.html:            Warning: Read-only file system',
+			commandLine: 'touch /home/testing/openai-api-docs.html'
+		});
+
+		strictEqual(requestedPaths[0], '/home/testing');
+		ok(/\/home\/testing/.test(result ?? ''));
+	});
+
+	test('should extract an inline path followed by plain text without a colon', async () => {
+		const requestedPaths: string[] = [];
+		const analyzer = createAnalyzer({
+			sandboxService: {
+				promptToAllowWritePath: async path => {
+					requestedPaths.push(path);
+					return true;
+				}
+			}
+		});
+
+		const result = await analyzer.analyze({
+			exitCode: 1,
+			exitResult: 'Warning: Failed to create the file /home/testing/openai-api-docs.html Warning Read-only file system',
+			commandLine: 'touch /home/testing/openai-api-docs.html'
+		});
+
+		strictEqual(requestedPaths[0], '/home/testing');
+		ok(/\/home\/testing/.test(result ?? ''));
+	});
+});
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/sandboxedCommandLinePresenter.test.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/sandboxedCommandLinePresenter.test.ts
index b1a8fed729a73..56bd8ffca9031 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/sandboxedCommandLinePresenter.test.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/sandboxedCommandLinePresenter.test.ts
@@ -8,6 +8,7 @@ import { SandboxedCommandLinePresenter } from '../../browser/tools/commandLinePr
 import { OperatingSystem } from '../../../../../../base/common/platform.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../../base/test/common/utils.js';
 import type { TestInstantiationService } from '../../../../../../platform/instantiation/test/common/instantiationServiceMock.js';
+import type { ISandboxRuntimeConfig } from '../../../../../../platform/sandbox/common/sandboxHelperIpc.js';
 import { workbenchInstantiationService } from '../../../../../test/browser/workbenchTestServices.js';
 import { ITerminalSandboxService } from '../../common/terminalSandboxService.js';
 
@@ -15,16 +16,31 @@ suite('SandboxedCommandLinePresenter', () => {
 	const store = ensureNoDisposablesAreLeakedInTestSuite();
 	let instantiationService: TestInstantiationService;
 
+	class TestTerminalSandboxService implements ITerminalSandboxService {
+		readonly _serviceBrand: undefined;
+
+		constructor(private readonly _enabled: boolean) { }
+
+		async isEnabled(): Promise<boolean> {
+			return this._enabled;
+		}
+
+		async promptToAllowWritePath(_path: string): Promise<boolean> {
+			return false;
+		}
+
+		async wrapCommand(command: string): Promise<string> {
+			return command;
+		}
+
+		async wrapWithSandbox(_runtimeConfig: ISandboxRuntimeConfig, command: string): Promise<string> {
+			return command;
+		}
+	}
+
 	const createPresenter = (enabled: boolean = true) => {
 		instantiationService = workbenchInstantiationService({}, store);
-		instantiationService.stub(ITerminalSandboxService, {
-			_serviceBrand: undefined,
-			isEnabled: async () => enabled,
-			wrapCommand: command => command,
-			getSandboxConfigPath: async () => '/tmp/sandbox.json',
-			getTempDir: () => undefined,
-			setNeedsForceUpdateConfigFile: () => { },
-		});
+		instantiationService.stub(ITerminalSandboxService, new TestTerminalSandboxService(enabled));
 		return instantiationService.createInstance(SandboxedCommandLinePresenter);
 	};
 
@@ -42,6 +58,17 @@ suite('SandboxedCommandLinePresenter', () => {
 		strictEqual(result.languageDisplayName, undefined);
 	});
 
+	test('should prefer the original command line when provided', async () => {
+		const presenter = createPresenter();
+		const result = await presenter.present({
+			commandLine: { forDisplay: 'wrapped', original: 'echo hello' },
+			shell: 'bash',
+			os: OperatingSystem.Linux
+		});
+		ok(result);
+		strictEqual(result.commandLine, 'echo hello');
+	});
+
 	test('should return command line for non-sandboxed command when enabled', async () => {
 		const presenter = createPresenter();
 		const commandLine = 'echo hello';
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/terminalSandboxService.test.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/terminalSandboxService.test.ts
index e48d807dec883..9b8ed1241c6df 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/terminalSandboxService.test.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/browser/terminalSandboxService.test.ts
@@ -9,18 +9,32 @@ import { TestInstantiationService } from '../../../../../../platform/instantiati
 import { workbenchInstantiationService } from '../../../../../test/browser/workbenchTestServices.js';
 import { TerminalSandboxService } from '../../common/terminalSandboxService.js';
 import { IConfigurationService } from '../../../../../../platform/configuration/common/configuration.js';
-import { IFileService } from '../../../../../../platform/files/common/files.js';
-import { IEnvironmentService } from '../../../../../../platform/environment/common/environment.js';
 import { ILogService, NullLogService } from '../../../../../../platform/log/common/log.js';
 import { IRemoteAgentService } from '../../../../../services/remote/common/remoteAgentService.js';
 import { ITrustedDomainService } from '../../../../url/common/trustedDomainService.js';
 import { URI } from '../../../../../../base/common/uri.js';
 import { TerminalChatAgentToolsSettingId } from '../../common/terminalChatAgentToolsConfiguration.js';
 import { Event, Emitter } from '../../../../../../base/common/event.js';
+import { mock } from '../../../../../../base/test/common/mock.js';
 import { TestConfigurationService } from '../../../../../../platform/configuration/test/common/testConfigurationService.js';
-import { VSBuffer } from '../../../../../../base/common/buffer.js';
 import { OperatingSystem } from '../../../../../../base/common/platform.js';
 import { IRemoteAgentEnvironment } from '../../../../../../platform/remote/common/remoteAgentEnvironment.js';
+import { IDialogService } from '../../../../../../platform/dialogs/common/dialogs.js';
+import { ISandboxPermissionRequest, ISandboxRuntimeConfig } from '../../../../../../platform/sandbox/common/sandboxHelperIpc.js';
+import { ISandboxHelperService } from '../../../../../../platform/sandbox/common/sandboxHelperService.js';
+import { IWorkspaceContextService, IWorkspaceFolder, toWorkspaceFolder } from '../../../../../../platform/workspace/common/workspace.js';
+
+type CapturedSandboxRuntimeConfig = ISandboxRuntimeConfig & {
+	network: {
+		allowedDomains: string[];
+		deniedDomains: string[];
+	};
+	filesystem: {
+		denyRead: string[];
+		allowWrite: string[];
+		denyWrite: string[];
+	};
+};
 
 suite('TerminalSandboxService - allowTrustedDomains', () => {
 	const store = ensureNoDisposablesAreLeakedInTestSuite();
@@ -28,8 +42,8 @@ suite('TerminalSandboxService - allowTrustedDomains', () => {
 	let instantiationService: TestInstantiationService;
 	let configurationService: TestConfigurationService;
 	let trustedDomainService: MockTrustedDomainService;
-	let fileService: MockFileService;
-	let createdFiles: Map<string, string>;
+	let workspaceContextService: MockWorkspaceContextService;
+	let sandboxHelperService: MockSandboxHelperService;
 
 	class MockTrustedDomainService implements ITrustedDomainService {
 		_serviceBrand: undefined;
@@ -41,14 +55,6 @@ suite('TerminalSandboxService - allowTrustedDomains', () => {
 		}
 	}
 
-	class MockFileService {
-		async createFile(uri: URI, content: VSBuffer): Promise<any> {
-			const contentString = content.toString();
-			createdFiles.set(uri.path, contentString);
-			return {};
-		}
-	}
-
 	class MockRemoteAgentService {
 		async getEnvironment(): Promise<IRemoteAgentEnvironment> {
 			// Return a Linux environment to ensure tests pass on Windows
@@ -77,14 +83,80 @@ suite('TerminalSandboxService - allowTrustedDomains', () => {
 				isUnsupportedGlibc: false
 			};
 		}
+
+		getConnection() {
+			return null;
+		}
+	}
+
+	class PersistingTestConfigurationService extends TestConfigurationService {
+		override updateValue(key: string, value: unknown, ..._rest: unknown[]): Promise<void> {
+			return this.setUserConfiguration(key, value);
+		}
+	}
+
+	class MockWorkspaceContextService extends mock<IWorkspaceContextService>() {
+		override _serviceBrand: undefined;
+		private readonly _onDidChangeWorkspaceFolders = new Emitter<any>();
+		override readonly onDidChangeWorkspaceFolders = this._onDidChangeWorkspaceFolders.event;
+		folders: IWorkspaceFolder[] = [];
+
+		override getWorkspace() {
+			return {
+				id: 'test-workspace',
+				folders: this.folders,
+			};
+		}
+	}
+
+	class MockSandboxHelperService implements ISandboxHelperService {
+		_serviceBrand: undefined;
+		private readonly _onDidRequestSandboxPermission = new Emitter<ISandboxPermissionRequest>();
+		readonly onDidRequestSandboxPermission = this._onDidRequestSandboxPermission.event;
+		private readonly _pendingPermissionResponses = new Map<string, (allowed: boolean) => void>();
+		resetSandboxCallCount = 0;
+		lastWrapRuntimeConfig: ISandboxRuntimeConfig | undefined;
+
+		async resetSandbox(): Promise<void> {
+			this.resetSandboxCallCount++;
+		}
+
+		async resolveSandboxPermissionRequest(requestId: string, allowed: boolean): Promise<void> {
+			this._pendingPermissionResponses.get(requestId)?.(allowed);
+			this._pendingPermissionResponses.delete(requestId);
+		}
+
+		async wrapWithSandbox(runtimeConfig: ISandboxRuntimeConfig, command: string): Promise<string> {
+			this.lastWrapRuntimeConfig = runtimeConfig;
+			return `wrapped:${command}`;
+		}
+
+		fireSandboxPermissionRequest(request: ISandboxPermissionRequest): void {
+			this._onDidRequestSandboxPermission.fire(request);
+		}
+
+		waitForSandboxPermissionResponse(requestId: string): Promise<boolean> {
+			return new Promise<boolean>(resolve => {
+				this._pendingPermissionResponses.set(requestId, resolve);
+			});
+		}
+	}
+
+	class TestTerminalSandboxService extends TerminalSandboxService {
+		readonly permissionRequests: ISandboxPermissionRequest[] = [];
+
+		override async promptForSandboxPermission(request: ISandboxPermissionRequest): Promise<boolean> {
+			this.permissionRequests.push(request);
+			return true;
+		}
 	}
 
 	setup(() => {
-		createdFiles = new Map();
 		instantiationService = workbenchInstantiationService({}, store);
-		configurationService = new TestConfigurationService();
+		configurationService = new PersistingTestConfigurationService();
 		trustedDomainService = new MockTrustedDomainService();
-		fileService = new MockFileService();
+		workspaceContextService = new MockWorkspaceContextService();
+		sandboxHelperService = new MockSandboxHelperService();
 
 		// Setup default configuration
 		configurationService.setUserConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxEnabled, true);
@@ -95,17 +167,29 @@ suite('TerminalSandboxService - allowTrustedDomains', () => {
 		});
 
 		instantiationService.stub(IConfigurationService, configurationService);
-		instantiationService.stub(IFileService, fileService);
-		instantiationService.stub(IEnvironmentService, <IEnvironmentService & { tmpDir?: URI; execPath?: string }>{
-			_serviceBrand: undefined,
-			tmpDir: URI.file('/tmp'),
-			execPath: '/usr/bin/node'
-		});
 		instantiationService.stub(ILogService, new NullLogService());
 		instantiationService.stub(IRemoteAgentService, new MockRemoteAgentService());
 		instantiationService.stub(ITrustedDomainService, trustedDomainService);
+		instantiationService.stub(IWorkspaceContextService, workspaceContextService);
+		instantiationService.stub(ISandboxHelperService, sandboxHelperService);
+		instantiationService.stub(IDialogService, new class extends mock<IDialogService>() {
+			override async confirm() {
+				return { confirmed: true };
+			}
+		});
 	});
 
+	async function getWrappedRuntimeConfig(sandboxService: TerminalSandboxService): Promise<CapturedSandboxRuntimeConfig> {
+		await sandboxService.isEnabled();
+		await sandboxService.wrapCommand('echo test');
+		ok(sandboxHelperService.lastWrapRuntimeConfig, 'Sandbox helper should receive a runtime config');
+		ok(sandboxHelperService.lastWrapRuntimeConfig.network, 'Sandbox helper config should include network settings');
+		ok(Array.isArray(sandboxHelperService.lastWrapRuntimeConfig.network.allowedDomains), 'Sandbox helper config should include allowed domains');
+		ok(sandboxHelperService.lastWrapRuntimeConfig.filesystem, 'Sandbox helper config should include filesystem settings');
+		ok(Array.isArray(sandboxHelperService.lastWrapRuntimeConfig.filesystem.allowWrite), 'Sandbox helper config should include writable paths');
+		return sandboxHelperService.lastWrapRuntimeConfig as CapturedSandboxRuntimeConfig;
+	}
+
 	test('should filter out sole wildcard (*) from trusted domains', async () => {
 		// Setup: Enable allowTrustedDomains and add * to trusted domains
 		configurationService.setUserConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxNetwork, {
@@ -116,13 +200,7 @@ suite('TerminalSandboxService - allowTrustedDomains', () => {
 		trustedDomainService.trustedDomains = ['*'];
 
 		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
-		const configPath = await sandboxService.getSandboxConfigPath();
-
-		ok(configPath, 'Config path should be defined');
-		const configContent = createdFiles.get(configPath);
-		ok(configContent, 'Config file should be created');
-
-		const config = JSON.parse(configContent);
+		const config = await getWrappedRuntimeConfig(sandboxService);
 		strictEqual(config.network.allowedDomains.length, 0, 'Sole wildcard * should be filtered out');
 	});
 
@@ -136,13 +214,7 @@ suite('TerminalSandboxService - allowTrustedDomains', () => {
 		trustedDomainService.trustedDomains = ['*.github.com'];
 
 		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
-		const configPath = await sandboxService.getSandboxConfigPath();
-
-		ok(configPath, 'Config path should be defined');
-		const configContent = createdFiles.get(configPath);
-		ok(configContent, 'Config file should be created');
-
-		const config = JSON.parse(configContent);
+		const config = await getWrappedRuntimeConfig(sandboxService);
 		strictEqual(config.network.allowedDomains.length, 1, 'Wildcard domain should be included');
 		strictEqual(config.network.allowedDomains[0], '*.github.com', 'Wildcard domain should match');
 	});
@@ -157,13 +229,7 @@ suite('TerminalSandboxService - allowTrustedDomains', () => {
 		trustedDomainService.trustedDomains = ['*', '*.github.com', 'microsoft.com'];
 
 		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
-		const configPath = await sandboxService.getSandboxConfigPath();
-
-		ok(configPath, 'Config path should be defined');
-		const configContent = createdFiles.get(configPath);
-		ok(configContent, 'Config file should be created');
-
-		const config = JSON.parse(configContent);
+		const config = await getWrappedRuntimeConfig(sandboxService);
 		strictEqual(config.network.allowedDomains.length, 3, 'Should have 3 domains (excluding *)');
 		ok(config.network.allowedDomains.includes('example.com'), 'Should include configured domain');
 		ok(config.network.allowedDomains.includes('*.github.com'), 'Should include wildcard domain');
@@ -181,13 +247,7 @@ suite('TerminalSandboxService - allowTrustedDomains', () => {
 		trustedDomainService.trustedDomains = ['*', '*.github.com'];
 
 		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
-		const configPath = await sandboxService.getSandboxConfigPath();
-
-		ok(configPath, 'Config path should be defined');
-		const configContent = createdFiles.get(configPath);
-		ok(configContent, 'Config file should be created');
-
-		const config = JSON.parse(configContent);
+		const config = await getWrappedRuntimeConfig(sandboxService);
 		strictEqual(config.network.allowedDomains.length, 1, 'Should only have configured domain');
 		strictEqual(config.network.allowedDomains[0], 'example.com', 'Should only include example.com');
 	});
@@ -202,13 +262,7 @@ suite('TerminalSandboxService - allowTrustedDomains', () => {
 		trustedDomainService.trustedDomains = ['*.github.com', 'github.com'];
 
 		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
-		const configPath = await sandboxService.getSandboxConfigPath();
-
-		ok(configPath, 'Config path should be defined');
-		const configContent = createdFiles.get(configPath);
-		ok(configContent, 'Config file should be created');
-
-		const config = JSON.parse(configContent);
+		const config = await getWrappedRuntimeConfig(sandboxService);
 		strictEqual(config.network.allowedDomains.length, 2, 'Should have 2 unique domains');
 		ok(config.network.allowedDomains.includes('github.com'), 'Should include github.com');
 		ok(config.network.allowedDomains.includes('*.github.com'), 'Should include *.github.com');
@@ -224,13 +278,7 @@ suite('TerminalSandboxService - allowTrustedDomains', () => {
 		trustedDomainService.trustedDomains = [];
 
 		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
-		const configPath = await sandboxService.getSandboxConfigPath();
-
-		ok(configPath, 'Config path should be defined');
-		const configContent = createdFiles.get(configPath);
-		ok(configContent, 'Config file should be created');
-
-		const config = JSON.parse(configContent);
+		const config = await getWrappedRuntimeConfig(sandboxService);
 		strictEqual(config.network.allowedDomains.length, 1, 'Should have only configured domain');
 		strictEqual(config.network.allowedDomains[0], 'example.com', 'Should only include example.com');
 	});
@@ -245,25 +293,159 @@ suite('TerminalSandboxService - allowTrustedDomains', () => {
 		trustedDomainService.trustedDomains = ['*'];
 
 		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
-		const configPath = await sandboxService.getSandboxConfigPath();
+		const config = await getWrappedRuntimeConfig(sandboxService);
+		strictEqual(config.network.allowedDomains.length, 0, 'Should have no domains (* filtered out)');
+	});
 
-		ok(configPath, 'Config path should be defined');
-		const configContent = createdFiles.get(configPath);
-		ok(configContent, 'Config file should be created');
+	test('should expand workspace write access defaults for multi-root workspaces', async () => {
+		workspaceContextService.folders = [
+			toWorkspaceFolder(URI.file('/workspace-one')),
+			toWorkspaceFolder(URI.file('/workspace-two')),
+		];
+		configurationService.setUserConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxLinuxFileSystem, {
+			denyRead: [],
+			allowWrite: ['.'],
+			denyWrite: []
+		});
 
-		const config = JSON.parse(configContent);
-		strictEqual(config.network.allowedDomains.length, 0, 'Should have no domains (* filtered out)');
+		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
+		const config = await getWrappedRuntimeConfig(sandboxService);
+		ok(config.filesystem.allowWrite.includes('/workspace-one'), 'Should include the first workspace folder path');
+		ok(config.filesystem.allowWrite.includes('/workspace-two'), 'Should include the second workspace folder path');
+		ok(config.filesystem.allowWrite.includes('~/.npm'), 'Should include the default npm write path');
+	});
+
+	test('should delegate wrapping to sandbox helper', async () => {
+		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
+		const wrappedCommand = await sandboxService.wrapCommand('echo test');
+		strictEqual(wrappedCommand, 'wrapped:echo test');
 	});
 
-	test('should add ripgrep bin directory to PATH when wrapping command', async () => {
+	test('should preserve the full command when delegating wrapping', async () => {
 		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
-		await sandboxService.getSandboxConfigPath();
 
-		const wrappedCommand = sandboxService.wrapCommand('echo test');
+		const command = '";echo SANDBOX_ESCAPE_REPRO; # $(uname) `id`';
+		const wrappedCommand = await sandboxService.wrapCommand(command);
+		strictEqual(wrappedCommand, `wrapped:${command}`);
+	});
+
+	test('should preserve variable and command substitution payloads', async () => {
+		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
+
+		const command = 'echo $HOME $(curl eth0.me) `id`';
+		const wrappedCommand = await sandboxService.wrapCommand(command);
+		strictEqual(wrappedCommand, `wrapped:${command}`);
+	});
+
+	test('should preserve single-quote breakout payloads', async () => {
+		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
+
+		const command = `';curl eth0.me; #'`;
+		const wrappedCommand = await sandboxService.wrapCommand(command);
+		strictEqual(wrappedCommand, `wrapped:${command}`);
+	});
+
+	test('should preserve embedded single quotes', async () => {
+		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
+
+		const wrappedCommand = await sandboxService.wrapCommand(`echo 'hello'`);
+		strictEqual(wrappedCommand, `wrapped:echo 'hello'`);
+	});
+
+	test('should route sandbox permission requests through terminal sandbox service', async () => {
+		const sandboxHelperService = new MockSandboxHelperService();
+		instantiationService.stub(ISandboxHelperService, sandboxHelperService);
+
+		const sandboxService = store.add(instantiationService.createInstance(TestTerminalSandboxService));
+		await sandboxService.wrapWithSandbox({
+			network: {
+				allowedDomains: [],
+				deniedDomains: []
+			},
+			filesystem: {
+				denyRead: [],
+				allowWrite: [],
+				denyWrite: []
+			}
+		}, 'echo test');
+
+		const responsePromise = sandboxHelperService.waitForSandboxPermissionResponse('request-1');
+		sandboxHelperService.fireSandboxPermissionRequest({
+			requestId: 'request-1',
+			host: 'example.com',
+			port: 443,
+		});
+
+		strictEqual(await responsePromise, true);
+		strictEqual(sandboxService.permissionRequests.length, 1);
+		strictEqual(sandboxService.permissionRequests[0].host, 'example.com');
+		strictEqual(sandboxService.permissionRequests[0].port, 443);
+	});
+
+	test('should persist approved sandbox hosts to settings', async () => {
+		const sandboxHelperService = new MockSandboxHelperService();
+		instantiationService.stub(ISandboxHelperService, sandboxHelperService);
+		configurationService.setUserConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxNetwork, {
+			allowedDomains: ['existing.com'],
+			deniedDomains: ['example.com'],
+			allowTrustedDomains: false
+		});
+
+		const sandboxService = store.add(instantiationService.createInstance(TestTerminalSandboxService));
+		await sandboxService.wrapWithSandbox({
+			network: {
+				allowedDomains: [],
+				deniedDomains: []
+			},
+			filesystem: {
+				denyRead: [],
+				allowWrite: [],
+				denyWrite: []
+			}
+		}, 'echo test');
+
+		const responsePromise = sandboxHelperService.waitForSandboxPermissionResponse('request-2');
+		sandboxHelperService.fireSandboxPermissionRequest({
+			requestId: 'request-2',
+			host: 'example.com',
+			port: 443,
+		});
+
+		strictEqual(await responsePromise, true);
+		const updatedSettings = configurationService.getValue<{
+			allowedDomains?: string[];
+			deniedDomains?: string[];
+		}>(TerminalChatAgentToolsSettingId.TerminalSandboxNetwork);
+		ok(updatedSettings?.allowedDomains?.includes('existing.com'));
+		ok(updatedSettings?.allowedDomains?.includes('example.com'));
+		ok(!updatedSettings?.deniedDomains?.includes('example.com'));
+	});
+
+	test('should persist approved sandbox write paths to settings', async () => {
+		configurationService.setUserConfiguration(TerminalChatAgentToolsSettingId.TerminalSandboxLinuxFileSystem, {
+			denyRead: [],
+			allowWrite: ['/existing/path'],
+			denyWrite: ['/tmp/blocked.txt']
+		});
+
+		const sandboxService = store.add(instantiationService.createInstance(TerminalSandboxService));
+		strictEqual(await sandboxService.promptToAllowWritePath('/tmp/blocked.txt'), true);
+
+		const updatedSettings = configurationService.getValue<{
+			allowWrite?: string[];
+			denyWrite?: string[];
+		}>(TerminalChatAgentToolsSettingId.TerminalSandboxLinuxFileSystem);
+		ok(updatedSettings?.allowWrite?.includes('/existing/path'));
+		ok(updatedSettings?.allowWrite?.includes('/tmp/blocked.txt'));
+		ok(!updatedSettings?.denyWrite?.includes('/tmp/blocked.txt'));
+	});
+
+	test('should not reset sandbox when unrelated settings change', async () => {
+		store.add(instantiationService.createInstance(TerminalSandboxService));
+		strictEqual(sandboxHelperService.resetSandboxCallCount, 0);
+
+		configurationService.setUserConfiguration('window.zoomLevel', 1);
 
-		ok(
-			wrappedCommand.includes('PATH') && wrappedCommand.includes('ripgrep'),
-			'Wrapped command should include PATH modification with ripgrep'
-		);
+		strictEqual(sandboxHelperService.resetSandboxCallCount, 0);
 	});
 });
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/electron-browser/commandLineSandboxRewriter.test.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/electron-browser/commandLineSandboxRewriter.test.ts
index 46fe1a19203a7..09135b729136b 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/electron-browser/commandLineSandboxRewriter.test.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/electron-browser/commandLineSandboxRewriter.test.ts
@@ -22,10 +22,9 @@ suite('CommandLineSandboxRewriter', () => {
 		instantiationService.stub(ITerminalSandboxService, {
 			_serviceBrand: undefined,
 			isEnabled: async () => false,
-			wrapCommand: command => command,
-			getSandboxConfigPath: async () => '/tmp/sandbox.json',
-			getTempDir: () => undefined,
-			setNeedsForceUpdateConfigFile: () => { },
+			promptToAllowWritePath: async () => false,
+			wrapWithSandbox: async (_runtimeConfig, command) => command,
+			wrapCommand: command => Promise.resolve(command),
 			...overrides
 		});
 	};
@@ -46,29 +45,13 @@ suite('CommandLineSandboxRewriter', () => {
 		strictEqual(result, undefined);
 	});
 
-	test('returns undefined when sandbox config is unavailable', async () => {
-		stubSandboxService({
-			isEnabled: async () => true,
-			wrapCommand: command => `wrapped:${command}`,
-			getSandboxConfigPath: async () => undefined,
-		});
-
-		const rewriter = store.add(instantiationService.createInstance(CommandLineSandboxRewriter));
-		const result = await rewriter.rewrite(createRewriteOptions('echo hello'));
-		strictEqual(result, undefined);
-	});
-
-	test('wraps command when sandbox is enabled and config exists', async () => {
+	test('wraps command when sandbox is enabled', async () => {
 		const calls: string[] = [];
 		stubSandboxService({
 			isEnabled: async () => true,
 			wrapCommand: command => {
 				calls.push('wrapCommand');
-				return `wrapped:${command}`;
-			},
-			getSandboxConfigPath: async () => {
-				calls.push('getSandboxConfigPath');
-				return '/tmp/sandbox.json';
+				return Promise.resolve(`wrapped:${command}`);
 			},
 		});
 
@@ -76,6 +59,6 @@ suite('CommandLineSandboxRewriter', () => {
 		const result = await rewriter.rewrite(createRewriteOptions('echo hello'));
 		strictEqual(result?.rewritten, 'wrapped:echo hello');
 		strictEqual(result?.reasoning, 'Wrapped command for sandbox execution');
-		deepStrictEqual(calls, ['getSandboxConfigPath', 'wrapCommand']);
+		deepStrictEqual(calls, ['wrapCommand']);
 	});
 });
diff --git a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/electron-browser/runInTerminalTool.test.ts b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/electron-browser/runInTerminalTool.test.ts
index e362782b44b24..269da136d5f80 100644
--- a/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/electron-browser/runInTerminalTool.test.ts
+++ b/src/vs/workbench/contrib/terminalContrib/chatAgentTools/test/electron-browser/runInTerminalTool.test.ts
@@ -41,11 +41,14 @@ import { ShellIntegrationQuality } from '../../browser/toolTerminalCreator.js';
 import { terminalChatAgentToolsConfiguration, TerminalChatAgentToolsSettingId } from '../../common/terminalChatAgentToolsConfiguration.js';
 import { TerminalChatService } from '../../../chat/browser/terminalChatService.js';
 import type { IMarkdownString } from '../../../../../../base/common/htmlContent.js';
+import { IAgentSessionsService } from '../../../../chat/browser/agentSessions/agentSessionsService.js';
+import { IAgentSession } from '../../../../chat/browser/agentSessions/agentSessionsModel.js';
 
 class TestRunInTerminalTool extends RunInTerminalTool {
 	protected override _osBackend: Promise<OperatingSystem> = Promise.resolve(OperatingSystem.Windows);
 
 	get sessionTerminalAssociations() { return this._sessionTerminalAssociations; }
+	get sessionTerminalInstances() { return this._sessionTerminalInstances; }
 	get profileFetcher() { return this._profileFetcher; }
 
 	setBackendOs(os: OperatingSystem) {
@@ -63,6 +66,7 @@ suite('RunInTerminalTool', () => {
 	let workspaceContextService: TestContextService;
 	let terminalServiceDisposeEmitter: Emitter<ITerminalInstance>;
 	let chatServiceDisposeEmitter: Emitter<{ sessionResource: URI[]; reason: 'cleared' }>;
+	let chatSessionArchivedEmitter: Emitter<IAgentSession>;
 
 	let runInTerminalTool: TestRunInTerminalTool;
 
@@ -79,6 +83,7 @@ suite('RunInTerminalTool', () => {
 		setConfig(TerminalChatAgentToolsSettingId.BlockDetectedFileWrites, 'outsideWorkspace');
 		terminalServiceDisposeEmitter = new Emitter<ITerminalInstance>();
 		chatServiceDisposeEmitter = new Emitter<{ sessionResource: URI[]; reason: 'cleared' }>();
+		chatSessionArchivedEmitter = new Emitter<IAgentSession>();
 
 		instantiationService = workbenchInstantiationService({
 			configurationService: () => configurationService,
@@ -86,7 +91,14 @@ suite('RunInTerminalTool', () => {
 		}, store);
 
 		instantiationService.stub(IChatService, {
-			onDidDisposeSession: chatServiceDisposeEmitter.event
+			onDidDisposeSession: chatServiceDisposeEmitter.event,
+			getSession: () => undefined,
+		});
+		instantiationService.stub(IAgentSessionsService, {
+			onDidChangeSessionArchivedState: chatSessionArchivedEmitter.event,
+			model: {
+				onDidChangeSessionArchivedState: chatSessionArchivedEmitter.event,
+			} as IAgentSessionsService['model']
 		});
 		instantiationService.stub(ITerminalChatService, store.add(instantiationService.createInstance(TerminalChatService)));
 		instantiationService.stub(IWorkspaceContextService, workspaceContextService);
@@ -96,10 +108,9 @@ suite('RunInTerminalTool', () => {
 		instantiationService.stub(ITerminalSandboxService, {
 			_serviceBrand: undefined,
 			isEnabled: async () => false,
-			wrapCommand: command => command,
-			getSandboxConfigPath: async () => undefined,
-			getTempDir: () => undefined,
-			setNeedsForceUpdateConfigFile: () => { }
+			promptToAllowWritePath: async () => false,
+			wrapWithSandbox: async (_runtimeConfig, command) => command,
+			wrapCommand: command => Promise.resolve(command),
 		});
 
 		const treeSitterLibraryService = store.add(instantiationService.createInstance(TreeSitterLibraryService));
@@ -504,8 +515,7 @@ suite('RunInTerminalTool', () => {
 
 			// Verify that auto-approve information is included
 			ok(result?.toolSpecificData, 'Expected toolSpecificData to be defined');
-			// eslint-disable-next-line local/code-no-any-casts
-			const terminalData = result!.toolSpecificData as any;
+			const terminalData = result!.toolSpecificData as IChatTerminalToolInvocationData;
 			ok(terminalData.autoApproveInfo, 'Expected autoApproveInfo to be defined for auto-approved background command');
 			ok(terminalData.autoApproveInfo.value, 'Expected autoApproveInfo to have a value');
 			ok(terminalData.autoApproveInfo.value.includes('npm'), 'Expected autoApproveInfo to mention the approved rule');
@@ -1139,13 +1149,149 @@ suite('RunInTerminalTool', () => {
 	});
 
 	suite('chat session disposal cleanup', () => {
+		const createMockTerminal = (processId: number): ITerminalInstance => ({
+			dispose: () => { /* Mock dispose */ },
+			processId
+		} as unknown as ITerminalInstance);
+
+		test('should restore all terminals into the session terminal map and dispose them when archived', () => {
+			const sessionId = 'test-session-restored-archive';
+			const sessionResource = LocalChatSessionUri.forSession(sessionId);
+
+			let terminal1Disposed = false;
+			let terminal2Disposed = false;
+			const terminal1DisposedEmitter = new Emitter<void>();
+			const terminal2DisposedEmitter = new Emitter<void>();
+			const mockTerminal1 = {
+				dispose: () => {
+					terminal1Disposed = true;
+					terminal1DisposedEmitter.fire();
+				},
+				onDisposed: terminal1DisposedEmitter.event,
+				processId: 55555,
+			} as unknown as ITerminalInstance;
+			const mockTerminal2 = {
+				dispose: () => {
+					terminal2Disposed = true;
+					terminal2DisposedEmitter.fire();
+				},
+				onDisposed: terminal2DisposedEmitter.event,
+				processId: 66666,
+			} as unknown as ITerminalInstance;
+
+			storageService.store('chat.terminalSessions', JSON.stringify({
+				[mockTerminal1.processId!]: {
+					sessionId,
+					id: 'restored-1',
+					shellIntegrationQuality: ShellIntegrationQuality.None,
+					isBackground: true,
+				},
+				[mockTerminal2.processId!]: {
+					sessionId,
+					id: 'restored-2',
+					shellIntegrationQuality: ShellIntegrationQuality.None,
+					isBackground: false,
+				}
+			}), StorageScope.WORKSPACE, StorageTarget.USER);
+
+			instantiationService.stub(ITerminalService, {
+				onDidDisposeInstance: terminalServiceDisposeEmitter.event,
+				instances: [mockTerminal1, mockTerminal2],
+				setNextCommandId: async () => { }
+			});
+
+			const restoredRunInTerminalTool = store.add(instantiationService.createInstance(TestRunInTerminalTool));
+			const restoredSessionTerminals = restoredRunInTerminalTool.sessionTerminalInstances.get(sessionResource);
+			strictEqual(restoredSessionTerminals?.size, 2, 'Both restored terminals should be tracked for the session');
+
+			chatSessionArchivedEmitter.fire({
+				resource: sessionResource,
+				isArchived: () => true,
+			} as unknown as IAgentSession);
+
+			strictEqual(terminal1Disposed, true, 'Restored background terminal should have been disposed');
+			strictEqual(terminal2Disposed, true, 'Restored foreground terminal should have been disposed');
+			ok(!restoredRunInTerminalTool.sessionTerminalAssociations.has(sessionResource), 'Foreground terminal association should be removed after archive');
+			ok(!restoredRunInTerminalTool.sessionTerminalInstances.has(sessionResource), 'All restored terminals for the session should be removed after archive');
+		});
+
+		test('should dispose all terminals associated with a single chat session when archived', () => {
+			const sessionId = 'test-session-archive';
+			const sessionResource = LocalChatSessionUri.forSession(sessionId);
+			const mockTerminal1 = { dispose: () => { /* Mock dispose */ }, processId: 33333 } as unknown as ITerminalInstance;
+			const mockTerminal2 = { dispose: () => { /* Mock dispose */ }, processId: 44444 } as unknown as ITerminalInstance;
+
+			let terminal1Disposed = false;
+			let terminal2Disposed = false;
+			mockTerminal1.dispose = () => { terminal1Disposed = true; };
+			mockTerminal2.dispose = () => { terminal2Disposed = true; };
+
+			runInTerminalTool.sessionTerminalAssociations.set(sessionResource, {
+				instance: mockTerminal2,
+				shellIntegrationQuality: ShellIntegrationQuality.None
+			});
+			runInTerminalTool.sessionTerminalInstances.set(sessionResource, new Set([mockTerminal1, mockTerminal2]));
+
+			// Initialize lazy archive listener before firing the archive event.
+			const ensureArchivedSessionListener = (runInTerminalTool as unknown as Record<string, () => void>)['_ensureArchivedSessionListener'];
+			ensureArchivedSessionListener.call(runInTerminalTool);
+
+			chatSessionArchivedEmitter.fire({
+				resource: sessionResource,
+				isArchived: () => true,
+			} as unknown as IAgentSession);
+
+			strictEqual(terminal1Disposed, true, 'Terminal 1 should have been disposed');
+			strictEqual(terminal2Disposed, true, 'Terminal 2 should have been disposed');
+			ok(!runInTerminalTool.sessionTerminalAssociations.has(sessionResource), 'Terminal association should be removed after archive');
+			ok(!runInTerminalTool.sessionTerminalInstances.has(sessionResource), 'All tracked terminals for the session should be removed after archive');
+		});
+
+		test('should not access agent sessions model when initializing archive listener', () => {
+			let modelAccessed = false;
+			instantiationService.stub(IAgentSessionsService, {
+				onDidChangeSessionArchivedState: chatSessionArchivedEmitter.event,
+				get model() {
+					modelAccessed = true;
+					throw new Error('model should not be accessed when wiring archive listener');
+				},
+			} as unknown as IAgentSessionsService);
+
+			const noModelAccessRunInTerminalTool = store.add(instantiationService.createInstance(TestRunInTerminalTool));
+			const ensureArchivedSessionListener = (noModelAccessRunInTerminalTool as unknown as Record<string, () => void>)['_ensureArchivedSessionListener'];
+			ensureArchivedSessionListener.call(noModelAccessRunInTerminalTool);
+
+			strictEqual(modelAccessed, false, 'Agent sessions model should not be accessed when initializing archive listener');
+		});
+
+		test('should dispose all terminals associated with a single chat session', () => {
+			const sessionId = 'test-session-multiple-terminals';
+			const mockTerminal1 = createMockTerminal(11111);
+			const mockTerminal2 = createMockTerminal(22222);
+
+			let terminal1Disposed = false;
+			let terminal2Disposed = false;
+			mockTerminal1.dispose = () => { terminal1Disposed = true; };
+			mockTerminal2.dispose = () => { terminal2Disposed = true; };
+
+			const sessionResource = LocalChatSessionUri.forSession(sessionId);
+			runInTerminalTool.sessionTerminalAssociations.set(sessionResource, {
+				instance: mockTerminal2,
+				shellIntegrationQuality: ShellIntegrationQuality.None
+			});
+			runInTerminalTool.sessionTerminalInstances.set(sessionResource, new Set([mockTerminal1, mockTerminal2]));
+
+			chatServiceDisposeEmitter.fire({ sessionResource: [sessionResource], reason: 'cleared' });
+
+			strictEqual(terminal1Disposed, true, 'Terminal 1 should have been disposed');
+			strictEqual(terminal2Disposed, true, 'Terminal 2 should have been disposed');
+			ok(!runInTerminalTool.sessionTerminalAssociations.has(sessionResource), 'Terminal association should be removed after disposal');
+			ok(!runInTerminalTool.sessionTerminalInstances.has(sessionResource), 'All tracked terminals for the session should be removed after disposal');
+		});
+
 		test('should dispose associated terminals when chat session is disposed', () => {
 			const sessionId = 'test-session-123';
-			// eslint-disable-next-line local/code-no-any-casts
-			const mockTerminal: ITerminalInstance = {
-				dispose: () => { /* Mock dispose */ },
-				processId: 12345
-			} as any;
+			const mockTerminal = createMockTerminal(12345);
 			let terminalDisposed = false;
 			mockTerminal.dispose = () => { terminalDisposed = true; };
 
@@ -1166,16 +1312,8 @@ suite('RunInTerminalTool', () => {
 		test('should not affect other sessions when one session is disposed', () => {
 			const sessionId1 = 'test-session-1';
 			const sessionId2 = 'test-session-2';
-			// eslint-disable-next-line local/code-no-any-casts
-			const mockTerminal1: ITerminalInstance = {
-				dispose: () => { /* Mock dispose */ },
-				processId: 12345
-			} as any;
-			// eslint-disable-next-line local/code-no-any-casts
-			const mockTerminal2: ITerminalInstance = {
-				dispose: () => { /* Mock dispose */ },
-				processId: 67890
-			} as any;
+			const mockTerminal1 = createMockTerminal(12345);
+			const mockTerminal2 = createMockTerminal(67890);
 
 			let terminal1Disposed = false;
 			let terminal2Disposed = false;
@@ -1277,7 +1415,11 @@ suite('RunInTerminalTool', () => {
 	});
 
 	suite('session auto approval', () => {
-		test('should auto approve all commands when session has auto approval enabled', async () => {
+		setup(() => {
+			setAutoApprove({ rm: false });
+		});
+
+		test('should return policy denial details for denied commands when session has auto approval enabled', async () => {
 			const sessionId = 'test-session-123';
 			const sessionResource = LocalChatSessionUri.forSession(sessionId);
 			const terminalChatService = instantiationService.get(ITerminalChatService);
@@ -1301,8 +1443,61 @@ suite('RunInTerminalTool', () => {
 			assertAutoApproved(result);
 
 			const terminalData = result!.toolSpecificData as IChatTerminalToolInvocationData;
-			ok(terminalData.autoApproveInfo, 'Expected autoApproveInfo to be defined');
-			ok(terminalData.autoApproveInfo.value.includes('Auto approved for this session'), 'Expected session approval message');
+			ok(terminalData.alternativeRecommendation, 'Expected policy denial alternative recommendation');
+			ok(terminalData.alternativeRecommendation.includes('POLICY_DENIED'), 'Expected policy denial marker');
+			ok(terminalData.alternativeRecommendation.includes('rm dangerous-file.txt'), 'Expected denied command details');
+		});
+
+		test('should still show confirmation when forceConfirmationReason is provided', async () => {
+			const sessionId = 'test-session-123-force';
+			const sessionResource = LocalChatSessionUri.forSession(sessionId);
+			const terminalChatService = instantiationService.get(ITerminalChatService);
+
+			terminalChatService.setChatSessionAutoApproval(sessionResource, true);
+
+			const context: IToolInvocationPreparationContext = {
+				parameters: {
+					command: 'rm dangerous-file.txt',
+					explanation: 'Remove a file',
+					goal: 'Remove a file',
+					isBackground: false
+				} as IRunInTerminalInputParams,
+				chatSessionResource: sessionResource,
+				forceConfirmationReason: 'test'
+			} as IToolInvocationPreparationContext;
+
+			const result = await runInTerminalTool.prepareToolInvocation(context, CancellationToken.None);
+			assertConfirmationRequired(result);
+		});
+
+		test('should circuit break repeated denied command attempts in auto approval sessions', async () => {
+			const sessionId = 'test-session-123-circuit-break';
+			const sessionResource = LocalChatSessionUri.forSession(sessionId);
+			const terminalChatService = instantiationService.get(ITerminalChatService);
+
+			terminalChatService.setChatSessionAutoApproval(sessionResource, true);
+
+			const context: IToolInvocationPreparationContext = {
+				parameters: {
+					command: 'rm dangerous-file.txt',
+					explanation: 'Remove a file',
+					goal: 'Remove a file',
+					isBackground: false
+				} as IRunInTerminalInputParams,
+				chatSessionResource: sessionResource
+			} as IToolInvocationPreparationContext;
+
+			const first = await runInTerminalTool.prepareToolInvocation(context, CancellationToken.None);
+			const second = await runInTerminalTool.prepareToolInvocation(context, CancellationToken.None);
+			const third = await runInTerminalTool.prepareToolInvocation(context, CancellationToken.None);
+
+			const firstData = first!.toolSpecificData as IChatTerminalToolInvocationData;
+			const secondData = second!.toolSpecificData as IChatTerminalToolInvocationData;
+			const thirdData = third!.toolSpecificData as IChatTerminalToolInvocationData;
+
+			ok(firstData.alternativeRecommendation?.includes('POLICY_DENIED'), 'Expected initial policy denial message');
+			ok(secondData.alternativeRecommendation?.includes('POLICY_DENIED'), 'Expected second policy denial message');
+			ok(thirdData.alternativeRecommendation?.includes('POLICY_DENIED_CIRCUIT_BREAKER'), 'Expected circuit breaker policy denial message');
 		});
 	});
 
diff --git a/src/vs/workbench/contrib/testing/common/testingChatAgentTool.ts b/src/vs/workbench/contrib/testing/common/testingChatAgentTool.ts
index 94cb8a0f18271..cf9ae07107fe1 100644
--- a/src/vs/workbench/contrib/testing/common/testingChatAgentTool.ts
+++ b/src/vs/workbench/contrib/testing/common/testingChatAgentTool.ts
@@ -31,14 +31,14 @@ import {
 	ToolProgress,
 } from '../../chat/common/tools/languageModelToolsService.js';
 import { TestId } from './testId.js';
-import { FileCoverage, getTotalCoveragePercent } from './testCoverage.js';
+import { FileCoverage, TestCoverage, getTotalCoveragePercent } from './testCoverage.js';
 import { TestingContextKeys } from './testingContextKeys.js';
 import { collectTestStateCounts, getTestProgressText } from './testingProgressMessages.js';
 import { isFailedState } from './testingStates.js';
 import { LiveTestResult } from './testResult.js';
 import { ITestResultService } from './testResultService.js';
 import { ITestService, testsInFile, waitForTestToBeIdle } from './testService.js';
-import { IncrementalTestCollectionItem, TestItemExpandState, TestMessageType, TestResultState, TestRunProfileBitset } from './testTypes.js';
+import { DetailType, IncrementalTestCollectionItem, TestItemExpandState, TestMessageType, TestResultState, TestRunProfileBitset } from './testTypes.js';
 import { Position } from '../../../../editor/common/core/position.js';
 import { ITestProfileService } from './testProfileService.js';
 
@@ -70,7 +70,7 @@ interface IRunTestToolParams {
 	mode?: Mode;
 }
 
-class RunTestTool implements IToolImpl {
+export class RunTestTool implements IToolImpl {
 	public static readonly ID = 'runTests';
 	public static readonly DEFINITION: IToolData = {
 		id: this.ID,
@@ -101,7 +101,7 @@ class RunTestTool implements IToolImpl {
 				coverageFiles: {
 					type: 'array',
 					items: { type: 'string' },
-					description: 'When mode="coverage": absolute file paths to include detailed coverage info for. Only the first matching file will be summarized.'
+					description: 'When mode="coverage": absolute file paths to include detailed coverage info for. If not provided, a file-level summary of all files with incomplete coverage is shown.'
 				}
 			},
 		},
@@ -168,7 +168,7 @@ class RunTestTool implements IToolImpl {
 			};
 		}
 
-		const summary = await this._buildSummary(result, mode, coverageFiles);
+		const summary = await buildTestRunSummary(result, mode, coverageFiles);
 		const content = [{ kind: 'text', value: summary } as const];
 
 		return {
@@ -177,132 +177,6 @@ class RunTestTool implements IToolImpl {
 		};
 	}
 
-	private async _buildSummary(result: LiveTestResult, mode: Mode, coverageFiles: string[] | undefined): Promise<string> {
-		const failures = result.counts[TestResultState.Errored] + result.counts[TestResultState.Failed];
-		let str = `<summary passed=${result.counts[TestResultState.Passed]} failed=${failures} />\n`;
-		if (failures !== 0) {
-			str += await this._getFailureDetails(result);
-		}
-		if (mode === 'coverage') {
-			str += await this._getCoverageSummary(result, coverageFiles);
-		}
-		return str;
-	}
-
-	private async _getCoverageSummary(result: LiveTestResult, coverageFiles: string[] | undefined): Promise<string> {
-		if (!coverageFiles || !coverageFiles.length) {
-			return '';
-		}
-		for (const task of result.tasks) {
-			const coverage = task.coverage.get();
-			if (!coverage) {
-				continue;
-			}
-			const normalized = coverageFiles.map(file => URI.file(file).fsPath);
-			const coveredFilesMap = new Map<string, FileCoverage>();
-			for (const file of coverage.getAllFiles().values()) {
-				coveredFilesMap.set(file.uri.fsPath, file);
-			}
-			for (const path of normalized) {
-				const file = coveredFilesMap.get(path);
-				if (!file) {
-					continue;
-				}
-				let summary = `<coverage task=${JSON.stringify(task.name || '')}>\n`;
-				const pct = getTotalCoveragePercent(file.statement, file.branch, file.declaration) * 100;
-				summary += `<firstUncoveredFile path=${JSON.stringify(path)} statementsCovered=${file.statement.covered} statementsTotal=${file.statement.total}`;
-				if (file.branch) {
-					summary += ` branchesCovered=${file.branch.covered} branchesTotal=${file.branch.total}`;
-				}
-				if (file.declaration) {
-					summary += ` declarationsCovered=${file.declaration.covered} declarationsTotal=${file.declaration.total}`;
-				}
-				summary += ` percent=${pct.toFixed(2)}`;
-				try {
-					const details = await file.details();
-					for (const detail of details) {
-						if (detail.count || !detail.location) {
-							continue;
-						}
-						let startLine: number;
-						let endLine: number;
-						if (Position.isIPosition(detail.location)) {
-							startLine = endLine = detail.location.lineNumber;
-						} else {
-							startLine = detail.location.startLineNumber;
-							endLine = detail.location.endLineNumber;
-						}
-						summary += ` firstUncoveredStart=${startLine} firstUncoveredEnd=${endLine}`;
-						break;
-					}
-				} catch { /* ignore */ }
-				summary += ` />\n`;
-				summary += `</coverage>\n`;
-				return summary;
-			}
-		}
-		return '';
-	}
-
-	private async _getFailureDetails(result: LiveTestResult): Promise<string> {
-		let str = '';
-		let hadMessages = false;
-		for (const failure of result.tests) {
-			if (!isFailedState(failure.ownComputedState)) {
-				continue;
-			}
-
-			const [, ...testPath] = TestId.split(failure.item.extId);
-			const testName = testPath.pop();
-			str += `<testFailure name=${JSON.stringify(testName)} path=${JSON.stringify(testPath.join(' > '))}>\n`;
-			// Extract detailed failure information from error messages
-			for (const task of failure.tasks) {
-				for (const message of task.messages.filter(m => m.type === TestMessageType.Error)) {
-					hadMessages = true;
-
-					// Add expected/actual outputs if available
-					if (message.expected !== undefined && message.actual !== undefined) {
-						str += `<expectedOutput>\n${message.expected}\n</expectedOutput>\n`;
-						str += `<actualOutput>\n${message.actual}\n</actualOutput>\n`;
-					} else {
-						// Fallback to the message content
-						const messageText = typeof message.message === 'string' ? message.message : message.message.value;
-						str += `<message>\n${messageText}\n</message>\n`;
-					}
-
-					// Add stack trace information if available (limit to first 10 frames)
-					if (message.stackTrace && message.stackTrace.length > 0) {
-						for (const frame of message.stackTrace.slice(0, 10)) {
-							if (frame.uri && frame.position) {
-								str += `<stackFrame path="${frame.uri.fsPath}" line="${frame.position.lineNumber}" col="${frame.position.column}" />\n`;
-							} else if (frame.uri) {
-								str += `<stackFrame path="${frame.uri.fsPath}">${frame.label}</stackFrame>\n`;
-							} else {
-								str += `<stackFrame>${frame.label}</stackFrame>\n`;
-							}
-						}
-					}
-
-					// Add location information if available
-					if (message.location) {
-						str += `<location path="${message.location.uri.fsPath}" line="${message.location.range.startLineNumber}" col="${message.location.range.startColumn}" />\n`;
-					}
-				}
-			}
-
-			str += `</testFailure>\n`;
-		}
-
-		if (!hadMessages) { // some adapters don't have any per-test messages and just output
-			const output = result.tasks.map(t => t.output.getRange(0, t.output.length).toString().trim()).join('\n');
-			if (output) {
-				str += `<output>\n${output}\n</output>\n`;
-			}
-		}
-
-		return str;
-	}
-
 	/** Updates the UI progress as the test runs, resolving when the run is finished. */
 	private async _monitorRunProgress(result: LiveTestResult, progress: ToolProgress, token: CancellationToken): Promise<void> {
 		const store = new DisposableStore();
@@ -451,3 +325,202 @@ class RunTestTool implements IToolImpl {
 		});
 	}
 }
+
+/** Builds the full summary string for a completed test run. */
+export async function buildTestRunSummary(result: LiveTestResult, mode: Mode, coverageFiles: string[] | undefined): Promise<string> {
+	const failures = result.counts[TestResultState.Errored] + result.counts[TestResultState.Failed];
+	let str = `<summary passed=${result.counts[TestResultState.Passed]} failed=${failures} />\n`;
+	if (failures !== 0) {
+		str += await getFailureDetails(result);
+	}
+	if (mode === 'coverage') {
+		str += await getCoverageSummary(result, coverageFiles);
+	}
+	return str;
+}
+
+/** Gets a coverage summary from a test result, either overall or per-file. */
+export async function getCoverageSummary(result: LiveTestResult, coverageFiles: string[] | undefined): Promise<string> {
+	let str = '';
+	for (const task of result.tasks) {
+		const coverage = task.coverage.get();
+		if (!coverage) {
+			continue;
+		}
+
+		if (!coverageFiles || !coverageFiles.length) {
+			str += getOverallCoverageSummary(coverage);
+			continue;
+		}
+
+		const normalized = coverageFiles.map(file => URI.file(file).fsPath);
+		const coveredFilesMap = new Map<string, FileCoverage>();
+		for (const file of coverage.getAllFiles().values()) {
+			coveredFilesMap.set(file.uri.fsPath, file);
+		}
+
+		for (const path of normalized) {
+			const file = coveredFilesMap.get(path);
+			if (!file) {
+				continue;
+			}
+			str += await getFileCoverageDetails(file, path);
+		}
+	}
+	return str;
+}
+
+/** Gets a file-level coverage overview sorted by lowest coverage first. */
+export function getOverallCoverageSummary(coverage: TestCoverage): string {
+	const files = [...coverage.getAllFiles().values()]
+		.map(f => ({ path: f.uri.fsPath, pct: getTotalCoveragePercent(f.statement, f.branch, f.declaration) * 100 }))
+		.filter(f => f.pct < 100)
+		.sort((a, b) => a.pct - b.pct);
+
+	if (!files.length) {
+		return '<coverageSummary>All files have 100% coverage.</coverageSummary>\n';
+	}
+
+	let str = '<coverageSummary>\n';
+	for (const f of files) {
+		str += `<file path="${f.path}" percent=${f.pct.toFixed(1)} />\n`;
+	}
+	str += '</coverageSummary>\n';
+	return str;
+}
+
+/** Gets detailed coverage information for a single file including uncovered items. */
+export async function getFileCoverageDetails(file: FileCoverage, path: string): Promise<string> {
+	const pct = getTotalCoveragePercent(file.statement, file.branch, file.declaration) * 100;
+	let str = `<coverage path="${path}" percent=${pct.toFixed(1)} statements=${file.statement.covered}/${file.statement.total}`;
+	if (file.branch) {
+		str += ` branches=${file.branch.covered}/${file.branch.total}`;
+	}
+	if (file.declaration) {
+		str += ` declarations=${file.declaration.covered}/${file.declaration.total}`;
+	}
+	str += '>\n';
+
+	try {
+		const details = await file.details();
+
+		const uncoveredDeclarations: { name: string; line: number }[] = [];
+		const uncoveredBranches: { line: number; label?: string }[] = [];
+		const uncoveredLines: [number, number][] = [];
+
+		for (const detail of details) {
+			if (detail.type === DetailType.Declaration) {
+				if (!detail.count) {
+					const line = Position.isIPosition(detail.location) ? detail.location.lineNumber : detail.location.startLineNumber;
+					uncoveredDeclarations.push({ name: detail.name, line });
+				}
+			} else {
+				if (!detail.count) {
+					const startLine = Position.isIPosition(detail.location) ? detail.location.lineNumber : detail.location.startLineNumber;
+					const endLine = Position.isIPosition(detail.location) ? detail.location.lineNumber : detail.location.endLineNumber;
+					uncoveredLines.push([startLine, endLine]);
+				}
+				if (detail.branches) {
+					for (const branch of detail.branches) {
+						if (!branch.count) {
+							let line: number;
+							if (branch.location) {
+								line = Position.isIPosition(branch.location) ? branch.location.lineNumber : branch.location.startLineNumber;
+							} else {
+								line = Position.isIPosition(detail.location) ? detail.location.lineNumber : detail.location.startLineNumber;
+							}
+							uncoveredBranches.push({ line, label: branch.label });
+						}
+					}
+				}
+			}
+		}
+
+		if (uncoveredDeclarations.length) {
+			str += 'uncovered functions: ' + uncoveredDeclarations.map(d => `${d.name}(L${d.line})`).join(', ') + '\n';
+		}
+		if (uncoveredBranches.length) {
+			str += 'uncovered branches: ' + uncoveredBranches.map(b => b.label ? `L${b.line}(${b.label})` : `L${b.line}`).join(', ') + '\n';
+		}
+		if (uncoveredLines.length) {
+			str += 'uncovered lines: ' + mergeLineRanges(uncoveredLines) + '\n';
+		}
+	} catch { /* ignore - details not available */ }
+
+	str += '</coverage>\n';
+	return str;
+}
+
+/** Merges overlapping/contiguous line ranges and formats them compactly. */
+export function mergeLineRanges(ranges: [number, number][]): string {
+	if (!ranges.length) {
+		return '';
+	}
+	ranges.sort((a, b) => a[0] - b[0]);
+	const merged: [number, number][] = [ranges[0]];
+	for (let i = 1; i < ranges.length; i++) {
+		const last = merged[merged.length - 1];
+		const [start, end] = ranges[i];
+		if (start <= last[1] + 1) {
+			last[1] = Math.max(last[1], end);
+		} else {
+			merged.push([start, end]);
+		}
+	}
+	return merged.map(([s, e]) => s === e ? `${s}` : `${s}-${e}`).join(', ');
+}
+
+/** Formats failure details from a test result into an XML-like string. */
+export async function getFailureDetails(result: LiveTestResult): Promise<string> {
+	let str = '';
+	let hadMessages = false;
+	for (const failure of result.tests) {
+		if (!isFailedState(failure.ownComputedState)) {
+			continue;
+		}
+
+		const [, ...testPath] = TestId.split(failure.item.extId);
+		const testName = testPath.pop();
+		str += `<testFailure name=${JSON.stringify(testName)} path=${JSON.stringify(testPath.join(' > '))}>\n`;
+		for (const task of failure.tasks) {
+			for (const message of task.messages.filter(m => m.type === TestMessageType.Error)) {
+				hadMessages = true;
+
+				if (message.expected !== undefined && message.actual !== undefined) {
+					str += `<expectedOutput>\n${message.expected}\n</expectedOutput>\n`;
+					str += `<actualOutput>\n${message.actual}\n</actualOutput>\n`;
+				} else {
+					const messageText = typeof message.message === 'string' ? message.message : message.message.value;
+					str += `<message>\n${messageText}\n</message>\n`;
+				}
+
+				if (message.stackTrace && message.stackTrace.length > 0) {
+					for (const frame of message.stackTrace.slice(0, 10)) {
+						if (frame.uri && frame.position) {
+							str += `<stackFrame path="${frame.uri.fsPath}" line="${frame.position.lineNumber}" col="${frame.position.column}" />\n`;
+						} else if (frame.uri) {
+							str += `<stackFrame path="${frame.uri.fsPath}">${frame.label}</stackFrame>\n`;
+						} else {
+							str += `<stackFrame>${frame.label}</stackFrame>\n`;
+						}
+					}
+				}
+
+				if (message.location) {
+					str += `<location path="${message.location.uri.fsPath}" line="${message.location.range.startLineNumber}" col="${message.location.range.startColumn}" />\n`;
+				}
+			}
+		}
+
+		str += `</testFailure>\n`;
+	}
+
+	if (!hadMessages) {
+		const output = result.tasks.map(t => t.output.getRange(0, t.output.length).toString().trim()).join('\n');
+		if (output) {
+			str += `<output>\n${output}\n</output>\n`;
+		}
+	}
+
+	return str;
+}
diff --git a/src/vs/workbench/contrib/testing/test/common/testingChatAgentTool.test.ts b/src/vs/workbench/contrib/testing/test/common/testingChatAgentTool.test.ts
new file mode 100644
index 0000000000000..a6ede42a9983a
--- /dev/null
+++ b/src/vs/workbench/contrib/testing/test/common/testingChatAgentTool.test.ts
@@ -0,0 +1,721 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { CancellationToken } from '../../../../../base/common/cancellation.js';
+import { Event } from '../../../../../base/common/event.js';
+import { URI } from '../../../../../base/common/uri.js';
+import { upcastPartial } from '../../../../../base/test/common/mock.js';
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+import { Range } from '../../../../../editor/common/core/range.js';
+import { Position } from '../../../../../editor/common/core/position.js';
+import { NullTelemetryService } from '../../../../../platform/telemetry/common/telemetryUtils.js';
+import { IExtUri } from '../../../../../base/common/resources.js';
+import { IUriIdentityService } from '../../../../../platform/uriIdentity/common/uriIdentity.js';
+import { IWorkspace, IWorkspaceContextService, IWorkspaceFolder } from '../../../../../platform/workspace/common/workspace.js';
+import { IToolInvocation, IToolInvocationPreparationContext, IToolProgressStep } from '../../../chat/common/tools/languageModelToolsService.js';
+import { FileCoverage, ICoverageAccessor, TestCoverage } from '../../common/testCoverage.js';
+import { LiveTestResult } from '../../common/testResult.js';
+import { ITestResultService } from '../../common/testResultService.js';
+import { IMainThreadTestCollection, ITestService } from '../../common/testService.js';
+import { CoverageDetails, DetailType, IBranchCoverage, IDeclarationCoverage, IFileCoverage, IStatementCoverage, ResolvedTestRunRequest, TestMessageType, TestResultState, TestRunProfileBitset } from '../../common/testTypes.js';
+import { ITestProfileService } from '../../common/testProfileService.js';
+import { observableValue } from '../../../../../base/common/observable.js';
+import { VSBuffer } from '../../../../../base/common/buffer.js';
+import { TestId } from '../../common/testId.js';
+import { RunTestTool, buildTestRunSummary, getCoverageSummary, getOverallCoverageSummary, getFileCoverageDetails, mergeLineRanges, getFailureDetails } from '../../common/testingChatAgentTool.js';
+
+suite('Workbench - RunTestTool', () => {
+	const ds = ensureNoDisposablesAreLeakedInTestSuite();
+
+	let insertCounter = 0;
+	let tool: RunTestTool;
+
+	const noopProgress = {
+		report: (_update: IToolProgressStep) => { },
+	};
+	const noopCountTokens = () => Promise.resolve(0);
+
+	function createLiveTestResult(request?: ResolvedTestRunRequest): LiveTestResult {
+		const req = request ?? {
+			group: TestRunProfileBitset.Run,
+			targets: [{ profileId: 0, controllerId: 'ctrlId', testIds: ['id-a'] }],
+		};
+		return ds.add(new LiveTestResult(
+			`result-${insertCounter++}`,
+			false,
+			req,
+			insertCounter,
+			NullTelemetryService,
+		));
+	}
+
+	function createTestCoverage(files: { uri: URI; statement: { covered: number; total: number }; branch?: { covered: number; total: number }; declaration?: { covered: number; total: number }; details?: CoverageDetails[] }[]): TestCoverage {
+		const result = createLiveTestResult();
+		const accessor: ICoverageAccessor = {
+			getCoverageDetails: (id, _testId, _token) => {
+				const entry = files.find(f => f.uri.toString() === id);
+				return Promise.resolve(entry?.details ?? []);
+			},
+		};
+		const uriIdentity = upcastPartial<IUriIdentityService>({
+			asCanonicalUri: (uri: URI) => uri,
+			extUri: upcastPartial<IExtUri>({
+				isEqual: (a: URI, b: URI) => a.toString() === b.toString(),
+				ignorePathCasing: () => false,
+			}),
+		});
+		const coverage = new TestCoverage(result, 'task-1', uriIdentity, accessor);
+		for (const f of files) {
+			const fileCoverage: IFileCoverage = {
+				id: f.uri.toString(),
+				uri: f.uri,
+				statement: f.statement,
+				branch: f.branch,
+				declaration: f.declaration,
+			};
+			coverage.append(fileCoverage, undefined);
+		}
+		return coverage;
+	}
+
+	function makeStatement(line: number, count: number, endLine?: number, branches?: IBranchCoverage[]): IStatementCoverage {
+		return {
+			type: DetailType.Statement,
+			count,
+			location: new Range(line, 1, endLine ?? line, 1),
+			branches,
+		};
+	}
+
+	function makeDeclaration(name: string, line: number, count: number): IDeclarationCoverage {
+		return {
+			type: DetailType.Declaration,
+			name,
+			count,
+			location: new Range(line, 1, line, 1),
+		};
+	}
+
+	function makeBranch(line: number, count: number, label?: string): IBranchCoverage {
+		return {
+			count,
+			label,
+			location: new Range(line, 1, line, 1),
+		};
+	}
+
+	function createResultWithCoverage(coverageData: TestCoverage): LiveTestResult {
+		const result = createLiveTestResult();
+		result.addTask({ id: 'task-1', name: 'Test Task', running: true, ctrlId: 'ctrlId' });
+		const taskCov = result.tasks[0].coverage as ReturnType<typeof observableValue<TestCoverage | undefined>>;
+		taskCov.set(coverageData, undefined);
+		return result;
+	}
+
+	function createResultWithTests(tests: { extId: string; label: string; state: TestResultState; messages?: { type: TestMessageType; message: string; expected?: string; actual?: string; location?: { uri: URI; range: Range }; stackTrace?: { uri?: URI; position?: { lineNumber: number; column: number }; label: string }[] }[] }[]): LiveTestResult {
+		const result = createLiveTestResult();
+		result.addTask({ id: 't', name: 'Test Task', running: true, ctrlId: 'ctrlId' });
+
+		for (const t of tests) {
+			const chain = TestId.split(t.extId);
+			const items = chain.map((segment, i) => ({
+				extId: new TestId(chain.slice(0, i + 1)).toString(),
+				label: i === chain.length - 1 ? t.label : segment,
+				busy: false,
+				description: null,
+				error: null,
+				range: null,
+				sortText: null,
+				tags: [],
+				uri: undefined,
+			}));
+			result.addTestChainToRun('ctrlId', items);
+		}
+
+		for (const t of tests) {
+			result.updateState(t.extId, 't', t.state);
+			if (t.messages) {
+				for (const msg of t.messages) {
+					result.appendMessage(t.extId, 't', {
+						type: msg.type as TestMessageType.Error,
+						message: msg.message,
+						expected: msg.expected,
+						actual: msg.actual,
+						contextValue: undefined,
+						location: msg.location ? { uri: msg.location.uri, range: msg.location.range } : undefined,
+						stackTrace: msg.stackTrace?.map(f => ({
+							uri: f.uri,
+							position: f.position ? new Position(f.position.lineNumber, f.position.column) : undefined,
+							label: f.label,
+						})),
+					});
+				}
+			}
+		}
+
+		return result;
+	}
+
+	function createFileCov(uri: URI, statement: { covered: number; total: number }, details: CoverageDetails[], opts?: { branch?: { covered: number; total: number }; declaration?: { covered: number; total: number } }): FileCoverage {
+		const result = createLiveTestResult();
+		const accessor: ICoverageAccessor = {
+			getCoverageDetails: () => Promise.resolve(details),
+		};
+		return new FileCoverage({ id: 'file-1', uri, statement, branch: opts?.branch, declaration: opts?.declaration }, result, accessor);
+	}
+
+	setup(() => {
+		insertCounter = 0;
+
+		const mockTestService = upcastPartial<ITestService>({
+			collection: upcastPartial<IMainThreadTestCollection>({
+				rootItems: [],
+				rootIds: [],
+				expand: () => Promise.resolve(),
+				getNodeById: () => undefined,
+				getNodeByUrl: () => [],
+			}),
+			runTests: () => Promise.resolve(upcastPartial({})),
+			cancelTestRun: () => { },
+		});
+
+		const mockResultService = upcastPartial<ITestResultService>({
+			onResultsChanged: Event.None,
+		});
+
+		const mockProfileService = upcastPartial<ITestProfileService>({
+			capabilitiesForTest: () => TestRunProfileBitset.Run | TestRunProfileBitset.Coverage,
+		});
+
+		const mockUriIdentity = upcastPartial<IUriIdentityService>({
+			asCanonicalUri: (uri: URI) => uri,
+			extUri: upcastPartial<IExtUri>({ isEqual: (a: URI, b: URI) => a.toString() === b.toString() }),
+		});
+
+		const mockWorkspaceContext = upcastPartial<IWorkspaceContextService>({
+			getWorkspace: () => upcastPartial<IWorkspace>({ id: 'test', folders: [upcastPartial<IWorkspaceFolder>({ uri: URI.file('/workspace') })] }),
+		});
+
+		tool = new RunTestTool(
+			mockTestService,
+			mockUriIdentity,
+			mockWorkspaceContext,
+			mockResultService,
+			mockProfileService,
+		);
+	});
+
+	suite('invoke', () => {
+		test('returns error when no tests found', async () => {
+			const result = await tool.invoke(
+				upcastPartial<IToolInvocation>({ parameters: { files: ['/nonexistent/test.ts'] } }),
+				noopCountTokens, noopProgress, CancellationToken.None,
+			);
+			assert.ok(result.toolResultError);
+			assert.ok(result.content[0].kind === 'text' && result.content[0].value.includes('No tests found'));
+		});
+	});
+
+	suite('_buildSummary', () => {
+		test('includes pass/fail counts', async () => {
+			const result = createResultWithTests([
+				{ extId: new TestId(['ctrlId', 'a']).toString(), label: 'a', state: TestResultState.Passed },
+				{ extId: new TestId(['ctrlId', 'b']).toString(), label: 'b', state: TestResultState.Failed, messages: [{ type: TestMessageType.Error, message: 'boom' }] },
+			]);
+			result.markComplete();
+
+			const summary = await buildTestRunSummary(result, 'run', undefined);
+			assert.ok(summary.includes('<summary passed=1 failed=1 />'));
+		});
+
+		test('combines errored and failed in failure count', async () => {
+			const result = createResultWithTests([
+				{ extId: new TestId(['ctrlId', 'a']).toString(), label: 'a', state: TestResultState.Failed, messages: [{ type: TestMessageType.Error, message: 'fail' }] },
+				{ extId: new TestId(['ctrlId', 'b']).toString(), label: 'b', state: TestResultState.Errored, messages: [{ type: TestMessageType.Error, message: 'error' }] },
+				{ extId: new TestId(['ctrlId', 'c']).toString(), label: 'c', state: TestResultState.Passed },
+			]);
+			result.markComplete();
+
+			const summary = await buildTestRunSummary(result, 'run', undefined);
+			assert.ok(summary.includes('failed=2'));
+		});
+
+		test('includes coverage when mode is coverage', async () => {
+			const coverageData = createTestCoverage([
+				{ uri: URI.file('/src/a.ts'), statement: { covered: 8, total: 10 } },
+			]);
+			const result = createResultWithCoverage(coverageData);
+			result.markComplete();
+
+			const summary = await buildTestRunSummary(result, 'coverage', undefined);
+			assert.ok(summary.includes('<coverageSummary>'));
+		});
+
+		test('omits coverage when mode is run', async () => {
+			const result = createLiveTestResult();
+			result.addTask({ id: 't', name: 'n', running: true, ctrlId: 'ctrl' });
+			result.markComplete();
+
+			const summary = await buildTestRunSummary(result, 'run', undefined);
+			assert.ok(!summary.includes('<coverage'));
+		});
+	});
+
+	suite('getCoverageSummary', () => {
+		test('returns overall summary when no coverageFiles specified', async () => {
+			const fileA = URI.file('/src/a.ts');
+			const fileB = URI.file('/src/b.ts');
+			const coverageData = createTestCoverage([
+				{ uri: fileA, statement: { covered: 5, total: 10 } },
+				{ uri: fileB, statement: { covered: 10, total: 10 } },
+			]);
+			const result = createResultWithCoverage(coverageData);
+
+			const summary = await getCoverageSummary(result, undefined);
+			assert.ok(summary.includes('<coverageSummary>'));
+			assert.ok(summary.includes(fileA.fsPath));
+			assert.ok(!summary.includes(fileB.fsPath)); // 100% covered, excluded
+		});
+
+		test('returns detailed summary for specified coverageFiles', async () => {
+			const fileA = URI.file('/src/a.ts');
+			const details: CoverageDetails[] = [
+				makeDeclaration('uncoveredFn', 10, 0),
+				makeStatement(20, 0, 25),
+			];
+			const coverageData = createTestCoverage([
+				{ uri: fileA, statement: { covered: 8, total: 10 }, declaration: { covered: 0, total: 1 }, details },
+			]);
+			const result = createResultWithCoverage(coverageData);
+
+			const summary = await getCoverageSummary(result, [fileA.fsPath]);
+			assert.ok(summary.includes(`<coverage path="${fileA.fsPath}"`));
+			assert.ok(summary.includes('uncovered functions:'));
+			assert.ok(summary.includes('uncoveredFn(L10)'));
+			assert.ok(summary.includes('uncovered lines:'));
+		});
+
+		test('returns empty string when no coverage data exists', async () => {
+			const fileA = URI.file('/src/a.ts');
+			const result = createLiveTestResult();
+			result.addTask({ id: 't', name: 'n', running: true, ctrlId: 'ctrl' });
+
+			const summary = await getCoverageSummary(result, [fileA.fsPath]);
+			assert.strictEqual(summary, '');
+		});
+
+		test('handles multiple coverageFiles', async () => {
+			const fileA = URI.file('/src/a.ts');
+			const fileB = URI.file('/src/b.ts');
+			const coverageData = createTestCoverage([
+				{ uri: fileA, statement: { covered: 8, total: 10 }, details: [makeStatement(5, 0)] },
+				{ uri: fileB, statement: { covered: 3, total: 10 }, details: [makeDeclaration('fn', 1, 0)] },
+			]);
+			const result = createResultWithCoverage(coverageData);
+
+			const summary = await getCoverageSummary(result, [fileA.fsPath, fileB.fsPath]);
+			assert.ok(summary.includes(fileA.fsPath));
+			assert.ok(summary.includes(fileB.fsPath));
+		});
+
+		test('skips non-matching coverageFiles gracefully', async () => {
+			const fileA = URI.file('/src/a.ts');
+			const nonExistent = URI.file('/src/nonexistent.ts');
+			const coverageData = createTestCoverage([
+				{ uri: fileA, statement: { covered: 8, total: 10 } },
+			]);
+			const result = createResultWithCoverage(coverageData);
+
+			const summary = await getCoverageSummary(result, [nonExistent.fsPath]);
+			assert.strictEqual(summary, '');
+		});
+	});
+
+	suite('getOverallCoverageSummary', () => {
+		test('returns all-covered message when everything is 100%', () => {
+			const coverage = createTestCoverage([
+				{ uri: URI.file('/src/a.ts'), statement: { covered: 10, total: 10 } },
+				{ uri: URI.file('/src/b.ts'), statement: { covered: 5, total: 5 } },
+			]);
+			assert.strictEqual(
+				getOverallCoverageSummary(coverage),
+				'<coverageSummary>All files have 100% coverage.</coverageSummary>\n',
+			);
+		});
+
+		test('sorts files by coverage ascending', () => {
+			const high = URI.file('/src/high.ts');
+			const low = URI.file('/src/low.ts');
+			const mid = URI.file('/src/mid.ts');
+			const coverage = createTestCoverage([
+				{ uri: high, statement: { covered: 9, total: 10 } },
+				{ uri: low, statement: { covered: 3, total: 10 } },
+				{ uri: mid, statement: { covered: 7, total: 10 } },
+			]);
+			const summary = getOverallCoverageSummary(coverage);
+			const lowIdx = summary.indexOf(low.fsPath);
+			const midIdx = summary.indexOf(mid.fsPath);
+			const highIdx = summary.indexOf(high.fsPath);
+			assert.ok(lowIdx < midIdx && midIdx < highIdx);
+		});
+
+		test('excludes 100% files from listing', () => {
+			const partial = URI.file('/src/partial.ts');
+			const full = URI.file('/src/full.ts');
+			const coverage = createTestCoverage([
+				{ uri: partial, statement: { covered: 5, total: 10 } },
+				{ uri: full, statement: { covered: 10, total: 10 } },
+			]);
+			const summary = getOverallCoverageSummary(coverage);
+			assert.ok(summary.includes(partial.fsPath));
+			assert.ok(!summary.includes(full.fsPath));
+		});
+
+		test('includes percentage in output', () => {
+			const coverage = createTestCoverage([
+				{ uri: URI.file('/src/a.ts'), statement: { covered: 7, total: 10 } },
+			]);
+			const summary = getOverallCoverageSummary(coverage);
+			assert.ok(summary.includes('percent=70.0'));
+		});
+	});
+
+	suite('getFileCoverageDetails', () => {
+		test('shows header with statement counts', async () => {
+			const uri = URI.file('/src/foo.ts');
+			const file = createFileCov(uri, { covered: 8, total: 10 }, []);
+			const output = await getFileCoverageDetails(file, uri.fsPath);
+			assert.ok(output.includes('statements=8/10'));
+			assert.ok(output.includes('percent=80.0'));
+			assert.ok(output.startsWith(`<coverage path="${uri.fsPath}"`));
+			assert.ok(output.endsWith('</coverage>\n'));
+		});
+
+		test('includes branch counts when available', async () => {
+			const uri = URI.file('/src/foo.ts');
+			const file = createFileCov(uri, { covered: 8, total: 10 }, [], { branch: { covered: 3, total: 5 } });
+			const output = await getFileCoverageDetails(file, uri.fsPath);
+			assert.ok(output.includes('branches=3/5'));
+		});
+
+		test('includes declaration counts when available', async () => {
+			const uri = URI.file('/src/foo.ts');
+			const file = createFileCov(uri, { covered: 8, total: 10 }, [], { declaration: { covered: 2, total: 4 } });
+			const output = await getFileCoverageDetails(file, uri.fsPath);
+			assert.ok(output.includes('declarations=2/4'));
+		});
+
+		test('omits branch/declaration when not available', async () => {
+			const uri = URI.file('/src/foo.ts');
+			const file = createFileCov(uri, { covered: 8, total: 10 }, []);
+			const output = await getFileCoverageDetails(file, uri.fsPath);
+			assert.ok(!output.includes('branches='));
+			assert.ok(!output.includes('declarations='));
+		});
+
+		test('lists uncovered declarations', async () => {
+			const uri = URI.file('/src/foo.ts');
+			const details: CoverageDetails[] = [
+				makeDeclaration('handleError', 89, 0),
+				makeDeclaration('processQueue', 120, 0),
+				makeDeclaration('coveredFn', 50, 3),
+			];
+			const file = createFileCov(uri, { covered: 8, total: 10 }, details, { declaration: { covered: 1, total: 3 } });
+			const output = await getFileCoverageDetails(file, uri.fsPath);
+			assert.ok(output.includes('uncovered functions: handleError(L89), processQueue(L120)'));
+			assert.ok(!output.includes('coveredFn'));
+		});
+
+		test('lists uncovered branches with labels', async () => {
+			const uri = URI.file('/src/foo.ts');
+			const details: CoverageDetails[] = [
+				makeStatement(34, 5, undefined, [
+					makeBranch(34, 5, 'then'),
+					makeBranch(36, 0, 'else'),
+				]),
+				makeStatement(56, 2, undefined, [
+					makeBranch(56, 0, 'case "foo"'),
+					makeBranch(58, 2, 'case "bar"'),
+				]),
+			];
+			const file = createFileCov(uri, { covered: 8, total: 10 }, details, { branch: { covered: 2, total: 4 } });
+			const output = await getFileCoverageDetails(file, uri.fsPath);
+			assert.ok(output.includes('uncovered branches: L36(else), L56(case "foo")'));
+		});
+
+		test('lists uncovered branches without labels', async () => {
+			const uri = URI.file('/src/foo.ts');
+			const details: CoverageDetails[] = [
+				makeStatement(10, 1, undefined, [makeBranch(10, 0)]),
+			];
+			const file = createFileCov(uri, { covered: 8, total: 10 }, details);
+			const output = await getFileCoverageDetails(file, uri.fsPath);
+			assert.ok(output.includes('uncovered branches: L10\n'));
+		});
+
+		test('uses parent statement location when branch has no location', async () => {
+			const uri = URI.file('/src/foo.ts');
+			const details: CoverageDetails[] = [
+				makeStatement(42, 1, undefined, [{ count: 0, label: 'else' }]),
+			];
+			const file = createFileCov(uri, { covered: 8, total: 10 }, details);
+			const output = await getFileCoverageDetails(file, uri.fsPath);
+			assert.ok(output.includes('L42(else)'));
+		});
+
+		test('lists merged uncovered line ranges', async () => {
+			const uri = URI.file('/src/foo.ts');
+			const details: CoverageDetails[] = [
+				makeStatement(23, 0, 27),
+				makeStatement(28, 0, 30),
+				makeStatement(45, 0),
+				makeStatement(67, 0, 72),
+				makeStatement(100, 0, 105),
+				makeStatement(50, 5), // covered
+			];
+			const file = createFileCov(uri, { covered: 5, total: 11 }, details);
+			const output = await getFileCoverageDetails(file, uri.fsPath);
+			assert.ok(output.includes('uncovered lines: 23-30, 45, 67-72, 100-105'));
+		});
+
+		test('omits uncovered sections when all covered', async () => {
+			const uri = URI.file('/src/foo.ts');
+			const details: CoverageDetails[] = [
+				makeDeclaration('fn', 10, 3),
+				makeStatement(20, 5),
+				makeStatement(30, 1, undefined, [makeBranch(30, 1, 'then'), makeBranch(32, 2, 'else')]),
+			];
+			const file = createFileCov(uri, { covered: 10, total: 10 }, details);
+			const output = await getFileCoverageDetails(file, uri.fsPath);
+			assert.ok(!output.includes('uncovered'));
+		});
+
+		test('handles details() throwing gracefully', async () => {
+			const uri = URI.file('/src/err.ts');
+			const result = createLiveTestResult();
+			const accessor: ICoverageAccessor = {
+				getCoverageDetails: () => Promise.reject(new Error('not available')),
+			};
+			const file = new FileCoverage({ id: 'err', uri, statement: { covered: 5, total: 10 } }, result, accessor);
+			const output = await getFileCoverageDetails(file, uri.fsPath);
+			assert.ok(output.includes(`<coverage path="${uri.fsPath}"`));
+			assert.ok(output.includes('</coverage>'));
+			assert.ok(!output.includes('uncovered'));
+		});
+
+		test('full output snapshot', async () => {
+			const uri = URI.file('/src/foo.ts');
+			const details: CoverageDetails[] = [
+				makeDeclaration('uncoveredFn', 10, 0),
+				makeDeclaration('coveredFn', 20, 3),
+				makeStatement(30, 0, 32),
+				makeStatement(40, 5, undefined, [
+					makeBranch(40, 5, 'then'),
+					makeBranch(42, 0, 'else'),
+				]),
+				makeStatement(50, 3),
+			];
+			const file = createFileCov(
+				uri,
+				{ covered: 8, total: 10 },
+				details,
+				{ branch: { covered: 1, total: 2 }, declaration: { covered: 1, total: 2 } },
+			);
+			assert.deepStrictEqual(
+				await getFileCoverageDetails(file, uri.fsPath),
+				`<coverage path="${uri.fsPath}" percent=71.4 statements=8/10 branches=1/2 declarations=1/2>\n` +
+				'uncovered functions: uncoveredFn(L10)\n' +
+				'uncovered branches: L42(else)\n' +
+				'uncovered lines: 30-32\n' +
+				'</coverage>\n',
+			);
+		});
+	});
+
+	suite('mergeLineRanges', () => {
+		test('returns empty for empty input', () => {
+			assert.strictEqual(mergeLineRanges([]), '');
+		});
+
+		test('single range', () => {
+			assert.strictEqual(mergeLineRanges([[5, 10]]), '5-10');
+		});
+
+		test('single line', () => {
+			assert.strictEqual(mergeLineRanges([[5, 5]]), '5');
+		});
+
+		test('merges contiguous ranges', () => {
+			assert.strictEqual(mergeLineRanges([[1, 3], [4, 6]]), '1-6');
+		});
+
+		test('keeps non-contiguous ranges separate', () => {
+			assert.strictEqual(mergeLineRanges([[1, 3], [10, 12]]), '1-3, 10-12');
+		});
+
+		test('merges overlapping ranges', () => {
+			assert.strictEqual(mergeLineRanges([[1, 5], [3, 8]]), '1-8');
+		});
+
+		test('merges adjacent single-line ranges', () => {
+			assert.strictEqual(mergeLineRanges([[5, 5], [6, 6], [10, 10]]), '5-6, 10');
+		});
+
+		test('handles unsorted input', () => {
+			assert.strictEqual(mergeLineRanges([[10, 12], [1, 3], [4, 6]]), '1-6, 10-12');
+		});
+
+		test('handles complex mixed ranges', () => {
+			assert.strictEqual(mergeLineRanges([[1, 1], [3, 5], [2, 2], [7, 9], [10, 10]]), '1-5, 7-10');
+		});
+	});
+
+	suite('getFailureDetails', () => {
+		test('formats expected/actual outputs', async () => {
+			const result = createResultWithTests([{
+				extId: new TestId(['ctrlId', 'suite', 'myTest']).toString(),
+				label: 'myTest',
+				state: TestResultState.Failed,
+				messages: [{
+					type: TestMessageType.Error,
+					message: 'Assertion failed',
+					expected: 'hello',
+					actual: 'world',
+				}],
+			}]);
+			result.markComplete();
+
+			const output = await getFailureDetails(result);
+			assert.ok(output.includes('<expectedOutput>\nhello\n</expectedOutput>'));
+			assert.ok(output.includes('<actualOutput>\nworld\n</actualOutput>'));
+		});
+
+		test('formats plain message when no expected/actual', async () => {
+			const result = createResultWithTests([{
+				extId: new TestId(['ctrlId', 'myTest']).toString(),
+				label: 'myTest',
+				state: TestResultState.Failed,
+				messages: [{
+					type: TestMessageType.Error,
+					message: 'Something went wrong',
+				}],
+			}]);
+			result.markComplete();
+
+			const output = await getFailureDetails(result);
+			assert.ok(output.includes('<message>\nSomething went wrong\n</message>'));
+		});
+
+		test('includes test name and path', async () => {
+			const result = createResultWithTests([{
+				extId: new TestId(['ctrlId', 'suite1', 'suite2', 'myTest']).toString(),
+				label: 'myTest',
+				state: TestResultState.Failed,
+				messages: [{ type: TestMessageType.Error, message: 'fail' }],
+			}]);
+			result.markComplete();
+
+			const output = await getFailureDetails(result);
+			assert.ok(output.includes('name="myTest"'));
+			assert.ok(output.includes('path="suite1 > suite2"'));
+		});
+
+		test('includes stack trace frames', async () => {
+			const testUri = URI.file('/src/test.ts');
+			const helperUri = URI.file('/src/helper.ts');
+			const result = createResultWithTests([{
+				extId: new TestId(['ctrlId', 'myTest']).toString(),
+				label: 'myTest',
+				state: TestResultState.Failed,
+				messages: [{
+					type: TestMessageType.Error,
+					message: 'fail',
+					stackTrace: [
+						{ uri: testUri, position: { lineNumber: 10, column: 5 }, label: 'testFn' },
+						{ uri: helperUri, position: undefined, label: 'helperFn' },
+						{ uri: undefined, position: undefined, label: 'anonymous' },
+					],
+				}],
+			}]);
+			result.markComplete();
+
+			const output = await getFailureDetails(result);
+			assert.ok(output.includes(`path="${testUri.fsPath}" line="10" col="5"`));
+			assert.ok(output.includes(`path="${helperUri.fsPath}">helperFn</stackFrame>`));
+			assert.ok(output.includes('>anonymous</stackFrame>'));
+		});
+
+		test('includes location information', async () => {
+			const testUri = URI.file('/src/test.ts');
+			const result = createResultWithTests([{
+				extId: new TestId(['ctrlId', 'myTest']).toString(),
+				label: 'myTest',
+				state: TestResultState.Failed,
+				messages: [{
+					type: TestMessageType.Error,
+					message: 'fail',
+					location: { uri: testUri, range: new Range(42, 8, 42, 20) },
+				}],
+			}]);
+			result.markComplete();
+
+			const output = await getFailureDetails(result);
+			assert.ok(output.includes(`path="${testUri.fsPath}" line="42" col="8"`));
+		});
+
+		test('skips passing tests', async () => {
+			const result = createResultWithTests([
+				{ extId: new TestId(['ctrlId', 'pass']).toString(), label: 'pass', state: TestResultState.Passed },
+				{ extId: new TestId(['ctrlId', 'fail']).toString(), label: 'fail', state: TestResultState.Failed, messages: [{ type: TestMessageType.Error, message: 'boom' }] },
+			]);
+			result.markComplete();
+
+			const output = await getFailureDetails(result);
+			assert.ok(!output.includes('name="pass"'));
+			assert.ok(output.includes('name="fail"'));
+		});
+
+		test('shows task output when no per-test messages', async () => {
+			const result = createResultWithTests([{
+				extId: new TestId(['ctrlId', 'myTest']).toString(),
+				label: 'myTest',
+				state: TestResultState.Failed,
+			}]);
+			result.appendOutput(VSBuffer.fromString('raw test output'), 't');
+			result.markComplete();
+
+			const output = await getFailureDetails(result);
+			assert.ok(output.includes('<output>\nraw test output\n</output>'));
+		});
+	});
+
+	suite('prepareToolInvocation', () => {
+		test('shows file names in confirmation', async () => {
+			const prepared = await tool.prepareToolInvocation(
+				upcastPartial<IToolInvocationPreparationContext>({ parameters: { files: ['/path/to/test1.ts', '/path/to/test2.ts'] }, toolCallId: 'call-1', chatSessionResource: undefined }),
+				CancellationToken.None,
+			);
+			assert.ok(prepared);
+			const msg = prepared.confirmationMessages?.message;
+			assert.ok(msg);
+			const msgStr = typeof msg === 'string' ? msg : msg.value;
+			assert.ok(msgStr.includes('test1.ts'));
+			assert.ok(msgStr.includes('test2.ts'));
+		});
+
+		test('shows all-tests message when no files', async () => {
+			const prepared = await tool.prepareToolInvocation(
+				upcastPartial<IToolInvocationPreparationContext>({ parameters: {}, toolCallId: 'call-2', chatSessionResource: undefined }),
+				CancellationToken.None,
+			);
+			assert.ok(prepared);
+			const msg = prepared.confirmationMessages?.message;
+			assert.ok(msg);
+			const msgStr = typeof msg === 'string' ? msg : msg.value;
+			assert.ok(msgStr.toLowerCase().includes('all tests'));
+		});
+	});
+});
diff --git a/src/vs/workbench/contrib/themes/test/node/colorRegistry.releaseTest.ts b/src/vs/workbench/contrib/themes/test/node/colorRegistry.releaseTest.ts
index 4c89442974b54..33f120ddfeb63 100644
--- a/src/vs/workbench/contrib/themes/test/node/colorRegistry.releaseTest.ts
+++ b/src/vs/workbench/contrib/themes/test/node/colorRegistry.releaseTest.ts
@@ -121,7 +121,7 @@ suite('Color Registry', function () {
 
 		const docUrl = 'https://raw.githubusercontent.com/microsoft/vscode-docs/vnext/api/references/theme-color.md';
 
-		const reqContext = await new RequestService('local', new TestConfigurationService(), environmentService, new NullLogService()).request({ url: docUrl }, CancellationToken.None);
+		const reqContext = await new RequestService('local', new TestConfigurationService(), environmentService, new NullLogService()).request({ url: docUrl, callSite: 'colorRegistry.releaseTest' }, CancellationToken.None);
 		const content = (await asTextOrError(reqContext))!;
 
 		const expression = /-\s*\`([\w\.]+)\`: (.*)/g;
diff --git a/src/vs/workbench/contrib/update/browser/media/releasenoteseditor.css b/src/vs/workbench/contrib/update/browser/media/releasenoteseditor.css
index 4210055bfeb65..a4a092d83492f 100644
--- a/src/vs/workbench/contrib/update/browser/media/releasenoteseditor.css
+++ b/src/vs/workbench/contrib/update/browser/media/releasenoteseditor.css
@@ -2,8 +2,3 @@
  *  Copyright (c) Microsoft Corporation. All rights reserved.
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
-
-.file-icons-enabled .show-file-icons .webview-vs_code_release_notes-name-file-icon.file-icon::before {
-	content: ' ';
-	background-image: url('../../../../browser/media/code-icon.svg');
-}
diff --git a/src/vs/workbench/contrib/update/browser/media/updateStatusBarEntry.css b/src/vs/workbench/contrib/update/browser/media/updateStatusBarEntry.css
index a35bad5f4696a..c6bf5c799158f 100644
--- a/src/vs/workbench/contrib/update/browser/media/updateStatusBarEntry.css
+++ b/src/vs/workbench/contrib/update/browser/media/updateStatusBarEntry.css
@@ -3,135 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-.update-status-tooltip {
-	display: flex;
-	flex-direction: column;
-	padding: 4px 0;
-	min-width: 310px;
-	max-width: 410px;
-}
-
-/* Header with title and gear icon */
-.update-status-tooltip .header {
-	display: flex;
-	justify-content: space-between;
-	align-items: center;
-	margin-bottom: 12px;
-}
-
-.update-status-tooltip .header .title {
-	font-weight: 600;
-	font-size: var(--vscode-bodyFontSize);
-	color: var(--vscode-foreground);
-	margin-bottom: 0;
-}
-
-.update-status-tooltip .header .monaco-action-bar {
-	margin-left: auto;
-}
-
-/* Product info section with logo */
-.update-status-tooltip .product-info {
-	display: flex;
-	gap: 12px;
-	margin-bottom: 16px;
-}
-
-.update-status-tooltip .product-logo {
-	width: 48px;
-	height: 48px;
-	border-radius: var(--vscode-cornerRadius-large);
-	padding: 5px;
-	flex-shrink: 0;
-	background-image: url('../../../../browser/media/code-icon.svg');
-	background-size: contain;
-	background-position: center;
-	background-repeat: no-repeat;
-}
-
-.update-status-tooltip .product-details {
-	display: flex;
-	flex-direction: column;
-	justify-content: center;
-}
-
-.update-status-tooltip .product-name {
-	font-weight: 600;
-	color: var(--vscode-foreground);
-	margin-bottom: 4px;
-}
-
-.update-status-tooltip .product-version,
-.update-status-tooltip .product-release-date {
-	color: var(--vscode-descriptionForeground);
-	font-size: var(--vscode-bodyFontSize-small);
-}
-
-.update-status-tooltip .release-notes-link {
-	color: var(--vscode-textLink-foreground);
-	text-decoration: none;
-	font-size: var(--vscode-bodyFontSize-small);
-	cursor: pointer;
-}
-
-.update-status-tooltip .release-notes-link:hover {
-	color: var(--vscode-textLink-activeForeground);
-	text-decoration: underline;
-}
-
-/* What's Included section */
-.update-status-tooltip .whats-included .section-title {
-	font-weight: 600;
-	color: var(--vscode-foreground);
-	margin-bottom: 8px;
-}
-
-.update-status-tooltip .whats-included ul {
-	margin: 0;
-	padding-left: 16px;
-	color: var(--vscode-descriptionForeground);
-	font-size: var(--vscode-bodyFontSize-small);
-}
-
-.update-status-tooltip .whats-included li {
-	margin-bottom: 2px;
-}
-
-/* Progress bar */
-.update-status-tooltip .progress-container {
-	margin-bottom: 8px;
-}
-
-.update-status-tooltip .progress-bar {
-	width: 100%;
-	height: 4px;
-	background-color: color-mix(in srgb, var(--vscode-progressBar-background) 30%, transparent);
-	border-radius: var(--vscode-cornerRadius-small);
-	overflow: hidden;
-}
-
-.update-status-tooltip .progress-bar .progress-fill {
-	height: 100%;
-	background-color: var(--vscode-progressBar-background);
-	border-radius: var(--vscode-cornerRadius-small);
-	transition: width 0.3s ease;
-}
-
-.update-status-tooltip .progress-text {
-	display: flex;
-	justify-content: space-between;
-	margin-top: 4px;
-	font-size: var(--vscode-bodyFontSize-small);
-	color: var(--vscode-descriptionForeground);
-}
-
-.update-status-tooltip .progress-details {
-	color: var(--vscode-descriptionForeground);
-	margin-bottom: 4px;
-}
-
-.update-status-tooltip .speed-info,
-.update-status-tooltip .time-remaining {
-	color: var(--vscode-descriptionForeground);
-	font-size: var(--vscode-bodyFontSize-small);
+.monaco-workbench .part.statusbar > .items-container > #status\.update > a > span {
+	color: var(--vscode-button-background);
+	font-size: 16px;
 }
diff --git a/src/vs/workbench/contrib/update/browser/media/updateTitleBarEntry.css b/src/vs/workbench/contrib/update/browser/media/updateTitleBarEntry.css
new file mode 100644
index 0000000000000..266a0a4484895
--- /dev/null
+++ b/src/vs/workbench/contrib/update/browser/media/updateTitleBarEntry.css
@@ -0,0 +1,90 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+.monaco-action-bar .update-indicator {
+	display: flex;
+	align-items: center;
+	border-radius: var(--vscode-cornerRadius-medium);
+	white-space: nowrap;
+	padding: 0px 12px;
+	height: 22px;
+	background-color: transparent;
+	border: 1px solid transparent;
+}
+
+.monaco-action-bar .update-indicator:hover {
+	background-color: var(--vscode-toolbar-hoverBackground);
+}
+
+.monaco-action-bar .update-indicator .indicator-label {
+	font-size: var(--vscode-bodyFontSize-small);
+	position: relative;
+}
+
+/* Prominent state (action required) — primary button style */
+.monaco-action-bar .update-indicator.prominent {
+	background-color: var(--vscode-button-background);
+	color: var(--vscode-button-foreground);
+	border-color: var(--vscode-button-background);
+}
+
+.monaco-action-bar .update-indicator.prominent:hover {
+	background-color: var(--vscode-button-hoverBackground);
+	border-color: var(--vscode-button-hoverBackground);
+}
+
+/* Disabled state */
+.monaco-action-bar .update-indicator.update-disabled .indicator-label {
+	color: var(--vscode-disabledForeground);
+}
+
+/* Progress underline bar (shared base) */
+.monaco-action-bar .update-indicator.progress-indefinite .indicator-label::after,
+.monaco-action-bar .update-indicator.progress-percent .indicator-label::after {
+	content: '';
+	position: absolute;
+	left: 0;
+	bottom: 1px;
+	height: 1px;
+	border-radius: 1px;
+}
+
+/* Progress: indefinite — animated shimmer underline */
+.monaco-action-bar .update-indicator.progress-indefinite .indicator-label::after {
+	width: 100%;
+	background: linear-gradient(
+		90deg,
+		transparent 0%,
+		var(--vscode-progressBar-background) 80%,
+		transparent 100%
+	);
+	background-size: 200% 100%;
+	animation: update-indicator-shimmer 1.5s ease-in-out infinite;
+}
+
+@keyframes update-indicator-shimmer {
+	0% { background-position: 100% 0; }
+	100% { background-position: -100% 0; }
+}
+
+/* Progress: percentage — left-to-right fill underline */
+.monaco-action-bar .update-indicator.progress-percent .indicator-label::after {
+	width: 100%;
+	background: linear-gradient(
+		90deg,
+		var(--vscode-progressBar-background) var(--update-progress, 0%),
+		color-mix(in srgb, var(--vscode-progressBar-background) 25%, transparent) var(--update-progress, 0%)
+	);
+	transition: background 0.3s ease;
+}
+
+/* Reduced motion */
+.monaco-workbench.monaco-reduce-motion .update-indicator.progress-indefinite .indicator-label::after {
+	animation: none;
+}
+
+.monaco-workbench.monaco-reduce-motion .update-indicator.progress-percent .indicator-label::after {
+	transition: none;
+}
diff --git a/src/vs/workbench/contrib/update/browser/media/updateTooltip.css b/src/vs/workbench/contrib/update/browser/media/updateTooltip.css
new file mode 100644
index 0000000000000..96e62c029c339
--- /dev/null
+++ b/src/vs/workbench/contrib/update/browser/media/updateTooltip.css
@@ -0,0 +1,159 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+.update-tooltip {
+	display: flex;
+	flex-direction: column;
+	gap: 12px;
+	padding: 6px 6px;
+	min-width: 320px;
+	max-width: 320px;
+	color: var(--vscode-descriptionForeground);
+	font-size: var(--vscode-bodyFontSize-small);
+}
+
+/* Header */
+.update-tooltip .header {
+	display: flex;
+	justify-content: space-between;
+	align-items: center;
+}
+
+.update-tooltip .header .title {
+	font-weight: 600;
+	font-size: var(--vscode-bodyFontSize);
+	color: var(--vscode-foreground);
+}
+
+/* Product info */
+.update-tooltip .product-info {
+	display: flex;
+	gap: 12px;
+}
+
+.update-tooltip .product-logo {
+	width: 48px;
+	height: 48px;
+	border-radius: var(--vscode-cornerRadius-large);
+	padding: 5px;
+	flex-shrink: 0;
+	background: url('../../../../browser/media/code-icon.svg') center / contain no-repeat;
+}
+
+.update-tooltip .product-details {
+	display: flex;
+	flex-direction: column;
+	justify-content: center;
+}
+
+.update-tooltip .product-name {
+	font-weight: 600;
+	color: var(--vscode-foreground);
+	margin-bottom: 4px;
+}
+
+.update-tooltip .product-version {
+	display: flex;
+	align-items: center;
+	gap: 4px;
+}
+
+.update-tooltip .copy-version-button {
+	cursor: pointer;
+	opacity: 0;
+	color: var(--vscode-descriptionForeground);
+	transition: opacity 0.1s;
+	margin-top: -2px;
+}
+
+.update-tooltip .product-version:hover .copy-version-button,
+.update-tooltip .product-version:focus-within .copy-version-button {
+	opacity: 1;
+}
+
+.update-tooltip .copy-version-button:hover,
+.update-tooltip .copy-version-button:focus-visible {
+	color: var(--vscode-foreground);
+}
+
+.update-tooltip .release-notes-link {
+	color: var(--vscode-textLink-foreground);
+	text-decoration: none;
+}
+
+.update-tooltip .release-notes-link:hover {
+	color: var(--vscode-textLink-activeForeground);
+	text-decoration: underline;
+}
+
+/* Progress bar */
+.update-tooltip .progress-bar {
+	height: 4px;
+	background-color: color-mix(in srgb, var(--vscode-progressBar-background) 30%, transparent);
+	border-radius: var(--vscode-cornerRadius-small);
+	overflow: hidden;
+}
+
+.update-tooltip .progress-fill {
+	height: 100%;
+	background-color: var(--vscode-progressBar-background);
+	border-radius: var(--vscode-cornerRadius-small);
+	transition: width 0.3s ease;
+}
+
+.monaco-workbench.monaco-reduce-motion .update-tooltip .progress-fill {
+	transition: none;
+}
+
+.update-tooltip .progress-text,
+.update-tooltip .download-stats {
+	display: flex;
+	justify-content: space-between;
+}
+
+.update-tooltip .progress-text {
+	margin-top: 4px;
+}
+
+.update-tooltip .state-message {
+	display: flex;
+	align-items: flex-start;
+	font-size: var(--vscode-bodyFontSize);
+	gap: 4px;
+}
+
+.update-tooltip .state-message-icon.codicon[class*='codicon-'] {
+	font-size: 16px;
+	flex-shrink: 0;
+	margin-top: 2px;
+}
+
+.update-tooltip .state-message-icon.codicon.codicon-warning {
+	color: var(--vscode-editorWarning-foreground);
+}
+
+.update-tooltip .state-message-icon.codicon.codicon-error {
+	color: var(--vscode-editorError-foreground);
+}
+
+/* Markdown */
+.update-tooltip .update-markdown {
+	background: var(--vscode-editor-background);
+	border-radius: var(--vscode-cornerRadius-large);
+	padding: 12px;
+}
+
+.update-tooltip .update-markdown p {
+	margin-bottom: 16px;
+}
+
+.update-tooltip .update-markdown p:last-child {
+	margin-bottom: 0;
+}
+
+.update-tooltip .update-markdown .codicon[class*='codicon-'] {
+	font-size: 16px;
+	vertical-align: text-top;
+}
diff --git a/src/vs/workbench/contrib/update/browser/releaseNotesEditor.ts b/src/vs/workbench/contrib/update/browser/releaseNotesEditor.ts
index 550329a85ef9a..2d41bd125bee9 100644
--- a/src/vs/workbench/contrib/update/browser/releaseNotesEditor.ts
+++ b/src/vs/workbench/contrib/update/browser/releaseNotesEditor.ts
@@ -3,8 +3,8 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import './media/releasenoteseditor.css';
 import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { Codicon } from '../../../../base/common/codicons.js';
 import { onUnexpectedError } from '../../../../base/common/errors.js';
 import { escapeMarkdownSyntaxTokens } from '../../../../base/common/htmlContent.js';
 import { KeybindingParser } from '../../../../base/common/keybindingParser.js';
@@ -124,7 +124,7 @@ export class ReleaseNotesManager extends Disposable {
 				},
 				'releaseNotes',
 				title,
-				undefined,
+				Codicon.vscode,
 				{ group: ACTIVE_GROUP, preserveFocus: false });
 
 			const disposables = new DisposableStore();
@@ -222,7 +222,7 @@ export class ReleaseNotesManager extends Disposable {
 					const file = this._codeEditorService.getActiveCodeEditor()?.getModel()?.getValue();
 					text = file ? file.substring(file.indexOf('#')) : undefined;
 				} else {
-					text = await asTextOrError(await this._requestService.request({ url }, CancellationToken.None));
+					text = await asTextOrError(await this._requestService.request({ url, callSite: 'releaseNotesEditor.fetchReleaseNotes' }, CancellationToken.None));
 				}
 			} catch {
 				throw new Error('Failed to fetch release notes');
diff --git a/src/vs/workbench/contrib/update/browser/update.contribution.ts b/src/vs/workbench/contrib/update/browser/update.contribution.ts
index 35a6855e8f9e4..4f19831828be3 100644
--- a/src/vs/workbench/contrib/update/browser/update.contribution.ts
+++ b/src/vs/workbench/contrib/update/browser/update.contribution.ts
@@ -10,7 +10,8 @@ import { IWorkbenchContributionsRegistry, Extensions as WorkbenchExtensions } fr
 import { Categories } from '../../../../platform/action/common/actionCommonCategories.js';
 import { MenuId, registerAction2, Action2 } from '../../../../platform/actions/common/actions.js';
 import { ProductContribution, UpdateContribution, CONTEXT_UPDATE_STATE, SwitchProductQualityContribution, showReleaseNotesInEditor, DefaultAccountUpdateContribution } from './update.js';
-import { UpdateStatusBarEntryContribution } from './updateStatusBarEntry.js';
+import { UpdateStatusBarContribution } from './updateStatusBarEntry.js';
+import { UpdateTitleBarContribution } from './updateTitleBarEntry.js';
 import { LifecyclePhase } from '../../../services/lifecycle/common/lifecycle.js';
 import product from '../../../../platform/product/common/product.js';
 import { IUpdateService, StateType } from '../../../../platform/update/common/update.js';
@@ -30,7 +31,8 @@ workbench.registerWorkbenchContribution(ProductContribution, LifecyclePhase.Rest
 workbench.registerWorkbenchContribution(UpdateContribution, LifecyclePhase.Restored);
 workbench.registerWorkbenchContribution(SwitchProductQualityContribution, LifecyclePhase.Restored);
 workbench.registerWorkbenchContribution(DefaultAccountUpdateContribution, LifecyclePhase.Eventually);
-workbench.registerWorkbenchContribution(UpdateStatusBarEntryContribution, LifecyclePhase.Restored);
+workbench.registerWorkbenchContribution(UpdateStatusBarContribution, LifecyclePhase.Restored);
+workbench.registerWorkbenchContribution(UpdateTitleBarContribution, LifecyclePhase.Restored);
 
 // Release notes
 
diff --git a/src/vs/workbench/contrib/update/browser/update.ts b/src/vs/workbench/contrib/update/browser/update.ts
index a9a3ee1932ec6..36f7d09d2dde1 100644
--- a/src/vs/workbench/contrib/update/browser/update.ts
+++ b/src/vs/workbench/contrib/update/browser/update.ts
@@ -26,11 +26,13 @@ import { IHostService } from '../../../services/host/browser/host.js';
 import { IProductService } from '../../../../platform/product/common/productService.js';
 import { IUserDataSyncEnablementService, IUserDataSyncService, IUserDataSyncStoreManagementService, SyncStatus, UserDataSyncStoreType } from '../../../../platform/userDataSync/common/userDataSync.js';
 import { IsWebContext } from '../../../../platform/contextkey/common/contextkeys.js';
-import { Promises } from '../../../../base/common/async.js';
+import { Promises, Throttler } from '../../../../base/common/async.js';
 import { IUserDataSyncWorkbenchService } from '../../../services/userDataSync/common/userDataSync.js';
 import { Event } from '../../../../base/common/event.js';
 import { toAction } from '../../../../base/common/actions.js';
 import { IDefaultAccountService } from '../../../../platform/defaultAccount/common/defaultAccount.js';
+import { getInternalOrg } from '../../../../platform/assignment/common/assignment.js';
+import { IVersion, preprocessError, tryParseVersion } from '../common/updateUtils.js';
 
 export const CONTEXT_UPDATE_STATE = new RawContextKey<string>('updateState', StateType.Uninitialized);
 export const MAJOR_MINOR_UPDATE_AVAILABLE = new RawContextKey<boolean>('majorMinorUpdateAvailable', false);
@@ -145,26 +147,6 @@ export function appendUpdateMenuItems(menuId: MenuId, group: string): void {
 	});
 }
 
-interface IVersion {
-	major: number;
-	minor: number;
-	patch: number;
-}
-
-function parseVersion(version: string): IVersion | undefined {
-	const match = /([0-9]+)\.([0-9]+)\.([0-9]+)/.exec(version);
-
-	if (!match) {
-		return undefined;
-	}
-
-	return {
-		major: parseInt(match[1]),
-		minor: parseInt(match[2]),
-		patch: parseInt(match[3])
-	};
-}
-
 function isMajorMinorUpdate(before: IVersion, after: IVersion): boolean {
 	return before.major < after.major || before.minor < after.minor;
 }
@@ -192,8 +174,12 @@ export class ProductContribution implements IWorkbenchContribution {
 				return;
 			}
 
-			const lastVersion = parseVersion(storageService.get(ProductContribution.KEY, StorageScope.APPLICATION, ''));
-			const currentVersion = parseVersion(productService.version);
+			if (configurationService.getValue<string>('update.titleBar') !== 'none') {
+				return;
+			}
+
+			const lastVersion = tryParseVersion(storageService.get(ProductContribution.KEY, StorageScope.APPLICATION, ''));
+			const currentVersion = tryParseVersion(productService.version);
 			const shouldShowReleaseNotes = configurationService.getValue<boolean>('update.showReleaseNotes');
 			const releaseNotesUrl = productService.releaseNotesUrl;
 
@@ -228,6 +214,7 @@ export class UpdateContribution extends Disposable implements IWorkbenchContribu
 	private overwriteNotificationHandle: INotificationHandle | undefined;
 	private updateStateContextKey: IContextKey<string>;
 	private majorMinorUpdateAvailableContextKey: IContextKey<boolean>;
+	private titleBarEnabled: boolean;
 
 	constructor(
 		@IStorageService private readonly storageService: IStorageService,
@@ -246,6 +233,7 @@ export class UpdateContribution extends Disposable implements IWorkbenchContribu
 		this.state = updateService.state;
 		this.updateStateContextKey = CONTEXT_UPDATE_STATE.bindTo(this.contextKeyService);
 		this.majorMinorUpdateAvailableContextKey = MAJOR_MINOR_UPDATE_AVAILABLE.bindTo(this.contextKeyService);
+		this.titleBarEnabled = this.configurationService.getValue<string>('update.titleBar') !== 'none';
 
 		this._register(updateService.onStateChange(this.onUpdateStateChange, this));
 		this.onUpdateStateChange(this.updateService.state);
@@ -267,6 +255,13 @@ export class UpdateContribution extends Disposable implements IWorkbenchContribu
 			this.storageService.remove('update/updateNotificationTime', StorageScope.APPLICATION);
 		}
 
+		this._register(this.configurationService.onDidChangeConfiguration(e => {
+			if (e.affectsConfiguration('update.titleBar')) {
+				this.titleBarEnabled = this.configurationService.getValue<string>('update.titleBar') !== 'none';
+				this.onUpdateStateChange(this.updateService.state);
+			}
+		}));
+
 		this.registerGlobalActivityActions();
 	}
 
@@ -275,7 +270,7 @@ export class UpdateContribution extends Disposable implements IWorkbenchContribu
 
 		switch (state.type) {
 			case StateType.Disabled:
-				if (state.reason === DisablementReason.RunningAsAdmin) {
+				if (!this.titleBarEnabled && state.reason === DisablementReason.RunningAsAdmin) {
 					this.notificationService.notify({
 						severity: Severity.Info,
 						message: nls.localize('update service disabled', "Updates are disabled because you are running the user-scope installation of {0} as Administrator.", this.productService.nameLong),
@@ -316,8 +311,8 @@ export class UpdateContribution extends Disposable implements IWorkbenchContribu
 			case StateType.Ready: {
 				const productVersion = state.update.productVersion;
 				if (productVersion) {
-					const currentVersion = parseVersion(this.productService.version);
-					const nextVersion = parseVersion(productVersion);
+					const currentVersion = tryParseVersion(this.productService.version);
+					const nextVersion = tryParseVersion(productVersion);
 					this.majorMinorUpdateAvailableContextKey.set(Boolean(currentVersion && nextVersion && isMajorMinorUpdate(currentVersion, nextVersion)));
 				}
 				this.onUpdateReady(state);
@@ -327,14 +322,16 @@ export class UpdateContribution extends Disposable implements IWorkbenchContribu
 
 		let badge: IBadge | undefined = undefined;
 
-		if (state.type === StateType.AvailableForDownload || state.type === StateType.Downloaded || state.type === StateType.Ready) {
-			badge = new NumberBadge(1, () => nls.localize('updateIsReady', "New {0} update available.", this.productService.nameShort));
-		} else if (state.type === StateType.CheckingForUpdates) {
-			badge = new ProgressBadge(() => nls.localize('checkingForUpdates', "Checking for {0} updates...", this.productService.nameShort));
-		} else if (state.type === StateType.Downloading || state.type === StateType.Overwriting) {
-			badge = new ProgressBadge(() => nls.localize('downloading', "Downloading {0} update...", this.productService.nameShort));
-		} else if (state.type === StateType.Updating) {
-			badge = new ProgressBadge(() => nls.localize('updating', "Updating {0}...", this.productService.nameShort));
+		if (!this.titleBarEnabled) {
+			if (state.type === StateType.AvailableForDownload || state.type === StateType.Downloaded || state.type === StateType.Ready) {
+				badge = new NumberBadge(1, () => nls.localize('updateIsReady', "New {0} update available.", this.productService.nameShort));
+			} else if (state.type === StateType.CheckingForUpdates) {
+				badge = new ProgressBadge(() => nls.localize('checkingForUpdates', "Checking for {0} updates...", this.productService.nameShort));
+			} else if (state.type === StateType.Downloading || state.type === StateType.Overwriting) {
+				badge = new ProgressBadge(() => nls.localize('downloading', "Downloading {0} update...", this.productService.nameShort));
+			} else if (state.type === StateType.Updating) {
+				badge = new ProgressBadge(() => nls.localize('updating', "Updating {0}...", this.productService.nameShort));
+			}
 		}
 
 		this.badgeDisposable.clear();
@@ -347,25 +344,34 @@ export class UpdateContribution extends Disposable implements IWorkbenchContribu
 	}
 
 	private onError(error: string): void {
-		if (/The request timed out|The network connection was lost/i.test(error)) {
+		if (this.titleBarEnabled) {
 			return;
 		}
 
-		error = error.replace(/See https:\/\/github\.com\/Squirrel\/Squirrel\.Mac\/issues\/182 for more information/, 'This might mean the application was put on quarantine by macOS. See [this link](https://github.com/microsoft/vscode/issues/7426#issuecomment-425093469) for more information');
-
-		this.notificationService.notify({
-			severity: Severity.Error,
-			message: error,
-			source: nls.localize('update service', "Update Service"),
-		});
+		const processedError = preprocessError(error);
+		if (processedError) {
+			this.notificationService.notify({
+				severity: Severity.Error,
+				message: processedError,
+				source: nls.localize('update service', "Update Service"),
+			});
+		}
 	}
 
 	private onUpdateNotAvailable(): void {
+		if (this.titleBarEnabled) {
+			return;
+		}
+
 		this.dialogService.info(nls.localize('noUpdatesAvailable', "There are currently no updates available."));
 	}
 
 	// linux
 	private onUpdateAvailable(update: IUpdate): void {
+		if (this.titleBarEnabled) {
+			return;
+		}
+
 		if (!this.shouldShowNotification()) {
 			return;
 		}
@@ -396,6 +402,10 @@ export class UpdateContribution extends Disposable implements IWorkbenchContribu
 
 	// windows fast updates
 	private onUpdateDownloaded(update: IUpdate): void {
+		if (this.titleBarEnabled) {
+			return;
+		}
+
 		if (isMacintosh) {
 			return;
 		}
@@ -433,6 +443,12 @@ export class UpdateContribution extends Disposable implements IWorkbenchContribu
 
 	// windows and mac
 	private onUpdateReady(state: Ready): void {
+		if (this.titleBarEnabled) {
+			this.overwriteNotificationHandle?.progress.done();
+			this.overwriteNotificationHandle = undefined;
+			return;
+		}
+
 		if (state.overwrite && this.overwriteNotificationHandle) {
 			const handle = this.overwriteNotificationHandle;
 			this.overwriteNotificationHandle = undefined;
@@ -484,6 +500,10 @@ export class UpdateContribution extends Disposable implements IWorkbenchContribu
 
 	// macOS overwrite update - overwriting
 	private onUpdateOverwriting(state: Overwriting): void {
+		if (this.titleBarEnabled) {
+			return;
+		}
+
 		if (!state.explicit) {
 			return;
 		}
@@ -675,9 +695,14 @@ export class SwitchProductQualityContribution extends Disposable implements IWor
 
 export class DefaultAccountUpdateContribution extends Disposable implements IWorkbenchContribution {
 
+	private static readonly STORAGE_KEY = 'update/internalOrg';
+	#internalOrg: string | undefined = undefined;
+	private throttler: Throttler = this._register(new Throttler());
+
 	constructor(
 		@IUpdateService private readonly updateService: IUpdateService,
-		@IDefaultAccountService private readonly defaultAccountService: IDefaultAccountService
+		@IDefaultAccountService private readonly defaultAccountService: IDefaultAccountService,
+		@IStorageService private readonly storageService: IStorageService
 	) {
 		super();
 
@@ -685,25 +710,36 @@ export class DefaultAccountUpdateContribution extends Disposable implements IWor
 			return; // Electron only
 		}
 
+		this.#internalOrg = this.storageService.get(DefaultAccountUpdateContribution.STORAGE_KEY, StorageScope.APPLICATION, undefined);
+		this.throttler.queue(() => this.updateService.setInternalOrg(this.#internalOrg));
+
 		// Check on startup
-		this.checkDefaultAccount();
+		this.refresh();
 
 		// Listen for account changes
-		this._register(this.defaultAccountService.onDidChangeDefaultAccount(() => {
-			this.checkDefaultAccount();
-		}));
+		this._register(this.defaultAccountService.onDidChangeDefaultAccount(() => this.refresh()));
 	}
 
-	private async checkDefaultAccount(): Promise<void> {
+	private refresh(): void {
+		this.throttler.queue(() => this.doRefresh());
+	}
+
+	private async doRefresh(): Promise<void> {
 		try {
 			const defaultAccount = await this.defaultAccountService.getDefaultAccount();
-			const shouldDisable = defaultAccount?.entitlementsData?.organization_login_list?.some(
-				org => org.toLowerCase() === 'visual-studio-code'
-			) ?? false;
+			const internalOrg = getInternalOrg(defaultAccount?.entitlementsData?.organization_login_list);
+
+			if (internalOrg === this.#internalOrg) {
+				return;
+			}
+
+			this.#internalOrg = internalOrg;
+			await this.updateService.setInternalOrg(this.#internalOrg);
 
-			if (shouldDisable) {
-				await this.updateService.disableProgressiveReleases();
-				this.dispose();
+			if (this.#internalOrg) {
+				this.storageService.store(DefaultAccountUpdateContribution.STORAGE_KEY, internalOrg, StorageScope.APPLICATION, StorageTarget.MACHINE);
+			} else {
+				this.storageService.remove(DefaultAccountUpdateContribution.STORAGE_KEY, StorageScope.APPLICATION);
 			}
 		} catch (error) {
 			// Silently ignore errors - if we can't get the account, we don't disable background updates
diff --git a/src/vs/workbench/contrib/update/browser/updateStatusBarEntry.ts b/src/vs/workbench/contrib/update/browser/updateStatusBarEntry.ts
index 3d2d6d1c8e0bd..6a9ea130312e4 100644
--- a/src/vs/workbench/contrib/update/browser/updateStatusBarEntry.ts
+++ b/src/vs/workbench/contrib/update/browser/updateStatusBarEntry.ts
@@ -3,39 +3,33 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import * as dom from '../../../../base/browser/dom.js';
-import { ActionBar } from '../../../../base/browser/ui/actionbar/actionbar.js';
-import { toAction } from '../../../../base/common/actions.js';
-import { CancellationToken } from '../../../../base/common/cancellation.js';
-import { Codicon } from '../../../../base/common/codicons.js';
-import { Disposable, DisposableStore, MutableDisposable } from '../../../../base/common/lifecycle.js';
+import { Disposable, MutableDisposable } from '../../../../base/common/lifecycle.js';
 import { isWeb } from '../../../../base/common/platform.js';
-import { ThemeIcon } from '../../../../base/common/themables.js';
-import * as nls from '../../../../nls.js';
-import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { Command } from '../../../../editor/common/languages.js';
+import { localize } from '../../../../nls.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
-import { IHoverService, nativeHoverDelegate } from '../../../../platform/hover/browser/hover.js';
-import { IProductService } from '../../../../platform/product/common/productService.js';
-import { Downloading, IUpdate, IUpdateService, Overwriting, StateType, State as UpdateState, Updating } from '../../../../platform/update/common/update.js';
+import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
+import { Downloading, IUpdateService, StateType, State as UpdateState, Updating } from '../../../../platform/update/common/update.js';
 import { IWorkbenchContribution } from '../../../common/contributions.js';
-import { IStatusbarEntry, IStatusbarEntryAccessor, IStatusbarService, ShowTooltipCommand, StatusbarAlignment, TooltipContent } from '../../../services/statusbar/browser/statusbar.js';
+import { IStatusbarEntry, IStatusbarEntryAccessor, IStatusbarService, ShowTooltipCommand, StatusbarAlignment } from '../../../services/statusbar/browser/statusbar.js';
+import { computeProgressPercent, formatBytes } from '../common/updateUtils.js';
 import './media/updateStatusBarEntry.css';
+import { UpdateTooltip } from './updateTooltip.js';
 
 /**
  * Displays update status and actions in the status bar.
  */
-export class UpdateStatusBarEntryContribution extends Disposable implements IWorkbenchContribution {
-	private static readonly NAME = nls.localize('updateStatus', "Update Status");
-	private readonly statusBarEntryAccessor = this._register(new MutableDisposable<IStatusbarEntryAccessor>());
+export class UpdateStatusBarContribution extends Disposable implements IWorkbenchContribution {
+	private static readonly actionableStates = [StateType.AvailableForDownload, StateType.Downloaded, StateType.Ready];
+	private readonly accessor = this._register(new MutableDisposable<IStatusbarEntryAccessor>());
+	private readonly tooltip!: UpdateTooltip;
 	private lastStateType: StateType | undefined;
 
 	constructor(
-		@IUpdateService private readonly updateService: IUpdateService,
+		@IConfigurationService private readonly configurationService: IConfigurationService,
+		@IInstantiationService instantiationService: IInstantiationService,
 		@IStatusbarService private readonly statusbarService: IStatusbarService,
-		@IProductService private readonly productService: IProductService,
-		@ICommandService private readonly commandService: ICommandService,
-		@IHoverService private readonly hoverService: IHoverService,
-		@IConfigurationService private readonly configurationService: IConfigurationService
+		@IUpdateService updateService: IUpdateService,
 	) {
 		super();
 
@@ -43,536 +37,139 @@ export class UpdateStatusBarEntryContribution extends Disposable implements IWor
 			return; // Electron only
 		}
 
-		this._register(this.updateService.onStateChange(state => this.onUpdateStateChange(state)));
+		this.tooltip = this._register(instantiationService.createInstance(UpdateTooltip, false));
+
+		this._register(updateService.onStateChange(this.onStateChange.bind(this)));
 		this._register(this.configurationService.onDidChangeConfiguration(e => {
-			if (e.affectsConfiguration('update.statusBar')) {
-				this.onUpdateStateChange(this.updateService.state);
+			if (e.affectsConfiguration('update.statusBar') || e.affectsConfiguration('update.titleBar')) {
+				this.onStateChange(updateService.state);
 			}
 		}));
-		this.onUpdateStateChange(this.updateService.state);
+
+		this.onStateChange(updateService.state);
 	}
 
-	private onUpdateStateChange(state: UpdateState) {
-		if (this.lastStateType !== state.type) {
-			this.statusBarEntryAccessor.clear();
-			this.lastStateType = state.type;
+	private onStateChange(state: UpdateState) {
+		const titleBarMode = this.configurationService.getValue<string>('update.titleBar');
+		if (titleBarMode !== 'none') {
+			this.accessor.clear();
+			return;
 		}
 
-		const statusBarMode = this.configurationService.getValue<string>('update.statusBar');
-
-		if (statusBarMode === 'hidden') {
-			this.statusBarEntryAccessor.clear();
+		const mode = this.configurationService.getValue<string>('update.statusBar');
+		if (mode === 'hidden' || mode === 'actionable' && !UpdateStatusBarContribution.actionableStates.includes(state.type)) {
+			this.accessor.clear();
 			return;
 		}
 
-		const actionRequiredStates = [
-			StateType.AvailableForDownload,
-			StateType.Downloaded,
-			StateType.Ready
-		];
-
-		// In 'actionable' mode, only show for states that require user action
-		if (statusBarMode === 'actionable' && !actionRequiredStates.includes(state.type)) {
-			this.statusBarEntryAccessor.clear();
-			return;
+		if (this.lastStateType !== state.type) {
+			this.accessor.clear();
+			this.lastStateType = state.type;
 		}
 
-		const productIcon = this.productService.quality === 'insider' ? '$(vscode-insiders)' : '$(vscode)';
+		this.tooltip.renderState(state);
 		switch (state.type) {
-			case StateType.Uninitialized:
-			case StateType.Idle:
-			case StateType.Disabled:
-				this.statusBarEntryAccessor.clear();
-				break;
-
 			case StateType.CheckingForUpdates:
-				this.updateStatusBarEntry({
-					name: UpdateStatusBarEntryContribution.NAME,
-					text: nls.localize('updateStatus.checkingForUpdates', "$(sync~spin) Checking for updates..."),
-					ariaLabel: nls.localize('updateStatus.checkingForUpdatesAria', "Checking for updates"),
-					tooltip: this.getCheckingTooltip(),
-					command: ShowTooltipCommand,
-				});
+				this.updateEntry(
+					localize('updateStatus.checkingForUpdates', "$(loading~spin) Checking for updates..."),
+					localize('updateStatus.checkingForUpdatesAria', "Checking for updates"),
+					ShowTooltipCommand,
+				);
 				break;
 
 			case StateType.AvailableForDownload:
-				this.updateStatusBarEntry({
-					kind: 'prominent',
-					name: UpdateStatusBarEntryContribution.NAME,
-					text: nls.localize('updateStatus.updateAvailableStatus', "{0} Update available, click to download.", productIcon),
-					ariaLabel: nls.localize('updateStatus.updateAvailableAria', "Update available, click to download."),
-					tooltip: this.getAvailableTooltip(state.update),
-					command: 'update.downloadNow'
-				});
+				this.updateEntry(
+					localize('updateStatus.updateAvailableStatus', "$(circle-filled) Update available, click to download."),
+					localize('updateStatus.updateAvailableAria', "Update available, click to download."),
+					'update.downloadNow'
+				);
 				break;
 
 			case StateType.Downloading:
-				this.updateStatusBarEntry({
-					name: UpdateStatusBarEntryContribution.NAME,
-					text: this.getDownloadingText(state),
-					ariaLabel: nls.localize('updateStatus.downloadingUpdateAria', "Downloading update"),
-					tooltip: this.getDownloadingTooltip(state),
-					command: ShowTooltipCommand
-				});
+				this.updateEntry(
+					this.getDownloadingText(state),
+					localize('updateStatus.downloadingUpdateAria', "Downloading update"),
+					ShowTooltipCommand
+				);
 				break;
 
 			case StateType.Downloaded:
-				this.updateStatusBarEntry({
-					kind: 'prominent',
-					name: UpdateStatusBarEntryContribution.NAME,
-					text: nls.localize('updateStatus.updateReadyStatus', "{0} Update downloaded, click to install.", productIcon),
-					ariaLabel: nls.localize('updateStatus.updateReadyAria', "Update downloaded, click to install."),
-					tooltip: this.getReadyToInstallTooltip(state.update),
-					command: 'update.install'
-				});
+				this.updateEntry(
+					localize('updateStatus.updateReadyStatus', "$(circle-filled) Update downloaded, click to install."),
+					localize('updateStatus.updateReadyAria', "Update downloaded, click to install."),
+					'update.install'
+				);
 				break;
 
 			case StateType.Updating:
-				this.updateStatusBarEntry({
-					name: UpdateStatusBarEntryContribution.NAME,
-					text: this.getUpdatingText(state),
-					ariaLabel: this.getUpdatingText(state),
-					tooltip: this.getUpdatingTooltip(state),
-					command: ShowTooltipCommand
-				});
+				this.updateEntry(
+					this.getUpdatingText(state),
+					undefined,
+					ShowTooltipCommand
+				);
 				break;
 
-			case StateType.Ready: {
-
-				this.updateStatusBarEntry({
-					kind: 'prominent',
-					name: UpdateStatusBarEntryContribution.NAME,
-					text: nls.localize('updateStatus.restartToUpdateStatus', "{0} Update is ready, click to restart.", productIcon),
-					ariaLabel: nls.localize('updateStatus.restartToUpdateAria', "Update is ready, click to restart."),
-					tooltip: this.getRestartToUpdateTooltip(state.update),
-					command: 'update.restart'
-				});
+			case StateType.Ready:
+				this.updateEntry(
+					localize('updateStatus.restartToUpdateStatus', "$(circle-filled) Update is ready, click to restart."),
+					localize('updateStatus.restartToUpdateAria', "Update is ready, click to restart."),
+					'update.restart'
+				);
 				break;
-			}
 
 			case StateType.Overwriting:
-				this.updateStatusBarEntry({
-					name: UpdateStatusBarEntryContribution.NAME,
-					text: nls.localize('updateStatus.downloadingNewerUpdateStatus', "$(sync~spin) Downloading update..."),
-					ariaLabel: nls.localize('updateStatus.downloadingNewerUpdateAria', "Downloading a newer update"),
-					tooltip: this.getOverwritingTooltip(state),
-					command: ShowTooltipCommand
-				});
+				this.updateEntry(
+					localize('updateStatus.downloadingNewerUpdateStatus', "$(loading~spin) Downloading update..."),
+					localize('updateStatus.downloadingNewerUpdateAria', "Downloading a newer update"),
+					ShowTooltipCommand
+				);
+				break;
+
+			default:
+				this.accessor.clear();
 				break;
 		}
 	}
 
-	private updateStatusBarEntry(entry: IStatusbarEntry) {
-		if (this.statusBarEntryAccessor.value) {
-			this.statusBarEntryAccessor.value.update(entry);
+	private updateEntry(text: string, ariaLabel: string | undefined, command: string | Command) {
+		const entry: IStatusbarEntry = {
+			text,
+			ariaLabel: ariaLabel ?? text,
+			name: localize('updateStatus', "Update Status"),
+			tooltip: this.tooltip?.domNode,
+			command
+		};
+
+		if (this.accessor.value) {
+			this.accessor.value.update(entry);
 		} else {
-			this.statusBarEntryAccessor.value = this.statusbarService.addEntry(
+			this.accessor.value = this.statusbarService.addEntry(
 				entry,
 				'status.update',
 				StatusbarAlignment.LEFT,
-				{
-					location: { id: 'status.host', priority: Number.MAX_VALUE },
-					alignment: StatusbarAlignment.LEFT
-				}
+				-Number.MAX_VALUE
 			);
 		}
 	}
 
-	private getCheckingTooltip(): TooltipContent {
-		return {
-			element: (token: CancellationToken) => {
-				const store = this.createTooltipDisposableStore(token);
-				const container = dom.$('.update-status-tooltip');
-
-				this.appendHeader(container, nls.localize('updateStatus.checkingForUpdatesTitle', "Checking for Updates"), store);
-				this.appendProductInfo(container);
-
-				const message = dom.append(container, dom.$('.progress-details'));
-				message.textContent = nls.localize('updateStatus.checkingPleaseWait', "Checking for updates, please wait...");
-
-				return container;
-			}
-		};
-	}
-
-	private getAvailableTooltip(update: IUpdate): TooltipContent {
-		return {
-			element: (token: CancellationToken) => {
-				const store = this.createTooltipDisposableStore(token);
-				const container = dom.$('.update-status-tooltip');
-
-				this.appendHeader(container, nls.localize('updateStatus.updateAvailableTitle', "Update Available"), store);
-				this.appendProductInfo(container, update);
-				this.appendWhatsIncluded(container);
-
-				return container;
-			}
-		};
-	}
-
 	private getDownloadingText({ downloadedBytes, totalBytes }: Downloading): string {
 		if (downloadedBytes !== undefined && totalBytes !== undefined && totalBytes > 0) {
-			return nls.localize('updateStatus.downloadUpdateProgressStatus', "$(sync~spin) Downloading update: {0} / {1} • {2}%",
+			const percent = computeProgressPercent(downloadedBytes, totalBytes) ?? 0;
+			return localize('updateStatus.downloadUpdateProgressStatus', "$(loading~spin) Downloading update: {0} / {1} • {2}%",
 				formatBytes(downloadedBytes),
 				formatBytes(totalBytes),
-				getProgressPercent(downloadedBytes, totalBytes) ?? 0);
+				percent);
 		} else {
-			return nls.localize('updateStatus.downloadUpdateStatus', "$(sync~spin) Downloading update...");
+			return localize('updateStatus.downloadUpdateStatus', "$(loading~spin) Downloading update...");
 		}
 	}
 
-	private getDownloadingTooltip(state: Downloading): TooltipContent {
-		return {
-			element: (token: CancellationToken) => {
-				const store = this.createTooltipDisposableStore(token);
-				const container = dom.$('.update-status-tooltip');
-
-				this.appendHeader(container, nls.localize('updateStatus.downloadingUpdateTitle', "Downloading Update"), store);
-				this.appendProductInfo(container, state.update);
-
-				const { downloadedBytes, totalBytes } = state;
-				if (downloadedBytes !== undefined && totalBytes !== undefined && totalBytes > 0) {
-					const percentage = getProgressPercent(downloadedBytes, totalBytes) ?? 0;
-
-					const progressContainer = dom.append(container, dom.$('.progress-container'));
-					const progressBar = dom.append(progressContainer, dom.$('.progress-bar'));
-					const progressFill = dom.append(progressBar, dom.$('.progress-fill'));
-					progressFill.style.width = `${percentage}%`;
-
-					const progressText = dom.append(progressContainer, dom.$('.progress-text'));
-					const percentageSpan = dom.append(progressText, dom.$('span'));
-					percentageSpan.textContent = `${percentage}%`;
-
-					const sizeSpan = dom.append(progressText, dom.$('span'));
-					sizeSpan.textContent = `${formatBytes(downloadedBytes)} / ${formatBytes(totalBytes)}`;
-
-					const speed = computeDownloadSpeed(state);
-					if (speed !== undefined && speed > 0) {
-						const speedInfo = dom.append(container, dom.$('.speed-info'));
-						speedInfo.textContent = nls.localize('updateStatus.downloadSpeed', '{0}/s', formatBytes(speed));
-					}
-
-					const timeRemaining = computeDownloadTimeRemaining(state);
-					if (timeRemaining !== undefined && timeRemaining > 0) {
-						const timeRemainingNode = dom.append(container, dom.$('.time-remaining'));
-						timeRemainingNode.textContent = `~${formatTimeRemaining(timeRemaining)} ${nls.localize('updateStatus.timeRemaining', "remaining")}`;
-					}
-				} else {
-					const message = dom.append(container, dom.$('.progress-details'));
-					message.textContent = nls.localize('updateStatus.downloadingPleaseWait', "Downloading, please wait...");
-				}
-
-				return container;
-			}
-		};
-	}
-
-	private getReadyToInstallTooltip(update: IUpdate): TooltipContent {
-		return {
-			element: (token: CancellationToken) => {
-				const store = this.createTooltipDisposableStore(token);
-				const container = dom.$('.update-status-tooltip');
-
-				this.appendHeader(container, nls.localize('updateStatus.updateReadyTitle', "Update is Ready to Install"), store);
-				this.appendProductInfo(container, update);
-				this.appendWhatsIncluded(container);
-
-				return container;
-			}
-		};
-	}
-
-	private getRestartToUpdateTooltip(update: IUpdate): TooltipContent {
-		return {
-			element: (token: CancellationToken) => {
-				const store = this.createTooltipDisposableStore(token);
-				const container = dom.$('.update-status-tooltip');
-
-				this.appendHeader(container, nls.localize('updateStatus.updateInstalledTitle', "Update Installed"), store);
-				this.appendProductInfo(container, update);
-				this.appendWhatsIncluded(container);
-
-				return container;
-			}
-		};
-	}
-
 	private getUpdatingText({ currentProgress, maxProgress }: Updating): string {
-		const percentage = getProgressPercent(currentProgress, maxProgress);
+		const percentage = computeProgressPercent(currentProgress, maxProgress);
 		if (percentage !== undefined) {
-			return nls.localize('updateStatus.installingUpdateProgressStatus', "$(sync~spin) Installing update: {0}%", percentage);
+			return localize('updateStatus.installingUpdateProgressStatus', "$(loading~spin) Installing update: {0}%", percentage);
 		} else {
-			return nls.localize('updateStatus.installingUpdateStatus', "$(sync~spin) Installing update...");
+			return localize('updateStatus.installingUpdateStatus', "$(loading~spin) Installing update...");
 		}
 	}
-
-	private getUpdatingTooltip(state: Updating): TooltipContent {
-		return {
-			element: (token: CancellationToken) => {
-				const store = this.createTooltipDisposableStore(token);
-				const container = dom.$('.update-status-tooltip');
-
-				this.appendHeader(container, nls.localize('updateStatus.installingUpdateTitle', "Installing Update"), store);
-				this.appendProductInfo(container, state.update);
-
-				const { currentProgress, maxProgress } = state;
-				const percentage = getProgressPercent(currentProgress, maxProgress);
-				if (percentage !== undefined) {
-					const progressContainer = dom.append(container, dom.$('.progress-container'));
-					const progressBar = dom.append(progressContainer, dom.$('.progress-bar'));
-					const progressFill = dom.append(progressBar, dom.$('.progress-fill'));
-					progressFill.style.width = `${percentage}%`;
-
-					const progressText = dom.append(progressContainer, dom.$('.progress-text'));
-					const percentageSpan = dom.append(progressText, dom.$('span'));
-					percentageSpan.textContent = `${percentage}%`;
-				} else {
-					const message = dom.append(container, dom.$('.progress-details'));
-					message.textContent = nls.localize('updateStatus.installingPleaseWait', "Installing update, please wait...");
-				}
-
-				return container;
-			}
-		};
-	}
-
-	private getOverwritingTooltip(state: Overwriting): TooltipContent {
-		return {
-			element: (token: CancellationToken) => {
-				const store = this.createTooltipDisposableStore(token);
-				const container = dom.$('.update-status-tooltip');
-
-				this.appendHeader(container, nls.localize('updateStatus.downloadingNewerUpdateTitle', "Downloading Newer Update"), store);
-				this.appendProductInfo(container, state.update);
-
-				const message = dom.append(container, dom.$('.progress-details'));
-				message.textContent = nls.localize('updateStatus.downloadingNewerPleaseWait', "A newer update was released. Downloading, please wait...");
-
-				return container;
-			}
-		};
-	}
-
-	private createTooltipDisposableStore(token: CancellationToken): DisposableStore {
-		const store = new DisposableStore();
-		store.add(token.onCancellationRequested(() => store.dispose()));
-		return store;
-	}
-
-	private runCommandAndClose(command: string, ...args: unknown[]): void {
-		this.commandService.executeCommand(command, ...args);
-		this.hoverService.hideHover(true);
-	}
-
-	private appendHeader(container: HTMLElement, title: string, store: DisposableStore) {
-		const header = dom.append(container, dom.$('.header'));
-		const text = dom.append(header, dom.$('.title'));
-		text.textContent = title;
-
-		const actionBar = store.add(new ActionBar(header, { hoverDelegate: nativeHoverDelegate }));
-		actionBar.push([toAction({
-			id: 'update.openSettings',
-			label: nls.localize('updateStatus.settingsTooltip', "Update Settings"),
-			class: ThemeIcon.asClassName(Codicon.gear),
-			run: () => this.runCommandAndClose('workbench.action.openSettings', '@id:update*'),
-		})], { icon: true, label: false });
-	}
-
-	private appendProductInfo(container: HTMLElement, update?: IUpdate) {
-		const productInfo = dom.append(container, dom.$('.product-info'));
-
-		const logoContainer = dom.append(productInfo, dom.$('.product-logo'));
-		logoContainer.setAttribute('role', 'img');
-		logoContainer.setAttribute('aria-label', this.productService.nameLong);
-
-		const details = dom.append(productInfo, dom.$('.product-details'));
-
-		const productName = dom.append(details, dom.$('.product-name'));
-		productName.textContent = this.productService.nameLong;
-
-		const productVersion = this.productService.version;
-		if (productVersion) {
-			const currentVersion = dom.append(details, dom.$('.product-version'));
-			const currentCommitId = this.productService.commit?.substring(0, 7);
-			currentVersion.textContent = currentCommitId
-				? nls.localize('updateStatus.currentVersionLabelWithCommit', "Current Version: {0} ({1})", productVersion, currentCommitId)
-				: nls.localize('updateStatus.currentVersionLabel', "Current Version: {0}", productVersion);
-		}
-
-		const version = update?.productVersion;
-		if (version) {
-			const latestVersion = dom.append(details, dom.$('.product-version'));
-			const updateCommitId = update.version?.substring(0, 7);
-			latestVersion.textContent = updateCommitId
-				? nls.localize('updateStatus.latestVersionLabelWithCommit', "Latest Version: {0} ({1})", version, updateCommitId)
-				: nls.localize('updateStatus.latestVersionLabel', "Latest Version: {0}", version);
-		}
-
-		const releaseDate = update?.timestamp ?? tryParseDate(this.productService.date);
-		if (typeof releaseDate === 'number' && releaseDate > 0) {
-			const releaseDateNode = dom.append(details, dom.$('.product-release-date'));
-			releaseDateNode.textContent = nls.localize('updateStatus.releasedLabel', "Released {0}", formatDate(releaseDate));
-		}
-
-		const releaseNotesVersion = version ?? productVersion;
-		if (releaseNotesVersion) {
-			const link = dom.append(details, dom.$('a.release-notes-link')) as HTMLAnchorElement;
-			link.textContent = nls.localize('updateStatus.releaseNotesLink', "Release Notes");
-			link.href = '#';
-			link.addEventListener('click', (e) => {
-				e.preventDefault();
-				this.runCommandAndClose('update.showCurrentReleaseNotes', releaseNotesVersion);
-			});
-		}
-	}
-
-	private appendWhatsIncluded(container: HTMLElement) {
-		/*
-		const whatsIncluded = dom.append(container, dom.$('.whats-included'));
-
-		const sectionTitle = dom.append(whatsIncluded, dom.$('.section-title'));
-		sectionTitle.textContent = nls.localize('updateStatus.whatsIncludedTitle', "What's Included");
-
-		const list = dom.append(whatsIncluded, dom.$('ul'));
-
-		const items = [
-			nls.localize('updateStatus.featureItem', "New features and functionality"),
-			nls.localize('updateStatus.bugFixesItem', "Bug fixes and improvements"),
-			nls.localize('updateStatus.securityItem', "Security fixes and enhancements")
-		];
-
-		for (const item of items) {
-			const li = dom.append(list, dom.$('li'));
-			li.textContent = item;
-		}
-		*/
-	}
-}
-
-/**
- * Returns the progress percentage based on the current and maximum progress values.
- */
-export function getProgressPercent(current: number | undefined, max: number | undefined): number | undefined {
-	if (current === undefined || max === undefined || max <= 0) {
-		return undefined;
-	} else {
-		return Math.max(Math.min(Math.round((current / max) * 100), 100), 0);
-	}
-}
-
-/**
- * Tries to parse a date string and returns the timestamp or undefined if parsing fails.
- */
-export function tryParseDate(date: string | undefined): number | undefined {
-	if (date === undefined) {
-		return undefined;
-	}
-	const parsed = Date.parse(date);
-	return isNaN(parsed) ? undefined : parsed;
-}
-
-/**
- * Formats a timestamp as a localized date string.
- */
-export function formatDate(timestamp: number): string {
-	return new Date(timestamp).toLocaleDateString(undefined, {
-		year: 'numeric',
-		month: 'short',
-		day: 'numeric'
-	});
-}
-
-/**
- * Computes an estimate of remaining download time in seconds.
- */
-export function computeDownloadTimeRemaining(state: Downloading): number | undefined {
-	const { downloadedBytes, totalBytes, startTime } = state;
-	if (downloadedBytes === undefined || totalBytes === undefined || startTime === undefined) {
-		return undefined;
-	}
-
-	const elapsedMs = Date.now() - startTime;
-	if (downloadedBytes <= 0 || totalBytes <= 0 || elapsedMs <= 0) {
-		return undefined;
-	}
-
-	const remainingBytes = totalBytes - downloadedBytes;
-	if (remainingBytes <= 0) {
-		return 0;
-	}
-
-	const bytesPerMs = downloadedBytes / elapsedMs;
-	if (bytesPerMs <= 0) {
-		return undefined;
-	}
-
-	const remainingMs = remainingBytes / bytesPerMs;
-	return Math.ceil(remainingMs / 1000);
-}
-
-/**
- * Formats the time remaining as a human-readable string.
- */
-export function formatTimeRemaining(seconds: number): string {
-	const hours = seconds / 3600;
-	if (hours >= 1) {
-		const formattedHours = formatDecimal(hours);
-		return formattedHours === '1'
-			? nls.localize('timeRemainingHour', "{0} hour", formattedHours)
-			: nls.localize('timeRemainingHours', "{0} hours", formattedHours);
-	}
-
-	const minutes = Math.floor(seconds / 60);
-	if (minutes >= 1) {
-		return nls.localize('timeRemainingMinutes', "{0} min", minutes);
-	}
-
-	return nls.localize('timeRemainingSeconds', "{0}s", seconds);
-}
-
-/**
- * Formats a byte count as a human-readable string.
- */
-export function formatBytes(bytes: number): string {
-	if (bytes < 1024) {
-		return nls.localize('bytes', "{0} B", bytes);
-	}
-
-	const kb = bytes / 1024;
-	if (kb < 1024) {
-		return nls.localize('kilobytes', "{0} KB", formatDecimal(kb));
-	}
-
-	const mb = kb / 1024;
-	if (mb < 1024) {
-		return nls.localize('megabytes', "{0} MB", formatDecimal(mb));
-	}
-
-	const gb = mb / 1024;
-	return nls.localize('gigabytes', "{0} GB", formatDecimal(gb));
-}
-
-/**
- * Formats a number to 1 decimal place, omitting ".0" for whole numbers.
- */
-function formatDecimal(value: number): string {
-	const rounded = Math.round(value * 10) / 10;
-	return rounded % 1 === 0 ? rounded.toString() : rounded.toFixed(1);
-}
-
-/**
- * Computes the current download speed in bytes per second.
- */
-export function computeDownloadSpeed(state: Downloading): number | undefined {
-	const { downloadedBytes, startTime } = state;
-	if (downloadedBytes === undefined || startTime === undefined) {
-		return undefined;
-	}
-
-	const elapsedMs = Date.now() - startTime;
-	if (elapsedMs <= 0 || downloadedBytes <= 0) {
-		return undefined;
-	}
-
-	return (downloadedBytes / elapsedMs) * 1000;
 }
diff --git a/src/vs/workbench/contrib/update/browser/updateTitleBarEntry.ts b/src/vs/workbench/contrib/update/browser/updateTitleBarEntry.ts
new file mode 100644
index 0000000000000..7c8912a27cbbb
--- /dev/null
+++ b/src/vs/workbench/contrib/update/browser/updateTitleBarEntry.ts
@@ -0,0 +1,361 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../base/browser/dom.js';
+import { BaseActionViewItem, IBaseActionViewItemOptions } from '../../../../base/browser/ui/actionbar/actionViewItems.js';
+import { IManagedHoverContent } from '../../../../base/browser/ui/hover/hover.js';
+import { IAction } from '../../../../base/common/actions.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
+import { isWeb } from '../../../../base/common/platform.js';
+import { localize } from '../../../../nls.js';
+import { IActionViewItemService } from '../../../../platform/actions/browser/actionViewItemService.js';
+import { Action2, MenuId, registerAction2 } from '../../../../platform/actions/common/actions.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
+import { IContextKey, IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
+import { IHoverService } from '../../../../platform/hover/browser/hover.js';
+import { IInstantiationService } from '../../../../platform/instantiation/common/instantiation.js';
+import { IProductService } from '../../../../platform/product/common/productService.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
+import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
+import { DisablementReason, IUpdateService, State, StateType } from '../../../../platform/update/common/update.js';
+import { IWorkbenchContribution } from '../../../common/contributions.js';
+import { IHostService } from '../../../services/host/browser/host.js';
+import { computeProgressPercent, isMajorMinorVersionChange } from '../common/updateUtils.js';
+import './media/updateTitleBarEntry.css';
+import { UpdateTooltip } from './updateTooltip.js';
+
+const UPDATE_TITLE_BAR_ACTION_ID = 'workbench.actions.updateIndicator';
+const UPDATE_TITLE_BAR_CONTEXT = new RawContextKey<boolean>('updateTitleBar', false);
+
+const ACTIONABLE_STATES: readonly StateType[] = [StateType.AvailableForDownload, StateType.Downloaded, StateType.Ready];
+const DETAILED_STATES: readonly StateType[] = [...ACTIONABLE_STATES, StateType.CheckingForUpdates, StateType.Downloading, StateType.Updating, StateType.Overwriting];
+
+const LAST_KNOWN_VERSION_KEY = 'updateTitleBarEntry/lastKnownVersion';
+
+interface ILastKnownVersion {
+	readonly version: string;
+	readonly commit: string | undefined;
+	readonly timestamp: number;
+}
+
+registerAction2(class UpdateIndicatorTitleBarAction extends Action2 {
+	constructor() {
+		super({
+			id: UPDATE_TITLE_BAR_ACTION_ID,
+			title: localize('updateIndicatorTitleBarAction', 'Update'),
+			f1: false,
+			menu: [{
+				id: MenuId.CommandCenter,
+				order: 10003,
+				when: UPDATE_TITLE_BAR_CONTEXT,
+			}]
+		});
+	}
+
+	override async run() { }
+});
+
+/**
+ * Displays update status and actions in the title bar.
+ */
+export class UpdateTitleBarContribution extends Disposable implements IWorkbenchContribution {
+	private readonly context!: IContextKey<boolean>;
+	private readonly tooltip!: UpdateTooltip;
+	private mode: 'always' | 'detailed' | 'actionable' | 'none' = 'none';
+	private state!: State;
+	private entry: UpdateTitleBarEntry | undefined;
+	private tooltipVisible = false;
+
+	constructor(
+		@IActionViewItemService actionViewItemService: IActionViewItemService,
+		@IConfigurationService private readonly configurationService: IConfigurationService,
+		@IContextKeyService contextKeyService: IContextKeyService,
+		@IHostService private readonly hostService: IHostService,
+		@IInstantiationService instantiationService: IInstantiationService,
+		@IProductService private readonly productService: IProductService,
+		@IStorageService private readonly storageService: IStorageService,
+		@ITelemetryService private readonly telemetryService: ITelemetryService,
+		@IUpdateService updateService: IUpdateService,
+	) {
+		super();
+
+		if (isWeb) {
+			return; // Electron only
+		}
+
+		this.context = UPDATE_TITLE_BAR_CONTEXT.bindTo(contextKeyService);
+		this.tooltip = this._register(instantiationService.createInstance(UpdateTooltip, true));
+
+		this.mode = configurationService.getValue<string>('update.titleBar') as typeof this.mode;
+		this._register(configurationService.onDidChangeConfiguration(e => {
+			if (e.affectsConfiguration('update.titleBar')) {
+				this.mode = configurationService.getValue<string>('update.titleBar') as typeof this.mode;
+				this.onStateChange();
+			}
+		}));
+
+		this.state = updateService.state;
+		this._register(updateService.onStateChange((state) => {
+			this.state = state;
+			this.onStateChange();
+		}));
+
+		this._register(actionViewItemService.register(
+			MenuId.CommandCenter,
+			UPDATE_TITLE_BAR_ACTION_ID,
+			(action, options) => {
+				this.entry = instantiationService.createInstance(UpdateTitleBarEntry, action, options, this.tooltip, () => {
+					this.tooltipVisible = false;
+					this.updateContext();
+				});
+				if (this.tooltipVisible) {
+					this.entry.showTooltip();
+				}
+				return this.entry;
+			}
+		));
+
+		void this.onStateChange(true);
+	}
+
+	private updateContext() {
+		switch (this.mode) {
+			case 'always':
+				this.context.set(true);
+				break;
+			case 'detailed':
+				this.context.set(DETAILED_STATES.includes(this.state.type));
+				break;
+			case 'actionable':
+				this.context.set(ACTIONABLE_STATES.includes(this.state.type));
+				break;
+			default:
+				this.context.set(false);
+				break;
+		}
+	}
+
+	private async onStateChange(detectVersionChange = false) {
+		this.updateContext();
+		if (this.mode === 'none' || this.tooltipVisible || !await this.hostService.hadLastFocus()) {
+			return;
+		}
+
+		let showTooltip = detectVersionChange && this.detectVersionChange();
+		if (showTooltip) {
+			this.tooltip.renderPostInstall();
+		} else {
+			this.tooltip.renderState(this.state);
+			switch (this.state.type) {
+				case StateType.Disabled:
+					showTooltip = this.state.reason === DisablementReason.InvalidConfiguration || this.state.reason === DisablementReason.RunningAsAdmin;
+					break;
+				case StateType.Idle:
+					showTooltip = !!this.state.error || !!this.state.notAvailable;
+					break;
+				case StateType.AvailableForDownload:
+				case StateType.Downloaded:
+				case StateType.Ready:
+					showTooltip = true;
+					break;
+			}
+		}
+
+		if (showTooltip) {
+			this.tooltipVisible = true;
+			this.context.set(true);
+			this.entry?.showTooltip();
+		}
+	}
+
+	private detectVersionChange() {
+		let from: ILastKnownVersion | undefined;
+		try {
+			from = this.storageService.getObject(LAST_KNOWN_VERSION_KEY, StorageScope.APPLICATION);
+		} catch { }
+
+		const to: ILastKnownVersion = {
+			version: this.productService.version,
+			commit: this.productService.commit,
+			timestamp: Date.now(),
+		};
+
+		if (from?.commit === to.commit) {
+			return false;
+		}
+
+		this.storageService.store(LAST_KNOWN_VERSION_KEY, JSON.stringify(to), StorageScope.APPLICATION, StorageTarget.MACHINE);
+
+		if (from) {
+			this.trackVersionChange(from, to);
+			return isMajorMinorVersionChange(from.version, to.version);
+		}
+
+		return false;
+	}
+
+	private trackVersionChange(from: ILastKnownVersion, to: ILastKnownVersion) {
+		type VersionChangeEvent = {
+			fromVersion: string | undefined;
+			fromCommit: string | undefined;
+			fromVersionTime: number | undefined;
+			toVersion: string;
+			toCommit: string | undefined;
+			timeToUpdateMs: number | undefined;
+			updateMode: string | undefined;
+			titleBarMode: string | undefined;
+		};
+
+		type VersionChangeClassification = {
+			owner: 'dmitriv';
+			comment: 'Fired when VS Code detects a version change on startup.';
+			fromVersion: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The previous version of VS Code.' };
+			fromCommit: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The commit hash of the previous version.' };
+			fromVersionTime: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'Timestamp when the previous version was first detected.' };
+			toVersion: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The current version of VS Code.' };
+			toCommit: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The commit hash of the current version.' };
+			timeToUpdateMs: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; isMeasurement: true; comment: 'Milliseconds between the previous version install and this version install.' };
+			updateMode: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The update mode configured by the user.' };
+			titleBarMode: { classification: 'SystemMetaData'; purpose: 'FeatureInsight'; comment: 'The title bar update indicator mode configured by the user.' };
+		};
+
+		this.telemetryService.publicLog2<VersionChangeEvent, VersionChangeClassification>('update:versionChanged', {
+			fromVersion: from.version,
+			fromCommit: from.commit,
+			fromVersionTime: from.timestamp,
+			toVersion: to.version,
+			toCommit: to.commit,
+			timeToUpdateMs: from.timestamp !== undefined ? to.timestamp - from.timestamp : undefined,
+			updateMode: this.configurationService.getValue<string>('update.mode'),
+			titleBarMode: this.mode
+		});
+	}
+}
+
+/**
+ * Custom action view item for the update indicator in the title bar.
+ */
+export class UpdateTitleBarEntry extends BaseActionViewItem {
+	private content: HTMLElement | undefined;
+	private showTooltipOnRender = false;
+
+	constructor(
+		action: IAction,
+		options: IBaseActionViewItemOptions,
+		private readonly tooltip: UpdateTooltip,
+		private readonly onUserDismissedTooltip: () => void,
+		@ICommandService private readonly commandService: ICommandService,
+		@IHoverService private readonly hoverService: IHoverService,
+		@IUpdateService private readonly updateService: IUpdateService,
+	) {
+		super(undefined, action, options);
+
+		this.action.run = () => this.runAction();
+		this._register(this.updateService.onStateChange(state => this.onStateChange(state)));
+	}
+
+	public override render(container: HTMLElement) {
+		super.render(container);
+
+		this.content = dom.append(container, dom.$('.update-indicator'));
+		this.updateTooltip();
+		this.onStateChange(this.updateService.state);
+
+		if (this.showTooltipOnRender) {
+			this.showTooltipOnRender = false;
+			dom.scheduleAtNextAnimationFrame(dom.getWindow(container), () => this.showTooltip());
+		}
+	}
+
+	public showTooltip(focus = false) {
+		if (!this.content?.isConnected) {
+			this.showTooltipOnRender = true;
+			return;
+		}
+
+		this.hoverService.showInstantHover({
+			content: this.tooltip.domNode,
+			target: {
+				targetElements: [this.content],
+				dispose: () => {
+					if (!!this.content?.isConnected) {
+						this.onUserDismissedTooltip();
+					}
+				}
+			},
+			persistence: { sticky: true },
+			appearance: { showPointer: true, compact: true },
+		}, focus);
+	}
+
+	protected override getHoverContents(): IManagedHoverContent {
+		return this.tooltip.domNode;
+	}
+
+	private runAction() {
+		switch (this.updateService.state.type) {
+			case StateType.AvailableForDownload:
+				this.commandService.executeCommand('update.downloadNow');
+				break;
+			case StateType.Downloaded:
+				this.commandService.executeCommand('update.install');
+				break;
+			case StateType.Ready:
+				this.commandService.executeCommand('update.restart');
+				break;
+			default:
+				this.showTooltip(true);
+				break;
+		}
+	}
+
+	private onStateChange(state: State) {
+		if (!this.content) {
+			return;
+		}
+
+		dom.clearNode(this.content);
+		this.content.classList.remove('prominent', 'progress-indefinite', 'progress-percent', 'update-disabled');
+		this.content.style.removeProperty('--update-progress');
+
+		const label = dom.append(this.content, dom.$('.indicator-label'));
+		label.textContent = localize('updateIndicator.update', "Update");
+
+		switch (state.type) {
+			case StateType.Disabled:
+				this.content.classList.add('update-disabled');
+				break;
+
+			case StateType.CheckingForUpdates:
+			case StateType.Overwriting:
+				this.renderProgressState(this.content);
+				break;
+
+			case StateType.AvailableForDownload:
+			case StateType.Downloaded:
+			case StateType.Ready:
+				this.content.classList.add('prominent');
+				break;
+
+			case StateType.Downloading:
+				this.renderProgressState(this.content, computeProgressPercent(state.downloadedBytes, state.totalBytes));
+				break;
+
+			case StateType.Updating:
+				this.renderProgressState(this.content, computeProgressPercent(state.currentProgress, state.maxProgress));
+				break;
+		}
+	}
+
+	private renderProgressState(content: HTMLElement, percentage?: number) {
+		if (percentage !== undefined) {
+			content.classList.add('progress-percent');
+			content.style.setProperty('--update-progress', `${percentage}%`);
+		} else {
+			content.classList.add('progress-indefinite');
+		}
+	}
+}
diff --git a/src/vs/workbench/contrib/update/browser/updateTooltip.ts b/src/vs/workbench/contrib/update/browser/updateTooltip.ts
new file mode 100644
index 0000000000000..56e15f6a0cf64
--- /dev/null
+++ b/src/vs/workbench/contrib/update/browser/updateTooltip.ts
@@ -0,0 +1,483 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../base/browser/dom.js';
+import { ActionBar } from '../../../../base/browser/ui/actionbar/actionbar.js';
+import { toAction } from '../../../../base/common/actions.js';
+import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { MarkdownString } from '../../../../base/common/htmlContent.js';
+import { Disposable, MutableDisposable } from '../../../../base/common/lifecycle.js';
+import { ThemeIcon } from '../../../../base/common/themables.js';
+import { localize } from '../../../../nls.js';
+import { IClipboardService } from '../../../../platform/clipboard/common/clipboardService.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
+import { IHoverService, nativeHoverDelegate } from '../../../../platform/hover/browser/hover.js';
+import { IMarkdownRendererService, openLinkFromMarkdown } from '../../../../platform/markdown/browser/markdownRenderer.js';
+import { IMeteredConnectionService } from '../../../../platform/meteredConnection/common/meteredConnection.js';
+import { IOpenerService } from '../../../../platform/opener/common/opener.js';
+import { IProductService } from '../../../../platform/product/common/productService.js';
+import { asTextOrError, IRequestService } from '../../../../platform/request/common/request.js';
+import { AvailableForDownload, Disabled, DisablementReason, Downloaded, Downloading, Idle, IUpdate, Overwriting, Ready, State, StateType, Updating } from '../../../../platform/update/common/update.js';
+import { computeDownloadSpeed, computeDownloadTimeRemaining, computeProgressPercent, formatBytes, formatDate, formatTimeRemaining, getUpdateInfoUrl, tryParseDate } from '../common/updateUtils.js';
+import './media/updateTooltip.css';
+
+/**
+ * A stateful tooltip control for the update status.
+ */
+export class UpdateTooltip extends Disposable {
+	public readonly domNode: HTMLElement;
+
+	// Header section
+	private readonly titleNode: HTMLElement;
+
+	// Product info section
+	private readonly productInfoNode: HTMLElement;
+	private readonly productNameNode: HTMLElement;
+	private readonly currentVersionNode: HTMLElement;
+	private readonly currentVersionCopyValue: { value: string };
+	private readonly latestVersionNode: HTMLElement;
+	private readonly latestVersionCopyValue: { value: string };
+	private readonly releaseDateNode: HTMLElement;
+	private readonly releaseNotesLink: HTMLAnchorElement;
+
+	// Progress section
+	private readonly progressContainer: HTMLElement;
+	private readonly progressFill: HTMLElement;
+	private readonly progressPercentNode: HTMLElement;
+	private readonly progressSizeNode: HTMLElement;
+
+	// Extra download info
+	private readonly downloadStatsContainer: HTMLElement;
+	private readonly timeRemainingNode: HTMLElement;
+	private readonly speedInfoNode: HTMLElement;
+
+	// Update markdown section
+	private readonly markdownContainer: HTMLElement;
+	private readonly markdown = this._register(new MutableDisposable());
+
+	// State-specific message
+	private readonly messageNode: HTMLElement;
+
+	private releaseNotesVersion: string | undefined;
+
+	constructor(
+		private readonly hostedByTitleBar: boolean,
+		@IClipboardService private readonly clipboardService: IClipboardService,
+		@ICommandService private readonly commandService: ICommandService,
+		@IConfigurationService private readonly configurationService: IConfigurationService,
+		@IHoverService private readonly hoverService: IHoverService,
+		@IMarkdownRendererService private readonly markdownRendererService: IMarkdownRendererService,
+		@IMeteredConnectionService private readonly meteredConnectionService: IMeteredConnectionService,
+		@IOpenerService private readonly openerService: IOpenerService,
+		@IProductService private readonly productService: IProductService,
+		@IRequestService private readonly requestService: IRequestService,
+	) {
+		super();
+
+		this.domNode = dom.$('.update-tooltip');
+
+		// Header section
+		const header = dom.append(this.domNode, dom.$('.header'));
+		this.titleNode = dom.append(header, dom.$('.title'));
+
+		const actionBar = this._register(new ActionBar(header, { hoverDelegate: nativeHoverDelegate }));
+		actionBar.push(toAction({
+			id: 'update.openSettings',
+			label: localize('updateTooltip.settingsTooltip', "Update Settings"),
+			class: ThemeIcon.asClassName(Codicon.gear),
+			run: () => this.runCommandAndClose('workbench.action.openSettings', '@id:update*'),
+		}), { icon: true, label: false });
+
+		// Product info section
+		this.productInfoNode = dom.append(this.domNode, dom.$('.product-info'));
+
+		const logoContainer = dom.append(this.productInfoNode, dom.$('.product-logo'));
+		logoContainer.setAttribute('role', 'img');
+		logoContainer.setAttribute('aria-label', this.productService.nameLong);
+
+		const details = dom.append(this.productInfoNode, dom.$('.product-details'));
+
+		this.productNameNode = dom.append(details, dom.$('.product-name'));
+		this.productNameNode.textContent = this.productService.nameLong;
+
+		const currentVersionRow = this.createVersionRow(details);
+		this.currentVersionNode = currentVersionRow.label;
+		this.currentVersionCopyValue = currentVersionRow.copyValue;
+
+		const latestVersionRow = this.createVersionRow(details);
+		this.latestVersionNode = latestVersionRow.label;
+		this.latestVersionCopyValue = latestVersionRow.copyValue;
+
+		this.releaseDateNode = dom.append(details, dom.$('.product-release-date'));
+
+		this.releaseNotesLink = dom.append(details, dom.$('a.release-notes-link')) as HTMLAnchorElement;
+		this.releaseNotesLink.textContent = localize('updateTooltip.releaseNotesLink', "Release Notes");
+		this.releaseNotesLink.href = '#';
+		this._register(dom.addDisposableListener(this.releaseNotesLink, 'click', (e) => {
+			e.preventDefault();
+			if (this.releaseNotesVersion) {
+				this.runCommandAndClose('update.showCurrentReleaseNotes', this.releaseNotesVersion);
+			}
+		}));
+
+		// Progress section
+		this.progressContainer = dom.append(this.domNode, dom.$('.progress-container'));
+		const progressBar = dom.append(this.progressContainer, dom.$('.progress-bar'));
+		this.progressFill = dom.append(progressBar, dom.$('.progress-fill'));
+
+		const progressText = dom.append(this.progressContainer, dom.$('.progress-text'));
+		this.progressPercentNode = dom.append(progressText, dom.$('span'));
+		this.progressSizeNode = dom.append(progressText, dom.$('span'));
+
+		// Extra download stats
+		this.downloadStatsContainer = dom.append(this.progressContainer, dom.$('.download-stats'));
+		this.timeRemainingNode = dom.append(this.downloadStatsContainer, dom.$('.time-remaining'));
+		this.speedInfoNode = dom.append(this.downloadStatsContainer, dom.$('.speed-info'));
+
+		// Update markdown section
+		this.markdownContainer = dom.append(this.domNode, dom.$('.update-markdown'));
+
+		// State-specific message
+		this.messageNode = dom.append(this.domNode, dom.$('.state-message'));
+
+		// Populate static product info
+		this.updateCurrentVersion();
+	}
+
+	private updateCurrentVersion() {
+		const productVersion = this.productService.version;
+		if (productVersion) {
+			const currentCommitId = this.productService.commit?.substring(0, 7);
+			this.currentVersionNode.textContent = currentCommitId
+				? localize('updateTooltip.currentVersionLabelWithCommit', "Current Version: {0} ({1})", productVersion, currentCommitId)
+				: localize('updateTooltip.currentVersionLabel', "Current Version: {0}", productVersion);
+			this.currentVersionCopyValue.value = currentCommitId ? `${productVersion} (${this.productService.commit})` : productVersion;
+			this.currentVersionNode.parentElement!.style.display = '';
+		} else {
+			this.currentVersionNode.parentElement!.style.display = 'none';
+		}
+	}
+
+	private hideAll() {
+		this.productInfoNode.style.display = '';
+		this.progressContainer.style.display = 'none';
+		this.speedInfoNode.textContent = '';
+		this.timeRemainingNode.textContent = '';
+		this.messageNode.style.display = 'none';
+		this.markdownContainer.style.display = 'none';
+		this.markdown.clear();
+	}
+
+	public renderState(state: State) {
+		this.hideAll();
+		switch (state.type) {
+			case StateType.Uninitialized:
+				this.renderUninitialized();
+				break;
+			case StateType.Disabled:
+				this.renderDisabled(state);
+				break;
+			case StateType.Idle:
+				this.renderIdle(state);
+				break;
+			case StateType.CheckingForUpdates:
+				this.renderCheckingForUpdates();
+				break;
+			case StateType.AvailableForDownload:
+				this.renderAvailableForDownload(state);
+				break;
+			case StateType.Downloading:
+				this.renderDownloading(state);
+				break;
+			case StateType.Downloaded:
+				this.renderDownloaded(state);
+				break;
+			case StateType.Updating:
+				this.renderUpdating(state);
+				break;
+			case StateType.Ready:
+				this.renderReady(state);
+				break;
+			case StateType.Overwriting:
+				this.renderOverwriting(state);
+				break;
+		}
+	}
+
+	private renderUninitialized() {
+		this.renderTitleAndInfo(localize('updateTooltip.initializingTitle', "Initializing"));
+		this.renderMessage(localize('updateTooltip.initializingMessage', "Initializing update service..."));
+	}
+
+	private renderDisabled({ reason }: Disabled) {
+		this.renderTitleAndInfo(localize('updateTooltip.updatesDisabledTitle', "Updates Disabled"));
+		switch (reason) {
+			case DisablementReason.NotBuilt:
+				this.renderMessage(
+					localize('updateTooltip.disabledNotBuilt', "Updates are not available for this build."),
+					Codicon.info);
+				break;
+			case DisablementReason.DisabledByEnvironment:
+				this.renderMessage(
+					localize('updateTooltip.disabledByEnvironment', "Updates are disabled by the --disable-updates command line flag."),
+					Codicon.warning);
+				break;
+			case DisablementReason.ManuallyDisabled:
+				this.renderMessage(
+					localize('updateTooltip.disabledManually', "Updates are manually disabled. Change the \"update.mode\" setting to enable."),
+					Codicon.warning);
+				break;
+			case DisablementReason.Policy:
+				this.renderMessage(
+					localize('updateTooltip.disabledByPolicy', "Updates are disabled by organization policy."),
+					Codicon.info);
+				break;
+			case DisablementReason.MissingConfiguration:
+				this.renderMessage(
+					localize('updateTooltip.disabledMissingConfig', "Updates are disabled because no update URL is configured."),
+					Codicon.info);
+				break;
+			case DisablementReason.InvalidConfiguration:
+				this.renderMessage(
+					localize('updateTooltip.disabledInvalidConfig', "Updates are disabled because the update URL is invalid."),
+					Codicon.error);
+				break;
+			case DisablementReason.RunningAsAdmin:
+				this.renderMessage(
+					localize(
+						'updateTooltip.disabledRunningAsAdmin',
+						"Updates are not available when running a user install of {0} as administrator.",
+						this.productService.nameShort),
+					Codicon.warning);
+				break;
+			default:
+				this.renderMessage(localize('updateTooltip.disabledGeneric', "Updates are disabled."), Codicon.warning);
+				break;
+		}
+	}
+
+	private renderIdle({ error, notAvailable }: Idle) {
+		if (error) {
+			this.renderTitleAndInfo(localize('updateTooltip.updateErrorTitle', "Update Error"));
+			this.renderMessage(error, Codicon.error);
+			return;
+		}
+
+		if (notAvailable) {
+			this.renderTitleAndInfo(localize('updateTooltip.noUpdateAvailableTitle', "No Update Available"));
+			this.renderMessage(localize('updateTooltip.noUpdateAvailableMessage', "There are no updates currently available."), Codicon.info);
+			return;
+		}
+
+		this.renderTitleAndInfo(localize('updateTooltip.upToDateTitle', "Up to Date"));
+		switch (this.configurationService.getValue<string>('update.mode')) {
+			case 'none':
+				this.renderMessage(localize('updateTooltip.autoUpdateNone', "Automatic updates are disabled."), Codicon.warning);
+				break;
+			case 'manual':
+				this.renderMessage(localize('updateTooltip.autoUpdateManual', "Automatic updates will be checked but not installed automatically."));
+				break;
+			case 'start':
+				this.renderMessage(localize('updateTooltip.autoUpdateStart', "Updates will be applied on restart."));
+				break;
+			case 'default':
+				if (this.meteredConnectionService.isConnectionMetered) {
+					this.renderMessage(
+						localize('updateTooltip.meteredConnectionMessage', "Automatic updates are paused because the network connection is metered."),
+						Codicon.radioTower);
+				} else {
+					this.renderMessage(
+						localize('updateTooltip.autoUpdateDefault', "Automatic updates are enabled. Happy Coding!"),
+						Codicon.smiley);
+				}
+				break;
+		}
+	}
+
+	private renderCheckingForUpdates() {
+		this.renderTitleAndInfo(localize('updateTooltip.checkingForUpdatesTitle', "Checking for Updates"));
+		this.renderMessage(localize('updateTooltip.checkingPleaseWait', "Checking for updates, please wait..."));
+	}
+
+	private renderAvailableForDownload({ update }: AvailableForDownload) {
+		this.renderTitleAndInfo(localize('updateTooltip.updateAvailableTitle', "Update Available"), update);
+		if (this.hostedByTitleBar) {
+			this.renderMessage(localize('updateTooltip.clickToDownload', "Click the Update button to download."));
+		}
+	}
+
+	private renderDownloading(state: Downloading) {
+		this.renderTitleAndInfo(localize('updateTooltip.downloadingUpdateTitle', "Downloading Update"), state.update);
+
+		const { downloadedBytes, totalBytes } = state;
+		if (downloadedBytes !== undefined && totalBytes !== undefined && totalBytes > 0) {
+			const percentage = computeProgressPercent(downloadedBytes, totalBytes) ?? 0;
+			this.progressFill.style.width = `${percentage}%`;
+			this.progressPercentNode.textContent = `${percentage}%`;
+			this.progressSizeNode.textContent = `${formatBytes(downloadedBytes)} / ${formatBytes(totalBytes)}`;
+			this.progressContainer.style.display = '';
+
+			const speed = computeDownloadSpeed(state);
+			if (speed !== undefined && speed > 0) {
+				this.speedInfoNode.textContent = localize('updateTooltip.downloadSpeed', '{0}/s', formatBytes(speed));
+			}
+
+			const timeRemaining = computeDownloadTimeRemaining(state);
+			if (timeRemaining !== undefined && timeRemaining > 0) {
+				this.timeRemainingNode.textContent = `~${formatTimeRemaining(timeRemaining)} ${localize('updateTooltip.timeRemaining', "remaining")}`;
+			}
+
+			this.downloadStatsContainer.style.display = '';
+		} else {
+			this.renderMessage(localize('updateTooltip.downloadingPleaseWait', "Downloading update, please wait..."));
+		}
+	}
+
+	private renderDownloaded({ update }: Downloaded) {
+		this.renderTitleAndInfo(localize('updateTooltip.updateReadyTitle', "Update is Ready to Install"), update);
+		if (this.hostedByTitleBar) {
+			this.renderMessage(localize('updateTooltip.clickToInstall', "Click the Update button to install."));
+		}
+	}
+
+	private renderUpdating({ update, currentProgress, maxProgress }: Updating) {
+		this.renderTitleAndInfo(localize('updateTooltip.installingUpdateTitle', "Installing Update"), update);
+
+		const percentage = computeProgressPercent(currentProgress, maxProgress);
+		if (percentage !== undefined) {
+			this.progressFill.style.width = `${percentage}%`;
+			this.progressPercentNode.textContent = `${percentage}%`;
+			this.progressSizeNode.textContent = '';
+			this.progressContainer.style.display = '';
+		} else {
+			this.renderMessage(localize('updateTooltip.installingPleaseWait', "Installing update, please wait..."));
+		}
+	}
+
+	private renderReady({ update }: Ready) {
+		this.renderTitleAndInfo(localize('updateTooltip.updateInstalledTitle', "Update Installed"), update);
+		if (this.hostedByTitleBar) {
+			this.renderMessage(localize('updateTooltip.clickToRestart', "Click the Update button to restart and apply."));
+		}
+	}
+
+	private renderOverwriting({ update }: Overwriting) {
+		this.renderTitleAndInfo(localize('updateTooltip.downloadingNewerUpdateTitle', "Downloading Newer Update"), update);
+		this.renderMessage(localize('updateTooltip.downloadingNewerPleaseWait', "A newer update was released. Downloading, please wait..."));
+	}
+
+	public async renderPostInstall() {
+		this.hideAll();
+		this.renderTitleAndInfo(localize('updateTooltip.installedDefaultTitle', "New Update Installed"));
+		this.renderMessage(
+			localize('updateTooltip.installedDefaultMessage', "See release notes for details on what's new in this release."),
+			Codicon.info);
+
+		let text = null;
+		try {
+			const url = getUpdateInfoUrl(this.productService.version);
+			const context = await this.requestService.request({ url, callSite: 'updateTooltip' }, CancellationToken.None);
+			text = await asTextOrError(context);
+		} catch { }
+
+		if (!text) {
+			return;
+		}
+
+		this.titleNode.textContent = localize('updateTooltip.installedTitle', "New in {0}", this.productService.version);
+		this.productInfoNode.style.display = 'none';
+		this.messageNode.style.display = 'none';
+
+		const rendered = this.markdownRendererService.render(
+			new MarkdownString(text, {
+				isTrusted: true,
+				supportHtml: true,
+				supportThemeIcons: true,
+			}),
+			{
+				actionHandler: (link, mdStr) => {
+					openLinkFromMarkdown(this.openerService, link, mdStr.isTrusted);
+					this.hoverService.hideHover(true);
+				},
+			});
+
+		this.markdown.value = rendered;
+		dom.clearNode(this.markdownContainer);
+		this.markdownContainer.appendChild(rendered.element);
+		this.markdownContainer.style.display = '';
+	}
+
+	private renderTitleAndInfo(title: string, update?: IUpdate) {
+		this.titleNode.textContent = title;
+
+		// Latest version
+		const version = update?.productVersion;
+		if (version) {
+			const updateCommitId = update.version?.substring(0, 7);
+			this.latestVersionNode.textContent = updateCommitId
+				? localize('updateTooltip.latestVersionLabelWithCommit', "Latest Version: {0} ({1})", version, updateCommitId)
+				: localize('updateTooltip.latestVersionLabel', "Latest Version: {0}", version);
+			this.latestVersionCopyValue.value = updateCommitId ? `${version} (${update.version})` : version;
+			this.latestVersionNode.parentElement!.style.display = '';
+		} else {
+			this.latestVersionNode.parentElement!.style.display = 'none';
+		}
+
+		// Release date
+		const releaseDate = update?.timestamp ?? tryParseDate(this.productService.date);
+		if (typeof releaseDate === 'number' && releaseDate > 0) {
+			this.releaseDateNode.textContent = localize('updateTooltip.releasedLabel', "Released {0}", formatDate(releaseDate));
+			this.releaseDateNode.style.display = '';
+		} else {
+			this.releaseDateNode.style.display = 'none';
+		}
+
+		// Release notes link
+		this.releaseNotesVersion = version ?? this.productService.version;
+		this.releaseNotesLink.style.display = this.releaseNotesVersion ? '' : 'none';
+	}
+
+	private renderMessage(message: string, icon?: ThemeIcon) {
+		dom.clearNode(this.messageNode);
+		if (icon) {
+			const iconNode = dom.append(this.messageNode, dom.$('.state-message-icon'));
+			iconNode.classList.add(...ThemeIcon.asClassNameArray(icon));
+		}
+		dom.append(this.messageNode, document.createTextNode(message));
+		this.messageNode.style.display = '';
+	}
+
+	private createVersionRow(parent: HTMLElement): { label: HTMLElement; copyValue: { value: string } } {
+		const row = dom.append(parent, dom.$('.product-version'));
+		const label = dom.append(row, dom.$('span'));
+		const copyValue = { value: '' };
+
+		const copyButton = dom.append(row, dom.$('a.copy-version-button'));
+		copyButton.setAttribute('role', 'button');
+		copyButton.setAttribute('tabindex', '0');
+		const title = localize('updateTooltip.copyVersion', "Copy");
+		copyButton.title = title;
+		copyButton.setAttribute('aria-label', title);
+
+		const copyIcon = dom.append(copyButton, dom.$('.copy-icon'));
+		copyIcon.classList.add(...ThemeIcon.asClassNameArray(Codicon.copy));
+		this._register(dom.addDisposableListener(copyButton, 'click', e => {
+			e.preventDefault();
+			e.stopPropagation();
+			if (copyValue.value) {
+				this.clipboardService.writeText(copyValue.value);
+			}
+		}));
+
+		return { label, copyValue };
+	}
+
+	private runCommandAndClose(command: string, ...args: unknown[]) {
+		this.commandService.executeCommand(command, ...args);
+		this.hoverService.hideHover(true);
+	}
+}
diff --git a/src/vs/workbench/contrib/update/common/updateUtils.ts b/src/vs/workbench/contrib/update/common/updateUtils.ts
new file mode 100644
index 0000000000000..ae1c66e88122d
--- /dev/null
+++ b/src/vs/workbench/contrib/update/common/updateUtils.ts
@@ -0,0 +1,227 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { localize } from '../../../../nls.js';
+import { Downloading } from '../../../../platform/update/common/update.js';
+
+/**
+ * Returns the progress percentage based on the current and maximum progress values.
+ */
+export function computeProgressPercent(current: number | undefined, max: number | undefined): number | undefined {
+	if (current === undefined || max === undefined || max <= 0) {
+		return undefined;
+	}
+
+	return Math.max(Math.min(Math.round((current / max) * 100), 100), 0);
+}
+
+/**
+ * Computes an estimate of remaining download time in seconds.
+ */
+export function computeDownloadTimeRemaining(state: Downloading): number | undefined {
+	const { downloadedBytes, totalBytes, startTime } = state;
+	if (downloadedBytes === undefined || totalBytes === undefined || startTime === undefined) {
+		return undefined;
+	}
+
+	const elapsedMs = Date.now() - startTime;
+	if (downloadedBytes <= 0 || totalBytes <= 0 || elapsedMs <= 0) {
+		return undefined;
+	}
+
+	const remainingBytes = totalBytes - downloadedBytes;
+	if (remainingBytes <= 0) {
+		return 0;
+	}
+
+	const bytesPerMs = downloadedBytes / elapsedMs;
+	if (bytesPerMs <= 0) {
+		return undefined;
+	}
+
+	const remainingMs = remainingBytes / bytesPerMs;
+	return Math.ceil(remainingMs / 1000);
+}
+
+/**
+ * Computes the current download speed in bytes per second.
+ */
+export function computeDownloadSpeed(state: Downloading): number | undefined {
+	const { downloadedBytes, startTime } = state;
+	if (downloadedBytes === undefined || startTime === undefined) {
+		return undefined;
+	}
+
+	const elapsedMs = Date.now() - startTime;
+	if (elapsedMs <= 0 || downloadedBytes <= 0) {
+		return undefined;
+	}
+
+	return (downloadedBytes / elapsedMs) * 1000;
+}
+
+/**
+ * Computes the version to use for fetching update info.
+ * - If the minor version differs: returns `{major}.{minor}` (e.g., 1.108.2 -> 1.109.5 => 1.109)
+ * - If the same minor: returns the target version as-is (e.g., 1.109.2 -> 1.109.5 => 1.109.5)
+ */
+export function computeUpdateInfoVersion(currentVersion: string, targetVersion: string): string | undefined {
+	const current = tryParseVersion(currentVersion);
+	const target = tryParseVersion(targetVersion);
+	if (!current || !target) {
+		return undefined;
+	}
+
+	if (current.minor !== target.minor || current.major !== target.major) {
+		return `${target.major}.${target.minor}`;
+	}
+
+	return `${target.major}.${target.minor}.${target.patch}`;
+}
+
+/**
+ * Computes the URL to fetch update info from.
+ * Follows the release notes URL pattern but with `_update` suffix.
+ */
+export function getUpdateInfoUrl(version: string): string {
+	const versionLabel = version.replace(/\./g, '_').replace(/_0$/, '');
+	return `https://code.visualstudio.com/raw/v${versionLabel}_update.md`;
+}
+
+/**
+ * Formats the time remaining as a human-readable string.
+ */
+export function formatTimeRemaining(seconds: number): string {
+	const hours = seconds / 3600;
+	if (hours >= 1) {
+		const formattedHours = formatDecimal(hours);
+		if (formattedHours === '1') {
+			return localize('update.timeRemainingHour', "{0} hour", formattedHours);
+		} else {
+			return localize('update.timeRemainingHours', "{0} hours", formattedHours);
+		}
+	}
+
+	const minutes = Math.floor(seconds / 60);
+	if (minutes >= 1) {
+		return localize('update.timeRemainingMinutes', "{0} min", minutes);
+	}
+
+	return localize('update.timeRemainingSeconds', "{0}s", seconds);
+}
+
+/**
+ * Formats a byte count as a human-readable string.
+ */
+export function formatBytes(bytes: number): string {
+	if (bytes < 1024) {
+		return localize('update.bytes', "{0} B", bytes);
+	}
+
+	const kb = bytes / 1024;
+	if (kb < 1024) {
+		return localize('update.kilobytes', "{0} KB", formatDecimal(kb));
+	}
+
+	const mb = kb / 1024;
+	if (mb < 1024) {
+		return localize('update.megabytes', "{0} MB", formatDecimal(mb));
+	}
+
+	const gb = mb / 1024;
+	return localize('update.gigabytes', "{0} GB", formatDecimal(gb));
+}
+
+/**
+ * Tries to parse a date string and returns the timestamp or undefined if parsing fails.
+ */
+export function tryParseDate(date: string | undefined): number | undefined {
+	if (date === undefined) {
+		return undefined;
+	}
+
+	try {
+		const parsed = Date.parse(date);
+		return isNaN(parsed) ? undefined : parsed;
+	} catch {
+		return undefined;
+	}
+}
+
+/**
+ * Formats a timestamp as a localized date string.
+ */
+export function formatDate(timestamp: number): string {
+	return new Date(timestamp).toLocaleDateString(undefined, {
+		year: 'numeric',
+		month: 'short',
+		day: 'numeric'
+	});
+}
+
+/**
+ * Formats a number to 1 decimal place, omitting ".0" for whole numbers.
+ */
+export function formatDecimal(value: number): string {
+	const rounded = Math.round(value * 10) / 10;
+	return rounded % 1 === 0 ? rounded.toString() : rounded.toFixed(1);
+}
+
+export interface IVersion {
+	major: number;
+	minor: number;
+	patch: number;
+}
+
+/**
+ * Parses a version string in the format "major.minor.patch" and returns an object with the components.
+ */
+export function tryParseVersion(version: string | undefined): IVersion | undefined {
+	if (version === undefined) {
+		return undefined;
+	}
+
+	const match = /^(\d{1,10})\.(\d{1,10})\.(\d{1,10})/.exec(version);
+	if (!match) {
+		return undefined;
+	}
+
+	try {
+		return {
+			major: parseInt(match[1]),
+			minor: parseInt(match[2]),
+			patch: parseInt(match[3])
+		};
+	} catch {
+		return undefined;
+	}
+}
+
+/**
+ * Processes an error message and returns a user-friendly version of it, or undefined if the error should be ignored.
+ */
+export function preprocessError(error?: string): string | undefined {
+	if (!error) {
+		return undefined;
+	}
+
+	if (/The request timed out|The network connection was lost/i.test(error)) {
+		return undefined;
+	}
+
+	return error.replace(
+		/See https:\/\/github\.com\/Squirrel\/Squirrel\.Mac\/issues\/182 for more information/,
+		'This might mean the application was put on quarantine by macOS. See [this link](https://github.com/microsoft/vscode/issues/7426#issuecomment-425093469) for more information'
+	);
+}
+
+/**
+ * Determines whether there is a major or minor version change between two versions.
+ */
+export function isMajorMinorVersionChange(previousVersion?: string, newVersion?: string): boolean {
+	const previous = tryParseVersion(previousVersion);
+	const current = tryParseVersion(newVersion);
+	return !!previous && !!current && (previous.major !== current.major || previous.minor !== current.minor);
+}
diff --git a/src/vs/workbench/contrib/update/test/browser/updateStatusBarEntry.test.ts b/src/vs/workbench/contrib/update/test/common/updateUtils.test.ts
similarity index 50%
rename from src/vs/workbench/contrib/update/test/browser/updateStatusBarEntry.test.ts
rename to src/vs/workbench/contrib/update/test/common/updateUtils.test.ts
index aa8c2a4693f0b..b6d7cf0ff9b55 100644
--- a/src/vs/workbench/contrib/update/test/browser/updateStatusBarEntry.test.ts
+++ b/src/vs/workbench/contrib/update/test/common/updateUtils.test.ts
@@ -7,9 +7,9 @@ import assert from 'assert';
 import * as sinon from 'sinon';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
 import { Downloading, StateType } from '../../../../../platform/update/common/update.js';
-import { computeDownloadSpeed, computeDownloadTimeRemaining, formatBytes, formatDate, formatTimeRemaining, getProgressPercent, tryParseDate } from '../../browser/updateStatusBarEntry.js';
+import { computeDownloadSpeed, computeDownloadTimeRemaining, computeProgressPercent, computeUpdateInfoVersion, formatBytes, formatDate, formatTimeRemaining, getUpdateInfoUrl, isMajorMinorVersionChange, tryParseDate } from '../../common/updateUtils.js';
 
-suite('UpdateStatusBarEntry', () => {
+suite('UpdateUtils', () => {
 	ensureNoDisposablesAreLeakedInTestSuite();
 
 	let clock: sinon.SinonFakeTimers;
@@ -22,30 +22,30 @@ suite('UpdateStatusBarEntry', () => {
 		clock.restore();
 	});
 
-	function createDownloadingState(downloadedBytes?: number, totalBytes?: number, startTime?: number): Downloading {
+	function DownloadingState(downloadedBytes?: number, totalBytes?: number, startTime?: number): Downloading {
 		return { type: StateType.Downloading, explicit: true, overwrite: false, downloadedBytes, totalBytes, startTime };
 	}
 
-	suite('getProgressPercent', () => {
+	suite('computeProgressPercent', () => {
 		test('handles invalid values', () => {
-			assert.strictEqual(getProgressPercent(undefined, 100), undefined);
-			assert.strictEqual(getProgressPercent(50, undefined), undefined);
-			assert.strictEqual(getProgressPercent(undefined, undefined), undefined);
-			assert.strictEqual(getProgressPercent(50, 0), undefined);
-			assert.strictEqual(getProgressPercent(50, -10), undefined);
+			assert.strictEqual(computeProgressPercent(undefined, 100), undefined);
+			assert.strictEqual(computeProgressPercent(50, undefined), undefined);
+			assert.strictEqual(computeProgressPercent(undefined, undefined), undefined);
+			assert.strictEqual(computeProgressPercent(50, 0), undefined);
+			assert.strictEqual(computeProgressPercent(50, -10), undefined);
 		});
 
 		test('computes correct percentage', () => {
-			assert.strictEqual(getProgressPercent(0, 100), 0);
-			assert.strictEqual(getProgressPercent(50, 100), 50);
-			assert.strictEqual(getProgressPercent(100, 100), 100);
-			assert.strictEqual(getProgressPercent(1, 3), 33);
-			assert.strictEqual(getProgressPercent(2, 3), 67);
+			assert.strictEqual(computeProgressPercent(0, 100), 0);
+			assert.strictEqual(computeProgressPercent(50, 100), 50);
+			assert.strictEqual(computeProgressPercent(100, 100), 100);
+			assert.strictEqual(computeProgressPercent(1, 3), 33);
+			assert.strictEqual(computeProgressPercent(2, 3), 67);
 		});
 
 		test('clamps to 0-100 range', () => {
-			assert.strictEqual(getProgressPercent(-10, 100), 0);
-			assert.strictEqual(getProgressPercent(200, 100), 100);
+			assert.strictEqual(computeProgressPercent(-10, 100), 0);
+			assert.strictEqual(computeProgressPercent(200, 100), 100);
 		});
 	});
 
@@ -54,42 +54,110 @@ suite('UpdateStatusBarEntry', () => {
 			const now = Date.now();
 
 			// Missing parameters
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState()), undefined);
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(500, undefined, now)), undefined);
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(undefined, 1000, now)), undefined);
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(500, 1000, undefined)), undefined);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState()), undefined);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(500, undefined, now)), undefined);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(undefined, 1000, now)), undefined);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(500, 1000, undefined)), undefined);
 
 			// Zero or negative values
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(0, 1000, now - 1000)), undefined);
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(500, 0, now - 1000)), undefined);
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(500, 1000, now + 1000)), undefined);
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(-100, 1000, now - 1000)), undefined);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(0, 1000, now - 1000)), undefined);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(500, 0, now - 1000)), undefined);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(500, 1000, now + 1000)), undefined);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(-100, 1000, now - 1000)), undefined);
 		});
 
 		test('returns 0 when download is complete or over-downloaded', () => {
 			const now = Date.now();
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(1000, 1000, now - 1000)), 0);
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(1500, 1000, now - 1000)), 0);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(1000, 1000, now - 1000)), 0);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(1500, 1000, now - 1000)), 0);
 		});
 
 		test('computes correct time remaining', () => {
 			const now = Date.now();
 
 			// Simple case: Downloaded 500 bytes of 1000 in 1000ms => 1s remaining
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(500, 1000, now - 1000)), 1);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(500, 1000, now - 1000)), 1);
 
 			// 10 seconds remaining: Downloaded 100MB of 200MB in 10s
 			const downloadedBytes = 100 * 1024 * 1024;
 			const totalBytes = 200 * 1024 * 1024;
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(downloadedBytes, totalBytes, now - 10000)), 10);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(downloadedBytes, totalBytes, now - 10000)), 10);
 
 			// Rounds up: 900 of 1000 bytes in 900ms => 100ms remaining => rounds to 1s
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(900, 1000, now - 900)), 1);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(900, 1000, now - 900)), 1);
 
 			// Realistic scenario: 50MB of 100MB in 50s => 50s remaining
 			const downloaded50MB = 50 * 1024 * 1024;
 			const total100MB = 100 * 1024 * 1024;
-			assert.strictEqual(computeDownloadTimeRemaining(createDownloadingState(downloaded50MB, total100MB, now - 50000)), 50);
+			assert.strictEqual(computeDownloadTimeRemaining(DownloadingState(downloaded50MB, total100MB, now - 50000)), 50);
+		});
+	});
+
+
+	suite('computeDownloadSpeed', () => {
+		test('returns undefined for invalid or incomplete input', () => {
+			const now = Date.now();
+			assert.strictEqual(computeDownloadSpeed(DownloadingState(undefined, 1000, now - 1000)), undefined);
+			assert.strictEqual(computeDownloadSpeed(DownloadingState(500, 1000, undefined)), undefined);
+			assert.strictEqual(computeDownloadSpeed(DownloadingState(undefined, undefined, undefined)), undefined);
+		});
+
+		test('returns undefined for zero or negative elapsed time', () => {
+			const now = Date.now();
+			assert.strictEqual(computeDownloadSpeed(DownloadingState(500, 1000, now + 1000)), undefined);
+		});
+
+		test('returns undefined for zero downloaded bytes', () => {
+			const now = Date.now();
+			assert.strictEqual(computeDownloadSpeed(DownloadingState(0, 1000, now - 1000)), undefined);
+		});
+
+		test('computes correct download speed in bytes per second', () => {
+			const now = Date.now();
+
+			// 1000 bytes in 1 second = 1000 B/s
+			const speed1 = computeDownloadSpeed(DownloadingState(1000, 2000, now - 1000));
+			assert.ok(speed1 !== undefined);
+			assert.ok(Math.abs(speed1 - 1000) < 50); // Allow small timing variance
+
+			// 10 MB in 10 seconds = 1 MB/s = 1048576 B/s
+			const tenMB = 10 * 1024 * 1024;
+			const speed2 = computeDownloadSpeed(DownloadingState(tenMB, tenMB * 2, now - 10000));
+			assert.ok(speed2 !== undefined);
+			const expectedSpeed = 1024 * 1024; // 1 MB/s
+			assert.ok(Math.abs(speed2 - expectedSpeed) < expectedSpeed * 0.01); // Within 1%
+		});
+	});
+
+	suite('computeUpdateInfoVersion', () => {
+		test('returns minor .0 version when minor differs', () => {
+			assert.strictEqual(computeUpdateInfoVersion('1.108.2', '1.109.5'), '1.109');
+			assert.strictEqual(computeUpdateInfoVersion('1.108.0', '1.109.0'), '1.109');
+			assert.strictEqual(computeUpdateInfoVersion('1.107.3', '1.110.1'), '1.110');
+		});
+
+		test('returns target version as-is when same minor', () => {
+			assert.strictEqual(computeUpdateInfoVersion('1.109.2', '1.109.5'), '1.109.5');
+			assert.strictEqual(computeUpdateInfoVersion('1.109.0', '1.109.3'), '1.109.3');
+		});
+
+		test('returns minor .0 version when major differs', () => {
+			assert.strictEqual(computeUpdateInfoVersion('1.109.2', '2.0.1'), '2.0');
+		});
+
+		test('returns undefined for invalid versions', () => {
+			assert.strictEqual(computeUpdateInfoVersion('invalid', '1.109.5'), undefined);
+			assert.strictEqual(computeUpdateInfoVersion('1.109.2', 'invalid'), undefined);
+		});
+	});
+
+	suite('getUpdateInfoUrl', () => {
+		test('constructs correct URL for .0 versions', () => {
+			assert.strictEqual(getUpdateInfoUrl('1.109.0'), 'https://code.visualstudio.com/raw/v1_109_update.md');
+		});
+
+		test('constructs correct URL for patch versions', () => {
+			assert.strictEqual(getUpdateInfoUrl('1.109.5'), 'https://code.visualstudio.com/raw/v1_109_5_update.md');
 		});
 	});
 
@@ -178,38 +246,38 @@ suite('UpdateStatusBarEntry', () => {
 		});
 	});
 
-	suite('computeDownloadSpeed', () => {
-		test('returns undefined for invalid or incomplete input', () => {
-			const now = Date.now();
-			assert.strictEqual(computeDownloadSpeed(createDownloadingState(undefined, 1000, now - 1000)), undefined);
-			assert.strictEqual(computeDownloadSpeed(createDownloadingState(500, 1000, undefined)), undefined);
-			assert.strictEqual(computeDownloadSpeed(createDownloadingState(undefined, undefined, undefined)), undefined);
+	suite('isMajorMinorVersionChange', () => {
+		test('returns true for major version change', () => {
+			assert.strictEqual(isMajorMinorVersionChange('1.90.0', '2.0.0'), true);
 		});
 
-		test('returns undefined for zero or negative elapsed time', () => {
-			const now = Date.now();
-			assert.strictEqual(computeDownloadSpeed(createDownloadingState(500, 1000, now + 1000)), undefined);
+		test('returns true for minor version change', () => {
+			assert.strictEqual(isMajorMinorVersionChange('1.90.0', '1.91.0'), true);
 		});
 
-		test('returns undefined for zero downloaded bytes', () => {
-			const now = Date.now();
-			assert.strictEqual(computeDownloadSpeed(createDownloadingState(0, 1000, now - 1000)), undefined);
+		test('returns false for patch-only change', () => {
+			assert.strictEqual(isMajorMinorVersionChange('1.90.0', '1.90.1'), false);
 		});
 
-		test('computes correct download speed in bytes per second', () => {
-			const now = Date.now();
+		test('returns false for identical versions', () => {
+			assert.strictEqual(isMajorMinorVersionChange('1.90.0', '1.90.0'), false);
+		});
 
-			// 1000 bytes in 1 second = 1000 B/s
-			const speed1 = computeDownloadSpeed(createDownloadingState(1000, 2000, now - 1000));
-			assert.ok(speed1 !== undefined);
-			assert.ok(Math.abs(speed1 - 1000) < 50); // Allow small timing variance
+		test('returns false when previous version is undefined', () => {
+			assert.strictEqual(isMajorMinorVersionChange(undefined, '1.90.0'), false);
+		});
 
-			// 10 MB in 10 seconds = 1 MB/s = 1048576 B/s
-			const tenMB = 10 * 1024 * 1024;
-			const speed2 = computeDownloadSpeed(createDownloadingState(tenMB, tenMB * 2, now - 10000));
-			assert.ok(speed2 !== undefined);
-			const expectedSpeed = 1024 * 1024; // 1 MB/s
-			assert.ok(Math.abs(speed2 - expectedSpeed) < expectedSpeed * 0.01); // Within 1%
+		test('returns false when new version is undefined', () => {
+			assert.strictEqual(isMajorMinorVersionChange('1.90.0', undefined), false);
+		});
+
+		test('returns false when both versions are undefined', () => {
+			assert.strictEqual(isMajorMinorVersionChange(undefined, undefined), false);
+		});
+
+		test('returns false for unparseable versions', () => {
+			assert.strictEqual(isMajorMinorVersionChange('invalid', '1.90.0'), false);
+			assert.strictEqual(isMajorMinorVersionChange('1.90.0', 'invalid'), false);
 		});
 	});
 });
diff --git a/src/vs/workbench/contrib/welcomeAgentSessions/browser/agentSessionsWelcome.ts b/src/vs/workbench/contrib/welcomeAgentSessions/browser/agentSessionsWelcome.ts
index 70191eea31ab4..9e6ca135e0840 100644
--- a/src/vs/workbench/contrib/welcomeAgentSessions/browser/agentSessionsWelcome.ts
+++ b/src/vs/workbench/contrib/welcomeAgentSessions/browser/agentSessionsWelcome.ts
@@ -293,7 +293,7 @@ export class AgentSessionsWelcomePage extends EditorPane {
 			button.appendChild(document.createTextNode(entry.label));
 			button.onclick = () => {
 				this.telemetryService.publicLog2<AgentSessionsWelcomeActionEvent, AgentSessionsWelcomeActionClassification>(
-					'gettingStarted.ActionExecuted',
+					'agentSessionsWelcome.ActionExecuted',
 					{ welcomeKind: 'agentSessionsWelcomePage', action: 'executeCommand', actionId: entry.command }
 				);
 				this.commandService.executeCommand(entry.command);
@@ -652,7 +652,7 @@ export class AgentSessionsWelcomePage extends EditorPane {
 		card.onclick = () => {
 			const walkthrough = activeWalkthroughs[currentIndex];
 			this.telemetryService.publicLog2<AgentSessionsWelcomeActionEvent, AgentSessionsWelcomeActionClassification>(
-				'gettingStarted.ActionExecuted',
+				'agentSessionsWelcome.ActionExecuted',
 				{ welcomeKind: 'agentSessionsWelcomePage', action: 'openWalkthrough', actionId: walkthrough.id }
 			);
 			// Open walkthrough with returnToCommand so back button returns to agent sessions welcome
diff --git a/src/vs/workbench/contrib/workspace/browser/media/workspaceTrustEditor.css b/src/vs/workbench/contrib/workspace/browser/media/workspaceTrustEditor.css
index 3bd850fb25bf5..7ac6aaa7c3799 100644
--- a/src/vs/workbench/contrib/workspace/browser/media/workspaceTrustEditor.css
+++ b/src/vs/workbench/contrib/workspace/browser/media/workspaceTrustEditor.css
@@ -4,10 +4,10 @@
  *--------------------------------------------------------------------------------------------*/
 
 .workspace-trust-editor {
-	max-width: 1000px;
-	padding-top: 11px;
-	margin: auto;
-	height: calc(100% - 11px);
+	max-width: 1600px;
+	padding-top: 12px;
+	margin: 0;
+	height: calc(100% - 12px);
 }
 
 .workspace-trust-editor:focus {
@@ -15,12 +15,16 @@
 }
 
 .workspace-trust-editor > .workspace-trust-header {
-	padding: 14px;
+	padding: 16px 24px;
 	display: flex;
 	flex-direction: column;
 	align-items: center;
 }
 
+.workspace-trust-editor > .workspace-trust-header:focus:not(:focus-visible) {
+	outline: none;
+}
+
 .workspace-trust-editor .workspace-trust-header .workspace-trust-title {
 	font-size: 24px;
 	font-weight: 600;
@@ -35,7 +39,7 @@
 }
 
 .workspace-trust-editor .workspace-trust-header .workspace-trust-title .workspace-trust-title-icon {
-	color: var(--workspace-trust-selected-color) !important;
+	color: var(--workspace-trust-selected-color);
 }
 
 .workspace-trust-editor .workspace-trust-header .workspace-trust-description {
@@ -43,7 +47,8 @@
 	user-select: text;
 	max-width: 600px;
 	text-align: center;
-	padding: 14px 0;
+	padding: 8px 0;
+	line-height: 20px;
 }
 
 .workspace-trust-editor .workspace-trust-section-title {
@@ -64,59 +69,67 @@
 
 /** Features List */
 .workspace-trust-editor .workspace-trust-features {
-	padding: 14px;
+	padding: 24px;
 	cursor: default;
 	user-select: text;
 	display: flex;
 	flex-direction: row;
-	flex-flow: wrap;
-	justify-content: space-evenly;
+	flex-wrap: wrap;
+	justify-content: center;
+	gap: 16px;
 }
 
 .workspace-trust-editor .workspace-trust-features .workspace-trust-limitations {
-	min-height: 315px;
 	border: 1px solid var(--workspace-trust-unselected-color);
-	margin: 4px 4px;
+	border-radius: var(--vscode-cornerRadius-medium);
 	display: flex;
 	flex-direction: column;
-	padding: 10px 40px;
+	padding: 8px 36px;
 }
 
 .workspace-trust-editor.trusted .workspace-trust-features .workspace-trust-limitations.trusted,
 .workspace-trust-editor.untrusted .workspace-trust-features .workspace-trust-limitations.untrusted {
-	border-width: 2px;
-	border-color: var(--workspace-trust-selected-color) !important;
-	padding: 9px 39px;
-	outline-offset: 2px;
+	outline: 2px solid var(--workspace-trust-selected-color);
+	outline-offset: -2px;
+}
+
+.workspace-trust-editor .workspace-trust-features .workspace-trust-limitations:focus:not(:focus-visible) {
+	outline: none;
+}
+
+.workspace-trust-editor .workspace-trust-features .workspace-trust-limitations:focus-visible {
+	outline: 1px solid var(--vscode-focusBorder);
+	outline-offset: -1px;
 }
 
 .workspace-trust-editor .workspace-trust-features .workspace-trust-limitations ul {
 	list-style: none;
 	padding-inline-start: 0px;
+	margin: 16px 0;
 }
 
 .workspace-trust-editor .workspace-trust-features .workspace-trust-limitations li {
 	display: flex;
-	padding-bottom: 10px;
+	padding-bottom: 4px;
 }
 
 .workspace-trust-editor .workspace-trust-features .workspace-trust-limitations .list-item-icon {
-	padding-right: 5px;
 	line-height: 24px;
+	padding: 0 6px 0 0;
 }
 
 .workspace-trust-editor .workspace-trust-features .workspace-trust-limitations.trusted .list-item-icon {
-	color: var(--workspace-trust-check-color) !important;
-	font-size: 18px;
+	color: var(--workspace-trust-check-color);
+	font-size: 16px;
 }
 
 .workspace-trust-editor .workspace-trust-features .workspace-trust-limitations.untrusted .list-item-icon {
-	color: var(--workspace-trust-x-color) !important;
-	font-size: 20px;
+	color: var(--workspace-trust-x-color);
+	font-size: 16px;
 }
 
 .workspace-trust-editor .workspace-trust-features .workspace-trust-limitations .list-item-text {
-	font-size: 16px;
+	font-size: 14px;
 	line-height: 24px;
 }
 
@@ -130,7 +143,7 @@
 	font-size: 16px;
 	font-weight: 600;
 	line-height: 24px;
-	padding: 10px 0px;
+	padding: 16px 0px;
 	display: flex;
 }
 
@@ -143,12 +156,13 @@
 .workspace-trust-editor.trusted .workspace-trust-features .workspace-trust-limitations.trusted .workspace-trust-limitations-header .workspace-trust-limitations-title .workspace-trust-title-icon,
 .workspace-trust-editor.untrusted .workspace-trust-features .workspace-trust-limitations.untrusted .workspace-trust-limitations-header .workspace-trust-limitations-title .workspace-trust-title-icon {
 	display: unset;
-	color: var(--workspace-trust-selected-color) !important;
+	color: var(--workspace-trust-selected-color);
 }
 
 .workspace-trust-editor .workspace-trust-features .workspace-trust-untrusted-description {
 	font-style: italic;
-	padding-bottom: 10px;
+	color: var(--vscode-descriptionForeground);
+	padding-bottom: 8px;
 }
 
 /** Buttons Container */
@@ -170,7 +184,7 @@
 }
 
 .workspace-trust-editor .workspace-trust-settings .trusted-uris-button-bar {
-	margin-top: 5px;
+	margin-top: 8px;
 }
 
 .workspace-trust-editor .workspace-trust-settings .trusted-uris-button-bar .monaco-button {
@@ -183,7 +197,7 @@
 .workspace-trust-editor .workspace-trust-features .workspace-trust-buttons-row .workspace-trust-buttons > .monaco-button,
 .workspace-trust-editor .workspace-trust-features .workspace-trust-buttons-row .workspace-trust-buttons > .monaco-button-dropdown,
 .workspace-trust-editor .workspace-trust-settings .trusted-uris-button-bar .monaco-button {
-	margin: 4px 5px; /* allows button focus outline to be visible */
+	margin: 8px 4px; /* allows button focus outline to be visible */
 }
 
 .workspace-trust-editor .workspace-trust-features .workspace-trust-buttons-row .workspace-trust-buttons .monaco-button-dropdown .monaco-dropdown-button {
@@ -192,7 +206,7 @@
 
 .workspace-trust-limitations {
 	width: 50%;
-	max-width: 350px;
+	max-width: 400px;
 	min-width: 250px;
 	flex: 1;
 }
@@ -208,7 +222,7 @@
 }
 
 .workspace-trust-intro-dialog .workspace-trust-dialog-image-row.badge-row img {
-	max-height: 40px;
+	max-height: 36px;
 	padding-right: 10px;
 }
 
@@ -218,7 +232,9 @@
 }
 
 .workspace-trust-editor .workspace-trust-settings {
-	padding: 20px 14px;
+	padding: 24px 36px;
+	border-top: 1px solid var(--vscode-editorWidget-border);
+	margin-top: 8px;
 }
 
 .workspace-trust-editor .workspace-trust-settings .workspace-trusted-folders-title {
@@ -229,6 +245,10 @@
 	display: none;
 }
 
+.workspace-trust-editor .trusted-uris-table {
+	margin-top: 16px;
+}
+
 .workspace-trust-editor .monaco-table-tr .monaco-table-td .path {
 	width: 100%;
 }
@@ -292,3 +312,28 @@
 .workspace-trust-editor .workspace-trust-settings .monaco-list-row:hover .monaco-table-tr .monaco-table-td .actions .monaco-action-bar {
 	display: flex;
 }
+
+/** Responsive: single-column layout for narrow widths */
+@container (max-width: 600px) {
+	.workspace-trust-editor .workspace-trust-features {
+		flex-direction: column;
+		align-items: center;
+	}
+
+	.workspace-trust-limitations {
+		width: 100%;
+		max-width: 400px;
+	}
+}
+
+@media (max-width: 600px) {
+	.workspace-trust-editor .workspace-trust-features {
+		flex-direction: column;
+		align-items: center;
+	}
+
+	.workspace-trust-limitations {
+		width: 100%;
+		max-width: 400px;
+	}
+}
diff --git a/src/vs/workbench/electron-browser/desktop.contribution.ts b/src/vs/workbench/electron-browser/desktop.contribution.ts
index fd09050e5333c..4c3893ac7ed0f 100644
--- a/src/vs/workbench/electron-browser/desktop.contribution.ts
+++ b/src/vs/workbench/electron-browser/desktop.contribution.ts
@@ -455,6 +455,10 @@ import product from '../../platform/product/common/product.js';
 			'remote-debugging-port': {
 				type: 'string',
 				description: localize('argv.remoteDebuggingPort', "Specifies the port to use for remote debugging.")
+			},
+			'js-flags': {
+				type: 'string',
+				description: localize('argv.jsFlags', "Specifies V8 JavaScript engine flags to pass (e.g. \"--max-old-space-size=4096\"). These flags are applied to the main process, renderer and utility processes.")
 			}
 		}
 	};
diff --git a/src/vs/workbench/services/accounts/browser/defaultAccount.ts b/src/vs/workbench/services/accounts/browser/defaultAccount.ts
index 9cc1b8bc96089..2992998a9c384 100644
--- a/src/vs/workbench/services/accounts/browser/defaultAccount.ts
+++ b/src/vs/workbench/services/accounts/browser/defaultAccount.ts
@@ -3,35 +3,35 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-import { Emitter } from '../../../../base/common/event.js';
-import { Disposable } from '../../../../base/common/lifecycle.js';
-import { IProductService } from '../../../../platform/product/common/productService.js';
-import { AuthenticationSession, AuthenticationSessionAccount, IAuthenticationExtensionsService, IAuthenticationService } from '../../authentication/common/authentication.js';
-import { asJson, IRequestService, isClientError, isSuccess } from '../../../../platform/request/common/request.js';
-import { CancellationToken } from '../../../../base/common/cancellation.js';
-import { IExtensionService } from '../../extensions/common/extensions.js';
-import { ILogService } from '../../../../platform/log/common/log.js';
-import { IContextKey, IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
-import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../common/contributions.js';
+import { distinct } from '../../../../base/common/arrays.js';
 import { Barrier, RunOnceScheduler, ThrottledDelayer, timeout } from '../../../../base/common/async.js';
-import { IHostService } from '../../host/browser/host.js';
-import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
+import { CancellationToken } from '../../../../base/common/cancellation.js';
+import { ICopilotTokenInfo, IDefaultAccount, IDefaultAccountAuthenticationProvider, IEntitlementsData, IPolicyData } from '../../../../base/common/defaultAccount.js';
 import { getErrorMessage } from '../../../../base/common/errors.js';
-import { IDefaultAccount, IDefaultAccountAuthenticationProvider, IEntitlementsData, IPolicyData } from '../../../../base/common/defaultAccount.js';
-import { isString, isUndefined, Mutable } from '../../../../base/common/types.js';
-import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
-import { IWorkbenchEnvironmentService } from '../../environment/common/environmentService.js';
-import { isWeb } from '../../../../base/common/platform.js';
-import { IDefaultAccountProvider, IDefaultAccountService } from '../../../../platform/defaultAccount/common/defaultAccount.js';
-import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
-import { distinct } from '../../../../base/common/arrays.js';
+import { Emitter } from '../../../../base/common/event.js';
+import { Disposable } from '../../../../base/common/lifecycle.js';
 import { equals } from '../../../../base/common/objects.js';
+import { isWeb } from '../../../../base/common/platform.js';
 import { IDefaultChatAgent } from '../../../../base/common/product.js';
+import { isString, isUndefined, Mutable } from '../../../../base/common/types.js';
 import { IRequestContext } from '../../../../base/parts/request/common/request.js';
-import { IInstantiationService, ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
-import { ICommandService } from '../../../../platform/commands/common/commands.js';
 import { localize2 } from '../../../../nls.js';
 import { Action2, registerAction2 } from '../../../../platform/actions/common/actions.js';
+import { ICommandService } from '../../../../platform/commands/common/commands.js';
+import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
+import { IContextKey, IContextKeyService, RawContextKey } from '../../../../platform/contextkey/common/contextkey.js';
+import { IDefaultAccountProvider, IDefaultAccountService } from '../../../../platform/defaultAccount/common/defaultAccount.js';
+import { IInstantiationService, ServicesAccessor } from '../../../../platform/instantiation/common/instantiation.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
+import { IProductService } from '../../../../platform/product/common/productService.js';
+import { asJson, IRequestService, isClientError, isSuccess } from '../../../../platform/request/common/request.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
+import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
+import { IWorkbenchContribution, registerWorkbenchContribution2, WorkbenchPhase } from '../../../common/contributions.js';
+import { AuthenticationSession, AuthenticationSessionAccount, IAuthenticationExtensionsService, IAuthenticationService } from '../../authentication/common/authentication.js';
+import { IWorkbenchEnvironmentService } from '../../environment/common/environmentService.js';
+import { IExtensionService } from '../../extensions/common/extensions.js';
+import { IHostService } from '../../host/browser/host.js';
 
 interface IDefaultAccountConfig {
 	readonly preferredExtensions: string[];
@@ -115,6 +115,7 @@ export class DefaultAccountService extends Disposable implements IDefaultAccount
 
 	private defaultAccount: IDefaultAccount | null = null;
 	get policyData(): IPolicyData | null { return this.defaultAccountProvider?.policyData ?? null; }
+	get copilotTokenInfo(): ICopilotTokenInfo | null { return this.defaultAccountProvider?.copilotTokenInfo ?? null; }
 
 	private readonly initBarrier = new Barrier();
 
@@ -124,6 +125,9 @@ export class DefaultAccountService extends Disposable implements IDefaultAccount
 	private readonly _onDidChangePolicyData = this._register(new Emitter<IPolicyData | null>());
 	readonly onDidChangePolicyData = this._onDidChangePolicyData.event;
 
+	private readonly _onDidChangeCopilotTokenInfo = this._register(new Emitter<ICopilotTokenInfo | null>());
+	readonly onDidChangeCopilotTokenInfo = this._onDidChangeCopilotTokenInfo.event;
+
 	private readonly defaultAccountConfig: IDefaultAccountConfig;
 	private defaultAccountProvider: IDefaultAccountProvider | null = null;
 
@@ -164,6 +168,7 @@ export class DefaultAccountService extends Disposable implements IDefaultAccount
 			this.initBarrier.open();
 			this._register(provider.onDidChangeDefaultAccount(account => this.setDefaultAccount(account)));
 			this._register(provider.onDidChangePolicyData(policyData => this._onDidChangePolicyData.fire(policyData)));
+			this._register(provider.onDidChangeCopilotTokenInfo(tokenInfo => this._onDidChangeCopilotTokenInfo.fire(tokenInfo)));
 		});
 	}
 
@@ -201,10 +206,16 @@ interface IAccountPolicyData {
 	readonly mcpRegistryDataFetchedAt?: number;
 }
 
+interface ICachedAccountData {
+	readonly accountPolicyData: IAccountPolicyData;
+	readonly copilotTokenInfo?: ICopilotTokenInfo;
+}
+
 interface IDefaultAccountData {
 	accountId: string;
 	defaultAccount: IDefaultAccount;
 	policyData: IAccountPolicyData | null;
+	copilotTokenInfo: ICopilotTokenInfo | null;
 }
 
 type DefaultAccountStatusTelemetry = {
@@ -227,12 +238,18 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 	private _policyData: IAccountPolicyData | null = null;
 	get policyData(): IPolicyData | null { return this._policyData?.policyData ?? null; }
 
+	private _copilotTokenInfo: ICopilotTokenInfo | null = null;
+	get copilotTokenInfo(): ICopilotTokenInfo | null { return this._copilotTokenInfo; }
+
 	private readonly _onDidChangeDefaultAccount = this._register(new Emitter<IDefaultAccount | null>());
 	readonly onDidChangeDefaultAccount = this._onDidChangeDefaultAccount.event;
 
 	private readonly _onDidChangePolicyData = this._register(new Emitter<IPolicyData | null>());
 	readonly onDidChangePolicyData = this._onDidChangePolicyData.event;
 
+	private readonly _onDidChangeCopilotTokenInfo = this._register(new Emitter<ICopilotTokenInfo | null>());
+	readonly onDidChangeCopilotTokenInfo = this._onDidChangeCopilotTokenInfo.event;
+
 	private readonly accountStatusContext: IContextKey<string>;
 	private initialized = false;
 	private readonly initPromise: Promise<void>;
@@ -256,7 +273,9 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 	) {
 		super();
 		this.accountStatusContext = CONTEXT_DEFAULT_ACCOUNT_STATE.bindTo(contextKeyService);
-		this._policyData = this.getCachedPolicyData();
+		const cachedAccountData = this.getCachedAccountData();
+		this._policyData = cachedAccountData?.accountPolicyData ?? null;
+		this._copilotTokenInfo = cachedAccountData?.copilotTokenInfo ?? null;
 		this.initPromise = this.init()
 			.finally(() => {
 				this.telemetryService.publicLog2<DefaultAccountStatusTelemetry, DefaultAccountStatusTelemetryClassification>('defaultaccount:status', { status: this.defaultAccount ? 'available' : 'unavailable', initial: true });
@@ -264,14 +283,31 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 			});
 	}
 
-	private getCachedPolicyData(): IAccountPolicyData | null {
+	private getCachedAccountData(): ICachedAccountData | null {
 		const cached = this.storageService.get(CACHED_POLICY_DATA_KEY, StorageScope.APPLICATION);
 		if (cached) {
 			try {
-				const { accountId, policyData } = JSON.parse(cached);
+				const parsed = JSON.parse(cached);
+
+				// TODO: Remove old format migration after August 2026.
+				// Previously, the cache stored a flat IAccountPolicyData shape
+				// (e.g. { accountId, policyData, ... }). We now wrap it inside
+				// ICachedAccountData ({ accountPolicyData, copilotTokenInfo }).
+				// This branch migrates the old flat format to the new shape and
+				// re-stores it so subsequent reads use the new format directly.
+				const { accountId, policyData, tokenEntitlementsFetchedAt, mcpRegistryDataFetchedAt, copilotTokenInfo } = parsed;
 				if (accountId && policyData) {
+					this.logService.debug('[DefaultAccount] Initializing with cached policy data (migrating old format)');
+					const result: ICachedAccountData = { accountPolicyData: { accountId, policyData, tokenEntitlementsFetchedAt, mcpRegistryDataFetchedAt }, copilotTokenInfo };
+					this.storageService.store(CACHED_POLICY_DATA_KEY, JSON.stringify(result), StorageScope.APPLICATION, StorageTarget.MACHINE);
+					return result;
+				}
+
+				// New format
+				const { accountPolicyData, copilotTokenInfo: wrappedCopilotTokenInfo } = parsed;
+				if (accountPolicyData?.accountId && accountPolicyData?.policyData) {
 					this.logService.debug('[DefaultAccount] Initializing with cached policy data');
-					return { accountId, policyData };
+					return { accountPolicyData, copilotTokenInfo: wrappedCopilotTokenInfo };
 				}
 			} catch (error) {
 				this.logService.error('[DefaultAccount] Failed to parse cached policy data', getErrorMessage(error));
@@ -408,6 +444,7 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 		this.logService.trace('[DefaultAccount] Updating default account:', account);
 		if (account) {
 			this._defaultAccount = account;
+			this.setCopilotTokenInfo(account.copilotTokenInfo);
 			this.setPolicyData(account.policyData);
 			this._onDidChangeDefaultAccount.fire(this._defaultAccount.defaultAccount);
 			this.accountStatusContext.set(DefaultAccountStatus.Available);
@@ -415,6 +452,7 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 		} else {
 			this._defaultAccount = null;
 			this.setPolicyData(null);
+			this.setCopilotTokenInfo(null);
 			this._onDidChangeDefaultAccount.fire(null);
 			this.accountDataPollScheduler.cancel();
 			this.accountStatusContext.set(DefaultAccountStatus.Unavailable);
@@ -431,10 +469,22 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 		this._onDidChangePolicyData.fire(this._policyData?.policyData ?? null);
 	}
 
+	private setCopilotTokenInfo(copilotTokenInfo: ICopilotTokenInfo | null): void {
+		if (equals(this._copilotTokenInfo, copilotTokenInfo)) {
+			return;
+		}
+		this._copilotTokenInfo = copilotTokenInfo;
+		this._onDidChangeCopilotTokenInfo.fire(this._copilotTokenInfo);
+	}
+
 	private cachePolicyData(accountPolicyData: IAccountPolicyData | null): void {
 		if (accountPolicyData) {
 			this.logService.debug('[DefaultAccount] Caching policy data for account:', accountPolicyData.accountId);
-			this.storageService.store(CACHED_POLICY_DATA_KEY, JSON.stringify(accountPolicyData), StorageScope.APPLICATION, StorageTarget.MACHINE);
+			const cachedAccountData: ICachedAccountData = {
+				accountPolicyData,
+				copilotTokenInfo: this._copilotTokenInfo ?? undefined,
+			};
+			this.storageService.store(CACHED_POLICY_DATA_KEY, JSON.stringify(cachedAccountData), StorageScope.APPLICATION, StorageTarget.MACHINE);
 		} else {
 			this.logService.debug('[DefaultAccount] Removing cached policy data');
 			this.storageService.remove(CACHED_POLICY_DATA_KEY, StorageScope.APPLICATION);
@@ -495,9 +545,9 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 				tokenEntitlementsFetchedAt = tokenEntitlementsResult.fetchedAt;
 				const tokenEntitlementsData = tokenEntitlementsResult.data;
 				policyData = policyData ?? {};
-				policyData.chat_agent_enabled = tokenEntitlementsData.chat_agent_enabled;
-				policyData.chat_preview_features_enabled = tokenEntitlementsData.chat_preview_features_enabled;
-				policyData.mcp = tokenEntitlementsData.mcp;
+				policyData.chat_agent_enabled = tokenEntitlementsData.policyData.chat_agent_enabled;
+				policyData.chat_preview_features_enabled = tokenEntitlementsData.policyData.chat_preview_features_enabled;
+				policyData.mcp = tokenEntitlementsData.policyData.mcp;
 				if (policyData.mcp) {
 					const mcpRegistryResult = await this.getMcpRegistryProvider(sessions, accountPolicyData);
 					mcpRegistryDataFetchedAt = mcpRegistryResult?.fetchedAt;
@@ -517,7 +567,12 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 				entitlementsData,
 			};
 			this.logService.debug('[DefaultAccount] Successfully created default account for provider:', authenticationProvider.id);
-			return { defaultAccount, accountId, policyData: policyData ? { accountId, policyData, tokenEntitlementsFetchedAt, mcpRegistryDataFetchedAt } : null };
+			return {
+				defaultAccount,
+				accountId,
+				policyData: policyData ? { accountId, policyData, tokenEntitlementsFetchedAt, mcpRegistryDataFetchedAt } : null,
+				copilotTokenInfo: tokenEntitlementsResult?.data.copilotTokenInfo ?? null,
+			};
 		} catch (error) {
 			this.logService.error('[DefaultAccount] Failed to create default account for provider:', authenticationProvider.id, getErrorMessage(error));
 			return null;
@@ -572,16 +627,16 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 		return expectedScopes.every(scope => scopes.includes(scope));
 	}
 
-	private async getTokenEntitlements(sessions: AuthenticationSession[], accountPolicyData: IAccountPolicyData | undefined): Promise<{ data: Partial<IPolicyData>; fetchedAt: number } | undefined> {
+	private async getTokenEntitlements(sessions: AuthenticationSession[], accountPolicyData: IAccountPolicyData | undefined): Promise<{ data: { policyData: Partial<IPolicyData>; copilotTokenInfo: ICopilotTokenInfo }; fetchedAt: number } | undefined> {
 		if (accountPolicyData?.tokenEntitlementsFetchedAt && !this.isDataStale(accountPolicyData.tokenEntitlementsFetchedAt)) {
 			this.logService.debug('[DefaultAccount] Using last fetched token entitlements data');
-			return { data: accountPolicyData.policyData, fetchedAt: accountPolicyData.tokenEntitlementsFetchedAt };
+			return { data: { policyData: accountPolicyData.policyData, copilotTokenInfo: this._copilotTokenInfo ?? {} }, fetchedAt: accountPolicyData.tokenEntitlementsFetchedAt };
 		}
 		const data = await this.requestTokenEntitlements(sessions);
 		return data ? { data, fetchedAt: Date.now() } : undefined;
 	}
 
-	private async requestTokenEntitlements(sessions: AuthenticationSession[]): Promise<Partial<IPolicyData> | undefined> {
+	private async requestTokenEntitlements(sessions: AuthenticationSession[]): Promise<{ policyData: Partial<IPolicyData>; copilotTokenInfo: ICopilotTokenInfo } | undefined> {
 		const tokenEntitlementsUrl = this.getTokenEntitlementUrl();
 		if (!tokenEntitlementsUrl) {
 			this.logService.debug('[DefaultAccount] No token entitlements URL found');
@@ -589,7 +644,7 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 		}
 
 		this.logService.debug('[DefaultAccount] Fetching token entitlements from:', tokenEntitlementsUrl);
-		const response = await this.request(tokenEntitlementsUrl, 'GET', undefined, sessions, CancellationToken.None);
+		const response = await this.request(tokenEntitlementsUrl, 'GET', undefined, sessions, CancellationToken.None, 'defaultAccount.tokenEntitlements');
 		if (!response) {
 			return undefined;
 		}
@@ -604,11 +659,17 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 			if (chatData) {
 				const tokenMap = this.extractFromToken(chatData.token);
 				return {
-					// Editor preview features are disabled if the flag is present and set to 0
-					chat_preview_features_enabled: tokenMap.get('editor_preview_features') !== '0',
-					chat_agent_enabled: tokenMap.get('agent_mode') !== '0',
-					// MCP is disabled if the flag is present and set to 0
-					mcp: tokenMap.get('mcp') !== '0',
+					policyData: {
+						// Editor preview features are disabled if the flag is present and set to 0
+						chat_preview_features_enabled: tokenMap.get('editor_preview_features') !== '0',
+						chat_agent_enabled: tokenMap.get('agent_mode') !== '0',
+						// MCP is disabled if the flag is present and set to 0
+						mcp: tokenMap.get('mcp') !== '0',
+					},
+					copilotTokenInfo: {
+						sn: tokenMap.get('sn'),
+						fcv1: tokenMap.get('fcv1'),
+					},
 				};
 			}
 			this.logService.error('Failed to fetch token entitlements', 'No data returned');
@@ -627,7 +688,7 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 		}
 
 		this.logService.debug('[DefaultAccount] Fetching entitlements from:', entitlementUrl);
-		const response = await this.request(entitlementUrl, 'GET', undefined, sessions, CancellationToken.None);
+		const response = await this.request(entitlementUrl, 'GET', undefined, sessions, CancellationToken.None, 'defaultAccount.entitlements');
 		if (!response) {
 			return undefined;
 		}
@@ -670,7 +731,7 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 		}
 
 		this.logService.debug('[DefaultAccount] Fetching MCP registry data from:', mcpRegistryDataUrl);
-		const response = await this.request(mcpRegistryDataUrl, 'GET', undefined, sessions, CancellationToken.None);
+		const response = await this.request(mcpRegistryDataUrl, 'GET', undefined, sessions, CancellationToken.None, 'defaultAccount.mcpRegistryProvider');
 		if (!response) {
 			return undefined;
 		}
@@ -698,9 +759,9 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 		}
 	}
 
-	private async request(url: string, type: 'GET', body: undefined, sessions: AuthenticationSession[], token: CancellationToken): Promise<IRequestContext | undefined>;
-	private async request(url: string, type: 'POST', body: object, sessions: AuthenticationSession[], token: CancellationToken): Promise<IRequestContext | undefined>;
-	private async request(url: string, type: 'GET' | 'POST', body: object | undefined, sessions: AuthenticationSession[], token: CancellationToken): Promise<IRequestContext | undefined> {
+	private async request(url: string, type: 'GET', body: undefined, sessions: AuthenticationSession[], token: CancellationToken, callSite: string): Promise<IRequestContext | undefined>;
+	private async request(url: string, type: 'POST', body: object, sessions: AuthenticationSession[], token: CancellationToken, callSite: string): Promise<IRequestContext | undefined>;
+	private async request(url: string, type: 'GET' | 'POST', body: object | undefined, sessions: AuthenticationSession[], token: CancellationToken, callSite: string): Promise<IRequestContext | undefined> {
 		let lastResponse: IRequestContext | undefined;
 
 		for (const session of sessions) {
@@ -716,7 +777,8 @@ class DefaultAccountProvider extends Disposable implements IDefaultAccountProvid
 					disableCache: true,
 					headers: {
 						'Authorization': `Bearer ${session.accessToken}`
-					}
+					},
+					callSite
 				}, token);
 
 				const status = response.res.statusCode;
diff --git a/src/vs/workbench/services/actions/common/menusExtensionPoint.ts b/src/vs/workbench/services/actions/common/menusExtensionPoint.ts
index 7f5c8e64d149f..e9e6d9d2cca20 100644
--- a/src/vs/workbench/services/actions/common/menusExtensionPoint.ts
+++ b/src/vs/workbench/services/actions/common/menusExtensionPoint.ts
@@ -52,6 +52,11 @@ const apiMenus: IAPIMenu[] = [
 		id: MenuId.EditorTitle,
 		description: localize('menus.editorTitle', "The editor title menu")
 	},
+	{
+		key: 'modalEditor/editorTitle',
+		id: MenuId.ModalEditorEditorTitle,
+		description: localize('menus.modalEditorEditorTitle', "The editor title menu in the modal editor")
+	},
 	{
 		key: 'editor/title/run',
 		id: MenuId.EditorTitleRun,
@@ -479,6 +484,12 @@ const apiMenus: IAPIMenu[] = [
 		description: localize('menus.chatEditingSessionChangesToolbar', "The Chat Editing widget toolbar menu for session changes."),
 		proposed: 'chatSessionsProvider'
 	},
+	{
+		key: 'chat/input/editing/sessionApplyActions',
+		id: MenuId.ChatEditingSessionApplySubmenu,
+		description: localize('menus.chatEditingSessionApplySubmenu', "Submenu for apply actions in the Chat Editing session changes toolbar."),
+		proposed: 'chatSessionsProvider'
+	},
 	{
 		// TODO: rename this to something like: `chatSessions/item/inline`
 		key: 'chat/chatSessions',
diff --git a/src/vs/workbench/services/assignment/common/assignmentFilters.ts b/src/vs/workbench/services/assignment/common/assignmentFilters.ts
index 024c915e1eebd..1f6487e9a207b 100644
--- a/src/vs/workbench/services/assignment/common/assignmentFilters.ts
+++ b/src/vs/workbench/services/assignment/common/assignmentFilters.ts
@@ -4,13 +4,15 @@
  *--------------------------------------------------------------------------------------------*/
 
 import type { IExperimentationFilterProvider } from 'tas-client';
-import { IExtensionService } from '../../extensions/common/extensions.js';
+import { Emitter } from '../../../../base/common/event.js';
 import { Disposable } from '../../../../base/common/lifecycle.js';
+import { getInternalOrg } from '../../../../platform/assignment/common/assignment.js';
+import { IDefaultAccountService } from '../../../../platform/defaultAccount/common/defaultAccount.js';
 import { ExtensionIdentifier } from '../../../../platform/extensions/common/extensions.js';
 import { ILogService } from '../../../../platform/log/common/log.js';
-import { Emitter } from '../../../../base/common/event.js';
 import { IStorageService, StorageScope, StorageTarget } from '../../../../platform/storage/common/storage.js';
 import { IChatEntitlementService } from '../../chat/common/chatEntitlementService.js';
+import { IExtensionService } from '../../extensions/common/extensions.js';
 
 export enum ExtensionsFilter {
 
@@ -43,6 +45,16 @@ export enum ExtensionsFilter {
 	 * The tracking ID of the user from Copilot entitlement API.
 	 */
 	CopilotTrackingId = 'X-Copilot-Tracking-Id',
+
+	/**
+	 * Whether the `sn` flag is set to `'1'` in the copilot token.
+	 */
+	CopilotIsSn = 'X-GitHub-Copilot-IsSn',
+
+	/**
+	 * Whether the `fcv1` flag is set to `'1'` in the copilot token.
+	 */
+	CopilotIsFcv1 = 'X-GitHub-Copilot-IsFcv1',
 }
 
 enum StorageVersionKeys {
@@ -52,6 +64,8 @@ enum StorageVersionKeys {
 	CopilotSku = 'extensionsAssignmentFilterProvider.copilotSku',
 	CopilotInternalOrg = 'extensionsAssignmentFilterProvider.copilotInternalOrg',
 	CopilotTrackingId = 'extensionsAssignmentFilterProvider.copilotTrackingId',
+	CopilotIsSn = 'extensionsAssignmentFilterProvider.copilotIsSn',
+	CopilotIsFcv1 = 'extensionsAssignmentFilterProvider.copilotIsFcv1',
 }
 
 export class CopilotAssignmentFilterProvider extends Disposable implements IExperimentationFilterProvider {
@@ -63,6 +77,8 @@ export class CopilotAssignmentFilterProvider extends Disposable implements IExpe
 	private copilotInternalOrg: string | undefined;
 	private copilotSku: string | undefined;
 	private copilotTrackingId: string | undefined;
+	private copilotIsSn: string | undefined;
+	private copilotIsFcv1: string | undefined;
 
 	private readonly _onDidChangeFilters = this._register(new Emitter<void>());
 	readonly onDidChangeFilters = this._onDidChangeFilters.event;
@@ -72,6 +88,7 @@ export class CopilotAssignmentFilterProvider extends Disposable implements IExpe
 		@ILogService private readonly _logService: ILogService,
 		@IStorageService private readonly _storageService: IStorageService,
 		@IChatEntitlementService private readonly _chatEntitlementService: IChatEntitlementService,
+		@IDefaultAccountService private readonly _defaultAccountService: IDefaultAccountService,
 	) {
 		super();
 
@@ -81,6 +98,8 @@ export class CopilotAssignmentFilterProvider extends Disposable implements IExpe
 		this.copilotSku = this._storageService.get(StorageVersionKeys.CopilotSku, StorageScope.PROFILE);
 		this.copilotInternalOrg = this._storageService.get(StorageVersionKeys.CopilotInternalOrg, StorageScope.PROFILE);
 		this.copilotTrackingId = this._storageService.get(StorageVersionKeys.CopilotTrackingId, StorageScope.PROFILE);
+		this.copilotIsSn = this._storageService.get(StorageVersionKeys.CopilotIsSn, StorageScope.PROFILE);
+		this.copilotIsFcv1 = this._storageService.get(StorageVersionKeys.CopilotIsFcv1, StorageScope.PROFILE);
 
 		this._register(this._extensionService.onDidChangeExtensionsStatus(extensionIdentifiers => {
 			if (extensionIdentifiers.some(identifier => ExtensionIdentifier.equals(identifier, 'github.copilot') || ExtensionIdentifier.equals(identifier, 'github.copilot-chat'))) {
@@ -92,8 +111,13 @@ export class CopilotAssignmentFilterProvider extends Disposable implements IExpe
 			this.updateCopilotEntitlementInfo();
 		}));
 
+		this._register(this._defaultAccountService.onDidChangeCopilotTokenInfo(() => {
+			this.updateCopilotTokenInfo();
+		}));
+
 		this.updateExtensionVersions();
 		this.updateCopilotEntitlementInfo();
+		this.updateCopilotTokenInfo();
 	}
 
 	private async updateExtensionVersions() {
@@ -135,10 +159,7 @@ export class CopilotAssignmentFilterProvider extends Disposable implements IExpe
 	private updateCopilotEntitlementInfo() {
 		const newSku = this._chatEntitlementService.sku;
 		const newTrackingId = this._chatEntitlementService.copilotTrackingId;
-		const newIsGitHubInternal = this._chatEntitlementService.organisations?.includes('github');
-		const newIsMicrosoftInternal = this._chatEntitlementService.organisations?.includes('microsoft') || this._chatEntitlementService.organisations?.includes('ms-copilot') || this._chatEntitlementService.organisations?.includes('MicrosoftCopilot');
-		const newIsVSCodeInternal = this._chatEntitlementService.organisations?.includes('Visual-Studio-Code');
-		const newInternalOrg = newIsVSCodeInternal ? 'vscode' : newIsGitHubInternal ? 'github' : newIsMicrosoftInternal ? 'microsoft' : undefined;
+		const newInternalOrg = getInternalOrg(this._chatEntitlementService.organisations);
 
 		if (this.copilotSku === newSku && this.copilotInternalOrg === newInternalOrg && this.copilotTrackingId === newTrackingId) {
 			return;
@@ -156,6 +177,25 @@ export class CopilotAssignmentFilterProvider extends Disposable implements IExpe
 		this._onDidChangeFilters.fire();
 	}
 
+	private updateCopilotTokenInfo() {
+		const tokenInfo = this._defaultAccountService.copilotTokenInfo;
+		const newIsSn = tokenInfo?.sn === '1' ? '1' : '0';
+		const newIsFcv1 = tokenInfo?.fcv1 === '1' ? '1' : '0';
+
+		if (this.copilotIsSn === newIsSn && this.copilotIsFcv1 === newIsFcv1) {
+			return;
+		}
+
+		this.copilotIsSn = newIsSn;
+		this.copilotIsFcv1 = newIsFcv1;
+
+		this._storageService.store(StorageVersionKeys.CopilotIsSn, this.copilotIsSn, StorageScope.PROFILE, StorageTarget.MACHINE);
+		this._storageService.store(StorageVersionKeys.CopilotIsFcv1, this.copilotIsFcv1, StorageScope.PROFILE, StorageTarget.MACHINE);
+
+		// Notify that the filters have changed.
+		this._onDidChangeFilters.fire();
+	}
+
 	/**
 	 * Returns a version string that can be parsed by the TAS client.
 	 * The tas client cannot handle suffixes lke "-insider"
@@ -184,6 +224,10 @@ export class CopilotAssignmentFilterProvider extends Disposable implements IExpe
 				return this.copilotInternalOrg ?? null;
 			case ExtensionsFilter.CopilotTrackingId:
 				return this.copilotTrackingId ?? null;
+			case ExtensionsFilter.CopilotIsSn:
+				return this.copilotIsSn ?? null;
+			case ExtensionsFilter.CopilotIsFcv1:
+				return this.copilotIsFcv1 ?? null;
 			default:
 				return null;
 		}
diff --git a/src/vs/workbench/services/authentication/test/browser/authenticationQueryServiceMocks.ts b/src/vs/workbench/services/authentication/test/browser/authenticationQueryServiceMocks.ts
index 4a2ca0e628436..2528c9f41ae17 100644
--- a/src/vs/workbench/services/authentication/test/browser/authenticationQueryServiceMocks.ts
+++ b/src/vs/workbench/services/authentication/test/browser/authenticationQueryServiceMocks.ts
@@ -64,7 +64,7 @@ export abstract class BaseTestService extends Disposable {
 	/**
 	 * Track a method call for verification in tests
 	 */
-	protected trackCall(method: string, ...args: any[]): void {
+	protected trackCall(method: string, ...args: unknown[]): void {
 		this._methodCalls.push({
 			method,
 			args: [...args],
diff --git a/src/vs/workbench/services/browserElements/browser/browserElementsService.ts b/src/vs/workbench/services/browserElements/browser/browserElementsService.ts
index 0f56a1edf3a4d..1a94f8a529cc8 100644
--- a/src/vs/workbench/services/browserElements/browser/browserElementsService.ts
+++ b/src/vs/workbench/services/browserElements/browser/browserElementsService.ts
@@ -16,6 +16,8 @@ export interface IBrowserElementsService {
 	// no browser implementation yet
 	getElementData(rect: IRectangle, token: CancellationToken, locator: IBrowserTargetLocator | undefined): Promise<IElementData | undefined>;
 
+	getFocusedElementData(rect: IRectangle, token: CancellationToken, locator: IBrowserTargetLocator | undefined): Promise<IElementData | undefined>;
+
 	startDebugSession(token: CancellationToken, locator: IBrowserTargetLocator): Promise<void>;
 
 	startConsoleSession(token: CancellationToken, locator: IBrowserTargetLocator): Promise<void>;
diff --git a/src/vs/workbench/services/browserElements/browser/webBrowserElementsService.ts b/src/vs/workbench/services/browserElements/browser/webBrowserElementsService.ts
index a98c4de1ba587..614ffc444f953 100644
--- a/src/vs/workbench/services/browserElements/browser/webBrowserElementsService.ts
+++ b/src/vs/workbench/services/browserElements/browser/webBrowserElementsService.ts
@@ -18,6 +18,10 @@ class WebBrowserElementsService implements IBrowserElementsService {
 		throw new Error('Not implemented');
 	}
 
+	async getFocusedElementData(rect: IRectangle, token: CancellationToken, locator: IBrowserTargetLocator | undefined): Promise<IElementData | undefined> {
+		throw new Error('Not implemented');
+	}
+
 	async startDebugSession(token: CancellationToken, locator: IBrowserTargetLocator): Promise<void> {
 		throw new Error('Not implemented');
 	}
diff --git a/src/vs/workbench/services/browserElements/electron-browser/browserElementsService.ts b/src/vs/workbench/services/browserElements/electron-browser/browserElementsService.ts
index fa2ddc772882d..1d88e15309bbe 100644
--- a/src/vs/workbench/services/browserElements/electron-browser/browserElementsService.ts
+++ b/src/vs/workbench/services/browserElements/electron-browser/browserElementsService.ts
@@ -90,6 +90,22 @@ class WorkbenchBrowserElementsService implements IBrowserElementsService {
 			disposable.dispose();
 		}
 	}
+
+	async getFocusedElementData(rect: IRectangle, token: CancellationToken, locator: IBrowserTargetLocator | undefined): Promise<IElementData | undefined> {
+		if (!locator) {
+			return undefined;
+		}
+		const cancelSelectionId = cancelSelectionIdPool++;
+		const onCancelChannel = `vscode:cancelElementSelection${cancelSelectionId}`;
+		const disposable = token.onCancellationRequested(() => {
+			ipcRenderer.send(onCancelChannel, cancelSelectionId);
+		});
+		try {
+			return await this.simpleBrowser.getFocusedElementData(rect, token, locator, cancelSelectionId);
+		} finally {
+			disposable.dispose();
+		}
+	}
 }
 
 registerSingleton(IBrowserElementsService, WorkbenchBrowserElementsService, InstantiationType.Delayed);
diff --git a/src/vs/workbench/services/browserView/electron-browser/playwrightWorkbenchService.ts b/src/vs/workbench/services/browserView/electron-browser/playwrightWorkbenchService.ts
index f50672fd91398..12dcd6a2b038d 100644
--- a/src/vs/workbench/services/browserView/electron-browser/playwrightWorkbenchService.ts
+++ b/src/vs/workbench/services/browserView/electron-browser/playwrightWorkbenchService.ts
@@ -3,7 +3,26 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
+import { mainWindow } from '../../../../base/browser/window.js';
+import { IChannel, ProxyChannel } from '../../../../base/parts/ipc/common/ipc.js';
 import { IPlaywrightService } from '../../../../platform/browserView/common/playwrightService.js';
 import { registerSharedProcessRemoteService } from '../../../../platform/ipc/electron-browser/services.js';
+import { ILogService } from '../../../../platform/log/common/log.js';
 
-registerSharedProcessRemoteService(IPlaywrightService, 'playwright');
+class PlaywrightChannelClient {
+	constructor(
+		channel: IChannel,
+		@ILogService logService: ILogService
+	) {
+		/**
+		 * send the current window's ID once via `__initialize`, so the server-side {@link PlaywrightChannel}
+		 * can create a per-window {@link PlaywrightWindowInstance}. All subsequent calls and events are proxied directly.
+		 */
+		void channel.call('__initialize', mainWindow.vscodeWindowId).catch((e) => {
+			logService.error(`Failed to initialize Playwright service`, e);
+		});
+		return ProxyChannel.toService<IPlaywrightService>(channel);
+	}
+}
+
+registerSharedProcessRemoteService(IPlaywrightService, 'playwright', { channelClientCtor: PlaywrightChannelClient });
diff --git a/src/vs/workbench/services/chat/common/chatEntitlementService.ts b/src/vs/workbench/services/chat/common/chatEntitlementService.ts
index 919d79dc291ee..02c83ae04b924 100644
--- a/src/vs/workbench/services/chat/common/chatEntitlementService.ts
+++ b/src/vs/workbench/services/chat/common/chatEntitlementService.ts
@@ -772,9 +772,9 @@ export class ChatEntitlementRequests extends Disposable {
 		return quotas;
 	}
 
-	private async request(url: string, type: 'GET', body: undefined, sessions: AuthenticationSession[], token: CancellationToken): Promise<IRequestContext | undefined>;
-	private async request(url: string, type: 'POST', body: object, sessions: AuthenticationSession[], token: CancellationToken): Promise<IRequestContext | undefined>;
-	private async request(url: string, type: 'GET' | 'POST', body: object | undefined, sessions: AuthenticationSession[], token: CancellationToken): Promise<IRequestContext | undefined> {
+	private async request(url: string, type: 'GET', body: undefined, sessions: AuthenticationSession[], token: CancellationToken, callSite: string): Promise<IRequestContext | undefined>;
+	private async request(url: string, type: 'POST', body: object, sessions: AuthenticationSession[], token: CancellationToken, callSite: string): Promise<IRequestContext | undefined>;
+	private async request(url: string, type: 'GET' | 'POST', body: object | undefined, sessions: AuthenticationSession[], token: CancellationToken, callSite: string): Promise<IRequestContext | undefined> {
 		let lastRequest: IRequestContext | undefined;
 
 		for (const session of sessions) {
@@ -790,7 +790,8 @@ export class ChatEntitlementRequests extends Disposable {
 					disableCache: true,
 					headers: {
 						'Authorization': `Bearer ${session.accessToken}`
-					}
+					},
+					callSite
 				}, token);
 
 				const status = response.res.statusCode;
@@ -843,7 +844,7 @@ export class ChatEntitlementRequests extends Disposable {
 			public_code_suggestions: 'enabled'
 		};
 
-		const response = await this.request(defaultChatAgent.entitlementSignupLimitedUrl, 'POST', body, sessions, CancellationToken.None);
+		const response = await this.request(defaultChatAgent.entitlementSignupLimitedUrl, 'POST', body, sessions, CancellationToken.None, 'chatEntitlementService.signUpFree');
 		if (!response) {
 			const retry = await this.onUnknownSignUpError(localize('signUpNoResponseError', "No response received."), '[chat entitlement] sign-up: no response');
 			return retry ? this.doSignUpFree(sessions) : { errorCode: 1 };
diff --git a/src/vs/workbench/services/configuration/browser/configurationService.ts b/src/vs/workbench/services/configuration/browser/configurationService.ts
index b6b3e48dcd3e1..a9813b527550b 100644
--- a/src/vs/workbench/services/configuration/browser/configurationService.ts
+++ b/src/vs/workbench/services/configuration/browser/configurationService.ts
@@ -47,6 +47,8 @@ import { IBrowserWorkbenchEnvironmentService } from '../../environment/browser/e
 import { workbenchConfigurationNodeBase } from '../../../common/configuration.js';
 import { mainWindow } from '../../../../base/browser/window.js';
 import { runWhenWindowIdle } from '../../../../base/browser/dom.js';
+import { renderAsPlaintext } from '../../../../base/browser/markdownRenderer.js';
+import { fixSettingLinks } from '../../preferences/common/preferencesModels.js';
 
 function getLocalUserConfigurationScopes(userDataProfile: IUserDataProfile, hasRemote: boolean): ConfigurationScope[] | undefined {
 	const isDefaultProfile = userDataProfile.isDefault || userDataProfile.useDefaultFlags?.settings;
@@ -194,6 +196,10 @@ export class WorkspaceService extends Disposable implements IWorkbenchConfigurat
 		return WorkbenchState.EMPTY;
 	}
 
+	public hasWorkspaceData(): boolean {
+		return this.getWorkbenchState() !== WorkbenchState.EMPTY;
+	}
+
 	public getWorkspaceFolder(resource: URI): IWorkspaceFolder | null {
 		return this.workspace.getFolder(resource);
 	}
@@ -1172,6 +1178,15 @@ class RegisterConfigurationSchemasContribution extends Disposable implements IWo
 	}
 
 	private registerConfigurationSchemas(): void {
+		// Ensure deprecationMessage is plain text for properties where it was derived from
+		// markdownDeprecationMessage, since the JSON editor diagnostics don't support markdown.
+		for (const key of Object.keys(allSettings.properties)) {
+			const prop = allSettings.properties[key];
+			if (prop.markdownDeprecationMessage && prop.deprecationMessage === prop.markdownDeprecationMessage) {
+				prop.deprecationMessage = renderAsPlaintext({ value: fixSettingLinks(prop.markdownDeprecationMessage) });
+			}
+		}
+
 		const allSettingsSchema: IJSONSchema = {
 			properties: allSettings.properties,
 			patternProperties: allSettings.patternProperties,
diff --git a/src/vs/workbench/services/dialogs/browser/abstractFileDialogService.ts b/src/vs/workbench/services/dialogs/browser/abstractFileDialogService.ts
index 6300496bd4ee4..8786b4ed5f660 100644
--- a/src/vs/workbench/services/dialogs/browser/abstractFileDialogService.ts
+++ b/src/vs/workbench/services/dialogs/browser/abstractFileDialogService.ts
@@ -229,7 +229,8 @@ export abstract class AbstractFileDialogService implements IFileDialogService {
 		const title = nls.localize('openFileOrFolder.title', 'Open File or Folder');
 		const availableFileSystems = this.addFileSchemaIfNeeded(schema);
 
-		const uri = await this.pickResource({ canSelectFiles: true, canSelectFolders: true, canSelectMany: false, defaultUri: options.defaultUri, title, availableFileSystems });
+		const uris = await this.pickResource({ canSelectFiles: true, canSelectFolders: true, canSelectMany: false, defaultUri: options.defaultUri, title, availableFileSystems });
+		const uri = uris?.[0];
 
 		if (uri) {
 			const stat = await this.fileService.stat(uri);
@@ -251,7 +252,8 @@ export abstract class AbstractFileDialogService implements IFileDialogService {
 		const title = nls.localize('openFile.title', 'Open File');
 		const availableFileSystems = this.addFileSchemaIfNeeded(schema);
 
-		const uri = await this.pickResource({ canSelectFiles: true, canSelectFolders: false, canSelectMany: false, defaultUri: options.defaultUri, title, availableFileSystems });
+		const uris = await this.pickResource({ canSelectFiles: true, canSelectFolders: false, canSelectMany: false, defaultUri: options.defaultUri, title, availableFileSystems });
+		const uri = uris?.[0];
 		if (uri) {
 			this.addFileToRecentlyOpened(uri);
 
@@ -271,7 +273,8 @@ export abstract class AbstractFileDialogService implements IFileDialogService {
 		const title = nls.localize('openFolder.title', 'Open Folder');
 		const availableFileSystems = this.addFileSchemaIfNeeded(schema, true);
 
-		const uri = await this.pickResource({ canSelectFiles: false, canSelectFolders: true, canSelectMany: false, defaultUri: options.defaultUri, title, availableFileSystems });
+		const uris = await this.pickResource({ canSelectFiles: false, canSelectFolders: true, canSelectMany: false, defaultUri: options.defaultUri, title, availableFileSystems });
+		const uri = uris?.[0];
 		if (uri) {
 			return this.hostService.openWindow([{ folderUri: uri }], { forceNewWindow: options.forceNewWindow, remoteAuthority: options.remoteAuthority });
 		}
@@ -282,7 +285,8 @@ export abstract class AbstractFileDialogService implements IFileDialogService {
 		const filters: FileFilter[] = [{ name: nls.localize('filterName.workspace', 'Workspace'), extensions: [WORKSPACE_EXTENSION] }];
 		const availableFileSystems = this.addFileSchemaIfNeeded(schema, true);
 
-		const uri = await this.pickResource({ canSelectFiles: true, canSelectFolders: false, canSelectMany: false, defaultUri: options.defaultUri, title, filters, availableFileSystems });
+		const uris = await this.pickResource({ canSelectFiles: true, canSelectFolders: false, canSelectMany: false, defaultUri: options.defaultUri, title, filters, availableFileSystems });
+		const uri = uris?.[0];
 		if (uri) {
 			return this.hostService.openWindow([{ workspaceUri: uri }], { forceNewWindow: options.forceNewWindow, remoteAuthority: options.remoteAuthority });
 		}
@@ -316,16 +320,14 @@ export abstract class AbstractFileDialogService implements IFileDialogService {
 			options.availableFileSystems = this.addFileSchemaIfNeeded(schema, options.canSelectFolders);
 		}
 
-		const uri = await this.pickResource(options);
-
-		return uri ? [uri] : undefined;
+		return this.pickResource(options);
 	}
 
 	protected getSimpleFileDialog(): ISimpleFileDialog {
 		return this.instantiationService.createInstance(SimpleFileDialog);
 	}
 
-	private pickResource(options: IOpenDialogOptions): Promise<URI | undefined> {
+	private pickResource(options: IOpenDialogOptions): Promise<URI[] | undefined> {
 		return this.getSimpleFileDialog().showOpenDialog(options);
 	}
 
diff --git a/src/vs/workbench/services/dialogs/browser/simpleFileDialog.ts b/src/vs/workbench/services/dialogs/browser/simpleFileDialog.ts
index 65b1d6b58ce8b..a5236c4b08204 100644
--- a/src/vs/workbench/services/dialogs/browser/simpleFileDialog.ts
+++ b/src/vs/workbench/services/dialogs/browser/simpleFileDialog.ts
@@ -105,7 +105,7 @@ enum UpdateResult {
 export const RemoteFileDialogContext = new RawContextKey<boolean>('remoteFileDialogVisible', false);
 
 export interface ISimpleFileDialog extends IDisposable {
-	showOpenDialog(options: IOpenDialogOptions): Promise<URI | undefined>;
+	showOpenDialog(options: IOpenDialogOptions): Promise<URI[] | undefined>;
 	showSaveDialog(options: ISaveDialogOptions): Promise<URI | undefined>;
 }
 
@@ -189,7 +189,7 @@ export class SimpleFileDialog extends Disposable implements ISimpleFileDialog {
 		return this.filePickBox.busy;
 	}
 
-	public async showOpenDialog(options: IOpenDialogOptions = {}): Promise<URI | undefined> {
+	public async showOpenDialog(options: IOpenDialogOptions = {}): Promise<URI[] | undefined> {
 		this.scheme = this.getScheme(options.availableFileSystems, options.defaultUri);
 		this.userHome = await this.getUserHome();
 		this.trueHome = await this.getUserHome(true);
@@ -198,7 +198,11 @@ export class SimpleFileDialog extends Disposable implements ISimpleFileDialog {
 			return Promise.resolve(undefined);
 		}
 		this.options = newOptions;
-		return this.pickResource();
+		const result = await this.pickResource();
+		if (Array.isArray(result)) {
+			return result;
+		}
+		return result ? [result] : undefined;
 	}
 
 	public async showSaveDialog(options: ISaveDialogOptions): Promise<URI | undefined> {
@@ -215,8 +219,8 @@ export class SimpleFileDialog extends Disposable implements ISimpleFileDialog {
 		this.options.canSelectFiles = true;
 
 		return new Promise<URI | undefined>((resolve) => {
-			this.pickResource(true).then(folderUri => {
-				resolve(folderUri);
+			this.pickResource(true).then(result => {
+				resolve(Array.isArray(result) ? result[0] : result);
 			});
 		});
 	}
@@ -281,7 +285,14 @@ export class SimpleFileDialog extends Disposable implements ISimpleFileDialog {
 			: this.fileDialogService.preferredHome(this.scheme);
 	}
 
-	private async pickResource(isSave: boolean = false): Promise<URI | undefined> {
+	private normalizeUri(uri: URI): URI {
+		uri = resources.addTrailingPathSeparator(uri, this.separator); // Ensures that c: is c:/ since this comes from user input and can be incorrect.
+		// To be consistent, we should never have a trailing path separator on directories (or anything else). Will not remove from c:/.
+		uri = resources.removeTrailingPathSeparator(uri);
+		return uri;
+	}
+
+	private async pickResource(isSave: boolean = false): Promise<URI[] | URI | undefined> {
 		this.allowFolderSelection = !!this.options.canSelectFolders;
 		this.allowFileSelection = !!this.options.canSelectFiles;
 		this.separator = this.labelService.getSeparator(this.scheme, this.remoteAuthority);
@@ -302,7 +313,7 @@ export class SimpleFileDialog extends Disposable implements ISimpleFileDialog {
 			}
 		}
 
-		return new Promise<URI | undefined>((resolve) => {
+		return new Promise<URI[] | URI | undefined>((resolve) => {
 			this.filePickBox = this._register(this.quickInputService.createQuickPick<FileQuickPickItem>());
 			this.busy = true;
 			this.filePickBox.matchOnLabel = false;
@@ -345,13 +356,15 @@ export class SimpleFileDialog extends Disposable implements ISimpleFileDialog {
 			this.filePickBox.value = this.pathFromUri(this.currentFolder, true);
 			this.filePickBox.valueSelection = [this.filePickBox.value.length, this.filePickBox.value.length];
 
-			const doResolve = (uri: URI | undefined) => {
-				if (uri) {
-					uri = resources.addTrailingPathSeparator(uri, this.separator); // Ensures that c: is c:/ since this comes from user input and can be incorrect.
-					// To be consistent, we should never have a trailing path separator on directories (or anything else). Will not remove from c:/.
-					uri = resources.removeTrailingPathSeparator(uri);
+			const doResolve = (uriOrUris: URI | URI[] | undefined) => {
+				if (uriOrUris) {
+					if (Array.isArray(uriOrUris)) {
+						uriOrUris = uriOrUris.map(uri => this.normalizeUri(uri));
+					} else {
+						uriOrUris = this.normalizeUri(uriOrUris);
+					}
 				}
-				resolve(uri);
+				resolve(uriOrUris);
 				this.contextKey.set(false);
 				this.dispose();
 			};
@@ -373,7 +386,7 @@ export class SimpleFileDialog extends Disposable implements ISimpleFileDialog {
 					});
 				} else {
 					return this.fileDialogService.showOpenDialog(this.options).then(result => {
-						doResolve(result ? result[0] : undefined);
+						doResolve(result);
 					});
 				}
 			}));
diff --git a/src/vs/workbench/services/dialogs/test/electron-browser/fileDialogService.test.ts b/src/vs/workbench/services/dialogs/test/electron-browser/fileDialogService.test.ts
index 8f55c547ee9c3..6406763524e95 100644
--- a/src/vs/workbench/services/dialogs/test/electron-browser/fileDialogService.test.ts
+++ b/src/vs/workbench/services/dialogs/test/electron-browser/fileDialogService.test.ts
@@ -89,10 +89,10 @@ suite('FileDialogService', function () {
 
 	test('Local - open/save workspaces availableFilesystems', async function () {
 		class TestSimpleFileDialog implements ISimpleFileDialog {
-			async showOpenDialog(options: IOpenDialogOptions): Promise<URI | undefined> {
+			async showOpenDialog(options: IOpenDialogOptions): Promise<URI[] | undefined> {
 				assert.strictEqual(options.availableFileSystems?.length, 1);
 				assert.strictEqual(options.availableFileSystems[0], Schemas.file);
-				return testFile;
+				return [testFile];
 			}
 			async showSaveDialog(options: ISaveDialogOptions): Promise<URI | undefined> {
 				assert.strictEqual(options.availableFileSystems?.length, 1);
@@ -111,10 +111,10 @@ suite('FileDialogService', function () {
 
 	test('Virtual - open/save workspaces availableFilesystems', async function () {
 		class TestSimpleFileDialog {
-			async showOpenDialog(options: IOpenDialogOptions): Promise<URI | undefined> {
+			async showOpenDialog(options: IOpenDialogOptions): Promise<URI[] | undefined> {
 				assert.strictEqual(options.availableFileSystems?.length, 1);
 				assert.strictEqual(options.availableFileSystems[0], Schemas.file);
-				return testFile;
+				return [testFile];
 			}
 			async showSaveDialog(options: ISaveDialogOptions): Promise<URI | undefined> {
 				assert.strictEqual(options.availableFileSystems?.length, 1);
@@ -137,11 +137,11 @@ suite('FileDialogService', function () {
 
 	test('Remote - open/save workspaces availableFilesystems', async function () {
 		class TestSimpleFileDialog implements ISimpleFileDialog {
-			async showOpenDialog(options: IOpenDialogOptions): Promise<URI | undefined> {
+			async showOpenDialog(options: IOpenDialogOptions): Promise<URI[] | undefined> {
 				assert.strictEqual(options.availableFileSystems?.length, 2);
 				assert.strictEqual(options.availableFileSystems[0], Schemas.vscodeRemote);
 				assert.strictEqual(options.availableFileSystems[1], Schemas.file);
-				return testFile;
+				return [testFile];
 			}
 			async showSaveDialog(options: ISaveDialogOptions): Promise<URI | undefined> {
 				assert.strictEqual(options.availableFileSystems?.length, 2);
@@ -170,8 +170,8 @@ suite('FileDialogService', function () {
 
 	test('Remote - filters default files/folders to RA (#195938)', async function () {
 		class TestSimpleFileDialog implements ISimpleFileDialog {
-			async showOpenDialog(): Promise<URI | undefined> {
-				return testFile;
+			async showOpenDialog(): Promise<URI[] | undefined> {
+				return [testFile];
 			}
 			async showSaveDialog(): Promise<URI | undefined> {
 				return testFile;
diff --git a/src/vs/workbench/services/editor/browser/editorService.ts b/src/vs/workbench/services/editor/browser/editorService.ts
index 839e48159e636..29189be6086de 100644
--- a/src/vs/workbench/services/editor/browser/editorService.ts
+++ b/src/vs/workbench/services/editor/browser/editorService.ts
@@ -579,6 +579,16 @@ export class EditorService extends Disposable implements EditorServiceImpl {
 			}
 		}
 
+		// Modal group: override `preserveFocus` to move focus into the modal because there is nothing to preserve if this is the first modal editor
+		if (
+			options?.preserveFocus &&
+			this.editorGroupService.activeModalEditorPart?.groups.some(modalGroup => modalGroup.id === group.id) &&
+			this.editorGroupService.activeModalEditorPart.count === 1 &&
+			this.editorGroupService.activeModalEditorPart.groups[0].isEmpty
+		) {
+			options = { ...options, preserveFocus: false };
+		}
+
 		return group.openEditor(typedEditor, options);
 	}
 
@@ -637,6 +647,16 @@ export class EditorService extends Disposable implements EditorServiceImpl {
 				}
 			}
 
+			// Modal group: override `preserveFocus` to move focus into the modal there is nothing to preserve if this is the first modal editor
+			if (
+				typedEditor.options?.preserveFocus &&
+				this.editorGroupService.activeModalEditorPart?.groups.some(modalGroup => modalGroup.id === group.id) &&
+				this.editorGroupService.activeModalEditorPart.count === 1 &&
+				this.editorGroupService.activeModalEditorPart.groups[0].isEmpty
+			) {
+				typedEditor = { ...typedEditor, options: { ...typedEditor.options, preserveFocus: false } };
+			}
+
 			// Update map of groups to editors
 			let targetGroupEditors = mapGroupToTypedEditors.get(group);
 			if (!targetGroupEditors) {
diff --git a/src/vs/workbench/services/editor/common/editorGroupFinder.ts b/src/vs/workbench/services/editor/common/editorGroupFinder.ts
index 96f6c8d112fc3..e7f6ae7e6bce7 100644
--- a/src/vs/workbench/services/editor/common/editorGroupFinder.ts
+++ b/src/vs/workbench/services/editor/common/editorGroupFinder.ts
@@ -146,10 +146,10 @@ function doFindGroup(input: EditorInputWithOptions | IUntypedEditorInput, prefer
 
 		// Respect option to reveal an editor if it is open (not necessarily visible)
 		// Still prefer to reveal an editor in a group where the editor is active though.
-		// We also try to reveal an editor if it has the `Singleton` capability which
-		// indicates that the same editor cannot be opened across groups.
+		// We also try to reveal an editor if it has the `ForceReveal` or `Singleton`
+		// capability which indicates that editor prefers to be revealed.
 		if (!group) {
-			if (options?.revealIfOpened || configurationService.getValue<boolean>('workbench.editor.revealIfOpen') || (isEditorInput(editor) && editor.hasCapability(EditorInputCapabilities.Singleton))) {
+			if (options?.revealIfOpened || configurationService.getValue<boolean>('workbench.editor.revealIfOpen') || (isEditorInput(editor) && (editor.hasCapability(EditorInputCapabilities.ForceReveal) || editor.hasCapability(EditorInputCapabilities.Singleton)))) {
 				let groupWithInputActive: IEditorGroup | undefined = undefined;
 				let groupWithInputOpened: IEditorGroup | undefined = undefined;
 
diff --git a/src/vs/workbench/services/editor/common/editorGroupsService.ts b/src/vs/workbench/services/editor/common/editorGroupsService.ts
index 9fcff97208a66..0e25a7e3803f5 100644
--- a/src/vs/workbench/services/editor/common/editorGroupsService.ts
+++ b/src/vs/workbench/services/editor/common/editorGroupsService.ts
@@ -543,6 +543,16 @@ export interface IModalEditorPart extends IEditorPart {
 	 */
 	toggleMaximized(): void;
 
+	/**
+	 * Size set by the user via resizing, if any.
+	 */
+	readonly size: IDimension | undefined;
+
+	/**
+	 * Position set by the user via dragging, if any.
+	 */
+	readonly position: { left: number; top: number } | undefined;
+
 	/**
 	 * The current navigation context, if any.
 	 */
diff --git a/src/vs/workbench/services/editor/test/browser/editorService.test.ts b/src/vs/workbench/services/editor/test/browser/editorService.test.ts
index 1300308ab628c..f11930103f879 100644
--- a/src/vs/workbench/services/editor/test/browser/editorService.test.ts
+++ b/src/vs/workbench/services/editor/test/browser/editorService.test.ts
@@ -8,7 +8,7 @@ import { EditorActivation, IResourceEditorInput } from '../../../../../platform/
 import { URI } from '../../../../../base/common/uri.js';
 import { Event } from '../../../../../base/common/event.js';
 import { DEFAULT_EDITOR_ASSOCIATION, EditorCloseContext, EditorsOrder, IEditorCloseEvent, EditorInputWithOptions, IEditorPane, IResourceDiffEditorInput, isEditorInputWithOptions, IUntitledTextResourceEditorInput, IUntypedEditorInput, SideBySideEditor, isEditorInput, EditorInputCapabilities } from '../../../../common/editor.js';
-import { workbenchInstantiationService, TestServiceAccessor, registerTestEditor, TestFileEditorInput, ITestInstantiationService, registerTestResourceEditor, registerTestSideBySideEditor, createEditorPart, registerTestFileEditor, TestTextFileEditor, TestSingletonFileEditorInput, workbenchTeardown } from '../../../../test/browser/workbenchTestServices.js';
+import { workbenchInstantiationService, TestServiceAccessor, registerTestEditor, TestFileEditorInput, ITestInstantiationService, registerTestResourceEditor, registerTestSideBySideEditor, createEditorPart, registerTestFileEditor, TestTextFileEditor, TestForceRevealFileEditorInput, workbenchTeardown } from '../../../../test/browser/workbenchTestServices.js';
 import { EditorService } from '../../browser/editorService.js';
 import { IEditorGroup, IEditorGroupsService, GroupDirection, GroupsArrangement } from '../../common/editorGroupsService.js';
 import { EditorPart } from '../../../../browser/parts/editor/editorPart.js';
@@ -40,7 +40,7 @@ suite('EditorService', () => {
 	let testLocalInstantiationService: ITestInstantiationService | undefined = undefined;
 
 	setup(() => {
-		disposables.add(registerTestEditor(TEST_EDITOR_ID, [new SyncDescriptor(TestFileEditorInput), new SyncDescriptor(TestSingletonFileEditorInput)], TEST_EDITOR_INPUT_ID));
+		disposables.add(registerTestEditor(TEST_EDITOR_ID, [new SyncDescriptor(TestFileEditorInput), new SyncDescriptor(TestForceRevealFileEditorInput)], TEST_EDITOR_INPUT_ID));
 		disposables.add(registerTestResourceEditor());
 		disposables.add(registerTestSideBySideEditor());
 	});
@@ -264,11 +264,11 @@ suite('EditorService', () => {
 		assert.strictEqual(editor2?.input, input);
 	});
 
-	test('openEditor() - singleton typed editors reveal instead of split', async () => {
+	test('openEditor() - force-reveal typed editors reveal instead of split', async () => {
 		const [part, service] = await createEditorService();
 
-		const input1 = disposables.add(new TestSingletonFileEditorInput(URI.parse('my://resource-basics1'), TEST_EDITOR_INPUT_ID));
-		const input2 = disposables.add(new TestSingletonFileEditorInput(URI.parse('my://resource-basics2'), TEST_EDITOR_INPUT_ID));
+		const input1 = disposables.add(new TestForceRevealFileEditorInput(URI.parse('my://resource-basics1'), TEST_EDITOR_INPUT_ID));
+		const input2 = disposables.add(new TestForceRevealFileEditorInput(URI.parse('my://resource-basics2'), TEST_EDITOR_INPUT_ID));
 
 		const input1Group = (await service.openEditor(input1, { pinned: true }))?.group;
 		const input2Group = (await service.openEditor(input2, { pinned: true }, SIDE_GROUP))?.group;
diff --git a/src/vs/workbench/services/editor/test/browser/modalEditorGroup.test.ts b/src/vs/workbench/services/editor/test/browser/modalEditorGroup.test.ts
index 865cb028552ff..7d37cde03e3cf 100644
--- a/src/vs/workbench/services/editor/test/browser/modalEditorGroup.test.ts
+++ b/src/vs/workbench/services/editor/test/browser/modalEditorGroup.test.ts
@@ -14,10 +14,14 @@ import { MockScopableContextKeyService } from '../../../../../platform/keybindin
 import { SideBySideEditorInput } from '../../../../common/editor/sideBySideEditorInput.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
 import { Registry } from '../../../../../platform/registry/common/platform.js';
-import { MODAL_GROUP, MODAL_GROUP_TYPE } from '../../common/editorService.js';
+import { IEditorService, MODAL_GROUP, MODAL_GROUP_TYPE } from '../../common/editorService.js';
 import { findGroup } from '../../common/editorGroupFinder.js';
 import { IConfigurationService } from '../../../../../platform/configuration/common/configuration.js';
 import { TestConfigurationService } from '../../../../../platform/configuration/test/common/testConfigurationService.js';
+import { EditorService } from '../../browser/editorService.js';
+import { IStorageService, StorageScope, StorageTarget } from '../../../../../platform/storage/common/storage.js';
+import { TestStorageService } from '../../../../test/common/workbenchTestServices.js';
+import { Memento } from '../../../../common/memento.js';
 
 suite('Modal Editor Group', () => {
 
@@ -506,6 +510,36 @@ suite('Modal Editor Group', () => {
 		modalPart.close();
 	});
 
+	test('modal editor part remembers maximized state across instances', async () => {
+		const instantiationService = workbenchInstantiationService({ contextKeyService: instantiationService => instantiationService.createInstance(MockScopableContextKeyService) }, disposables);
+		instantiationService.invokeFunction(accessor => Registry.as<IEditorFactoryRegistry>(EditorExtensions.EditorFactory).start(accessor));
+		const parts = await createEditorParts(instantiationService, disposables);
+		instantiationService.stub(IEditorGroupsService, parts);
+
+		// Open modal and maximize it
+		const modalPart1 = await parts.createModalEditorPart();
+		modalPart1.toggleMaximized();
+		assert.strictEqual(modalPart1.maximized, true);
+		modalPart1.close();
+
+		// Open a new modal - should remember maximized state
+		const modalPart2 = await parts.createModalEditorPart();
+		assert.strictEqual(modalPart2.maximized, true);
+		modalPart2.close();
+
+		// Open another modal after un-maximizing
+		const modalPart3 = await parts.createModalEditorPart();
+		assert.strictEqual(modalPart3.maximized, true);
+		modalPart3.toggleMaximized();
+		assert.strictEqual(modalPart3.maximized, false);
+		modalPart3.close();
+
+		// Should now remember non-maximized state
+		const modalPart4 = await parts.createModalEditorPart();
+		assert.strictEqual(modalPart4.maximized, false);
+		modalPart4.close();
+	});
+
 	suite('useModal: all', () => {
 
 		test('findGroup creates modal and returns its active group', async () => {
@@ -581,6 +615,64 @@ suite('Modal Editor Group', () => {
 
 			assert.strictEqual(parts.activeModalEditorPart, undefined);
 		});
+
+		test('shows tabs when multiple editors are open', async () => {
+			const instantiationService = workbenchInstantiationService({ contextKeyService: instantiationService => instantiationService.createInstance(MockScopableContextKeyService) }, disposables);
+			instantiationService.invokeFunction(accessor => Registry.as<IEditorFactoryRegistry>(EditorExtensions.EditorFactory).start(accessor));
+			const configurationService = new TestConfigurationService();
+			await configurationService.setUserConfiguration('workbench.editor.useModal', 'all');
+			instantiationService.stub(IConfigurationService, configurationService);
+			const parts = await createEditorParts(instantiationService, disposables);
+			instantiationService.stub(IEditorGroupsService, parts);
+
+			const editorService = disposables.add(instantiationService.createInstance(EditorService, undefined));
+			instantiationService.stub(IEditorService, editorService);
+
+			const input1 = createTestFileEditorInput(URI.file('foo/bar'), TEST_EDITOR_INPUT_ID);
+			await editorService.openEditor(input1, { pinned: true }, MODAL_GROUP);
+
+			const modalPart = parts.activeModalEditorPart!;
+			assert.ok(modalPart);
+
+			// With 1 editor, tabs should be hidden
+			assert.strictEqual(modalPart.partOptions.showTabs, 'none');
+
+			// Open a second editor
+			const input2 = createTestFileEditorInput(URI.file('foo/baz'), TEST_EDITOR_INPUT_ID);
+			await editorService.openEditor(input2, { pinned: true }, MODAL_GROUP);
+
+			// With 2 editors, tabs should be visible
+			assert.strictEqual(modalPart.partOptions.showTabs, 'multiple');
+
+			modalPart.close();
+		});
+
+		test('hides tabs when not in all mode even with multiple editors', async () => {
+			const instantiationService = workbenchInstantiationService({ contextKeyService: instantiationService => instantiationService.createInstance(MockScopableContextKeyService) }, disposables);
+			instantiationService.invokeFunction(accessor => Registry.as<IEditorFactoryRegistry>(EditorExtensions.EditorFactory).start(accessor));
+			const configurationService = new TestConfigurationService();
+			await configurationService.setUserConfiguration('workbench.editor.useModal', 'some');
+			instantiationService.stub(IConfigurationService, configurationService);
+			const parts = await createEditorParts(instantiationService, disposables);
+			instantiationService.stub(IEditorGroupsService, parts);
+
+			const editorService = disposables.add(instantiationService.createInstance(EditorService, undefined));
+			instantiationService.stub(IEditorService, editorService);
+
+			const input1 = createTestFileEditorInput(URI.file('foo/bar'), TEST_EDITOR_INPUT_ID);
+			await editorService.openEditor(input1, { pinned: true }, MODAL_GROUP);
+
+			const modalPart = parts.activeModalEditorPart!;
+			assert.ok(modalPart);
+
+			const input2 = createTestFileEditorInput(URI.file('foo/baz'), TEST_EDITOR_INPUT_ID);
+			await editorService.openEditor(input2, { pinned: true }, MODAL_GROUP);
+
+			// With 'some' mode, tabs should remain hidden even with multiple editors
+			assert.strictEqual(modalPart.partOptions.showTabs, 'none');
+
+			modalPart.close();
+		});
 	});
 
 	test('modal editor part editors can be moved to another group', async () => {
@@ -613,5 +705,66 @@ suite('Modal Editor Group', () => {
 		assert.strictEqual(parts.activeModalEditorPart, undefined);
 	});
 
+	test('openEditor with MODAL_GROUP ignores preserveFocus', async () => {
+		const instantiationService = workbenchInstantiationService({ contextKeyService: instantiationService => instantiationService.createInstance(MockScopableContextKeyService) }, disposables);
+		instantiationService.invokeFunction(accessor => Registry.as<IEditorFactoryRegistry>(EditorExtensions.EditorFactory).start(accessor));
+		const parts = await createEditorParts(instantiationService, disposables);
+		instantiationService.stub(IEditorGroupsService, parts);
+
+		const editorService = disposables.add(instantiationService.createInstance(EditorService, undefined));
+		instantiationService.stub(IEditorService, editorService);
+
+		const input = createTestFileEditorInput(URI.file('foo/bar'), TEST_EDITOR_INPUT_ID);
+		const pane = await editorService.openEditor(input, { pinned: true, preserveFocus: true }, MODAL_GROUP);
+
+		assert.ok(pane);
+		assert.strictEqual(pane.options?.preserveFocus, false);
+
+		parts.activeModalEditorPart?.close();
+	});
+
+	test('modal editor part state is remembered on close and reused on next open', async () => {
+		const instantiationService = workbenchInstantiationService({ contextKeyService: instantiationService => instantiationService.createInstance(MockScopableContextKeyService) }, disposables);
+		instantiationService.invokeFunction(accessor => Registry.as<IEditorFactoryRegistry>(EditorExtensions.EditorFactory).start(accessor));
+		const parts = await createEditorParts(instantiationService, disposables);
+		instantiationService.stub(IEditorGroupsService, parts);
+
+		// Create maximized modal and close it
+		const modalPart1 = await parts.createModalEditorPart({ maximized: true });
+		modalPart1.close();
+
+		// Create a new modal — it should restore maximized state
+		const modalPart2 = await parts.createModalEditorPart();
+		assert.strictEqual(modalPart2.maximized, true);
+
+		modalPart2.close();
+	});
+
+	test('modal editor part state restores from profile storage', async () => {
+		const instantiationService = workbenchInstantiationService({ contextKeyService: instantiationService => instantiationService.createInstance(MockScopableContextKeyService) }, disposables);
+		instantiationService.invokeFunction(accessor => Registry.as<IEditorFactoryRegistry>(EditorExtensions.EditorFactory).start(accessor));
+		const storageService = instantiationService.get(IStorageService) as TestStorageService;
+
+		// Pre-populate storage with modal state and clear memento cache
+		// so the next EditorParts instance reads fresh from storage
+		storageService.store('memento/workbench.editorParts', JSON.stringify({
+			'editorparts.modalState': {
+				maximized: true,
+				size: { width: 500, height: 400 },
+				position: { left: 100, top: 50 }
+			}
+		}), StorageScope.PROFILE, StorageTarget.MACHINE);
+		Memento.clear(StorageScope.PROFILE);
+
+		const parts = await createEditorParts(instantiationService, disposables);
+		instantiationService.stub(IEditorGroupsService, parts);
+
+		// Create modal — it should use state from storage
+		const modalPart = await parts.createModalEditorPart();
+		assert.strictEqual(modalPart.maximized, true);
+
+		modalPart.close();
+	});
+
 	ensureNoDisposablesAreLeakedInTestSuite();
 });
diff --git a/src/vs/workbench/services/environment/browser/environmentService.ts b/src/vs/workbench/services/environment/browser/environmentService.ts
index d0bc952a87478..a42fb531bdf51 100644
--- a/src/vs/workbench/services/environment/browser/environmentService.ts
+++ b/src/vs/workbench/services/environment/browser/environmentService.ts
@@ -255,7 +255,7 @@ export class BrowserWorkbenchEnvironmentService implements IBrowserWorkbenchEnvi
 	get disableWorkspaceTrust(): boolean { return !this.options.enableWorkspaceTrust; }
 
 	@memoize
-	get isSessionsWindow(): boolean { return false; }
+	get isSessionsWindow(): boolean { return this.payload?.get('isSessionsWindow') === 'true'; }
 
 	@memoize
 	get profile(): string | undefined { return this.payload?.get('profile'); }
@@ -322,6 +322,13 @@ export class BrowserWorkbenchEnvironmentService implements IBrowserWorkbenchEnvi
 					case 'inspect-extensions':
 						extensionHostDebugEnvironment.params.port = parseInt(value);
 						break;
+					case 'extensionEnvironment':
+						try {
+							extensionHostDebugEnvironment.params.env = JSON.parse(value);
+						} catch (error) {
+							onUnexpectedError(error);
+						}
+						break;
 					case 'enableProposedApi':
 						extensionHostDebugEnvironment.extensionEnabledProposedApi = [];
 						break;
diff --git a/src/vs/workbench/services/extensionManagement/electron-browser/extensionGalleryManifestService.ts b/src/vs/workbench/services/extensionManagement/electron-browser/extensionGalleryManifestService.ts
index 79e79f3a28307..47f7d460fb3c1 100644
--- a/src/vs/workbench/services/extensionManagement/electron-browser/extensionGalleryManifestService.ts
+++ b/src/vs/workbench/services/extensionManagement/electron-browser/extensionGalleryManifestService.ts
@@ -180,6 +180,7 @@ export class WorkbenchExtensionGalleryManifestService extends ExtensionGalleryMa
 				type: 'GET',
 				url,
 				headers,
+				callSite: 'extensionGalleryManifestService.fetchManifest'
 			}, CancellationToken.None);
 
 			const extensionGalleryManifest = await asJson<IExtensionGalleryManifest>(context);
diff --git a/src/vs/workbench/services/extensionManagement/electron-browser/extensionManagementService.ts b/src/vs/workbench/services/extensionManagement/electron-browser/extensionManagementService.ts
index 68eddb835ba69..0e4a999a5827e 100644
--- a/src/vs/workbench/services/extensionManagement/electron-browser/extensionManagementService.ts
+++ b/src/vs/workbench/services/extensionManagement/electron-browser/extensionManagementService.ts
@@ -76,7 +76,7 @@ export class ExtensionManagementService extends BaseExtensionManagementService {
 	protected override async installVSIXInServer(vsix: URI, server: IExtensionManagementServer, options: InstallOptions | undefined): Promise<ILocalExtension> {
 		if (vsix.scheme === Schemas.vscodeRemote && server === this.extensionManagementServerService.localExtensionManagementServer) {
 			const downloadedLocation = joinPath(this.environmentService.tmpDir, generateUuid());
-			await this.downloadService.download(vsix, downloadedLocation);
+			await this.downloadService.download(vsix, downloadedLocation, 'extensionManagement.downloadRemoteVsix');
 			vsix = downloadedLocation;
 		}
 		return super.installVSIXInServer(vsix, server, options);
diff --git a/src/vs/workbench/services/extensionManagement/electron-browser/nativeExtensionManagementService.ts b/src/vs/workbench/services/extensionManagement/electron-browser/nativeExtensionManagementService.ts
index cb1e06e97c8a5..6d5a51432b416 100644
--- a/src/vs/workbench/services/extensionManagement/electron-browser/nativeExtensionManagementService.ts
+++ b/src/vs/workbench/services/extensionManagement/electron-browser/nativeExtensionManagementService.ts
@@ -55,7 +55,7 @@ export class NativeExtensionManagementService extends ProfileAwareExtensionManag
 		}
 		this.logService.trace('Downloading extension from', vsix.toString());
 		const location = joinPath(this.nativeEnvironmentService.extensionsDownloadLocation, generateUuid());
-		await this.downloadService.download(vsix, location);
+		await this.downloadService.download(vsix, location, 'extensionManagement.downloadNativeVsix');
 		this.logService.info('Downloaded extension to', location.toString());
 		const cleanup = async () => {
 			try {
diff --git a/src/vs/workbench/services/extensions/common/abstractExtensionService.ts b/src/vs/workbench/services/extensions/common/abstractExtensionService.ts
index a0e599cd4b4b1..16ace8d597d8b 100644
--- a/src/vs/workbench/services/extensions/common/abstractExtensionService.ts
+++ b/src/vs/workbench/services/extensions/common/abstractExtensionService.ts
@@ -1024,9 +1024,13 @@ export abstract class AbstractExtensionService extends Disposable implements IEx
 		let managers: IExtensionHostManager[];
 		if (activationKind === ActivationKind.Immediate) {
 			// For immediate activation, only activate on local extension hosts
-			// and defer remote activation until the remote host is ready
+			// and on remote extension hosts that are already ready.
+			// Defer activation for remote hosts that are not yet ready to avoid
+			// blocking (e.g. during remote authority resolution).
 			managers = this._extensionHostManagers.filter(
-				extHostManager => extHostManager.kind === ExtensionHostKind.LocalProcess || extHostManager.kind === ExtensionHostKind.LocalWebWorker
+				extHostManager => extHostManager.kind === ExtensionHostKind.LocalProcess
+					|| extHostManager.kind === ExtensionHostKind.LocalWebWorker
+					|| extHostManager.isReady
 			);
 			this._pendingRemoteActivationEvents.add(activationEvent);
 		} else {
diff --git a/src/vs/workbench/services/extensions/common/extensionHostManager.ts b/src/vs/workbench/services/extensions/common/extensionHostManager.ts
index 88e8fd1d2571f..c7e1f8b626194 100644
--- a/src/vs/workbench/services/extensions/common/extensionHostManager.ts
+++ b/src/vs/workbench/services/extensions/common/extensionHostManager.ts
@@ -71,6 +71,7 @@ export class ExtensionHostManager extends Disposable implements IExtensionHostMa
 	private readonly _customers: IDisposable[];
 	private readonly _extensionHost: IExtensionHost;
 	private _proxy: Promise<IExtensionHostProxy | null> | null;
+	private _hasStarted: boolean = false;
 
 	public get pid(): number | null {
 		return this._extensionHost.pid;
@@ -152,6 +153,7 @@ export class ExtensionHostManager extends Disposable implements IExtensionHostMa
 			}
 		);
 		this._proxy.then(() => {
+			this._hasStarted = true;
 			initialActivationEvents.forEach((activationEvent) => this.activateByEvent(activationEvent, ActivationKind.Normal));
 			this._register(registerLatencyTestProvider({
 				measure: () => this.measure()
@@ -196,6 +198,10 @@ export class ExtensionHostManager extends Disposable implements IExtensionHostMa
 		};
 	}
 
+	public get isReady(): boolean {
+		return this._hasStarted;
+	}
+
 	public async ready(): Promise<void> {
 		await this._proxy;
 	}
diff --git a/src/vs/workbench/services/extensions/common/extensionHostManagers.ts b/src/vs/workbench/services/extensions/common/extensionHostManagers.ts
index 6c0947ddb9d0c..8b534771e44c1 100644
--- a/src/vs/workbench/services/extensions/common/extensionHostManagers.ts
+++ b/src/vs/workbench/services/extensions/common/extensionHostManagers.ts
@@ -22,6 +22,7 @@ export interface IExtensionHostManager {
 	readonly onDidChangeResponsiveState: Event<ResponsiveState>;
 	disconnect(): Promise<void>;
 	dispose(): void;
+	readonly isReady: boolean;
 	ready(): Promise<void>;
 	representsRunningLocation(runningLocation: ExtensionRunningLocation): boolean;
 	deltaExtensions(extensionsDelta: IExtensionDescriptionDelta): Promise<void>;
diff --git a/src/vs/workbench/services/extensions/common/extensionsRegistry.ts b/src/vs/workbench/services/extensions/common/extensionsRegistry.ts
index 6704355abae66..f9d57d5a53ef6 100644
--- a/src/vs/workbench/services/extensions/common/extensionsRegistry.ts
+++ b/src/vs/workbench/services/extensions/common/extensionsRegistry.ts
@@ -179,8 +179,8 @@ export const schema: IJSONSchema = {
 			properties: {
 				'vscode': {
 					type: 'string',
-					description: nls.localize('vscode.extension.engines.vscode', 'For VS Code extensions, specifies the VS Code version that the extension is compatible with. Cannot be *. For example: ^0.10.5 indicates compatibility with a minimum VS Code version of 0.10.5.'),
-					default: '^1.22.0',
+					description: nls.localize('vscode.extension.engines.vscode', 'For VS Code extensions, specifies the VS Code version that the extension is compatible with. Cannot be *. For example: ^1.105.0 indicates compatibility with a minimum VS Code version of 1.105.0.'),
+					default: '^1.105.0',
 				}
 			}
 		},
@@ -266,7 +266,7 @@ export const schema: IJSONSchema = {
 				defaultSnippets: [
 					{
 						label: 'onWebviewPanel',
-						description: nls.localize('vscode.extension.activationEvents.onWebviewPanel', 'An activation event emmited when a webview is loaded of a certain viewType'),
+						description: nls.localize('vscode.extension.activationEvents.onWebviewPanel', 'An activation event emitted when a webview is loaded of a certain viewType'),
 						body: 'onWebviewPanel:viewType'
 					},
 					{
@@ -421,7 +421,7 @@ export const schema: IJSONSchema = {
 					},
 					{
 						label: 'onMcpCollection',
-						description: nls.localize('vscode.extension.activationEvents.onMcpCollection', 'An activation event emitted whenver a tool from the MCP server is requested.'),
+						description: nls.localize('vscode.extension.activationEvents.onMcpCollection', 'An activation event emitted whenever a tool from the MCP server is requested.'),
 						body: 'onMcpCollection:${2:collectionId}',
 					},
 					{
diff --git a/src/vs/workbench/services/extensions/common/lazyCreateExtensionHostManager.ts b/src/vs/workbench/services/extensions/common/lazyCreateExtensionHostManager.ts
index f9acb2a03c971..8662618b1b94b 100644
--- a/src/vs/workbench/services/extensions/common/lazyCreateExtensionHostManager.ts
+++ b/src/vs/workbench/services/extensions/common/lazyCreateExtensionHostManager.ts
@@ -90,6 +90,10 @@ export class LazyCreateExtensionHostManager extends Disposable implements IExten
 		return actual;
 	}
 
+	public get isReady(): boolean {
+		return this._startCalled.isOpen() && (this._actual?.isReady ?? false);
+	}
+
 	public async ready(): Promise<void> {
 		await this._startCalled.wait();
 		if (this._actual) {
diff --git a/src/vs/workbench/services/extensions/electron-browser/localProcessExtensionHost.ts b/src/vs/workbench/services/extensions/electron-browser/localProcessExtensionHost.ts
index af93d8558dea5..93fac9a488913 100644
--- a/src/vs/workbench/services/extensions/electron-browser/localProcessExtensionHost.ts
+++ b/src/vs/workbench/services/extensions/electron-browser/localProcessExtensionHost.ts
@@ -268,7 +268,7 @@ export class NativeLocalProcessExtensionHost extends Disposable implements IExte
 			const inspectorUrlMatch = output.data && output.data.match(/ws:\/\/([^\s]+):(\d+)\/([^\s]+)/);
 			if (inspectorUrlMatch) {
 				const [, host, port, auth] = inspectorUrlMatch;
-				const devtoolsUrl = `devtools://devtools/bundled/inspector.html?experiments=true&v8only=true&ws=${host}:${port}/${auth}`;
+				const devtoolsUrl = `devtools://devtools/bundled/js_app.html?v8only=true&ws=${host}:${port}/${auth}`;
 				if (!this._environmentService.isBuilt && !this._isExtensionDevTestFromCli) {
 					console.debug(`%c[Extension Host] %cdebugger inspector at ${devtoolsUrl}`, 'color: blue', 'color:');
 				}
diff --git a/src/vs/workbench/services/extensions/test/browser/extensionService.test.ts b/src/vs/workbench/services/extensions/test/browser/extensionService.test.ts
index fa3b8370531ed..86c11e9e1bf61 100644
--- a/src/vs/workbench/services/extensions/test/browser/extensionService.test.ts
+++ b/src/vs/workbench/services/extensions/test/browser/extensionService.test.ts
@@ -192,12 +192,15 @@ suite('ExtensionService', () => {
 		private _extHostId = 0;
 		public readonly order: string[] = [];
 		public readonly activationEvents: { event: string; activationKind: ActivationKind; kind: ExtensionHostKind }[] = [];
+		public remoteExtHostIsReady = true;
+		public localExtHostIsReady = true;
 		protected _pickExtensionHostKind(extensionId: ExtensionIdentifier, extensionKinds: ExtensionKind[], isInstalledLocally: boolean, isInstalledRemotely: boolean, preference: ExtensionRunningPreference): ExtensionHostKind | null {
 			throw new Error('Method not implemented.');
 		}
 		protected override _doCreateExtensionHostManager(extensionHost: IExtensionHost, initialActivationEvents: string[]): IExtensionHostManager {
 			const order = this.order;
 			const activationEvents = this.activationEvents;
+			const extService = this;
 			const extensionHostId = ++this._extHostId;
 			const extHostKind = extensionHost.runningLocation.kind;
 			order.push(`create ${extensionHostId}`);
@@ -205,6 +208,7 @@ suite('ExtensionService', () => {
 				override onDidExit = Event.None;
 				override onDidChangeResponsiveState = Event.None;
 				override kind = extHostKind;
+				override get isReady() { return extHostKind === ExtensionHostKind.Remote ? extService.remoteExtHostIsReady : extService.localExtHostIsReady; }
 				override disconnect() {
 					return Promise.resolve();
 				}
@@ -334,16 +338,41 @@ suite('ExtensionService', () => {
 		assert.strictEqual(events[0].activationKind, ActivationKind.Immediate);
 	});
 
-	test('Immediate activation only activates local extension hosts', async () => {
+	test('Immediate activation includes ready remote extension hosts (issue #297019)', async () => {
 		extService.activationEvents.length = 0; // Clear any initial activations
 
 		await extService.activateByEvent('onTest', ActivationKind.Immediate);
 
-		// Should only activate on local hosts (LocalProcess and LocalWebWorker), not Remote
+		// When remote host is ready, Immediate activation should include it
 		const activatedKinds = extService.activationEvents.map(e => e.kind);
 		assert.ok(activatedKinds.includes(ExtensionHostKind.LocalProcess), 'Should activate on LocalProcess');
 		assert.ok(activatedKinds.includes(ExtensionHostKind.LocalWebWorker), 'Should activate on LocalWebWorker');
-		assert.ok(!activatedKinds.includes(ExtensionHostKind.Remote), 'Should NOT activate on Remote');
+		assert.ok(activatedKinds.includes(ExtensionHostKind.Remote), 'Should activate on ready Remote host');
+	});
+
+	test('Immediate activation excludes not-ready remote extension hosts', async () => {
+		extService.remoteExtHostIsReady = false;
+		extService.activationEvents.length = 0; // Clear any initial activations
+
+		await extService.activateByEvent('onTest', ActivationKind.Immediate);
+
+		// When remote host is not ready, Immediate activation should skip it
+		const activatedKinds = extService.activationEvents.map(e => e.kind);
+		assert.ok(activatedKinds.includes(ExtensionHostKind.LocalProcess), 'Should activate on LocalProcess');
+		assert.ok(activatedKinds.includes(ExtensionHostKind.LocalWebWorker), 'Should activate on LocalWebWorker');
+		assert.ok(!activatedKinds.includes(ExtensionHostKind.Remote), 'Should NOT activate on not-ready Remote host');
+	});
+
+	test('Immediate activation still activates local extension hosts even when not ready', async () => {
+		extService.localExtHostIsReady = false;
+		extService.activationEvents.length = 0; // Clear any initial activations
+
+		await extService.activateByEvent('onTest', ActivationKind.Immediate);
+
+		// Local hosts should always be activated for Immediate, regardless of isReady
+		const activatedKinds = extService.activationEvents.map(e => e.kind);
+		assert.ok(activatedKinds.includes(ExtensionHostKind.LocalProcess), 'Should activate on LocalProcess even when not ready');
+		assert.ok(activatedKinds.includes(ExtensionHostKind.LocalWebWorker), 'Should activate on LocalWebWorker even when not ready');
 	});
 
 	test('Normal activation activates all extension hosts', async () => {
diff --git a/src/vs/workbench/services/policies/test/browser/accountPolicyService.test.ts b/src/vs/workbench/services/policies/test/browser/accountPolicyService.test.ts
index db6c6bc4aa5ed..a61c00d64aec0 100644
--- a/src/vs/workbench/services/policies/test/browser/accountPolicyService.test.ts
+++ b/src/vs/workbench/services/policies/test/browser/accountPolicyService.test.ts
@@ -4,18 +4,18 @@
  *--------------------------------------------------------------------------------------------*/
 
 import assert from 'assert';
+import { IDefaultAccount, IDefaultAccountAuthenticationProvider, IPolicyData } from '../../../../../base/common/defaultAccount.js';
 import { Event } from '../../../../../base/common/event.js';
-import { NullLogService } from '../../../../../platform/log/common/log.js';
-import { IDefaultAccountProvider, IDefaultAccountService } from '../../../../../platform/defaultAccount/common/defaultAccount.js';
-import { DefaultAccountService } from '../../../accounts/browser/defaultAccount.js';
-import { AccountPolicyService } from '../../common/accountPolicyService.js';
+import { PolicyCategory } from '../../../../../base/common/policy.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
-import { Registry } from '../../../../../platform/registry/common/platform.js';
 import { Extensions, IConfigurationNode, IConfigurationRegistry } from '../../../../../platform/configuration/common/configurationRegistry.js';
 import { DefaultConfiguration, PolicyConfiguration } from '../../../../../platform/configuration/common/configurations.js';
-import { IDefaultAccount, IDefaultAccountAuthenticationProvider, IPolicyData } from '../../../../../base/common/defaultAccount.js';
-import { PolicyCategory } from '../../../../../base/common/policy.js';
+import { IDefaultAccountProvider, IDefaultAccountService } from '../../../../../platform/defaultAccount/common/defaultAccount.js';
+import { NullLogService } from '../../../../../platform/log/common/log.js';
+import { Registry } from '../../../../../platform/registry/common/platform.js';
 import { TestProductService } from '../../../../test/common/workbenchTestServices.js';
+import { DefaultAccountService } from '../../../accounts/browser/defaultAccount.js';
+import { AccountPolicyService } from '../../common/accountPolicyService.js';
 
 const BASE_DEFAULT_ACCOUNT: IDefaultAccount = {
 	authenticationProvider: {
@@ -32,6 +32,8 @@ class DefaultAccountProvider implements IDefaultAccountProvider {
 
 	readonly onDidChangeDefaultAccount = Event.None;
 	readonly onDidChangePolicyData = Event.None;
+	readonly copilotTokenInfo = null;
+	readonly onDidChangeCopilotTokenInfo = Event.None;
 
 	constructor(
 		readonly defaultAccount: IDefaultAccount,
diff --git a/src/vs/workbench/services/policies/test/browser/multiplexPolicyService.test.ts b/src/vs/workbench/services/policies/test/browser/multiplexPolicyService.test.ts
index 512d8d9111084..6af55b8bf7caf 100644
--- a/src/vs/workbench/services/policies/test/browser/multiplexPolicyService.test.ts
+++ b/src/vs/workbench/services/policies/test/browser/multiplexPolicyService.test.ts
@@ -4,25 +4,25 @@
  *--------------------------------------------------------------------------------------------*/
 
 import assert from 'assert';
+import { VSBuffer } from '../../../../../base/common/buffer.js';
+import { IDefaultAccount, IDefaultAccountAuthenticationProvider, IPolicyData } from '../../../../../base/common/defaultAccount.js';
 import { Event } from '../../../../../base/common/event.js';
-import { NullLogService } from '../../../../../platform/log/common/log.js';
-import { IDefaultAccountProvider, IDefaultAccountService } from '../../../../../platform/defaultAccount/common/defaultAccount.js';
-import { DefaultAccountService } from '../../../accounts/browser/defaultAccount.js';
-import { AccountPolicyService } from '../../common/accountPolicyService.js';
+import { PolicyCategory } from '../../../../../base/common/policy.js';
+import { URI } from '../../../../../base/common/uri.js';
 import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
-import { Registry } from '../../../../../platform/registry/common/platform.js';
 import { Extensions, IConfigurationNode, IConfigurationRegistry } from '../../../../../platform/configuration/common/configurationRegistry.js';
 import { DefaultConfiguration, PolicyConfiguration } from '../../../../../platform/configuration/common/configurations.js';
-import { MultiplexPolicyService } from '../../common/multiplexPolicyService.js';
-import { FilePolicyService } from '../../../../../platform/policy/common/filePolicyService.js';
-import { URI } from '../../../../../base/common/uri.js';
+import { IDefaultAccountProvider, IDefaultAccountService } from '../../../../../platform/defaultAccount/common/defaultAccount.js';
 import { IFileService } from '../../../../../platform/files/common/files.js';
-import { InMemoryFileSystemProvider } from '../../../../../platform/files/common/inMemoryFilesystemProvider.js';
 import { FileService } from '../../../../../platform/files/common/fileService.js';
-import { VSBuffer } from '../../../../../base/common/buffer.js';
-import { IDefaultAccount, IDefaultAccountAuthenticationProvider, IPolicyData } from '../../../../../base/common/defaultAccount.js';
-import { PolicyCategory } from '../../../../../base/common/policy.js';
+import { InMemoryFileSystemProvider } from '../../../../../platform/files/common/inMemoryFilesystemProvider.js';
+import { NullLogService } from '../../../../../platform/log/common/log.js';
+import { FilePolicyService } from '../../../../../platform/policy/common/filePolicyService.js';
+import { Registry } from '../../../../../platform/registry/common/platform.js';
 import { TestProductService } from '../../../../test/common/workbenchTestServices.js';
+import { DefaultAccountService } from '../../../accounts/browser/defaultAccount.js';
+import { AccountPolicyService } from '../../common/accountPolicyService.js';
+import { MultiplexPolicyService } from '../../common/multiplexPolicyService.js';
 
 const BASE_DEFAULT_ACCOUNT: IDefaultAccount = {
 	authenticationProvider: {
@@ -39,6 +39,8 @@ class DefaultAccountProvider implements IDefaultAccountProvider {
 
 	readonly onDidChangeDefaultAccount = Event.None;
 	readonly onDidChangePolicyData = Event.None;
+	readonly copilotTokenInfo = null;
+	readonly onDidChangeCopilotTokenInfo = Event.None;
 
 	constructor(
 		readonly defaultAccount: IDefaultAccount,
diff --git a/src/vs/workbench/services/preferences/browser/preferencesService.ts b/src/vs/workbench/services/preferences/browser/preferencesService.ts
index a1ca22b3c4a2d..f871d6dd5d9e1 100644
--- a/src/vs/workbench/services/preferences/browser/preferencesService.ts
+++ b/src/vs/workbench/services/preferences/browser/preferencesService.ts
@@ -48,6 +48,7 @@ import { IURLService } from '../../../../platform/url/common/url.js';
 import { compareIgnoreCase } from '../../../../base/common/strings.js';
 import { IExtensionService } from '../../extensions/common/extensions.js';
 import { IProgressService, ProgressLocation } from '../../../../platform/progress/common/progress.js';
+import { IWorkbenchEnvironmentService } from '../../environment/common/environmentService.js';
 
 const emptyEditableSettingsContent = '{\n}';
 
@@ -90,7 +91,8 @@ export class PreferencesService extends Disposable implements IPreferencesServic
 		@ITextEditorService private readonly textEditorService: ITextEditorService,
 		@IURLService urlService: IURLService,
 		@IExtensionService private readonly extensionService: IExtensionService,
-		@IProgressService private readonly progressService: IProgressService
+		@IProgressService private readonly progressService: IProgressService,
+		@IWorkbenchEnvironmentService private readonly environmentService: IWorkbenchEnvironmentService,
 	) {
 		super();
 		// The default keybindings.json updates based on keyboard layouts, so here we make sure
@@ -273,7 +275,7 @@ export class PreferencesService extends Disposable implements IPreferencesServic
 			...options,
 			focusSearch: true
 		};
-		const group = this.getEditorGroupFromOptions(false, options);
+		const group = this.getEditorGroupFromOptions(options);
 		return this.editorService.openEditor(input, validateSettingsEditorOptions(options), group);
 	}
 
@@ -354,11 +356,11 @@ export class PreferencesService extends Disposable implements IPreferencesServic
 					this.editorService.openEditor({ resource: editableKeybindings, options }, sideEditorGroup.id)
 				]);
 			} else {
-				await this.editorService.openEditor({ resource: editableKeybindings, options }, options.groupId);
+				await this.editorService.openEditor({ resource: editableKeybindings, options }, this.getEditorGroupFromOptions(options));
 			}
 
 		} else {
-			const group = this.getEditorGroupFromOptions(false, options);
+			const group = this.getEditorGroupFromOptions(options);
 			const editor = (await this.editorService.openEditor(this.instantiationService.createInstance(KeybindingsEditorInput), { ...options }, group)) as IKeybindingsEditorPane;
 			if (options.query) {
 				editor.search(options.query);
@@ -371,8 +373,11 @@ export class PreferencesService extends Disposable implements IPreferencesServic
 		return this.editorService.openEditor({ resource: this.defaultKeybindingsResource, label: nls.localize('defaultKeybindings', "Default Keybindings") });
 	}
 
-	private getEditorGroupFromOptions(isTextual: boolean, options: { groupId?: number; openToSide?: boolean }): PreferredGroup {
-		if (!isTextual && this.configurationService.getValue<string>('workbench.editor.useModal') !== 'off') {
+	private getEditorGroupFromOptions(options: { groupId?: number; openToSide?: boolean }): PreferredGroup {
+		if (
+			this.configurationService.getValue<string>('workbench.editor.useModal') !== 'off' &&					// modal editors enabled in settings
+			!this.environmentService.enableSmokeTestDriver && !this.environmentService.extensionTestsLocationURI	// but not in smoke test or extension test environments to reduce flakiness
+		) {
 			return MODAL_GROUP;
 		}
 		if (options.openToSide) {
@@ -385,7 +390,7 @@ export class PreferencesService extends Disposable implements IPreferencesServic
 	}
 
 	private async openSettingsJson(resource: URI, options: IOpenSettingsOptions): Promise<IEditorPane | undefined> {
-		const group = this.getEditorGroupFromOptions(true, options);
+		const group = this.getEditorGroupFromOptions(options);
 		const editor = await this.doOpenSettingsJson(resource, options, group);
 		if (editor && options?.revealSetting) {
 			await this.revealSetting(options.revealSetting.key, !!options.revealSetting.edit, editor, resource);
diff --git a/src/vs/workbench/services/preferences/common/preferencesModels.ts b/src/vs/workbench/services/preferences/common/preferencesModels.ts
index 84fa12bc44db0..1d399cefc9503 100644
--- a/src/vs/workbench/services/preferences/common/preferencesModels.ts
+++ b/src/vs/workbench/services/preferences/common/preferencesModels.ts
@@ -28,6 +28,14 @@ import { isString } from '../../../../base/common/types.js';
 export const nullRange: IRange = { startLineNumber: -1, startColumn: -1, endLineNumber: -1, endColumn: -1 };
 function isNullRange(range: IRange): boolean { return range.startLineNumber === -1 && range.startColumn === -1 && range.endLineNumber === -1 && range.endColumn === -1; }
 
+/**
+ * Strips VS Code's custom `#settingId#` link syntax from a markdown string so the setting key
+ * remains as inline code (e.g. `` `settingId` ``). Useful for contexts that don't render markdown links.
+ */
+export function fixSettingLinks(text: string): string {
+	return text.replace(/`#([^#`]*)#`/g, (_, settingName) => `\`${settingName}\``);
+}
+
 abstract class AbstractSettingsModel extends EditorModel {
 
 	protected _currentResultGroups = new Map<string, ISearchResultGroup>();
@@ -1072,13 +1080,11 @@ class SettingsContentBuilder {
 	}
 
 	private pushSettingDescription(setting: ISetting, indent: string): void {
-		const fixSettingLink = (line: string) => line.replace(/`#(.*)#`/g, (match, settingName) => `\`${settingName}\``);
-
 		setting.descriptionRanges = [];
 		const descriptionPreValue = indent + '// ';
 		const deprecationMessageLines = setting.deprecationMessage?.split(/\n/g) ?? [];
 		for (let line of [...deprecationMessageLines, ...setting.description]) {
-			line = fixSettingLink(line);
+			line = fixSettingLinks(line);
 
 			this._contentByLines.push(descriptionPreValue + line);
 			setting.descriptionRanges.push({ startLineNumber: this.lineCountWithOffset, startColumn: this.lastLine.indexOf(line) + 1, endLineNumber: this.lineCountWithOffset, endColumn: this.lastLine.length });
@@ -1088,7 +1094,7 @@ class SettingsContentBuilder {
 			setting.enumDescriptions.forEach((desc, i) => {
 				const displayEnum = escapeInvisibleChars(String(setting.enum![i]));
 				const line = desc ?
-					`${displayEnum}: ${fixSettingLink(desc)}` :
+					`${displayEnum}: ${fixSettingLinks(desc)}` :
 					displayEnum;
 
 				const lines = line.split(/\n/g);
diff --git a/src/vs/workbench/services/telemetry/browser/telemetryService.ts b/src/vs/workbench/services/telemetry/browser/telemetryService.ts
index f666488665257..d5e60f72b213a 100644
--- a/src/vs/workbench/services/telemetry/browser/telemetryService.ts
+++ b/src/vs/workbench/services/telemetry/browser/telemetryService.ts
@@ -20,6 +20,7 @@ import { IRemoteAgentService } from '../../remote/common/remoteAgentService.js';
 import { IMeteredConnectionService } from '../../../../platform/meteredConnection/common/meteredConnection.js';
 import { resolveWorkbenchCommonProperties } from './workbenchCommonProperties.js';
 import { experimentsEnabled } from '../common/workbenchTelemetryUtils.js';
+import { IRequestService, NO_FETCH_TELEMETRY } from '../../../../platform/request/common/request.js';
 
 export class TelemetryService extends Disposable implements ITelemetryService {
 
@@ -42,7 +43,8 @@ export class TelemetryService extends Disposable implements ITelemetryService {
 		@IStorageService storageService: IStorageService,
 		@IProductService productService: IProductService,
 		@IRemoteAgentService remoteAgentService: IRemoteAgentService,
-		@IMeteredConnectionService meteredConnectionService: IMeteredConnectionService
+		@IMeteredConnectionService meteredConnectionService: IMeteredConnectionService,
+		@IRequestService requestService: IRequestService
 	) {
 		super();
 
@@ -54,6 +56,29 @@ export class TelemetryService extends Disposable implements ITelemetryService {
 				this.impl = this.initializeService(environmentService, loggerService, configurationService, storageService, productService, remoteAgentService, meteredConnectionService);
 			}
 		}));
+
+		this._register(requestService.onDidCompleteRequest(e => {
+			if (e.callSite === NO_FETCH_TELEMETRY) {
+				return;
+			}
+			type FetchCallClassification = {
+				owner: 'lramos15';
+				comment: 'Tracks fetch requests made through the request service';
+				callSite: { classification: 'SystemMetaData'; purpose: 'PerformanceAndHealth'; comment: 'The call site that initiated the request.' };
+				latency: { classification: 'SystemMetaData'; purpose: 'PerformanceAndHealth'; isMeasurement: true; comment: 'Time in milliseconds for the request to complete.' };
+				statusCode: { classification: 'SystemMetaData'; purpose: 'PerformanceAndHealth'; isMeasurement: true; comment: 'HTTP status code of the response.' };
+			};
+			type FetchCallEvent = {
+				callSite: string;
+				latency: number;
+				statusCode: number | undefined;
+			};
+			this.publicLog2<FetchCallEvent, FetchCallClassification>('fetchCall', {
+				callSite: e.callSite,
+				latency: e.latency,
+				statusCode: e.statusCode,
+			});
+		}));
 	}
 
 	/**
diff --git a/src/vs/workbench/services/telemetry/electron-browser/telemetryService.ts b/src/vs/workbench/services/telemetry/electron-browser/telemetryService.ts
index 7dd70946844d5..108147e271690 100644
--- a/src/vs/workbench/services/telemetry/electron-browser/telemetryService.ts
+++ b/src/vs/workbench/services/telemetry/electron-browser/telemetryService.ts
@@ -18,6 +18,7 @@ import { InstantiationType, registerSingleton } from '../../../../platform/insta
 import { ClassifiedEvent, StrictPropertyCheck, OmitMetadata, IGDPRProperty } from '../../../../platform/telemetry/common/gdprTypings.js';
 import { process } from '../../../../base/parts/sandbox/electron-browser/globals.js';
 import { experimentsEnabled } from '../common/workbenchTelemetryUtils.js';
+import { IRequestService, NO_FETCH_TELEMETRY } from '../../../../platform/request/common/request.js';
 
 export class TelemetryService extends Disposable implements ITelemetryService {
 
@@ -38,7 +39,8 @@ export class TelemetryService extends Disposable implements ITelemetryService {
 		@IProductService productService: IProductService,
 		@ISharedProcessService sharedProcessService: ISharedProcessService,
 		@IStorageService storageService: IStorageService,
-		@IConfigurationService configurationService: IConfigurationService
+		@IConfigurationService configurationService: IConfigurationService,
+		@IRequestService requestService: IRequestService
 	) {
 		super();
 
@@ -70,6 +72,29 @@ export class TelemetryService extends Disposable implements ITelemetryService {
 		}
 
 		this.sendErrorTelemetry = this.impl.sendErrorTelemetry;
+
+		this._register(requestService.onDidCompleteRequest(e => {
+			if (e.callSite === NO_FETCH_TELEMETRY) {
+				return;
+			}
+			type FetchCallClassification = {
+				owner: 'lramos15';
+				comment: 'Tracks fetch requests made through the request service';
+				callSite: { classification: 'SystemMetaData'; purpose: 'PerformanceAndHealth'; comment: 'The call site that initiated the request.' };
+				latency: { classification: 'SystemMetaData'; purpose: 'PerformanceAndHealth'; isMeasurement: true; comment: 'Time in milliseconds for the request to complete.' };
+				statusCode: { classification: 'SystemMetaData'; purpose: 'PerformanceAndHealth'; isMeasurement: true; comment: 'HTTP status code of the response.' };
+			};
+			type FetchCallEvent = {
+				callSite: string;
+				latency: number;
+				statusCode: number | undefined;
+			};
+			this.publicLog2<FetchCallEvent, FetchCallClassification>('fetchCall', {
+				callSite: e.callSite,
+				latency: e.latency,
+				statusCode: e.statusCode,
+			});
+		}));
 	}
 
 	setExperimentProperty(name: string, value: string): void {
diff --git a/src/vs/workbench/services/terminal/common/embedderTerminalService.ts b/src/vs/workbench/services/terminal/common/embedderTerminalService.ts
index 0d0bd4f349d8b..3665fe2bbe666 100644
--- a/src/vs/workbench/services/terminal/common/embedderTerminalService.ts
+++ b/src/vs/workbench/services/terminal/common/embedderTerminalService.ts
@@ -56,7 +56,7 @@ class EmbedderTerminalService implements IEmbedderTerminalService {
 	declare _serviceBrand: undefined;
 
 	private readonly _onDidCreateTerminal = new Emitter<IShellLaunchConfig>();
-	readonly onDidCreateTerminal = Event.buffer(this._onDidCreateTerminal.event);
+	readonly onDidCreateTerminal = Event.buffer(this._onDidCreateTerminal.event, 'onDidCreateTerminal');
 
 	createTerminal(options: IEmbedderTerminalOptions): void {
 		const slc: EmbedderTerminal = {
diff --git a/src/vs/workbench/services/themes/browser/cssExtensionPoint.ts b/src/vs/workbench/services/themes/browser/cssExtensionPoint.ts
index cdeca23bd2dd9..69b74111341b0 100644
--- a/src/vs/workbench/services/themes/browser/cssExtensionPoint.ts
+++ b/src/vs/workbench/services/themes/browser/cssExtensionPoint.ts
@@ -157,6 +157,10 @@ export class CSSExtensionPoint {
 				// Check if this extension's theme is currently active
 				if (this.isExtensionThemeActive(extensionId)) {
 					this.activateExtensionCSS(extension);
+				} else if (this.stylesheetsByExtension.has(extensionId)) {
+					// Theme is no longer active but cached CSS is still loaded — remove it
+					this.removeStylesheets(extensionId);
+					this.clearCacheForExtension(extensionId);
 				}
 			}
 		});
@@ -173,14 +177,17 @@ export class CSSExtensionPoint {
 	}
 
 	private onThemeChange(): void {
-		// Check all pending extensions and activate/deactivate as needed
+		// Activate pending extensions whose theme just became active
 		for (const [extensionId, extension] of this.pendingExtensions) {
-			const isActive = this.stylesheetsByExtension.has(extensionId);
-			const shouldBeActive = this.isExtensionThemeActive(extensionId);
-
-			if (shouldBeActive && !isActive) {
+			if (!this.stylesheetsByExtension.has(extensionId) && this.isExtensionThemeActive(extensionId)) {
 				this.activateExtensionCSS(extension);
-			} else if (!shouldBeActive && isActive) {
+			}
+		}
+
+		// Deactivate all extensions whose theme is no longer active,
+		// including cached CSS that may not yet be in pendingExtensions
+		for (const extensionId of this.stylesheetsByExtension.keys()) {
+			if (!this.isExtensionThemeActive(extensionId)) {
 				this.removeStylesheets(extensionId);
 				this.clearCacheForExtension(extensionId);
 			}
diff --git a/src/vs/workbench/services/themes/browser/workbenchThemeService.ts b/src/vs/workbench/services/themes/browser/workbenchThemeService.ts
index 1a4648762e31f..a7911a941611f 100644
--- a/src/vs/workbench/services/themes/browser/workbenchThemeService.ts
+++ b/src/vs/workbench/services/themes/browser/workbenchThemeService.ts
@@ -525,7 +525,7 @@ export class WorkbenchThemeService extends Disposable implements IWorkbenchTheme
 					publisherDisplayName: string;
 					themeId: string;
 				};
-				this.telemetryService.publicLog2<ActivatePluginEvent, ActivatePluginClassification>('activatePlugin', {
+				this.telemetryService.publicLog2<ActivatePluginEvent, ActivatePluginClassification>('activateThemeExtension', {
 					id: themeData.extensionId,
 					name: themeData.extensionName,
 					isBuiltin: themeData.extensionIsBuiltin,
diff --git a/src/vs/workbench/services/themes/common/workbenchThemeService.ts b/src/vs/workbench/services/themes/common/workbenchThemeService.ts
index a214818b29ce2..8fefa7297ca33 100644
--- a/src/vs/workbench/services/themes/common/workbenchThemeService.ts
+++ b/src/vs/workbench/services/themes/common/workbenchThemeService.ts
@@ -11,6 +11,7 @@ import { ConfigurationTarget } from '../../../../platform/configuration/common/c
 import { isBoolean, isString } from '../../../../base/common/types.js';
 import { IconContribution, IconDefinition } from '../../../../platform/theme/common/iconRegistry.js';
 import { ColorScheme, ThemeTypeSelector } from '../../../../platform/theme/common/theme.js';
+import product from '../../../../platform/product/common/product.js';
 
 export const IWorkbenchThemeService = refineServiceDecorator<IThemeService, IWorkbenchThemeService>(IThemeService);
 
@@ -38,17 +39,19 @@ export enum ThemeSettings {
 	SYSTEM_COLOR_THEME = 'window.systemColorTheme'
 }
 
-export enum ThemeSettingDefaults {
-	COLOR_THEME_DARK = 'Default Dark Modern',
-	COLOR_THEME_LIGHT = 'Default Light Modern',
-	COLOR_THEME_HC_DARK = 'Default High Contrast',
-	COLOR_THEME_HC_LIGHT = 'Default High Contrast Light',
+const isOSS = !product.quality;
 
-	COLOR_THEME_DARK_OLD = 'Default Dark+',
-	COLOR_THEME_LIGHT_OLD = 'Default Light+',
+export namespace ThemeSettingDefaults {
+	export const COLOR_THEME_DARK = isOSS ? 'Experimental Dark' : 'Default Dark Modern';
+	export const COLOR_THEME_LIGHT = isOSS ? 'Experimental Light' : 'Default Light Modern';
+	export const COLOR_THEME_HC_DARK = 'Default High Contrast';
+	export const COLOR_THEME_HC_LIGHT = 'Default High Contrast Light';
 
-	FILE_ICON_THEME = 'vs-seti',
-	PRODUCT_ICON_THEME = 'Default',
+	export const COLOR_THEME_DARK_OLD = 'Default Dark+';
+	export const COLOR_THEME_LIGHT_OLD = 'Default Light+';
+
+	export const FILE_ICON_THEME = 'vs-seti';
+	export const PRODUCT_ICON_THEME = 'Default';
 }
 
 export const COLOR_THEME_DARK_INITIAL_COLORS = {
diff --git a/src/vs/workbench/services/update/browser/updateService.ts b/src/vs/workbench/services/update/browser/updateService.ts
index 611eef4f9463c..d9cb9499f8801 100644
--- a/src/vs/workbench/services/update/browser/updateService.ts
+++ b/src/vs/workbench/services/update/browser/updateService.ts
@@ -98,7 +98,7 @@ export class BrowserUpdateService extends Disposable implements IUpdateService {
 		// noop
 	}
 
-	async disableProgressiveReleases(): Promise<void> {
+	async setInternalOrg(_internalOrg: string | undefined): Promise<void> {
 		// noop - not applicable in browser
 	}
 }
diff --git a/src/vs/workbench/services/userAttention/test/browser/userAttentionService.test.ts b/src/vs/workbench/services/userAttention/test/browser/userAttentionService.test.ts
index 07886188bb60e..287550a7532bd 100644
--- a/src/vs/workbench/services/userAttention/test/browser/userAttentionService.test.ts
+++ b/src/vs/workbench/services/userAttention/test/browser/userAttentionService.test.ts
@@ -44,7 +44,7 @@ suite('UserAttentionService', () => {
 		};
 
 		const originalCreateInstance = insta.createInstance;
-		sinon.stub(insta, 'createInstance').callsFake((ctor: any, ...args: any[]) => {
+		sinon.stub(insta, 'createInstance').callsFake((ctor: any, ...args: unknown[]) => {
 			if (ctor === UserAttentionServiceEnv) {
 				return hostAdapterMock;
 			}
diff --git a/src/vs/workbench/services/userDataProfile/browser/userDataProfileImportExportService.ts b/src/vs/workbench/services/userDataProfile/browser/userDataProfileImportExportService.ts
index db73853690f19..a45bd6dc1aff2 100644
--- a/src/vs/workbench/services/userDataProfile/browser/userDataProfileImportExportService.ts
+++ b/src/vs/workbench/services/userDataProfile/browser/userDataProfileImportExportService.ts
@@ -432,7 +432,7 @@ export class UserDataProfileImportExportService extends Disposable implements IU
 			}
 		}
 
-		const context = await this.requestService.request({ type: 'GET', url: resource.toString(true) }, CancellationToken.None);
+		const context = await this.requestService.request({ type: 'GET', url: resource.toString(true), callSite: 'userDataProfileImportExportService.resolveContent' }, CancellationToken.None);
 		if (context.res.statusCode === 200) {
 			return await asText(context);
 		} else {
diff --git a/src/vs/workbench/services/userDataProfile/browser/userDataProfileInit.ts b/src/vs/workbench/services/userDataProfile/browser/userDataProfileInit.ts
index 6df19e5a98e59..8e2b632d1fe7c 100644
--- a/src/vs/workbench/services/userDataProfile/browser/userDataProfileInit.ts
+++ b/src/vs/workbench/services/userDataProfile/browser/userDataProfileInit.ts
@@ -130,7 +130,7 @@ export class UserDataProfileInitializer implements IUserDataInitializer {
 		}
 		try {
 			const url = URI.revive(this.environmentService.options.profile.contents).toString(true);
-			const context = await this.requestService.request({ type: 'GET', url }, CancellationToken.None);
+			const context = await this.requestService.request({ type: 'GET', url, callSite: 'userDataProfileInit.initializeProfile' }, CancellationToken.None);
 			if (context.res.statusCode === 200) {
 				return await asJson(context);
 			} else {
diff --git a/src/vs/workbench/services/userDataProfile/browser/userDataProfileManagement.ts b/src/vs/workbench/services/userDataProfile/browser/userDataProfileManagement.ts
index cc56d9a6ac537..43da461974125 100644
--- a/src/vs/workbench/services/userDataProfile/browser/userDataProfileManagement.ts
+++ b/src/vs/workbench/services/userDataProfile/browser/userDataProfileManagement.ts
@@ -161,7 +161,7 @@ export class UserDataProfileManagementService extends Disposable implements IUse
 	async getBuiltinProfileTemplates(): Promise<IProfileTemplateInfo[]> {
 		if (this.productService.profileTemplatesUrl) {
 			try {
-				const context = await this.requestService.request({ type: 'GET', url: this.productService.profileTemplatesUrl }, CancellationToken.None);
+				const context = await this.requestService.request({ type: 'GET', url: this.productService.profileTemplatesUrl, callSite: 'userDataProfileManagement.getProfileTemplates' }, CancellationToken.None);
 				if (context.res.statusCode === 200) {
 					return (await asJson<IProfileTemplateInfo[]>(context)) || [];
 				} else {
diff --git a/src/vs/workbench/test/browser/componentFixtures/agentSessionsViewer.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/agentSessionsViewer.fixture.ts
new file mode 100644
index 0000000000000..2b098ab315827
--- /dev/null
+++ b/src/vs/workbench/test/browser/componentFixtures/agentSessionsViewer.fixture.ts
@@ -0,0 +1,709 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { URI } from '../../../../base/common/uri.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { MarkdownString } from '../../../../base/common/htmlContent.js';
+import { mock } from '../../../../base/test/common/mock.js';
+import { FuzzyScore } from '../../../../base/common/filters.js';
+import { ITreeNode } from '../../../../base/browser/ui/tree/tree.js';
+import { observableValue } from '../../../../base/common/observable.js';
+import { IMarkdownRendererService, MarkdownRendererService } from '../../../../platform/markdown/browser/markdownRenderer.js';
+import { IProductService } from '../../../../platform/product/common/productService.js';
+import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
+import { TestConfigurationService } from '../../../../platform/configuration/test/common/testConfigurationService.js';
+import { EditorMarkdownCodeBlockRenderer } from '../../../../editor/browser/widget/markdownRenderer/browser/editorMarkdownCodeBlockRenderer.js';
+import { AgentSessionRenderer, AgentSessionSectionRenderer, IAgentSessionRendererOptions } from '../../../contrib/chat/browser/agentSessions/agentSessionsViewer.js';
+import { AgentSessionStatus, IAgentSession, AgentSessionSection, IAgentSessionSection } from '../../../contrib/chat/browser/agentSessions/agentSessionsModel.js';
+import { AgentSessionProviders } from '../../../contrib/chat/browser/agentSessions/agentSessions.js';
+import { AgentSessionApprovalModel, IAgentSessionApprovalInfo } from '../../../contrib/chat/browser/agentSessions/agentSessionApprovalModel.js';
+import { HoverPosition } from '../../../../base/browser/ui/hover/hoverWidget.js';
+import { ComponentFixtureContext, createEditorServices, defineComponentFixture, defineThemedFixtureGroup, registerWorkbenchServices } from './fixtureUtils.js';
+
+import '../../../contrib/chat/browser/agentSessions/media/agentsessionsviewer.css';
+
+// ============================================================================
+// Mock helpers
+// ============================================================================
+
+function createMockSession(overrides: Partial<IAgentSession> & { label: string; status: AgentSessionStatus; providerType: string }): IAgentSession {
+	const now = Date.now();
+	return new class extends mock<IAgentSession>() {
+		override readonly resource = overrides.resource ?? URI.parse(`vscode-chat-session://${overrides.providerType}/session-${Math.random().toString(36).slice(2)}`);
+		override readonly label = overrides.label;
+		override readonly status = overrides.status;
+		override readonly providerType = overrides.providerType;
+		override readonly providerLabel = overrides.providerLabel ?? overrides.providerType;
+		override readonly icon = overrides.icon ?? Codicon.vm;
+		override readonly badge = overrides.badge;
+		override readonly description = overrides.description;
+		override readonly tooltip = overrides.tooltip;
+		override readonly changes = overrides.changes;
+		override readonly timing = overrides.timing ?? {
+			created: now - 60 * 60 * 1000,
+			lastRequestStarted: undefined,
+			lastRequestEnded: undefined,
+		};
+		override isArchived(): boolean { return overrides.isArchived?.() ?? false; }
+		override setArchived(): void { }
+		override isRead(): boolean { return overrides.isRead?.() ?? true; }
+		override setRead(): void { }
+	}();
+}
+
+function wrapAsTreeNode<T>(element: T): ITreeNode<T, FuzzyScore> {
+	return {
+		element,
+		children: [],
+		depth: 0,
+		visibleChildrenCount: 0,
+		visibleChildIndex: 0,
+		collapsible: false,
+		collapsed: false,
+		visible: true,
+		filterData: undefined,
+	};
+}
+
+const rendererOptions: IAgentSessionRendererOptions = {
+	disableHover: true,
+	getHoverPosition: () => HoverPosition.BELOW,
+};
+
+// ============================================================================
+// Render helpers
+// ============================================================================
+
+function createMockApprovalModel(sessionResource: URI, info: IAgentSessionApprovalInfo): AgentSessionApprovalModel {
+	const obs = observableValue<IAgentSessionApprovalInfo | undefined>('mockApproval', info);
+	return new class extends mock<AgentSessionApprovalModel>() {
+		override getApproval(resource: URI) {
+			if (resource.toString() === sessionResource.toString()) {
+				return obs;
+			}
+			return observableValue<IAgentSessionApprovalInfo | undefined>('mockApproval.empty', undefined);
+		}
+	}();
+}
+
+function renderSessionItem(ctx: ComponentFixtureContext, session: IAgentSession, approvalModel?: AgentSessionApprovalModel): void {
+	const { container, disposableStore } = ctx;
+
+	const instantiationService = createEditorServices(disposableStore, {
+		colorTheme: ctx.theme,
+		additionalServices: (reg) => {
+			registerWorkbenchServices(reg);
+			reg.define(IMarkdownRendererService, MarkdownRendererService);
+			reg.defineInstance(IProductService, new class extends mock<IProductService>() {
+				override readonly urlProtocol = 'vscode';
+			}());
+		},
+	});
+
+	const configService = instantiationService.get(IConfigurationService) as TestConfigurationService;
+	configService.setUserConfiguration('editor', { fontFamily: 'monospace' });
+	const markdownRendererService = instantiationService.get(IMarkdownRendererService);
+	markdownRendererService.setDefaultCodeBlockRenderer(instantiationService.createInstance(EditorMarkdownCodeBlockRenderer));
+
+	const renderer = disposableStore.add(
+		instantiationService.createInstance(AgentSessionRenderer, rendererOptions, approvalModel ?? undefined, observableValue<URI | undefined>('activeSessionResource', undefined))
+	);
+
+	container.style.width = '350px';
+	container.style.height = 'auto';
+	container.style.backgroundColor = 'var(--vscode-sideBar-background)';
+	container.classList.add('agent-sessions-viewer');
+
+	const listRow = document.createElement('div');
+	listRow.classList.add('monaco-list-row');
+	listRow.style.position = 'relative';
+	container.appendChild(listRow);
+
+	const template = renderer.renderTemplate(listRow);
+	renderer.renderElement(wrapAsTreeNode(session), 0, template);
+}
+
+function renderSectionItem(ctx: ComponentFixtureContext, section: IAgentSessionSection): void {
+	const { container, disposableStore } = ctx;
+
+	const instantiationService = createEditorServices(disposableStore, {
+		colorTheme: ctx.theme,
+		additionalServices: (reg) => {
+			registerWorkbenchServices(reg);
+		},
+	});
+
+	const renderer = instantiationService.createInstance(AgentSessionSectionRenderer);
+
+	container.style.width = '350px';
+	container.style.height = 'auto';
+	container.style.backgroundColor = 'var(--vscode-sideBar-background)';
+	container.classList.add('agent-sessions-viewer');
+
+	const listRow = document.createElement('div');
+	listRow.classList.add('monaco-list-row');
+	listRow.style.position = 'relative';
+	container.appendChild(listRow);
+
+	const template = renderer.renderTemplate(listRow);
+	renderer.renderElement(wrapAsTreeNode(section), 0, template);
+}
+
+// ============================================================================
+// Fixtures
+// ============================================================================
+
+const now = Date.now();
+
+export default defineThemedFixtureGroup({
+
+	// --- Status variants ---
+
+	CompletedRead: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Refactor auth middleware',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Local,
+			timing: {
+				created: now - 2 * 60 * 60 * 1000,
+				lastRequestStarted: now - 2 * 60 * 60 * 1000,
+				lastRequestEnded: now - 2 * 60 * 60 * 1000 + 45 * 1000,
+			},
+		})),
+	}),
+
+	CompletedUnread: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Add unit tests for parser',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Local,
+			isRead: () => false,
+			timing: {
+				created: now - 30 * 60 * 1000,
+				lastRequestStarted: now - 30 * 60 * 1000,
+				lastRequestEnded: now - 25 * 60 * 1000,
+			},
+		})),
+	}),
+
+	InProgress: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Implement dark mode toggle',
+			status: AgentSessionStatus.InProgress,
+			providerType: AgentSessionProviders.Local,
+			timing: {
+				created: now - 5 * 60 * 1000,
+				lastRequestStarted: now - 2 * 60 * 1000,
+				lastRequestEnded: undefined,
+			},
+		})),
+	}),
+
+	NeedsInput: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Fix CI pipeline configuration',
+			status: AgentSessionStatus.NeedsInput,
+			providerType: AgentSessionProviders.Local,
+			isRead: () => false,
+			timing: {
+				created: now - 10 * 60 * 1000,
+				lastRequestStarted: now - 8 * 60 * 1000,
+				lastRequestEnded: undefined,
+			},
+		})),
+	}),
+
+	FailedWithDuration: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Deploy staging environment',
+			status: AgentSessionStatus.Failed,
+			providerType: AgentSessionProviders.Local,
+			timing: {
+				created: now - 60 * 60 * 1000,
+				lastRequestStarted: now - 60 * 60 * 1000,
+				lastRequestEnded: now - 60 * 60 * 1000 + 3 * 60 * 1000,
+			},
+		})),
+	}),
+
+	FailedWithoutDuration: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Migrate database schema',
+			status: AgentSessionStatus.Failed,
+			providerType: AgentSessionProviders.Local,
+			timing: {
+				created: now - 3 * 60 * 60 * 1000,
+				lastRequestStarted: undefined,
+				lastRequestEnded: undefined,
+			},
+		})),
+	}),
+
+	// --- Content variants ---
+
+	WithDiffChanges: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Refactor settings page',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Local,
+			changes: { files: 5, insertions: 142, deletions: 87 },
+			timing: {
+				created: now - 45 * 60 * 1000,
+				lastRequestStarted: now - 45 * 60 * 1000,
+				lastRequestEnded: now - 40 * 60 * 1000,
+			},
+		})),
+	}),
+
+	WithFileChangesList: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Update API endpoints',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Background,
+			icon: Codicon.worktree,
+			changes: [
+				{ modifiedUri: URI.file('/src/api/routes.ts'), insertions: 25, deletions: 10 },
+				{ modifiedUri: URI.file('/src/api/handlers.ts'), insertions: 50, deletions: 30 },
+				{ modifiedUri: URI.file('/tests/api.test.ts'), insertions: 40, deletions: 5 },
+			],
+			timing: {
+				created: now - 2 * 60 * 60 * 1000,
+				lastRequestStarted: now - 2 * 60 * 60 * 1000,
+				lastRequestEnded: now - 90 * 60 * 1000,
+			},
+		})),
+	}),
+
+	WithBadge: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Optimize build pipeline',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Local,
+			badge: 'PR #1234',
+			timing: {
+				created: now - 4 * 60 * 60 * 1000,
+				lastRequestStarted: now - 4 * 60 * 60 * 1000,
+				lastRequestEnded: now - 3.5 * 60 * 60 * 1000,
+			},
+		})),
+	}),
+
+	WithMarkdownBadge: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Review security patches',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Cloud,
+			icon: Codicon.cloud,
+			badge: new MarkdownString('$(shield) Secure'),
+			timing: {
+				created: now - 6 * 60 * 60 * 1000,
+				lastRequestStarted: now - 6 * 60 * 60 * 1000,
+				lastRequestEnded: now - 5.5 * 60 * 60 * 1000,
+			},
+		})),
+	}),
+
+	WithDescription: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Upgrade dependencies',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Local,
+			description: 'Updated 12 packages to latest versions',
+			timing: {
+				created: now - 24 * 60 * 60 * 1000,
+				lastRequestStarted: now - 24 * 60 * 60 * 1000,
+				lastRequestEnded: now - 23.5 * 60 * 60 * 1000,
+			},
+		})),
+	}),
+
+	WithMarkdownDescription: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Fix accessibility issues',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Local,
+			description: new MarkdownString('$(check) All WCAG checks passed'),
+			timing: {
+				created: now - 48 * 60 * 60 * 1000,
+				lastRequestStarted: now - 48 * 60 * 60 * 1000,
+				lastRequestEnded: now - 47 * 60 * 60 * 1000,
+			},
+		})),
+	}),
+
+	WithBadgeAndDiff: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Implement search feature',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Local,
+			badge: 'draft',
+			changes: { files: 8, insertions: 320, deletions: 45 },
+			timing: {
+				created: now - 3 * 60 * 60 * 1000,
+				lastRequestStarted: now - 3 * 60 * 60 * 1000,
+				lastRequestEnded: now - 2.5 * 60 * 60 * 1000,
+			},
+		})),
+	}),
+
+	// --- State variants ---
+
+	Archived: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Old migration script',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Local,
+			isArchived: () => true,
+			timing: {
+				created: now - 7 * 24 * 60 * 60 * 1000,
+				lastRequestStarted: now - 7 * 24 * 60 * 60 * 1000,
+				lastRequestEnded: now - 7 * 24 * 60 * 60 * 1000 + 10 * 60 * 1000,
+			},
+		})),
+	}),
+
+	ArchivedUnread: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Archived unread task',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Local,
+			isArchived: () => true,
+			isRead: () => false,
+			timing: {
+				created: now - 5 * 24 * 60 * 60 * 1000,
+				lastRequestStarted: now - 5 * 24 * 60 * 60 * 1000,
+				lastRequestEnded: now - 5 * 24 * 60 * 60 * 1000 + 5 * 60 * 1000,
+			},
+		})),
+	}),
+
+	// --- Provider-type variants ---
+
+	CloudProvider: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Generate API documentation',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Cloud,
+			icon: Codicon.cloud,
+			timing: {
+				created: now - 90 * 60 * 1000,
+				lastRequestStarted: now - 90 * 60 * 1000,
+				lastRequestEnded: now - 80 * 60 * 1000,
+			},
+		})),
+	}),
+
+	BackgroundProvider: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Run linter across codebase',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Background,
+			icon: Codicon.worktree,
+			timing: {
+				created: now - 120 * 60 * 1000,
+				lastRequestStarted: now - 120 * 60 * 1000,
+				lastRequestEnded: now - 110 * 60 * 1000,
+			},
+		})),
+	}),
+
+	ClaudeProvider: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Analyze code complexity',
+			status: AgentSessionStatus.Completed,
+			providerType: AgentSessionProviders.Claude,
+			icon: Codicon.claude,
+			timing: {
+				created: now - 150 * 60 * 1000,
+				lastRequestStarted: now - 150 * 60 * 1000,
+				lastRequestEnded: now - 140 * 60 * 1000,
+			},
+		})),
+	}),
+
+	CloudProviderInProgress: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Build integration tests',
+			status: AgentSessionStatus.InProgress,
+			providerType: AgentSessionProviders.Cloud,
+			icon: Codicon.cloud,
+			isRead: () => false,
+			timing: {
+				created: now - 10 * 60 * 1000,
+				lastRequestStarted: now - 3 * 60 * 1000,
+				lastRequestEnded: undefined,
+			},
+		})),
+	}),
+
+	// --- In-progress with description override ---
+
+	InProgressWithDescription: defineComponentFixture({
+		render: (ctx) => renderSessionItem(ctx, createMockSession({
+			label: 'Scaffold new microservice',
+			status: AgentSessionStatus.InProgress,
+			providerType: AgentSessionProviders.Background,
+			icon: Codicon.worktree,
+			description: 'Installing dependencies...',
+			timing: {
+				created: now - 5 * 60 * 1000,
+				lastRequestStarted: now - 60 * 1000,
+				lastRequestEnded: undefined,
+			},
+		})),
+	}),
+
+	// --- Section headers ---
+
+	SectionToday: defineComponentFixture({
+		render: (ctx) => renderSectionItem(ctx, {
+			section: AgentSessionSection.Today,
+			label: 'Today',
+			sessions: [],
+		}),
+	}),
+
+	SectionYesterday: defineComponentFixture({
+		render: (ctx) => renderSectionItem(ctx, {
+			section: AgentSessionSection.Yesterday,
+			label: 'Yesterday',
+			sessions: [],
+		}),
+	}),
+
+	SectionLastWeek: defineComponentFixture({
+		render: (ctx) => renderSectionItem(ctx, {
+			section: AgentSessionSection.Week,
+			label: 'Last 7 days',
+			sessions: [],
+		}),
+	}),
+
+	SectionOlder: defineComponentFixture({
+		render: (ctx) => renderSectionItem(ctx, {
+			section: AgentSessionSection.Older,
+			label: 'Older',
+			sessions: [],
+		}),
+	}),
+
+	SectionArchived: defineComponentFixture({
+		render: (ctx) => renderSectionItem(ctx, {
+			section: AgentSessionSection.Archived,
+			label: 'Archived',
+			sessions: [],
+		}),
+	}),
+
+	SectionMore: defineComponentFixture({
+		render: (ctx) => renderSectionItem(ctx, {
+			section: AgentSessionSection.More,
+			label: 'More',
+			sessions: [],
+		}),
+	}),
+
+	// --- Approval row variants ---
+
+	ApprovalRowJson: defineComponentFixture({
+		render: (ctx) => {
+			const resource = URI.parse('vscode-chat-session://local/approval-json');
+			const approvalModel = createMockApprovalModel(resource, {
+				label: '{ "action": "deleteFile", "path": "/src/old-module.ts" }',
+				languageId: 'json',
+				confirm: () => { },
+			});
+			renderSessionItem(ctx, createMockSession({
+				resource,
+				label: 'Clean up deprecated modules',
+				status: AgentSessionStatus.InProgress,
+				providerType: AgentSessionProviders.Local,
+				timing: {
+					created: now - 5 * 60 * 1000,
+					lastRequestStarted: now - 2 * 60 * 1000,
+					lastRequestEnded: undefined,
+				},
+			}), approvalModel);
+		},
+	}),
+
+	ApprovalRowBash: defineComponentFixture({
+		render: (ctx) => {
+			const resource = URI.parse('vscode-chat-session://local/approval-bash');
+			const approvalModel = createMockApprovalModel(resource, {
+				label: 'npm install --save express@latest',
+				languageId: 'sh',
+				confirm: () => { },
+			});
+			renderSessionItem(ctx, createMockSession({
+				resource,
+				label: 'Update server dependencies',
+				status: AgentSessionStatus.InProgress,
+				providerType: AgentSessionProviders.Local,
+				timing: {
+					created: now - 3 * 60 * 1000,
+					lastRequestStarted: now - 60 * 1000,
+					lastRequestEnded: undefined,
+				},
+			}), approvalModel);
+		},
+	}),
+
+	ApprovalRowPowerShell: defineComponentFixture({
+		render: (ctx) => {
+			const resource = URI.parse('vscode-chat-session://local/approval-powershell');
+			const approvalModel = createMockApprovalModel(resource, {
+				label: 'Start-Job -ScriptBlock { Set-Location \'c:\\some\\path\'; npm install } | Out-Null',
+				languageId: 'pwsh',
+				confirm: () => { },
+			});
+			renderSessionItem(ctx, createMockSession({
+				resource,
+				label: 'Clean up old log files',
+				status: AgentSessionStatus.InProgress,
+				providerType: AgentSessionProviders.Local,
+				timing: {
+					created: now - 4 * 60 * 1000,
+					lastRequestStarted: now - 2 * 60 * 1000,
+					lastRequestEnded: undefined,
+				},
+			}), approvalModel);
+		},
+	}),
+
+	ApprovalRowLongLabel: defineComponentFixture({
+		render: (ctx) => {
+			const resource = URI.parse('vscode-chat-session://local/approval-long');
+			const approvalModel = createMockApprovalModel(resource, {
+				label: 'rm -rf node_modules && npm cache clean --force && npm install --legacy-peer-deps --ignore-scripts',
+				languageId: 'sh',
+				confirm: () => { },
+			});
+			renderSessionItem(ctx, createMockSession({
+				resource,
+				label: 'Reset and reinstall all dependencies',
+				status: AgentSessionStatus.NeedsInput,
+				providerType: AgentSessionProviders.Cloud,
+				icon: Codicon.cloud,
+				isRead: () => false,
+				timing: {
+					created: now - 10 * 60 * 1000,
+					lastRequestStarted: now - 5 * 60 * 1000,
+					lastRequestEnded: undefined,
+				},
+			}), approvalModel);
+		},
+	}),
+
+	ApprovalRow1Line: defineComponentFixture({
+		render: (ctx) => {
+			const resource = URI.parse('vscode-chat-session://local/approval-1line');
+			const approvalModel = createMockApprovalModel(resource, {
+				label: 'npm install --save express@latest',
+				languageId: 'sh',
+				confirm: () => { },
+			});
+			renderSessionItem(ctx, createMockSession({
+				resource,
+				label: 'Install express',
+				status: AgentSessionStatus.InProgress,
+				providerType: AgentSessionProviders.Local,
+				timing: {
+					created: now - 3 * 60 * 1000,
+					lastRequestStarted: now - 60 * 1000,
+					lastRequestEnded: undefined,
+				},
+			}), approvalModel);
+		},
+	}),
+
+	ApprovalRow2Lines: defineComponentFixture({
+		render: (ctx) => {
+			const resource = URI.parse('vscode-chat-session://local/approval-2lines');
+			const approvalModel = createMockApprovalModel(resource, {
+				label: 'cd /workspace/project\nnpm install',
+				languageId: 'sh',
+				confirm: () => { },
+			});
+			renderSessionItem(ctx, createMockSession({
+				resource,
+				label: 'Setup project dependencies',
+				status: AgentSessionStatus.InProgress,
+				providerType: AgentSessionProviders.Local,
+				timing: {
+					created: now - 3 * 60 * 1000,
+					lastRequestStarted: now - 60 * 1000,
+					lastRequestEnded: undefined,
+				},
+			}), approvalModel);
+		},
+	}),
+
+	ApprovalRow3Lines: defineComponentFixture({
+		render: (ctx) => {
+			const resource = URI.parse('vscode-chat-session://local/approval-3lines');
+			const approvalModel = createMockApprovalModel(resource, {
+				label: 'cd /workspace/project\nnpm install\nnpm run build',
+				languageId: 'sh',
+				confirm: () => { },
+			});
+			renderSessionItem(ctx, createMockSession({
+				resource,
+				label: 'Build the project',
+				status: AgentSessionStatus.InProgress,
+				providerType: AgentSessionProviders.Local,
+				timing: {
+					created: now - 2 * 60 * 1000,
+					lastRequestStarted: now - 60 * 1000,
+					lastRequestEnded: undefined,
+				},
+			}), approvalModel);
+		},
+	}),
+
+	ApprovalRow4Lines: defineComponentFixture({
+		render: (ctx) => {
+			const resource = URI.parse('vscode-chat-session://local/approval-4lines');
+			const approvalModel = createMockApprovalModel(resource, {
+				label: 'cd /workspace/project\nnpm install\nnpm run build\nnpm run test -- --coverage',
+				languageId: 'sh',
+				confirm: () => { },
+			});
+			renderSessionItem(ctx, createMockSession({
+				resource,
+				label: 'Build and test project',
+				status: AgentSessionStatus.InProgress,
+				providerType: AgentSessionProviders.Local,
+				timing: {
+					created: now - 2 * 60 * 1000,
+					lastRequestStarted: now - 60 * 1000,
+					lastRequestEnded: undefined,
+				},
+			}), approvalModel);
+		},
+	}),
+
+	ApprovalRow3LongLines: defineComponentFixture({
+		render: (ctx) => {
+			const resource = URI.parse('vscode-chat-session://local/approval-3longlines');
+			const approvalModel = createMockApprovalModel(resource, {
+				label: 'RUSTFLAGS="-C target-cpu=native -C opt-level=3" cargo build --release --target x86_64-unknown-linux-gnu\nfind ./target/release -name "*.so" -exec strip --strip-unneeded {} \\; && tar czf release-bundle.tar.gz -C target/release .\ncurl -X POST https://deploy.internal.example.com/api/v2/artifacts/upload --header "Authorization: Bearer $DEPLOY_TOKEN" --form "bundle=@release-bundle.tar.gz"',
+				languageId: 'sh',
+				confirm: () => { },
+			});
+			renderSessionItem(ctx, createMockSession({
+				resource,
+				label: 'Build and deploy native release',
+				status: AgentSessionStatus.InProgress,
+				providerType: AgentSessionProviders.Local,
+				timing: {
+					created: now - 2 * 60 * 1000,
+					lastRequestStarted: now - 60 * 1000,
+					lastRequestEnded: undefined,
+				},
+			}), approvalModel);
+		},
+	}),
+});
diff --git a/src/vs/workbench/test/browser/componentFixtures/aiStats.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/aiStats.fixture.ts
index 001d6010501d6..0ab26885d3edd 100644
--- a/src/vs/workbench/test/browser/componentFixtures/aiStats.fixture.ts
+++ b/src/vs/workbench/test/browser/componentFixtures/aiStats.fixture.ts
@@ -9,12 +9,14 @@ import { ISessionData } from '../../../contrib/editTelemetry/browser/editStats/a
 import { Random } from '../../../../editor/test/common/core/random.js';
 import { ComponentFixtureContext, defineComponentFixture, defineThemedFixtureGroup } from './fixtureUtils.js';
 
-export default defineThemedFixtureGroup({
+export default defineThemedFixtureGroup({ path: 'chat/' }, {
 	AiStatsHover: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: (context) => renderAiStatsHover({ ...context, data: createSampleDataWithSessions() }),
 	}),
 
 	AiStatsHoverNoData: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: (context) => renderAiStatsHover({ ...context, data: createEmptyData() }),
 	}),
 });
diff --git a/src/vs/workbench/test/browser/componentFixtures/baseUI.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/baseUI.fixture.ts
index 0c8ab56d71f6c..2bc08dd758784 100644
--- a/src/vs/workbench/test/browser/componentFixtures/baseUI.fixture.ts
+++ b/src/vs/workbench/test/browser/componentFixtures/baseUI.fixture.ts
@@ -22,34 +22,42 @@ import { ComponentFixtureContext, defineComponentFixture, defineThemedFixtureGro
 
 export default defineThemedFixtureGroup({
 	Buttons: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: renderButtons,
 	}),
 
 	ButtonBar: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: renderButtonBar,
 	}),
 
 	Toggles: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: renderToggles,
 	}),
 
 	InputBoxes: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: renderInputBoxes,
 	}),
 
 	CountBadges: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: renderCountBadges,
 	}),
 
 	ActionBar: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: renderActionBar,
 	}),
 
 	ProgressBars: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: renderProgressBars,
 	}),
 
 	HighlightedLabels: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: renderHighlightedLabels,
 	}),
 });
diff --git a/src/vs/workbench/test/browser/componentFixtures/chatProgressContentPart.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/chatProgressContentPart.fixture.ts
new file mode 100644
index 0000000000000..cdb3ec7edb9df
--- /dev/null
+++ b/src/vs/workbench/test/browser/componentFixtures/chatProgressContentPart.fixture.ts
@@ -0,0 +1,154 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../base/browser/dom.js';
+import { MarkdownString } from '../../../../base/common/htmlContent.js';
+import { Event } from '../../../../base/common/event.js';
+import { observableValue } from '../../../../base/common/observable.js';
+import { Codicon } from '../../../../base/common/codicons.js';
+import { ThemeIcon } from '../../../../base/common/themables.js';
+import { mock, upcastPartial } from '../../../../base/test/common/mock.js';
+import { IMarkdownRendererService, MarkdownRendererService } from '../../../../platform/markdown/browser/markdownRenderer.js';
+import { ChatProgressContentPart } from '../../../contrib/chat/browser/widget/chatContentParts/chatProgressContentPart.js';
+import { ChatContentMarkdownRenderer } from '../../../contrib/chat/browser/widget/chatContentMarkdownRenderer.js';
+import { IChatContentPartRenderContext, InlineTextModelCollection } from '../../../contrib/chat/browser/widget/chatContentParts/chatContentParts.js';
+import { IChatMarkdownAnchorService } from '../../../contrib/chat/browser/widget/chatContentParts/chatMarkdownAnchorService.js';
+import { IChatProgressMessage } from '../../../contrib/chat/common/chatService/chatService.js';
+import { IChatResponseViewModel } from '../../../contrib/chat/common/model/chatViewModel.js';
+import { ComponentFixtureContext, createEditorServices, defineComponentFixture, defineThemedFixtureGroup } from './fixtureUtils.js';
+
+import '../../../contrib/chat/browser/widget/media/chat.css';
+
+function createMockContext(opts?: { isComplete?: boolean; hasFollowingContent?: boolean }): IChatContentPartRenderContext {
+	const element = new class extends mock<IChatResponseViewModel>() {
+		override readonly isComplete = opts?.isComplete ?? false;
+	}();
+	return {
+		element,
+		inlineTextModels: upcastPartial<InlineTextModelCollection>({}),
+		elementIndex: 0,
+		container: document.createElement('div'),
+		content: opts?.hasFollowingContent ? [{ kind: 'progressMessage', content: new MarkdownString('test') }] : [],
+		contentIndex: 0,
+		editorPool: undefined!,
+		codeBlockStartIndex: 0,
+		treeStartIndex: 0,
+		diffEditorPool: undefined!,
+		codeBlockModelCollection: undefined!,
+		currentWidth: observableValue('currentWidth', 400),
+		onDidChangeVisibility: Event.None,
+	};
+}
+
+function createProgressMessage(text: string): IChatProgressMessage {
+	return {
+		kind: 'progressMessage',
+		content: new MarkdownString(text),
+	};
+}
+
+function renderProgressPart(
+	context: ComponentFixtureContext,
+	message: IChatProgressMessage,
+	renderContext: IChatContentPartRenderContext,
+	opts?: {
+		forceShowSpinner?: boolean;
+		forceShowMessage?: boolean;
+		icon?: ThemeIcon;
+		shimmer?: boolean;
+	},
+): void {
+	const { container, disposableStore } = context;
+
+	const mockAnchorService = new class extends mock<IChatMarkdownAnchorService>() {
+		override register() { return { dispose() { } }; }
+	}();
+
+	const instantiationService = createEditorServices(disposableStore, {
+		colorTheme: context.theme,
+		additionalServices: (reg) => {
+			reg.define(IMarkdownRendererService, MarkdownRendererService);
+			reg.defineInstance(IChatMarkdownAnchorService, mockAnchorService);
+		},
+	});
+
+	const markdownRenderer = instantiationService.createInstance(ChatContentMarkdownRenderer);
+
+	const part = disposableStore.add(
+		instantiationService.createInstance(
+			ChatProgressContentPart,
+			message,
+			markdownRenderer,
+			renderContext,
+			opts?.forceShowSpinner,
+			opts?.forceShowMessage,
+			opts?.icon,
+			undefined, // toolInvocation
+			opts?.shimmer,
+		)
+	);
+
+	// .interactive-session provides CSS custom properties (--vscode-chat-font-size-body-s, etc.)
+	// .interactive-item-container .progress-container is the selector for layout styles
+	container.style.width = '400px';
+	container.style.padding = '8px';
+	container.classList.add('interactive-session');
+
+	const itemContainer = dom.$('.interactive-item-container');
+	itemContainer.appendChild(part.domNode);
+	container.appendChild(itemContainer);
+}
+
+export default defineThemedFixtureGroup({ path: 'chat/' }, {
+	WithSpinner: defineComponentFixture({
+		labels: { kind: 'animated' },
+		render: (ctx) => renderProgressPart(
+			ctx,
+			createProgressMessage('Searching workspace for relevant files...'),
+			createMockContext({ isComplete: false }),
+			{ forceShowSpinner: true, forceShowMessage: true, shimmer: false },
+		),
+	}),
+
+	Completed: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (ctx) => renderProgressPart(
+			ctx,
+			createProgressMessage('Found 12 relevant files'),
+			createMockContext({ isComplete: true }),
+			{ forceShowSpinner: false, forceShowMessage: true },
+		),
+	}),
+
+	WithCustomIcon: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (ctx) => renderProgressPart(
+			ctx,
+			createProgressMessage('Running tests...'),
+			createMockContext({ isComplete: false }),
+			{ forceShowSpinner: true, forceShowMessage: true, icon: Codicon.beaker },
+		),
+	}),
+
+	WithInlineCode: defineComponentFixture({
+		labels: { kind: 'animated' },
+		render: (ctx) => renderProgressPart(
+			ctx,
+			createProgressMessage('Reading `src/vs/workbench/contrib/chat/browser/chatWidget.ts`'),
+			createMockContext({ isComplete: false }),
+			{ forceShowSpinner: true, forceShowMessage: true, shimmer: false },
+		),
+	}),
+
+	LongMessage: defineComponentFixture({
+		labels: { kind: 'animated' },
+		render: (ctx) => renderProgressPart(
+			ctx,
+			createProgressMessage('Searching across multiple workspace folders for TypeScript files matching the pattern you described, including test files and configuration'),
+			createMockContext({ isComplete: false }),
+			{ forceShowSpinner: true, forceShowMessage: true, shimmer: false },
+		),
+	}),
+});
diff --git a/src/vs/workbench/test/browser/componentFixtures/chatQuestionCarousel.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/chatQuestionCarousel.fixture.ts
new file mode 100644
index 0000000000000..db26a9199e6e3
--- /dev/null
+++ b/src/vs/workbench/test/browser/componentFixtures/chatQuestionCarousel.fixture.ts
@@ -0,0 +1,180 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import * as dom from '../../../../base/browser/dom.js';
+import { IMarkdownRendererService, MarkdownRendererService } from '../../../../platform/markdown/browser/markdownRenderer.js';
+import { IChatQuestion, IChatQuestionCarousel } from '../../../contrib/chat/common/chatService/chatService.js';
+import { ChatQuestionCarouselPart, IChatQuestionCarouselOptions } from '../../../contrib/chat/browser/widget/chatContentParts/chatQuestionCarouselPart.js';
+import { IChatContentPartRenderContext, InlineTextModelCollection } from '../../../contrib/chat/browser/widget/chatContentParts/chatContentParts.js';
+import { ComponentFixtureContext, createEditorServices, defineComponentFixture, defineThemedFixtureGroup } from './fixtureUtils.js';
+import { mock, upcastPartial } from '../../../../base/test/common/mock.js';
+import { Event } from '../../../../base/common/event.js';
+import { observableValue } from '../../../../base/common/observable.js';
+import { IChatRequestViewModel } from '../../../contrib/chat/common/model/chatViewModel.js';
+import '../../../contrib/chat/browser/widget/chatContentParts/media/chatQuestionCarousel.css';
+
+function createCarousel(questions: IChatQuestion[], allowSkip: boolean = true): IChatQuestionCarousel {
+	return {
+		questions,
+		allowSkip,
+		kind: 'questionCarousel',
+	};
+}
+
+function createMockContext(): IChatContentPartRenderContext {
+	return {
+		element: new class extends mock<IChatRequestViewModel>() { }(),
+		inlineTextModels: upcastPartial<InlineTextModelCollection>({}),
+		elementIndex: 0,
+		container: document.createElement('div'),
+		content: [],
+		contentIndex: 0,
+		editorPool: undefined!,
+		codeBlockStartIndex: 0,
+		treeStartIndex: 0,
+		diffEditorPool: undefined!,
+		codeBlockModelCollection: undefined!,
+		currentWidth: observableValue('currentWidth', 400),
+		onDidChangeVisibility: Event.None,
+	};
+}
+
+function createOptions(): IChatQuestionCarouselOptions {
+	return {
+		onSubmit: () => { },
+		shouldAutoFocus: false,
+	};
+}
+
+function renderCarousel(context: ComponentFixtureContext, carousel: IChatQuestionCarousel): void {
+	const { container, disposableStore } = context;
+
+	const instantiationService = createEditorServices(disposableStore, {
+		additionalServices: (reg) => {
+			reg.define(IMarkdownRendererService, MarkdownRendererService);
+		},
+	});
+
+	const part = disposableStore.add(
+		instantiationService.createInstance(
+			ChatQuestionCarouselPart,
+			carousel,
+			createMockContext(),
+			createOptions(),
+		)
+	);
+
+	container.style.width = '400px';
+	container.style.padding = '8px';
+	container.classList.add('interactive-session');
+
+	// The CSS uses `.interactive-session .interactive-input-part > .chat-question-carousel-widget-container`
+	// for most layout rules, so we need those wrapper elements.
+	const inputPart = dom.$('.interactive-input-part');
+	const widgetContainer = dom.$('.chat-question-carousel-widget-container');
+	inputPart.appendChild(widgetContainer);
+	container.appendChild(inputPart);
+
+	widgetContainer.appendChild(part.domNode);
+}
+
+// ============================================================================
+// Sample questions
+// ============================================================================
+
+const textQuestion: IChatQuestion = {
+	id: 'project-name',
+	type: 'text',
+	title: 'Project name',
+	message: 'What is the name of your project?',
+	defaultValue: 'my-project',
+};
+
+const singleSelectQuestion: IChatQuestion = {
+	id: 'language',
+	type: 'singleSelect',
+	title: 'Language',
+	message: 'Which language do you want to use?',
+	options: [
+		{ id: 'ts', label: 'TypeScript - Strongly typed JavaScript', value: 'typescript' },
+		{ id: 'js', label: 'JavaScript - Dynamic scripting language', value: 'javascript' },
+		{ id: 'py', label: 'Python - General purpose language', value: 'python' },
+		{ id: 'rs', label: 'Rust - Systems programming', value: 'rust' },
+	],
+	defaultValue: 'ts',
+};
+
+const multiSelectQuestion: IChatQuestion = {
+	id: 'features',
+	type: 'multiSelect',
+	title: 'Features',
+	message: 'Which features should be enabled?',
+	options: [
+		{ id: 'lint', label: 'Linting', value: 'linting' },
+		{ id: 'fmt', label: 'Formatting', value: 'formatting' },
+		{ id: 'test', label: 'Testing', value: 'testing' },
+		{ id: 'ci', label: 'CI/CD Pipeline', value: 'ci' },
+	],
+	defaultValue: ['lint', 'fmt'],
+};
+
+// ============================================================================
+// Fixtures
+// ============================================================================
+
+export default defineThemedFixtureGroup({ path: 'chat/' }, {
+	SingleTextQuestion: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (context) => renderCarousel(context, createCarousel([textQuestion])),
+	}),
+
+	SingleSelectQuestion: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (context) => renderCarousel(context, createCarousel([singleSelectQuestion])),
+	}),
+
+	MultiSelectQuestion: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (context) => renderCarousel(context, createCarousel([multiSelectQuestion])),
+	}),
+
+	MultipleQuestions: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (context) => renderCarousel(context, createCarousel([
+			textQuestion,
+			singleSelectQuestion,
+			multiSelectQuestion,
+		])),
+	}),
+
+	NoSkip: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (context) => renderCarousel(context, createCarousel([singleSelectQuestion], false)),
+	}),
+
+	SubmittedSummary: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (context) => {
+			const carousel = createCarousel([textQuestion, singleSelectQuestion, multiSelectQuestion]);
+			carousel.isUsed = true;
+			carousel.data = {
+				'project-name': 'my-app',
+				'language': { selectedValue: 'typescript', freeformValue: undefined },
+				'features': { selectedValues: ['linting', 'formatting'], freeformValue: undefined },
+			};
+			renderCarousel(context, carousel);
+		},
+	}),
+
+	SkippedSummary: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (context) => {
+			const carousel = createCarousel([textQuestion, singleSelectQuestion]);
+			carousel.isUsed = true;
+			carousel.data = {};
+			renderCarousel(context, carousel);
+		},
+	}),
+});
diff --git a/src/vs/workbench/test/browser/componentFixtures/codeActionList.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/codeActionList.fixture.ts
new file mode 100644
index 0000000000000..9e54ad9819612
--- /dev/null
+++ b/src/vs/workbench/test/browser/componentFixtures/codeActionList.fixture.ts
@@ -0,0 +1,104 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { Codicon } from '../../../../base/common/codicons.js';
+import { Event } from '../../../../base/common/event.js';
+import { mock } from '../../../../base/test/common/mock.js';
+import { ComponentFixtureContext, createEditorServices, defineComponentFixture, defineThemedFixtureGroup, registerWorkbenchServices } from './fixtureUtils.js';
+import { ActionList, ActionListItemKind, IActionListDelegate, IActionListItem } from '../../../../platform/actionWidget/browser/actionList.js';
+import { ILayoutService } from '../../../../platform/layout/browser/layoutService.js';
+
+import '../../../../platform/actionWidget/browser/actionWidget.css';
+import '../../../../base/browser/ui/codicons/codiconStyles.js';
+import '../../../../editor/contrib/symbolIcons/browser/symbolIcons.js';
+
+interface CodeActionFixtureOptions extends ComponentFixtureContext {
+	items: IActionListItem<string>[];
+	width?: string;
+}
+
+function renderCodeActionList(options: CodeActionFixtureOptions): void {
+	const { container, disposableStore, theme } = options;
+	container.style.width = options.width ?? '300px';
+
+	const instantiationService = createEditorServices(disposableStore, {
+		colorTheme: theme,
+		additionalServices: (reg) => {
+			registerWorkbenchServices(reg);
+			reg.defineInstance(ILayoutService, new class extends mock<ILayoutService>() {
+				declare readonly _serviceBrand: undefined;
+				override get mainContainer() { return container; }
+				override get activeContainer() { return container; }
+				override get mainContainerDimension() { return { width: 300, height: 600 }; }
+				override get activeContainerDimension() { return { width: 300, height: 600 }; }
+				override readonly mainContainerOffset = { top: 0, quickPickTop: 0 };
+				override readonly onDidLayoutMainContainer = Event.None;
+				override readonly onDidLayoutActiveContainer = Event.None;
+				override readonly onDidLayoutContainer = Event.None;
+				override readonly onDidChangeActiveContainer = Event.None;
+				override readonly onDidAddContainer = Event.None;
+				override get containers() { return [container]; }
+				override getContainer() { return container; }
+				override whenContainerStylesLoaded() { return undefined; }
+			});
+		},
+	});
+
+	const delegate: IActionListDelegate<string> = {
+		onHide: () => { },
+		onSelect: () => { },
+	};
+
+	const anchor = container;
+
+	const list = disposableStore.add(instantiationService.createInstance(
+		ActionList,
+		'codeActionWidget',
+		false,
+		options.items,
+		delegate,
+		undefined,
+		undefined,
+		anchor,
+	));
+
+	// Render the list directly into the container instead of using context view
+	const wrapper = document.createElement('div');
+	wrapper.classList.add('action-widget');
+	wrapper.appendChild(list.domNode);
+	container.appendChild(wrapper);
+
+	list.layout(0);
+	list.focus();
+}
+
+const quickFixItems: IActionListItem<string>[] = [
+	{ kind: ActionListItemKind.Header, group: { title: 'Quick Fix' } },
+	{ kind: ActionListItemKind.Action, item: 'fix-import', label: 'Add missing import for \'useState\'', group: { title: 'Quick Fix', icon: Codicon.lightBulb } },
+	{ kind: ActionListItemKind.Action, item: 'fix-typo', label: 'Change spelling to \'initialCount\'', group: { title: 'Quick Fix', icon: Codicon.lightBulb } },
+	{ kind: ActionListItemKind.Action, item: 'fix-type', label: 'Add explicit type annotation', group: { title: 'Quick Fix', icon: Codicon.lightBulb } },
+	{ kind: ActionListItemKind.Header, group: { title: 'Extract', icon: Codicon.wrench } },
+	{ kind: ActionListItemKind.Action, item: 'extract-const', label: 'Extract to constant in enclosing scope', group: { title: 'Extract', icon: Codicon.wrench } },
+	{ kind: ActionListItemKind.Action, item: 'extract-fn', label: 'Extract to function in module scope', group: { title: 'Extract', icon: Codicon.wrench } },
+	{ kind: ActionListItemKind.Header, group: { title: 'Source Action', icon: Codicon.symbolFile } },
+	{ kind: ActionListItemKind.Action, item: 'organize-imports', label: 'Organize Imports', group: { title: 'Source Action', icon: Codicon.symbolFile } },
+];
+
+const simpleFixes: IActionListItem<string>[] = [
+	{ kind: ActionListItemKind.Action, item: 'fix-1', label: 'Convert to arrow function', group: { title: 'Quick Fix', icon: Codicon.lightBulb } },
+	{ kind: ActionListItemKind.Action, item: 'fix-2', label: 'Remove unused variable', group: { title: 'Quick Fix', icon: Codicon.lightBulb } },
+	{ kind: ActionListItemKind.Action, item: 'fix-3', label: 'Add \'await\' to async call', group: { title: 'Quick Fix', icon: Codicon.lightBulb } },
+];
+
+export default defineThemedFixtureGroup({ path: 'editor/' }, {
+	GroupedCodeActions: defineComponentFixture({
+		labels: { kind: 'animated' },
+		render: (context) => renderCodeActionList({ ...context, items: quickFixItems }),
+	}),
+	SimpleQuickFixes: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (context) => renderCodeActionList({ ...context, items: simpleFixes }),
+	}),
+});
diff --git a/src/vs/workbench/test/browser/componentFixtures/codeEditor.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/codeEditor.fixture.ts
index c752df7da146c..5e155a37d5e89 100644
--- a/src/vs/workbench/test/browser/componentFixtures/codeEditor.fixture.ts
+++ b/src/vs/workbench/test/browser/componentFixtures/codeEditor.fixture.ts
@@ -68,8 +68,9 @@ function renderCodeEditor({ container, disposableStore, theme }: ComponentFixtur
 	editor.setModel(model);
 }
 
-export default defineThemedFixtureGroup({
+export default defineThemedFixtureGroup({ path: 'editor/' }, {
 	CodeEditor: defineComponentFixture({
+		labels: { kind: 'screenshot', blocksCi: true },
 		render: (context) => renderCodeEditor(context),
 	}),
 });
diff --git a/src/vs/workbench/test/browser/componentFixtures/findWidget.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/findWidget.fixture.ts
new file mode 100644
index 0000000000000..c187a3e530f9f
--- /dev/null
+++ b/src/vs/workbench/test/browser/componentFixtures/findWidget.fixture.ts
@@ -0,0 +1,131 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { URI } from '../../../../base/common/uri.js';
+import { IContextViewProvider } from '../../../../base/browser/ui/contextview/contextview.js';
+import { ComponentFixtureContext, createEditorServices, createTextModel, defineComponentFixture, defineThemedFixtureGroup } from './fixtureUtils.js';
+import { CodeEditorWidget, ICodeEditorWidgetOptions } from '../../../../editor/browser/widget/codeEditor/codeEditorWidget.js';
+import { FindReplaceState } from '../../../../editor/contrib/find/browser/findState.js';
+import { FindWidget, IFindController } from '../../../../editor/contrib/find/browser/findWidget.js';
+import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
+import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
+import { IHoverService } from '../../../../platform/hover/browser/hover.js';
+import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
+import { IAccessibilityService } from '../../../../platform/accessibility/common/accessibility.js';
+
+import '../../../../editor/contrib/find/browser/findWidget.css';
+import '../../../../base/browser/ui/codicons/codiconStyles.js';
+
+const SAMPLE_CODE = `import { useState } from 'react';
+
+function Counter({ initialCount }: { initialCount: number }) {
+	const [count, setCount] = useState(initialCount);
+
+	return (
+		<div>
+			<p>Count: {count}</p>
+			<button onClick={() => setCount(count + 1)}>Increment</button>
+			<button onClick={() => setCount(count - 1)}>Decrement</button>
+		</div>
+	);
+}
+
+export default Counter;
+`;
+
+interface FindFixtureOptions extends ComponentFixtureContext {
+	searchString?: string;
+	replaceString?: string;
+	showReplace?: boolean;
+	matchesCount?: number;
+	matchesPosition?: number;
+}
+
+async function renderFindWidget(options: FindFixtureOptions): Promise<void> {
+	const { container, disposableStore, theme } = options;
+	container.style.width = '600px';
+	container.style.height = '350px';
+	container.style.border = '1px solid var(--vscode-editorWidget-border)';
+
+	const instantiationService = createEditorServices(disposableStore, { colorTheme: theme });
+
+	const textModel = disposableStore.add(createTextModel(
+		instantiationService,
+		SAMPLE_CODE,
+		URI.parse('inmemory://find-fixture.tsx'),
+		'typescript'
+	));
+
+	const editorWidgetOptions: ICodeEditorWidgetOptions = {
+		contributions: []
+	};
+
+	const editor = disposableStore.add(instantiationService.createInstance(
+		CodeEditorWidget,
+		container,
+		{
+			automaticLayout: true,
+			minimap: { enabled: false },
+			lineNumbers: 'on',
+			scrollBeyondLastLine: false,
+			fontSize: 14,
+			cursorBlinking: 'solid',
+			find: { addExtraSpaceOnTop: false },
+		},
+		editorWidgetOptions
+	));
+
+	editor.setModel(textModel);
+	editor.focus();
+
+	const state = disposableStore.add(new FindReplaceState());
+
+	const mockController: IFindController = {
+		replace: () => { },
+		replaceAll: () => { },
+		getGlobalBufferTerm: async () => '',
+	};
+
+	const mockContextViewProvider: IContextViewProvider = {
+		showContextView: () => { },
+		hideContextView: () => { },
+		layout: () => { },
+	};
+
+	disposableStore.add(new FindWidget(
+		editor,
+		mockController,
+		state,
+		mockContextViewProvider,
+		instantiationService.get(IKeybindingService),
+		instantiationService.get(IContextKeyService),
+		instantiationService.get(IHoverService),
+		undefined,
+		undefined,
+		instantiationService.get(IConfigurationService),
+		instantiationService.get(IAccessibilityService),
+	));
+
+	state.change({
+		searchString: options.searchString ?? 'count',
+		isRevealed: true,
+		isReplaceRevealed: options.showReplace ?? false,
+		replaceString: options.replaceString ?? '',
+	}, false);
+
+	// Wait for the CSS transition (top: -64px → 0, 200ms linear)
+	await new Promise(resolve => setTimeout(resolve, 300));
+}
+
+export default defineThemedFixtureGroup({ path: 'editor/' }, {
+	Find: defineComponentFixture({
+		labels: { kind: 'animated' },
+		render: (context) => renderFindWidget({ ...context, searchString: 'count' }),
+	}),
+	FindAndReplace: defineComponentFixture({
+		labels: { kind: 'animated' },
+		render: (context) => renderFindWidget({ ...context, searchString: 'count', replaceString: 'value', showReplace: true }),
+	}),
+});
diff --git a/src/vs/workbench/test/browser/componentFixtures/fixtureUtils.ts b/src/vs/workbench/test/browser/componentFixtures/fixtureUtils.ts
index 62bbbcb65d737..2a7f7faf22fea 100644
--- a/src/vs/workbench/test/browser/componentFixtures/fixtureUtils.ts
+++ b/src/vs/workbench/test/browser/componentFixtures/fixtureUtils.ts
@@ -10,6 +10,7 @@ import { DisposableStore, toDisposable } from '../../../../base/common/lifecycle
 import { URI } from '../../../../base/common/uri.js';
 // eslint-disable-next-line local/code-import-patterns
 import '../../../../../../build/vite/style.css';
+import '../../../browser/media/style.css';
 
 // Theme
 import { IEnvironmentService } from '../../../../platform/environment/common/environment.js';
@@ -28,20 +29,6 @@ import { ServiceCollection } from '../../../../platform/instantiation/common/ser
 import { TestInstantiationService } from '../../../../platform/instantiation/test/common/instantiationServiceMock.js';
 
 // Test service implementations
-import { TestCodeEditorService, TestCommandService } from '../../../../editor/test/browser/editorTestServices.js';
-import { TestLanguageConfigurationService } from '../../../../editor/test/common/modes/testLanguageConfigurationService.js';
-import { TestEditorWorkerService } from '../../../../editor/test/common/services/testEditorWorkerService.js';
-import { TestTextResourcePropertiesService } from '../../../../editor/test/common/services/testTextResourcePropertiesService.js';
-import { TestTreeSitterLibraryService } from '../../../../editor/test/common/services/testTreeSitterLibraryService.js';
-import { TestAccessibilityService } from '../../../../platform/accessibility/test/common/testAccessibilityService.js';
-import { TestClipboardService } from '../../../../platform/clipboard/test/common/testClipboardService.js';
-import { TestConfigurationService } from '../../../../platform/configuration/test/common/testConfigurationService.js';
-import { TestDialogService } from '../../../../platform/dialogs/test/common/testDialogService.js';
-import { MockContextKeyService, MockKeybindingService } from '../../../../platform/keybinding/test/common/mockKeybindingService.js';
-import { TestNotificationService } from '../../../../platform/notification/test/common/testNotificationService.js';
-import { NullOpenerService } from '../../../../platform/opener/test/common/nullOpenerService.js';
-import { TestThemeService } from '../../../../platform/theme/test/common/testThemeService.js';
-import { TestMenuService } from '../workbenchTestServices.js';
 import { Emitter, Event } from '../../../../base/common/event.js';
 import { mock } from '../../../../base/test/common/mock.js';
 import { ICodeEditorService } from '../../../../editor/browser/services/codeEditorService.js';
@@ -58,31 +45,45 @@ import { ModelService } from '../../../../editor/common/services/modelService.js
 import { ITextResourcePropertiesService } from '../../../../editor/common/services/textResourceConfiguration.js';
 import { ITreeSitterLibraryService } from '../../../../editor/common/services/treeSitter/treeSitterLibraryService.js';
 import { ICodeLensCache } from '../../../../editor/contrib/codelens/browser/codeLensCache.js';
+import { TestCodeEditorService, TestCommandService } from '../../../../editor/test/browser/editorTestServices.js';
+import { TestLanguageConfigurationService } from '../../../../editor/test/common/modes/testLanguageConfigurationService.js';
+import { TestEditorWorkerService } from '../../../../editor/test/common/services/testEditorWorkerService.js';
+import { TestTextResourcePropertiesService } from '../../../../editor/test/common/services/testTextResourcePropertiesService.js';
+import { TestTreeSitterLibraryService } from '../../../../editor/test/common/services/testTreeSitterLibraryService.js';
 import { IAccessibilityService } from '../../../../platform/accessibility/common/accessibility.js';
+import { TestAccessibilityService } from '../../../../platform/accessibility/test/common/testAccessibilityService.js';
 import { IActionViewItemService, NullActionViewItemService } from '../../../../platform/actions/browser/actionViewItemService.js';
 import { IMenuService } from '../../../../platform/actions/common/actions.js';
 import { IClipboardService } from '../../../../platform/clipboard/common/clipboardService.js';
+import { TestClipboardService } from '../../../../platform/clipboard/test/common/testClipboardService.js';
 import { ICommandService } from '../../../../platform/commands/common/commands.js';
 import { IConfigurationService } from '../../../../platform/configuration/common/configuration.js';
+import { TestConfigurationService } from '../../../../platform/configuration/test/common/testConfigurationService.js';
 import { IContextKeyService } from '../../../../platform/contextkey/common/contextkey.js';
 import { IContextMenuService, IContextViewService } from '../../../../platform/contextview/browser/contextView.js';
 import { IDataChannelService, NullDataChannelService } from '../../../../platform/dataChannel/common/dataChannel.js';
 import { IDefaultAccountService } from '../../../../platform/defaultAccount/common/defaultAccount.js';
 import { IDialogService } from '../../../../platform/dialogs/common/dialogs.js';
+import { TestDialogService } from '../../../../platform/dialogs/test/common/testDialogService.js';
 import { IHoverService } from '../../../../platform/hover/browser/hover.js';
 import { IKeybindingService } from '../../../../platform/keybinding/common/keybinding.js';
+import { MockContextKeyService, MockKeybindingService } from '../../../../platform/keybinding/test/common/mockKeybindingService.js';
 import { ILabelService } from '../../../../platform/label/common/label.js';
 import { ILoggerService, ILogService, NullLoggerService, NullLogService } from '../../../../platform/log/common/log.js';
 import { INotificationService } from '../../../../platform/notification/common/notification.js';
+import { TestNotificationService } from '../../../../platform/notification/test/common/testNotificationService.js';
 import { IOpenerService } from '../../../../platform/opener/common/opener.js';
+import { NullOpenerService } from '../../../../platform/opener/test/common/nullOpenerService.js';
 import { IApplicationStorageValueChangeEvent, IProfileStorageValueChangeEvent, IStorageEntry, IStorageService, IStorageTargetChangeEvent, IStorageValueChangeEvent, IWillSaveStateEvent, IWorkspaceStorageValueChangeEvent, StorageScope, StorageTarget, WillSaveStateReason } from '../../../../platform/storage/common/storage.js';
 import { ITelemetryService } from '../../../../platform/telemetry/common/telemetry.js';
 import { NullTelemetryServiceShape } from '../../../../platform/telemetry/common/telemetryUtils.js';
+import { TestThemeService } from '../../../../platform/theme/test/common/testThemeService.js';
 import { IUndoRedoService } from '../../../../platform/undoRedo/common/undoRedo.js';
 import { UndoRedoService } from '../../../../platform/undoRedo/common/undoRedoService.js';
 import { IUserDataProfile } from '../../../../platform/userDataProfile/common/userDataProfile.js';
 import { IUserInteractionService, MockUserInteractionService } from '../../../../platform/userInteraction/browser/userInteractionService.js';
 import { IAnyWorkspaceIdentifier } from '../../../../platform/workspace/common/workspace.js';
+import { TestMenuService } from '../workbenchTestServices.js';
 
 // Editor
 import { ITextModel } from '../../../../editor/common/model.js';
@@ -90,12 +91,12 @@ import { ITextModel } from '../../../../editor/common/model.js';
 
 
 // Import color registrations to ensure colors are available
+import { isThenable } from '../../../../base/common/async.js';
 import '../../../../platform/theme/common/colors/baseColors.js';
 import '../../../../platform/theme/common/colors/editorColors.js';
 import '../../../../platform/theme/common/colors/listColors.js';
 import '../../../../platform/theme/common/colors/miscColors.js';
 import '../../../common/theme.js';
-import { isThenable } from '../../../../base/common/async.js';
 
 /**
  * A storage service that never stores anything and always returns the default/fallback value.
@@ -244,10 +245,11 @@ function getThemeStyleSheet(theme: ColorThemeData): CSSStyleSheet {
 		return lightThemeStyleSheet;
 	}
 
+	const scopeSelector = '.' + theme.classNames[0];
 	const sheet = new CSSStyleSheet();
 	const css = generateColorThemeCSS(
 		theme,
-		':host',
+		scopeSelector,
 		themingRegistry.getThemingParticipants(),
 		mockEnvironmentService
 	);
@@ -261,20 +263,40 @@ function getThemeStyleSheet(theme: ColorThemeData): CSSStyleSheet {
 	return sheet;
 }
 
-/**
- * Applies theme styling to a shadow DOM container.
- * Adds theme class names and adopts shared stylesheets.
- */
+let globalStylesInstalled = false;
+
+function installGlobalStyles(): void {
+	if (globalStylesInstalled) {
+		return;
+	}
+	globalStylesInstalled = true;
+	document.adoptedStyleSheets = [
+		...document.adoptedStyleSheets,
+		getGlobalStyleSheet(),
+		getIconsStyleSheetCached(),
+		getThemeStyleSheet(darkTheme),
+		getThemeStyleSheet(lightTheme),
+	];
+}
+
 export function setupTheme(container: HTMLElement, theme: ColorThemeData): void {
-	container.classList.add(...theme.classNames);
-
-	const shadowRoot = container.getRootNode() as ShadowRoot;
-	if (shadowRoot.adoptedStyleSheets !== undefined) {
-		shadowRoot.adoptedStyleSheets = [
-			getGlobalStyleSheet(),
-			getIconsStyleSheetCached(),
-			getThemeStyleSheet(theme),
-		];
+	installGlobalStyles();
+	container.classList.add('monaco-workbench', getPlatformClass(), ...theme.classNames);
+}
+
+function getPlatformClass(): string {
+	const alwaysUseMac = true;
+	if (alwaysUseMac) {
+		return 'mac';
+	} else {
+		const ua = navigator.userAgent;
+		if (ua.includes('Macintosh')) {
+			return 'mac';
+		}
+		if (ua.includes('Linux')) {
+			return 'linux';
+		}
+		return 'windows';
 	}
 }
 
@@ -381,6 +403,8 @@ export function createEditorServices(disposables: DisposableStore, options?: Cre
 		onDidChangeDefaultAccount: new Emitter<null>().event,
 		onDidChangePolicyData: new Emitter<null>().event,
 		policyData: null,
+		copilotTokenInfo: null,
+		onDidChangeCopilotTokenInfo: new Emitter<null>().event,
 		getDefaultAccount: async () => null,
 		getDefaultAccountAuthenticationProvider: () => ({ id: 'test', name: 'Test', scopes: [], enterprise: false }),
 		setDefaultAccountProvider: () => { },
@@ -472,6 +496,24 @@ export function createTextModel(
 // Fixture Adapters
 // ============================================================================
 
+export interface ThemedFixtureGroupLabels {
+	readonly kind?: 'screenshot' | 'animated';
+	readonly blocksCi?: true;
+}
+
+function resolveLabels(labels: ThemedFixtureGroupLabels | undefined): string[] {
+	const result: string[] = [];
+	if (labels?.kind === 'screenshot') {
+		result.push('.screenshot');
+	} else if (labels?.kind === 'animated') {
+		result.push('animated');
+	}
+	if (labels?.blocksCi) {
+		result.push('blocks-ci');
+	}
+	return result;
+}
+
 export interface ComponentFixtureContext {
 	container: HTMLElement;
 	disposableStore: DisposableStore;
@@ -480,6 +522,7 @@ export interface ComponentFixtureContext {
 
 export interface ComponentFixtureOptions {
 	render: (context: ComponentFixtureContext) => void | Promise<void>;
+	labels?: ThemedFixtureGroupLabels;
 }
 
 type ThemedFixtures = ReturnType<typeof defineFixtureVariants>;
@@ -494,7 +537,7 @@ type ThemedFixtures = ReturnType<typeof defineFixtureVariants>;
  */
 export function defineComponentFixture(options: ComponentFixtureOptions): ThemedFixtures {
 	const createFixture = (theme: typeof darkTheme | typeof lightTheme) => defineFixture({
-		isolation: 'shadow-dom',
+		isolation: 'none',
 		displayMode: { type: 'component' },
 		properties: [],
 		background: theme === darkTheme ? 'dark' : 'light',
@@ -507,18 +550,33 @@ export function defineComponentFixture(options: ComponentFixtureOptions): Themed
 		},
 	});
 
-	return defineFixtureVariants({
+	const labels = resolveLabels(options.labels);
+	return defineFixtureVariants(labels.length > 0 ? { labels } : {}, {
 		Dark: createFixture(darkTheme),
 		Light: createFixture(lightTheme),
 	});
 }
 
-type ThemedFixtureGroupInput = Record<string, ThemedFixtures>;
+interface ThemedFixtureGroupOptions {
+	readonly path?: string;
+	readonly labels?: ThemedFixtureGroupLabels;
+}
+
+type ThemedFixtureGroupFixtures = Record<string, ThemedFixtures>;
 
 /**
  * Creates a nested fixture group from themed fixtures.
  * E.g., { MergeEditor: { Dark: ..., Light: ... } } becomes a nested group: MergeEditor > Dark/Light
  */
-export function defineThemedFixtureGroup(group: ThemedFixtureGroupInput): ReturnType<typeof defineFixtureGroup> {
-	return defineFixtureGroup(group);
+export function defineThemedFixtureGroup(options: ThemedFixtureGroupOptions, fixtures: ThemedFixtureGroupFixtures): ReturnType<typeof defineFixtureGroup>;
+export function defineThemedFixtureGroup(fixtures: ThemedFixtureGroupFixtures): ReturnType<typeof defineFixtureGroup>;
+export function defineThemedFixtureGroup(optionsOrFixtures: ThemedFixtureGroupOptions | ThemedFixtureGroupFixtures, fixtures?: ThemedFixtureGroupFixtures): ReturnType<typeof defineFixtureGroup> {
+	if (fixtures) {
+		const options = optionsOrFixtures as ThemedFixtureGroupOptions;
+		return defineFixtureGroup({
+			labels: resolveLabels(options.labels),
+			path: options.path,
+		}, fixtures as ThemedFixtureGroupFixtures);
+	}
+	return defineFixtureGroup(optionsOrFixtures as ThemedFixtureGroupFixtures);
 }
diff --git a/src/vs/workbench/test/browser/componentFixtures/inlineCompletions.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/inlineCompletions.fixture.ts
index 8d4fe0ae30655..8a598804fea36 100644
--- a/src/vs/workbench/test/browser/componentFixtures/inlineCompletions.fixture.ts
+++ b/src/vs/workbench/test/browser/componentFixtures/inlineCompletions.fixture.ts
@@ -107,9 +107,10 @@ function renderInlineEdit(options: InlineEditOptions): void {
 // Fixtures
 // ============================================================================
 
-export default defineThemedFixtureGroup({
+export default defineThemedFixtureGroup({ path: 'editor/' }, {
 	// Side-by-side view: Multi-line replacement
 	SideBySideView: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: (context) => renderInlineEdit({
 			...context,
 			code: `function greet(name) {
@@ -123,6 +124,7 @@ export default defineThemedFixtureGroup({
 
 	// Word replacement view: Single word change
 	WordReplacementView: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: (context) => renderInlineEdit({
 			...context,
 			code: `class BufferData {
@@ -139,6 +141,7 @@ export default defineThemedFixtureGroup({
 
 	// Insertion view: Insert new content
 	InsertionView: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: (context) => renderInlineEdit({
 			...context,
 			code: `class BufferData {
diff --git a/src/vs/workbench/test/browser/componentFixtures/inlineCompletionsExtras.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/inlineCompletionsExtras.fixture.ts
new file mode 100644
index 0000000000000..e06984438ec8a
--- /dev/null
+++ b/src/vs/workbench/test/browser/componentFixtures/inlineCompletionsExtras.fixture.ts
@@ -0,0 +1,368 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { constObservable, IObservableWithChange } from '../../../../base/common/observable.js';
+import { URI } from '../../../../base/common/uri.js';
+import { ComponentFixtureContext, createEditorServices, createTextModel, defineComponentFixture, defineThemedFixtureGroup, registerWorkbenchServices } from './fixtureUtils.js';
+import { EditorExtensionsRegistry } from '../../../../editor/browser/editorExtensions.js';
+import { CodeEditorWidget, ICodeEditorWidgetOptions } from '../../../../editor/browser/widget/codeEditor/codeEditorWidget.js';
+import { observableCodeEditor } from '../../../../editor/browser/observableCodeEditor.js';
+import { IEditorOptions } from '../../../../editor/common/config/editorOptions.js';
+import { Position } from '../../../../editor/common/core/position.js';
+import { Range } from '../../../../editor/common/core/range.js';
+import { ILanguageFeaturesService } from '../../../../editor/common/services/languageFeatures.js';
+import { InlineCompletionsController } from '../../../../editor/contrib/inlineCompletions/browser/controller/inlineCompletionsController.js';
+import '../../../../editor/contrib/inlineCompletions/browser/inlineCompletions.contribution.js';
+import { InlineCompletionsSource, InlineCompletionsState } from '../../../../editor/contrib/inlineCompletions/browser/model/inlineCompletionsSource.js';
+import { InlineEditItem } from '../../../../editor/contrib/inlineCompletions/browser/model/inlineSuggestionItem.js';
+import { TextModelValueReference } from '../../../../editor/contrib/inlineCompletions/browser/model/textModelValueReference.js';
+import { JumpToView } from '../../../../editor/contrib/inlineCompletions/browser/view/inlineEdits/inlineEditsViews/jumpToView.js';
+import { GutterIndicatorMenuContent } from '../../../../editor/contrib/inlineCompletions/browser/view/inlineEdits/components/gutterIndicatorMenu.js';
+import { InlineSuggestionGutterMenuData } from '../../../../editor/contrib/inlineCompletions/browser/view/inlineEdits/components/gutterIndicatorView.js';
+import { IUserInteractionService, MockUserInteractionService } from '../../../../platform/userInteraction/browser/userInteractionService.js';
+
+import '../../../../editor/contrib/inlineCompletions/browser/hintsWidget/inlineCompletionsHintsWidget.css';
+import '../../../../editor/contrib/inlineCompletions/browser/view/inlineEdits/view.css';
+import '../../../../base/browser/ui/codicons/codiconStyles.js';
+
+const SAMPLE_CODE = `function fibonacci(n: number): number {
+	if (n <= 1) return n;
+	return fibonacci(n - 1) + fibonacci(n - 2);
+}
+
+const result = fibonacci(10);
+console.log(result);
+`;
+
+const LONG_DISTANCE_CODE = `import { readFile, writeFile } from 'fs';
+import { join } from 'path';
+
+interface Config {
+	inputDir: string;
+	outputDir: string;
+	verbose: boolean;
+}
+
+function loadConfig(): Config {
+	return {
+		inputDir: './input',
+		outputDir: './output',
+		verbose: false,
+	};
+}
+
+function processLine(line: string): string {
+	return line.trim().toUpperCase();
+}
+
+function validateInput(data: string): boolean {
+	return data.length > 0 && data.length < 10000;
+}
+
+async function processFile(config: Config, filename: string): Promise<void> {
+	const inputPath = join(config.inputDir, filename);
+	const data = await readFile(inputPath, 'utf8');
+	if (!validateInput(data)) {
+		throw new Error('Invalid input');
+	}
+	const lines = data.split('\\n');
+	const processed = lines.map(processLine);
+	const outputPath = join(config.outputDir, filename);
+	await writeFile(outputPath, processed.join('\\n'));
+	if (config.verbose) {
+		console.log(\`Processed \${filename}\`);
+	}
+}
+
+async function main() {
+	const config = loadConfig();
+	const files = ['a.txt', 'b.txt', 'c.txt'];
+	for (const file of files) {
+		await processFile(config, file);
+	}
+}
+
+main();
+`;
+
+interface HintsToolbarOptions extends ComponentFixtureContext {
+	simulateHover?: boolean;
+}
+
+const HINTS_CODE = `function greet(name: string): string {
+	return "Hello, " + name
+}
+
+greet("World");
+`;
+
+async function renderHintsToolbar(options: HintsToolbarOptions): Promise<void> {
+	const { container, disposableStore, theme } = options;
+	container.style.width = '500px';
+	container.style.height = '180px';
+	container.style.border = '1px solid var(--vscode-editorWidget-border)';
+
+	const instantiationService = createEditorServices(disposableStore, {
+		colorTheme: theme,
+		additionalServices: (reg) => {
+			registerWorkbenchServices(reg);
+			if (options.simulateHover) {
+				reg.defineInstance(IUserInteractionService, new MockUserInteractionService(true, true));
+			}
+		},
+	});
+
+	const textModel = disposableStore.add(createTextModel(
+		instantiationService,
+		HINTS_CODE,
+		URI.parse('inmemory://hints-toolbar.ts'),
+		'typescript'
+	));
+
+	// Register an inline completion provider (not an inline edit) so the result is ghost text
+	const languageFeaturesService = instantiationService.get(ILanguageFeaturesService);
+	disposableStore.add(languageFeaturesService.inlineCompletionsProvider.register({ pattern: '**' }, {
+		provideInlineCompletions: () => ({
+			items: [{
+				insertText: ' + "!";',
+				range: new Range(2, 28, 2, 28),
+			}],
+		}),
+		disposeInlineCompletions: () => { },
+	}));
+
+	const editor = disposableStore.add(instantiationService.createInstance(
+		CodeEditorWidget,
+		container,
+		{
+			automaticLayout: true,
+			minimap: { enabled: false },
+			lineNumbers: 'on',
+			scrollBeyondLastLine: false,
+			fontSize: 14,
+			cursorBlinking: 'solid',
+			inlineSuggest: { showToolbar: 'always' },
+		},
+		{ contributions: EditorExtensionsRegistry.getEditorContributions() } satisfies ICodeEditorWidgetOptions
+	));
+
+	editor.setModel(textModel);
+	editor.setPosition({ lineNumber: 2, column: 28 });
+	editor.focus();
+
+	const controller = InlineCompletionsController.get(editor);
+	controller?.model?.get()?.triggerExplicitly();
+
+	await new Promise(resolve => setTimeout(resolve, 100));
+}
+
+function renderJumpToHint({ container, disposableStore, theme }: ComponentFixtureContext): void {
+	container.style.width = '500px';
+	container.style.height = '200px';
+	container.style.border = '1px solid var(--vscode-editorWidget-border)';
+
+	const instantiationService = createEditorServices(disposableStore, { colorTheme: theme });
+
+	const textModel = disposableStore.add(createTextModel(
+		instantiationService,
+		SAMPLE_CODE,
+		URI.parse('inmemory://jump-to-hint.ts'),
+		'typescript'
+	));
+
+	const editor = disposableStore.add(instantiationService.createInstance(
+		CodeEditorWidget,
+		container,
+		{
+			automaticLayout: true,
+			minimap: { enabled: false },
+			lineNumbers: 'on',
+			scrollBeyondLastLine: false,
+			fontSize: 14,
+			cursorBlinking: 'solid',
+		},
+		{ contributions: [] } satisfies ICodeEditorWidgetOptions
+	));
+
+	editor.setModel(textModel);
+	editor.setPosition({ lineNumber: 1, column: 1 });
+	editor.focus();
+
+	const editorObs = observableCodeEditor(editor);
+	disposableStore.add(instantiationService.createInstance(
+		JumpToView,
+		editorObs,
+		{ style: 'label' },
+		constObservable({ jumpToPosition: new Position(6, 18) }),
+	));
+}
+
+function createLongDistanceEditor(options: {
+	container: HTMLElement;
+	disposableStore: import('../../../../base/common/lifecycle.js').DisposableStore;
+	theme: import('./fixtureUtils.js').ComponentFixtureContext['theme'];
+	code: string;
+	cursorLine: number;
+	editRange: { startLineNumber: number; startColumn: number; endLineNumber: number; endColumn: number };
+	newText: string;
+	editorOptions?: IEditorOptions;
+}): void {
+	const { container, disposableStore, theme } = options;
+	container.style.width = '600px';
+	container.style.height = '500px';
+	container.style.border = '1px solid var(--vscode-editorWidget-border)';
+
+	const instantiationService = createEditorServices(disposableStore, { colorTheme: theme });
+
+	const textModel = disposableStore.add(createTextModel(
+		instantiationService,
+		options.code,
+		URI.parse('inmemory://long-distance.ts'),
+		'typescript'
+	));
+
+	instantiationService.stubInstance(InlineCompletionsSource, {
+		cancelUpdate: () => { },
+		clear: () => { },
+		clearOperationOnTextModelChange: constObservable(undefined) as IObservableWithChange<undefined, void>,
+		clearSuggestWidgetInlineCompletions: () => { },
+		dispose: () => { },
+		fetch: async () => true,
+		inlineCompletions: constObservable(new InlineCompletionsState([
+			InlineEditItem.createForTest(
+				TextModelValueReference.snapshot(textModel),
+				new Range(
+					options.editRange.startLineNumber,
+					options.editRange.startColumn,
+					options.editRange.endLineNumber,
+					options.editRange.endColumn
+				),
+				options.newText
+			)
+		], undefined)),
+		loading: constObservable(false),
+		seedInlineCompletionsWithSuggestWidget: () => { },
+		seedWithCompletion: () => { },
+		suggestWidgetInlineCompletions: constObservable(InlineCompletionsState.createEmpty()),
+	});
+
+	const editorWidgetOptions: ICodeEditorWidgetOptions = {
+		contributions: EditorExtensionsRegistry.getEditorContributions()
+	};
+
+	const editor = disposableStore.add(instantiationService.createInstance(
+		CodeEditorWidget,
+		container,
+		{
+			automaticLayout: true,
+			minimap: { enabled: false },
+			lineNumbers: 'on',
+			scrollBeyondLastLine: false,
+			fontSize: 14,
+			cursorBlinking: 'solid',
+			inlineSuggest: {
+				edits: { showLongDistanceHint: true },
+			},
+			...options.editorOptions,
+		},
+		editorWidgetOptions
+	));
+
+	editor.setModel(textModel);
+	editor.setPosition({ lineNumber: options.cursorLine, column: 1 });
+	editor.focus();
+
+	const controller = InlineCompletionsController.get(editor);
+	controller?.model?.get();
+}
+
+function renderGutterMenu({ container, disposableStore, theme }: ComponentFixtureContext): void {
+	container.style.width = '250px';
+	container.style.height = '280px';
+
+	const instantiationService = createEditorServices(disposableStore, {
+		colorTheme: theme,
+		additionalServices: (reg) => {
+			registerWorkbenchServices(reg);
+		},
+	});
+
+	const textModel = disposableStore.add(createTextModel(
+		instantiationService,
+		'const x = 1;',
+		URI.parse('inmemory://gutter-menu.ts'),
+		'typescript'
+	));
+
+	const editor = disposableStore.add(instantiationService.createInstance(
+		CodeEditorWidget,
+		document.createElement('div'),
+		{ minimap: { enabled: false } },
+		{ contributions: [] } satisfies ICodeEditorWidgetOptions
+	));
+	editor.setModel(textModel);
+
+	const editorObs = observableCodeEditor(editor);
+	const menuData = new InlineSuggestionGutterMenuData(
+		undefined,
+		'Copilot',
+		[],
+		undefined,
+		undefined,
+		undefined,
+	);
+
+	const content = disposableStore.add(
+		instantiationService.createInstance(
+			GutterIndicatorMenuContent,
+			editorObs,
+			menuData,
+			() => { },
+		).toDisposableLiveElement()
+	);
+
+	container.style.background = 'var(--vscode-editorHoverWidget-background)';
+	container.style.border = '2px solid var(--vscode-editorHoverWidget-border)';
+	container.style.borderRadius = '3px';
+	container.style.color = 'var(--vscode-editorHoverWidget-foreground)';
+	container.appendChild(content.element);
+}
+
+export default defineThemedFixtureGroup({ path: 'editor/' }, {
+	HintsToolbar: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (context) => renderHintsToolbar(context),
+	}),
+	HintsToolbarHovered: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (context) => renderHintsToolbar({ ...context, simulateHover: true }),
+	}),
+	JumpToHint: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: renderJumpToHint,
+	}),
+	LongDistanceHint: defineComponentFixture({
+		labels: { kind: 'animated' },
+		render: (context) => createLongDistanceEditor({
+			...context,
+			code: LONG_DISTANCE_CODE,
+			cursorLine: 1,
+			editRange: { startLineNumber: 28, startColumn: 1, endLineNumber: 35, endColumn: 100 },
+			newText: `async function processFile(config: Config, filename: string): Promise<void> {
+	const inputPath = join(config.inputDir, filename);
+	const outputPath = join(config.outputDir, filename);
+	const data = await readFile(inputPath, 'utf8');
+	if (!validateInput(data)) {
+		throw new Error(\`Invalid input in \${filename}\`);
+	}
+	const processed = data.split('\\n').map(processLine).join('\\n');
+	await writeFile(outputPath, processed);`,
+		}),
+	}),
+	GutterMenu: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: renderGutterMenu,
+	}),
+});
diff --git a/src/vs/workbench/test/browser/componentFixtures/promptFilePickers.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/promptFilePickers.fixture.ts
index 6692adf6bcdfa..306b921cac50b 100644
--- a/src/vs/workbench/test/browser/componentFixtures/promptFilePickers.fixture.ts
+++ b/src/vs/workbench/test/browser/componentFixtures/promptFilePickers.fixture.ts
@@ -50,8 +50,9 @@ class FixtureQuickInputService extends QuickInputService {
 	}
 }
 
-export default defineThemedFixtureGroup({
+export default defineThemedFixtureGroup({ path: 'chat/' }, {
 	PromptFiles: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: context => renderPromptFilePickerFixture({
 			...context,
 			type: PromptsType.prompt,
@@ -69,6 +70,7 @@ export default defineThemedFixtureGroup({
 	}),
 
 	InstructionFilesWithAgentInstructions: defineComponentFixture({
+		labels: { kind: 'screenshot' },
 		render: context => renderPromptFilePickerFixture({
 			...context,
 			type: PromptsType.instructions,
@@ -115,6 +117,10 @@ async function renderPromptFilePickerFixture({ container, disposableStore, theme
 					return promptsState.userPromptFiles.filter(file => file.type === type);
 				case PromptsStorage.extension:
 					return promptsState.extensionPromptFiles.filter(file => file.type === type);
+				case PromptsStorage.plugin:
+					return [];
+				default:
+					return [];
 			}
 		}
 
diff --git a/src/vs/workbench/test/browser/componentFixtures/renameWidget.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/renameWidget.fixture.ts
new file mode 100644
index 0000000000000..0d85c6e0da449
--- /dev/null
+++ b/src/vs/workbench/test/browser/componentFixtures/renameWidget.fixture.ts
@@ -0,0 +1,119 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { CancellationTokenSource } from '../../../../base/common/cancellation.js';
+import { URI } from '../../../../base/common/uri.js';
+import { ComponentFixtureContext, createEditorServices, createTextModel, defineComponentFixture, defineThemedFixtureGroup } from './fixtureUtils.js';
+import { CodeEditorWidget, ICodeEditorWidgetOptions } from '../../../../editor/browser/widget/codeEditor/codeEditorWidget.js';
+import { RenameWidget } from '../../../../editor/contrib/rename/browser/renameWidget.js';
+
+import '../../../../editor/contrib/rename/browser/renameWidget.css';
+import '../../../../base/browser/ui/codicons/codiconStyles.js';
+
+const SAMPLE_CODE = `class UserService {
+	private _users: Map<string, User> = new Map();
+
+	getUser(userId: string): User | undefined {
+		return this._users.get(userId);
+	}
+
+	addUser(user: User): void {
+		this._users.set(user.id, user);
+	}
+}
+`;
+
+interface RenameFixtureOptions extends ComponentFixtureContext {
+	cursorLine: number;
+	cursorColumn: number;
+	currentName: string;
+	rangeStartColumn: number;
+	rangeEndColumn: number;
+}
+
+function renderRenameWidget(options: RenameFixtureOptions): void {
+	const { container, disposableStore, theme } = options;
+	container.style.width = '500px';
+	container.style.height = '280px';
+	container.style.border = '1px solid var(--vscode-editorWidget-border)';
+
+	const instantiationService = createEditorServices(disposableStore, { colorTheme: theme });
+
+	const textModel = disposableStore.add(createTextModel(
+		instantiationService,
+		SAMPLE_CODE,
+		URI.parse('inmemory://rename-fixture.ts'),
+		'typescript'
+	));
+
+	const editorWidgetOptions: ICodeEditorWidgetOptions = {
+		contributions: []
+	};
+
+	const editor = disposableStore.add(instantiationService.createInstance(
+		CodeEditorWidget,
+		container,
+		{
+			automaticLayout: true,
+			minimap: { enabled: false },
+			lineNumbers: 'on',
+			scrollBeyondLastLine: false,
+			fontSize: 14,
+			cursorBlinking: 'solid',
+		},
+		editorWidgetOptions
+	));
+
+	editor.setModel(textModel);
+	editor.setPosition({ lineNumber: options.cursorLine, column: options.cursorColumn });
+
+	const renameWidget = instantiationService.createInstance(
+		RenameWidget,
+		editor,
+		['editor.action.rename', 'editor.action.rename'],
+	);
+	disposableStore.add(renameWidget);
+
+	const cts = new CancellationTokenSource();
+	disposableStore.add(cts);
+
+	renameWidget.getInput(
+		{
+			startLineNumber: options.cursorLine,
+			startColumn: options.rangeStartColumn,
+			endLineNumber: options.cursorLine,
+			endColumn: options.rangeEndColumn,
+		},
+		options.currentName,
+		false,
+		undefined,
+		cts
+	);
+}
+
+export default defineThemedFixtureGroup({ path: 'editor/' }, {
+	RenameVariable: defineComponentFixture({
+		labels: { kind: 'animated' },
+		render: (context) => renderRenameWidget({
+			...context,
+			cursorLine: 4,
+			cursorColumn: 2,
+			currentName: 'getUser',
+			rangeStartColumn: 2,
+			rangeEndColumn: 9,
+		}),
+	}),
+	RenameClass: defineComponentFixture({
+		labels: { kind: 'animated' },
+		render: (context) => renderRenameWidget({
+			...context,
+			cursorLine: 1,
+			cursorColumn: 7,
+			currentName: 'UserService',
+			rangeStartColumn: 7,
+			rangeEndColumn: 18,
+		}),
+	}),
+});
diff --git a/src/vs/workbench/test/browser/componentFixtures/suggestWidget.fixture.ts b/src/vs/workbench/test/browser/componentFixtures/suggestWidget.fixture.ts
new file mode 100644
index 0000000000000..8e04b43bc15a6
--- /dev/null
+++ b/src/vs/workbench/test/browser/componentFixtures/suggestWidget.fixture.ts
@@ -0,0 +1,172 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import { URI } from '../../../../base/common/uri.js';
+import { ComponentFixtureContext, createEditorServices, createTextModel, defineComponentFixture, defineThemedFixtureGroup } from './fixtureUtils.js';
+import { EditorExtensionsRegistry } from '../../../../editor/browser/editorExtensions.js';
+import { CodeEditorWidget, ICodeEditorWidgetOptions } from '../../../../editor/browser/widget/codeEditor/codeEditorWidget.js';
+import { EditorOption, IEditorOptions } from '../../../../editor/common/config/editorOptions.js';
+import { CompletionItemKind, CompletionList } from '../../../../editor/common/languages.js';
+import { SuggestController } from '../../../../editor/contrib/suggest/browser/suggestController.js';
+import { ISuggestMemoryService } from '../../../../editor/contrib/suggest/browser/suggestMemory.js';
+import { mock } from '../../../../base/test/common/mock.js';
+import { IMenuChangeEvent, IMenuService } from '../../../../platform/actions/common/actions.js';
+import { Emitter } from '../../../../base/common/event.js';
+import { CompletionModel, LineContext } from '../../../../editor/contrib/suggest/browser/completionModel.js';
+import { CompletionItem } from '../../../../editor/contrib/suggest/browser/suggest.js';
+import { WordDistance } from '../../../../editor/contrib/suggest/browser/wordDistance.js';
+import { FuzzyScoreOptions } from '../../../../base/common/filters.js';
+
+// CSS imports for the suggest widget
+import '../../../../editor/contrib/suggest/browser/media/suggest.css';
+import '../../../../editor/contrib/symbolIcons/browser/symbolIcons.js';
+import '../../../../base/browser/ui/codicons/codiconStyles.js';
+
+interface SuggestFixtureOptions extends ComponentFixtureContext {
+	code: string;
+	cursorLine: number;
+	cursorColumn: number;
+	completions: CompletionList;
+	width?: string;
+	height?: string;
+	editorOptions?: IEditorOptions;
+}
+
+function renderSuggestWidget(options: SuggestFixtureOptions): void {
+	const { container, disposableStore, theme } = options;
+	container.style.width = options.width ?? '500px';
+	container.style.height = options.height ?? '300px';
+	container.style.border = '1px solid var(--vscode-editorWidget-border)';
+
+	const instantiationService = createEditorServices(disposableStore, {
+		colorTheme: theme,
+		additionalServices: (reg) => {
+			reg.defineInstance(ISuggestMemoryService, new class extends mock<ISuggestMemoryService>() {
+				override memorize(): void { }
+				override select(): number { return 0; }
+			});
+			reg.defineInstance(IMenuService, new class extends mock<IMenuService>() {
+				override createMenu() {
+					return { onDidChange: new Emitter<IMenuChangeEvent>().event, getActions: () => [], dispose: () => { } };
+				}
+			});
+		},
+	});
+
+	const textModel = disposableStore.add(createTextModel(
+		instantiationService,
+		options.code,
+		URI.parse('inmemory://suggest-fixture.ts'),
+		'typescript'
+	));
+
+	const editorWidgetOptions: ICodeEditorWidgetOptions = {
+		contributions: EditorExtensionsRegistry.getEditorContributions()
+	};
+
+	const editor = disposableStore.add(instantiationService.createInstance(
+		CodeEditorWidget,
+		container,
+		{
+			automaticLayout: true,
+			minimap: { enabled: false },
+			lineNumbers: 'on',
+			scrollBeyondLastLine: false,
+			fontSize: 14,
+			cursorBlinking: 'solid',
+			suggest: {
+				showIcons: true,
+				showStatusBar: true,
+			},
+			...options.editorOptions,
+		},
+		editorWidgetOptions
+	));
+
+	editor.setModel(textModel);
+	const position = { lineNumber: options.cursorLine, column: options.cursorColumn };
+	editor.setPosition(position);
+	editor.focus();
+
+	const controller = SuggestController.get(editor)!;
+	const widget = controller.widget.value;
+
+	const completionList = options.completions;
+	const provider = { _debugDisplayName: 'suggestFixture', provideCompletionItems: () => completionList };
+	const items = completionList.suggestions.map(s => new CompletionItem(position, s, completionList, provider));
+
+	const lineContent = textModel.getLineContent(position.lineNumber);
+	const leadingLineContent = lineContent.substring(0, position.column - 1);
+
+	const completionModel = new CompletionModel(
+		items,
+		position.column,
+		new LineContext(leadingLineContent, 0),
+		WordDistance.None,
+		editor.getOption(EditorOption.suggest),
+		'inline',
+		FuzzyScoreOptions.default,
+		undefined
+	);
+
+	widget.showSuggestions(completionModel, 0, false, false, false);
+}
+
+const typescriptCompletions: CompletionList = {
+	suggestions: [
+		{ label: 'addEventListener', kind: CompletionItemKind.Method, insertText: 'addEventListener', range: { startLineNumber: 3, startColumn: 10, endLineNumber: 3, endColumn: 10 }, detail: '(method) addEventListener(type: string, listener: EventListener): void' },
+		{ label: 'appendChild', kind: CompletionItemKind.Method, insertText: 'appendChild', range: { startLineNumber: 3, startColumn: 10, endLineNumber: 3, endColumn: 10 }, detail: '(method) appendChild(node: Node): Node' },
+		{ label: 'attributes', kind: CompletionItemKind.Property, insertText: 'attributes', range: { startLineNumber: 3, startColumn: 10, endLineNumber: 3, endColumn: 10 } },
+		{ label: 'blur', kind: CompletionItemKind.Method, insertText: 'blur', range: { startLineNumber: 3, startColumn: 10, endLineNumber: 3, endColumn: 10 }, detail: '(method) blur(): void' },
+		{ label: 'childElementCount', kind: CompletionItemKind.Property, insertText: 'childElementCount', range: { startLineNumber: 3, startColumn: 10, endLineNumber: 3, endColumn: 10 } },
+		{ label: 'children', kind: CompletionItemKind.Property, insertText: 'children', range: { startLineNumber: 3, startColumn: 10, endLineNumber: 3, endColumn: 10 } },
+		{ label: 'classList', kind: CompletionItemKind.Property, insertText: 'classList', range: { startLineNumber: 3, startColumn: 10, endLineNumber: 3, endColumn: 10 } },
+		{ label: 'className', kind: CompletionItemKind.Property, insertText: 'className', range: { startLineNumber: 3, startColumn: 10, endLineNumber: 3, endColumn: 10 } },
+		{ label: 'click', kind: CompletionItemKind.Method, insertText: 'click', range: { startLineNumber: 3, startColumn: 10, endLineNumber: 3, endColumn: 10 }, detail: '(method) click(): void' },
+		{ label: 'cloneNode', kind: CompletionItemKind.Method, insertText: 'cloneNode', range: { startLineNumber: 3, startColumn: 10, endLineNumber: 3, endColumn: 10 }, detail: '(method) cloneNode(deep?: boolean): Node' },
+		{ label: 'closest', kind: CompletionItemKind.Method, insertText: 'closest', range: { startLineNumber: 3, startColumn: 10, endLineNumber: 3, endColumn: 10 }, detail: '(method) closest(selectors: string): Element | null' },
+		{ label: 'contains', kind: CompletionItemKind.Method, insertText: 'contains', range: { startLineNumber: 3, startColumn: 10, endLineNumber: 3, endColumn: 10 }, detail: '(method) contains(other: Node | null): boolean' },
+	],
+};
+
+const mixedKindCompletions: CompletionList = {
+	suggestions: [
+		{ label: 'MyClass', kind: CompletionItemKind.Class, insertText: 'MyClass', range: { startLineNumber: 1, startColumn: 1, endLineNumber: 1, endColumn: 1 }, detail: 'class MyClass' },
+		{ label: 'myFunction', kind: CompletionItemKind.Function, insertText: 'myFunction', range: { startLineNumber: 1, startColumn: 1, endLineNumber: 1, endColumn: 1 }, detail: 'function myFunction(): void' },
+		{ label: 'myVariable', kind: CompletionItemKind.Variable, insertText: 'myVariable', range: { startLineNumber: 1, startColumn: 1, endLineNumber: 1, endColumn: 1 }, detail: 'const myVariable: string' },
+		{ label: 'IMyInterface', kind: CompletionItemKind.Interface, insertText: 'IMyInterface', range: { startLineNumber: 1, startColumn: 1, endLineNumber: 1, endColumn: 1 }, detail: 'interface IMyInterface' },
+		{ label: 'MyEnum', kind: CompletionItemKind.Enum, insertText: 'MyEnum', range: { startLineNumber: 1, startColumn: 1, endLineNumber: 1, endColumn: 1 }, detail: 'enum MyEnum' },
+		{ label: 'MY_CONSTANT', kind: CompletionItemKind.Constant, insertText: 'MY_CONSTANT', range: { startLineNumber: 1, startColumn: 1, endLineNumber: 1, endColumn: 1 }, detail: 'const MY_CONSTANT = 42' },
+		{ label: 'myKeyword', kind: CompletionItemKind.Keyword, insertText: 'myKeyword', range: { startLineNumber: 1, startColumn: 1, endLineNumber: 1, endColumn: 1 } },
+		{ label: 'mySnippet', kind: CompletionItemKind.Snippet, insertText: 'mySnippet', range: { startLineNumber: 1, startColumn: 1, endLineNumber: 1, endColumn: 1 }, detail: 'snippet' },
+	],
+};
+
+export default defineThemedFixtureGroup({ path: 'editor/' }, {
+	MethodCompletions: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (context) => renderSuggestWidget({
+			...context,
+			code: `const element = document.getElementById('app');
+if (element) {
+	element.
+}`,
+			cursorLine: 3,
+			cursorColumn: 10,
+			completions: typescriptCompletions,
+		}),
+	}),
+
+	MixedKinds: defineComponentFixture({
+		labels: { kind: 'screenshot' },
+		render: (context) => renderSuggestWidget({
+			...context,
+			code: '',
+			cursorLine: 1,
+			cursorColumn: 1,
+			completions: mixedKindCompletions,
+		}),
+	}),
+});
diff --git a/src/vs/workbench/test/browser/contributions.test.ts b/src/vs/workbench/test/browser/contributions.test.ts
index 6eb3087bbbac4..cbd2984e56a2b 100644
--- a/src/vs/workbench/test/browser/contributions.test.ts
+++ b/src/vs/workbench/test/browser/contributions.test.ts
@@ -17,7 +17,7 @@ import { EditorService } from '../../services/editor/browser/editorService.js';
 import { IEditorGroupsService } from '../../services/editor/common/editorGroupsService.js';
 import { IEditorService, SIDE_GROUP } from '../../services/editor/common/editorService.js';
 import { LifecyclePhase } from '../../services/lifecycle/common/lifecycle.js';
-import { ITestInstantiationService, TestFileEditorInput, TestServiceAccessor, TestSingletonFileEditorInput, createEditorPart, registerTestEditor, workbenchInstantiationService } from './workbenchTestServices.js';
+import { ITestInstantiationService, TestFileEditorInput, TestServiceAccessor, TestForceRevealFileEditorInput, createEditorPart, registerTestEditor, workbenchInstantiationService } from './workbenchTestServices.js';
 
 suite('Contributions', () => {
 	const disposables = new DisposableStore();
@@ -48,7 +48,7 @@ suite('Contributions', () => {
 		bCreated = false;
 		bCreatedPromise = new DeferredPromise<void>();
 
-		disposables.add(registerTestEditor(TEST_EDITOR_ID, [new SyncDescriptor(TestFileEditorInput), new SyncDescriptor(TestSingletonFileEditorInput)], TEST_EDITOR_INPUT_ID));
+		disposables.add(registerTestEditor(TEST_EDITOR_ID, [new SyncDescriptor(TestFileEditorInput), new SyncDescriptor(TestForceRevealFileEditorInput)], TEST_EDITOR_INPUT_ID));
 	});
 
 	teardown(async () => {
diff --git a/src/vs/workbench/test/browser/notificationsPosition.test.ts b/src/vs/workbench/test/browser/notificationsPosition.test.ts
index 7b39370d37c73..fac02b907daf5 100644
--- a/src/vs/workbench/test/browser/notificationsPosition.test.ts
+++ b/src/vs/workbench/test/browser/notificationsPosition.test.ts
@@ -9,7 +9,7 @@ import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../base/test/comm
 import { DEFAULT_CUSTOM_TITLEBAR_HEIGHT } from '../../../platform/window/common/window.js';
 import { NotificationsPosition, NotificationsSettings } from '../../common/notifications.js';
 import { Codicon } from '../../../base/common/codicons.js';
-import { hideIcon, hideUpIcon } from '../../browser/parts/notifications/notificationsActions.js';
+import { hideIcon, hideUpIcon, getNotificationExpandIcon, getNotificationCollapseIcon } from '../../browser/parts/notifications/notificationsActions.js';
 
 suite('Notifications Position', () => {
 
@@ -142,4 +142,31 @@ suite('Notifications Position', () => {
 			assert.strictEqual(Codicon.chevronUp.id, 'chevron-up');
 		});
 	});
+
+	suite('Expand/Collapse Notification Icons', () => {
+
+		test('bottom-right expand uses notifications-expand icon', () => {
+			assert.strictEqual(getNotificationExpandIcon(NotificationsPosition.BOTTOM_RIGHT).id, 'notifications-expand');
+		});
+
+		test('bottom-left expand uses notifications-expand icon', () => {
+			assert.strictEqual(getNotificationExpandIcon(NotificationsPosition.BOTTOM_LEFT).id, 'notifications-expand');
+		});
+
+		test('top-right expand uses notifications-expand-down icon', () => {
+			assert.strictEqual(getNotificationExpandIcon(NotificationsPosition.TOP_RIGHT).id, 'notifications-expand-down');
+		});
+
+		test('bottom-right collapse uses notifications-collapse icon', () => {
+			assert.strictEqual(getNotificationCollapseIcon(NotificationsPosition.BOTTOM_RIGHT).id, 'notifications-collapse');
+		});
+
+		test('bottom-left collapse uses notifications-collapse icon', () => {
+			assert.strictEqual(getNotificationCollapseIcon(NotificationsPosition.BOTTOM_LEFT).id, 'notifications-collapse');
+		});
+
+		test('top-right collapse uses notifications-collapse-up icon', () => {
+			assert.strictEqual(getNotificationCollapseIcon(NotificationsPosition.TOP_RIGHT).id, 'notifications-collapse-up');
+		});
+	});
 });
diff --git a/src/vs/workbench/test/browser/parts/editor/breadcrumbModel.test.ts b/src/vs/workbench/test/browser/parts/editor/breadcrumbModel.test.ts
index 14d2d9512ef28..b48e8fe034919 100644
--- a/src/vs/workbench/test/browser/parts/editor/breadcrumbModel.test.ts
+++ b/src/vs/workbench/test/browser/parts/editor/breadcrumbModel.test.ts
@@ -20,7 +20,7 @@ suite('Breadcrumb Model', function () {
 	let model: BreadcrumbsModel;
 	const workspaceService = new TestContextService(new Workspace('ffff', [new WorkspaceFolder({ uri: URI.parse('foo:/bar/baz/ws'), name: 'ws', index: 0 })]));
 	const configService = new class extends TestConfigurationService {
-		override getValue<T>(...args: any[]): T | undefined {
+		override getValue<T>(...args: Parameters<TestConfigurationService['getValue']>): T | undefined {
 			if (args[0] === 'breadcrumbs.filePath') {
 				return 'on' as T;
 			}
diff --git a/src/vs/workbench/test/browser/parts/editor/modalEditorResize.test.ts b/src/vs/workbench/test/browser/parts/editor/modalEditorResize.test.ts
new file mode 100644
index 0000000000000..8b17d85b0e04c
--- /dev/null
+++ b/src/vs/workbench/test/browser/parts/editor/modalEditorResize.test.ts
@@ -0,0 +1,230 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+import assert from 'assert';
+import { Emitter } from '../../../../../base/common/event.js';
+import { Disposable, DisposableStore } from '../../../../../base/common/lifecycle.js';
+
+import { ensureNoDisposablesAreLeakedInTestSuite } from '../../../../../base/test/common/utils.js';
+
+interface ISize {
+	readonly width: number;
+	readonly height: number;
+}
+
+/**
+ * Simple test harness that mimics the ModalEditorPartImpl resize behavior
+ * without requiring the full editor part infrastructure.
+ */
+class TestModalEditorResizeHost extends Disposable {
+
+	private readonly _onDidChangeMaximized = this._register(new Emitter<boolean>());
+	readonly onDidChangeMaximized = this._onDidChangeMaximized.event;
+
+	private readonly _onDidRequestLayout = this._register(new Emitter<void>());
+	readonly onDidRequestLayout = this._onDidRequestLayout.event;
+
+	private _maximized = false;
+	get maximized(): boolean { return this._maximized; }
+
+	private _size: ISize | undefined;
+	get size(): ISize | undefined { return this._size; }
+	set size(value: ISize | undefined) { this._size = value; }
+
+	private _position: { left: number; top: number } | undefined;
+	get position(): { left: number; top: number } | undefined { return this._position; }
+	set position(value: { left: number; top: number } | undefined) { this._position = value; }
+
+	private savedSize: ISize | undefined;
+	private savedPosition: { left: number; top: number } | undefined;
+
+	toggleMaximized(): void {
+		this._maximized = !this._maximized;
+
+		if (this._maximized) {
+			this.savedSize = this._size;
+			this.savedPosition = this._position;
+		} else {
+			this._size = this.savedSize;
+			this._position = this.savedPosition;
+			this.savedSize = undefined;
+			this.savedPosition = undefined;
+		}
+
+		this._onDidChangeMaximized.fire(this._maximized);
+	}
+
+	handleHeaderDoubleClick(): void {
+		if (this._maximized) {
+			this.savedSize = undefined;
+			this.savedPosition = undefined;
+			this.toggleMaximized(); // un-maximize to default
+		} else if (this._size) {
+			this._size = undefined;
+			this._position = undefined;
+			this._onDidRequestLayout.fire();
+		} else {
+			this.toggleMaximized(); // maximize
+		}
+	}
+
+}
+
+suite('Modal Editor Resize', () => {
+
+	const disposables = new DisposableStore();
+
+	teardown(() => disposables.clear());
+
+	ensureNoDisposablesAreLeakedInTestSuite();
+
+	test('double-click from default size maximizes', () => {
+		const host = disposables.add(new TestModalEditorResizeHost());
+
+		const events: boolean[] = [];
+		disposables.add(host.onDidChangeMaximized(v => events.push(v)));
+
+		host.handleHeaderDoubleClick();
+
+		assert.deepStrictEqual(
+			{ maximized: host.maximized, size: host.size, events },
+			{ maximized: true, size: undefined, events: [true] }
+		);
+	});
+
+	test('double-click from maximized restores default', () => {
+		const host = disposables.add(new TestModalEditorResizeHost());
+
+		host.handleHeaderDoubleClick(); // maximize
+
+		const events: boolean[] = [];
+		disposables.add(host.onDidChangeMaximized(v => events.push(v)));
+
+		host.handleHeaderDoubleClick(); // restore
+
+		assert.deepStrictEqual(
+			{ maximized: host.maximized, size: host.size, events },
+			{ maximized: false, size: undefined, events: [false] }
+		);
+	});
+
+	test('double-click from custom size restores default without firing maximized event', () => {
+		const host = disposables.add(new TestModalEditorResizeHost());
+
+		host.size = { width: 800, height: 600 };
+
+		const maximizedEvents: boolean[] = [];
+		let layoutRequested = false;
+		disposables.add(host.onDidChangeMaximized(v => maximizedEvents.push(v)));
+		disposables.add(host.onDidRequestLayout(() => { layoutRequested = true; }));
+
+		host.handleHeaderDoubleClick();
+
+		assert.deepStrictEqual(
+			{ maximized: host.maximized, size: host.size, maximizedEvents, layoutRequested },
+			{ maximized: false, size: undefined, maximizedEvents: [], layoutRequested: true }
+		);
+	});
+
+	test('double-click cycle: custom → default → maximized → default', () => {
+		const host = disposables.add(new TestModalEditorResizeHost());
+
+		const events: boolean[] = [];
+		disposables.add(host.onDidChangeMaximized(v => events.push(v)));
+
+		// Start with custom size
+		host.size = { width: 800, height: 600 };
+
+		// First double-click: custom → default (fires layout, not maximized)
+		host.handleHeaderDoubleClick();
+		assert.strictEqual(host.maximized, false);
+		assert.strictEqual(host.size, undefined);
+
+		// Second double-click: default → maximized
+		host.handleHeaderDoubleClick();
+		assert.strictEqual(host.maximized, true);
+		assert.strictEqual(host.size, undefined);
+
+		// Third double-click: maximized → default
+		host.handleHeaderDoubleClick();
+		assert.strictEqual(host.maximized, false);
+		assert.strictEqual(host.size, undefined);
+
+		assert.deepStrictEqual(events, [true, false]);
+	});
+
+	test('toggleMaximized preserves custom state through maximize/un-maximize cycle', () => {
+		const host = disposables.add(new TestModalEditorResizeHost());
+
+		host.size = { width: 800, height: 600 };
+		host.position = { left: 100, top: 50 };
+
+		host.toggleMaximized();
+		assert.strictEqual(host.maximized, true);
+
+		host.toggleMaximized();
+		assert.deepStrictEqual(
+			{ maximized: host.maximized, size: host.size, position: host.position },
+			{ maximized: false, size: { width: 800, height: 600 }, position: { left: 100, top: 50 } }
+		);
+	});
+
+	test('double-click from maximized clears saved custom state', () => {
+		const host = disposables.add(new TestModalEditorResizeHost());
+
+		// Set custom size then maximize via toggleMaximized (saves state)
+		host.size = { width: 800, height: 600 };
+		host.toggleMaximized();
+		assert.strictEqual(host.maximized, true);
+
+		// Double-click to un-maximize: should go to default, not restore custom
+		host.handleHeaderDoubleClick();
+		assert.deepStrictEqual(
+			{ maximized: host.maximized, size: host.size },
+			{ maximized: false, size: undefined }
+		);
+	});
+
+	test('double-click clears custom position along with size', () => {
+		const host = disposables.add(new TestModalEditorResizeHost());
+
+		host.size = { width: 800, height: 600 };
+		host.position = { left: 100, top: 50 };
+
+		host.handleHeaderDoubleClick();
+
+		assert.deepStrictEqual(
+			{ size: host.size, position: host.position, maximized: host.maximized },
+			{ size: undefined, position: undefined, maximized: false }
+		);
+	});
+
+	test('session persistence: state can be saved and restored across instances', () => {
+		const host1 = disposables.add(new TestModalEditorResizeHost());
+
+		host1.size = { width: 900, height: 700 };
+		host1.position = { left: 200, top: 100 };
+
+		// Simulate saving state on close
+		const savedState = {
+			size: host1.size,
+			position: host1.position,
+			maximized: host1.maximized,
+		};
+
+		// Simulate restoring state on new modal
+		const host2 = disposables.add(new TestModalEditorResizeHost());
+		host2.size = savedState.size;
+		host2.position = savedState.position;
+		if (savedState.maximized) {
+			host2.toggleMaximized();
+		}
+
+		assert.deepStrictEqual(
+			{ size: host2.size, position: host2.position, maximized: host2.maximized },
+			{ size: { width: 900, height: 700 }, position: { left: 200, top: 100 }, maximized: false }
+		);
+	});
+});
diff --git a/src/vs/workbench/test/browser/window.test.ts b/src/vs/workbench/test/browser/window.test.ts
index f758f9900d8c8..1290fef45c35e 100644
--- a/src/vs/workbench/test/browser/window.test.ts
+++ b/src/vs/workbench/test/browser/window.test.ts
@@ -41,7 +41,7 @@ suite('Window', () => {
 			function createWindow(id: number, slow?: boolean) {
 				// eslint-disable-next-line local/code-no-any-casts
 				const res = {
-					setTimeout: function (callback: Function, delay: number, ...args: any[]): number {
+					setTimeout: function (callback: Function, delay: number, ...args: unknown[]): number {
 						setTimeoutCalls.push(id);
 
 						return mainWindow.setTimeout(() => callback(id), slow ? delay * 2 : delay, ...args);
diff --git a/src/vs/workbench/test/browser/workbenchTestServices.ts b/src/vs/workbench/test/browser/workbenchTestServices.ts
index 529c27d720d98..3762453a62c7f 100644
--- a/src/vs/workbench/test/browser/workbenchTestServices.ts
+++ b/src/vs/workbench/test/browser/workbenchTestServices.ts
@@ -1639,9 +1639,9 @@ export class TestFileEditorInput extends EditorInput implements IFileEditorInput
 	}
 }
 
-export class TestSingletonFileEditorInput extends TestFileEditorInput {
+export class TestForceRevealFileEditorInput extends TestFileEditorInput {
 
-	override get capabilities(): EditorInputCapabilities { return EditorInputCapabilities.Singleton; }
+	override get capabilities(): EditorInputCapabilities { return EditorInputCapabilities.ForceReveal; }
 }
 
 export class TestEditorPart extends MainEditorPart implements IEditorGroupsService {
diff --git a/src/vs/workbench/test/common/workbenchTestServices.ts b/src/vs/workbench/test/common/workbenchTestServices.ts
index e625aa79e5bbd..f9e3a45bb4fa3 100644
--- a/src/vs/workbench/test/common/workbenchTestServices.ts
+++ b/src/vs/workbench/test/common/workbenchTestServices.ts
@@ -9,7 +9,7 @@ import { CancellationToken } from '../../../base/common/cancellation.js';
 import { Emitter, Event } from '../../../base/common/event.js';
 import { Iterable } from '../../../base/common/iterator.js';
 import { Disposable, IDisposable, toDisposable } from '../../../base/common/lifecycle.js';
-import { ResourceMap } from '../../../base/common/map.js';
+import { ResourceMap, ResourceSet } from '../../../base/common/map.js';
 import { Schemas } from '../../../base/common/network.js';
 import { observableValue } from '../../../base/common/observable.js';
 import { join } from '../../../base/common/path.js';
@@ -120,6 +120,10 @@ export class TestContextService implements IWorkspaceContextService {
 		return WorkbenchState.EMPTY;
 	}
 
+	hasWorkspaceData(): boolean {
+		return this.getWorkbenchState() !== WorkbenchState.EMPTY;
+	}
+
 	getCompleteWorkspace(): Promise<IWorkspace> {
 		return Promise.resolve(this.getWorkspace());
 	}
@@ -376,7 +380,8 @@ export class TestWorkspaceTrustManagementService extends Disposable implements I
 
 
 	constructor(
-		private trusted: boolean = true
+		private trusted: boolean = true,
+		private trustedUris: ResourceSet = new ResourceSet()
 	) {
 		super();
 	}
@@ -402,11 +407,11 @@ export class TestWorkspaceTrustManagementService extends Disposable implements I
 	}
 
 	getUriTrustInfo(uri: URI): Promise<IWorkspaceTrustUriInfo> {
-		throw new Error('Method not implemented.');
+		return Promise.resolve({ trusted: this.trustedUris.has(uri), uri });
 	}
 
 	async setTrustedUris(folders: URI[]): Promise<void> {
-		throw new Error('Method not implemented.');
+		this.trustedUris = new ResourceSet(folders);
 	}
 
 	async setUrisTrust(uris: URI[], trusted: boolean): Promise<void> {
diff --git a/src/vs/workbench/workbench.common.main.ts b/src/vs/workbench/workbench.common.main.ts
index be64fd940aaae..1d89cb13a5652 100644
--- a/src/vs/workbench/workbench.common.main.ts
+++ b/src/vs/workbench/workbench.common.main.ts
@@ -212,6 +212,7 @@ import './contrib/inlineChat/browser/inlineChat.contribution.js';
 import './contrib/mcp/browser/mcp.contribution.js';
 import './contrib/chat/browser/chatSessions/chatSessions.contribution.js';
 import './contrib/chat/browser/contextContrib/chatContext.contribution.js';
+import './contrib/imageCarousel/browser/imageCarousel.contribution.js';
 
 // Interactive
 import './contrib/interactive/browser/interactive.contribution.js';
diff --git a/src/vs/workbench/workbench.desktop.main.ts b/src/vs/workbench/workbench.desktop.main.ts
index 8291f38e8d17d..68821267b8613 100644
--- a/src/vs/workbench/workbench.desktop.main.ts
+++ b/src/vs/workbench/workbench.desktop.main.ts
@@ -178,7 +178,7 @@ import './contrib/remoteTunnel/electron-browser/remoteTunnel.contribution.js';
 
 // Chat
 import './contrib/chat/electron-browser/chat.contribution.js';
-import './contrib/inlineChat/electron-browser/inlineChat.contribution.js';
+
 // Encryption
 import './contrib/encryption/electron-browser/encryption.contribution.js';
 
diff --git a/src/vs/workbench/workbench.web.main.ts b/src/vs/workbench/workbench.web.main.ts
index aee7366ed5353..939822a241a16 100644
--- a/src/vs/workbench/workbench.web.main.ts
+++ b/src/vs/workbench/workbench.web.main.ts
@@ -174,4 +174,7 @@ import './contrib/remote/browser/remoteStartEntry.contribution.js';
 // Process Explorer
 import './contrib/processExplorer/browser/processExplorer.web.contribution.js';
 
+// Browser View
+import './contrib/browserView/browser/browserView.contribution.js';
+
 //#endregion
diff --git a/src/vscode-dts/vscode.proposed.authIssuers.d.ts b/src/vscode-dts/vscode.proposed.authIssuers.d.ts
index 4496226011355..70b3094f7e22a 100644
--- a/src/vscode-dts/vscode.proposed.authIssuers.d.ts
+++ b/src/vscode-dts/vscode.proposed.authIssuers.d.ts
@@ -15,7 +15,7 @@ declare module 'vscode' {
 	export interface AuthenticationProviderSessionOptions {
 		/**
 		 * When specified, the authentication provider will use the provided authorization server URL to
-		 * authenticate the user. This is only used when a provider has `supportsAuthorizationServers` set
+		 * authenticate the user. This is only used when a provider has `supportedAuthorizationServers` set
 		 */
 		authorizationServer?: Uri;
 	}
@@ -23,7 +23,7 @@ declare module 'vscode' {
 	export interface AuthenticationGetSessionOptions {
 		/**
 		 * When specified, the authentication provider will use the provided authorization server URL to
-		 * authenticate the user. This is only used when a provider has `supportsAuthorizationServers` set
+		 * authenticate the user. This is only used when a provider has `supportedAuthorizationServers` set
 		 */
 		authorizationServer?: Uri;
 	}
diff --git a/src/vscode-dts/vscode.proposed.browser.d.ts b/src/vscode-dts/vscode.proposed.browser.d.ts
new file mode 100644
index 0000000000000..a15d432b3b71a
--- /dev/null
+++ b/src/vscode-dts/vscode.proposed.browser.d.ts
@@ -0,0 +1,92 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+declare module 'vscode' {
+
+	// @kycutler https://github.com/microsoft/vscode/issues/300319
+
+	/**
+	 * An integrated browser page displayed in an editor tab.
+	 */
+	export interface BrowserTab {
+		/** The current URL of the page. */
+		readonly url: string;
+
+		/** The current page title. */
+		readonly title: string;
+
+		/** The page icon (favicon or a default globe icon). */
+		readonly icon: IconPath;
+
+		/** Create a new CDP session that exposes this browser tab. */
+		startCDPSession(): Thenable<BrowserCDPSession>;
+
+		/** Close this browser tab. */
+		close(): Thenable<void>;
+	}
+
+	/**
+	 * A CDP (Chrome DevTools Protocol) session that provides a bidirectional message channel.
+	 *
+	 * Create a session via {@link BrowserTab.startCDPSession}.
+	 */
+	export interface BrowserCDPSession {
+		/** Fires when a CDP message is received from an attached target. */
+		readonly onDidReceiveMessage: Event<unknown>;
+
+		/** Fires when this session is closed. */
+		readonly onDidClose: Event<void>;
+
+		/** Send a CDP request message to an attached target. */
+		sendMessage(message: unknown): Thenable<void>;
+
+		/** Close this session and detach all targets. */
+		close(): Thenable<void>;
+	}
+
+	/** Options for {@link window.openBrowserTab}. */
+	export interface BrowserTabShowOptions {
+		/**
+		 * The view column to show the browser in. Defaults to {@link ViewColumn.Active}.
+		 * Use {@linkcode ViewColumn.Beside} to open next to the current editor.
+		 */
+		viewColumn?: ViewColumn;
+
+		/** When `true`, the browser tab will not take focus. */
+		preserveFocus?: boolean;
+
+		/** When `true`, the browser tab will open in the background. */
+		background?: boolean;
+	}
+
+	export namespace window {
+		/** The currently open browser tabs. */
+		export const browserTabs: readonly BrowserTab[];
+
+		/** Fires when a browser tab is opened. */
+		export const onDidOpenBrowserTab: Event<BrowserTab>;
+
+		/** Fires when a browser tab is closed. */
+		export const onDidCloseBrowserTab: Event<BrowserTab>;
+
+		/** The currently active browser tab. */
+		export const activeBrowserTab: BrowserTab | undefined;
+
+		/** Fires when {@link activeBrowserTab} changes. */
+		export const onDidChangeActiveBrowserTab: Event<BrowserTab | undefined>;
+
+		/** Fires when a browser tab's state (url, title, or icon) changes. */
+		export const onDidChangeBrowserTabState: Event<BrowserTab>;
+
+		/**
+		 * Open a browser tab at the given URL.
+		 *
+		 * @param url The URL to navigate to.
+		 * @param options Controls where and how the browser tab is shown.
+		 * @returns The {@link BrowserTab} representing the opened page.
+		 */
+		export function openBrowserTab(url: string, options?: BrowserTabShowOptions): Thenable<BrowserTab>;
+	}
+}
diff --git a/src/vscode-dts/vscode.proposed.chatDebug.d.ts b/src/vscode-dts/vscode.proposed.chatDebug.d.ts
index 604cc0f0ef710..ed91aa806a147 100644
--- a/src/vscode-dts/vscode.proposed.chatDebug.d.ts
+++ b/src/vscode-dts/vscode.proposed.chatDebug.d.ts
@@ -3,7 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-// version: 1
+// version: 3
 
 declare module 'vscode' {
 	/**
@@ -142,6 +142,37 @@ declare module 'vscode' {
 		 */
 		durationInMillis?: number;
 
+		/**
+		 * The number of cached input tokens reused from a previous request.
+		 */
+		cachedTokens?: number;
+
+		/**
+		 * The time in milliseconds from sending the request to receiving the
+		 * first response token.
+		 */
+		timeToFirstTokenInMillis?: number;
+
+		/**
+		 * The maximum number of prompt/input tokens allowed for this request.
+		 */
+		maxInputTokens?: number;
+
+		/**
+		 * The maximum number of response/output tokens allowed for this request.
+		 */
+		maxOutputTokens?: number;
+
+		/**
+		 * The short name or label identifying this request (e.g., "panel/editAgent").
+		 */
+		requestName?: string;
+
+		/**
+		 * The outcome status of the model turn (e.g., "success", "failure", "canceled").
+		 */
+		status?: string;
+
 		/**
 		 * Create a new ChatDebugModelTurnEvent.
 		 * @param created The timestamp when the event was created.
@@ -447,13 +478,130 @@ declare module 'vscode' {
 		constructor(type: ChatDebugMessageContentType, message: string, sections: ChatDebugMessageSection[]);
 	}
 
+	/**
+	 * Structured tool call content for a resolved chat debug event,
+	 * containing the tool name, status, arguments, and output for rich rendering.
+	 */
+	export class ChatDebugEventToolCallContent {
+		/**
+		 * The name of the tool that was called.
+		 */
+		toolName: string;
+
+		/**
+		 * The outcome of the tool call (e.g., "success" or "error").
+		 */
+		result?: ChatDebugToolCallResult;
+
+		/**
+		 * How long the tool call took to complete, in milliseconds.
+		 */
+		durationInMillis?: number;
+
+		/**
+		 * The serialized input (arguments) passed to the tool.
+		 */
+		input?: string;
+
+		/**
+		 * The serialized output (result) returned by the tool.
+		 */
+		output?: string;
+
+		/**
+		 * Create a new ChatDebugEventToolCallContent.
+		 * @param toolName The name of the tool that was called.
+		 */
+		constructor(toolName: string);
+	}
+
+	/**
+	 * Structured model turn content for a resolved chat debug event,
+	 * containing request metadata, token usage, and timing for rich rendering.
+	 */
+	export class ChatDebugEventModelTurnContent {
+		/**
+		 * The short name or label identifying this request (e.g., "panel/editAgent").
+		 */
+		requestName: string;
+
+		/**
+		 * The identifier of the model used (e.g., "claude-sonnet-4.5").
+		 */
+		model?: string;
+
+		/**
+		 * The outcome status of the model turn (e.g., "success", "failure", "canceled").
+		 */
+		status?: string;
+
+		/**
+		 * How long the model turn took to complete, in milliseconds.
+		 */
+		durationInMillis?: number;
+
+		/**
+		 * The time in milliseconds from sending the request to receiving the
+		 * first response token.
+		 */
+		timeToFirstTokenInMillis?: number;
+
+		/**
+		 * The maximum number of prompt/input tokens allowed for this request.
+		 */
+		maxInputTokens?: number;
+
+		/**
+		 * The maximum number of response/output tokens allowed for this request.
+		 */
+		maxOutputTokens?: number;
+
+		/**
+		 * The number of tokens in the input/prompt.
+		 */
+		inputTokens?: number;
+
+		/**
+		 * The number of tokens in the model's output/completion.
+		 */
+		outputTokens?: number;
+
+		/**
+		 * The number of cached input tokens reused from a previous request.
+		 */
+		cachedTokens?: number;
+
+		/**
+		 * The total number of tokens consumed (input + output).
+		 */
+		totalTokens?: number;
+
+		/**
+		 * An error message, if the model turn failed.
+		 */
+		errorMessage?: string;
+
+		/**
+		 * Optional structured sections containing the full request/response details
+		 * (e.g., system prompt, user prompt, tools, response).
+		 * Rendered as collapsible sections in the detail view alongside the metadata.
+		 */
+		sections?: ChatDebugMessageSection[];
+
+		/**
+		 * Create a new ChatDebugEventModelTurnContent.
+		 * @param requestName The short name identifying this request.
+		 */
+		constructor(requestName: string);
+	}
+
 	/**
 	 * Union of all resolved event content types.
 	 * Extensions may also return {@link ChatDebugUserMessageEvent} or
 	 * {@link ChatDebugAgentResponseEvent} from resolve, which will be
 	 * automatically converted to structured message content.
 	 */
-	export type ChatDebugResolvedEventContent = ChatDebugEventTextContent | ChatDebugEventMessageContent | ChatDebugUserMessageEvent | ChatDebugAgentResponseEvent;
+	export type ChatDebugResolvedEventContent = ChatDebugEventTextContent | ChatDebugEventMessageContent | ChatDebugEventToolCallContent | ChatDebugEventModelTurnContent | ChatDebugUserMessageEvent | ChatDebugAgentResponseEvent;
 
 	/**
 	 * Union of all chat debug event types. Each type is a class,
@@ -494,6 +642,37 @@ declare module 'vscode' {
 			eventId: string,
 			token: CancellationToken
 		): ProviderResult<ChatDebugResolvedEventContent>;
+
+		/**
+		 * Export the debug log for a chat session as a serialized byte array.
+		 * The extension controls the format (e.g., OTLP JSON with Copilot extensions).
+		 * Core provides the save dialog and writes the returned bytes to disk.
+		 *
+		 * @param sessionResource The resource URI of the chat session to export.
+		 * @param options Export options including core events and session metadata.
+		 * @param token A cancellation token.
+		 * @returns The serialized debug log data, or undefined if export is not available.
+		 */
+		provideChatDebugLogExport?(
+			sessionResource: Uri,
+			options: ChatDebugLogExportOptions,
+			token: CancellationToken
+		): ProviderResult<Uint8Array>;
+
+		/**
+		 * Import a previously exported debug log from a serialized byte array.
+		 * Core provides the open dialog and reads the file bytes.
+		 * The extension deserializes the data and returns a session URI that can be
+		 * opened in the debug panel via {@link provideChatDebugLog}.
+		 *
+		 * @param data The serialized debug log data (as returned by {@link provideChatDebugLogExport}).
+		 * @param token A cancellation token.
+		 * @returns The imported session info, or undefined if import failed.
+		 */
+		resolveChatDebugLogImport?(
+			data: Uint8Array,
+			token: CancellationToken
+		): ProviderResult<ChatDebugLogImportResult>;
 	}
 
 	export namespace chat {
@@ -505,5 +684,44 @@ declare module 'vscode' {
 		 * @returns A disposable that unregisters the provider.
 		 */
 		export function registerChatDebugLogProvider(provider: ChatDebugLogProvider): Disposable;
+
+		/**
+		 * Fired when a core-originated debug event is received (e.g., prompt discovery,
+		 * skill loading). Extensions can use this to capture events that originate
+		 * inside Core.
+		 */
+		export const onDidReceiveChatDebugEvent: Event<ChatDebugEvent>;
+	}
+
+	/**
+	 * Options passed to {@link ChatDebugLogProvider.provideChatDebugLogExport}.
+	 */
+	export interface ChatDebugLogExportOptions {
+		/**
+		 * Core-originated debug events (prompt discovery, skill loading, etc.)
+		 * for the session. The extension may include these in the export alongside its own data.
+		 */
+		readonly coreEvents: readonly ChatDebugEvent[];
+
+		/**
+		 * Session title, if available.
+		 * Used to provide a human-readable label in the exported file.
+		 */
+		readonly sessionTitle?: string;
+	}
+
+	/**
+	 * Result of importing a debug log via {@link ChatDebugLogProvider.resolveChatDebugLogImport}.
+	 */
+	export interface ChatDebugLogImportResult {
+		/**
+		 * The session resource URI for the imported session.
+		 */
+		readonly uri: Uri;
+
+		/**
+		 * The session title from the imported file, if available.
+		 */
+		readonly sessionTitle?: string;
 	}
 }
diff --git a/src/vscode-dts/vscode.proposed.chatHooks.d.ts b/src/vscode-dts/vscode.proposed.chatHooks.d.ts
index eec28002b77d1..85323b85156cc 100644
--- a/src/vscode-dts/vscode.proposed.chatHooks.d.ts
+++ b/src/vscode-dts/vscode.proposed.chatHooks.d.ts
@@ -10,7 +10,7 @@ declare module 'vscode' {
 	/**
 	 * The type of hook to execute.
 	 */
-	export type ChatHookType = 'SessionStart' | 'UserPromptSubmit' | 'PreToolUse' | 'PostToolUse' | 'PreCompact' | 'SubagentStart' | 'SubagentStop' | 'Stop';
+	export type ChatHookType = 'SessionStart' | 'SessionEnd' | 'UserPromptSubmit' | 'PreToolUse' | 'PostToolUse' | 'PreCompact' | 'SubagentStart' | 'SubagentStop' | 'Stop' | 'ErrorOccurred';
 
 	/**
 	 * A resolved hook command ready for execution.
diff --git a/src/vscode-dts/vscode.proposed.chatParticipantAdditions.d.ts b/src/vscode-dts/vscode.proposed.chatParticipantAdditions.d.ts
index f122a55550a83..286b87dd85cc7 100644
--- a/src/vscode-dts/vscode.proposed.chatParticipantAdditions.d.ts
+++ b/src/vscode-dts/vscode.proposed.chatParticipantAdditions.d.ts
@@ -839,6 +839,12 @@ declare module 'vscode' {
 		 */
 		readonly completionTokens: number;
 
+		/**
+		 * The number of tokens reserved for the response.
+		 * This is rendered specially in the UI to indicate that these tokens aren't used but are reserved.
+		 */
+		readonly outputBuffer?: number;
+
 		/**
 		 * Optional breakdown of prompt token usage by category and label.
 		 * If the percentages do not sum to 100%, the remaining will be shown as "Uncategorized".
@@ -1059,9 +1065,15 @@ declare module 'vscode' {
 	}
 
 	export interface ChatRequestModeInstructions {
+		/** set when the mode a custom agent (not built-in), to be used as identifier */
+		readonly uri?: Uri;
 		readonly name: string;
 		readonly content: string;
 		readonly toolReferences?: readonly ChatLanguageModelToolReference[];
 		readonly metadata?: Record<string, boolean | string | number>;
+		/**
+		 * Whether the mode is a builtin mode (e.g. Ask, Edit, Agent) rather than a user or extension-defined custom mode.
+		 */
+		readonly isBuiltin?: boolean;
 	}
 }
diff --git a/src/vscode-dts/vscode.proposed.chatParticipantPrivate.d.ts b/src/vscode-dts/vscode.proposed.chatParticipantPrivate.d.ts
index 16c8ff488a027..d9041946408a8 100644
--- a/src/vscode-dts/vscode.proposed.chatParticipantPrivate.d.ts
+++ b/src/vscode-dts/vscode.proposed.chatParticipantPrivate.d.ts
@@ -3,7 +3,7 @@
  *  Licensed under the MIT License. See License.txt in the project root for license information.
  *--------------------------------------------------------------------------------------------*/
 
-// version: 14
+// version: 15
 
 declare module 'vscode' {
 
@@ -116,6 +116,13 @@ declare module 'vscode' {
 		 */
 		readonly parentRequestId?: string;
 
+		/**
+		 * The permission level for tool auto-approval in this request.
+		 * - `'autoApprove'`: Auto-approve all tool calls and retry on errors.
+		 * - `'autopilot'`: Everything autoApprove does plus continues until the task is done.
+		 */
+		readonly permissionLevel?: string;
+
 		/**
 		 * Whether any hooks are enabled for this request.
 		 */
@@ -393,6 +400,13 @@ declare module 'vscode' {
 		 * will immediately follow up with a new request in the same conversation.
 		 */
 		readonly yieldRequested: boolean;
+
+		/**
+		 * The resource URI identifying the chat session this context belongs to.
+		 * Available when the context is provided for title generation, summarization,
+		 * or other session-scoped operations. Extracted from the session's history entries.
+		 */
+		readonly sessionResource?: Uri;
 	}
 
 	// #endregion
diff --git a/src/vscode-dts/vscode.proposed.chatPromptFiles.d.ts b/src/vscode-dts/vscode.proposed.chatPromptFiles.d.ts
index e683d6ce6005b..898b0cfbe27ef 100644
--- a/src/vscode-dts/vscode.proposed.chatPromptFiles.d.ts
+++ b/src/vscode-dts/vscode.proposed.chatPromptFiles.d.ts
@@ -103,6 +103,39 @@ declare module 'vscode' {
 	// #region Chat Provider Registration
 
 	export namespace chat {
+		/**
+		 * An event that fires when the list of {@link customAgents custom agents} changes.
+		 */
+		export const onDidChangeCustomAgents: Event<void>;
+
+		/**
+		 * The list of currently available custom agents. These are `.agent.md` files
+		 * from all sources (workspace, user, and extension-provided).
+		 */
+		export const customAgents: readonly ChatResource[];
+
+		/**
+		 * An event that fires when the list of {@link instructions instructions} changes.
+		 */
+		export const onDidChangeInstructions: Event<void>;
+
+		/**
+		 * The list of currently available instructions. These are `.instructions.md` files
+		 * from all sources (workspace, user, and extension-provided).
+		 */
+		export const instructions: readonly ChatResource[];
+
+		/**
+		 * An event that fires when the list of {@link skills skills} changes.
+		 */
+		export const onDidChangeSkills: Event<void>;
+
+		/**
+		 * The list of currently available skills. These are `SKILL.md` files
+		 * from all sources (workspace, user, and extension-provided).
+		 */
+		export const skills: readonly ChatResource[];
+
 		/**
 		 * Register a provider for custom agents.
 		 * @param provider The custom agent provider.
diff --git a/src/vscode-dts/vscode.proposed.chatProvider.d.ts b/src/vscode-dts/vscode.proposed.chatProvider.d.ts
index 1ded6ac9ba730..b19b106205b8e 100644
--- a/src/vscode-dts/vscode.proposed.chatProvider.d.ts
+++ b/src/vscode-dts/vscode.proposed.chatProvider.d.ts
@@ -13,7 +13,8 @@ declare module 'vscode' {
 	export interface ProvideLanguageModelChatResponseOptions {
 
 		/**
-		 * What extension initiated the request to the language model
+		 * What extension initiated the request to the language model, or
+		 * `undefined` if the request was initiated by other functionality in the editor.
 		 */
 		readonly requestInitiator: string;
 	}
diff --git a/src/vscode-dts/vscode.proposed.chatSessionsProvider.d.ts b/src/vscode-dts/vscode.proposed.chatSessionsProvider.d.ts
index f0f1e7fb27916..69679ab35c7e9 100644
--- a/src/vscode-dts/vscode.proposed.chatSessionsProvider.d.ts
+++ b/src/vscode-dts/vscode.proposed.chatSessionsProvider.d.ts
@@ -93,7 +93,14 @@ declare module 'vscode' {
 	export type ChatSessionItemControllerRefreshHandler = (token: CancellationToken) => Thenable<void>;
 
 	export interface ChatSessionItemControllerNewItemHandlerContext {
-		readonly request: ChatRequest;
+		// TODO: Use a better type but for now decrease this down to just the prompt and command since that's all we currently need.
+		// The problem with ChatRequest is that it has a resourceUri which is not good for this code path.
+		readonly request: {
+			readonly prompt: string;
+			readonly command?: string;
+		};
+
+		readonly sessionOptions: ReadonlyArray<{ optionId: string; value: string | ChatSessionProviderOptionItem }>;
 	}
 
 	/**
@@ -442,10 +449,13 @@ declare module 'vscode' {
 		 *
 		 * @param resource The URI of the chat session to resolve.
 		 * @param token A cancellation token that can be used to cancel the operation.
+		 * @param context Additional context for the chat session.
 		 *
 		 * @return The {@link ChatSession chat session} associated with the given URI.
 		 */
-		provideChatSessionContent(resource: Uri, token: CancellationToken): Thenable<ChatSession> | ChatSession;
+		provideChatSessionContent(resource: Uri, token: CancellationToken, context: {
+			readonly sessionOptions: ReadonlyArray<{ optionId: string; value: string | ChatSessionProviderOptionItem }>;
+		}): Thenable<ChatSession> | ChatSession;
 
 		/**
 		 * @param resource Identifier of the chat session being updated.
@@ -456,9 +466,8 @@ declare module 'vscode' {
 
 		/**
 		 * Called as soon as you register (call me once)
-		 * @param token
 		 */
-		provideChatSessionProviderOptions?(token: CancellationToken): Thenable<ChatSessionProviderOptions | ChatSessionProviderOptions>;
+		provideChatSessionProviderOptions?(token: CancellationToken): Thenable<ChatSessionProviderOptions>;
 	}
 
 	export interface ChatSessionOptionUpdate {
@@ -615,6 +624,13 @@ declare module 'vscode' {
 		 * Provider-defined option groups (0-2 groups supported).
 		 * Examples: models picker, sub-agents picker, etc.
 		 */
-		optionGroups?: ChatSessionProviderOptionGroup[];
+		readonly optionGroups?: readonly ChatSessionProviderOptionGroup[];
+
+		/**
+		 * The set of default options used for new chat sessions, provided as key-value pairs.
+		 *
+		 * Keys correspond to option group IDs (e.g., 'models', 'subagents').
+		 */
+		readonly newSessionOptions?: Record<string, string | ChatSessionProviderOptionItem>;
 	}
 }
diff --git a/src/vscode-dts/vscode.proposed.languageModelToolSupportsModel.d.ts b/src/vscode-dts/vscode.proposed.languageModelToolSupportsModel.d.ts
index ab481a3d9d88f..7d3b546e9c2f5 100644
--- a/src/vscode-dts/vscode.proposed.languageModelToolSupportsModel.d.ts
+++ b/src/vscode-dts/vscode.proposed.languageModelToolSupportsModel.d.ts
@@ -42,7 +42,7 @@ declare module 'vscode' {
 		 * Registers a language model tool along with its definition. Unlike {@link lm.registerTool},
 		 * this does not require the tool to be present first in the extension's `package.json` contributions.
 		 *
-		 * Multiple tools may be registered with the the same name using the API. In any given context,
+		 * Multiple tools may be registered with the same name using the API. In any given context,
 		 * the most specific tool (based on the {@link LanguageModelToolDefinition.models}) will be used.
 		 *
 		 * @param definition The definition of the tool to register.
diff --git a/src/vscode-dts/vscode.proposed.taskRunOptions.d.ts b/src/vscode-dts/vscode.proposed.taskRunOptions.d.ts
new file mode 100644
index 0000000000000..4f874a3354f2b
--- /dev/null
+++ b/src/vscode-dts/vscode.proposed.taskRunOptions.d.ts
@@ -0,0 +1,34 @@
+/*---------------------------------------------------------------------------------------------
+ *  Copyright (c) Microsoft Corporation. All rights reserved.
+ *  Licensed under the MIT License. See License.txt in the project root for license information.
+ *--------------------------------------------------------------------------------------------*/
+
+declare module 'vscode' {
+
+	/**
+	 * Controls when a task should be run.
+	 */
+	export enum TaskRunOn {
+		/**
+		 * The task is not run automatically.
+		 */
+		Default = 1,
+
+		/**
+		 * The task runs when a folder is opened.
+		 */
+		FolderOpen = 2,
+
+		/**
+		 * The task runs when an Agent Session worktree is created.
+		 */
+		WorktreeCreated = 3,
+	}
+
+	export interface RunOptions {
+		/**
+		 * Controls when a task is run automatically.
+		 */
+		runOn?: TaskRunOn;
+	}
+}
\ No newline at end of file
diff --git a/test/automation/package-lock.json b/test/automation/package-lock.json
index ceeff39f6fbc6..cbc02be2a4a49 100644
--- a/test/automation/package-lock.json
+++ b/test/automation/package-lock.json
@@ -474,10 +474,11 @@
       }
     },
     "node_modules/minimatch": {
-      "version": "3.1.2",
-      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-3.1.2.tgz",
-      "integrity": "sha512-J7p63hRiAjw1NDEww1W7i37+ByIrOWO5XQQAzZ3VOcL0PNybwpfmV/N05zFAzwQ9USyEcX6t3UO+K5aqBQOIHw==",
+      "version": "3.1.5",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-3.1.5.tgz",
+      "integrity": "sha512-VgjWUsnnT6n+NUk6eZq77zeFdpW2LWDzP6zFGrCbHXiYNul5Dzqk2HHQ5uFH2DNW5Xbp8+jVzaeNt94ssEEl4w==",
       "dev": true,
+      "license": "ISC",
       "dependencies": {
         "brace-expansion": "^1.1.7"
       },
diff --git a/test/componentFixtures/.screenshots/baseline/agentSessionsViewer/ApprovalRow1Line/Dark.png b/test/componentFixtures/.screenshots/baseline/agentSessionsViewer/ApprovalRow1Line/Dark.png
new file mode 100644
index 0000000000000..a5e5f2c31d508
--- /dev/null
+++ b/test/componentFixtures/.screenshots/baseline/agentSessionsViewer/ApprovalRow1Line/Dark.png
@@ -0,0 +1,3 @@
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new file mode 100644
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--- /dev/null
+++ b/test/componentFixtures/.screenshots/baseline/agentSessionsViewer/ApprovalRow1Line/Light.png
@@ -0,0 +1,3 @@
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new file mode 100644
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--- /dev/null
+++ b/test/componentFixtures/.screenshots/baseline/agentSessionsViewer/ApprovalRow2Lines/Dark.png
@@ -0,0 +1,3 @@
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diff --git a/test/componentFixtures/.screenshots/baseline/agentSessionsViewer/ApprovalRow2Lines/Light.png b/test/componentFixtures/.screenshots/baseline/agentSessionsViewer/ApprovalRow2Lines/Light.png
new file mode 100644
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--- /dev/null
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@@ -0,0 +1,3 @@
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new file mode 100644
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--- /dev/null
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new file mode 100644
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--- /dev/null
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@@ -0,0 +1,3 @@
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new file mode 100644
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new file mode 100644
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new file mode 100644
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diff --git a/test/componentFixtures/component-explorer-config.schema.json b/test/componentFixtures/component-explorer-config.schema.json
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-{
-	"$schema": "https://json-schema.org/draft/2020-12/schema",
-	"type": "object",
-	"properties": {
-		"screenshotDir": {
-			"description": "Directory for storing screenshots (default: .screenshots)",
-			"type": "string"
-		},
-		"sessions": {
-			"minItems": 1,
-			"type": "array",
-			"items": {
-				"type": "object",
-				"properties": {
-					"name": {
-						"type": "string",
-						"description": "Unique session name"
-					},
-					"source": {
-						"anyOf": [
-							{
-								"type": "string",
-								"const": "current"
-							},
-							{
-								"type": "object",
-								"properties": {
-									"worktree": {
-										"type": "object",
-										"properties": {
-											"ref": {
-												"type": "string",
-												"description": "Git ref (branch, tag, or commit) to check out"
-											},
-											"name": {
-												"description": "Directory name for the worktree (default: component-explorer-baseline)",
-												"type": "string"
-											},
-											"install": {
-												"anyOf": [
-													{
-														"type": "string",
-														"const": "auto"
-													},
-													{
-														"type": "string",
-														"const": "npm"
-													},
-													{
-														"type": "string",
-														"const": "pnpm"
-													},
-													{
-														"type": "string",
-														"const": "yarn"
-													},
-													{
-														"type": "object",
-														"properties": {
-															"command": {
-																"type": "string",
-																"description": "Custom install command to run in the worktree"
-															}
-														},
-														"required": [
-															"command"
-														],
-														"additionalProperties": false
-													},
-													{
-														"type": "boolean",
-														"const": false
-													}
-												],
-												"description": "Dependency install strategy for the worktree"
-											}
-										},
-										"required": [
-											"ref"
-										],
-										"additionalProperties": false,
-										"description": "Git worktree configuration for a baseline session"
-									}
-								},
-								"required": [
-									"worktree"
-								],
-								"additionalProperties": false
-							}
-						],
-						"description": "Session source: \"current\" for the working tree, or a worktree config for a baseline"
-					},
-					"viteConfig": {
-						"description": "Path to vite config file, relative to this config (overrides top-level viteConfig)",
-						"type": "string"
-					}
-				},
-				"required": [
-					"name"
-				],
-				"additionalProperties": false,
-				"description": "A component explorer session"
-			},
-			"description": "List of explorer sessions"
-		},
-		"compare": {
-			"type": "object",
-			"properties": {
-				"baseline": {
-					"type": "string",
-					"description": "Session name to use as the baseline for comparisons"
-				},
-				"current": {
-					"type": "string",
-					"description": "Session name to use as the current version for comparisons"
-				}
-			},
-			"required": [
-				"baseline",
-				"current"
-			],
-			"additionalProperties": false,
-			"description": "Screenshot comparison configuration"
-		},
-		"viteConfig": {
-			"description": "Default vite config file path, relative to this config (default: vite.config.ts)",
-			"type": "string"
-		},
-		"vite": {
-			"type": "object",
-			"properties": {
-				"hmr": {
-					"type": "object",
-					"properties": {
-						"allowedPaths": {
-							"type": "array",
-							"items": {
-								"type": "string"
-							},
-							"description": "Glob patterns for files that keep HMR; everything else triggers a full reload"
-						}
-					},
-					"required": [
-						"allowedPaths"
-					],
-					"additionalProperties": false,
-					"description": "Vite HMR configuration"
-				}
-			},
-			"additionalProperties": false,
-			"description": "Vite configuration overrides"
-		},
-		"redirection": {
-			"type": "object",
-			"properties": {
-				"port": {
-					"type": "integer",
-					"minimum": 1,
-					"maximum": 65535,
-					"description": "Port for the redirection HTTP server"
-				},
-				"host": {
-					"description": "Host to bind the redirection server to (default: localhost)",
-					"type": "string"
-				}
-			},
-			"required": [
-				"port"
-			],
-			"additionalProperties": false,
-			"description": "HTTP redirection server that redirects to the session URL"
-		},
-		"$schema": {
-			"type": "string",
-			"description": "URL of the JSON Schema for this config file"
-		}
-	},
-	"required": [
-		"sessions"
-	],
-	"additionalProperties": false,
-	"description": "Component Explorer configuration"
-}
diff --git a/test/componentFixtures/component-explorer.json b/test/componentFixtures/component-explorer.json
index 2f24a100b0273..cc0a459626936 100644
--- a/test/componentFixtures/component-explorer.json
+++ b/test/componentFixtures/component-explorer.json
@@ -1,11 +1,17 @@
 {
-	"$schema": "./component-explorer-config.schema.json",
+	"$schema": "../../node_modules/@vscode/component-explorer-cli/dist/component-explorer-config.schema.json",
 	"screenshotDir": ".screenshots",
 	"sessions": [
 		{
 			"name": "current"
 		}
 	],
+	"worktree": {
+		"maxSlots": 1,
+		"setup": {
+			"command": "echo 'test'"
+		}
+	},
 	"redirection": {
 		"port": 5337
 	},
diff --git a/test/integration/browser/package-lock.json b/test/integration/browser/package-lock.json
index 538e7c4c3e979..90ce261a01be9 100644
--- a/test/integration/browser/package-lock.json
+++ b/test/integration/browser/package-lock.json
@@ -135,10 +135,11 @@
       "dev": true
     },
     "node_modules/minimatch": {
-      "version": "3.1.2",
-      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-3.1.2.tgz",
-      "integrity": "sha512-J7p63hRiAjw1NDEww1W7i37+ByIrOWO5XQQAzZ3VOcL0PNybwpfmV/N05zFAzwQ9USyEcX6t3UO+K5aqBQOIHw==",
+      "version": "3.1.5",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-3.1.5.tgz",
+      "integrity": "sha512-VgjWUsnnT6n+NUk6eZq77zeFdpW2LWDzP6zFGrCbHXiYNul5Dzqk2HHQ5uFH2DNW5Xbp8+jVzaeNt94ssEEl4w==",
       "dev": true,
+      "license": "ISC",
       "dependencies": {
         "brace-expansion": "^1.1.7"
       },
diff --git a/test/mcp/package-lock.json b/test/mcp/package-lock.json
index f3a0ceb0bfffd..25b41f55f7995 100644
--- a/test/mcp/package-lock.json
+++ b/test/mcp/package-lock.json
@@ -22,9 +22,9 @@
       }
     },
     "node_modules/@hono/node-server": {
-      "version": "1.19.9",
-      "resolved": "https://registry.npmjs.org/@hono/node-server/-/node-server-1.19.9.tgz",
-      "integrity": "sha512-vHL6w3ecZsky+8P5MD+eFfaGTyCeOHUIFYMGpQGbrBTSmNNoxv0if69rEZ5giu36weC5saFuznL411gRX7bJDw==",
+      "version": "1.19.10",
+      "resolved": "https://registry.npmjs.org/@hono/node-server/-/node-server-1.19.10.tgz",
+      "integrity": "sha512-hZ7nOssGqRgyV3FVVQdfi+U4q02uB23bpnYpdvNXkYTRRyWx84b7yf1ans+dnJ/7h41sGL3CeQTfO+ZGxuO+Iw==",
       "license": "MIT",
       "engines": {
         "node": ">=18.14.1"
@@ -489,12 +489,12 @@
       }
     },
     "node_modules/express-rate-limit": {
-      "version": "8.2.1",
-      "resolved": "https://registry.npmjs.org/express-rate-limit/-/express-rate-limit-8.2.1.tgz",
-      "integrity": "sha512-PCZEIEIxqwhzw4KF0n7QF4QqruVTcF73O5kFKUnGOyjbCCgizBBiFaYpd/fnBLUMPw/BWw9OsiN7GgrNYr7j6g==",
+      "version": "8.3.0",
+      "resolved": "https://registry.npmjs.org/express-rate-limit/-/express-rate-limit-8.3.0.tgz",
+      "integrity": "sha512-KJzBawY6fB9FiZGdE/0aftepZ91YlaGIrV8vgblRM3J8X+dHx/aiowJWwkx6LIGyuqGiANsjSwwrbb8mifOJ4Q==",
       "license": "MIT",
       "dependencies": {
-        "ip-address": "10.0.1"
+        "ip-address": "10.1.0"
       },
       "engines": {
         "node": ">= 16"
@@ -702,9 +702,9 @@
       }
     },
     "node_modules/hono": {
-      "version": "4.12.0",
-      "resolved": "https://registry.npmjs.org/hono/-/hono-4.12.0.tgz",
-      "integrity": "sha512-NekXntS5M94pUfiVZ8oXXK/kkri+5WpX2/Ik+LVsl+uvw+soj4roXIsPqO+XsWrAw20mOzaXOZf3Q7PfB9A/IA==",
+      "version": "4.12.7",
+      "resolved": "https://registry.npmjs.org/hono/-/hono-4.12.7.tgz",
+      "integrity": "sha512-jq9l1DM0zVIvsm3lv9Nw9nlJnMNPOcAtsbsgiUhWcFzPE99Gvo6yRTlszSLLYacMeQ6quHD6hMfId8crVHvexw==",
       "license": "MIT",
       "engines": {
         "node": ">=16.9.0"
@@ -753,9 +753,9 @@
       "license": "ISC"
     },
     "node_modules/ip-address": {
-      "version": "10.0.1",
-      "resolved": "https://registry.npmjs.org/ip-address/-/ip-address-10.0.1.tgz",
-      "integrity": "sha512-NWv9YLW4PoW2B7xtzaS3NCot75m6nK7Icdv0o3lfMceJVRfSoQwqD4wEH5rLwoKJwUiZ/rfpiVBhnaF0FK4HoA==",
+      "version": "10.1.0",
+      "resolved": "https://registry.npmjs.org/ip-address/-/ip-address-10.1.0.tgz",
+      "integrity": "sha512-XXADHxXmvT9+CRxhXg56LJovE+bmWnEWB78LB83VZTprKTmaC5QfruXocxzTZ2Kl0DNwKuBdlIhjL8LeY8Sf8Q==",
       "license": "MIT",
       "engines": {
         "node": ">= 12"
diff --git a/test/monaco/.npmrc b/test/monaco/.npmrc
index a9c57709666b2..efe233421c4cc 100644
--- a/test/monaco/.npmrc
+++ b/test/monaco/.npmrc
@@ -1,2 +1,3 @@
 legacy-peer-deps="true"
 timeout=180000
+min-release-age="1"
diff --git a/test/monaco/package-lock.json b/test/monaco/package-lock.json
index 513d33eeb3444..3e3df8a1775fe 100644
--- a/test/monaco/package-lock.json
+++ b/test/monaco/package-lock.json
@@ -8,11 +8,79 @@
       "name": "test-monaco",
       "version": "1.0.0",
       "license": "MIT",
+      "dependencies": {
+        "postcss": "^8.5.6"
+      },
       "devDependencies": {
         "@types/chai": "^4.2.14",
         "axe-playwright": "^2.1.0",
         "chai": "^4.2.0",
-        "warnings-to-errors-webpack-plugin": "^2.3.0"
+        "css-loader": "^6.9.1",
+        "file-loader": "^6.2.0",
+        "style-loader": "^3.3.2",
+        "warnings-to-errors-webpack-plugin": "^2.3.0",
+        "webpack": "^5.105.0",
+        "webpack-cli": "^5.1.4"
+      }
+    },
+    "node_modules/@discoveryjs/json-ext": {
+      "version": "0.5.7",
+      "resolved": "https://registry.npmjs.org/@discoveryjs/json-ext/-/json-ext-0.5.7.tgz",
+      "integrity": "sha512-dBVuXR082gk3jsFp7Rd/JI4kytwGHecnCoTtXFb7DB6CNHp4rg5k1bhg0nWdLGLnOV71lmDzGQaLMy8iPLY0pw==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=10.0.0"
+      }
+    },
+    "node_modules/@jridgewell/gen-mapping": {
+      "version": "0.3.13",
+      "resolved": "https://registry.npmjs.org/@jridgewell/gen-mapping/-/gen-mapping-0.3.13.tgz",
+      "integrity": "sha512-2kkt/7niJ6MgEPxF0bYdQ6etZaA+fQvDcLKckhy1yIQOzaoKjBBjSj63/aLVjYE3qhRt5dvM+uUyfCg6UKCBbA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@jridgewell/sourcemap-codec": "^1.5.0",
+        "@jridgewell/trace-mapping": "^0.3.24"
+      }
+    },
+    "node_modules/@jridgewell/resolve-uri": {
+      "version": "3.1.2",
+      "resolved": "https://registry.npmjs.org/@jridgewell/resolve-uri/-/resolve-uri-3.1.2.tgz",
+      "integrity": "sha512-bRISgCIjP20/tbWSPWMEi54QVPRZExkuD9lJL+UIxUKtwVJA8wW1Trb1jMs1RFXo1CBTNZ/5hpC9QvmKWdopKw==",
+      "dev": true,
+      "license": "MIT",
+      "engines": {
+        "node": ">=6.0.0"
+      }
+    },
+    "node_modules/@jridgewell/source-map": {
+      "version": "0.3.11",
+      "resolved": "https://registry.npmjs.org/@jridgewell/source-map/-/source-map-0.3.11.tgz",
+      "integrity": "sha512-ZMp1V8ZFcPG5dIWnQLr3NSI1MiCU7UETdS/A0G8V/XWHvJv3ZsFqutJn1Y5RPmAPX6F3BiE397OqveU/9NCuIA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@jridgewell/gen-mapping": "^0.3.5",
+        "@jridgewell/trace-mapping": "^0.3.25"
+      }
+    },
+    "node_modules/@jridgewell/sourcemap-codec": {
+      "version": "1.5.5",
+      "resolved": "https://registry.npmjs.org/@jridgewell/sourcemap-codec/-/sourcemap-codec-1.5.5.tgz",
+      "integrity": "sha512-cYQ9310grqxueWbl+WuIUIaiUaDcj7WOq5fVhEljNVgRfOUhY9fy2zTvfoqWsnebh8Sl70VScFbICvJnLKB0Og==",
+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/@jridgewell/trace-mapping": {
+      "version": "0.3.31",
+      "resolved": "https://registry.npmjs.org/@jridgewell/trace-mapping/-/trace-mapping-0.3.31.tgz",
+      "integrity": "sha512-zzNR+SdQSDJzc8joaeP8QQoCQr8NuYx2dIIytl1QeBEZHJ9uW6hebsrYgbz8hJwUQao3TWCMtmfV8Nu1twOLAw==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@jridgewell/resolve-uri": "^3.1.0",
+        "@jridgewell/sourcemap-codec": "^1.4.14"
       }
     },
     "node_modules/@types/chai": {
@@ -21,6 +89,42 @@
       "integrity": "sha512-G+ITQPXkwTrslfG5L/BksmbLUA0M1iybEsmCWPqzSxsRRhJZimBKJkoMi8fr/CPygPTj4zO5pJH7I2/cm9M7SQ==",
       "dev": true
     },
+    "node_modules/@types/eslint": {
+      "version": "9.6.1",
+      "resolved": "https://registry.npmjs.org/@types/eslint/-/eslint-9.6.1.tgz",
+      "integrity": "sha512-FXx2pKgId/WyYo2jXw63kk7/+TY7u7AziEJxJAnSFzHlqTAS3Ync6SvgYAN/k4/PQpnnVuzoMuVnByKK2qp0ag==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@types/estree": "*",
+        "@types/json-schema": "*"
+      }
+    },
+    "node_modules/@types/eslint-scope": {
+      "version": "3.7.7",
+      "resolved": "https://registry.npmjs.org/@types/eslint-scope/-/eslint-scope-3.7.7.tgz",
+      "integrity": "sha512-MzMFlSLBqNF2gcHWO0G1vP/YQyfvrxZ0bF+u7mzUdZ1/xK4A4sru+nraZz5i3iEIk1l1uyicaDVTB4QbbEkAYg==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@types/eslint": "*",
+        "@types/estree": "*"
+      }
+    },
+    "node_modules/@types/estree": {
+      "version": "1.0.8",
+      "resolved": "https://registry.npmjs.org/@types/estree/-/estree-1.0.8.tgz",
+      "integrity": "sha512-dWHzHa2WqEXI/O1E9OjrocMTKJl2mSrEolh1Iomrv6U+JuNwaHXsXx9bLu5gG7BUWFIN0skIQJQ/L1rIex4X6w==",
+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/@types/json-schema": {
+      "version": "7.0.15",
+      "resolved": "https://registry.npmjs.org/@types/json-schema/-/json-schema-7.0.15.tgz",
+      "integrity": "sha512-5+fP8P8MFNC+AyZCDxrB2pkZFPGzqQWUzpSeuuVLvm8VMcorNYavBqoFcxK8bQz4Qsbn4oUEEem4wDLfcysGHA==",
+      "dev": true,
+      "license": "MIT"
+    },
     "node_modules/@types/junit-report-builder": {
       "version": "3.0.2",
       "resolved": "https://registry.npmjs.org/@types/junit-report-builder/-/junit-report-builder-3.0.2.tgz",
@@ -28,6 +132,333 @@
       "dev": true,
       "license": "MIT"
     },
+    "node_modules/@types/node": {
+      "version": "25.4.0",
+      "resolved": "https://registry.npmjs.org/@types/node/-/node-25.4.0.tgz",
+      "integrity": "sha512-9wLpoeWuBlcbBpOY3XmzSTG3oscB6xjBEEtn+pYXTfhyXhIxC5FsBer2KTopBlvKEiW9l13po9fq+SJY/5lkhw==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "undici-types": "~7.18.0"
+      }
+    },
+    "node_modules/@webassemblyjs/ast": {
+      "version": "1.14.1",
+      "resolved": "https://registry.npmjs.org/@webassemblyjs/ast/-/ast-1.14.1.tgz",
+      "integrity": "sha512-nuBEDgQfm1ccRp/8bCQrx1frohyufl4JlbMMZ4P1wpeOfDhF6FQkxZJ1b/e+PLwr6X1Nhw6OLme5usuBWYBvuQ==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@webassemblyjs/helper-numbers": "1.13.2",
+        "@webassemblyjs/helper-wasm-bytecode": "1.13.2"
+      }
+    },
+    "node_modules/@webassemblyjs/floating-point-hex-parser": {
+      "version": "1.13.2",
+      "resolved": "https://registry.npmjs.org/@webassemblyjs/floating-point-hex-parser/-/floating-point-hex-parser-1.13.2.tgz",
+      "integrity": "sha512-6oXyTOzbKxGH4steLbLNOu71Oj+C8Lg34n6CqRvqfS2O71BxY6ByfMDRhBytzknj9yGUPVJ1qIKhRlAwO1AovA==",
+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/@webassemblyjs/helper-api-error": {
+      "version": "1.13.2",
+      "resolved": "https://registry.npmjs.org/@webassemblyjs/helper-api-error/-/helper-api-error-1.13.2.tgz",
+      "integrity": "sha512-U56GMYxy4ZQCbDZd6JuvvNV/WFildOjsaWD3Tzzvmw/mas3cXzRJPMjP83JqEsgSbyrmaGjBfDtV7KDXV9UzFQ==",
+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/@webassemblyjs/helper-buffer": {
+      "version": "1.14.1",
+      "resolved": "https://registry.npmjs.org/@webassemblyjs/helper-buffer/-/helper-buffer-1.14.1.tgz",
+      "integrity": "sha512-jyH7wtcHiKssDtFPRB+iQdxlDf96m0E39yb0k5uJVhFGleZFoNw1c4aeIcVUPPbXUVJ94wwnMOAqUHyzoEPVMA==",
+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/@webassemblyjs/helper-numbers": {
+      "version": "1.13.2",
+      "resolved": "https://registry.npmjs.org/@webassemblyjs/helper-numbers/-/helper-numbers-1.13.2.tgz",
+      "integrity": "sha512-FE8aCmS5Q6eQYcV3gI35O4J789wlQA+7JrqTTpJqn5emA4U2hvwJmvFRC0HODS+3Ye6WioDklgd6scJ3+PLnEA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@webassemblyjs/floating-point-hex-parser": "1.13.2",
+        "@webassemblyjs/helper-api-error": "1.13.2",
+        "@xtuc/long": "4.2.2"
+      }
+    },
+    "node_modules/@webassemblyjs/helper-wasm-bytecode": {
+      "version": "1.13.2",
+      "resolved": "https://registry.npmjs.org/@webassemblyjs/helper-wasm-bytecode/-/helper-wasm-bytecode-1.13.2.tgz",
+      "integrity": "sha512-3QbLKy93F0EAIXLh0ogEVR6rOubA9AoZ+WRYhNbFyuB70j3dRdwH9g+qXhLAO0kiYGlg3TxDV+I4rQTr/YNXkA==",
+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/@webassemblyjs/helper-wasm-section": {
+      "version": "1.14.1",
+      "resolved": "https://registry.npmjs.org/@webassemblyjs/helper-wasm-section/-/helper-wasm-section-1.14.1.tgz",
+      "integrity": "sha512-ds5mXEqTJ6oxRoqjhWDU83OgzAYjwsCV8Lo/N+oRsNDmx/ZDpqalmrtgOMkHwxsG0iI//3BwWAErYRHtgn0dZw==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@webassemblyjs/ast": "1.14.1",
+        "@webassemblyjs/helper-buffer": "1.14.1",
+        "@webassemblyjs/helper-wasm-bytecode": "1.13.2",
+        "@webassemblyjs/wasm-gen": "1.14.1"
+      }
+    },
+    "node_modules/@webassemblyjs/ieee754": {
+      "version": "1.13.2",
+      "resolved": "https://registry.npmjs.org/@webassemblyjs/ieee754/-/ieee754-1.13.2.tgz",
+      "integrity": "sha512-4LtOzh58S/5lX4ITKxnAK2USuNEvpdVV9AlgGQb8rJDHaLeHciwG4zlGr0j/SNWlr7x3vO1lDEsuePvtcDNCkw==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@xtuc/ieee754": "^1.2.0"
+      }
+    },
+    "node_modules/@webassemblyjs/leb128": {
+      "version": "1.13.2",
+      "resolved": "https://registry.npmjs.org/@webassemblyjs/leb128/-/leb128-1.13.2.tgz",
+      "integrity": "sha512-Lde1oNoIdzVzdkNEAWZ1dZ5orIbff80YPdHx20mrHwHrVNNTjNr8E3xz9BdpcGqRQbAEa+fkrCb+fRFTl/6sQw==",
+      "dev": true,
+      "license": "Apache-2.0",
+      "dependencies": {
+        "@xtuc/long": "4.2.2"
+      }
+    },
+    "node_modules/@webassemblyjs/utf8": {
+      "version": "1.13.2",
+      "resolved": "https://registry.npmjs.org/@webassemblyjs/utf8/-/utf8-1.13.2.tgz",
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+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/@webassemblyjs/wasm-edit": {
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+    "node_modules/webpack/node_modules/ajv-keywords": {
+      "version": "5.1.0",
+      "resolved": "https://registry.npmjs.org/ajv-keywords/-/ajv-keywords-5.1.0.tgz",
+      "integrity": "sha512-YCS/JNFAUyr5vAuhk1DWm1CBxRHW9LbJ2ozWeemrIqpbsqKjHVxYPyi5GC0rjZIT5JxJ3virVTS8wk4i/Z+krw==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "fast-deep-equal": "^3.1.3"
+      },
+      "peerDependencies": {
+        "ajv": "^8.8.2"
+      }
+    },
+    "node_modules/webpack/node_modules/json-schema-traverse": {
+      "version": "1.0.0",
+      "resolved": "https://registry.npmjs.org/json-schema-traverse/-/json-schema-traverse-1.0.0.tgz",
+      "integrity": "sha512-NM8/P9n3XjXhIZn1lLhkFaACTOURQXjWhV4BA/RnOv8xvgqtqpAX9IO4mRQxSx1Rlo4tqzeqb0sOlruaOy3dug==",
+      "dev": true,
+      "license": "MIT"
+    },
+    "node_modules/webpack/node_modules/schema-utils": {
+      "version": "4.3.3",
+      "resolved": "https://registry.npmjs.org/schema-utils/-/schema-utils-4.3.3.tgz",
+      "integrity": "sha512-eflK8wEtyOE6+hsaRVPxvUKYCpRgzLqDTb8krvAsRIwOGlHoSgYLgBXoubGgLd2fT41/OUYdb48v4k4WWHQurA==",
+      "dev": true,
+      "license": "MIT",
+      "dependencies": {
+        "@types/json-schema": "^7.0.9",
+        "ajv": "^8.9.0",
+        "ajv-formats": "^2.1.1",
+        "ajv-keywords": "^5.1.0"
+      },
+      "engines": {
+        "node": ">= 10.13.0"
+      },
+      "funding": {
+        "type": "opencollective",
+        "url": "https://opencollective.com/webpack"
+      }
+    },
+    "node_modules/which": {
+      "version": "2.0.2",
+      "resolved": "https://registry.npmjs.org/which/-/which-2.0.2.tgz",
+      "integrity": "sha512-BLI3Tl1TW3Pvl70l3yq3Y64i+awpwXqsGBYWkkqMtnbXgrMD+yj7rhW0kuEDxzJaYXGjEW5ogapKNMEKNMjibA==",
+      "dev": true,
+      "license": "ISC",
+      "dependencies": {
+        "isexe": "^2.0.0"
+      },
+      "bin": {
+        "node-which": "bin/node-which"
+      },
+      "engines": {
+        "node": ">= 8"
+      }
+    },
+    "node_modules/wildcard": {
+      "version": "2.0.1",
+      "resolved": "https://registry.npmjs.org/wildcard/-/wildcard-2.0.1.tgz",
+      "integrity": "sha512-CC1bOL87PIWSBhDcTrdeLo6eGT7mCFtrg0uIJtqJUFyK+eJnzl8A1niH56uu7KMa5XFrtiV+AQuHO3n7DsHnLQ==",
+      "dev": true,
+      "license": "MIT"
+    },
     "node_modules/xmlbuilder": {
       "version": "15.1.1",
       "resolved": "https://registry.npmjs.org/xmlbuilder/-/xmlbuilder-15.1.1.tgz",
diff --git a/test/monaco/package.json b/test/monaco/package.json
index c73739194315a..89902f2304fe4 100644
--- a/test/monaco/package.json
+++ b/test/monaco/package.json
@@ -6,7 +6,7 @@
   "private": true,
   "scripts": {
     "compile": "node ../../node_modules/typescript/bin/tsc",
-    "bundle-webpack": "node ../../node_modules/webpack/bin/webpack --config ./webpack.config.js --bail",
+    "bundle-webpack": "webpack --config ./webpack.config.js --bail",
     "esm-check": "node esm-check/esm-check.js",
     "test": "node runner.js"
   },
@@ -14,6 +14,14 @@
     "@types/chai": "^4.2.14",
     "axe-playwright": "^2.1.0",
     "chai": "^4.2.0",
-    "warnings-to-errors-webpack-plugin": "^2.3.0"
+    "css-loader": "^6.9.1",
+    "file-loader": "^6.2.0",
+    "style-loader": "^3.3.2",
+    "warnings-to-errors-webpack-plugin": "^2.3.0",
+    "webpack": "^5.105.0",
+    "webpack-cli": "^5.1.4"
+  },
+  "dependencies": {
+    "postcss": "^8.5.6"
   }
 }
diff --git a/test/monaco/tsconfig.json b/test/monaco/tsconfig.json
index dcc46d24c5aec..75bd907e41a01 100644
--- a/test/monaco/tsconfig.json
+++ b/test/monaco/tsconfig.json
@@ -9,6 +9,9 @@
 		"sourceMap": true,
 		"skipLibCheck": true,
 		"declaration": true,
+		"types": [
+			"mocha"
+		],
 		"lib": [
 			"esnext", // for #201187
 			"dom"
diff --git a/test/sanity/package-lock.json b/test/sanity/package-lock.json
index 27d7cd8110ed8..c441eb7cf188c 100644
--- a/test/sanity/package-lock.json
+++ b/test/sanity/package-lock.json
@@ -648,12 +648,12 @@
       }
     },
     "node_modules/minimatch": {
-      "version": "9.0.5",
-      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-9.0.5.tgz",
-      "integrity": "sha512-G6T0ZX48xgozx7587koeX9Ys2NYy6Gmv//P89sEte9V9whIapMNF4idKxnW2QtCcLiTWlb/wfCabAtAFWhhBow==",
+      "version": "9.0.9",
+      "resolved": "https://registry.npmjs.org/minimatch/-/minimatch-9.0.9.tgz",
+      "integrity": "sha512-OBwBN9AL4dqmETlpS2zasx+vTeWclWzkblfZk7KTA5j3jeOONz/tRCnZomUyvNg83wL5Zv9Ss6HMJXAgL8R2Yg==",
       "license": "ISC",
       "dependencies": {
-        "brace-expansion": "^2.0.1"
+        "brace-expansion": "^2.0.2"
       },
       "engines": {
         "node": ">=16 || 14 >=14.17"
@@ -918,15 +918,6 @@
         "node": ">=18"
       }
     },
-    "node_modules/randombytes": {
-      "version": "2.1.0",
-      "resolved": "https://registry.npmjs.org/randombytes/-/randombytes-2.1.0.tgz",
-      "integrity": "sha512-vYl3iOX+4CKUWuxGi9Ukhie6fsqXqS9FE2Zaic4tNFD2N2QQaXOMFbuKK4QmDHC0JO6B1Zp41J0LpT0oR68amQ==",
-      "license": "MIT",
-      "dependencies": {
-        "safe-buffer": "^5.1.0"
-      }
-    },
     "node_modules/readdirp": {
       "version": "4.1.2",
       "resolved": "https://registry.npmjs.org/readdirp/-/readdirp-4.1.2.tgz",
@@ -949,33 +940,13 @@
         "node": ">=0.10.0"
       }
     },
-    "node_modules/safe-buffer": {
-      "version": "5.2.1",
-      "resolved": "https://registry.npmjs.org/safe-buffer/-/safe-buffer-5.2.1.tgz",
-      "integrity": "sha512-rp3So07KcdmmKbGvgaNxQSJr7bGVSVk5S9Eq1F+ppbRo70+YeaDxkw5Dd8NPN+GD6bjnYm2VuPuCXmpuYvmCXQ==",
-      "funding": [
-        {
-          "type": "github",
-          "url": "https://github.com/sponsors/feross"
-        },
-        {
-          "type": "patreon",
-          "url": "https://www.patreon.com/feross"
-        },
-        {
-          "type": "consulting",
-          "url": "https://feross.org/support"
-        }
-      ],
-      "license": "MIT"
-    },
     "node_modules/serialize-javascript": {
-      "version": "6.0.2",
-      "resolved": "https://registry.npmjs.org/serialize-javascript/-/serialize-javascript-6.0.2.tgz",
-      "integrity": "sha512-Saa1xPByTTq2gdeFZYLLo+RFE35NHZkAbqZeWNd3BpzppeVisAqpDjcp8dyf6uIvEqJRd46jemmyA4iFIeVk8g==",
+      "version": "7.0.4",
+      "resolved": "https://registry.npmjs.org/serialize-javascript/-/serialize-javascript-7.0.4.tgz",
+      "integrity": "sha512-DuGdB+Po43Q5Jxwpzt1lhyFSYKryqoNjQSA9M92tyw0lyHIOur+XCalOUe0KTJpyqzT8+fQ5A0Jf7vCx/NKmIg==",
       "license": "BSD-3-Clause",
-      "dependencies": {
-        "randombytes": "^2.1.0"
+      "engines": {
+        "node": ">=20.0.0"
       }
     },
     "node_modules/shebang-command": {
diff --git a/test/sanity/package.json b/test/sanity/package.json
index 0b281e7a2ca3c..93d586f98e0f1 100644
--- a/test/sanity/package.json
+++ b/test/sanity/package.json
@@ -20,5 +20,8 @@
     "@types/mocha": "^10.0.10",
     "@types/node": "22.x",
     "typescript": "^6.0.0-dev.20251110"
+  },
+  "overrides": {
+    "serialize-javascript": "^7.0.3"
   }
 }
diff --git a/test/sanity/src/context.ts b/test/sanity/src/context.ts
index d04fc6703b4a9..62eee018d0687 100644
--- a/test/sanity/src/context.ts
+++ b/test/sanity/src/context.ts
@@ -38,6 +38,7 @@ export class TestContext {
 	private readonly tempDirs = new Set<string>();
 	private readonly wslTempDirs = new Set<string>();
 	private nextPort = 3010;
+	private currentTestName: string | undefined;
 
 	public constructor(public readonly options: Readonly<{
 		quality: 'stable' | 'insider' | 'exploration';
@@ -47,6 +48,7 @@ export class TestContext {
 		checkSigning: boolean;
 		headlessBrowser: boolean;
 		downloadOnly: boolean;
+		screenshotsDir: string | undefined;
 	}>) {
 	}
 
@@ -88,6 +90,7 @@ export class TestContext {
 
 		const self = this;
 		return test(name, async function () {
+			self.currentTestName = name;
 			self.log(`Starting test: ${name}`);
 
 			const homeDir = os.homedir();
@@ -102,6 +105,8 @@ export class TestContext {
 				throw error;
 
 			} finally {
+				self.currentTestName = undefined;
+
 				process.chdir(homeDir);
 				self.log(`Changed working directory to: ${homeDir}`);
 
@@ -1070,6 +1075,26 @@ export class TestContext {
 		return page;
 	}
 
+	/**
+	 * Captures a screenshot of the current page if one is active.
+	 */
+	public async captureScreenshot(page: Page) {
+		if (!this.currentTestName) {
+			return;
+		}
+
+		try {
+			const screenshotDir = this.options.screenshotsDir ?? path.join(this.osTempDir, 'vscode-sanity-screenshots');
+			fs.mkdirSync(screenshotDir, { recursive: true });
+			const sanitizedName = this.currentTestName.replace(/[^a-zA-Z0-9_-]/g, '_');
+			const screenshotPath = path.join(screenshotDir, `${sanitizedName}.png`);
+			await page.screenshot({ path: screenshotPath, fullPage: true });
+			this.log(`Screenshot saved to: ${screenshotPath}`);
+		} catch (e) {
+			this.log(`Failed to capture screenshot: ${e instanceof Error ? e.message : String(e)}`);
+		}
+	}
+
 	/**
 	 * Constructs a web server URL with optional token and folder parameters.
 	 * @param port The port number of the web server.
@@ -1165,7 +1190,7 @@ export class TestContext {
 			await new Promise<void>((resolve, reject) => {
 				app.stderr.on('data', (data) => {
 					const text = `[${name}] ${data.toString().trim()}`;
-					if (/ECONNRESET/.test(text)) {
+					if (/ECONNRESET|ECONNABORTED/.test(text)) {
 						this.log(text);
 					} else {
 						reject(new Error(text));
diff --git a/test/sanity/src/desktop.test.ts b/test/sanity/src/desktop.test.ts
index abb37db72f009..c2d65c157db1c 100644
--- a/test/sanity/src/desktop.test.ts
+++ b/test/sanity/src/desktop.test.ts
@@ -249,12 +249,13 @@ export function setup(context: TestContext) {
 
 		context.log(`Starting VS Code ${entryPoint} with args ${args.join(' ')}`);
 		const app = await _electron.launch({ executablePath: entryPoint, args });
-		const window = await context.getPage(app.firstWindow());
-
-		await test.run(window);
-
-		context.log('Closing the application');
-		await app.close();
+		try {
+			const window = await context.getPage(app.firstWindow());
+			await test.run(window);
+		} finally {
+			context.log('Closing the application');
+			await app.close();
+		}
 
 		test.validate();
 	}
diff --git a/test/sanity/src/index.ts b/test/sanity/src/index.ts
index 6439018a9b601..60fc2cab5a0ed 100644
--- a/test/sanity/src/index.ts
+++ b/test/sanity/src/index.ts
@@ -10,9 +10,9 @@ import path from 'path';
 import { fileURLToPath } from 'url';
 
 const options = minimist(process.argv.slice(2), {
-	string: ['fgrep', 'grep', 'test-results', 'timeout'],
+	string: ['fgrep', 'grep', 'test-results', 'timeout', 'screenshots-dir'],
 	boolean: ['help'],
-	alias: { fgrep: 'f', grep: 'g', help: 'h', 'test-results': 't' },
+	alias: { fgrep: 'f', grep: 'g', help: 'h', 'test-results': 't', 'screenshots-dir': 's' },
 });
 
 if (options.help) {
@@ -28,6 +28,7 @@ if (options.help) {
 	console.info('  --fgrep, -f <string>            Only run tests containing the given <string>');
 	console.info('  --test-results, -t <path>       Output test results in JUnit format to the specified path');
 	console.info('  --timeout <sec>                 Set the test-case timeout in seconds (default: 600 seconds)');
+	console.info('  --screenshots-dir, -s <path>    Save failure screenshots to the specified directory');
 	console.info('  --verbose, -v                   Enable verbose logging');
 	console.info('  --help, -h                      Show this help message');
 	process.exit(0);
@@ -51,8 +52,22 @@ if (testResults) {
 const mocha = new Mocha(mochaOptions);
 mocha.addFile(fileURLToPath(new URL('./main.js', import.meta.url)));
 await mocha.loadFilesAsync();
-mocha.run(failures => {
+const runner = mocha.run(failures => {
+	if (options.verbose) {
+		console.log(`Mocha test run finished: ${failures} failure(s)`);
+	}
 	process.exitCode = failures > 0 ? 1 : 0;
 	// Force exit to prevent hanging on open handles (background processes, timers, etc.)
-	setTimeout(() => process.exit(process.exitCode), 1000);
+	setTimeout(() => {
+		if (options.verbose) {
+			console.log(`Exiting with code ${process.exitCode}`);
+		}
+		process.exit(process.exitCode);
+	}, 1000);
 });
+
+if (options.verbose) {
+	runner.on('test', (test) => console.log(`Starting: ${test.fullTitle()}`));
+	runner.on('pass', (test) => console.log(`Passed: ${test.fullTitle()}`));
+	runner.on('fail', (test, err) => console.log(`Failed: ${test.fullTitle()} - ${err.message}`));
+}
diff --git a/test/sanity/src/main.ts b/test/sanity/src/main.ts
index cf3a7780350af..840364e68a52a 100644
--- a/test/sanity/src/main.ts
+++ b/test/sanity/src/main.ts
@@ -13,7 +13,7 @@ import { setup as setupServerWebTests } from './serverWeb.test.js';
 import { setup as setupWSLTests } from './wsl.test.js';
 
 const options = minimist(process.argv.slice(2), {
-	string: ['commit', 'quality'],
+	string: ['commit', 'quality', 'screenshots-dir'],
 	boolean: ['cleanup', 'verbose', 'signing-check', 'headless', 'detection'],
 	alias: { commit: 'c', quality: 'q', verbose: 'v' },
 	default: { cleanup: true, verbose: false, 'signing-check': true, headless: true, 'detection': true },
@@ -35,6 +35,7 @@ const context = new TestContext({
 	checkSigning: options['signing-check'],
 	headlessBrowser: options.headless,
 	downloadOnly: !options['detection'],
+	screenshotsDir: options['screenshots-dir'],
 });
 
 context.log(`Arguments: ${process.argv.slice(2).join(' ')}`);
diff --git a/test/sanity/src/serverWeb.test.ts b/test/sanity/src/serverWeb.test.ts
index 4b765c0cd1083..3099ba70d5a6d 100644
--- a/test/sanity/src/serverWeb.test.ts
+++ b/test/sanity/src/serverWeb.test.ts
@@ -91,18 +91,20 @@ export function setup(context: TestContext) {
 
 				const url = context.getWebServerUrl(port, token, test.workspaceDir).toString();
 				const browser = await context.launchBrowser();
-				const page = await context.getPage(browser.newPage());
+				try {
+					const page = await context.getPage(browser.newPage());
 
-				context.log(`Navigating to ${url}`);
-				await page.goto(url, { waitUntil: 'networkidle' });
+					context.log(`Navigating to ${url}`);
+					await page.goto(url, { waitUntil: 'networkidle' });
 
-				context.log('Waiting for the workbench to load');
-				await page.waitForSelector('.monaco-workbench');
+					context.log('Waiting for the workbench to load');
+					await page.waitForSelector('.monaco-workbench');
 
-				await test.run(page);
-
-				context.log('Closing browser');
-				await browser.close();
+					await test.run(page);
+				} finally {
+					context.log('Closing browser');
+					await browser.close();
+				}
 
 				test.validate();
 				return true;
diff --git a/test/sanity/src/uiTest.ts b/test/sanity/src/uiTest.ts
index f6dda6bc1a4a2..65f8b14a49ea1 100644
--- a/test/sanity/src/uiTest.ts
+++ b/test/sanity/src/uiTest.ts
@@ -52,9 +52,14 @@ export class UITest {
 	 * Run the UI test actions.
 	 */
 	public async run(page: Page) {
-		await this.dismissWorkspaceTrustDialog(page);
-		await this.createTextFile(page);
-		await this.installExtension(page);
+		try {
+			await this.dismissWorkspaceTrustDialog(page);
+			await this.createTextFile(page);
+			await this.installExtension(page);
+		} catch (error) {
+			await this.context.captureScreenshot(page);
+			throw error;
+		}
 	}
 
 	/**
@@ -80,9 +85,11 @@ export class UITest {
 	private async runCommand(page: Page, command: string) {
 		this.context.log(`Running command: ${command}`);
 		await page.keyboard.press('F1');
-		await page.getByPlaceholder(/^Type the name of a command/).fill(`>${command}`);
-		await page.locator('span.monaco-highlighted-label', { hasText: new RegExp(`^${command}$`) }).click();
-		await page.waitForTimeout(1000);
+		const input = page.getByPlaceholder(/^Type the name of a command/);
+		await input.fill(`>${command}`);
+		const item = page.locator('span.monaco-highlighted-label', { hasText: new RegExp(`^${command}$`) });
+		await item.click();
+		await input.waitFor({ state: 'hidden' });
 	}
 
 	/**
@@ -125,15 +132,37 @@ export class UITest {
 
 		this.context.log('Typing extension name to search for');
 		await page.getByText('Search Extensions in Marketplace').focus();
-		await page.keyboard.insertText('GitHub Pull Requests');
+		await page.keyboard.type('GitHub Pull Requests', { delay: 50 });
+
+		this.context.log('Waiting for extension to appear in search results');
+		const extensionItem = page.locator('.extension-list-item').getByText(/^GitHub Pull Requests$/);
+		const messageContainer = page.locator('.extensions-viewlet .message-container:not(.hidden)').first();
+
+		for (let attempt = 0; attempt < 3; attempt++) {
+			const result = await Promise.race([
+				extensionItem.waitFor().then(() => 'found' as const),
+				messageContainer.waitFor().then(() => 'message' as const),
+			]);
+
+			if (result === 'found') {
+				break;
+			}
+
+			const message = await messageContainer.locator('.message').innerText();
+			this.context.log(`Marketplace message: ${message} (attempt ${attempt + 1}/3), clicking Refresh`);
+			await page.getByRole('button', { name: 'Refresh' }).click();
+			await messageContainer.waitFor({ state: 'hidden', timeout: 30_000 });
+		}
+
+		await extensionItem.waitFor();
 
 		this.context.log('Clicking Install on the first extension in the list');
-		await page.locator('.extension-list-item').getByText(/^GitHub Pull Requests$/).waitFor();
-		await page.locator('.extension-action:not(.disabled)', { hasText: /Install/ }).first().click();
-		await page.waitForTimeout(1000);
+		const installButton = page.locator('.extension-action:not(.disabled)', { hasText: /Install/ }).first();
+		await installButton.waitFor();
+		await installButton.click();
 
 		this.context.log('Waiting for extension to be installed');
-		await page.locator('.extension-action:not(.disabled)', { hasText: /Uninstall/ }).waitFor();
+		await page.getByRole('button', { name: 'Uninstall' }).first().waitFor({ timeout: 5 * 60_000 });
 	}
 
 	/**
diff --git a/test/sanity/src/wsl.test.ts b/test/sanity/src/wsl.test.ts
index ab2c581763460..77df84d72758f 100644
--- a/test/sanity/src/wsl.test.ts
+++ b/test/sanity/src/wsl.test.ts
@@ -117,18 +117,20 @@ export function setup(context: TestContext) {
 
 				const url = context.getWebServerUrl(port, token, wslWorkspaceDir).toString();
 				const browser = await context.launchBrowser();
-				const page = await context.getPage(browser.newPage());
+				try {
+					const page = await context.getPage(browser.newPage());
 
-				context.log(`Navigating to ${url}`);
-				await page.goto(url, { waitUntil: 'networkidle' });
+					context.log(`Navigating to ${url}`);
+					await page.goto(url, { waitUntil: 'networkidle' });
 
-				context.log('Waiting for the workbench to load');
-				await page.waitForSelector('.monaco-workbench');
+					context.log('Waiting for the workbench to load');
+					await page.waitForSelector('.monaco-workbench');
 
-				await test.run(page);
-
-				context.log('Closing browser');
-				await browser.close();
+					await test.run(page);
+				} finally {
+					context.log('Closing browser');
+					await browser.close();
+				}
 
 				test.validate();
 				return true;
@@ -152,18 +154,20 @@ export function setup(context: TestContext) {
 
 		context.log(`Starting VS Code ${entryPoint} with args ${args.join(' ')}`);
 		const app = await _electron.launch({ executablePath: entryPoint, args });
-		const window = await context.getPage(app.firstWindow());
+		try {
+			const window = await context.getPage(app.firstWindow());
 
-		context.log('Installing WSL extension');
-		await window.getByRole('button', { name: 'Install and Reload' }).click();
+			context.log('Installing WSL extension');
+			await window.getByRole('button', { name: 'Install and Reload' }).click();
 
-		context.log('Waiting for WSL connection');
-		await window.getByText(/WSL/).waitFor();
+			context.log('Waiting for WSL connection');
+			await window.getByText(/WSL/).waitFor();
 
-		await test.run(window);
-
-		context.log('Closing the application');
-		await app.close();
+			await test.run(window);
+		} finally {
+			context.log('Closing the application');
+			await app.close();
+		}
 
 		test.validate();
 	}
diff --git a/test/smoke/src/areas/accessibility/accessibility.test.ts b/test/smoke/src/areas/accessibility/accessibility.test.ts
index ac3868eb55b74..7c7e3689c0a5e 100644
--- a/test/smoke/src/areas/accessibility/accessibility.test.ts
+++ b/test/smoke/src/areas/accessibility/accessibility.test.ts
@@ -34,7 +34,7 @@ export function setup(logger: Logger, opts: { web?: boolean }, quality: Quality)
 					selector: '.monaco-workbench',
 					excludeRules: {
 						// Links in chat welcome view show underline on hover/focus which axe-core static analysis cannot detect
-						'link-in-text-block': ['command:workbench.action.chat.generateInstructions'],
+						'link-in-text-block': ['command:workbench.action.chat.generateAgentInstructions'],
 						// Monaco lists use aria-multiselectable on role="list" and aria-setsize/aria-posinset/aria-selected on role="dialog" rows
 						// These violations appear intermittently when notification lists or other dynamic lists are visible
 						// Note: patterns match against HTML string, not CSS selectors, so no leading dots
@@ -85,7 +85,7 @@ export function setup(logger: Logger, opts: { web?: boolean }, quality: Quality)
 						selector: 'div[id="workbench.panel.chat"]',
 						excludeRules: {
 							// Links in chat welcome view show underline on hover/focus which axe-core static analysis cannot detect
-							'link-in-text-block': ['command:workbench.action.chat.generateInstructions']
+							'link-in-text-block': ['command:workbench.action.chat.generateAgentInstructions']
 						}
 					});
 				});
@@ -109,15 +109,19 @@ export function setup(logger: Logger, opts: { web?: boolean }, quality: Quality)
 					// Send a simple message that does not require tools to avoid external path confirmations
 					await app.workbench.chat.sendMessage('Explain what "Hello World" means in programming. Include a short fenced code block that shows "Hello World".');
 
-					// Wait for the response to complete (1500 retries ~= 150 seconds at 100ms per retry)
-					await app.workbench.chat.waitForResponse(1500);
+					// Wait for the response to complete - skip test if AI service is unavailable
+					try {
+						await app.workbench.chat.waitForResponse(1500);
+					} catch {
+						this.skip();
+					}
 
 					// Run accessibility check on the chat panel with the response
 					await app.code.driver.assertNoAccessibilityViolations({
 						selector: 'div[id="workbench.panel.chat"]',
 						excludeRules: {
 							// Links in chat welcome view show underline on hover/focus which axe-core static analysis cannot detect
-							'link-in-text-block': ['command:workbench.action.chat.generateInstructions'],
+							'link-in-text-block': ['command:workbench.action.chat.generateAgentInstructions'],
 							// Monaco lists use aria-multiselectable on role="list" and aria-selected on role="listitem"
 							// These are used intentionally for selection semantics even though technically not spec-compliant
 							'aria-allowed-attr': ['monaco-list', 'monaco-list-row'],
@@ -149,15 +153,19 @@ export function setup(logger: Logger, opts: { web?: boolean }, quality: Quality)
 					// Send a terminal command request
 					await app.workbench.chat.sendMessage('Run ls in the terminal');
 
-					// Wait for the response to complete (1500 retries ~= 150 seconds at 100ms per retry)
-					await app.workbench.chat.waitForResponse(1500);
+					// Wait for the response to complete - skip test if AI service is unavailable
+					try {
+						await app.workbench.chat.waitForResponse(1500);
+					} catch {
+						this.skip();
+					}
 
 					// Run accessibility check on the chat panel with the response
 					await app.code.driver.assertNoAccessibilityViolations({
 						selector: 'div[id="workbench.panel.chat"]',
 						excludeRules: {
 							// Links in chat welcome view show underline on hover/focus which axe-core static analysis cannot detect
-							'link-in-text-block': ['command:workbench.action.chat.generateInstructions'],
+							'link-in-text-block': ['command:workbench.action.chat.generateAgentInstructions'],
 							// Monaco lists use aria-multiselectable on role="list" and aria-selected on role="listitem"
 							// These are used intentionally for selection semantics even though technically not spec-compliant
 							'aria-allowed-attr': ['monaco-list', 'monaco-list-row'],
diff --git a/test/unit/node/index.js b/test/unit/node/index.js
index 4dc32d7a0cf35..3f9d4a8424207 100644
--- a/test/unit/node/index.js
+++ b/test/unit/node/index.js
@@ -60,7 +60,8 @@ const excludeGlobs = [
 	'**/{browser,electron-browser,electron-main,electron-utility}/**/*.test.js',
 	'**/vs/platform/environment/test/node/nativeModules.test.js', // native modules are compiled against Electron and this test would fail with node.js
 	'**/vs/base/parts/storage/test/node/storage.test.js', // same as above, due to direct dependency to sqlite native module
-	'**/vs/workbench/contrib/testing/test/**' // flaky (https://github.com/microsoft/vscode/issues/137853)
+	'**/vs/workbench/contrib/testing/test/**', // flaky (https://github.com/microsoft/vscode/issues/137853)
+	'**/vs/sessions/test/web.test.js', // web-only E2E test that imports CSS — cannot run in Node
 ];
 
 const REPO_ROOT = fileURLToPath(new URL('../../../', import.meta.url));
@@ -104,7 +105,7 @@ function main() {
 		__mkdirPInTests: (/** @type {string} */ path) => fs.promises.mkdir(path, { recursive: true }),
 	});
 
-	process.on('uncaughtException', function (e) {
+	process.on('uncaughtException', function(e) {
 		console.error(e.stack || e);
 	});
 
@@ -113,7 +114,7 @@ function main() {
 	 * @param onLoad
 	 * @param onError
 	 */
-	const loader = function (modules, onLoad, onError) {
+	const loader = function(modules, onLoad, onError) {
 		const loads = modules.map(mod => import(`${baseUrl}/${mod}.js`).catch(err => {
 			console.error(`FAILED to load ${mod} as ${baseUrl}/${mod}.js`);
 			throw err;
@@ -124,7 +125,7 @@ function main() {
 
 	let didErr = false;
 	const write = process.stderr.write;
-	process.stderr.write = function (...args) {
+	process.stderr.write = function(...args) {
 		didErr = didErr || !!args[0];
 		return write.apply(process.stderr, args);
 	};
@@ -162,11 +163,11 @@ function main() {
 				loadModules(modulesToLoad).then(() => cb(null), cb);
 			};
 
-			glob(args.runGlob, { cwd: src }, function (err, files) { doRun(files); });
+			glob(args.runGlob, { cwd: src }, function(err, files) { doRun(files); });
 		};
 	} else if (args.run) {
 		const tests = (typeof args.run === 'string') ? [args.run] : args.run;
-		const modulesToLoad = tests.map(function (test) {
+		const modulesToLoad = tests.map(function(test) {
 			test = test.replace(/^src/, 'out');
 			test = test.replace(/\.ts$/, '.js');
 			return path.relative(src, path.resolve(test)).replace(/(\.js)|(\.js\.map)$/, '').replace(/\\/g, '/');
@@ -176,7 +177,7 @@ function main() {
 		};
 	} else {
 		loadFunc = (cb) => {
-			glob(TEST_GLOB, { cwd: src }, function (err, files) {
+			glob(TEST_GLOB, { cwd: src }, function(err, files) {
 				/** @type {string[]} */
 				const modules = [];
 				for (const file of files) {
@@ -189,7 +190,7 @@ function main() {
 		};
 	}
 
-	loadFunc(function (err) {
+	loadFunc(function(err) {
 		if (err) {
 			console.error(err);
 			return process.exit(1);
@@ -199,8 +200,8 @@ function main() {
 
 		if (!args.run && !args.runGlob) {
 			// set up last test
-			Mocha.suite('Loader', function () {
-				test('should not explode while loading', function () {
+			Mocha.suite('Loader', function() {
+				test('should not explode while loading', function() {
 					assert.ok(!didErr, `should not explode while loading: ${didErr}`);
 				});
 			});
@@ -208,10 +209,10 @@ function main() {
 
 		// report failing test for every unexpected error during any of the tests
 		const unexpectedErrors = [];
-		Mocha.suite('Errors', function () {
-			test('should not have unexpected errors in tests', function () {
+		Mocha.suite('Errors', function() {
+			test('should not have unexpected errors in tests', function() {
 				if (unexpectedErrors.length) {
-					unexpectedErrors.forEach(function (stack) {
+					unexpectedErrors.forEach(function(stack) {
 						console.error('');
 						console.error(stack);
 					});
@@ -223,7 +224,7 @@ function main() {
 
 		// replace the default unexpected error handler to be useful during tests
 		import(`${baseUrl}/vs/base/common/errors.js`).then(errors => {
-			errors.setUnexpectedErrorHandler(function (err) {
+			errors.setUnexpectedErrorHandler(function(err) {
 				const stack = (err && err.stack) || (new Error().stack);
 				unexpectedErrors.push((err && err.message ? err.message : err) + '\n' + stack);
 			});